I knew something wasn't quite right in my parent's marriage, but didn't know what. Mom had been sleeping on the couch for several years, while Daddy slept in the master bedroom, and he seemed to go to bed early each night. One Saturday morning Mom had taken the rest of the brood shopping (I was oldest of six) and I was home alone with Daddy. He called me into his bedroom and had me sit down on the edge of his bed for a talk. He was just in a robe and seemed nervous.
What made him nervous was "the talk". I was about thirteen and had already discovered the joys of masturbation - I was rubbing up against a little pillow - humping up against it. In fact, I couldn't stop doing it. I would rub myself off three or four times a day! Daddy started asking me if I was masturbating, and I told him what I was doing. Guess he had seen the telltale stains on my little cum pillow. He told me to strip and instructed me in the proper way to masturbate, as well as tell me what sex was all about. I was fascinated, and listened intently. A lot of it seemed kind of gross, but I listened and tried to learn. He had me practice stroking myself in front of him, to make sure I was doing it right, he said, and decided I wasn't doing it properly. He knelt down between my legs and put his big hands on my little cock.
"Does that feel good, Donny?"
"Yes, Daddy!"
"This is the way to properly beat off , son. Back and forth... why don't you lay down and relax." You have a nice little cock, son. It's not very big, but it sure is hard. I imagine it will grow up as big as mine."
I leaned back and laid myself down on the white chenille bedspread, my legs wide open, and let Daddy stroke my young cock. It felt really great, and my little cock was really hard. I had a little bit of hair down there, but none on my boy balls.
I was enjoying the feeling of that big hand on my tool, and the other hand stroking the inside of my thighs, up under my balls. I just closed my eyes and went with it.
Suddenly I felt something warm and hot engulf my little cock. I leaned up and saw Daddy with my cock in his mouth. He used a hand to softly push me back down on the bed.
"This is what's called a blowjob, Donny. Doesn't it feel great?"
Yes it did! It was incredible, and the way his tongue was licking my cock, then my smooth balls and down below them was really making me horny. He sensed this and took the entire shaft back into his mouth. I shuddered and knew my boycum was churning in my little balls and would soon erupt into Daddy's hot mouth if I didn't warn him.
"Daddy you'd better stop doing that! I'm getting ready to shoot!"
His big hand just pushed me back down on the bed and I couldn't help it - I arched my back and shot like crazy into Daddy's mouth! He was making growling groaning noises as he swallowed all of my cum. He then licked me clean all over as I laid there and tried to sort out what just happened. I knew what had happened was wrong - wasn't it? But it sure felt good. I was all sticky and wet down between my legs, and I liked the feeling
I sat up and when I did I could see Daddy was standing before me, his face was all wet and his robe was wide open. Daddy was a big man - 6'4" tall - and had no body hair. His cock was huge - and unlike mine had a foreskin, which fascinated me. It was big - it had to be about 10 inches long and the skin was pulled back at the tip revealing a purple head, and a little drop of clear liquid at the tip only a foot or so from my face.
I looked up at Daddy.
"Touch it son, feel what a grown man's cock feels like."
I reached out and touched it. It was hot. I grabbed it and stroked it a few times, enjoying the feeling of the skin sliding over the shaft in my hand.
"Good Boy! See how happy you're making it? You have the touch, son."
I smiled. It made me happy to please him, and to receive his praise. I didn't often get it.
"You know, Donny - I will teach you all you need to know about sex, but this is guy stuff - and it's between us. You can't talk to anyone else about this. Now that's enough for now. You get dressed and I'll meet you in the living room in a little while. We have some chores to do."
I reluctantly took my hand off his big Daddy cock , left the bedroom and he closed the door. He was in there for awhile and I listened at the door. I think he was masturbating himself from the sounds he was making. Like a good boy I went to the living room and waited for him, anxious for our next lesson on sex and being a man.
I wondered why he had used his mouth on me like that, and figured my cum must taste allright. I had never thought to taste it - but I decided I would the next time I jacked off, to see what it was like. If it was good enough for Daddy it should be good enough for me.
After the mind blowing experience of having my Dad sucking on my young cock my interest in sex really exploded. I had so many questions - so many nasty thoughts. I wondered what a cock tasted like, and wondered why Daddy's body was so smooth, and why he and Mommy didn't sleep together. I was soon to be exposed to a world I never imagined.
A few weeks later Daddy and I were again alone in the house. It was late morning, and Mom and the girls had gone out somewhere. Daddy and I were to work on some kind of home improvement project that day. He called to me from his room and I went in to find him pacing in his bathrobe. He had me sit on the edge of the bed and I eagerly awaited what was to come - I hoped it was something sexy!
Daddy seemed very upset - he was trying to tell me something. He finally told me that he had been living a secret life for some time - he like to dress in women's clothes! How weird, I thought! I felt sorry for him because he seemed so upset confessing to me. I told him it was OK, he was still my Daddy, and he smiled. He then opened his robe and my mouth dropped when I saw my Daddy wearing what I now know to be a vintage lady's girdle in a pale gold color, and a matching bra and panties. The first thing I noticed was how big his cock looked in the silky golden panties.
He studied my face for a reaction and I just smiled back at him. I didn't really mind him doing this, it was his business after all - and I felt honored he trusted me enough to share this secret. He came over and sat on the bed and hugged me, obviously relieved.
"Daddy, why do you wear this stuff?"
"Because Donny it makes me feel good."
"Your outfit is very pretty, Daddy. Can I touch it?"
He placed my hand on his bra, and I then worked my way down his girdle to feel the panties he was wearing. I was bold and rubbed my hand over the outline of his cock in the panties. It jumped when I did that.
Daddy leaned his head back and moaned, and spread his legs as I explored his feminized body with my hands. His frillies felt so nice...such a contrast from the itchy white cotton undies I always wore.
"When I'm dressed like this you must call me Jane, Donny. This is my "femme" name."
I giggled. "OK' Jane. Your underwear sure is pretty - and feels very sexy?"
Jane leaned over and kissed me. Not a parent to child kiss, but a woman to man kiss like I saw on TV. It was really weird. Jane put her hand on my jeans and felt my little cock hardening in my pants.
This was so weird - it was like I was with a different person. Jane was still very much in charge, just like Daddy. It's as if because he was Jane he had lost his inhibitions.
Jane unzipped my jeans and pulled them down along with my underpants. She pulled me up to a position lying on top of the bed and lay next to me, although she was facing the other way.
Turning me on my side Jane took my young cock into her mouth and started to suck it like mad. I just moaned, and she was right next to me with her cock straining against her panties. I could see a wet spot, and I decided to pull down her panties. Her big cock popped out and she moaned. I took my hand and tried to wrap it around the monster.
Jane's cock was a good 10 inches long, thick and smooth. Unlike me it was uncircumcised, and that fascinated me. I moved the skin back and forth and it got even harder. I was stroking Jane's cock when I couldn't stand it any more and my own little cock exploded into Jane's mouth.
Jane moaned and swallowed every drop as I shook.
"That's enough for today", Jane said, and she got off the bed. "Get dressed now and I'll do the same".
I got myself all zipped up and went outside to wait for Daddy. He came out about a half hour later in his normal clothes, but I could see the outline of a bra strap under his shirt.
I felt very special, like my Dad and I had shared something unique. Daddy talked to me a bit later, and made me promise to keep his secret of his life as Jane.
The next few weeks went on as though nothing had ever happened. I happened to be alone in the house one day and I knew it was safe, so I stripped down for a nice jack off session. I loved to stroke myself and cum two or three times in a row.
After the first jack off, which was pretty quick and extremely spermy, I got curious and went into Daddy's room. I carefully went through his dresser and then his closet until I found where he hid Jane's clothes. He had them in a soft-sided suitcase way in the back of the closet. I pulled it out and carefully opened it on the floor.
Inside were all kinds of feminine articles! I found bras, panties, some girdles, and stockings and what I now know to be garter belts. It was amazing! All these pretty things...the pretty pastel colors! I took a particularly silky pair of pink panties and rubbed it over my face...it felt so smooth! I wondered what it would feel like against my cock and balls.
Standing up, I nervously stepped first one, then my second foot into the leg openings of the panties. A slowly pulled them up.
To this day I can still remember the thrill of being pantied. The feelings of the luxurious panties enveloping my cock, balls and ass. I got super hard immediately!
Continuing to rummage through Jane's things I found a slender white plastic cylinder that had ribs on it. I turned the dial at the bottom and it became alive in my hand! It felt really sexy! I took it and rubbed it over the top of my pantied cock and it felt incredible. I then explored with it, and rubbed it all over the panties, front and rear. It really excited me having it up against my pantied cheeks, and I lowered the front of the panties and stroked my aching hardon until I shot huge globs of boycum all over the place. I think some ended up on the panties, and in the suitcase of Jane's clothes below me.
I was scared and got out of the panties, cleaned up and tried to put everything back where I found it. I managed to get it all together with only a few minutes to spare before my family returned.
Later that night, alone in bed, with my hand on my cock I tried to sort out what happened today. I guess I understood a little why Daddy liked to be Jane. I knew it was kind of weird, but I liked wearing her things, and the way that vibrating thing felt poking around my private parts. I knew I could tell no one about this. Daddy would probably be very angry if he knew I was in Jane's things. I decided to keep it to myself and to try to not think about it too much. But when I stroked off before going to sleep all I could think about was wearing those panties and feeling that vibration between my butt cheeks.
It had been a few months since my big strong ironworker Daddy had admitted to me his secret life as a cross dresser, and introduced me to Jane, his alter ego. The visits from Jane were sporadic, although I was always on the lookout for telltale signs.... a glimpse of pink panties peeking out from under the waistline of his pants, or realizing Daddy was wearing a brassiere while helping me with my homework.
The talks about sex and protecting myself occurred every few weeks or so, and I sometimes used those opportunities to ask Daddy about dressing up. Yes, he wore more than lingerie - he had dresses and heels, makeup and a few wigs. And he admitted he shaved his legs to feel a little extra "girly" when he wore stockings. Hmmm, I wonder what those feel like?
I made sure I investigated the panty wardrobe the other girls in the house owned. Mommy's panties were rather boring - all white, and with a good deal of cotton, which frankly did nothing for me when I rubbed them up against my little equipment. My sister Suzy though had more interesting tastes. She was 2 years younger and I found her panties to be all silky - nylon or satin - and some had ruffles or little floral accents.
I was like Goldilocks....Daddy Jane's panties were ever so big but very pretty; Mommy's were smaller yet boring....Suzy's panties were... just right! They fit me so tightly and gave me an incredible rush whenever I wore them, which was pretty often. I tried to stay away from them, telling myself that boy's don't wear panties...I even prayed at church for the strength to resist the temptation of encasing my little cock and balls in the ecstasy of silk. But it was no use...I was hooked.
A few panties I simply could no longer share with their real owners, and I decided to keep them for myself. I found a small gym bag and kept my absolute favorites where I could get at them whenever the need overtook me. There were a pair of the sheerest pale gold panties I stole from Jane....they were the silkiest ones I had ever seen, and after I had filled them with an incredible load of boycum I figured getting rid of that copious stain was impossible...they were mine now! I didn't really want any of Mommy's boring panties....but poor Suzy must have thought either she was going crazy or our clothes dryer was a panty eating machine as she lost 2 of her frilliest silkiest pairs....her lime green silk panties with yellow daisies framed my hard cock so sweetly, they were tight and pushed my little balls flat to my body, and when I turned to examine how I looked in the mirror they had a seam up the back that even at my young age filled me with excitement at the way they clung to my smooth round cheeks, and then there were the hot pink ones....every sissyboy should have a pair of hot pink panties - don't you think? They were so pretty and felt incredible on me. This was the first of many stashes I would make during my young life of sexy girly things.
The thrill of putting them on - of being in panties - was so arousing to me....watching and feeling the panties slide up my smooth legs and then snugly into place always made me shiver and made my cock jump. I discovered baby powder - how nice it smelled and how smooth it made my skin feel - and I began using it liberally after a shower and before pantying myself or jacking off.
Since Jane had sucked my young cock a few times and swallowed my jiz I began to wonder what it tasted like, and one day after a nice cum I licked some of my hot load from my fingers. I found the taste to be not unpleasant, and from then on usually tasted at least a bit every time I came. If I accidentally came in a pair of my secret panties I would remove them and sometimes clean them with my mouth, leaving the soiled panties laying over my face and sucking off the slimy goo from underneath.
My occasional visits to my father's bedroom...I had become very efficient at searching drawers and closets without detection....yielded several new surprises...nudist magazines! They were hidden in a big manila envelope that said "Dick's Welding Shop". The black and white magazines were intended to promote the healthful aspects of the nudist lifestyle...pictures of men and women playing volleyball nude, casually chatting...it was wild! I must admit that I was more interested in the pictures of the naked men rather than the naked women...even at that young age, noting the sizes and shapes of their cocks and their firm round asses and their muscles.
It was around this time that my family had to sell our home to accommodate a new junior college to be built on our property, those of my neighbors, and the huge sod farm right behind us. It was a very exciting time and my parents bought us a lovely older home about an hour way from us, in the far west suburbs of Chicago. We had several months to move, and Daddy and I began the process of moving our belongings out to the new house every weekend. It usually involved just the two of us staying overnight there to unpack and it was during those times that Jane felt safe and bold enough to dress fully before me, and spend her evenings with me watching TV en femme. Jane was and is a tall girl - 6'4" and did her best to be feminine and pretty - and I encouraged her. I would sometimes dress in a way that accentuated my young body and tease her - I know it was wicked! Sometimes I would get a lipsticked kiss on the cheek or the lips, an occasional grope and every now and then a blowjob. I would wear my tight white BVDs around her, or sometimes nothing at all, and I must have been driving her crazy! I know she felt guilty after sucking me off and then there would be a dry spell and Jane would hide from me.
One late Saturday afternoon, after unpacking, Daddy stripped down to his white nylon boxers (the only kind of male undies he wore) and decided to nap on the newly moved couch in the new living room. I was instructed to wake him in 2 hours. And knew if I didn't do so there would be hell to pay. Daddy was not above taking me over his knee when angry. I explored our new house and property for 2 hours and went in to wake him. It was hot, and I was in a pair of skimpy shorts. Daddy was on his side, snoring lightly and facing the back of the couch, his long body filling the couch. I nudged him a few times.
"Daddy, it's time to wake up - it's 6:00...c'mon..."
A grunt was all I got.
"C'mon Daddy it's been over 2 hours..."
Try as I might he just wasn't waking. This went on for a good half an hour. I would get as grunt or a mumble but that was it. I decided to kneel and then sit down beside him on the carpet since this was going to take a while. I was positioned near his butt, and kept nudging him every few minutes, annoyed at his reluctance to wake and that this was somehow going to be all my fault that he overslept.
I nudged him yet again, and he rolled completely over so that the front of his body was facing me. His body was smooth and hairless, and well muscled. I gasped when I saw that he had a hard on, and it was sticking out of the fly of his boxers and was right by my face. Daddy was uncircumcised and the skin was pulled back a bit and the tip of his cock revealed a small drop of precum. I sat there for a few minutes staring at the monster - it had to be 10 inches long, and seemed to be growing before me. Daddy was still sleeping and snoring a bit.
It fascinated me. It was so big, so juicy looking. I wrestled with my emotions and then slowly leaned closer to smell it. It smelled hot and sticky.
I wanted it!
Sticking out my tongue I touched the gob of sticky precum at the tip and shuddered. I licked it clean and wanted more. I was shaky I was so turned on, and my own cock was hard as a rock. I watched Daddy's face for a reaction - there was none.
I scooted closer and licked the hot head - it was a different taste...not unpleasant...I loved the way his skin tasted. I found I could move his foreskin back and forth with my mouth. I didn't have a foreskin, so this was really exciting to me. My eager mouth encircled the entire head and began to suck. I moved my mouth down over the foreskin and found I had taken about 3 inches of the shaft into my mouth. It felt so hot, so dirty to be doing this...he stirred in his sleep, several inches of his throbbing cock down my throat. Whew, that was close! He was still sleeping! I figured I'd take a few more sucks from the cock that created me before I got caught. Oh, it was so good...it felt so natural, so right in my mouth!
"Take more of it"
I shot a glance up at Daddy, who was obviously awake now!
"I can't, it's too big!" I looked directly into his eyes, and he did the same to me.
I felt my Daddy's big hand reach over and hold the back of my head, caressing my hair.
"You have to learn!"
And with that Daddy took control and forced another couple inches of cock into his son's throat. I accepted my submissive position and let him take over and fuck my face. It felt wonderful! He told me to relax my throat muscles and breathe through my nose, and I found I could take more and more of it down my throat.
Daddy said I had to learn, so I tried my best. I was rewarded with the thrill of his cock pulsing in my mouth, and filling me with his hot cum. There was so much I felt a little dribble out of my mouth as I gulped down what I could. I swear I saw stars when he shot in my mouth, and my own cock spurted into my shorts. He wiped his dribbling cum off my cheeks and fed me his sticky fingers, which I licked clean.
"That's right...always swallow every drop of a man's cum, Donny. Don't waste any! You're a natural cocksucker I think!"
I smiled and softly nursed on his softening cock and he let me just suck on it for a while - a good 15 or 20 minutes nursing on it. I could feel it getting hard again but he pulled me off it, and told me to clean up as we had some work to do.
Not another word was said that day about the whole incident. I was a cocksucker now, and it had been by my own choice. Nothing would ever be the same for me.
After the mind blowing experience of sucking my Dad's cock I was full of all kinds of thoughts and questions about myself, and who I really was. My friends at school were all kind of nerdy achievers and frankly there wasn't much talk amongst us about sex. None of us had girlfriends or talked much about girls. I imagine they, like myself masturbated privately. Two of my friends were identical twin guys and I started fantasizing about the two of them getting it on, and joining them for a twin sandwich. After sucking a cock, and wearing panties and things I was looking at my friends in a whole new light. When we had gym class I would casually check out the other boys in the shower and while changing. A lot of them were so much further developed than me.
Bruce Hartman was a neighbor who rode on the same bus I did. He was the leader of a small gang of guys who were into dirt bikes and tearing around the local countryside. He was about 6 foot tall and really built - he had muscles like you wouldn't believe. One day after gym class I entered the shower and there he was - nude. He was blonde and fair skinned. The water from the shower cascaded over his chest and down between his legs, where he was equipped with a meaty soft 6 inches of cock, full balls, and a lot of pubic hair. He was soaping himself and he saw me openly staring at him. He just smiled at me - that smile that said, "I know you want me, fag" and turned around, giving me a shot of his firm round butt cheeks. I tried to regain control and soaped quickly and showered and got out of there - but we both knew I wanted him. From that point on he always looked right through me, and I started wondering if I would ever have a girlfriend and be a normal guy. I also wondered what it would be like to worship Bruce's hot cock and eat his cum.
At home I was still slipping into silky panties whenever I had the chance. I always had my most powerful orgasm while my balls were encased in silk. I was out looking for something in the garage one day and up in the rafters I found a big box that interested me. When I pulled it down and opened it I was thrilled to discover it was filled with all kinds of feminine things!
A jackpot!
This must have been Jane's backup wardrobe...things collected through the years that didn't quite fit right or were replaced with something that suited her fancy more. My cock was hard in my jeans as I started sorting through the box. I immediately stripped naked and started dressing up - right there in the garage! I found a small white girdle of very shiny nylon spandex and slipped it on. It felt incredible, the way it smashed my cock and balls flat and pushed in my tummy and gathered the excess at the top, making my chest more fleshy. I kept poking through, feeling all of the delightful silky panties and bras, and found a pretty light pink full slip, which I put over it. The material slid across my nipples making them harden and me shudder. There were even some heels in the box, and a few skirts and blouses, carefully folded. I put my boy clothes back on over the slip and girdle and took a small bag with a few other things - a white cotton blouse and a plaid pleated skirt. I couldn't wait to try them on! I carefully put the box back where I found it up in the rafters and snuck back into the house without raising any suspicion.
Daddy was nowhere to be found. I imagined he was locked in his room the way he was most evenings - dressed up as Jane and enjoying his feminine life.
I went to my room and locked the door. I stripped out of my boy clothes and put on the pretty white cotton blouse. It was a little big but when I slipped on the skirt I tucked it all in and it looked pretty good. I couldn't help myself - I twirled in front of the mirror and giggled as I enjoyed the sensation of being a girl. I fell back on my bed, spread my legs, undid the snap crotch on the girdle and freed my boy parts. I stroked myself and got so hard it was painful. I imagined being with my neighbor Bruce - and he was feeling me up under the skirt. I shot gallons of cum all over myself, and licked up a good deal of it. I imagined it was Bruce's cum and I got all shaky and my cock twitched.
The following night - it was late. I was sitting in a recliner in the living room, wearing only a robe as I had just showered. The smell of baby powder that I had liberally applied all over myself was powerful. It made me feel clean fresh and somehow pure. I was in the perfect line of sight to see my father's bedroom door. I heard something and when I glanced down there I noticed the door was open a little and he had his robe open. He was looking right at me, and under the robe he was wearing a pale blue nightie and I could see his big cock was fully hard and sticking straight out. He looked into my eyes as he peeled back the foreskin slowly a few times.
There was no one else awake in the house so I quietly got up, walked down the hall, and pushed open his door and entered. I closed the door and walked over to him. Without saying a word I dropped to my knees and kissed the head of his cock and he sighed. I took a few inches in, holding the shaft and moving the foreskin back and forth in my mouth. I found I could slide my tongue under the skin and Jane really seemed to like that. My own cock, all covered in baby powder, was stiff. The blue nightie was dropped over my head and I was surrounded by silk and the aroma of hot cock and balls full of hot sperm.
Jane pulled me to my feet and kissed me full on the lips - not a parental kiss, but a kiss two lovers would enjoy. Jane forced her tongue into my mouth and I felt her wet erection poking at my soft tummy. Jane then broke our kiss and dropped down to her knees. She devoured the entire length of my cock and I fought back the urge to moan. I began shaking. Suddenly Jane arose and kissed me again, putting my hand around her throbbing cock. With her other hand she put a glob of Vaseline on her finger and proceeded to poke it between my butt cheeks at my tight little hole.
Wow! What a feeling! It was incredible the way she worked that sticky finger in and out of me. I knew what was happening was wrong but it felt fantastic...and I didn't want it to stop. Jane worked a second finger in and I couldn't help but moan. She put her other hand over my mouth and I got the message.
Jane then turned me around and rubbed my bottom as she kissed my neck. I felt her hard cock poking at me, and then she held me tight and pushed the intruder at my tight little hole. I froze up and she whispered at me to relax. I felt he head of that big cock poke into my hole. The pain! I thought I would scream but I didn't. She tried to push more in but standing like that - me bracing myself against her tall dresser, my robe at my feet - it just wasn't going any further into me. She just kept it there - about three inches or so inside my virgin hole and she felt my body all over, rubbing and pinching my nipples. She felt down between my legs and found that my cock had gone completely soft and my balls were shrunken. Though my cock was almost always hard or at least jerking around it was now so small it was like it was retreating into my body.
To this day the same thing happens whenever a man fucks me. Even sometimes when I am dressing up for a new date and I'm trying to be 100% female...it's as if my mind is telling me I'm a girl and I shouldn't have a penis...it withdraws into my body like a frightened turtle. It actually turns me on since it's such a small nub at this point. I've found it's an incredible turn on both for my men and me when they take their hard manly cocks and push the head of their cocks directly against my little nub and make it disappear. It makes them feel more manly and dominant. And it makes me feel ever so submissive! In fact one of my guys likes to poke it at until he shoots all over me, and I pull up my panties and feel his stickiness inside them.
So here I am, late at night, my Dad is dressed as Jane and has his hard cock a few inches into my incredibly tight boy hole....I think we both knew it wasn't going in any farther.
I felt so helpless. I knew I was being used, but it somehow seemed right. I tried to open my hole more to accept my fate. Another inch slid in and I could feel it all the way to my toes. I started to panic, wondering if I was expected to take the entire 10 inches of cock that created me.
Jane pulled out, dropped down to her knees and used her mouth to make my little boycock all hard again, and when it was rock solid she applied some Vaseline to it and turned her back to me, raising her nightie, and guided my cock into her hot hole.
It was wild...so hot in there...and Jane tensed up at first then relaxed. She had no problem taking my 4 inches of dick. I started humping and she was shaking. I couldn't help it - I shot my load into her tight hole.
My first fuck....my Daddy lover Jane.
After having a cock a few inches inside my young bottom a whole new area of pleasure had been opened up to me. Yes, it hurt - but it was also terribly exciting! And my masturbation sessions now almost always invariably included silky panties or more, and me fingering my tight little hole.
I wasn't so keen on putting my own cock into another hole though...what I was craving was a pair of big strong hands massaging my firm young butt through a pair of silky panties, having them roughly pulled down and then a wet finger forcing it's way inside me, opening me up as I wiggled and moaned and was unable to stop what was happening.
A few weeks after the intrusion into my hot little hole Daddy called me into his room one Saturday afternoon for a little chat. I should say it was Jane who called me in - as he was in full dress with a shoulder length brown wig and makeup. Jane was wearing a royal blue silk blouse and a tight black skirt, black stockings and black heels. I thought she looked pretty hot.
"Wow! You look great today. I really like the blouse and the skirt!"
"Umm, thanks, son", Jane blushed.
"Donny, we need to have a talk. You're not into this shit, are you?"
"What shit?"
"You know - the dressing up."
I swallowed hard. The way Jane said it and looked at me sternly I knew what she wanted me to say and I said it.
"No, but I don't mind it when you do it."
She seemed relieved. What she didn't know is under my T-shirt and shorts I was wearing a pair of Suzy's pink panties, and I had been wearing them all day. I had begun wearing panties most of the time under my boy clothes. I loved the way they felt, and I couldn't stand wearing itchy white cotton BVDs any more. The panties just felt right for me - they were smooth and made me feel sexy.
"You know, son we've done some things I'm not too proud of. I don't want you to think I've forced you to do things against your will. But I have to ask you- how do you feel about what we've done?"
I thought carefully before answering.
"We were just messing around, Dad - having fun, right?"
"Yes, but it seems like you really like sucking on my cock - do you think you're becoming gay? Have you sucked any other cocks?"
"Oh No, Daddy! Just yours!"
"What did you think about fucking?"
"It hurt. A lot. I think your cock is too big for me! I'm not sure I liked that too much."
"Well, that's good, because you know pretty soon you will be fucking around with girls and this will all be behind you! Otherwise you may end up being a homosexual - gay!"
He said it like it was a really bad thing. I received a long talk about women and the excitement of making love to them. I listened of course, but the thought of me being the aggressor in sex just didn't seem right for me. As he talked instead of putting myself in the place of a guy doing some girl I was imagining what it would be like to be a real girl and to be satisfying my boyfriend. My cock started to harden, straining against the tight pink silk of my panties under my cargo shorts.
I was thinking how odd this conversation was. My Dad, dressed up to the nines as his alter ego, Jane, was parenting me on what was and was not normal when it comes to sex. In the past every time I was around Jane I found her to be insecure and unable to control her sexual desires and using me to satisfy those needs. She seemed stronger today - more in control - and it's as if Jane and my father were becoming one person.
I was worried Jane would be unable to control herself - she would undo my pants to get at my cock and discover me in panties....but that didn't happen. This was strictly a parent to child talk. When we were finished we went about our business for the day. Since the family was out for the day Jane simply remained in her persona for the better part of the day, even tinkering in the garage for a bit, although she lost the high heels and wore a pair of work gloves over her painted nails.
A few days later I was out in the garage myself when I heard the whiny sound of a dirt bike making it's way up our long driveway. I looked out and it was Bruce, the local hot guy who everybody looked up to. He had seen me looking at his cock in the locker room shower and ever since had been giving me strange piercing looks with a crooked smile on his face.
Bruce roared up to the garage and turned off his bike. He thought he was all that - with his Honda 120. Still too young to drive, he drove through fields and sometimes chanced it and drove on the streets of the neighboring subdivision. I was surprised to see him at my place.
Bruce was wearing a tight T-shirt that clung to his well-developed chest. His muscled arms strained against the fabric. He was wearing a tight pair of jeans and I could see his hard cock stretching out down his right leg.
"Hey, what's going on?"
"Nothing much", I replied.
"Wanna go for a ride with me?"
"Where, man?"
"Oh, down the trails a bit - I'll show you where me and the guys hang out."
I told my sister Suzy, who has hanging around to tell Mom I would be back in a bit. I hopped on the back of Bruce's bike.
"Hang on tight, Don"
He took off quickly and I grabbed on tight to him. It felt really hot to have my arms wrapped around his firm body. He took off through the fields and after about 10 minutes we had entered into a small stand of trees. He cut the motor and we hopped off. It was a cool place. There was a tree trunk on one side, and remnants of a fire pit. There were empty beer bottles lying around. The spot was pretty secluded by brush.
Bruce showed me around. I was so happy he was being nice to me. Maybe I was going to be part of the group he was in of local kids and their dirt bike. Bruce and I began chatting a bit about school and things. I had only lived here a few months so he asked me a lot about where I used to live.
"So did you have any girlfriends where you used to live?"
"No Bruce"
"Well you know I see Jennifer, right?"
Everybody knew that. They were all over each other in school.
"Jennifer's hot, man. You're a lucky guy!"
"Yeah well she really can't get enough of my dick"' he laughed and grabbed his cock, which was obviously hard in his tight faded jeans. I looked and gulped, and he noticed it.
"She likes to fuck but she won't suck it for me"
"Really?"
"Yeah, and I love to get it sucked."
With that he pulled his jeans down and off. He wore no underwear. He sat back on the log and started stroking it. I was mesmerized.
"You know some chicks will suck a guy's dick and some won't. I miss having a pair of lips around my cock!"
"I'll bet you'd like to suck it for me, wouldn't you, man?"
I looked into his eyes and couldn't deny my feelings. He wouldn't let me anyway.
"Get over here and suck it, dude!"
As if in a trance I walked a few steps, dropped to my knees and his dick was right in my face. It was about 7 1/2 inches, thick, and with a fair amount of soft brown hair around it. He was circumcised like me. His balls were really big. His smell was intoxicating - like he hadn't showered for a day or so.
"Do it. I know you want it."
I leaned over and seeing the wetness at the tip I quickly licked it off. Yum! I then kissed the head and down the shaft as he moaned and spread his legs further. It bounced around my face. I then licked up and down the head and the shaft until it was all wet. I went down and gave his sweaty balls a lick as he gasped.
"Oh yeah, faggot. Lick those sweaty nuts!"
I got his balls all wet with my juices and then returned to his cock, taking the head into my mouth and slowly sucking it for him - not wanting to rush things. He moaned and grabbed my ears, forcing his cock in and out of my mouth. I couldn't help but choke as he forced me to swallow the entire length.
"Man! No girl ever took my whole shaft! I just knew you would be a hot cocksucker!"
His words only encouraged me. I felt my cock hardening in my panties under my shorts.
He pulled me off his cock, and I was disappointed.
"Strip. I want to see what you've got down there!"
I hesitated.
He jumped up and before I could stop him he undid my shorts and yanked them down. I tried to stop him but he was too strong. He laughed when he saw what I was wearing. It was my favorite pair of lime green satin panties, with the daisies.
"Well isn't that sweet! You really are a sissy aren't you, Don? Maybe I should call you Donna!"
"Turn around for me Donna. Let me see your ass in those sissy panties!"
I turned around and he let out a low whistle. I was SO embarrassed! Here I was in a secluded spot posing in tight little panties. I felt so vulnerable, and I knew I had to do whatever Bruce told me. Somehow that really excited me. His hands grabbed my cheeks and I felt him caress my bottom. His hands felt so good, but I knew I would pay dearly for this.
Bruce pushed his rough hand up against my throbbing tight little hole, pushing the panties deeper and deeper, right into my hole. I gasped.
"You like that don't you, Donna? Having a guy play with your pussy!"
I mumbled.
"What's that? Tell Bruce what you need?"
"Oh Bruce that feels good, man! Do what you want with me!"
He laughed. "Oh don't worry. I will do just that. I fucked my cousin's ass a few times. It was really hot, and he never wore sissy panties. I think I'll do the same to you!"
With that Bruce pulled down my panties and reached around to grab my cock and balls.
"Oh yeah, there's that small little boy's dick of yours. It must be fun to play with a real man's cock like mine!"
Bruce then told me to turn around and get on my knees.
"Get it wet, Donna so I can fuck you!"
I slobbered all over the cock, getting it as wet as I could.
Bruce pushed me over the log, my panties pulled halfway down my legs and he spread my legs apart. He put some spit on his finger and worked it into my hole.
"Yeah, this is gonna be good! Get ready for cock, sissy!"
Bruce lined up his big rock hard dick and pushed it against my hole. I gasped and tried to relax, and I felt it slip inside. Bruce didn't let me get used to it - he just kept pushing and pushing until it slipped in a few inches.
I started screaming a bit and he just laughed.
"No one can hear you, bitch. I know you want it!"
I started crying a bit as I accepted his manhood into my hole. After a few minutes he had it all the way inside me and he got into a steady fucking motion. I started to relax and actually enjoyed what he was doing to me. I started to feel tingly inside but my cock was all shriveled up and scared. Bruce was saying all kinds of nasty things to me, calling me a fag and a whore. I started to believe him. He was right of course, I was both. I tried to open my hole as much as possible so Bruce could enjoy my hot hole as much as possible.
"Man, you have got one tight ass! I'm gonna fuckin cum!"
With a few hard thrusts and a grunt or two I could feel him start to spurt inside me.
The feeling was incredible. I knew he was pumping his cum deep into my belly, I could feel it exploding inside me, spurting great globs of his manly cum.
After he was done Bruce pulled out his cock with a loud pop. I felt empty without it.
He took a Kleenex from his pocket and wiped his spent cock. I pulled up my panties and then my shorts.
Not much was said. Bruce said we'd better get going and I rode behind him through the fields and back to my house. I could feel his cum start to dribble out of my ass as we bounced along. I held his body tightly, and was somehow proud that I had pleased him and taken his cock.
We got back to my house and he dropped me off.
"Listen, Don - what happened today is between us - if you tell anyone I'll kick your hot little ass! From now on when I need it you'll do what I tell you -do you understand? Unless you want everyone to know you wear girl's underwear?"
"I understand Bruce, I won't tell a soul!"
With that he took off down the driveway. I could feel his hot sticky cum leaking out of my sore butt into my panties, and I loved the feeling.
Alone in my room one night, after showering and putting some sweet smelling lotion I found in the bathroom onto my entire body I felt that incredible insatiable urge again and opened the small duffel bag containing bits and pieces of feminine attire I had assembled. I found a pretty gold satin camisole and chose a pair of lavender panties I had found in Jane's box of femmy delights, and it felt so wonderful slipping them on and relaxing on my bed.
I thought about the last few months and what had happened in my young life. A few weeks ago I had sucked Bruce's cock and he had forcefully fucked me over a log, after discovering me in panties. I tried to rationalize what had happened, since I had tried to block it out of my head since the event. Bruce had picked up on my gay tendencies, the discovery of me in panties only cemented his perception of me I guess. I was sore for days, but I had to admit, looking back at it that I liked what happened. I liked making a guy feel good and get his rocks off. I had submitted to him and did what he told me...like a girl would do I thought. Maybe I was some kind of mistake...maybe I should have been born a girl, because I liked what we did and I sure liked wearing girl's clothes!
And then there's the matter of my father, who obviously has some gender issues! Like father, like son...like father, like son....I kept running through that in my mind. Did I inherit his confused sexual genes or something? We learned about chromosomes in school...X and Y and combinations and such....maybe mine were all wearing panties and in a chorus line! I giggled at that thought and started to rub my little cock through my pretty lavender panties.
Visions of Bruce's cock popped into my head immediately, and I tried to force them out. I decided to concentrate on the girls at school. I didn't really have a girlfriend - some of the girls like the ones Bruce dated were kind of aggressive and mean to me and to my nerdy friends. I thought about Sarah, a girl in a few of my classes. She was always nice to me. I thought about her small blossoming chest and what it would be like to kiss her. When I thought about what kind of undies she might wear that got me a little excited...but then Bruce's cock popped back into my head again. I wet my finger and pushed it into my tight hole and poked around. My cock was rock hard and felt so hot in the pretty panties. I removed my finger and moved to my chest, rubbing my breasts and pinching my nipples through the silky camisole. That really got me hot! I stroked myself to a strong cum. Carefully removing my undies I put them away. I had managed to do so without getting my spooge all over them, thank God! I decided to sleep nude that night and went to sleep.
The next day I had passed Bruce in the hall. He never mentioned what happened between us until today - there was no one else around.
"Hey, Donna...do you have your panties on today?"
"No, Bruce"
He just laughed.
"Hey, who are you taking to the dance next Saturday...one of your geek friends ...which one Tom or Mark?"
"Ha Ha. Actually I was going to ask Sarah."
"Which one of you will be in the dress?"
He nudged up against me and walked past me. I felt a rush feeling his body up against mine, even for a second. I watched him stagger down the hall in his tight black jeans.
That same day I asked Sarah to the dance and she agreed. I was happy! My father was happy too! His boy was going out with a girl! Such a big deal I thought, it was just a dance.
The day of the dance, Saturday, Daddy had a talk with me again, this time he was dressed in all male clothes, at least from what I could tell - who knows, he could have had on a corset or something under the plaid shirt and the work pants.
"Here - since you're dating girls now you need protection. We don't want any pregnancies!"
I blushed as he put a few packets of rubbers into my hand. This was just a date to a dance!
Daddy had let me use the family car, since I had just gotten my driver's license.
"Don't leave any pecker tracks on my seats!"
I was embarrassed and dressed as smartly as I could, and with boy's underpants on, I picked up Sarah. She looked kind of pretty, not a raving beauty, but I felt good about being seen with her. We drove to the dance and had a pretty good time. There was a band there and everybody was dancing like crazy. I could see Bruce there and he winked at me. His date was gorgeous and to be honest he looked pretty handsome.
A few hours into the evening I went in to the men's room and was standing at the long urinal trough relieving myself. There was no one else in there until Bruce came in, stood right next to me and pulled out his big cock. I
tried not to look but couldn't help but watch the stream of hot yellow piss arch out from his cock and into the trough. He caught me staring at it and after he finished it, he turned to me. My own cock had stopped peeing and I was just standing there with it in my hand. It was getting hard.
"Clean it off for me, Donna"
I looked into his eyes, and then bent over and took the end of his cock into my mouth. I could taste the salty piss droplet at the end and licked it clean. I swallowed the head and started to suck.
"Whoa there, faggot! Somebody might catch us!"
Bruce gave me a slap on my ass, zipped up and left me standing there. What had just happened? Why did I do that? God, he tasted good!
I heard the door swing open and I zipped u and got out of there. As I reentered the gym and all my classmates I felt like I had a sign on my jacket that said "Cock Whore" and all could see it.
After a few more minutes of dancing I convinced Sarah to leave. We drove a bit, and went to the wayside out of town to park and talk a bit.
Sarah slid up next to me and we kissed. She was a little aggressive and soon had her hands on me and was rubbing my crotch. I tentatively was feeling her small chest through the material of her dress. It was cotton, but very pretty I thought.
Suddenly Sarah unzipped my pants and put her hand into my pants as we kissed. She felt around and then pulled her hand away.
"Pull down your pants, Don. Let me see it! I'll pull down my panties too!"
Wow! This was something! I quickly lowered my pants and she dropped her panties to the floor. I tried to see what they looked like but in the dim light I couldn't.
We returned to kissing and my hand went down between her legs and I felt a hot wet pussy for the first time. It was hairy and sticky. Sarah reached down to find my manhood.
"Why aren't you hard?"
"I don't know. I guess I'm nervous!"
Sarah stroked my cock and felt my balls. I started to get hard, but it wasn't much. My hand was fingering her and all I could think about was how gross it smelled.
"You know, I don't want to be mean...but your cock is SO small! Does it get hard?"
"Sure'" I said shakily.
"I don't want to be mean...but my little seven year old brother has a bigger cock! "
The semi-hardness I was experiencing went away and my cock retreated.
"You're not fingering me the right way! Here let me do it!"
I pulled back my trembling sticky hand and watched as Sarah spread her legs wide apart and worked her finger as she pleasured herself. Her left hand was on my cock, which still remained soft.
I tried to concentrate and make it hard. This was never a problem for me, but try as I might her little grunts and the permeating smell of her young pussy in the car only made me think how much I didn't want to be here.
Sarah shuddered and climaxed. I watched her, my limp dick in her hand. She let go of it and relaxed for a moment.
"You know, I don't understand you. You have a chance to have some fun with a girl and your cock just stays small and soft! It's useless!"
"But, Sarah, I don't...."
She cut me off.
"Are you deformed or something? Why is it so small, and why doesn't it work?"
"Well it works for me."
"I find that hard to believe! You know, I think you must be a homo! Here!"
She took her panties from the floor of the car and threw them at me.
"I think you'd better wear these - you're as much a girl as I am!"
Trembling, I lifted Sarah's panties up and looked at them. They were white satin and lace, with a little rose decoration in the middle of the waistband.
"Put them on, sissy!"
I did as Sarah ordered and my cock immediately responded. She watched and took note of it.
"Well it looks like that's one thing that does excite you! Those panties are yours, now, Don. You're sick! Take me home!"
I pulled up my pants and put my shoes back on. Silently I drove her home. There was no goodnight kiss or any pleasantries. She got out and slammed her door.
I drove home from my date and thankfully everyone was asleep. I went to my room and stripped down to Sarah's panties. I had a wet spot in the front of them. I sighed, pulled down the front of the panties and stood there before the mirror jacking off my hard cock. The panties fit me really well, and I especially liked the lace around the leg openings and along the waistband.
I shot huge globs of cum all over my dresser and cleaned everything up. I took a tissue, cleaned my cock and wrapped it in a fresh tissue so no cum stains would soil the panties. I tucked it back into the panties and slept in them that night. I couldn't think anymore about the event s of the evening. I was exhausted. I would think about it tomorrow.
After the humiliating date with Sarah I was kind of wierded out. I had the chance to mess around with a girl and I blew it (actually I didn't blow it...I didn't even get hard!) I added her panties to my secret collection and tried not to think about it too much. Whenever I saw Sarah at school after that she was polite but obviously wanted nothing to do with me, and I got the same treatment from her friends as well.
After the date I always had my hottest mind blowing cums when I had her tight panties on! The white satin and lace really framed my cock and I loved to rub myself right through them until I got close, then I would free my hard little cock and shoot into and all over my hand and arms. Sometimes getting spooge in my face or my hair.
I saw Bruce at school and around the neighborhood and he was actually pretty cool - he would rub his crotch in front of me and watch my reaction with a sarcastic smile on his face, but it didn't stop me from looking or thinking about it. He found time and opportunity to make me suck his cock every month or so and from his reactions I knew I was learning how to do it really well! I always swallowed every drop of his hot cream. He only fucked me once or twice after the first time, and the last time he took great delight in making me beg for it.
It was especially humiliating because I was wearing a matching pale yellow bra and thong panty set, plus a white garter belt and stockings under my boy clothes, and as soon as I got to the private place with Bruce I stripped down to them to see his reaction. He squeezed my titties and rubbed my ass and put my hand on his throbbing erection before he made me start the begging. He celled me all kinds of nasty names, which I just accepted. But beg I did...I was craving his hot meat and boy did I get it!
At home I had swiped a few candles from inside the house and with a knife shaped the fat end of the candles into the shape of a dick head, and used them to scratch that itch I sometimes had to have something hard up my ass. Candles, cucumbers, the heads of screwdrivers...I was resourceful and horny!
Jane was more and more in control of my daddy's life. Jane would swoop into my bedroom in the morning, a male robe covering her full lingerie, and wake me for school. I hadn't been getting any from Jane for a while, so one morning I pretended to be asleep, but was fully awake, naked and horny in bed. I made it so that my bedcovers were barely hiding my semi or fully erect young cock. Jane would stand over me, sigh, and then open her robe, kneel next to the bed and be powerless to resist her urges...she would suck my cock until I pretended to "awaken". It felt great, and I started doing it pretty regularly. A few times instead of sucking me she would release her cock from her panties and slide it over my sleeping lips. I would start sucking it like a baby on a bottle! I would suck and nibble on her foreskin and feel it getting harder in my suckling mouth.
I know it was wicked to torment poor Jane like that, but I had felt she had been ignoring me for a few weeks, and I considered it an experiment.
Jane started appearing before me fully dressed, and she was starting to really get her look together. She had obviously been adding to her wardrobe, and put a lock on her closet door. I wonder if she knew I had been snooping and trying on her things?
When the opportunity arose I loved dressing up in as feminine a wardrobe as I could manage, with bits and pieces of stolen clothes that had fallen into my secret wardrobe. I managed to go outside and walk around a bit while dressed, and loved the feeling. I felt so natural and at peace while dressed...and yes, I felt sexy.
One day when I was outside in a little blue top, a yellow floral skirt, hose and pretty lingerie underneath I was surprised to find one of the neighbor guys behind me. It was Rich - one of Bruce's friends, and we were both shocked to see each other.
He told me to relax - Bruce had told him about me.
"You look kinda cute!"
"I'm so embarrassed!"
"Don't be...let's go inside so I can talk to you."
I led Rich into the house and up into my room. I was trembling. He pulled me to him and held me tightly. I relaxed and as I looked into his eyes he kissed me!
"I want to make love to you! Like it should be...not rough like Bruce!"
"What has he told you?"
"Everything I guess. Come and sit by me on the bed."
I sat next to Rich. He was being really nice. I always liked him - he was so laid back, and seemed to have mind of his own, not a mindless follower. He was kind of handsome, with tousled red hair and a pretty athletic body. He was in a tight T shirt and a pair of jeans and sneakers. He kissed me again, and forced me to lie back on the bed.
Rising from the bed he looked into my eyes as he pulled off his shirt, then lowered his jeans. I was mesmerized. He stripped out of his jeans and his BVDs and sneakers and I saw his cock. It was hard already - a good 6 inches and he had a nice hairy set of full balls as well. He got back on the bed, lay on his side and then began kissing me again. I kissed him back, and he took one hand and started kneading my breast through the top, and with his other hand he put it under my skirt and started working his way up to my crotch.
I moaned and wiggled under him
"You're just like a girl! I love the way you move!"
His one hand was on my panties now, and he was rubbing my erect little cock straining against my panties. They were an incredibly silky pair of hot pink panties. His other hand had lifted up my top and was feeling my matching bra.
Rich then lifted me a little while continuing to kiss me, and with a swift movement undid my bra. I sighed and lay back down on the bed. He lowered his mouth and put it right over my left nipple. I moaned and he kissed and sucked my nipple and pulled as much skin as he could around my breast to make it fuller. Switching to the other side I thought I would faint. He began to gently nibble on my breasts.
I felt so powerless to stop him and was putty in his hands.
After what seemed like an eternity Rich moved down and lifted my skirt. He lowered his face to my panties and he began to lick my erect sissy cock through the pink material of my panties. He made them all slick with his mouth juices and kept sucking at my cock through the panties.
I couldn't help myself, I came right there, inside my panties and my entire body shook.
Rich then laid back on the bed and told me it was my turn to make him feel good. I kissed his mouth, then his strong chest and worked my tongue down to his cock. He had just a bit of hair on his chest, which worked its way to his cock. When I got to his cock I first kissed the head, then licked the entire shaft. Rich just moaned. I lowered my tongue and licked every inch of his hairy balls, knowing the special treat that was stored inside for me, provided I was a good girl.
I put every ounce of my being into making my man happy. I sucked his cock lovingly and tickled his balls with my fingers. His cock was delicious and jumped and throbbed in my mouth. Before I knew it I could feel him tensing up and I got just the head into my mouth so I could take his yummy spermies. God did he cum! I swallowed every drop.
After he came I figured he's dress and get out of there - but he didn't he pulled me up to him and we rested, softly kissing and feeling each other's bodies. I played with his soft cock, and then felt it getting hard again.
"This time I want to fuck you, baby. Would you like that?"
"Oh yes, I need it Rich!"
I got up from the bed, got out of my skirt and sticky panties, grabbed a small jar of Vaseline and returned to the bed. I put several globs in my puss and got his hard shaft all slippery.
As he lay there I straddled his body facing him, lined up his cock, and leaned over to kiss him as I made my hole come into contact with his hot erect cock time and again. When I felt I had teased him enough I straightened up and put the head of his cock into my hole.
I gasped. It was so big! And I was so tight!
I slowly eased back on it and after a minute or so I had taken the entire shaft into my boypussy. I moved up and down on it, fucking myself on his hot rod. He reached up and pinched my nipples or played with my cock, which was small and soft and bouncing against his hairy tummy.
I could feel Rich start bucking from underneath and then the explosion began. I could feel spurt after spurt of his hot cum bathing my insides. I felt so tingly, so excited inside I started to shake and saw stars.
I collapsed on top of him, he pulled me close to him and we lay there together - two young lovers who had shared something special.
"I'm glad you don't mind that I'm a gay boy, Rich! "
"I don't think of you as a gay boy...I don't think of you as a boy at all! I think you're really a girl and you're just doing what comes natural to you."
I sighed and laid my head on his chest. We stayed that way for about 10 minutes but he had to go home. I cleaned up and put my boy drag back on reluctantly.
I thought about what Rich had said. Was I born some kind of mistake? Was I really a girl inside?
I never was much for sports, or guy stuff. I like to watch football, but I guess I was really attracted to the players in their tight pants. Being raised by a cross dresser was taking it's toll - every day I was becoming less and less masculine...and following in Jane's heel prints. I tried to deny it, to reassure myself that every boy did what I did, but I knew deep inside that wasn't true, and I was different.
I had such a great time with Rich after he discovered me in my skirt and blouse. We did it, but it was different from Bruce, who was kind of mean. Rich was nice to me, affectionate, and I loved the way he treated me like a girl and the way it made me feel. I started to have feelings for him, and wanted to see more of him. My circle of friends was pretty small, and he was a part of a whole different group - guys and girls that were more athletic, more popular. He always winked at me when I passed him in the hall at school, and though I saw him with a couple of different girls, I took comfort in knowing that he and I had shared something special.
Rich got me alone one Friday and asked me to go to the movies. He told me there was a drive in theater about 40 miles away where we could go and have some privacy. I accepted right away of course - I longed to be alone with him! He told me to wear something sexy for him, and we arranged to meet the following night about 7 p.m. He was going to pick me up.
I told the family I was going to the movies with a buddy, and then I prepared for my date. I decided I was getting a little too hairy down below and trimmed my pubic region back quite a bit, hoping no one would notice in the shower after gym class. I now had just short fuzz over my little cock, and I shaved the few hairs I had on my cock and balls so I was smooth and sweet. I took a nice bubble bath and after a delicious soak I applied lotion to my body, sweet smelling baby powder and put on a robe, returning to my room to get dressed. For the date I had rummaged through the box of lingerie and clothes Daddy Jane had hidden up in the garage and selected a few things.
I had found a great foundation garment in the box. It was pale pink and must have been too small for Jane. Luckily it fit me perfectly! It had straps to go over the shoulders, softly padded cups over my breasts, the midriff was actually very tight and pulled in my tummy a bit, giving me a more girlish shape! There were garter straps on the bottom, and it ended shortly above my crotch. The garment pulled my waist in a bit, and gave my breasts a little added cushion but I wanted more! I took a few pairs of panties, bunched them up and stuck one in each bra cup. The result was very pleasing, and I rubbed my new breasts over the fabric, loving the fullness it gave me. My cock started getting hard and I found a pair of silk panties that were fairly close in color to the pale pink girdle/foundation garment and tucked it away properly.
I attached some sheer stockings to the garter straps, loving the way they felt on my legs. I stepped back to see my reflection in the mirror and liked what I saw! I knew I couldn't get out of the house with boobs like that, so I removed the bunched up panties from my cups. I then grabbed a short little plaid skirt in springy colors of leaf green, pink, white and yellow, and a white blouse that I had borrowed from my sister Suzie's closet. I put them and the panties into a bag and opened my window and screen and dropped them into the bushes one floor below. I knew I couldn't walk out of the house with the bag in my hand without having to answer a bunch of questions, and I want to be dressed pretty for Rich tonight.
I put on a pair of loose fitting jeans and a loose button down shirt, which I left untucked, sweat socks and my sneakers. I saw Rich's ca pull up the drive, and I quickly ran downstairs, said a fleeting goodbye, grabbed my bag quickly from the bushes and jumped in the car.
I was so excited to see Rich, and he seemed really nervous. We pulled out of the driveway and made small talk as we drove to the drive in theater some 40 minutes away. We talked about school and things, nothing naughty. When we got there he parked in the back row, and to one side so we had some privacy. He surprised me by having a cooler with beer in the car, and after we parked and got settled, hanging the speaker in his car window he opened a few and we relaxed. It was already dark and he pulled me over next to him. He was driving his parent's Buick, with a nice comfortable bench seat.
"What's in the bag?"
"Oh a skirt and blouse to change into"
"Really? Cool! Do it!"
I giggled and pulled off my boy clothes. He really liked my undergarments and couldn't take his eyes off me. One hand was on his beer bottle, the other was rubbing his crotch, which I could see was sporting a bit of a boner.
I put my blouse on, and then the skirt and he told me I looked hot. He laughed when I stuffed up the panties and shoved them into my bra cups.
"I've got a surprise for you - look in the glove box"
I opened it and found a small bag. Opening it I saw there were cosmetics inside - some makeup, eye shadow and lipstick.
"There's a mirror under the visor - go ahead - make yourself pretty"
I nervously put on a little makeup and the eye shadow was kind of a light purple - I put some on my eyelids. I finished by applying the lipstick to
my lips. What a sensation! It was red and I loved the way it tasted on my
lips.
"Come and sit by me baby!"
I giggled and slid next to Rich. He put his arm around me and we had another beer and started to watch the show. It was a James Bond movie, and really good. Rich started to play with my hair a little and then leaned over to kiss me on the neck. I sighed.
We made out for a little bit. Rich kissed me and I instinctively opened my mouth and let his tongue invade my mouth. I sucked on his tongue like it was a cock and we both liked that a lot. I put my hand on his hard on, and he felt me up. His hand unbuttoned my blouse and he cupped my breasts and squeezed. He was definitely the one in charge, and I liked that! I let him do as he wished and was excited at the thought of surrendering to his wishes.
I was so turned on!
Rich stopped and pulled down his jeans and his plaid boxers and I could smell his heat as his bone popped straight up. It looked so juicy and I couldn't take my eyes off it!
"I'll bet you'd like to suck on a real man's cock wouldn't you, girl?"
"Um hmm"
Well go ahead - we've got all night. Get to know my dick - make it feel good. Let's take our time, though...I want this to last a while"
I giggled and lay down on the bench set, on my tummy and started to kiss his cock. First I kissed the head and the drop of precum he had waiting for me. It was yummy!
"Oh yeah - that's candy for bad little girls like you!"
God, that turned me on.
He spread his legs really wide and I explored the manly area before me. I thoroughly licked his cock and his balls and kissed his upper thighs, leaving lipstick marks.
I discovered I loved the taste of lipstick on a cock, and still thrill to it this very day.
I stopped periodically to sit up, check my makeup and reapply more lipstick.
"Just like a chick. Come on - suck it some more!"
As I lay there worshipping his cock Rich lifted my plaid skirt and pulled down my panties. He started to softly slap my smooth white asscheeks. His slaps became harder and I loved it.
"You're a bad girl! All dressed up and down on your stomach swallowing cock! If you were my sister I'd kick your ass!"
"You're a whore aren't you, sissy? Answer me!"
"Yes, Rich!"
"Say yes sir, when I talk to you!"
I loved it.
"Yes sir"
"You should always say that when you're with a real man, because you're just a sissy and not a real man!"
"Yes sir!"
"Well get back to pleasing me, because that's what your purpose in life should be - taking a cock in your mouth or in your ass, where they belong!"
I sucked him with gusto. He was right, I thought. I was craving his cock and his cum, and only wanted to please him. I sucked him with a fervor, and could feel him starting to tense up.
"That's it...good girl! You're going to get a mouthful of manjuice here in a minute! I know you want it, baby...here...it.....comes!!!!"
His body tensed and I felt him start to spurt into my mouth. He shot seven times, and I greedily gulped every drop down my hungry throat!
He relaxed then, and I sat up, a satisfied smile on my face.
"I gotta take a leak sissy!"
"Well, so do I... Sir!" remembering my place. He smiled.
"There's nobody around us, come back around the back of the car, by the fence."
Rich pulled up his underwear and jeans, put on his shoes and waited as I
straightened up my blouse and climbed out of the car, hoping no one would see me all dressed up.
Rich opened his jeans and pulled out his cock.
"Hold it for me baby while I piss"
I reached out and took his cock into my hand. It felt so weird to hold his cock for him while he peed. There was a lot - he really had to go!
"Use your mouth and clean it off for me baby"
I knew it was dirty but I leaned over and licked the head, tasting his piss for the first time. I knew it was a dirty thing to do, but I was sure no real girl would do this for him. I was special!
"Oh God! I have to pee too!"
I started to free my cock from under my skirt and panties.
"What are you doing? Girls squat to pee...and you didn't say Sir!"
So there behind the Buick and protected by the fence in the back, I squatted down and forced my cock to relieve itself down between my legs. It somehow seemed right. I had to go really bad, after drinking a few beers. Rich got excited by me peeing like a girl, squatted down like a slut in a parking lot and put his soft cock in my mouth to suck on while I finished relieving myself. I don't know if I was more shocked by him spurting some more piss into my mouth, or that I actually swallowed it for him - but swallow it I did!
We got back into the car before anyone could see us, but Rich insisted we get into the back seat. He had me strip off my blouse and skirt, and then my panties. He stripped completely nude. I admired his lean smooth body, and traced my finger down the hair from his chest to his cock where it was very thick and manly.
We sat next to each other and he pulled down the straps on my corset and pulled out the silky panties from the cups, freeing my nipples. He kissed me down from my neck to my nipples, where he started to softly bite them. They were erect and ready for a man.
I moaned and he then took his hand and started to feel my cock and balls. My cock started to get really hard.
"Man you sure are small down there! It's like you never developed all the way!"
I sighed and my cock shrunk up from shame.
"Yeah that's nice. Keep it small and out of the way for me. I don't want to be reminded of it when I fuck you! And I AM going to fuck you raw!"
I just moaned. Rich bit my nipples even harder and I loved it. He laid me back on the car seat and spread my legs. He put on a rubber while I watched him and grabbed a tube of something from his jeans pocket. He put a big gob inside my hole and worked his finger in and out of me.
"I'm gonna fuck you now, baby. Spread your legs for me!"
I spread wide and Rich maneuvered his cock so it was at the entrance to my tight hole. He pushed the head inside and I cried out just a bit.
He laughed and said I'd better get used to it.
"You wouldn't know this - because I know you've never fucked a pussy - you probably never will, being a fag and all - but your ass is so tight...it's better than any pussy I've ever fucked!"
I smiled back at him, relaxed a little and he shoved a few more inches inside me.
"That's it! Take my big hard cock into your tight little pussy, baby!"
Rich kept pushing and he got the whole thing inside me. It hurt but I wanted it. It was my place to take his cock and make it feel good. I tried to open myself up as far as possible so he could enjoy it more.
I wrapped my legs around his strong back and he began fucking me like an animal. Hard thrusts, then short jabs, showing me his talents as a cocksman.
We were both grunting and moaning as he kept up his relentless assault. He leaned over and started kissing and sucking on my neck as I wrapped my arms around him, feeling his strong back and his shoulders. I wanted him to kiss me on the lips but he wouldn't. I couldn't blame him though - I had cum and now his piss on my breath after all.
For a young guy he had incredible stamina, fucking me for a good twenty minutes. Of course it was his second cum of the night, having shot already down my throat a little while ago.
With a few deep mighty thrust he was buried deep when he started to shoot inside me. I held him tight, so excited inside at his orgasm. I was shaking and saw stars as he came inside me.
He lay on top of me, panting and I held him tight, not wanting it to end. I felt his cock soften inside me and slip out.
We both eventually sat back up. He had me take the rubber off his deflated cock. It was full of his warm juice. I took the rubber, and as he watched me with his mouth wide open I whorishly emptied the used condom into my mouth. I just had to have more of his juice. I then threw it out the car window....it becoming yet another discarded tool of love on the dirty gravel of the Stardust drive in theater lot.
To this very day I still savor the look on a man's face when I suck all of his juice out of his rubber. It makes him feel more powerful and makes me feel more whorish! But back to my memories...
We laughed, and then got dressed and settled down for a bit. We drove back home and he dropped me off. I managed to wear the skirt, though bunched up, and the blouse under my boy clothes and I quietly snuck into the house and upstairs. As I tried to enter the bathroom Jane saw and pulled me into her room, locking the door.
"What have we here? It looks like smeared makeup on your face!"
Jane roughly kissed me and forced her tongue into my mouth. I'm sure she tasted Rich in my mouth and she seemed to get really turned on,
"You little whore!"
Jane pulled my shirt off me, ripping off a few buttons in the process, and pulled off my sneakers and roughly removed my jeans and socks to reveal myself in my outfit.
Jane removed her robe to reveal herself in bra, panties, garter belt and nylons - all in black.
Her cock was very hard and she stripped off her panties and threw them at me. I could tell she was angry.
She pushed me over the edge of the bed and pulled up my skirt. Down on her knees she pulled down my panties and spread my ass cheeks apart, exposing my well-fucked hole. Like a madwoman she licked and sucked on my hole while feeling my pretty legs through my stockings. She slapped my bottom a bit as she ate me, then rose up and put the head of her cock at the opening of my hole.
Jane pushed her cock into me with one long slow thrust - all the way to the base. She had a good 10 inches and it really hurt! I squirmed and tried to get away from it but she pulled me back on it and started to fuck.
I accepted my fate and after a few minutes I liked my daddy's big cock pounding my hole. I wondered if this was how my mom felt when he impregnated her.
It was so big - not like the teenaged cock I had been getting. I knew from sucking it how much I loved the foreskin covering the big purple head of Jane's cock, and I tried to imagine that foreskin moving back and forth dragging on the muscles of my boypussy. It was so big and I was so tight I swore I could actually feel it. All the pent up frustration Jane had felt the first few times her cock tried to fuck me and she couldn't get it in me...now that I had been opened up by my young lover she was able to do what she wanted all along...fuck her sweet little boy's ass senseless.
Jane fucked me good. Not a word was spoken. I was getting fucked and that was that. I spread my legs as far as possible and shocked her I think when I started to push back and impale myself on the big cock. I wasn't just passive - I was aggressively participating and trying to get the big cock deeper and deeper.
My entire being concentrated on being fucked. I didn't care about my own cock - it was pretty soft - my primary sexual organ was my hot itching boycunt and it needed to be fed. I squeezed my breasts and pinched my nipples while she continued.
My ass was pounded relentlessly and then with a mighty thrust Jane unloaded her juices directly into her own son's tight ass. God, there was a lot of cum! She must have been saving it up for a while.
She pulled out and I felt empty. She pulled me up - threw a yellow chiffon nightie at me and told me to sleep in it tonight - we would talk tomorrow.
I went to the bathroom, cleaned myself up and then to my room. The nightie was very pretty and teased my sore nipples as it brushed against them. I laid in bed thinking about the course of the night, and felt Jane's cum start to leak out of my sore bottom. I scooped some on my fingers and tasted it.
I had become a whore.
I awoke the next morning with a sore bottom and a bit of a headache. My date with Rich - yes, I thought of it as a date even if he hadn't - was rather a wild night at the drive in. I had drunk a bunch of beer, something I was not used to, and I had been totally used as a girl. And I had loved being dominated and making him happy. To make matters worse, when I got home Jane was waiting for me and discovered not only my secret love of wearing girly things but also the fact that I had been fucked that night and was so overcome with lust, and was it jealousy?...anyway, Jane had fucked me as well. I guess she was so overcome with my love of frilly things and finding the telltale signs that a man had been in my boycunt she couldn't control herself.
I awoke and carefully put away all of my girly things. Knowing I was probably in trouble I put on a scratchy pair of fruit of the looms, a pair of cut offs and a T-shirt and went down to breakfast. I found Daddy, my Mom and my sister Suzie all sitting around the table.
"How was your movie last night, Donny"' Mom asked.
"It was OK I guess"
"Well you must have come home late because I didn't hear you!"
"Oh it was late all right! I talked to him for a minute when he got home!" Daddy added. He was dressed in a very manly way and was acting the part of a concerned parent. I wondered what my Mom would think if she knew he fucked me when I got home.
My ass was still sore from taking Daddy's big uncircumcised 10-inch cock last night. It was the first time he had ever gotten it all the way inside me. Rich had loosened me up just enough when I lost my virginity on the back seat of his parents Buick Roadmaster.
Mom announced that she and Suzy were going to visit my grandmother today in Chicago, and that they would be gone the better part of the day. This made me nervous because I knew I had to answer for my behavior last night with Daddy Jane.
After they left Daddy went to his room and was there for a bit. I heard him call me to his room after about an hour or so.
There stood Jane - with a makeup and a shoulder length brown wig that seemed to match his natural hair color. Jane was wearing a two-piece outfit in lavender - a skirt with a matching buttoned jacket. His legs looked stunning - they were shaved and he wore the sheerest of hose. His feet were in white high heels. To complete the outfit he had on a white pearl necklace and white pearl dangly earrings and long white gloves. She looked as though she was off to a PTA meeting or something!
"We need to have a talk, son...about last night. I want you to take off all your clothes first"
I nervously stripped and Jane examined my body. My little cock was hard and sticking straight out. She took her white-gloved hand and gently stroked the shaft and tickled under my balls. I shivered at her touch. She then turned me around, dropped to her knees and spread my cheeks apart to examine my hole.
"Is it still sore?"
"Yes, Jane"
"Well that's the price you pay when you dress up like a slut and you fuck at the drive in"
"How big was the boy's cock...it was Rich, wasn't it?"
"Yes. I guess it's about six or seven inches when it's hard"
"How did it feel to be fucked by a boy?"
"Honestly - I liked it! It felt very natural for me!"
"Did you fuck him too?"
"No, of course not!"
"Does this mean you're homosexual?"
"I don't know...I just know what's right for me!"
"Tell me everything - including when you started wearing girl's clothes, and who else you've been playing around with."
I sat on the bed and nervously told Jane how long I had been dressing, what garments I had assembled and from where, and about Bruce making me pleasure him, and my experiences with Rich. It seemed to arouse Jane.
"Here, put these on, son"
Jane had rummaged in her drawers and produced a pale yellow camisole, matching silky panties, a white garter belt and white stockings. She watched me intently as I first put on the garter belt and rolled the stockings up my legs and attached them into place.
"You do that like a pro! I guess you've been learning from me!"
I sighed and then put on the camisole - it felt so smooth and nice... then I stood and slid the silky panties up over my throbbing little erection. The panties made me feel so good - I had grown to love the feeling of silk surrounding my boy parts.
"You know, Donny I'm not mad at you for messing around with your friends or for dressing up - but you've been into my things and that's wrong. You have to be punished for that!"
I lowered my head and knew what was coming. From the time I was little I had been spanked. Daddy was spanked as a boy, and he believed in it. Usually I had to pull down my pants and underwear and lay across his lap for him to spank me with his big bare hands.
Jane sat next to me on the bed, and told me to stand before her. I did, and looked at her composed feminine appearance. She removed her white gloves and then her skirt, exposing her stocking tops and her purple satin panties she wore underneath the incredibly feminine lavender suit. She spread her legs a bit and I could see she was fairly hard in the panties, and a wet spot appeared at the tip of her cock.
"Bend over my lap, sissy!"
Sissy! She called me sissy!
I bent over and Jane slowly the pretty yellow panties she had forced me to wear. Not far, just low enough to expose my ass cheeks. My cock, which was still kinda hard, was rubbing up against her stockinged leg.
The first slap of her hand landed on my left cheek and surprised me. I jumped and winced at the pain. Then another slap, this time to my other cheek. She went back and forth, telling me she was disappointed that I had become a sissy and a whore - she expected grandchildren from me, and that I'd better learn to start liking pussy.
A few more slaps landed on my reddening bottom.
"Doesn't the thought of a girl's juicy pussy, waiting for your hard cock excite you?"
"No, Daddy, please!"
"Don't you want to bury your hard on into a tight pussy hole?"
"No Daddy, that's gross! The girls think I have a tiny cock and they make fun of me!"
"Nonsense. Your cock is perfectly sweet and boyish!"
He continued to slap first one cheek, then the other.
"This is for stealing my clothes! And this is for teasing me and making me do things to you I shouldn't!"
My ass was burning, yet my cock was hard as ever. I thought about the way I had teased Jane in the morning, presenting my hard young cock to her in the morning when she tried to wake me, and the delight I felt when she took it into her hot mouth or put her own throbbing tool at my lips, I was enjoying the feeling of my cock rubbing against Jane's stockings and with another two slaps I couldn't help myself...I shot all over Jane's leg. My body shuddered and Jane felt it, she stopped spanking me and softly rubbed my sore bottom, holding me tight until my body stopped spasming. I could feel her hard cock poking at my tummy from below.
"You're a very naughty sissy!"
Jane pushed me to the floor and I looked up to between her legs.
"You've made a terrible mess here! Clean it up!"
She was a little shocked when I leaned between her legs and ate my sticky goo from her stockinged legs. I think she was expecting me to run for a tissue. With my bottom red and sore, and my lust for cock and cum overtaking me - I licked her stockings clean and then looked at her cock.
I wanted to make things up to Jane - for steeling her clothes, and teasing her like I had. I knew a lot of this was my own fault. The front of her panties were bulging and very wet. I pushed her back on the bed and licked her cock through the pretty purple panties. I ran my tongue along her shaft and the panties were soon soaked from her juices as well as my own tonguing.
I pulled her panties away with my mouth, exposing her throbbing cock and she sighed. I then took the head into my mouth, aching with desire to suck the hot cum right out of her and down my throat. I wanted to do this for several reasons - first, I realized that I was so turned on by being dressed and spanked I just had to have a cock in my mouth, and I wanted to make up for my bad behavior - to make it up to Jane for being such a bad boy.
I moved the foreskin back with my hand and licked the sensitive head as Jane moaned. I moved the foreskin back up and stuck my tongue inside it, licking all around the inside, my tongue surrounded by skin on one side and cock head on the other.
I then used my mouth to move the skin up and down over the head. Jane was breathing heavy and thrashing around the bed a bit. I then pushed the skin down and started slowly sucking most of the shaft. It surprised me how much I was now able to swallow, and I think I surprised her as well.
I took one of my fingers, licked it, and then fingered my hole as I continued sucking cock. I could feel it pulsing in my mouth, and I applied pressure to the underside of the shaft. My mouth and the cock were now one.
I felt her getting close, and I stopped sucking her cock and licked her big shaved balls. They tasted good, and my tongue explored all around the balls and to the little ridge of skin underneath. I concentrated on that ridge of skin and Jane gasped. She spread her legs even further and I worked my tongue back to her hole. It was smooth and clean and properly shaved like you would expect from a cross dresser. I kissed the hole and then pushed my tongue inside. I slipped another finger into my own pussy as well. This was so hot!
Jane was shaking and convulsing as I darted my tongue in and out of her pussy. I sensed she couldn't take much more and returned to her cock. She lowered her legs and I took the cock back into my mouth, concentrating on making her cum. I soon felt her cock spasming and I moved up to take just the head in my mouth. I concentrated on sucking the head and felt her explode into my mouth. One, two three, four spurts of hot jism shot into my mouth, and I swallowed each one like a precious gift.
I was a good boy...a good girl...what did it matter. I had showed Jane what I had learned and what a good little cocksucker I was. After all a few years ago she told me I had to learn how to suck a cock. I didn't just learn how to suck cock...I now craved it and being rewarded for a good job with a mouthful of hot tasty cum.
She sat up on the bed, a dazed look in her eyes, and looked directly into my own eyes as I softly nursed on her softening dick. I felt so sweet and sissy in my little yellow lingerie set.
I was her own creation. I hoped she was satisfied.
After the humiliating spanking I had received on the lap of my transvestite father Jane while dressed as a sissy I was one confused boy/girl. To atone for my sins I had pleasured Jane by giving her the most incredible blowjob. I know she enjoyed it. Judging by the amount of sperm she pumped down my young throat, and I had enjoyed showing Jane what I had learned.
But there was something else to deal with...she seemed disappointed that I was not at all interested in girls (other than their clothes) and that I had been going down the path of a sissy who enjoyed pleasing men.
A strange reaction I thought, from the person who introduced me to this lifestyle.
In the next year I didn't see much of Jane. She hid from me, and I saw more of my father in an outwardly male role. He seemed to be watching me, and testing me. I got the impression that he was ashamed that in his mind he had turned me into a fag. The feelings I had were very conflicting, as you can imagine.
I still dressed up in private, and got together with Rich now and then to satisfy my occasional need for cock. I even hooked up with Bruce a few times and subjected myself to his sneering attitude and delicious hard cock that always made me feel like a slut. I enjoyed that - it excited me and only made me want to suck his cock longer and better, teasing him and making sure that he would never forget my mouth on his cock...and I started developing a feeling inside that I was a failure as a man and somehow beneath real men like Bruce and Rich. I also began to appreciate the power I had in making a man cum. I simply loved having a dick in my mouth, and in making a man squirm before letting him bury his load down my throat. The longer I made him wait to cum I found the sweeter the load, and the more I wanted it. By the time I had it spurting inside me I was tingly inside and dizzy, sometimes shaking. I had begun having girly orgasms.
My cock had not grown from it's small size, and here I was graduating from high school with a cock that was only four inches long when fully hard and only an inch or so long when soft. I didn't feel I could satisfy anyone with it and decided it was best kept in panties and used as my personal plaything.
I was making plans to attend college about 45 minutes from home. While my family could not afford for me to board there, we were able to manage me commuting. I was taking general college courses with the hope of becoming an architect.
Jane had joined a support group for cross dressers and was going out every Saturday afternoon to attend these meetings. Often she did not come home until Sunday night. I assumed she stayed dressed all day Sunday with another friend. She told me about her meetings and one spring day when I was nearing the completion of my first year in college she had a heart to heart talk with me.
I was called into Jane's room one day when we were alone in the house. She was upset.
"What's wrong?"
"I have something to tell you and I hope you won't hate me!"
"I couldn't hate you."
I've decided I'm packing up my things and leaving."
"What? Why?"
"I can't live like this any more, and I am going to become a woman"
I sat there dumbfounded.
"I am living a lie. I can't be a man anymore. Your mother and I are selling the house and splitting the proceeds so I have enough money for my operation."
"What about us, Daddy?"
"Oh, you'll be all right I suppose. You will have to be the man of the house!"
"You will have to get a job, and I think going to college may be through for you"
Jane broke down into tears and I sat there dumbfounded. The sense of betrayal I felt was overwhelming. Jane was sacrificing my future for her own, and the future of my family was very uncertain.
I left his bedroom and in fact left the house, going for a drive to think things over. I stopped at a park and took a nice walk to clear my head. When I had to go to the bathroom I went into the crude wooden men's room built there. It had several stalls and a few urinals. It was a smelly place. I sat down in one of the stalls and immediately noticed the large glory holes on either side of me.
In one stall was a middle-aged man, and he was leaning back on the toilet stroking a big hairy 8-inch cock. I instinctively licked my lips and he saw it and stood up. He forced his cock through the hole and into my space. I did what I had been trained to do - I leaned over and took it into my mouth. It tasted good...it was warm, it was throbbing. I was a cocksucker and I did what I loved. I blew him and swallowed his load. He left and a cock appeared on the other side. It was a black cock and I was amazed at its size. It was a good 11 inches long and it fascinated me. I got on my knees in the filthy toilet so I could get a good shot at swallowing it and I thrilled at the first black cock down my throat. I sucked on it and it was making me crazy with desire. The guy pulled out and told me to stand up and put my own cock through the hole.
I stood and shoved all 4 inches of my cock through the hole. I heard a snicker and then a hot mouth engulfed it. It felt great! Then my balls were being licked.
"Turn around!"
I did as I was told, and I felt a wet finger enter my ass hole. Then the finger was replaced by a hot tongue. God that felt good! All my troubles at home had vanished. All I could think about was what could happen next. I didn't have long to wait. The tongue pulled out and I heard the guy get up and leave the stall. He pushed my stall door open and I was still standing there, my pants and panties down on the floor, my ass and hard little cock exposed.
The guy was big - really big - well over 6 foot tall, and his pants were undone enough for me to see his big drooling cock sticking out of his jeans. He came into my stall, dropped hi jeans to the floor and took me in his arms, kissing me deeply. I accepted his tongue and moaned as I felt his hot cock poking at my own much smaller one. He guided his cock between my thighs and I could fee the monster rubbing back and forth between my legs. I wanted it in my boycunt!
He broke our kiss, turned me around so I was facing the toilet and bent me over. I felt his big finger put cool gel on my tight little hole and I sighed and accepted my role.
He then lined up behind me and shoved his cock about half way in! I cried out and his hand covered my mouth. He then slowly began pumping in and out, shoving his cock further and further into me a little at a time, until I had the entire length inside me.
There in the smelly rest room he fucked me raw. I had never had such a big cock, nor been fucked by a guy who was so into it and knew what he was doing. He varied his thrusting and pinched my nipples from behind. He called me a little white slut and told me to shut up and take his cock like the whore I was. I just tried to spread my legs further and further so he could use me as he liked. After about 15 minutes he bucked into me three times and held my ass tight to his body with his big black hands.
"Oh yeah, Oh yeah, I'm fillin this bitch up with my cum now! You ain't never gonna be satisfied with no white boy after this!"
His words burned into my brain. His cum shot deep inside me and I moaned.
He then pulled his dick out of me and I felt empty. He slapped my ass and told me he'd be back here the same time next week. He zipped up and left. I was stunned, having been fucked almost senseless by a big black man in a public rest room.
I heard a voice from the next stall.
"Hey, whore - get that sloppy asshole over by the hole so I can fuck you next!"
I looked over to see a creepy looking guy. He was missing a few teeth and looked dirty - but he had a big hard cock. He was the kind of guy I would avoid in public. But he was still my better, because he was a man after all.
I lined my ass up to the hole and he shoved it all the way in. He fucked
me right through the hole. I was nothing but a place for him to stick his cock. I enjoyed the feeling of being a whore and started matching his thrusts, fucking him back with my needy hole.
I left the men's room after about an hour and a half. I was sore and my face was all sticky. I had been fucked 6 times, and I had sucked off 10 guys. I never came myself - it didn't matter. I smelled like cum and sex. The entire time I was there being used I didn't think about what was going on at home - just cock.
I went back the same time the next week, though. I wanted more of that black cock. Unfortunately he didn't show up, but there were others there needing me to help them with their needs. Men needed a warm place to deposit their seed, and I felt it my duty to help them out.
This became very typical of my behavior for a good many years. When the need overtook me I cruised public areas, adult stores and video arcades, sex clubs and gay bathhouses. I've had sex in the stalls of major shopping malls, in cars behind gay clubs, right out in the open surrounded by nature in forest preserves and behind bushes in wayside rest areas. But I digress...
After my debauchery for the first time in a public rest room, I went to a gas station restroom and tried to clean up. I couldn't go home like this!
The situation at home deteriorated. Jane quit his job and only came home to get more things for her new life, or to take something of value to sell to keep supporting her until our house sold. I was angry when she sold our lawn tractor and I was expected to keep up with our 2-acre property with a push mower.
My mother became very worried about finances and poured her heart out to me. I dropped out of college and got a full time job to help make ends meet. When she began divorce proceedings I got to see how destructive my father's cross-dressing had become to my family.
I threw out all my feminine things. I tried to put dressing up out of my head.
Our house sold and Mom, my sister and I moved into a much smaller house of less value in a town about a half hour away. Bruce and Rich both went off to college and dated real girls and I never got with them again. It was quite a move down the social ladder. My father came by for a few awkward visits but then they stopped.
I tried to work and be normal, not wanting to end up like my father and hurting people. I occasionally slipped into a pair of Suzie's panties but felt guilty. I tried dating a girl and we became more friends than the typical boyfriend/girlfriend relationship.
When I couldn't stand it anymore and needed to satisfy my crazing for cock I would return to the rest room in the park and hunt for cock. I also discovered the opportunities that were available for cock at adult bookstores with video arcades. I spent many a night there whoring myself and satisfying my need for dick, and helping real men relieve their sexual pressure. I found delight in satisfying all different ages and races of men...learning how different they tasted, the different tastes of cum and how much a man could control his urge to spurt when my mouth got on him.
I found if I wanted a man to cum quick - if his dick wasn't tasty or I was just in a hurry, or there was another juicier cock waiting for me - I could make him cum quick with my mouth. I also found I could tease and prolong a cock for both our pleasure. Some cocks were just too tasty to give up quickly, and frankly I wanted some guys to become addicted to my mouth - to ruin them for real girls. I know, kinda bitchy, right?
I did not start collecting more girly clothes until several years later when I got my own small apartment. I would assemble a small wardrobe, and then destroy it in shame, only to start replacing it a few months later.
I didn't see Jane again for quite a few years. She went off to begin her new life and left us behind. I was the son of a transsexual now, and it embarrassed me. I fought the thought that I would follow in her footsteps and hurt the ones I loved.
Well that's all for this chapter. I don't think I can write more about my life under this series since Daddy was out of my life at this point in time. If I get sufficient response I will write more about my evolution into the man-pleasing sissy I am to this day.
I have been with a number of men who really got into me dressing up and encouraged me to explore my potential there. I also have pleasured literally hundreds of cocks as a gay man.
I have assembled quite a wardrobe, and perfected my makeup and hair. I
only have sex as a girl with men now - I wouldn't have it any other way at this point. I feel like I'm not even really gay - after all I'm really a girl deep inside and my attraction to men is only natural.
I did meet with Jane a few years ago after tracking her down, and it was quite an odd experience for me. If you wish I will share it with you!
The road I have traveled has been an exciting one and I am pleased with the unique sensual creature I have become. It has been fun sharing the journey with you of my formative years.
For you sissies out there my advice to you is "Don't dream it, be it!" a wonderful song from the Rocky Horror Picture Show, as sung by the incredibly erotic Frank N Furter, the sweet transvestite from transsexual Transylvania.
For you men out there keep feeding us sissies your hot cocks - we need them so!









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