Howie Returns to PennsylvaniaChapter 3
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How Rebeca Started
Then, out of the blue, I received a friend request on F-book from the man who started me out. At 43, he was 31 years older than me when he and I played.
I was on summer vacation and discovered masturbation in an unlikely way. Mom and dad had split up, so mom was at work during the week.
I’d watched a series of movies that involved prostitutes that looked really hot and easily captured my imagination.
I had been touching myself, but not really beating off. I was ignorant to actual masturbation. I noticed that I got hard for no reason, and that when I watched sex in movies, especially with whores, I got very hard. I thought about how hot it would be to be with a professional fuck-toy. I romanticized prostitution and imagined girls seeking and then loving work as a whore.
With mom at work, I began by playing with her makeup and pretending to be a sexy prostitute. I added some leotards and eventually an old sexy tight dress that I couldn’t believe my mom had ever worn. At one point I began imitating the whores in the movie, preening, licking my lips, and smiling in a slutty manner. I would rub myself, but had no idea what an orgasm was, so I played dress up and let my imagination run wild. About the fourth or fifth time I dressed up to play I found an angle-headed muscle-massager with a cup-shaped massage head, not at all designed for sex, and added that to the mix. I knelt in front of a bathroom mirror straddling nothing but air, and acted like the whores I’d seen in movies. I used the massager on my shaft and learned to enjoy it on the bottom side of my little cock head. I buzzed myself and made my slender six-inches (yes, I measured it out of curiosity) numb several times before something strange happened. I lost control of my dick and creamy stuff flowed out as it throbbed. I panicked momentarily and considered if I’d broken something, then realized that it felt different and good. Very good. In fact, after I stopped freaking out, I tried again and got even more intense results.
Summer vacation had just begun and rather than play with the other k**s on my street, I began playing with myself. I felt a deep rutting ache every morning as mom got ready for work and almost leaped out of my skin when she left. I began looking at mom’s cosmopolitan magazines and sales catalogs for sexy looks. I began imitating the makeup and poses and then began stroking myself instead of vibrating.
My orgasms began ruling me, so I took power and learned to ‘edge’ and prolong the playtime. My recharge time was pretty quick, and occasionally served as time to change my look and add or subtract clothes. I loved my time as a slut. I began searching the house for things to add to my play and found an old box with theater props and four wigs in it. I immediately began adding a wig to my private play. I had a choice of a platinum blonde, a curly dark mousey brown, a long straight dark brown (almost black) and a short curly red. The red was my favorite for color, but the long dark brown was super sexy and feminine. Of all my limited choices, these two were my go-to slutty wigs.
I experimented with makeup and learned.
One day, about two months into the three and a half that made up summer vacation, I was in my room, kneeling on the playroom floor the way I had seen in a cosmo magazine and jacking myself off. I watched myself in the mirror, preening and calling myself a whore and other tantalizing titles.
I remember that I was close to cumming for the second time that day when there was a knock on my window. I dove behind the doorway and peered at the window to see that it was the man next door – Jerry, or Mr. Carlton, as I knew him at that point.
Jerry peered at me through the window with a slight smile and said loud enough through the window that he’d seen me in there playing for several weeks and that he wanted to talk with me. I said he’d seen me and it was ok. Eventually, he wore me down and I accepted his suggestion to go out back and talk to him through the back fence.
I slipped on a pair of my mom’s high-heels, they were very tight, and walked out back. I came around the corner of the back room to see him standing at the back gate of our tall brown wood-picket fence. His thumbs were looped through his belt loops on his jeans and his hands were relaxed, albeit in front of his mature dick.
I realized that another man or a dick of any sort hadn’t been in any part of my whore play. Seeing his hands there triggered something in me, a curiosity about how excited he was to see me dressed like a slut. There I stood, wavy long brown hair, a short stretch-satin sea-blue dress, pulled-up to make it even shorter, ‘nude’ pantyhose, pre-cum and lotion soaked red panties, black high-heeled sandals, an old satiny black bra with socks rolled to make boobs on my slender frame, and way too much makeup on my face- particularly around the eyes, and a racing heart.
Mr. Carlton smiled and reassured me that I was not in trouble and that he wouldn’t tell anyone about me. I remember that at the time I didn’t believe him. He was believed to have beaten his actual c***dren and then after a short re-marriage his step c***dren also. I remember fearing him. After some talk about him watching me playing dress-up in my room from his house on the days he didn’t have to work until night time, he asked me “What do you imagine when you are dressed up and playing by yourself?”
I thought for a moment and stupidly answered with the truth, “I imagine I am a prostitute, the prostitute I want to meet and play with some day.”
He lit up with a smile and shook his head, undoubtedly at his amazing luck. He considered the situation a moment and asked me if I knew what prostitutes really did.
I answered slowly, and somewhat thoughtfully, “I do. They have sex for money with lots of men because they are good at it, and because they like it.”
As I produced my answer, he opened his pants and began rubbing himself. I couldn’t see his cock, but I knew he was doing that. He asked me why I thought that was so sexy.
I answered something like, “They are sex. They have sex and are good at it because they know what they want…and what the men want…and they do what they know is sexy.”
Mr. Carlton, Jerry as I would later call him asked, “Have you ever seen any movies of women having sex with men?”
I replied with an indignant yes, and then after being challenged listed off several ‘r’ rated movies. He snickered and said he meant something much different, people actually having sex and showing it all – ‘porno’. I confessed I had not.
He said, “Well, let me make you a deal, I know your mom will be home in about two hours, so there is no time today, but if you let me watch you posing like you were and rubbing yourself like you were right now, and, if you let me put myself up against this knot-hole in the fence and keep doing your poses like I just said until I am done, I will let you see a movie with men and women actually fucking in it tomorrow.”
My instinct was “Oh my god yes!” but I said no at first and then relented after he asked me what the harm was. We had a date…of sorts.
I posed for a few minutes and stroked myself, re-gaining my hard dick in no time. I realized that I liked the attention and loved doing the poses. After about five minutes he pressed his cockhead against the golf-ball sized knot-hole and told me to hold my dress up above my waist and turn to let him see both my butt and my dick. I did as asked and just as I wondered how long this would continue, his orgasm shot through the knot-hole. He pulled away after a few seconds and looked around and then back at me as he zipped up. “I’ll see you tomorrow morning. Bring your things over and change at my house if you like.”
The first day I didn’t bring my things and he let me watch a movie with porn legend Traci Lords in it. I came three times before he came in. I went home after some more discussions about sex and prostitutes…I don’t remember them any more…but I do remember that I agreed to come over again the next day and to dress up for him.
Over the remainder of that week and up to the end of the next week I went over every week day. He told me he had taken vacation just to help me out. He provided me with several key items of clothing and accessories. Among those was a garter belt and stockings, black high-heeled pumps that fit, skin-appropriate makeup (I was far more pale than my mom), and a long wavy orange-red wig. Our visits amounted to him watching me as I watched myself in a mirror dancing or posing and otherwise acting like a whore as I watched various porn movies he had rented for me to watch. I knew he was masturbating out of view, but I didn’t care. I considered that I might be gay, but since I didn’t get excited at the sight of the men, I didn’t worry about it too much.
Then, about the third or fourth week, he tricked me and showed me a tranny movie. He lied and said they had given him the wrong movie, but the t-gurl was a red-head and was very young. The movie was a tranny-trick plot, in which you didn’t really know it was a tranny, and neither did the unsuspecting guy, until she made him suck her dick and then he fucked her from behind. That was the first notion I had about anal sex – it hadn’t occurred to me.
We only made it into the second sex scene when he heard my mom pull into our driveway and come home early.
I freaked out and quickly changed and cleaned up. Jerry told me it was perfectly alright to leave my things with him that night and that he would see me tomorrow. I left out the opposite side door and walked to my house from a completely different direction to seem like I was at a street-friends house. My mom had come home early for some trivial reason and never suspected much less discovered what I had been doing.
Overnight I obsessed about the red-haired tranny and the things she had done. She’d been Hispanic and was very exotic and I confessed to myself, very sexy. I came about four times overnight as I obsessed and dreamed of her sucking cock and bending over to get fucked. By morning I came to the conclusion that she was probably an even better prostitute than a real woman because she knew how to make a dick feel good. Then I began to realize I was becoming part-gay, or as I later learned, bisexual.
The summer vacation was nearly over and I was more ready than ever to explore. Jerry began to openly masturbate in the same room and then seated right next to me.
The Monday that marked only two more weeks to the start of school Jerry game me a few new things including a black corset with red piping and lace designs, a longer more luxurious red wig, a black collar like the one we’d seen in several movies, and some lip gloss. I looked amazing and actually quite similar to a no-name tranny we’d seen in a few of the movies (I wish I could figure out who it was, but I can’t seem to see her anywhere!!!). I came out and Jerry smiled approvingly and said, as a compliment tailored to me, “You look like a hot fucking whore…so cute and sexy…”
I sat on what had become my position on the couch, on the left side, so I could rub myself and see both the movie and my reflection in the mirror. Jerry had insisted that I watch myself as I came, just like when I was alone, so he’d placed a floor mirror next to the TV stand and I used it. I loved it.
This time Jerry sat pants down and then after a while, he kicked them off. He’d never done that before. After a few minutes I was about to have my first orgasm. As I came I looked at myself and his hand snuck over and caught my cum. I looked at him as he watched me and just as I finished he said, “Taste your sex,” and then wiped my glossed lips with my cum shot. Without thought I was repulsed and turned away only to open my mouth and have some of it slide in. I tasted it just as I was about to protest and then I stopped myself from saying anything at all.
Jerry paused the movie, as we often did, and allowed me to go clean up. I went to the upstairs rest room, is step-daughter’s old bathroom, and fixed my makeup. I emerged with newly glossed lips and a dirty taste in my mouth- my own cum.
I sat to resume the playtime. After only about ten minutes I was well on my way to another orgasm and began a prolonged edging experience. At the start of the next scene the Tranny knelt to suck a guy off. I had not noticed Jerry stopping his own edge-stroking. He leaned over and said, “Now let’s find out if you have learned anything…lets find out what kind of whore you are going to make…”
I didn’t fight it. I didn’t know it was coming, but I had already known it probably would get to this. Jerry placed his hand on the back of my neck and skull and pulled-pushed me to his adult-size penis. Without being told to, I opened and accepted him, then more of him, and more until I felt his cock hit my throat and I gagged. He allowed me up slightly then forced me back down. He did this until I go the idea and began doing it on my own. Then, without warning, his hand returned with a heavy determination and he controlled me back and forth as he came in my mouth.
I was smitten and disgusted all at once. I couldn’t let go of my own false narrative that I was a normal boy with a bisexual secret. I now knew what I was secretly afraid of- that I really like being a dirty slutty girl and now, really knew I liked my mouth used like the girls in the porn movies.
Jerry pulled out and complemented me and wasn’t at all shocked when I went to change and clean up.
That night I relived the experience over and over and then began adding nuances to it. I added the notion of doing it in car, or on a street, or with a stranger in a restaurant – all different scenes from the porn movies he’d shown me.
By this point Jerry and I had established a signaling system to indicate when the other wanted to play and was available. I got up in the dark hours of the morning to put my signal, a book, on the shelf at the same window Jerry had spied on me at the start of summer.
I obsessed and couldn’t sleep. I wanted to relive the intensity and lust of the moment.
I had trouble identifying it at the time, but I was instantly addicted to the degrading whore-like lust and wanton nature of being willingly used by someone who also wanted to use me. Finally, almost on time, but a bit late, mom left for work. I went to begin the first part of my dressing ritual and put on my stockings, garter, panties, form-less bra, and my corset. I put a baggy sweatshirt and sweat pants on and waited until I saw Jerry’s hand put a candlestick in his window. I went out the back door, over my fence, over Jerry’s fence and arrived at his door just short of two minutes later.
In twenty more minutes I was made-up and practically running to the couch in the upstairs family room where we’d watched hundreds of hours of straight and now tranny porn on.
I looked like a slender slutty red-headed teenage girl- totally passable at no more than 100 pounds and with a great bubble ass.
Jerry came into the room and opened his pants. He didn’t start a movie, instead, a sound track of people having sex taken from movies began playing on his sound system and he stood next to the floor mirror.
Jerry looked at me and said, “Good gawd, you look like such a hot girl…I know what you want. Now come over here and watch yourself getting what you want. Watch yourself as the porn star.” He opened his pants and produced his hard adult cock.
I stood, preened at myself in the mirror, looked at his cock straight on, then in the mirror and strutted over. I sunk to my knees and began imitating the porn stars we’d watched together. I willingly and wantonly sucked his cock. I watched myself being the whore I had been watching all along.
Jerry told me in a loud domineering voice, “Rub that dick of yours, rub yourself as you suck my dick you little whore.”
I can never explain how electric that moment was for me, like a d**g experience it was euphoric. However, unlike a d**g experience I have been able to take it to new heights on many occasions.
This was when Rebeca, even though she hadn’t been named yet, arrived. On a Tuesday morning in mid-August.
Three days and about 20 blow jobs later, on Friday, this same unnamed whorish girl-boy got fucked the first time.
Much like the first blowjob, she was expecting it as she was positioned standing behind the couch’s back rest with her arms stretched out toward the ends. Later, she shared with a dominatrix that her first time was like being on a bondage cross without the bonds, and using a couch. I was positioned, legs spread, arms spread and useless watching everything as it happened. I, or my alter ego Rebeca, began having second thoughts at the beginning when Jerry’s thumb had to press hard to force some lube into me.
Much different from the first blow job in which the slight suffocation and complete submission was an aphrodisiac, I hated the pain and the loss of control. I struggled to break free and to stop, but he was big and I was not. I even cried as I was stretched without consent thinking he might stop, but he didn’t.
In short, Jerry had seduced me so he could lie to me and take me.
Jerry lied and said a small dildo was not the right way to prepare.
Jerry lied and told me there would be a very slight stretch and almost instantly, just like the gurls in the movies, it would feel amazing.
And finally, Jerry’s supreme lie was that we would stop whenever I wanted…yeah, right. I cant and don’t really blame him for these lies- I was a very hot, totally passable piece of jailbait ass.
Jerry ****d me and didn’t stop till he had cum deep inside me right after jerking me off and making me cum as he fucked me.
After he finished and sent me to the bathroom, my alter ego let me stop…for a while. She, the yet unnamed Rebeca, apologized as I cleaned off my tear stained face and my creamy ass.
Just before I removed my wig ‘She’ swore she would never want to do that again, but secretly she knew it was a grand lie and that being fucked like a whore was now a part of her.
It would be years before the second actual fuck from a real person with a penis. As the school year began I tried to forget and part ways with my whorish alter ego. I purged and disposed of my things in cycles that occurred several times only lead back to acquiring new things at great cost.
Mid-way through the next summer, while I was struggling to pass summer school and make up for failed classes, Mr. Carlton was visited by the Sheriff’s department and a week later I was told that he was arrested in the morning just after the school bus drove off. A week later my mom and dad sat me down with me and asked I had been in any contact with the estranged and now arrested Mr. Carlton.
Without a beat and in what must have been a convincing enough manner I lied and said no, and that I barely knew him. This was an era before digital media, so I had no pictures or recordings to worry about and nothing ever became of the relationship. Later I learned that he had been accused by actual son, now an adult, along with his step daughter, his step son, and his second wife of, well, you know what, and he was locked up for a while.
I secretly played by myself and effectively kept my alter ego chained inside me for years. I graduated high school and while I was accepted at the local community state colleges, I couldn’t afford them and wasn’t really interested. I joined the Air force to learn a skill and earn for school. There was no war, except the war on d**gs, so I bounced from place to place and about a year into my term of service I let Rebeca back out.
I was in amazing shape and could afford nearly anything I wanted. I had a car and a paycheck. I had freedom and was not yet 20. I became a hot slutty whore in private, playing for hours on end and at anytime of day that I could.
Some weekends I began renting a motel room and playing non-stop. I developed a ritual of purchasing new items and then playing with them on the weekend.
Then, I discovered adult arcades and theaters.
At first I would let others suck me, a hot 20 year old just getting a blowjob from a nameless guy I would never see again. Then I began sucking cock and participating in group jack-off play and finger-fucking.
Then, one night, I was driving near the nasty part of town and met a real live tranny whore on the street. She was cute, somewhat older, yet smaller than me, and sucked me off in a dark alley doorway just like I had imagined a nasty whore-tgurl would. She was a cute Hispanic and really looked like a woman until you got close and knew what to look for. I came so hard with her blowjob that I was convinced no real girl could ever match her (I have been right so far).
About six months after the tgurl BJ I met a white tgurl named Annabel, and found myself actually talking with her in a parking lot. I learned that she didn’t like to play with other tgurls, but exactly like my later ego, Annabel loved being a slutty whore.
I met Annabel on and off a few times over a couple of months, never having sex or her turning a trick with me. We talked and shared embellished sex stories. She knew my secret alter ego things and I knew she’d been abused by her uncle after her parents died. She exclaimed many times that she now really liked being a whore, and loved the money. She told me do’s and don’ts. She told me where or where not to buy new kinky things. She gave me all the knowledge someone about 15 years older could. She was always fun to b.s. with.
Then, really late one night, after I ran into her on the main cruising drag. She recognized me as I parked next to her and got out. She’d chatted with me many times and knew she could shoo me away if business with someone was possible. From her parked car near a dark area where she had done probably thousands of car dates with guys we talked. As she often did, she gave me her nightly tally – eight married-man blowjobs, one guy wanted to try sucking cock with her, and four black guys wanted her “tight white ass”. At one point she explained that she was done working for the night and showed me her cum-stained tight white blouse and her smaller than perfect implanted tits. She looked at me reached over and pinched my shaft through my pants and then ran her hand under my balls toward my ass. She looked at me and said she wanted me to come home with her. I was naive and didn’t realize that she really wanted to fuck me the way she’d been fucked all night long.
About a half hour later she had me naked in a nearly pitch-black guest room of some sugar daddy’s house. She wore only a bra and panties, and had lost her Capri pants and blouse. I was face-down as her tongue pushed deep inside my ass. She circled me over and over, whispering “relax” every once in a while. I was harder than ever, but I couldn’t jack off. Then I felt her sit up, crawl forward and place her forearm on the center of my shoulders, holding me down and controlling me. Then, a huge glob of cool thick KY jelly expertly dropped into my asshole in the dark. Then, without any words, I felt a shift of body weight and more downward pressure on my torso as she lowered herself, her tits, her hips, and her hard seven inches onto my back. I felt her hand snake between us and make her cock angle to my ass as she pushed. I protested, “No, please I am not ready,” but the answer was a more urgent push into my ass, and a feminine whisper of “Just breathe out and push out…and let it happen…”
Her cock pushed into me and I felt that same virgin-like pain of sphincter stretching. I breathed out, almost into a scream, and then I did as this gurl, this professional, this whore who was now inside me told me to do. I breathed out and pushed out and took her into me. She was gentle for three or four pumps and then began to use me. I got past the pain very quickly and felt her popping my male g-spot, the prostate. She lasted longer than I would have wanted, but she’d decided to savor my ass and gave me no choice in the matter. Then, I felt her hitting my gspot just right several times in a row. I couldn’t touch myself, I was holding to edges of a really nice cotton comforter that I was getting fucked on. Her movement created friction between my hard cock against that really nice comforter. That combined with the prostate popping took me over the edge. I came, hands free, the exact inverse of when I came in my girl friends. Annabel felt and heard me cum and popped me harder and faster, prolonging the orgasm and taking me somewhere new. She fucked me forever and my gspot reacted over and over…it wasn’t an orgasm in the traditional sense after my ejaculation, it was something else. Then I felt her head tilt up and her cock shove into me deep in a final thrust of pleasure for her in a delicious mix of pain and pleasure for me. She came in me.
Annabel savored the orgasm and pulled out after a full minute. I laid there in total darkness and after I realized she wasn’t coming right back I rolled over to sit on the edge of the bed. My contracted asshole relaxed and I was worried I was about to shit in the bed. Something leaked out and out of reflex I shifted to wipe it up, only to find that Annabel had barebacked me and her cum was dropping out. I was in a special indescribable personal heaven.
After that fuck, I again retreated away from my inner whore, Rebeca and went straight for months, purging a last time.
Then, somehow on a Tuesday of a nothing-special week, I became alright with myself and my needs. I became alright with my inner whore. I accepted Rebeca. I began getting new things, very nice and expensive, built to last things, like leather and durable lingerie. During the week I revisited my old ritual of buying amazingly sexy things and then on Friday afternoon I drove to the same cheap motel and got dressed for a night of fucking and sucking. At about nine at night I walked to the counter to purchase entry to the arcade (eight dollars for entry and an hour of unlimited play and movies) and the clerk asked me how I was doing and seemed impressed with my femme-voice. He complimented me and held out his hand to shake mine and asked me my name. I offered my hand in a soft feminine manner and answered in a very femme voice, “I am Rebeca.”
How Rebeca Started
Then, out of the blue, I received a friend request on F-book from the man who started me out. At 43, he was 31 years older than me when he and I played.
I was on summer vacation and discovered masturbation in an unlikely way. Mom and dad had split up, so mom was at work during the week.
I’d watched a series of movies that involved prostitutes that looked really hot and easily captured my imagination.
I had been touching myself, but not really beating off. I was ignorant to actual masturbation. I noticed that I got hard for no reason, and that when I watched sex in movies, especially with whores, I got very hard. I thought about how hot it would be to be with a professional fuck-toy. I romanticized prostitution and imagined girls seeking and then loving work as a whore.
With mom at work, I began by playing with her makeup and pretending to be a sexy prostitute. I added some leotards and eventually an old sexy tight dress that I couldn’t believe my mom had ever worn. At one point I began imitating the whores in the movie, preening, licking my lips, and smiling in a slutty manner. I would rub myself, but had no idea what an orgasm was, so I played dress up and let my imagination run wild. About the fourth or fifth time I dressed up to play I found an angle-headed muscle-massager with a cup-shaped massage head, not at all designed for sex, and added that to the mix. I knelt in front of a bathroom mirror straddling nothing but air, and acted like the whores I’d seen in movies. I used the massager on my shaft and learned to enjoy it on the bottom side of my little cock head. I buzzed myself and made my slender six-inches (yes, I measured it out of curiosity) numb several times before something strange happened. I lost control of my dick and creamy stuff flowed out as it throbbed. I panicked momentarily and considered if I’d broken something, then realized that it felt different and good. Very good. In fact, after I stopped freaking out, I tried again and got even more intense results.
Summer vacation had just begun and rather than play with the other k**s on my street, I began playing with myself. I felt a deep rutting ache every morning as mom got ready for work and almost leaped out of my skin when she left. I began looking at mom’s cosmopolitan magazines and sales catalogs for sexy looks. I began imitating the makeup and poses and then began stroking myself instead of vibrating.
My orgasms began ruling me, so I took power and learned to ‘edge’ and prolong the playtime. My recharge time was pretty quick, and occasionally served as time to change my look and add or subtract clothes. I loved my time as a slut. I began searching the house for things to add to my play and found an old box with theater props and four wigs in it. I immediately began adding a wig to my private play. I had a choice of a platinum blonde, a curly dark mousey brown, a long straight dark brown (almost black) and a short curly red. The red was my favorite for color, but the long dark brown was super sexy and feminine. Of all my limited choices, these two were my go-to slutty wigs.
I experimented with makeup and learned.
One day, about two months into the three and a half that made up summer vacation, I was in my room, kneeling on the playroom floor the way I had seen in a cosmo magazine and jacking myself off. I watched myself in the mirror, preening and calling myself a whore and other tantalizing titles.
I remember that I was close to cumming for the second time that day when there was a knock on my window. I dove behind the doorway and peered at the window to see that it was the man next door – Jerry, or Mr. Carlton, as I knew him at that point.
Jerry peered at me through the window with a slight smile and said loud enough through the window that he’d seen me in there playing for several weeks and that he wanted to talk with me. I said he’d seen me and it was ok. Eventually, he wore me down and I accepted his suggestion to go out back and talk to him through the back fence.
I slipped on a pair of my mom’s high-heels, they were very tight, and walked out back. I came around the corner of the back room to see him standing at the back gate of our tall brown wood-picket fence. His thumbs were looped through his belt loops on his jeans and his hands were relaxed, albeit in front of his mature dick.
I realized that another man or a dick of any sort hadn’t been in any part of my whore play. Seeing his hands there triggered something in me, a curiosity about how excited he was to see me dressed like a slut. There I stood, wavy long brown hair, a short stretch-satin sea-blue dress, pulled-up to make it even shorter, ‘nude’ pantyhose, pre-cum and lotion soaked red panties, black high-heeled sandals, an old satiny black bra with socks rolled to make boobs on my slender frame, and way too much makeup on my face- particularly around the eyes, and a racing heart.
Mr. Carlton smiled and reassured me that I was not in trouble and that he wouldn’t tell anyone about me. I remember that at the time I didn’t believe him. He was believed to have beaten his actual c***dren and then after a short re-marriage his step c***dren also. I remember fearing him. After some talk about him watching me playing dress-up in my room from his house on the days he didn’t have to work until night time, he asked me “What do you imagine when you are dressed up and playing by yourself?”
I thought for a moment and stupidly answered with the truth, “I imagine I am a prostitute, the prostitute I want to meet and play with some day.”
He lit up with a smile and shook his head, undoubtedly at his amazing luck. He considered the situation a moment and asked me if I knew what prostitutes really did.
I answered slowly, and somewhat thoughtfully, “I do. They have sex for money with lots of men because they are good at it, and because they like it.”
As I produced my answer, he opened his pants and began rubbing himself. I couldn’t see his cock, but I knew he was doing that. He asked me why I thought that was so sexy.
I answered something like, “They are sex. They have sex and are good at it because they know what they want…and what the men want…and they do what they know is sexy.”
Mr. Carlton, Jerry as I would later call him asked, “Have you ever seen any movies of women having sex with men?”
I replied with an indignant yes, and then after being challenged listed off several ‘r’ rated movies. He snickered and said he meant something much different, people actually having sex and showing it all – ‘porno’. I confessed I had not.
He said, “Well, let me make you a deal, I know your mom will be home in about two hours, so there is no time today, but if you let me watch you posing like you were and rubbing yourself like you were right now, and, if you let me put myself up against this knot-hole in the fence and keep doing your poses like I just said until I am done, I will let you see a movie with men and women actually fucking in it tomorrow.”
My instinct was “Oh my god yes!” but I said no at first and then relented after he asked me what the harm was. We had a date…of sorts.
I posed for a few minutes and stroked myself, re-gaining my hard dick in no time. I realized that I liked the attention and loved doing the poses. After about five minutes he pressed his cockhead against the golf-ball sized knot-hole and told me to hold my dress up above my waist and turn to let him see both my butt and my dick. I did as asked and just as I wondered how long this would continue, his orgasm shot through the knot-hole. He pulled away after a few seconds and looked around and then back at me as he zipped up. “I’ll see you tomorrow morning. Bring your things over and change at my house if you like.”
The first day I didn’t bring my things and he let me watch a movie with porn legend Traci Lords in it. I came three times before he came in. I went home after some more discussions about sex and prostitutes…I don’t remember them any more…but I do remember that I agreed to come over again the next day and to dress up for him.
Over the remainder of that week and up to the end of the next week I went over every week day. He told me he had taken vacation just to help me out. He provided me with several key items of clothing and accessories. Among those was a garter belt and stockings, black high-heeled pumps that fit, skin-appropriate makeup (I was far more pale than my mom), and a long wavy orange-red wig. Our visits amounted to him watching me as I watched myself in a mirror dancing or posing and otherwise acting like a whore as I watched various porn movies he had rented for me to watch. I knew he was masturbating out of view, but I didn’t care. I considered that I might be gay, but since I didn’t get excited at the sight of the men, I didn’t worry about it too much.
Then, about the third or fourth week, he tricked me and showed me a tranny movie. He lied and said they had given him the wrong movie, but the t-gurl was a red-head and was very young. The movie was a tranny-trick plot, in which you didn’t really know it was a tranny, and neither did the unsuspecting guy, until she made him suck her dick and then he fucked her from behind. That was the first notion I had about anal sex – it hadn’t occurred to me.
We only made it into the second sex scene when he heard my mom pull into our driveway and come home early.
I freaked out and quickly changed and cleaned up. Jerry told me it was perfectly alright to leave my things with him that night and that he would see me tomorrow. I left out the opposite side door and walked to my house from a completely different direction to seem like I was at a street-friends house. My mom had come home early for some trivial reason and never suspected much less discovered what I had been doing.
Overnight I obsessed about the red-haired tranny and the things she had done. She’d been Hispanic and was very exotic and I confessed to myself, very sexy. I came about four times overnight as I obsessed and dreamed of her sucking cock and bending over to get fucked. By morning I came to the conclusion that she was probably an even better prostitute than a real woman because she knew how to make a dick feel good. Then I began to realize I was becoming part-gay, or as I later learned, bisexual.
The summer vacation was nearly over and I was more ready than ever to explore. Jerry began to openly masturbate in the same room and then seated right next to me.
The Monday that marked only two more weeks to the start of school Jerry game me a few new things including a black corset with red piping and lace designs, a longer more luxurious red wig, a black collar like the one we’d seen in several movies, and some lip gloss. I looked amazing and actually quite similar to a no-name tranny we’d seen in a few of the movies (I wish I could figure out who it was, but I can’t seem to see her anywhere!!!). I came out and Jerry smiled approvingly and said, as a compliment tailored to me, “You look like a hot fucking whore…so cute and sexy…”
I sat on what had become my position on the couch, on the left side, so I could rub myself and see both the movie and my reflection in the mirror. Jerry had insisted that I watch myself as I came, just like when I was alone, so he’d placed a floor mirror next to the TV stand and I used it. I loved it.
This time Jerry sat pants down and then after a while, he kicked them off. He’d never done that before. After a few minutes I was about to have my first orgasm. As I came I looked at myself and his hand snuck over and caught my cum. I looked at him as he watched me and just as I finished he said, “Taste your sex,” and then wiped my glossed lips with my cum shot. Without thought I was repulsed and turned away only to open my mouth and have some of it slide in. I tasted it just as I was about to protest and then I stopped myself from saying anything at all.
Jerry paused the movie, as we often did, and allowed me to go clean up. I went to the upstairs rest room, is step-daughter’s old bathroom, and fixed my makeup. I emerged with newly glossed lips and a dirty taste in my mouth- my own cum.
I sat to resume the playtime. After only about ten minutes I was well on my way to another orgasm and began a prolonged edging experience. At the start of the next scene the Tranny knelt to suck a guy off. I had not noticed Jerry stopping his own edge-stroking. He leaned over and said, “Now let’s find out if you have learned anything…lets find out what kind of whore you are going to make…”
I didn’t fight it. I didn’t know it was coming, but I had already known it probably would get to this. Jerry placed his hand on the back of my neck and skull and pulled-pushed me to his adult-size penis. Without being told to, I opened and accepted him, then more of him, and more until I felt his cock hit my throat and I gagged. He allowed me up slightly then forced me back down. He did this until I go the idea and began doing it on my own. Then, without warning, his hand returned with a heavy determination and he controlled me back and forth as he came in my mouth.
I was smitten and disgusted all at once. I couldn’t let go of my own false narrative that I was a normal boy with a bisexual secret. I now knew what I was secretly afraid of- that I really like being a dirty slutty girl and now, really knew I liked my mouth used like the girls in the porn movies.
Jerry pulled out and complemented me and wasn’t at all shocked when I went to change and clean up.
That night I relived the experience over and over and then began adding nuances to it. I added the notion of doing it in car, or on a street, or with a stranger in a restaurant – all different scenes from the porn movies he’d shown me.
By this point Jerry and I had established a signaling system to indicate when the other wanted to play and was available. I got up in the dark hours of the morning to put my signal, a book, on the shelf at the same window Jerry had spied on me at the start of summer.
I obsessed and couldn’t sleep. I wanted to relive the intensity and lust of the moment.
I had trouble identifying it at the time, but I was instantly addicted to the degrading whore-like lust and wanton nature of being willingly used by someone who also wanted to use me. Finally, almost on time, but a bit late, mom left for work. I went to begin the first part of my dressing ritual and put on my stockings, garter, panties, form-less bra, and my corset. I put a baggy sweatshirt and sweat pants on and waited until I saw Jerry’s hand put a candlestick in his window. I went out the back door, over my fence, over Jerry’s fence and arrived at his door just short of two minutes later.
In twenty more minutes I was made-up and practically running to the couch in the upstairs family room where we’d watched hundreds of hours of straight and now tranny porn on.
I looked like a slender slutty red-headed teenage girl- totally passable at no more than 100 pounds and with a great bubble ass.
Jerry came into the room and opened his pants. He didn’t start a movie, instead, a sound track of people having sex taken from movies began playing on his sound system and he stood next to the floor mirror.
Jerry looked at me and said, “Good gawd, you look like such a hot girl…I know what you want. Now come over here and watch yourself getting what you want. Watch yourself as the porn star.” He opened his pants and produced his hard adult cock.
I stood, preened at myself in the mirror, looked at his cock straight on, then in the mirror and strutted over. I sunk to my knees and began imitating the porn stars we’d watched together. I willingly and wantonly sucked his cock. I watched myself being the whore I had been watching all along.
Jerry told me in a loud domineering voice, “Rub that dick of yours, rub yourself as you suck my dick you little whore.”
I can never explain how electric that moment was for me, like a d**g experience it was euphoric. However, unlike a d**g experience I have been able to take it to new heights on many occasions.
This was when Rebeca, even though she hadn’t been named yet, arrived. On a Tuesday morning in mid-August.
Three days and about 20 blow jobs later, on Friday, this same unnamed whorish girl-boy got fucked the first time.
Much like the first blowjob, she was expecting it as she was positioned standing behind the couch’s back rest with her arms stretched out toward the ends. Later, she shared with a dominatrix that her first time was like being on a bondage cross without the bonds, and using a couch. I was positioned, legs spread, arms spread and useless watching everything as it happened. I, or my alter ego Rebeca, began having second thoughts at the beginning when Jerry’s thumb had to press hard to force some lube into me.
Much different from the first blow job in which the slight suffocation and complete submission was an aphrodisiac, I hated the pain and the loss of control. I struggled to break free and to stop, but he was big and I was not. I even cried as I was stretched without consent thinking he might stop, but he didn’t.
In short, Jerry had seduced me so he could lie to me and take me.
Jerry lied and said a small dildo was not the right way to prepare.
Jerry lied and told me there would be a very slight stretch and almost instantly, just like the gurls in the movies, it would feel amazing.
And finally, Jerry’s supreme lie was that we would stop whenever I wanted…yeah, right. I cant and don’t really blame him for these lies- I was a very hot, totally passable piece of jailbait ass.
Jerry ****d me and didn’t stop till he had cum deep inside me right after jerking me off and making me cum as he fucked me.
After he finished and sent me to the bathroom, my alter ego let me stop…for a while. She, the yet unnamed Rebeca, apologized as I cleaned off my tear stained face and my creamy ass.
Just before I removed my wig ‘She’ swore she would never want to do that again, but secretly she knew it was a grand lie and that being fucked like a whore was now a part of her.
It would be years before the second actual fuck from a real person with a penis. As the school year began I tried to forget and part ways with my whorish alter ego. I purged and disposed of my things in cycles that occurred several times only lead back to acquiring new things at great cost.
Mid-way through the next summer, while I was struggling to pass summer school and make up for failed classes, Mr. Carlton was visited by the Sheriff’s department and a week later I was told that he was arrested in the morning just after the school bus drove off. A week later my mom and dad sat me down with me and asked I had been in any contact with the estranged and now arrested Mr. Carlton.
Without a beat and in what must have been a convincing enough manner I lied and said no, and that I barely knew him. This was an era before digital media, so I had no pictures or recordings to worry about and nothing ever became of the relationship. Later I learned that he had been accused by actual son, now an adult, along with his step daughter, his step son, and his second wife of, well, you know what, and he was locked up for a while.
I secretly played by myself and effectively kept my alter ego chained inside me for years. I graduated high school and while I was accepted at the local community state colleges, I couldn’t afford them and wasn’t really interested. I joined the Air force to learn a skill and earn for school. There was no war, except the war on d**gs, so I bounced from place to place and about a year into my term of service I let Rebeca back out.
I was in amazing shape and could afford nearly anything I wanted. I had a car and a paycheck. I had freedom and was not yet 20. I became a hot slutty whore in private, playing for hours on end and at anytime of day that I could.
Some weekends I began renting a motel room and playing non-stop. I developed a ritual of purchasing new items and then playing with them on the weekend.
Then, I discovered adult arcades and theaters.
At first I would let others suck me, a hot 20 year old just getting a blowjob from a nameless guy I would never see again. Then I began sucking cock and participating in group jack-off play and finger-fucking.
Then, one night, I was driving near the nasty part of town and met a real live tranny whore on the street. She was cute, somewhat older, yet smaller than me, and sucked me off in a dark alley doorway just like I had imagined a nasty whore-tgurl would. She was a cute Hispanic and really looked like a woman until you got close and knew what to look for. I came so hard with her blowjob that I was convinced no real girl could ever match her (I have been right so far).
About six months after the tgurl BJ I met a white tgurl named Annabel, and found myself actually talking with her in a parking lot. I learned that she didn’t like to play with other tgurls, but exactly like my later ego, Annabel loved being a slutty whore.
I met Annabel on and off a few times over a couple of months, never having sex or her turning a trick with me. We talked and shared embellished sex stories. She knew my secret alter ego things and I knew she’d been abused by her uncle after her parents died. She exclaimed many times that she now really liked being a whore, and loved the money. She told me do’s and don’ts. She told me where or where not to buy new kinky things. She gave me all the knowledge someone about 15 years older could. She was always fun to b.s. with.
Then, really late one night, after I ran into her on the main cruising drag. She recognized me as I parked next to her and got out. She’d chatted with me many times and knew she could shoo me away if business with someone was possible. From her parked car near a dark area where she had done probably thousands of car dates with guys we talked. As she often did, she gave me her nightly tally – eight married-man blowjobs, one guy wanted to try sucking cock with her, and four black guys wanted her “tight white ass”. At one point she explained that she was done working for the night and showed me her cum-stained tight white blouse and her smaller than perfect implanted tits. She looked at me reached over and pinched my shaft through my pants and then ran her hand under my balls toward my ass. She looked at me and said she wanted me to come home with her. I was naive and didn’t realize that she really wanted to fuck me the way she’d been fucked all night long.
About a half hour later she had me naked in a nearly pitch-black guest room of some sugar daddy’s house. She wore only a bra and panties, and had lost her Capri pants and blouse. I was face-down as her tongue pushed deep inside my ass. She circled me over and over, whispering “relax” every once in a while. I was harder than ever, but I couldn’t jack off. Then I felt her sit up, crawl forward and place her forearm on the center of my shoulders, holding me down and controlling me. Then, a huge glob of cool thick KY jelly expertly dropped into my asshole in the dark. Then, without any words, I felt a shift of body weight and more downward pressure on my torso as she lowered herself, her tits, her hips, and her hard seven inches onto my back. I felt her hand snake between us and make her cock angle to my ass as she pushed. I protested, “No, please I am not ready,” but the answer was a more urgent push into my ass, and a feminine whisper of “Just breathe out and push out…and let it happen…”
Her cock pushed into me and I felt that same virgin-like pain of sphincter stretching. I breathed out, almost into a scream, and then I did as this gurl, this professional, this whore who was now inside me told me to do. I breathed out and pushed out and took her into me. She was gentle for three or four pumps and then began to use me. I got past the pain very quickly and felt her popping my male g-spot, the prostate. She lasted longer than I would have wanted, but she’d decided to savor my ass and gave me no choice in the matter. Then, I felt her hitting my gspot just right several times in a row. I couldn’t touch myself, I was holding to edges of a really nice cotton comforter that I was getting fucked on. Her movement created friction between my hard cock against that really nice comforter. That combined with the prostate popping took me over the edge. I came, hands free, the exact inverse of when I came in my girl friends. Annabel felt and heard me cum and popped me harder and faster, prolonging the orgasm and taking me somewhere new. She fucked me forever and my gspot reacted over and over…it wasn’t an orgasm in the traditional sense after my ejaculation, it was something else. Then I felt her head tilt up and her cock shove into me deep in a final thrust of pleasure for her in a delicious mix of pain and pleasure for me. She came in me.
Annabel savored the orgasm and pulled out after a full minute. I laid there in total darkness and after I realized she wasn’t coming right back I rolled over to sit on the edge of the bed. My contracted asshole relaxed and I was worried I was about to shit in the bed. Something leaked out and out of reflex I shifted to wipe it up, only to find that Annabel had barebacked me and her cum was dropping out. I was in a special indescribable personal heaven.
After that fuck, I again retreated away from my inner whore, Rebeca and went straight for months, purging a last time.
Then, somehow on a Tuesday of a nothing-special week, I became alright with myself and my needs. I became alright with my inner whore. I accepted Rebeca. I began getting new things, very nice and expensive, built to last things, like leather and durable lingerie. During the week I revisited my old ritual of buying amazingly sexy things and then on Friday afternoon I drove to the same cheap motel and got dressed for a night of fucking and sucking. At about nine at night I walked to the counter to purchase entry to the arcade (eight dollars for entry and an hour of unlimited play and movies) and the clerk asked me how I was doing and seemed impressed with my femme-voice. He complimented me and held out his hand to shake mine and asked me my name. I offered my hand in a soft feminine manner and answered in a very femme voice, “I am Rebeca.”
Grace
- 27.04.2021
- 18
- 0
