My childhood was a little traumatic, growing up in a working-class family in South Boston in the 1990s. My mother and father are both pure-blooded, Irish Catholics, and I inherited their pale skin, freckles, and bright red hair. I was teased mercilessly and picked on by many of the other kids. They derisively called me a ‘ginger’, and some of the boys even bullied and beat me up.
I couldn't defend myself very well either. I'm short, slimly built, effeminate looking, and even considered to be pretty for a boy, partially due to my shoulder-length, red hair and cushy, girly ass. I have thick, soft lips too. The teasing and bullying got even worse in middle school and high school, and I became a loner who didn’t participate in sports or other school activities. The only real friend I had was my older brother. He's four years older than me, though, and we didn’t hang out together very much.
My name is Danny, and looking back now at the age of thirty-six, with only slightly more muscle tone and a family of my own, it’s hard to recognize the boy I was back then. I hadn’t thought about my past for quite some time, until my wife, Megan, started losing interest in sex. I started looking elsewhere for sexual relief, and this story will enlighten the reader about the experiences I had as a teenager, that influenced how I found the sexual satisfaction I was seeking as an adult.
I turned sixteen in the summer of 1996, before my junior year in high school. My parents always felt sorry for me since I was picked on so much and alone most of the time, so they surprised me with a gift of a refurbished, desktop computer that they bought from a local repair shop. With both of my parents working, and my brother out of the house by then, I spent a lot of time alone on the computer. As a teenager, I was obviously very curious about sex, especially since I had no sexual experiences before then.
It didn’t take me long to start searching for porn sites on the internet, and I found dozens of sites that I viewed for all kinds of sex. I was obviously interested in seeing naked girls, and even sex videos of them being fucked, but I also saw plenty of gay and bisexual material that was fascinating to me. There seemed to be a focus on the male actors and participants with large and uncircumcised cocks, and that's one part of my body that I'm not ashamed of.
At the age of sixteen, my uncircumcised cock was thick, almost nine inches long on hard, and six inches long and still thick when soft. I had little to no facial or body hair, except for the bright red hair on my head and pubic bush, and my soft cock looked huge on my rather effeminate body. I found several websites where mature men went to look at pictures of and to contact boys my age and older for sex. They call boys like me, with slight builds, little body hair, and effeminate characteristics ‘twinks’.
There seemed to be a significant number of mature men who wanted to have sex of all kinds with twinks. Even though I could certainly identify my outward appearance as a twink, I still hadn’t thought much about what kind of sex I was interested in having with the men, or if I was interested at all.
I thought for a long time about posting a message to make myself available to those horny men. I resisted the urge, though, since most of the websites had members from all over the country, and I thought that the chances of making a connection with anyone in my area would be slight. Then I discovered a fairly new website called Craigslist, where people posted messages to buy and sell things of all types. They also have a ‘Personals’ section, where I quickly learned men and women advertise for sex.
It didn’t take me long to get familiar with the site, and I was soon reading dozens of messages a day, from people in my area looking for all kinds of sex acts. I learned that the age of consent is sixteen in Massachusetts, and many of the men were clear that, although they wanted to have sex with teenagers, they had to be of legal age.
Some of the men specifically advertised for twinks, and many of their descriptions fit me perfectly. They like twinks with large cocks, so they can suck or even be fucked by them, and in other cases it was just the opposite. They really seemed to be turned on by the thought of having sex with an inexperienced, effeminate teen with a big cock, and I could only guess that their fantasies had something to do with thinking of twinks as girls, except with big cocks.
Many of the men included words about them being ‘generous’, or ‘willing to show my appreciation’, as a way to let the reader know that they would be willing to pay for the sex. I guessed that they did that since they couldn’t come right out and solicit on a public internet site, by talking about payment, without being arrested for solicitation. And since I hadn’t been able to get a physically demanding summer job like many of the other boys, I was thinking that would be a good way to make some money.
After getting turned on enough reading those posts, I finally got the nerve to respond to an ad looking for a twink. The man included pictures of his upper body, cock and ass, and his post read, “Forty-two-year-old MWM seeks barely-legal twink for a good time. Very generous for the right girly-boy who is willing to be my bitch.”
I had seen plenty of cock pictures of grown men on the internet, but it was different and more exciting to finally email a man that I could possibly meet. He had two pictures of his cock and balls, one soft and the other on hard, and his cock looked to be maybe six and a half inches long in the hard picture, about medium thickness, and with big, low-hanging balls. I still didn’t know what would be expected of me, since I had no experience, but it was arousing to think about the possibilities.
It was a little scary putting together a response, and I included two pictures. One was from the front, from my nose down to my knees, with an impish smile on my face, and the other was from the back, showing my plump, girlish ass. I didn’t fully realize just how feminine I looked until I saw those pictures, and I thought that they would really excite the man who posted the ad. Even though he couldn’t see my whole face, he still saw that I was attractive, young, feminine looking, and with long red hair and red pubic bush.
I was hoping to get as much money as possible from him. I included the major cross streets two blocks from my home in my response, to give him an idea of my location, along with my two pictures, and continued with, “My name is Danny, and I’m a virgin, Southie, barely-sixteen boy who is willing to learn, from a very generous man. What does ‘generous’ mean to you, and where would we meet?”
He responded, “My goodness, sweetie, you’re so cute and sexy. And what a marvelously big, cream-filled clitty you have, that’s just begging to be sucked. I’m willing to pay you one hundred dollars, just for meeting with me and exploring the possibilities, with another fifty if you let me do everything I want, with such a sweet, virgin boy. My name is Gavin, and I’m a Southie too. I can pick you up on that corner in my car, and I have a safe place nearby where we can meet.”
It was apparent from his response, which I received in only a few minutes, that I might have underestimated how attractive I would be to at least some older men. The amount of money he was offering was amazing, though, and most of the guys that I knew from high school who had summer jobs, were only earning the minimum wage, which was around four dollars and seventy-five cents an hour back then. I mean shit, just my base payment of one hundred dollars would be over a half week’s pay for them, and I wouldn’t be paying any taxes.
My parents wouldn’t be home until 7:00 pm or so, and it was only 2:00 pm when I first made contact with Gavin. I was eager to meet with him, and I replied, “Okay, Gavin, sounds good to me. What if we meet on that corner at 2:30 pm?”
He responded right away, and after giving me a description of his car, he said, “It would be a lot better for me if we met at 3:00 pm, Danielle. I want you to have time to take a shower, and be sure to wash your yummy clitty and ass crack really well for me. Please confirm, and I’ll see you then.”
I confirmed the time, and got into the shower and washed myself well. He had been using such feminized terms for me, like girly-boy, cutie and sweetie, and referring to my cock as a clitty. In addition, he referred to me as Danielle in his last email, and I thought I would dress in a way that played to his apparent fantasy of me being a young girl. I wore an androgynous, sleeveless t-shirt, and a pair of simple, tight, cotton shorts, with no underwear, that accentuated my plump ass, and even showed my cock bulge.
It was really scary standing on that corner, not knowing what to expect or whether I would be safe. I got there about five minutes early, and I was looking the other way when he showed up, right on time.
I must have looked nervous when he pulled up, and called out to me through the open window, “Hi, Danielle. My, but don’t you look pretty. Don’t be nervous, sweetie, I’m a really nice guy, and you’re safe with me.”
He's a respectable looking, handsome man, and I thought that he looked a little familiar to me. I got in and we had driven for only a few blocks, when he turned into a narrow alley behind a hardware store. That’s when I remembered why he looked so familiar. My father had taken me to that store with him one time when I was only twelve years old. Gavin didn’t recognize me, and I sure wasn’t about to tell him who I really am.
We got out of his car, and he led me up a narrow staircase on the back of the store, as he leaned down to me and whispered, “We have to be really quiet, Danielle. We’re going up to my private office on the second floor, and I don’t want any of my employees to know that we’re up there. It’s really comfortable, and I have a small bed that I use sometimes, when I’m working late at the store.”
It felt strange walking into that room, alone with a man older than my father, but it was also exciting since I would be learning new things. He quickly took off all his clothes and sat on the bed, as he held out his hand to me and said, “Come stand in front of me, Danielle, and let’s get a good look at you.”
I couldn’t help looking down and staring at his very hairy crotch and semi-hard cock, as I got a whiff of his mature, musky smell, and stood in front of him. He put his hands on my hips, and then ran his hands over my ass, before lifting my t-shirt and pulling it off over my head. His hands were trembling as he leaned in and kissed me on the neck, and then slowly licked and kissed his way down my upper chest, until he began sucking my right nipple. He continued sucking me there as he gripped my ass cheeks with his hands and massaged and rubbed them, as he pulled me up against his crotch.
It became even more obvious that he was reveling in the fantasy of me being a girl, as he pulled down my shorts, and I kicked them off my feet. He cupped my ass again, and stopped sucking my nipple as he said, “Me oh my, what a naughty girl you are, not wearing any panties when you came to visit old Gavin.”
To this day, I still don’t know what motivates men like Gavin to treat boys like girls. Maybe those types of men can’t accept the idea of themselves being gay, and fantasizing that the boys are girls, and treating them that way, allows them the illusion of normalcy.
Gavin continued kneading my ass as he began to lick and kiss down my stomach, until he was only inches above my crotch. My cock was still soft, and it felt wonderful when he finally leaned in and sucked my cock head into his mouth, as he fondled my balls. I had never been sucked before, and I loved the warmth and wetness of his mouth. My cock got hard in seconds, and he was choking on it as he tried to take it all the way to my balls.
After sucking me for a couple of minutes, he lay back on the bed and pulled me on top of him in the opposite direction, as he said, “Come on, sweetie, get a taste of my cock while I suck your nice clit. If this really is your first time, just go slow, and I think you’ll enjoy it.”
He resumed sucking my cock, with his hands gripping my ass and pulling me tightly against him. I had never been attracted to other boys, and despite my rather feminine appearance, I had never considered myself to be gay, and I didn’t even know what bisexual was. But lying on top of him, with his then-hard cock in my face, I was overwhelmed by the pure sexuality of it all. I tentatively tasted his precum-oozing cock head, and then sucked it into my mouth. I really liked the taste and texture of his cock and began sucking him.
I could tell that I was doing a good job sucking him, because he was moaning on my cock and pushing his hips up to push his cock farther into my sucking mouth. I also began to fuck his mouth, and my ejaculation was approaching quickly, since that was my first time having any kind of sex with anyone.
I didn’t know what I should do, and whether he wanted me to cum in his mouth, so I pulled off his cock and said, “I’m getting very close, Gavin, you’d better stop now if you don’t want me to cum in your mouth.”
When I told him that I was close, he held me even tighter, and sucked on my cock harder. In just a few more seconds, I had the most wonderful feeling, as my cock throbbed and jerked as I had my biggest and best ejaculation ever. He kept sucking and swallowing, as pulse after pulse of my teen cum flooded his mouth, and continued even after I had gone soft. That was the most wonderful feeling ever, and I loved being sucked off by him.
I didn’t know if he wanted me to suck him all the way off or not, and I got my answer when he rolled me off to the side and said, “Your pussy juices were so sweet, but you have to stop sucking me before I cum too soon. Let’s try another position.”
Gavin stacked a couple of pillows in the middle of the bed, and had me lie face down on them with my hips on the pillows. That pushed my bubble butt way up in the air, and I wasn’t sure what he had in mind.
He got behind me, between my legs, and the next thing I felt was him kissing and licking my ass. Then he put his hands on my ass cheeks, as he spread them apart and began licking and sucking up and down my ass crack. That was another totally new and wonderful experience for me, and it became especially erotic when he started to suck my asshole and try to push his tongue inside of me.
I had heard the expression ‘eating ass’ before, and he had his face buried in my ass, sucking on my asshole, like he was starving for it. He reached up and rubbed and caressed my back as he continued eating my ass. He ate me that way for what seemed like ten minutes, and then he abruptly pulled away for a few seconds. Then I felt what must have been a kind of warm oil poured in my crack, just before he moved up and began sliding his hard cock up and down in the cleavage of my ass.
He fucked me that way for a few minutes, with his cock sandwiched between my oiled ass cheeks, until he leaned down near my ear and whispered, “I’ll give you that extra fifty dollars if you let me fuck your virgin ass-pussy bareback. I’ll be very gentle, so just let me know if I’m hurting you.”
That was a day of many firsts for me, and I decided that it would be fun to see what it was like to be ass-fucked. I was thankful that his cock is shorter and thinner than mine, and I replied, “Okay, Gavin, but please do take it easy with me.”
He poured a little more oil in my crack, and after sliding his cock back and forth to distribute the oil, I felt him press his cock head to my sphincter. He pressed gently until I felt his cock head start to enter me, and he said, “Just breathe deeply, sweetie, and relax. I’ll take it slow in your pussy, so let me know if it hurts.”
I felt a lot of pressure as his cock head popped inside of me, and he stopped pushing for a few seconds. Then he started a fucking motion, going in and out slowly, with constantly lengthening strokes. Before I knew what was happening, he was buried to the balls in my ass, and I loved the feeling of his cock rubbing, what I now know is my prostate. He paused for a few more seconds to make sure that I was okay, and when I didn’t say anything, he began taking long strokes, with his balls slapping up against my ass each time.
It's hard to adequately explain how much I enjoyed being under him that way and being used like I was a girl taking his mature cock. It was a mixture of emotions; on the one hand knowing that I had some power over him because of his perverted desire for me, and on the other, that I was being used as his little bitch.
He had been fucking my ass for only a few minutes, when he stiffened up, pushed all the way inside of me, and I felt his cock pulsing as he filled me with his cum. The idea that I was being inseminated by him made me feel even more like a girl.
He stayed in me until his cock softened, and then he pulled out and moved back down between my legs as he said, “Just relax, Danielle, we can’t take you home with your pussy all soiled like this.”
The next thing I knew, he was spreading my ass cheeks with his hands again and sucking his cum out of my ass. I learned later that's called felching, and I knew that his fantasies and perversions had to be very strong for him to do something so nasty. After he finished cleaning my ass, he pulled me on top of him to suck his cock clean, as he sucked me off again. I would find out with more experience, that he really got his money’s worth that day. Being allowed to suck two loads out of me, while I sucked his cock and let him fuck my ass, were a lot of activities for one meeting.
It was almost 4:30 pm when we were in his car, with him taking me back to where he picked me up. He handed me seven twenty-dollar bills and a ten as he said, “It was wonderful meeting you and being with you today, Danielle. You did really well, especially if this was really your first time. I hope that we can meet regularly, maybe at least once a week, and I have some friends that would enjoy being with you two. Maybe you can be with two of us next time.”
I really felt self-conscious and guilty when he dropped me off on that corner, and it seemed like everyone was staring at me and knew what I had done. I felt somehow dirty, and I soaked in the bathtub when I got home, partly to help sooth my sore ass. The guilt soon passed, and the realization that I had made one hundred and fifty dollars in only an hour and a half made me happy.
Then I thought about everything we did together, and I jerked off in the bathtub. I could hardly believe how much I enjoyed sucking his cock, and of course being sucked off, and being fucked in the ass was amazingly erotic. I even enjoyed being treated like a girl, and a whole new world had been opened to me. Finally, there was something positive about my feminine appearance, instead of it being a negative.
It was only 5:00 pm when I got out of the bathtub, and I still had plenty of time to go online again before my parents got home. I tried to use what I learned from Gavin, and his hunger for girly-boys like me, to focus my search on similar men who would likely be willing to pay more to satisfy their taboo perversions with a feminized boy.
I looked for about a half hour, and then found an interesting posting. It was from a man who described himself as ‘Uncle Colin’, and his message read, “Fifty-year-old, married uncle is seeking a cute, young boy to be my ‘niece’ tomorrow afternoon, while my wife is away from home on business. You must be between sixteen and seventeen years old, and not have done this very often before. I will make it well worth your time. I will provide all of the clothing to make our time together special.”
He included several pictures, and his cock looked to be bigger than Gavin’s, and maybe about the size of mine. He also included a picture of himself lying face down on his bed, with his arms reached back and spreading his ass cheeks with his hands, exposing his asshole. That probably would have grossed me out, if I hadn’t had my experience with Gavin earlier that day.
I included the same pictures as before in my response and took another one of my ass spread like Colin was doing. I gave the location as those same cross streets, and then sent him the following message, “My name is Danny, but you can call me Danielle. I just turned sixteen, and I would enjoy being your ‘niece’ for the afternoon. I’ve only had one previous experience with another ‘uncle’, and I’m excited to learn more. Your generosity will be expected and appreciated.”
My hand was shaking as I hit the key to send the message, and when I didn’t get a response after ten minutes, I thought that I might have pushed too hard about the money. It was a big relief when I finally got his response, which read, “My dear, sweet, Danielle. Thanks for your reply to my ad. I can tell from your message and pictures that you are just what I’m looking for, and you will be well worth the money. I’ll pick you up on that corner at 1:00 pm tomorrow, and I’ll be driving a black Lexus with darkly tinted windows. Please shower and wash yourself well, just before you meet me. I live about six miles from you, and I know that we’ll have fun together.”
I was so excited to have made arrangements with Colin, and I could hardly wait to see what he meant about providing clothing, but I assumed that it would have something to do with me dressing up like a girl. It was hard to sleep that night, thinking about what we might be doing together.
The next morning, I selected a sleeveless t-shirt and tight cotton shorts to wear again, and made sure that I was showered and on the corner, a few minutes before 1:00 pm. He drove up just a little late, and rolled down the window to say, “Sorry I’m late, Danielle, the traffic was horrendous coming over here. Get in honey, and we’ll be on our way.”
He was mostly quiet on the drive to his home, except for telling me how pretty I was. About fifteen minutes later, we pulled into his garage, attached to a beautiful home in an upscale neighborhood. We went inside, and he led me to his bedroom on the second floor, and had me stand in front of him as he sat on the bed.
There was a small pile of clothes on the bed next to him, and he started pulled off my shirt as he said, “Go ahead and take off those shorts, Danielle, I have something special for you to wear.”
He licked his lips as he had me step into a pair of girl’s white cotton, bikini panties. My balls were hanging out both sides of the gusset, and my soft cock was straining at the fabric and poking out the side. Then he dressed me in a short, plaid skirt like the girls wear in parochial school. Next was a bra, already fitted with very realistic rubber inserts that made me look like I had C-cup breasts. Finally, he pulled on a sleeveless, white blouse that complimented the outfit.
Colin reached out and cupped my ass with his hands, before he got up and led me over to a chair in front of a vanity mirror, as he said, “This outfit looks very nice on you, Danielle, but now we have to complete your transformation. Here, cutie, sit on my lap facing me, while we get this makeup on you.”
He scrunched down a little in the chair, as I straddled his lap, and I was sitting on his very hard cock. He applied eyelash thickener and eye liner, and then applied several types of makeup to my face. Then he applied lipstick and sprayed my neck with perfume, before getting a spray bottle, brush, and hair dryer, and brushing and shaping my hair.
When he was finished, he said, “There you go, sweetie, turn around and see what a pretty girl you are.”
I could hardly believe the transformation, and I was staring at a very pretty version of myself. I think I was starting to understand, at least a little, how those men were motivated to have perverse thoughts, when they saw a boy like me. He closed his eyes and pulled my balls and ass slowly back and forth over his hard cock lump, and then he pushed me to my feet, as he stood up, and I slipped on some stylish saddle oxford shoes to complete my outfit.
I stood there, turning around and from side to side, looking at my entire body in the mirror, and I thought that I looked fantastic. I was wondering what he would do next when he said, “Let’s go for a short ride, honey, I want to show you off to my friend, Tony. He might want to invite you over himself, one of these days.”
We got back into his car, and drove a few blocks to a little strip mall, pulling up in front of a store called ‘Tony’s Barbershop’. We went inside, and Colin pushed me in front of him as he said, “Hi, Tony, I’d like to introduce you to Danielle. She’s my niece, and I thought that you might like to get to know her.”
Tony is a rugged-looking, Italian barber with a scruffy beard and medium-olive complexion, and not too bad looking except for being a little overweight. He stepped up to me, kissed me on the cheek, and then cupped my ass cheek with one hand, and my crotch with the other, under my skirt, as he said, “Oh yes, Colin, she is a fine young lady, and smells so lovely. I’ll have to get her email address from you, so I can set something up with her.”