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.”

I was looking into his big mirrors as I was standing there, and I was amazed all over again at how pretty and sexy I looked. We talked for a few more minutes, until Colin led me out of the shop, as he looked back over his shoulder at Tony, and winked as he said, “Well, we’ve got to be going, Tony. I just wanted to introduce you two, and I have to get her back home. We’ve only got a little time to spend together this afternoon, and I plan to make the most of it.”

That was really a strange feeling, being introduced to his friend, who undoubtedly liked being with barely-teen boys too, and I felt like a piece of meat being shown off. It made me feel sexy and desired, though, and I could hardly wait to get home with Colin.

We pulled into the garage, and as the door closed behind us, Colin started unfastening his pants as he looked at me and said, “You’re so pretty and sexy, and I can’t wait for you to get my first load. Come on, honey, take the edge off ‘Uncle Colin’s’ big cock for him, so we can fuck longer a little later.”

His cock was at it’s full, rock-hard, eight inches as I leaned over the console to suck him. I tasted his precum, and I liked sucking a bigger cock than Gavin’s. I sucked his cock hard, and fondled his balls, and it only took him a couple of minutes to fill my mouth with a huge load of cum. I kept sucking his cock, as it softened, and swallowing, making sure that I got ever drop of his delicious cock juice. 

We got upstairs and sat on the bed together, and he turned to me, tenderly brushing the hair out of my eyes. Just before he leaned in to kiss me, he said, “My goodness, honey, it looks as if you smeared your lipstick, sucking my cock. Oh well, I’m going to kiss your sweet lips anyway, so I guess it doesn’t matter. Now does it?”

I had never even kissed a girl before, and I was surprised when he pressed his lips to mine. Then he pushed his long tongue into my mouth, as I did the same to him, and we were kissing passionately. I really liked the taste of his mouth and the feeling of his tongue probing mine. We continued kissing as he cradled my head, and slowly laid me back on the bed, as he leaned partially over me. He was breathing hard in the passion of the moment, and he began to squeeze and fondle my fake tits, as he pressed his hardening cock against my thigh.

We scooted back together, until we were fully on the bed, and he broke our kiss and started pulling down my panties as he whispered in my ear, “You’re so pretty, Danielle honey, and I just love fucking barely-legal little whores like you. I’m going to get a taste of your pussy before I fuck and inseminate you.”

I looked into his wild eyes and could tell that he was completely obsessed with using me as his little girly-boy whore. He moved down between my legs, after pushing up my skirt, and pulled my panties down and off my legs. Then he pushed my legs back to my chest, which tilted my hips back. He sucked my cock and balls for a few seconds before pushing my legs back even farther, as he began to lick and suck my asshole. 

He sucked me that way for a few minutes, and then quickly pulled back and removed all his clothes. He pulled out a tube of lubricant and covered his hard cock with it, as he moved back between my legs. He had me wrap my legs around his waist, as he moved in and pressed his big cock head to my asshole. I told him in my email that it wasn’t my first time, and he shoved his cock into me, slow and steady, until he was in me to his balls. It was a little tight, but his thick cock felt better than Gavin’s did pressing against my prostate. 

Fucking me from the front like that, I really did feel like a girl, especially when he leaned down to resume kissing me, as he pummeled my young ass. It took him longer to cum the second time, and he fucked and kissed me for at least fifteen minutes, before I thought he was ready to ejaculate. 

He gave me a hard, final thrust, and I felt his big cock expanding in my bowels as he moaned into my mouth, “Oh shit yeah, take my cum you little fucking whore.”

Colin began kissing me again, as his cock deflated in my ass, until he pulled away again and said, “Come sit on my face, Danielle, I want to suck all of my cum out of your tight pussy.”

I quickly moved to straddle his face, and I loved the feeling of him tongue-fucking and sucking my asshole, as his cum load drained out of me. He gripped my thighs with his hands and held me on top of his face that way for another ten minutes. I rolled off his face and lay back on the bed, and Colin immediately moved down to suck my cock. 

He had me hard in only a minute or so, and then he placed a couple of pillows under himself, as he rolled over on his stomach. He reached back and spread his ass cheeks with his hands and said, “Come on, honey, it’s time for you to suck my pussy and then fuck me.”

I knew what to do from my experience with Gavin, and as disgusting as it seemed at first, I pressed my face between his cushy ass cheeks. I licked and sucked him there until I located his asshole, and then I sucked and tongued him like I had experienced.

After a couple of minutes, Colin looked back at me and said, “Put some of the lube on your cock, and fuck me now.”

That would be my first time fucking anything, and I lubed my cock before pressing it against his sphincter. I pushed hard, and it was the most wonderful feeling when my cock slipped into his tight ass. It seemed like he was used to being fucked, because he swiveled and pressed his ass back against me, as I bottomed out in him. I fucked him hard for only couple of minutes, and then, because of the excitement of the other things we had done together, I ejaculated into his receptive ass. 

After my cock softened in him, he told me to lay back on the bed, and I knew that he was going to feed me my own cum, just as I had done for him. I loved having him sit on my face that way, keeping me pinned down under his big ass, as my cum drained into my mouth. When I finished draining him, Colin had me lay on my side facing him, and we kissed as we humped our soft cocks against one another, until we were both hard again.

We cuddled and kissed that way for what seemed like a half hour, until Colin pulled away and said, “It’s getting late, and my wife will be home in a few hours. Let’s take a shower together, and get you cleaned up, and remove the makeup and perfume.”

He has a big, travertine shower, and we soaped up and washed one another, until Colin sat on a low, built-in seat, and pulled me over to him. Just before he began sucking my cock, he smiled and said, “I just love how you young girls can cum again and again with so little rest in between.”

Colin first sucked and nuzzled my balls, and then focused sucking my cock. He took me deep into his mouth, all the way to my balls, and within five minutes I was shooting my second load of day down his throat. He sat there for the longest time, with his eyes closed, sucking my soft cock and enjoying the remaining ooze of my cum, and the feeling of my thick meat in his mouth.

We got dressed and went back to his car, and on the way home he handed me six, fifty-dollar bills. That was certainly generous payment for the almost three hours that I was with him, especially considering that I enjoyed every minute of it. 

As I was getting out of his car at the corner, he patted me on the ass and said, “When I see you again, we’ll get you dressed, and then spend a little time on a shopping trip, buying you some of your own, pretty clothes, and some makeup. You might find that you’ll enjoy being dressed up, and I want you to feel pretty when you do.”

It was hard to believe that I had made four hundred and fifty dollars in two days, and when I got home, I hid the money in my secret hiding place, in the wall behind some loose boards in my closet. Over the next couple of days, when I made even more money, I finally opened a savings account at a bank near my home. After two weeks, I had become an experienced little whore, and I was able to meet with at least one man a day, including repeat customers like Gavin. 

Most of my connections weren’t as elaborate or financially lucrative as with Gavin and Colin. Many of them were just quick meetings, where I would be picked up from the corner by a car or van, and we’d park some place private and safe, while I either sucked them off, or they sucked me off, or both. I even met with the barber, Tony, and that was an interesting experience. 

Tony met with me on Mondays, when his shop is closed for business, and he took me back to a little storage room behind his shop. He is very hairy, and with his darker complexion and that beer belly, he might have been a turn off for someone else.

He has a very thick, ten-inch cock, and he always wants me to suck him off right away when we got there. Then I’d spend an hour or so sucking his musky, aromatic balls, perineum and ass, until he was ready to feed me his second load. He loves sitting on my face and calling me names as I'm smothered in his fat, hairy ass, and I love being demeaned by him. He always makes me undress, but he never touches my cock.

The second time I met with Colin, he took me shopping, as he promised, and bought me a small wardrobe of cute girl’s clothing and makeup, including a bra with realistic falsies. He wanted me to be dressed for him when he picked me up, to help reinforce his fantasies. I didn’t wear those outfits and the makeup all the time, just when my customer asked me to. I hid my apparel and makeup in that secret place in my closet.

I had been having sex with men for about six weeks, always being picked up and dropped off on that same corner. I thought that no one had noticed my activities, even though it was a daily occurrence, and I was sometimes dressed as a girl. But one day, I found out differently. There is a small, neighborhood grocery store that I stood in front of on that corner, and I knew the owner, from the many times I had picked up groceries for my mother. He is a Greek man, named Gus, who was in his early-sixties.

After being dropped off by a rugged construction worker, that I had sucked off in his van, Gus was arranging some fruit on the display in front of his store when he said, “Hey, Danny boy, how’s it going? Do you have a few minutes to talk in my office? Come on into the back with me.”

Gus told his clerk that he wasn’t to be disturbed, as we walked back to his small office. He locked the door and sat in his chair, pushing it back from his desk, inviting me to lean up against the desk right in front of him. 

He looked me up and down for a few seconds and said, “I’ve known your family for a long time, and I’m a little worried about you, Danny. I’ve seen you coming and going with dozens of different men for the past month or so. Imagine my surprise when I realized that you're sometimes dressed like a pretty girl. I just wanted to be sure that you aren’t being taken advantage of in some way. Believe me when I tell you, that I know how some older men are attracted to a, well, let’s just say a pretty boy like you, especially when you wear that tight skirt and your makeup so well.”

I had been with enough men by that time, that I recognized the hunger in his eyes, as he stared at my crotch and ass, and licked his lips. So, I saw no reason not to admit what I was doing, since I thought that he would be interested in me too.

I ran my hands down over my cock bulge, which was plainly visible in those shorts, and replied, “A lot of the bigger and stronger boys from school, have gotten summer jobs working in warehouses and construction. I’m not well suited for those jobs, so I had to find something else. And while my slight build doesn’t lend itself to hard, manual labor, I do have at least some assets."

I paused for a moment and adjusted my cock, right in front of his face, and kept rubbing it as I continued, “I have learned that a lot of older men find girly-boys like me attractive, especially since I am big in one particular area. You couldn’t blame me for trying to make some money, could you, Gus?’

He looked stunned at my frank admission, while continuing to stare at my cock lump, and he asked, “So, you really go with those men for money? How much do they pay you?”

I wanted to entice him further, so I fibbed a little and said, “Well, it depends on what we do, and how much I like the man. For a handsome man like you, that I’ve known for many years, I would be happy with only fifty dollars.”

He kept staring at my crotch, and I took the initiative to pull down my shorts. He reached out and fondled my balls with one hand and stroked my cock with the other. I smiled at him and said, “Go ahead, Gus, you can suck it if you want to.”

Gus let go of my cock and balls and said, “You have a really nice cock here, Danny boy, but I’m not a cock sucker. Change places with me, because you have to take care of old Gus.” 

He stood up and leaned against the desk, as I sat in the chair in front of him. He quickly pushed down his pants and underwear, and I was staring at a huge hairy cock, that was still soft, but about six inches long and very thick. I took his cock into my hand and began stroking it, as I leaned down to suck his egg-sized, low hanging balls. He leaned back on the desk and moaned, as he placed his legs on my shoulders, to give me better access. 

Gus was sweaty and had a strong musky smell from working in the store all day, and he seemed surprised when I leaned down even farther and began sucking his perineum and ass, before moving up to take his precum-oozing cock into my mouth. His cock got hard within a few seconds, and I guessed that it's a little over nine inches long, and even thicker than Tony’s cock. 

I sucked his big cock for a few minutes, until he pushed me back and said, “Change positions with me again, Danny, I’ve got to fuck your pretty ass.”

He moved behind me as I stood up, and he pushed me face down on his desk. Then he pulled down my shorts, and poured some olive oil, that he had in a bottle on his desk, down my ass crack. He rubbed his big cock up and down in the oil until he pressed against my asshole and pushed into to me. His was the thickest cock I had ever taken in my ass, and I breathed deeply as he sank inch after inch into me. He was fucking me all the way to his balls. 

I was pounded hard and fast for about five minutes, until he held himself buried in my ass and began ejaculating. He was moaning as he said, “Oh fuck yeah, you little cunt, take my fucking cum.”

It was surprising how long his cock throbbed in me, given his age. When his cock finally softened and pulled out of me, he sat in the chair and pulled me down to suck his cock clean, as his cum ran down my legs.

I sucked him until his cock started getting hard again, when he pushed me away and said, “No, no, no more for now, Danny. I’ll need to rest up before I can go again, and you can suck me all the way off another time. I want to use your mouth or ass or both every day that I see you out there. I’ve been watching you standing outside for weeks, and I just had to tap that cute ass of yours first.”

He gave me some paper towels, and I cleaned up my ass and legs as best I could. Then he handed me two twenties and a ten-dollar bill and said, “You earned this, Danny, and you’re going to keep earning it. Now that I know what a little slut you are, I’m going to use you anytime I want to, and I’m not going to pay anymore. If you’re going to use my corner like a little whore, then you can suck my cock and let me fuck you for the privilege.”

I could have easily gone to another corner, but I liked Gus, and I liked the way his thick cock felt rubbing my prostate. And in my mind, what was the difference if I was already sucking, fucking, and being fucked by other men anyway.   

School was going to start in one week, and I had already been meeting with men for eight weeks by then. I had already saved over eight thousand dollars, and I learned time and time again that I got paid more by the men who had strong fetishes to be with pretty girly-boys who were dressed for the occasion.

I was scanning the Craigslist postings one day and came across one from a man who said that he was a teacher, and forty years old. His name is Ryan, and his message read, “Seeking pretty, barely-legal, big-cocked twink, that can put me in my place this afternoon. Come dressed and be prepared for anything, and you will be richly rewarded.”

My success rate attracting men with my responses was almost one hundred percent, and I felt confident as I replied, using the name, Danielle. I started getting dressed and applying my makeup even before he replied, so I was ready to meet him on the corner, in only fifteen minutes. 

I looked very pretty that day, with my red hair framing my face, with carefully applied makeup. And the short skirt hanging off my cushy ass, which emphasized my long, slender legs that looked sexy too. I was standing there on the corner when he arrived, with my hand on one hip and my hip cocked, as women sometimes do. I got into his car and got the shock of my life.

The man driving the car is a good-looking man, who I immediately recognized as Mr. James, my high school math teacher. I knew that he was married with two kids, and I had already signed up for another of his classes for the coming year. He seemed pleased with my appearance but didn’t recognize me as his student. I usually wear my long, red hair in a ponytail, and he wasn’t used to seeing me with makeup.

We had been driving for a few minutes, when he ran his hand up my leg, and under my skirt, and began rubbing my soft cock and balls. He smiled when he felt my big package, and said, “I’m a really lucky man, Danielle. You’re such a pretty girl, and it seems that you have that extra special something for me too. I don’t get that many opportunities to be with a pretty, young girl like you. My wife and kids are out of town until tomorrow, and I can hardly wait to get you home.”

He lives in a modest home, about four miles away from me, and we went immediately up to his bedroom. We were standing by his bed, and he kissed me, pushing his tongue into my mouth, as he gripped one of my ass cheeks with one hand, and rubbed the side of my fake breast with the other. He held me tightly, and because he's taller than me, he pressed what felt like a small cock into my lower stomach. 

We kissed for maybe five minutes that way, and he was trembling as he probed my mouth with his tongue, because he was so aroused being with me. He pushed me back to sit on the bed, and got on his knees in front of me, unbuttoning my blouse. He then took off my blouse and bra and began sucking my nipples as he fumbled to unfasten my skirt and throw it aside. After my skirt was off, he kissed, sucked and licked down my torso, until just above the top of my panties.

My big cock and ball lumps and red hair were showing through the thin, white cotton panties, and he started mouthing and sucking my genitals over my panties, as he muttered incoherently to himself, “Heaven help me, with this big-cocked ginger.” 

I got hard quickly as he continued sucking my genitals, and he pulled my panties down and off my legs. He sucked my balls into his mouth, one at a time, for several minutes, and then took my oozing cock into his mouth. He hugged my waist and sucked me aggressively, until I felt my ejaculation was close.

I decided to tease him and get him even more turned on, when I said, in the sweetest, girly voice that I could, “Keep sucking me, Ryan, and I’ll be feeding you my sweet, girl juices in just a few more seconds.”

He moaned and started sucking me even harder then, and my cock erupted in his mouth as he continued sucking and swallowing my teen cum. He kept sucking me for about five minutes, and then stood up to take off all his clothes. His dick was rock hard, and only about four inches long and thin, and I saw why he would be so excited about my cock.

Ryan looked at me and said, “I want you to suck me off, while you recover so you can fuck me.”

He laid on his back and pulled me on top of him in a sixty-nine. I took his dick and both of his small testicles into my mouth, as he reached back and pulled my legs forward, fully exposing my ass. I sucked and licked his genitals for only a couple of minutes, until his cock jerked and pulsed, and he ejaculated into my mouth. I continued sucking him as he was eating out my ass, and when he didn’t stop, I decided to do the same for him.

Ryan really started moaning when I pulled his legs back and leaned down to suck his ass. I had never done a double-anal sucking like that and it was a big turn on for me. We sucked each other’s asses for about a half hour, until he felt my cock getting hard again. Then he got on the bed face down, and said, “Fuck me, Danielle, please fuck me with your big cock.”

He had some lube by the bed that I poured into his ass crack. When my thick cock pushed so easily into ass, I knew that he wasn’t an ass virgin. I fucked him hard as he moaned beneath me, saying things like, “Yes, fuck me and fuck me hard, I deserve it for being such a bad teacher.”

Ryan was getting off by being dominated by a girly teen, as much as he was by me just looking like a girl. I fucked him for another ten minutes before pumping my cum into his bowels. He lay on the bed, panting and whimpering, as my cock slowly deflated in his rectum. When I pulled out of him, with a slurping plop, he turned around and sucked my cock clean.

We then cuddled on the bed, kissing and humping our cocks together, for almost an hour, until I almost fell asleep. He moved down to suck my cock again, and it took me almost twenty minutes to cum that third time. After that, we got dressed, and he gave me three hundred dollars as we drove back to the corner. Gus just happened to be outside the store when I stepped out of Ryan’s car, and he called me into his office to suck his cock. 

I kept sucking and fucking men for the rest of the week before school started, and I knew that it would be more difficult and take more planning to meet with men when the summer was over. I would have to make excuses to go out in the evenings and on weekends, which wouldn’t be that hard with both of my parents working long hours. 

It was strange sitting in Mr. James’ class, with him not knowing that I'm the Danielle who sucked and fucked him. And even though I am a good student, and was an active participant in class discussions, he didn’t suspect that it was me. The fact was that I enjoyed fucking him and having him suck my cock, and I wanted to be with him again and again. I knew that it was a stretch for him to pay me the way he did, on a teacher’s salary, and I decided that I would fuck him for free.

One day I asked if I could see him after school, for help with a math problem. He said that he already had two students that had made appointments to see him, and I could only come if I was willing to come later and make it a quick question. 

I stopped in the restroom and put on just a touch of makeup and perfume, before I walked down to his classroom. No one else was in the school at that time, except some kids playing volleyball in the gym, and I walked up to his desk. He was looking down, grading some test papers, and I unfastened my ponytail, and pulled my hair down around my face.

He still hadn’t noticed me, so I whispered in my faint, girly voice, “I sure had fun with you last summer, Ryan, and I was hoping that you wanted to be with me again.”

Ryan looked up at me, shocked at the realization that the Danielle who fucked him was really Danny. He just stared for a few seconds, and stammered as he said, “Oh, oh , oh shit, oh fuck, th..., th..., this can’t be happening. I can’t get involved with my students.”

I stepped closer and pressed my cock up against his arm and said, “It’s okay, Ryan, I won’t tell anybody if you won’t. I really enjoyed fucking you and having you suck my cock, and I won’t charge you anything, if you want to meet again.”

He kept staring at me in disbelief, and said, “Damn, Danny, Danielle, I mean, Danny, you really changed your appearance a lot when we met a week ago, and I had no idea that it was you. I guess now that you know about my secret perversions, you’ll probably want to use it to blackmail me or something.”

I smiled, as I pushed my soft cock harder against his arm, “No sir, Mr. James. It’s entirely up to you, and I won’t pressure you. I’ll also never try to take advantage of you regarding my school work. It’s your choice, with no harm and no foul if you aren’t interested.”

He looked down at my cock lump pressed against his arm, and when I saw the look on his face I knew that I had him. We went into the small storage room behind the black board, and he sucked me off, before sucking my balls and ass as I recovered. Then I fucked him right there, leaning over some boxes. That was the beginning of almost weekly meetings with Ryan, and we found various places to get together.

I continued meeting men for sex for the rest of high school and college and stopped when I met and started dating the girl who would become my wife. And as I said in the beginning, since she had slowly lost interest in sex, I have decided to bring a somewhat older and wiser Danielle back to life, to satisfy my growing sexual urges.