Never Going Back Again

My dick was rigid, sticking straight out its full three inches.

"It's so cute!" Eileen said. These aren't the words that a guy likes to hear—especially not in the tone she uttered them. But, she touched me again and there was no way I was going to do or say anything to stop this.

Eileen took my penis between her thumb and her first two fingers—just like you would pinch something—and began stroking me rhythmically. I looked down and I didn't like what I saw. The way she was holding me made my dick look so tiny—like it had to be held by tweezers. But I loved how she was making me feel. When I realized that she wasn't just going to tease me, I let myself go and came to an intense orgasm. It was the first orgasm I'd ever felt from another person's touch.

Even in the dim light, Eileen could tell that my ejaculation was feeble and tiny. Again, she said, "That's so cute!" in a tone that was completely humiliating. She used her fingers to wipe up the drops of clear fluid that were clinging to the end of my softening penis and brought them to my mouth, pressing them between my lips for me to taste. I yielded to the pressure and cleaned her fingers of my semen.

I felt as if there was something I should do for her, after she'd caused me such pleasure. But she seemed intent on leaving the scene and heading home. I had to hurry to catch up with her after I'd managed to pull up my pants and fasten them. I tried to strike up a conversation with Eileen on the way to her house but she didn't seem interested. I wasn't really a very good conversationalist, anyway. So, we walked in silence.

When we finally reached her house, she turned to me to say goodnight. I knew there was no kiss coming. I didn't know yet what tonight meant, but I was under no illusions that she liked me. I decided, though, to be bold. I didn't want to go home completely confused about what tonight was about. So, I asked—right out. Maybe I shouldn't have. The answer wasn't easy to hear.

"Why did you ask me to take you to the party tonight," I asked in all innocence. There was a long pause; I guess Eileen was thinking about whether to be honest or to tell a kind lie. She chose honesty.

"Jerry said I couldn't go alone cause other guys would hit up on me and he said I certainly couldn't go with anyone else—then he added, unless it was you." She paused leaving me in suspense just as Jerry had left her in suspense until she asked him to explain. I didn't have to ask Eileen to go on. She volunteered the explanation.

"Jerry said that I could go with you because he'd seen you in the shower and he knew that you weren't any competition. I pressed him to say more and he said that you had the tiniest dick he'd ever seen on a guy older than eight. He said that if I wanted to go to the party, I could go with you as my date. I did want to go, so I asked you."

"And just back there...in the park...?"

"Yeah, well, I guess that was kind of mean. But I was curious so I thought I'd check you out."

Eileen could see my face flush with embarrassment and humiliation. I think, maybe, she felt guilty.

"Aw, come on. Don't feel bad. It's not like it's your fault you're small there. And, hey, you got a hand job out of it. That wasn't so bad, was it?"

I turned before she could see me start to cry. And I walked home with very mixed emotions. I still felt the warm, post-orgasmic glow. But I also felt the sting of humiliation. I decided that I didn't like Eileen very much, even though I really liked the sensations her hand had caused me just a few minutes ago.

As it turned out, I had a lot of sort-of dates in the coming months—especially after I bought beater to drive around in. It usually wasn't like real date—you know, we didn't go to a movie or a dance together. No, usually some girl would ask me if I could take her to the downtown library one night to do school research or drive her home from some school dance. Some of the guys thought it was pretty strange that girls seemed always to want to get a ride with me. It certainly wasn't my car—a 15 year-old clunker.

It took me a while to figure out what was going on. I started putting two and two together when I realized how similar these "dates" turned out to be. There wasn't perfect consistency or I would have figured it out sooner. But after a while I realized that there was a pattern. It went like this. Girl finagles a ride on some pretext. I agree, cause I'm a nice guy. I have pleasant enough conversation with her until we get to our destination. Then, she acts like she's very appreciative, leaning over to give me a peck on the cheek—never more of a kiss than a quick peck—to thank me for being such a "dear" and giving her a ride.. But her hand "accidently" rests on my crotch. And that starts it off.

She usually says something like, "Oh...what do we have here?" as if she's really interested. At first—before I figured out what was going on—I was flattered. She'd massage me a little though my pants, which always got me hard really fast. (I guess it doesn't take much time to fill a small vial.) And then she'd say, "Oooohh!" and unbuckle my belt and unzip my pants to get her hand down inside my briefs. And then...well, then it felt wonderful. A soft hand was caressing my little penis and I loved the feeling.

"Let me see," she would plead. And I didn't want her to stop touching me so I'd raise up so she could push my pants down to my knees. Then I was completely exposed to her. I knew she had to be thinking that I was tiny compared to e other guys she'd seen. I mean, we were all eighteen; it's not as if any of these girls were virgins. I can't say I didn't care about what they thought about the size of my penis. I did. It made me feel awful about myself. But the girl would continue holding and stroking my rigid dick and I was willing to take a lot of humiliation to feel that.

Sometimes a girl would just feel me and then leave me hard and yearning for release. That was frustrating, but at least I felt the touch of a woman. Sometimes a girl would stroke me until I spurted my little load on my stomach or thighs. That felt wonderful. A few terrific times, a girl would take me in her mouth. What a fantastic feeling that was. And, once—just once—a very cute girl, Josie Markam, sucked me until I shot in her mouth. Jesus! What a sensation that was! I didn't even object when Josie immediately kissed me and pushed my cum into my mouth for me to swallow.

Most of the time, the wonderful feelings these girls' touches produced in me compensated for the feeling of inadequacy and shame I had at being exposed to them. But sometimes it wasn't worth it. I didn't like it when a girl would hold my penis between her thumb and first two fingers. That made me feel even more inadequate. It reminded me of the way Eileen had held me that day in the park. And once, a girl couldn't hide her hilarity at seeing the size of my equipment. It was even worse that she kept trying. But once her first snorting laugh at my expense had come out, she couldn't contain herself despite her best attempts.

It took me a while to figure out that my puny penis was a matter of girl gossip and lots of girls wanted to see for themselves whether an eighteen year-old guy could really be as small as they'd heard I was. Before I figured this out, I had started to think that all girls found some excuse to handle all the guys they were alone with. I liked that hypothesis better. But, when it was finally impossible to keep believing it, I resolved myself to the conclusion that I was the laughing stock of all of the girls in my high school.

Of course this humiliated me. And for some time, I avoided situations where a girl could get her hands on me. But finally I came to the conclusion that doing that wouldn't stop them from talking about me. It wouldn't keep me from being the butt of their cruel jokes. It would only keep me from feeling their soft hands on my hard little penis. So, I steeled myself to the humiliation in order to feel the human touch. I kept on agreeing to give girls rides when they asked. I was getting something out of it.

Once I wound up being the only guy at a sleep-over that one of the girls, Penny, had arranged, without her parent's knowledge of course, when they were out of town. (I thought it was pretty strange for eighteen year-olds to have a sleep-over party, but I really didn't know much about such things.) Six girls and one guy with a very small penis. There was lots of drinking and groping. (Well, the groping was all one way. When I tried to feel any of the girls up, they would stop me.) It felt good, at least if I ignored the remarks that were humiliating. Really, how many guys have had the soft hands of six cute teenage girls fondling them at the same time? The feeling of being touched was enough to make up even for humiliation of being measured in all sorts of ways. They measured me soft and hard. They measured my balls and by ball sack. In the end, they knew more about my genitals than I did.

In the course of all this, they got me hard lots of times and made me squirt my juice twice in just three hours, which was a record for me. They also got me, and themselves, pretty drunk. They still seemed in control, though. I was at the point where I would do pretty much whatever they suggested.

And what they suggested was that I get dressed up in girl clothes. I put up a bit of a protest, but not for too long. I just didn't have the energy to fight. After all, it was a girl sleep-over. So what if I was just one of the girls.

At first, I thought it was just going to be panties and a nightie. But they wanted to make me up completely: paint my nails, do my face and curl my longish hair. This all took about an hour. Just when I thought the conversion was complete, one girl suggested that I was showing a little too much hair to be a pretty girl. I'm not very hairy, but I did have a bit on my calves and in my arm pits; and, of course, I had pubic hair. Not for long, though. They sat me on the side of the tub and I was soon clean shaven; except for the hair on my scalp, every bit of hair on my body was gone.

When they put my panties back on, I could feel the silky smoothness of the fabric on my body much more vividly than before. I found it very arousing, but I was too spent from having two orgasms to get hard from it. Before putting the nightie back on me, they fitted me with a bra and filled the cups with stockings so that I looked like I had breasts. After they had finished dressing me, I got a chance to see myself in the mirror. I looked okay. Slightly skinny, but not bad. When I looked down, I saw my "breasts" tenting out my nightie nicely.

We all went into the family room where we would sleep on the floor in our sleeping bags. Everyone wanted one more drink and we sat around like girl friends talking. The girls were all treating me like a girl, too. They dubbed me 'Valerie' and referred to me as 'she'. It was all kind of nice. Since I felt completely spent, I wasn't yearning for them to touch me and just being "one of the girls" felt good. It gave me a peek into girl culture as they talked about boys, what they liked, and didn't like, about each of the guys in their crowd.

Predictably, I guess, the talk turned explicitly sexual. Before long, people were recounting the stories of when they lost their virginity, or (as they put it) had their cherry popped. I was surprised that every one of them had a story to tell. I guess from my experience and what I'd read, I just assumed that most kids our age were having oral sex but waiting a bit for the real thing. I was wrong.

At some point, one of the girls drew attention to me. They all started saying how sorry they were that I hadn't had my cherry popped. I tried to laugh this off. I certainly had no intention of telling them that Jerry had popped my cherry. That would have been too demeaning in front of all of these girls. So I played the virgin. What was the harm in playing along, I thought. I said things like: "Oh, well. What's a girl to do? I'm sure someday the right boy will come along." They all laughed and I thought the topic was closed and we would move on to telling more stories about these girls and their experiences with boys. I was wrong.

Suddenly, Penny piped up and told us to "hold everything"—that she had a great idea. Penny ran from the room and came back holding something behind her back. "I know just want Valarie needs," Penny said. Several of the girls went over to her and she showed them something. They squealed with delight at something I couldn't see. Then the girls who were in on the secret came over to keep me busy while the others took a look. More squeal

I was really quite drunk at this point so I guess I was easy to manipulate. Two of the girls gently laid me back on my sleeping bag and began caressing me. They were lying on my arms, subtly but very effectively incapacitating me.

"Oh, you're going to love this Valerie," one of them said.

When I got a chance to see what was in store for me, I sincerely doubted that. Penny was walking toward me with a strap-on dildo—the kind that you see in porn movies on the internet. It was realistic, except for the size, which was bigger than any penis I'd seen in real life or on the internet. I remember wondering where Penny found this. (I learned later that she had discovered her parents' store of sex toys and, apparently, they were into some kinky stuff.) But thoughts about practical issues like that were soon driven from my mind.

Penny told the girls that it was time that I became a woman and they should help me by taking off my panties. My bottom was soon exposed to Penny's assault. To give her clear access, two of the girls held my knees up and spread them wide. I was rocked back so much that my asshole was almost sticking up straight for Penny to penetrate.

She slathered some lotion on the fake cock and, then, I felt it pressing against my asshole. It felt enormous—like it couldn't possibly fit in me, at least not without doing major damage. But, as the girls cheered her on, the pressure from Penny was insistent. Before too long, I felt my asshole yielding. It didn't happen easily, and it certainly didn't happen without pain. But eventually, the head of the dildo had opened me and I could feel the back-and-forth motion of Penny fucking me. It actually crossed my mind that I should be grateful to Jerry for popping my cherry. This would have probably hurt a lot more if I hadn't gotten an initiation on his cock.

The sight of the huge dildo pistoning in and out of my ass really got the girls cheering—and not just Penny. They were cheering me on as if this was an accomplishment of mine. I heard them say things about my not being a virgin anymore and about Penny really popping my cherry big time. As this went on, the pain receded. I didn't think I was enjoying it but at least I wasn't in excruciating pain anymore.

I say I didn't think I was enjoying it because, I guess, at some level, I was. The girls soon began commenting on the fact that my dick was hard again. I hadn't realized that; my attention was focused on the sensations in my asshole. I wouldn't have believed it could happen. I'd already cum twice and I'd been hard much of the evening. But, I could feel it now. And when I looked at my crotch, I saw that, sure enough, my penis was standing at full mast. It wasn't much, of course, but it was as big as it ever got.

The girls started arguing over who was going to get the next turn fucking me with the dildo. I don't remember who won next dibs on my ass but I know that over the next hour, every one of the six girls had their turn fucking me and they took me in every position imaginable. I was fucked missionary style, doggy style, bent over a table, and riding the enormous dildo like a cowgirl. With the exception of a few times when I was being re-positioned, I stayed hard the entire time. And, by the end, I felt as if I really wanted to cum.

They wouldn't let me, though. During all of this, the girls often touched my penis, but only to show each other how hard getting fucked in the ass made me. They never stroked me. And when I tried to stroke my penis myself, they stopped me. They told me that I was the girl here and this wasn't about my pleasure. It was about me pleasing my man. Well, there wasn't a man in the room. (Ooops, Freudian slip. I should have said, "other than me.) And I didn't really see how I was supposed to please a piece of plastic. But it was clear enough that I wasn't going to get any relief for now.

When the girls had tired of fucking me, they decided that I should be allowed to cum. I was looking forward to a hand job from one of the girls, or maybe a blow job. (I didn't dare to wish for more than that.) But, as it turned out, I had to settle for a hand job from me. And they insisted that I do it while I fucked myself with the huge dildo.

I didn't care. I wanted to cum so much that I would have done just about anything. I lay there, in my bra and nightie, thrusting the fake cock in and out of my ass while I stroked myself to my third orgasm of the night. Even though I'd cleared my prostate out twice already, I produced quite a bit of semen (for me). I shot it onto my stomach and some of it reached as far as my raised up nightie and bra. The girls had me smear my semen around on my stomach and then lick off my hand.

With that, the night's activities were over. I fell asleep with my nightie sticking to the drying semen on my stomach. I suppose I should have slept fitfully after the sort of humiliation I'd been through. In fact, though, I slept like a baby.

I didn't wake up until some of the girls were up and going. It was strange to wake up in the nightie and to feel my "breasts." I went into the bathroom to pee and, when I saw myself in the mirror, I decided to strip off the girl clothes. When I looked in the mirror again, I guess I looked a little better. But it was strange to have bra marks on my body.

Leaving the nightie and bra in the bathroom, I went back out to the family room to get dressed in my clothes and get my things together so I could leave. As I walked into the family room, I was immediately sorry that I didn't have the nightie, or at least a towel around me. The girls started talking about me and I quickly turned red with embarrassment. This made them talk more and, before long, I found myself sporting a very hard erection.

"Oh, look," one said. "He has a morning woody."

"More of a morning splinter, I'd say," another corrected.

Some of them fondled my hard little dick a bit—not enough to get me off though. They just wanted to tease me for a while. Finally, they made me stick my finger up my ass and beat off onto the top of a cinnamon roll. That roll turned out to be my breakfast. But, once that little humiliation was over, the girls let me get my stuff together and leave.

On my way home, I wondered about how I should think of last night's experiences. On the one hand, I'd seen, and been touched by six very cute teen girls. And, I'd had three orgasms in one night. Something I'd never done before. But, the cost had been extended humiliation and feminization.

* * *

I guess everyone's excited about going off to college. But I was looking forward to it for special reasons. I was a very good student and had lots of options about where to go. I chose a small school, very far from my home town. More than anything, I wanted to go somewhere where no one would know me. I could start afresh. And I did.

Unlike most freshmen, I had a private room in my dorm. My parents had to pay extra for this, but I'd gotten a great scholarship and, so, it wasn't costing them too much send me through a great school. My room had a private bathroom and I certainly wasn't going to sign up for any physical education courses. So, I never had to shower in front of another person. This was going to be great! And it was. I loved my life here and I resolved that I was never going back again.