When Susan Met Dawn
[This is a fictional account of the consensual (if sometimes duplicitous) sissification of a teenage boy by adult men, friends, and family. It is the second part of a planned trilogy, following the "Free Haircuts" story in the Young-Friends section of the Transgender page.]
My name is Dawn, although it used to be Don. I'm a twenty-nine-year-old sissy cuckold and my wife Alice has recently decided it's time to fully feminize me. We have a 9-year daughter, Tina, who used to be Timmy. It seems that things are finally working out well for us after plenty of confusion and denial for most of our marriage.
Alice has asked me—ordered, really--to write down my all of my formative experiences with as much detail and backstory as possible, so that friends, family and coworkers can have a better understanding of what's happening as I begin looking and acting more feminine in public and start growing breasts. Tina has written her story already, so I need to get going with mine. It starts out when I was still a young teen, not too surprisingly, shortly after reaching puberty.
I was a geeky, awkward, shy and nervous kid, good academically but never at all popular. And I was certainly never successful attracting girls. Other boys and girls were dating, petting, even fucking almost instinctively by late middle school or early high school, but for me it was just hopeless. I felt like a complete outcast, getting crushes on cute girls but almost never finding the courage to ask them out. And I only got turned down or even laughed at whenever I did.
I started ninth grade in high school at age thirteen since I had skipped a grade, and that made me even smaller and less developed in comparison with other boys. By then I was jacking off to dad's Playboys. I searched around his desk and bedroom drawers to see what else I might find and uncovered more of his porn. It included plenty of stories about sex between adults and teens, frequently men with boys. I jerked off to that, too, whenever I had the house to myself for a few hours during weekends or when my parents went out to dinner. I was careful about returning things to where I found them, or so I thought.
There was a large park near my new high school campus. I explored it one afternoon and found a secluded restroom off in one corner behind a rarely used casting pool. By accident I discovered that there were all sorts of graffiti decorating the walls of the two stalls. Looking at these notes and images quickly became my substitute for spending any time with girls. Almost all of it described gay sex— pictures of cocks, pictures of men sucking cocks, and brief notes from men hoping to hook up. Most of these notes were written by cocksuckers seeking men who wanted blowjobs.
It was a lot like dad's porn collection but much more exciting because it was real. I thought about what must be happening at that place and was highly curious.
At first all I did was read the graffiti, visiting about once a week to see what was new and jack off. It was pretty secluded and I had the place to myself as long as I wanted. I later learned that most of the action went on during evening and early morning hours when the park was practically deserted. The floors frequently smelled of urine, but that wasn't surprising and you got used to it.
But one day I was startled to find an adult man occupying the last stall. I didn't know it then, but he had been watching me from his car for several weeks and had decided it was finally time to make a move. He smiled at me, but I was so nervous I nearly ran out the door. I wasn't a cocksucker, after all. But I still needed to check for any new graffiti, so I lay down on the grass and waited for him to leave.
He emerged from the restroom a few minutes later. He was just a guy around thirty, not particularly tall, short, thin, or fat. But he wasn't leaving. He looked at me, smiled again, and gestured to the restroom door with a turn of his head. Then he walked back inside.
I had to decide what to do. I understood that the man wanted to play, but I was very shy and too young and inexperienced to know the next steps. But I was also very interested, and after a few more minutes I couldn't keep from going back in. There were two stalls, after all, so there was space for both of us.
I sat down in the open stall, pulled down my pants, and was immediately hard reading the graffiti. There was a short story about a son sucking his dad's cock on a camping trip and a crude drawing of an orgy involving five guys and one woman. Two of the men were eating the girl's pussy and fucking her in the ass, and they in turn were getting fucked, sucked, or sucking cock for the three other guys. Pretty hot stuff for a thirteen-year-old.
I lost track of the time and eventually forgot I wasn't alone.
"You enjoying the pictures?" I heard the man's voice to my right.
"Um, yeah," I replied, a little embarrassed to be caught stroking my cock next to somebody else.
"There's more stuff over here you might like," he said casually.
My pants were down but I shuffled over to the next stall. "It's down here," he said, pointing to some new writing on the far wall slightly above the floor.
I knelt down, and it read "Suck my cock here, 3 pm Tuesdays." It was Tuesday and just about a quarter past three. I was impressed--the guy had found a way to suggest I could suck him off without frightening me away in the process.
I looked up at his face, down at his hard cock, and back up at his face again. It was obviously up to me to make the next move, but I still wasn't sure I wanted to be a cocksucker.
But I also felt this strong, almost hypnotic urge to go on. This was really the whole reason I kept hanging around the restroom, after all. Maybe I could just touch it, I thought. I hold my own cock all the time when I'm jerking off.
I reached over and grasped his hard cock. I felt the warmth and stiffness under the skin and started stroking him just like I did with myself. I felt his cock getting harder and then pulse as a drop of clear liquid appeared at the tip.
The same thing happened with me sometimes while I jacked off, of course. I decided to lick it, just to see if his taste was any different from mine. But I couldn't help myself once I felt the tip of his cock on my tongue with my mouth open. I moved my lips down around the head and took his first few inches in my mouth, kneeling on the floor between his legs while he sat on the toilet.
I thought that I knew how cocks felt from jacking myself off, but this experience was very different. First off, this man's cock was way bigger than my little thing, and definitely much, much thicker. Secondly, I could focus on all of the interesting textures and sensations from the cockhead, glans, skin and shaft without being so distracted by my own arousal. And there was greater sensitivity since I was feeling his cock with my lips and tongue instead of my fingers and palm. This was getting interesting and I was pretty excited. It felt as if I was actually a character in one of my dad's stories instead of just reading it.
But I honestly didn't know what to do next with such a mouthful, other than the obvious part of being careful not to bite.
"Am I your first? You might want to take your glasses off now. If you're finished reading the graffiti, I mean." That was a little embarrassing, but I put them in my pocket and went back to sucking.
"That's great. Just relax and get used to it. Suck gently, bob up and down a little, and lick right beneath the head. Not too hard yet—yeah, like that..." He rested a hand on the back of my head. I tried following his instructions, and must have been doing something right because his cock went from being reasonably hard to nearly rock hard. That made it easier to work my way up and down the shaft, moving faster as my mouth filled with saliva and his cock got really wet. Spit was dripping out the corners of my mouth. I sucked harder and realized he was already close to cumming.
It didn't take long after that. "Fuck, yeah—cumming..." It was a statement, not a request. I was sucking only the top half of his big cock, so he started stroking the root with a thumb and two fingers. I backed off slightly and stopped bobbing so we didn't collide. He groaned, and I felt his shaft pulse between my lips and three or four big spurts of cum shoot into my mouth. Once again, something I thought I was pretty familiar with felt entirely different from this end.
"Easy now—no, don't stop..." I did as he asked, pleasuring and cleaning his cock with my mouth until he was soft and smaller. He stood up and I got out of his way. We made eye contact again, but I suddenly felt nervous again and quickly looked down at the floor. My pants were down around my ankles and my little baby cock was still hard.
"Thanks, kid." He patted my shoulder but I didn't say anything. "Don't be so shy—you're a natural, and a good cocksucker like you can have lots of fun here if he's just a little careful and discrete. I know you liked it--be here again next week, sport."
"Um, sure." He was right, it had been fun. Making his cock stiffen, spasm, and cum in my mouth had been special, and I really was ready to try it again.
He left and I was finally on my own in the back stall. I sat down and jacked off reading the graffiti, just as I had originally planned.
I don't need to tell you that I went back the next week to suck his cock as requested. It became a regular habit even if I was somewhat conflicted at first. Sometimes I felt humiliated thinking about it, such as when I was staring at all the hot girls at school every day. But it also turned me on and I thought about it most nights while jacking off in bed. I would often cum twice before falling asleep and once more in the morning, since I was only 13 and still incredibly horny.
I simply couldn't resist the urge to suck cock every Tuesday afternoon. It got easier for me every time until I didn't feel so ashamed about being a cocksucker. And I learned much more about properly giving head, about how a cock could actually tell you what it needed if you just paid some attention. The man said his name was John but never added anything more about himself. "John" told me I was getting pretty good, and I think he enjoyed our sessions almost as much as I did. Pretty soon I could usually make him cum using only my mouth, without requiring any extra stroking at all on his part.
At that point John started bringing along a friend and it was simply understood I was supposed to suck off both of them. In principle that meant we had a lookout for any unexpected interruptions, but the wingman would mostly just watch me suck and made occasional comments about my performance. It felt a little degrading, but a part of me actually enjoyed being exposed and treated that way.
It wasn't always the same friend, either. Eventually there would also be one or two other guys waiting in their cars on the street when I arrived, or extra men who would arrive once I got started. I was sucking off four or five cocks every time by that point. I could have easily done more but needed to get home after an hour or so. I didn't want my folks to notice and I usually had homework to do.
John and his "friends" had groomed me into an eager and cumpliant little cocksucker before very much longer. They were always appreciative and encouraging, telling me just how good I was at giving head. But most of my reinforcement was less explicit, actually coming from within me instead of from them. I was the one repeatedly telling myself how desirable and talented I was when I got down between a man's legs to suck his cock and swallow his load. And I always felt much better once I'd sucked a cock or three after being rejected by yet another girl.
All that positive energy eventually became a very powerful reward just by itself. I closed my eyes when I started sucking and the rest of the world simply vanished. There was a cock in my mouth and my entire purpose in life was to worship it. I didn't think that in words, of course, but the craving was as powerful as anything I've ever desired.
My classmates noticed how I was lurking around at the park and before very long I was servicing them, too. Soon I was busy both Tuesdays and Thursdays just keeping up with demand. I dropped in on weekends, too, and by then I was sucking at least ten or more cocks every week pretty regularly.
I needed it more than the guys did, honestly. One slow day I had time to read some of the graffiti again. Someone had written "Don sucks cocks here." All I did was add "3-4 Tuesdays and Thursdays" underneath. I came to understand why most of the graffiti was written by cocksuckers.
The next summer was even busier. I was down at the park more and more frequently, usually for an entire morning or afternoon at a time. My cover story was that it was a good place to read, which was true. I brought a book and would find a nice spot to lay down, not too close or far away from the restroom. Then I kept an eye out for any guys gathering in my general vicinity.
Pretty soon there would be five or six men and teens talking together, playing cards, and so on. All I had to do was get up and go to the restroom, and guys would start drifting in for blowjobs every 10 or 15 minutes. You wouldn't even realize I was in there giving head unless you noticed the bulges in the guys' pants on their way in, and how contented they all were going out.
After a while there would be a longer pause and I would take a break. It might take another hour or two for another group of horny guys to form, so I did catch up on my reading.
I started out as a freshmen, so it's hard to estimate just how many cocks I might have sucked during high school. It was certainly a lot. Sucking cock several afternoons each week and more often than that during the summer was the majority of my social life. My entire social life, honestly; it was the one way I had fun with other people outside of going to school. But I never let it interfere with my grades or getting home on time. And it didn't make me any less successful with girls or more of a social pariah than I already was, since those things were just hopeless to begin with.
I guess about half the boys and a fair number of girls at school were eventually aware of my passion for cocksucking. They were all surprisingly good about not bringing it up to embarrass me. But all of this is still just the backstory to the backstory; events started moving even faster and further along during my senior year...
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