Recently, matty7853 and I got chatting about past lovers, and he asked if I had been with any transgender girls or femboys. I told him I had, and gave some details about a certain xHamster encounter some of you may recall (and who, I hope, will contact me again one day). He then asked about the two femboys I had been with, and it seems that my response was too wordy for xHam’s chat system. So, instead, I’ve decided to post it as a story – for Matty’s enjoyment and for yours. This takes the form of a letter, rather than proper fiction; but I hope you find the story enjoyable nonetheless.
My first femboy experience was with a young man named Eric, with whom I went to high school. We had been friends for some time and, as we started to develop and explore sex, we did a lot of talking (and no small amount of showing) about our discoveries. Eventually, it got to the point that we were loaning one another our ill-gotten porn magazines (rare and precious commodities in those days) – and when I managed to obtain a video tape my uncle had “lost,” we ended up jerking off together.
After that, we were 100% open with each other and, one day, when he opened the chest where he kept his naughty stash, I discovered a pair of frilly pink panties among the magazines and improvised sex toys. He told me that he has taken them from a clothesline after reading an article about a crossdresser in one of my mags (Penthouse Variations) – “just to try it out.” I asked if he liked them and he said he kinda did – whereupon I dared him to wear them under his jeans all night. We both considered ourselves straight at this point, and had never looked at each other with much more than curiosity – so the idea seemed more funny to me than arousing.
He had just slipped into them (and we didn’t get a chance to enjoy our usual beat-off session) when Eric’s mother came home, and we were called downstairs to help carry in groceries, help with dinner, and the other assorted things teenagers get drafted into around the house. The entire time (probably about four hours), he had a raging hard-on – which his jeans did a fair job of tucking back; but, knowing what I knew, there was no mistaking it for a mere fold in the fabric. Eric noticed me noticing, and was uncharacteristically bashful – even blushing when I jokingly waved at him in an effeminate way behind his f****y’s backs.
That night, we finally got free of the f****y (I think we claimed we were going up to play video games or something) and Eric’s hands were on his fly almost before the door closed. His cock sprang out in its silky confinement, making an instant tent – and, as he was cuircumcized, there was no holding back the pre-come that soaked fabric.
I made a comment to the effect of “Look how wet your panties are, Erica,” using the female version of his name. He got so flustered he couldn’t even lower his pants. Jokingly, I said “You’re cute when you blush.”
Eric was quiet for a long moment, and then softly asked: “Do you really think so?” He wasn’t joking at all; his voice was demure, vulnerable and almost girlish. It shocked me quite a bit, and I immediately opted for bravado – something like: “Well, you know, I wouldn’t take you to the prom or anything.”
Things were awkward for a few minutes, and we just sort of sat together on his bed (the only furniture in his room). After a while, he commented that he saw me looking at his cock all night, and I said something like: “Those things really made you horny, huh?” He nodded and, with the tension slightly eased, we went about our usual ritual (a few hours delayed) of looking at our mags.
A little while later, I noticed that Eric was watching me, and I was like: “What?”
That was when he asked if I would let him stroke me off while I read the magazine (Variations, in case you don’t know, is a write-in and fiction-based mag, with lots of “I can’t believe something like this happened to me” stories). I didn’t give him one of those “Don’t tell anyone” lines (our little hobby was already a shared secret), but I was still more than a little grudging in my agreement. Eventually, I decided that one hand was as good as another – and it would leave me free to hold the mag and turn pages at the same time. Besides, it seemed to be something my buddy really wanted to try.
I was wrong about one hand being as good as another. Rather than just grabbing ahold and pumping as we usually did, he made a real event of it – a massaging, caressing, sensual handjob. I couldn’t help but get heated up as I read the article (though, in retrospect, I have no memory of what that article was about) and, still trying to be macho and joking, I asked, “Enjoying yourself, Erica?” He blushed again and, in an awkward shot at a woman’s tones, answered: “You know it, stud.”
It wasn’t long after that I hit my peak. Eric stroked me all the way through it, and I came all over his hands. He stared at the dribble for a long moment and then, tentatively, licked it from his skin. That sight was a huge turn-on, and was the moment I realized there was more to this than my being horny and his being interested. This was damned hot!
We sat for a moment, him lapping my semen off his hands, and me watching. Finally, I asked: “Do you want me to do the same for you?” It only seemed fair.
He replied with a “Hell yes!” and I reached for the hem of his panties, not sure of where to begin. In the end, I sat behind him, reached around his torso, and tried to stroke him the way I would myself. I recall thinking how different it was – he was cut and I wasn’t, so his skin had less give. Besides, he was so hard that I could feel his pulse through his shaft. Anyway, he was slick with fluid, so I simply wrapped my hand around and pumped – and, in less than a minute, he hit a moaning, bucking, shuddering climax. To this day, I have never seen a man come that hard in person, and his seed shot several feet onto the carpet.
He laid back, panting despite the short stroking, and I noticed that I had some spillage on my hands now as well. “You want it?” I asked, holding my hand out in offering and, without hesitation this time, he leaned forward and began licking away. The sensation was new, strange, and sexy – and my cock got hard again as I watched him. He looked at it, looked into my eyes and – without words this time, moved to take me into his mouth.
It was my first blowjob – and probably Eric’s too. What he lacked in experience, though, he made up for in enthusiasm, and I crooked my elbow over my mouth to keep myself from moaning like a retard through the pleasure.
I told Eric it felt great, and he kept sucking; I told him I was getting close, and he kept sucking; I warned him I was going to come right now, and he kept sucking – swallowing everything I had to give.
Surprisingly, we didn’t really talk about it afterward. I guess we were still young enough to except the weird things of the world at face value. Sometimes, after that, he would reach over during our afternoon meetings and help me to blow off steam; but things were otherwise the same. We biked, we messed around on the computer, we read comic books. In short, we were teenaged chums. This new aspect seemed so perfectly natural that it just fell in with the rest.
A few weeks later, my f****y was donating a few garbage bags full of clothing to the local Goodwill charity. When no one was looking, I surreptitiously wheedled a skirt, a top and some leggings, and delivered them to my buddy. When he looked at me questioningly, I said: “For Erica.”
It was another week before we got a chance to use the clothes (Eric said he wanted to “save them”) – but, that weekend, we decided to go fishing at a secluded spot that few people went to, and Eric brought the clothes in a backpack. It required a long hike up a creek (wading through the water at several points, due to thick brush) and, about ten minutes in, Eric skipped off into the scrub. When he emerged, he was dressed in the clothes I had brought – and also wearing some lipstick he has gleaned from his s****r.
“Ain’t you cute?” I grinned. He seemed pleased with this. Maybe he was expecting me to mock again, but I had gotten over the need to impress anyone on this point. In any case, it wasn’t half as weird as some of the things the magazines mentioned.
He was wearing the panties under the leggings and skirt – and none of the layers did anything to hide what the clothes were doing for him. At the thought of his arousal, I felt myself getting hard as well – in no small part because of the memory of the last time he’d worn his silky undies. We didn’t do much fishing that day, but our rods certainly saw a lot of action. When we finally did decide to call it quits, it was because of soreness, rather than a lack of enthusiasm. In the end, he discovered he got the most enjoyment by stroking as he sucked me off – and that suited me just fine. He liked timing his own movements so that he would come just as I shot into his mouth – and I passed the time by talking dirty to “Erica,” asking if he liked the taste of cock.
Eric never did become “Erica.” However, he “accidentally” bought a large bag of women’s socks. They looked a lot like men’s sock, just more sheer – but that didn’t seem to dampen his spirits. He began wearing them under his shoes and pants as everyday clothing, but admitted that he loved the secret knowledge that he was wearing “girls’ clothes” – no matter how little anyone noticed.
Once the excitement of his first foray mellowed a bit, he began wearing his panties whenever he was sure he’d stay undiscovered. He slowly acquired more, but he had to wash these by hand, lest his mother find them in the laundry, so the collection remained small. Nevertheless, his day-to-day wardrobe also became steadily more effeminate. His jeans grew tighter, he took to wearing small tank tops and jewelry (chunky male stuff at first, but increasingly delicate) and, when he went to college, he began wearing make-up. Dresses were rare (mostly because his physique was that of a male surfer, and he could never pass fully as a girl) – but within a few years, he definitely fit anyone’s definition of “femboy.”
There was some ugly business when Eric came out to his parents; but, by then, he had a good group of friends to support him, and his s****r actually said she wished he’d said something sooner – she totally would have dressed him up when they were k**s. The world moved on and we grew increasingly distant – or hang-outs (and, likewise, our playtime) growing increasingly rare. However, by the time we parted, we had made a few clumsy attempts at anal play, before settling on me thrusting into his tightly-closed legs from behind. He loved the feel of my cock caressing his perineum, nudging his balls, and I often gave his thighs a good soaking from my enjoyment.
It’s something I don’t speak of very often, but my experiences with Eric remain something I treasure. He was a good friend and a very pretty boy, and I feel privileged to have known him.