When I was fourteen, I dressed up like a girl and had a threesome with two of my friends. When my parents and sister went to visit relatives for a weekend, I held a house party in which a couple dozen or so people showed up.
Everyone cleared out after the cops showed up concerning noise complaints, with the exception of two of my close friends, who had received permission from their parents to stay the night.
Growing up, plenty of my straight guy friends hit on me. They would playfully dry hump me or want to practice what it was like going up a girl’s shirt, with me being the closest thing they could get to a real girl. I was small in stature with androgynous features. I was often mistaken for a girl and sometimes picked on for it. I enjoyed my male friends’ attention, but never felt the need to take it further for a few reasons:
1. The social ramifications were too much. I often fantasized about making out with a friend while jerking him off, but there was no way I could act on these thoughts in my small, suburban hometown.
2. I wasn’t ready for sex. The thought of sticking my hand down a guy’s pants when he came on to me never crossed my mind.
3. Even to this day, I’m a complete prude when sober. Sadly, I need alcohol to open up. Seriously. After three drinks however, I turn into a complete slut.
On this night, I had more than three drinks. Too trashed to clean up the house, we ended up watching *Crash*. Not the emotional tear-jerker *Crash*, but the David Cronenberg 90s movie which was basically a softcore porn. We were all turned on and making jokes to mask our discomfort. Being drunk and adventurous, I decided to say, “the hell with social ramifications” and commented on one of the actors, who in one scene, stripped down to her lingerie:
“I could pull off those stockings better than her.”
And I truly believed it. For years, I covertly dressed up in my sister’s old clothes. We had a “To Goodwill” pile in our laundry room for clothes she no longer wanted. Although they were a little big on me, the vast majority of them never made it out the door. Instead, they found themselves tucked into the crevices of my bedroom: crammed behind dresser drawers, stuffed under my mattress, and so on.
One of my friends sarcastically quipped, “I’d *love* to see that.” Joking or not, I took that as an invitation. They clutched their beer-filled bellies and claimed they were kidding. Ignoring them, I shot off to my room, adrenaline pumping.
I still remember the outfit perfectly: green satin panties, a black bra, black stockings, and black heels. I dabbed on a little Clinique Happy. Sorry to hit you over the head with details, but it’s exactly what I wore.
Unlike most guys my age, I hardly showed any signs of hitting puberty. I was often mocked for my high pitched voice. My body hair was either nonexistent or light and blonde. As it followed, my skin was hypersensitive to the tantalizing touch of silk lingerie. I got hard every time I put on a pair of panties. I didn’t bother trying to hide my excitement.
I took too much time admiring myself: “What’s taking so long?!” Apparently, they couldn’t hide their excitement either.
I walked out, strutting like a runway model. I was and still am really good at walking in heels. They burst out laughing but my confidence never wavered. It was the first time I had worn womens clothing in front of anyone. What’s more, they couldn’t remove their eyes from me.
“That’s enough!” They were having difficulty making out the words in between laughs. So I took a seat… on one their laps. Considering how he had been checking me out, I knew he would like it. It came as no surprise when he wrapped an arm around me.
My other friend chimed in, “Ohhh! I don’t get any attention, huh?” I answered in as girly a voice as possible. It wasn’t totally convincing, but I felt like a girl in front of them and knew what they wanted: “You can come over too.” I was shocked by my own bravery.
The mood in the room changed when he took a seat next to us, resting his hand on my thigh. The beers were put down. The laughs were gone. We were all wondering what to do next as we watched the movie, suddenly uninterested in fast cars and topless actors. They started exploring.
One of them was massaging my thigh, running his fingers under the waist band of my panties. Honestly, he looked like he was in a trance staring at my legs. The other felt up my “tits” i.e. my padded bra. I broke the silence, shyly trying to talk like a girl again: “I like it when you touch me like that.”
I can’t remember how the sex was initiated, but I do recall not overthinking things like I do when I’m sober. I just remember neither of them protesting when I reached down their pants.
They talked to me like I was a whore, there for their entertainment. “Stroke my cock, slut.” One of them kept commenting about how small and smooth my hands were. I felt him flinch when I kissed him. He couldn’t hold it in, ignominiously cumming all over himself. Later on, I found out I was the first person to make him cum. Apparently, he could never get it up with previous girlfriends.
The one left standing took control. I learned how to give head on the fly. He was much more mature and larger than I was, but I had no problem deepthroating him. I know men talk about how great that feels, but in my opinion, taking a cock all the way to the base is equally gratifying. I tasted pre-cum but didn’t want to swallow it. So I said in my most feminine voice yet, “Don’t cum in my mouth.”
I was taken by surprise when he got behind me. In private, I played with vibrators and fantasized about the real thing. Prostate orgasms were easily my favorite way of masturbating. Also, if you’re curious about getting fucked or pegged for the first time, have a couple drinks beforehand. You’ll relax and moan louder than you ever have.
He kept my panties on, moving them to the side. I know he didn’t want me naked. The lingerie let him keep the fantasy that he was fucking an actual girl.
He made me suck his cock once more, telling me, “Get it as wet as you can. It’s going inside you.”
When he entered me, I moaned uncontrollably. This time, I legitimately sounded like a girl. He kept spitting on his cock to keep me wet. It sounds kinda gross but when you’re in the moment it’s pretty hot. I remember feeling so degraded. Here I was on all fours, dressed in skimpy lingerie, getting fucked by my one of my classmates. My ass was providing pleasure for his cock. The taboo nature of it all added to my excitement.
Maybe he had a fantasy involving a cock sucking crossdresser, because he couldn’t take it. I must’ve been too tight for him because he came in less than five minutes. I remember feeling so emasculated when he came inside, as if my last traces of masculinity were stolen. I felt like I was his property.
As for me, I didn’t get off but was more than okay with that. My panties were like a chastity device.
With both guys passed out after cumming, I returned to my room. I remember sitting on my bed smoking a cigarette, reflecting on my first sexual experience, when the friend who fucked me entered. I was still wearing lingerie when he crawled into bed beside me. Taking me by surprise, he pulled me close against against him and guided my hand towards his crotch. He was ready for round two. He fucked me in a spooning position, but yet again, he couldn’t hold his cum for more than a few minutes. It wasn’t the amazing sex I had hoped for, but it was kinda sad-cute which I found entertaining. He didn’t bother apologizing anyways.
Surprisingly, he talked to me afterwards, opening up quite a bit. He expressed worry about his sexuality after hooking up with me. I told him to calm down since he only fucked me because I looked like a girl. Plus, I wasn’t going to tell anyone. He was being paranoid, but he eventually relaxed while I fell asleep in his arms.
I’d love to say we continued having sex from time-to-time, but we never did. Instead, he and the other guy ignored me and broke off our friendship. I’m sensitive, so I was pretty hurt, especially since I envisioned a secret relationship forming.
What’s worse, the two of them warped the story of that night. They told people at school that only I did gay things and that they had no part in it. According to them, I dressed up like a girl and tried to come on to them, so they left.
The rumor went around school and led to a lot of bullying for me. I wanted to tell people what actually happened, but then I would have to admit I got fucked by a guy. It was a double edged sword. Plus, they were much more popular than me so no one was going to take my side anyways. I stopped dressing up as a girl in front of people and repressed most of my sexual desires. I didn’t recover until after high school, when I stopped seeing the same circle of people on a daily basis.
So, I wish I could’ve ended this story on a happier note, because the fallout did cause some torment for me during high school. But don’t worry, sports fans, it also caused me to move to an open-minded city where I could dress like a girl and have as much (safe) sex as I wanted. I don’t hold a grudge against the two anymore. Looking back, I can divorce the emotions that followed and appreciate that night for how kinky it was.
Last year, I had a one night stand with a guy, which turned into another one night stand with him… and another. We’ve now been together for over a year and it’s the happiest I’ve ever been in my life. It’s safe to say, I’m at peace with myself.
Source: reddit.com/r/gonewildstories/comments/474d59/mmm_when_i_was_in_high_school_i_dressed_like_a
Whoa. Any other stories like this?