[M]y attempt to seduce a lesbian [F]riend results in a hot, genderfluid hookup

I’m a straight guy who’s been experimenting with genderfluidity for a couple years now. This story is one of the first incidents that got the ball rolling, back from when I was just out of college, working an office job with a bunch of other young people.

The co-worker I hit it off with the most was Sam, a girl who I swear to god looked exactly like Kristen Stewart. She was an alpha personality and had a really androgynous vibe, cute face and an amazing body. Our dress code at work was pretty loose and she constantly wore short shorts that showed off her long, sexy legs. She told me she only dated girls and I told her I understood, but that didn’t stop me from developing a huge crush on her.

As the months went by, we would go out drinking. We talked a lot about gender and sexuality because I was really intrigued by the types of girls she hooked up with: they were all a lot more femme than Sam was. They wore dresses, had longer hair, etc. I asked her if that meant she saw herself as more of a guy. Sam told me she didn’t think of herself as a guy, but she felt more confident and sexy when she was dressed in a more masculine style. I told her I agreed and I thought she looked a lot sexier in sambas than most other girls looked in heels.

I guess I brought gender stuff up enough that she finally asked me if I had any gender issues. And the truth was, I’d always felt genderfluid but had never acted on it because I was raised in a traditional family where the emphasis for boys was always on sports. But I knew my fluidity was part of the reason that I was always attracted to athletic tomboys. I knew I didn’t want to be a girl, but I wasn’t comfortable being super masculine either. Skinny jeans, Toms, longer hair, etc, that was my style. I’d never had trouble dating in high school or college, but I was definitely more “cute” than “handsome”. I was 5’9″, slender, not very hairy, etc. Sam told me I shouldn’t be afraid to try out a more femme look if I wanted to. She said if I ever wanted to do a private fashion show, I could come over to her apartment, we could drink wine and try on clothes.

Okay, so this is where my brain immediately went: “Holy shit, if I could dress hot for Sam, maybe she’d hook up with me.”

Obviously it’s not the smartest thought I’ve ever had and OBVIOUSLY this is not how sexuality works, but I had a crush, and also I’ll admit I was really excited to try on female clothes for Sam.

So like a week later we made a plan and I came over to her place with an outfit I’d bought on amazon. I even shaved my legs for the occasion. Sam answered the door barefoot, wearing tiny adidas shorts and a Nirvana shirt, and asked if I was ready to to be a fashion model. I was so fucking nervous and we immediately opened a bottle of wine, then I went to the bathroom to change.

The girls Sam liked were femme, but not super femme. In my head I thought I’d look good in kind of a prep-school uniform style. I bought a grey pleated skirt and a tight, white women’s polo shirt. The skirt ended just above my knee, and the shirt actually could’ve passed as a men’s shirt except the sleeves were higher and showed off more of my arms.

My legs are really lean and I’ve always thought I had good ankles. They looked good shaved, but they were pale so I bought tights. As someone who’s been intrigued by girls clothes since childhood, tights were the one thing I had some experience with. I wore mens tights for cross country and tennis in high school. In college I wore leggings under shorts to class and around campus. Tonight with Sam I wanted to wear something sexier, so I bought a pair of the thinnest sheer black tights I could find. Sliding the silky material up my legs felt incredible, and I couldn’t believe how good my legs looked in them.

I didn’t buy shoes because they were too expensive for a night of dress up, so I decided to just go in stocking feet. And I didn’t think make up was a good idea because I had zero idea how to put it on. So I was done getting ready.

It was the moment of truth, so I downed the rest of my wine and rejoined Sam in the living room. She jumped up from the couch and looked me up and down with a huge smile on her face. She hugged me and told me I looked awesome. She was like, “Look at those legs, holy shit!”

She asked me how I felt dressed femme, and I thought hard about it. There were two major things going through my head… the first was that I was dressing to be sexy for Sam, and I wondered if it was working, but I didn’t know how to ask her. The second was that I actually felt great in the clothes. I didn’t feel stupid or emasculated. I felt hot. So I told her that, and she was really happy. She got us more wine and we sat on the couch to watch TV and talk.

Both of us had our legs up on the coffee table in front of us, and I was so turned on looking from her amazing bare legs to my legs in the tights. At one point I started rubbing my legs together to feel the silky material better. Sam noticed and smirked. “Enjoying those tights?” My face got a little red and I told her yeah, they felt really good on my legs.

Sam reached over and rubbed my thigh to feel the material. I laughed, then pulled my leg away. I told her we had to be careful, it felt a little too good to have her rubbing my legs like that. She rolled her eyes, gave me an evil look and then got up to go to the kitchen. While she was gone, my head was SWIMMING. Was she flirting? Did she think this was hot, too? I honestly couldn’t tell.

She came back with the bottle of wine and some snacks. She stepped over my legs, brushing hers against mine as she put everything down on the coffee table. I almost exploded, both from the touch and from the mystery of whether she did it on purpose.

She sat back down, then leaned over to pour more wine for both of us. As she leaned, her bare thigh rested fully against my leg. I could feel the warmth through my tights and I was DYING. This HAD to be intentional. I had to know what was going on. So I casually dropped my hand onto her thigh and gave it a little rub as I said, “Thanks for the wine!”

I felt like I could hear her inhale a little bit, then she said, “No prob.” Meanwhile, my hand was still resting on her thigh. Her skin was so warm and perfectly smooth. If this was all that happened tonight, it felt like it was still the achievement of a fantasy I’d had since I met Sam.

She finished pouring, and my hand was still sitting there. She locked eyes with me and I was totally frozen. I had no clue what was going to happen next, but all I knew is it was her move.

She stood up and walked away. Fuck. I was destroyed. I made it weird. I drank some wine and adjusted my skirt, trying to get rid of my boner. Then Sam came back and sat down. I didn’t look at her, so it was a surprise when I heard her take the top off a tube of lipstick. She told me, “I don’t think you need full makeup but you have such great lips. Let’s try this.”

She turned my head and carefully put lipstick on me. All I could feel was her hand on my chin. Her face was so close to mine. I literally couldn’t breathe I was so turned on.

“There, that looks fucking great.” Sam took out her phone and showed me my face. My lips were a nice, deep red, and she was right – it pulled everything together. It wasn’t drag. It was just this sexy, androgynous look that for whatever reason really worked on my face.

“Thanks,” I said. I could feel the big smile on my face. I put my hand on Sam’s forearm, partly out of genuine excitement and partly because I wanted to keep touching her.

And that’s when Sam made her move. She pushed me back on the couch, climbed on top and fully straddled me. She didn’t say a word, she just dove in and we made out. For the first thirty seconds or so I couldn’t form any thoughts. But then I found my footing and started kissing her back. It was the most amazing makeout of my life. She ran her hand up my shirt and rubbed my chest. I slid my hands under her silky soccer shorts and cupped her perfect butt. Her legs slid against mine, up and down, and it was this explosive feeling I’d never felt before… her smooth skin, my smooth skin, the silky tights I was wearing. In that moment, I was like, “Lesbians… I totally get it.”

We made out for a really long time. She stayed on top the entire time, and I know she could feel my dick pushing against her because after a while she was grinding on it. I was starting to wonder what was going to happen next, when Sam sat up and leaned back on her knees. She was still on top of me, out of breath, a satisfied, mischievous look on her face. She started rubbing her hands up and down my silky thighs. I moaned and told her she was killing me. I asked her what she wanted to do next?

She told me she didn’t want to have sex. It was too weird for her. I was disappointed, but told her I understood. She got back down on top of me and resumed grinding on my dick. I knew it was basically the consolation prize, and I took it. I started grinding back. We kissed some more, and I relaxed into the feeling of her on top of me and my tights sliding against my dick. It didn’t take long before I had a HUGE, brain busting orgasm, completely soaking my tights.

Sam got off of me and we both went away to change. When we sat back down on the couch we talked for a while about what happened. She told me she thought it was a really hot experience, but that she didn’t want to date me. I confessed my crush (she knew) but said I’d keep it under control so we could keep hanging out. We both agreed it would be fun to go out somewhere with me dressed, etc. She was like, “we’ll find you a straight girl who likes this.”

At the end of the night, she hugged me and I went home, completely buzzed by the whole experience. Now I can say that one of the hottest nights of my life didn’t include any actual sex.

Source: reddit.com/r/gonewildstories/comments/dal24t/my_attempt_to_seduce_a_lesbian_friend_results_in