My First Time: I Kissed a Girl Who is a Guy

As I’ve mentioned, I started to really make friends in high school because everyone fits in somewhere. I mostly nerded out with the music department, but I also found a home with the ‘goth’ kids. Not emo, but goth – dark clothes, wallet chains, skulls, angry music, platform leather boots, and pants with legs you could fit two of your friends in. Because of my depression, I’ve always identified with the more macabre things in life and really found comfort in that crowd.

I often sat with the goth kids at lunch, usually with my best friend. For no apparent reason one day during our junior year, she told our friend Heidi that she should kiss me. I’d never kissed a girl before, but the idea didn’t actually sound terrible to me. Heidi had long, blonde hair, eyes as blue as the ocean, big tits, and a smile that warmed your soul. She’s absolutely gorgeous, so I didn’t exactly protest.

Heidi was sitting across from me, so to my surprise she stood up and started walking down the length of the long tables. I wasn’t sure if she was walking away or headed my way, but I felt a twitch in my loins when I saw her round the corner to my side. There was an empty seat next to me, so Heidi sat down next to me, grabbed my face with one hand, and started kissing me. Her lips were so warm and full; her tongue just barely found mine but it was enough to make my nipples harden. We kissed for several seconds, then she got up and returned to her seat.

kissing5I was somewhat embarrassed having done this in the middle of the school cafeteria, but I didn’t care too much because it was incredibly hot. I told my best friend I liked it, so she made the ‘suggestion’ a few more times for my sake over the course of the school year. (One of those times was witnessed by my super hot guidance counselor who did a double-take walking by the cafeteria one day.) Another time I managed to find myself in a three-way kiss with Heidi and another girl.

The next time she kissed me, her hand found its way to my breast and she gently stroked my nipple. It would have been rude to not reciprocate, so I grabbed her and couldn’t believe how full, firm, and soft they were. Yes, NEWS FLASH – high school girls play with each others’ tits all the time, it really is quite awesome. At least my friends and I did anyway. After that, it was as if we had earned some ‘right’ and we would touch each other whenever we wanted.

Fortunately, people felt comfortable enough to start ‘coming out’ by the time I was in high school, so I had several gay and lesbian friends. I was friends with a pair of sisters, one of whom was a lesbian. I kept getting the feeling that Jess was flirting with me; then one day after telling me she’s nervous around me, she confessed to having a huge crush on me.

I was incredibly flattered, but I wasn’t quite sure what to make of it. I definitely have always liked the cock and knew I’m not a lesbian, so I didn’t want to lead her on. I told another best friend who had already proclaimed to be bisexual back then about what had happened, and she convinced me to give it a try. I had never done anything more than kiss and grope Heidi, so I really wasn’t sure how I felt about vaginas. I knew FOR SURE I like men, and vaginas always seemed sort of gross to me. But after several months, I decided to go for it anyway.

The friend I had told about Jess volunteered to be my wing-woman, so we invited Jess to hang out together one day. At the end of the night, my best friend ‘asked’ to be dropped off at home, so I invited Jess to sleep over at my place after we dropped her off. Of course she accepted, so we went back to my house.

We hung out in my room and eventually ended up lying in bed talking. She’d been flirting with me all day but for some reason, she wouldn’t make a move on me. I knew she’d fuck me in an instant, but I think she respected me too much to put me in that position. So I knew what I had to do – I had to initiate.

We laid there facing each other so I leaned in and kissed her. I ran my hand up the back of her neck and through her hair as I pulled my body in close against hers. She wrapped her arms around me and I held the small of her back as I kissed her.


We made out for a while but she seemed hesitant to take any next steps, so I pushed her onto her back on my bed and straddled her. I continued kissing her as I slowly pressed my hips against hers. I took her shirt off to reveal her bra and kissed my way down her neck and onto her breasts. I exposed her nipples and her breath caught as I slowly took them into my mouth. I learned that her nipples are her most sensitive and pleasurable areas.

I made my way past her ribs and down her stomach, then took her jeans off. In her bra and panties she sat up and gently pushed me onto my back to do the same to me. With both of us stripped we kissed and touched each other, but she still seemed hesitant to go any further. So I reached down into her panties and played with her pussy – someone had to get this party started.

It was pretty scary for me since I’d never played with anyone’s vagina but my own, so I wished she would just take over. She was incredibly into it but probably wasn’t sure how far I was willing to go, so I took the lead again and went down on her. I’m very intuitive and often imagine in my head what something feels like to the other person, so I had a general idea of what I was doing and she seemed to be enjoying herself.

Having never been able to keep my hand out of my own panties, I know what feels good so I licked and fingered her while monitoring her breathing and moaning. As I fingered her I noticed that her moaning was proliferating, so I increased the speed of what I was doing and shortly I had her screaming.

Once she caught her breath, she dragged me to the edge of my bed and stood on the floor between my legs. She leaned over, kissed me to taste her own juices; then sucked on my nipples as her fingers grazed my labia. I remember she spent a lot of time on my tits, and I silently begged her to eat me out.

Eventually she knelt down on the floor, spread my legs, and licked and kissed my inner thighs. She gracefully spread my lips apart and began gently massaging around my clit, though I was already quite wet. She licked me while crooking a finger inside of me, and soon enough I was cumming just like she had only minutes before.

She climbed up off of her knees, I readjusted lengthwise on my bed, and she rested beside me. I turned off my lamp, and we held each other as we fell asleep. Overall, a successful first girl-on-girl experience for me, I thought.


She’s a year or two older than me so she graduated high school first, and we lost contact after that since Facebook was only founded the year after I graduated. I’ve been with a few girls since her, but turns out I really just like cock. However, I stand by the fact that women are AMAZING kissers (and boobs are FANTASTIC), so I’d kiss the right lady as long as my husband is present to enjoy watching.

Fast-forward to last year. Now that Facebook is alive and well, I’m able to stay in contact with friends from high school, college, and other random places. One day on my feed, I noticed that a friend had commented on a picture of someone who looked REALLY fucking familiar, but not quite the same.

Upon further inspection, I realized it was Jess from high school – only Jess is now Jeff. Turns out that Jeff began his transgender transformation about 4 years ago and has legally changed his name to Jeff.

As you know, I’m an avid advocate for transgender rights, so I wasn’t disgusted or appalled and was really happy to see that he’s becoming the person he always knew he was. I added him on Facebook, and we’ve been ‘friends’ for several months now. He had sent me a couple of invitations on Facebook to attend rallies to support transgender rights, but I was always out of town. Finally, I made it out to one to support a transgender equality bill.

We had been messaging on Facebook about a rally and ended up exchanging numbers and texting the night before it. Texting is pretty impersonal so we didn’t talk about anything deep, but we had a brief conversation and I wanted him to know that I would be coming to the rally. Being transgender is difficult enough; so in the event that he needed to process anything before seeing me again after a decade, I wanted him to have some time to prepare.

I was a bit nervous myself as I usually am when meeting up with new-ish people, but the second he recognized me I felt instantly comfortable. He was standing on the sidewalk with a clipboard greeting people who came to the rally as I walked toward him. When I was about 5 feet away from him I smiled and raised my sunglasses; he instantly gasped, smiled, and said “Well aren’t you a sight for sore eyes?”

I ended up spending the day with him and a few new friends as we waited for transgender testimonies to be heard and the bill to be voted on. After a long day a few of us decided to go back to Jeff’s house and have some drinks. We spent a lot of time alone on his balcony talking about high school, depression, and his transformation, and I truly felt at home with him. He took care of me while we were drinking, loaned me some pj’s, and I slept over because he didn’t want me to feel pressured to drive after drinking. We talked in his bed until 3 A.M., cuddled a little, and slept a few hours; then he made me breakfast when we woke up. It was like not even a day had passed by in our friendship, nevermind a decade.

It’s been really wonderful having him in my life again, and I think it’s going to open up a lot of other doors for me. I’ve already made new friends by attending a couple of rallies, it’s forcing me to get out of the house and pushed out of my social comfort zone, and it seems like the start (or continuation) of a really close friendship. Funny how things turn out in life.

So ya, I guess I kissed a girl who really is a guy.

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