My [M] experience with a trans woman [F] at a local concert in my late teens.

In my late teens I used to be wrapped up in the metal/punk scene on the local level. If you grew up going through a rough existence it was the place that reliably had a place for you regardless of who you were or where you came from. I remember putting great stock into what band was on my t-shirt, the boots on my feet and the cut of my hair. I worked warehouses as a kid, so I could get away with a Mohawk slicked back in those days. There was always alchohol and buds if you asked nicely, and if your heart had the beat of a war drum the music was the sound track to the fires of your soul.

Those days were untamed and unsustainable, but the best of them are some of the best memories I’ve ever had.

I’d been looking forward to this Friday for some time. A local band had whispers of touring with some Europeans, a sign that they’d be too big for our city soon. Our city has an agricultural district on the east end. Someone, knew someone, knew someone who’s family member owned a building that had once been used for processing strawberries. That was going to be the venue for our little garage band concert, and supposedly it was as good as certain. At least as certain as impromptu venues go.

I used to work Tuesday through Saturday but I’d taken it off the moment I knew that the show was more than talk. There were some grumbles of their being a door fee of $10 but I didn’t care. They played at bars that I’d been turned away at for being under 21, so I was in even if it was $20. The biggest oaf of us drove a mini van we’d pile into, by 8 one of the local bands was already sloppily belting out some of their songs and the early birds were tolerating them, us included. The power situation was sketchy and one of our dudes had to be there early to help.

One of my cousins bought a bottle of Espolon for me, it was dirt cheap at the time. And showing up to a party with a bottle of tequila to pass around cemented me as “hard as fuck”. I’d grown up in a big Mexican family and tequila and beer were always at family parties, so the taste that scared off the weak did nothing to me. Plus after passing it around a few times I realistically only took four or five shots max. It was mostly an ego boost, and someone was more than happy to kick me all of the water and sprite to keep me from dying so I really avoided a hang over while catching a mighty buzz. The beginnings of my method were in full swing, and I was starting to figure out that this was going to be a bigger thing than I’d invisioned. The standard crowd for a house party concert was already here. People from shows I’d been to in other towns were showing up. The group I came with had dissipated into the crowd, some of the opening groups had real talent.

A woman about my age nudged my shoulder. And asked me if my bottle was for sharing, I was already nearing my tipping point so wasn’t hesitant to share. We were next to eachother in the crowd for a time enjoying the spectacle. The mosh pit was calling my name. But the cute girl sharing booze with me was much more of an interesting prospect to a 19 year old boy. In between bands setting up we sparked up a conversation. We were both excited to see Warbringer “make it”. They were local heroes at the time, living legends. We’d grown up on opposite ends of the same city, we were on her side of town.

She was smaller than me by at least 5 inches, with a cute pointed chin. Dark pointed eye make up and deep red lipstick. She had a Toxic Holocaust t shirt cut into a crop top wich scored huge points with me. Skinny torn black jeans with a pair of serious Doc Martens. She had an emo hair cut with hair covering most of one eye. Everything commenting a small slender frame on milky pale skin. She had a hell of an ass, and I know what you’re thinking, no real Adam’s apple to speak of. I could easily see someone cracking a joke about the tequila or weed impairing my ability to detect these things. But if you put her in a line up of similarly dressed woman, most men would fail to pick her out if not all. The curves, the way she carried herself, the way she moved, it all screamed woman.

We actually parted ways for a few sets to link up with friends. Someone had brought a large bong with what seemed like a limitless supply of shake near it. A few rips and I was a mad man in the pit. Most of these bands were belting out fan favorite covers. I’d transitioned to music and water, I was flirting dangerously with the edge of my limits. But I had great success with the exercise the pit provided, water replenished me, and a mighty piss purged me. I remember we linked back up when a band said something like “These next ones are songs we learned when we first started playing, if you don’t like them, go fuck yourselves”. Than immediately went into a cover of ‘I Want You to Want Me’. My parents listened to that song growing up all the time, I love that song. Only a few of us stayed on for this song. Of course, she was there. This song dragged out the ladies wich naturally brought out a bunch of guys to. I took her by the hand and we danced together. The band ended with some ‘Burning for You’ and a few other lighter toned songs.

There were still a few groups to go on before Warbringer, but we were hooked. We spent that time talking on the outskirts. Since I was known to pour a heroic pour of tequila in my sprite with lemon no one pressured me into drinking if they saw a drink like that in my hand. It was just sprite and lemon though, I let her know my secret. Warbringer came and went with both of us going wild in the crowd. It was about 1am now and anyone who wanted to plug in could. We were far away from the action now, the side of the building facing the feild offered us a quiet area to talk.

Our conversation was interrupted by the flash of red and blue, the crowd came alive with panic, cops. They were working the crowd in the front of the building. I had no booze on me but I’d clearly been drinking and smoking. She took my hand and guided me down the dirt road. We ran till we got to a street that had a road where the backs of houses made an alley that was separated from the strawberry feilds by chain link fence. I helped her over and hopped the fence. We laughed and called to see who made it out as we walked side streets to her friends house near by.

Out of the six guys I came with only one picked up. Found out later that our driver had seen cops questing someone before back up arrived and took the van elsewhere so it wouldn’t get locked up. We were all technically parking illegally. One of my buddies caught a possession charge that night for an 8th of weed, dumb ass didn’t ditch it when he had the chance.

But I was out a ride and her friend took us in. It was a 3 bedroom that a few ladies rented together. One of them was out of town so we were offered her bedroom for the night, we’d figure out transport in the morning. No one here had been to the show so they asked that if we stayed up to be quiet, it was late. I told her that I usually go in to work early Saturday, so a coworker would be able to pick me up around 10am. “I can sleep on the chair, you can have the bed. Unless you want to share ?” I asked.

She said nothing for a uncomfortably long silence, staring at the floor the whole time. I put a hand on her shoulder “hey, don’t worry, it’s ok. I’ll take the chair.” We just met so I didn’t want to pressure her into something she didn’t want. When my hand left her shoulder she sprung forward and crossed her wrists around my neck. The smell of tequila, weed, and make up was strong. Her lips searched mine expertly, she knew how to use her tongue without being heavy handed with anything. I laid her down on the bed and we continued kissing. At the time I thought she was either inexperienced or a virgin so I took it slow.

I never asked after, I didn’t want to be rude. But her chest felt natural, it didn’t feel like she’d had any work done. It felt like she had a natural B cup despite having a slender body. The trouble came when my hands started to fumble with the button of her jeans. She immediately pulled away and tensed up. I associated this with trauma related to assault so I stopped and told her we can stop. Tears started to drip down her face. I told her we could talk about it if she wanted or if she wanted space I had no trouble dropping it and giving her space. She kept repeating that I wouldn’t understand. I told her that I’d gone through rough situations as a kid and had talked to others who had to. She told me that it wasn’t like that, and that she hadn’t been through anything like that. I asked her if I overstepped or did something wrong.

She told me that she was the one who was in the wrong. That she hadn’t been truthful with me. My mind was on her having a boyfriend, maybe even a husband, an STD maybe ? I still had no clue. I already knew what a trans person was, so when she started describing to me what it was it hit me. She was trembling as she explained, I later learned that she thought I was going to hurt her in this moment. She thought I’d be furious that we’d gone this far. I was shocked, sure, I won’t deny that. I’d just spent a hell of a night having fun and getting to know her, I was a little hurt that she didn’t tell me sooner. I let her know that, I told her that I couldn’t imagine what she’d been thinking.

I told her that she was fine, she initially hesitated when I tried to hold her. She was still trembling and still tearing up. I felt compelled to comfort her. I assured her that everything was fine and that I held no resentment. She asked if I’d noticed anything off about her. I laughed and told her far from it. I confessed that I fully expected to find a wet pussy waiting for me under her jeans. We talked about sexuality, when she felt comfortable transitioning. We complained about past relationships. But than she asked about my sexuality, how I knew I was straight. Relatively easy to answer, I’d never been turned on by another man before. I guess at this point she felt comfortable enough to say “a guy got you pretty hard a second ago, I felt you not so subtly pressing your cock against me,” her words not mine.

The proof was out there, I couldn’t lie. She did get me hard. I confessed that everything we’d done so far felt great. She was getting bold now. She asked me if I felt comfortable seeing if she could get me hard again, now that I knew, so I’d learn something about myself. I hesitated, but I’d already kissed her. I couldn’t see why it would matter if I kissed her again.

So we did.

And surely enough after she pressed her chest against me and kissed my collar bone, I was hard again. She squeezed my dick through my jeans and we both laughed a little. I made the decision than to feel the situation out. Bolder and bolder she unzipped and pulled down my pants. She licked the tip of my cock and made it hard to be quiet. After a few generous passes of the tongue she took my whole cock in, I felt the back of her throat and heard her suppress her gag reflex. No 9ne had ever taken me that deep into their mouth before. She took me in, in long deep gagging strokes. I’d never been blown like this before. When she came up for air she’d keep faster short strokes with her hand. Occasionally she’d suck and lick my balls, another first for me. She was driving me crazy. At some point she wiggled her pants off. She was down to her bra and panties. “Want to try and fuck me ?,” she asked.

I hesitated and she felt it. “Ever stuck it in a cute girl’s ass ? It’s really similar” she said bending over. I’d gone this far, it felt this good. She was on all fours in front of me, I was on my knees behind her. She kept her panties to the side with one handvand guided my cock to her hole with the other. I was still hard and my dick was drenched with her saliva. It was slow going, she was super tight. It took a while to get any momentum going, but it felt good. We were quietly moaning, I couldn’t give it to her super hard. I pushed into her deep when it happened. I’d felt it a little on the first few thrusts, but on one long one I couldn’t ignore it. The bottom of my balls hit the top of hers. It shut my dick off like a light, I pushed rope for a thrust or two. I pulled out and tipped over. We both started laughing “looks like you’re just a hair too straight for me,” she said rolling over to look at me. I told her that she had me guessing with that blow job, she almost made me cum.

She set her cheek down on my chest and said “go rinse off that cock, third time is a charm.” I laughed and needed to piss any way so I obliged. I used hand soap to and wrinsed off, whiping with a hand towel I felt a little guilty about. I tossed the hand towel on a dirty clothes pile I’d noticed earlier. I was trying to respect that we were in someone else’s space, though the anal sex may have disrupted that already. She admired me as I came back to bed entirely nude. I was way more into weight lifting than, I worked a physical job, and I was in and out of boxing training so I was incredibly in shape. She warned me that I better have scrubbed well. I told her that my cock was drenched in pre-cum, I needed to scrub it. She set her cheek down on my lap and played with my cock lightly. Her ass looked great in her panties and her chest looked indistinguishable from a woman with smaller breasts.

I told her that no one had ever deep throat me like that before. That the woman that had tried before had nearly vomited and didn’t go nearly as far down. This stiffened me, she adjusted and made her strokes a little longer as she stared at my cock. She told me that she’d never had much of a gag reflex and only recently learned that it wasn’t a common skill to have. She had me going again. This time she dropped her mouth down slowly, everything she’d just done had me sensitive. When she came back up she let my cock go with a little pop. “Tell me when you’re close,” she said. She took my cock down to the root and kept it there, swirling her tongue around it. I was back in that state of bliss. A moan escaped me that was a hair too loud wich earned me a slap on the stomach. She picked up the pace again. Long, slow, gagging strokes that were just a hair faster than before. She had my balls in her hand and was ever so slightly massaging them while she blew me. When she came up for air and started rubbing my cock her pace with her hand was slightly faster than before too.

This is what was doing it for me. A lot of girls at the time would death grip my cock in a hand job, she had just the right amount of grip. I took a hand full of her hair to keep it out of her space. The sound of her light gagging noises as she blew me were so raw that I couldn’t deal with it. “Almost.. there.. ” I moaned softly. She added a small twist at the end of her stroke that sealed the deal. Each one nearly did it. I squeezed her ass and she moaned as she went down. I could barely speak, it only took a few of those to get me. “I’m gonna.. cum…” I managed to get out. She held her throat down and I shot my load straight into her. That was so beyond what any woman I’d been with before was comfortable with. She pulled off of my dick slowly with that same pop as earlier. This time with a strand of cum stringing from my dick to her mouth.

I was damn near hyperventilating and astonished at how little cum came out of her mouth. She caught her breath and rested the back of her head on my lap like a pillow. We both started laughing “but I’m just a hair more gay now than I was this morning,” I said in between breaths.

We cleaned up and laid back in bed together. Our conversation went all over the place. Sex, love, society, changing times, past experiences, and what we wanted out of life. Before I knew it I was asleep. It felt like I was only gone for 30 minutes but my phone woke me up. I’d texted a coworker to pick me up after he got off. It was 10:30am and he was outside. I scrambled to get dressed and lightly jostled her awake.

I told her that my ride was here and that I had a great night. I told her to look for her phone. When I told her to take my number down she said “I don’t expect you to be my boyfriend, nothing has to happen because of this,”. I ruffled her hair and said “when did I say boyfriend  ? We had a great time. Do you want to be my friend ? I feel like we know eachother for that to make sense, yea ?,” she nodded and I made my way out as quietly as possible. No one was awake yet.

She’s been my friend for over a decade now. We used to hang out pretty regularly, we still message eachother and comment on eachother’s posts. We both moved a few states away but have loose plans to visit once covid dies down. I’m married now, I never had another relationship of any kind with a trans woman after her. But I learned a lot about my self and how sexuality works.

I did a lot of growing that night, I’d do it all again if I had the chance.

Source: reddit.com/r/gonewildstories/comments/o0jrui/my_m_experience_with_a_trans_woman_f_at_a_local