Episode 5 - Jaelynn "Don't Touch The Hair"

Jaelynn shares stories from her life growing up queer in Mississippi and her evolution as a trans woman. Her stories include misadventures in the sex trade and valuable advice for anyone who wants to get frisky with black women: “Don’t Touch The Hair.”

EPISODE TRANSCRIPT

So my first name is Jaelynn. I'm 41 and my hometown is Jackson, Mississippi. 

So I think I first learned about sex with friends casually and usually pretty wrong about it. And family members having fun in their drunkenness in barbershops, lots of barbershop talk. There was a lot of jokes, but things that I took seriously beause I didn't know a lot about sex. And I actually recall one instance when one of the barbers was talking about someone putting a mouse up their ass. And he essentially was using the F word in reference to who it was. And so I thought that's what it meant to be gay is that you had to put mice up your ass. But I mean, I later learned better. And at the time I was presenting as a male and identifying as well, I didn't know what gay was, but as a gay man. 

My earliest memories of expressing my sexuality was a lot of watching HBO late at night after parents go to bed and doing a lot of exploring on whatever I could find on Showtime. Thankfully we had cable. I think Real Sex was happening at that time. And then there was a series, oh Emmanuel? I think they played every single night. That may have been on Cinemax, or Skinemax is what we called it. The show was totally about Emmanuel's sexual adventures. And I don't remember a lot, but there was always a new guy, a new exploration. There was a lot of travel in it too, I think. And I was obsessed with getting out of Mississippi. It was a fem character. In retrospect I identified a lot with her and the way that she expressed her sexuality. There were like five different series of Emmanuel and it was really seductive. And so it was actually a good place to sort of learn sexual play and romance. It wasn't too hard. And there was Emmanuel Seductress. Oh, it's all coming back to me now. There were a few Emmanuels, like part three, four, and 10. I swear to God. It was every night.

I do remember one friend that we used to talk a lot and do some, you know, cautious exploration. He was on the couch under the cushions of the couch and I was on top. And we were, I was humping him as I had seen of course, on HBO. So that's sort of my first explorations and they were all around this one guy too. He was a neighbor kid from around the corner. He was my best friend. And I think he was just curious, like me about sex. He was the exact same age as I was and we were really close. 

What's really strange is I'm trying to think of my first time and I don't quite, it happened really early. There were levels of engagement with sex. There's blow jobs that happened first and then dry humping. And then of course, eventually anal sex, and vaginal sex, and et cetera. Later on, I think the first impactful had to be with another neighbor. I apparently was the little slut of the neighborhood. But it was another neighbor who wasn't always there, but only came in the summers. And I don't quite remember the first time, but I know that it was him that I did the most exploration with. For every following summer when he came until I didn't see him again in high school, he was the first one that I attempted to give a blow job. 

So I didn't really know what a blowjob was. Like sucking dick wasn't really in my vocabulary at the time. And so what does it sound like? We knew it had to do with a penis and a mouth, and so somehow we thought it was blowing. So there was some oral involved. I would get it wet and then I thought the purpose was to actually get the cold feeling on his penis. So I'd get it wet with my mouth and then just start blowing on it. And he liked it, so I guess it did work. And he is the first one where we attempted anal sex. And it was too much, particularly for me. But eventually over the course of summers, we figured out how to do it and he'd come back with more knowledge that he was getting from somewhere in Texas. I don't know where, but he'd come back with more knowledge and we'd do more exploration. 

The experience was very positive for me. The only negative was, of course both of us were Christian. And we were in black Christian society in the south, him in Texas and me in Mississippi. And so we had to hide it, our sexual explorations and felt really guilty about it. It would eventually happen that we'd go through a series of explorations. And before he left for the end of the summer, he would just stop talking to me because he got either shamed, embarrassed or something happened. But then we'd repeat the cycle the next year.

So the most embarrassing sexual experience that I've had. I was living in DC. I had just moved from the south and gotten a job as a flight attendant. I got laid off and so I needed some money. And I was doing a lot of partying, having a lot of sex with a lot of people. And one of my friends suggested, "Hey, why don't you just see if you can make some money doing it because you're already whoring." And so I thought in my mind at the time, that was a really good idea. And I had a lot of friends who were actually sex workers and they had good lives and they were rolling in dough. So they hooked me up with this person. I called and I was a little nervous and he seemed nice. And he said, "Hey I'll take you out to a really nice dinner and then we can hook up later and figure out if it's going to work."

So we go to dinner. It was a hole in the wall and he ordered food for me, it was like a rotting salad. It's really disgusting. But I was like, "Okay, this is fine." The whole time he just kept talking about himself and all the things he did. He was a fashion designer, he was a backup singer. He traveled to Paris and traveled to London. It was just on and on and on. So finally the date was over and we made it to his house, which happened to be next door to the restaurant. So he didn't make much of an effort. The house was cute, but it looked like he had inherited it from his grandmother because it was decorated in 1950s style. I was expecting something different. 

We went to his room and he was a really big boy. And I remember my friend told me, when I thought about doing it like, "He's a big boy." And I was like, "That's fine. I like big boys, love big boys".  But he was a big, really big boy. And so we got to his room and he took his clothes off and I'm like, "Yeah, this is still cool. This is cute." And then he starts talking again about like, "Oh, I sang backup for Anita Baker. And I sang backup for blah, blah, blah. And I designed for P Diddy. And I did this, I did that." And so this is going on while he's naked. And so I'm like, "Okay, well, what do I do?" And so I say, "Okay, I just need to like suck his dick." And so I start taking my clothes off. And I think the words were like, "Bitch, dance for me." Or something like, "Bitch, strip for me." And so I'm like, "Okay." I'm a horrible dancer. So I'm taking my clothes off and jerking, like I do. And I dance because I'm not a great dancer and trying to be sexy. And he's still talking about himself this whole time.

And he pulls out this wad of cash, which was awesome. And he starts balling it up and throwing it at me. And throwing it at my head while I'm trying to dance. And I'm like avoiding the dollar bills coming at my head. And he's still talking like, "I blah, blah, blah. I own this house. And I make so much money." And I'm like, "Jesus fucking Christ." So I think in my mind, "I need to get out of here. This is feeling a little unsafe." And then he's like, "Don't you want this money?" And I'm like, "Yeah, it's a shit load of money. So I'm going to go ahead and do this." 

So he turns around. And bends over and he spreads his ass. And he says, "Stick your fucking face in this." And I'm like, "Okay this is normally fine with me. But in this context I wasn't feeling it." But I was like, "Okay, I'm going to do it." And I got close. And the sides of his cheeks were leathery. And there were like, what do you call them? Dingleberries. And I'm like, "I can't. There's no way I can do this. I need to get out of here." And so I say, "I got to go to the bathroom." And I don't know how, but I got my clothes and I started running for the door. And halfway out the door, I'm halfway naked. I hear him yelling in the background, "I sang for Patti LaBelle!"

It's hard to figure out what my best move is. I think not injuring the other person is a pretty damn good move for me. I can be awkward and clumsy. And oftentimes my good sexual experiences are with people who have a sense of humor so that we can actually laugh about clumsiness. Inevitably, you're going to get hit in the eye with the elbow or something is going to happen. Or I'm going to fall. Or my hair falls off or something. It hasn't been that dramatic yet. I do enjoy sucking guys off. And getting as deep as I can and really getting into it. And it almost feels like I have a full body orgasm when it's really good. Well, I'm not sure how the guys felt about it because apparently, in reflection, I don't know whether or not they liked it or not. But I enjoyed myself.

I wish someone told me that monogamy wasn't a hard and set rule. That I could be proud to explore my sex and sexuality with as many partners as I want to. And within my own boundaries. I wish someone had told me the importance of actually having boundaries around what I want and what I don't want to do. And that fundamentally, the other person will appreciate that more because you're in your zone sexually.