Best of Both Worlds - Cover

Best of Both Worlds

Copyright© 2017 by TransChick

Chapter 1

BDSM Sex Story: Chapter 1 - A trans woman meets a couple for a BDSM relationship.

Caution: This BDSM Sex Story contains strong sexual content, including Ma/Fa   Consensual   BiSexual   TransGender   BDSM   MaleDom   Group Sex  

So I want to tell you about a pretty crazy period of my life. Like a lot of fun, exciting things it ultimately couldn’t last forever, but I definitely look back on the time with a big smile, and I appreciate it both for how hot it was to be a sub in a BDSM triad and for the fact that it helped me a lot. I’m in a much better place now, and I think a lot of it was because I had the space in a safe environment to sort my life out. From here, it simultaneously seems so far away and like it was yesterday.

To go back to where it started, your sex life doesn’t have to stop just because you’ve got problems, so I had gotten on the computer at the public library and posted a personal ad in a local FetLife group.

BEST OF BOTH WORLDS

Submissive trans woman seeks MF couple for fun and sexytimes. At least one of you should be dominant, and I’d love to meet up for fun with impact toys, rope, and other ideas bounded only by our imaginations. (And a safeword!) Hit me up if you want to meet and see if we connect.

Ok, so it wasn’t the best ad ever, but with a couple of sexy pics of my cute, chubby self, I sent it off into the world and hoped for the best. Life is too short to wordsmith things to death.

The phrase “best of both worlds” was sarcastic -- some people think of trans women that way, as having the basic sexy attributes of a woman but also having a penis. I probably shouldn’t have used sarcasm among folks who may not get it, but it’s not like this was a particularly well thought out enterprise on my part.

Oh, right, I should introduce myself. I’m Alanna (I picked that name myself!) and I am indeed a trans woman. I’m also a Scorpio, but I can never keep track of what that’s supposed to mean. And I’m an ENFP, which I think backs up the fact that I like too many things to stay focused on any of them for very long. Because that’s definitely me.

Once upon a time, I used to think I was lucky or something, because being trans didn’t seem like it was as hard as everyone had warned me. I’m never sure how well I pass, but I don’t get harassed like some trans folks do. I didn’t lose any jobs because I was trans, or have someone refuse to rent to me or anything. Like I said, I thought I was lucky.

But regardless, my life fell apart, and I pretty much just blamed myself. Which is certainly true, but I’ve come to realize that being trans is an intensifier for problems. All that time keeping who I was stuffed deep down inside me, trying to pretend I’m normal, it made my other problems worse. While I wasn’t dealing with who I was, I also wasn’t dealing with what else was wrong with me.

See, I had a thing. I wasn’t sure what thing it was because I couldn’t get a doctor to sort it out for me, but I wondered if it might be ADD. I had trouble focusing, and my trouble focusing tended to mean that I fucked up jobs even when I wanted to try really hard to keep them. I made mistakes, I lost concentration, everything went to shit.

I had another thing, too. I got these anxiety attacks where I kind of freaked out and can’t really deal unless I take some vistaril, at which point I’m sedated and I kind of stop thinking or even really being present. Apparently doctors are down with giving out vistaril because it’s not one of those benzo-whatevers that people get addicted to.

When my anxiety spiked, I also did this thing where I troed to avoid all my problems and think about anything else, which more or less meant that the worse things got, the less likely I was to be able to fix things. It was super helpful, as I’m sure you can imagine.

So as I was hiding from my real gender in my earlier years, I was hiding from all this other shit too. Which meant that the statute of limitations on people giving a crap about helping me solve my problems kind of expired when I wasn’t looking. So at that point I kind of owned all of it and it was an uphill battle to get any treatment. Well, any treatment that helped anyway.

And again, I don’t want to make it sound like it’s not my fault that I fucked up my life, I’m just saying that being trans and being mentally ill or whatever made everything harder.

So yeah, I lost my job and I couldn’t find another one. And I didn’t really have savings left at that point, so I couldn’t pay rent that month and the big, soulless property company tossed me out on my ass.

Being homeless basically sucked. I mean, I stayed in a shelter, so it wasn’t the living-on-the-streets kind of sucking, but it still sucked. I was sleeping on a thin mat on the floor in a big-ass room with several dozen other people. You have to be in by a certain time, lights out at a certain time, up at a certain time, and out on the street again way too early in the morning. And you pretty much have to carry all your shit with you -- if you don’t want to drag it along with you, you say goodbye to it.

Most people at the shelter were pretty decent, but there were some who caused problems, and we ended up with the cops there every couple of weeks or so. Some of the problem folks had drinking or drug problems, others just had mental problems too big for them to stay within the shelter rules. As far as I could tell, no one really helped any of these folks get real help for their problems, so they bounced in and out of shelters.

So anyway, I placed a personal ad using the library computer. Public libraries are super useful if you’re homeless. And over the next few days, I fielded various responses. Most of them were from trans chasers, of course. And, I mean, look, if you’re attracted to trans women in particular, cool. That works out. But if I’m a faceless dick with a pair of tits and not a person to you, well, no thanks. And if you’re going to want to dump my ass if I ever decide to change my genital configuration then you’re going to make a complicated decision even more complicated, which really sucks.

But anyway, since I was looking for couples, it was really easy to filter the chasers out -- if a chaser has a girlfriend, he definitely doesn’t want me to meet her. Beyond that, there were creepy dominant dudes who wanted to impress me with their domliness by ordering me around right in the first email. Yeah, that shit doesn’t work.

What does work is responding like a human being and treating me like one, too. There were a few couples in the first batch of messages who seemed promising, but a couple of them flaked pretty early on, and one of them just seemed creepy over Messenger. But I exchanged a few messages with the remaining couple. It seemed like it was worth meeting so we set something up.


We got together for coffee at a local Vietnamese place I suggested, just a simple meetup to start. It was a small place with only a few tables, and for some reason it was shaped like a boat. Everything was a little beat-up looking, so it felt like it was lived in. A lot of the local places now were overrun with hipsters, and they were either restored older places or designed to look like they were, but they were absolutely immaculate looking, which kind of spoiled the atmosphere unless you were basically slumming and you expected your quaint little spots to look like they belonged in a magazine spread. Here, there was very little decor on the walls, and it was mostly older photos that commemorated that they’d been open a long time. Judging from what the photos looked like, probably since the 70s.

Jon was tall, maybe 6’2”, and was White with a dark, well-trimmed beard that looked good on him. He was a development manager at a local tech company, and seemed to have more social skills than a lot of the computer guys I’d met. Lissa was 5’4” and pale-skinned with freckles and striking red hair. She was a project manager at a different local tech firm. They were both on the chubby side, like a lot of the folks I knew in the BDSM scene, which was great with me.

I easily spotted them from the pictures they’d sent when we messaged. They were dressed in earthtones in pretty typical Pacific Northwest casual, whereas my purple dress and black cardigan were casual, but somewhat hinted at goth influences. Now that I’d transitioned and I could wear what I wanted, I did. I didn’t go out of my way to call attention to myself, but I had my own inner sense of what I liked, and my clothes rarely looked like anyone else’s.

I walked over to join them. They had grabbed a table near the prow. “Um, hi.” I always know how to bust out a cunning icebreaker like that. Well, ok, sometimes I get shy at frustrating times. It’s pretty annoying.

“Hello! You’re Alanna? So nice to meet you.” Fortunately, Jon had more social grace than I did. He smiled and reached out his hand. I shook it, grateful for some sort of ritual to help me settle down a little.

“Hi, I’m Lissa, this is my husband Jon. Please, sit down.” Her big warm smile was disarming, and she gestured to the other side of the booth.

“Thanks!” I did indeed take a seat. “Wow, it’s great that the sun’s finally out today.” The weather, really? Nice work, fat girl. (And yes, I really do sometimes call myself “fat girl” in my internal monologue. Some of it’s internalized fatphobia, but it’s also partially a statement of self-love. As a trans woman, it’s glorious that I finally get to be a girl in real life. Even several years after my transition, it’s still something I don’t take for granted.)

“It really is. We don’t get nearly enough days like this.”

At that point the waitress appeared with tea and to take our orders. We always smiled at each other when I went there, but we couldn’t really converse -- she wasn’t fluent in English and I didn’t speak a word of Vietnamese. Neither did Jon or Lissa, so we just ordered. Lissa joined me in ordering the noodle salad with grilled pork and Jon ordered a banh mi. The menu items were numbered up on the wall with pictures, so ordering was pretty easy.

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