Best of Both Worlds
Chapter 1

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

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

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.


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.

I was also the weirdo who insisted on ordering a soda there. I have kind of a thing for diet soda. It’s a bad habit. I didn’t indulge it very often given my financial situation, but as long as I was splurging on a sit down meal (though admittedly a pretty affordable one) I decided to have one.

After the waitress left, I gestured at Jon’s navy logo shirt. “So, Mariners fan? Is it baseball season already?” I was still trying to ease into the conversation and slow my heart rate.

“Yeah.” He smiled excitedly. “They’re actually pretty decent this year.”

“Sorry, I only have the vaguest awareness of sportsball. I barely know which end of the ball they hit.”

That got a laugh out of him.

Of course, I do actually know the rules of baseball, from back when masculinity was something expected of me. But now I’m pretty done with sports. I was vaguely happy when one of my old teams did well, but not happy enough to want to watch any of it.

He rattled off some more details about that year’s Mariners team anyway. I tried to listen politely, but I couldn’t tell you a word he said. I glanced over at Lissa and we shared a bemused look. It was a guy thing and, ok, it was kind of adorable sometimes.

Finally he wrapped up, then took a beat before changing the subject. “So, what kind of thing are you looking for? I know we’re hoping to get to know someone and have an actual relationship. Is that something you’re interested in?”

“Yeah, definitely.” Ok, come on, I thought, I can do better than that. “No, um, it can be pretty hard sometimes to find a couple and have chemistry with both partners. And it’s hard to have a relationship that works at all without that kind of connection. I’m ok with meeting someone and just having fun for a little while, but yeah, if the chemistry was there, a relationship would be awesome.”

“I know what you mean,” Lissa confided, gesturing as she talked. “The first couple of times we did this, we thought, you know, we’d just meet someone. But it’s hard. Way harder than finding someone to date one-on-one. But we had someone we were seeing for a while last year, and it was so worth it, so we keep trying.”

The food was really quick. The waitress showed up with our order, complete with a can of Diet Coke and a glass of ice. They didn’t sell enough soda to bother with a fountain.

The noodle salad is pretty much what it sounds like -- a salad with lettuce, mint leaves, and basil leaves topped with rice noodles and some grilled pork that has a ton of flavor. I added the dressing and a little extra fish sauce, and I mixed it all up before diving in, and Lissa seemed to be taking her cues from me to do the same.

Jon smiled after trying his banh mi. “This is fantastic!” Vietnam was colonized by the French, and they serve their sandwiches on these wonderful baguettes. Jon’s had the same grilled pork and the sandwich comes with some tasty vegetables and a bunch of cilantro that really makes the flavor pop.

We ate quietly for a couple of minutes, but then I continued from where we left off. “As far as dating a couple goes, I’ve only done this once before, a couple of years ago. Like I said, the chemistry was hard. It was there with her but not really with him. But even for the little while it lasted, it was enough fun that I totally want to give it another try.”

“Makes sense,” Jon agreed.

“So have y’all dated trans women before?”

“We did once before, one of those times when it didn’t work out. She was really sweet, it just wasn’t quite right,” Lissa said.

“So you learned that it’s not like in porn?” I involuntarily winced a little as I asked. People who watch trans porn often have some terrible ideas about what sex with us is like.

“Oh, for sure,” she said. “We understand that it comes down to whatever you’re comfortable with. We definitely won’t ask you to do anything you’re not enthusiastic about.”

“Ok, cool. Sometimes people get some bad ideas from porn, and things can get pretty awkward.”

“I bet, yeah,” she said sympathetically.

Jon’s phone made some notification sound, so he pulled it out. It seemed like it was some really fancy huge one, maybe a Samsung, but I had stopped keeping track of new phone models some years back. He apologized to me and started whipping through the interface and typing something, though I couldn’t tell what.

While he was distracted for a minute, Lissa chuckled and rolled her eyes in a good-natured way, then followed up with, “So, what do you do for a living?”

“Well, I work as a contract graphic designer, but I’m between contracts at the moment. What about y’all?” A basic get-to-know-you question, but kind of an awkward one for me. Hopefully we could move on without dwelling on it.”

“Oh, Jon is a Development Manager at one of the big tech firms here,” she explained, “and I’m the Office Manager at a law firm. It’s a bit hectic, but I like coordinating all the chaos when I’m at work.”

Jon had just finished his message and come back to Earth with us. “And you like not having to once you clock out,” he added, smiling at her.

“Yeah, pretty much.” She smiled back.

“So, what kinds of experiences have you had with BDSM?” asked Jon.

“Well, I had a relationship with a domme that lasted several years, but it started becoming less BDSM-focused over time, and the whole thing kind of fell apart as I worked through my issues and realized I wanted to transition. That wasn’t really something she was comfortable with. Since then I’ve been to play events and such, but I haven’t been ready to try another D/s relationship until more recently, and haven’t been in anything serious.”

“Ouch, that’s tough,” he said, then took the last bite of his sandwich. Lissa and I both still had some salad left. She had stopped picking at hers, but I was still slowly working on the last of mine.

“Yeah, for sure. What about y’all?”

“Well, we definitely make BDSM a part of our lives, but it’s not like we live by some kind of elaborate protocol or something,” Lissa said. “We go to work like anyone else, eat dinner like a normal couple, and so on. But there is a subtle D/s feel underlying our lives, and sometimes we do more overt BDSM things. Usually at home, but once in a while we go out to a club and play in public.”

“Oh fun! I’ve done that before, but it’s been a while.” Which is because I can’t afford the membership fee or non-member cover charge, but it seemed a bit early to share that detail. My finances weren’t really anyone’s business until there was some reason for them to be.

I tried to move the conversation along. “How much do you practice D/s in how you run your household?”

“Well, he likes to think he’s in charge, and I like to let him,” Lissa said. She had a playful smirk on her face.

“You’re just saying that because you want a spanking when we get home, “ Jon shot back, smiling. He looked back at me, “Sorry, I try to get her to behave, but sometimes she’s just difficult. What about you?”

I blushed and looked down. “Well, mostly I just like being a good girl.”

Jon turned to Lissa. “See, girl? We could use more of that around the house.” His smiled as he said it, and I could tell that it was all in fun.

She laughed and stuck her tongue out at him.

“Oh really?” he responded. There was still some laughter in his eyes, but something more serious, too.

He looked back at me. “We’ll be back in a minute.” He climbed out of the booth and pointed to the floor in front of him. Lissa followed him out and stood on that spot, looking a little nervous, then the two of them walked off toward the bathroom.”

I had a little of my soda and fidgeted with the straw a bit as I waited, but the two of them came back after just a few minutes. Lissa’s eyes seemed a bit glassy like she wasn’t quite as present as before, and she sat down gingerly.

Jon had a satisfied smile on his face. “I’m sorry to make you wait, but sometimes these things can’t wait until we get home. I hope you can understand.”

“Um, of course.” I looked at them a bit longingly.

Jon smiled knowingly. “You miss it a lot, don’t you?”

I’ve always been pretty easy to read. “Yeah, I guess it’s obvious, isn’t it?”

“Well, if you’re interested, we can fix that.”

“Yeah, yes...” -- I almost said “Sir,” but caught myself in time. He wasn’t my Sir yet, so it wasn’t my place. Not yet, anyway. “ ... I mean, yes, I’m interested.”

“Oh good. I really like you. And Lissa doesn’t let this side of herself show in public unless she likes someone. Isn’t that right, girl?”

“Yes, Sir.” Lissa still had stars in her eyes.

“That’s a good girl.” Jon held his hand up to her face and she smiled as she nuzzled it.

“Ok. I think it might be time to get her home. Would you be comfortable with some light play next time we meet?”

I smiled eagerly. Like I said, I’m pretty easy to read. “Yes, I’d love to!” I paused for a moment, wondering whether I had been too enthusiastic. “I mean, that would be great.”

“Ok, wonderful. I’ll send you a quiz about your interests and limits, and we can use that as a starting point.” The waitress had given us plenty of space, but Jon managed to flag down the check as we talked.

“Thank you. It was really great to meet you.”

“It was great to meet you too.” Jon smiled. “I’m very much looking forward to next time.”

He secured the check from the waitress, and I reached for my wallet, but he gestured for me to put it away. “I’ve got it. Don’t worry about it.”

I got up to leave. “Ok, well thank you. Talk to you soon.”

“Yeah, talk to you soon.”

Lissa woke up just enough to say “Bye” as I left. She was clearly still pretty much in la-la-land from being beaten.

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Story tagged with:
Ma/Fa / Consensual / BiSexual / TransGender / BDSM / MaleDom / Group Sex /