“If you’re sure... I don’t want to pressure you or make you feel like you owe me.”

 

“Tell me what you want,” I said. “I can’t promise I’ll do it, but I’ll at least consider it. And I won’t judge you for it.”

 

He was silent again. Then: “All right... promise not to laugh or freak out?”

Two First Times

by Trismegistus Shandy

This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 3.0 United States License. So are my last several stories posted here, although I forgot to put the CC license notice in some of them.

We’d been taking it slow, at my request. This was our sixth date, and it was only on our fifth that I’d let Will touch my breasts. But I was pretty sure I was ready now. When he took me home after dinner, I invited him up to my apartment.

I made a pot of decaf coffee — we’d already had plenty of wine with dinner — and we sat down on the sofa. We talked about the movie we’d seen for a while, then I got cups of coffee and returned to the sofa.

“You’ve been really patient with me,” I said. “But I think I’m ready now.”

“If you’re sure,” he said, taking my hand in his, “then let’s get started. Do you want to talk about how you want to do it, or just wing it...?” He kissed the back of my hand.

“Let’s... let’s take it slow, okay? I haven’t had sex since — some traumatic things happened. And now — I think I’m recovered, I think I’m ready now, or I wouldn’t have invited you in. But maybe — we could pretend this is my first time, and all that other stuff never happened. Could you do that?”

He closed his eyes for a couple of moments, and when he opened them again, he said: “Kathleen, I’m honored that you’ve chosen me for your first. Remember, you can say ‘no’ or ‘stop’ at any point, and we won’t go any farther. I don’t want to do anything you’re uncomfortable with.”

“Thank you,” I said in a small voice. “Let’s — um — let’s not undress all the way until we’re in the bedroom, with the lights out, okay? And let’s keep it kind of plain vanilla the first time... no fancy positions or anything. It’s all new to me.”

“I’ve heard that it can be easier for women, their first time, if they’re on top. It give you more control over how fast things go... maybe makes breaking your hymen less painful, I’m not sure. Is that okay?” He was stroking my thigh as he talked.

“That would be fine,” I said, gasping a little as he got close to my crotch. I took his hand and guided it to my breast.

“Before we turn off the lights in there,” he said, unbuttoning my blouse and gently kissing the tops of my breasts, “we should probably spread an old towel or something over the middle of the bed. Since this is your first time, there’s going to be a little blood.”

“I’ve got an old tattered T-shirt, will that do?”

“Sure.”

Soon we moved to the bedroom, coffee forgotten after only a few sips. I took the old T-shirt out of its drawer and spread it unnecessarily on the bed. Well, maybe not unnecessarily. We could toss it aside and be rid of the wet spot. He turned off the lights, and only the dim glow of my phone charger and the street lights seeping in around the blinds illuminated us as we removed the rest of each other’s clothes and laid down.

Afterward, I said: “Thank you. That was wonderful... you were wonderful.”

“So were you. Did it... did it hurt when we broke your hymen?”

“A little,” I fibbed, playing along. He had really gotten into it. When I said we should pretend this was my first time, I just meant I wanted him to be slow and gentle.

“Do you want to get rid of the bloody rag before we go again? If you want to go again, that is. We don’t have to.”

“Sure,” I said, rolling aside to get off the damp T-shirt and tossing it onto the floor near the hamper. “You’ve been really good to me. Can I make it up to you? Is there something you want to pretend next time, like we pretended this was my first?”

He was silent for a long moment. Then: “If you’re sure... I don’t want to pressure you or make you feel like you owe me.”

“Tell me what you want,” I said. “I can’t promise I’ll do it, but I’ll at least consider it. And I won’t judge you for it.”

He was silent again. Then: “All right... promise not to laugh or freak out?”

“I’ll try my best, if you promise to be patient and listen when I tell you... why I haven’t had sex with anybody in a long time.” I wasn’t quite ready yet, but I thought I would tell him. If we were getting this serious, he deserved to know.

“Then... could you pretend like you used to be a man, but you got changed into a woman by a witch or a magic necklace or alien abductors or something? And you were freaked out by it at first, but you’ve been a woman long enough that you start being attracted to men, and we’ve dated for a while and you’re finally ready to have sex?”

I admit it, it took a supreme effort to keep my promise and not laugh.

“Of course,” I said. “Just give me a minute to get ready. Hmm, maybe if we’re pretending like this is our first time, we should get dressed and go back in the living room to start over?”

“Sure.”

A few minutes later we were sitting on the sofa again, with fresh cups of coffee.

“It looks like we’re getting serious,” I said, taking a sip. “But before we go any farther there’s something you should know about me.”

“What is it?”

“Eight months ago, I was a man.”

He looked me up and down. “You’re transgender? That’s fine, I don’t have a problem with that. I never would have guessed; you look perfect.”

“Kind of sort of,” I said. “It’s more complicated than that. I didn’t feel like I was a woman in a man’s body, or whatever. I was fine being a man. But... things happened, and here I am.” I took a deep breath. “So, back in May I took a vacation from the job I had at the time. I went hiking and camping in Yosemite. I used to do a lot of that... maybe this summer we can do some more, but I’m not sure... anyway. My third night out, I went to sleep in my tent and woke up — somewhere else.

“I was lying on a bed or stretcher or something. I was naked, with no sheet or blanket or anything, but the place was warm enough that I didn’t feel cold. I had an oxygen cannula in my nose, an IV in my arm, and a catheter in my penis, and there was some kind of apparatus strapped to my head — I couldn’t see what it looked like. And I couldn’t move, though there weren’t any visible restraints. My body just wouldn’t do anything but breathe. I couldn’t control anything but my eyelids.

“After I’d been awake for a while, someone came in and approached my bedside. And they weren’t human, or even humanoid... I’m having a hard time remembering what they looked like. I think I was probably drugged, so I’m not sure how reliable those memories are. But they had a lot more than two arms, or tentacles, or whatever those appendages were... anyway. They made some noises that might have been speech or might have just been involuntary like a cough or belch, I couldn’t tell.

“They came and went — there might have been more than one of them, but I only ever saw one at a time. I slept and woke several times, and then one time, I woke up with a different body. This body.

“I freaked out, as you can imagine, but I could still only move my eyelids. I slept and woke a couple more time, and then I woke up again — in my sleeping bag in my tent, in the same campsite as before. And I could move. But when I sat up, I realized I was a woman — it hadn’t been a dream.

“When I hiked out of the park, I found out over a week had passed. I was several days late getting back to work, not that I could have gone back like this. I wasn’t sure what to do — I was still in shock. It had taken me four days to hike back to where I’d parked my car, instead of the three it had taken on the way out — not because my stride was slower, although that was part of it, but because every little while I’d just fugue out, staring down at my body in disbelief for a few minutes before I shook myself and made myself keep walking.

“By the time I got to my car, I thought I was recovered enough to drive. I went home and took stock. I thought I wouldn’t be able to get access to most of my money; the bank wouldn’t believe I was me. I wouldn’t be able to pay rent, so I’d be homeless in less than a month.

“I spent some time on the Internet researching ways to get new ID, and things like that — trying to find a way out. I thought I might disappear for a while — a plausible few months — and show up again saying I’d gotten sex reassignment surgery. But I checked, and I not only didn’t have the same fingerprints as before — I didn’t have any fingerprints. And I’d lost too much height and weight for surgery to be a plausible explanation anyway, not for people who knew me well before.

“Then a couple of days after I returned home, there was a knock at my door. I didn’t answer — whoever it was, I didn’t feel like talking to them. But then someone called out, ‘Mr. Derby, we know you’re in there. And we know what happened to you. We can help.’

“So I opened it up, and there were a man and woman in suits, looking grave and sympathetic. They told me I wasn’t the only person those aliens had abducted. They’d set me up with a new identity if I’d let their doctor examine me, and answer some questions about what I’d seen and experienced. I was a little afraid they’d disappear me and experiment on me, but if I didn’t get new ID I was looking at being homeless within a couple of weeks, so I took the risk. And they kept their word. I found out some interesting things when they examined me — aside from the fingerprints, the aliens left out several vestigial organs when they made my new body. I don’t have a hymen or an appendix, for instance. And no belly-button; this body wasn’t grown in a womb.” We’d made love in the dark, so he hadn’t seen my belly yet.

“They set up the new ID they’d promised, and I was interviewing for jobs a week later. I started this job at Y-Tech and met you a few weeks after that.

“Once I stopped holing up in my apartment, and started going out and meeting people, I realized I was attracted to guys now. I was in denial about it for a long time — you remember I wore only pantsuits for the first few months we worked together, and I didn’t start wearing skirts until recently? It’s taken me a while to admit that this is who I am now. I’ve... not just gotten used to being a woman, I've gotten to like it... and I want you to take me the rest of the way. The aliens made me female, but I want you to make me a woman.”

Okay, that last bit was kind of cheesy, but I could tell it was the right thing to say. He was more turned on than I’d seen him yet.

“Kathleen, it doesn’t matter to me who you used to be. I see the beautiful, confident woman you are now, and I’m overwhelmed that you want to be with me.”

We were in the bedroom and naked a minute or two later, and this time wasn’t quite as slow or gentle, though he wasn’t rough by any means.

Afterward, he said: “Thank you for being so accepting of my fantasy, and playing along so well... that was a great story to make up on short notice. The last time I shared that fantasy with someone, she thought it was weird, and she broke up with me not long afterward; I haven’t told anyone else since then.”

In response, I took his hand and placed it on my belly.

“What do you feel?”

He ran his fingers along my belly. “Smooth skin, a little fat and a decent amount of muscle...”

“Any sign of a belly-button?” And I turned on the bedside lamp.

Thank you for reading. Please leave a comment, even if you're reading this months or years after the story was posted; I keep reading new comments posted on older stories. I can't improve if I don't know what parts of my stories worked or didn't work for people.

I'm looking for beta readers to give feedback on a Twisted novel of almost 41,000 words. I've also got a stand-alone science fiction novella (around 21,000 words) which needs beta readers. I'll serialize them after I get feedback from beta readers or fail to get any volunteers to beta-read it. Anyone volunteering to beta-read one or both of these stories should respond by private message to this post.

Meanwhile, I'll probably post another short story in two or three weeks.

I recently did an illustrated version of my short-short story "Silent Squee", which appeared on Zapper's Twisted TG Files. Some of the other illustrated short-shorts on that site are R or X rated, but mine is G.

Four of my novels and one short fiction collection are available from Smashwords in ePub format and from Amazon in Kindle format. Smashwords pays its authors better than Amazon.