Pre-Op Roommate


I was a few months away from graduating college with my Theater Arts degree when Mark, my roommate, told me he was going in for the sex change operation.

We popped a couple of beers and talked about this thing… he wasn’t sure whether he liked guys or not, he’d never done anything with them. But he liked dressing up like a woman, like acting like one, and felt like a woman trapped in a man’s body. It was weird as hell… Mark and I had been roommates since he started college just a couple of years before, and I’d never known any of this.

He didn’t think he was gay… he was going to get the surgery and become a lesbian, or something, though. He seemed really embarrassed, and asked me if I wanted him to move out.

It WAS going to be a freaky situation. Neither Mark nor I had much of a social life. I had the group from the Theater classes, and he had his marketing club, but this was they guy I hung out with most nights, eating pizza and watching TV. How this change in his life came about with me knowing absolutely nothing about it, I had NO idea, but I wasn’t gonna stop being his friend. I told him there was no need for him to move out, and that he was just as much a renter of the apartment as I was. It seemed settled.

He started the treatments just after I graduated. He had a couple of years of college to go, yet, but the apartment would still suit both of us, since I was looking for work close by. I managed to land a pretty good paying job at a local social clinic, since I had a lot of psychology under my belt. It turned out I was going to need all that training at home, too.

Mark started a program of hormone replacement therapy, and a few other chemical processes. After a couple of months of the treatment, his body chemistry was a raging mess, his emotional states would jump wildly, and he did indeed start looking much more feminine. He’d never been really built, as a guy, so it was gradually apparent that he was getting some curves… and some boobs. Not big ones, but they were there. He was going to get implants, at some point.

Even with all the female body chemistry, though, he still hadn’t undergone the major operation to alter his genitals, so he still had a pair of testicles filling him up with testosterone. The mood swings were, in large part, the two body chemistries fighting each other.

I guess I became a little distant… between getting a lot of overtime at the clinic, and not knowing how to handle his new status as a becoming “her,” I kinda kept to my room. But then there was that one day.

I came home really tired, and tossed my dress jacket over a chair, when I heard Mark crying, in the bathroom. I may have been uncomfortable with him, at the time, but I wasn’t a bastard. The door was open, and I poked my head in.

Mark was wearing a skirt and a blouse, trying to get accustomed to the female clothing. His hair had softened, and gotten a little longer, since he hadn’t cut it since before the treatments began. But his face looked like he’d been mugged by the Avon lady.

“What’s up, Mark?” I asked, leaning on the door jamb. He jumped, a little, and looked at me, huge rivers of badly-placed Mascara running down his cheeks.

“I… I wanted to try… try to look nice… and I got this stuff… and… it’s STUPID! STUPID!” He threw a handful of application sponges across the counter, and sat there crying.

I stepped forward, and examined the make-up he’d gotten. It was top of the line stuff… Mark’s folks were rich, and they apparently approved of his change, so he could afford the best makeup. But he had no idea how to apply it.

I put my hand on his shoulder… and it felt different. WAY different. Not the shoulder of the guy I would punch in the ribs when he was kicking my ass on the game system. It was softer… nicer… warmer. It was a woman’s shoulder. I continued on, though.

“Hey, it’s ok. You haven’t ever done this before, right?”

He looked up at me with that clownish disaster of a face and nodded, quieting a little bit. I smiled.

“Look… Theater Arts degree, here. I’ve done more women’s make-up than I’ve had hot lunches. Let’s clean you up, and start all over, ok?”

He smiled… and it wasn’t a man’s smile. ‘Cause when guys smile at me, I don’t get warm in the crotch. I shoved the feelings down, though… this was Mark, my roommate. I showed him how to use Cold Cream to get the makeup off, and about a roll of toilet paper later, sat him down, facing the mirror, and began to apply the makeup myself.

“Start with the base… this is a good color. Pretty close to your own skin color. It’ll smooth out lines and such, not that you’ve got any to deal with, really. Gives you a good even tone. The lady at the makeup counter helped you pick this stuff, right?”

“Yeah,” he said, watching my hands deftly coat his face in a thin layer of the powder.

“She made some good choices,” I said. I applied the blush, showing him how to accentuate his cheek bones, and the eye-shadow, which was a really sexy dark blue. His eyebrows were a little on the bushy side, but it had kind of a Brooke-Shields in the ‘80’s appeal, so we left them alone. The mascara brought out his naturally long lashes, and a deep maroon lipstick really set his lips off. I caught myself wondering if his lips had always been in that shape, or if the therapy was changing that, too.

A little powder, and some fixatives for the lipstick, and he was done… looking like anything BUT a “he.”

He gave me that smile again, in the mirror… and with the makeup, it got me a little hard. I was admonishing myself for needing a cold shower after spending time with my roommate, of all people, when he turned to me.

“Can you do something with my hair, too? It still looks too much like… well… like it’s always looked.”

“I’ll give it a try,” I said. “I didn’t do much with hair that wasn’t wigs, but it shouldn’t be too hard.”

And, really, it wasn’t… some styling gel, a couple of brushes, and his hair went from his usual unruly, parted-in-the-center mop to a gentle wave, down the sides of his face. He looked in the mirror and smiled… and I realized that I had made him look fucking hot.

“Oh, Dan… that looks GREAT!” he said, primping a little. His small, rounded breasts thrust against his blouse, when he did, and I had to start thinking about baseball. “How can I thank you?”

“Hey, I was glad to help,” I said. “I don’t like to see you upset.”

He looked down at his lap, and started to sniffle a little, again. I guess I might have had a little panic.

“Hey, hey, hey… let’s not mess up that mascara, that’s some of my best work! What’s wrong?”

“It… it’s nothing,” he said, as he rushed past me to the living room. I followed him, not sure of what to do or say.

“I’d like to know,” I said, sitting on the couch. He sat next to me… at the other end of the couch.

“I just… it seems like… you… you don’t want anything to do with me, any more…” he said, and started crying, and I felt like a COMPLETE heel.

“Hey,” I said, touching his shoulder again. Again, it was a different shoulder… not a “His” shoulder, but most definitely a “her” shoulder. He turned to me… and it wasn’t a “he” turning towards me, but most definitely a “she.”

“What?” she asked, eyes brimming with tears. I couldn’t think about him as a “he,” any more. Even though he still had some equipment between his thighs, Mark was definitely a “she” now.

“I… I guess I don’t know how to react to this… to you, and what’s happening,” I said. Honesty. It’s caused MORE problems…

“Well,” said Mark, “just… like always, right? I mean… I’m still the same person… just… well…”

“…Different,” I finished. She nodded, looking into my eyes.

“I’ve been kind of lonely,” she said, shrugging. “I mean… none of the people in the marketing club know how to handle this, and with no classes… I’ve been kind of stuck here, in the days… and at night… you don’t want to even look at me…”

I swallowed, feeling absolutely rotten. “Hey, Mark… I’m sorry. I guess I didn’t think about what you were going through… you know, with people. I’ll try to do better, ok?”

She smiled, and reached out, and squeezed my hand. It wasn’t a gesture he’d ever used before… but I liked it. Liked it because a pretty girl had just touched me.

“Man,” I said, “I’m gonna need a cold shower, or two, though.”

Mark seemed surprised, and pulled back a little. “What? Why?”

I looked at her again, and blinked. “’Cause you’re hot and gorgeous all at the same time, that’s why.”

She blushed… even through the makeup, she blushed. “I… I don’t think so… I’ve been thinking that it wasn’t working out. That I was gonna be so ugly that it wouldn't work…”

“Hey, now,” I said, and squeezed her hand back. “Stop that. Believe me, you’re beautiful. And it isn’t just the makeup, either… I just did stuff to accentuate what you’ve got. You’ve been getting really pretty… seriously. I think that’s why it’s been hard for me to… you know… be out here, and stuff.”

The look in her eyes was shock and disbelief. “You think I’m pretty?”

I shrugged. “To put it mildly,” I said.

Then, she was sliding closer to me on the couch, and her hand was on my knee, and things were about to get WAY out of hand.

“Mark,” I started. She put her finger on my lips.

“Marcie,” she said. “I’m Marcie now, Dan.”

“Marcie,” I said, trying to get used to it, “You’re one of the best friends I’ve ever had… but this is a little… kinda, you know… weird…”

“I still don’t think I like guys,” said Marcie. “But I like you, Dan.”

And then, she was kissing me, and, well, it’s been a while since a pretty girl had given me attention, and I kissed her back. And it was nice. My brain kind of turned off.

“Show me how pretty you think I am,” she said, as she unbuttoned her blouse. Her pert little tits came into view, round and soft, and I took them in my hands, and gently caressed them, my thumbs playing with her nipples. She gasped, and kissed me again… and there was no going back.

In the back of my mind, I was wondering what was going to happen when we got to her “below the waist” area, but it was a minor concern, compared with my now raging hardon. Her hand brushed over the front of my pants, and she looked me in the eyes with surprise and delight.

“You’re not kidding… I AM turning you on!” she said. In response, I kissed her, hard, took her hand in mine, and guided her fingers up and down my hard shaft. Marcie knew how to handle the equipment, she started stroking me just right, just the way a man likes it.

I let her hand go, and watched as she made the moves on her own, every stroke and caress just right. She pressed closer to me, and I leaned back on the couch, her touches on my cock feeling so good that I could do little more than lay there, and let her continue.

She unzipped my pants, after a few minutes, and pulled my raging hard cock out through the fly. She stroked it’s hardness, seemingly amazed at the look and feel of it.

“I figured you were big, Dan,” she said, as she caressed my nine inches, “but I… I never knew…”

I just smiled. “Wasn’t like it was going to come up in casual conversation, before, you know?” I said.

She nodded, eyes transfixed on it. Then, she leaned down, and kissed the tip of the head, and I moaned. I couldn’t control myself… my hips thrust upward, just a little, and she took the head of my cock into her hot, wet mouth.

My roommate was blowing me. My roommate, who was a guy a month ago, was sucking on the head of my cock. And she was good at it, too.

Her hand continued to stroke the lower four or five inches of my cock as she sucked on the top of it… slowly letting it slide into her mouth, and sucking hard as she slid off of it. Her tongue played with the tip of my dick, pressing into my piss-slit, and wriggling, just the way I like it.

Soon, she was bobbing up and down on me, as my hands caressed her back and hair through her clothes. My cock was throbbing, and I was moaning with the sheer pleasure of it. She was going to make me cum in her mouth.

But she stopped… just stopped, after a few wonderful minutes, and looked me in the eye.

“Dan?” she said, her eyes filling with tears, “Will you… will you make me a woman? A real woman? Your woman?”

There wasn’t enough blood above my neck to choose what to have for dinner, much less make a decision about this. The brain below my waist, though, knew just what to do.

“Fuck yes,” I said. Marcie smiled at me, clutching me, tears wetting my shirt.

“I want you SO bad,” she said. “I have… I have since this started… I just… I was afraid…”

I kissed her. I kissed her hard… partially, to shut her up. Partially, because I really wanted to.

She stood up, and took my hand, and led me to her bedroom.

We’d never really gone into each other’s bedrooms, while we’d been living together. We did a lot of stuff together in the living room, but our bedrooms were kind of our sanctums, where nothing would bother us.

Marcie’s bedroom wasn’t really feminine… it wasn’t masculine, either. Like it’s owner, it seemed to be in transition. Not decorated much, with soft blue tones, for the most part. She led me in, and I closed the door behind us.

She looked at me, and bit her lip, a little. “You know, Dan… I haven’t had the final surgery yet… I’m… I’ve still got a…”

“Yeah, I know,” I said.

“How do you want to… you know…”

“Take your clothes off, Marcie,” I said, as I stroked my cock, leaning against the closed door. “I don’t care what you’ve got. I want you.”

She almost shrieked, as she smiled… and peeled off her very sensible outfit, very quickly. And nothing I saw did anything but turned me on more.

Her skin was soft, and clear, and her breasts, though small, were round, with pert little nipples. She had a woman’s curves, and a woman’s softness, and a hard cock sticking up over smooth, shaved balls.

She had no body hair at all… probably part of the treatments she’d been having, or a preparation for the surgery to come. But her cock was hard, for me. And somehow, that turned me on, too.

I peeled out of my clothes, as well. She came over to where I was standing, and helped me out of my pants; taking my belt in her hands, and dropping down to her knees, dragging my pants and underwear down to my ankles.

I stepped out of them as she leaned forward, and took my cock in her mouth again. She moaned as she took it deep… and gagged, as she took it all. My hands fell to her hair as she choked herself on my big dick, over and over… and I could feel her cock rubbing against my shin as she did it.

She even swallowed around the head of my cock as she took it into her throat. No girl I had ever been with had done that, and Marcie was doing it because she wanted to, not because I asked for it. She was sucking my cock better than I had ever had it sucked before; her warm, moist, soft lips sliding up and down my shaft like a seasoned professional whore, bringing me closer and closer to cumming.

Before that happened, I pushed her head off of me, and looked down into her eyes.

“I want you,” I said.

She nodded, and got up, onto her bed. I knelt on the bed next to her, as she thought.

“I… I want it on my back,” she said. “I want you to take my cherry while I look at you.”

“I’ve got no problems with that,” I said, as I helped her over onto her back. She spread her legs, and lifted them, taking her knees in her hands. Her thighs were spread wide for me, and I could see, under her dangling balls, the little pink rosette of her ass.

I knew she was a virgin, I knew I hadn’t had any contacts with risky partners. She had lubricated my cock with her spit, liberally, and I was leaking pre-cum. I knelt between her thighs, and rubbed the pre-cum around the head of my cock onto her hot, tight little asshole.

Her cock still pointed straight up at me, and somehow, that made it better. I knew how excited she was, there was no denying it.

“I’m ready,” she said, her eyes wide, looking into mine. I slowly started to apply pressure… feeling the heat of her ass slowly, SO slowly, engulfing the head of my dick.

Suddenly, I felt her relax, just a little, and the whole head of my cock popped into her. Her eyes went even wider, and she clapped both her hands over her mouth, to hold in the scream. I stopped… afraid I’d hurt her horribly.

“It… It’s ok,” she said, when she could speak, after a minute. “I knew it would hurt, but you’re so big… more. Give me more?”

I happily obliged. I continued to shove my big cock into her ass, until she had it all… all nine inches, firmly wedged into her virgin shitter. Virgin no more, that is. I’d taken her cherry… she was mine.

I slowly started to slide it out, and then back in, as she closed her eyes, and hissed from the feelings… pleasure, or pain, it didn’t matter to me, at the moment. I wanted her… wanted to spill my seed in her, wanted to make her mine.

“Yes… fuck me,” she hissed. She let go of her legs, and reached down to fondle her own cock. As I fucked her faster, and harder, she began stroking herself with one hand, and stroking her balls with the other.

I took her legs up onto my shoulders, and started to really pound her ass. I knew it wasn’t going to take long, with the expert attention she’d been giving me with her hand and mouth, so I determined to make it intense.

“Oh, Dan… oh, GOD… DAN…” she called, just as her cock started to shoot. The spasms through her groin and ass were a feeling I’d never expected, never anticipated… it made me shout, and cum up her ass, hard.

She milked the cum out of her cock as her ass milked my cock, totally and completely. Slowly, I withdrew my softening member, and laid down next to her.

She turned towards me, and I kissed her again, sweat covering both our bodies.

“Can… can we do that again, sometime?” she asked. “I… I really liked it.”

“Sometime?” I asked. “We’re going to do that again a lot. That was the best sex I’ve ever had, Marcie… and I think it’s only going to get better.”

She just clung to me, then, and her soft cock, slippery with her cum, rubbed against mine. As exhausted as I was from that historic fuck, I started to rise, a little.

“I never knew it could be like this,” she said, as she rubbed her face in my shoulder. “I… I think I’ve wanted you for a long time,” she said.

I shrugged, and caressed her soft, shapely ass. “I think I’m going to want you for a long time,” I said.

We’ve been together for a while, and it keeps getting better. She hasn’t had the surgery yet, and she might not. I’ve gotten used to taking care of her needs, a little, and it gets more fun as time goes on… but that’s another story.

Report Story

byDracthyus© 20 comments/ 178432 views/ 90 favorites

Share the love

Also in this series

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartbarzulboy, gin0aki56 and 88 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous01/14/19


This was one of the best stories I've ever read! Continue it PLEASE!

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

Show more comments or
Read All 20 User Comments  or
Click here to leave your own comment on this submission!

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

Refresh ImageYou may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: