Russian Roommate

Author’s Note: This is my first story like this, but I plan on making it a series. I love to write, and will be basing things off real things that happened to me. This story is loosely based on my college experience. Feel free to let me know what you think in the comments!

---

Going into college, I had a bit of a secret. No, it wasn’t the fact that I was gay, which you could tell from a mile away. It was that I already knew my roommate.

You see, at this college, a prestigious Catholic university, there were strict rules about freshmen roommate assignments. You were supposed to be paired up randomly in order to promote, as they put it, “social learning.” I said, fuck that noise, and went about trying to find a loophole.

I spent my summer before my first semester working on social media to find somebody who would be going to the same college as me, was a man (no co-ed housing in Jesus land) and, maybe, was gay.

I managed to find a Facebook group with other incoming freshmen, and started to chat online with some guys via posts made in the group. Finally, some other guy decided to post, “Any Other LGBTQ People?” and that thread is where I started really finding leads. Unfortunately, no one seemed to have any ideas of how they could get a room assigned instead of being random. No excruciating circumstances to be found. I talked to at least three gay guys who all said they’d love a gay roommate because they’d feel more free to be themselves, and that’s great and all but I really just wanted to not have to deal with a total stranger. I didn’t care what the guy was like, I just wanted to know his name before we walked in on the first day. Social anxiety, it’s a bitch.

I decided to make my own post in the group. I didn’t want to seem too desperate or obvious, so I decided to post some interesting facts about me, and invite other students to post the same underneath in the comments.

My post read, “Hey everyone, why don’t we share more about ourselves to see if we can make some friends before the year starts! My name is James, I’m from a small town in Pennsylvania, I play the violin, I’m the oldest of 4, I’m majoring in Biology, and I speak Russian! Tell me about yourselves below!”

Out of all of that, I hadn’t expected that the Russian part would change my life. I studied Russian all through school, and happened to just be really good at it. My grandfather was from Moscow, so maybe it was just in my blood. But, as all the fellow students took turns blowing up my notifications posting about their boring hobbies and whatever random places they were from, I noticed I had a notification about a filtered message. I went into the spam section and realized a guy from the group who had liked my post had messaged me. His name was Danyl, and his profile picture was of a car, how very charming.

He said, in Russian, “How are you?”

I replied in Russian also, “I am well, how are you? You’re a freshman too right?”

He took a while to respond, but when he did, he simply replied with, in English, “Where did you learn Russian?”

“In school lol” I said back instantly. So much for not seeming desperate.

“I am from Russia, I will be studying in the United States for the first time this Fall.”

Wow, that’s so cool, someone who could actually help me learn!

“That’s awesome,” I messaged, “how is your spoken English?”

“Bad. I do not speak it at home. I am nervous.”

I felt bad for the guy.

“Well, I could always help you out a bit, if you’d like. Your written skills are great so far! When we get to campus we can meet up!”

“What do you look like.” He asked.

I realized my account was pretty private, so he likely only saw my profile pic which admittedly was me in sunglasses and a big hat, which blocked my hair and took up most of the shot.

I decided to send him a picture of me at Pride in Philly this last year. I was in tight jeans, showing off how slim I am. My pale face and arms were washed out by the bright pink shirt I wore with the words “Love is Love” blasted across the chest. It also was a crop-top, so you could see my stomach which is very flat, hairless, and narrow.

“You are a boy? Or a girl?” he asked.

I blushed at this. I purposely sent him this knowing Russians can be homophobic, but I did it as a sort of litmus test. I know that with my longer dark hair, and my lack of any facial hair I looked young, but sometimes people did confuse me for being a girl.

“I’m a boy lol. I’m just gay.” I pushed further.

“Okay.” He answered.

I didn’t really know what to say to that, so I just didn’t reply. I assumed he wanted to stop talking, but then the next day he messaged me with a picture of himself.

“Since you forgot to ask for it” he said in Russian.

He was wearing sunglasses in this picture, standing outside on a clearly dreary day in very plain clothes. His hair was buzz-cut length, closing in on shaved, and he had a very square jaw. The picture breathed heterosexual. It was hard to judge, but it looked like he was at least a foot taller than me, maybe 6’4”, and slim, but not skinny. And yet, he was hot. On top of that, his sandy colored hair was a very cute trait. His lack of smile was not.

“Nice picture,” I responded.

“I have a question.” He said.

My anxiety hates those words.

“Yes?”

“Do you think they would let us be roommates, since it would help me with my English?”

Wow, this man really came into my life and answered my prayers, I thought.

“Why don’t we email housing and see what we can do?”

We ended up sending a joint email to the housing department, who was reluctant at first but eventually caved as long as we did not tell people we had been given a special accommodation. Danyl and I were officially roommates.

We started getting to know each other over messages, and he told me all about his life in Russia. He wasn’t a particularly exciting dude, but I was fine with that. Up until about a month before move-in, we would just have daily getting-to-know-you convos. I was fine with this, and did not push for anything more. It was he that threw me for a loop one day in early August, less than 25 days until we’d be living together.

“Do you plan on bringing men over to fuck you?” he asked.

I mean, duh, I thought. But that might not be a good answer, so I decided to be a bit less harsh.

“I wouldn’t do anything that would make you uncomfortable in your own room,” and I was telling the truth.

“But you let men fuck you, they go inside you not you in them?”

“That is a personal question Danyl.” I put my foot down there, thinking he’d stop.

“I think you are very girly looking, barely boy at all.”

That stung a little, but at the same time, my dick was pressing against my pants with that message. He turned me on the second he made me feel feminine, and I was getting the feeling he’d likely keep going if I instigated it.

“Oh yeah? What about me is so feminine?”

“You have women’s hips, small waist, girl hair, and you dress like girl. And you let men fuck you.”

I was a little stunned, but insanely turned on by how much he was degrading me.

“I have never let a man fuck me.” I replied. I wish I didn’t say that. Somehow I think that came off as a challenge.

“But you would, because you would never be the one fucking them.” God he was getting bold out of nowhere.

“Does that bother you?” I asked.

“No.” was all he said.

“Okay.”

Then we didn’t talk again for a couple days. I was going out and buying everything I’d need for my dorm including new clothes. I was in the mall, and happened to pass the women’s section in my favorite store. I noticed the panties, a few of which were lacy and extremely feminine.

I did it without really thinking. I grabbed my phone, snapped a photo and sent it to Danyl with the comment, ‘should I get these :P’ . I was telling myself I wanted to make him laugh, make him think I was not taking what he was saying seriously, but part of me had other ideas.

He answered immediately, “Get them. They would look hot on you. You’d be even more of a girl. Since you’re already a sissy.”

Fuck. I’d never been called that before but it was making me insanely horny. I decided to buy them with the rest of my stuff, and rushed home to put them on.

This was the moment of truth. I put them on, over my smooth ass and below average cock that was rock hard, and stood in front of the mirror. My slim body and wider hips really did make me look feminine. I decided to risk it all, and too a picture of myself in the panties, and send it to Danyl. I sent it with “I got them for you”

Waiting for his response would have been stressful if it hadn’t taken less than five seconds.

“Faggot” was all he said. My heart broke, because I thought he meant it in a bad way, that he was grossed out by me.

A few seconds later, before I could respond, came the photo of his cock.

I should mention that I had only fooled around with a couple guys so far in my life, mostly head and handjobs, so my perception of dick was based on that and of porn. I would say his dick looked straight out of a gay porn.

It was huge, he took the picture from the perspective of his face, looking down at his dick while he was sitting in a chair. It was hard, and with his other hand he was pushing it down so it was parallel with his legs. It reached almost to his knees, it was very veiny, and uncut, with foreskin completely covering the head despite being erect.

“Wow. That looks huge.” I said back, unsure of what to say. I wanted to say a million things but had never considered I’d get this far.

“25cm” he replied. A couple seconds later he said “show me your pussy”

After looking that up and finding out that equals over 9.5 inches, which is 5.5 inches bigger than my dick, I sent him a photo of mine.

“No faggot, I don’t ever want to see your tiny dick ever again. I want to see your pussy.”

After getting over the embarrassment, I sent him a pic of my ass. “I’m sorry sir” I said.

“Good girl. You need to shave your legs before we move in. I do not like hairy girls.”

“But Danyl, I’m not a girl, and you’re not gay are you?”

“No faggot I’m not gay, but you’re going to be my girl while we live together, while we’re alone.”

‘What does that mean?” I asked, both scared and so horny it hurt.

“It means I’m going to fuck you whenever I want, you will dress like a girl, and you will do whatever I say.”

I stared at that message, wanting to tell him to fuck off, that I wasn’t a girl, and preserve my manhood. But my throbbing dick told me to reconsider. Before I even had a chance to reply, he messaged me again, this time with a screenshot.

It was a post, drafted so not posted yet, in the group for all the incoming freshmen. It was the picture of me in the lacey underwear.

“No, omg please do not post that.”

“Then you agree to be my bitch?”

“Yes.” I replied immediately this time.

“Good girl.”

He logged off with that and left me reeling. I was being blackmailed, but it was so hot that I actually loved it. Gosh, what was wrong with me? Was I really this much of a faggot?

***

The next morning, I went about my day as usual, trying to focus on getting ready for my classes. Bio wasn’t going to be an easy major, and I needed to make sure I was prepared.

I went back out shopping, and while I was in the mall’s bookstore, I got a message from Danyl.

“What are you doing today?” he asked. Very normal and casual like last night never happened.

“Just shopping for books before school starts. How about you?”

“I am also shopping today. Would you like to see what I got?”

Uh oh.

“Sure.” I said, shielding my phone screen from the view of the other customers around me.

He sent the photo, and my jaw dropped. He had bought women’s lingerie, entirely red, with a lacey bra but a solid front to the panties.

“I got them in a few colors.” He said.

I was now completely hard in the store.

“Wow that is so sweet of you.” I said, trying to seem appreciative to this boy who was showing me so much interest. I’d never felt so sexy before, or so pursued. Although, he really didn’t have to try at all given that he could just blackmail me. I guess he wasn’t trying to be kind, maybe he was just feminizing me even more. Either way, I liked it.

“I am sending you a list of things to buy before we move in. Do not forget anything on the list or the picture gets posted. Message me when you are done.” He said, and sent along with it a photo of a handwritten note. It was in English, but was difficult to read. I managed to figure it out;

Chastity cage. Makeup. Nipple pumps. Dildo. Hair removal cream.

Well, that list was both simple and alarming. I went to work on the makeup while at the mall, feeling confident that my gayness was obvious enough that no one questioned why I was looking for lipstick that matched me. The hair removal cream was easy too. The rest, well, you had to be 21, (I think?) to get into a sex shop in my state, but I didn’t really want to go to one anyway, so I decided to turn to the internet. Within two days, I had it all.

I ordered a pink chastity cage that was pretty small. I realized he’d likely want me to wear it often, so I needed something that would be hidden under my clothes. I spent a lot of time on Reddit reading about people who did this for fun (how could you have fun without touching your dick?) and learned about pretty much everything I’d need to know.

I sent Danyl a picture of everything from the list laying on my bed, together with another fem outfit I bought online that looked like a maid’s outfit. Corny, but cute I thought.

“Good girl. Daddy is excited to meet you. Only a couple weeks left until you’re my bitch full time.”

And with that he sent me another photo of his dick, this time with his foreskin being pulled down. It didn’t quite completely uncover the head, but I could see that it was pink, and thick.

“Yes daddy I can’t wait to be your sissy. Your dick looks huge, I don’t know how well I will take it,” I said both being honest and wanting to stroke his ego.

“Then right now, fuck yourself with the dildo. I want to see your pussy getting stretched.”

I had never actually put anything bigger than a finger in my ass, and neither had anyone else. And I knew I had limited time. I pulled out my Vaseline, and rubbed it up and down the dildo. It was only about 6 inches, which was still maybe two inches bigger than my dick.

I got another notification, him saying “and I better not see your faggot dick”

Shit. I had to put on the chastity already. I was so nervous, especially since my dick kept getting hard at the thought, how was I supposed to get it on? Then I remembered reddit. I quickly went to the kitchen and got a glass of ice water. I went back to my room, locked the door, and dipped my cock and balls into the glass. It worked pretty much instantly, and I took advantage of how tiny it made my dick to shove it into the chastity device. Before I even knew what I was doing, and a few pinches later, my dick was locked into a tiny pink cage. I looked at myself and felt my dick getting hard, but the cage made it painful, and even though I was still aroused, I didn’t get fully hard.

I turned my attention back to the dildo. I knew I had to work fast, so I stuck it to the hardwood floor of my room, set up my phone to record, and lined it up with my hole. Without much thought, I pushed my whole weight down onto it.

My whole body was screaming in pain for a second as I felt about half of the toy go inside me with nothing to prepare me. I could see my face on my phone screen, and it was a face of pure pain. I realized I still had my shirt on, and trying to distract myself from the pain, I went to the trouble of taking it off, exposing my skinny and smooth body. I accidently rubbed my nipple, and it sent chilled down my body. I felt my hole relax a bit with that. I was careful not to show my armpits too, the only place with hair besides my legs and pubic area.

I decided to bite the bullet and plunged myself down onto the toy balls deep. This hurt, but much less than it did first going in. Knowing that this video would be sent directly to Danyl, I forced myself up, and then back down. I did this over and over, filling up at least three minutes of video before I noticed my dick was leaking precum. I was actually enjoying this.

“I am your girl, sir, I can’t wait for you to fuck my pussy,” I said out loud, surprising myself.

I decided to end it there before I said anything else. I couldn’t believe how into this I was getting. My hole was virgin, and I was begging a random man who was still living in Russia to fuck my ass. My ass, which I referred to as my pussy.

I hit send.

About five minutes later, as I was cleaning things up and packing away my things, I got the message back. It was a video of him jerking his dick, with a view from his phone on the table in front of him. The video cut out his face, but his huge dick took up most of the screen. You could see his huge bush of public hair, hairy legs, and a thick happy trail on his stomach. It was a short video compared to mine, but I put on my headphones to listen while I watched.

“Good girl,” his deep, masculine voice said in Russian. “You will be a perfect slut for me and my big dick. Keep your cage on until we meet. I want updates, daily, until then. You are not a man, and with me you will be called Jess. Yeah, baby girl I’m going to get you pregnant.” And with that, he came. His cum shot out in ropes all over his stomach.

I looked down at my caged dick, wishing I had jerked off before putting it on. Technically I knew I could take it off and just put it back on for whenever he asked for a picture, but something inside me loved that I was submitting to this man.

I messaged him back with a picture of the keys to my chastity device. “These will be yours soon.”

“They’re mine now.” He replied. He added “you can only take it off to shave, which I expect you to remain clean shaven.”

“Yessir.” I replied, not knowing that I would be repeating that a lot going forward.

(End Part 1)