Sister's Roommate

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"Just hold up there."

"Oh, I'm sorry. I thought you wouldn't mind."

Wouldn't mind! What?

"Um it's a bit fast, don't you think?"

"I'm sorry. But my boyfriend will be here in half an hour so we don't have much time."

"Boyfriend?" I shook my head. "Uh ... If you have a boyfriend then ..."

"It's ok. He said I could be with other women."

I was going to have to make a little business card to hand out to people to explain to them that I was NOT A FUCKING WOMAN.

"That's great but this is too sudden for me. And I just got home from a date. And right now I really need to go wind down. But I think you're nice. I think, you're so nice. I'd love to spend some time with you and maybe after we've known each other for a bit longer ..."

"I understand. You're shy." She smiled and then she kissed the palm of my hand. "You take all the time you need, sweetie."

I got the hell out of there. What was that about? No, don't answer that. I didn't want to fucking know. Like her boyfriend would actually be ok with my dick going in her just because she thought that I thought I was a woman. These fucking people are all crazy and here I thought I was fucked up.

"Hi." I said as I entered my room.

"How'd it go?"

"Good."

"Where's Kim?"

"Home."

"Why?"

"Elana, I'm not going to bring her back here for sex on the first date."

"You could if you just tried harder."

"I don't want to talk about it. We agreed to go on another date so it was a good date."

I had a choice in front of me. I could either go all the way across the street and maybe even have to go farther down the street to take a shower; or I could just take a shower here in the girls dorm in the bathroom that was right there on the hall. They did say I was welcome to it.

I was being cautious as I approached the bathroom. I was ready to change course the moment someone objected. Then, wouldn't you know, it was that girl Kelly who walked up to me. I guess they let her out of jail. She came and stood in front of me while I had my towel, soap, and other stuff in hand. It took a second for me to recognize her actually because she didn't have her pasty makeup with black lipstick on. I started to back away from her.

"Hey. Can I talk to you?" she asked in a much gentler tone than she'd used before.

"Not really. I'm busy."

"I just wanted to say I was sorry for before. I know what you're going through."

No. No, she did not know what I was going through. But I had to acknowledge her apology and make peace.

"I hope they weren't too rough with you."

"It's ok. I can handle it." she said. "I'm tougher than I look."

Right, which is why she was crying like a baby when they put her in the cop car.

Anyway, I let her know I needed a shower and she moved out of the way. I passed her and as I did she came close to my side.

"You know, we might make a good fit. I mean, we're sort of compatible if you think about it."

"Ok. I'll ... keep that in mind."

She smiled at me and walked off.

As I took a shower I played with all the gender vocabulary in my head for a while. That might sound sick but my other option was imagining myself fucking my sister. That girl Kelly was just messed up in the head. So she figured that since she was trans to a man and she thought that I was trans to a woman that we could hook up. If I did that with her, in objective reality, we'd just be a normal heterosexual couple. The only difference would be some delusion she had in her head.

Just a side note but I had to say it. The girls sure had a nicer shower than the guys did.

I went back to my room and got myself ready for bed and made a plan for how I was going to manage the women on the hall. I was going to have to address this stupid transitioning crap somehow.

"Hey" my sister said. "Can you come here?"

"What do you want?"

"Get in." she said as she offered a place in her bed to me.

"Why?"

"I want to finish that movie. Hop in."

"That's ok. I saw the whole thing."

"Just get your butt over here."

She started the movie and fast forwarded to the part where the main guy was in a bar talking to a guy with one leg and then four or five guys all started shooting at each other.

Of course, I couldn't care less about the movie. I was more interested in the fact that my sister was wearing a long tshirt and if I had to guess, NO PANTIES. I did my best to hide my erection but my boxers just weren't up to the task.

My sister had her arm around me and she was pulling me close to her every other minute of the film.

How could this be both heaven and hell at the same time? If I wasn't careful I was going to cum again just by sitting here.

"Are you going to have a boner all the time?" she asked me and I was startled by the question.

"I told you, it's automatic."

"Do I need to call Kim to come over and take care of that for you?"

"No. Just ignore it."

"You're not getting off to this movie, are you?"

"No."

"Then what?"

"Nothing. And I'm not the only one having an automatic reaction either. So unless you want me to point out your thing then just leave me alone."

"What thing?"

"I'm warning you."

"Warn away. What thing?"

"Your ... nipples are very hard, don't you think?"

"What are you doing looking at my nipples?"

"What are you doing looking at my dick?"

"The thing is so big, no one could help but notice it."

"Well, same to you. You asked me to get into your bed and you expect me not to see your nipples getting hard?"

"Well here." She sat up and pulled her shirt off. "Get a good look."

What was my next move? I looked her body over. I had been wrong about her wearing panties. She did have some on but they were little more than a gstring.

It dawned on me that it would be really nice to be able to tell her how I felt. Would there be a way to do that? No. If she knew she'd explode at me. But maybe I could tell her in a way where I knew what it meant but she didn't. Or maybe I could tell her such that if she was ok with it then it would mean one thing but if she was against that sort of thing then it would mean something else.

In my mind I was searching for words. What could I say? I needed more time and I didn't have it.

"Finished?" she asked. "Or do you need to pull your thing out and take care of yourself?"

"I can't do that. You'd be grossed out."

"This is your room, Paul. If you need to do that, don't let me stop you."

I called her bluff. I let my cock slip out of my boxers and I started stroking it in front of her. I expected her to tell me to stop that, or at least get off her bed if I was going to do that. But she didn't. She watched me. The longer I did that the more her body, specifically, her hips started to move with the rhythm I was going at. She bit her bottom lip and a hand came to one of her breasts.

I slowly reached out to her. I wanted to give her ample warning and plenty of time to reject the movement. My left hand went to her other breast. I squeezed it a bit and she locked eyes with me. I was touching her breast and she was letting me do it. I gently pinched her nipple and her body had a reaction. I started to be able to smell her.

This was way, WAY too much for me. I brought the head of my dick close to her tits and I started to shoot cum all over her chest. That was amazing. That was really something special. I had the coolest sister in the universe. Well, I thought I did for about ten seconds.

"Sick, Paul. You put your stuff on me. Gross. What's wrong with you?"

I tried to respond verbally but I had nothing.

"Get a towel. Hurry up." she commanded.

"Sorry." I was able to finally say.

"I said hurry up. Fuck! Cumming on your sister! You're mental, you know that!"

Yeah, I knew that. Thanks for pointing it out and making me feel like shit.

I put my dick away and helped get her cleaned up. She put her shirt back on and I sort of felt ashamed of what I had done so I was going to go to my side of the room. Before I could get away my sister yanked at my arm and ordered me back to the bed. She reversed the film a little ways and we started watching it again.

I will say this, my hard on was gone. I wasn't all the way soft but my hard on was gone. She was watching the movie but I was actually very sleepy. I dozed off a bit. I opened my eyes and the film was almost over. I closed my eyes. I opened my eyes again and the computer was off and the room was dark. I closed my eyes. I just let myself snuggle next to my sister.

At some point in the night something happened. I think my sister masturbated while I was laying next to her. She was trying to be stealthy about it but she was moving enough to wake me up. I didn't move. I didn't know exactly what she was doing but if I had to guess she had some of her fingers going in and out of herself. The hand that was not on pussy duty came over to me and in an awkward manner tried to feel my dick through my shorts.

She finished a lot sooner than I thought girls could reach orgasm and then she settled in next to me and we both drifted off to sleep again.

I awoke first the next morning. For just a split second I didn't know where I was and I didn't know who was next to me. Then it all came back to me. This was my sister and I had my hand under her shirt and I was cupping one of her breasts. My morning wood was pressing up against her ass. This was going to have to stop. I couldn't be around her all the time or I was going to have a permanent hard on.

Very carefully I detached from her and got out of her bed. She didn't wake up from what I could tell. I threw on some weekend clothes and bounced. I went to get breakfast and when I returned to my room I found my sister working out. I don't know what exactly she was doing. It wasn't yoga but it was something derived from yoga. Anyway, I didn't know the particulars. I did know that if I stayed in that room and just watched her do that stuff I was going to cum on her again and she'd made it clear she didn't appreciate that so I had to get out of there.

I grabbed some text books and went to the lobby to read. Before I was able to get too far into the subject one of the girls from the hall came and sat next to me. She was asking all of these personal questions and she eventually got around to asking when I knew I wanted to be a girl.

I started to set the record straight with her and before I knew it a group of them including Kelly and that girl that tried to rape me were all gathered around me and hanging on my every word. The rapy girl's name was M'kalee by the way (sorry, don't know how to spell it). We called her Allie for short.

"So when everyone talks about the spectrum, they usually envision a line. And they usually think that female is at one end of the line and male is at the other end. But really, if you think about it, why should those be the stopping points. The line can be longer than we think and that's where I am. You know how there's infrared and ultraviolet? We can't see those colors but they are out there. Well, right now they don't have a word or a designation for what I am but that doesn't mean I can't be the equivalent of infrared. And for all I know there might be the equivalent of ultraviolet out there somewhere. Some lonely person who just wants to be loved and accepted for who she is but is forced to live a life between these two end points when she's really outside."

Internally I was laughing my ass off at these stupid people but they were eating it all up. So I made it official that even though I was outside their normal understanding of gender, I did still like girls and no, I was not a girl myself. I was perfectly happy with male pronouns because those were the limits of human language and I wasn't going to college to change anyone else. I just came to learn. I didn't come to instruct.

I hoped that was the end of people thinking I was a tranny. In a way it was but they seemed to all just not hear or not understand what I was talking about. They paid lip service to me not being a girl but then they still treated me like I was one of their girlfriends. They felt like they could just hug me or kiss my cheek. A lot of them felt like they had the right to just run their fingers through my hair. What was that about? They didn't do that to each other. Why were they doing it to me?

After lunch I went and met up with some friends of mine to play basketball. They asked me where my skirt was. Ha, ha, it wasn't fucking funny anymore. So then I had to correct them but thankfully I was able to use far fewer words.

"The truth is, I've got two dicks, so I'm more male than you." For the guys, that was all I needed to say. They caught on right away that I was just playing the system to get a long.

That was a good game. My side lost but it was a good game and it was close. We were all hungry after that. Then some asshole had to come and be a jerk around us.

We were all eating lunch in peace and talking about who we thought would win such and such preseason game. Then some gay guy comes over and starts hitting on me. No, I don't mean he was punching me. I mean he was trying to ask me out on a date. The guy would just not take no for an answer.

When he tried to sit next to me and kiss me I lost my cool and I decked the faggot right in the mouth. The piece of shit fell to the floor of the cafeteria and I was about to start beating the piss out of him. All the other guys jumped up and grabbed me to hold me back.

So for the second time in three days I was answering questions posed to me by police. This time it looked like I might be the one they handcuffed. Even though I had all my friends there telling the police that I acted in self defense, the other guy was pulling the gay card and saying that I had targeted him.

But I was lucky. The cafeteria, like most of the buildings on campus, had cameras. On the one hand, I didn't like the loss of privacy, but on the other I sure was glad the video made it clear that we repeatedly told the gay guy to go away. It was clear as day that I only punched him after he had come into physical contact with me on his own volition. That was sexual assault and the school had a zero tolerance policy.

PSA: if someone tells you not to touch them, DON'T touch them.

By the time I went back to the dorm, word had already spread. Again my sister was angry with me on the surface but concerned for me inside. I took a shower in the girls bathroom and then got ready for my second date with Kim. I noticed a couple of girls who lived on the hall happened to get peeks at my dick when I was reaching for my towel.

Kim came and picked me up and then she drove me out to a spot between two lakes. It was very pretty with the sunset reflecting off the water. The end result of the date was that we did kiss a little bit. She made a move like she wanted to touch my cock through my pants but then I guess she got scared and it didn't happen. We just kissed and when it started to get late, she brought me home.

"Another bust?" my sister asked me when again I returned with no Kim in tow.

"I got to kiss her this time."

"That's good. Is that all?"

"We talked about it and she's now almost officially my girlfriend."

"Almost?"

"Yeah, but she said if we kept seeing each other then it might happen soon."

"Oh, thank heaven. So now maybe if she's taking care of you, then you won't need to jerk off in front of me any more."

"I thought you said this was my room."

"It is and if you need to do that I won't stop you. I'm just saying, you'll probably be happier with her doing that for you than you having to do it yourself."

"One thing that bothers me though."

"What's that?"

"Well, I wasn't very good at kissing. But I guess I'll get better with time and experience."

"Are you asking me to help you practice?"

"No, I was just mentioning that I wanted to do better. ... But I wouldn't turn it down if you were offering."

She turned away from me and sat on her bed. She took in a deep breath and then she called me over to her.

"Just kissing. Nothing else. Keep your hands to yourself."

"Really? You're going to let me kiss you?"

"Just to help you out. Don't go getting a crush on me. That's what Kim is for. I'm just going to let you practice so you can do a better job with her."

Was this real? Was this really happening? Did she mean it when she said just practice or was she giving me a window for more? Dare I think, dare I hope that maybe she felt for me what I felt for her?

"Wait. I think I should warn you;" I said; "if I kiss you, I might need to masturbate tonight."

"I said I wouldn't stop you."

This was so dangerous but I couldn't not take her up on it if she was going to let me kiss her.

I got closer to her. I sat on her bed next to her. She turned her body towards mine. She was looking at me. Then she looked down at my body. She was interested after all. I smiled and she smiled back at me. I got closer. I closed my eyes and I was just about to get the kiss to connect when her palm went flat up to my nose and she pushed me away.

"Gross, Paul. You were actually going to kiss me? I was only joking with you."

"Yeah ... I knew that. I was just ... seeing how far you'd go."

"You're really starting to worry me. You need to get your head on right."

I went back to my side and just tried to play it off like I wasn't affected. It wouldn't look very manly of me if I put my head into my pillow and started crying. I couldn't do that even if it was what I felt like doing.

I didn't want my sister to see me like that so I left and went to the lobby with my textbook to read in a place where I wouldn't be tempted to fuck my sister. While I was reading there, Allie came into the lobby in just her pajamas. She saw me and decided to come over and sit next to me.

She was talking about something. I was only half listening. Then she started laughing and she reached over to me, grabbed my arm and put her head down to it as she laughed some more.

"I mean, can you blame me?"

A question. What was the question about? I just shrugged.

"Thank you for understanding."

I just nodded and then she hugged me.

"You're such a good listener. I wish my boyfriend listened as well as you."

Then she gave me a kiss on the cheek and let me know I could go to her room any time I might need to talk. I thanked her for that. She kissed me on the cheek again and looked like she didn't want to leave right away but she eventually sighed and left.

My classes the next day were all very early so I needed to get some sleep. When I got back to my room I ignored my sister's attempts at getting my attention when she changed into her night clothes. For a few moments she was naked so of course I had to look at that. But then I got hold of myself and I just hid under my covers and forced myself to get to sleep.

About an hour later, I had actually been sleeping for some time. I was awoken by the feeling of someone getting close to me. I half opened my eyes and my sister was getting into bed with me. I was too sleepy to really understand the implications of this.

I awoke the next morning with my sister next to me and without an immediate memory of why. Again, I awoke with no boxers on. I couldn't let her know that. This was a school day and my classes started early so I had no time to deal with this.

On Monday the teachers actually started teaching. Finally. Real college had begun and I hoped that before everyone knew it, we would all be so wrapped up in studying that there'd be no time for my sister. I had a good plan. I was going to date Kim and if not her than someone. Elana as going to date some guy and then we'd be back to just being brother and sister. Regular, boring siblings.

After classes that day I had lunch with Kim. She wasn't finished for the day yet but she had time to see me for lunch. I was resigned. I could accept the reality around me. Sure, I had these feelings that I couldn't control and should not give into but I had it under control. I could manage it. Later that day I played basketball and had dinner with my friends again and all the gender talk was getting left out. Good. I was just a regular guy like everybody else.