The greatest sex with my roommate


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I fucked my classmate and want to tell you that story. 2020 sex stories with GIFs, best sex gif with captions, xxx porn gifs, fucking classmate.

Disclaimer: a bit of romance and emotion in this one, so if you’re looking for pure erotica, you’ll have to wait until the end. But hopefully it’s worth it!

As a 24 year old physician assistant student in Chicago, I had to try to make ends meet however I could. When my roommate moved out to take a job in another city, I had to get a new roommate to pay the bills. I interviewed several less than desirable candidates and just about settled on one when a female emailed me in search of a place to live. I hadn’t considered a girl for a roommate, but, yeah, why not. This, I interviewed her and she seemed neat, responsibleness, and normal so I agreed to let her take over the lease.

Her name was El. She was attractive, but nothing that I felt I couldn’t resist. I mean, I went out with a lot of cute girls. I thought El was of Middle Eastern descent, but I wasn’t sure. She had dark eyes and dark complected. She had an athletic build with broad shoulders and somewhat of a booty on her. There were quite a few tattoos on her forearm and she had some piercings. El worked as a server and bartender at several places in the city. She seemed rather private, but that was okay by me; I just needed her to be a decent roommate and pay her share of the bills. I also got the impression that she had a tough life so far and maybe made some interesting choices up to this point. But that was none of my business.

i fucked my classmate

For the first couple months, El pretty much kept to herself. She did her thing and I did mine. My buddies kept asking me if I was banging her as I maybe had a bit of a reputation for being with quite a few girls. Without sounding obnoxious, I do alright appearance-wise. But with El, nothing could be further from the truth. She wasn’t interested in that at all. Just roommates. There was an occasion where I brought a girl home for the evening, and the next morning El kind of gave me some grief about it. But totally in a joking way. El actually had a guy overnight once and after he left, I asked her to give me the thumbs up or thumbs down on his performance. She said she rather would have read a good book. We both got a laugh out of it.

Eventually, I got to know her better. And I soon became an admirer. She just did things that you respected. She was neat, ate super healthy, took great care of her appearance, religiously went to the gym, spent quiet time reading, and just seemed to have her act together. She was always impeccably dressed. Makeup and nails were always done. Always. But she could also dress down and look great in a Chicago Bears sweatshirt and little short shorts. She could also talk football with more insight and intelligence than any of my friends. Was I becoming attracted to her? I guess it’s fair to say yes.

So about after three months into our arrangement, I finally talked El into going to a bar that I frequent and meet some of my friends. She was personable and could easily talk to my buddies, which I guess was a skill she had to possess as part of her job as a bartender. That night the bar had karaoke and after quite a few drinks, we were all amusing ourselves by taking turns singing.

We talked El into it and she sang Adele’s “Someone Like You” and just knocked it out of the park. I mean, the girl had some pipes. So when you have a talent like singing, naturally you get attention. And in this case, my buddies were all over her after that. And I didn’t like it. It was the first time I realized I was becoming attracted to her. She noticed I got quiet and was watching her as one of my friends had his arm around her and was chatting her up. She looked at me and mouthed, “What?”

i fucked my classmate

“Nothing,” was all I could say. But she kind of flashed me a mischievous smile like she sensed my jealousy. She soon broke away from their attention and we went home together. But damnit, I think she started to pick up on what I was thinking and I didn’t want that.

A few nights later, El went out to her bars with her friends. I got a text from her late saying she was too drunk to drive and was wondering if I would come pick her up. I stayed in to study and I needed a break anyway, so I agreed. When I got to the bar, she was outside waiting with a group of her friends. Guys and girls. When I pulled up, El didn’t immediately get in. It was almost like I was set up to be on display for them so they could check me out.

They were trying to get me to come in and drink with them, but it was just a friendly invitation, nothing serious. El just let them check me out before hopping in to head home. It made me wonder what she said to them prior. Was she interested in me? I let it go because I certainly couldn’t bring it up to her.

Over time we became closer and closer. Out of respect, neither of us brought home a girl or guy to spend the night anymore. It was like something was happening between us. But that all changed one evening when I came home from class. I was going to ask El if she wanted to grab something to eat. I heard her in her room and I knocked on her door and called out her name, but got no response. I took the liberty of opening her door. She was in her room getting dressed. She had her earbuds in which is why she didn’t answer me calling out to her. All she had on was a t-shirt, nothing else. Thus, when I saw her and we made eye contact, I also saw essentially her secret…she had boy parts. El was transgender.

She screamed, “Brian, what the fuck!” and tried to cover up. But she knew I saw.

I said, “Oh my god, I’m so sorry,” and quickly shut the door.

I was stunned. Stunned wasn’t even the word. The only thing rolling through my head was WTF, WTF, WTF. I sat down on the couch and just tried to think this through. But a lot of things were starting to make sense. The pieces were starting to come together.

I sat there in silence for about an hour. El came out of her room. Since it was quiet, I assumed she thought I had left. She saw me sitting there and went into the kitchen to get a spoon and yogurt out of the fridge. I tried to talk to her, “El, I am so sorry. I thought you heard…”

She quickly cut me off, “Brian, you fucking invaded my privacy.” Then she headed quickly back to her room.

I followed, the whole way calling her name. “El, please listen to me. El? Just let me explain.”

She was standing in her room with her back to me when I caught up to her. “What?! Fucking what?!” Then she drew in a deep breath and started to sob.

I consider myself a caring person and I certainly cared about her at this point. It broke my heart to see her in this much pain because I was sure this entire journey had been difficult enough without having this happen. I got straight to the point, “El, I apologise. But you have to know it doesn’t matter to me at all.”

i fucked my classmate

She quickly responded between sobs, “I’ll just move out. I’ll be gone tomorrow.”

Hearing this crushed me and I carefully approached her. I was right behind her and I debated touching her, but thought it was worth the risk. I put my hand gently on her shoulder to comfort her. “No. Absolutely not. There’s no reason to move out. Please don’t do that.” I waited for a response, but got none; she was just shaking from crying. I continued, “Even if you moved out tomorrow, nobody will ever find out about this. It’s completely between us no matter what.” I kept gently rubbing her shoulder in hope to make her understand that I was sincere.

“Just leave me alone. Just go, please.”

Defeated, I gave her shoulder a squeeze and left the room, but not before saying, “I’m going, but please talk to me when you’re ready.” I felt horrible for her and maybe myself to a degree because I thought I just lost a close friend. It was also becoming apparent to me that I was developing strong feelings for her.

I didn’t see El for three days after that. She either stayed somewhere else or timed it to be there when I was gone. But her things were still there. She didn’t move out. I was cautiously relieved every time I came home and saw her stuff was still there. Yet, I missed her.

That Friday, three days after the incident, I was getting ready to go out and watch a Cubs game at the bar with my buddies when El came home. I was surprised and relieved to see her. We exchanged uncomfortable “Heys” and maybe a little small talk. El finally said, “I uh, I rented a movie and was wondering if you’d want to watch it with me. But it looks like you’re going out, so…”

“No, not at all. I have no plans. Yeah, I’ll watch it with you. What movie? Maybe we can order some food and watch it.” I was babbling, but I was just so excited that she wanted me to join her. Total relief, which surprised even myself.

We ordered pizza and I secretly texted by friends saying I couldn’t make it. One responded back asking if I got a better offer to “hit” my hot roommate. At that point, I didn’t care what they thought.

El and I ate and put the movie in. Things started to seem to be getting back to normal. She sat on one side of the couch and I on the other. I felt good about where this was going. But El is full of surprises and about half way through the movie, she paused it and moved closer to me. I was a bit confused. She asked, “Why don’t you want me to move out?”.

Her question caught me off guard. I hesitated with an adequate response. I certainly couldn’t tell her that I was falling for her for fear of screwing up the appropriate roommate relationship, especially given what just went down between us. “I…just…uhhh… I just don’t want you to.” Brilliant response.

She kind of laughed and said, “I know. You said that. But WHY?”

I was between a rock and a hard place. I began fidgeting nervously. I couldn’t look her in the eye. I felt like I had a knot in my throat and no words would come out. And I was embarrassed that I was so chicken shit that I couldn’t tell her.

She sensed my struggle and said, “Relax. It’s okay.” Then we went back to watching the movie. I felt like an idiot. I felt like I lost an opportunity to be honest with her and even myself.

But I noticed El didn’t move away from me. About five minutes after restarting the movie, she leaned her head toward me and rested it on my shoulder. Although a bit of a surprise, it felt so good when she did that. I turned and put my cheek on her head as if to affirm that her action was certainly wanted. When I did that, she laced her arm around my arm and held onto it. We watched the rest of the movie like that.

After the movie was over, I shut the TV off and she looked up at me and simply asked, “Are you sure about this?” We both knew what she was referring to.

I had to come clean and express my real hesitation, “El, I’m not gay. I’m not even sure that in bisexual. I’m so messed up because I’m pretty sure I’m hetero, but I want you so bad.”

El reached up and held my cheek and said, “No, that’s perfect. I don’t want you to be gay. I want you to be the man and I want you to treat me like your woman.” What she said made total sense to me. She then reached up and softly kissed me, which I gladly returned. It felt so right.

We kissed for about five minutes when she said, “We probably have a lot to talk about, but we can do that tomorrow, okay?”

i fucked my classmate

I was disappointed that the night was ending so suddenly. It was like she was teasing me. And it frustrated me that I knew I was going to be beating off tonight thinking about my transgender roommate, but I told myself to be patient with her.

El got up and went to the bathroom. I went to bed, still a bit frustrated. But after about 20 minutes, El opened my door and came in. She had a t-shirt and panties on. She said, “I didn’t say the night was over, just that we’d talk more tomorrow.” With that she pulled back the covers and got into bed with me.

I was nervous and wondering if this was really happening. And certainly hoped I knew how to handle this situation. But my apprehension was soon relieved when El started kissing me again. It all became natural. Hand and lips were exploring each other’s bodies. I loved kissing her neck and listening to her little moans. It was definitely her Achilles heel. She started pushing my shorts down. She stripped off her t-shirt revealing her smallish breasts to me.

I wanted to enjoy them, but she, in her excited state, moved down under the sheets. It didn’t take her tongue long to begin teasing me with licks, graduating to sucks, all over my cock and balls. She didn’t suck dick like a girl. It wasn’t a chore. She took her time and obviously enjoyed the teasing process. So did I. Finally, she took me into her mouth. So warm and deep and with the perfect amount of suction. Slowly tracing her lips up and down my shaft. Now it was my turn to moan and squirm. But she knew what she was doing. She knew how far to take it, then ease off again.

Finally, she popped her head out of the covers and worked her way up to my lips. The kisses weren’t soft anymore; they were pure lust. Two tongues that couldn’t seem to get enough of each other. But she broke the kiss and said, “I’ll be right back. Gotta get something.”

A rubber? I wasn’t sure what she was getting. But when she returned, she slid her panties down revealing a hard, but small cock. She was only about four inches fully hard. It was in a odd way incredibly cute.

I discovered what El went to get from her room. She squirted a large glob of lubricant on her hand and transfered it to my raging, desperate cock. She stroked up and down, teasing me as she did, “There we go. That’s what you need. We have to get you nice and slick for me. I don’t have a condom, is that okay?”.

i fucked my classmate

She was just teasing me and she knew it. “Yeah, that’s okay,” I panted. Damn, she was good at this. I could have cum in her hand, but I was so anxious to try anal sex. I’d never done it that way before. I’d heard stories, but had never experienced it for myself.

When El was done teasing me, she put some lube on her add and swung herself over the top of me to ride me. She said, “Last chance to back out of this.” Again, more teasing.

“Please,” I begged, “I want to be inside of you.”

“Mmmmm, you do. Poor baby. Let’s see what we can do about that.” And with that she lined my cock up to her ass and lowered herself down on me.

When I entered El, I immediately knew I was in trouble. The warm, wet incredible tightness felt so good. Too good. She breathed out in deep gasps and whimpering moans which only enhanced my excitement. She worked herself slowly up and down, but soon picked up the pace. Her little tits were grazing across my bare chest and her long hair was all over my face. She would occasionally, between moans and gasps, reach down and kiss me as she fucked my brains out. Suddenly, she interlocked her hands with mine and sat up on my cock. She ground her hips in a circular motion around my pole.

Finally, while gripping my hands hard, began a forward and backward motion of grinding. She went crazy by doing this. She was a little dirty talker too. With her eyes tighly closed and her ass working me over, she kept repeating, “Fuck my pussy, fuck my pussy, fuck my pussy.” I thought that was insanely hot and I also made a mental note of it Her little cock was on my stomach and it was leaking her precummies like a faucet, making a big slick spot on me. I loved it. I loved it all far too much. I’d like to say I was some great lover, but truth be known, I was just trying not to cum.

Finally, I had to tell her, “El, I need to stop; I don’t want to cum yet.”

She reluctantly stopped and it wasn’t a moment too soon. I told her, ” I want to make you feel good too.”

“You already are.”

“No, I want to go down on you like you did me.”. This surprised her, but she was like, oh, okay since you’re offering.

She rolled off me and put her arms above her head. She looked so sexy and seductive as I lowered myself under the sheets to suck my first cock. I couldn’t believe I was doing it, but I wanted to please her so much.

i fucked my classmate

As I reached her cock, I began k**ding around her stuff like she did me. In the moment of truth, I took her precum-coated little cock in my mouth. I took two inches and was immediately struck by what I was feeling. It was hard, yet spongy soft. It was warm and throbbing and I love the way it reacted to my mouth going up and down. I licked and sucked and enjoyed the intense sensation of my first cock. I think it was safe to say that I was pretty much addicted to sucking cock from that moment on.

I looked up and El was watching me do this. She had a huge smile on her face. I kept my eyes locked on her and said, “I want to make you cum.”

El explained, “Well, it’s probably not going to happen that way, but I know how it can happen. I want you back inside of me.”

She didn’t have to tell me twice. I crawled up her body and she again lubed my cock up. With the remaining lube she grabbed her little cock and began to stroke it while offering her ass, I mean her pussy, to me. I slid slowly back into El. It was as good as before. El moaned and began stroking herself intensely. All she said was, “Don’t be shy, fuck me hard.”

I picked up my rhythm and thought I would return her dirty talk. “God I love fucking your tight pussy.” She looked up at me in pleasant surprise that I called it her pussy.

“You like your new pussy?” She was stroking herself even harder now.

“Oh, yeah. You’re going to take my cum. I’m going to breed my new pussy.”

“Yeah, breed me!” she said through clenched teeth. “Cum in my pussy!”

I was fucking hard and fast and was just about to cum. “I’m going to get you pregnant now.”

“God yes shoot your babies in me!”

i fucked my classmate

I started cumming like a volcano eruption. It tore the roof off as I filled my new girlfriend with my cum.

The dirty talk and my orgasm set El off as well. She didn’t cum a lot. It was more like a dribble, but she got her cum too. Then she grabbed my ass and held it firm to her while saying, “Stay inside of me. No reason to rush out. Stay in me, baby.”

We fell asleep together after the greatest sex of my life.


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