[MF] The time I fucked my lesbian friend

Jen and I had been friends since we were in middle school, and this story took place during our freshman year of college. Jen was a lesbian and it wasn't a secret. She was always a tomboy and was very open about the fact that she liked girls even in our early high school years back before it was as accepted as it is now. She exclusively had girlfriends and to my knowledge had never so much as kissed a guy. Jen was Dominican, tan skin, short, petite with medium sized tits and a little bubble butt, and always kept her dark hair short on top, buzzed on the sides, and parted to the side. She always dressed in pants or shorts and t shirts and was truly just one of the guys. I couldn't deny that she was sexy in her own way, but obviously kept that to myself and never expected to do anything about it.

Jen came to visit me at college one weekend and the two of us went out to a party. We both got really drunk and both hooked up with a couple of girls, but had no luck in going home with either of them. We got back to my dorm and my roommate was out. He had a girlfriend on campus and would regularly sleep at her place but sometimes he would come back at 3am so there was no real pattern to when he would be back and for that reason I knew we couldn't crash in his bed. I put on basketball shorts, took off my shirt, and laid in my bed then I tossed a pillow and blanket onto the floor for Jen.

"Fuck you dude. You think I'm laying on this hard ass floor while you lay in a bed?" Jen said

"What? You think I'm going to lay on the floor?" I said while laughing

"What happened to chivalry?" she asked with a smirk

I burst out laughing. "I don't think that applies to our relationship, no offense."

"Alright fine, let me just sleep in bed with you."

"Fuck fine, but if it's too cramped you're the one who's moving to the floor, not me." I said

Jen made me turn around while she changed and when I turned back she was in a baggy t shirt and black basketball shorts. She turned off the light and climbed into bed with me. We both laid down on our sides facing the same direction so that we could fit in the small bed. Picture a spoon position but we weren't cuddling or touching each other.

In the silent darkness all I could think about was the girl I hooked up with that night and how badly I wished I could've fucked her. Instead now I was laying in bed with a half hard dick and a bad case of blue balls. A few minutes later Jen shifted to get comfortable and her ass grazed on my dick. She stopped moving almost immediately after coming into contact with it and then after a few seconds of silence she spoke.

"Is that your fucking dick?" she said

"Yeah, sorry. I didn't mean to." I said and I fumbled around trying to flip my dick up into the waistband of my shorts.

She rolled over to face me and we were inches from each other.

"Can I see it?" she said

I laughed in her face "What the fuck are you talking about?"

"I asked if I could see it" she said

"Yeah I heard what you said. But you're kidding. I'm not showing you my dick. You're going to punch me in the balls or something if I show you." I said

"I'd never have the balls to mention this if I wasn't this fucked up, but even though I'm not attracted to guys I'm just curious. And it's not like I'm going to go hookup with some random dude. Besides, I just want to see."

I hesitated for quite a bit.

"Well?" Jen prodded me.

I didn't say a word, but just pulled the drawstring to my shorts and slipped them down just enough so that my cock was out. Jen leaned over and flipped the lamp on my nightstand on to get a better look and proceeded to stare at my cock like some kind of alien object.

"Does it hurt?" she asked innocently

I laughed at her again "Hurt? Why would it hurt?"

"I don't know man, I just figured it would hurt after a while if it was that hard."

"I mean yeah, if you stay hard after a while it can get a little achy, but I'm not even that hard right now so I'm good." And I pulled my shorts back up.

"You're not that hard? It gets bigger than that?" she said with a shocked look

"It's not that big Jen." I couldn't help but keep laughing at her

"Lemme see it again." she said

I pulled my shorts back down and now the situation was getting really hot, at least to me. Having her ogle my dick like this was making all my blood rush to my cock and I could feel it pulsating in the head of my dick. I watched Jen's eyes widen as it grew to it's full size. Without thinking I gripped my dick and started stroking it slowly. Jen looked at me briefly but then moved her eyes back down to my dick and was fixated on what I was doing with my hand. A few seconds of this and I saw her hand slip into her shorts and she was biting her lip. I couldn't believe this was happening, I felt like I could cum any second, but wanted to hold off as long as possible.

"Hey do you....." Jen started and then stopped

"What?" I stopped stroking.

"I mean can I...." she stopped again but reached forward and replaced my hand with her own and gave my dick a hard squeeze that made me groan which in turn made Jen chuckle.

She clumsily tried stroking me, and I placed my hand on top of hers to guide her in how to do it. She looked at me with a clearly nervous face but then slowly moved her head down to my crotch.

"You don't-" but before I could say anything else Jen had the head of my dick in her mouth and I was completely speechless.

She gave me a pretty pathetic blowjob for a minute, but any blowjob is better than no blowjob. She stopped and came back up to me and then sat up to take her shirt off. Her tits were a decent sized for her frame and had just the right amount of hang to them. She proceeded to take off her basketball shorts and laid on her side again and presented me with her ass. I reached my hand down and felt her pussy and was shocked at how wet it was. She shivered at my touch. I gripped my cock firmly and rubbed it on her slit and just before I pressed into her she said "Hey. Gently please." I just nodded even though she wasn't looking at me and I pressed just the head inside of her. Jen let out a loud gasp and I simultaneously groaned. I waited a second to let Jen get used to me inside of her and then she started to push her ass back onto me prompting me to go deeper. I fucked her with slow and shallow strokes because I didn't want to hurt her, and after a minute or so I reached around to rub her clit. I couldn't tell if she came or not, my guess was no, but I was far past the point of no return.

"Jen, I'm going to cum. Where do you want it?" I grunted in her ear

Without answering she got back between my legs and started sucking me until I sprayed everything I had into her mouth. She gagged and coughed a little bit, but didn't let any of the cum drip out. She took my dick out of her mouth and gulped down my cum with a disgusted look on her face.

"Jesus. Girls actually like that? What the fuck." she said shaking her head

I burst out laughing and then slowly let the reality dawn on me that I had just fucked one of my best friends. We got dressed quietly and both went to sleep. We never spoke of it again and wordlessly agreed it would be just an experience that we shared and it didn't need to be more than that.