Making My Friend's Day with my First Post-Breakup Sex [m/f] | 2016

I'm heading into my second year of college, and until the beginning of summer I had been dating my high school boyfriend. After summer started, I decided to take summer classes and stay at another dorm on campus while my boyfriend went back home. One thing kind of led to another (well, mostly it was him hooking up with my mom's friend which is a story in and of itself I'm sure) and we broke up.

That was in May, and even while I was going through the sadness of the breakup I couldn't help but, well, crave the dick. I love my fingers and my various once-used-to-be-useful-but-now-kinda-just-for-my-pleasure items, but they just don't satisfy me the same, especially when I suck on them.

Unfortunately for me, almost all of my friends are from the same club, so everyone knew my business with my boyfriend and was all sympathetic and no help. Don't get me wrong, I appreciated the sympathy but I sort of became "untouchable" in a sense. It was nice at first, because there were those asshats who hounded me immediately after the breakup (there was a friend of his who literally, I mean literally, texted me within an hour of us breaking up and offered his cock for me to dry my tears with), but after a while I was pretty ready to move on. I didn't want to get in a relationship, though, and I wasn't so desperate to go out and meet a stranger to fuck. I just wanted something casual that everyone else in the club seemed to have which was this weird friends-with-benefits-but-only-when-you-need-it relationship with each other. I probed around a bit, but my girl friends told me that a lot of people were afraid to be that asshole.

Anyway, a couple of days ago I finally had enough and I needed it and I needed it bad. There was a guy, Dan, who I had secretly wanted to suck his cock even while I was dating my past boyfriend (the difference though is that I didn't while dating, and my asshat boyfriend did). He was there for the summer, and I figured he may be into me, so I made up some lie about needing help cleaning my room. I figured if he would help me clean my room, he had to like me a little bit. And he did.

Dan came over to my room, and thankfully I live in one of those apartment-style dorms so I didn't have to worry about my roommate since she was in her own room.

"Uh, Allison, your room isn't messy at all," he said. I blushed at that, because I completely forgot about that part. I told him there were some papers that needed to be sorted and we halfheartedly worked on de-cluttering my desk. After I did so I invited him to take a break and sit on my bed.

I gave him a hug while we were sitting on the bed, and I figured he would surely get the hint by now. He seemed a bit tense, but I told him to relax. He seemed to get it then and picked my head up to kiss me. I kissed him back and he pushed me down onto my back, rubbing my chest over my tanktop. I needed that. I tore off my tank and bra while he took off his shirt and we got back into touching each other some more.

I rolled him onto his back and I pulled off his pants. His cock was beautiful, nice and thick. He was well-trimmed, too. I couldn't handle it. Well, I guess I did handle it in my mouth. I went down on him immediately, skipping the crap and trying to take all of his length into my mouth. The tip of his cock hit the back of my throat and I gagged a bit and had to pull back.

"Sorry," I said. "Out of practice for a bit." He was speechless. I loved it. I went back to working on his cock, getting it nice and wet with my spit. I relished the sound of his moans but always stopped so he wouldn't cum, at least not yet.

He sat up and pushed me back onto my back again and pulled off my shorts and panties. I got a little nervous then. I was so wet, which was a little embarrassing, but he got on top of me.

"Fuck, what do I do? I don't have a condom," he said.

"I, um, wait, actually," I said, not knowing how to really phrase it. "You don't need one."

"What? Are you on the pill?" he asked.

"No, um, actually I'm a virgin," I admitted, blushing. He looked a little confused and backed off a bit.

"You don't need to lie if you don't want to have sex," he said. I asserted I wasn't lying. "I know you're not a virgin. Emily said you and your boyfriend fucked real loud all the time." I blushed at that. I guess the walls were thinner than I thought. I wondered what else was said about me.

"No, you don't understand, we did it, like... anal all the time." Admitting that to him made me even wetter, and I couldn't really tell how he felt. I didn't know how he felt about anal, which is why I kept it quiet. "So you don't need to use a condom. I clean myself so..."

He kinda just hovered over me for a second, then he lifted my ass a bit and positioned his cock over my ass. He asked if I was sure. I nodded, but asked him to finger me first and use the lube in my drawer before he entered me. He seemed a little hesitant to finger my ass, so I told him to use the sharpie that I kept in my drawer and work that in my ass, too. He did so, and I asked him to mount me backwards so that I could suck his cock while he sharpied my asshole. It felt so good and I was already moaning really hard.

I couldn't wait any longer, so I pushed him off of me and asked him to fuck my ass. He obliged, lubing himself up and slowly entering my ass. He let out a loud moan as he slowly started to fuck my ass, his cock only going halfway in before he started pumping.

"Go all the way," I asked between breaths. He grunted and pushed himself in hard. The pain of his cock splitting my anus was a little more than my ex, but it felt even better. He began to fuck me harder, and whispered in my ear that he had always wanted to try anal but never had the chance. I couldn't formulate a good response as he got more into his rhythm and I could barely keep a thought together. I moaned and shouted and begged him to keep fucking me.

It felt all too quick, but he suddenly stopped, and, out of breath, announced that he was going to cum and should he pull out. No, I shouted, and backed my hips up and forced as much of his cock into my ass as possible before feeling that rush of warm cum shoot into me. It felt amazing.

I got up, and quickly grabbed a towel and put it beneath me to catch any dripping cum.

"Can you squat?" he asked. Apparently, he loved to watch cum drip out of girls. I obliged, squatting above my towel and letting him watch the cum drip out of me. I caught some with my hands and licked it. "Fuck," he said.

We sat there like that for a while, each catching our breaths. He eventually cleaned up, I cleaned up. I asked him to try to not mention my little anal secret to anyone, and he said he would keep it between us.

....I feel like he's going to tell. And I kind of hope he does.