I tend to have more guy friends than girl friends. I’ve heard a million times that it’s because they all want to fuck me, and that’s occasionally true. I have no issues having sex with my friends if it’s handled correctly. Know your boundaries and all that.

Occasionally, I also want to have sex with my male friends. Typically, I abstain in order to avoid any potential issues that arise from someone becoming emotionally involved. Other times, I know I could probably get away with a hookup or two.

One of these times was with a friend of mine that I’ll call Ollie. Ollie used to love to bitch to me about various hookups gone wrong. One thing he refused to do was go down on a girl. He just refused. I assumed it was because he was bad at it.

One day he was griping about striking out the night before. For whatever reason, in his very drunken state, he had wanted to do anal with the girl. He took her to his place. They fucked. And, while still half naked in his bed, she suddenly got up and left. He thought it was because she didn’t want to do anal. I’m pretty sure it was because she came to her senses.

Not that he was bad looking, it’s just that when he was drunk he could be over the top. Paired with him requesting anal… I guess she just was over him that night.

“Maybe you’re just bad in bed,” I suggested.

He glared at me. “I think she just didn’t want to do anal, what’s up with that?”

“Some girls just don’t like it,” I shrugged, “just like you don’t like to eat girls out, cause you’re bad at it, but you can just pretend you don’t like it. People understand that sex is different for everyone.”

“I’m not bad at eating girls out,” he told me. Of course that’s the takeaway he got from my statement.

“Okay…” I told him. “I just figured you don’t do it cause you can’t get someone off that way. It’s not a big deal.”

He was pissed but he kept it together. “I bet I could get you off, and I know you would like it.”

“I mean… it’s not…” I started.

“Let’s make a wager then?” He asked. “I will get you off and then you have to get me off… with anal. Cause last night sucked.”

I laughed. “You want to do this now?” I was intrigued, I had wanted to take this particular ride for a while now. He was giving me the perfect opening. I wasn’t totally sold on going right to anal, but it did give me the opening for more no matter what.

“Yes, let’s go in my room and we will see who comes out the winner,” he seemed sure of himself. I was pretty sure we would both win though, either way, I would fuck him.

Once in his room, he closed the door behind us, and I sat on his bed. “So what now I asked?”

“Take your skirt and panties off.”

“You just want to go for it? We’re not going to build up to that?” I laughed.

“Are you fucking with me?” He asked. I noticed that his erection was already straining against his pants. Apparently the concept was turning him on.

I stopped smiling and did as he asked. Pulling off my clothes and then moving back onto the bed with my back against his pillows. He smirked and climbed up after me.

Now that he realized I was actually into it, he wanted to take it a little slower. He ran his tongue up the inside of my thigh. I shuddered under his touch. Knowing what was coming made heat build between my legs.

As he moved towards my core, he would circle around and come close to licking my clit before stopping and then move his mouth somewhere further out. It was driving me insane. Right when I thought I couldn’t take anymore, he moved his mouth right over my core and took my clit lightly between his teeth.

I don’t know what I had been expecting, but Ollie being good at cunnilingous was something I had never considered before entering our arrangement. I assumed maybe I would humor him a little and then talk him into just having sex, but that plan went out the window pretty fast.

I didn’t even have the presence of mind to think that maybe I could prolong getting off by distracting myself or moving my hips at crucial times. Instead, I moved my hips in time with his strokes and I felt the warmth build between my legs until I peaked over the edge.

As my last moan faded, I looked up and sighed. He pushed himself up into a sitting position, his hand unbuckling his pants as he watched me.

“Well… fuck,” I told him, that was not what I thought would happen. I felt torn between a mix of nerves and at the same time a great deal of want and need to get fucked.

He laughed, “Are you ready for your part?”

“A deal’s a deal,” I told him. He was now working his dick in his hand as he watched me. “How do you want to do this?”

“Turn around and get on your knees,” he instructed, “I will handle the rest.”

I did as he asked, my legs shaking from anticipation. He moved up behind me and rubbed his hand over my ass. I heard him pull something from a drawer beside his bed and felt the wetness of the lube as he rubbed some on me and then his dick. I took a deep breath and squirmed under his hand. Hopefully he would be good at this part too, otherwise I was in for an uncomfortable night.

He slid into me, and then he started to move. Faster and faster he plunged into me from behind. I cried out from the build up of pleasure. His hands gripped my hips hard and he rocked into me over and over. I bumped my head into the pillows as I tried and failed to keep upright. My legs were shaking and I moaned into the pillows.

He reached around the front of my body and pinched and rubbed my clit between his fingers. When his hands moved back to my waist, I moved my hand to replace where his had been. I spread my legs wider as he continued to pump into me and I rubbed harder and faster, building up to an orgasm that had me crying out.

After a while, he was so into it, I could tell that he wouldn’t notice unless the bed fell apart. His hands tightened on my hips and I felt him pull out as he finished on my ass.

He used his shirt to wipe me off and I sat up in the bed next to him, shoulder to shoulder with our legs dangling over the side of the bed.

“I win,” he told me, laughing as he got up.

“I think we both won.”