“I’m kicking your ass, how does it feel to lose to a girl?” I asked.
“Be nice,” Ryan replied.
We played a few more games of Wii baseball and I kicked his ass a few more times. Eventually we had to take a break though. We both just sat down on the couch for a few minutes, but then I had to get something off my chest.
“Ryan, I’ve noticed that you haven’t had any other ladies around lately,” I said.
“Well, the dating game has been down, but I guess miss right is out there somewhere. I’ll find her sooner or later,” Ryan replied.
“Well, I haven’t had much luck either and it’s been hard not doing it every now and then,” I said.
“Trust me I know what you are talking about. I guess I was spoiled for awhile,” Ryan replied.
Then I laughed for a minute.
“What’s so funny?” Ryan asked.
“Nothing, but can I ask you something?” I asked.
“What’s on your mind?” Ryan asked.
I hesitated for a minute.
“Have you ever felt that way about me?” I asked.
I looked at him and he had to think about it for a minute.
“Maybe once or twice, but we’re best friends. I think sex might change our relationship. We wouldn’t be best friends and we might drift rather than get closer,” Ryan replied.
“OK,” I said.
He saw I must have had something going on.
“Have you thought about it Amy? I mean we’ve been best friends for years now and I guess I just thought we’d stay friends until we died. I knew we’d get married to other people, but we’d still have each other to hang out with,” Ryan said.
“I understand what you are saying, but what if we tried it once?” I asked.
He had a skeptical look on his face for a moment, but I think he knew I was more than curious about this idea.
“Sure, if you really want to,” Ryan replied.
Then I got close to him and I kissed him once.
“That wasn’t too bad,” Ryan said.
We began making out for a few minutes. He put his arms around me and held me close as we made out. I put my hand on the bulge in his pants and his cock was really hard. So obviously he did have a thing for me.
“You are turned on by the idea of us doing it,” I said.
Then he knew there was no turning back, he kissed me again and pulled me right on top of him. We both put our arms around each other and made out passionately for a few minutes.
“This is hot,” I said.
He picked me up and brought me to his bedroom. He set me down on his bed, got down on his knees and lifted up my shirt. He leaned down towards my stomach and began kissing it a few times. It tickled and then I put my hands on his head. Then he put his right hand into my panties and felt my wet pussy.
“Your pussy is very wet,” Ryan said.
I just smiled at him and he kissed me once again. After that he took his hand out of my panties and got up on the bed on the side of me. He felt my boobs with his right hand and I saw the bulge in his pants get bigger.
“Can I see it now please?” I asked.
“I’m not stopping you,” Ryan replied.
So I undid his pants and I saw his cock poked out through his pants, but it wasn’t as big as I imagined. It looked like it was about 6 inches, but I was expecting it to be about 8 inches honestly.
“Wow, that’s nice,” I said.
“I know it’s not very big, I’m not a player you could say,” Ryan replied.
Then I got really close to him and whispered in her ear.
“Well I can make it bigger for you,” I said.
“Prove it,” Ryan replied.
I leaned down and took his cock into my mouth. I never would have truly thought I’d be sucking on his cock, but I was gonna make every second count. I started going up and down slowly, but I didn’t waste too much time going slowly. I picked up some speed rather quickly and made him have to lay back. He took in a very deep breath and exhaled deeply. He was just loving this whether he wanted to admit it or not.
“Oh shit Amy, I had no idea you could take a dick like that,” Ryan said.
I didn’t answer him, I just kept sucking on his cock like mad for about 10 minutes straight and he was moaning like mad as well. It was as if no one ever sucked on his cock before, so I wondered something, but I kept to myself, I didn’t wanna ruin anything.
“Holy shit Amy, that’s so damn good, keep going up and down like that and don’t stop,” Ryan said.
I just kept going faster and faster until I got a little tired, but even then I didn’t wanna stop. He put his hands on my head and made me take even more of his cock. I began to deep throat him for the first time. That was maybe a little much for the first time we had sex, but still it was so damn sexy and nice. He was still taking some deep breaths for about 5 minutes straight and then he began moaning very loudly.
“Oh shit Amy, I’m gonna blow everywhere now, I can’t fucking hold it anymore,” Ryan said.
I backed away a little bit and saw him just erupt big time.
“Holy shit dude,” I said.
He couldn’t answer. I got on top of him and kissed him again. After that I leaned up and took off my shirt. I only had B-cup breasts, but he seemed to really like them. He put his hands onto my boobs and felt them just through my bra that time.
“They maybe small but they are nice, I like them,” Ryan said.
Then I took off my bra as well and threw it on the floor. He looked at my boobs and I thought he was mesmerized by them. It was as if he never saw boobs up close before either. I thought of something again, but once again I kept it to myself though. Then he put his hands on my bare boobs and just kept them there for a few minutes. He gave them a few gentle squeezes and I think he wanted cum again.
“Do you like them?” I asked.
“Yes, they are so damn soft and beautiful,” Ryan replied.
“Do you have any condoms?” I asked.
“No, I’m all out now,” Ryan replied.
“Good thing I got one in my purse, I’ll be right back,” I said.
I ran back to the living room and got a condom out of my purse. I couldn’t help but wonder why he had no condoms. He really could have been all out, but still I dismissed it for the time being. I came back in the room and he was completely naked. Judging by the look on his face, he was more than ready for me.
“Someone is hot and ready,” I said.
“You could say that,” Ryan replied.
So I stripped completely. I stood in front of the bed and his eyes were glued to me.
“Oh my god Amy, you are beautiful,” Ryan said.
“Thank you,” I replied as I got on the bed with him.
Then we began making out once again as he got on top of me. He put his hands on my boobs once again and just rubbed his hands on them for a few minutes.
“You have some really soft hands too,” I said.
“Thank you,” Ryan replied.
Then he leaned down and kissed me again. We made out for a few more minutes and he still hadn’t put the condom on yet. I had to wonder if he really wanted to have sex or not.
“Remember, I have a condom here,” I said.
“I know, I’ll put it on right now,” Ryan replied with a small tone.
“What’s wrong, do you not wanna do it now?” I asked.
“No, I just have a confession to make,” Ryan replied.
I had a feeling about this.
“What?” I asked.
He sat on the edge of the bed.
“I never had sex before,” Ryan replied.
He was embarrassed, but I had to crack a little smile.
“Really?” I asked.
“Yes, I guess you are the only one I’ve had any luck with,” Ryan replied as he put his head down.
I felt bad for him, really bad. He was 26 was still a virgin? So I kissed him on the lips.
“Well I’m very happy to be your first, now let’s do this. It’ll be extra special sense we’re best friends,” I said.
Then I took out the condom from it’s package and put it on his cock.
“Well at least you have been good at making me feel good. Now come on, I’ll be gentle with you,” I said as I laid down.
Then he got over me and put his cock right in front of my pussy.
“Don’t be nervous, just stick it in slowly,” I said.
Then about 20 seconds later he slowly inserted his cock into my pussy. It was a little weird having sex with a virgin. Honestly it never entered my mind until that day that he might be a virgin. I didn’t look at him as being different, I just showed him the ropes. As he had his cock inside me, I pulled him down to me and kissed him a few times.
“It’s OK, now slowly thrust your cock in and out, you’ll like it,” I said.
He began thrusting very slowly. I think that he thought it was gonna hurt me if he went any faster. After a few minutes he got more and more comfortable doing it. He put his hands back on my boobs and squeezed them a bit as well.
“OK, are you used to the training wheels now?” I asked.
“Yes,” Ryan replied.
“Let me have it now, I want you to fuck me hard,” I said.
Then he gave me another kiss and started thrusting his cock a little faster in and out of my pussy. It may have been because he was my best friend, but I loved it to no end. It felt really damn good to say the least. Even though he didn’t have a very big dick, it still felt amazing in my pussy.
“Oh yes Ryan, now that’s what I’m talking about. Just don’t be nervous, have some confidence and you’ll be fine,” I said.
Then he kissed me again and then he leaned his head down a little bit towards my boobs. He began licking my nipples. I noticed he knew what he was doing though, he made me feel good licking them the first time.
“Have you licked nipples before?” I asked.
“Maybe once or twice, but it never got any further than that though,” Ryan replied.
Then he kissed me on the forehead.
“My lips are down here,” I said.
“I know,” Ryan replied just before he kissed me on the lips.
Then I kept him down there with me and we made out as he had to stop thrusting. He still had his hands on my boobs though. We made out like that for about 10 minutes straight until it just became too much for him and he couldn’t hold it anymore. He began moaning really loudly.
“Your first anal orgasm, enjoy it,” I said.
He wanted to see it, so he pulled out his cock and ripped the condom off. Then he came all over himself mostly and I watched as well. As he was done, I grabbed onto it and stroked it for a minute. I kissed him a few more times. Then we both tried to catch our breaths for a minute.
“Seriously if you are best friend or not, if you told me you were a virgin at 26. Well, I would have stripped and said ‘Fuck me now Ryan’. Why didn’t you tell me you were virgin?” I asked.
“I was embarrassed I guess, and I wasn’t about to sacrifice our friendship for that,” Ryan replied.
I suppose he had a point there.
“Now you are officially not a virgin, how does it feel?” I asked.
“Pretty damn good,” Ryan replied.
Then we just cuddled for a few more minutes. He seemed to be very happy about his very first sexual encounter, and it was with me. Well, except for the nipple licking though.
“So whose nipples did you lick?” I asked.
“Just a girlfriend’s a few years ago, I don’t think you ever met her,” Ryan replied.
“Why the fuck not, we’ve introduced all of our boyfriends and girlfriends to each other, why not her?” I asked.
“I don’t know, I guess I just never introduced you to her,” Ryan replied.
“OK then, I guess her loss is my gain,” I said.
“I guess so,” Ryan replied just before he kissed me.
Then we stayed in silence for a few more minutes as we cuddled.
“So you wanna do it again?” I asked.
“I thought you’d never ask,” Ryan replied.
Then we did it again, and let’s just say we weren’t best friends anymore after that. If it gets really serious, we’ll see.