[M]y best [F]riend: A One Night Special Event | 2016

At the time of this trip I was still in a 2 yr on again/off again relationship and the 2 girls knew each other. I never thought I could cheat on her and prob never would have if this night never happened. There was always just some strong connection between me and Kirsten.

So spring semester of my freshman year me and my roommate plan a trip to see some friends at a university across the state. It was going to be a guys weekend, first time all of us hanging out there. I had been warned not to tell Kirsten I would be there and we could see her next trip, especially since we apparently spent too much time together when they visited us a few months earlier, and I agreed I wouldn't tell her. So we get there, get some food and then head to a house party my friend had been talking about. I think I'm in the clear, we didn't run into her and she prefers to stay downtown so I won't have to hear my friends bitch. About an hour in, I walk outside to make a phone call, right before I hit send, there's Kirsten walking up the path with a few other girls. The guys are not gonna be happy, but I was. We split up inside but as the night progressed, we gravitated to each other, it's just what we do, we entertain the hell out of each other. Next thing I know, my friends are gone (they claim they told, and they prob did) so she offers to take me to them, but I know it's way out of her way so I suggest we keep hanging out at her place and I'll crash on the couch, this seemed to make her quite happy.

We had been gradually getting more flirty with each other all night so when we laid down on her bed I began to wonder how the night would end. We began to chat about all the summer nights we spent out by her pool, the many hot tub nights, and wondering why a relationship never worked for us given how close we were. She started rubbing her neck so I volunteered a massage, which she definitely knew I would do bc I always had. So I start in, her on her stomach, me to her side with her face toward me as we keep on talking. After maybe 10 mins or so she seems real relaxed, eyes closed and conversation dying off, I assume she is about to fall asleep. In the silence, I began to take her all in again, always such a hot attractive body with small firm but squeezable ass, and I have always wanted to get my hands on it. But my favorite physical quality was her face. She was beautiful, that sweet girl next door type, with amazingly bright light blue eyes. Now my mind is racing, did I really misread the night and her "signals" that badly? At about that moment she let out a deep moan and seductively opened her eyes and looked up at me. Something we had done so many times now just brought on a totally different feeling. I stopped massaging her shoulders as we locked eyes and I leaned down and kissed her. We were locked in the kiss for a few minutes then both pulled back. It was clearly a much different feeling than the first time we kissed years ago. Seemed we were waiting for the other to speak, both wanting the same thing but not sure the other felt the same. I finally said "sooo that was a hell of a lot better than our first kiss" as we both laughed. There was a slight concern on her face, I leaned in, kissed her and said "don't worry, we both finally want this, we can keep a secret." That was the go ahead she needed as she pushed me down on the bed and hopped on top of me.

Holy shit, so this is happening, I thought. Almost immediately my hands go directly to her ass, I survey ever inch of her small firm ass before squeezing it tight. She lets out a small laugh "how long have you been waiting to do that" (she knows I'm an ass man) "since the day I first saw you walk by." But don't get me wrong, I really enjoy tits too, I'm just not picky about size and all. I was in luck though, Kirsten was in the C range so I was about to have a lot to play with, and since we had already gotten ready for bed, she was braless in a loose shirt so they were already rubbing on me. My hands move to her chest, shortly after, she sits up to pull her shirt off and a moan comes out of us both. I only have boxers on and given how soaked through her shorts are, thats all she has. Nearly nothing between us, we've never been this close. With a mischievous look, she starts sliding up and down my cock teasing me and herself in the process. I begin caressing her tits and playing with her now very perky nipples. After some more kissing she slides down the bed pulling my boxers with her.

She slowly runs her fingertips up both my thighs to my stomach and back down. She gave me a cute grin as I twitched a bit. She ran her tongue up my shaft and around the tip as she gripped it in her hand. "It's a bit bigger than I pictured" she said. I give her a confused look, "did you really think I never snuck a peak as you were getting out of the hot tub, or that I never felt it at the dance" I laugh a bit and say "yeah, I think I chose to ignore those potential embarrassments." So one thing I didn't know about Kirsten, she loves cock. I could see it in her eyes how much she enjoyed making me squirm and how she just stared as she ran her hands around it. There was something she was doing with her tongue, like she had multiple ones in her mouth wrapped around the tip while she stroked my shaft and played with my balls. It was so hot watching her and having her look back at me. This went on till I was about to explode, and I wanted to save it all for when I finally got inside her. I pull her up to me and we share a long wet kiss. I roll her over on her back and start kissing my way down her neck to her chest and down her stomach.

I really enjoy going down on a girl. All of it is great, the taste, the smell, watching her twitch in pleasure. So I'm very excited as I pull her shorts off, and what they reveal is a thing of beauty. Her smooth glistening lips pucker out and she has a nicely groomed bush above. I start kissing up her calves to her thighs with my fingertips leading the way. Once I get my head in between her legs I get one handful of ass and the other hand continues gently exploring around pussy making sure not to touch any part of the vagina. I keep kissing and touching all around the one spot she really wants it. I can hear her breathing start to pick up and she is starting to buck her hips and that's when I go in mouth first. She lets out a much louder squeal/moan and quickly covers her mouth (she had a roommate). I laugh and go to work alternating a bit between tongue and fingers on her clit. She seems to like it best with 2 fingers inside and circular tongue pressure on her clit. Things start getting very wet and her stomach and thighs start to spasm and twitch. That doesn't go on too long before she raises up panting and says "get inside me."

We already had the condom talk and I knew she had been on the pill for yrs for health reasons, and we clearly trust each other so I waste no time responding to her request. I kiss my way up her chest and neck. I see a passion in her eyes I had never seen before and immediately kiss her while teasing her with my cock sliding it up and down her lips. It gets nice and wet and slides right in, we both pull from the kiss releasing a heavy moan. I don't know if it was bc I had fantasized about this moment so many times or what, but that was the best entry feeling I have ever had and with the way her eyes rolled back she seemed to enjoy it as well. I start out slow, gradually going deeper, just enjoying how warm, wet, and tight she is. I can tell when she is comfortable and ready to go as she starts bucking her hips at me and grabbing my ass. I start playing with her nipples and pull one leg up to get a better deeper angle and well, I just had to have a grip on her ass. We get into a nice rhythm and it is feeling fanfuckingtastic. We both start laughing, not believing this is finally happening and that it feels so damn good. She tells me she is getting close but that she has her strongest orgasm on top. Now I could have easily rolled us over, but no way was I going to miss out on watching her lower herself on me.

It was very hot watching her slowly allow me inside her. She lowered herself all the way down and cocked her head back in ecstasy just enjoying the moment. I raised myself up to her and it was like our lips wouldn't separate. I grabbed ahold of her ass, pulling her into me and she wrapped her legs around me and we were both rocking up and down. Even though we weren't actually together, our history plus the passion of the moment and this position, prob made this the most intimate moment I've ever been in. I thought it felt good earlier, no, this right now is the best I've ever had. We were perfectly in sync with each other, both with huge smiles on our face every time we made eye contact. I make a few comments about her "amazing" ass that cause her to blush and then earn me a playful slap to the side of my ass for joking on her blushing. So this has been great and so much fun, the anticipation of climax starts to grow.

I start to feel a rush of wetness and tightening as she begins to buck hard and deliberate in one spot. I start kissing her neck and playing with her nipples and she pants "I hope you're getting close, I want to cum together". She lowers her head for one last kiss and then it's like all the air left her. Her eyes rolled back, her hands dug into my back, her thighs were like a vice grip around my waist, and as I'm taking in this beautiful sight, she exhales and the inside of up pussy starts pulsating all over me. I make it a thrust or two and then I lose it. I bury my head in her neck and try not to squeeze her ass too hard as I pull her as close as possible to ride out the most powerful orgasm I had ever had. We stayed like that for a few mins, letting the pleasure slowly fade as we calmed down, and I was in no hurry to pull out. We finally collapsed to our sides, she leaned in for a kiss that went on for awhile. We were a tangled body of limbs for awhile and then she said "ok...I think I can walk now" to which I replied "good, I could use some water." She gave me a look I've seen a million times with a slight slap, and just like that we were back to being friends.

(By the way, I got us water while she cleaned up and looked for new, dry shorts)