I’ll try to keep this short and sweet, but this story has a lot of juicy bits, and I have a lot of back story to fill in since this is my first post, so bear with me if you will. I’ll label the parts of the stories so you can skip if you want.
It’s Friday night of Halloween weekend 2010. I’m sitting at home finishing up some last minute assignments before I go out for the weekend where I can forget about University. My friend Melissa sends me a Facebook Chat message saying my roommate Dan invited her over to party (this is quite normal, I hang with Melissa a lot, especially since- this is notable- her roommate is probably my most steady fuck buddy in 2 years).
Some background on Melissa- She’s been in a year long relationship that went long distance about 3-4 months ago. It’s been really tough on her, and she broke up with her boyfriend earlier this week. Shortly before she met her boyfriend, she met me, and obviously was a little interested in me (I pick up on these thingspretty well), but I had informed her I’m only doing friends and casual sex, so I was friend-zoned pretty quickly after that (which is totally cool with me. A part of living a drama free sex life is being open about your intentions and realizing it’s not a good idea to push it with someone who’s uncomfortable with the idea).
Melissa has also been talking to Dan a LOT. She thinks he has a nice ass (as she drunkenly said at one of my parties). I’d bet she wants to fuck him.
Melissa gets over, and I just finished my assignment. I cook up a burger (can’t drink without food) and have a couple beers while I put on some music to pump everyone up. Dan starts taking shots of rum and vodka, Melissa starts drinking her trademark bottle of wine.
After I eat, I put on my Halloween costume, and head over to the nearby apartment we were invited to a party at. Usually their parties are low key, but they were significantly packed, almost as much as one of my parties (I like to throw big parties- just not for holidays).
We had fun, met a whole bunch of people. I was more drunk than I planned. Dan’s costume was a huge hit. Melissa was raging drunk (in a good way) and bit Dan’s ass. It began to become increasingly obvious that Melissa was like a cat in heat- fair enough, she hadn’t been laid in 3 months!
WOOP! Fire alarm goes off. We walk back to our apartment, cause it’s been a few hours and everyone’s toasted.
I put on music again, and we’re all drunkenly wandering about. I sent Dan a text message telling him what to do if he wants to get laid (Melissa had been telling me earlier she wanted someone to pull her hair and smack her ass). Dan disappeared briefly, and I walked over to my room.
In the hallway, Melissa appeared and looked at me. Something just sort of connected when I looked her in the eye, and she walked towards me where we made out for maybe half a minute.
And then I pulled off and was like “look, I’m trying to push Dan onto you, since I know you want him.”
Dan is a little weird. He hasn’t been laid in a long time, and I think he’s afraid of casual sex. Despite my further attempts to get him laid (He needs the sex more than I do- I’m already fucking Melissa’s room mate), he responded to my text saying he wasn’t up for it.
Dan said he was gunna go and left me in my room with Melissa on my bed.
It was obviously my job now. Not that I have a problem with that. I always thought Melissa was hot. She’s a skinny little blonde girl; very feisty. I have a huge thing for skinny chicks.
I close my door and hop on the bed. She turns; we kiss. We furiously make out. I’m drunk, and try to unclip her bra with my left hand. I’m a righty. I apologize and do it first time with the other hand. Clothes come off, one by one, and soon enough, I’m face down in the crotch of my hot friend who I thought would forever be off limits.
(I’m glossing over a lot of details cause I was drunk, and this isn’t supposed to be erotic fiction. Timeline will seem shorter than it was)
She comes once, maybe twice. Damn she’s easier to please than her room mate. I love that. I get up off that and we furiously make out again. I get my condoms out, and she’s lying on my bed spread eagle.
I fuck her like there’s no fucking tomorrow, and you can goddamn hear it. Hand over throat, rough as you could imagine. It was 2 am and I felt bad for the guy living next to me cause she’s a borderline screamer.
I flip her over to fuck her from behind; we fuck like animals. I’m beating the shit out of her ass and she’s loving it. She must have come like 5 times or so at this point. I pull out for a bit and finger her while she’s bent over.
The Danger Zone
As I was fingering her, she was repeating “Oh Mack….you can do anything you want to me…” In my experience previously, that statement is nothing more than fantasy talk, but I was drunk and adventurous. Since I was fingering her, my thumb was already rubbing on her asshole little. I decided I’d push in, gently, just a little. Worst case she says “Woah what’s up with that” and I go “my bad.” But I had a gut feeling about this.
I start on it. I didn’t think she could get louder, but she did. She LOVES it. next thing you know, I’m fingering her ass, and she’s in absolute fucking ecstasy. This is unprecedented. I pull back her hair and call her my slut. She asks me to put it in her.
I had never done anything with anyones ass before. I had read up on it, but it wasn’t particularly a fantasy of mine- I’ve always held that I would only ever do it if the girl wanted me to. And well, she really wanted me to.
I worked up my fingers, 2 fingers, 3 fingers, and then replaced it with my cock. She moaned so hard. I pounded her ass and I could have swore she was going to have a heart attack.
eventually I stopped, I didnt want to do damage.
I pulled out and told her I was pretty much done. For explanation- I have a condition called delayed ejaculation- it’s pretty DAMN hard to get me to come. And that’s sober. Drunk? I can’t really feel much of anything.
We layed back in post coital bliss and she thanked me for everything repeatedly. She told me she was seriously impressed, and that guys are usually afraid to go for that.
Not me, I’m more adventurous now than ever.
We fucked again in the morning, just as loud. She gave me some AMAZING head. I hope I can get more of that from her soon. We fucked some more and did the anal thing again- I wasn’t dreaming, she LOVES it. Weird to me, but hey, I’m cool with it.
Anal sex doesn’t really feel any better than vaginal. I’m still fine without it. On the other hand, I am SUPER dominant in bed, so the dominant aspect off it was really getting me off. And the taboo aspect got me off too.
I finished this time, came inside her (condom! I always use a condom! And yes, no anal-to-vaginal penetration).
So that was my first ever entry into the world of anal play/sex. We’re talking now about possibly arranging a threesome with her and her roommate now. We’ll see about that.
Anywho, I think that’s enough story for now. I could seriously go on and on….