Midnight Fantasies

Welcome to a sexy new edition of Midnight Fantasies. Here I explore your deepest, darkest fantasies and bring them to life for your pleasure. Today, our anonymous writer fantasizes about doing naughty things to his friends during a sleepover. Are you ready to shock your mind?

DRUNK SLEEPOVER

I am 18 years old and in my senior year of high school. I've always had that inner
urge to get with a guy but at this point I've only done it "by myself". My friends and I have sleepovers from time to time and I would always fantasize about experimenting with them.

Who doesn't love sleepovers, seriously, I would never miss an opportunity to sleep over at a friend's house with my good looking guy friends. I was part of the "popular" group in highs chool and have always been able to get with pretty much any girl I wanted, give or take a few. I was about 6' with kinda curly brown hair that I flipped up in the front and, so I hear, gorgeous blue eyes. Ive never been
touched by acne so my face has always been clear.

I played lacrosse from 5th grade up untill the time when this happened and we always had to run a lot for practice, I was more or less in shape but never one of the big football jocks, but I was toned in my torso with well defined musles that cut into my belt line. I'd only ever pushed myself in lacrosse because I loved just changing clothes in the locker room with all the guys and those occasions when we showered together were even more a reason to stay on the team.

Well my fantasy involves a pretty usual, boring night. My friends and I usually buy some beer and somehow sneak it into my friend Matt's basement where we could drink then sleepover there. We all called our parents and got the OK. Matt was the same height as me with dark blond hair that he always kept pretty short, he had a kind of hazel eyes and a nice face. We had been best friends since we were born literally, our mothers had been pregnant together and we grew up as neighbors and were always hanging out and playing Cowboys and Indians. We were friends to the point where I had a key to his house and would often go there and chill until he got there. He played football but was never so good, but he was in great shape as you would be if you ran and lifted weights every day. But the thing that I was attracted to the most were his legs and his ass, he had the perfect amount of hair on the back of his legs and I was dying to see how that hair pattern continued up under his boxers.

There were two other guys with us, one named Alex and the other named Derek. Us four together were known as best friends and whenever one of us went to a party the others were never far behind. Derek was a little shorter and had a nice tan, he was skinnier than the rest of us but had a great body. He had black hair and brown eyes just like his dad (who happened to be a great looking guy). Alex had dark skin like a mexican which we always joked about and a birthmark that started just above his waistline and continued downward.... He played lacrosse too but was always too shy to take a shower with us and ran home to take showers after games and practices. He was a little flabby but not many people knew how he looked under his shirt, just
his good friends.

We got to Matt's house and I parked my car on the street and we all got out. Derek and Alex put the beer by a basement window to be pulled in later that night. We all went in and Matt's parents were already in bed! What luck. We made some pizza and went downstairs. Derek was the biggest drinker, then Matt, then Me, then Alex. But
tonight Alex had drinken even more than Derek and had passed out on the couch in his clothes before we had even finished our beer. We finished it a couple hours later and were completely wasted.

It was about 3:15 and we started to get into sleeping positions. Matt slept on a couch with just a blanket and Alex was still passed out on his right side, facing the wall, on the other one. Me and Derek slept on the ground with sleeping bags. I was careful to sleep on the left side of Derek because his sleeping bag's zipper was on that side. Derek, having drunk the second most was passed out sleeping in a
matter of minutes quickly followed by Matt. I tryed super hard to stay awake to do a little 'exploring'.

I waited a couple minutes and listened to see how hard Derek was breathing. He was breathing steadily and I was sure he drank a lot so he would be sleeping soundly. I pulled my upper body out of my sleeping bag and moved my hands over to unzip Derek's. I started to unzip it and felt the warm air come out from inside. I got it unzipped down to his knees and started to move my hands inside his sleeping bag. I had done this a few times before but only ever felt legs and stuff on drunk nights
but lucky for me we had all decided to sleep in boxers this night, except Alex, that would be a task. I felt Derek's hairy legs with the back of my hand and started to push up his boxers.

My dick started to get hard immediately and I let it pop out of my boxers to relieve the tension. I moved my hand to Derek's inner thigh and put it up into his boxers, I felt his balls with my fingers and then put his limp 4 and a half inch dick into my hand, I though about jacking myself right then but thought I could get more out of this, after all there were two other drunk friends in the room. I started to jack him off even though the angle was wierd and I felt him getting hard in my hand, god and his dick was so hot. I started jacking myself with my other hand and then right before I was going to squirt, he rustled and turned his body over onto his side. God! Just one more second and I would have had it, but my boner died quickly thinking that Derek had caught me touching him while he was sleeping. Luckily, he didnt say anything so i stayed where I was untill I was sure that he was
sleeping again.

I heard his breathing get steady again and started moving over to Matt. He was in a tight undershirt and boxers but he had thrown his blanket off of him while he was sleeping...less work for me. There was a little light from the computer on the other side of the room and I could see Matt's well toned body in the dim lighting. His
boxers were down a little low and I could see his happy trail starting to widen into his pubes, I also saw his love handles fading down into his legs which is my favorite part of a guys body.

I took a different approach with Matt when I noticed that the hole in the front of his boxers was almost wide open! I started to put my fingers in the hole and I felt his pubes touching my hands and tried to find the base of his shaft, his dick was flopped on its back pointing towards his head, I grabbed it lightly and let it lay down outside his boxers. I looked at it intensely and saw the 'V' on the back of
it's head. I gave it a little lick and moved my toung to the base of his dick. Then I moved to his balls, which were bigger than Derek's were but not as hairy, I pulled them out one by one so that his cock and nuts were just sitting out in the open air. I got up off my side and got on my knees.

Matt was still breathing good so I stood up and went to get a flashlight from upstairs, it seemed like it took forever but thank god I was so familiar with Matt's house. I came slowly back down the basement steps and went over to Matt, I turned
on the flashlight and saw that he had turned himself over and was laying on top of his dick. I touched his ass and he stirred a little so I dove to my sleeping back and pretended to be asleep.

I considered that a lost cause and waited about ten minutes, which went by super slowly. I climbed over Derek and moved toward Alex, my last chance for a good jack off session. It was promising seeing how he was completely passed out, and earlier that night we were hitting him with pillows and he wasn't waking up. I went straight to his belt not wasting a minute, by now it was 4:25 which I couldnt believe! I
undid his belt and then the button and zipper on his pants. I pulled his pants down to the middle of his thighs and then slowly pulled down the side of his boxers that he wasnt laying on.

I grabbed the flashlight from the floor nearby and turned it on, being careful not to let too much light get out. I shined it on his crotch and saw that beautiful birthmark, it went all the way down into his pubes and I touched it and caressed his pubes. I started to move my face nearer when I realized how close his ass was to me. I put my hand between my legs to warm it up for a second so I wouldnt wake him up. Then I slipped my left hand under his boxers, stretching the elastic but not too much, and felt his flat back subtly part and turn into two plump cheeks. I kept my hand on the crack and let my middle finger slide throught the twisted hair finally to come to his hole. I thought for a minute with my finger touching his hole if I should try to slip it in. I decided yes and pulled my hand out.

I put my finger in my mouth and got a little taste of his ass, which I thought would gross me out but turned out to be a huge turn on. After my finger was totally wet
I put my hand back in and found his hole again. I started to put my middle finger in and was so afraid that he was going to wake up, it slowly eased in to the first knuckle. Then I moved my hand in a little more and put my finger in to the second knuckle. I could feel his warm insides on my finger and moved it around a little. It was a texture like I had never felt before in my life. I pulled down my boxers and started to feel my huge boner, the biggest I'd ever had, and let my finger slip in his hot asshole a centimeter past the big knuckle.

I was so horny and started to jackoff real fast, I started to pump my finger in and out of his asshole, then I tried to get two fingers in and he stirred, but I kept jacking. I couldnt lose it again. I pulled my finger out and stopped with both hands for a second, I listened, and realized that he was asleep again already! I used both hands very slowly to turn him over and at the same time pulling his boxers lower, exposing him down to under his balls. I now understood why he never wanted to shower with us after lacrosse, his dick was bigger limp than I had ever seen in my life, it was about 6 and a half inches, limp.

While one my knees staring with my dick resting on the couch, his left hand flopped down and layed directly on top of my exposed boner. I'd never felt that hot in my life. I turned his hand a little and put my huge boner inside it. My dick was wider than normal because I had wanked it so much that night. I closed his fingers and started to pump with my body as if I was masturbating myself. I naturally started to bend over with the motion and then crouched myself closer to his dick. I grabbed his dick and let it limply sit in my mouth. It immediatley started to get bigger and was starting to harden, I was 30 seconds from an orgasm and I had a guy jacking me off and his dick was in my mouth!

I started to suck him hard and I couldnt belive he wasnt waking up, I was ten seconds away when I tasted his precum and I was about to blow the biggest load of my life, I kept pumping with my dick and pulled my mouth away with the taste of his cum in my mouth! I had just got a guy to cum in my mouth, but that wasnt the situation at hand...where was I going to put all this cum that was seconds from coming out? Then I knew, and you would have too. I thought to myself...Is he drunk enough?....Of
course he is. So I quickly pulled up his hip with my left hand putting him on his side again and laying him against the back of the couch.

I pulled up his left ass cheek and put my knob against his hole. This was the moment of truth, I shoved with all my might and got three fourths of my 7 and a half inch, unusually wide cockin his virgin asshole. He stirred but it was too late, I was already unloading, and pulse after pulse of my hot cum was streaming into his asshole. Six or seven huge loads entered and he stirred again. I pulled out and dove over to my bed to hear him stirring even more. He moved around for about a minute and then stayed still. I waited ten minutes and knew that if I didnt put his clothes on I might get caught. I moved over and started to pull up his clothes. I regretfully put his clothes back on. There was no way I was going to get caught. I went back to my bed and by this time it was 5:30 so I fell right asleep but couldnt help thinking about all that had just happened.

So that's my fantasy. Every sleepover we have I really want to try this but I fear getting caught. I guess it will always be a fantasy.