Greatest Night of my Life

Go over to a friend's house for the weekend. His sister has some friends over: Nicole - tall, slender brunette with little tits, but a great ass, Nikki - chubby, huge tits, Brandy (sister) - petite, decent tits, Jennifer - petite redhead with non-existent tits and a little bitty ass, Rachel - quiet, shy, undeveloped really.

We hang out throwing the football around, girls jumping on the trampoline in their bathing suits. I can't take my eyes off of Nicole. Girls ask the Dad if he would buy alcohol so we could have a party. I go to take a shower and when I get out, the fridge is packed with all kinds of drink. Dad goes to work and since he is a fireman, will be gone 24 hours. Buddy gets called in to work at fast-food joint for a couple of hours, leaving me and the girls.

We start to drink, awkward at first, playing music, talking bullshit. Night goes on and we get a little looser, dancing, telling secrets. As we start to get drunk, we start playing truth or dare, but nothing too exciting. Rachel admits she has never kissed anyone is the only thing that really sticks out. A while later, we are all pretty drunk, stumbling back and forth from the kitchen. Brandy pours wine cooler on my head, staining my t-shirt, so they tell me to take it off. Nicole asks me to come sit by Rachel and is basically trying to talk Rachel into kissing me for her first kiss. I say I will, but Rachel doesn't want to. Nicole says she will kiss me and for Rachel to watch. So that happened.

Little while later I am dancing with Nikki and get a boner. Nikki asks what is poking her and reaches down and wraps her hand around it. I panic. Never had a girl touch my dick before. Had just barely sucked a titty nipple at this time. She says, "Oh..." and pulls her hand away. I'm embarrassed, but nothing is said about it. Little while later, Brandy is straddling me on the couch and I pour a wine cooler on her head. Tell her she needs to take her shirt off, so she does, giving me this look of defiance like - oh, you didn't think I would do it. My dick gets hard and she tells everyone. They tell her to get up and for me to take it out. So I do. Everyone turns to Nicole and asks her if it is big because apparently she is the only one that has done anything with a guy. She says yeah, it's pretty big, but not the biggest she has had. I get a little embarrassed, self-conscious about it now. Jennifer says she is going to bed, but they tell her she can't. She said she doesn't want to stay up if we are pulling my dick out. They tell her she can go to bed, but first she has to put my dick in her mouth. After a bunch of bullshit, me sitting in silence like a fool, she finally kneels down and puts it to the back of her throat without wrapping her lips around it. Hooray my first experience putting my penis in a girl's mouth for 2 seconds. Then she gets up and goes to bed.

Somehow we start to play who has the nicest ass, with all of them mooning me. Nicole wins. Who has the nicest tits, with everyone flashing me. Nikki wins. Who kisses the best - except Rachel. Brandy wins. Brandy passes out on the couch. Everyone starts talking about going upstairs to bed. Nicole has trouble walking, so I pick her up and carry her upstairs. When we get to the door to Brandy's room, we pause to discuss where everyone is going to sleep for some reason. Nikki and Rachel say they both want to sleep with me, Nicole is about passed out. We walk in the room, I lay Nicole on the bed with Rachel and crawl into bed with Nikki. She says she is cold so I pull the blanket up like a moron. She turns her back to me and pulls my arm around me. Her tits are resting on my arm, so I start rubbing her stomach, moving my arm to get the sensation of her tits moving on it. She turns to me and we start kissing. I slide my hand up her shirt and squeeze her soft boobs.

Then Nicole starts freaking out, having a nightmare. Yelling about someone attacking her, some ex-bf. Nikki gets up to deal with it and I go to help. Nicole slaps me telling me to get away from her. Nikki tells her I am not that guy, so Nicole apologizes and hugs me. She kisses my neck, but I pull away trying not to jeopardize time with Nikki. Nicole says she wants to dance so we stand in the room in the dark. Nicole turns the radio on and Nikki climbs back in bed. Boyz II Men CD... yes, sir, that'll work. Nicole is dancing with me, says she is hot in her bra and takes it off under her shirt and pulls it out. As we are dancing, I cop a feel of her perky tits through her shirt and she faces away from me, putting my hands on her tits and squeezing them. Her hips are grinding back against me and we fall onto the bed that Nikki is in. Nicole climbs on top of me and starts gyrating her hips, kissing me. I reach over and try to touch Nikki, but she very abruptly pushes my hand away. So I get up and move to the floor with Nicole. I slide off her shorts and lick her pussy. She pushed her hips up against my mouth, while I reach up to squeeze and pinch her nipples. She comes and gets on top of me. We kiss for a while and I slide my finger into her pussy again while she is on top of me, but the angle is horrible. She says, "Ouch!" and moves off of me to the floor. Then she gets up and into bed with Nikki.

Well, fuck. No go with Nicole anymore. No fucking way anything is happening with Nikki now. So I go downstairs to see if Jennifer is still awake, but she isn't. I pass by the living room and Brandy is still asleep on the couch with no shirt. I rub her tits a little bit, ashamed that my dick is so hard. I pull it out and jerk off until I cum all over her tits. I walk upstairs and climb into bed with Rachel, planning to just crash.

Rachel rolls over until she is basically nose-to-nose with me. She leans forward and kisses me. Just a peck at first, and then presses her lips to mine awkwardly. I part mine and she parts hers. I slide my tongue out a little to meet hers and she shoves her whole tongue into my mouth. I roll with it and rub her back, pulling her closer to me. I run my hand down her back and squeeze her ass. She pulls her leg up and puts it over me, subtly moving her hips to dry hump my hip. For some reason, I didn't want to wait any longer and moved her hand down to touch my cock through my shorts. She rubs it two or three times and then patted it. Then she rolled over and wouldn't respond when I tried to turn her back. I moved down to the floor and went to sleep.

The next morning, my buddy was giving me shit saying he heard Nicole moaning when he came home. We went to the water park and Nicole looked amazing in her bathing suit. When we got back to the house, the girls were on the trampoline with the water hose and I sat out there talking to them, hoping to make progress with one. When Nicole's dad came to get her, she ran back to the backyard and gave me a hug and a kiss, told me to call her. After she left, Nikki was being a bitch, saying Nicole was a slut and would cheat on me if I dated her. I told Nikki to come upstairs with me and maybe I would date her, but she wasn't having it.

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Anonymous

by Anonymous on Oct 2, 2016 at 5:30 PM

Teenage years, what a learning process. My experiences were very simular to yours. My wife got fucked at 15 yrs old by a college stud.

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Anonymous

by Anonymous on Nov 24, 2016 at 7:51 PM

I had an experience that started out in a similar fashion but then went in a totally different direction. The biggest difference was age. My then 15 year old sister asked if she could have a sleepover with her best friends. There were seven of the altogether Some of the guys at school called them the crazy eights because there were 8 of them and they were a bit crazy. My parents put a condition that my sister had to baby sit me. I was 13 at the time and did NOT need a baby sitter much less my sister who was only two years older than me and technically not quite even that much. My parents emphasized the phrase "babysit" just a little too much and my sister caught on to it and then all the girls went on about how I needed to be "baby sat" "like a BABY!" You get the picture, typical older sister taunting of a younger brother. So I hid in my room doing nerdy things like pasting stamps in my stamp album when my sister comes into my room, dad gave her the key, and informs me that the girls held a vote and it was unanimous, I was going do a strip dance for them, whatever that was. I'd heard of female strippers but didn't know guys did it. So I was dragged out and down into the basement rec room where they sleep over was being held and music was playing, very suggestive stripper music was playing and the girls started to chant "take it off!" "Take it off!" You get the picture.

I was scared and embarrassed but slightly excited that these older beautiful girls wanted to see me naked. Naive I went along with it and did my best impersonation of a stripper based on what little I'd seen on cable, late at night, when I wasn't supposed to be watching those channels. But when it came time to take off the last piece of clothes, my underwear, I got jeered and laughed at. The girls started to chant about my tiny pecker "baby dick, baby dick, baby dick!" I was so embarrassed. They said mockingly that no girl would ever want me or ever want to touch me and I'd never get fucked. Oddly, the whole time, my tiny erection was bobbing and throbbing.

I ran naked to my room and locked the door, this time with the dead bold and chain and I moved my dresser in front of it and a chair in front of the dresser and pulled down my curtains and locked my windows and shut off the light and ran into the closet and closed the doors and tied my neck tie around the door knobs together and shut off the light and climbed to the back of the closet and climbed behind a bunch of boxes which I then stacked up as high as I could then got another box behind that stack of boxes and climbed inside and pulled the flaps shut and rolled over until I was sitting on the only flaps that could open without tearing the box and thinking about suffocating and realized that was not a bad thing to happen and then cried myself into a tizzy, as my grandmother sometimes said.

At some point I had to take a piss and realized that regardless of how much I was loathing myself I really didn't not want to fall asleep in a piss soaked cardboard box so I climbed my way back out and moved the chair and dresser and undid the locks and crept down into the bathroom to piss. The problem was somebody was already there. We had four bathrooms. Our parent's bathroom. The main upstairs bathroom. The half bath behind the kitchen next to the mud room and the guest bath in the basement which I assumed the girls would be using. Even if there was more than one that needed to use the bathroom the half bath on the main floor was still available. I just then realized that there must be at least two other teenage girls peeing on a toilet in my house and at least two of the girls' weren't my sister and I started to imagine what it might be like to watch them pee.

Meanwhile, I had to pee really really bad and my parents bathroom was off limits and besides that they kept it locked because dad didn't want anyone to discover his vast porn collection and mom didn't want anyone to discover her vast toy collection and neither wanted anyone to discover the bondage chair they kept folded up under the bed, you know, the one with leather straps and over two dozen eye bolts you could tie rope to. Yes, that one.

So I had to wait for someone to exit a bathroom and there was no way I was going down stairs. I'd piss a puddle on the floor first and blame it on the girls before I'd let them see my existence for one second more. But I still had to piss and this bitch was taking forever. I don't know what she was doing but she was being damned inconsiderate. Yet at the same time I didn't want her to catch me standing there doing the pee pee dance so I hid around the corner. Finally I felt the releaf of hearing the toilet flush, the water run and a door unlatch. A second later she crept down the hall towards me and called out my name in a low whisper. I was caught. But she was one of the less evil of the crazy eights. She very softly apologized, taking the trouble to make sure she was whispering it so the other girls could not hear her from two stories below in dad's expensive sound proof rec room.

What she did next was shock me. She offered, in the way of an apology, to give me a blow job. Meanwhile I was still doing the pee pee dance and the shock of her words caused me to completely relax my bladder and I peed myself right in front of the co-captain of the varsity cheerleader squad, the second most beautiful girl in the high school, the first most beautiful one being another crazy eight presumably somewhere about thirty feet below. Instead of litting into me with a barrage of ridicule, she apologized for making me pee myself and offered to help me clean it up which turned out to be her doing all the cleaning while she just had me sit on the toilet seat in my wet pajamas.

Then she helped me out of my wet pajamas, washed them by hand in the sink and then went down the hall and popped them into the dryer for me. She then asked if she could suck my cock in my room. She said not to worry about the other girls as she had told them she was sick and was going to be spending a LOOONNNNGGGG time puking and shitting diarrhea. Then she got on her knees, I was still naked from the waist down but somehow didn't feel embarrassed as nice as she was. She then gave me my very first blow job and it was wonderful.

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Anonymous

by Anonymous on Nov 25, 2016 at 4:00 PM

Continued from above.

When my first blow job had completed and I was certain I was either halucinating or dead from suffication and this was heaven, this delicious centerfold contender licked me all clean, pee and all. She then told me she liked my little dick, thought it was cute and enjoyed sucking on it and asked me not to tell the others about her giving me a blow job. She then said she would like to do it again sometimes when nobody was watching if I didn't mind. Like I would mind the second most beautiful girl in the high school sucking on my dick. You never forget your first blow job. This wasn't your average unforgetable first blow job. It was with the perfect female. I was in love.

I strutted back into my bedroom and climbed into bed totally forgetting to lock the door. A couple of hours later I was woken up by a very pleasant sensation between my legs. At first I thought it was that girl coming back for seconds but it wasn't. The hair wasn't quite right. The first one had long straight soft silky hair. this was very curly hair, also soft but also somewhat stiff with curls. I asked who it was and she said "shhhhhh!" I can take a hint and said nothing as she sucked me off. I came in her mouth and I could feel her swallow. Not as gentle and finessed as the first one but it was urgent and passionate. This one was hungry. Then she cuddled up to me and apologized for acting like a KUNNT before and said she could not resist my adorable little cock and told me that it was not tiny for a boy my age and was in fact about average and could grow much bigger and I should not worry about it anyways because lot of girls like her enjoyed sucking on smaller cocks. This one was the first most beautiful girl in the high school and the one with the biggest tits and best smile. But I couldn't see a damned thing since it was dark. She did however let me play with her tits for a few minutes and feel her up.

I know you are not going to believe this but around 4 am there was a soft knock on my door. Not soft enough for me to remain asleep but not loud enough to be heard two stories below. This one turned the lights on. She was yet another member of the crazy eights. She was completely naked. She said that since they made me dance naked for them she owed me a naked dance. She hummed while dancing naked in front of me and then offered to let me fuck her. She said I should finger her first though to stretch it out. I thought she was sarcastically mocking me but what 13 year old horny boy is going to let a little mockery keep him from fingering a gorgeous teen girl's pussy.

I was surprised. She was very tight. I mean extremely tight. I could barely get my pinky in and it was small, like a little girl's pinky. But I worked at it and finally managed to get it in. Then she confessed that she was a virgin and said my dick was the perfect size for taking virginity because it wouldn't hurt. Without further ado she mounted me and descended on my hard little cock and began rithmic fucking and in a matter of minutes I came yet again. Of course I came, my cock was in a WOMAN'S KUNTT and it felt TIGHT! And not only that but she was a gorgious woman at that. They don't let dogs into the crazy eights. Not counting my sister, I had officially cum inside 42.8% of the crazy eights. I was left alone to get some sleep for the rest of the morning but later that day I was cornered outside in a more secluded part of the yard by yet one more member of my sister's gang of bitches and this one was begging me to let her play with IT! So I did and she gave me a very nice hand job which led her to compliment me on having a pretty little cock and she said she wished her boyfriend's cock wasnt so damned big because it hurt when she tried to suck it and she's afraid to let him take her virginity. I offered but she declined and said only her boyfriend was going to do that but she thanked me for letting her play with it and apologized for being such a bitch the day before.

I was begining to be convinced that indeed I had died from soffocating in that box because these kinds of things don't really happen.

By this point my parents had come home and the party was over.

Three days later my sister and one of the crazy eights, one who had not yet approached me with an offer to please me sexually, were studdying together. That was something out of charactor for them but I dind't think anything of it.

but then as I was passing through the dining room where they had set up to study, my sister's friend stops me. My sister had gone up to her bedroom for something and her friend apologized for what they had done and begged me not to tell the others that she had apologised because she had to keep up a reputation of being a bitch and then she told me that some girls preferred smaller dicks and said that any time I want her to suck it she would do it providing nobody was around to see and I didn't tell anyone. I said how about now and she unzipped me and gave me a very quick and satisfying blow job on the spot and almost got caught by my sister but I cleaned up just in time. I figured five out of eight ain't bad.

A month went by and I had all but forgotten about the incident though I was fixated on all the sex I was getting from crazy 8 girls. Several of the girls kept coming back for more of my "cute tiny dick." But there were two holdouts until that day when one of the two remaining girls came to apologize and told me not to say anything. She said that while my dick was way below average size, a lot of girls like that though she wasn't one of them but since she had been so mean, if I kept my mouth shut she'd do a strip show and let me touch her. Touching her meant playing with her tits while she sucked my dick. She said she still preferred bigger ones but she owed me at least that. She never came back and the last holdout never came to me with either an apology or an offer of sex. My sister meanwhile also apologized but not for another three years. she didn't offer me sex but why would she? she's my sister.

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