Topic: playing dress up lead to my first anal gang bangAt age 18 I had already had sex with severval girls. But was still alittle confused about my body. It was alittle girlie. I was 5' 6" and 124lbs. And both the boys and the girls would tell me what a nice ass I had. I was pretty much straight. That was except when it came to my best friend Matt. Matt had the most beautiful cock in the school. I looked at everyones in the shower. It's was about 8" and not too thick. Nice balls to go with it. Jim my other friend had the biggest. 18 0r 12"s easy. but it was ugly. The rest of my other 4 friends were average. But Matt was the one I would sometimes beat off to.
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One day all 6 of us were at Matt's house all drinking beere and smoking pot. When Monica, Matt's fine older sister asked if she could dress me up. What the hell it's summer and just to be near her. Plus I had a good buzz going. It did not take her long. I looked fine. I just stared at myself in the minnor. Tight t-shirt with a nicely stuff bra. Black mini showing of my newly shaven legs. Flat stomach, no bulge. She made me wear a jockstrap. Which she had painted the jock black to look like pussy hair. I looked like a girl. During the whole make over Monica was feeding me beers and shots after shots. Now she planted a big wet kiss on me and said" watch and learn".
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She was then on her knees giving me the best blowjob I ever had. Before I knew it I was unloading a large amount of cum in her mouth. I almost passed out. As she lead me out to the guys she wispered to me " Your are going to have cock in you all night, enjoy".
The guys just froze. Nobody said a word. Then Jim yelled "Me first!". He came over and gave me a big hug and trying to kiss me on the mouth. I pushed him away and everyone started laughing. The party had grown as it was dark now. All the guys were hitting on me, trying to feel me up alittle. It was weird at first but the more I drank the more I enjoyed it. Then Matt pulled me close to him face to face. His body was hard and strong as I weakened against him. His hand quickly found my ass and began to squeeze.
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I just allowed him. Then he started to push me towards his bedroom. He was kissing my neck and both hands were under my skirt by the time we entered his room. I could hear the music from the party fade into the back ground as I tried to focus on Matt. He was just a blur. I was so drunk at this piont I could not see straight. But that didn't stop me from knowing that my best friend was going to fuck my ass. Matt was on top of me between my legs dry humping me. We were kissing eachother wildly. Then he yanked of my little panties and threw them in to the corner. Her placed my legs over his shoulders and began to take his cock out. My legs began to shake, I was so scared. All the girls I've talked to said that the first time hurt like hell. Matt spit on his cock then placed it against my virgen hole. Then he just jammed it in.
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I let out a scream. It hurt good. "put it all in Matt" I heard myself beg. He pulled back then filled me up with his big cock. Thank God I was so drunk. Cause Matt just pounded my ass. And I just loved it. I wanted him to slow down so I could enjoy the feeling of his cock but it was over. He was shooting his cum deep into me. It felt hot and wet and I could feel his cock pulsing inside of me. Then he quickly jumped off of me and left the room. There I was freshly fuck. Cum oozing out of my ass and strangely wanting more. As I got up to find my panties I straighten myself out. I picked up my panties from the corner.
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As I tried to turn around when someone grabbed me from behind. I could not see who it was because it was dark and my vision was still blurred. He was strong. I did not even try to fight him. He took me back to the bed and bent me over it. His cock slipped in easy do to being smaller than Matt's . And all of Matt lube. I looked back to try to see who was fucking me. All I saw was how hot my ass looked as I was being fucked. I looked sexy as hell. He must of thought so too. Cause he was now unloading his nuts in me. I loved the feeling of being squirted in. He pulled out and gone before I could turn around. Now as I wiped his cum from running down my legs.
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I was dissapointed. 2 guys 2 minutes. Then I looked up. Jim was standing there with his huge close to my face. And a evil grin on hie face. "Watch and learn" I heard Monica say. I had that monster cock in my mouth before he knew what was going on. It tastes great. And the feeling of his soft skin tight around his hard shaft was great. I worked about 6" of Jim's cock with my mouth. Then yanked me away "next time I'll cum in your mouth. Right now I want that ass. ". I felt sick as I was laying back on the bed. Jim's cock looked way too big and mean.
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Like it was going to hurt this time. No matter how drunk I was. Then he ripped through me. I screamed out of pain this time. It hurt like hell. He just held there. Making sure I felt every inch. Then to my suprise he started fucking me very gentle. Almost caringly. The tears were rolling down my cheeks as his huge manhood stretched me out. It felt like I was going to shit myself. He began to make love to me. Not just pound me like the other two. His hips began to grind side to side. He was kissing me softly on my mouth and neck.
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Telling me how much he love my asshole. How good I felt. This did not stop it from hurting but it sure turned me on. I began to suck on his neck and grind my hips up to meet his downward thrust. Making him go even deeper into me. To my suprise I loved that big bone buried inside of me. I was enjoying the pain now. Even wanting it. I just lost control. The thought of this huge cock going in and out of me was too much. "Don't move Jim". Jim held still as I rode in and down his hot meat. It slipped in an out with some ease. I was cumming. My cock was not even fully hard and I was cumming my jockstrap.
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Jim must of felt this and took over. He pinned me down for his final assualt. Man. he puonded me deep. Causing me to scream in pain from is cock. And pleasure from causing me to cum even more. Then he unloaded in me. It felt like he was peeing in me. Then he pulled out. Squeezing his cock he brought it up to my mouth. Once it was in my mouth he let go. Sending his final loads into my mouth. As I swollowed it all I was turned on by how big his cock was and that I was able to take it all. We cleaned up and went back to the party, minus my panties.
Everyone high fived Jim.
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Cause they knew that he broke me in good. Then they all just pasted me around. Like Monica said I'll have alot of cock in me. I sure did.
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