Heather's Night With The Boys

The following is my third story I've posted to Literotica and my third real life experience. My first two stories dealt with my sexual experiences involving my boyfriend at the time and his roommate and occurred about 3 years ago when I was 22.

I stopped dating Steve, my former boyfriend, about 6 weeks after my second threesome with him and his roommate Brian. The subsequent story occurred when I was 23 years old, about 1 year after my first threesome. Over the 10 months after I stopped seeing Steve, I dated a few different guys but nothing very serious. I certainly never came close to experiencing anything like those two amazing nights. That's not to say I didn't think about it. In fact, I thought about it a great deal. It's just that I wasn't prepared to walk into a bar and grab the first two guys I saw and tell them, 'You two, I need you to come with me.'

As I said, I was 23 years old when I met Damon. He was cute, but not the type of guy I usually dated. I tend to go for the well-built jock types and while Damon had a decent build, he wasn't huge. Damon was about 5' 10'' and 180 lbs. with dirty blonde hair and blue eyes. He was also kinda weird and very laid back. Anyway, we weren't super serious and definitely had a lot of fun together. I was in a pretty crazy stage at this point in my life as far as socializing goes, hitting the bars or clubs maybe 4 or 5 times a week. Often, the two of us went out with groups of my friends or groups of Damon's friends and sometimes both.

On this particular day in the late summer we had a bunch of friends over to Damon's apartment. There were about 20 people there and we did lots of drinking, dancing, listening to music, etc. This went on for most of the afternoon. At about 6:00 pm the last of our guests left. Damon and I had some more drinks and he asked if I was going to get ready for tonight

''Jason and Ben should be here in an hour so you might want to hop in the shower if you want to be ready before they get here.'' Said Damon.

Damon and I were planning on going out this evening to a few clubs with his friend Jason and Jason's roommate Ben. I had never met Ben before, but Jason, well let me tell you about him. I met Damon's friend, Jason, a few weeks after I began dating Damon. I was instantly attracted to him. I often wondered what would have happened if I had met Jason before Damon. Jason was definitely my type, about 6' 1'' and 195 lbs. and built like a model for a men's fitness magazine. He had short dark hair and gorgeous blue eyes. Jason and I flirted shamelessly, especially when Damon wasn't around, but it had never amounted to anything.

I finished my vodka and tonic and grabbed a bottle of beer as I headed to the bathroom and started the shower. The steaming water felt great cascading onto my body as I sipped the beer from the bottle and enjoyed my ever-increasing ''buzz''. I took my time shaving my legs and trimming my pubic hair to a small strip. I finished showering, turning off the water as I stepped out of the shower and dried my self off. I wrapped myself in a big towel and headed for the bedroom to get dressed. I undid the towel wrapped around my head and my red hair spilled out, just touching my shoulders. I'm not sure why, but for some reason, I decided to let the towel on my body fall to the floor, as I stood naked in front of the full-length mirror on the closet door. I was pleased with what I saw. My shapely legs took up a good bit of my 5' 5'' frame. I've always been built pretty well, but since beginning to work out regularly about a year and a half ago, my 110 lbs. were now distributed quite well across my body. I ran my fingers across my flat stomach and noticed how well my perky 34C breasts stood out. Finally, I went to my bag to decide what to wear tonight.

First I pulled out a pair of black thong panties and slipped them on. I had been turned on to them about 6 months ago, and after a few days of discomfort, I now loved how they felt. I also loved how guys went nuts when they saw them on me. Next I pulled a white bra out of my bag and strapped it on. It wasn't too fancy, but it did push my breasts together a bit, not that I needed the help, but I like to show some cleavage. Then I grabbed a short black leather mini-skirt I had just picked up and slid it on. It came down just a few inches past my butt and thanks to the thong, the leather felt quite sexy against my bare ass. Then I pulled out my shoes, a pair of black mules with an open toe and 3 inch heels and stepped into them. Next I pulled out a white blouse that fit pretty tightly and looked quite awesome with the top 2 buttons undone.

I came back out to the living room and Damon and I had a few more drinks. He commented on how nice I looked. Soon the doorbell rang and I hopped up to get the door. Jason and Ben were waiting on the other side.

''Wow! Great outfit Heather!'' said Jason excitedly, ''This is my roommate Ben.''

''Thanks, nice to meet you Ben.'' I said.

Ben seemed nice enough, but quiet. He was average looking, maybe 5' 9'' and 180 lbs. with blonde hair. Jason looked terrific as usual. He had on a pair of khaki shorts that showed off his hairy muscular legs and a black polo short.

''Damn! That skirt should be illegal!'' exclaimed Jason as he followed me into the living room.

I mentioned how we flirted frequently and he always commented when I wore anything particularly tight or revealing. It seemed like the skirt was a hit.

Well, we were only going to spend an hour or so at the apartment before heading out for the night, but that turned into about 3 hours. We were playing some drinking games and Jason seemed quite intent on getting me wasted, although I certainly didn't need the help. Finally, we decided it was time to hit the club.

We arrived at the club and didn't slow down a bit. We had a few drinks and I pulled Damon up on the dance floor with me a number of times, much to his dismay. It seemed like every time we got back to our table, Jason had a shot or a fresh drink waiting for me. After maybe an hour and a half of this we settled down at the table for a while. Sometimes, when I'm out with a group of Damon's friends, I'll try and find some women to hook them up with. I usually have no trouble finding someone for Jason, but tonight he didn't seem interested in any one I introduced him to. I remember pointing out this sexy blonde at one point, she had on a tight red dress and her breasts were practically spilling out of it.

''No, I don't think she's my type.'' Said Jason as he leaned towards me. Speaking directly into my ear now he said, ''But I'd love to see you in that dress. I bet you'd look fucking fabulous in it''

It was getting pretty late and we had all tied one on by now. I decided I wanted to dance again before the club closed, but Damon didn't want to dance anymore. Instead he turned to Jason and asked him to join me.

''Jason, take Heather and go dance with her, will ya? I've had my share of dancing tonight.'' Damon said.

Jason took my hand and followed me onto the dance floor. It was quite crowded so we were very close, not that I was complaining. By the second song are bodies were separated by mere inches. Thanks to the alcohol, I had no inhibitions and I felt Jason's eyes blazing into me. His hand moved to my hip, slid down and under my skirt, and back up to my ass. Jason's eyes widened as he felt my exposed ass, I smiled and leaned into him, burying my head in his chest. Jason pulled me close to him and I felt his growing hard-on as our hips pressed against each other. Our bodies began to sway together to the music. I felt Jason's hot breath on my neck as he began to nibble on my earlobe. Suddenly, I felt someone pressing up against me from behind. I turned to see Damon with a sly smile on his face. He leaned forward and kissed me passionately. The three of us continued to dance and grind against each other for the next two or three songs. My head spun as I considered the possibilities. Finally, as the club started closing, Jason and Damon led me to the car for the ride home.

Ben got in to drive and I sat in the back between Damon and Jason. I don't think I breathed for the first 5 minutes of the ride, and then Damon put his hand on my left leg and ran in up my thigh and under my skirt. I turned and pressed my lips against his. I reached back to Jason who had moved his hand to my right thigh. My tongue was entwined with Damon's as he slid his hand inside my thong, feeling for my clit. Jason had moved his hands up to my blouse, undoing a few buttons and reaching into my bra. I reached back and placed my right hand on the bulge in his shorts. I moved my left hand to Damon's crotch and began to unzip his fly as he slid his finger into my pussy.

''My God Heather they are so beautiful!'' Jason exclaimed as he freed my breasts and leaned forward to place his mouth on them.

I grabbed Jason's hand to help me unzip his fly and grabbed his cock as it sprang out from his shorts. It felt so full and hard in my hand and Jason moaned as I grabbed it. Damon was now working his middle finger into my cunt as he continued to stroke my clit with his thumb. I now had both of their cocks in my hands, stroking them furiously. We carried on like this for another 10 minutes or so, groaning and stroking, but no one quite going over the edge.

We pulled into Damon's apartment complex and he stopped to zip back up. Jason did the same and helped me button my blouse and pull my skirt back down. Ben parked and the four of us headed into Damon's apartment. Damon went to make us drinks, Ben turned on some music, and Jason and I started to slow dance. As we danced, I reached up and began softly kissing Jason. I soon felt Damon behind me pressing his hard-on into me and lifting up my hair to kiss the back of my neck. I was so excited I began kissing Jason feverishly and he responded. I reached down and felt between his legs, grabbing his bulge. Damon's left hand groped my breast through my blouse as his right hand began pushing down on my shoulder. I went to my knees, looking up at Jason as I undid his belt and fly. I pulled his shorts and boxers down and his giant cock (maybe 8 ½ inches) popped out, standing almost straight up in the air. I trembled a bit as I reached forward, and as I wrapped my fingers around it, his cock looked huge in my small hand. I slowly began running my hand up and down his beautiful shaft and Jason started to moan softly. Then I opened my mouth and ran my tongue all over the head of Jason's cock, causing him to cry out.

''Oh Shit Heather, that feels so fucking good!''

Feeling crazed with sexuality, I reached down with my left hand to finger my throbbing clit. Just as I did this, I felt Damon behind me move his hands under my skirt and grab my thong underwear, pulling them over my but and off my legs. Damon moved my legs apart slightly and slid beneath me on his back. He grabbed his my ass in both hands and began running his tongue across my clit. I felt my orgasm approaching as I grinded my hips into Damon. I stopped licking Jason's cock to cry out in pleasure but continued to stroke him with my hand.

''Oh Oh Oh Shit Yes! Oh My God!'' I wailed as I came for the first time.

As I was screaming Jason reached down and undid a few buttons of my blouse, pulling my tits out of my bra. After I finished cumming he moved my head back to his dick. I turned back to him and took his cock as deep as I could in my mouth, pulling him closer to me by grabbing his ass. I greedily bobbed my head up and down on his wonderful prick. I was now sucking hard and fast and pumping Jason's cock with my hand as I slurped him; trying to make him cum. Jason reached for my head and stopped me.

I stopped and looked across the room to see Ben sitting on the couch. I had completely forgotten about him. He was sitting with his legs slightly spread and had an obvious hard-on. Now I had been constantly thinking about having sex with 2 men again in the past year, but had never even imagined 3. Considering the frenzied state I was in I wasn't surprised when I said something like the following.

''Well are you going to sit there and watch us all night or are you going to join us?''

Ben's jaw dropped, then he hopped up and walked toward us, standing next to Jason. Ben began fumbling with his belt, trying to remove his pants. I looked up and Jason was stroking his cock slowly as smiled at me. Damon was still beneath me licking my wet pussy. Ben's pants fell to his ankles and his 6-½ inch penis stood at attention. I grasped Ben in my right hand and took him in my mouth. I alternated between Jason and Ben for a few minutes, sucking one while stroking the other, until Damon finally gave my pussy a break and pulled me to my feet.

My head swam with possibilities and scenarios as the 3 studs led me to the bedroom. Damon stood beside me and pulled my tight skirt over my ass and off my legs. Jason finished unbuttoning my blouse and removed my bra, fully exposing my breasts.

''Oh shit, they are amazing!'' said Ben.

Damon leaned forward and whispered something to Jason. Jason smiled at me as he pulled his shirt over his head. He lay on the bed on his back, looking like a Greek god, with his cock curved up to his stomach. Damon bent to me and placed his lips just above my ear.

''You want to fuck him don't you? Why don't you climb on top of him and ride his cock?'' Damon whispered into my ear.

I tried to speak, but could not form words in my mouth. I approached the bed and climbed on top of Jason, straddling him. Jason moved his hands from my hips to my chest and began kneading my breasts. I moved my hands up his hard stomach to his muscular chest. I leaned forward and pressed my lips against Jason's, plunging my tongue into his mouth. I felt his cock pressing up against my ass and I tried to move him inside of me.

''Wait, sit up baby, I want to see you.'' Said Jason.

I sat up and Jason moved his hands under my ass, easily holding me just above his cock, which I held in my hand. Jason gradually lowered me onto his pole. I was extremely wet but the Jason's thick cock did not go in easily. Jason slowly worked his cock into me, at first just an inch or two, then three or four.

''Oh, Oh, Oh God! Yes Baby!'' I moaned out loud as Jason began bouncing me up and down on his cock.

He began sliding deeper into me, now five and six inches at a time. I was pinching my left nipple and fingering my clit as Jason was thrusting up into me. I looked up to see Ben, naked and standing next to us beside the bed. His eyes were transfixed on my tits as they bounced up and down with each of Jason's thrusts. He reached out and grasped my right breast and I took his cock in my right hand.

Jason was now moving me quicker, pumping nearly all of his 8-½ inches deep into my pussy. I felt another orgasm approaching until Jason began to slow his pace. Damon was behind me now, pushing me forward so I was lying on Jason's chest. Damon began spreading my ass and working a finger into my asshole. I realized what he meant to do and I was a bit scared. Damon seemed to enjoy anal sex quite a bit. Personally, I don't mind it I get worked up enough, although it wasn't something we did more than once every few weeks. Also, in my two previous threesomes, neither involved anal, so I couldn't fathom what this was going to feel like. Damon had about 3 inches of his finger in my ass. He removed it and placed the head of his cock against my asshole. I started moaning softly. Meanwhile, Jason had pulled his cock almost completely out of my pussy and was whispering softly in my ear.

''Its ok baby, just relax. Its ok.'' Jason said lovingly.

Damon began to force his cock into my ass now. An inch, then 2 and then 3. I started moaning loudly and Damon responded with some hot dirty talk, he usually enjoyed that and I liked it as well sometimes.

''That's it Heather, take it you Bitch! Take my cock in your ass!'' Damon sneered.

Finally, Damon plunged all 7 inches of his cock into my ass. He did this again and then a third time. The fourth time he did this, Jason joined him by thrusting all 8 ½ inches of his cock into my pussy. I came violently. I can't describe the sound I made, but Jason later told me it was like the sound a nail makes when it is being pulled from a piece of wood. They remained like this for a few moments and then Ben came forward and thrust his dick into my mouth, quieting my screams. I sucked him hard as Damon and Jason now alternated their assault on my ass and pussy. Damon was thrusting hard now and digging his nails into my ass cheeks. He pulled out and began cumming all over my ass. Jason continued plunging deep into my pussy. He soon began to pant and effortlessly lifted me off his cock as cum shot from his prick, sailing into the air and landing on my stomach and tits and his chest. I immediately fell upon him, trying to catch my breath.

I sensed the men moving about and felt Damon sliding me towards him and off of Jason. I realized this evening was far from over. Damon put me on my side, straddling my left leg and holding my right leg up in the air on his shoulder. Damon leaned forward, rubbing his hardening erection up and down my wet slit. Jason was on knees on the bed, right beside my head, his cock, now semi-erect between his legs. Jason began to caress my right breast. I took Jason's cock in my mouth, licking the remaining cum off of it. Damon lifted my leg and drove his hard manhood into my pussy. He began to fuck me slow and hard. Ben was behind me now, his cock pushing clumsily against my ass cheeks. Damon reached down and started rubbing my clit intensely while he continued to fuck me hard. Again an orgasm approached and I took Jason deep inside my mouth. Ben now worked his dick into my ass; it slid in easily after Damon had just fucked it. Ben pumped my ass a few times between Damon's strokes and started moaning, pulling out and cumming. Jason's cock now was growing hard again in my mouth. Jason began pinching my nipples and I verbalized my approval as I tried to keep all of his cock in my mouth.

''Mm hmm! Mm hmm! Mm hmmpf!'' I uttered, keeping Jason's prick between my lips.

''That's it you little slut, suck on that big cock!'' said Damon.

Damon crashed into my pussy with amazing force, rubbing my clit vigorously. This, and Jason squeezing my nipples hard, drove me over the edge as I came yet again, my whole body going rigid. Jason managed to pry his cock from my lips and I gasped for air through my mouth.

I tried to stop my head from spinning as I whined, whimpered, and cried, ''Oh my God you guys! Oh my God you sons of bitches!''

Damon was moving me again now, getting me on all fours on the edge of the bed. I was between his spread legs and his hard erection stood up in the air.

''Come on Baby. Take me in your mouth like a good little slut.'' He said.

I wearily reached for his shaft and stroked him as I sucked his cock into my mouth. I was exhausted so I worked his cock hard, trying to get him to cum quickly. Damon was trying to hold out, talking dirty and enjoying the moment. I felt someone grab my hips and pull me back. My feet were now on the floor as Damon scooted forward to the edge of the bed and I continued to suck him. Ben was beneath me, on his back, his dick pointing up at me. I came down on him hard, his dick easily entering my pussy. Ben reached up and grabbed my big tits, squeezing them hard. I rode him feverishly for the next 5 minutes or so with Damon's prick still deep in my mouth. I looked for Jason and found him next to us watching me, with his cock still rock hard from me sucking him.

''Well, what are you waiting for?'' I said, motioning to my backside.

''No baby.'' Said Jason, shaking his head.

''What!'' I exclaimed. ''No! Fuck my ass baby! Please!'' I had never said this before, but I crazed at this point.