My girlfriend Katie and I had been friends since second grade and serious boyfriend/girlfriend since High School. Katie was girl-next-door pretty and stood 5’8″ tall, weight 120 pounds, had dark blonde hair and brown eyes. All they guys were always complimenting me on her great body. We went steady throughout High School and were always a couple. Along the way we had experimented sexually and eventually consummated the relationship, several times. Katie was on the pill and had parents who trusted her completely so we had many opportunities others might not have had. It was a wonderful relationship for a somewhat shy High School boy as I was. For better or worse we were the only sex partners either had when we graduated High School.
Katie and I had selected different colleges and this caused her great anxiety. As we would be several hundred miles apart, we agreed we should see other people at college. She was concerned that as we had been together so long she was not sure even how to act on a date with someone else or what to expect from other boys. I shared some of those anxieties and frankly was looking forward to “seeing” some other girls for variety. I really liked Katie and I knew she liked me but there was a lot of life or us to experience. We knew what each other liked sexually but were not sure what to expect from others. This really bothered Katie as she had discovered she REALLY liked sex but didn’t want to be embarrassed or damage our relationship. She was just so uncertain.
I had hung out in High School, when not with Katie, with a “gang” of three guys. We even had a combination clubhouse/apartment over a garage at one of their parent’s houses that used to be servants quarters. All of us came from fairly well to do families. Ken was a good looking 6’2″, dark haired, guy whose dad owned a construction company. Ken was not going to college, as he was not much of a student but rather into the family business. He would be leaving in the fall for his first job with the company, several hundred miles away. Herb was an average, good-looking thin kid whose Mom and Dad were both well-known doctors and lived in a mansion with the aforementioned garage/apartment we used. He was going to an Ivy League school to study medicine. If anything he was kind of a nerd. George was my oldest friend who was going to Notre Dame in the Fall. George was the least good looking of the group, a bit short and stocky and quite shy. He dated the least of the group. As noted, Katie was going to College locally and I was going several hundred miles away. While Katie was not a full fledged “gang” member she knew the guys well as we hung around together throughout our High School years when I wasn’t with her. As noted, they all had dated to some degree but none had a serious relationship such as ours. We all knew our friendships would probably change dramatically as we went our separate ways.
Katie and I were driving around town in her convertible one hot late summer night, enjoying several beers and getting ready to leave for college. She had become more and more obsessed with her concerns on lack of experience dating, with sex and with other boys and the beer caused her to talk more about it. Admittedly it was driving me a little nuts. I feared that Katie and I were growing a bit apart. I told her I wanted to go to see the guys at the apartment and asked if she wanted me to drop her off at home.
She said she would come along, as she had nothing else to do. I had just turned 18 so I picked up a couple more six packs of beer and we were soon at Herby’s. The house was dark as his parents were apparently out but I could see light in the apartment and the guy’s cars were there. Katie and I went upstairs and found Herb and George playing pool and Ken watching baseball TV. There already had beer so I threw the six packs in the frig, grabbed another one for Katie and I sat on the couch watching TV with Ken. Soon Herb and George finished their game and sat down with us. We got to talking about the future. We were all excited but anxious about what was ahead for us. The beer must have affected Katie as she opened up to the guys about her anxiety about never having been with other guys much. I rolled my eyes but Ken grinned at me and said he would be glad to help if she and I had not been such a number for so long. I laughed and said whatever she wanted was OK with me if it got her off the subject and I could get back to baseball. Katie smiled, got up and grabbed another beer. When she got back, she sat next to Ken, looked at me and said:
“Would it really be OK with you if Ken and I got it on?”
I was a bit surprised with her comment but not taken back.
“Why not,” I replied. “We know how we feel about each other and I know your concerns about what the next few years hold for you dating-wise. And besides, these are my best friends. Who better to learn from if you really want to party?”
Katie looked a little confused for a moment. I think she may have been playing mind games with me and did not get the answer she at first expected. And she had said “Ken” but I had brought the whole group in. She drained the beer (she usually doesn’t drink much but this was her sixth, a record for her) took a deep breath and said, “OK. Let’s do this. What next?”
We all kind of looked around at each other nervously. I could see from growing bulges in each of the guys pants that they were for this. As Katie had been my girl I felt I should take charge. I slowly walked over and helped her stand up. I gave her a long, passionate kiss. I then pulled back and started to unbutton her blouse. With the last button undone, I slid it down her arms, leaving her there in just her bra and shorts. I asked her one more time:
“Are you sure this is what you want?”
“Yea, I’m sure” she replied. She had a wild look of excitement and anticipation in her eyes I had never seen before. I could tell she was getting hot.
I reached around and undid her bra and slid if off. She was now naked from the waist up. She has slightly different sized breasts as the result of a youthful operation but that somehow turned me on. The guys whistled in admiration of her gently swaying tits. I could see their hands unzipping pants and stroking dicks. I then slid her shorts and bikini panties down her legs in one motion. She kicked off her sandals and stood naked in front of my three best friends. The guys immediately surrounded her and kissed her while they explored her every opening and great tits. She threw her arms around each of them in turn and engaged in a slurping French kiss with each. While all this was going on Ken had stepped back, stripped and was stroking a massive 9″, thick cock. There was pure lust in his eyes. Katie turned her attention to him, slowly walked over, dropped down on all fours, and began licking his dick and balls. Soon she had as much of it as she could handle in her mouth and was sucking furiously. George and Herb were now both also totally naked and each was fondling a drooping tit, squeezing and pulling on her nipples as they hung down. I had an erection pushing so hard through my pants that it hurt. I could not believe how into it Katie was. Soon Ken pulled out of Katie’s mouth and lay back on the floor, pulling her on top of him. He had her mount his cock and then worked it slowly into her pussy. She was dripping wet and had little problem taking it all the way until her ass checks were bouncing off his balls. Herb placed his 8″cock at her lips and she readily opened up and began to suck again. For the first time Katie had not only strange cock but also two holes penetrated at the same time. Katie rocked on Ken’s dick while sucking hard on Herb. She was in another world. George continued to suck and fondle her tits until red welts appeared in several places and her nipples went purple. I removed my pants now and was slowly stroking my own 7″ cock at the scene before me. Herb came first and exploded in Katie’s mouth with a guttural groan. She was good at cock sucking but being doubly used for the first time excited her and magnified her first climax. A shudder went through her body as she swallowed as much cum as she could. I was now ready to explode so I walked over and slipped my cock in her mouth. She glanced up at me, smiled with her eyes, and took it deep in her throat. She was really liking this. Ken started pounding harder and soon popped a massive load into her hot pussy. As he lay there, he slowly pulled his now semi-hard cock from her pussy, moving his attention to her now aching, swaying tits. George was standing next to her now furiously pounding his rather slim 4″ cock. A crazy idea came into my head and I suggested George move behind Katie to maximize his pleasure in a tighter spot. I had him spit in his hand and told him to rub it on her ass hole and his dick. A look of first confusion and then fear appeared in Katie’s eyes but she kept sucking away on me. George quickly got the idea and did as instructed. He placed his small cock at her ass hole and pushed it in. Katie initially jerked in pain as she had never been fucked in the ass before but after a few moments relaxed as the pain was replaced with a sense of fullness. George worked it in slowly, caught the rhythm and rocked with the two of us. Katie seemed lost in the moment, eyes closed, and moaning softly. My guess was George had been a while between sex as he came almost immediately, filling her ass hole with his hot cum. He pulled out with a sense of huge satisfaction on his face. I could feel the gusher coming so at the last minute pulled out and came all over her hair and face. Katie sat there motionless, eyes still closed and on all fours while cum dripped off her face, out of the corners of her mouth and out of her pussy and ass. Herb got to his knees and gently rolled her on her back. He placed his now again hard dick between her oddly shaped tits. She squeezed them together and using the spent and readily available cum as lubricant he stroked back and forth. Soon another load of jizz was deposited on her chest and face. Katie collapsed, looking incredibly content with a huge smile on her shinny face.
Being young, we all recovered quickly. Cocks began to spring back to life and we got back into the action. Several more beers were consumed. Katie seemed to have two for every one we had (probably all that salty seaman) and was flying high. It seemed like at least one of the guys was always ready and Katie was still incredibly horny. I guess she was making up for four years of just one sex partner. At one point Katie was even bent over the pool table and taken from behind by Herb and then George. Ken tried, unsuccessfully, to get his 9″ dick up her ass so settled for a promise of blowjob. Cum dripped from Kati’s tits and face onto the green felt table. George was thoroughly plastered now and decided she need a diversion. Katie was up for any and everything so a pool cue was lubricated with glycerin Herb’s dad had in a storage box in the apartment and inserted first in her pussy and then her now stretched asshole as far as it would go. She squealed like a pig and eyes rolled back in her head as it was pumped in and out. The sight of this kinky insertion brought all the cocks back to life and Katie spent the remainder of the evening servicing them all with her mouth, pussy and tits. Finally, naked and exhausted, she went from guy to guy thanking them with a long, passionate kiss and one last chance to feel her up. She washed herself off in the bathroom and then put on her blouse, slacks and sandals. She threw her underwear and bra in the paper bag the beer came in. Everyone agreed she would no longer have to worry about inexperience in dating in collage. As we drove home Katie continually thanked me for being so understanding and caring. She said she was at ease with the future. I think we both kind of knew this was the beginning of the end for us. College awaited and we would be far apart. We agreed to let whatever happens happen. It had been a great ride.