First Time Group Sex

My thanks to lesliejones for her review and editing assistance

[All characters in this story are over 18 and were over 18 at all times in the story.]

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I went to boarding school about two hours from my home city. Two years after I graduated, I was going to college on the West Coast at a school that didn't start until mid September. With nothing to do and most of my friends already gone to colleges that started in August I decided to drive down to my high school for the first football game of the year.

I was sitting in the stands close to two girls who had come to watch because one of them had been dating one of the football players over the summer. He was a senior, while they were freshman at one of the major universities in the state. Since they were not students at either my school or the corresponding girls' school in town, we started to talk during the game.

I found out that they were roommates and had only known each other since the school year had started a few weeks earlier. The girlfriend of the player was Annie, and her roommate was Carrie. Both were cute, but in different ways. Annie was a little taller, with long legs and blonde hair that fell halfway down her back. Carrie had dark hair that was naturally curly and shorter. Both looked sexy in jeans and tight shirts that were somewhat revealing.

I was sitting just behind them so when they turned to talk to me, I got a good look, and probably stared a little too much. At the time I was not a virgin but not far from that. I was a late bloomer so no action in high school at all, but my first year of college had been pretty good with a few short-term girlfriends and an introduction to what I missed in high school.

During the game Carrie was very flirty with me so when the game ended, I was a little disappointed to have to drive the two hours back home. They changed that when they asked if I wanted to go with them to a local bar after Annie's boyfriend showered and changed. We could drink beer at 18 in my state so there were a few places you could go in town to drink and play pool or listen to music, but not too many since it was a pretty small town.

Carrie and I got in my car, and Annie and Craig got in her car to go to town. They played pool and had a few beers, but I didn't drink because I was nervous about the two-hour drive back and needing to stay awake. They were giving me a hard time about joining them when Carrie said that I should stay over. She came close to me, gave me slow, soulful kiss, and said that she didn't want me driving home alone. The other two were laughing and said that I could join them in the room the girls had reserved in the motel that was across the street from the school. With that settled, I got a beer and loosened up a little, anticipating being in the room with Carrie.

We got back to the motel about 12 and sat around drinking and talking but that didn't last too long because Craig and Annie were starting to kiss and touch each other while we were talking. They got up and moved to one of the two beds in the room, then the kissing became more intense. Carrie and I sat on the other bed and watched, almost in silence as Craig removed Annie's top to reveal her beautiful, round, perky boobs with little inverted nipples that he was touching and kissing. Carrie sat close to me, with her hand on my leg, watching this progress. Craig had his hand inside Annie's jeans, massaging her pussy in little circles while they continued kissing passionately.

I turned to Carrie and told her how hot her kiss at the bar had been, then moved to bring her lips to mine. She had very full lips that were much softer to the touch than any of the girls I had kissed before. We alternated between kissing and watching Craig and Annie on the other bed. Annie had now removed her jeans and was just in panties. Craig had his hand inside and continued to use his finger on her pussy.

Of course, by now I was hard as a rock and enjoying the show with Carrie. She had moved her hand up my leg and was rubbing my cock on the outside of my jeans. I had my hand inside her shirt touching and circling her nipple with my thumb and index finger. The combination of her kissing and touching me while watching another couple was driving me crazy. Annie and Craig had spent the summer fucking, so they moved quickly to removing all clothes and starting to fuck. She got on all fours facing us as he entered her from behind. The look on her face was one of pure lust, her eyes rolling to the back of her head as he entered her.

Then she looked at me and motioned for me to take off my pants. Carrie immediately undid the buttons on my jeans, then took them and my underwear off in one quick motion. My cock jumped out at full attention, which Annie seemed to like to see as she was being fucked from behind on the other bed. Carrie took off her clothes so that I could see for the first time what I had been imagining all night. She had slender legs, a tight athletic ass and cute rounded boobs with slightly bigger nipples that were hard and tender to my touch.

Now that we were all naked, each couple were looking at the other two while playing. Craig had moved to his back and Annie was on top of him, facing us and watching me lick and suck on Carrie's hairy pussy as she rode my face. She was much more experienced than I was, so she rubbed back forth over my tongue while I tasted her sweet juices.

I couldn't see what was going on in the other bed, but Carrie and Annie were looking at each other as they sat up on top of Craig and I. Carrie was pinching her nipples while I licked her, then I heard Annie say she was coming, moaning and laughing at the same time. Craig must have come at about then because Carrie had moved from my tongue, down to my cock, to put me inside her. I could see that Craig and Annie had stopped, watching Carrie go up and down slowly on my shaft. At one point Annie moved over and kissed Carrie's nipples, then bent down and gave her a lick on the clit while I was inside her.

This was about all I could handle, and I think Carrie sensed this because she got off me quickly and began to lick my cock while she stroked the head up and down. Annie and Craig watched as I exploded in her hand, followed by her mouth where she took the second wave and all the spasms after, swallowing the combination of her juices and my cum. Annie came over and gave her a big kiss, then went back to Craig for round two.

Carrie told me she totally got off rubbing herself on my tongue, but she hoped I would be ready to go again so that she could ride me some more. It was probably 4 A.M. before we finally fell asleep. The next day I drove back, but not before getting their contact info. I had to drive to school the following weekend; since their university was right off the highway I needed to take, they invited me to come to see them the day before I was going to leave, then continue on from there. That night in their dorm room was also memorable, but that story is for a different day.