I was lying on my back looking up at my best friend’s gentle, smiling face. He was sexually experienced and I was not. But I guess I had known for a while that if anybody was going to take my virginity it was him. We had known each other since we met in pre-school. After our mothers found our families lived just five blocks from each other, the inevitable car pools and play dates began. It was fine with Glen and me, we seemed to take to each other immediately. When we started kindergarten together, we clung to each other for security until we settled into our new surroundings.
Our friendship continued all the way into high school and college. By freshman year, many of my girlfriends were experimenting with sex. The reviews were varied, some loved it, some thought it was over rated. Regardless, I was eager to try it. I finished my freshman year with my virginity intact but as summer vacation progressed, my two closest girl friends took the big plunge.
Katie, my tall, beautiful blonde friend with spectacular long legs had sex with a guy at soccer camp then followed up with a long, satisfying afternoon in bed with her college aged neighbor. Alisha, my drop dead gorgeous brunette friend with magnificent 35D breasts had sex with her grandparent’s neighbor’s son, with a guy at cheerleader’s camp, then had a threesome with two guys she knew from the town where her family had a summer home. The beauty of their situations is that they found guys who didn’t go to school with us so they were able to keep their sexual encounters a secret from anybody that shouldn’t know.
I hadn’t found the right situation for giving my virginity away. It’s not that I didn’t have some chances. I’m not as classically beautiful as my two best girl friends – they both have faces that belong on fashion magazine covers – but I am cute. I’m blonde with a round baby face, big green eyes, a button nose and an infectious dimpled smile. Body wise, I’m not blessed with big breasts or long, gorgeous legs. I’m barely 5 feet tall and my measurements are 33A-22-32. While I’m not exactly voluptuous, I have enough curves to look good in a bikini, and I have pretty if not long legs and a great ass. I had my share of older guys flirt with me or even make out right propositions, but I didn’t want to just be a convenient fuck for some upper classman trying to add to his yearly scorecard.
So it was late in the summer, just two weeks before school was scheduled to start again and I was having some anxiety about being the only virgin in my crowd of girl friends. I had been thinking about asking Glen to make love with me before school started up but I wasn’t sure how to broach the topic.
I went over to Glen’s house to splash around in his above ground pool like I had done many times before. It wasn’t really a swimming pool, it was only 4 feet deep and 12 feet across, but it was fine for keeping cool. As he and I floated around on inner tubes, three guys showed up. Dave, Glen’s cousin, Robbie and Kenny, two friends from school. They plunged into the pool creating a huge splash and wave, than they intentionally flipped my inner tube. I was accustomed to rough housing with the guys and we were soon all splashing and dunking each other.
Somewhere in our game, my top came loose and it was dangling down exposing my cute but small tits. Of course I covered up by crossing my arms in front of me and I was sooooooo embarrassed, The guys made jokes, I think it was Dave who said they’re like breasts only smaller.
I defiance I dropped my arms and exposed my tits. They might be small but they are nicely shaped. I have small, perky, pinkish/tan nipples and perfectly round nickel sized circles surrounding them. They are cute. My flat tummy and lean narrow waist made me look sexy, especially to four horny high school guys.
I stood there for a moment, wavering between feeling sexy and frightened. Glen asked what I was doing and I responded by saying that they might make fun of my smallish sized tits, but they were still looking at them. Dave said they’re cute and that he wasn’t seriously trying to make fun of them. I looked at him and smiled saying “So do you really think they’re cute?”. He reached over and gently squeezed my right breast in response. Next thing I knew Glen was gently caressing left side.
It wasn’t long before I was having my breasts sucked for the first time and the warmth of those lips and tongues felt so good.
Soon we were heading into the house and my bikini briefs were being gently slipped down my legs. My sparse patch of fine blonde pubic hair was dark and plastered down with pool water, and Robby, who was sitting remarked that he could see my lips. He told me to sit down and give them all a better look. I complied without hesitating.
The guys took turns exploring my small pussy. I do have a pretty little pussy, with small delicate lips that press tight together. I knew they were probably swollen with excitement, but even then they are still small and tight looking. Each gently finger banged me then tasted me. I knew for a fact that Glen had fucked two other girls by then, and the other guys claimed to be experienced and I had no reason to doubt them. Glen asked me if I wanted to finally go all the way, and Kenny added “With all of us?”
This isn’t how I had envisioned my first time. I thought it would be romantic, with a much older guy who had the looks and body of a male model/super athlete. But I nodded to let them know I was ready to find out what all the fuss was about.
We were in the family room and Glen ran to get a big towel to spread on the couch to prevent staining it with sexual fluids, or maybe even blood. He also grabbed tube of spermicide cream from his sister’s stash. The guys grabbed a pair of dice from some game and they rolled to see who got to go first. I was hoping it would be Glen, and it was.
I had never seen an erect penis, or even a mature penis. I had baby sat but an undeveloped ½ inch organ isn’t anything like a full grown, erect dick. I was looking at four of them. Luckily, none of the guys was exactly huge.
Glen had me lie down and spread my legs wide while he squeezed some of the contraceptive cream into me. It’s strange that I didn’t perform oral sex on any of them.
Glen then stretched out on top of me and asked if I was sure I wanted to do this. He said nobody was going to force me. I looked at the other guys, and they nodded in agreement, I could get up and get dressed if I wanted to, but I didn’t want to.
I told him to “Just go ahead and do it.” He reached down and guided his penis toward my tight little pussy. The head felt so warm and soft and smooth against my labia. He gently worked it in and I was surprised that it was painless. It didn’t take long for me to feel his crotch pressed firmly against mine. He just lingered there for a while and it felt nice. He asked me if I was OK, “I didn’t hurt you did I?”
I told him I was fine and he began stroking in and out of me, kind of slow and tentative at first. It was feeling really good, in fact I think I was on the verge of an orgasm when he stopped stroking and shoved deep into me. I felt his penis start to throb and twitch, and then I felt his cum squirting into me. It was so nice to know that I could give a guy an orgasm.
He said “Oh God guys, you’re gonna love this, she’s so good.” One by one, each of the other three guys took his turn, and each was just as gentle with me.
Robbie said “Oh man, you have not idea how awesome a pussy you have.” He did bring me to an orgasm.
So my pussy was “awesome”. I can’t describe how much loved hearing that. Kenny told me it’s so soft inside.
Each guy filled me with his cum, than came back for seconds. I got to experience missionary, doggie and cowgirl position sex that day. I had never imagined that my first sexual experience would be a gang bang.
The next day I went over and let all four of them make love with me again and I continued to pull train for all of until we all graduated. I also had one on one lovemaking sessions with each of them. Sometimes other guys joined us in the gang bangs, there were several times when I had sex with 8 guys at a time. I had sex with my share of other guys too, generally guys from outside of my school. The original four guys, and the few guys from school who we let join us were all willing to keep our sessions secret.
I’m now in my second year of college, and I have had several gang bang experiences here on campus, once taking on 14 guys in a row at a fraternity party. I know getting gang banged isn’t for everybody, but if you have ever contemplated it, I highly recommend it.
– The End –