Chrissy was the daughter of friends of my parents. They lived in Michigan and Chrissy went to a Catholic girls' boarding school in upstate New York, so she would visit us on short school holidays, like three-day weekends, when it was impractical and too expensive to go back to Michigan.
When Chrissy was a senior after she turned 18, I found out from friends that every time she came to our house, she would fuck one of my friends. She had never come on to me, but, of course, as a horny teen I was intrigued.
One weekend when Chrissy was visiting, I had my friend, Tommy, from New York City staying over. We went out with some of my friends. Chrissy was the only girl among five boys. During the ride, she began to make out with one of my friends, passionately. It was a little uncomfortable, and we tried to ignore them.
After I dropped off my friends, it was just Chrissy, Tommy and me in the car. I commented to Chrissy that she had gotten all worked up but hadn't had a release. I told her Tommy and I could take care of that if she wanted. Chrissy quickly consented and I drove to a small, deserted park in a secluded part of town.
I took a blanket from the trunk and we walked over to a dark corner of the park where we couldn't be observed. Chrissy quickly shed her clothes and got on her knees. Tommy and I produced our cocks and Chrissy went to work sucking us off. She had an amazing technique and was obviously quite experienced at sucking cock.
She would move back and forth from one cock to the other, careful to switch when it seemed like one of us was about to come. I got on the ground on my back and told Chrissy to mount me. She straddled me and lowered her cunt onto my pulsing cock. Tommy moved over her and she continued to blow him.
Tommy couldn't last any longer and shot his enormous teenage load into her mouth. So much cum exploded into Chrissy's mouth that she couldn't contain it all and some leaked onto her tits. Chrissy began grinding in earnest on my cock and it wasn't long before I shot my load into her.
I rolled Chrissy off and onto her back and Tommy and I took turns licking her clit and fingering her cunt. I love cunnilingus, even with a cunt full of cum. Chrissy was anxious to have her fun and it didn't take long for her to cum in an explosive orgasm.
We all lay there recuperating, contented in the afterglow of amazing sex. As two 18-year-old boys, it didn't take long for us to be hard and ready for more action. This time, Tommy laid on his back and Chrissy took him into her pussy for sloppy seconds. I got behind and bent her forward. I began reaming her brown, wrinkled hole until it was nice and wet and pliant. I slowly inserted my cock and waited for her sphincter to give way. Chrissy's asshole slowly opened up and admitted my cock. I slowly pushed it in while Chrissy continued to fuck Tommy.
I pushed my cock in all the way, to the hilt. It was amazing. I could feel Tommy's cock in her pussy thrusting away. I began to push in and out, filling Chrissy's ass. Chrissy groaned, in pain and pleasure. She never asked me to stop or ease up. I asked her if she was alright and she moaned contently and said, "Keep going."
That was all the encouragement I need to pound away in her ass. Meanwhile, Tommy groaned and I could feel him cum inside her. I continued to pound away at Chrissy's ass until I eventually couldn't hold back and shot my load up her ass.
After we recovered, we dressed and drove back to my house. The next day, both Chrissy and Tommy left. We exchanged knowing smiles, but didn't discuss the events of the previous evening.
I called Chrissy's dorm a few days later to see how she was doing. The person who answered the phone went and got her and we started talking. Chrissy told me that her friend was turning 18 and wanted to lose her virginity for her birthday. Chrissy asked me if I was willing to oblige. I assured her I was and told Chrissy to take her to a doctor to get contraception and, in the meantime, I would bring condoms.
I drove up to the town in upstate NY where their school was and got a room at a motel. I got the room in the back farthest from any other occupied rooms so we could have our fun unmolested and the girls wouldn't be seen entering the motel.
Chrissy and Ginny showed up about an hour later. Chrissy embraced me with a long passionate kiss. I reached behind her and raised her school skirt. Sure enough, she wasn't wearing any underwear and I grabbed and kneaded her buttocks while we kissed.
I checked Ginny to see how she reacted, but she was raring to go, so I took her in my arms and kissed her too. She put her tongue in my mouth and I reciprocated. I lifted her skirt and massaged her butt, but she was wearing panties.
I told the girl to strip and lean over the bed so I could perform a butt exam. They both jumped to it; Ginny didn't seem the least bit shy, especially for a virgin.
I first examined Ginny's lovely bottom. She was well proportioned, with small tits and a generous bottom. I grabbed her butt with both hand and massaged it. I spread her cheeks and examined her brown, wrinkled hole. I began licking it and moistened it the best I could. It was closed tightly so I couldn't get my tongue inside it. I introduced a finger and slid it in.
Ginny wriggled her bottom but didn't seem bothered by my finger being inside. I began working the finger in and out, turning it this way and that. After her hole relaxed and moistened naturally, I introduced a second finger. Ginny groaned, but didn't say anything. I began frigging her with two fingers. I reached around with my left hand and started massaging her cunt. It was already wet and dying for action.
I started stroking her clit and she started groaning and gyrating her hips. Ginny was really into it.
"Ginny," I said. "I understand you're a virgin and want your cherry popped."
"Yes, please," Ginny moaned.
"Do you masturbate? Have you had orgasms, Ginny?"