Where it happened: cottage
Langauge: English
Sex: Male
Rating: 6
Category: Straight
Okay, for a variety of reasons I was still a virgin at 23. I guess I’d never really been able to find anyone I could really trust. Trust is an important thing for me and although I’ve had flings that have lead to oral sex and masturbation and stuff like that, I’d never been able to go through with the whole thing.
Around about my 23rd birthday my best friend Bo came to see me. Bo is my best friend in the world and I love him completely. He’s been going out with this girl Jane for about five years, they’re really tight and they’re going to get married. Bo and I used to talk about losing our virginity together until he met her, then there came that fateful night when he came to me and told me he’d had sex. I felt left behind, to say the least.
So Bo came to see me and said he and Jane had a special present for me. I asked him what it was and he told me. At first I couldn’t really believe it. He said he knew how important trust was to me, and he knew how much I wanted to lose his virginity, and so basically the plan was for me to have a threesome with him and Jane. At first I thought he was crazy or just pulling my leg but after a lot of explanations I started to believe him. Him and Jane were moving into more experimental areas in their sex life and they wanted to try sex with other people. Neither of them much wanted to have sex with strangers–trust is as important to them as it is to me. So Jane hit on the idea of the three of us doing it, as a kind of warm-up for all of us: them for group sex, and me for sex in general.
Well, I gave the matter a LOT of thought but finally we decided to go for it. We went up to my cottage where nobody else was around and just basically hung out. As the day progressed things started getting more and more sexual between us , but nobody had yet really mentioned what we were planning to do. We went swimming a lot and kind of got all chummy with each other. We cooked dinner and then settled down in the master bedroom to watch TV. We were kind of just messing around and telling jokes and stuff when Jane rolled over and said to me, “do you want to see my pussy?”
I said, “sure,” and she pulled off her shorts and panties and kneeled right in front of me. She was being all kid-like and playful and said “do you like it?” I told her I sure did.
Bo told me he was thinking it was about time. Bo and I had used to masturbate together when we were 14 so we were used to each other’s cocks, but here I was getting ready to do it with his girlfriend, so I kind of needed confirmation. I told him I would hang back for a while and just kind of get comfortable if that was all right. So Bo got up and wrapped his arms around Jane from behind, and started massaging her breasts through her tank top. Jane started kissing him and pretty soon had removed his T-shirt and shorts, so that he was completely naked. His cock was a little bigger than mine, about seven and a half inches, and it was really a sight to behold.
Bo asked me if I liked his dick and I told him I did. He pulled off Jane’s top and I saw my best friend’s girl completely nude for the first time. She had an amazing body. Her tits were not too big not too small, just the way I like them. Jane said, “I love you Andy. You’re Bo’s best friend and you’re like family to me. Do you think I have a pretty cunt and tits?” I told her yes. She said, “do you want to touch them now?” I told her I wasn’t quite ready yet. So Bo put Jane onto her back and started kissing her. They made out for a good long while, and Bo started finger-fucking Jane. She was moaning and rubbing his cock with her hand.
By this time I was really, really aroused. I started slipping out of my clothes. Soon I was naked, lazily stroking my seven-inch dick. Bo and I call ourselves “the curve brothers” because his dick curves up and mine curves left. Jane opened her eyes at one point and saw that I was naked. She smiled, the most beautiful smile I’ve ever seen. “Look baby, Andy’s getting ready.” Bo looked over and grinned. Jane started to move her hand towards my dick, but stopped just short and looked at Bo. He nodded happily, and so she started lightly stroking my cock while Bo buried himself in her tits.
After a few minutes of this Bo turned to me and said, “are you ready to try it out?” I said I wanted to see them first, so Jane flipped them over and mounted Bo, then gently eased Bo’s dick into her pussy. She started rocking back and forth and both of them started to moan. It was so beautiful, seeing my two best friends in the world making love. It was the warmest, most intimate feeling I’d ever had. I slowly crept up beside them and, with a deep breath, got going. I took Jane’s head and started to kiss her. She slowly slipped off of Bo, leaving him to rub his slick spike while he happily watched me make love to his woman. Jane sucked my dick, better than anybody ever had in my life, and then rolled onto her back and spread her legs wide, so that her knees were almost at her tits level. I crept in, and with one more look at Bo, slid my dick into her pussy.
It was heaven. Jane and I fucked for almost half an hour before I finally dumped the biggest load of cum of my life into her pussy. During our fucking she had come at least three times but had told me to keep going. Bo had come twice, once by his hand and then a second time by Jane’s as she continued to fuck me. Once we were done, we all just curled up and cuddled until it was time for round two.
Roundn two was significantly more aggressive. It started with a surprise: Bo started playing with my dick, and then sucked it. Then he and Jane got to fucking and I decided to sneak up behind them and put my dick in Jane’s ass. WE tried all kinds of combinations that night and I had anal sex with Bo, too.
To this day I think I could not possibly have lost my virgnity in a more perfect, beautiful way. I love you GUYSSSSS….
Processing your request, Please wait....
