This is a series of stories about experiences with Jill, my first long term girlfriend and sexual partner. They are based on true events except that they are revised into what could have happened if we had been focused differently. If we'd known then how to have a relationship good enough to do the things we could have, then we would have been mature enough to have things turn out this way.
Jill was a few years older than me and we learned a lot about sex during the few years we were together. She was nearly as willing to experiment as I was, that is, when she was willing to have sex. And that was not as often as I wanted. But even between times we talked about positions and techniques that we had heard about but not tried. We thought sex could be just for fun under the right circumstances. We talked about what it would be like to do other people we would see walking by, even threesomes and more.
Jill had large boobs for her size and she came to enjoy the attention they brought her. She never liked wearing a bra so I always encouraged her to take it off as soon as we left for our dates. Although she didn't always wear revealing tops, I still liked knowing she had no bra.
She had an older cousin, Jenny, who spent summers with her ever since their teen years. Jenny was very much into sex. She enjoyed the excitement of a new guy. She claimed to be an expert in the Kama Sutra. I think her mother was a French relationship psychologist. Some of Jenny's attitude influenced Jill because she became much more sexual when Jenny was around. Those two slept in the same bed as they had since they were children, because there was no spare bedroom.
Although we wouldn't have sex, Jill and I would still make out while Jenny was there. Late one night, I unbuttoned Jill's night shirt and rubbed her clit while kissing her boobs. Jill was lying on my left arm so my left hand was free. Jenny found my hand and moved it under her shirt to her boobs. I think she was rubbing her own clit while I rubbed her boobs with my left hand. My right hand and mouth were busy pleasing Jill.
Orgasms weren't a big event so things just died down. I left without telling Jill about Jenny's activities. Jill was a little jealous when Jenny would walk around in skimpy clothes. I never made a big deal about it but Jill could tell I noticed. So I thought it was best to not mention it.
Jill's college class organized a charity golf game and needed Jenny and I to play the next day. Another student, John, who was from our hometown and the roommate of a good friend joined our team to complete the foursome. Jill and I knew John but hadn't spent much time around him. I thought Jenny would probably like him since he was one of people Jill said would be fun to do. But she said there wasn't much attraction, other than that.
John was the only one who was decent at the game. He and my friend lived next to the golf course so we met there. It was unusually hot for a spring day. As the game began it became obvious that we had not dressed for the heat. We sucked as golfers but we had fun with it. John was trying to help the girls with technique but it didn't make much difference. The longer we played the higher the temperature climbed. I told the girls that at least John and I can take our shirts off, which we both did. We bragged about how much better it felt with the breeze on our skin. Jenny said the best she could do was to take her bra off. She did that without removing her shirt and stuck the bra in her golf bag. Jill told us she wasn't wearing a bra, but could only tie the shirt up around her waist.
Jill wore a flannel button up shirt while Jenny had on a football jersey. John offered to go get t shirts for them back at his place since it was just next door. They would still be shirts but would have to be cooler than what they were wearing. The girls thanked him as he ran off.
John caught up on the next hole. He gave each of the girls a plain white man's t shirt. Jill and Jenny hid behind a golf cart to change. I tried to peek but didn't see anything other than their backs.
As we finished the game John and I paid more attention to the girls than our game. The view had improved substantially. Jill and Jenny didn't seem to either know or care that we could see through the t shirts. We stopped even keeping score. By the time we finished most people had gone so we went back to John's apartment for our cars. We were all very thirsty so we went in for cold water. The girls took their tops in so they could return the t shirts.
After getting us large glasses of water, John sat on a small sofa while the girls and I sat on another small sofa near the door. John fiddled with the stereo as we drank our water. John and I thanked them for their choice of outfits and said we were sorry they had to change back to their normal tops. We also said we hoped they enjoyed our shirtless outfits. We still had not put our shirts back on. We pointed out the fact that we had been undressed that way for much longer than the girls wore the t shirts.
Jenny stood up and said she enjoyed our show very much and said, "And here's a little gesture of appreciation." She then took off the t shirt, standing for us to see. Jill hopped up and took her shirt off as well, saying that she appreciated the show also.
I was shocked. John and I were didn't know what to say so we just looked. All I could say was, "Wow." Neither made a move to put their other top on.
After what seemed like hours, Jill, my girlfriend, walked over to John and sat on his lap with her boobs right in his face. She leaned over and kissed John. I was so shocked, it took a minute to notice that Jenny was straddling me the same way. Jenny kissed me for a long time then whispered in my ear that she had wanted to fuck me since we met. She said, "Relax and enjoy; Jill is OK with this. You might even like the show."
I started kissing her all around her boobs and neck as she rubbed herself into my crotch. As she stood me up to take off my shorts, I looked over to see Jill on her knees blowing John. He was obviously enjoying himself, moaning as he laid back on the couch. Jenny pushed me down. I moved around to get a view of Jill as Jenny took off her shorts. She took my dick into her mouth for just a few seconds before sitting on my lap again. She slowly guided me into her.
Jenny took her time fucking me. There was no wild humping, only slow moves as she alternated kissing me and putting her boobs in my mouth.
Jenny told me to look over at Jill. She stood up and took her shorts and panties off, then pulled John up onto his feet. She sat on the sofa and pulled John down on her, guiding his dick into her. She laid back on the couch with her legs around John and her arms back over her head. She moaned as she took him deep inside.
Jenny asked what I saw. I told that I saw Jill having a good time. She then asked what I thought. My response was this was the hottest thing I'd ever done. She then stood up and got on her hands and knees facing Jill and John. She told me to come in behind so I could get an even better view of them. I played with her boobs from the back.
Jill got up then put John on his back with his head toward us. She straddled him and guided him in as she looked at me and smiled. She sat straight up giving me the best view ever. I couldn't last long looking at that so I came quickly and even more intensely than normal. It seemed to take hours. We watched Jill and John for a few more minutes before Jenny suggested a shower. She went straight in and waited for me a bit while I caught the last glances of Jill.
After soaping each other up I moved around behind her and began rubbing her clit with one hand and her nipples with the other. It didn't take long for Jenny to have such a strong orgasm I had to hold her up.
After drying off, Jenny guided me back into the living room where Jill and John were having a rest. Jenny, assuming the role of director, spread her towel out on the floor and invited Jill to lay on it. She then directed John to get down and lick her clit. I started kissing and rubbing her all over. Jenny kissed one nipple while I kissed the other. Within a minute Jill was having an orgasm.
She then put John on the floor and had Jill straddle him facing away. She held his dick as Jill sat back on it. Jenny wanted me to stand in front of Jill so she could give me "the best blow job ever." As Jill took me in her mouth Jenny started kissing John. Jill bounced on John which led to another orgasm quickly. I was so horny I didn't last long either. Jenny told Jill to stroke me with her hand as I came, with instructions not to stop until she said. After a few minutes she told her to push upward behind my balls, wait a minute and do it again.
I'd never experienced that before but I had to admit that it felt good. It seems that Jenny had done this a time or two. I didn't even notice when Jill got off of John because I had to sit on the couch for a few minutes after that.
Jill and I found our clothes and got dressed. Jill put on her original top but didn't bother to button it. We sat and finished our waters just like nothing had happened.
It was getting dark so we said our goodbyes. Jill and I got in the car for the 45 minute trip home. Jenny stayed behind to have dinner with John. She would be along later.
Jill asked how I liked their surprise. It was one of the biggest and best surprises I've ever had. I loved it. She said it was also fun for her. But since she'd done John, she didn't need to do him again. But she thought Jenny might take care of that.
I told her I missed seeing what all she did while I was in the shower. And I wanted to hear about it. But first, there was something we had to take care of. I drove into the parking lot of an old store that was no longer in business. I told her to get into the back seat. I got in the other side and pulled her shirt off. She kicked off her shorts. We had to work quickly before someone saw us so I jumped on top of her. She was still very wet so I slid in easily. We both came quickly before getting dressed again.
During the drive I asked her to tell me about the experience and what brought this on. She said that John and I spending the day without shirts was a big turn on. But the biggest thing was spending afternoon showing off in a see through top was very sexy. She wanted to jump me several times before we got back to John's. "But you jumped John," I said.
"Well, I had to pay you back for playing with Jenny last night while you were playing with me, right?" So she knew. Jenny had already told her that she moved my hand there. I asked, "Are you mad?" She wasn't.
She told me that the two of them had been discussing sexual attitudes. Even before today Jill was trying to get over the guilt associated with sex. Jenny had been explaining that sex just for the sake of sex can be fun if you don't worry that it has to mean something. And it makes for a much more healthy relationship when you get by all of that baggage, she reckons. "Jenny explained the appeal of a new guy every now and then. It's something different to be explored. But you can't hang any more meaning on it other than fun. And it's actually a lot of fun when you can let go of all the needless garbage," she told me. "Jenny was always very comfortable with sex and her body and I wanted I wanted her help in getting past the hang ups I've had about our relationship and sex in general."
"Besides, Jenny said you would enjoy watching as long as you weren't threatened. Guys are like that," she continued.
