I have two stories about masturbating with other people, one old and one new.
My first experience was with my girlfriend, Donna. She was 19 and I was 22 at the time. Our sexual relationship had started slowly, but once we got going, we had a lot of fun at it. One evening we were at my apartment and had just finished making love. We were lounging on my bed sipping a beer and chatting. Donna began to tease me about the girly magazines I had in may room. The mags were the Penthouse/Playboy type.
I told her that I liked the pictures, but that there was good reading published in them also. She came back with, "They're really for jacking-off, right?" I admitted that they were good for that also. That started a series of questions from her that lead up to whether I jacked-off or not. I told her I did - a little (a small lie). She acted hurt, but I could tell she was just kidding. Even though I knew she was acting, I still reassured her that it did not take the place of sex with her. That I only did it during the week when she was at school.
That bit of conversation got my juices running again and my cock got hard again. Donna began stroking me softly and asked me if that was the way I did it. I told her it was very similar. Then she asked me to tell her how I did it. Rather than tell her, I offered to show her. She agreed right away with a big smile and a giggle.
We were laying back against the pillows on the bed, so it was easy for me to take over from her. I used my right hand to stroke my cock and my left to rub my balls. Donna was watching intently and it was really turning me on.
After a couple of minutes of careful, but enjoyable stroking, Donna asked me how I could look at the magazines if that was the way I jacked-off. I told her I had to change position to do that, and sure enough, she wanted me to show her.
I got a towel and one of my Penthouses. I spread the towel on the bed and knelt at one end of it so that my cock was aimed over it. I opened the magazine and laid it on the bed next to the towel. Donna sat up cross-legged next to me and looked over to see what pictures I had opened the magazine to. I do not remember exactly what I had selected, but it was some sort of pictorial showing a guy and a girl together.
I continued my show, taking my time and using several different hand techniques. After I had to pause to turn the page, Donna offered to do it for me. I was looking at the pictures part of the time, but I was looking at Donna just a much. Between the look on her face and her nakedness she was just as enticing as the people in the mag.
I probably could have held my orgasm off a long time (I was practiced at that already), but the scene was getting to me. I told Donna I was getting close and she told me to go ahead. She had seen me come before when she had given me a hand-job, but this was going to be her first time watching me do it for her. It was a good, strong orgasm. I shot a half-dozen big globs of come onto the towel and just as many short shots that covered my cock and hand. She did get a good show and said so.
I didn't hesitate; I was still kneeling there and asked her, "Are you going to do it now?" She was ready and willing. I asked her to do it just like she did normally. Donna laid back on the bed pillows, spread her legs and used two fingers to rub her clit. I moved around to sit cross-legged in front of her and lifted her legs over my knees so that her feet were resting on either side of my hips.
She took her time also. At first she only used one hand and had her eyes closed, but after she got going, she used both hands and watched me watching her. The whole time she kept two fingers on her clit. The other hand alternated between rubbing her inner thigh and plunging two fingers in and out of her pussy. Like the rest of our sex, she was being completely open and relaxed the whole time.
When she came was furiously working her clit and pussy with both hands. Her back arched off the bed and she let out a long low moan. After the first strong orgasm, she just lay there several minutes gently rubbing her clit and having many smaller after shocks.
That week we repeated the same scene several times. As time went on we kept masturbation as an occasional part of our sex play. At my encouragement, Donna never hesitated to stimulate her clit while I was in her if she felt like it. I still think it is an extremely sexy site to look down at my cock going in and out of a woman's pussy while she rubs her clit. Women have told me that they find it very liberated of me to encourage them to help us to a mutual orgasm, and I can truthfully tell them that I enjoy it just as much.
Since that first experience I've had the occasional opportunity to masturbate with my ex-wife and a few girlfriends. However, none of them warmed up to the practice the way Donna did and it didn't become a regular thing, as much as I would have liked to be. That was OK though, because they usually made up for it other ways.
Now to the recent event. I have been single for 12 years now. When I am between lady friends (or dating one who is not especially sexually adventurous) I employ the assistance of an escort service. Sometimes for just a one hour meeting to relieve the urge. More often I make it a preplanned, several hour event. For the past year I have met several times with a young woman who does a really good job of making the experience worthwhile. Allison is employed at a regular job, and does the escort thing for fun and profit. She is an attractive, well-groomed person who you couldn't tell from any other local yuppie type.
Last month we were doing a couple of hours of our usual thing. We were kicking back in my living room, watching erotic movies, playing with each other, giving each other head and a little screwing. I had done a little masturbating during some of our meetings, but it had not been a main event. We were both more interested in oral sex most of the time.
During that meeting I asked Allison if she could set up a threesome with another girl. She said she could and we discussed the possibilities. It turned out that a two or three hour meeting with two girls from the service would have been prohibitively expensive and I had to tell her I was going to pass it up. She offered to meet off the service if I could do it on a weekday evening. We agreed on a very reasonable price for a full evening that would also put both the girls ahead because they would not have to give the service a cut. I arranged to take a Wednesday off and we three met on a Tuesday night two weeks ago.
The girls arrived a seven in the evening and were going to stay until the next morning. We had some dinner and I got to know Brandi a little. She was cool, just like Allison. There was no embarrassment or awkwardness about the situation. After dinner the girls changed into some garter and stockings outfits I had bought for them, I got naked and we settled onto the couch have drinks and watch some flicks.
We took our time. Allison already knew and I had told Brandi to not get in a hurry to make me come. At 45 years old, I now like to save my first orgasm for a while. I like to be kept on the edge and build up to it because my subsequent orgasms in an evening do not produce much semen. They are plenty good, just short on volume.
We were very oral with each other. Lots of cock, pussy and nipple sucking. Real wet tongue kissing and licking each other all over. There was a little touching between the girls, but it was more incidental than bi.
A scene on the movie of the female star having a five-some with four guys had just finished. Brandi asked me to replay it. I asked her if she liked the group sex scenes. She said yes, but what she really liked, "...was the guys doing their dicks." "You mean jacking-off," I asked? "Yeah, the guys jacking-off turns me on."
Sure enough, toward the end of the segment, just before the big come scene, the guys in the film were sitting around the star stroking their cocks while one of them took a turn making it with her.
Seeing Brandi's interest, I began stroking my cock right along with them. With that Brandi leaned back and did herself with her hand, looking back and forth between the film and me. Allison joined in also.
Brandi really got into it. She told us she liked watching us beat off and she kept telling us to watch her. She liked watching both "...girls and boys getting it off." Allison and I both got off during that little spontaneous episode, but Brandi got off several times. We repeated that scene at least twice more during the evening with Allison and Brandi adding a dildo they had brought. Allison and I both enjoyed it, but Brandi was the leader. The next morning, just before they left, I jacked-off once more at Brandi's request. All in all, I was very happy with the meeting. But it did not end there.
The following Saturday I received a call from Brandi. She wanted to know if I wanted to get together again. I had to tell there my recreation budget for the month was used up and that I would have to postpone. Instead she offered a freebie. She was at my place an hour later. It was two in the afternoon.
At her suggestion I undressed and beat off while she did a slow striptease. Once she was naked except for stockings she played with her pussy and breast while standing in front of me. I held off and she came twice during her little dance. Then she asked if I wanted to watch some movies. She had brought some. We snuggled on the couch and watched the first. It was all guys jacking-off. One, two and many at a time. There was even a some oral between the guys. We masturbated while we watched and talked about the techniques and come scenes. By the end of that flick Brandi had come a bunch of times, some loud and strong, others small and quiet. I had not let loose, but my hands and cock were covered with pre-come.
Brandi had another one that was a full-length bi feature. It was about a man and woman who both had bi lovers, but kept it a secret from each other. The film went through their discovery of the secret and finished with a really well done threesome between the two guys and the girl. There was lots of guy on guy oral and fucking during the film and I found I liked watching it. After all, it was just the girls getting some equal time for all the girl on girl bi in the movies.
Brandi asked me if I had ever sucked another guy. I had to tell her no, but was able to tell her I had been in several two on one threesomes and that I had touched other men's cocks during it. She loved the part about me 69-ing a girl while the other guy fucked her doggy style. I guess I did too, because I came like crazy while I told her.
As you might guess, Brandi wants me to do a bi threesome with another guy. I have agreed in principle, but we haven't come up with a candidate that we would feel comfortable with. In the meantime, she has me practicing on her dildo.