Some really nice mutual fun from an unexpected place...
I have been masturbating for a good portion of my life now. I enjoy it quite thoroughly. All throughout high school and even afterward, I had a really strong interest in masturbation. A majority of the porn that I watch is typically of people masturbating. I mostly enjoy watching women by themselves, but it's even better when it is women masturbating together. On occasion, I even enjoy watching a good mutual session between a man and woman or multiple men. I guess it just turns me on to know that other people are enjoying this wonderful thing as much as I am.
My parents were really open about sex and stuff like that when I was growing up, so I never felt like I would be disciplined for jerking it. It seemed to be pretty much encouraged, we just didn't openly talk about it all the time.
Anyway, I have always fantasized about masturbating with someone else, male or female, it just didn't matter who. I always wanted it to happen. None of my friends really talked about masturbating too often other than when joking about it. We never had serious conversations about it. There were a couple times when I came close to living out this dream, but it never quite happened. When I was about 13, my friend showed me his dad's collection of pornos stashed in the garage. We started getting together on a semi regular basis to look at them, but we never went further than that. A year or so later, I was at a friend's house and we came across some late night soft core while I was sleeping over. I played it off like I wasn't interested in watching it for some reason and we only watched for a few minutes and nothing further happened. I totally could have jerked it with my best friend, but I didn't let it happen. I have kinda regretted that since then. I never really pursued the subject with any of my more recent friends, but it has always been in the back of my mind somewhere waiting to come out. And now, I live in San Francisco where it should be easy to find someone that would jerk it with me, but I just haven't pursued it even now. I have taken a slight interest in possibly joining in on one of the bi-weekly SF Jacks get-togethers, but I don't quite know if I'm up for it yet. Plus, it would kind of make me feel like I was cheating on my girlfriend.
A few years ago, I met my wonderful girlfriend. She's a great person and I love her to death. She knows about my love of masturbation and related porn and totally accepts it without question. The one struggle we have always had, however, is that it is very difficult for her to have an orgasm. Even masturbating on her own, she hasn't been able to cum. No matter how hard I have tried for the last four years, I have not been able to make her cum from sex, dildos or masturbation. That was, however until we got her a really nice, small version of the Hitachi wand. She has recently discovered what it is to have an orgasm. Now, it's as if she is making up for lost orgasms. She has been tearing through batteries in that thing like crazy. If she has a day off, she'll text me throughout the day to tell me how many times she's cum. It makes me horny as all hell to hear about this.
We have used the wand in our sex sessions, but she has really been enjoying it on her own and has come to call the vibrator 'Cupid.' It seems like she has been emboldened by her recent discoveries, which is all to my delight. A few weeks ago, we were about to go to sleep, but she was a bit restless. She was tossing and turning and the finally turns to me and says 'Hand me Cupid. I wanna 'bate.' I reach into my drawer and gladly hand it to her. I was quite tired, much to tired for sex, but this definitely got me interested. She reached under the covers and turned on Cupid and started to go at it. It was dark, but I could see the outline of her body and the motion of the vibrator as she moved it around and worked her little clit with it. She started to moan quietly. This made my cock rise in a second. I was watching the outline of her face as she started to writhe in her pre-orgasmic pleasure. At this point, I reach down and pull out my now throbbing cock and start to jack it along with her. I threw the covers off of me and increased my pace along with the sound of her moans. We realized how much we were turning the other on and got louder and faster. I heard the vibrator switch from low to high and her moaning got louder and her breathing more labored. We were both close to cumming. I continued to stroke my rod with increasing intensity as she worked her clit with her new favorite toy. Suddenly, we both let out our respective grunts as we both came at the same time. We both lay there with our own euphoric highs wearing off. She turn to me and asked, 'Did you cum.' I couldn't even say anything, I just moaned a quick, 'Uh huh.'
I loved sharing this moment with her. This fantasy turned into a reality with someone from whom I never expected it. We have been more frequently masturbating together lately and on some nights replacing this with our sex sessions, but sometimes incorporating it. It is now even more of a turn on to think about masturbating with someone else because I have finally had it happen. I am still open to the possibility of masturbating with another man down the line. I just think it could be a really great bonding experience with some close friends, but I don't quite know if they would feel the same. For now, however, I am entirely content openly masturbating with my wonderful, sexy girlfriend. Just thinking about it makes me want to stroke the hell out of my cock. Especially since last night she ended her night by getting herself off in bed next to me and I ended up falling asleep before I had a chance to join in. I have been horny as all hell the entire day and she's out of town, so it is now time for me to go and rub out one of my own. Thanks for reading the lengthy story and happy stroking. I hope you enjoyed it.