When I was younger, jacking-off was deemed to be a thing "faggots" did. We know that isn't true, but how many totally straight young men suffered through years of guilt because they could not seem to keep their hands off their dicks? I think today's youth are much more adapted and open to "different" sexual things, if not due to exposure in TV, Movies, Books and games, then certainly due to the Internet and the free access to erotica and informative articles online. Even though, with all this information, I still think that to the average young person, if you told them that you knew a guy who loved things up his ass - fingers, dildos, dicks, etc., they would immediately equate that with gay. But through my research on various web pages, I have found that there are quite a few men who are by all accounts straight, who love the ass play.
I can't claim to be totally straight but I'm here to tell you that my first experience with a well lubed finger up the ass (someone elses anyway) came from a woman who was demonstrating the perfect blowjob. This was an unplanned threesome where I was simply supposed to be filming a friend and his fuckbuddy having sex. I suspect they knew they would lure me into the game once I saw how much fun they were having.
At the time, I was in my late 20's or early 30's and the man was at least 60 while the woman involved was not much younger. These two were not going to be on the cover of any magazines, but they had met via old dial-up BBS's and had begun meeting for sexual relief. I had met the man by joining a BBS he owned and eventually we began to share stories of our common desire for MFM threesomes. He was probably one of the first people I ever confessed to the fact that I had Bi desires. When he sent me a picture of his huge, and I mean HUGE dick, I was turned on, but I never really had an urge to blow him.
Anyway, he invited me to his home to film he and his FB and I did. We ate dinner, cleaned up then the two of them very casually prepared for the fuck session. I was so nervous I was literally shaking. Out came a gym bag full of sex toys and lotions and such and once in the bedroom, the two of them stripped. I took the small video camera and began looking for artistic views of the foreplay, but to be really honest, these were not two porn stars. Things went very slow, at least from my point of view. The man was flaccid for the most part, but even then his dick was so much bigger than mine fully erect. As he used a series of different tools on his friends vagina, she played with, licked and sucked his enormous dick trying to get it motivated enough for some penetration.
I know at one point the lady looked up at me and asked if I would like to try sucking. Honestly, as impressive as it was, that was the furthest thing from my mind. Nerves just really were working on me. I don't know how long this really boring, slow, drawn out licking and rubbing went on, but it seemed like a lifetime. And because I was fully dressed standing there, with a camera, I was actually starting to get bored and a little tired. Then there was some whispering and the older gentleman advised me that his friend would like for me to join them.
My first response was, "No, thanks. I'll just film the action." But then, I was offered a blow job. "Seriously, the lady said, you aren't going to turn down a blow job, are you?"
I nervously handed the older guy with the huge flaccid penis the camera and I pulled my jeans down to my ankles and sat on the edge of the bed. The nice lady positioned herself on the carpeted floor in front of me and began to fondle my dick which went from slightly interested to fully erect in a matter of seconds.
Probably the result of a lifelong masturbation habit, I am not the kind of guy who can cum from a few minutes of my wife blowing me. Though she gladly tries it, I just don't seem to get off on it. As good as it felt, in my mind I expected this lady to suck my dick for a while and simply give up or at least allow me to assist her by jacking my own dick.
Turns out my wife had no idea what she was doing. This not very attractive, portly woman at least 20 years my senior engulfed my dick to the balls and began doing some sort of special tongue gymnastics on me. Then, she let a gob of spit drop out to my balls and used it as a special lubricant. Now I have always known that I have a special good feeling place just between my bass and my asshole, but this lady found that and immediately went for more. I unconsciously lifted my ass from the bed to give her access to my hole and within a few seconds, she had the entire length of her finger in my ass. I am convinced that at some point I feinted from pleasure because what should have been about 20 minutes of blowing apparently lasted about two minutes or less. My body simply went limp and when I looked up, the lady was giggling and walking toward the bathroom. Lets just say she needed to wash her hands.
At that point, that was probably one of the top two or three sexual experiences in my life, but it was also a bit embarrassing. I real pro, the lady just laughed it off. Now I wish I could tell you that I took off the rest of my clothes, got comfortable and joined the two for the remainder of the evening, but my inexperience in these matters caused me to make a hasty exit. I had a bit of a drive home and had to work early the next day.
Just like the guys who equated jacking-off as being for faggots, I recall that most of my friends would never admit to wanting to engage in a threesome involving two guys and a lady. For some reason, there is this manly dream of the wife bringing home a cute friend from work and they engage in a FMF threesome. I have always preferred the MFM theme. I just imagine the pressure I would be under trying to please two women. And just imagine what would happen if the lady my wife brought home could stick her finger up my ass and make me cum in under two minutes. Geeze, my wife would be filing for divorce! At least when two guys are involved, when you cum, you have the other guy to fill in while you go out and get a beer or just sit back and watch. Believe me, the wife won't mind at all.
Recently, I have been visiting some blogs that have a theme of "pegging". That is, woman using a strap-on on a guy. I have never been fucked with a strap-on but I dream of it. My wife has used a vibe on me (which is great by the way), but my fantasies don't involve her being the one to use a strap-on on me.
Twenty years ago when I was in the military, I found myself in a dorm room with two female co-workers. I'll skip to the chase and tell you that after a game of strip poker and after letting me get a gander at their goods, I was sitting there in front of these two ladies stroking my dick because they wanted to watch me jack-off. I did and then I left.
As I think about that experience I wonder what it would have been like if these ladies had been a little more daring in their request for me. Would I have allowed them to fondle me in some way? There was no chance of me fucking either one of these ladies - both had boyfriends and both were friends with my wife. Strip poker and jacking-off are one thing, fucking was out of the question. But I think about that experience and wonder if in today's Internet savvy world if one of these ladies might have suggested something more. I have this vision of one lady taking me from behind with a well-lubed small strap-on as I go down on the other. Now that would be my idea of a FMF threesome. And there is nothing gay about that!