Guest post: Walk on the wild side

EDITOR'S NOTE: Male and female readers tell me their stories. Often they don't want them shared. When they do, and I think readers might enjoy them, I put them on the site. So, here's one from a guy. Enjoy, and keep the letters coming. All I ask is that they be true, not fantasies. — Linda Sue


I don't look kinky. I look a guy who would never do such things. That's my secret, and that's my appeal. It doesn't hurt that I'm over six feet tall, have an in-shape body and dress like the successful Wallstreeter that I am. I'm in my late 30's but look much younger (everyone says it but it really is true.) I've never had issues finding sexual partners - be it women or men. My numbers skew heavily in favor of women (100+) and only a handful of men (5). I have had a hard time finding female partners as willing as I am to push the boundaries; the few bi/gay men I've experienced seemed more than comfortable with my propensity for kink. (Please note - there are plenty of women I've been with that challenge this statement - I am speaking generally of course.)

Using that logic - I expect you are wondering why I haven't had more experiences with men? Sexuality is a tricky concept and mine is no exception. I basically identify as a straight man. I love women - love the female form in every way - love fucking and sucking every conceivable part of a woman. My male partners have always just satisfied a curiosity or fulfilled a sexual experience - never crossing into the realm of emotional that can arise with women.

Living in NYC - I tend to mainly play with women there, leaving the road for my same sex dalliances. I like the discreet nature of the road for this and there is the added benefit it is just so much easier to find a male partner willing to engage in casual sex. For guys curious - I'd recommend manhunt or grindr; google it - very easy and very effective. As men are an occasional thing for me - I'm very picky: I like a tall, masculine, athletic man. This last trip I found out that being hung doesn't hurt as well.

This brings us to MLK weekend and my trip to DC. I had begun chatting with a guy online via manhunt and arranged a late drink at a local gay bar in DC on Friday night. The bar was trendy and mid 30s. We had a few martinis and quickly figured out we were attracted to each other. He was late 20's - dark hair, 6 feet +, swimmers build, and very good looking. He seemed like me but only gay identified - he had a good job and seem very interested in the fact I had limited experience with men. A little disclaimer - my same-sex prior to DC consisted mainly of oral interactions or with me topping. I've never really been too interested into topping or bottoming but my only real opposition to it was risk of disease and the potential exposing position of it. We discussed only playing safely but he also assured me he did not have any STDs.

After three martinis he suggested we go back to his apartment instead of my hotel room. His reason were simple - it was closer and cabs weren't readily available. I gladly accepted his invitation. His apartment was a few blocks away - very nice and well appointed. He quickly showed me he latest health test and that put my mind at rest. As I figure most women or men reading this haven't witnessed a gay hook-up - the time from entry into the room to fully naked is pretty quick - less than few minutes. I'm not into kissing men but after we got naked we began exploring each others body.

He took the more dominant position and licked his way down my body. I have to say - I enjoyed playing the more passive role as he pushed me back into the bed and played with my nipples and cock. I was rock hard by the time he actually took me into his mouth. This was clearly the first stop for him, not the end destination... after teasing me a bit he pushed my legs back and dove into my ass with his tongue. I've never had a guy do this to me before but it definitely will not be the last time. He introduced a few fingers into my ass and slowly opened me up along with his tongue. It felt good but I was also hesitant in the direction this hook up was heading.

I suggested a more equitable position and took his cock in his mouth. Sucking cock is an interesting experience - I suggest all guys should try it a few times. I'm not great at it but I can get the job done. I should practice more but again its not my main interest. That being said - I don't like being mediocre at it. I'm not sure if I was terrible or he saw an opportunity but he clearly didn't want me to get him off with my mouth. As he pulled me off his dick he told me he wanted to take my ass.

We proceed to have yet another conversation about safety but unbelievably I heard myself agreeing as long as he used a condom, lube and would stop immediately upon my request. This might be a good time to describe his dick - over 7 inches, pretty thick and cut. I'm not sure why I decided my first time would be with a monster dick like this but I did. He went back between my legs and went quickly to the job of opening me up with his fingers. It wasn't long before he started putting on a condom and lubing my ass. I was on my back having a minor mental freak-out about what was to come all the while he was slowly stroking my very erect cock. As he moved off my cock - he slowly placed the head of his cock into me. Did it hurt? Every single 7 inches. It took about 5 minutes for him to get fully into me. Then he just stayed in me - I was still on my back on the bed and he was standing with my legs splayed. We stayed this way for awhile - he was playing with my dick and letting my get used to that full filling one gets with a cock in your ass.

At this point I need to share two observations - the most astonishing one for me was that I was still hard and the second one being I was actually getting used to his dick being inside me. Then the fucking started slowly at first... Over the next 15 minutes or so it got pretty intense but very enlightening. I learned to take his cock, I learned to manipulate my ass so I could squeeze his cock as it came in, and I found myself legitimately enjoying getting fucked. After we really got into the business of fucking - he came fairly quickly. He returned the favor by going down on me -- it wasn't long before I blew a thick load down his throat. I wanted to go again but it was really late and he didn't seem "up" for round two. A bit disappointing on that front but we had had a lot to drink and it was pushing 3am.

I hope you liked my story. I'm still straight, still kinky, but maybe just bit more open minded. Will I do it again? Who am I kidding - I'm sure I will. I think next time would be more fun with a bi couple.