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The Coach and The Apprentice

"The Apprentice Awakens to Inner Gay Urges in Mid Life"

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Author's Notes

"My personal story about sexual awakening after divorce. <p> [ADVERT] </p>First installment in new gay exploration."

I never considered myself homosexual, or even inclined that way. I mean, I had thought about it - what it would be like and would I find it weird or gross, and I determined that I would never go there. Never had a gay fling growing up, got married in my mid-twenties and was always attracted to women. I never stepped out on my wife and never acted out on any sexual fantasies.

But then I got divorced and flung myself into a sexual reawakening in my mid-forties. I started dating a lot of women, and had the odd hooker when I was in a different city. I loved my newly single life, and became a slut and proud of it. Not so much one and done, but more having multiple women on the go at any time. I imagine the women suspected something and weren’t so happy about it, especially when I was doing two on back-to-back nights over a weekend or taking off to another city, or skipping Valentine’s Day with some lame travel excuse.

My ex and I had had threesome fantasies, but only fantasies. As the sex between two long-married people got boring and infrequent, we would masturbate together talking about another woman in the mix - even her best friend (who I banged after we split) - or in some cases a man. We both found this very taboo and very exciting and would cum with an explosion that would never be possible between the two of us. One guy in the fantasy was her piano teacher who was about our age and in a long-time relationship with a younger man. The teacher was a very good-looking guy and I found it very exciting to jerk off and talk about him to my wife. When we split, we made a compact that, come what may in our divorce, we would never hold our threesome fantasies against each other.

As I was actively dating in the late-forties singles scene, I started to get very curious about all sorts of kinky sex or gay sex: this was the time in my life when my libido matched my desires and I could go ethnic or small or large, old or young; anything for diversity. If there were trannies, dwarves or amputees around, I would have gone there too.

It wasn’t long before I went down a slippery slope by looking at gay porn or cutting out personals. Remember the old 900 numbers? Well, I never called one – too fearful of having any record on my credit card – but just thinking about it was an easy way to satisfy my gay itch.

The next step was a place I came across that was a sex club for guys who just want to go jerk off with each other. Totally legit place under the law. I figured that I could do this in an anonymous and safe setting without fear of getting in over my head. No sucking or fucking or inserting anything anywhere. Pay your entry fee, strip down to shoes and socks and wander around until you make eye contact and sidle up to someone. Very little talking and lots of wanking. This place was really horny; guys are there for one thing which is anonymous mutual masturbating. Lots of lube around and some paper towels and albolene cleaning product to wipe off. I was in and out fast because I got off with some stranger. Fun pulling some other guy and have him cum in my hand, jizz and all. No sense staying around after you’ve cum. I went two or three times and liked it.

I was still extremely active in my straight life, but in my new gay experimenting one, I wanted more than the partial experience of getting my cock pulled by another guy, and vice versa. Then came the moment I went on the on-line personals and started cruising the men-looking-for-men section (this section has since been taken down due to some bad incidents). What a smorgasbord of ages, interests, and opportunity!

So I placed an ad as a bi-curious seeker and got a response. He seemed like a dedicated member of the gay community and we met for drinks. Very light conversation about stuff in general, and then the talk turned to what a sexual encounter would be like between a newbie like me and a gay guy in a committed live-in relationship; what we would do this being my first time, and what logistics would work, neither of us wanting to use our home base.

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We decided on a date a few weeks out and found a sleazy low-end rent-by-the-hour motel on the highway where we would split the cost. Man, was I nervous, not least because I had no idea what having full gay sex with a man would be like, and he was a very experienced guy. How would I handle the rough skin and beard and how would I react? Would it be a turn-on or off-putting?

Well, I didn’t have to wait long. For my first time, drinks are a must, so a flask of rum and some OJ and my courage was up. So was my cock. We had one purpose meeting here: he to scratch an itch for a newbie bi, and me to get my rocks off in my first full-blown gay sex. His name was Mike and he knew just how to handle the situation and coach me along. First off were showers for both, so we smelled - and tasted - squeaky clean. I struggled with the kissing part – too intimate, too gay I thought. I tried it but I was more interested in the raw sex instead of the kissing. His equipment was of average size, but it showed well because his boner pointed upwards, so you just know he’s really really hard and ready for action. His ball sack became shrunken up as he got harder.

He wasted no time in going down on me. What a feeling, like the best blow job ever! I had been with a number of women including pros who were not nearly as good. I loved it, especially the beard on my thighs, and the aggressive sucking. He lay me down on the bed in this cheap motel room, so my legs were dangling over the edge, and he got right down to it kneeling on the floor between my thighs. Mike took me in and swallowed me right down. I had to slow him down or the fun would be over too fast. But I couldn’t hold back very long and came in his mouth. He was a swallower which was great since women are a mixed bag on this. In my books, swallowing is always hornier compared to the bukkake stuff (although I tried that on a subsequent occasion).

Now came the moment of truth where I would have to, or rather want to, reciprocate. I would have to take a guy’s hard cock in my mouth and satisfy him to climax. I wasn’t sure about it since I had never done oral on a guy. Would I fumble it, would I be able to get him off, would I gag, what would it taste like? I tried to get all of it in, right to the back of my throat (which I felt the next day, bringing a grin to my face). I went as far as I could and had his pubes in my nose. And what horny fragrance. Much better than my own sweaty smell. I gagged slightly, but I wanted to gag so he and I were getting the whole benefit.

Mike was a good coach. I took him in my mouth but wasn’t sure about the sucking versus the thrusting. Mike just laid me back down on the bed, and he pulled himself off and came on my right thigh. What a trip, with rope after rope of jizz on my thigh, a large puddle of greyish white cream, and that great smell.

I really liked this! I wanted more!

But the cheap motel routine has its limitations – you cannot really hang out and have a dinner or more intimate time, and then go at it again. The sex was so raw and horny, but the intimacy side never got explored. So, we left and agreed to think it over, and get the coach and the apprentice back together again.

 

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Written by SteppingOut
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