I'd been having sex with another guy for about 6 months, I guess. We'd been friends for years, introduced by our wives. Our wives were both flight attendants for the same airline and tended to be away from home for days or weeks at a time. My wife and I had been drifting apart for a while up to this point and when Mark told me about him and his wife, I understood completely what he was going through. We talked and drank and drank a bunch more that night and complained much about how neither of our wives wanted to have sex anymore. It's kind of hazy for me about how it began, but I ended up the evening by giving him a handjob on his couch. His cock was a bit larger than my seven inches and thick. The head was large and there was a huge blue vein running its length. I remember thinking it was a better looking cock than my own, which was an odd thing to think at the time. It was interesting to feel another cock besides my own. It felt hotter and heavier. His balls were hanging low. He had very thin patch of pubes above his cock, as if he'd trimmed them and his balls were shaved. I watched as my hand moved up and down his shaft, slowly, then faster. I stroked him to conclusion and marveled at the massive amount of cum he sprayed all over. He returned the favor later on.
And that's how it began for us. When the wives were away, we'd jerk each other off. Then one night, we got high and he asked me for a blowjob. I'd never done that before and never really thought about doing it, but I figured that I'd already done something gay with him and what the hell? So, I sucked his cock and let him cum in my mouth. Having seen the massive loads of cum he sprays during a handjob, I didn't swallow his load that night, but rather let it leak out my mouth as he finished. I didn't mind the taste at all. In fact, I kind of liked it. We ended that night by 69-ing with me on top. He surprised me as he sucked my cock by sticking a finger in my asshole. I surprised myself by liking it.
We progressed along those lines with blowjobs while our wives were away, but Mark consistently would insert a finger or two into me and finger fucked me while he sucked me. We were both enjoying what we were doing. We weren't passionate or falling in love by any means. There was little to no kissing involved. Just a bit of sexual tension being released as our wives were away. We'd drink or get high or both, get naked, watch some porn on a laptop and go at it. Now that I think about it, I don't recall us ever watching gay porn together. We watched some tranny stuff a few times, but most times it was straight stuff.
I'm sure it won't surprise the reader that anal was next on the agenda.
We were at my place, sitting at my desk in front of my computer. We were both naked, next to each other with our chairs close together. We each had hand on the other's cock stroking slightly. Since we were at my place and it was "dealer's choice" for what porn we watched, I chose an old favorite from my youth. It was pretty much 30 minutes of this hot chick getting it in every hole and taking a load in her mouth at the end, but it always turned me on. When we got to the anal part, Mark asked me if I'd ever thought about it before.
"Thought about what?" I asked. "Anal?"
He looked at me and said "Yea, dumbass. Have you ever thought about anal?"
I reminded him that his cock is way too large for anything like that.
"Why?" he asked. "My wife can take it. I bet you would like it."
"What makes you think that?" I asked.
"You like it when I finger your asshole, right? It's just a little bigger than that," he said.
"Just a little?" I asked as I looked at his erection.
We went back and forth for a while and when it seemed that I'd run out of excuses not to try it, I gave up and got down in my knees in front of him and blew him in the hopes that he would just drop it. As I sucked him off (and I'd gotten quite good at blowjobs, he would tell me later on that night), I couldn't shake the thought of having his magnificent cock in my ass. Every tranny video we watched sure seemed to look like it was enjoyable. I'd never nailed my wife in the can, so I had no point of reference to go with. I'd heard that it can be very pleasurable and the orgasm associated with it can be fierce. I was curious and willing to try it, but not yet. I sucked and sucked and stroked his beautiful cock until it exploded in my mouth with force. The first shot slammed into the back of my throat and I had no choice but to swallow it. The cum kept flowing from his cock and I just kept swallowing. It was the first time I'd ever done that.
So, then next day I began to do some research. I read about 25 or 30 articles on my phone while at work about anal and how to do it right. I even took a few notes because I'm such a dork. But the underlying theme of the articles I read seemed to be preparation was the key to a pleasurable experience. On the way home from work I stopped at a drug store and purchased my supplies. I actually went to five different stores because I knew that a guy buying enemas, four different types of lube, and a big box of condoms was going to scream "guy doing some anal" to anyone who saw me. So, I shopped around and got what I needed without raising too much suspicion.
My next stop was the adult store. I bought a small butt-plug and lube. One article I read suggested having the plug in for a little while before the act in order to stretch out the anus. Seemed like a decent enough idea, so I bought one.
We messed around a little and got down to business when we got together the next time. I have to say that the lead up and foreplay was amazing. He laughed when I showed him the butt-plug lodged in my ass. When he removed the plug, he rimmed me for a bit, but then went with the fingers as he stroked my cock. I was practically begging him to put it in me as he teased me. I finally rolled over onto all fours and stuck my ass in the air for him. The initial penetration was uncomfortable. Not painful, just uncomfortable. He'd pull out all the way and back in again, over and over until I was more receptive. Eventually, he stayed inside me and fucked me nice and slow. I loved it. I reached under myself and stroked my cock in time with his movements. I came after about 30 seconds, but never lost my erection as he continued. I thought I was going to cum a second time but I felt his cock explode into the condom inside me.
Needless to say, anal was definitely on the menu from then on.
He offered to let me return the favor to him that night, but I declined. He did ask one favor of me that night, though.
"I need you to trim up. Down there," He told me. "You don't have much hair there, but it's distracting."
"You want me to shave my pubes?" I asked him as I was getting dressed.
"And your ass," he told me. "Or get waxed. It's not like your wife's going to notice."
He has a point and since I'm a total dork, I did a little research. I found a waxing studio nearby and decided to give it a try. It wasn't as painful as I thought. It just stings a bit for a brief period. But I liked the feeling of not having hair, so it was worth the bit of pain to go through every month or so.
The first two or three times, a female did my waxing. Then, Bruce stepped into my life.
Bruce was younger than my 35 years. I guessed he was about 25 or six and I wasn't far off, I later learned. He was handsome and fit, a few tattoos visible on his arms, and a well cropped beard. The first time I went to him it was a little strange. I'm not sure why it felt weird, considering I was letting Mark do any and all to me whenever he wanted. But, I liked the way my skin felt the day after getting a wax so I those feelings aside. The more I went to him, the friendlier we got with each other and chat as he was doing his thing.
Things were great. Then my wife filed for divorce which wasn't much of a surprise. We split amicably, sold the house, split the money and the other assets, and I moved into a single bedroom apartment in a cool area. Mark would come over and we'd fuck in the privacy of my apartment and no one was the wiser.
Then he died in a terrible car crash. His wife as well. I was devastated and felt all alone. I had other friends, but Mark was special in that we had a secret.
But, I kept going to Bruce even though I was no longer active sexually.
One day, Bruce asked me if I was gay.
"I mean to say," he stammered quickly, "that you're one of my few male clients and I know that the others are sex workers. You don't really fit the bill of a sex worker, so I'm just wondering why you're getting regular waxing."
I laughed. "I'm not like 'gay-gay'," I tried to explain poorly. "I was messing around with a guy when I was married and he liked me without body hair, so that's why I started getting waxed. I like the way my skin feels without the hair."
"You were messing around with him? Not anymore?" he asked.
"No," I said. "He died a few months ago."
He apologized and I told him not to worry about. I quickly changed the subject and asked if working in this place was his only job.
"Actually, I'm a drummer in a band. We're playing tomorrow night if you want to swing by," he said. He told me the name of the place and the time. I told him that if I went out, I'd swing by.
