First, a little background. I was forty-five, married for twenty years, and increasingly frustrated from a sexual point of view. My great-looking wife progressively throttled back sex to the point it was mainly a chore on our anniversary, birthdays or after the rare occasion she’d had a couple drinks.

I finally gave up just jerking off in the shower and visited an adult bookstore with an arcade. The theater area was a U shape, with three rooms in the front and three around the back. I developed a routine of visiting around 10 am, always using one of the front booths. I’d put on a hetero film and within minutes, blow my load and leave.

One Friday I was horny as hell, but couldn’t get to the ABS until around five. There were at least a half dozen cars in the lot. I thought about driving on, but I already had a wet spot of precum on my khakis and a case of blue balls. I went in, bought my tokens, and headed back into the darkness. Because the front three booths were occupied, I ventured to the back. The two outside booths were in use, but the center one was open. I slipped in, fed the machine, vaguely noticed the adjacent glory holes, and pulled out my cock. Up popped a video of a sixty-nine with two very attractive CDs. I was mesmerized until the spell was broken by a shadow in the adjacent GH to my right. Soon two fingers appeared, sliding in and out. I can’t tell you what came over me; but without hesitation, I stuck my junk and balls deep through the orifice. A warm mouth surrounded my cock head and within seconds, I blew rope after rope from my previously virgin meat. My knees were buckling as I pulled out of the talented mouth. Quietly my servicer whispered a thank you, stating he’d be there the next Friday at five.

As I drove home, I couldn’t believe I’d let another guy suck my cock. Was I gay? No, I told myself. This was no different than sticking my dick into any vegetable or fruit I could get my hands on as a collegian. No, I wasn’t gay. Well, you all know where I was the next Friday at five. This weekly routine continued for thirteen months, almost up to the present.

Present day: 3 pm and I’m at a downtown Chicago hotel lobby bar. I’d just finished a stressful certification exam and was unwinding over a bottle of Bud. As I was finishing, the bartender brought me another bottle and pointed to the only other patron: a guy maybe forty-five, clean-cut and with a smile on his face. As I nodded a thank you, he motioned me to join him around the corner from where I was sitting. I thought what the heck, I could use some conversation. As I moved to the adjacent stool, he rotated 90 degrees in my direction, putting his left knee between mine; all well and good, no foul. As we talked, he’d lean forward and frequently put his left hand on my right thigh, finally just leaving it there. Again, no foul. I guess I was starting to get buzzed from the second beer. Much of the conversation dealt with my stress level and my tightening shoulder and neck musculature.

At around 4:30, he asked if I’d join him for dinner later, his treat. I explained that I had planned on asking the concierge to arrange a massage in my room and I was just in the bar to loosen up.

He laughed and said, “Why blow the money?” He suggested he was an amateur masseuse and always looking for a Guinea pig. He asked for the tab, settled up and motioned toward the elevator.

Was I game?

His room was a suite, upper floor, facing the lake. As I stood in the window facing the setting sun, he eased up behind me and began kneading my tight traps. I could feel his body against mine and particularly his erection pressing against my rear. He leaned forward even more and told me to slip off my clothes while he’d turn back the covers. He suggested I lay across the bottom of the bed and get comfortable as he used the bathroom.

When he returned he was carrying a bottle of massage oil and save for a towel wrapped around his waist, was also naked. He sat on the bottom of the bed and liberally applied the oil, spreading it up and down my torso, dripping an extra amount on my exposed crack and rosebud. He slowly began kneading my achy muscles, starting at the traps and moving downward. He grasped each butt cheek firmly, moving his hands in a circular fashion, each rotation bringing his thumbs closer and closer to my waiting anus. After what seemed like hours, a fingertip lightly touched my anus, producing an almost involuntary rising of my hips to meet his penetrating finger. I let out a deep guttural moan, causing him to laugh and say, “I guess you like that!”

You can imagine my nonverbal response. I bucked my hips backward, forcing his finger up to the knuckle, deep in my ass. I couldn’t get enough; but to my surprise and disappointment, he pulled out and moved up to the side of the bed near my head.

He leaned over my head, massaging again my upper torso. With each downward pass, he’d lean farther forward, finally putting his left knee on the bed close to my face. Now as he leaned forward his beautiful rock-hard cock would brush across my face, leaving a trail of precum on my cheek. I’m not sure what came over me, but I reached for his seven-inch throbbing cock and pulled its dripping velvety head across my lips, lubricating them for what I hoped would soon happen. Without pause, he inched forward, slowly sliding his purple mushroom into my waiting mouth. He was surprisingly gentle, holding my head while slowly fucking my mouth. Just as I was anticipating my first taste of cum, he withdrew and moved again to the bottom of the bed.

I was putty in his hands. He told me to get on all fours, pulling my knees to the edge of the bed. I could feel him kissing my cheeks, then his 5 o’clock shadow rasping near my ass, and finally his tongue probing my hole. Again and totally without thought, I pushed backward. He backed off and grabbed the oil, dripping it liberally onto my rosebud. He leaned onto my back and with a hot breath asked, “You want it, don’t you?”

I had a pretty good idea what he was asking and said pleadingly, “Yes, fuck me. Fuck me hard.”

I assumed he would finger fuck me again, adding a second and maybe a third digit to prepare my cherry hole - but he had other plans. He grabbed my pelvis with one hand and used his other to direct the head of his precum-dripping cock against my anus; at first just making small teasing circles. Slowly but surely, he applied more pressure until the mushroom popped past the sphincter. I can’t say it was painless, but any discomfort quickly abated and was replaced by a warm sensation that made me want all seven inches crammed as far into my hole as possible.

He sensed I was cherry, almost moaning, “Baby, you’re so tight. I might not last long.”

I told him I didn’t care and began slowly rocking back and forth on his meat stick to prove it. With each cycle, he pushed deeper, until I could both hear and feel his balls slapping my taint. Within a minute or two, I developed a deep anal pressure and involuntarily began dripping cum.

My arms were starting to get rubbery and I was unsure I could remain on all fours much longer; but luckily he was getting close. He sped up his rhythm, brutally assaulting my hole. Just when I didn’t think I could take much more pounding, he moaned, “Ugh, I’m cumming, I’m cumming.”

After a final thrust, he collapsed onto my sweaty back, pinning me to the cum covered sheet. After he caught his breath and without further ado, he pushed up, pulled his dripping cock from my violated anus, and stated, “I guess it’s time for you to go.”