I had been "hobbying," as it is so euphemistically put, for about a decade. Through two marriages, I am ashamed to say. At leat with regard to the second.
In my first, the sex was nonexistent, and I looked elsewhere. There were a few "real-life" encounters -- at work, a married old college flame in town -- but most of the time I found it safest to peruse the Backpage ads. I was innocent by "hobbying" standards, and began with a variety of "body rubs" that amounted to two-bit massages with a very satisfying happy-ending. After about a half-dozen of this, I met an Asian woman named Ariel at a motel. She was exquisite. Slim, gorgeous, European features. And in the midst of the handjob I was shocked (again, innocent) when she reached into the bedside table drawer and pulled out a condom. I didn't even know that was on the table. And I hadn't even contemplated whether I was willing to cross this line, to further betray my wife, and to risk all that came with fucking a stranger off Backpage -- and a sex worker at that. But it all happened so fast, and before I knew it Ariel was guiding my latex-clad cock into her tiny, wet pussy. And I mean tiny. And then it happened. Fast. As I slid all the way in and buried myself to the hilt, I started to explode into the condom, cumming incredibly hard. She burst out laughing (not mockingly, but playfully), "So tiny, right?" in that Asian accent. I couldn't help but laugh too, and for the first time I had fucked a sex worker.
It wouldn't be the last.
Over the remainder of the marriage, every so often I struck up Backpage for a release. I justified that I was scratching that itch, so that the lack of sex at home would be less of a point of friction with my wife, and I could focus on the platonic relationship that was, in fact, enjoyable and pleasant. And good times were had. Some women that I wouldn't have picked up in a bar. Others that were among the most beautiful women I'd ever been with. And every couple of months or so, I'd find release in the arms -- and vaginal walls -- of purchased release. But a marriage without physical intimacy was doomed to fail, and fail it did.
A few years later I remarried, and the sex was amazing. Hot and heavy. She was in her 40s (as was I), a mom, and I couldn't keep up with her appetite if I tried. As the marriage progressed, life began to happen. And since two or three times a day turned into two or three times a week and then two or three times a month... I could live with the reduced sex. What I couldn't live with was the general frostiness that grew. And before I knew it, I was back exploring the forbidden fruit. Of course, the web sites had changed -- and I was no longer scrolling the (defunct, of course) Backpage, but instead found myself mesmerized by the beautiful women on Tryst, Eros, or 411. Typically the encounters were much the same. Texting a set up, meeting a girl at a hotel, enjoying her mouth on my bare cock followed by my wrapped penis in her vagina. As with before, some were amazing. Others were a disappointment. But even the best of times never felt quite the same with that however-thin layer of latex between our bodies. It just was a constant reminder of the nature of the arrangement, the artificial tryst, the risk of being inside a woman who had four other cocks in her that day already.
As I tried to remain as "loyal" and "faithful" as I could, I tried to focus on the spas. Returning to the "body rub," getting the release I sought, but justifying that it was only a handjob... or maybe oral at most. Not sex. I was being a "true" husband, right?
At one such encounter, I met Finley. She was beautiful in a "real life" sort of way. Not a "10" by any standard, but certainly a woman who would catch your eye in a bar. Late 20s, tall (maybe 5'10"), with a very nice body, 34B or -C tits, and the tiniest bit of baby fat on her that made her seem like a real woman. She had amazing hair though, a dirty blonde with waves that extended just beyond her shoulders. And piercing blue eyes that were somehow warm and icy all at once. As I lay naked on the table, she offered the perfunctory massage, before sliding her hand to my now-hard cock. She stood at the head of the table, leaning over my body so her tits were dangling in my face, as she stroked my cock. My hands wandered to her out-of-this-world ass, and once slid under her panties, where she let me trace her outer lips until I felt her grow wet. I slid a finger in, where she allowed me for just a moment, before pulling my hand away. There was something different about Finley. She wasn't the most beautiful woman I'd ever seen naked, but she had a girl-next-door innocence, and an "attainable" nature that made me think she would be the kind of woman I would love to (and be able to) pick up in a bar and take home for the night. I imagined we weren't in a seedy spa, but rather in my bed at home after a night out, and she was rubbing my cock to completion -- and I exploded. A couple feet in the air, with far more of a shuddering orgasm than I usually enjoyed even inside of a woman. It was unreal. Finley cleaned me up, I got in the car to drive home, feeling guilty of course. But something else. I couldn't stop thinking about her.
I resolved to try monogamy again and settle into the stale sex that comes after five years together. I succeeded for several months. But I could not stop thinking about Finley.
I looked at the spa site again one afternoon, saw she was on the roster, and went to see her again. She remembered me, and this time the action was a little hotter. She climbed up on the table, dragged her body over mine and I enjoyed the feel of those natural, girlish tits along my chest and down to my cock. And then she cooed, "$100 more gets you in my mouth." I said "yes" without thinking, and soon I found myself enjoying a wonderful blowjob. Not a porn-star gagging and slurping, but what you might expect from a college girlfriend. Without thinking, I muttered "God I'd love to be inside you..." and she pulled her mouth off my hard member long enough to ponder the proposal. "We're not supposed to," she said with some hesitance. Of course, I thought. "...but what the hell. Do you have a condom?" Not expecting this progression, I did not. And I settled in for a sweet blowjob, warning her before I finished so she replaced her lips with my hand and I exploded again, this time splashing onto her pretty face. She gave me a warm embrace, cum still dripping off her cheek, cleaned herself and me up, and I was on my way.
But I couldn't stop thinking about her. I pictured her when my wife crawled atop me, and I imagined I was inside Finley. Her youthful, soft but perky tits bouncing as she slid up and down me. This was a girl that, in another life, I would date in a heartbeat. And I found myself continuing to daydream about what she would be like.
Several more months went by as I tried to stifle down my desire, and not risk blowing up my life which -- all in all -- was one that I enjoyed.
But after a particularly trying and tense week at home, my wife left for a business trip and I found myself driving toward the spa that afternoon instead of home to the nanny and the children. This time I stopped for a condom, just in case, and I brought far more money than had exchanged hands previously -- I wanted to leave nothing to chance this time.
I called ahead to confirm her availability on my way, and entered the blacked-out doors of the sketchy spa on a main artery heading out of town. I entered the foyer, finding another blacked-out window and solid door. I rang the bell, and a few moments later, Finley greeted me. She looked incredible. A sequined silver mini-skirt, and matching bra. Her eyes lit up as she remembered me, we shared a side-hug and she walked me back to the "treatment room." I always got anxious, even when a repeat customer at a place, irrationally worrying that this was the time I'd enter a room and be met by a cop. Or a pimp with a gun who was ready to separate me from my wallet. I stifled down that anxiety, and Finley closed the door behind me.
I knew that "full-service" wasn't typically on the menu here. But I sheepishly said, "Last time I think you were willing to consider full-service. I didn't bring a condom that time, but I have one today." I watched her mind race and consider the possibility, before she said, "Sure." It would run $600 she said, far more than the $300 customary service. But I was prepared, and I wasn't about to let money get in the way. I flipped out six $100 bills, she took them and left the room saying, "Get yourself comfortable."
I'm not entirely proud of what happened next, but I certainly don't regret it. As I undressed, I slipped my phone -- with video camera on -- among my clothes, wedged together by my shoes, just the lens poking out. I didn't know what it might capture, but I knew I'd want to relive whatever happened next. As I lay naked on the table waiting for her return, I started to get nervous. Surely, she'll notice... And then what would happen next? I pictured all kinds of horribles, the least of which might be her jumping up angrily and chasing me out -- never to see her again. But before I could hop off the bed and change my mind and put the phone away, I heard footsteps coming down the hall and Finley entered the room. I write the remainder of this story while the video plays on my laptop screen, ensuring I don't miss a moment of memory.
I sensed immediately that this time was different. Rather than chastely staying clothed and starting a massage, Finley immediately discarded her clothing. Treating me to those long beautiful legs. Another view of those beautiful breasts, with light-pink perky nipples poking an inch or so off her athletic breasts. A little less than a handful, and looking smaller even on her tall frame, but beautiful nonetheless. She turned the music up (not wanting to betray to the other staff what was about to happen) and climbed on top of me, swinging her leg over my body and lowering down to begin kissing my throat. My hands roamed her perfect young skin. Up and down her back, down to her ass (which is probably her best physical attribute) and then through her hair. For her part, Finley slid her body up and down mine, grazing me with her skin, and nuzzled her face into my neck where she kissed my throat. My wife would be gone for almost a week, so I didn't worry about the possible marks she might leave. Her mouth alternate between my throat and my earlobe, where she flicked her tongue in my ear. She stopped short of offering her mouth to mine, but still -- something was different this time. It was real. And she was charged with an intimacy that reminded me of a one-night stand from a bar.
