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.
