Finley Becomes Hannah

I had been "hobbying," as it is so euphemistically put, for about a decade. Through two marriages, I am ashamed to say. At least I am ashamed 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 (see "Emily"), a married old college flame in town, a business acquaintance (see "Leah") -- 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 satisfying happy-ending...sometimes very satisfying.

After about a half-dozen of these, I met an Asian woman from Backpage named Ariel at a motel. She was exquisite. Slim, gorgeous, European features. And in the midst of the handjob I was shocked (again, I was innocent) when she reached into the bedside table drawer and pulled out a condom. I didn't even know that full service (as I would later learn it to be called) was on the table. And I hadn't even contemplated whether I was willing to cross that 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 component of the relationship that was, in fact, enjoyable and pleasant. Nonetheless, 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 so 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 by now, the web sites had changed -- and I was no longer scrolling the (now defunct) 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 (somedady I'll write y'all about a beauty named Skye). 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 already four other cocks in her that day.

As I tried to remain as "loyal" and "faithful" as I could, I focused on the spas. The ones where full service wasn't even an offering. 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,", but certainly a woman who would catch your eye in a bar. A solid 8+. She was in her 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.

Finley looked a little eastern European. And maybe a little bit trailer park. As I lay naked on the table, she offered the perfunctory massage, before sliding her hand to my 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 feeling something else: I couldn't stop thinking about her.

I resolved to try monogamy again and settle into the ho-hum 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's web 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?" My mind raced at the possibility. And then I began cursing myself that I did not -- for I had not expected this progression at all. Everything I read on TER was clear: no full-service. And the reviews of Finley echoed that general rule, where she reviewed lots of solid 7's... but never once more.

And so I settled in for a sweet blowjob, warning her before I finished so she replaced her lips with her hands 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 again, I couldn't stop thinking about her. And now it was even worse. 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 (Finley's, that is). 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 Finley's 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 pretty white 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 get 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 on the menu here. But I sheepishly said to her, "Last time I think you were willing to... well, I brought a condom this time?" I watched her mind race and consider the possibility, before she smiled, "Sure! " It would run $600 she said, far more than the $180 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 most certainly do not regret it. As I undressed, I slipped my phone -- with video camera on -- among my clothes, wedged together by my shoes, with just the lens poking out. I didn't know what it might capture, but I knew I'd want to relive whatever happened next. Worst case, I had nothing. But maybe I'd get lucky (in a second sense of the phrase).

As I lay naked on the massage table waiting for her return, I started to get nervous. Surely, she'll notice... and then what would happen next? I imagined 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 captured video of this encounter 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 almost nonchalantly. 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. Taut, firm, perfectly shaped and youthful. She turned up the music (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, second only to those tits) and then through her beautiful wavy blonde 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. She gazed deeply into my eyes, with equal parts tenderness and need. And she was charged with an intimacy that reminded me of a one-night stand from a bar.

She locked eyes with me and shocked me by cooing, "You're fucking hot." And her tone indicated that she meant it. Now, I'm nothing special. Forties, a typical dad bod that had improved as I committed to the gym the last few months, and I lost most of the paunch and watched my arms and shoulders grow and harden. I know I'm not a "10" either, but Finley seemed authentic in her attraction.

She slid her mouth down my body and took my hardened penis between her lips, and I was in heaven. It was a gentle, tender blowjob, almost cautious. But it didn't matter. It felt loving... and wonderful. Her mouth was so wet and she slid down once taking me into her throat as her nose pressed against my body. Something about this intimacy felt just so genuine, that I wanted to imagine - as much as possible - that this was not a currency-driven transaction, but rather a real tryst between soon-to-be-lovers.

And so I grabbed her hand and pulled her up my body and guided her ass so that her pussy lips rested against the underside of my now-rock-hard shaft as it lay against my body. Using my hands on her ass, I encouraged her to begin grinding on me. She quickly took the hint, and I felt the wetness seem out as her pussy lips stretched around the shaft of my cock -- not taking me in, but instead sliding up and down the underside of my shaft as it pinned against my body. The pressure and warmth and wetness were exquisite.

Finley seemed to be enjoying it too and before long she was grinding her clit up and down my cock, focused on the ridge of my cockhead. My hands found her breasts as she closed her eyes, looked up, and started to moan "Oh my God." I guided her hips to slide harder on my, as her moans increased and I thought - against all odds - that she was about to reach orgasm. As she built toward that moment, her moans grew louder and sexier, and she locked eyes with me and suddenly I worried it would all be over before it started as I felt an orgasm start to build in my balls. I pulled her up off me before she could finish, apologizing sincerely and saying I wasn't ready to finish. I could tell her body was frustrated, but she remained sweet-as-could-be and nuzzled her nose against mine as she gave my hard cock a minute to calm back down.

After a minute of eskimo kisses, she started to slide her pussy on me again. It was wetter than before. Lots wetter. She closed her eyes again and pleasured herself on my cock, and my hands returned to her breasts -- which she enjoyed more than I expected her to. I took note at how sensitive her nipples were and then she lowered one down to my mouth and I took it in. She moaned even more and her ministrations picked up in intensity when suddenly -- OOPS -- her eyes shot open in dismay as the head of my cock, and just the head, found her wetness and accidentally entered just the very entrance of her vagina. It felt incredible. Tight. Warm. And soaking wet.

She was off me before I could barely process what had just happened, and I apologized profusely. "It's okay, it was an accident," she cooed. And for a moment I started to worry: what if she wasn't "clean"? My wife and I did not have sex often, but it was often enough that it would be difficult for me to wait out any testing window before something would happen at home. And the thought of my bare cock inside her pussy, however fleeting, got me to worrying.

But my anxiety lasted only as long as it took for Finley to start grinding on me again. And suddenly I could think about nothing else besides the feeling of being inside her, skin against skin, no barrier, and the intimacy that came with that. I wanted it to happen again. But I knew it wouldn't.

Until it did. As Finley slid up and down me, once again she moved an inch too far and my cock slid out from between our bodies, popped upward due to the intensity of my erection, and poked itself into her waiting pussy again. This time she waited a second longer before she slid off me. She gave me a loving smirk, sort of a: "That one wasn't an accident."

She lowered her body down to mine again, her chest on mine, her cheek against my own. Her pussy again sliding on my shaft pressed against my stomach. And I didn't know it at the time but as I watch the video now, I see her hands grabbing fistfuls of the sheet. Her mouth gapes open in pleasure. And I can see the exact moment I slid inside her again. She pulls her head up just enough to look in my eyes, and without words I see a "fuck it" flash on her pretty face, and she started to slide down my shaft -- intentionally this time. Inch after inch, with a little uncertainty. Her eyes glance to the condom, still in its wrapper, next to us on the bed. But then her gaze returns to mine as I feel myself bottom out in her, and her clit nudge up against my body.

I hadn't felt anything like this in so long. There is something so exquisite about the first time a new vagina wraps itself around your cock in a tight grip. And I was here for it, savoring every moment. In between heartbeats, I suddenly wasn't in the spa any more. No treatment room. It was like we were in my bed, or flashing back it almost felt like being in a college dorm (the massage table about the size of a twin bed and all, and a youthful twenty-something allowing me inside her most intimate space). She put her hand on the top of my head, lowered her forehead to mine, and began to fuck me. It wasn't mechanical, rote, full of phony moans that were typical of "dates" in the hobby-world. This was sincere, genuine lust and affection and intimacy.

My hands found Finley's magnificent ass again and pulled her down on me, filling her as deep as my six inches were able. "Oh God," she gasped. And she continued to massage my cock with her pussy... gently, softly, but nonetheless with a perfect passion that could not be feigned.

Finley sat up now, and I was treated to a look of her beautiful breasts, and her wavy dirty-blonde hair tossed. I felt myself getting close to cumming -- and far too soon -- and I guided her off me while I whispered, "I better pull out before I cum in you." Her eyes looked at me quizically: "You came in me?" But it was not with any outrage, or even exasperation. Just surprise. "No, no" I explained, and she smiled that pretty smile (that makes me smile from ear-to-ear as I write this) and teases, "I was going to say: 'That escalated quickly!'" As she giggled. "No, I just need a minute" I assure her. And I suggest we change positions.

Finley laid back on the table and I climbed atop her. I love the visual of watching myself disappear into a woman, and I looked down as my cock found her beautiful pussy, nudged itself between her lips, found the epicenter of her wetness, and slid inside again. She was shaved cleanly, with puffy outer lips, and just the slightest hint of inner labia emerging before I spread her open. Everything about her was simply perfect. And I don't know if I'd ever felt a woman wetter. Finley wrapped her legs around my hips, put her heels on my ass, and pulled me in.

"I'm so wet for you, Mike," she whispered in my ear. And I started to fuck her. Not hard and fast -- I knew I couldn't hold back if I did -- but with slow, purposeful strokes, gently guiding myself as deep as I could inside her, trying to convey tenderness and affection. A cascade and chorus of her moans started to build. She whimpered. She heaved. And her voice quivered as she let out an "Ohhhhhhh myyyyy Goooo-ooo--oooooddddd." And then it happened. Finley's pussy clamped down on my cock as she shuddered in orgasm. It was a sight to behold, as her beautiful face revealed the intense pleasure that waved through her body.

I couldn't believe I managed to hold back. "Fuuuuuuuucccckkkk," she exclaimed as her eyes opened and locked mine. "I can't believe that happened," she heaved. And I smiled bigger than I had in forever. I continued to rock my cock inside her, and she moaned, "I just came all over your dick. Shiiiiiiiittt. What the fuuuuuuuck are you doing to me?"

As excited as I was, I found a reset and a second wind and I started to thrust in her again. Her legs bent back and I held them with her heels on my shoulder, allowing me even deeper inside. I stopped for a minute and remembered the camera, and thought I would take an extra risk for the sake of a potential amazing angle, and I lifted her into the doggy-position, nudged her to the edge of the table facing my pile of clothes and the not-too-well hidden camera lens on my iphone. And I slid back inside her.