In Flagrante Toronto [MF][Cheating][Long]

Author’s note:

People that don’t cheat will never understand the impulse; the burrowing, creeping compulsion that drives otherwise content people to stray from their partner. This may partly stem from the common misconception that people cheat because they’re unhappy, or missing something in their relationships.

I don’t think that’s it. Or at least, it never was for me. The thing is: sometimes you just want to fuck someone else.

This is a story about fucking someone else. This is also my story, which means that names have been changed to protect the innocent and the not-so-innocent.

And before I begin let me also say that I love my husband. Madly. Truly.

That’s not what this is about.

###

It started with a work trip, as I suppose these things often do. I had gotten a text from my boss on Wednesday asking me if I could cover a conference in Toronto the following week.

Normally I declined these events because they involved a lot of mindless standing around a booth answering the same 3 or 4 questions for hours on end. Plus the schedule at these things was usually such that I didn’t have time to get out and see the city except from the back seat of the cab to and from the airport.

But I hadn’t been to Toronto in a while and the weather actually looked better there than it had been in Chicago so I thought “why not” and texted my boss back.

It was a tougher sell at home. My husband didn’t make too much of a fuss, but I could tell he was annoyed. We had already had some mild clashes over what he saw as my mounting lack of availability during the week and habit of getting distracted at dinner with the latest crisis unfolding over email. And while he didn’t come out and say it this time, I could tell he’d been hoping we’d finally have time to do normal couple stuff like sit around and argue over what to watch on Netflix.

Of course, as was usually the case when it came to low-grade fights with my husband, I got my way, and by the end of the week he even seemed somewhat happy with the prospect of having the whole house to himself for a few days. As I was leaving, I teased him with an inside joke dating from early in our marriage. “Remember, no strippers inside the house after 9:00.”

###

The flight to Toronto was short and uneventful. I had planned on getting in around 8:00, still plenty of time to walk around and find a restaurant, but by the time I got to the hotel it was almost 9:30, and so I opted instead to order a sandwich from room service. I had noticed on my way to the elevators that the bar was pretty packed, and I briefly considered heading down for a glass of wine after eating. By the time I unpacked and dashed off a few quick emails though I was already feeling tired and decided to get ready for bed.

There’s that scene in movies where the protagonist is in the bathroom, usually towards the end, staring at themselves in the mirror as they Realize Something Important about themselves. Sometimes they’ll even say words to their reflection in the mirror, like “I *can* do this” or whatever. It’s one of those tropes that happen frequently in movies and almost never in actual life.

Yet there I stood in the bathroom of a hotel in downtown Toronto. Staring at myself. More accurately, staring at my body. Which brings us nicely to that point in these stories where I’m supposed to describe said body so you can picture what it would be like to put your dick in it. Or I guess other things.

And it might be a reflection of my short attention span, but my mind tends to gloss over this aspect. Words like ‘tight,’ ‘firm’ and ‘smooth’ are descriptive in only the most forgettable sense.

But because part of my motivation in writing this story is to get off at the thought of strangers imaging themselves fucking me, I suppose I should probably try anyway.

According to my driver’s license I’m 5’1″, although if you asked my husband he’d tell you I’m closer to 5’3″. Either way, I’ve always been what’s considered a petite girl. This used to be a major annoyance — I remember being jealous of my friends in high school and college who were taller and more ‘developed’ than I was. This was tempered by the later realization that boy’s didn’t care about my height — that when they were around it was me they seemed to gravitate towards.

Another thing about me: I have incredible tits. Like seriously incredible. They’re textbook 36Cs and still hold their own at 41. The rest of me is still holding up well, too. Maybe I’m not as toned as some of the 20-something interns at the office, but my stomach is flat-ish and my ass still looks good in jeans.

I’m pretty. I’m not a supermodel, but the men in my life have repeatedly and with varying degrees of conviction told me I’m beautiful. Personally I’m on the fence. I think I have my moments, and sometimes when I’m studying myself in the mirror I’ll see flashes of what I think men see, but most of the time I think I look too serious, and I’m worried about the increasing mass of wrinkles at the corners of my eyes. Lately, I’ve been experimenting with going back to shorter hair, although the last time I did this in college I thought it looked mannish and so I’m still debating how far I want to take it.

All in all though, not bad. I mean, I’d fuck me.

Speaking of, and I’m 95% sure this is something I would have never noticed if guys hadn’t brought it up to me, but apparently I have a very visually-pleasing vagina. I’ve never been quite sure exactly what men mean when they say this — I’ve asked and gotten conflicting answers — but there you go.

###

The actual convention took place in a cavernous space attached to the hotel, which meant the walk to the show floor was at most 10 minutes. Perfect for me. Just long enough for the lobby Starbucks to kick in, just short enough to keep me from regretting the choice to wear heels.

I got there early, in time to see the convention floor still a chaotic jumble of hotel workers and confused-looking attendees who had shown up early. I made my way towards the back of the room, where I recognized a small booth with our company logo emblazoned on a banner running across the top.

There was a young man already standing and facing the booth with his back to me, carefully placing what I assumed were business cards in neat piles along the edges of the table. The fact that our company had sent a guy was somewhat unexpected. Normally the DC office would run these things, and they almost always sent women to staff these events.

I was about 30 feet away and still walking towards the table when he suddenly straightened and turned around. He saw me instantly but it wasn’t until I waved that his eyes seemed to hitch on mine. He waved back.

“Hello!”
“Hey!”
“Are you Samantha?”
“Yeah. Hey. It’s just Sam.“

I have great conversational skills.

His name was James. I had him pegged at 25 although I later learned he had turned 30 a few weeks earlier. And unlike the people who usually ran these events, he was up from the New York office instead of DC.

He was attractive. About medium height, thin, with brown glasses that made him look bookish. He was wearing slim, black jeans and a light blue button-down underneath a grey blazer. The total effect was something of a cross between a scruffy-looking Harry Potter and a film critic. It was nice.

I wish I could tell you that we spent that first morning of the convention exchanging witty repartee amid increasingly flirtatious looks, but we actually didn’t interact much. It got busy as soon as they opened the doors, an unending blur of faces, questions, handshakes, more questions. At one point I looked over and caught James staring at me, but he quickly looked away and when I looked back over at him a few minutes later he was talking to someone with his back to me.

Around 5:00 the crowds began to thin out. One minute I was handing out business cards and explaining our go-to-market strategy in the face of an increasingly commoditized space, the next I found myself suddenly standing behind the booth next to James, both of us looking out at a mostly-deserted convention floor.

“You staying through tomorrow?”

“Yeah, although I don’t know if I’ll be able to stay through the whole thing. You?”

“Same. I’m supposed to stick around but I’m going to try and sneak away as soon as it empties out. The hotel guy that came by earlier said they’ll take care of all the packing up stuff for us.”

And then:

“Hey if you’re not doing anything tonight we should get dinner. I was here a few months ago and I found this awesome place not too far from the hotel. It’s too early to go now but I was thinking of going over there in a little bit and you should come.”

He said all this in a very casual way, not looking at me. But I felt it. 41 years as a woman and you learn things about men making suggestions.

It was tempting. I didn’t have any plans that night, unless you counted going back to the hotel room, taking off my shoes and catching up on email. And it was still pretty early. I could get dinner with James and, with any luck, be back in my pajamas well before 10:00.

And James *was* cute. It had occurred to me that he had maybe the most expressive eyes I had ever seen in a man, and when he had shook my hand earlier it felt like a furnace.

Plus it had been a long time since I had been out to dinner with a man who wasn’t my husband, and even though this was strictly a work thing and not in any way a date, I felt a small, secret thrill at how unexpectedly excited I was.

I’m not sure what exactly I said, but I must have agreed because the next thing I know James was saying “Great!” and telling me we should meet up in the lobby at 6:30.

As he spoke, I had the sudden impression he was staring at my lips.

###

I should probably remind the reader that up until this point I had exactly zero intentions, sexual or otherwise, towards James. And today, when I think about what happened — how it happened — there’s a part of me that has a hard time believing it myself.

Even there in the hotel room, getting ready and deciding whether or not to switch to flats, the only thing on my mind that was even remotely sexual was the way I could still feel how warm the palm of his hand had been against mine.

###

The dinner was far more pleasant than it had any right to be. James turned out to be a surprisingly versatile and wry companion. I learned that he had only recently arrived in NYC, where he lived in a very tiny apartment in Park Slope. That before NYC he had worked in San Francisco doing marketing for various startups, but decided to come back east to be closer to most of his friends and family. That he liked his job but didn’t want to do marketing forever, just long enough to get the money together to start his own film business.

“Film business? Like, you want to make movies?”

“Kinda. I want to make movies, but so does everyone in New York. I think I need to get some commercial video work going first, just enough to pay the bills and give me a cushion.”

After dinner we walked slowly back towards the hotel. Perhaps it was the two glasses of wine I’d had at dinner, but I felt strangely comfortable with James. It was still pretty early, so I surprised myself by suggesting we get a nightcap somewhere near the hotel. I surprised myself again a few minutes later when, walking next to him, it occurred to me that I had forgotten to check in with my husband that night. And that I hadn’t told James I had one.

###

I couldn’t tell you the name of the bar. I’m not even sure I could have found it the next morning, even though it was only a block or two away from the hotel. What I can tell you is that the following happened in roughly some semblance of order:

I got a drink.
James got a drink.
I got another drink.
James got another drink.
I told James about growing up in Chicago in the 80s. What high school was like before the Internet.
James told me about growing up in a suburb of Boston in the 90s. Seeing his first live band in a friend’s basement.
We compared our cities’ respective winters and the merits of various pizza styles.

At some point I went to the bathroom and, making my way back through the throng of people clustered near the bar, I caught James in profile. He was saying something to the bartender, his hand absently scratching the scruff of his cheek. He must have sensed me looking at him because at that moment he turned and looked right at me and smiled. As it turns out, that moment also happened to be the exact moment I realized I wanted him to fuck me.

###

I remember leaving with James. I remember walking back towards the hotel, both of us commenting on how loud the bar had been. I remember standing next to him in the lobby as we waited for the elevators — the electric, unspoken excitement when we both realized we were staying on the same floor.

What I don’t remember are the seconds between us getting off the elevator and me finding myself in his room, standing very, very close to him and feeling his breath against mine, his lips brushing my cheek. Both of us still wearing our coats.

It turns out James was a fantastic kisser.

I don’t know how long we made out standing by the door, but it was long enough for me to become very aware of the erection pressing against my stomach through his jeans. That and his hands, which had started to tentatively explore the soft undercurve of my bra.

I should point out I’m normally not the aggressor in bed. Or if I am, it’s always in the context of play-acting to fulfill my partner’s fantasy versus being aggressive because *I* actually want something. And on any other night, I would have followed the pattern I’d established for myself as a young woman in her early 20s — namely, wait for him to touch me Down There first and then, and only then, would I touch his dick in return.

Well, I touched his dick first. Just like that.

More accurately I started to rub his dick through the outside of his jeans. This was immediately met with a sharp intake of breath, and his whole body seemed to imperceptibly sag into me. It was also at this time I realized my bra had become unhooked, and that one of his hands was gently pinching my nipple. Not hard, but hard enough.

His cock felt intriguingly warm through the denim and I wanted to touch it. Emboldened by my own surprise at what I was doing, I unbuckled his belt, felt his pants unceremoniously drop to his ankles and slipped my hand in over the top of his boxer briefs.

It wasn’t huge, but it was nice-sized and heavy in my hand. I was keenly aware of how ridiculous this must have looked: me, fully-dressed and awkwardly holding the penis of a man who was most definitely not my husband. A man who was currently cupping my tits in an upscale Toronto hotel room.

I started slowly stroking his shaft as he gently pushed me up against the wall, which meant that his dick was soon vertical and pressed somewhat between us. I could feel it throbbing against the palm of my hand as he kissed my neck. One of his hands slid down my stomach and I felt his fingertips lightly tracing the elastic across the top of my panties, occasionally dipping under to graze the soft rise above my clit.

I could feel my pussy getting hot and slick, and I began to almost involuntarily grind myself against his hand. He responded by pressing his finger into the wet furrow between my lips and sliding it up and down the length. It was one thing for me to touch his dick. Quite another to let him touch me like this. Him touching me like this meant something different, although I couldn’t tell you what exactly.

His other hand was trying, somewhat unsuccessfully, to unbutton my shirt and remove my bra. I had to take my hand off his dick to help, and was about to start removing my underwear too, when he surprised me by simply pulling the fabric to the side and slipping his finger into me in one quick movement.

We stayed like that for a minute or two. James fingerfucking me up against the wall as my hands grew increasingly slippery with the precum leaking out of his cock. At one point I heard moaning and realized it had been coming from me.

###

James’ eyes followed mine as I disentangled myself from his hands and gently pushed him backwards towards the chair next to the window. He had somehow managed to step out of his pants, but he was still fully-clothed from the waist up, and his dick bobbed wildly as he stumbled backwards into the chair.

Without really thinking about it, I knelt between James’ legs. The head of his cock looked raw and it jerked away from his stomach when I grasped it. It was covered in pre-cum and I could feel its slick otherness in my hands. Leaning forward, I placed my lips around the crown and let it slide into my mouth. His eyes closed briefly then, and he seemed to sigh into the chair.

It’s fun to look at their faces when you put it in your mouth. Just that first second when your lips, warm and wet from kissing seconds earlier, slide over the head of their cock. I’ve always found it fascinating, the way men’s eyelids will flutter, almost femininely, when they first feel you taking them into your mouth.

I like to look at them, too. Not intently. Not pornstar-ish. But I like to watch them watch me suck their dick. The way their bodies alternately hunch and sag over me.

Some men don’t look of course. My husband doesn’t, for example. When I’ve asked him why he doesn’t look at me when I’m sucking his dick he just says it makes him feel like he’s slightly demeaning me. Like he’s leering at me. Which, I tell him afterwards, is either missing or entirely the point.

###

I didn’t actually watch porn of any sort until I was well into my twenties, which meant that by the time I finally saw two professionals having sex with each other I had already done most of it on my own already. I remember being struck by how the girl in the video never once used her hand when she was giving a blowjob, and how instead she seemed to inhale the guy’s dick all the way down to the base. Up and down, up and down. Like it was nothing.

I found this surprising, as I’d always instinctively used my hand just as much as my mouth when giving a blowjob. I was never one of those girls who could deep throat a guy, but I didn’t need to. Where my mouth couldn’t travel my hand could, and I knew from many afternoons of joyous experimentation with my college boyfriend that the end result was the same.

I was careful not to overdo it with James. I wanted him to fuck me. I didn’t want him to cum in my mouth. Not yet at least. I wanted to get him as close to the edge as possible, that moment when I could feel his legs start to tense and the head of his cock begin to imperceptibly bulge. But not before. So when I sensed he was getting close, when I felt that initial bucking sensation, I backed off a bit.

But god his dick was nice. Not too big. Not too small. Just a warm bar of iron, insistent and mine. I quickly discovered that if I licked the underside where the head met the shaft, that little striated area less than a half-inch in diameter, I could make him shudder and squirm about the chair.

After a few minutes of this I could tell James was getting close. His breathing had become more ragged and he began to match my rhythm with his hips, thrusting almost absently in time with my movements. I thought at one point he was going to grab my hair and start shoving his cock into my mouth, but instead he suddenly reached under my arms, stood up and and pulled me up with him.

He held me there somewhat awkwardly for a second before I felt his hands turning me around and pushing me towards the bed. I wasn’t sure if he wanted me to climb up on the bed or simply lean over it, and I didn’t get a chance to ask because his hands had begun to tug my panties down.

(I should note that somehow, miraculously through all this, my underwear was still on, although the rest of my clothes had long since been discarded).

Stepping out of my panties, I climbed up on the bed somewhat uncertainly. With my ass facing him, I was conscious now of how utterly exposed I was. I could feel the sudden coolness of the room as my pussy, puffy and almost alarmingly wet with excitement, lay open to him. I could smell myself in the room now too, and felt momentarily self-conscious. His hands trailed along my hips and I wondered briefly if he was going to just shove himself into me then and there. Instead he did something I wasn’t expecting: he pulled my hips towards him, spread my lips with his thumbs and started licking me from behind.

I’ve had men go down on me before. But not like this. Definitely not like this. My husband, as dependable as he is unadventurous, would never think to shove me facedown into a pillow and thrust his tongue into me like that. I’m not even sure he knew it was a thing people did.

But James knew. I felt his thumbs splaying me, opening me to him, as his tongue pushed into me everywhere at once. My hands alternated between clenching and unclenching the comforter as he licked the length of my slit. I could feel the faint stubble of his cheeks scrape against my inner thigh and found myself subconsciously arching my back and spreading my knees wider as he licked my pussy. It wasn’t long before my thighs began to shake with the first far-off rumblings of an orgasm.

Now I definitely needed James to fuck me.

I scooted forward on the bed a bit and looked back at him. I was still looking back at him as he positioned the head of his cock right outside my opening and began pushing into me. He didn’t push it all in right away either. Instead he let the head of his dick ever so slightly part and distend my lips until just the head was in. I think he was trying to prolong the sensation, but being the impatient sort I began to wiggle myself back onto him.

We went slowly. At one point I had to reach backwards and put one of my hands against his thigh to give myself a second to adjust, but soon he was all the way inside and I felt what I have only ever been able to describe to myself as being ‘full.’

James began to fuck me then. Slowly at first. I could feel his fat head stretching me as he drove his cock into my swollen pussy. At one point I looked back and saw him looking intently at the place where he was disappearing into me. I’ve always wondered what it must look like to guys. Do they feel like they’re making something disappear when they put it in? Or are they making something appear when they pull it out?

James began to speed up, but on his own time. And he never got too fast. Nor was there a lot of grace. Just his hands around my hips and his dick pounding methodically into me from behind, pushing me inexorably towards the headboard.

Somehow I found myself on my stomach, with my legs closed together and James still sawing into me from behind, but now his weight was there and his breath was in my ear and I could feel my own wetness and felt my body pushing up into him as he thrust, willing him deeper.

After a few minutes of this I felt James tense and I knew he was close. He started to pull out and I should have let him but what came out instead was “it’s okay don’t stop.” I felt his dick throb then and I cried out as he grabbed my hips suddenly and buried his cock in me. There was a split second where we were both completely still before the first warm spurt of his cum flooded my pussy, and I instinctively moaned as I felt it fill me. This was followed by a second, thick rope of cum as James murmured ”oh fuck” and ground me against the base of his dick.

My own orgasm came seconds later like an avalanche and surprised me with its suddenness. One second I could feel his semen blooming inside me, the next I could feel my pussy clamping down on his dick as my body was convulsed with an orgasm that caused my knees to buckle and my forearms to collapse completely onto the bed.

I know that, clinically-speaking, the orgasm couldn’t have lasted more than a few seconds. But whether dilated by alcohol or excitement, it seemed to stretch on for minutes, and I felt, unusually for me, exhausted when it was over. Another kind of full.

After some time our bodies began to slow, and although James was still on top of me he had started to kiss my neck and had propped himself up on his forearms. I felt his penis soften and it began to slip out little by little until it finally lay wet against my thigh.

We laid in bed together then, cooling pleasantly. He had rolled me onto my side and was spooning me. I could feel his heart beating and his breath tickled my neck as cum slowly seeped out of me and onto the bed. Gradually I became aware of the sound of the hotel. The soft chime of the elevator. Muffled footsteps passing by the door. And then we were both asleep. I woke up a few hours later and quietly collected my clothes and made my way back to my room. Which it turned out was literally 4 doors down.

By the time we were both on the convention floor again later that morning something had passed. Probably more for me than James. It wasn’t unpleasant. It wasn’t even awkward. It just wasn’t the same. Which I think in some ways we were both grateful for.

I flew home later that day and never saw James again, although I did hear a few months ago that he had left the company and was living in LA doing something with film. I’ve toyed ever since with the idea of sending him an email (he was all over the Internet and easy to find), but for right now I’m happy just leaving things as they are.

Source: reddit.com/r/gonewildstories/comments/6zk2ys/in_flagrante_toronto_mfcheatinglong