Were I to grab myself from the past, the one about to answer that call, I would’ve proceeded to call him an idiot whose libido roared over basic self-preservation. If ever I lived up to the male stereotype of having two heads but lacking the blood flow to run both at the same time, that night was it.
The whole thing was shady from the get-go, but something in me just wanted to believe, like Mulder with UFOs. So when “Tina” posted in a public chat room if there were any men in my then age range without any plans for the night, I reflexively replied. Fifteen minutes later, she messaged me privately, asking to call me.
“Hi there,” an anxious female voice greeted me when I picked up.
“Hi,” I greeted her back, “so what are you looking for?”
“Here’s what I really wanted to try. Can you get a hotel for the night?”
“I suppose so, but…”
“Perfect,” she excitedly cut me off, “so I would meet you there and we’ll have sex.”
“Hold on, hold on. I can get a hotel, that’s not a problem. But can we maybe exchange some pictures or…?”
“No, no… That’s the fantasy. I hook up with someone I’ve never seen before at just a random hotel somewhere. Not knowing what we look like is the whole point!”
It’s almost certain that a reg flag factory somewhere was working at full capacity, churning out enough to fill a whole container ship’s worth just to adequately describe this situation. But the hormones were firmly in charge, demanding to be given the wheel, and I agreed, heading to the hotel on which we decided.
Along the way, she called twice to make sure everything was still proceeding as planned. She talked a mile a minute and asked the same questions repeatedly. With adrenaline now steering and testosterone keeping my ears shut, I made it to the hotel and uneventfully checked into a nice room, dropping off my overnight bag with basic toiletries. My human brain, shocked at just how far this situation managed to unfold with minimal input from it, silenced its lizard core and started asking some serious questions.
Before it could get answers, my phone rang once again.
“Hey, are you at the hotel?” asked Tina.
“Yeah, yeah, I’m in the room.”
“Ok, I’ll be there in five minutes. Will you wait for me outside?”
I once again agreed to the unknown and stepped outside. Pacing nervously, I waited, bracing myself for the worst. My mind finally began to come up with fevered scenarios, wondering who would show up and what would happen next. Could this be a trap? It sure sounded like a trap. Do you have a backup plan, you horny fickwit? What if this is some new scam to rob gullible twits with more cum than brains at gunpoint or kidnap them to drain their bank accounts? Did you think of that? Huh?
My brain was not being kind to me, although, to be fair, I deserved the abuse. But before we could negotiate, a now familiar woman’s voice asked for my name over the click of two inch stiletto heels. I whipped my head around to finally find out who lured me to this place.
My eyes met a woman who could have easily been on the cover of a fashion magazine. The kind of woman whose racy social media photos would drive an incel commit an act of terror in desparate rage. The kind of woman who would make Imugr’s horny male hordes ask “does she, and please say yes?!” The kind of woman to fantasies of whom almost every hetero or bisexual male has masturbated at least twenty times.
Her caramel skin, long, dark hair, shapely legs, perky C cups, with a perfect, lithe hourglass figure in a flattering skirt and blazer completely took me off guard, so much so that she smirked with an almost evil delight.
“See, I told you not to worry because I used to be a model,” she said.
“I can absolutely believe that,” I nodded in reply.
She was right. I was no longer worried about her looks. What I was starting to worry about as we made our way to the room, is if someone thought I hired an escort and called the police to report the attempted vice. Now, I don’t exactly send small children crying in fear to their mothers and the word “cute” has been used a number of times to describe me, but the woman following me was so far out of my league, we played different sports.
What was I going to tell the cops? That if anything, I was the escort to fulfill a fantasy, found on the web on the blind lark of an absolute knockout? Pretty sure the damage caused by laughing so hard they’d erupt in tears and hiccups could be construed as an assault on an officer. Okay, my brain finally said as we entered the room, let’s just tackle one problem at a time, and see what happens next.
“Would you mind if I use the shower?” she asked.
“Of course not,” I shrugged. “Everything okay?”
“Absolutely,” she smiled. “I’m just a little sweaty and wanted to freshen up.”
“By all means,” I pointed her towards the bathroom with an outstretched hand like a butler at a luxury hotel, you know, the kind who wears white gloves and expects his tips in euros.
As the muted sound of running water manifested, I strategically positioned myself and dove into her purse. Not my proudest moment, but at this point, anxiety was starting to eat at me. To my great relief, there were no guns, knives, mace, poison, or todo list with “lure guy to hotel, kill him, dispose of body” scrawled in blood. So far, so… okay? Ish?
Just as I thought about taking a minute to relax and maybe ask if she might like company in the shower, the unmistakable sound of someone sitting on a bed snapped me out of it. Walking into the bedroom, I saw her in a short, sheer nightie, eagerly expecting me after taking off the thick comforter on top. She patted the space next to her.
Time to turn on the charm. Or rather it would be if all the anxiety hadn’t had me playing human possum. Somehow, I quickly ended up on top of her, fully clothed, but frozen as awkwardly as possible to her great and ever more visible consternation. The look on her face reminded me of watching someone trying to open clamshell packaging with a box cutter as the blade slipped out after barely making it through an inch of plastic.
“Are you nervous because this is your first time with a dark skinned woman?” she asked, trying whatever she could to make this work.
“No, that’s not it,” I stammered out. “My previous partner was black, so that’s definitely not it.”
“I see,” she mused aloud. “Then what do you think it might be?”
“I just…” I sighed. “I’ve never done this before and I don’t know how to start.”
“Maybe something that requires you to touch me?” she offered.
“How about a massage?”
“That sounds wonderful!”
“Oh, and I have some oil for that in my bag.”
“Maybe I should take off my clothes so you can use it?”
“I think that’s perfect.”
Clearly relieved at finally getting a plan of action for me together, she jumped off the bed, threw off her nightie, and sent it flying across the room. My eyes finally beheld her perfect breasts, a stomach as flat as anything leveled by Rick Sanchez, and a curvaceous bottom I consciously had to stop my hand from trying to touch as she got comfortable on her stomach.
With bated breath, I warmed up and lubricated my hands, and began the massage, rubbing down from her shoulders to her waist, down her butt, thighs, and calves. I didn’t hurry, and her approving little moans told me that whatever was happening at least felt halfway decent. The moment I paused, she flipped over to her back.
“Now the front?” she winked.
I nodded and threw off my hoodie. Gingerly my hands worked their way down her shoulders, after which I decided to finally take the goddamn hint that was being smashed between my eyes like a two by four for the past ten minutes straight, and let my oiled fingers cradle and squeeze her breasts.
She moaned, half with pleasure and half with relief that her partner finally understood what was being asked. Her hands grabbed my face and her lips met mine for a tender kiss. I kissed her back, deeper and more passionately as my hands stopped massaging and started caressing, feeling her curves through my t-shirt. I kissed down her neck, let my tongue play with her now erect nipples, made my way down her stomach as she spread her legs in anticipation.
Diving straight for her clit, my tongue making delicate circles around and over it between a little suction from my mouth, I felt her getting wetter and wetter. My tongue slipped inside her to her enthusiastic purring, but very quickly, it became apparent that this was nowhere near enough.
“Why the fuck are you still dressed?” she sighed, trying to tear my clothes off, clearly upset at how slowly this was all going.
Finally getting me naked in front of her, she kissed me again as she stroked my thankfully hard cock. I stopped her with a light touch.
“Wait, before we continue,” I said, “I just wanted to make sure you’re happy with what you got. You had no idea what I looked like and I just didn’t want you to be disappointed.”
For the first time, Tina smiled warmly, her strokes easing up and becoming much more gentle and sensual instead of almost mechanically reflexive.
“Yes, I’m happy,” she replied. “I think you’re cute.”
She kissed me and quickly bobbed her head down for a few slow but determined attempts to deepthroat me. But just as I started to relax and feel good, she told me to put on a condom. I agreed, did as I was asked, and laid down to let her do what she wanted. She swiftly straddled me and very carefully positioned her mound to gently touch my tip. Given license to move at her own pace, it felt like she was releasing her frustration at my slow warmup by speedrunning to the main event.
With a deep, anxious sigh, she pushed herself down on me. At first, she struggled to properly mount me, but very quickly, pressure gave way to pleasure and a gush of wetness. With a relieved gasp, she grinned and started to grind on me with a shudder.
“Oh, you’re big,” she smiled, settling into her preferred rhythm.
“And you’re very tight,” I reciprocated the compliment. I think.
She rode me as I first squeezed her thighs, then lightly smacked her ass, then played with her breasts, fondling them, bringing them closer so my tongue could play with her nipples as she rocked her hips, putting both in my mouth at the same time. My hips tried to match her pace to sounds I could only describe as delighted solace.
She finally looked like she was genuinely enjoying herself, smiling, moaning, and giggling. We switched positions until I was pounding her in doggy, still not quite sure whether to relax and enjoy myself or whether the weirdness of this encounter should be taken as a signal to give up on spontaneous sex for at least a little while, setting up some screening procedures at the very least.
Obviously, not satisfying her wasn’t an option. The lady came first, literally and figuratively, but maybe I should lay low for a while. Be more careful. Who knows how the next one would end? Just as I snapped out of it, she withdrew from me, shaking, leaving my cock swaying by inertia.
“Did you cum yet?” she asked.
I shook my head. There hadn’t even been any build up yet. Sighing a little, she laid on her back, parting her legs and beckoning me closer. As I started to fuck her in missionary, she wrapped her legs around me and ran her fingers up and down my back. I grabbed her ass and ground my hips into her, which was met with happy, labored sighs, and a little whimpering in my ear.
There was still no real buildup to anything on my part. It felt like she had one, but I missed it, and the anxious, invasive hum of my thoughts made it frustratingly impossible to focus on what it was I was doing. It was almost as if my body was going through the motions and my brain was on for the ride, periodically registering a flash of pleasure, as if it was tapped on the shoulder and pointed to it by the rest of the nervous system.
“How come you’re not having fun?” my brain seemed to ask. “Look at what you’re doing! Shit, look at who you’re doing! Doesn’t she feel amazing? Doesn’t her soft, silky skin feel wonderful under your fingertips? Don’t her curves feel like they were made for your hands? Don’t you love the feel of her soft breasts against your chest? And how about that tight, hot, pulsating pussy wrapped around your throbbing cock?!”
“Yeah, listen,” I countered. “So I’m totally with you on this, conceptually. But can you tell my body this? Because I’m really not feeling very much right now and I’m still anxious, which I’m pretty sure is your domain.”
Giving up, I pulled out of Tina. Breathing heavily she asked me again if I came as my hands ran up and down her stomach and legs.
“Sorry, no,” I shook my head.
“Holy shit, how is that even possible?” she sighed in frustration.
You’d think that having frequent difficulty in ejaculating would make you a rock star in bed, and while in some cases it can, more often than not you get frustrated moans and groans from the women who think it’s their duty to get you off too and are getting sore from trying. Tina was definitely one of these women, and it was now her mission to get me to cum, come Hell or high water.
While this was a selfless proposition on the surface, the reality I’d experienced thus far involved a lot of roughness while my confidence to speak up was still absent. This was only a few weeks after very gentle, pleasant sex with another partner, and despite the bizarre nature of the night so far, Tina was also quite tender, which I really didn’t want to suddenly change.
Rolling over on all fours for just a moment, Tina stretched and caught her breath. She got up, walked around the bed and laid back down on a different side where she pulled me on top of her as soon as I took off my condom to change it before it broke. There was no biting, or rough stroking, or penetration. Just light kisses as she ran her fingers through my hair and periodically slipped to caressing my stomach and chest.
She flipped me over on my back and wrapped her body around me, her lips playing with mine, the tips of our tongues teasing each other. My cock was being caressed by her hot, soaking wet mound, gently circling itself around the swollen head. She guided my hand to it and encouraged me to stroke myself while she started whispering how much she wanted me to cum, how she loved feeling me stroke as the tip of my cock pushed against her in my ear, grinning with delight when she could tell by my labored breathing that it was working.
“I’m going to…” I started to gasp out.
“Yes,” she purred, “all over me.”
Silent detonations launched blast after blast of cum across her ass and down to her lower back, releasing the pressure of more than an hour of sex. Dripping with sweat, we lay in a pleasantly relaxed heap for a few minutes. Then came the standard order of business. We cleaned up, took a shower, caressing and soaping up each other’s bodies and giving me the excuse to retroactively tease her perky breasts, lithe stomach, and smooth, shaved pussy with my fingers, tongue, and mouth, feeling more comfortable and far less anxious.
As we dried off, I took my time, but she quickly got dressed citing her need to get back home to relieve her babysitter. In my post-coital haze, this new detail failed to make an impression as I admired her in a skirt, blouse, and jacket, holding her shoes, all impeccable and more than likely top notch. She paused, came over to the bed, and ran her fingertips down my body in a way she now knew would get me hard.
Her tongue slowly circled around the tip of my cock as the head met her lips, and then ever so slowly went deeper into her mouth. Tenderly, she also took in as much of my shaft as would fit, her nose tickling my lower stomach as she just as slowly reversed her motion. After a few more such slow, teasing maneuvers, she smiled, kissed me, and walked out of the bedroom.
I followed as soon as I put most of my clothes back on.
“So what do you think?” she asked, suddenly turning into, well, me at the beginning of the night, awkward and looking for some guidance. “Can we meet again?”
“Yeah, of course,” I agreed.
If I managed to make such a good impression on such a stunning woman, enough for her to ask for more, what right did I have to question my luck?
“What did you think of me? Did you like fucking me?”
Her initially fierce persona suddenly melted away. Without her heels, trying to avoid direct eye contact, she suddenly looked as tiny and fragile as a porcelain doll. Unsure of what to do, I just kissed her as deeply and tenderly as I could, hoping it would calm this inexplicable burst of shy anxiety.
“Yes, we can fuck anytime you’d like,” I smiled.
“Ok, how about next week?”
“Sure, next week it is.”
“Not sure when next week though, my husband is going to be back in town and…” she cut herself off the minute that last phrase left her mouth.
Gears in my mind started turning again as the post-nut clarity wore off. Son of a bitch! Now all that sneaking around and nervousness made sense! After blurting this out, she was panicking like a fox caught in a snare.
“Let me get this straight,” I growled, “you’re married, and you’re having sex with random strangers who don’t know that?”
“It’s not like that!” she protested. “I really just take care of his money.”
“That’s not the problem! You’re married and sneaking around behind his back. Why would you be meeting men in random hotels and planning your next session for when he’s out of town? I know what an open relationship looks like, it’s not something you spring on your people after you got what you wanted!”
She interrupted herself twice trying to come up with something even remotely plausible, and knowing it wasn’t forthcoming, stopped.
“Can I call you again?” she asked, the corners of her mouth slightly twitching as if she was about to cry.
“No.” I didn’t raise my voice. “Please leave.”
Silently, she turned around and left me alone in the room. I sighed, plopped down on the couch and turned on the TV. Ignoring what was actually playing, I thought about what just happened and how lucky I was that she slipped up and gave away something that really should have been one of the most important things I should’ve asked.
Perhaps she randomly fucked who knows how many men and found someone with whom she wanted to have an affair? There is no scenario where this kind of arrangement ends well. It’s one thing when there’s explicit blessing from the husband, or he’s even there to watch and enjoy the show, which I’ve experienced several times. But this clearly wasn’t the case here. She was just cheating on him.
Of course there just had to be a catch in this straight-out-of-a-South-Korean-porn-drama-comic situation, and to some extent, I’m sure my only requirements for sex with this beautiful woman given the context were a pulse and a face that didn’t make her queasy — or maybe just a face, period — along with the ability to get an erection and keep it.
Amazingly, a week later, she called and texted me again, begging for sex. Trying flattery and then outright questioning my masculinity, she pressed on for a solid hour to get me to agree.
“You were a 10/10,” she texted. “Please! It was so good!”
“Please lose my number,” I responded.
Maybe she had a legitimate-sounding reason for having sex with others. Maybe her husband was emotionally icy and sexually arid, and the only way she can get some human affection, no matter her looks, was by sleeping with random strangers. Maybe the relationship is basically over and they want nothing to do with each other, but don’t want to announce that they want to see other people.
Maybe, to an extent, Tina’s story is true and she was just managing her husband’s money with no love or affection between them, just some contractual obligation from a prenup that has to be enforced for some amount of time before she can be free. And I can empathize with that, but only to an extent. It’s not others’ job to help someone’s failing or failed marriage, and if anything, allowing a married person whose spouse you never met, or talked to, to have sex with you can make situations that seemingly have nowhere to go but up collapse even farther.
It’s one thing when spouses who lost their spark are theoretically talking about sex with others. Being that person makes you the face of all that went wrong, that lost spark, the years of fights, sleepless nights, and family drama. And in some extreme cases, it could absolutely get you killed. This is why Tina could never see me again. I would not be her outlet for something her husband wasn’t providing, or a stunt cock on call. After that night, I had no reason to believe literally anything she said, and acted accordingly.
Source: reddit.com/r/gonewildstories/comments/vd77f9/mf_how_to_have_sex_with_a_beautiful_stranger_with
Great internal monologue! Well written