[MF] A bizarre night with a woman out of my league [long][plot twist] | 2016

Hi fellow redditors. So far, there's been positive response to these stories and they're a kind of therapy for me, giving me a chance to replay events and contextualize the good and the bad. But before I keep going with these, I'd like to know what you think and if you'd like to see more stories after these ones. If you like what you're reading, I'm happy to keep going. All these stories are 100% real, and I assure you, so is this one, even though it was every bit as bizarre as it reads.

Were I to grab myself from the past about to answer the phone that night, I would proceed to call my past self an idiot whose sex drive was clearly shouting over his basic sense of 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 was it. The whole thing was shady from the get go, but something in me just wanted to believe. So when “Tina” posted in a public chat room if there were any men in my then age range in my city without any plans for the night, I replied. She messaged me privately, asking to call me.

“Hi there,” an anxious female voice greeted me when I picked up.

“Hi,” I greeted her, “so what are you looking for tonight?”

“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 pics or something?”

“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!”

So, so many red flags. But the hormones pressed me and I agreed. Along my way to the hotel, she called twice to make sure everything was still proceeding as planned. She was very nervous, her voice shook, she talked a mile a minute, and she asked the same questions repeatedly. Somehow not quite registering this as a big enough red flag, I got to the hotel, checked in, found the room, and dropped off my overnight bag with a change of clothes and all the toiletries I’d need in the morning. The sane voice asking if I was in my right mind was being outshouted by the far, far less sane voice wondering if I’d lost my sense of adventure. 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, I’m on my way right now. 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 and positioning myself near a door that would lock behind me should I have to make a run for it for some reason. As my mind finally began to come up with fevered scenarios, as if the lag between the promise of sex and realization that what was happening was dangerous has been finally compensated for, a now familiar woman’s voice asked for my name. I turned around to find out who lured me here and was instantly stunned.

She looked like a fashion model. Caramel skin, long, dark hair, shapely legs, perky 36Cs, perfect hourglass figure, nearly as tall as me, and dressed in business attire, Tina strolled towards me. Imagine a taller, darker skinned Chrissy Teigen with less pronounced cheekbones. We shook hands and I led her to the room. A new thought appeared in my head. What if someone thought I hired an escort and called the police? From the side, it didn’t look good, and what was I going to tell the cops? This woman was so obviously out of my league. How hard would they laugh at the idea that if anything, I was the escort to fulfill a fantasy, found on the web?

As we came in, she asked if she could dive into the shower to freshen up, and of course I said she could. For the next ten minutes, my mind fought between whether I should try to surprise her in the shower or I should search through her purse for guns and knives. Before I could make up my mind though, I heard her uncovering the bed and sitting on it. Walking into the bedroom, I saw her in a short, sheer nightie, eagerly expecting me. Time to turn on the charm. Or rather it would be if all the anxiety hadn’t tuned the charm into playing a human possum. Somehow, early on, I ended up on top of her, fully clothed, but completely frozen as awkwardly as possible.

“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 managed to stammer out, “my previous partner was black so this is not the issue. I just… 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 threw off her lingerie and laid on her stomach, giving me a great view of her perfect breasts and butt as she spun around. 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. She turned around so I could do a front massage, but it quickly turned into massaging her breasts and kissing down to get between her legs where I dove straight for her clit with my tongue and after getting her into it, slipping my tongue inside her to enthusiastic purring. After five minutes of this, she clearly wanted things to progress.

“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 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 that I should 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, very carefully positioned her mound on the tip of my cock, and pushed herself down on me. At first, she seemed to struggle to properly mount me, but it soon, pressure gave way to pleasure. With a relieved giggle, she grinded on me with a shudder.

“You’re big,” she smiled.

“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 and I could suck them as she rocked her hips. To my relief, she looked like she was genuinely enjoying herself, smiling, moaning, and giggling. We switched positions until I was pounding her pussy in doggy, still not quite sure whether to relax and enjoy myself or whether the weirdness of this encounter should just make me give up on sex for a while. Not satisfying her was obviously not an option, 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. There was still no real buildup to an orgasm. It felt like she had one, but I missed it, and my anxious thoughts made it impossible to focus on what 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 here and there as if tapped on the shoulder and pointed to it by the rest of the nervous system; “how come you’re not having fun?” Giving up on, I pulled out of Tina. Breathing heavily she asked me again if I came. The response was again negative.

“Holy shit, how?” 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 had experienced thus far involved a lot of roughness that did very little for me, and at the time, the confidence to speak up just wasn’t there. 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 and I really didn’t want that to suddenly change.

But lucky for me, she just said “come here” and pulled me on top of her. There was no biting or rough stroking, or penetration. Just light kisses. She flipped me over on my back and wrapped her body around me, her lips playing with mine, the tip of her tongue teasing the tip of mine. My cock was being caressed by her hot, soaking 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 while the tip of my cock was pushing against her in my ear, grinning with delight when she could tell by my labored breathing that it was working.

Finally, I came all over her perfect round ass and she excitedly gave me a deep, passionate kiss while my body still spasmed. Over an hour of buildup resulted in an explosion that reached all the way up her back. 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, a jacket, and high heels, 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 instantly 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, wonderful, teasing maneuvers, she smiled, kissed me, and walked out of the bedroom. I followed.

“So what do you think?” she asked suddenly turning into me at the beginning of the night, awkward and looking for some guidance. “Can we meet again?”

“Yeah, definitely,” I agreed. If I managed to make such a good impression on such an attractive woman, who am I to question my luck, right?

“What did you think of me? Did you like fucking me?”

Unsure of what to do, I just kissed her as deeply and tenderly as I could, hoping that would calm her down and comfort her apparent burst of 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…”

Son of a bitch! Of course! Now all that hurried sneaking around and anxiety made sense! Without saying a word, I turned around and quickly got dressed because while I had no intention to leave the hotel for the night since after all, I paid for it, there was no way that I’d be arguing naked, remembering Mark Twain’s immortal words about the relative lack of power in society of those bereft of clothes. She was panicking.

“Let me get this straight,” I growled, now fully dressed, “you’re married, and you’re having sex with strangers who don’t know it?” “It’s not like that!” she protested. “I really just take care of his money.”

“Fine, but that’s not the issue, that issue is that you’re married and are obviously 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 is like, it’s not something you spring on your partner 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, but I tried my best to sound as firm as possible. “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 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 and under no circumstances would I do that to someone. It’s one thing when there’s explicit blessing from the husband or he’s even there to watch and enjoy the show, but this clearly wasn’t the case here. She was just cheating on him.

Amazingly, a week later, she called and texted me again, begging for sex. Trying flattery and outright questioning my masculinity, she pressed on for a solid hour to get me to agree. In the end, I told her to lose my number and never call me again, blocking her wherever I could. The ethical and possibly physical consequences of sex with her, even though she was beautiful and a generous lover, were just not worth it. While my hormones blinded me from the initial red flags, I wasn’t about to let them blind me again, no matter how fun the night actually ended up being.