[MF] I [F] Had the The First Amazing Sex of My Life With an Older Stranger [M] in His Hotel Room Assuming I’d Never See Him Again… He’s now my Fiance’s Boss

# Intro

I’m going to start with some context. This all took place a little more than three years ago after flying back home for the holidays to spend time with family. It was also about a year before I started dating my now fiance. I don’t remember all of it perfectly, but some of it is pretty vividly imprinted. I apologize if some parts are vaguer than others though. I also apologize for how long this is… I really got going and to be honest I mostly wrote it for myself, so hopefully people are just okay with that, and any spelling errors…

**Disclaimer:** I can see, after writing this, how the title might lead people on to thinking that I’ve done something with the man in question since. I haven’t. There’s no cheating here, and no follow up to speak of. Sorry to disappoint if you were hoping for that.

# Context and Setup

The flight back out to where I attended school had a short layover and plane transfer, with a different airline for the second leg. I met the man in question as he was seated next to me. I’m a really introverted person, and I usually hate talking to people on planes, but Andrew (which is what I’ll call him for now) had a real talent for sort of just coaxing me into conversation.

He was interesting, and had a sort of charm. He got me talking about the internship I’d just been offered, and since he was in the field we talked about that for a while, and then we talked some about the conference he was flying out to. This was pretty consistently interspersed with questioning what was taking so long to take off.

So it turns out the plane was leaking something and having some sort of issue, so they actually had us get off and wait. We chatted briefly for a bit, but he had to make some calls and then started working on his laptop while we waited. I have a lot of anxiety traveling, even today but it was much worse at the time, and called my mom about what was going on. Eventually we were told that we were going to be put on a different flight… the next morning. I was on the verge of having a panic attack and that’s when Andrew reappeared.

He seemed to know exactly how to handle it, and only once I was more calm started reassuring me about the situation itself. The airline helped with a room at one of those typical airport hotels and provided a $20 food voucher that could be redeemed in the airport. When all that was done, Andrew encouraged me not to bother trying to use the voucher and invited me to join him for dinner, which he offered to pay for, under the pretense of just wanting company.

I believed him, I remember thinking maybe he was planning something but dismissing the idea and thinking that the idea of the this articulate, confident, older guy being interested in me like that was a bit silly, and assuring myself that he hadn’t been weird at all. I think on some level I knew though. In any case, I agreed, probably a little too readily.

I had baggage, and it certainly wasn’t going with us to some restaurant in town. That fact occurred to me embarrassingly late into walking to the ride-share pickup spot. I retrospect, while I don’t think he planned for that, I feel like he definitely came up with a plan pretty quickly. He pretty immediately suggested that we could drop things off at his hotel since it was on the way to the restaurant, and I don’t think he even actually changed anything on Uber, but that’s based on just my feeling looking back. We didn’t really talk much in the car, because the driver was really talkative.

I waited while he checked in, which didn’t take long enough for me to start questioning whether this was a good idea until we were already headed up to his room. Even then, I was only sort of nervous at first, but even as I started to catch him looking at me more I dismissed that idea and started to rationalize.

I dropped off my bag, and remarked that I always felt gross after flying. He encouraged me to shower and change if I wanted, while he worked at pushing back the reservation he’d prematurely grabbed. I hesitantly took him up on this, but it didn’t feel that weird after I embraced it.

The room was insanely nice, but the bathroom was arranged so that the main sink area and bath tub were essentially open to the rest of the room, and the shower and toilet where kind of in their own, separate, tiny room. I showered quickly, and changed into a black skater dress which was really the only outfit I had that worked, but also made things start to feel weirdly date like even as we chatted while I put my makeup on.

Pretty much the second we left the room is when there was a shift in his demeanor. He became more overt in his glances, complimented my appearance (even though I didn’t necessarily feel like I looked so great, which was nice). There was a decidedly flirty edge to everything he said, and I sort of just found myself matching him without giving it too much thought. It was organic, and at the same time I started to notice him more. His carefree confidence had already been evident, and was possibly the most attractive part of him, but he was also just hot.

He had piercing blue eyes, he was I think a foot taller than me (I’m 5’2″), he clearly took care of himself, and he was almost fully gray with a short beard and short hair. He also had the top button of his white button up shirt undone, and I could see some of his chest hair which is a thing I didn’t really realize I was into until that moment. I think he noticed me looking at him, because he got a lot more brazen by the time we reached the restaurant.

Enough time has passed that while I remember parts of this dinner vividly, I can’t accurately relay the dialogue and I’m not going to try. Basically he got more and more flirty though, and he was really smooth. He also actually started to come across as a little patronizing, and he definitely briefly teased me (or maybe more properly was engaging in that bullshit negging some guys do, but more subtle) about how my dress was a little too “girl next door” for the restaurant we were in.

I was weirdly into it, and while the tension was obvious neither of us addressed it during the meal. He asked about my relationship status, I told him I was single, he told me he was divorced (which turned out to be a lie). He ordered wine, and I was a little tipsy by the time we finished. Then, when I asked about the possibility of desert, genuinely tempted by this chocolate souffle, he replied, bluntly, looking right into my eyes and said, “We’re not getting dessert here. We’re ordering room service once I finish fucking you.”

I was a little warmed up and turned on at this point, but that the way he just matter-of-factly said that… stating it as fact, just completely did me in. I could feel myself grow so flush, and I’m pale enough I knew he could see it. I paused, and only really said a soft “okay.” I was surprised at myself, but in a way it was kind of perfect. I’d only had sex with two people at this point, both boyfriends, and I’d wanted to finally have a hookup. This presented the perfect opportunity to do just that with no blow back whatsoever. I’d never see him again. He paid, we left, and the drive back, and even the walking, were almost dead silent.

# The Sex Part For Those Who Are Only Here For That (no judgement, I get it)

The tension was palpable. When we got to the elevator, he kind of all at once took my hands, pushed me to the wall, and pinned them over my head before leaning in to kiss me. It was really hot, the way he held me there and pressed into me, and good god was he an amazing kisser. It was electric, and I remember kind of just melting into the kiss.

We didn’t even break the kiss when the door opened, thankfully nobody was there, and when he finally did and let me go he sort of bit my lower lip with almost a growl before pulling away. He then took my hand and led me to the door of the room. He opened it, then turned around and stood in the doorway.

“You have a choice now Sophie. I can bring your things to the door and order you an Uber back to your hotel… or you can remove your dress and hand it to me, and I’ll let you in and decide when you can have it back.”

I think I blinked at him a million times in disbelief. He was growing a lot more commanding, and the idea was both really hot and made me really nervous. I asked if he was serious, I pointed out that someone might see, that he was more than twice my age, that we’d just met. He told me not to pretend I cared about any of that beyond how it excited me and then stretched out his hand expectantly.

This was really the first indication that I was signing up for a lot more than I’d realized. I’d never experienced a dominant guy before this, and that was a pretty strong fantasy of mine so I couldn’t really resist going along with it. And the risk just made it so much more intense.

I look around the hall, my heart pounding in my chest. It was silent though. There was not a trace of anyone. So I went for it. I pulled the dress off over my head and handed it to him. I remember feeling for a moment like the world might end, or like I might die of embarrassment, and then feeling strangely liberated when neither of those things happened. He took my dress in hand and looked down at me with a self-satisfied smirk, and I realized I had never been this turned on, let alone without any actual foreplay.

He didn’t even move out of the way at all. Even when I heard the ding of the elevator in the distance and expectantly stepped forward with a nervous look, he simply said, “I change my mind, that bra is terrible, give it to me as well.” He glanced out of the doorway for affect and then said something to the effect of “You might want to hurry.”

I complied once again, and he threw my dress on the floor behind him before yanking my bra out of my hand with a smirk and doing the same to it. He didn’t wait this time though, and instead pulled me into the entryway and pressed me into the wall while letting the door close. His face was so close.

This time I pressed my head forward and met his lips. Once again, he was a seriously fantastic kisser. He brought one hand up behind my head and the other on the small of my back, and we made out for a moment. He then took my hands and pinned them over my head again, all without breaking the kiss.

I feel like being able to kiss someone the way he could, without any drop in quality while multitasking, is a seriously underrated skill. Like, he kept my arms pinned with one hand, while reaching down with the other and pulling my panties to the side. The kissing didn’t stop, or slow, or become more clumsy though, even as he started to tease between the folds of my lips, and just around but never on the hood of my clit. I moaned into the kiss and slowly started squirming.

He started breaking the kiss long enough to tease me with somewhat humiliating questions. “What kind of woman undresses in a hotel hallway?” “For a stranger?” “One twice her age?” “What kind of woman?”

I assumed this was just dirty talk, designed to turn me on more, because he never gave me enough time to respond. It was certainly working. But once he asked the last one he broke the kiss again and sort of growled, “I asked you a question. Tell me what you are.”

I knew exactly what he was asking me to call myself, and I feel like normally I would have resisted doing it since, especially at the time, I had *very* conflicted feelings about that word, even in the bedroom between consenting adults. I was really turned on though, and it was all just insanely hot so I kind of just decided to embrace it. As soon as I opened my mouth to say, “a slut,” though, he pushed a finger inside me and curled it forward while thumbing down on my clit so that I moaned sharply and it was hard to understand me (Or at least, he acted like it was).

He was clearly having fun making it as difficult as possible for me to answer him, and the power over me combined with how cocky he was about it was pretty great to look back up at. I was still able to get it out the next try, saying “A slut,” but then he leaned in, kissed my neck and whispered, “I asked what *you* are,” so I moaned in response, “I’m a slut.” I’m pretty sure having me repeat it that way wasn’t just a power trip, but a response to the fact that I intentionally grinned up at him lustfully the first time I said it so he’d know I was enjoying it… but it was definitely also a power trip.

He then told me to take “these” off, snapping the waistband of my panties, and put them on the bedside table next to the phone before kneeling facing the bed. At the time, I recall being confused by that set of instructions. The kneeling part was pretty clear in its intent though and I did what he asked.

I think I’ve been into CMNF stuff pretty much since the second I watched him walk over to me, rolling up his sleeves, still fully clothed, while I waited kneeling naked. It was symbolically objectifying, and highlighted the control dynamic. He put his hands behind his back, told me to undo his belt, and told me, “You’re going to get me hard now. I trust you can put together how.”

Now, I’d never had to get a guy hard before, and was kind of used to me being naked being enough. Since I kind of had some toxic ideas about guys always wanting sex at the time, there was a moment where I took this personally in my head. I kind of just got over it, because after struggling with his belt and pulling his pants down I came face to face with what was, even semi-erect, the largest penis I’d ever seen in person.

I feel like with a lot of these stories, there’s an obligatory part where I say how big and rave about how into it I was. I can’t really do either. If I had to guess looking back, I’d say he’s was at least a little above average, it was more that he stacked up incredibly favorably against my two exes. He’s actually still the biggest I’ve had, but only if we’re excluding toys. As to the second part, honestly, in the moment it was just daunting.

I think he saw this on my face because with possibly the smuggest, most self-satisfied tone I’ve ever heard from a man to date (seriously saying something) he said, “I take it your exes were on the small side… you’ll do fine.” I think the fact that he new he was the largest I’d had but didn’t cartoonishly fixate on the fact definitely worked in his favor.

He put his hand on the back of my head, intertwining his fingers slightly with my hair but applying no pressure, and I started. I have to admit, I wasn’t great at blowjobs. I’d never given one for particularly long, and always felt fairly indifferent toward the act. I was kind of just bobbing my head, admittedly monotonously. I’m not really sure whether it was due to disappointment with my efforts, or just because he felt like it, but he started telling me what to do.

He told me to lick up and down his shaft. Then swirl my tongue at the tip. Then kiss it. Then lick his balls, which was new, and not as gross as I thought, and dirty in a fun way. Looking back, I would credit this blowjob with revealing to me that I could enjoy giving them for their own sake and with making me significantly better at them. Putting in the effort and variation, and getting to feel his enjoyment in the way he tensed and hear it in increasing groans was just really hot.

He then had me take him in my mouth again. I started twisting my head more than before and using my tongue more of my own volition. Eventually, he said, “good girl,” while stroking my hair, and I just melted. Seriously one of my favorite things from the night, I can still hear that gravely, confident voice half groaning the words. It was like sexy, verbal crack.

Eventually he told me, while stroking my hair, that he wanted me to deepthroat him, and asked if I thought I could do that and to shake my head yes or no while pulling back. I told him not on my own. I don’t really know what came over me, though I believe the idea came from the way his arms had been tensed like they were going to force my head down but he restrained himself, but I told him that, if he pushed my head down, I thought I could do it.

I think I half wanted to pull it off just so I could say I had. I’d always fantasized about rougher “manhandling” but had had a hard time getting my prior ex to really do it, and it seemed liked he had it in him so I was definitely trying get him to. I actually broke that cocky look for a fraction of a second, and he looked down with quizzical surprise.

I looked up at him, and in retrospect was surprisingly blunt and forward about it. I don’t remember exactly what I said, but it was something along the lines of telling him that I could feel he’d wanted to do it, appreciated the fact that he didn’t, but was happy to have him do it once as long as he released right after. I took him in my mouth again, and he didn’t wait for further permission, running his fingers through my hair and pulling my head forward.

At first I moved with him, but then he pushed further and I involuntarily resisted. It was quick though, but like I could feel it in my throat and gagged *hard,* he groaned “You really are a slut aren’t you,” and kept pressing. I felt him like, reach the part I swallow with I guess. It was insane and kind of alarming. And he let go and I coughed. The look of satisfied approval on his face was pretty great, but while I was glad I tried I wouldn’t have done it again.

He looked down and told me I had more than earned my turn, and after a pause told me to stand up and lay on the side of the bed and spread my legs. He knelt between them and started kissing around my inner thighs, back and forth, his warm breath over me as he switched sides and each kiss moved a little closer. I think I called him a tease right before he kissed me in the middle and sort of dragged his lower lip up so that there was first upward pressure on my clit and then it just rolled over. He repeated this several times. It was amazing, because it wasn’t really too much direct contact, more pressure based to start, and more intermittent I guess.

He started fingering me at the same time, and slowly started to switch to sucking and using his tongue more. He pretty easily pushed me right up to the edge, and then just stopped. I said no, and he said something about it being better. He ended up being right, but I think I was actually whimpering by the time he let me. The orgasm was seriously amazing though, I was shaking for a while, and then it sort of just turned into a second.

I haven’t actually managed to duplicate that, with or without a partner, like I feel like there’s usually a sort of mental block where I have to stop and that time I just didn’t. I did push his head away after the second though, and I know I was pretty effusively singing his praises and not even really so much for dirty talk but just because I was pretty wowed.

He then stood up and fucked me on the side of the bed. He didn’t quite start right away though, like he ran his dick up and down a bit and then very slowly pushed in. I was actually surprised it didn’t hurt (remember, both my exes before this point were seriously small). I was more surprised how different it felt without a condom. It felt really great, but… that was my first time, and he was a stranger. I managed to sort of moan “condom?”, but he just replied, “I don’t have any,” and didn’t stop. I tried to mention it again, but kind of gave up.

His thrusts were slow but hard. Maybe not quite slow, but not like… fast. Over time the pace didn’t really change but they got harder. It was pretty great, and it was deeper with more pressure than I was used to. Plus he started playing with my clit at the same time. It was really intense, and he leaned in and we kissed while fucking. I wrapped my legs around him and sort of pulled (which really wasn’t that effective as I recall, but whatever).

He started telling me I felt really good, and called me a slut, and had me call myself a slut. He even had me tell him my “pussy” was his. (As an aside, I hate that word and think it’s super stupid, usually takes me out of the moment, so kudos to him for being good enough I didn’t care at all). I kind of got off on feeding his ego, and told him he was the biggest I’d had, that I’d never felt so good. All of it was true, it just usually feels silly to say stuff like that, but the energy he got out of it was just intoxicating.

When I felt myself getting close to orgasm there was a lot of surprised exclamation on my part. I’d never actually orgasmed during sex before, so it caught me by surprise. It also was weirdly fast once I got close, like one second I was at the point I’d expect to plateau at and the next it was imminent. I was really really loud (this becomes important) without fully realizing it. And then it sort of washed over me. This one wasn’t actually as intense as from oral, but was more whole body. I was still shaking when he pulled out pushed me up on the bed, and rolled me over so I was on my stomach.

Then the phone rang. I tensed up, but he just answered it. I don’t remember what he said exactly, but it ended with something about apologizing, but also saying while we’d try he couldn’t promise anything. I felt so embarrassed, but he got up and pushed into me before I could respond. My mouth was agape, and he had my own panties in his hand actually and stuffed them into my mouth while telling me to be quieter. That was really hot, and then he lifted me and sort of through me up more on the bed, and then roughly rolled me over.

He said something then, and I kind of wish I knew what it was, but I didn’t really hear it. He thrust into me all at once without too much warning, as I lay prone on the bed. It was a lot rougher than before. Like, before he was clearly trying to make it as good as possible for me, which was really hot, and now he was making it as good as possible for himself, which as also hot in a different way. I could feel his full weight behind me as he thrust, and it kind of pushed forward I guess. I haven’t been able to duplicate the position with any partners since, but the angle was like perfect. He alternated between pulling back on my hair, and smacking my ass honestly a little too hard.

I could feel myself building towards an orgasm, or close, but was pretty sure it wouldn’t happen without any clit stimulation. Then his thrusting changed, and he started growing. I only really felt the warmth, but that was enough to realize what was happening. I’m not sure if it was just perfectly timed, or if it was the realization that he was cumming in me and how bad an idea that was that did it, but I came again and he continued thrusting through it despite having finished.

I laid there recovering for a bit after pretty immediately pulling my panties out of my mouth (they were mostly out anyways at this point), and he collapsed beside me. I said something like wow, and he chuckled. Then I stood up and looked down, then back at him a little pissed and he just said sorry in an obviously unapologetic tone, self-satisfied tone. I didn’t really press the issue further. I went to the bathroom, then helped myself to a shower and tried to clean up. It just kept coming out though. Super annoying. He actually followed through on room service dessert though, which was pretty great, and after that I pretty much collapsed.

I woke up super sore, and super embarrassed, but we both had to rush out the door, so it was all so suddenly over.

# And Now He’s My Fiance’s Boss

I really can’t overstate how impactful that encounter was. Like, it’s single-handedly responsible for turning me from someone who was really meh about sex, and never engaged in casual sex, into pretty much the opposite. It also sort of kick-started a year long “hoe phase” for me that lasted pretty much up until the second my now fiance and I decided to become exclusive.

Like, I fantasized about this guy so much, and so exclusively, that it was kind of a problem. I would project him onto new sexual fantasies, and while I’ve had other similarly spectacular experiences, and even kinkier ones, this one will always have a special place. All this to say, his voice is burned in my psyche…

… So, my fiance (who we’ll call David) started a new job remotely and about two months in now his headphones were broken, so I was able to hear one of his meetings, and I swore I recognized that voice. Like it all came flooding back in freakish, alarming detail. I didn’t believe it though, because the name was different, and seriously what are the odds?

So I looked him up on LinkedIn (this was a really stupid idea, he has since also looked at my profile and I’m left with no idea if he recognized me). Sure enough, definitely him, (different name, also learned from David that he’s married, we’ll say his “real” name is John). Honestly not my favorite situation, but it’s not as bad as it could be.

I’ve told my fiance about my encounter with John before, just, not that it was with John specifically. He has a cuckold fetish that I’ve tentatively agreed to build towards engaging in, and mostly for now that just means telling him stories from my past. The issue that concerns me is that, the way he reacted to this story, he might be too clouded by his fetish to see that bringing John in is a deeply stupid idea on every conceivable level, with John being David’s boss and me being completely unwilling to knowingly sleep with a married man.

Or I could be wrong, and the fact I’ve slept with the man who’s now his boss (who he hates) could be too real and it could be a problem that way. I’m also really hoping John didn’t catch on and doesn’t make a thing out of it if he does, because based on David’s description he might be the type.

Source: reddit.com/r/gonewildstories/comments/p6zn3s/mf_i_f_had_the_the_first_amazing_sex_of_my_life

3 comments

  1. If your cuckold fiancé tries to engage in this I see this going very poorly.

  2. Tbh, I actually came to see how your fiancé reacted. I wouldn’t engage the boss though, that could turn bad real quick. & when games like that get played, rules get broken.

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