Sexiest hotel encounter?

My experience

In the mid eighties my ex and I were traveling to a family reunion in Arizona. She disliked driving almost as much as she disliked sex. After driving for 12+ hrs, I rented a room and knowing she'd go to sleep immediately, I grabbed some beer and a skin mag at the corner quick mart. I grabbed a small empty trash can from the room and headed down the hall to get ice for my beer. As I approached the machine a could here giggling, and it was Female giggling. I strolled pass the ice machine, and peeked around the corner. I saw a lady in her early to mid 20's posing by a cigarette machine wearing a pair of heels, and nothing else. For the next 2-3 minutes her husband snapped pictures as she flirted and posed. She was a strawberry blonde with large jiggly boobs, and a sexy ass that was really white compared to the tan she had otherwise. It was such a sexy sight, but I began to feel intrusive so I snuck back down the hall to my room. I was afraid that scooping the ice would scare the girl, or at least ruin their moment. Kinda sucked drinking warm beer that night, at least I had a dirty magazine to distract me.
 
I have never had one of the serendipitous experiences some have described here (my sexy encounters have been planned), but some of the most memorable have been with women I met on Lit. Hotels in Ann Arbor, Chicago and Montreal have all been home to encounters I will treasure forever.
 
Sucking off the Manager

I was staying in a hotel with a few of my friends one day and we had just checked in. There was some sort of complaint from my friends about the room so I volunteered to go speak with the front desk about it.
I walked up to the front desk and the manager was there with one other staff person. I explained the issue with the room and he quickly walked out from behind the desk and asked me to follow him. He took me to a couple of the other rooms and opened the door to et me look at the room and asked if I would like to switch rooms. He then said that he had an even better room that he would let us switch over to it was just down the hall.
When he opened the door I walked inside and he followed me in. Just as the door shut by itself neither one of us said a word and as I dropped to my knees he unzipped his pants and pulled out a long thick cock. I immediately buried it as far down my throat as I could. He took over and started moving his cock in and out of my mouth and quickly put my head in his hands as he picked up the pace with his hips by now he was going all the way down my throat with that big cock of his when suddenly he shot his load
 
It could be the overeager maid. It could be the, um, open blinds. It could be the B&B with the thin walls and the 80-year-old owner. It could be the out-of-town encounter.

Please share your tales.

he stranger -- reviving your thread again hoping you set that PM active again.. want to share another story :)

D.
 
Stories aside…
I'm not lucky enough to have tens or hundreds of fun events in hotels, yet… I have some :)
We were a group of experts and students (mixed in order to get maximum efficiency and effectiveness) in a conference and following trip to see how theory works in real life.
We have been travelling for a week and one of last stops was a highway hotel - that type of a place where isn't much entertainment or "hotel star facilities".
During the trip I have gotten close with a young lady (she was 20-something student).
Our rooms were not far from each other and I texted her an invite to watch a movie together.
We had some vine, some chat and decided that current movie is rather boring.
She started to switch channels and stopped on an adult channel (I believe that bypassing truck drivers did appreciate the open adult movie channel).
A simple hardcore action was on the screen - guy was fucking a girl on a kitchen table. She was quite vocal - a typical porn…
I did assume my young friend would switch to another movie, but she fixated her eyes on a TV screen.
Then suddenly she said that she needed to go to lavatory.
She bursted in to the bathroom and porn continued…
Must say - my dick started to stiffen, and I kind of tried to imagine how it would be…
I was genuinely surprised when she came back to the room completely naked.
Her little perky tits with hard nipples, her eyes saying "frisky" and…
Well - let me just say - she was a hot and wet fuck. She insisted that TV show continues.
After our first cumming (we both finished almost in the same time), there was another movie with a girl masturbating.
Oh my, she did jerk me off and suck me while looking at porn on TV and masturbating at the same time.
Really - hot one.
After this we did go to shower together (;
 
I met a woman on an on-line dating site, and it was quickly obvious we both didn't want to date (but rather, to fuck). During our conversations prior to the rendezvous, it was apparent that she was an exhibitionist and got off on being watched. I met her in a bar across the street - she was a tall redhead wearing a long red cocktail dress and nothing underneath. (I had booked a room at a Courtyard by Marriott.) As soon as we walked in the door, she dropped to her knees and sucked me off as took off her dress.

I walked her over to the balcony that opened up to the courtyard, facing dozens of windows. She hung onto the railing as I fucked her hard from behind. Her red hair was flailing all over the place, and she was shouting pretty much at the top of her lungs, "Oh, yes, fuck me, give me that big, hard cock, fuck my cunt..."

It was obvious she was trying to attract attention and solicit more of an audience. She succeeded. I was getting off on this now and I fucked her like a rabid animal. When I emptied my load into her, she screeched and shouted wildly as she came herself.

We got a rousing round of applause from several windows and many catcalls. She dropped to her knees again to clean me off as our new fans no doubt enjoyed the finale..

Then she thanked me, put her dress back on, told me she was married and just wanted some "strange cock". She left.

The whole episode lasted about 45 minutes, but it's my hottest hotel fuck to this day.
 
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I had met a woman on an out of town trip (my cousin's wife) and when my wife had to go to Europe for a family emergency, Ms. x came to my city and I booked a room in an older hotel with a certain amou t of "faded elegance" you might say.

I picked her up at the airport and we rushed to the room and started undressing she went into the bathroom and came out in a faded, worn flannelette nightie and fuzzy slippers.

Even though we were new and horny lovers, it felt like we'd been together forever.
 
Great stories, I love this thread.

I met a girl walking down the street in Hawaii. We went to a bar, talked for a while and then ended up at my hotel room.

We kissed a lot and rolled around on the bed. Soon she had my pants down to my ankles. She put me in her mouth and gave me an amazing blowjob. I tried to get her to stop so I would not cum too soon, but she would not stop and I came in her mouth, rolling about, moaning loudly. She held on tight, her hands on my butt as I jerked about, she did not miss a drop.

ES
 
Share a room

I got to a hotel on one of those nights when they are down to their last room. I was a head of a woman who also wanted a room. Trying to be the gentleman I told her she could have the room and I grabbed my bag to leave.

She told me that she would happily share to room with me. We had talked on the Bus from the hotel and she seemed like a nice person so I told her sure. Once we got in the room I suggested I sleep on the floor. She told me she is okay sleeping in the same bed with me, knowing I would get much better rest that way. She asked me which side I wanted and we both got undressed. She got undressed in the bathroom and when she was ready I had turned out the light in the main room so she could slip in the bed without me seeing her. In addition, I assured her I would not touch her during the night.

About Midnight, I started to fantasize about fucking her. I got an erection and it made a "tent" in the covers since I was laying on my back. At this time there was a little light coming in from the window that put a "spotlight" on my tent. The bed was not large enough for me to move further away from her and out of the spotlight, I certainly could not move closer to her or she would wake up. I just sat there wondering what to do.

About 5 min later I heard her stirring a bit and move to sleep on her side. Next I felt her hand on my thigh and slowly move into my shorts on my dick. I was shocked. She slowly stroked it getting me real hard. She pulled my shorts out of the way, barely below my balls, and got on top of me slipping me inside her.

She fucked me in the Cowgirl position for about 5 min until she had an orgasm. She road me a bit longer to trying to get me to cum inside her. I did have an amazing orgasm, so she rolled off me and went back to sleep. The only words spoken during our sex was her telling me to cum inside her, she was on the pill, and a Shssh here and there from her trying keep our sex quiet.

The next morning no words were spoken of what happened that night before. She got dressed in the bathroom, acting shy again like I did not have any carnal knowledge of her the night before.

If I had not seen the wet spot on the sheets of the bed when I walked out, I would have thought the whole thing was a dream.

ES
 
In my country it's common for people to stay at their family house till their mid-20's, and the sexual activity of the young couples contains a lot of action in the so called "half-overnight hotels". But those encounters aren't probably the subject of this thread, so I 'll pick something from my later life.

I had met a woman in a chat room (yes, it was soooo long ago when chat rooms were extremely popular) about gardening. A phd in literature who had quit her career in order to follow her husband in a small country town, very soon she had discovered that the only thing she could do was to take care of their daughter and kill time on the net until his return from work. We started exchanging mails, which gradually became hotter and hotter.

One day, after some months of written communication, we decided to meet at a motel, something that we repeated many times in the following year. Every encounter could be classified as the "sexiest hotel encounter"; she was a real volcano who used to squeeze every last drop of mine. The best thing I remember, is that she had the strongest orgasm contractions I 've ever met! While licking her clit, I used to sink two fingers in her pussy and, when she was cuming, it was like pliers grasping them.
 
Sure wish I could add to this tonight. I'm stuck in a hotel and have no options here.

But a few years ago I met a girl online and we chatted off and on for several months. I ended up at a conference in her city, so the chat got more involved so to speak.

We ended up meeting, going to dinner and coming back to my hotel room. She had told me ahead of time that she would feel bad about having sex (she was married but separated at the time) and I was ok with that. We ended up making out in my room and lots of touching and groping. She had great breasts and I enjoyed them immensely and she was rubbing my cock through my pants and believe me I was unbelievably aroused.

After probably an hour or so of off and on making out and groping, she start gathering herself like she was going to leave. She gave me the "Well it's about that time" look. So she gave me one last kiss, long, deep, wet kiss.... and then told me she couldn't bare to leave me like that. So she dropped to her knees and gave me a really fast (I was so turned on it didn't take long!) blowjob before she left. It was amazing.
 
An ex and I, and she was an EX at the time, spent a weekend in Duluth. I don't remember what happened but we started to talk about our dead relationship and ended up having REALLY physical sex, physical enough that I bruised some muscles and was unable to walk for 24 hours. That was no question that neighbors heard us as employees and visitors alike stared at us over the next 36 hours. It was sad and amazing at the same time.
 
Like many others here, when I stay in a hotel for business travel,I inevitably enjoy a nice masturbation session. The other morning I had some time to kill before checking out. I jerked off and went back to sleep, naked of course.

Despite having the do not disturb sign out, I heard a knock on the door. I rose from the bed and headed for the door. As I was heading towards it, the door opened. The maid entered saw me, quickly apologized and headed back out. She sounded young at least.

After my shower and packing up I headed out, hoping to at least get a good look at whoever saw me. The cart was next door and the girl stepped in to the hallway. She was a young smaller black girl, probably early twenties. Much nicer than the typical hotel maid. She apologized to me again, saying that someone said I had left already. I told her its no big deal and that she was probably more embarrassed than me. She said "yeah probably" kind of shyly. I told her it might have been a bit of a thrill too (meaning for me) but she agreed nervously. I smiled and wished her a good day. Im sure she was relieved I didnt over react or complain to the managers.

My only regret was that I was not more erect but i have decent enough size that she got a good look. Im sure she'll be more careful going forward but at least she has a memory of walking in on a good looking naked older man.

Obviously not the kinkiest or hottest hotel story but it was a thrill,hopefully for both of us.

Nice one! Yes the same thing happened to me and my fantasy is that she comes into the room closes the door behind her and we end up having a nice long fuck.

ES
 
One night stand in Vegas. Gave an amazing handjob to a guy as we stood, kissed and looked out at the great view outside our window. He cummed so hard he hit the ceiling, my stomach, chin, cheek, etc
 
I have one sexy hotel encounter for sure that keeps coming back to me each time I see this thread in my subscribed index.

Here it the story:
Around the year 2000, I was partying in the summer all day on a local lake on a boat with booze and sun etc. I got pretty drunk. We then went to a bar on the lake that often has some sexy cougars married to wealthy guys with boats on the lake. One of these cougars saw me and didn't let it go......fast forward some hours and I am in downtown Minneapolis in a bar and at the outside rooftop bar a woman makes eyes at me and never takes em off. As I offer to buy a round for my friends I forget about her but then am quickly reminded as soon as I get to the bar. She comes in to meet me. She has short soccer mom hair, a tight white sleeveless blouse with no bra. She also has platform heels and a skirt that is way way above the knee. She introduces herself, we have one drink and she asks if I would want to go for a walk. I say yes. We get to the sidewalk and we kiss, She grabs my ass and touches my muscles and body and tells me how she could not take her eyes off me at the lakeside bar (I never saw her) and how she wanted to be naked with me. As we kissed she revealed she had no panties and I could feel her wetness down around the inside of her knees. Our gaze went to the Double Tree hotel next door and I asked if she was game and she said yes. We got some looks as we entered but I was not phased. We entered and got into the elevator and started kissing. She lifted her skirt in the elevator to reveal a perfectly lean shaven pussy that was wet and ready. We got into the room and her shoes came off and she undressed me in about 1 minute. Next thing I know I am on the bed with her on top in a 69. She still has her clothes on and I am eating her sopping wet pussy. AS I lick her she tells me how she "cannot wait to fuck me." She then gets off my face and kneels next to me. She removes her top to reveal her gorgeous breasts with implants. They were perfect and her nipples were soo hard. She then stands and turns to me and has me unzip her skirt. I do so as she rubs my cock. She then sucks me some while standing and quickly moves to straddle me still sucking....she climbed me like creeping ivy next and started to rub my chest and asked if I'd fuck her now. I made eye contact as she sucked my finger and nodded. She took me inside her inch by inch, lowering herself down in a squat position. She took me all the way in and out and was so wet and squeezed me so tight I was in heaven. Yes I was bareback too. "The moment" was so hot I didn't even think of it....anyway...she rode me hard...very hard until she orgasmed at least 2 or 3 times.....screaming loudly. It was awesome to watch her 48 year old body bounce on me over and over. I then stood up with her while I was still inside her. She was about 5'4" 115 lbs I would guess and I am 6'6" 255. I walked with her on my cock to a table where I had her pussy just off the edge and I fucked her very hard...I could feel my balls on the table's edge as I pounded her...until I felt them tighten and I pulled out and came all over her stomach and tits...it was soo hot. She screamed so loud I thought surely security might come. Well, we proceeded to fuck 3 more times until almost 5 a.m. It was unreal. She got me hard again each time and was soo wet each time. I came in her mouth once inside her and on her tits again. I cannot count the orgasms she had but she was amazing.

So hot! I definitely need to revisit this thread and read other posts today! This is the first one I stumbled upon and now I'm all tingly!!
 
Several

But one that is hard to forget was in a downtown hotel, maybe tenth floor and she was at the window with her hands on the sill, bent over, back arched and I had her from the back.
 
Being asked to drop my towel by two ladies about to get on the elevator. To their surprise, I did!........:D
 
It could be the overeager maid. It could be the, um, open blinds. It could be the B&B with the thin walls and the 80-year-old owner. It could be the out-of-town encounter.

Please share your tales.

This is difficult because I can't really choose among them. If pressed on it, I'd say the first time I was taken to a motel to meet a group of men was probably the most memorable because it was my first. Plus I was blindfolded during it and spent a lot of time tied up.
 
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