Sexiest hotel encounter?

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.
 
Oddly, I think my sexiest hotel encounter was not one that involved sex or someone else. I was on vacation alone and since I was out doing some city photography I decided to turn the camera on myself and capture some sexy and kinky photos. Good times! :)
 
Helsinki

Spa at a hotel in Helsinki. Late night. I asked the receptionist if I could swim in the nude provided no customers came, but she said that it was Finland and no one would care. I had the pool and hot tub to myself, so it was never an issue. At 11, she came in and said the pool was closing, so I got out of the water, an erection quickly forming as I could feel her eyes on my. She said I could stay if I wanted and said she was going to swim, stepped out of her dress and dove into the pool in her light blue bra and panties. We had lots of pool sex that night and the next!
 
Fantastic post for a newbie, Saustin. No apologies needed. It was a very hot story.
 
My story

My encounter was with my wife, but it was under unusual circumstances. I had come out to my wife as bisexuals about 2 months earlier. With her OK I was meeting with a man. It was my first time. We live in a small town, and I agreed not to have sex with anyone In our town. My hoOK up was with a guy in a city about 60 miles away. My wife wanted to meet me at a hotel in the city after my meeting with the guy. Previously she had told me not to expect sex with her for several days after I had been with a man.

I arrived first and as she requested I showered. When she arrived she was very curious about my first gay encounter. Soon she was stroking my cock. She made it obvious she wanted me to give her oral sex. I eagerly accepted. She was obviously very aroused. Soon she said "Go lower". I knew what she wanted. I had serviced her an us before, but this was the first time she had requested it. Actually it was more of a demand. She had a very intense orgasm and then had me jack off as she watched.

Later I learned this was called reclaiming sex and is often very hot. I also knew she accepted my bisexuality.
 
Just few days ago returned from the trip.
I had kinkiest hotel fuck so far. Staying at Homewood Suites and having evenings free I went to the hotel reception with the intention to drink some wine at local restaurant. I noticed nice midget lady asking something to the front desk.
I turned around and went to the elevator together with her.
Tiny, but with firm tits and really sexy ass.
My cock was semi hard.
I asked how to get rid of the boredom…
She did look upwards and said she was bored too and smiled.
I played bold and suggested that we can drink wine at hotel pool. As I checked before that place was dead quiet for three consecutive days so…
It was surprisingly good - she said OK. And still not believing that evening will turn out somewhat interesting, I pressed lobby button. We agreed to meet at pool at fifth floor in fifteen minutes.
When I was there with glasses and opened bottle she was there too. In a bikini.
Despite the late evening and dusk, she was wearing bikini (!) that was leaving for imagination only the colour of the pussy lips. All other nice things - her tits with surprisingly long nipples, her round ass and other really good grown-up woman's body elements, framed in the midgets body shape.
She said she was 26 and she's been knowing what I have in mind.
I laughed at this, but agreed that she has made quite an impression.
"I know - some men think of me as their nasty dream " she said.
I kissed her. Starting with lips, neck, shoulders and going down to the beautiful tits.
She said" I'm shy about the nipples" - but I kept kissing and touching her.
I invited her to sit down on my lap and feel my bulge. I kissed her and massaged all the hot body.
She started to get really wet.
After couple of minutes she said - OK, let us go in to the jakuzi (it was more like simple bubble bath). Water was warm and I did enjoy all the things here. As I did enjoy her hands jerking me under the water…
>>>>
 
Mine was a lost weekend with my girlfriend. She was the hottest woman I've ever been with. We tried everything - a karma sutra of different positions, oral, light punishment, massages, locations - shower, bed, table, items (banana, toys, ice, food), lots of excitement, laughs, moans - and dozens of orgasms (mostly hers - she was phenomenally multi-orgasmic). We only had sex or slept when we were in the room and we didn't leave (or sleep) for more than about 12 hours out of the entire 48 hours we were there. I pretty well exhausted all of my one on one sexual fantasies with her.
 
I just remembered a hotel sex scene that actually changed my life.

Over 25 years ago I was at a dance club in Seattle. There were four of us guys who went to the club. I met by accident, I thought, a petite woman with a nice curves sitting by herself. We talked, danced, talked, and danced some more. When it was time to go home she told me she would love to go to my hotel room. All five of us piled in the car and off we drove to the hotel. She was sitting on my lap during the drive and made it a point to show me discreetly she was wearing a garter belt, stockings, and no underwear.

Once we got to my room, there was no talk, just moaning kissing, and fucking. From the beginning she took over. She gave me a BJ and when I told her to please stop I was about to cum, she did not and drank it all down as I came in her mouth. But within a few minutes she had me hard again and fucking her. Like a wrestler with amazing moves, she would move a leg, pull on my arm, lift her hips, and we would be in a different position. I would continue to fuck her until she had an orgasm then we would switch positions right before I was about to cum.

She had this amazing ability to control my orgasms, while at the same time letting her own orgasms flow and flow. She came maybe 5 times total and I had about 3 orgasms. She did not do much talking, just lots of moaning. When she decided it was time for me to cum, I did very intensely losing complete control. I tried to resist at first but it was no use, so I submitted to her whims.

After about 2 hours we were done and just resting on the bed. There was very little conversation, certainly not like when we met, she had a smoke, and told me to take her home.

It was the first time in my life that I was "used" like a piece of meat by woman. I did not like it at first that I was tricked and overpowered like that. But the more I thought about it, the more it turned me on. Trying out life as a sub, was my next step.

ES
 
My hubby ordering delivery pizza at the hotel and then tying me naked to the bed and when pizza came he opened the door let the guy in and then walked into the bathroom to get his wallet leaving me tied spread eagle on the bed with the pizza guy standing there
 
My hubby ordering delivery pizza at the hotel and then tying me naked to the bed and when pizza came he opened the door let the guy in and then walked into the bathroom to get his wallet leaving me tied spread eagle on the bed with the pizza guy standing there

Wow, what was the reaction of the pizza guy?

Love your hubby
 
Mohegan

My hottest encounter was about 5 years ago when I was in my mid 20s at the casino. While my man was in the poker room I sat at the bar drinking by myself. An older guy sits down next to me and we start talking about life, our relationships, etc. His wife stops by and he introduces us. She leaves and we continue to drink. He is buying me drink after drink and out discussion is getting more and more risque. Flash forward to him followimg me to the bathroom. Pushing me up against the wall to kiss and fondle me. He wanted me to come up to his room but as hot as it was I was too scared. Going back there tonight and hoping for a repeat :)
 
My hubby ordering delivery pizza at the hotel and then tying me naked to the bed and when pizza came he opened the door let the guy in and then walked into the bathroom to get his wallet leaving me tied spread eagle on the bed with the pizza guy standing there

DAMN, I had a college girlfriend that did that to me one time, I was in the living room tied to the sofa legs and the coffee table, when she let him in... he was laughing his ass off...
 
Dollie

My hubby ordering delivery pizza at the hotel and then tying me naked to the bed and when pizza came he opened the door let the guy in and then walked into the bathroom to get his wallet leaving me tied spread eagle on the bed with the pizza guy standing there
Why do all our husbands tease the pizza man?

We have so many stories they are in Lit.
 
Going four rounds in a row with my boo when we went on vacation.


He ended up exhausted with his ab muscles sore from humping me up and down. I have a pretty nice plump ass, so that's some heavy lifting.

I'm basically his workout machine. :D

Whew.
 
Girlfriend and I were on a balcony at our hotel in Key West, in the daytime and at night with people walking by. If they looked up they would have seen her fantastic tits. We could be seen easily from the adjacent hotel and buildings. At our hotel pool one evening we fucked. It was hot thinking someone could be watching or we could be caught at any moment. It was open all night and we could have been caught by a late swimmer. After a little while, we were playing around in the pool. She took off her swimsuit. She got out of the pool naked and walked about 30 feet around the pool to the hot tub. I followed her. The hot tub was protected by a thin layer of bushes surrounding it. Turned on again I had to have her. We heard people on the other side of the bushes. We fucked again in the hot tub. I had to cover her mouth to keep her from screaming. I'm really surprised the people nearby didn't hear her moaning. After that we stayed in the hot tub another 20 minutes. She didn't put on her swimsuit till we were ready to go back to the room. Once in the room, I was horny again and had her give me a blow job on the balcony.
 
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Ah! Hotels

So many experiences, memories.....

- Watching from my room across street to see a woman in window of another hotel, riding a guy as he sat is chair, her body brightly lit.

- Spanking a lover as she knelt by floor to ceiling window - low floor - her mouth filled with my cock. Much much younger she was.

- The lesbian who wanted....

- The anonymous woman who.... and I never knew her name.

- The others....

Details perhaps available when I have time and a female inquires.... or whatever/

Gabriel


My hottest encounter was about 5 years ago when I was in my mid 20s at the casino. While my man was in the poker room I sat at the bar drinking by myself. An older guy sits down next to me and we start talking about life, our relationships, etc. His wife stops by and he introduces us. She leaves and we continue to drink. He is buying me drink after drink and out discussion is getting more and more risque. Flash forward to him followimg me to the bathroom. Pushing me up against the wall to kiss and fondle me. He wanted me to come up to his room but as hot as it was I was too scared. Going back there tonight and hoping for a repeat :)
 
My experience is a little different, as it happened in the hotel parking lot.

It was my older sisters college graduation and I had been texting with a guy friend of hers I met at one of their parties over the years. I was 17 at the time and he was 23. So naturally she tried to steer me clear from him. But we had been talking for years at this point and did a lot of dirty talking, telling what we would do to each other if we had the chance. So there was no stopping us. The sexual attraction was there and it wasn't going away.

I was staying with my parents at a hotel near her school for the graduation when he texted me wanting to see me. it was 430am when he drove over. My parents wee sleeping so I slipped out of the hotel and into the backseat of his car in the lot.

We immediately start furiously kissing. He pulls me on top of him and I start grinding against his cock, hands in his hair. He's moaning, telling me how much he's wanted me. We keep kissing for a while. We just loved tasting each other. And I coudnt stop biting his lower lip. After our mouths were to the point of getting sore we pulled away from each other, just enough so he could fit his hand down my jeans. The feeling of him slowly unbuttoning my pants, knowing the pleasure I was about to finally get was incredible.

Feeling his hands finally explore me like that, I could have cum right then. But not before I got to play with his cock and suck him off. We had a good time finally getting to know each other on that level.

Anyway we fooled around for a couple hours and it was a very eventful hotel stay. Sneaking around is always fun too :)
 
Sneaking out of my room while my girlfriend was sleeping and pumping her sister (in room across hall) all night long, managed to just sneak back in before sunrise. Slut had been eye-fucking me all day, no way I was letting that slide.
 
Girlfriend and I were at the coast for the weekend. First night there she saw a hot guy at the bar and ended up flirting with him most of the night as I watched from across the room. Watched them leave and she showed back up at our room a couple hours later nice and used. I had so much fun playing with her as she told me all the details.
 
Great Stories

I love the stories on this thread. I travel for a living so I stay in hotels a lot. Unfortunately I dont have many sexual encounters or at least "sexiest" encounters.

I do remember one many years ago when I was in my late 20s. I was dating a girl at the time and her girlfriend met me one day as I was traveling through her city. My gf told me to meet her friend so we met. She was a bit overweight and average looking. She was a very nice older lady and we became friends. After knowing her for about a year, I saw her randomly passing through the same city. She needed a hotel room or she was going to sleep at the airport. I offered her to sleep in my room.

We slept in the same bed and it seemed perfectly innocent. But in the middle of the night I felt a hand on my thigh. I woke up and did not move it away. Soon it traveled to my crotch and her hand went inside my shorts finding my dick. She moved my shorts out of the way and soon I was inside her and thrusting away. She held me so tight as if to make sure I did not get away until she was satisfied. That along with her enthusiastic thrusting with my movements really turned me on and kept me very hard.

Then all of a sudden she stiffened up and came. She let out this very long sigh of relief like it had been 20 years since her last orgasm. I think I came as she was letting out her sigh, I really don't remember. It was more about her and her pleasure than it was about me.

I pulled out and lay next to her. I was surprised at how quickly it happened and within minutes we were both asleep and the next morning nothing was said about what happened that night.

I did not tell my gf, but got the feeling that she knew and had even encouraged her gf to have sex with me.

ES
 
In my case a group of us from the same company were traveling to another city and staying in the same hotel. One of my female co workers was flirting throughout lunch so I whispered to her that she should put her money where her mouth was and meet me in my room.

I went up to my rooms and she arrived 15 minutes later and we had the most mind blowing sex imaginable.

Throughout the time we worked together we made sure that about 4 or 5 time a year we ended up in the same city and spent many sex filled nights together.

Despite the fact we no longer work together we still try and get together for some straight forward good sex.
 
I got picked up hitchhiking by a guy and he wanted a blowjob in return. After the blowjob while I was still playing with his cock, he suggested we get a motel room for the night. We got there, took a shower together and spent the night sucking each other's cocks. The next morning, I rode another couple of hundred miles with him before we had to take different turns. And yes, he got a couple more blowjobs during that ride.
 
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