Fancy Hotel Sex



What’s your gender? Woman
How old are you? 39
What’s your race/ethnicity? Mixed / Multiracial
What continent do you live on? Europe
What country and/or city do you live in? Netherlands
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Pansexual
How many sexual partners have you had in your life (including oral sex)? I’d guess around 35
How many hookup stories have you here posted before? None

Fancy Hotel Sex

How long ago did this hookup happen? 8yrs

What was your relationship status at the time? Single

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? Just met that day

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? He was an American businessman visiting Canada for a conference. He was average looking, tall, heavy set body, brown hair, and blue eyes. I had only been on my own for a little while after a bad break up. I wasn’t having much luck finding dates or a fuck buddy and I decided to cruise online hook up ads. I answered the ad of a 52-year-old (I believe he was 22 years older than I was at the time) and we actually had some really good conversation during his day at the conference. We exchanged pictures and both liked what we saw. As it was his last night in town and the conference would wrap up a bit early, he wanted to ditch his colleagues and hook up at his hotel. We discussed what we each wanted to get out of this, health and safety etc. I was quite nervous but he was staying at a high-end hotel with an all-night concierge and after much discussion, arousal won out. It was about an hour’s drive for me. When I got there and went up to his room, I asked him what he could do to make me feel safer. He gave me his business card with ALL of his personal information. He said no self-respecting ax murderer would offer that up. I agreed, took a photo (while he watched) and sent it to a friend with the name of the hotel and room number and said it was an agreed one nighter and just a piece of insurance in case he turned out to be psycho.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? He didn’t rush things. We sat and talked on the bed, kissed and cuddled for quite a while. It was nice to gently explore touch by touch. He asked permission at every step along the way. Each piece of clothing came off with a “may I?” and a “can I touch you there?” He kissed, licked and massaged every inch of me that he uncovered. He’d never been with a tattooed woman and took extra time and care tracing the large design with his fingers and tongue. I was relaxed, insanely horny and dripping wet by the time he got around to touching and tasting my pussy. It was easily an hour or more from the time we sat on the bed to when sex started happening. I was completely naked and he was still dressed at that point.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? He laid down between my thighs and gently parted my pussy lips and just looked at me. He told me I was beautiful there too. He asked if he could taste me and all I could do was nod. He groaned at first lick and said I was sweet and better than dessert. He made me come expertly fast and hard, but he didn’t stop after one orgasm. He continued with his fingers and mouth and before I could warn him that I’m a squirter, the bed, his face, his arm and hand were drenched. I was apologetic but he was delighted and asked if I could do it more than once. I said I knew it was possible, but it was never guaranteed. He kept going and I came and squirted multiple times for him. It was hot since other partners had shamed me for it or were disgusted by it. He thought that I would just let him give me orgasms and that I would back out of penetrative sex or blowing him so he was pleasantly surprised when I asked to suck his cock.

I took his clothes off in a hurry but took my time touching him and kissing him. He was self-conscious about his body hair but I loved it’s softness and loved rubbing myself against it. I was his first partner to ever play with his nipples and it made his cock even harder. He was dripping pre-cum when I finally started to blow him. He tasted good to me, but he stopped me from finishing him with my mouth. He didn’t know how many times he could come in one night and asked if I wanted to be fucked. I brought condoms in my purse and grabbed one. He put it on and slowly slid inside me. His cock was circumcised, about seven inches, rock hard, and thick. The girth was delightful for me and I got a lot of sensation out of every thrust and was close to coming again. I was surprised at how long he lasted and as soon as he finished, he pulled out and started licking me again. He didn’t stop until I’d had multiple orgasms again, what a gentleman. He got hard again while licking me. He said he didn’t think he could come again but he’d like to be inside me so I passed him another condom. He flipped me over and took me from behind. He reached around and rubbed my clit and I came on his cock. My orgasm triggered another for him. He was shocked and collapsed on top of me. We cuddled in a sweaty heap on the bed. He was surprisingly tender and offered me a bath or shower. I asked him to join me. We soaked in a huge tub together and washed each other. The conversation was still good and we were both relaxed and happy. I was exhausted, I dried and dressed and left just before sunrise. He was packing and dressing for an early flight home. He said he’d sleep on the flight home and dream of me.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? I drove home thinking about him and what I’d learned about myself. Up to that point, I didn’t think that I was able to have a one night stand or that I would feel guilty about it. It was surprisingly liberating. I liked having an older and more experienced partner. I was surprised at the level of trust and consent I’d shared with him. We’d said that we’d stay in touch and maybe hook up again if he came back to my city or somewhere close by for work, but that never happened. We talked for a while and then I got curious. I still had his business card and I made the mistake of looking him up on Facebook. He was married with two teenage sons. I didn’t like that I had been lied to and I stopped talking to him after I confronted him about it. He said they had been separated for a while so he didn’t think it counted as cheating.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Sterilization, Discussed STI testing history

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Thought it was an important experience to have, To feel more desirable, To feel more confident, I was feeling lonely, It was easy / convenient

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? I had one friend at the time that was really adventurous and she was the one I sent the message and photo of his business card to. Her and I discussed it at length. She was into older men and completely understood how the sex was much better with him. I did have some feelings of slut shaming myself and she talked me out of that. Basically, if men are allowed to have casual sex, why aren’t women? Why should our number of partners matter or devalue us as people and potential mates? When my husband and I discussed our sexual experiences at length, it came to light that I had a lot more partners and much more interesting stories to tell. Thankfully, it doesn’t bother him and he feels he benefits greatly from a partner that knows her body and her needs, and gained a few useful skills along the way.

How would you best summarize people’s reactions about this hookup? Relatively positive

Did you get emotionally hurt as a result of this hookup? A little bit

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? I learned more about how much pleasure I could experience and that my threshold for multiple orgasms and squirting was much higher than previously known. I liked the feeling of intimacy and trust he created even though he was a stranger to me. There’s always a degree of risk in a one night stand but I felt really safe and actually kind of cherished. He appreciated what I was giving him in terms of trust and my body and understood that there’s more risk involved for women.

What was the WORST thing about this hookup? That he lied about his relationship status. If I knew in advance I would have had questions like how long were they separated, do they live separately and is there any hope of reconciliation. If I had satisfactory answers, I might have still gone ahead with the hook up but just omitting that discussion didn’t seem ethical to me. It still doesn’t.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It made me feel sexier and more confident. It made me able to be a better advocate for my own pleasure/orgasms in hook ups and relationships. I went on to have several more casual relationships, fuck buddies, one night stands and kink based relationships.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup? It was the best one night stand I’ve ever had.

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? There’s a lot of wrong in how our society views relationships/sex. You should experiment alone and with partners in order to understand your desires and needs. Most marriages that stem from high school sweethearts or untouched virgins are kind of doomed to fail because it’s human nature to want to explore and try different things and partners. Sometimes our sexuality or kinks and desires don’t fully develop until we’ve had some sexual experiences and experimented for a while. I don’t think we should push the marriage agenda until we feel the desire to settle down as individuals, then and only then can we feel satisfied and settled in the marriage/sex life that we’ve chosen. Also, the importance of sex and sexual compatibility in relationships (for people who experience sexual desire and attraction) needs to be emphasized. It’s not wrong to have good sex and sexual fulfillment as one of your relationship deal makers/breakers. I think that knowing myself has led me to finding a very compatible husband and we never disagree about frequency or kinks etc.

What do you think about the Casual Sex Project? I hope that the Casual Sex Project opens up more conversations around sex, pleasure, sexuality and encourages women to pursue their own pleasure and shed some of the shame around claiming/owning your sexuality.

You have a hookup story to share? Submit it here!