Mutual Pleasure In An Air BnB

by Tippy

What’s your gender? Woman
How old are you? 29
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
What’s your sexual orientation? Pansexual
How many sexual partners have you had in your life (including oral sex)? 9
How many hookup stories have you here posted before? 3

Mutual Pleasure In An Air BnB

How long ago did this hookup happen? A few months ago

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For less than a year

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? Cash was a friend I’d known nearly a year. Shorter than average (about my height, 5’6) with a broad face, dark brown hair, sharp haircut and a neat fine bread that framed his lower face. He wore glasses and had sexy hazel eyes that always looked devious to me, especially when he gives you a smug grin.

He’s very intelligent and calculative, and although pleasant can seem a little cold until you get to know him.

A few weeks ago I’d let slip about a casual sex experience to him to see how he reacted, knowing I’d become emotionally and physically attracted to him over the last while. We had a fun friendship and a mutual crush (he was bisexual) that I’d also slept with. He was in a long term monogamous relationship.

I met him through mutual friends with a shared interest.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Myself and Cash had been out drinking and become very flirty and dirty. At one point I tried inviting him into the toilet…I think we both thought about it but not sure either would’ve actually done it. We walked our friend to the station and by now we had toned down and sobered up. I’d had a great night and wasn’t looking for anything else, and assumed since we were sober now that it was off the table for him.

I overheard him tell our friend he was going to crash at my air Bnb (we were out in another city) rather than staying with him. This wasn’t too cheeky as I had platonically suggested it before the trip, but I knew we’d be sharing a bed and thought it was unlikely nothing would happen, I wish I’d known in advance so I could tell my hosts.
I was also perfectly open to nothing happening if he didn’t want to.

We got back very late and crept in. I showered quickly as I felt really sweaty, then got into my PJs. He politely looked away as I did and we chatted about plans for tomorrow and the days events.

Eventually we got into bed in our PJs and started spooning and cuddling. Still talking about various normal friend things.

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? We squeezed our bodies together and enjoyed the contact. He started lightly stroking my side and winding me up, I moaned repeatedly every time he went to squeeze my hip. I touched and rubbed his dick through his bottoms, we tried kissing but it didn’t seem to work too well for us. Eventually he told me to stop (running his dick) and I did. He continued to wind me up and make me moan, eventually I couldn’t take it anymore and told him if nothing was going to happen I’d have to get myself off. He seemed to quite like that idea and offered to help. I started to rub my clit and he touched, kissed and licked my nipples and breasts. I was extremely aroused and enjoyed it, eventually I had an average masturbatory orgasm and we went to sleep.

In the morning we started cuddling again, I kissed his neck and he took off his pj bottoms. I started to grind myself into him and he made encouraging murmurs. I started to touch his cock and rub his plentiful precum over the head and shaft. I really liked the head of his dick, it was big and round.
He then turned around and put his foot between mine, slide towards me opening my legs with his. I was naked from the waist down like the night before. We kissed again briefly and then he started to work his fingers over my wet clit.

To finally have him touch me when I had wanted him to so badly the night before felt amazing. I was an absolute slave to the sensation. He alternated in pressure and teased my opening repeatedly. I moaned and bucked my hips. A couple of times he got me really close then let the it slip away. Eventually though he lead me into a rapturous orgasm.
I’d just about shook off my grogginess when he guided my hand back to his cock. After working it a while he threw the covers back and he came over my hand and his stomach. We cleaned up and got dressed.

AirBnB hosts were absolutely ripping.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, one

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 felt fine, I had fun and he seemed to feel the same.
It became clear he had a lot of interest in sex and likely was more experienced than me. We continue to talk openly about sex, flirt and reminisce about our little experience. I wouldn’t write out it happening again or from having penetrative sex in the future, it really depends what he’s comfortable with and what opportunities present themselves. Our friendship is fun, functioning and closer than before. I feel he’s a great friend and I enjoy being around him, both in a sexual and platonic way.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Making new friends

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

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? I don’t know / I’m not sure

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

To whom did you talk about the hookup? How did they react? My husband, who was initially shocked but came round. Our mutual crush who I’d previously slept with (though not all the details) he had no strong reaction one way or the other, just knows I like to talk things over. A couple of close friends who don’t know/have never met him and am aware I’m in an open relationship. They congratulated me mostly and we laughed about it and my other hook-ups.

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

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

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

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Natural chemistry, sexy vibes and some seriously good fingering with a great orgasm. Making/having made a good friend who I can share an openness with and whom I enjoy spending time with.

What was the WORST thing about this hookup? Air BnB host losing his shit in the morning.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It’s made me want more if I’m totally honest.

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

All things considered, how NEGATIVE was this experience? Not at all negative

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? I just wish open marriages were the norm, it would be so much easier if we didn’t expect one person to be solely, sexually, ours forever and then to expect the same of you. I just think it’s idealistic and not realistic.

What do you think about the Casual Sex Project? This is my 4th story I’ve submitted, I love the project. I don’t read all but love popping in now and then for a look.

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