by Cara

Gender: Female
Age: 38
Race/ethnicity: White
Current location: UK
Highest education received: College degree (eg., BA, BS)
Occupation: Digital manager
Relationship status: Single
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 10+
How many hookup stories have you here posted before? 0

Hotel Friends

How long ago did this hookup happen? A week ago

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Friends with benefits

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 has been a friend for more than ten years. We dated briefly when we first met but found we worked better as friends. Sexually though we were really compatible so we would fuck occasionally. He moved away but is back in town 5 or 6 times a year and when he is we have sex. He’s a friend, a good friend who is amazing in bed.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? He messaged me to say he was going to be in town, asked if I was free and if so if I wanted to hook up. I said yeah of course I did…he let me know which hotel he was going to be staying at and I arranged to go over after work.

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 had drinks, talked a little, caught up, but then we both said we just wanted to fuck so we went up to the room. We last fucked three months ago so I was desperate for it.

He’s the best at eating pussy ever, I’ve never had a guy make me come with his tongue like he does. We started with oral, he went down on me and made me come pretty quick! I really love nipple play and he loves big boobs…he spent time sucking and biting my nipples and he was lying half on top of me so I could feel his semi-hard cock against my leg. While he was sucking my boobs he started to finger me and I came again really hard.

I went down on him then and started to suck his cock. He’s a pretty big guy and when he’s hard his girth is almost too much for me to get him right into my mouth but I love the feel of the head of it on my tongue. He was really hard by this point and I was so wet…he asked me stop and said he wanted to be inside me. We kissed for a few minutes and his fingers slipped into me again making sure I was wet and ready. I was sucking on his tongue and I was moaning into his mouth, I could feel his cock nudging at me ready to slide inside me. He pushed my knees up and lifted my legs over his shoulders and pushed really deep into me while he sucked on my neck. I’d forgotten just how good he feels in me and when he started stroking hard into me he moved his thumb to my clit and rubbed for only a minute before I came again. We kept going for I don’t know how long and he eventually came inside me, and I could feel the cum in me as I slid my hand down between us and played with clit so I could come again. He stayed inside me semi-hard and when he eventually pulled out I put my mouth around his cock and cleaned him up.

We slept and then he woke me at midnight with his tongue in my pussy. I rolled over onto my stomach and he fucked me from behind. This time it was slower and more intense and it took me longer to come but when I did the orgasm hit me hard. He came inside me again.

At 7 the next morning we fucked again, this time with me on top. I rode him solely at first while he sucked on my nipples and I came once just from the nipple play and then again vaginally, he’s one of only two guys who can find my spot and make me come that way.

Did you have an orgasm? Did your partner(s)? Yeah, between the evening and the next morning I came probably 7 or 8 times and he came inside me every time.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We know each other well, we trust each other when we say we’re both clean. I’m on the pill so we don’t use condoms because I like him to come into me.

What were your REASONS for having this hookup? He’s my semi-regular fuck date. I love him as a friend, he loves me in the same way. I was super horny and I like fucking someone I know and trust.

Were alcohol or drugs involved? If so, how much? Little bit of alcohol before we went to the hotel room but only a couple of drinks.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? We showered together, I sucked him off and then we ate breakfast before we left to go our separate ways. Nothing’s changed, he’ll always be my friend and someone I trust to fuck me.

To whom did you talk about the hookup? How did they react? I have a couple of friends who know about our arrangement and they’re cool with it.

Was this a consensual and/or wanted experience for you? For your partner? Totally!

Do you regret this hookup? If so, why? Nope, not at all.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Best thing was the release, having a bunch of orgasms with someone who knows me and knows my body. Nothing bad about it!

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

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

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

What’s Your Fantasy? Click here to be part of the largest survey on sexual fantasies ever!