by Starnan

What’s your gender? Man
How old are you? 45
What’s your race/ethnicity? Mixed / Multiracial
What continent do you live on? Australia
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Transport
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? Rampant
How many sexual partners have you had in your life (including oral sex)? 34
How many hookup stories have you here posted before? 1

First Threesome

How long ago did this hookup happen? Day before yesterday

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 more than 3 years

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? Partner 1: my regular friend with benefits. White, male, mid 40s, great body (fit). I’ve known him more than 20 years. At one time we almost dated so he’s almost an ex. I’ve been fooling around with him on and off pretty much all the time I’ve known him, with a break of about seven years in the middle, after I got married.

Partner 2: his partner. They are in an open relationship (although maybe this will change – see below). Asian, also mid 40s, slim. Cute. Met him through him being my FWB’s partner. I’ve known him about ten years but this was the first time I’ve done anything sexual with him.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? My FWB instigated it. Every few months he and I hook up. The last couple of times he’s told me that his partner would like to fuck me. I told him I was not averse to the idea of a threesome. My fwb warned me that his partner’s cock was quite large and I might have trouble getting him in (as I often feel pain when my FWB fucks me). Somehow this only made me more curious! So I went to their house and hung out for a while. We were all quite relaxed. Then my FWB asked if I wanted to get fucked.

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? My FWB & I took a shower together and he sucked me till I was hard. We towelled off and went to the bedroom. I asked if his partner would be joining us but he said not yet. We kissed passionately (I love kissing) and then I sucked him for a bit. He told me to lie on my back and put my feet in the air. He lubed my bum and his cock and slid inside me.

I mentioned before I always feel pain when my FWB fucks me. But when he goes in slowly and let’s me adjust it starts feeling good. Trouble is I lose my erection – it’s as if all the sensation goes to my arse and away from my cock. Whatever, it feels great! So my FWB fucked me slowly for a while, my feet up on his shoulders. Then he got up and called his partner in.

Now I saw my FWB wasn’t lying about his partner’s cock. It wasn’t ridiculous porn star huge but it was certainly bigger than many I’ve seen. He lay down beside me and kissed me while I turned onto my front and put my bum in the air. My fwb started to fuck me again while I sucked his partner’s cock. I loved the feeling of being between them, one cock in my arse, the other deep in my throat. They were kissing as they fucked me. From the noises they were making it sounded as if both were enjoying themselves! Suddenly my FWB stopped and pulled out. (I wasn’t sure at the time but later he said it was because if he hadn’t he would’ve come).

So he and I went down on his partner, kissing with his cock between us, alternating blowing him. Then his partner fucked him for a while while I kissed them both. Then his partner asked if he could fuck me.

I wondered if he’d get it in without hurting me, but I sure as hell wanted to try! I lay on my side as his partner lubed his large cock, lifted my leg and pushed into my bum. He was a very considerate lover, asking if I was okay, then as he got further in, saying “wow, you’re tight!” He kept pushing in and I pushed back until I had his entire dick in me. Then he began fucking me, first gently, then more insistently.

I honestly can’t remember all the positions and combinations of the three of us. My fwb got a bit sidelined at one point but it ended up with me blowing him till he came in my mouth while his partner fucked me. I lay on my back and his partner shot his load deep inside me. By this stage I still hadn’t cum so they both held me and wanked me till I came.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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? Afterwards I had a shower, dressed and went home. I don’t have any hopes or expectations that this will be repeated. I’m not even sure if I’d want to. But it was a wonderful experience for me, a great way to find out what sex with two people at once is like.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Discussed STI testing history

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

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? No one. I don’t kiss and tell (except here, anonymously!).

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? Somewhat

Do you regret this hookup? A little bit

Why do you regret this hookup? For me, I don’t regret it one bit. Firstly because on principle I don’t regret things I do, just things I don’t do. The past is the past, deal with it, learn from it, move forward. Secondly because I LOVED it.

But I do regret that my FWB has been emotionally hurt by this. Yes, he pushed for it, but having known him as long as I have, I know he sometimes gets into situations that take him out of his emotional comfort zone and I do wish I’d been a bit less selfish and talked more about HIS hopes / expectations / reasons for doing it.

What was the BEST thing about this hookup? I loved it. Loved getting fucked by those two gorgeous men. Loved that I could give them so much pleasure. Loved the pleasure they gave me.

What was the WORST thing about this hookup? I didn’t get to fuck my FWB. Would’ve loved that!

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really. Maybe just as regards the emotional effect it’s had on my FWB – more on that below.

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? As you will have worked out, my FWB and his partner have (or had) an open relationship. But my FWB has this funny habit of going back and forth over whether he really wants to be open or not. Deep down I think he might be more built for an exclusive relationship. He and his partner have had a serious talk following our encounter and they may go back to being exclusive. I honestly don’t mind if they do, though I will miss sex with my FWB. But primarily he is a friend and nothing that had happened will interfere with that.

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? As you will also note, I described myself as being in a “monogamous relationship”. So yes, I am cheating. I have made my peace with that years ago. It’s either that or go crazy. But I wish I didn’t have to cheat. I love my partner and I love sex with her but I need more. I wish we could be open and not worry about it. To me sex is very much just an act. Nothing I do with someone else can affect my partner if she isn’t even there (and the same applies to her, as regards me). Monogamy is unnatural and artificial.

What do you think about the Casual Sex Project? Love it! It’s great to read about peoples’ experiences.

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

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