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What’s your gender? Man
How old are you? 40
What’s your race/ethnicity? East Asian
What continent do you live on? Europe
What country and/or city do you live in? London
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Operations Manager
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Bisexual
How many sexual partners have you had in your life (including oral sex)? ~100
How many hookup stories have you here posted before? 1

A Crazy Weekend Long Threesome With A Crazy surprise (Part 1, Friday)

How long ago did this hookup happen? 10 years ago

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

How would you best classify this hookup? Group sex

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? Bee is a blonde and we have hooked up many times before, usually whenever I am around her city. She is around 5’6, 110 or so pounds, and is quite petite with a nice pair of c cups. I especially love her geeky, girly glasses.

Claudia is a friend of Bee’s, that I only first met that weekend. She is of East Asian origin, 5’11, medium build, long jet black hair that matches her eye colour, endless long legs, and some nice looking, perky tits.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I had a free weekend, so I decided to go visit Bee and spend a lusty weekend with her. During our planning, she told me her friend was staying with her and that we could all go party together, which I didn’t mind at all, so long as I could get some alone time with Bee. A threesome never even crossed my mind at this stage.

On the Friday night when I arrived in her city, we decided to meet in a bar first before heading off to do some clubbing. I arrived early and was enjoying a few drinks when Bee and Claudia walked in, both wearing figure-hugging tight dress that showed off their bodies perfectly. Bee was in an electric blue tube mini dress and Claudia in a bright yellow strappy dress. Both of them showing plenty of shoulders and legs. I’m pretty sure Bee had on a push-up bra as well, as she was showing more of her breasts than usual. Anyway, after the introduction to Claudia and a few more drinks, we decided to head to a trendy club for some dancing and sweating. The three of us were enjoying the music and were dancing together with plenty of close body contact and grinding. Bee and I were getting really close and started making out on the dance floor while Claudia headed to the ladies room. Upon her return, to my surprise, she joined in and started making out with Bee and then with me. We had all had a few more drinks, and it suddenly hit me that a threesome might just be on the table. After more dirty dancing, Bee suggested we head back to her place to smoke some weed before calling it a night.

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? Bee lit a bong and I started pouring some wine for the three of us. We were just sitting around chatting, drinking, smoking, and relaxing at this point. Then the conversation slowly beceme more suggestive and sexual. Before I knew it, I was watching Bee and Claudia having a major snog feast right in front of me, truly one of the hottest sights ever. Their hands started to romp around their bodies; both had hands cupping and feeling each other’s breasts. After a few minutes, I couldn’t just sit back and watch anymore! I moved over and joined in. It was a 3 way snog fest, tongues everywhere, my hard on was so hard that it started to hurt in my pants. I then suggested we move our little party to Bee’s bed. Claudia headed to freshen up while Bee and I jumped straight to the bed to continue where we left off.

Pulling Bee’s dress off gave me so much excitement! She had on a matching set of a black bra and crotchless panties. I stripped myself and wasted no time in putting my hands all over her. My romping hands arrived at her waiting pussy which was already super wet. I loved feeling her be so wet without even fingering her yet. I didn’t even realise that Claudia had returned. She just had on her heels and a pair of red panties at this point. Her shapely legs are amazing and her breasts looked so round with hard little nipples. We are all on the bed by now, with me furiously eating Bee’s super wet pussy and Claudia worshipping my cock. Claudia’s bj on me was average, but she made it up with her use of her hands, massaging my balls, which I love while having a bj. She continued with the sloppy bj, one hand massaging my balls, and her other hand exploring my prostate, to which I have no objection. I had to stop eating out Bee and concentrate to enjoy the prostate massage. I knew I was not going to last long. I told Claudia I was about to cum and she increased her effort on my prostate with her mouth on my cock, which felt like she was try to suck the soul out of me. I blasted in her mouth while she kept up the sucking and I’m pretty sure at this point in my life, that was properly the biggest amout of cum that came out of me, ever. She kept her mouth on my cock until it went soft. I expected to see cum leaking from her mouth, but nothing came out. She had swallowed it all. I had to lay back to catch my breath and so did Bee. Claudia was now jokingly complaining that we two had cum, but not her. They laid on either side of me and we shared another quick smoke.

Then, I was tongue dancing with Claudia as my hands explored her body. For the first time I touched her tits, they did look amazing, but definitely felt fake. My hands continued down her smooth body, expecting to find her wet pussy under those red panties, but surprise, instead of a wet pussy, she had a tiny little cock tucked away! I had seen a few trans before, but Claudia is truly the most passable I had ever laid eyes on. Bee was watching from her side and actually started giggling when my hands reached Claudia’s panties. I was way too horny now and certainly had no issues playing with a trans, especially one that is so passable! (Later Bee explained that she was waiting to see my reaction, but she was disappointed that I didn’t have one). Anyway, I ripped off her red panties and I mean literally ripped off to review her tiny girl cock. We continue snogging while I was stroking her tiny cock and Bee moved to the other side of Claudia and started massging her breasts. Claudia was now panting and twisting her body in ecstasy as four hands explored her body. Her cock must be only around 4’ when fully erect. She suddenly grabbed my hand and stopped me, saying she wanted to fuck. As soon as she said that, Bee climbed on top of Claudia and lowered her body down on that tiny girl cock. I moved behind Bee and started playing with her tits while she was grinding away at Claudia. Bee whispered to me in the sexiest voice ever: “put it in my ass”. I wasn’t going to argue. I spit on my hand to wet her asshole and slowly pushed my cock in. I’d done anal before with Bee, but this was my first DP experience and I was absolutely loving it! Bee slowly ground away as I was keeping it slow too so I wouldn’t cum too quickly with all the excitement. We then switched to a standing position, with me holding Bee and my cock in her pussy, while Claudia stood Bee, holding onto her waist with her girl cock in Bee’s ass. Me and Claudia were both pumping hard in this standing position. I had never seen Bee scream so much. Finally, the excitement got to be too much for me, and I blasted deep in her pussy while Claudia followed. We all fell heavily onto the bed and fell asleep pretty much right away. Bee had not even cleaned up and must have been dripping cum in her sleep.

Later in the night, I felt something warm on my cock and it was Claudia’s mouth. She said she was still horny and needed something to fill her ass. I was too tired at this point, so I just laid there and let her do the work. Once I was hard enough, she sit up and lowered her ass onto my cock, facing me. Her girl cock was now between our bellies as she press her lips down onto mine. It felt so hot with her tongue in my mouth, her girl cock between our now sweating bodies and my cock in her sexy plump ass. Fucking her ass, for whatever reason, felts very sensual. She had a thing for reaching her hand around and start playing with my balls too. She’s not a screamer, but does a lot of sexy moaning. She started to speed up with her movement and without warning, started cumming from her girl cock with me in her ass. Her cum reached all the way to my face and chest. She continue grinding and lowered her mouth to lick the cum off my face and chest, and started feeding me from her mouth. Then she whispered that she needed to feel my hot cum in her ass. As soon as she said that, I just couldn’t hold on anymore, and I came inside her ass and could feel her milking my cock with her ass. I was truly spent, and only then realised that Bee slept through Claudia and I fucking right beside her. She must have been so tired from the earlier DP.

Waking up the following morning will be another story. This was truly the craziest weekend of sex for me. Still has not been topped since.

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? The Saturday part of the story to come in due course.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Birth control pill / patch / ring / injection / implant

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

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

What substances did you consume? Alcohol, Marijuana, hashish

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

What substances did your partner(s) consume? Alcohol, Marijuana, hashish

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? A few close friends. All were surprised at Claudia being a tranny, especially when I show them her photos!

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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Intimacy and sex. Exploring and enjoying bodies together.

What was the WORST thing about this hookup? None. Just that it’s not happening regularly enough.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Always love casual sex, especially when it feels intimated too.

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

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

Anything else you want to add about this hookup? Maybe I should leave this to the end of the whole weekend story.

What do you think about the Casual Sex Project? Absolutely fantastic site.

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