The Tortoise, The Hare & The Anaconda

by The Hare

What’s your gender? Woman
How old are you? 36
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Canada
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? In a serious relationship (open)
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity? Open, curious, explorative
How many hookup stories have you here posted before? 0

The Tortoise, The Hare & The Anaconda

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

What was your relationship status at the time? In a relationship (open)

How would you best classify this hookup? Group sex

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? J (my male partner) is tall, slim, and fair with the best blue eyes and an awesome butt. Z is also tall and slim but beefier than J with dark features, a mischievous smile, and amazing hands. He’s very different from me and unlike anyone I’ve ever met. He’s also incredibly kind and thoughtful.

J and I have been together for about 6 years and we met Z about a month ago when the 3 of us were part of a group who cycled 3,000kms over the past month. The 3 of us got on really well and as the trip went on we began spending more time together and started to get to know each other relatively well.
Physically Z is quite attractive and the more I got to know him the more intriguing he became. I spent the last 3 weeks of the ride fantasizing about kissing him and wondering if he was doing the same.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The three of us went out for a post-ride celebration dinner. The food was fantastic, the wine was flowing, and the conversation was easy and interesting. After dinner we went out for more drinks and finally ended up back at my and J’s hotel room. After a bit more chit-chat J started kissing me and then asked Z if he wanted to have some fun with us.
I wouldn’t say planning was involved per say but J and I were both hoping that something would happen. I’d been fantasizing about it for weeks and the two of us definitely spent some time musing over the possibility and wondering if anything would actually happen between the three of us.

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? I was quite drunk by this point so events are kinda hazy…
J gently nudged me towards Z and we began kissing. It was good…better than I had imagined. He was sitting on the couch and I hiked my dress up and straddled him while we continued making out. I’m not sure what J was doing at this point as I was so into the make-out session. At some point, between kisses, Z looked at me and told me I was sexy (or something to that effect – too drunk to remember the words but I definitely remember the look in his eyes and how hot it made me feel). I also remember when I first got a hold of his cock – it was big and thick and beautiful and I couldn’t wait to get it in my mouth! We took turns going down on each other (I’m still unsure about what J was doing at this point) and then I declared “I want to fuck Z. Now.” J, being a great partner, went to get the condom and lube and then suggested we move into the bedroom.
Now things start to get really hazy. I remember worrying a bit that Z might tear me apart with his huge cock combined with the drying effects of the condoms. He was trying to stretch my legs out and open me up but I was apprehensive to surrender and let him take me as hard as he seemed to want to. I also have vague memories of blowing Z while J fucked me from behind (amazing!) and Z telling him to “fuck that pussy.” There were also a lot of totally blissed out moments for me when there was a lot of kissing and oral sex and hands all over my body and butt slapping and the best nipple play. Then my vibrator came into play and it was all pure awesomeness and I wanted to cum so. bad. but had way too much to drink and it just wasn’t meant to be. I don’t know how long we were all fucking and fooling around for but then it all came crashing down as my blood sugars went low (I’m a diabetic) and the action had to stop for a bit of a medical emergency where I was totally drunk and dazed and naked and enjoying candy and chocolate in bed…not a terrible way to end the evening really. J stuck close by to take care of me (as he does) while Z stayed long enough to make sure I was okay, and then said good night and let himself out.
Once my sugars stabilized, J wanted to finish what had started and we began fucking again. He finished by blowing a huge load all over my face and into my mouth and then I promptly passed out for night.

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, but I was close

Did your partner have an orgasm? No

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 next day Z texted to invite us for brunch and we spent a good part of the day enjoying each other’s company and “debriefing” on what happened the night before. We hesitantly parted ways as he had a prior commitment that afternoon. I made it quite clear that if he wanted to refresh my memory of the missing pieces from the night before that I’d be more than happy to “go another round” with him. He texted later that day and invited me/us over to his room and the three of us spent another wonderful evening together (but that’s another story for another time).
I don’t really have expectations/hopes for the future with Z, aside from the fact that I do hope we cross paths again (we live on different continents so it’s possible that I may never see him again.)
I do feel more connected to J now. Experiences like this bring us closer together and I love having a partner that I can share this with. It really makes me realize how lucky I am to have him.
I’m still intrigued by Z – probably more so than before. I wish I had more time to spend getting to know him better and exploring him sexually. We exchanged emails and I hope we do keep in touch but what we can share in an email will never compare to real life interactions. I think I feel more towards him than I ever expected to and I’m going to miss him. I miss him already actually.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, IUD (Intrauterine device), 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, Intoxication, Making new friends

How intoxicated were you? Completely wasted

What substances did you consume? Alcohol

How intoxicated was your partner? Drunk/high but not wasted

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? 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’ve only talked about it with J and Z. It was Z’s idea that we all share our version of the night on this platform which is adding another fun element.

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? There were so many good things it’s difficult to choose but I think I’ll say just the overall sense of fulfilling this fantasy that I’ve had for the past month and realizing the real thing is even better than I imagined.

What was the WORST thing about this hookup? That I couldn’t cum and that we’ll probably never see Z again.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I don’t think it’s changed how I think about casual sex or sexuality or myself really. If anything it just confirmed all of the things I’ve always thought /believed.

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? Casual sex has been a big part of my life and I wish it didn’t take me so long to stop feeling ashamed about this and to embrace the fact that I enjoy it. I think the reason I felt ashamed in the past is because of society and double standards and all that bullshit so I’d love to see all the judgement disappear and for everyone to just let others be and do what they enjoy.

What do you think about the Casual Sex Project? I think this is a great initiative and I hope that allowing people to share these experiences can help change the way society thinks about and judges casual sex.

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