The Happiest of Endings



What’s your gender? Woman
How old are you? 35
What’s your race/ethnicity? Hispanic / Latino/a
What continent do you live on? North America
What country and/or city do you live in? NY
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Healthcare
What’s your current relationship status? Engaged/Married (open)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Bisexual
How many sexual partners have you had in your life (including oral sex)? 40
How many hookup stories have you here posted before? None

The Happiest of Endings

How long ago did this hookup happen? 3 months

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? FWB planned MFF threesome

How long did you know the person before this hookup? For 1 to 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?

I met my male partner at a new job within a few weeks of being there. Let’s call him Jake. The next step started with an invitation to lunch some months later. There were a few lunches in a two months time during which we would chat, laugh and tell stories. Jake wanted to get to know me. He was so curious about my happenings in life. Whether I wanted to admit it then, I realize now, that I really enjoyed getting know a bit more about him as well. He is also very easy on the eyes. He is Caucasian, not American, 5’10, fit and has great lips and blue eyes. He wears glasses, clothes that fit well and are colorful. At the time, I found him to be ambiguous in terms of sexuality. He was not wearing a ring, so anything was possible. He revealed that he had a wife and the attraction was stronger. Let’s face it, I don’t care who you are after you hear that someone has a primary partner, your interest level peaks a bit.

“I believe that you cannot possibly get every need of yours for your ENTIRE lifetime from just one person. Seems like a lot of pressure.” As soon as I said that to Jake, I knew I had opened the door. Initially, I wanted to take it back, but looking back on the last year, it was the best thing I could have said. Throughout the year there were so many flings, that I will end up sharing on this site, for now, I will stick to one story.

Jake chose Josie and had a very PG and public meeting or for a better word “interview” before we agreed that this was the woman that we wanted to fuck together.
I stayed in touch with Josie separately while she was traveling. She was so cool and confident and sexy and I started to regret not making time to have the threesome while she was still in town, the first time! So, I knew Josie for about a month prior to the actual threesome. Basically a stranger.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it?

Jake’s desire to have an MFF was the catalyst. Jake’s wife gave him the go-ahead to have his threesome, and then they would close off their relationship to others. There were a few prospects, but Josie was perfect. She was everything we were looking for: sexy, smart, confident, sensual and conversant. Josie was traveling around the US and she would pass back through town in 3 weeks time after our initial meeting. We set a date for the threesome. I was excited. She was a bit older than I but hot, fit, light skin, well taken care of, hazel eyes, short light hair, playful, flirty and extremely fun. She is so sexy and I think of her often!
In those three weeks, the three of us were sexting and I had planned 1:1 time with Josie and Jake, separately, prior to our threesome.

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?

The actual threesome was incredible! Jake and I took each turn with Josie. We played with her together. I recall when we each were sucking on her breasts and met our eyes and smiled. I thoroughly enjoyed watching Jake fuck the shit out of Josie. It was so hot. She played with and ate my pussy so amazingly well and made me cum-hard. She treated my clit like a tiny cock and blew me. Jake fucked me while I kissed her. He loves the way I treat his cock with my mouth. He came in my mouth while kissing Josie.
Josie has incredible nipples and breasts. They are smaller, but I love that because my tits are big and I love to have smaller tits in my small hands and my mouth around a beautiful hard nipple.
We shared his cock while kissing one another. I loved sharing and sucking on Jake’s cock with another woman. It is so hot, so good, and the ball play was so fun!
I did something to him that I had never done with anyone else during this hook-up. I licked and played with and I may have inserted a fingertip into Jake’s asshole. This was something that I said previously I wouldn’t do and was not interested in. But honestly, while watching him fuck her, I wanted only to do that. He enjoyed it. I was a bit rough, probably because I was a bit drunk. He gave me a look of shock and awe and enjoyed the rest.
At one point I was between Jo and Jake. My body was on Jake’s lap and he sat at the edge of one bed and I was hanging off the edge of the other bed. My body lay across the small opening and Jake was supporting me, which was hot in and of itself. Josie was trying to make me squirt as Jake held me up and played with my tits and kissed me. I wanted to cum so badly. It just was not going to happen. I remember asking Jake if I could cum. I thought that would turn him on as it turned me on more and I think it did. He mentioned afterward that watching me get that flush in the face was a turn-on. Josie and I both played with our pussies as Jake watched and played with himself, which was so hot.
Nothing VERY kinky occurred but it was still incredible and left me wanting so much more. Like to DP Josie while I wear a strap-on!
We both knew that after the next morning, we could not be together any longer. We both wanted the last night together. We had sex two to three more times in the night and early morning hours before we both had to go to work.

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?

I felt amazing after the hookup. I was floating the next day at work!
Jake and I continued to fuck after Josie left. I will never forget the “after” moments. It was the last time (in a predictable long time) that I would be with Jake and I wanted that time to be so hot between the two of us! Fuck that, I earned it that alone time!

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Discussed STI testing history, Exchanged recent STI test results

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

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

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? I have not spoken to anyone other than Jake and Josie about this hookup and the three of us cannot wait for it to happen again as Josie visits yearly.

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? 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? Everything. And, because this is me: I gave someone something who deserved to get it.

What was the WORST thing about this hookup? I have had to conceal this from my husband.
Also, that Jake and I were entering a sex-free relationship after this threesome occurred.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Honestly, no not really.

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?

For anyone wondering, I still am attracted to Jake. I respect him so much. He is genuine. I feel so fortunate to have met him and to have had SO MANY intriguing, sexually enticing, inviting encounters with him. I long for the next time my skin touches his.  Since starting to compile this story and now writing it out for CSP, I have reflected on my past and how other casual, sex filled relationships ended.
In my past, it was not like me to adhere to “rules” of separation after a break-up. In the past, I would try to entice my ex-partner to be with me and fuck me. And it would be easy to get what I wanted. I am a master seductress. I have put every effort into NOT tempting him, not sexting him, not strutting past his office and not texting as often, but habits (esp bad ones) are the hardest to break. I am practicing restraint and getting better at it; when he is ready, I will welcome Jake back into my pussy with wide open lips.

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 is amazing if respected and boundaries and expectations are set among mature adults. Like anything else, if abused, it can be bad.

What do you think about the Casual Sex Project? A perfect forum for story sharing, great idea and execution. I appreciate CSP so much. The stories run the gamut on inspiring, sad, hot and intriguing.

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