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? USA
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: Atheist
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)? 30
How many hookup stories have you here posted before? none

The Happiest of Endings

How long ago did this hookup happen? about a month

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

How would you best classify this hookup? fwb, led to one threesome

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? Here’s my story:
I met my male partner at 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, 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, 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 it, 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.
Less than a week later, Jake suggested we make a lunch date, an after-work drink session, and I agreed. We drank, we laughed, we spoke openly and earnestly, (that was a theme for the past year, we always spoke openly and honestly to each other) we flirted, we touched, we kissed; Jake wanted to fuck me in the bathroom of the place. We could not take our hands or lips off of each other. As we spilled out of the door and continued to walk, he would pull me into a doorway every couple of feet and kiss me so passionately that I was, at this point, dripping wet. I could feel my wetness between my thighs. We made the decision that we were going to fuck that night, it was a question of where. He made that happen as easily as modern technology would make it to find a hotel room to use for a few hours. The room had a balcony, I went out, put my leg up on the ledge, my pussy was out, hot and extremely wet. Jake came up behind me and ran his fingers up my legs, touched my pussy, kissed my neck, turned me around made out hard with me, and led me inside and onto the bed. The details of the rest are a bit blurry because I was drunk. But I distinctly recall being pleasantly surprised by the size of his cock. I REALLY didn’t want to have to fake it with this guy. He fucked me so good and so hard. He knew how to use his cock to fill me and make me squeal. He wanted to only pleasure me. He was amazing at eating pussy. I mean, the man deserves a medal.
For the year to follow, we saw each other at least 2x per month, if not more. we would sext incessantly, flirt while in the office, we had crushes on each other and we both knew it. When given the opportunity, I would make sure to strut past his office because I knew watching me from behind got him going. If we had meeting together, we would eye fuck each other at every opp, he usually would start staring first.
I would see many a hotel room after work and during work.
Some of the hottest experiences ever took place during the lunch hour/ hour and a half 😉 We role played the hottest roles. One was the naive, young, aspiring porn star was so fun. He set up being able to watch ourselves, like an actual casting director. I saw angles of myself that turned me on so so much. One of the hottest role plays ever is “Daddy/“daughter”. The night I admitted that it was a fantasy of mine, I showed Jake my favorite porn short. We flowed so easily into the roles and he fucked me so hard as I said “I’m a good girl, daddy, I do what daddy wants.” We came together that night. This was one of the only times I have noticed his accent, it did something to me the night. My contractions were so hard, my cum, abundant. The weeks flew by, the sex better and better; more and more addictive. We would meet for lunch, actual lunch, where we would eat and chat. We would also make out and fondle each other in the elevator on the way to the restaurant. This was lust in its purest form. And I was enjoying every second. During these lunches, we would discuss anything and everything! But of course some part of the conversation would be discussing what we would like to experiment with next and it would also be in part, scheduling. We would have to schedule, “late nights” vs “over nights”. I know we both looked forward to our time together. During our overnights we would have sex all night long, literally.
Once lunch we attempted to role play doctor/ patient, but I recall wanting to fuck him so badly, I didn’t even give the roles a chance. A recurring role during lunch would be daddy/daughter. I would walk into a hotel room with Jake already being naked, under the sheets and daddy was waiting for his ‘angel” to come “home”. Writitng about this makes me wet!!
He made a meeting for us in his office, one day. OUtlook calendar and all. He instructed me on what to wear. When I got to his office, he instructed me to take off my panties. I did, all too willingly. The door was open behind me, we were so naughty. I continued to pull the “basic instinct” move by separating my legs and showing him my bare pussy. I played with it a bit. He was squirming behind his desk.
I knew this whole thing was temporary. I would break plans with friends to be able to fuck Jake. I didn’t know how temporary until Jake told me that he and his wife were going to be closed if and when they got pregnant. About a month after he told me the “boundaries” he revealed to me that she was pregnant. As you can imagine I was thrilled and bummed at the exact same time. One thing was outstanding – he had not has his FMF threesome. In the beginning when he expressed interest in wanting to fuck me on a regular basis, I told him that I was down to experience whatever!! So I was down to have that threesome 🙂

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Jake’s wife gave him the go-ahead to have his threesome, and then they would close off their relationship. The experience was awesome, but it left us in a grey area, and him on the search for a third. I, having had plenty of FMF threesomes, wanted to make this amazing for him. we agreed that we would meet this person first, together and see if there was chemistry. There were a few prospects, but there was one woman who was perfect. Confident, sensual, conversant, she was everything we were looking for. We will call her Jo.
She 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 is a bit older than I but hot, fit, light skin, well taken care of, hazel eyes, short pixie 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 planned 1:1 time with Jo and Jake, separately before 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 turns with Jo. We played with her together. I recall when we each were sucking on her breasts and met our eyes and smiled. we had an amazing time. I enjoyed watching Jo and Jake together. It was so hot. She ate my pussy and made me cum. He fucked me while I kissed her. He came in my mouth while kissing Jo.
Jo has incredible nipples and breasts. the 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, I loved sharing and sucking on a cock with another woman. It is so hot, so good, and the ball play was so fun!
I did something to him that I have never done with anyone else during this hook-up. I licked Jake’s asshole, I touched it,I played with it. This is something that I said I wouldn’t do and was not interested in. He enjoyed it. I was a bit rough, probably bc I was a bit drunk. He gave me a look of shock and awe and enjoyed the rest. We both knew what this meant.
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. Jo 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. I think it did even more. He mentioned afterward that watching me get that flush in the face was a turn-on.
Nothing VERY kinky occurred but it was still incredible and left me wanting so much more…
We both knew that after the next morning, we could not be together any longer. I wanted my night with him. We had sex two or three more times before we both had to go to work.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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? After the hook-up, we have kept in touch separately with Jo. Jake and I tried to severely decrease communication, but that seemed to not work out for either of us. We have maintained a flirty, text filled (minor sext), occasional lunches, friends only relationship. I want to stay involved with is life, and he wants to the same with me, for now. I invested so much in the past year. I lied, I fabricated, I spent time and money making this year one the best ones of my life.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, avoidance of eating her due to not being tested…

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), It was easy / convenient, A ceremonious end to my and Jake’s relationship

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

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

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 have not spoken to anyone other than Jake and Jo about this hookup and the three of us cannot wait for it to happen again. Jo 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? It ended my and Jake’s relationship. It was a new experience for Jake and me. It was so hot to watch his with another woman. This woman was so hot and sensual and she pleasured me so well!

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? No, it has just validated what I already have been thinking. I love sex, I love great sexual encounters. I am a free and confident in who I am and what I like and what I want and what more I want to experience.
This has made me think of what will happen when the three of use re-meet. I wonder if I can keep my hands off of Jake. I miss him, I cannot deny it. We both wonder what our sexual future hold for us.
This had made me think about how the last year of my life has been a complete whirlwind and how I so badly want to fuck Jake again! and again! and again!

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 have affection for Jake, 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 has SO MANY intriguing, sexually enticing, inviting, encounters with him. I long for the next time my flesh touches his.
Since starting to compile this story and now writing it out for CSP, we have “slipped a bit”.
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, fuck me, spend time with me, something! 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, not texting as often, but habits (esp bad ones) are the hardest to break. I await our next steps…

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? I want everyone to mind their own business and let people fuck whomever they want to fuck. Consensual sex doesn’t hurt, it is supposed to be fun!! be safe and have fun!!

What do you think about the Casual Sex Project? This site is phenomenal. It gives people an outlet, a place to put their emotions and stories being free of judgement.

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