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What’s your gender? Man
How old are you? 55
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Virginia
Highest education received: College degree (eg., BA, BS)
What’s your occupation? retired
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Pansexual
Any other term(s) that describe your sexuality or sexual identity? deeply closeted pansexual
How many sexual partners have you had in your life (including oral sex)? 21
How many hookup stories have you here posted before? 1

Pregnant Sister In Law Surprise

How long ago did this hookup happen? 2 weeks ago

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

How would you best classify this hookup? Short fling

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? She is my brother’s sister-in-law and I have met her several times on vacations and such. I always thought she was pretty and I am pretty sure she caught me checking out her breasts a few times over the years. I always felt comfortable around her as she was very easy to talk to and seemed less “scary” than most women. She has always impressed me with how she seems at ease in herself and with herself.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? My sister-in-law broke down on her way cross-country to her new home and I had to rescue her. Once we got to her new home there was no room for me to stay so her sister offered her guest room in the basement. The second night there I was in the only bathroom getting out of the shower when her sister- I’ll call her Jill- came rushing in apologizing profusely and dropped onto the toilet to pee. She explained how being pregnant meant a lot of peeing. Later she confessed that she had waited to pee until I got into the shower so she clearly had a plan.

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? As she peed, I got a little flustered and tried to politely cover myself with my towel. The bathroom was quite small and she stunned me by reaching over and snatching my towel away, leaving me exposed and starting to get aroused. She spread her legs to give me a clear view of her quite hairy crotch and my arousal completed quite quickly and painfully. She grinned up at me, finished peeing, dropped to her knees and without warning began to kiss, lick and suck my rather angry erection. I wanted to caress her hair but was still in shock but when she began to very seriously give me the single best blowjob I have ever had, I gave in and stroked her hair. The shock and the skill she showed brought me to climax very quickly and I started to push her head away, but she grabbed my ass and pulled me deep into her gagging a bit and swallowing. I have not had that large of an orgasm in years and my knees buckled. She finished wiped her mouth and stood up. She kissed me hard then told me to come see her when I finished cleaning up.
After she left I stood for a few minutes then cleaned up. I reached for my clothes and only then did I realize she had taken them. I took a few minutes more to work up the courage to leave the bathroom and go down the hall toward her room. I am not sure why I did not just go to the basement. When I got to her room, she was laying on her bed with a pillow under her ass, her legs spread and ready for me to do the obvious. I hesitated since, after all, she is my brother’s sister-in-law, married, and pregnant at that. She explained that her husband refused to touch her sexually once she entered her third month of pregnancy and she desperately needed a good fucking. Staring down at her massive breasts and very hairy crotch – one of my weaknesses- I gave in and for the next two hours we tried as many positions as I could get it up for. She was a spectacular partner and the ease that she put me in was so much more fun than my own wife.
I thought that would be the only “fling” for us, but every day for the next week I was there, she would come home from work at lunch and we would go at it hard. Three of the nights she snuck down to the basement and either gave me oral or me her oral, or we tried to quietly have sex.
Oddly, though I thought I would feel bad about cheating on my wife, and about her being pregnant, I only felt excitement and a warm happy feeling each time we got together. We would lie there afterward and chat about all kinds of things, no subject off limits. I do believe we have fallen in love at a certain level.

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? Several times during the week, she would pull me into a room, or hallway, closet, or the pantry once, to kiss me passionately and fondle me. After the third day, I even got into it and pulled her aside a few times. Whenever she sat across from me, she would lean over to give me a good look at her breasts, or spread her legs a bit for me. I would get nervous but could not help myself. She told me several times that she had no regrets and in fact, when it came time for me to leave, she made sure we were alone for a while and we had a long, serious-for me- chat about what might happen between us later. She told me that they were coming to visit my town in a few weeks to finish helping her sister with the final move and that she wanted to see me again. She arrived tonight and called me from her hotel room alone….it is as if we were never apart.
We talked about our feelings for each other and agreed that neither of us is interested in leaving our marriages, but that we do have a special, unique, wonderful relationship that is too good and too rare to just throw away.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, she is already pregnant.

What were your motives for this hookup? Attraction to partner(s), Emotional intimacy, closeness, connection, Just happened, I don’t know why, just went along with it, It was easy / convenient

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? I have only talked to her about it.

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? The sex of course was FANTASTIC but the intimacy of laying next to her and talking without her rolling over and pulling the covers up was so wonderful. The funny thing is, though she has a great body, she isn’t what many might call a beauty, but when I think of her, beauty is the only word that I can think of to describe her. I think it is because she is so comfortable in her own skin. It has made me more confident lately and I find myself smiling more.

What was the WORST thing about this hookup? The worst thing about it is that it will be hard for us to get together regularly.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? This whole thing has restored my sense of who I am and has pumped up my self-confidence. Before this, I was very hesitant to try new sexual things and though I had done a few things to explore my new view of being pansexual, I had not really given in to the urges and desires that have raged in me for many years now. After I got back home, I realized that one of my neighbors had been subtly flirting with me and I tried to flirt back a little. I performed oral sex on her in her back yard this week!

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? I told her about my neighbor and she was happy for me. I was surprised that she did not seem jealous or judgemental, and in fact, she asked a lot of questions about her. I am starting to wonder what she may be thinking.

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 wish we could get over ourselves where sex is concerned. I think prostitution should be legalized, casual sex safety and best practices should be taught in high school, and the govt. should generally stay out of our sexuality.

What do you think about the Casual Sex Project? love it!!

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