An Intimate Surprise

by T

Gender: Female
Age: Mid 40’s
Race/ethnicity: White
Location: Chicago
Highest education received: Some college (not currently in college)
Occupation: Sales
Religious affiliation: Christian
How religious are you? Not at all
Sexual orientation: Heterosexual
How many hookup stories have you here posted before? 0

An Intimate Surprise

How long ago did this hookup happen? Over the last 3 weeks

How would you best classify this hookup: An arranged encounter

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? We will call him J. J is cute, hand chosen by my husband and I had never met him, do not really know him now and I was nervous as hell before and during. We have had two encounters now and I am looking forward to his coming over again.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? My husband really enjoys the idea of seeing me with another man & interacting with me and another man.  We have had some fun experiences with couples but he wanted to try something new. The idea that he could fully enjoy my experience with another man without having to entertain another women was very appealing to him. This led him to take matters into his own hands. For safety and security, he screened many candidates from a lifestyle website. After finding a few likely subjects, it was just a matter of offering the opportunity and seeing who had the courage to follow through. J has been the bravest thus far.  He arrived as arranged. I was prepped with, “Shower, put on something sexy and sit on the couch.” He arrived with my husband, sat down on the couch next to me, said hi and began kissing me.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? He kisses really well. The first time he came by, we were both really nervous. That subsided after a while. I think hormones are a great equalizer. He reached for my breast and it felt like I remember high school experiences, only he fumbled much less. After much heavy petting, I reached for his package and was quite please with his size and hardness. I got him out of his pants. He enjoyed sucking on my breasts, which drives me wild. We both used our hands to play in our erogenous zones. Then, I focused my attention on pleasing him orally. The arrangement my husband and I share is that I have to do a good job giving these guys head a few times before I will be allowed to have sex with them. In lieu of getting to know them, some bonds can be formed by enthusiasm and pleasure. The first experience ended with him finishing himself off by covering me. The next time he came over, I was allowed to do all of the work. I pride myself on giving men the kind of oral experience they may not get at home or with other partners. I have had years on the job with my husband and I am a great learner.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Aside from the conversations I was not privy to beforehand, there were no discussions about such things. I am on birth control and we will use condoms. My husband and I get tested.

What were your REASONS for having this hookup? These experiences are fun for all parties. This kind of arrangement makes me feel slutty but safe. The anonymity of it is titillating. Once a good rapport is established, my husband will  join in. His stature can be quite intimidating, so we are going slowly so everyone feels comfortable.

Were alcohol or drugs involved? If so, how much? None that I am aware of.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? After the hookups, my husband and I have amazing sex.  We have no expectations of future meetings, but we are hopeful. J is fun, engaging and enthusiastic, all great things in sexual partner that you don’t have any conversations with.

To whom did you talk about the hookup? How did they react? I have only discussed these encounters with my husband.  It is great pillow talk and one of the main reasons for making it happen.

Was this a consensual and/or wanted experience for you? For your partner? All parties were on board.

Do you regret this hookup? If so, why? No regrets.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Best thing was the lasting stories that my husband and I share, in addition to the conversations about what future interludes will contain.

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

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