Location: Pacific Northwest
Highest education received: College degree (eg., BA, BS)
Relationship status: Single
Religious affiliation: Christian
How religious are you? A little
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 15
How long ago did this hookup happen? Two Months
How would you best classify this hookup? One Time Thing
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? Rita was a thin woman with curly brown hair. She had soft skin and was forty years old, about eleven years older than me but hardly the first older woman I had gone near. She had come in as an outside consultant for my company and we had been working together quite closely, Rita had brushed up against me a few times and made more than a few excuses to touch my hand. I could tell she was interested and I liked her and was attracted to her but as a rule I avoid coworkers due to a mistake in my youth.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We had gone to dinner and flirted a bit, but again as I said I stay away from women I work with. The week she was working for us came to and end and I went to see her at her hotel that morning. Since Rita technically no longer worked for us I know I went there looking for sex and Rita did not disappoint, she answered the door to her room in her underwear and a bra. She also had candles going.
We talked a little bit about work and then Rita asked me to get undressed and she moved to the bed and took her bra off. I will admit I really, really like boobs so this got me going and I could feel myself growing hard. We started to kiss and make out and I can remember she was really jamming her tongue down my throat.
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? I licked and sucked her breasts a bit and Rita laid there and let me. I am not sure how much she was really into this but I was enjoying myself. Finally after a few minutes she asked me to turn over and began to give me oral. She was careful to make sure I didn’t come and quite talented orally.
We decided we wanted to do the deed at this point. I remember her pussy wasn’t shaved but well groomed but this did turn me off a little. I have a back injury that prevents me from doing missionary very long so I took her in doggie. I penetrated her and she was pretty tight, and I remember thinking despite her age everything on Rita was still pretty firm. My back didn’t last long in doggie and we switched to girl on top. Rita was very understanding about my back, I am not used to all women being that way.
We did girl on top for a while, Rita was really into this. I put my hands on her hips, and moved them to her ass and breasts a few times. She would go up and down, and then lean forward and let her boobs hit me in the face and then kiss me. She started moaning a bit but I came and Rita was a little tired by this point so she climbed off. I fingered her to finish her off and she had an orgasm.
What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We didn’t discus STI history but I used a condom to be safe.
What were your REASONS for having this hookup? I had been single a while before this and I was horny, and I wanted Rita.
Were alcohol or drugs involved? If so, how much? Not by either of us
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? We cuddled for a while, I didn’t mind. Rita told me it had been a while for her and she had enjoyed herself, women don’t usually tell me that. Eventually we took a shower to wash the sex off, there was a lot of touching and kissing but no more sex. I got dressed to go, I did have to work that day. I can remember vividly Rita was still a little damp and naked when she kissed me goodbye, her body was almost glistening.
We have stayed in contact via email for work reasons. I enjoyed myself but I have no expectations for the future. However Rita did send me an email a few days ago saying she is coming to town for work again and asked if I would like to get together. I honestly haven’t decided yet.
To whom did you talk about the hookup? How did they react? Haven’t actually told anyone, Rita asked me not to. Part of the reason I decided to share it here.
Was this a consensual and/or wanted experience for you? For your partner? For both of us yes
Do you regret this hookup? If so, why? Not at all
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 part was some good sex with someone I liked. I can’t really think of anything bad about this one, other than my technical breaking of my no coworkers rule.
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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