Weeks In The Making



What’s your gender? Man
How old are you? 69
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 16
How many hookup stories have you here posted before? 0

Weeks In The Making

How long ago did this hookup happen? 1

What was your relationship status at the time? Same as current status

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 tall, slender and perfectly proportioned. A former model, she is a head turner even at age 70. First met her at a social gathering – dinner and drinks. Later I would go on group hikes that I knew she attended. I was strongly attracted to her from the start, but made no play for her the first four years.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The hookup was the culmination of conversations in person and on the phone that hinted at nothing more than sharing a glass of wine at sunset. Then cooking her dinner at both my place and hers followed by drinks and shoulder massages. It took weeks. Finally my hands that were rubbing her shoulders and neck slid down inside her blouse and caressed her breasts and I kissed her.

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? We ascend to her Queen bed, disrobed and kissed, touched etc. Her pussy hair was so soft and I enjoyed it on my cheeks as licked and sucked. Her pussy was juicy, still we used lubricant. It was difficult for me to penetrate because the experience was painful for her. I am larger than normal and she had not had sex in more than four years. Apparently the pain she experienced is something women may experience when they get older. —— We continued as gently and slowly as possible, which ultimately caused me to experience and huge climax just as I fully penetrated. After i climaxed, she climbed on top of me and vigorously rubbed her pussy against my cock until she climaxed – though no penetration. She made no attempt to give me oral.

How sexually satisfying was this hookup? Somewhat

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

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? It bothered me that it caused her pain and it bothered both of us that we could not simply engage in vigorous fucking, which is what we both craved. This all occurred while I was breaking up with my partner of six years, though in the end, my partner and I repaired our relationship. So, I feel badly about having led the other woman along, though in the end I am not certain we would be as compatible (personality-wise) as I first thought.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Attraction to partner(s), Hoping or expecting it would lead to something more, Thought it was an important experience to have, To feel more confident

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? no one

Did you get emotionally hurt as a result of this hookup? A little bit

Did your partner get emotionally hurt as a result of this hookup? Somewhat

Do you regret this hookup? Somewhat

What was the BEST thing about this hookup? To feel her touch – to touch

What was the WORST thing about this hookup? The pain she experienced – then later the emotional confusion.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? not really

All things considered, how POSITIVE was this experience? Fairly positive

All things considered, how NEGATIVE was this experience? A little negative

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