Late Awakening



What’s your gender? Man
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? US
Highest education received: Some college (not currently in college)
What’s your current relationship status? Engaged/Married (monogamous)
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? I married very young and only had a couple of very brief sexual experiences before. My wife had only ever had intercourse with me ever. While dating she had given a couple of handjobs to other guys. I always thought I had an average sized penis. It is about 7 ” long, but is very thick. I later learned that I am a little above average in length, and quite a bit above average in thickness.

Late Awakening

How long ago did this hookup happen? 30 years

What was your relationship status at the time? In a relationship (monogamous)

How would you best classify this hookup? Friends-with-benefits

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? I was 27 she was about 40. Pretty face, dark blue eyes Dark, thick short hair. Slightly thick, not fat, very solid. Large breasts, only a little saggy. She had two teenage children.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I knew her from church. She made an appointment for me to look at some home repairs she needed. She had to break and re-make the appointment a few times. Later she told me that she had to arrange a time when she knew we would be alone and uninterrupted.

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? Almost as soon as I entered her house, she reached down and started feeling me through my jeans, and then undoing them. She was wearing shorts and a casual shirt. She went to her knees and I was already hard, she remarked about the size if it, and sucked the head just a little. She told me to follow her and we went into a bedroom, where she told me to get undressed. I sat down to do that while she took off all her clothes standing right in front of me. She pushed me back and climbed up just far enough the take me into her mouth and started giving me slow amazing head. I told her I was going to cum pretty quickly, to which she said MMM MMM without taking her mouth from cock. She took one hand and caressed my balls and I exploded. She did not even hesitate and just kept going until I could feel myself getting a little bit softer. She then climbed up by my side. I didn’t see one bit of cum. I had never cum inside of someone’s mouth before. She asked if I liked to watch a woman touch herself. I said yes, even though I had never seen that before. She turned, spread her legs and started touching her clit and pussy, which was pretty close to my face. I watched her closely and saw her get very moist, which made me totally hard again. After a few minutes she climbed on top of me and put my cock inside. She did almost all of the work and I could tell she was getting very excited. She went between sitting up and laying on me a couple of times, and finally sat up and reached down to her clit area and moaned and squirmed. That made me cum again. She laid on me for a short while and then told me not to move. She went into the bathroom and came back with a warm washcloth and towel and thoroughly cleaned me, all the time telling me how much she liked my cock.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? I did go back to her house one other time and we had sex again. This included a doggy-style session which I loved. That was the last time with her, they moved away not too long afterward. It opened my eyes to other women that I did work for, and I had a number of other encounters over the years. None stands out like that first time.

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

What were your motives for this hookup? Just happened, I don’t know why, just went along with it

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? I don’t know / I’m not sure

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, I think that is why I am doing this.

What was the BEST thing about this hookup? I found out that women really liked me and liked sex with me

What was the WORST thing about this hookup? I found out that women really liked me and liked sex with me, but I was married.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes. Before this I often thought about other women, but after I looked for an opportunity.

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

All things considered, how NEGATIVE was this experience? Somewhat negative

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 am still married to my first love. I should be totally satisfied with her and wish I was. We have very different sexual desires and I really work at taking care of her needs, but I want way more. I don’t do things often, but I still do them at times.

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