Happy-Ending Virgin Gets Schooled

by Old Fool

What’s your gender? Man
How old are you? 62
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: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Health
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Vanilla?
How many sexual partners have you had in your life (including oral sex)? ~50
How many hookup stories have you here posted before? 0

Happy-ending virgin gets schooled

How long ago did this hookup happen? 1 yr

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

How long did you know the person before this hookup? Just met that day

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? Youngish (30?) asian woman, attractive. Met at the time of the incident. Traveling in Southeast Asia with spouse. Staying in a large chain hotel with attached shopping mall. Spouse was tired from the traveling and heat, wanted to nap for the afternoon, but I was restless so decided to check out the shopping area. There, I came across a massage place and got the bright idea that a massage might be what my old body needed to relax, so went in and arranged for an hour.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? No planning, it was a surprise.

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? The masseuse was an attractive, youngish (30ish?) asian woman, who spoke little English, but who readily conveyed the rates. She bid me undress and lie face down on the table, and left the room. After disrobing, I laid on my stomach and covered up as best I could with the small towel provided for privacy. The masseuse entered and began the massage in familiar fashion with my back. She was clearly experienced and competent. I zoned out and relaxed, lulled near sleep. After a while she moved to my lower extremities, working up from the calves to hamstrings. She was not shy about working my gluteus muscles, working up the hams, right under the towel to massage my butt. As she worked the inner thighs, I noticed her moving all the way up until she touched my scrotum. This happened repeatedly, and to be honest, I was beginning to feel a tingle there… but I ignored it and pretended not to notice. After a few more minutes, I heard her whisper something in my ear; I didn’t understand at first, what? I looked over at her and, with a questioning look, she made the universal gesture for hand job. I guess I was naive in not expecting this. After a few milliseconds my reptile brain took over from my shocked conscious, and said, “how much?” then, against better judgement, nodded yes.

She went back to work on my lower half, but now beginning to go further underneath, continuing to work the glutes, softly massaging my perineum, and gently reaching further to massage my balls and penis. I suddenly realized how horny I was! After a bit she asked me to roll over. A little embarrassed by my erection-not something I normally grow during massage-but under the circumstances I complied, trying to keep it covered with the little towel. When I looked up at her I saw she had a big grin on her face; she was amused. She flipped the towel off, and began gently stroking my now fully exposed and well oiled penis, while continuing to massage my balls and perineum. She worked sensually and slowly, taking her time, changing movements periodically. Stopping for a moment to reach under her skirt, she removed her panties and took off her top, moving my hand to her ass before continuing her ministrations. It was lovely! I hadn’t noticed how full her breasts were under her loose top. As she continued, I accepted her invitation to explore her ass with one hand, and reached up to her breasts with the other. My hand moved to her perineum, and forward to explore her vulva and clitoris, finding, to my surprise, a very wetness between her lips. All of this was extraordinarily exciting, and I felt myself building toward orgasm. I was breathing deeply, struggling to maintain control. She sensed my edging closer, too. She bent over me and gently teased my face with her lovely breasts, then moved down and suddenly, somehow, she had my penis between her breasts and was moving so that I was fucking them. Before long, I couldn’t control myself anymore and had a deep, satisfying orgasm, coming all over her breasts.

She stopped moving and held my penis gently between her breasts for a moment before excusing herself to clean up. She washed me up with a warm cloth, and for the remaining few minutes of the session finished by gently massaging my face and scalp which she used a towel to cover.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? No

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? When the time was up she left me, still sort of stunned, to dress. I went out to pay, which I did with a credit card, adding a modest tip. Because I wasn’t sure how much she got to keep, I also handed directly to her a larger tip, in my own currency (didn’t have much of the local on hand). We couldn’t communicate much in English, so I just thanked her, then put my hand on my heart, then on her heart, tipped my head and left.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, 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? 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? I don’t know / I’m not sure

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

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? Great orgasm! I slept like a rock that night. New experience, never before sought (or since), but glad my nether brain reacted as it did

What was the WORST thing about this hookup? Nothing really, except not knowing the woman’s circumstance, not knowing her.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No.

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? Wish we didn’t criminalize sex workers in this country. That is wrong, wrong, wrong.

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 would like to see the unjust stigma erased, especially as it’s directed selectively toward women.

What do you think about the Casual Sex Project? A helpful repository and outlet for those like me who cannot share their experiences otherwise

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