Losing My “Second Virginity”

by Del Monaco

What’s your gender? Man
How old are you? 56
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Los Angeles-The Valley
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Lawyer
What’s your current relationship status? Waiting for my divorce to be finalized, but still living in the same house on friendly terms.
Religious affiliation: Jewish-Agnostic
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity? Coming back to life after a long hiatus.
How many sexual partners have you had in your life (including oral sex)? About 25. Do handjobs at massage parlors count?
How many hookup stories have you here posted before? None

Losing My “Second Virginity”

How long ago did this hookup happen? Less than two weeks.

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

How would you best classify this hookup? Paid sex

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? I am in the middle of a divorce from a 25+ year marriage, 30+ year relationship, but we still live under the same roof on friendly terms. My wife only allowed me missionary sex and has never had an orgasm with any guy. We have not had sex for 10+ years. Apart from a few “rub and tugs,” I have been a good boy. This led to a condition I refer to as “2V,” Second Virginity. Aside from the frustration, after so long, one begins to have doubts about one’s talents and physical adroitness.

I thought about this long and hard (and joined a gym). Do I wait, and pick up a “civilian” chick, once the whole thing (sell the house, finalize the divorce), has been done? Or do I call in a professional? I chose the latter.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was on a trip with some friends, with three of us sleeping in my room one particular night. My roommates were partaking of a sporting event in our other buddies’ room, so I knew I had a couple of hours with the room to myself. I did a Google search and called a number. A half-hour, I was told. I showered, brushed my teeth, and put on a t-shirt and clean underwear.

Around 30 minutes after my call (but who’s counting), there was a knock at my door. I opened the door, and there stood a stunning Asian woman, wearing black-framed eyeglasses, just like mine. Holy moly, I hit the jackpot. Her name was Lucy. We spent about five minutes discussing the permissiveness of what we would do. Then we got to it.

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? She noticed my beer belly under my shirt, and I told her I was going for the Buddha look. We both undressed and got on the bed. She rolled a condom onto my erection and began to give me head.

After a while, we started missionary sex, with a new condom on, which was pretty vanilla. We changed to cowgirl style, the first time I had done that in 30+ years. I always enjoyed that position. Among other things, it allowed me to play with her pussy and rub her clit.

I rolled her onto her side in a flanquette (I had to look up the term) side by side position, with me more or less on top, and able to control the rhythm. There was much more pelvic contact in that position, and it felt much more intimate. The thrusts were not as deep in that position, but that is the position I liked the best. I think Lucy was relieved that it was less than wild sex.

I considered doggy style, but I was having fun and why spoil a good thing?
After about ten minutes, it became clear to me that I was not going to easily cum with a condom on, and Lucy had to be about her business. I asked her for a hand job. I think I used the Mandarin term, “da fegi,” guessing that she was Chinese. That is the only phrase I have ever learned to pronounce so a Mandarin speaker might possibly understand me. Whether I got it right or not, Lucy was pleased.

After five minutes of Lucy expertly stroking my cock, I blew my load. Lucy cleaned me up with Kleenex. I was in heaven.

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? Lucy asked if she could shower, and I said, “of course.” She went into the bathroom and came out five minutes later wearing a towel. (Both of our clothes were still scattered on the floor, where we left them.)

Lucy then walked over the full-length mirror that is present in almost every hotel room. She put down her cell phone just in front of the middle of the mirror. She dropped the towel, and got down on her knees in front of the phone, facing the mirror.

Then she made a video call to her manager, “Mama-san.” Given that Mama-san was staring right up at Lucy’s pussy, and I am pretty sure most of the rest of her was in view, too, I thought Mama-san was making sure Lucy was undamaged by her encounter with a guy with a very average sized cock.

But there was more to it. Mama-san was angry. She screamed at Lucy, who was naturally using the speakerphone, seeing that the phone’s camera was looking directly up her spread pussy.

I am pretty sure Mama-san was speaking Mandarin, a language in which I can only make a naughty request, but the gist of the conversation was pretty obvious. Mama-san sounded like Major Hochstetter from Hogan’s Heroes. “Who is this man!?!” I think Mama-san added, “What the hell are you still doing there?” Apparently, I had run a little overtime.

I showered and relished using the same towel that Lucy had used. My buddies came back to the room and we went to a dull club for about an hour. When we got back to the hotel, my buddies went to the room and I went to the food court to pick up a snack.

When I got back to the room, I was surprised to find my buddies with three girls one of them had met in the casino. They were there to party. I noticed that my cannabis cartridge vaporizer was nowhere to be seen.

Having blown my load, literally and figuratively, I was in no mood to party. Another guy was out, leaving just one man standing. Two of the girls left.

The third offered to drive the last man standing to a dispensary, as our cannabis supply had walked out the door. She asked for $100 up front, which my buddy paid. They left the room to go to her car. On the way, she had to stop to use the ladies’ room. She went in and never came back out. In the room, we noticed that certain other party supplies had walked out after my cannabis pipe.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Thought it was an important experience to have, To feel more confident

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol, Marijuana, hashish

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? 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? All of my buddies on the trip. They were amused at my “second virginity” theory and wondered why I have waited so long.

How would you best summarize people’s reactions about this hookup? Relatively positive

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? Having been limited in my sexual encounters for three decades, and having been embargoed for more than a decade, I was wondering whether I still had “it.” Also, I have a close female friend who talks about her lover’s endowment and his “knowing what to do with it.” I am now pretty sure I still have it and know what to do with it. I’m still good for a roll in the hay.

What was the WORST thing about this hookup? There was nothing at all wrong with this relationship. We both knew what we wanted and got what we wanted. Maybe the worst part is that I didn’t get a picture of her. But that would be frowned upon, at best, given the situation.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I have had a lot of “rub and tugs” in hotel rooms before, but I had discussed that with my wife and she did not consider it to be cheating. Now, with a technical separation in the court record, and a divorce pending, I am not concerned about the cheating aspect of it anymore. I still do not want my wife to find out because I think she would be hurt.

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? Wow! Just what I needed! I could not have asked for a better experience.

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 eager to get back on the scene, but the methods of meeting people have changed. That is probably for the better for me as I tend to be shy. I am also concerned about overstepping bounds. I hear everything from wild first dates to “me too.”

What do you think about the Casual Sex Project? Totally, totally awesome.

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