Popping My Adultery Cherry

by Sybil

Race/ethnicity: Caucasian
Location: California
Highest education received: College degree (eg., BA, BS)
Occupation: Tutor
Religious affiliation: Atheist
How religious are you? Not at all
Sexual orientation: Heterosexual
How many hookup stories have you here posted before? 0

Popping My Adultery Cherry

How long ago did this hookup happen? Almost two years

How would you best classify this hookup? One-Night Stand

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? At the time of the hookup, I had been married to the same man for 20 years. We had had our ups and downs and sex was definitely one of the downs. We rarely had sex and when we did, it was totally unsatisfying. The only way I could reach orgasm with him was by masturbating. My husband and I had a routine wherein I sucked his cock while I masturbated. After I came, he’d fuck me until he came. Yawn. Rewinding a little bit farther, I was not very experienced when I got married: I lost my virginity at the age of 21 and had had exactly three lovers before meeting and marrying the fourth.

Sex and I have never really gotten along. I truly believed that either sex was overrated or that there was something wrong with me. I swear, when I finally decided to lose my virginity, what went through my head was Peggy Lee’s song, “Is That All There Is?” Imagine my shock when at age 48, I reconnected with a high school classmate, was seduced by said classmate (he didn’t have to try very hard), and proceeded to have the most passionate, exciting and satisfying sex of my entire life!

My high school classmate, D, and I chatted a bit after our 30th high school reunion. When the reunion party was over, a bunch of us piled into a bar and I found myself face to face with someone I really didn’t like. I turned around and saw D. He and I didn’t really know each other in high school (it was a big school) but, coincidentally, his younger brother had been married to someone in my son’s elementary school, so it was easy to strike up a conversation. We chatted about that for a bit, then D told me that he had recently taken a job that was headquartered near my new home and that he’d be coming out for training in a few months. Did I want to get together then? I said of course, we exchanged information and went our separate ways.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Several months later I got an email from D reminding me about his upcoming visit and I asked him what he’d like to do while he was in my neck of the woods. He said he wanted to go out for a nice dinner and dancing. I arranged for us to do both.

We met at the restaurant where he gave me a huge hug. We sat down to eat and he made some flirty remarks. Or were they? I didn’t know for sure. Were those brushes against my hands by accident? I was confused. I swear, no one had flirted with me in 20 years! Later, at the dance club, D put his arms around my waist and touched me in a way that could not be confused with anything other than flirting. I liked it! We danced and touched until finally, I planted a big kiss on his lips and the making out began. My body was on fire and I could tell he was enjoying it, too. We stayed until the club closed. Then he drove me home and we made tentative plans to meet later that week.

Two days later, D called me and we made plans to go out to dinner. I was more nervous and excited than I had ever been for a date. During dinner we held hands and kissed and played footsie like teenagers, if teenagers do that sort of thing anymore. D said, “After dinner, we could go for cocktails or I could give you a foot massage.”  I said, “Where would the foot massage take place?”  He said, “My hotel is nearby.”  I said, “I’ll take the foot massage.”

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? My heart was pounding when we got to the hotel. I knew what was going to happen and I wanted it badly. We got to his room and he said, “I have to go to the bathroom. You take off all of your clothes.” I laughed and complied; when he finished in the bathroom, I was naked and ready to go. D kissed and caressed me and took his time loving my body. We fucked for hours in every position and, to my amazement, I had several orgasms just from penetration. I couldn’t believe how easy it was to fall into bed with someone after so many years — how easy it was to commit adultery. Most of all, I couldn’t believe how natural and wonderful it felt. I couldn’t believe what I had been missing.

I never got my foot massage.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? He had had a vasectomy and told me it was safe. That was good enough for me.

What were your REASONS for having this hookup? Lust.

Were alcohol or drugs involved? If so, how much? None.

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? I was delighted! I knew that D and I would remain friends. In fact, the next time I saw him some six months later, he and I had a threesome with a male coworker of his.

To whom did you talk about the hookup? How did they react? I told a very good friend of mine who lives far, far away. She was happy for me.

Was this a consensual and/or wanted experience for you? For your partner? Absolutely.

Do you regret this hookup? If so, why? Not for a second.

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? The best part was that it spurred me to file for divorce and it opened the floodgates for more wonderful casual sex. There was no worst part.

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

All things considered, how NEGATIVE was this experience? Not at all negative

If you’d like to read more about Sybil’s life, check out her blog Diary of a Late-Blooming Slut.

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