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On our first date after dinner my date said to me “I hope we are having safe sex tonight?”


I was naïve about sex when I was dating. Which is strange since I had dated in high school, college and was previously married. However, I did not expect sex until after I dated someone for a few times and we had a relationship. I was wrong. Sex sometimes happened earlier in dating then I expected.

Her name was Mindy. She worked as a mechanic for United Airlines. On our first date we went to Happi House which is a fast food Teriyaki place as she had a two for one coupon. After dinner, she suggested we get a bottle of wine and go back to my place. I was not expecting this.  She also said “I hope we are having safe sex tonight”. I replied, “Yes, but I need to stop at a drugstore first.”

Later in our dating period we had planned a date on a Saturday, but I called her and tried to cancel as my hot water heater had failed and I needed to change it. Mindy suggested she come over and help me. As she was a mechanic, she helped by doing the entire job as I held the flashlight and handled her tools.

After another lunch date, she took me on a tour of the United Airlines Maintenance Base at San Francisco airport. I was fascinated! Did you know the entire bathrooms and galleys come out of the planes in one piece? Mindy was fun while it lasted but she broke up with me so she could date another woman she met.

Another person I dated for about two years was Janice. Janice lived on the island of Kauai. We met in Honolulu when I was there performing my military duties as I was in the Reserves at the time.

Janice was open to almost anything sexually, I never did find her limits as my limits were less than hers. On our first date we did not have conventional sex but she masturbated in front of me and on the second date, sexual intercourse.

Janice was wild, she identified as a dyke, I never did understand why she dated me. Her favorite sexual activity was backdoor. She loved anal, the only woman I dated who did.

What broke us up was not the physical distance but the lifestyle differences. I paid more in taxes than Janice earned in a year, I know as I did her taxes the two years we dated.

Janice is a vegetarian, I am a meat and potatoes guy. Janice got her TV at the dump, I got mine at Best Buy. Janice got her clothes from Goodwill, I got mine from Mervyn’s. Janice was a devotee of Adidam that worships a spiritual guru Adi Da Samraj, I am an Atheist.

But we had some good times and a lot of fun together. I visited her in Kauai a few times a year and she came to California a couple of times while we were dating (usually I paid for her ticket). She even stayed with me on the boat I was currently living on at the time. In Kauai, we went hiking, kayaking, body surfing and explored the island. In California, we visited Monterey, went skiing in Tahoe, hiking and other activities.

On my first date with Debbie, after dinner she suggested we get a hotel room. We drove to a cheap motel and when I got out of the car to register, she suggested I ask for room 322, her favorite. Obviously she had been here previously.

We dated for a month or two, usually ending up at my place or a motel. I broke up with her after she borrowed $500 from me and never paid it back. I later heard from a mutual acquaintance that Debbie had a gambling addiction and was “borrowing” money from lots of people.

Another successful date was Leticia, with Leticia we did wait for sex. We talked on the phone and seemed to hit it off.  On Sunday she wanted to meet but I told her I already had plans. She inquired if she could fit into my plans. I hesitated and was embarrassed but did tell her I planned to go to the Folsom Street Fair that day, which is advertised as a festival for leather and fetish enthusiasts. She agreed to meet me there. We met and had a good time seeing the various people in various outfits.

The first booth we went to asked me if I was there for their contest. The contest was they would take a photo of your penis and display the photo, people would then vote on the best penis. I declined.

With Leticia the sex did wait for a month. One of the longest dates of my life was with Leticia. I picked her up in the morning, she had a couple of errands to run such as returning a video to the video rental store and we had lunch. Then we went to the Auto Show at Moscone Center in SF. We stayed at the Auto Show for over 7 hours, she sat in every car, looked in every trunk and under the hood, etc. What is ironic about this is she didn’t drive! Then we had dinner. After dinner we went back to my place and had sex for the first time. Afterwards I had to drive her home. It was about 3am at this time, our date started about 10 a.m., I was tired!

I had some relationships that we jumped into bed on the first date, others not until after dating for some time. One woman told me that she slept with me on the first date and she wanted to see if we were sexually compatible before putting too much time in the relationship.

There is no answer which is best. The timing of sex should be a mutual decision between the two people. There are no hard fast rules, but one often mentioned rule of thumb is the third date rule. However, my experience may be earlier, it may be later. It is up to both of you.

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