Monique was an attractive Italian-American girl. She had long brunette hair with giant brown eyes, perfect skin, and a pretty face. There was a small gap between her two front teeth. Her workouts were borderline obsessive so her body was great. Her tits were amazing and her ass was great. She was 29 years old, the upper age limit of what I date.
After sending her a few emails on OKCupid, we agreed to meet at a nice bar downtown. We did not speak on the phone or add each other on Facebook. This date was the first of two OKCupid dates I’d scheduled for that evening. It was still light outside when I walked into the lounge. Monique was waiting on a couch and stood up for a hug. I sat down next to her and we ordered drinks.
Despite her age, I was very attracted to her. I put my hands all over her. We talked about sex. I told her about losing my virginity at a young age. She thought this was very sad. This date stretched almost 90 minutes. I ran out of things to say by the end. I played the Cube routine with her as a last ditch effort. That was the second, and last, time I ever ran the Cube. She called me out and asked me if I played that game with all my dates. I shrugged that off. Once our time was up, I paid the tab. We walked for a block together before hugging and parting ways.
She sent a Facebook friend request the same night. I sent her a text right after that. I invited her to my house for dinner and a movie. Monique was a vegetarian, which meant preparing a special meal. That was a hassle but I did it anyway. She came over and we messed around but no sex. Our third date was a few days later. She got naked and I did oral on her but again no sex. I have a four-date rule. The next one was make or break. She came over for the final date and we fucked. We were highly compatible and the sex was great. We liked making each other cum at the same time.
We dated for two months until she asked me about other women. I told her the truth. She demanded monogamy. I wanted Monique and I was still perfecting my polyamory/relationship game at this time. I acted like a pussy. I promised her monogamy. That lasted for exactly one week. Of course I cheated on her. Then I told Monique I would never be monogamous. I said nothing about cheating and she agreed to stay. After one more month, she left me. She actually sent me a love letter in the mail telling me she missed me.
Two months went by and no contact. I sent her a text asking to meet. She was dating another man by then but she agreed. We met at a coffee shop and I seduced her all over again. It was dark by the time we said goodbye next to her parked car. We made out hard in the street. I slid my hand into her jeans and rubbed her pussy. She came after just a few minutes, but refused to come over that night.
We agreed to meet on Friday. She later texted and re-scheduled for the following day. On Saturday, she came over and we slept together. Then she quit dating the other man. We dated for a few more months before I found out why she re-scheduled. She had fucked the other man that Friday, the day before she fucked me. I did not care that she picked me. I was angry and I showed jealousy. It was not excessive, but enough to display my displeasure. The next time she came over, she ended our relationship and left me for good. She went back to him. I let her go with no drama. I licked my mental wounds and found solace in my diminished harem.
Monique texted me after she broke up with him. She was just feeling me out. She wanted to make sure I was still an option for her. I said yes but she refused my offer to meet. She said she loved me too much to see me in person. She began dating a third man. He turned out to be the provider she was hunting for. They are getting married soon.
Total Cost: $11 (First Date)
Time Spent: 90 Minutes (First Date)
Lessons Learned: First dates should be no more than 60 minutes. Any more is a waste of time (unless you are sure of same night sex).
Jealousy will always damage your frame and hurt your relationships. I lost months of sex because I could not keep my mouth shut.