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First Time at 25
I grew up in a conservative Irish Catholic family on the East Coast. My parents are both very religious and they expected me to go to church every Sunday.
I’ve always been shy and introverted. As I went through junior high and high school, I had a small circle of friends. I was too shy to talk to the girls. I didn’t have any female friends.
I started to discover my sexuality when I was 12 or 13. When I was thirteen, my pubic hair started to grow. At that age, I was becoming more and more fascinated with my penis. I used to look at it in the mirror. I was 12 or 13 when I first masturbated. I learned to masturbate when I was in the shower. I adjusted the shower head so that it would spray a jet-like massage spray. I laid down in the bath tub and let the spray of water land on my cock. I got hard and I enjoyed the new sensations. When I came, it was fantastic! I started masturbating every day in the shower.
During junior high, I started looking at catalog pictures of women in lingerie, bras and panties, and swimsuits.
During high school, I was attracted to a girl named Bridget. She was intelligent and I would have liked to date her. I was too shy to talk to her and I didn’t have any self confidence. I used to think about her while I masturbated.
In high school, I often masturbated while looking at the Sports Illustrated swimsuit issue. It always turned me on.
I went through high school without a single date. There were lots of girls that I found attractive but I was much too shy to talk to any of them. (My advice to any high school boys that are reading this: Talk to the girls that you like. You must learn to overcome your shyness. Don’t make the same mistakes that I did.)
I graduated from high school in June 1991.
I went to college in New York state. When I arrived on campus, I moved into my dorm room. The school provided orientation information for all the freshmen. Included in the materials condom and instructions on how to use it. I remember how erotic it was to put on a condom for the first time. I wanted to try it. I wanted to practice. I wanted to know what it would feel like to have a condom on my hard cock. I masturbated with the condom on my dick.
I lived in a co-ed dorm but there were no women that lived on my floor. Since my major was computer science, there were few women in my classes. I didn’t meet any women. I was too shy.
I transferred to a different college. The new school had an equally poor ratio of females to males. (My advice to any young men that are reading this: choose a college that has a balanced ratio of men to women.) I was still shy and introverted.
During my sophomore year, there was a 20 year old woman named Susan in one of my classes. She was Chinese. I started to fantasize having sex with her. I thought about her while I masturbated. (I am white) I developed a strong interest in Asian women.
My college years were uneventful. No dates and almost no contact with any women.
During college, I became interested in porn. I used to view porn from the Internet and I started buying pornographic magazines. I masturbated while looking at pictures of naked women and pictures of people engaged in intercourse.
I worked hard during college. I was always stressed out. I always needed a sexual release. I masturbated a lot.
After graduating from college, I moved to the West Coast. I went on two or three dates in 1995. Nothing happened.
I still don’t have any confidence and I had low self-esteem. I buried myself in my work. The only friends that I had were male friends.
I kept masturbating and fantasizing about sex with women. But I rarely spoke or interacted with any women. I was working long hours at a high tech computer company. It didn’t give me much opportunity for meeting women.
In March 1997, I was at a computer conference in San Francisco. I ran into a woman that I recognized from college. Her name was Mimi. Mimi was Chinese. She walked up to me because I was standing in my company’s display booth on the exhibition floor. We chatted and she was surprised that I knew where she went to college. We had been in two classes together, but she didn’t recognize me at all.
I casually kept in touch with Mimi via email. She lived on the East Coast. I lived on the West Coast. I later found out that she was married. She was nice to me and friendly. I was glad to have even this small friendship with her.
In February 1998, she and I started talking on the phone. Our first phone call lasted 7 or 8 hours. We had 3 or 4 long phone calls in February and March.
In March 1998, I was planning to make a business trip to a computer conference in San Francisco. Mimi made plans for herself to be in San Francisco the same week. She said that she needed a break from her hectic work and that she had friends in the San Francisco area that she was planning to visit. Also, she was planning to attend the conference that I was attending.
We met in San Francisco and spent a few hours talking. It got really late and she came back with me to my hotel. There were 2 beds. We slept on different beds that night.
As we spent time together that week, Mimi revealed that her marriage wasn’t working out. She and her husband were discussing planning to separate/divorce. I consoled Mimi.
Mimi seemed eager to spend time with me. She was also very comfortable sleeping in my hotel room. The night that she was in my room, she and I fell asleep in the same bed. Nothing sexual happened. But I could sense that we were getting more comfortable around each other. I was really glad to have some female companionship in San Francisco.
As the week progressed, she and I slowly started to become more phsyically intimate. She was sleeping in my bed and we held each other. It was nice.
On a Friday night, everything became more sexual. We spent hours in bed fooling around. I let my instincts be my guide. I touched her, held her, caressed her. I stripped her down to her panties. Eventually, I knew that I wanted to kiss her. I was afraid at first. I kissed her cheek. Then I moved to her lips and we kissed. It was my first kiss. I was 25 years old and finally had my first kiss.
The next day (Saturday), Mimi and I went to Fisherman’s Wharf. We spent the day together. It was great. We went back to the hotel and we were both eager to climb into bed.
Mimi was wearing a t-shirt and panties. I was wearing a pair of shorts.
In bed, we kissed, hugged and enjoyed being together. I took off her shirt and gave her a backrub. I enjoyed touching her breasts.
We kissed and stayed under the covers. To my surprise, Mimi had taken off her panties. I looked down and say her nake pussy and pubic hair. It was an amazing sight!
She kept asking me to fuck her. She revealed that she had not had sex with her husband in a year. I fingered her pussy. It was wet and warm.
I wasn’t sure that I wanted to fuck her. I was turned on but I didn’t want to rush anything. Before the night was over, Mimi sucked my cock. It was a nice feeling. She sucked me until I came in her mouth.
We both fell asleep. On Sunday morning, we said our goodbyes. She was flying back to the East Coast and I had to fly back home too.
About 2 weeks later, Mimi flew to the West Coast to spend a weekend with me. We fooled around. She gave me another blow job. I fingered her pussy, played with her breasts, and licked her pussy. We did 69 too. It was fun and exciting to touch her body. I was very turned on by her body and her pussy. Pussy is amazing. It’s soft, warm, wet, and inviting.
She asked me to fuck her but I didn’t. I wasn’t ready.
Two weeks after that (April 1998), I was in Los Angeles on business. Mimi was traveling during that time too. We had phone sex every night. I was thinking about sex all the time.
Mimi changed her travel plans so that she would have a connecting flight through Los Angeles. I met her at the airport. She said that she changed her flight so that she could spend the night in LA. We went back to my hotel.
It pm in the evening on April 30th. We started foolling around. Mimi is very attractive. And I definitely was turned on by the fact that she’s Asian.
We fooled around for 2 hours. I decided that I wanted to fuck her. I told her that I’d go buy some condoms.
We were in downtown LA. Everything was closed. There weren’t any stores open. I walked all over but didn’t find anything. I eventually found a gas station and bought a 3-pack of condoms.
When I got back to the hotel room, Mimi was asleep. I woke her up. I wanted to fuck her. We did some foreplay but I was eager to penetrate her. She took my cock in her hand and guided me towards her pussy. She teased me by touching the head of my cock against the wet exterior of her pussy. It was erotic.
I put the condom on and she laid down on her back. She spread her legs for me. It was beautiful. I slowly put my cock into her pussy. It was the most natural feeling in the world. I remember thrusting in and out of her pussy. I fucked her for 5 or 10 minutes and then I came. At age 25, I had finally had intercourse. It was something I had thought about daily since junior high.
The next morning, Mimi and I did it two more times. Once was in a chair by the window of the hotel room. The other time was on the bed in front of a mirror.
I really enjoyed the fact that Mimi was eager to have sex with me.
We kept dating. Mimi described herself as a “nympho”. We had sex often. Everytime we saw each other, we fucked in bed. It took time for me to get comfortable with sex. And it took time for the two of us to learn about the best type of sex for both of us. The sex got better and better.
The moral of this story is that I am glad that I did not wait until marriage. I am glad that I decided to engage in pre-marital sex. Sex with Mimi was magical, intense, erotic.
Even though Mimi and I aren’t together, I still think about her. I remember the great sex. If I see her again, I know I still want to fuck her. She is a sexy seductive Asian woman that knows how to turn me on.