My first sexual experience – Cecilia

marinesAfter Marine Corps. boot camp, I got a lot more attention than I had anticipated. I hadn’t developed true confidence in myself. I knew I wasn’t a total idiot, but until this point, I was just starting to challenge my emotions.

I was a single guy slowly realizing that women were finally more attracted to me. I hadn’t seen this superficial side of women before. I had always been close to women using my personality and friendships, but this new desire was new; its was my first encounter in building up “emotional walls”.

That’s when I started to look for women to talk to online. I was around 21 and never in an adult relationship. I hadn’t partied or taken advantage of college. I was the one in the corner staying quiet trying to learn everything he could in school but never brave enough to talk to a girl in class.


I met Cecilia on a dating site. Back then, we just posted one picture, and filled out a profile. That one picture was all we had to go on. We talked back and forth and that’s when we decided to exchange number and talk. I enjoyed talking on the phone. She couldn’t see me and I could be myself without fear of her expressions. We didn’t text back then, so the phone calls were valuable.

We decided to meet. The date went really well and we continued to see each other on weekends. On one of our phone calls, I shared some stories I had written and she was immediately intrigued, and then the tone changed when she learned I was still a virgin. She couldn’t believe “her luck”. She was determined to break me out of my shell. She had been with many guys but never vaginally. She was into everything but saving vaginal sex for someone special. This was all very new to me.

How I Lost “It” (“Sort of”)

After a month of dating, we ended making out in my small jeep in the parking lot of an abandoned middle school. It was late, but still early enough to see the moonlight and hear an occasional walker pass by our car. I didn’t know this would be “the” night. I was nervous nevertheless. She took me out to massage me and get me hard, and then put me in her mouth. It was an unbelievable feeling and quickly escalated. I was turned on but I was in shock most of the time. Sadly, she was leading most of the time.

She bent over the seat, pulling her pants down, and started to guide me closer to her. However, I did not expect her to put me in her ass!! This is how she had “always done it”. How she kept her own “virginity” intact. Confused, I didn’t refuse, and continued. It was tight and hurt some but she was determined to have me. I didn’t want to let her down. We had sex for a couple of minutes before I would get soft. We stopped but she really enjoyed herself. I took her home.

How I Lost “It” (for real this time)

After a week, I got more comfortable with Cecilia. I learned how to give her oral sex, which she insisted on doing once I learned to be “amazing” at it. We had anal sex regularly, and did it everywhere including the shower, on the couch while her roommate was away, and in an elevator at the mall. However, I wasn’t in control of my emotions. I got jealous and suspicious of her every move. I couldn’t relax and couldn’t cum during sex. Of course, this resulted in me staying harder for a longer period of time.

This got to me one day, and was in tears. It felt one sided. She was trying to reassure me that we were ok, but telling me she “loved” me was never part of the conversation. If that word was used, it was usually only to get me in bed. Still in tears, she kissed me, and started to undress me. I couldn’t help but get hard again, but this time I took over control and undressed her. She was hesitant to have me on top, but she gave in and I finally felt myself slide into her pussy. It took a while to get in. It felt far different and better than what we had been doing. I moved in deep and felt her hymen pop. She smiled excitedly, “you popped my cherry!”   Again, in shock, we continued for over an hour. We were very sore. She could no longer claim she was a “virgin” herself. I had taken something from her. It was not a healthy to see it this way. I still hadn’t cum.

Moving on

She dropped me off to work, and we told each other we “loved” each other. A day later, she jokingly questioned if I was really a virgin since I was able to last so long in bed “the first time”. This was upsetting especially since she had “trained” me for a week of anal sex. I started flirting with other girls in return. Perhaps my way to research what was “normal”. Funny enough, women talking to a “marine new to sex that could last long in bed” didn’t get me the best advice to stay with my girlfriend. Jealousy got the better of me especially when she was “too busy” to see me. I started checking her emails. She found out she was talking to guys (who turned out to be just friends but I was too jealous to care). She had her own insecurity issues that was fueling my need for security. Ultimately, we broke up.

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