Now that I am 42 and in a sexless marriage. I thought it was time to relive my glory days. I decided to document all of my past sexual exploits. All the stories I am going to post are true.
Before jumping into the story, I want to share a bit about my background. I grew up in as a very shy kid. I didn’t have my first girlfriend until 7th grade (and that relationship lasted for 2 hours). By the time I was in high school, I began making up stories of girlfriends and sexual exploits to my friends to make up for my lack of experience. This continued in college. I made up stories of being a ladies man even though I had never even kissed a girl. I had my first kiss sometime in college (a random drunk make out with a stranger in a college bar).
After graduating college, I started a job and moved in a two-bedroom condo with a roommate. Now that I had my own room and non-monitored internet, my first order of business was joining the website Adult Friend Finder. I posted a profile and was honest about being a virgin. Luckily, I have a very muscular body and a nice BBC. Once I posted my profile, I spent a lot of time searching profiles. I messaged every profile that I found interesting.
One day I received a message from a woman who was interested in meeting me. She was in her early 40s and was full figured. We exchanged a few emails and then exchanged phone numbers. On our first phone call I discovered that she had a thick Caribbean accent. We made arrangements to meet the following week at her place.
On the day of, I was extremely nervous. I left my condo and thought, “next time I am back here, I will no longer be a virgin”. I drove to her apartment. Once I got there, I rang the doorbell and took a deep breath. She answered the door and she luckily looked just like she did in the profile. She hugged me and invited me in. She lived in a studio apartment. As I looked around the apartment, it became very clear that she had young children. I also got the sense that she likely had a husband or boyfriend who was away at work.
She led me over to the bed and we made small talk as we sat on the bed. Finally, she asked, “are you sure you want to do this?” I quickly said, “YES”. She said “OK”, then she got up and walked to the bathroom. She was in the bathroom for a few minutes and came back wearing just a black bra and panties. She sat down next to me on the bed and asked, “what do you want?” I thought for a second and said, “I want you to suck my dick”. She stared at me and said, “I don’t do that”. Confused, I thought of something else. “I want to eat you out”, I said.
Without a word she lifted up and removed her panties. She laid back on the bed and spread her legs. I wasted no time and dove in head first. I didn’t really know what I was doing but she reached down and guided my head. Soon enough as I licked, she started moaning. I stopped and took off my shirt and stripped down to my boxer briefs. As I resumed licking, I began grinding my cock into the mattress below me. As she moaned louder and louder, I got so excited that I came before I even took my boxer briefs off. I really hoped she didn’t notice.
After a while she said, “I want you to fuck me”. Luckily, even though I had just came moments before, I was ready to go. I got off of the bed and turned away so she couldn’t see the wet spot on my boxer briefs. I took off the boxer briefs and put on a condom for the first time. I got the condom on and got on top of her. I managed to get inside her with a little help from her hand. Once inside her I started aimlessly thrusting. She tried to give me instructions but since those weren’t working, she just reached down and grabbed both of my ass cheeks in order to better control my thrusts. Apparently this did the trick because she began moaning again. And once again, I came within seconds. She clearly noticed this time.
I pulled out and pulled off my full condom. This time around I didn’t stay hard after I came. She was getting antsy and decided to help me get hard again. “Come over here and let me help”. It because clear that she was going to give me my first blow job. “I thought you didn’t do that”, I said. “Well, you have some good dick” she said with her thick accent. She began giving me a sloppy blowjob and my body began responding immediately. As she worked her craft, after a few minutes, I realized I was going to cum again. I pulled her head off of my cock and told her I wanted to fuck her again.
I went back and found my jeans and grabbed another condom. I quickly got it on and jumped back in to fucking her missionary. Within a few minutes I knew I was going to cum again as she started moaning heavily. I tried to stop it but, I came again.
After coming again, she told me that I needed to go because her “roommate” would be home soon. I gathered my clothes and got dressed. I went to throw away my used condoms in her trashcan. She grabbed them and handed them back to me. “You take your sperm with you. Never leave your sperm at someone’s house.” She handed me the trash bag and showed me the door. I’m pretty sure she just didn’t want her man to find the condoms in the trashcan.
I headed out of her place and went home no longer a virgin. Even though my performance wasn’t great, I had that milestone completed. Now I could move on.
I called her a few more times for round two but she never agreed.
Stay tuned for more stories of my sexual exploits!
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