The night I lost my V-card

Flash back to around this time last year. I (M20) was at work when I had an accident that required the cleaning group. She (F28) was the one who responded. After she was done, she had slipped me her number and asked to keep in touch. Over the next few months we talked and grew closer.

She had confessed that she had a crush on tall, bearded nerdy guys, and I hit all three marks. At the time, I was dating someone else, but come October, that relationship came to a rocky end. With nothing holding me back, I decided that it was time to move on and go further with… let’s call her Chris. We would sit together when I got into work. It started with simple hand holding and quiet whispering of sweet nothings. One day she teased me that i wouldn’t have the nerves to kiss her, and to which I proved her wrong. From there, things escalated quickly. Another week went by and we were making out, tongue included.

As a tall, nerdy virgin who had never gotten more than a hug from a girl, Chris was an exciting time. When I confided in her that I still had my V-card, she told me that she wouldn’t mind giving me my first experience. She also suggested that we should wait since I was still hung up on a possibility of getting back with my ex. Unfortunately, I falsely claimed that I was ready to go all the way. So we planned, and executed it early November.

After navigating the obstacles that was my family and our very noisy dog, I snuck her into my room for an overnight stay. She brought snacks and condoms, I provided entertainment. I often left videos and movies playing as I slept, so this provided the perfect cover. After we started our night, it wasn’t long before the intimacy began.

It started with a simple bj, and lemme tell you… my view of bjs has been forever changed. It wasn’t a long bj, but it was enough for me to find why people love them so much. After getting me nice and ready, she got a condom out and put it on, then took position for a ride. It took a minute of maneuvering (we’re both rather chubby), but soon she eased herself onto my length. The moment I could declare myself no longer a virgin was a fantastical moment. She road me for close to an hour, or at least what felt like an hour. When I came, it was the best feeling of my life. Far better than climaxing from masterbation.

When she came, she pulled herself off and laid next to me. We decided to cuddle for a bit so we could rest, so I disposed of the used condom and we cuddled. Of course, with sex still on my mind, I could stop myself from reaching between her legs. After giving me a quick tutorial on how to properly finger, I got to work. Let me tell you, the noises she made as she tried to keep herself quiet were the best noises I’d ever heard. I also sucked on her breast like a hungry toddler, and the combination of sensations caused her cum at least 2 more times.

Now rested and raring for my round 2, we got out the second condom and got into doggy style. This time… it wasn’t as nice, mostly due to my inexperienced. It still felt great, but was unfulfilling so we changed positions into good ol’ missionary. Now this? This felt *way* better. Watching her face twist in pleasure as I thrusted into her, getting to put my hand on her neck to help her keep quiet. The scene, to me at least, was magical. Missionary lasted a long while, resulting in her cumming again. I was getting tired, as the new experience was draining my stamina quickly. She offered to go for another ride, and so we switched back to her on top.

The second bought of cowgirl lasted for a bit before I finally came again, and we decided to call it a night. We removed the condom, snuggled up, and slept the night.

When we woke up, we had to wait a bit for the coast to be clear for her departure. To pass time, we decided go one more time. This time, no condom. We got into cowgirl and went to town. This time was slow and sensual, both to pass time and to be careful. When I came to burst, we made sure to pull out before I actually came. Disappointing, since I like myself a good breeding, but she was already a single mother so we decided not to take that risk.

We got cleaned up shortly after and she was on her way. I miss her deeply, because she was super sweet and caring. She broke off contact after I kept delaying a first date since I was *still* hung up on my ex. I regret not handling the situation better, and hope that maybe one day we’ll meet again.

NSFW: yes

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