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Shy Guy

Age when it happend: 17
Where it happened: Her Bedroom
Langauge: English
Sex: Male
Rating: 10
Category: Straight

I am not what you call a “ladies man”. Don’t get me wrong, I’m a good-looking guy but I am extremely shy. If it wasn’t for Kimberly, my first time may have not happened. Ok, so I might be exaggerting a bit. So let me give you the back drop.

I had been dating Kimberly for 2 months and things were getting progressively better. She was beautiful. Long dirty blonde hair that went just past her shoulders. She had brown, chestnut eyes and a bright smile. She weighed about 115 pounds and was 5’7″ tall. Not only was she gorgeous but she was smart and funny.

Anyway, during the first month we were into french kissing. I remember the first time was when I was leaving her house and we were at the door. I gave her my usual kiss goodnight, but this time she parted her lips and in went my tongue to dance with hers. Instant boner! It was great. The next time we were in her bed and I got bold and let me hands go up her shirt. I felt her tits for the first time and it felt like soft dough in my hands. I massaged her breasts and rolled her nipples between my thumb and forefinger. Things were getting hot and I found myself dry humping her. My cock was so hard it was peaking out of the elastic waist band of my underwear. She felt my erection and slowed me down.

The next time we got together was it! I stayed over her house but I had stayed in her sister’s room who was off at college. Her parents went upstairs to bed and she sneaked over to where I was sleeping. Of course, I wasn’t sleeping as I knew Kimberly was just in the next bedroom. She told me to come over to her room and I did not waste any time. When in her room, she set up some pillows and blankets on the floor. She was worried her parents might wake at the sound of the squeaky bed. Great idea! We lied down on the makeshift bed on the floor and started to french kiss and grope each other. At the time she was wearing a long t-shirt with only a pair of panties underneath. No bra. I was wearing a t-shirt and a pair of jeans.

“You have felt my breasts, now I want to show you other things,” she said. She took my hand and led it down below her tummy. She pushed my hand under her panties and told me to rub my hand on her pussy lips. My cock was rock hard at this point to say the least. As I was rubbing her pussy, she pulled my t-shirt off and was massaging my chest. She was really getting into it and she placed her had on my crotch over my jeans. By this time I had started to finger fuck her and her hand started to go up and down on my dick still on top of my jeans. I couldn’t take it anymore and I exploded all inside my underwear. I stifled my moans so Kim wouldn’t find out I already ejaculated. I stopped my hand motions and said I needed to go to the bathroom. She had to know but she didn’t lead on. While cleaning up in the bathroom, I was giving myself a pep talk on what was happening. I was so nervous.

I went back to her bedroom and admitted what had happened. She didn’t seem to care. “I just want us to have sex,” she told me. Boing! My cock was hard once again. She took off her t-shirt and she unzipped my jeans and pulled them off. Here we were I in only in my underwear and her in just her panties. My hands and her hands were all over each other while our tongues were intertwined. I started to hump her with her panties on and she whispered, “I want you inside of me before you cum again.” We took off our underwear and I positioned myself on top of her. At first, I had a hard time getting my cock inside her pussy (remember folks, this was my first time) so her hand led my dick inside her. I began rocking my ass, pumping my dick in her pussy. We both quieted our moans as to not alert her parents. She moved both of her hand on my ass and applied pressure with every pump inside her. I couldn’t keep my silence much longer, I started to moan. “Shhh..”, she said,”…ohh..uhh.. parents…ahhh.” She couldn’t keep too quiet herself. I felt extreme pleasure and felt my cum ready to burst.

“I’m gonna cum… Oh God, I’m gonna cum…” I moaned.

“Do it, Jack, cum all inside me,” she pleaded.

My cock exploded at her command. Every drop of semen bursted out inside her. I screamed in a whisper, “Oh Kim, I’m cumming…oh yes.. I’m cumming.” That most overwhelming feeling felt like it lasted forever. After that momemt subsided, I fell to my side, my dick still inside her. We kissed and caressed each other until I finally felt my limp dick fall out of her pussy.

I will always remember that night. We did it two more times later that evening. It was heavan!

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