Author's Note: I am in the process of putting my diary and journal entries online because I don't want my kids stumbling upon them some day. I exaggerate/fantasize where it is fun to do so, but I am staying true to where I was at the time. One journal entry doesn't necessarily fit together with another like puzzle pieces because I wrote them years after, just for the fun of it. I am writing this only for myself. (We were 18 when the events below occurred.)
We're Getting There
~1~
Will and I started going out in high school. What originally drew me to him was his blonde hair, blue eyes and big shoulders. It sounds corny, but when he asked me out, my first thought was what a Teddy bear he looked like, and how nice his hugs must be. It took him two weeks to muster up the courage to kiss me, so you can image how slowly our physical relationship developed.
On weekend nights we would go to his house and hope that his parents would go to bed early and leave us alone. They usually did. Once their door shut, we would make out for the rest of the night, hardly coming up for air. The first time he put his hand up my shirt, I was shocked. I didn't imagine THAT happening with his mother down the hall. I was all snuggled up between his legs with my back against his belly, and his arms in a bear hug around me. He was nuzzling my neck and telling me how good I smelled. I was warm, content, and barely watching the inane movie we had rented.
I felt his hands fiddling with my shirt, and I thought, "Well, here goes." I closed my eyes and felt my pussy starting to throb. When his hands touched my stomach, I gasped right out loud. His hands were freezing because he was so nervous! He asked, "Is this O.K.?" I laughed nervously and told him it was just that his hands were like ice. He continued to slide his hands up my belly to my breasts, where he quickly slid his big hands into my bra. I felt his cold fingers against my already hard nipples, and I leaned my head back against his chest and sighed.
My pussy was on fire, and I could feel the already familiar hardness of his erection against my lower back. I took a deep breath, arched my back a little, and said, "Mmmmmm..." as he rubbed his palms gently against my nipples. Occassionally he would take both breasts in his hands and squeeze them a little. I was so turned on, I felt dizzy.
He hesitated before opening my front-clasp bra, just long enough for me to whisper, "Please." I was trembling as he unhooked my bra and pulled my shirt higher in the front. We stayed like that for a long time, with his hands softly caressing me. Suddenly his parents' door opened, and I covered up in a big hurry. He took me home after that, and I fastened my bra in the car!
~2~
After that first interruption, we made sure we were under a blanket. I figured that his mother would surely be able to figure out what that was about, but at least she wouldn't see my tits!
The first time Will put his hand down my pants, I was really surprised by the wetness of my pussy. I had never masturbated before, so I really had no idea how much fluid could be coming out of me. I had just really learned that the throbbing between my legs was sexual arousal. My pants were on, so his wrist was at an awkward angle, but he rubbed my clit (way too hard, but I didn't really understand that then), and stuck one slippery finger into my vagina.
After that first time, he wouldn't do it unless I asked for it. It excited him to hear me say, "I want you to finger-fuck me, Will." I had a hard time saying it, but it was worth it. Eventually I was bold enough that I would pull down my pants and underwear under the blanket, but not bold enough to take them off. I would sit higher up on his lap, and he would finger my pussy, sometimes gently, sometimes a little roughly. Sometimes his whole hand would be dripping with my pussy juice. I felt like the whole room smelled like my cunt. I was a nervous wreck thinking that his father would come out and smell me.
Next it was his turn. One night I was sitting in my usual spot between his legs, and I felt something warm, hard, and smooth against the skin of my back. I giggled
when I realized that I was leaning against his naked hard-on. He said, "Do you think maybe you could touch it?" It was my first in-person cock, so I was really nervous and excited. I gently put my hand around it, and was surprised how silky the skin of his penis was. I stroked it slowly while I used my left hand to explore his balls. I had no idea that his scrotum would be so hairy. I could feel the pre-cum on my fingers and smell the saltiness of it.
It seemed like his cock got even harder as I rubbed, so I took my hands away so I could raise my shirt and open my bra. When I took him in my hands again, I started pumping hard and fast. He grabbed my tits and started pinching my nipples so hard it hurt a little bit. It didn't last long though. All of a sudden I felt his cock swell and his balls tighten. Through his clenched teeth, he grunted, "I'm cumming." and pulled me close to him. He shot his load all over my tits. I should have been bothered by the mess, but I was too damn pleased with myself. I had just given my first hand job, and it was definitely a success.
Fortunately there were tissues nearby (I was allergic to his Golden Retriever, and I sneezed incessantly.), so he took a handful, and tried to clean the cum off my tits. It was a little uncomfortable once I got my bra and shirt back on, but I tried to think of it as a little souvenir.