I first had sex with Jack much sooner than I was raised to believe a lady should. We had been on a couple dates, and it had been less than two weeks since we first met.
Our first “date” was a casual mid-week trip to Starbucks for coffee and an intimate chat. The second date was dinner followed by ice cream. Our third date was the first time we saw each other on a weekend. We went to a movie – he suggested Ladykillers, even though I would much rather have seen The Punisher – and then took a walk. We stopped at a pizza place we both liked and enjoyed a couple of slices and more conversation. Sometime during our dinner I decided I wanted him to stay the night. It was a Saturday, neither of us had to get up early the next morning, and I wanted to get to know Jack as intimately as possible. And I wanted him to get to know me the same way.
I had no desire to play hard to get, and when we finished our dinner I suggested we return to my place. He’d only been there once before, when he picked me up earlier that evening. As we went inside, I showed him my living room and asked if he’d like to watch television or a movie. I had a few DVDs, mostly chick flicks but I also had Goodfellas and Young Frankenstein. Jack said he’d love to watch a movie with me, and I took him into my bedroom, where I kept my DVDs at the time. Even though I’m sure it sounds like I brought him into the bedroom to seduce him, that was not what I had planned.
We stood in front of the shelf where I stored my small DVD collection, and after perusing it for a minute or two, he put his hand on my back. My entire body felt like it was electrified. My heart pounded, and I turned to meet his kiss. My hands were in his hair, and his were on my breasts. Our tongues met between our mouths and we kissed long and very slowly. My hands moved down his body, settling between his legs where I felt him hard and ready. Responding to my touch he lifted my skirt so that it gathered at my waist and began to fondle me as well.
I backed him up against my bed and we fell onto it, still locked in a delicious, hungry kiss. I got on top of him, straddling his waist, and when our kiss broke I reached down to open his pants and free his hardness. I took him into my mouth, feeling how responsive he was to me. Before long I was more aroused than he was. I stripped off my skirt, then removed my top as he took off his own clothes. We made out on the bed for awhile, touching each other, and then he slid down the bed so he could go down on me. I was already very wet, and very close to coming. When my first orgasm was inevitable, I hoped I wouldn’t be too loud or obvious, because I didn’t want him to stop. As it turned out, I had nothing to worry about.
I rode a wave of orgasms that seemed like they would go on forever. When he finally stopped, I had lost count of how many I’d had. I pulled him up so I could kiss him again, and while we kissed I felt his cock slip inside of me. He raised my legs up so that my feet were on his shoulders, and began to fuck me like I’d never had it before. We continued in that position until we needed a change of pace. We rolled over, with him still inside me, and I rode him until I came yet again, collapsing on top of him and kissing him passionately. When I’d caught my breath, Jack put me down on the bed, then lifted up my hips so that my ass was right in his face. He then proceeded to go down on me, practically burying his face in my pussy from behind. When I thought I couldn’t take it anymore, he started using his fingers too, and I came again almost instantly.
The next time I looked at the clock, it was 2:30 in the morning! I was exhausted, but I didn’t want to stop. I was on my hands and knees, with Jack behind me, as deep inside me as he could get. I wanted him to come so bad. When he finally climaxed he let out an intense moan that let me know that he was having as much fun as I was. Finally he lay down on his back, and I lay beside him, draping my arm across his chest. We kissed again, and then while we were lying there in silence I toyed with the idea of telling Jack that he was the best lover I had ever had, that no man had ever made me feel the way he did. But I decided not to. After all, I didn’t want to scare him away. There would be plenty of time for such revelations later.
-Jill
That was kinda sexy. I may have gotten a funny feeling in my tummy while reading it…
I’m impressed you remember so many details of your first time together. I remember a few details about my first time with Vincent, most amusingly this one: We were at my parent’s house; they were on vacation. We were playing around in the bedroom and a light turned on in the bathroom. We both had heart attacks thinking my parents were home but realized it was the automatic timer. Needless to say, the mood was spoiled (but only for a little bit!)
Mia Wallace
Great story! I’m sure we’d come close to heart attacks ourself if something like that happened.
Incidentally, Jack will be posting his version of that evening’s events tomorrow. I hope his memory is as good as mine.
-Jill
We were beginning to think you weren’t going to post anything today!
I agree that it was a sexy story and that it’s cool that you remember the details. Even if it was less than five years ago!
Your first time together sounds like it must have been amazing!
-M&L
That game me a boner.
-Vincent Vega
Wow! Thanks for the encouragement!
-Jill
I don’t know how but I missed this entry until now. Great read, and it gave me a boner too.
-D650
Two boners! Woo hoo!
-Jill
I remember you telling me this story right after it happened. That you remember all these details just shows how wonderful it was.
-KinkyCAgirl
A wonderful retelling that really captures the excitement and overwhelming passion of getting so initimate with someone so new for the first time. Absolutely fantastic….and a boner here too!!!