How are you all? Did you have a nice holiday in spite of the whole COVID-19 thing? We did. We were bad and went to visit family – but we did it in the least exposed way possible. We quarantined for two weeks before the trip and drove so that we limited our exposure to others. A little bit of a change from our original plan to stop and see Doctor Smith along our way. We decided to forgo that pleasure in the name of safety. That kinda sucks as I was looking forward to being naughty but I didn’t want to risk exposing the kids to anything. So the bad news for you all is no new three-way stories to titillate you (and me because I get off on your reading about me, and seeing me etc etc). All is not lost dear reader, how about I pull one out of the way-back machine for your enjoyment?
There’s a thread about women sharing their first experience seeing male genitalia that I contributed to. Writing the short entry really brought me back. I don’t usually play ‘let’s remember’ but sometimes you get a vivid memory where you’re almost there again. I had one thinking back on this. Ben Folds has a song, Brick, that includes the line “The smell of cold, car seat is freezing,” that captures that sort of vivid sense-memory I’m talking about. I suppose it’s not strange having strong memories of ‘firsts’ and that night had more than a few firsts for me.
I’ll call him ‘Tommy’. He was my second boyfriend. My first was in Middle School and was really very innocent. We would hold hands and kissed a few times. My relationship with Tommy was something different. I was a Freshman, he was a Junior. He had a car (a ‘75 Monte Carlo). We met at a local hang-out. At the time we started dating I had just turned fourteen. I looked a lot older, especially with make-up. We started dating, typical High Scholl stuff, movies, pizza, dances, and fairly quickly, parking. I got very familiar with the back-seat of that Monte. Don’t get me wrong, I was all for it. I don’t recall this particular night as our actually having ‘gone’ anywhere. I think we went to the dam and just drank wine and fooled around. I do remember it being cold but not super cold.
The dam was the local make-out spot. It was a semi-secluded road that went by the dam. Very low traffic. Anyone usually there were kids parking or the cops coming by to roust them out. After a couple of swigs of wine we started kissing and in typical fashion he went up my sweater fairly quickly. Again, this was something I was totally fine with. What was a little different is he pushed my sweater up around my shoulders exposing me. I remember it well because it was border-line too cold to be doing that and I almost pulled it down again but him actually getting to see my tits was something newer and I didn’t want to ‘go backwards’ or have him think I wanted to or something. You worry about stupid things when you’re young. I’m a fairly horny woman but in those days I was super horny. A different boyfriend joked that I had ‘guy horniness’. I love to have my nipples played with and those make-out sessions would usually leave me soaked. I’d pull his shirt up too so we could feel skin on skin. He started rubbing my mound through my jeans, again something new-ish but not something we hadn’t been doing for a while. One time I had a skirt on and he went up under it and felt me through my panties – I really liked that, in fact I still love to start a love-making session being caressed through my panties. Maybe it makes me feel young again, who knows. From that point it was under the jeans, over the panties.
Tommy was trying to slip his hand into my jeans but they were new and tight. He was having trouble. I unbuttoned them so he could have easier access and this time he slid his hand inside my panties as well. I remember a slight shock as I felt his fingers. I don’t think I was going to tell him to stop but I may have hesitated a second or two but oh God it felt really good. I know I opened my legs. By this point I was rubbing him through his pants and I knew he was hard. Tommy was still struggling with the tightness of the jeans and the angle his hand was at and started pushing my jeans down over my hips. I actually remember debating internally for a second as to whether or not I should let him do that but I was so damned horny I lifted my hips off the seat so he could pull them down.
He tried to take them off but I said, “No, leave them on.”
It was dark in the car but not totally dark. I could see but I remember it in gray-scale. I know he was looking at me because I was watching him watch me. It was the first time a boy had ever seen my pussy. I loved the fact that he was looking at me. He ran his fingers over my mound and through my slit. It felt really good. Fairly quickly he put a finger inside of me and started finger-fucking me as we both watched. I was still absently rubbing his cock through his jeans. His fingers felt good and he fingered and kissed me for a bit until he undid his own belt and jeans and pushed them down. I remember seeing his cock spring out of his underpants, like literally spring out of them. It looked huge to me, like a baseball bat. My literally first thought (after the ‘oh wow it sprung out of his pants) was ‘that thing would never fit inside of me’. Looking back, it was bigger than average but not the largest I’ve encountered. Maybe the second largest though.
He took my hand and put it on his cock and went back to fingering me. We were sort of half rolled onto each other in the back. Almost at a ninety degree angle. I recall being surprised at how soft it felt, the skin so smooth and warm. I sort of knew what to do with it so I started stroking him. After a little bit Tommy took my hand with the one that wasn’t inside of me and guided me as to what to do. With this direction I set to with a will and in a very short time he groaned and exploded onto my belly. The hot jet was a surprise but I loved it. I recall starting in fascination as his cum jetted out onto me, loving how his erection throbbed. I felt so grown up, so powerful, so in control.
Hand jobs and finger-fucks became the norm for us after that. He learned how to bring me off. I let him get me totally naked after his prom, something which was interrupted by a cop’s flashlight through the window. We scrambled out of there only to wind up someplace else where I later both gave my first blowjob and received cunnilingus. We broke up that summer, much to the relief of my parents who weren’t fans. I’ve still got that prom picture – though he is neatly cut out of it by my father haha. All you can see of him is his hand on my arm.