Kelly's Diary 015 - My First Date After Steve - Cover

Kelly's Diary 015 - My First Date After Steve

Copyright© 2024 by Kelly85

Chapter 4: A Date With Doug

Coming of Age Sex Story: Chapter 4: A Date With Doug - Steve had taken my virginity and until he moved away he'd been the only one I ever had sex with. Now he was gone so what would it be like to go out with someone new? How far would I let him go? How would it feel to have sex with someone other than Steve? So many questions! Just one to find out...

Caution: This Coming of Age Sex Story contains strong sexual content, including mt/ft   Consensual   Heterosexual   True Story   Oral Sex  

Not only do guys not come to the door anymore, apparently they don’t open car doors either as Doug remained planted in the driver’s seat while I let myself in from the passenger side.

Actually, I shouldn’t say “car” door as Doug was driving a large Ford pickup truck which I had to step up high to get into. I could just imagine the view my neighbors would have gotten had I worn my short skirt! The truck had a bench seat and as we drove off I felt like I was above all the traffic being so high up in the air. Come to think of it, this was my first date in a truck!

We just made small talk as I wondered where Doug was planning to take me. He didn’t seem to inclined to tell me right away as we wound our way through the south side of town.

When I had gotten in I had taken a seat on the passenger side as I would have with anyone. Since this was our first date, I figured he could make some of the moves first so if he wanted me to scoot over and sit next to him then he should ask. Since he didn’t, I stayed where I was with about two feet between us. It wasn’t a big deal one way or the other as it only took about ten minutes to get to the theater. He drive around the back of the shopping area to where the movie theater entrance was and parked.

“I hope you don’t mind seeing a movie,” he said, turning towards me after he had turned off the engine.

I just nodded and smiled, not sure what to say at this moment. Personally, we could have skipped the movie and stayed in his truck and made out all night. God he was gorgeous! The weather was mild so he had on a pair of jeans with a faded blue flannel shirt and no jacket. For a moment I thought of my old boyfriend Steve and then quickly put those thoughts away. Doug was so much older and he was built!

“Well, it starts in a few minutes so I guess we’d better get going,” he said, breaking the silence between us. We both got out and walked to the entrance but I noticed he didn’t try to take my hand or put his arm around me. Hmm, maybe he wasn’t quite as forward as some of the girls claimed he was.

Doug paid for the tickets and then we went to the snack bar for some popcorn and a drink which we took with us to the theater. He led me to some seats which were in the center but towards the top of the stadium seating area. There weren’t a lot of people in the theater yet and nobody behind us. Although we weren’t in a crowded area, it wasn’t exactly in the most private seats in the house either.

I tried to remember if this was one of the theater rooms Steve and I had fooled around in. Odds were it was as we had been her more times than I could remember. Steve liked to bring me to this particular theater as it featured arm rests that lifted up and out of the way which made life much easier when it came to being naughty during the movie. I couldn’t begin to count the number of hand jobs and blow jobs I had given Steve here not to mention he even fucked me a couple of times when the theater was pretty empty.

Again I pushed out the memories of Steve and concentrated on Doug. For the time being, I may as well be dating my dad for all the attention he was giving me. We both sat in our respective seats, hands in our laps while we shared the popcorn. It was almost quaint and had I been seeing a movie with my parents, I would have been perfectly satisfied. Only problem was, I wasn’t out with my parents, I was dating Doug! What’s the point of bringing your date to a theater like this one and then just sit there? I knew he wasn’t shy, at least nobody who ever dated him claimed he was. If anything, he was known more for going for a feel from the moment you got in the car with him!

Finally, about fifteen minutes or so into the movie, Doug shifted around in his seat and in the process his arm reached over and behind me. I felt his hand on my shoulder, just resting on it without applying any pressure. I waited in silence as thoughts of what he might do next raced through my head. God, my pussy was feeling so hot I wanted to reach between my legs and rub it but I didn’t think we were quite to THAT stage yet!

Then Doug finally did what I had been waiting all night for, he reached down and started to trace little circles on the upper portion of my sweater. He didn’t quite make it down to my boobs but he was getting closer. Not wanting him to get the wrong message and think I wasn’t OK with it, I twisted a little in my seat so I was actually turned away from him slightly and then leaned back against him. I made sort of a show out of being uncomfortable against the arm rest and he instantly took the hint and raised it up and out of the way, letting me lean back against him. This allowed him easier access to me and he didn’t hesitate to take advantage of it immediately. Oh well, I guess he just needed to get started because it was like he went from doing nothing to being quite forward, not that I minded of course.

His hand moved closer to my boobs until it was reaching the upper portion of my bosom consistently. As for me, I rested my hand on his leg and held on lightly to his upper thigh. God he felt so firm and strong! Knowing Doug would undoubtedly be telling all his buddies about our date, I decided I had better take a little initiative myself if I didn’t want to be known as a girl who “just sat there”. I put my free hand over his and then gently moved them both down to my breasts, planting his hand directly over my right boob and pressing down on it to indicate what I wanted from him. At least he could take a hint as my efforts were rewarded by a firm squeeze as his hand cupped my breast and began to massage it through my thin sweater.

For maybe half the movie, Doug just groped and fondled me. My sweater buttoned down the front and it didn’t take long for most of them to be undone. Without a bra underneath, he had easy access to my boobs and I loved the way his large hand would cover one and cup it while his fingers would pinch and pull at my nipples. God, if only his mouth was on them - then I would be in heaven!

Meanwhile, as Doug played with my boobs I was running my hand along Doug’s leg and playfully toying with his crotch a little. I never made any effort to go any further as it would have required me to be double-jointed in the position I was in at the time. Even so, he was plenty aroused and from what I could feel through his jeans, he was quite a bit bigger than Steve when it came to the cock department and Steve hadn’t exactly been a miniature!

Eventually I knew it was up to me to make the next move since it would require me changing my position to do anything more. As I also knew that if I should move it would be a clear signal to Doug of my intentions so I thought it through carefully. Well, maybe not TOO carefully as I wouldn’t have been surprised if my crotch didn’t look like I’d peed in my jeans as hot and wet as my pussy was feeling.

I leaned forward and twisted in the opposite direction so now I was facing towards him. With the armrest out of the way, I had pretty easy access to him and I wasn’t about to let the opportunity go by. My sweater hung open and I was conscious that my boobs were visible not only to him but to anyone else who had the right angle but that didn’t appear to be the case tonight. Just the light touch of the sweater brushing against my nipples made me practically jump out of the chair as I got into position.

I looked up at Doug and he grinned at me. It hit me then that we hadn’t even kissed yet and by now I was wondering if we would. I enjoy kissing a good looking guy as much as the next girl but it wasn’t the primary thing on my mind tonight. What I wanted to kiss was a little bit lower on his body! I licked my lips seductively for his benefit and turned my attention to his jeans. He was wearing some western style belt buckle that hard to unfasten and eventually he had to help me. I was OK after that ... unbuttoning his jeans and pulling down the zipper.

Damn, he was wearing jockey underwear - what was he thinking? If he was expecting to get a BJ tonight you would have thought he wouldn’t wear any underwear at all and if he felt it was necessary, then why not boxers? For him to wear jockey shorts is like me wearing a bra - it can be dealt with but what a pain. At least I was sensible enough to know what I was hoping for and left my damn bra at home!

As it was, Doug’s dick was already so hard and big it was practically pushing up past the elastic waistband so all I had to do was lift up a little on it and there before me was my Holy Grail - his beautiful cock head! I could barely see it in the dim light of the movie projector but I didn’t need any light to feel it with my fingertips. The head was so smooth and soft at first but then firm as I pressed harder on it. I pushed my hand under the elastic and took his stiff shaft in my hand, holding it like a runner grabbing the baton in a relay race.

“Is this what you wanted?” I whispered up to him, grinning as I held his hard dick in my hand.

“Oh yeah,” he whispered back, “Suck it girl.”

Finally we were getting somewhere! Doug helped push his underwear down enough to free his dick for me. My head was leaning on his shoulder as I tried to see it better in the flickering light from the screen. It wasn’t like I had held that many dicks in my life. Actually, Doug’s was only the fourth one for me and two of those really didn’t count. My first cock was a while ago. After catching me watching my dad masturbating, my mom had me hold him later that night in our hot tub to teach me what it was. It wasn’t a sexual experience for me as I had no idea what a cock was really all about. As for my dad ... well, that was a different story. I didn’t suck him, though, and I’ve never touched him since then. I doubt I’ll ever forget it though - not one of those things that’s easy to put out of your mind!

Steve was my second cock and not only did I touch and blow him, but his was the first cock to make it into my pussy - also known as losing my virginity in case you didn’t figure that one out. Over the course of the next seven to eight months, I wouldn’t even try guess how many times I held his incredible cock in my hand! There was ONE time when I did his younger brother Jim, but that was more to tease him than anything else so I don’t really count it as one of “my” cocks but technically I have to include him. Thus Doug was now my fourth cock, or my second ignoring my dad’s and Jim’s.

Finally my curiosity got the better of me. I HAD to know how he tasted, how his cock felt in my mouth compared to Steve. It may not be fair to compare two guys but I couldn’t help it. I knew Steve’s cock intimately, every spot where he liked it licked, how he liked it sucked, and when he preferred to fuck me instead of having me blow him. With Doug, it was all new territory and I found it to be a bit exciting as well.

I took a quick look around and saw nobody was paying us the slightest bit of attention. Inching back against the armrest behind me for support, I lowered my head to his lap until my outstretched tongue barely touched the tip of his dick. At first I just flicked my tongue on him, barely touching him yet letting him know I was around - as if he didn’t already know! He obviously liked it and wanted more as I felt his hand on the top of my head and then pressure as he pushed my head down further down into his lap. The strong male musky odor of his crotch filled my nostrils as my mouth descend on his shaft, taking more of him into my mouth.

“Ohhhhhh,” he moaned softly as my lips met the base of his shaft and held him there for a few moments. As I lifted my head off of his dick my lips caressed him while my tongue ran all over his nice hard shaft. I loved the way he felt in my mouth, the taste of his dick. God I missed sucking cock!

As I went to work on him, I tried to recall all the things that Steve use to like me to do to him. He seemed to love it in my mouth more than just licking the outside of it so I tried to keep Doug’s dick in my mouth as much as possible. My hand held his large hairy balls and I gently rolled them in my hands, mindful of my mom’s advice to never get too rough with them. Doug kept his hand on my hand, gently pressing down all the while, as if emphasizing his desire for me to keep him in my mouth.

My mom had taught me a few tricks back when I was sucking Steve to keep him from cumming too fast but I wasn’t interested in trying any of those with Doug, at least not this time. If anything, I was anxious for him to cum as soon as possible. It had been far too long since I felt a stiff dick shooting its gooey sperm into my mouth. How many nights had I masturbated dreaming of this moment, wishing I had a nice hard dick again all to myself?

Doug was getting close from all the signs. He was wiggling under me little boy squirming during a sermon in church. I could hear him breathing heavier and his cock had swelled up and become like a steel pipe it was so hard. God, I could only imagine how it would feel if he was fucking me with it!

“Oh god,” he whispered as his hips lifted up, ramming his dick into my mouth as if he was trying to push it down my throat. Sure enough, a few more strokes with my mouth and he started to cum, spurting a monstrous load of sperm into my mouth. I kept my lips sealed around the shaft, trying my best to keep every drop in my mouth and not waste any of it. Damn the boy had a load! He must have shot a half dozen or more good sized shots of cum followed by a number of smaller ones until he collapsed in the chair.

Dropping his spent dick from my mouth, I quickly sat up next to him and opened my mouth to so he could see his cum in my mouth, something I knew turned on Steve something fierce. I could feel it pooling on my tongue and I almost gagged as some it started to drain down my throat. Then I closed my mouth with a big grin and swallowed it down. It took a couple of gulps but I got it all down after which I showed him my open mouth, just like a little girl showing mom her that she had swallowed all her medicine, The difference was, in this case I WANTED to swallow it all down!

For most of the remainder of the movie I just leaned against his shoulder and held his nice cock in my hand. He softened just a little at after he came first but quickly rose back up again as my hand went to work on it. Meanwhile, he was back to groping my boobs, not that I minded one bit! As the movie came to a close we each got our own clothes in order, putting ourselves back together again to be “presentable” before the lights came back on.

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