“The Beginning of a Long Ride”
“Finally,.. I was 21. Now I could go to the bars, “legally” and get served. I felt like a king. I felt like I knew it all. I knew how to treat a woman, sexually, yet I needed to learn some other stuff. Actually, I needed to learn a lot. I’m still learning to this day. Women are stronger than men in so many ways, yet, they also are as delicate as a flower at the same time. A part of me loved being single, and a part of me was dying to settle down with someone. But who? I figured, okay, I’m 21 now. I am going to start taking notes on everyone I meet, date, or even sleep with, in order for me to find, “the one”.
My first candidate was a young, soon to be senior at a Catholic School. No, I wasn’t robbing the cradle, in fact, this girl was my neighbor. She used to send me love letters all the time growing up. When I was 18 and graduated I was looking ahead, and I frankly told her that when she turns 18, I will take her out. Well, I totally forgot about her Birthday, which was in July, and one day away. I would of never remembered this, of course, until she stopped me, to tell me, when I went over my parents house. Damn, she looked hot as fuck.
I asked her how she was doing and so on. She basically just came out and said it, “Where are you taking me for MY 18th birthday, Justin?” I thought, oh, yah. This is perfect. Kelly was “perfect”.
She gave me a big hug, and I could almost touch my hands around her waist, that went down to hips of a women and a small little bubble of a butt. She obviously worked out. And she obviously wears contacts now, and also, now, has blonde hair, instead of brown, and it looked so natural. She must also tan. But, doesn’t every girl? I thought.
I could see “the want” in her eyes. I remember thinking to myself that I wasn’t going to hurt this girl. I would take her out, show her a good time, and that’s that…..and, that’s that.?
My intentions are always good. When I get taken advantage of, I can’t help it. I guess I have to sexually defend myself. Lol. Well, knowing that she wouldn’t “legally” be 18 until tomorrow, I told Kelly that I’d pick her up at 7:00, and we’d go to a movie.
While at home, I kept thinking about how fucking hot she was. Then I’d tell myself, no, no, I’m just taking a girl, I know, out for a movie. Damn! Why did I say movie?! I should of thought of someplace, I don’t know, brighter? I tried to do some things around the house. But, the more that I was awake, and vertical, she kept entering my mind. I couldn’t help it. I have a weakness for beautiful girls. What can I say? Nothing. I’m a human being.
I was actually thinking about going upstairs and masturbate, to release some of the overproduction of cum filling my balls. But, no, I didn’t, and this evening was not going to go off as planned.
I just know myself too well.
When I arrived at Kelly’s house, her mom said she was upstairs getting ready and if I wanted I could go up there. Her mom was pretty fucking hot too. If that says anything about how Kelly would some day turn out. Her mom of course knew me for a long time, so she really didn’t have an issue with me going up to her daughter’s bedroom. But, I just said I’d wait in the living room.
When Kelly came down the stairs, I almost fainted. Truth. My dick was immediately hard, and I didn’t care who saw it, or, better yet, I didn’t even “think” about who saw it. I know her mom did. I’ll explain that one later. I was able to make it go down as I had to downplay my excitement as well. She was wearing ‘Daisy Dukes’, a cutoff shirt, exposing her belly button ring, and cowboy boots. Her ass looked fucking amazing in those shorts. A little bit of her tight fit ass was showing beneath her shorts. If you know me, you know that little bit of ass cleavage was enough to give me strength for the next eight hours, if need be.
When she bent over to pick up her stuff, I noticed she had on a black lace thong. So fucking hot. Aaaannnd, I had to remind myself that this girl was only 17. Well, for the next five hours, but still.
Now, when I see some of you girls with those tight little workout shorts on, it reminds me of Kelly. I’m sure you know who you are that I’m talking about. Fantastic fucking ass.
We left, chit-chatted on the way to the theater. We went to go see “War of the Worlds”. A descent sci-fi remake. Tom Cruise. During the movie, Kelly kept moving closer every time there was a scary scene.
Until finally she had her head on my shoulder. Which was fine. Everything was fine. Maybe she was tired? I thought. Then her hand made it onto my leg, after she was startled. Her hand never left that area. She was deliberately keeping it there. Ok, I thought. Maybe she just wanted a place to put her hand? Yah, “hands”, they’re such a pain having them attached to your body with no where to put them. ?
Then something came over me. I was not going to fight it. If Kelly wanted to truly “do it”, I was game. I just needed to test her to see how far she wanted to go. Her hand was on my left upper thigh. Luckily, my junk was hangin’ to the left, so she was only like four inches from the tip of my cock. I shifted myself down, as if I were getting more comfortable, than sitting straight up. There! The head of my dick was right underneath her pinky and ring finger. Within seconds it was past her palm, and elevated more than it was (I did say I was horny).
That’s what she was waiting for. Yep. She giggled and said, “what’s that?” She joked, while she cupped it with her hand. Just by her touching it thru my jeans, enlarged it another inch in diameter.
“Is this, what I think it is? Maybe licorice?” she said, playing dumb. Before I could even answer her, she unbuttoned my pants, unzipped me, and my cock jumped out like it was an animal gasping for air that got trapped with a net.
Luckily the movie was out for weeks, and we were sitting in the back corner of the nearly empty theater. Another subconscious decision of mine. She actually got my cock thru the opening in my boxer’s and went down on me in the movie theater. This was a first for me. She got good at doing that somehow. Maybe she got around at her school.
She was going to be a senior at a Catholic school, and maybe she didn’t believe in having sex before marriage? All these thoughts were going through my mind as she sucked my cock not holding back on the noise. It sounded exactly what it was, sucking dick. She was doing something with her tongue that was giving me a sensation that I didn’t know how it was going to end. What I mean is, I had to stop her, because with this sensation, I didn’t know when and if I was going to cum. She was swirling her tongue around the tip of my penis, which was doing it. It did feel good. But, I didn’t want to just cum in her mouth. Although I’d be able to do it again. It would just take longer.
Soon as the credits started, we got out of there. We drove around for a while, found a dead end to park, but that only lasted so long because a car came down the road. It was almost 10:30 at this point, and she said we could just go back to her house. Her Mom would be sleeping, and her Mom’s bf wouldn’t be there tonight, and I could just sneak upstairs into her room.
Her mom slept on the first floor, which kinda gave me room to breath. The stupid things people do when they want to get laid. And, at this point, I HAD to get laid and drain my balls or I was going to have blue balls from being erect for so long.
So we made it back to her house, and I literally got behind a plant when her mom came out of her room, right before the stairs. Erection, abort! . Kelly distracted her Mom, and waved for me to go upstairs. Soon as I got to her room, and Kelly shut the door. She came running over to me and kissed me, hard. Like, I want to fuck, right now, kiss. Erection, back up.
She unbuttoned my shirt and took it over my shoulders, while then unbuttoning my pants. She had my dick out and in her hand before my shirt hit the floor. She was beginning to go down on me, and I stopped her. I told her, it was her birthday, and I was going to give her a gift, a gift that might be awkward at first, but she will end up loving it.
Kelly said, “Hold that thought, I want to do something for you.” She had her own bathroom and went in for a couple minutes. When she came out, she used the remote and turned on her stereo. It was playing soft love music. Older stuff, that I really liked.
It was what she was wearing, and what she did that drove me nuts. Kelly had on one of her pleated skirts for school, and knee socks. But she had nothing on underneath it. She was doing a little dance, flipping her skirt up, just enough to show me her tiny slit of a pussy, completely shaved, and flinging it around in the back to show her tight tanned ass. I don’t even think that was actually her school uniform because it was too short.
It came ALMOST down past the bottom of her sexy ass. What kind of school would require that? A sex school, maybe. But, whatever. It turned me on. In fact, it still turns me on today. I wish more girls would post themselves in an outfit like that. I’d cum on my phone.
When she started dancing around like that, I think my hard on grew an extra inch. Kelly came over and started to grind my cock with her bare ass under that skirt. “I didn’t tell you, Justin…I talked to someone you may know, quite well.” Kelly said.
“Ummm, who?”I said. Kelly continued to rub her ass on my cock. “Do you remember Erin?”, she said biting her lower lip. “Maybe”, I said shifting my eyes. Of course I did. We grew up together. We fucked each on vacation. I had anal sex with her in the woods by her house, on a “Really Big Rock”.I have a story already written about her. Well, apparently Kelly knows Erin, and Kelly was always asking about me, and, I guess, Erin told her “everything”. So, I actually felt kind of like a stud. The word was getting out about me. That could be both good, aaaannd bad. In this case, it was good. That’s all Kelly said about it.
“Mmmmm, how do you like that, Justin..?” Kelly said, now rubbing my cock up the crack of her ass.
Her wetness and my pre-cum were mixing together to form a frothy lubricant. Watching that ass, going up and down her crack, feeling the slick bump of her anus on the head of my cock was just about all I could take. I put hand up her top, and played with one of her nipples. I took my free hand and put it up the front of her skirt to her warm, wet, pussy.
She stopped grinding on my dick, but sat down on it. Which was just as good. I could feel the base of my cock on her rigid, but wet, starfish asshole. As I fingered her, I could actually feel her ass constrict, and open from the pleasure I was giving her in her pussy. She started rubbing her own breasts, then put her head back and let out a few moans as I rubbed her clit.
After about a minute, she started to wiggle her ass from side to side. We moved off the chair and I told her to lie down on her stomach. She did, putting her skirt over only half her ass, and spreading her legs from corner to corner of her Queen size bed. Damn, I could cum just from the view.
So, what girl reading this, thinks that I would think, that you, have a sexy ass? Show me, and I’ll tell you. Yes, I’m just a horny storyteller. Just thinking out loud.
Her little ass cheeks showing with a clear view of her wet pussy was enough for me. I climbed on the bed. I wasn’t going to waste any time. I had to taste that ass. Kelly wanted me too. I put my hands under her skirt, lowered my head down and dragged my tongue up her ass. She immediately was into it. “Oh, God, yes, Justin”, she murmured. Again, and again I took long licks up her crack. My tongue would forcefully dip down into her bumpy asshole. Getting it wet and slick.
I started to actually suck on her hole. I put my tongue as far as I could in there. She was tight. But, I managed to loosen her up by multiple plunges in and out of her tangy ass. I loved spreading her ass and being able to see the sponginess of the inside of her ass. I fucked her ass good with my tongue.
Kelly was gripping the comforter on her bed. She just lied there with her eyes shut and her mouth agape. “I want you to fuck me Justin. You have me so turned on” Kelly said, as she took her hands, put them behind my head and made me force fuck her ass fast, and stiff. I wish I had a video. Hearing that, I got up on my knees, got over top her. She arched her ass up. Her pussy and asshole were so wet. That ass. That skirt. So fucking nice.
I slid my dick into her pussy. Kelly gasped. It wasn’t long before I was really fucking her. I reached under her and massaged her clit with my fingers. Kelly was enjoying it. She reached around and fingered her ass. In and out a few times she’d take her finger out and suck on it, and back she went as I went at a steady pace of in and out, in and out of her pussy.
“Mmm, Justin, you feel so big…I want that big cock in my bum.”, Kelly sheepishly said. That is what she wanted from the get go, from what I gathered. I think that was the reason she brought up Erin.
I few more pumps and I completely pulled out. She got up, and got on her knees, with her legs and feet under her. If I stroked my dick I could easily cum looking at her ass cheeks beneath her pleated skirt.
So motherfucking hot. Young. Oh shit! Kelly is still only 17. Well, for another 20 minutes. Oh well. We’re so bad.
I sat on my knees, with my legs spread to get under that ass. Kelly grabbed my cock and started rubbing it on her slick asshole. I could feel that familiar feeling of her anal muscles grasping the tip of my dick.
Small bounces, a little more shifting, and she slowly began to bring her ass down on my cock, while sitting on her knees, with her legs together.
I could feel the head of my dick pop thru the muscles contained in the rim of her ass, closing and opening so slightly conforming to every contour of my cock. It felt like a tight band going down my dick. It felt so good.
Kelly was spreading her ass as she continued to move down. She was making vocal noises of pleasure. Sitting on her knees, her legs together, spreading her ass, leaning slightly forward, that tight little bubble of an ass halfway hidden under that tiny school girl pleated skirt, was one of the sexiest things I have ever seen.
It’s like my cock just disappeared. She leaned forward bringing color back to my cock as she brought her body up, sliding up it. Her asshole looked it was stretching out, not wanting to let go of my veiny dick. The grip was tight. But, with all her pussy juice that ran down her legs earlier, found its way and settled into her crevice, supplying more than enough lubrication.
Just as I felt her rim reach the head of my dick, back down she came. She pumped up and down slowly for a while until her ass and her body got used to the motions. The view of my dick going up Kelly’s skirt, with her legs completely together, sitting on her knees almost caused me to blow my nut. I just had to concentrate on how it felt, rather than what it looked like, because the slow pace, at first, wasn’t enough to make me cum, but that visual, and the lust, and naughtiness could easily make it happen.
Holding the sides of her ass, Kelly began to ride my cock faster. “Oh, God, Justin, I WANTED THIS! You feel fantastic! Oh, God, why haven’t I done this before?!” Bouncing up and down as if she was on one of those big exercise balls. Slamming my cock, boring out her ass. Her outer rim muscles gave up the fight. Her inside muscles were her last line of defense, but they were giving up also. Soon, she was just riding my cock fast, making all the sexy sloppy ass sounds. Her ass smacking off the sides of my inner upper thighs, wasn’t causing a ripple of any kind on her ass. That’s how tight, her NOW, 18 year old body was. A cock, logically, shouldn’t fit in there. My dick looked like a baseball bat going in and out of her tiny ass. When a girl is that much into something, and is as loose as she was at this point, the cock sometimes pops out. Kelly fixed that without missing a beat.
My dick found its home. It didn’t want to leave either. I loved it in her ass and I knew I was about to cum all of my manliness.. The entire amount of built up cum that my testicles produced this whole horny day, needed to escape.
At this point, Kelly was leaning forward with her hands in front of her on the bed, still on her knees, just bouncing back and forth on my cock in her ass. I wasn’t doing any work, she was doing it all, and even though she was going pretty fast, I had to go faster. I took over.
I sat up, put my arms around her waist and started to really plow into that ass. My balls were slapping up against her. Kelly had tears in her eyes and wasn’t coherent in anything she was moaning. If the mystery about having your ass “actually” cumming is real, Kelly came all over my dick. We never put any other lube on, but I was gliding in and out of her chute with ease.
Her ass still felt so good. “I’m going to cum.. just like that, don’t stop, oh, Jesus, Justin, I never felt thissss!” Kelly squealed just as she clenched her ass, stopping my cock, jerking, screaming and squirting everywhere. Rubbing her clit at an amazing rate, spraying her pussy juice everywhere. This caused me to unleash a dam full of cum somewhere in her lower intestine, filling her up. Constant, split second jerks coming from both of us at the same time. Cumming together with someone is one of the greatest sexual experiences ever. It’s one you will always remember, and try to recreate every single time you have sex. It’s amazing.
I pulled my dick out, leaving the tip in and with my hand squeezed hard and milked my cock all the way up and out of my cock into her ass. Shit. We were both breathing so heavy. I could not believe her Mom didn’t hear that. I pulled the rest of the way out and some of my cum followed out her gaping, pulsating asshole. It looked beautiful with my warm milky cum pouring out of her ass. So fucking hot. I collapsed. Kelly fell into my arms. She asked if we just did that. I said yes, we did, and I told her “Happy 18th Birthday”. She smiled and feel asleep in my arms with that sexy as fuck ass right at my cock. I covered her up, and snuck down the stairs. Her Mom was in the kitchen. She said, “Oh, Justin? I didn’t know you were here? Come to think of it, I did hear ‘something’ going on upstairs. Hmm. Oh, well. I guess you two had a good time, making a connection, to still be together hours later.” She said.
I just told her, “Yes, Kelly is quite a girl.” Her Mom followed up with “Well, she’s a “woman” now”, and winked at me. I never knew which way she meant with that, but thinking about it, my instincts were right, and her Mom was drunk one night, called me over when Kelly was at her Dad’s, to look at her A/C in her bikini. This was an interesting day. One a may share with you all, someday… “
I hope you liked this! Let me know!
Source: reddit.com/r/eroticliterature/comments/d2jyoe/the_beginning_of_a_long_ride_mf_oc