Sex Files: Part 8, Aimee

On My Way

Sex Files: Part 8, Aimee

Back in that school I had only actually had sex with 2 girls, although there were more than a few I would have if given the opportunity. I guess you could say I actually dated 1, but for the most part, any of the girls I was with usually hung out in my bed whenever they came around. I'm particularly proud of this one though cause, for YEARS, I was the only guy she had sex with. Mostly because, after I took her virginity, she decided she was a lesbian because sex with guys hurt too much.

Aimee was another one of the girls who kind of hung out in the background, EMO fucking vampire chick. Bad attitude, really small... like REALLY SMALL. She had a body though, and for her size, it was perfectly proportioned. Her tiny figure made her perky C cups look like D's, and with her slender curves, even though I could use her hip bones as gripping points... her 0 waist stuck out and caught plenty of eyes. She always wore black, ripped up skinny jeans with pins in them, worn out hoodies with holes in the thumbs, her backpack was covered in pins and she always wore her headphones. She was very pretty, with her sharp K-9s she gave the most vindictive smile, with her doughy brown eyes she could melt your soul. This girl was unstoppable, but so emotionally imbalanced that she would kill herself trying NOT to kill herself. I know that doesn't read well but, between the lines it makes sense.

Me and Aimee didn't talk a TON but it didn't take much for sparks to fly when we did. It started slow and quickly escalated. See, Aimee had a girlfriend but she had never been with a guy, just kind of bounced around from girl to girl who was in their experimental phases. When she heard about the wild time Taylor had, she became a little more... curious, if you will. It didn't take a ton to get her in bed, we started hanging out every day, which was easy considering all she lived in the same trailer park as the rest of the people I generally hung out with. From there, Taylor's story kind of just put the icing on the cake before I whipped it out to serve.

It didn't take long before I had Aimee in my clutches, she was as fallen for me as I became for her. Soon enough, after a good little while of morning back rubs, lunch time chats, and after school closeness, I had her all to myself in my bedroom. I was ready for all of it, Aimee was unsure about it all. So we went slow, laying back with the T.V on, Aimee snuggled up against me. Laying her head on my chest, and curling her leg over mine. I'd caught her looking up at me more than a few times, but every time I would turn to her, she would nuzzle her face into my chest, giggle and then turn back to the T.V while running her fingers across my abs. As Aimee slid her hand up under my shirt and ran her fingers down my chest, I pulled her in closer, giving a firm grip on her side. It took a bit of a tussle but I got her to roll over on top of me. I watched her as she bit down on her lip, gazing into my eyes. She dipped down, reaching up under my shirt she dragged her nails down and unbuttoned my pants. I had to sit up and grab her ass while she did it, it just felt right. When I sat up she pulled up the bottom of my shirt, lifting it over my head and throwing it aside. So of course, I reached up under her tank top and unsnapped her bra so I could play with her titties. She looked at me cross, with her hands on her hips as I threw her tank top off to the side. Wrapping my arms around her back, I threw her body into mine. With my left hand around her waist, I cupped my right under her breast and gave a good squeeze while I leaned up to place her breast in my mouth. Twirling my tongue around her dime sized nipples, while I kept a firm grasp around her under-boob. Aimee pulled back, scooting herself between my legs as she ran her fingers down from my neck, over my abs, and finally peaking at the rim of my boxer briefs. She ran her fingers under the liner of my boxers, then stopped and cupped her hand around my hardened cock over my underwear. I pulled my pants down over my ass while she was arched down near my dick, so when I lifted up to get them off she got a face full of hard cock in boxer briefs. To which she responded by wrapping her mouth around the shaft of it as I kicked my pants off the rest of the way. When I leaned back, pants off to the side, Aimee quickly folded down the front of my underwear and flopped out my dick, held it at the base, looking me dead in the eye and said, "HOLY FUCK! Taylor wasn't lying." It was at THAT moment, I realized what I had become. I was a toy, but I was also 18 and had NO FUCKS to give if it didn't have to do with getting my dick wet, or paying the small amount of bills I had. So, looking back to her all I really had to say was, "Now why would she lie about that?"

Grabbing her hair up in a pony tail as she was sizing up my dick next to her face, then up next to her forearm, the look on her face was priceless. I nudged at her to give me a blowjob but, that idea didn't really last as she couldn't even fit the tip all the way in her mouth. She would rub up and down the shaft and TRY to fit what she could in there but, ultimately she couldn't get past the tip and what she did fit was being wretched on by her sharp K-9s. Needless to say, we stopped that real quick and I had her climb off and lay back on the bed. I pulled my boxers back up and climbed back on top of her. I gently kissed on her neck while ran my hands down her sides. Dragging my tongue down her neck and over her perky little breasts. I grabbed up under her left boob with my right hand and, gave it a good squeeze. Then leaning up and twirling around her nipple while I fiddled with her other using my index and thumb. I bit down a mouth full and gently let my teeth drag out until they encompassed the nipple. Holding her nipple in my teeth, I used my tongue to flicker it back and forth. Aimee's moans got ridiculously loud just then, so I reached up and placed my hand over her mouth while I continued. Gently caressing her other breast, I switched over and repeated these same actions on her other side. When I finished, I continued and drug my tongue down her abdomen, unbuttoned her pants and ripped them down. Flipping them inside out and throwing them off to the floor. She had on this neat little white thong, of course, that had to come off real quick too but first, I ran my fingers in the crease of her pussy lips watching as a wet spot formed on the outside of her panties. I did this a few more times and then grabbed waist of her thong and slowly peeled it down and off her legs. Grabbing onto the base of the shaft of my dick, I ran the tip just inside of her lips, not penetrating, but making sure EVERYTHING was stimulated. I would place my other hand on her abdomen and use my thumb to stimulate the clit while I balanced myself on my knees, still rubbing in the inside of her lips with the tip of my cock.

By the time I went to stick my dick in, there was a puddle on my bed and I was digging in if we're being honest here. I'm like the guy that's gonna MAKE SURE she's taken care of FIRST. I never mind waiting, especially when it comes to sex, I've played the game, been around blocks, ran cities if you will but, nothing compares to the pleasure like watching how much I give, and they get. So, I threw her legs up and started things off slow but escalated it quickly. It was tough trying to get my dick to fit inside. I could tell every millimeter hurt her SO MUCH but, when I asked if she wanted to stop, she would grip onto my sides with her nails and blurt out a hefty NO! Practically tearing into my skin pulling me forward. She would tell me not to worry about it and just to go for it. So I told her to brace herself, grabbing onto her hips I etched it in bit by bit with what I would consider half thrusts. Not so powerful but enough to get her to jump back while I worked it in. I got about a quarter of the way in and we decided it might be easier if she was on top first so, I rolled over onto my back and she got herself ready to climb up on top. She was really hesitant about it as she was a virgin at the time. I wasn't surprised in the slightest but DAMN, she was SUPER tight down there. She loosened up after I got a few in but the whole time she was on top, she just looked SUPER uncomfortable.

It started REALLY slow, Aimee was basically crouching over top of me, holding onto the base of my dick trying to line it up. Again, we made it about a quarter of the way in and she jumped up. I held onto her hips the whole way down and every tiniest bit down she went, her legs started shaking more and more rapidly. FINALLY, she got about 3/4 the way down and bounced herself RIGHT BACK OFF. Said she couldn't, it hurt too much, so I suggested that we go back to her laying on her back and, we went for it. With her on her back now, I went back to sliding my tip between her lips. Watching as she's dripping out the sides I grabbed onto her hips and said, "Hold on tight." Before she could get another word out I threw my dick in so hard when she jumped back, her eyes popped out of her head, knocking her dome off the wall behind her. I, of course, was going so fast, kind of just watching her with her mouth gaping and her eyes bulging out of her skull. I stopped briefly, not just cause I was running out of breath but, I realized Aimee wasn't breathing herself. She caught her breath with a HUGE inhale followed up by a lot of panting. I asked her if she was alright and I got back silence. She let out a hard exhale and finally said, "Yeah, just do me a favor. Not so rough right off the bat please?" I laughed and looked down at my dick, which was covered in bloody cum. I panicked for a quick second, looking back at her saying, "Shit. I think I broke you." Of course, she laughed and replied, "Well no but, you definitely popped my cherry though," as she smiled up at me. Relieved that I didn't break her, I gently slid myself back inside. Using my arm as a kickstand, I grabbed hold of Aimee's waist and slowed up with my thrusting, trying to be gentle as I went. She looked up at me like it wasn't good enough so, I sped up a little, went in deeper, watching as she bit down on her lip and mentally lost it. Pulling on the pillows above her, reaching out to, what felt like, etch her name in my back with her nails. The only thing she didn't do was scream but, she was so short of breath that that much didn't have a chance to come out. As I went faster I realized I had to stop every so often to make sure she could breathe. I had to switch things up, we had been going at it for a good solid 45 minutes or so, my bed was soaked, and I was running short on energy.

I tried holding her legs up in the air by her ankles while I thrust but, when I went in, she shouted "OW Stop Wait!... That's too much can we try something else?" So I switched her up into doggy style, got in real close, grabbed onto her hips and started at a slow comfortable pace. I can't lie, I got a little impatient and sped it up real quick. Slamming her ass into my pelvis while I thrust hard and fast, I could feel my dick capping out the bottom of her stomach. This went on for a good 15 minutes until the build up finally arose. After a good pause on my end, where I stuck my dick in all the way, grabbed hold of both her breasts and just breathed for a moment, I could feel it coming quick so I pulled out, flipped her on her back and laid my dick on her stomach and, watched cum shoot up across her stomach, on her tits, I almost got her in the face. It was BEAUTIFUL.

Turns out I ripped Aimee wide the fuck open, and bruised her internally. She had problems walking for the next week but, we decided it was all worth it in the end. Thus continued the legacy of "Chief Horse Dick." I met up again with Aimee a few years later, we both were going through some things but, that's definitely a story for another read. Which, I hope you continue to do. This is my life, and there's been a LOT of it in a short amount of time.

Read next: 9 Non-Pornographic Films Starring Pornographic Actresses
Zachery Lee

I'm just a loner kid who's been through some things in his life.I have mountains of stories to tell, if your willing to read, I'm always willing to share.I hope that my stories inspire, and maybe even teach you a bit of something about life

See all posts by Zachery Lee