Sex Files: Part 12, Holly

There was this girl, Holly, long time ago. She is another one of the few I met online and, while I cared about all of them, I didn't care about how things turned out, and or the way my life was at the time. Holly opened my eyes on a few different levels. When we met I was an 18-year-old kid working at Jimmy Johns. No path, no guidance, no sustainability towards a better life. When we split ways the first time, I was driven to do more, be more, and make more out of my life.

She was a big girl when we met. She's still a bigger girl but it's very healthy nowadays. While before, if I'm being honest, it was more of an obesity deal, but her personality was killer. We would get stoned and chill out most days, it wasn't till at least a good month or so after we met that we even got close to laying in the same bed. I did pursue but I have a certain level of respect and animosity toward her so I didn't push more than was worth it. I knew she would up and leave in a lick if I did more than she was comfortable with. As damaged as she was, she was nobody to toy with but, she didn't know it yet.

I learned a lot about Holly in a very short period of time, we talked for hours about how she had gone out of state to live with this guy, who she wound up staying with for WAY too long, being brutally mentally abused, and physically put in places she didn't feel right with. How she had a baby or would have but the stress load of her time basically ruined everything about her life and ended up causing a miscarriage. That was a big reason I didn't like to push her buttons, it was always fun but there's always a point where too far came too close. I would immediately retract and do whatever I could to mend whatever I had broken up. It usually would take a lot of cuddling and reassurance that she's more than what she makes herself feel like.

Holly would put herself down a lot, to a point where she would bring me down with her. Of course, I was already pretty down about myself and my life to begin with so, even though I wanted nothing but to make her happy and bring her up... neither of us were readily okay with life to work with one another on any level. In the meantime though, we did have a great amount of fun in the sheets when it was right. Speaking of, I think it's time for this read to dive into the time I spent the night with Holly at her mom's house a few years back.

It was late, Holly and I had been trying to get together for a few days but things kept coming up. Really late in the evening, I got a text from Holly asking if I wanted to come smoke. I had nothing better to do and I didn't work until 3 PM the next day so, I gave her a holler back after about 30 minutes or so and got the directions to her mom's condo. This place was gorgeous too. Walking in the front door, there was a stair case to the right that wrapped around up stairs where her mom and sisters rooms were. Holly's space was in the basement, which was more like a dope ass cave spot with a master bath and nice carpeting. She snuck me down there quietly, so we wouldn't wake up her mom or disturb anyone else. She showed me around briefly and encouraged me to relax in the bed while she get the bong set up. As I laid back in her queen bed, her cat approached and chilled out with us. Holly sparked the bowl and we took off. I had always been a light smoker, well, except for the few months where I was smoking non-stop day in and day out, that was a long time ago though.

So anyway, after we smoked a few bowls, I was pretty ripped and feeling like laying back with the lady. It was very interesting any which way you looked at it. I say this because, in Holly's room there was a wall of mirrors behind the pillows on the bed, definitely made for some trippy moments while we were laying back. In the meantime though, Holly got real comfortable with me laying in her bed. Crawling up next to me she threw her leg up onto my abdomen. Snuggled in close with her head on my chest, I would run my hand down her side, gently giving a little squeeze here and there. Holly would look up at me with her big doughy eyes, blinking her long dark eyelashes with a little pout on her face while she took her index finger and brushed it up and down my chest. Closing her eyes softly she would lean up, scooting herself up closer to face level. Looking down at her, I would kiss her forehead, to which she would respond with a brief "Hmph" and tucked her head back down on my chest. It wasn't long until a hand was reaching up and brushing across my cheek. It was then I reached down, pulling Holly up on top of me. She grabbed the back of my neck and I grabbed hers, pulling her in close I kissed her. When she kissed back she pulled my bottom lip out, snapping it back at my face. She would duck herself back down and roll off to the side after a short period, and when I would pull her up she would pull back. We laid there for a few minutes running out fingers through each others hair. I brought myself down to her level, then she scooted higher up onto the pillows. So I looked up at her and she was giving me this devious, little, crooked smile. It was cute, alluring, and strangely enough, got me more aroused all in one.

I'd be willing to bet you could guess what happened next, but lemme lay it out for you nice and slow.

So I'm looking up at Holly, and I got a little wood starting to peak out. She's looking down at me with this crooked ass smile and one brow raised up like she's hinting, "Come get me." I scooted myself closer to her, wrapping my arm around her while I moved up. I curled my arm around the back of her head and played with her hair while I kissed on her cheek. She took her other hand and pulled my face to her lips, kissing me deeply as I did to her. I pulled off to the side, now running my fingertips across her neck and blew in her ear a little. I could feel the chills run down her spine as soon as I did. I kissed on her neck and ran my fingers through her hair, we made out deeply with a certain lusty passionate love intertwined in every kiss. Kind of rolling around on the bed for a few, Holly lifted my shirt up and I threw it aside. I had her on her back and lifted up the bottom of her shirt, she pulled herself aside and sat on the corner of the mattress. Pulling off her shirt the rest of the way leaving me to unhook this crazy bra that had four hooks on it, and was laced thicker than shit on a pancake. God, she looked so good in it though, when it came off, my first reaction as I sat behind her was to wrap my arms around her sides and hold up her breasts, fondling them and pulling on her nipples while her moans filled the room. She stood up and pulled off her yoga pants, then leaned herself back up onto the pillows where I would creep up and pull off her black lace thong. I got up close to her, kissing her deeply while I ran my fingers between her pussy lips. Using my index and middle fingers I filled her bed with a solid puddle, then going down between her legs I dragged my tongue on the insides of her lips from base to clit. Fiddling with her clitoris while her moans got larger, I found myself in a position for her to wrap her legs around my head and push my head in with her hands. By then my face was basically coated in cum as it dripped off the sides of my mouth onto her comforter. I dug my face into her soaking wet, cum dripping pussy, drawing ABC's and the numbers 1 through 10. My end note before she let out her last moaning sigh as she drizzled another load onto the mattress.

I pulled myself back up off of her as her legs went limp and started quivering. Pulling myself up onto my knees I was grabbed, turned and pushed onto my back by Holly. As I lay there up against the pillows, Holly swooped up getting real close to my face, then dragging herself down very slowly. Slipping her nails down my chest, she reached the rim of my pants. She swiftly unbuttoned and threw down the zipper. Basically ripping down my pants at that point, I kicked them off to the side of the bed. While I reached out and grabbed on Holly's breast, she ran her fingertips under the rim of my underwear. Holding out and cupping her hand on my dick outside of my boxer briefs, she would stroke the shaft and watch in a sort of awe as my cock grew. Swiftly, my boxer briefs slung off and were thrown off to the side of the bed. I sat there, gazing down at Holly as she swooped in grabbing the base of my cock. She jerked it, slow, licking up the side of the shaft then twirling her tongue around the tip. She started to bob and twist, licking up and down with an intense yet soft grip around my cock. Jerking and twisting with a flick of her wrist, she would hold her own head down and gag on my dick like she chose it over breathing. Looking down at her as she would do this "S" motion with her head while she was pulling back off my dick, it was thus far the best blow job I had ever gotten at the age I was.

Holly preceded to prop herself up onto her knees, then crawling toward me as I grabbed on and fondled her breasts. She scooted herself up toward my waist and reached up under her, grabbing onto my hard cock and driving it into her pussy. I grabbed the base and flicked my dick back and forth between her pussy lips, watching her face as her moans coated the walls. She let out a very sexy "Hmhmmm" and then dropped hard all the way down on my cock. I'm balls deep in this girl and she is having the time of her life. Holly had probably given me the best ride ever that night. Her thrusting was so intense, with every bounce she dropped on I could feel my dick slamming against the back wall of her vagina. Grabbing onto her love handles, I would increase the force in her bounces by pulling her down while I thrust up into her. Her moans got super loud and amazingly sexy that I had to switch things up so it didn't end as quickly as she could have ended it.

It was a good thing she got tired of riding cause if I hadn't had the opportunity to breathe for a minute, we would have had a short night.

I crawled up on top of her as we set up in missionary position, throwing her legs open with her knees pointed at the ceiling. I grabbed hold under her knees as she reached down and guided my dick. Once I felt the keyhole, I jammed my dick in so deep, so fast, Holly jumped back and told me to be more gentle. I, of course, couldn't help myself so, I started to slow up a hair and then lost it. Grabbing onto her thighs I slung my dick in her so hard, so fast, she had to hold her hands on the mirror wall to keep from smacking her head on it and potentially breaking the mirror. This was when I looked up at the mirror, thinking it was kind of weird to be able to see myself fucking the shit out of this girl but in the end, it was also kind of great being able to catch her facial expressions from multiple angles. In fact, I dug it so much so, that when we switched up into doggy, I was holding her hair back and banging her out as hard as I could to make sure I caught every glimpse of change there was. I got her real hard from behind, she made me pull out for a moment so she could recuperate and try and get the sharp pains in her stomach to stop. Again when we hopped back in missionary and I threw her legs up in the air, I don't think she expected me to know where to go for it to hit deepest. Hell, sometimes I wasn't even expecting it. Each position we went to lasted at least a matter of ten minutes, or at least until one of us got tired of it and moved on to the next one.

I was having a blast, I didn't care, but I wanted to make sure she was good too so I would comply when she needed to chill. We took a few breaks in between position swaps. Which was good cause that gave my cock a moment to settle down a little bit. We were always right back at it just as hard and moving just as fast though. There was an admirable flame sparked between the two of us. Passion fueled the fire we would burn in, and even though it was all past life shit, love became a very real feeling between the 2 of us. It was damaged love, and in the future would be taken advantage of naming me off as a "STAG" cause I was down for some other shit as she was looking for a good dicking that night..but it's all whatever. The past is the past, and I digress with the future to build a better life ahead. Holly had always said she wanted a guy who had a solid head on his shoulders, driven to do more and keep out of the sleazy shit that she's now playing a decent roll in... Maybe one day she'll be back around but, until then, she's got a lot of learning to do in places I've already been.

The whole experience that night lasted a good three hours, ending with the both of us drenched in sweat, and her mattress coated in more than a few cum puddles. None of which were mine because she insisted on swallowing my load at the end, which is fine by me of course, less to clean up in a sense. I fell hard for Holly that night, but it was wrong in the long. I was just a kid, still fumbling around trying to make ends meet in a place he had no business in. Time goes on, we grow, we learn, we thrive to do more with our lives in so many different ways. It's both hurt and helped the people that surround us but, I've said it before and I'll keep on doing so... If it's right and it's real, she'll be back. If not, then it is what it is and that's how it stays. I'll remind you now that everything I say in these stories is real and actually happened to me in my travels. I have many to tell both filthy and not, so please, check out ALL of my readings and let's make the most of something beautiful.