SexFiles: Part 3 (Brittany)

On My Way

SexFiles: Part 3 (Brittany)

After Savannah, I was broken, I spent a while in and out of Juvi, found myself in a mental hospital on more than a few occasions, and basically gave up on love altogether. Then, I met Brittany. It IS kinda of messy how this all started with her, and I was older by a few years than she was. I was 18 when me and Brittany started fooling around, she had/has this childlike innocence that easily masks all of the pain and agony that she deals with on a daily. She's definitely someone who tends to try and find herself in other people. Now, at the time, I actually did care a lot about this girl. I was so blinded by having her around that I would even put myself in a position to be walked all over. She did mistreat me, but I took her purity and in that, she kind of just went crazy, became a slute for a while, and wound up with a daughter that she had to drop out of school for. This would be the story of WHEN I took her virginity.

Brittany is a very small girl, she has a bright smile, ungodly curves, and she always had her nails and makeup done up. She's not much for soaking herself in makeup anymore, but she was, and is Naturally beautiful. Standing at roughly 5'2... ish when we met, with a D cup bust, NOTHING that she said and or did could throw me off. We decided to make a note of her coming out to stay with me at my moms house one night, mom was out with the kids. Brittany and I were watching a movie and got caught up in talking through all of it, I held her close to my chest and we more or less just laid there for a while. I was feeling the moment so, I picked her up, and sat her back down in between my legs, sprawled out on the couch. Wrapping my arms around her, holding her tightly as I caressed her sides and played with her hair. She reached back, fairly hesitant of the whole thing but, reached behind my neck and ran her nails down the sides and around the back. I kissed her ear and blew on her neck, she stopped. Turned and looked up at me to say,

"You know, I've thought about this a few times..but I don't know if I'm ready for it."

I smiled back and said,

"Hun, you got nothing to worry about though, I'll take care of you."

-Mind you, it wasn't just a whoop swoop and pull between me and Brittany. I had put up with SO MUCH SHIT from her. Between the hours of phone calls, I stayed with her at her dads a few times to keep her company so she wouldn't feel so alone while her dad was out neglecting her for his new girlfriend..I went with her to this dance, carried her purse AND shoes, held myself up from BEATING THE LIVING SHIT out of more than a few kids for calling her slut/whore/skank ect.. Sitting with her on random occasions listening to her talk about how fucked up her home life is, and how she just wanted to escape everything. I actually put in the time to get to know this girl, inside and out BEFORE ANYTHING. We had/have history together, she just wasn't ready for the commitment I was down for. Anyway.

Sitting on the couch with her in my arms, I'm reaching up her shirt and squeezing on her breasts. She was wearing a pink, fuzzy, thin long sleeved shirt, with some skinny jeans that swayed perfectly with her hips. Snug enough to make me want to take a bite out of her ass. When she would tilt her head back and give me that smile, my heart would melt. Batting those long lashes at me, just made me want to attack her. Cold blooded BUT, I do respect women so, I couldn't ever really bring myself to do anything that would technically be considered RAPE. So, I endured. Continuing to kiss on her neck and, rub down her sides. Squeezing her bra and, lifting the bottom edge to get a good feel on her nipples. I blew on her ears just enough to get her to snap up. she would playfully say,

"Would you stop it, you have NO IDEA what you're doing to me right now."

I obviously had to respond with,

"Oh yes I do, but if you REALLY want me to stop, I will."

She just smiled and laid back, whipped her hair in my face and sat forward. She started grinding on my jeans, so naturally, I grabbed her hips and picked her up onto my lap. She stood up and turned around, straddled me like a horse and started grinding on me again. I grabbed her ass, and preceded to run my fingers down the back of her jeans. She dipped in and kissed me, deeply and full of passion. I grabbed her neck and pulled her in closer. We made out for a good 5 minutes or more, I pulled up her shirt and dragged my hands down her back and sides. Putting just enough pressure to get a rise out of her. Her soft subtle moans got a little louder with each stroke she made in grinding on my lap. Even more so when I smacked her ass, she would jump a bit each time I did. I would pull her in and kiss on her belly, feeling up her sides and running my hands under her bra while I did. I was ready to go, but she was still on edge about all of it. I stood up and tossed her down on the couch on her back. Brittany sat up off the couch and, lifted the bottom of my shirt up, running her nails down it as she stared intensely biting her lip. Completely ignoring the TV so, I shut it off. There was no space for us to go upstairs so, I picked her up and walked her into the spare bedroom where, I laid her down in the bed. I lifted up her shirt up and over her head, she bonked her head on the railing when she flung herself back. I had to stop and laugh for a moment, trying to muffle it as best I could, but low and behold, I burst out dying. She of course, was holding the back of her head, laying there in her pinkish/beige bra, laughing at herself as she hit my in the stomach for laughing at her. I leaned in, and kissed her on the forehead, then ran my fingers down her side. Kissing her cheek and down her neck, she pushed me back and grabbed on the bottom of my white t-shirt. Laughing as she spurted out,

"If mines coming off, so is yours."

I just said,

"Okay, I think we can do that."

And lifted my shirt up over my head and tossed it on the floor next to hers. She ran her hands down my abdomen and, pressed her nails into my sides as she tried to grab my waist. She followed the "Sex Lines" down and pulled on my pants. Going for the zipper I paused her, moved myself down toward the end of the bed, grabbed her ankles and pulled her down so she lay flat. I crept back up to her face level and ran my tongue down her neck, between her breasts and over her bra strap; Down her belly and bit her pants. I unbuttoned her pants and pulled the zipper down, revealing her white panties. They were nothing special, but she was so it didn't matter. I pulled them over her ass, had some trouble with it so, I went down to her feet and tried pulling them down from the edges. Very quickly I got tired of trying to get them off so I just yanked them down and inside out, they got stuck on her feet though so, she laughed and plucked them off herself. Off went her underwear to follow, the then gave me the sassiest look and said,

"Alright, it's your turn, drop em."

I laughed, stood up and said,

"You do it."

She jumped up, kneeled down and ripped open my pants, throwing them down around my ankles. I slid my pants the rest of the way off and tossed them to the side next to hers. Leaning back in to kiss up her thighs, grabbing around her ass and spreading her cheeks from the back. I pulled down her underwear and tossed them off to the side, that's when she really started getting a feel on my dick. She grabbed it through my boxer briefs and started stroking it, while she was sat up, she slid off her bra and threw it aside. I pushed her back on the bed, grabbing under her tits for a good squeeze while i dove in and licked around her areola. Twirling my tongue around her nipples, I would give them a little bite and kind of tug on them with my teeth. wrapping my mouth around her breast while I played the other like a violin, sucking up her nipple and leaning back, dragging it out until I got to the tip; Where I would clamp of with my lips and sometimes drag it out with my teeth. Just enough impact to make it sensual, but also adding the slightest bit of pain to make it orgasmic. She would moan load and hard, arching her back and scraping down mine as hard as she could. I bled a lot that night, literally bleeding out of my back by the end of this but, it was pretty worth it if I say so myself.

So, we're both laying there, I'm on my hands and knees, basically hovering over top of her, kissing and playing with her perky, full breasts; While I'm playing with her clit and slipping a few fingers in and around her tight little virgin pussy. She pulled down the front of my boxer briefs and gazed on my fully erect, throbbing cock. She grabbed it by the base and slowly slid her hand up the shaft, bringing her other hand in to play with my ball sack while she did. I laid to the side and slid my underwear the rest of the way off and climbed back over top of her. When I did, she grabbed back onto my dick, so I grabbed back onto her pussy. Putting 2 fingers in, and holding her with my thumb pressed up against her smooth, shaven pussy. She squeezed a little harder than I was ready for in reaction to the grab so I got a little rough with it. I let go of her vagina and threw her legs up over her head. She abruptly stopped and looked me dead in the face, FROZEN and uttered,


(I didn't know she was a virgin at that point)

Awestruck, I looked her in the eyes and said,

"Well shit, I guess just lemme know if it hurts too much."

We both laughed and I preceded to rub the tip between her lips, sliding it up and down, watching her face go from "OH FUCK" to "OH MY GOD". I slip the tip in and she seized up. I could feel her squeezing my dick with the muscle inside of her, she got so tensed up I had to pull out real quick. She snapped at me,

"Why'd you stop? I didn't say stop."

I said,

"It looked like I was hurting you."

And of course she comes back with,

"YOU WERE BUT, like the good kind of hurt. just, don't get too crazy with it ok."

So I went back in, letting her legs go down to the sides. I got about 3/4 of the way inside, and she started almost shouting, (as she covers her mouth)

"OW OW OW OW OW FUCK! Keep going, don't mind that!"

So I kept to a steady, slow thrust, only putting about 1/2 of my dick in. Stimulating the clit while I was inside of her, I watched her seeping juices out onto the bed. I had to pause, get up and grab a towel so I didn't have to worry about getting steam rolled when mom got back home with Barry. I came back and laid the towel down, kissed back up her thigh and slipped my dick back in. I put all of it in this time and as soon as I hit the back, I saw a bit of blood on my dick when I pulled out. I froze. Stuttering out,

"Uhm, you're not on your period are you?"

She said calmly,

"Nooo but, you DID just pop my cherry though..."

I had to pause for a moment cause, I REALLY wasn't expecting that.

"You'r- were a virgin?"

She just smiled and nonchalantly batted her eyes and said,

"Yep, that's not an issue is it?

Wide eyed I say,

"No, no no no, no it's cool I uh, just wasn't expecting that."

"Well, now you know right, so can we continue?"

I laughed and slid back in, she grabbed my back and scratched down it REALLY hard. I cringed, and that made me go in even harder. She let go of my back cause, I kind of hurt her when she did it. Brittany looked back up at me and told me to keep going, that she would be okay. SO, I went back to slow thrusting, she got REAL into it, grabbing on her breasts and biting down on her lips. Letting out SERIOUSLY sexual moans, she plead out

"Faster, faster! Harder!"

I went for it, and threw her legs back up over her head. Holding her ankles I went in as hard and as fast as I could go right off rip. She was basically screaming at this point, so I had to get her to bite on the pillow and, instead of killing my back with the nails, she grabbed onto the sheets. That didn't last too long though and she was quickly back to digging into my back. It sped up and slowed down for a good 20 minutes, I got bored so of course, I had to switch it up again. Trying out the scissor move again, Brittany wasn't digging it too much, so after about 5 minutes past, I went to doggy. Grabbed her hair up into a pony and started railing her from the back. She dug her face into the pillow and screamed her little heart out, pulling the covers off of the bed trying to get something to dig into with her nails. Repeatedly yelling

"Fuck, Fuck, Fuck me fuck me ffuuuck mee!"

It went on like that for a great added half hour, my legs got extremely tired, so I tried to convince her to ride. She wouldn't at first, but I got her on top for a very brief 5 minutes. She didn't like it too much so we went back to missionary to finish things off. I dropped everything I had into the last moments of this ride. This is where we found out my back was bleeding. She dug her nails SO DEEP into my back, that I really did feel her pain when I SLAMMED my dick so deep inside of her and watched her freeze up without a breath to be had. I pumped a good 10 more times feeling the build up and trying to get the most out of it. Watching her moans expand, and her tits bouncing, I really didn't even want to pull out. I let out an enormous sigh of relief as I blasted Brittany's stomach and chest with a massive cum shot. Surprised her about as much as it did me.

I wiped her down with the towel that we had in the room, snuggled up with each other and laid back in each others arms. Smiled and laughed at all of it, slid back on our clothes and went back out to the couch to cuddle up with the TV again. Me and Brittany have touched base and fooled around on a few other, more recent periods in our lives..but it's more than likely never going to go any further than that. We've talked about moving in with each other and having a family to build on..We almost had a child of our own too, but the universe works in kind of fucked up ways...It is what it is, and there will always be a piece of me that has some kind of love for her, but we both have learning to do. I think too far ahead, and she lives in the moment more than it's worth. Anyway, enough of that sappy shit, this is where I'll bring the article to an end. I hope you've been entertained, I have a lot more of these to go off of, in both stories, and SexFiles.

Written and lived by: Zachery Lee

This is part of a series. Check out the main series of "On My Way" over on Families here!

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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

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