Jen’s Journal [mf] [broken girl] [first time] sex stories

This was the worst day of my life. A month ago I felt like I was invulnerable like I could fly if I just jumped a little higher. Life was just so fucking cruel, to gift me with love, after waiting for it my whole life, and then just snuffing it out was the frosting on the shit cake life served up for me yet again.

Jen had moved in next door to me when we were both five and instantly became my best friend for the rest of my life. We played games, watched TV, even innocently learned about the difference between boys and girls hidden in my garage when we were eight. Naturally, she called me her boyfriend when we were eleven, and both our parents thought it was cute. Then something happened. Her parents got divorced and she had to move away with her mother.

We kept in touch, mailing letters back and forth, first every week, but eventually that dropped down to once a month or so, but never stopped. That whole time we still talked about someday getting together again. In highschool we agreed on the same college so we could get together again. Sure, there were other girls in classes that I became attracted to, but I already had Jen waiting for me.

It was like she could tell my urges were overpowering my devotion, as her next letter came with a picture of her and her mom in swimsuits complaining about how ‘cold’ the seventy-degree water was today. I’d never tell her the shameful way I visualized her, put dirty words in her mouth as I played with myself alone in my bed, wishing she were here with me so I could show her my love. Instead, I sent her back a picture of me in my swim trunks in front of the wall of snow outside and wrote a joke about how the water was still ‘a little cold’ up here.

I don’t know how we endured up to this point, but we had. Three months ago we got into college together, just as we’d planned, and it was so weird seeing her again for the first time in what felt like half a lifetime. I had imagined so many times that it would be just like a romance story, we’d kiss, and fade to black, happily ever after, and all that. Sadly it was a little more awkward.

The last six years had changed us, and I was so nervous I tried to hug her, and she seemed scared, so I didn’t. I wanted to kiss her so badly, she looked so beautiful, but I could tell she needed time. School started busy, so we took things slow, but every minute of every day I was in her room, making up for lost time. Fuck, I wanted to touch her so bad, but I held myself back, waiting until she was ready.

We watched TV and did homework together, just like old times. I thought things were going well, yet every time I innocently touched her she’d flinch. I didn’t know why, but I could tell she didn’t want to talk about it, so I tried to avoid doing it, fighting back so my natural desires. It was maddening, being so close to the one you loved, only to be kept at arm’s length. Two full months passed before she finally opened up to me.

The reason her parents divorced was because her father got caught abusing her. Maybe my parents knew, but I was sheltered from that part of the story, and Jen never talked about her dad with me. I was her escape to normalcy, the perfect friend and platonic love. I wouldn’t hurt her in any way, and she needed that. I recoiled, hating myself for wanting to do exactly what her perverted asshole of a father did, and that just made me even more confused and angry.

For a week I wrestled with my love for her and my teenage desire. Rationally, I knew everything in my head was due to hormones, but that didn’t make resisting them any easier. I promised her I’d never hurt her, but still wanted to do so many things I’d dreamt of doing for so long. Fuck, why did this have to go all wrong, just as it was going right?

I couldn’t stand it, I needed to break through to her, make her see that I wouldn’t be like her father. I’d never hurt her, and that my love for her was pure. We were in her dorm room sitting on her bed a few feet apart watching TV. It wasn’t yet so late that her roommate would be back, so I made my move and put my arm around her. She resisted just a little, but it stopped when I pulled her closer.

“Pleaseā€¦” she gasped, and I fell into her beautiful brown eyes, with just a few flecks of green, and I could tell she wanted me. I took her acceptance of being in my embrace as permission to continue, leaning close, bringing my lips to meet hers for the first time.

It was like a flood let loose, and all my desires for her were suddenly reflected at me tenfold. Kissing soon involved her tongue in my mouth, and buttons getting ripped off of my shirt as she tore it open. I pulled her shirt over her head, and she attacked my pants, pushing me on my back.

“We shouldn’t,” Jen sighed, but that didn’t stop her. The rest of our clothes didn’t even matter once my penis was freed. She looked like a strange goddess, still wearing her bra and skirt in the dark, only illuminated by the color-changing light of the TV and lava lamp she used as a nightlight. A viewpoint only further enforced as she adjusted her clothing so that when she mounted my lap she took me inside her.

I’d been wanting to do this with her for as long as I’d had erections, but for it to happen still felt like a miracle. The softness. The tightness. The wetness. It was everything I’d ever dreamed it could be and more. I tried to hold on, ensure that she enjoyed it as much as I was, but it was my first time and I was over-excited. Five minutes was all I could endure before my body convulsed inside of her. She got off my lap and fixed her clothing.

“Oh, wow!” I gasped in joyfulness, but Jen quickly left without a word for the bathroom. I hoped I hadn’t disappointed her too much, but I was in too good a mood to regret it. She came back fifteen minutes later, assured me that everything was fine, but she was tired now and needed some sleep. I was ushered out and practically skipping back to my room.

After that, our dynamic changed. Sometimes I would only just get in her room and she’d attack me, giving me blowjobs, or just fucking her right off. Almost every minute I was alone with her for almost a month was spent connecting with her through my loins, and I was in heaven. It’d been everything I ever wanted and more. It was my dream come true, only now in retrospect did I know it was the end of our relationship, not the beginning.

But yesterday I had walked into her room to find her in bed with another man. I was pissed and angry; calling her names no one should ever be called, but this massive betrayal just couldn’t stand. It justified every vile word I used to degrade her and more. I should have just left when her lover did, but I wanted to fight. How could the woman I loved my whole life could do something like this to me?

“Who do you fucking think I am?” she screamed at me. “I’m a fucking slut! I’ve spread my legs so many times, I’ve lost count of how many guys I’ve fucked!” That couldn’t be true, could it? Nothing made sense anymore. Jen pulled out a box from under her bed and extracted a worn black journal, crammed full of papers, but had one of those little elastic bands sewn into the cover to hold it closed. “You’re just like every one of them! Just a fucking man that wants to fuck me!” She screamed, pushing me out of her room, hitting me with the book to back me up, and then threw it at me before she slammed her door shut.

I was so confused and hurt. I pounded on her door, demanding she open it and talk to me. I could still hear her crying inside until she started blaring loud music, but her door stayed firmly locked. Some heads started peeking out of doors all up and down the hall, so I picked up the strange book and left. I didn’t even really look at it until I got to my room again, then wondered why she threw it at me.

Inside were many of the letters I’d sent her when I was younger, and the pages filled with her writing like a journal. Turns out she had viewed me as the one boy that was happy to just be her friend and not try to fuck her, and that was what she’d liked about me. There were my letters tapped on every page, and her talking about the most recent guy she fucked, often a complete stranger, and how she had to lie to me about who she had become to keep me as a friend, thinking I’d hate her if I knew who she really was.

The more I read the more I realized how much I’d fucked up, but also how much pain she was in. I spent the whole night reading her confessions of using her body to please men, sending her into all manner of depraved sexual acts. She didn’t say it, but I could read between the lines; this was her foolish attempt at trying to feel loved like her asshole father had messed her up doing. But only my letters and innocent and undemanding friendship had given her what she needed, until now.

Without sleep, I wondered what I should do next; what I could say to her? I loved her, and while I’d forever cherish making love to her, I knew she needed me more like her friend than anything else. But there was no way I could see her every day and not want to touch her again. That made what I had to do painfully clear.

By morning I had packed up everything and was ready to leave. I stopped by her room but didn’t knock, just set a box down in front of her door and left. In it was her journal with my letters and a new one that simply said ‘I’m sorry. I love you. Goodbye.’ Luckily we were still before the cutoff point for the bulk payment for the college, so I was able to drop out and still keep almost twenty thousand dollars in the college fund my parents started for me. I hated that I wouldn’t be using it as they intended, but it would get me by for a while.

Maybe after getting a job somewhere I’d try college again next year. Anywhere else, it didn’t matter. All I knew now was I had to do the one thing I swore I’d never do once I saw Jen again, and that was leave her. Once I was settled far from here I’d send her another letter, see if maybe we could get back to where we used to be, if I could somehow get things back to being right between us. I didn’t know if she’d let me, but I had to try. I loved her too much not to.

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