The thing was, she was very young. Certainly legal, but still, I really should have been ashamed of myself. I was a thirty-year-old man, and she was eighteen. It started out so simply, though. She sent me a picture because I wrote something silly, like, “if a picture is worth a thousand words, then a thousand words must be worth a picture?”
It was almost cliché, the dorm room nude. Bad lighting, bitten lip, odd angles. There was a very immediate and contemporary intimacy about it, something both forbidden and accessible. Innocent and slutty.
She was short. Tiny, actually. A thin waist, compared to her hips, which flared out, and her tits, which were ridiculously large for her frame. It would be silly to say that I wasn’t obsessed with her breasts. Her dimensions almost seem impossible, so small and curvy all at once.
When I received the pictures, I replied with thanks and not much more. Still, the images kept popping up in my head, and I kept opening up the email again and again to take another look. I couldn’t help myself. Eventually, after looking at them for the hundredth time, I hit reply and asked if she was near NYC because I “kinda wanted to make out with you or something.” I was aiming for that specific tone, where you are comically forward, but on some level, still very serious. It was classic Jack.
She replied that she was in college upstate but came into the city occasionally. In fact, she would be there that weekend. I mentioned that I would like to meet her if she had time. Maybe just a walk in the park, maybe for a kiss.
There was something in her tone, though. Her emails were specifically vague about the who and what her trips to the city were about. Vague in that way that I knew it demanded a little more investigation.
“So what exactly do you do in the city?”
She stalled, telling me specifics, but not the answer. She goes to museums. She goes to fancy restaurants. She sees movies.
“With whom do you do all of these wonderful things?”
Ah, there was the rub. A man. An older man. Older than me and I already felt like a fiend for attempting my little seduction. An older man with children and a career and a vicious ex-wife.
Once the cat was out of the bag, the details poured out of her. She was obviously waiting to tell someone all about her secret life. She liked being a secret, but liked to tell secrets almost as much. She told me how she was his pet and his little secret and how he cuddled and kissed her, how he spanked her and fucked her. She told me about her love of being marked up and walking around sore the next day.
There was drama, too. He had many other girls he played with. He didn’t hide his other affairs from her, but she tried not to ask, and he tried not to tell. Still, when they were alone, she was all his, and for the most part, he was all hers.
The emails went back and forth, fast and furious. We told the stories of our lovers and adventures, and always she sent pictures. The vitality and exuberance of youth. She sent so many little snapshots and bits of video that her room became a familiar place, and her crooked girlish smile and lush body became things I looked forward to every time I checked my mail.
A plan was forming—an odd little plan. We were just supposed to meet. I knew she had that risque appointment, but she had a few hours to kill beforehand. We were going to go to Central Park. A safe place where we could sit and talk, nothing more.
When she got to the city, it was raining. She looked wide-eyed and shy when I met her at the big clock in the middle of the Grand Central. I said hello, and she only blushed. I took her hand, and she squeezed it hard and smiled as she followed me out.
The city was a wet mess of black and gray. The park was out. I asked what else we could do. She shrugged and held my hand, moving close, so I could feel the heat of her body. What other choice did I have? I told her we were going to my place, where it was dry. She didn’t say yes or no, really, she just followed me. I got a cab.
I knew she was short, but in person, five feet is impressively tiny. She wore things I told her to wear. Thigh highs, a skirt. When we walked to get the cab, my hand was on her waist and then her hip, and I felt around for the line of her panties. Nothing, just as I had requested. Smooth hip. I groaned as I felt her hip, and she knew that I knew.
In the cab, she was blushing.
It was too soon. We really shouldn’t have been going to my apartment. We had emailed a lot, though. I felt comfortable. Plus, she would be leaving in a few hours. Hell, she was headed uptown anyway. My apartment was just on the way. Part of me really thought that we would kiss, talk, laugh. That other part of me knew exactly what would happen. These two parts of me were often at odds. The latter almost always won.
When we got to my apartment, I showed her around. We sat on my couch, and she was shy and blushing and silent. This, of course, forced me to not be shy.
Sometimes I get into this mood where I am aggressive and kind of sarcastic and mocking. Teasing a girl about her desires and goading her into doing things.
I put my hand on her knee, and I kissed her. She turned away. Now I wasn’t sure exactly what she wanted. Maybe I was too forward. I kissed her neck, and she sighed. I moved my hand up her skirt, and she gasped. I touched the very tip of her thigh, edging near heat and wetness, but I didn’t touch yet.
I moved away and watched her squirm. Then I moved in and took a hungry handful of her breasts.
Really, they are perfect. They might be the most perfect breasts I’ve ever seen. I’ve been with girls with large breasts before, and indeed I love breasts of all sizes, but hers are perfect. I felt the delicious weight of them. I pushed her back and squeezed them. She gasped.
This whole time there was a tugging in the back of my head. She was going to see “him” and so what was I doing? I slapped her breasts a little, and she gave me one of the first glimpses of that glazed look in her eyes—that perfect combination of desire, shame, and submission.
Some girls you hit, and they like it. They squeal and laugh and ask for more. Some girls turn around and take it, like a mission. They grit their teeth and see how much they can handle. Girls like her, though. Girls like her gave in to the pain with every inch of themselves. Their groans are animal, and they are hypnotized by the pain. They don’t like it; they need it. Every connection your hand makes, or your cane or your whip, completes them, and being a part of that is something profound.
When I bent her over my couch and spanked her, she froze. “No marks,” she whispered. It was her only request. It made me want to own her, brand her, whip her until she was bleeding, but I was good. This was just an appetizer. This was our first meeting and a brief one at that. Just a little playing.
I spanked her more. I knew the lines, and I kept to them. That kind of spanking doesn’t leave marks. I watched her skin and how much she could take. When my fingers slipped into her, she let out an animal groan. The want was palpable. Her body was so primed for sex. Young, wet, tight, bright, hungry, dirty, blushing, and wanton.
My fingers searched inside of her. The differences in women are fascinating. She has a very prominent g-spot. It seemed swollen, and my fingers curved to meet the little bumps and ridges of her cunt. She bucked and ground against my hand, her body far more lithe and tight than I imagined. She was already on her way, building as my fingers moved in and out, teasing and then tormenting that spot inside of her. When her hips started a slow, steady rhythm, I stopped.
The sound she made was perfect. A moan and a whine and a begging little whimper.
When I left her, I had no doubt she would stay put. The fact was I wished I had more time and more rope because I could only imagine the things she would have done if we had the means to take advantage of her in every way. She stayed put as I got a toy and some restraints. I bound her hands behind her back, and she obediently kept her face down in the pillows of my couch. I bound her ankle together as well, loving the way the lips of her cunt peaked out from her closed legs.
The toy slipped in easily, surprisingly easily. Everything was easy with her, except for the kissing. She was eager, in body if not in mind. Her body didn’t have any of the shames or guilts her mind did. She wanted it all, and she was wet for it. Her cunt took everything I gave it.
The chemistry of affairs like that amazed me. I don’t know how everyone reacts, but I see myself changing so much depending on who I am with. She needed complete ownership. She needed me to manhandle her and be physically overpowered. She didn’t want to answer questions or play little games. Really, she couldn’t. She was as much under the control of her own body as she was under my control.
I worked the toy into her, pressing the curve of it so that it hit her g-spot hard again and again. That would be far too much stimulation for most women, but she played rough, alone, or with her little friend. I wanted to see how much she could take. It wasn’t long before her whines turned into sobs of pleasure. She turned to the left and the right because the pressure was going to make something big happen, and she wasn’t sure she wanted it to.
She got nervous when she started to squirt. The wet drops on the floor between her legs made me smile. She moved around too much, and I didn’t get to really watch the waterworks, but it is always so satisfying when they squirt, especially when they didn’t think they would.
I stepped back and was overcome with the desire to fuck her. Her wet thighs and her shallow breath. I could see her face, blushing and one breasts pressed perfectly against my pillow. Her powerlessness to her own need to be dominated was too powerful an aphrodisiac.
When I left her again and came back with the condoms, I made sure she saw them. I made sure she heard the ripping of the package. I gave her time to say no, though I knew the word wasn’t in her vocabulary at this point. She might fight, she might struggle, she might do all sorts of things, but I don’t think there was anything I was capable of that she would really protest.
She shouldn’t fuck me. She knew it. She was going to meet him. She was going to be with him and do all sorts of things for hours, but here she was, bent over my couch and saying nothing as I slipped the condom on. Saying nothing as I put my hands on her perfect ass. Saying nothing as I brushed the head of my cock against her slightly swollen and shockingly pink cunt.
I pulled up her head by her hair, and I looked at her face. She wouldn’t really look me in the eye. My cock slipped against the wetness of her. I was looking for her answer.
Then I was sinking into her—inch by inch into this new wetness.
We didn’t have time to play any more games. With her legs together and her ass in my hand, and the restrictions making every moment taboo, things were moving quickly. The pleasure was distilled and intense. She moaned and whimpered as I pushed all the way into her. Her natural tightness and the added pressure of her legs bound together was intense and wild. She was so receptive to every thrust the whole thing quickly got out of my control. I started riding her fast, pulling her thick hips back and forth, the whole time looking down at much cock disappearing into her.
She just kept coming. I was almost jealous. Just getting fucked like that, bent over the arm of a couch, plus the dirtiness of knowing someone else would be doing the very same thing in a few hours. I watched her cycle through orgasms, her body tightening and her breath going faster and then suddenly stopping for a few seconds. I was enthralled, so much my own orgasm surprised me. There was no buildup. I just started coming, so hard I fell against her and grunted three times, loud and guttural.
After I came, I played with her a little more. She was a lovely plaything. I knew she had to go, and so I let her get dressed.
After her orgasms, her whole demeanor changed. She wasn’t shy anymore. She was calm and playful. She hugged me and hung on me as I took her to the bus. Where she was once embarrassed to even hold my hand, she was pressed against me, kissing me as we waited.
These were our first real kisses. She blossomed like a flower in the sunlight outside my apartment. She pressed against me, reveling in the spectacle of us kissing at the bus stop. My hand even sneaked up to cup her breasts for a moment when I was sure no one was looking.
The knowledge of where she was going, made my feelings confusing. I reached some new place, though, some understanding. I relished the whole dirty little game. Though I was sure any meeting with her would have been intense, the situation had made things even hotter than I could have expected.
I knew as I kissed her one last time that I would have her again. I wanted her fully for a day. I would play with her like a little toy for real and see every trick she had to show me.
And then the bus came, and she kissed me once more, and she was gone.
I did get her for that full day eventually, though, in total, we only saw each other a hand full of times. Eventually, she married a wealthy older man. She married young, just like her mother. I think she saw it as her destiny.
After that, there were no more trips to the city. Not to me or to anyone. It was impossible to keep up our correspondence because I couldn’t have her. As lovely as it was to talk to her and even get her occasional dirty pictures, knowing I could never touch her always became too much. It made me angry. It made me mean.
So I had to say goodbye and cherish the memories and the little folder that ended up having two hundred pictures and forty movies. Modern memories that I could always come back to, even if it did hurt a bit to look.