writingdirty

Dirty stories by Jack Stratton

Tag: sex (page 5 of 5)

Getting to the Point

In trying to write a dirty little story with Miss Lilly from DangerousLilly I find myself being far too verbose for my own good. I can’t just jump into the action, I tend to get caught up with characters’ back stories and motivation and all that. Not that these are inherently bad things, it’s just that when you want to write about fucking and you spend 2 pages just getting to someone’s panties you have a problem.

Maybe I need to read more erotica. I went through a phase where read a lot of it. I had around ten of those Best American/Womens/Lesbian/Southern Erotica of 2000. Not to mention the essentials of Anais Nin, Venus in Furs,, The Story of O, what have you. Even the unbecoming Sleeping Beauty series and Belinda. I’ve been on the outs with published erotica for the past few years though. Reading online erotica from places like Literorica or StoriesOnline can be a mixed bag. You get some wonderful things but more often then not you lots of horribly written garbage. Often when you do get well written things they are far too dirty for their own good. This prickles my propensity to pen far to perverse things so I try and steer clear. Thus the reason I try not to read ASSM/ASSTR anymore.

I’ve sort of trained myself to write in a certain way and when I try and write straight sex my head gets confused and keeps yelling “who are these people and why are they on a train?”

Sadly this leads to a folder with dozens of sex stories with no sex in them.

That being said… does anyone have any kinks/scenarios/wet dreams/ideas they would want to read a story about?

Fiction – The Wrong Smith Girl

They broke up on the train.

Trains push his memories to the surface. All the trips into the country as a child. All the trees passing by, leaves changing to red and gold.

The city fades fast, faster then you can imagine. It is so small compared to the stretches of country to the Jersey Shore, to Upstate, to Boston and Maryland and DC.

Looking at Maggie, he could see her fighting her childhood memories. At least he wanted to think she was fighting them, hoping they were there to be fought. She had her nose in a notebook, making a list of things to do.

They were going to Maggie’s parents’ house because Maggie’s father was sick. He had a heart attack, but it looked like he was going to be alright. She had a big Irish family and it was expected that a good daughter would come home in a time like this. So Maggie and her boyfriend Jack got on a train from New York to Virginia.

Maggie and Jack had been living together for three years. They had been dating for four and known each other since college six years ago. She was going for her BA in Fine Arts and he was going for his Masters in English back then.

She had their life planned out. She had a good steady job and he did freelance work. They had a nice apartment, which he loved, but she wanted to move out to the country soon. She wanted to get married, but he hadn’t asked her yet. She had plans and he wasn’t playing along. She didn’t break up with him because she had already put too much time into him. He didn’t break up with her because he was lazy and didn’t like confrontation.

There was something about the trip that started pushing Jack’s buttons from the start. They were taking the train out to her parents’ house and there was this air of expectance. She expected him to go, to be excited, to ask her to marry him, to want kids, to want a better job… but none of that was going to happen and both of them were starting to realize it.

A third of the way there after arguing over signing another lease for the apartment she said “If you don’t want to grow as a couple then maybe we should just break up.”

It wasn’t a threat, it was something that people said in the heat of the moment, but it just pushed Jack over the edge.

“Yeah. We should. This relationship is a joke. You don’t love me; you just need someone to help you afford a mortgage.”

And she cracked. She cried. There was no putting things back together.

For the next hour they agreed on things. Jack would be nice for the three day weekend with Maggie’s parents. They would take care of the breakup when they got back. And then like a switch when they got to their stop Maggie fixed her makeup and was back to herself.

*

They entered the big old house just after 4pm. It was an old southern house with white pillars outside and a big porch and a huge white door.

They entered to find silence and emptiness. Walking up the staircase they came to a long hall. Pictures hung along the walls, old school pictures of Maggie and her sisters Molly and Megan. Three smiling girls with white skin and black hair and matching skirts and sweaters. Three princesses at Halloween. Three girls on horses.

Jack followed Maggie as she navigated pass a dozen doors and finally found her old room. Jack was a stranger in this place. He was not a Smith.

Maggie’s room was white walled, filled with 2-foot boxes in one corner, an uncomfortable looking bed made up with yellow sheets and a pink and yellow quilt. One wall was all white bookshelves, but they were only a quarter filled. On one wall hung a large framed sketch of Maggie. He remembered her sitting in front of the mirror, sketching herself for her final project in still life, back in college.

In that frame was Maggie, the girl. Quiet in class, but boisterous when she was excited. Level headed, list making, but deep down an artist. Deep down filled with the same curiosity that Jack was filled with. Curiosity about books, history, art… and sex. The more he remembered their college years the more he realized that the Maggie he knew was gone.

When did she start longing for mediocre satisfaction? When did she stop needing to explore and started needing a bigger house, a better job, some mythical security she constantly talked about. When did she put her paints and her charcoal and her pads and canvas in her parents’ basement to go untouched?

The same time she started thinking of sex as a duty and rolling her eyes at the mere mention of sexual adventure. Sex was just relieving them both of some energy or maybe a way for her to get him to leave her alone so she could get enough sleep to wake up at 5 in the morning to jog.

She sighed and put her bags down.

“Listen, you can stay here. I will go to the hospital. Then everyone will come back for dinner. I know you don’t want to be here… but let’s just do this and then we can get back and…” she just trailed off. A horn honked outside and she looked out the window.

“That’s my aunt. Unpack, ok?”

Jack nodded. “I like your family. This weekend will be fine. Go check on your father, make sure he is alright.”

She looked at him, unsure if a hug was still ok. Then she just turned around and left.

*

He unpacked, he looked around. He ended up on the bed, drifting off into a nap. The train ride, the fight, all of it melted away.

When he awoke in darkness. He could hear people downstairs and smell the warm homey smells of chicken and potatoes.

He saw movement, the door opened and closed.

“Hey. You ok? Sorry I fell asleep… the fight and everything…”

“I don’t think your talking to the right Smith girl, mister.”

The light came on and that’s when he found out Maggie’s little sister grew up.

She was Maggie, but different. Shorter, but only slightly. Bustier, a little more hip, a little more ass. Same nose, same ears, fuller lips. Her eyes were blue, while Maggie’s where green.

“Molly.”

“That’s me.”

The last time he saw her it was about four years ago, she had just turned fifteen. Sitting up fully he couldn’t quiet comprehend that it was the same person. Molly the Mole, skinned knee tomboy who made gagging sounds if she saw him kissing her sister.

The first thing he noticed was a red and black nautical star tattoo between her neck and her breasts, half hidden by her white cotton tank top. Half perfect black and red ink on her white skin, half dark shadow under the thin cotton.

“Nice ink.”

She squirmed under his eyes. “Thanks.” Her arms came up and she folded them over her breasts. She was trying not to smile.

“So you two having a fight?”

“Um. No. Not really. Just an argument. Sort of.” He knew he had to look away from her, but he couldn’t. It was like looking at all the missing parts of Maggie, melted into a younger curvier tighter form. He walked over to the window and looked out at the greens and the grays.

She came into the room and walked to the bookshelf, looking at the remaining books, letting her finger drift over the spines.

“I was wondering what you would look like now,” she said. He could hear the smile in her voice.

“Oh? Do I look different?”

He looked over to her and she nodded. “You look old, but basically the same. You look better with your hair short. Your hair looked pretty dumb long. Plus those glasses are better, the dark frames. You’re still ugly, though.” There was the smile, the wicked brat smile. In those eyes was pure curiosity.

“I always thought you had
a crush on me.”

She let out a laugh, but she blushed.

“You wish.” she said, but eyed him and smiled.

He looked at her from the side now. It was like a lecture on the effects of puberty. At fifteen she was all legs and arms and wild nervous energy. At nineteen she was all hips and tits and calm sultry sex.

He noticed other tattoos, one on her wrist, this one just a black star. He could see the shadow of something on her back, it was large and not one of those little designs girls get right at their tailbone, this was long and it came up from around her butt to the middle of her back.

He stood up and moved closer to her, slowly and she tensed. She was still facing the books, pretending not to be curious about what he was going to do next. He walked behind her, moved closer until he was two feet away. He looked at the books, he looked at her neck, he looked at her eye as she turned her head to look at him.

“You got a tattoo on your back, too?”

She nodded, still facing her body away from him, but looking at him from over her shoulder.

He moved in and put his hands on her waist. She froze. He touched the edges of her thin shirt.

“Can I see?”

She swallowed and nodded. Their eyes met. Curiosity, lust.

He pulled up her shirt slowly and saw that there where two jet black f-hole, like the ones on a violin or cello. It was a lot of ink, a lot of time. He touched the edge of it and he could feel raised scarred skin.

Her back was smooth and her ass curved out from just below his hand.

“Wow. You got all this done in the last year?”

She moved forward, pulling her shirt out of his grip.

“Yeah. I was dating a tattoo artist for a while.”

He took her hand and looked at the tattoo on her wrist.

“Did they hurt?”

She smile. “That’s the best part.”

A voice from downstairs said “Kids… dinner.”

*

Dinner was huge and southern. Jack had forgotten that people ate like that. Fried chicken and mashed potatoes, greens and a million other things. Everyone was so busy catching up with Maggie and Molly, who had been off at Art School and also with Maggie’s older sister who had just had twins that no one really bothered talking to Jack, which was just the way he liked it.

Molly watched him though. Watched him like a cat watches a bird. It was a very different look then the fifteen year old awkward kid gave him four years ago.

When it was over Maggie said goodnight to all and went upstairs with Jack, got undressed without looking at him and then went to bed.

Jack laid there, uncomfortable because of the small bed and not really wanting to be too close to Maggie. He found himself thinking of Molly every time he closed his eyes. The way she looked in that white tank top, tough and sexy. He wanted to know what those tattoos looked like up close. What it felt like to trace them with his tongue.

Thoughts like that and the moonlight coming in from the window kept him up half the night. It seemed like only minutes, but the next time he opened his eyes it was morning. He awoke to feel the familiar sensation of Maggie next to him. He had turned around to face her in the night and now he was spooning her, with his arm around her.

She felt warm, she smelt good. Her ass against him made him stir inside. Without really realizing, his hand came up to cup her breast. It was such a natural thing.

She sighed and pushes his arm away.

“Yeah, right.” She said with disgust.

She sat up and climbed over him.

“Go back to bed, I’m taking a shower. Everyone is going to go to church in an hour. I know you don’t want to do that, so I’ll probably see you at lunch.”

She looked him in the eyes.

“Shave, ok?”

He nodded. He was still hard under the warm sheets. Memories, warm blanket comfort and the smell of her hair on the pillow made his mind swim. If he just relaxed he could fall back asleep. And then there was nothing.

*

He awoke to the sound of the door closing.

The room was too bright, the sun coming in through the half opened curtains. He was groggy, as only waking up from oversleeping can make you. The room was a dull white blur, then the blinds were closed and the curtains pulled shut so that the light filtered through the rust colored fabric, making the room dull yellow and red.

Then Maggie slipped into bed. Her arms around him, her lips on his neck. He pushed her hair back and kissed her. Her lips felt soft, there was some sweet lip gloss… and then he opened his eyes wider and saw who was really in bed with him.

There was Molly. There was Molly in her white tank top.

“Hello mister bedhead.”

He tried to comprehend what was going on.

Then Molly’s lips are on his again and he got the rush of the taste of a new mouth. Then Molly, squirming and turning around, and her soft round ass is against him. His arms are around her and they’re spooning. His mouth is on her neck and his hands are on her hips.

It is an interesting thing when you are so used to one person’s body, your hands remember where to go on them, your body understands how you are supposed to fit together, but now he was lost in this new geography. Her lips were too hot and soft, her kisses were too rough, her breasts too big, too heavy, too perfect.

Her hips flared out, giving him something to really hold on to when he pulled her against him. Her ass was soft and cool and when he hooked his fingers into the sides of her panties and pulled them down, he slipped right between her cheeks and it was perfection.

*******

She moved her head back as he moved forward and he was lost in her kiss again. She arched her whole body against him and her lips were on his ear, sucking, then biting, then whispering.

“Do you want to fuck me?”

Jack grunted and pulled at her hips roughly. His cock touching wetness and heat as it rubbed between her legs.

“You have to say it. I like to hear it.”

Her voice was steady, but wanton. It was new, not the silent simple sex Jack was used to. Jack liked this.

“Damn,” he groaned into her neck. “I want to fuck you… so badly.”

His hand squeezed her breast once more and then moved down to between her legs. He groaned again when he felt smoothness where he expected coarse hair. Then his fingers felt wet heat. Silk softness, perfect folds that made him growl.

As his finger passed over her lips and one finger slipped into her she pushed her ass back against him.

“I want you to go down on me.” She gasped, pushing his hand away and laying on her back.

Jack looked down at her, her face was red and a red blush ran down her neck and on her chest where his unshaven face rubbed against her. He went to push her shirt off, but instead smiled.

“Take off your shirt. I want to see your tits.”

She smiled wickedly and pulled off her shirt and then unhooked her bra and took that off.

He saw that red and black star on her chest and lower down another tattoo… a heart on fire with a gold crown above it, right over her heart.

He moved until he was kneeling between her open legs, then he moved down and kissed her neck again, then traced his tongue around the slightly raised thick black lines of each tattoo on her chest. She arched her hips and her breath caught.

He kissed down her chest and stomach until he got between her legs. By now she was growling and purring.

One lick and he was addicted. Her body moved like a snake as he licked at her and she whined and gasped.

“More.. fuck. Make me come.”

He licked her lips teasing and bit the tight skin of her thigh, then he moved in circling her clit and flicking it and he moved one hand up to slip one finger into her.
r />That was all it took. Fucking her with his finger and licking her made her body buck and made her grab the pillow behind her and squeeze it as she came hard.

Jack sat up, watching her come down from her amazing orgasm. He had never seen a woman come that hard. Maggie took a half an hour of work.. sometimes even a vibrator.

She smiled and looked into his eyes and then turned to look at the clock.

“Fuck, we only have 20 more minutes…”

She pushed him away and stood up, looking at him wickedly.

“I guess I got to make you come fast… stand up.”

He did and she kissed him hard, licking his bottom lip and tasting herself on him.

“What gets you off? You want to fuck me from behind? Want me to get on top and ride you? I want to make you get off hard.” She said all these things into his ear as she reached down and gripped his cock tightly.

Really, he didn’t even know. He was so used to getting what ever sad sex Maggie would give him he didn’t know what he really want. He had never been with someone so forward.

“You like that this is dirty? That my sister could come home any minute?” She whispered, jerking him off.

He gasped.

“You like that I am fucking 10 years younger then you?”

He grunted.

“You want me to be a little girl for you? I can bend over and you can fuck me?”

She turned in a flash and kneeled down, taking the head of his cock in her mouth. She sucked and licked around the head. Then she sucked half of his cock.

“Fuck yes.”

All thought disappeared. She broke every rule her sister set in bed. She was like a wet, writhing, perfect id of sex.

She stood up and then leaned over the bed, sticking her ass up in the air.

“Come on… fuck me… fuck me… fuck your little slut”

And then he was looking down at her back with the tattoos that looked like a cello and she was groaning and then he was inside of her. And it was tight wet perfection.

“Fuck me.” She whispered it over and over, like a mantra.

It took seconds for him to come. It was the most violent, mind numbing, powerful orgasm he could remember. He almost fell down, his knees went so weak.

He collapsed on the bed, hardly aware that she had laid down and started fingering herself.

“Fuck…”

Jack turned and weakly kissed her nipple, wanting her to get off one more time.

“Bite it hard.” She begged.

He bit it, reaching up and squeezing her other tit. Then he moved up to her ear and whispered.

“Come for me…”

And she came, loud against him.

And that’s when the door opened.

END

Online Identity

I recently had an interesting conversation with Lumpesse about internet identities and specifically sex blog identity.

At 32 I’ve been a pretty active watcher and member of the various online sex related subcultures. Not to say I was “part” of these subcultures, but I was aware of them, I watched them and occasionally I interacted with them. BDSM, erotica, LGBT, poly, Fan Fiction/Slash, all kinds of fetishes, henti, furry, you name it. I have certainly not been active in a lot of these groups, I’m definitely not into half those kinks, but I have watched them with facination. Back in the heady days of BBS’s and MoDems you put batteries in, to back when AOL was 1337. I have always been on Usenet, the single greatest place to get porn and find weirdness to this day. I am a firm believer in Rules 34 and 35 and I have watched them in action for more than half my life.

As for online identities, I’ve had more than a few. AOL chat room names back when I was in my teens. Changing my name, my age, sometimes even my gender. I had the prerequisite online romances, cybersex encounters, even awkward hookups. I am a child of the internet, it gives me information, entertainment and sex even now.

The problem comes when I started growing up and I realized that I have a more and more fragmented identity, online and IRL. I made friends online and off that knew certain sides of me and I tend to keep them separate. Sometimes worlds would collide by choice or happenstance and I would freak out.

Growing up I realize this was even true in my family because my parents divorced when I was an infant and thus I had two separate families that never spoke and whom in a lot of ways knew very different Jacks.

In relationships the same things tended to happen. I would have a girlfriend and we would be very vanilla and I was fine with that. We would break up and I would be with a girl that would be a practically 24/7 power exchange and I was just as happy with that, though somewhere in the middle was where I was happiest.

About two years ago I started posting very dirty stories on various forums online. I had a rather large following, mostly made up of rather creepy people. Still I liked having this little give and take. Posting things in that manner brought immediate and almost always positive feedback which is ego crack to someone like me.

About a year in I met the Librarian and we had this insanely passionate relationship. It started with a Craig’s list hook up that turned into this love affair type thing. She was very fond of the few pieces of writing I showed her and out of curiosity she decided to hunt down other things. A couple of the stories she found squicked her and I think it was one of the contributing factors that ended the relationship.

One of the many reasons why I only tell people and show people what I know they can handle.

These days, though, I’m getting tired of separating things. I find my circle of friends gets smaller as I cut off the people I don’t feel I can tell things, though my friendships get stronger with the people I actually trust.

On the other side, I like having secrets. I like having different identities. I even like having the ability to close out whole identities and start new ones up on a whim. It’s one of the many things that make the internet great. As I get older online friendships don’t really appeal to me as much. I tend to meet people online and then press to meet them in person because real life is a lot more fulfilling. Knowing real people and having real friendships make separate lives a lot more messy.

Does this happen to anyone else? How many people in your life know about your sex blog or fetish or kink? How much do you tell a new lover and when and has anyone ever reacted badly? Has anyone ever found you out?

Dating Archives: Comfort Food

My most recent ex, The Musician, and I have a pretty friendly relationship. Basically I broke up with her because I don’t think we would do well together for the long haul, we are too different.

That being said we are still good friends and she occasionally calls me and says something like “I really need to get fucked can I come over? If you cook for me and fuck me I will blow you and and let you do what ever you want to me.”

This works out well. It’s sort of funny that my cooking is just as much of an impedes for these booty calls as my cock. It’s nice to get my sex ego and my cooking ego stroked at the same time.

Deep down, hell most of the time even on the surface, I am a nice guy. So fucking a girl who is in love with me takes some moral sidestepping because I know she is going to get hurt. I brought this up and she said she is ok with it. She’s a grown up and the sex is amazing, so we will see how it works out in the long run. I’m expecting her to find a nice boy with a nice job to take care of her pretty soon, until then I will enjoy our little sleep overs.

She came over last night, but just for a home cooked meal. She was rather emphatic about this.

Chicken, potato and carrot curry over rice. Naan. Followed by a carbohydrate haze. We played a little Scrabble. We lounged on the couch. When my hand lazily grazed her breasts she said “No sex, mister.” which honestly I was fine with. I was tired. Of course knowing her the way I did all I had to do was not try and have sex with her if I really want it. So I smiled and eyed her and put on the television.

She tried to kiss me during a commercial, but I pulled away. She said no sex and so we shouldn’t even get started. She pouted. I smiled. She nuzzled my neck and I gave her a obviously fake look of annoyance. It was amazing how well ignoring her worked. By the next commercial she straddled me and pulled off her shirt.

Oh those tits. She is this tiny thing, 5 feet tall, those tits look like they are going to make her topple over. That size ten waist with those DD tits that she doesn’t even know what to do with, and damn how I missed that ass. So thick and so spankable. It’s too bad she can’t take much of a spanking. The first few slaps make her eyes glaze and her lips pout. Then she winces and squirms away. There are so many things I like about the Musician, but she is so very vanilla in a lot of ways.

Still, the fact that if she rubs her clit while I fuck her slowly from behind she squirts. The fact that she will come over just to suck my cock because sometimes she just needs to suck cock. All of this makes her a lovely pet to have around.

I remember a cute little moment. It was one of the first times we were together. She was trying hard to talk dirty, but her little girl voice made it almost comical. It was adorable.

“You like that big dick in my tight little pussy? Give me that dick! Do me with that dick!”

It was dick this and dick that and it sounded oddly childish the way she said it. I grabbed her and said “Cock. Say cock. And fuck!”

She kind of giggled, turned red and timidly tried out the harsher words.

“Fuck me with you thick… cock.”

Adorable.

For all of her vanilla she does have a streak of dirty. Wrist restrains and rope were out of the question, even calling me sir wasn’t her taste (let along Daddy… that was an awkward conversation). She does like to be called a slut, though only when she is primed for it. I pushed it a little farther and told her I should pay her for sucking dick so well. The idea made her eyes roll back in her head with shame and pleasure. The fact that I was rubbing the head of my dick over her clit at the time might have helped.

I wondered if I went to far for her, but in a few minutes when I had that big ass in both hands she looked back at me, hair across her face and asked how much. She said I should offer her money to fuck her. This led to a whole little prostitution game.

She ended up not even staying over. Leaving me alone on wet sheets to ponder what happened. She IMed me later that night to tell me the idea of me paying her for a blow job was all she could think about and she fingered herself in cab.

Date: The Mousy Museum Worker

I tend to talk big online, but most of the dates I go on are relatively boring. I was in a five year monogamous relationship that ended badly a little over a year ago and ever since I have been on a dating tear. So I tend to go on a lot of dates with new people all the time, most of which I find online. I’m looking for someone to hold my interest, but so far none have held it for any more than a week or two with the exception of The Librarian who I dated for about three months and met on Craig’s list and The Musician who actually lived with me for two months and who I met on some forum somewhere.

More than anything else online dating has become a thing to do. A hobby almost. I’m not specifically looking for sex most of the time. I’d actually be happy enough with some new friends, but new playmates are equally important. The primary qualification is intelligence, with sexy and open minded close behind.

Often my luck in dating over the last year has surprised me. I don’t consider myself a catch really, I’m a chubby sort of overly sarcastic wannabe intellectual who has fits of shyness and is much better on paper than real life. Still in the past 13 months I have had a good run. Before my long relationship I had some interesting times as well.

I’m giving you a little back up so that my stories make a little more sense.

This is leading up to last night and The Mouse.

The Mouse is a little thing, although roughly my height she is somehow shorter somehow. She doesn’t have the best posture. She is 22 and works in a museum. She finished her degree early and is going for a Masters in something vague and obscure. These are things that tend to turn me on.

When it comes to dating (as well as all things) I compartmentalize. I filter. I pre-judge. There are sex dates, kink dates, fun dates and smart dates. This was definitely the later.

It was our second date, the first time we just met for a drink and some dinner. It went well enough, nothing really memorable. She seemed painfully shy, which made me bolder and more outgoing. She has braces, which I find odd. Combined with her body language and sort of awkward Pretty in Pink handmade clothes she seemed even younger than her age which is already ten years my junior.

After the first date I had to go on a trip out of the country and I came back to a few messages from her wondering how things went, wondering when we would go out again. We made plans for a museum, discussion, possibly dinner after.

We ended up on my couch.

I have specific tastes, but sometimes it is fun to find someone with completely opposite (physical) characteristic from what I am used to. The Mouse is somewhat thin. Maybe a size 8. Hardly any breasts. Maybe an A cup. No tattoos here. No fancy underpants. Hell, she goes to church.

We flirted in the museum, we brought up a shared love of rice pudding. She commented that I should make her some. She commented on me making her something or showing her something at my place a few times. Eventually I got the point and the next thing I knew we were headed to my apartment.

On the couch after the perfunctory look around the apartment and banter, the kissing started. It’s always interesting finding new lips, new necks, new buttons to push and mysteries to solve. She is such a good girl I kept keeping my eye out for some speed bump, some stop sign. I didn’t want to go farther than she was comfortable with, but before I knew it she was naked on my couch and there didn’t seem to be any doubts.

I often find awkwardness attractive. She was certainly awkward. In nothing but glasses and braces she had an enthusiasm that was comical and hot at the same time.

She got shockingly wet. Impressively wet. I kissed every inch of her and when I went down on her she seemed shocked by the sensation. I wondered exactly how inexperienced she was. She mentioned in passing during the date former boyfriends, various dates, so on. Still as she came and then collapsed into a fit of giggles I felt like I was an experiment or an adventure.

In bed she grasped my cock with one hand tightly. It reminded me of high school. She pulled and examined.

“Show me how to… touch you…” she said, not meeting my eyes.

I took her hand, we played, I let her explore. Then we rolled around together, rubbing and gasping. I wondered exactly what I should do next. I moved to my nightstand, she watched with a questioning look. I pulled out a condom. She settled back.

Inexperience doesn’t turn me on, per se, but as I said variety is always interesting and taking a break from aggressive girls was fun.

What happened next was a little odd. You see… things didn’t exactly fit. There was certainly a lot of good intentions, not to mention lubrication, but it seemed like it just wasn’t happening so we settled for a lot of rubbing and grinding and so on which made her happy, but left me unsatisfied. She realized this and took me, awkwardly at first, into her mouth. I was concerned, her braces, her inexperience, but things went well. When I felt myself nearing I groaned out a warning. She kept going, never letting up.

We then fell asleep.

Today she told me she knew all along that this was going to happen. She even brought a change of underwear. Who would have known? This mousy girl who wanted to walk around in museums with me was a second date fuck.

Thus proving again that I am old and I can’t read women.

A Few of My Favorite Things, Part One

I don’t know if these are fetishes, but over the past few years I have become very keen on certain things. None of them are essential to any sort of sexual attraction, I love diversity, but they are all pluses.

Ok, one of them might be essential, I leave it up to you to guess which one.

Above the Knee Socks

This started with an ex of mine who had a fondness for really long socks she got from American Apparel. After a rather extended dalliance on my couch in which she wore only said socks I was hooked.

Tatoos (Specifically on the chest, collar and back)

Thick black and red lines on tender flesh is lovely. Lovely to look at, lovely to trace with fingers or tongues. It is just awesome.

Glasses

Oh how I hate contact lenses. Why stick things in your eyes when you can look so cute, geeky and hot?

Chubby Girls

From just a little tummy peeking out of low cut jeans to SSBW. I’ve been with the range and I enjoy everything in the middle. Softness and big tits and big asses and I am in heaven. Lately for some reason I have been dating smaller girls, but my heart always belongs to big girls.

Garter Belts

Attached to fishnets or stocking or even just dangling there. There is something about garter belts that turn me on to no end. Especially with nothing under them.

Boyshorts/Boy Cut Panties

Lacy, a little old fashioned, irresistibly hot.

Completely Hairless Pussy

How can I go back? I still remember the first time I slipped my hand down a pair of jeans and instead of rough coarse hair I found sweet smoothness. The very idea turns me on. It is tactile, visual, plus just knowing a girl went to he trouble just to make sex a little more fun is a great starting point. It’s only polite that I make an extra effort to go down on her twice as long if there is that much less of an obstacle for my teasing tongue.

Thoughts on an Ex

Sorry if this is a bit disjointed. I have some more stories, both fact and fiction, in the works but I was out of the country for two weeks and I’m am still recovering.

So, my most recent ex has been texting me and telling me that she “needs to suck cock” and offering to come over, blow me, fuck me and then leave.

Intriguing.

We met when I was on a business trip about a year ago. I was down south for two weeks in a city I’d never been to before. I went looking for information about the city and I found a forum and from there I found her.

She was a classical musician. That alone got me curious. She came to NY a lot because her family lives here and she was planning on moving back.

We met up here before me trip for a drink, hit it off. When I went on my trip she met up with me and what happened was very interesting.

I’d just gotten out of a long relationship with someone physically and intellectually the completely opposite of this girl. Let’s call her P.

Two weeks I was in a city I’d never been in on business and I had my own person hotel room slut. It’s a title she picked out, which was adorably hot because she wasn’t very experienced, sort of a “good girl” and a “daddy’s girl” but she wanted to be bad. I helped her as much as I could in those two weeks.

It’s fun to make a good girl go bad. I’m not one for fucking the innocent, I know guys like that and I don’t understand it. I like experienced girls, but once in a while a young woman who is a bit innocent but eager to learn can be a lot of fun.

Hotels are funny places. You can turn into someone else if your not careful. We were certainly not ourselves in that time. We played, fucked, spoke for hours on end. I sort of rediscovered the art of kissing with her and now it is back to being possibly my favorite sensual activity. Kissing for hours. Making out. Sublime when done right.

Coming back to the hotel every day after working in the office, finding her waiting in the lobby, a little red in the cheeks knowing the staff sees her waiting every day. Kissing her in the elevator, sneaking a hand up her skirt and feeling how she is already wet, her telling me how she was waiting for this all day. Getting to the room and pushing her over the little couch, fucking her hard until we both come and then taking a shower with her. Lounging around half naked for the rest of the night talking, eating dinner and fucking again for hours on end.

After it was over it was sad, but ok. Six months later she mentioned that she had a job offer in NYC. We hadn’t spoken much in the meantime, we tried but we were both dating and jealous. She asked to stay with me for a while until she could find a place. That turned into two months. We dated, but I sort of knew it wouldn’t work out.

I ended it, she moved out but we see each other occasionally. Now she says she wants sex. Just sex. I’m at one of those impasses I find myself at a lot when I know someone is asking for something that is going to hurt them emotionally at some point. Is it up to me to protect them or should I just go for the pleasure? She is an adult.

Fiction – Backroom

When I pushed her against the bookshelf and kissed her neck and pressed myself hard against her, she didn’t seem surprised. When will I learn to read women better?
Continue reading

From the Dating Archives – FancyJobGirl

(This happened about 7 months ago)

So… my second date with FancyJobGirl.

It went well. It lasted 18 hours. A solid 7 of those involved sex. With another 7 of talking heatedly about books, music, media, marketing, history, movies, gender politics, etymology, etc.

She is a short girl. Ridiculously intelligent. Mensa smart. Quicker than me. A wordsmith. We both came out no holds barred, our best material. We were both impressed and swooning.

She bought breakfast.

I don’t think either of us were expecting sex. She came back to my apartment and after nice conversation I kissed her. She kissed me. I kissed her neck, bit her ear, found her buttons. She reach down my pants and then we were on the bed.

She is very multiorgasmic. I found her g spot easily and when she comes that way it is violent and emotional and amazing to watch. After she is shaking and incoherent for a good 10 minutes. Her clitoral orgasms are little bursts that go on forever as one long orgasm.

She kept giving me this look, like how the fuck does this guy know how to do this, which made me feel very nice.

The fucking was good. Not great. She is a little body conscious and there are some other issue that I will get in to in a minute. I was good, she could be a little more active. Her oral sex was nice, but short.

So over breakfast she told me that she had lived with a women for five years, which explained so much. I think she thought I would have more of a reaction, but I kind of just smiled and said “this is very interesting.”

She said guys either recoil or act way too interested and say “I have this friend…”

It explains a lot about the sex. Her ability to receive a lot of stimulation. Her mature understanding of how to let herself have a lot of orgasms. Her sort of clumsiness around a cock. As nice as it was she does have a bit of that thing that a lot of bi girls have. That sort of greedy “I’m just going to lie here are you are going to pleasure me for a few hours” thing that I have experienced before. I mean, it is not a purely bi girl thing, but it is pretty prevalent in that demographic.

Still I can work with it. We will see where this goes. I was sort of up front about the whole “casual dating” thing and one of the first things she noticed when she came in to the apartment were the nails in the walls with no pictures on them.

“Almost looks like someone lived here with you and just recently moved out.” she said sarcastically.

Interesting.

Intro

I’m a reasonably normal person. Like a lot of people I think I am a little smarter than most. I’m witty, I’m sarcastic, I am occasionally arrogant. I am often fascinated. I like to examine things, situations and people. I can be very patient when I feel I need to be. I am very well read. I am addicted to Wikipedia. I like reading about sex and people’s sex lives. I like finding out secrets.

My kinks are varied. I am a very curious person. I am very willing to participate in someone else’s fantasy even if their kink isn’t exactly mine. I am a voyeur, though I like to be an acknowledged audience as opposed to a spy. I enjoy participating in a girl’s pleasure or more accurately being in control of it. More than any other kink I enjoy being in control of someone’s pleasure.

I like rough play, a little bondage, some spanking. I am certainly dominant, though I am not into lifestyle D/s master/slave type relationships. I think roles are a bit more fluid for me. I like to play. When I get into a role I am in it all the way, but I don’t like to live roles.

I am not a sadist, I do not get off hurting someone physically or emotionally, though I understand some people’s desire to be hurt or humiliated and I have been involved in things more intense than spanking and more humiliating than name calling when the need was made clear.

I like withholding pleasure or prolonging it. Long teasing sessions. I am patient and can hold out for long periods watching a girl squirm and beg.

As I said, I like writing about sex and reading about sex. I will read about pretty much any sex act as long as it is well written. There are some very wild stories online and I have read some of the darkest, filthiest and hottest. I see a real difference between fantasy and reality and how some things are better left as words on a page. I often read and write about things I do not condone in real life.

Physically I am usually attracted to women who are curvy, be that just buxom and sultry or chubby and soft. I tend to like short girls (under 5’4″). I’ll just say it outright, I like big tits. Big tits and big asses. Chubby little sluts are my favorite things in the world. Chubby little sluts who will call me Sir/Daddy… I’m pretty much powerless against them.

More than any physical trait, I’m attracted to intelligence. I like well read women. Librarians, teachers, professors, writers, musicians, etc are all a plus.

Last year I ended the longest relationship of my life which lasted about 5 years. I’m not particularly looking for something long term now. Now are the hunting days. I’m having a lot of fun out there, but I’m very safe and I haven’t found someone to share a lot of the secrets I have and will talk about in this journal.

Science Fiction/Erotica – The Long Run

tlr

Classic story. Boy meets girl. Boy falls for girl. Girl leaves boy. Boy buys four clones of girl to be his company on a long space flight. Continue reading

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