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