It was a Saturday, late summer – one of those days where you’re so horny it hurts, and before you know it you lose about 12 hours to frenzied masturbation and Internet porn. I had been stroking off and on all day, but hadn’t cum yet. At one point the penis pump even made an appearance, which only made things more swollen and tender.

When I logged into my Yahoo! instant messenger that evening, I knew that if Missy was logged in, we’d end up getting together. (Missy is a she-male that I’d had a previous experience with.) The hornier I got, the more my thoughts turned to her massive cock and tits. Sure enough, her little buddy icon was lit up, indicating she online and available. I knew trouble was on the way.

While our first encounter was definitely enjoyable, I only craved her presense when I got super horny. This was one of those times, so our IM exchange was brief and to the point: She wanted to taste my ass, and I wanted to taste cum for the first time. I showered up and drove over.

Missy answered the door in her robe (again) and the apartment was full of green haze (again). She led me straight to the bedroom, where she had an elaborate, lace canopy bed. Despite her 10-inch dick, this girl was completely feminine. Missy pulled shut the curtains and said, “I wanna taste that ass.” She had me bend over the side of the bed and undo my belt. I felt my jeans and boxers being pulled off, exposing my rear. The air was cool against my naked skin, still slightly damp from the shower – I felt completely vulnerable. Looking back, over my shoulder, I saw Missy licking her thick lips.

Her large hands seized my ass, both thumbs on the inside of each cheek, spreading me as far apart as possible. I could feel her hot breath on me, and then a savage tongue licking my crack up and down. Missy wasn’t subtle, or gentle. She was slurping away like this was the greatest feast ever. Whether I was ready for it or not, her strong tongue forced it’s way into my hole and stretched me open.

I’ve had the pleasure of having my ass eaten out before (by two different women) but this time was different. Her tongue was rough, course, probing, and seemed to be very, very long. I could feel the length of it lapping hungrily inside my hole as she pulled my hips back toward her face. Missy was completely owning my ass, and it was incredibly hot.

After satiating herself, she flipped me onto my back and crawled on top of the bed. Her took her huge dick into my hands as we assumed a 69 position. I’ve described it before, but I have to stress this again – Missy’s cock is unbelievably big. Like a circus penis. Straining to get my mouth around this monster, I coated it with as much saliva as possible and took her inch by inch. Before long, Missy was thrusting hard and the thick head was banging against the back of my throat. I had to come up for air many times.

After a few minutes of hot 69, she pulled back and asked “you want to taste my cum?” I nodded eagerly in agreement. Missy got up off the bed and pulled me down between her legs. I licked the slit of her cock head, teasing her while she worked herself with her right hand. Her stroking became faster, more insistent, and her breathing increased in pace. Missy’s left hand was on the back of my head and she was guiding her thick meat in and out of my mouth. She was really enjoying this, knowing that I was about to taste my first load.

Missy let out a moan, and I felt a warm rush in my mouth. Honestly, it was completely different than I expected – I was prepared to get choked with jet after forceful jet, but this was more of a slow stream. (Missy later revealed that she blew two loads earlier that day, which probably contributed to the lack of volume and power.) Regardless, the taste was salty, sweet and hot, and I formed a tight seal with my lips so I could capture and swallow every last drop. I popped her cock out of my mouth, took a deep breath and smiled up at her.

“You like that, huh?” she asked. “Fuck yes,” I responded.

Sure, I was extremely horny, but tasting cum for the first time sent me into overdrive. My dick was straining and hard as steel. After all the abuse I’d put it through that day, it felt like it was bigger, thicker and more swollen than ever before.

Missy told me to lay on my back. She leaned over my body, cupped her mountainous, fleshy tits and commanded “I want you to cum on these, baby.” That was all I needed to hear. It took about 10 seconds to stroke myself to one of the most intense orgasms I’d ever had. This load had been waiting all day to come out. Stream after stream of scalding, searing cum blasted out of my cock and splashed all over Missy’s chest. This was a money shot that Peter North himself would be proud of.

We took a few minutes to catch breath and clean up. I was still shocked at how powerful my orgasm was. (Wow, apparently tasting cum really gets me off. You learn something new every day.)

Missy and I wished each other well and went our seperate ways. We hooked up a third time after this encounter, but of course I’ll save that tale for another post. :-)

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“Catherine!” Elizabeth gasped between her thighs. “You are like heaven’s own scent.”

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“Under the cover of my long skirt, my legs are spread for him, and I’m dripping over his fingers.”

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Editor’s Choice
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See also: Fleshbot’s Sex Blog Roundup each Tuesday and Friday.

The definition of a MILF, if you go by the literal acronym itself (Mother I’d Like to Fuck), is a female who has children and happens to be fuckable. This doesn’t really narrow it down enough, so I’ve set my own criteria for what makes a MILF:

1. She has kids.
2. She’s married.
3. She lives a suburban lifestyle.
4. She actively stays in shape, but her body personifies motherhood: Big, full tits, wide hips, and ass cheeks that you can really grab hold of. Some padding here and there.
5. She’s in her prime and horny 24/7.

Again, this is what a MILF is to me. She’s the hot mom/wife I can’t have. Some guys prefer lots of hand jewelery (shiny rings and bracelets) on their MILFs, which I guess implies that she’s wealthy and married. How these preferences get hard-wired into our brains, I have no idea, but I strongly suspect that porn has something to do with it.

So, what’s your ideal MILF like?

One of the many people I met through AOL’s member directory was a woman in her early 30s, married, with children. (We’ll call her Leslie.) She was stuck in an unhappy, sexless marriage with a police officer who she claimed cheated on her all the time. Leslie was interested in two things: 1.) Making revenge love with another guy, preferably younger, and 2.) Tasting cum for the first time.

Seriously? This woman was over 30 and hadn’t taken a load in her mouth yet – even by accident? Of course I was more than happy to oblige – there’s nothing I love more than a woman who craves cum and specifically asks for it. So we started with the standard e-mail photo swap. At this time I had amassed quite a library of personal cock shots from my webcam, so I sent her everything I had. She responded with a lo-res bitmap headshot.

After a few weeks of chatting, Leslie was invited over to my townhouse. I was totally into the MILF fantasy at that time (well, I’ll always be into MILFs) so it was awesome that she arrived in a minivan. She didn’t quite fit the criteria of what I consider to be a true, 100% MILF (this topic will be tackled in a later post). Leslie was about 120 lbs. with shoulder-length, dark curly hair. And she walked with a half-limp, which was kind of strange.

She dropped by three or four times, and we’d get naked and have sex. (One time we went and got ice cream afterwards, so this wasn’t all about fucking.) Leslie would only be able to come over during the hours that her husband was on shift and her children were off doing their sports activities. Sometimes she’d park the minivan a block away, in case somebody was following her, I guess.

The intercourse itself wasn’t that memorable, but the blowjobs certainly were. Leslie really meant it when she said she wanted to taste cum – she worked my dick for half-hour before I finally spilled into her mouth. This wasn’t one of those “I want you to blow your load and coat my face Peter North-style” cravings. Her lips were a tight seal around my cock head as I came, and she siphoned out every last drop. There literally was no mess afterwards. She swallowed it all and told me how great it tasted.

Part of the pleasure of the relationship, for me, was being Leslie’s 23-year-old sex toy. I loved the way she would undress me and savor my body. I totally got off on the fact that I was this woman’s outlet for needs and fantasies she couldn’t fulfill with anyone else. My ego was stroked, and I liked that. (Surprise!)

Our communication broke off after her husband got into her AOL e-mail account and found my cock pics. I received a threatening e-mail from him, claiming that this was tantamount to sending pornography to their children, because they all shared a computer. He threatened to use his police connections to sniff me out and arrest me if I ever e-mailed Leslie again.

She IMed me once more after that incident, but didn’t bring it up, so I never knew if he told her that he found the pics or not. I didn’t mention it, either. We never saw each other again, but I hope Leslie got what she needed from our encounters.

But man, the pioneer days were rough – females on IRC were few and far between, and the ones that did exist were mutants. (I hooked up with a couple of them anyway. *Shudder.*) Since then, AOL’s member directory, Yahoo! IM and MySpace have all been effective tools in my aresenal to find women for casual dating and, of course, sex.

The art of the Web Hookup has evolved greatly. In the beginning, there was so much nonsencial back-and-forth chat with females who didn’t even have digital photos of themselves. You had to convince them to take a photo to the public library or Kinko’s and scan it – then you’d receive an enormous, 300-dpi tiff file of a 3×5 photograph and the inside of a scanner lid. One time I even had a photo faxed to me. (???)

Today, women are all business. When they use the web for random play, they aren’t shy about it. Not to mention they’re attractive and have tons of pics (or if I’m really lucky, a webcam).

However, I’ve not yet been able to milk anything from the “Casual Encounters” area of Craigslist. This could be due to the fact that the metro area I live in is considered small-ish, and CL just doesn’t have a huge number of users here. When I travel to large cities, I’m always amazed by the volume of w4m casual encounters postings, but I wonder how many of them are real. Supposedly the vast majority of these posts are made by spambots, e-mail harvesters and pic collectors.

Disclaimer: I have successfully found and arranged paid sex via Craigslist, which is a much easier task. :-)

So, guys, do you have any CL casual encounter success stories? Women, have you ever posted on the list? If yes to any of the above, what cities/areas are the most, um, bountiful?

I consider myself to be straight, but with an active she-male fetish. Go figure.

It has to do with cocks, of course. I’ve always been visually stimulated by dick (specifically big, thick, veiny and cut) as well as glorious, messy cum shots. However, the rest of the man’s body does little to turn me on. Does that make any sense?

Through my teen years, cocks would show up in my fantasies from time to time. I’d think about stroking them, sucking them, and even taking a load in my mouth. In college I experimented with a guy I met through IRC (it was the only chat option in those days) but just couldn’t get into the man-on-man action. The thoughts continued well into my early 20s and it became apparent that, in order to satiate these urges, I should either find some anonymous glory-hole action or find a she-male.

I actually think lots of straight guys can get hot by looking at dicks, but they’d never own up to it. This is where the she-male fetish comes in – big tits plus a juicy piece of meat between the legs is a win-win situation.

So I was 24 when I first communicated with a she-male online. He/she (let’s call her Missy) found me through AOL’s member profile search and we started casually chatting. Missy was quick to volunteer her stats – she was a 6-foot-tall black / puerto rican mix with 42DD boobs and (supposedly) an enourmous dick. Before long we were exchanging photos. I showed her my cock and ass, and she returned the favor with a face pic.

Every time we chatted, Missy would invite me over to her apartment. A few times I’d say “yes” and then cancel at the last minute like a jack-ass. I really wanted to explore the fantasy but seemed to always chicken out. About a year passed and we periodically stayed in touch. I remember the evening I logged on and finally agreed (and meant it): it was a bitterly cold December night and my girlfriend and I just had a epic blow-out fight.

Missy answered her door in a robe and panties – true Penthouse Forum style! She was well over six feet tall (kind of imposing at first) but completely feminine and smelled like a sexy woman should. Missy sat me at the end of her bed and approached slowly, opening her robe and burying my face between her warm, chocolate-y tits. They were massive, but very firm – we’re talking all implant, here. We both took a couple of hits off a joint and she undressed me and told me to stroke myself hard for her. I could see her licking her shimmering, luscious lips through the sweet-smelling haze. It was very clear who was in charge.

She had me get on my knees in front of her and guided my hand between her thighs, where I could feel something pulsing and growing. It was tucked back, but swelling by the second and straining against the fabric of her panties. Missy pushed the strings down across her hips and it popped out, bobbing in front of my face. I was in shock. This was truly a monster cock, as advertised. At least 10 inches and incredibly thick.

I wrapped my mouth around Missy’s dick as best I could and started to give her a novice blowjob. I know she had received better ones, but hey, I was learning. It was difficult to produce enough saliva to keep the cock wet and slippery, this thing was so big. There was just enough length to allow me to work both hands up and down the shaft with my lips and tongue around the head. The salty taste, coarse texture and the smell of pot and girl in the air had me completely intoxicated – I was finally fulfilling my fantasy.

As I sucked Missy, her large hands roughly seized my ass cheeks and I could feel a well-manicured fingertip probing my hole. (This felt surprisingly good.) I finally came up for air, then she pulled me onto the bed with her so I was straddling her hips. Watching me stroke myself, she shot a load onto her stomach and then instructed me to cum. I obeyed upon command – squirting hot jizz all over her horse cock. Missy continued pumping for a bit, slicking up her meat with my load. Fucking hot!

While cleaning up, she remarked that she was a Chicago native, so for some reason I asked if she was a Cubs or Sox fan. Missy didn’t know. To this day I have no idea why I tried to start a conversation about sports with a she-male. We both finished wiping ourselves down and bid each other farewell. She slapped my ass on the way out the door and announced that she’s “having that” next time we meet.

After this initial encounter, Missy and I would see each other two more times. But those are stories for future posts.

My she-male fetish is still active to this day, and I’ve developed a certain set of “standards” as to what I look for in a transsexual:

1. He/she must be passable as a female. Hair, makeup, perfume, smooth skin, clothes, tits, lips, heels - the whole package.
2. She must be fully functional. Lots of she-males get pumped full of hormones and their dicks resemble a weed sprayed with Round-Up. I prefer hard, thick and able to cum.
3. More cock requirements: I like them big and cut.

So – any other guys out there with she-male urges? I’m curious to know what men (and women) think about getting hot for transsexuals. Does it mean you’re gay? Bi? Does it even matter? What specific things do you look for when encountering, or fantasizing about, a she-male? Be sure to leave comments below!

Link to video on PornoTube: http://pornotube.com/media.php?m=1399763

It’s a lot easier (and more comfortable) to be a shameless perv on The Internets than in Meatspace. My day-to-day life is relatively normal, so I’m going to use this blog as an outlet for my depraved thoughts and sordid tales I can’t tell anyone else about. (Lucky you, Web Visitor!)

So here we go. Check back often and don’t be shy – feel free to leave comments and/or shoot me an e-mail.