http://picture-attached.tumblr.com/

[Show as slideshow]

12►

“I’m basically a fire-spinning and breathing gothboy gamer-geek art fag.  I quit smoking seven years ago so I don’t look quite so much like Spider Jerusalem.  As a child I wanted to be a vampire when I grew up. Obviously, that hasn’t worked out so well.  My venus flytrap is named Hibbert.  He is a constant disappointment to me.  I never got around to getting my driver’s license.”

Perhaps I should rename this post as “future father of the week”…and ladies, I’m not sure he’s the type that will pay for the abortion if you change your mind.

I scribbled page after page while chuckling to myself about each person that walked in bar. I can read their secrets on their face.

The 46 year old cougar who loves it up the ass. The innocent 18 year old who fantasizes about being called a whore. The married 35 year old who is here to play out his tranny fantasy.

The funny thing about a bar is nearly everyone who walks in wants the same thing…to find someone…to connect…to be wanted…even for just a moment…even if they already have someone. Even still…people are too afraid to say anything at all…they do anything they can to be invisible…and never say hello to the beautiful girl at the end of the bar…the girl who was wishing for hours you’d just come over.

Tonight.  I’m not that person, but I can see it on everyone else’s face.  Tonight I just want to watch.  I just want to drink.

Within less than an hour four people had interrupted me.  The quickest way to start or end a conversation is by saying, “I have a blog about sex.”  It always gets an interesting response.  You can immediately tell what someone is looking for…if they’re horny and stupid…uptight…or classy yet interested.  I’d already flat out rejected three offers for drinks, which began to catch the attention of a group of British businessmen across the bar.  A few more interruptions and I decided to give up.  The businessmen were just begging for something to talk about…something to break the tension in the stiff group…I was going to be that something.

Two fumbled to get me a drink.  I insisted on getting my own.  All were wearing wedding bands.

The conversation began with my blog, which then quickly went to the subject of craigslist…something British men knew nothing about.  They all quickly pulled out their blackberrys and it was time for an education.  A whole new world was opened up and the education advanced to the words in the ads…what was a snowball, a BBW, a donkey punch.  The hours ticked by and one by one the group got smaller and smaller.

And one by one each one found a clever way to pull me aside, feed me a line, and hand me their hotel room key.  Each one not knowing their colleagues had just done the exact same thing two minutes before.  I was grinning, flattered, and laughing inside at the what was unfolding.  Let me remind you they were all married, and I’d made it a point in the conversation to bring up each of their wives.

There in my hand…40 minutes later…were three keys.

I clipped the first strap over my hip.  Slowly but eagerly I slid one end of the cock into the aching between my thighs.  I tightened the second strap.  You can’t help but feel in charge with such power between your legs.  I hadn’t known what to expect, but I certainly didn’t anticipate the desire that welled up inside me to suddenly want to thrust my manhood into just about everything.  I felt this new animal instinct and couldn’t help myself from lying back to bring myself to ecstasy by jerking off my new toy.  It fit perfectly inside me and the waves of pleasure that exploded within made this whole adventure worth it…even if I lost the bet.

After I was done trying on my new get-up…I decided to select my first casualty.

Jonathan.  Broker.  Nice city apartment.  Pictures of family and his college days playing hockey.  Perfect hips. Perfect tan.  I was curious to know more about what type of man desires such a thing.  It was all entirely new to me.  I’d never even dominated someone.

He let me in, pressed me against hard the wall, and kissed me deeply.  It seems we would both be reversing our usual roles.  There’s nothing that I find more of a turn on that a man who knows what he wants and isn’t afraid to take it, but today that would be my job.

I sat on the couch and directed him to strip his clothes off in front of me.  Naked and hard with anticipation, I forced him to kneel on the floor and begin to satisfy me.  My eyes rolled back with pleasure.  I let myself enjoy it only for a moment as I was here for one reason only.  I handed my pet a bundle of rope and scissors and instructed him to cut four long pieces.  I walked up behind him…placed my hand on his hip and gently but forcibly begin to satisfy what he had been craving for so long.  With the glass anal plug in, he doubled over with ecstasy.  I instructed him to focus on his task, while teasing him some more.  He was fighting back his dominate nature to throw me on the bed and fuck me like a whore.

After tying him to the bed, I rewarded him for obedience and began to tease his ass with my tongue…then slowly taking the tip of his rock hard cock into my mouth.  Unsure if he was ready to take all of the strap on, he begged for his new glass toy again.  I gave him what he desired and immediately took his cock into the back of my throat.  My moans of enjoyment could barely be heard between gags.

Concentrating only on how much I was enjoying playing with my sub, I hadn’t noticed he had untied both of his hands.   Out of no where he flung me on the bed face down and instructed me he was going to use me exactly how he saw fit.  He quickly and roughly held both my hands behind my back and fucked me with no remorse.  Exactly as a sub like myself desires.  For the next few hours, I could barely remember my name much less that all of this was to win a bet.

Tgirls and ladyboys have always fascinated me. I have so much respect for anyone who is willing to face life’s challenges head on and declare this is who I am no matter what you think…something most straight people live their whole life afraid to do. Most tgirls are more woman than I’ll ever be. I won’t sacrifice comfort for style…I’ll never last 12 hours in heels.

But I confess…I am totally ignorant of the transworld. I wanted to know more and what was there to lose…maybe I could gain a few hot girl friends…

what could be better than a cock and amazing breasts all in one magical package?

And if my total ignorance was apparent, I knew someone would step up and give me an education.

A dozen posts later and I only had a handful of responses…but finally one beautiful lady stood out.   We started by phone…apparently I was the rarity to her.  A woman looking for a woman.  She didn’t think I was real…or serious.  I was.

She was sexy and adorable.  Intelligent…and funny.  And I was going to treat her to a great night like the deserving lady she was.

Opening doors.  Great wine.  Great food.  Great conversation.  We headed back to her place with all intents and purposes of introducing me to a whole new world.  As usual I had no idea what I was getting into, but I never turn down an opportunity to experience something I never have before.

On the outside her house was quaint and well kept…we shyly headed inside together…she took my coat and flipped on the light.

And BAM!

There in front of me were 20 gigantic aquariums…bubbling loomingly in the background…stuffed full of live lobsters and monster looking exotic fish.

It was weird. It was really weird. I felt like any man would probably feel like when it’s after the blow job that they discover that their sexy lady friend is carrying a little extra something below her belt.

In this case, I had been excited with what I would find below the belt. However, there was just no mentally blocking out this living room packed with finned friends.

We called it a night.

I needed an adventure. I needed to get away and write. I needed to cause some trouble. I packed a bag in 10 minutes and got dressed in my best suit and jewelry.

As I pulled up to the valet, my Adrenalin started to pump. I handed him the keys and headed inside. My heels echoed across the marble floor of the hotel lobby. I had picked one of the nicest places downtown that I couldn’t afford with one goal in mind. I was going to get a free room. I didn’t know how, but I wasn’t leaving until I did.

I coolly walked up to the counter, took off my sunglasses, and placed my ID on the counter. Twenty minutes later, a lot of egotistical huffing, three calls to different managers, and my unpaid hotel key was in my hand. Sometimes a simple lie that they screwed up your very expensive reservation and the threat of taking your business else ware can take you a long way.  That was easier than I thought.

I headed to my room and changed into cute sweatpants and a t-shirt. I already had a plan. Bar. Beer. Writing. People watching. Relaxing. And nothing more. Hotels are the perfect place to find cute intelligent men who are wild in bed, but tonight it wasn’t even on my mind.

I took  my spot in the bar.  My pen in hand and head down. It wouldn’t have mattered if Brad Pitt walked in.  I wouldn’t have cared. Shine, the bartender, handed me my usual beer with a smile and said, “Here you go ‘Jet Blue’.” He knew me. He’d given me the nickname Jet Blue after one of our previous conversations…I was the kind of girl that didn’t like to be attached to anyone or anything…or as he put it…*ding* “you are now free to move about the country”.

I’m not sure what it is about the night you decide to have nothing to do with sex that dozens of possibilities gravitate towards you, but by 9:30 the next morning I had probably broken up a business and taught an entire group of British men about Craigslist…and uh, snowballs.

It was my last year of grad school and the annual retreat where the second years are supposed to bond with the first years and take them under their wing…mostly by getting drunk around a bonfire and then ending the night singing karaoke at the local one-horse bar.

She had a sporty, but girlish look about her…like she’d out holler you watching a sporting match at the pub, but then later remind you that she owned what was between her legs and was going to make you beg for it.  I distinctly remembered her from her interview…those lips…that smile.  And as usual, I had the bad habit of fantasizing about everyone I find slightly attractive the second I meet them…over and over again.  She was no different.  I wanted her naked.  I wanted her legs wrapped around the back of my neck.  And I wanted her now.

I also have a bad habit of never assuming anyone’s sexual orientation far after everyone else already has.

The weekend came to a close and the school year started.

The whole year went by and we hardly even said more than a few words to one another except the times I taught class.  However, a couple of weeks into the year I did learn she was batting for the ladies team…the fantasy only increased.  Now if only there was an opportunity.  Yes, opportunity.

I wasn’t about to create one.  Oh the drama and whispers that would have occurred…not to mention that no one even knew that I enjoyed the occasional night eating a peach.

And then there it was…two weeks before graduate school was about to end…opportunity.

Opportunity that would lead to some of the most annoying sex of my life.