Anonymous: Budding boobs

Teddy was a real bad ass type during the day, when he had to make sure his macho side was able to handle the scene at work. On the busy construction site, if he put his mind to it, he knew there was no problem, he could handle himself.

He was a no nonsense type of guy, and in that way earned the respect of the rest of the men. He wasn't afraid of going up on the high grid, and handling tough situations.

That was all part of the game, as far as he was concerned.

You earned your money and you did your work, and then the rest of your life was your own…

He was that kind of a guy…

So when the end of the day came, and the work was put aside, he felt he earned the right to relax, and let off some steam.

By dressing up in his favorite clothes.

Now, that in itself wasn't so awful… lots of guys were into that…

But Teddy was little different than lots of other guys…

Because his favorite clothes consisted of women's panties, a garter belt, stockings with seams, high heels, a bra, a wig and lots of makeup.

He loved to get dressed that way, and go out for a night on the town.

He was never quite sure what he was going to pick up on once he was out…

And maybe that was all part of the fun…

For Teddy was really a lady, inside his head… he was the type of guy who should have been born without a cock… with a nice pussy and a good set of tits…

But that just wasn't the case…

Sure, he liked to fuck, and he always had a good time in the sack, but when he was dressed as Teddy, his feminine alter-ego, he liked nothing better than to pick up some guy at a bar, take him home, and surprise surprise…

It was just one of those things he liked to do.

He didn't see any harm in it…

In fact, most of the men he picked up were so grateful for the night of sex they got off him, they usually wanted to see him again.

Most of the time, though, Teddy wasn't into sharing, that way.

He didn't see the need for repeaters.

Not when there was so many good-looking guys out there just dying to be fucked!

And he was the guy to do it.

Sure, it was a well-known secret that most guys were really bi-sexual… that they hated their wives if they were married, or couldn't get laid if they weren't…

And that if they were only given the chance, they'd take fucking by a cock every time…

Every single time…

Which is what really drove him to want to get as many as he could…

It was a fucking public service he was performing.

Anyway, the construction site knocked off at four that Friday afternoon, and while most of the boys decided to retire to the corner pub and start their weekend binges early, Teddy found he didn't have time to stick around…

He had to split, to get out of there as soon as he could… because he had a hot night planned for himself.

He was home by six… to his small apartment on the lower east side of Manhattan… a place he'd had for a dozen years…

It wasn't much, but it was his and it was cheap… and that was enough for him…

Now, as he got home, he peeled off his clothes and got the shower ready.

He was going to take a nice long hot one, and get himself ready… to get ready…

He got out of the bath and dappled perfumy powder all over his body.

One that was done, he slipped into the pink, crotchless panties he'd bought specially for this weekend – why not splurge once in a while, he told himself – and then went to the kitchen to make himself a drink.

He did vodka and orange juice, his favorite, and while he sipped, he slipped on the radio, and filled the little apartment with music.

Now, as he went back to his bedroom, he took out the love pair of stockings he was going to wear that night.

They were very sheer, black ones, with a heavy seam going up the back.

He put them on, until the came above his knees, and then he reached for the satiny garter belt.

He slipped it on, did the fastener, turned it around and sat on the edge of the bed while he fastened it to his stockings…

Now he got up and checked his freshly shaved legs.

Beautiful, he said.

Unlike most crossers, his legs were full and smooth and shapely… much more like a woman's than a man's…

Now, he went to the closet and picked out his black tight dress… his favorite one, and slipped it over he head, wriggling down into it…

Next, he went to his dressing table.

There, he put on the blonde wig that he'd bought earlier in the week.

It wasn't one of the sidewalk specials, either…

No sir! This wig was a real expensive job… one that looked mighty fine on him… hard to tell that it wasn't the real thing, he was sure…

And then, when he was satisfied that it was just in the right place, he began to apply the make-up to his face…

He did his eyebrows, and his lipstick, and the rouge…

Now he checked his face in the mirror.

Perfect, Teddy thought. I'd fuck me. No question about it…

Now, he was back at his closet, slipping into his spike heels.

He liked that.

His look was complete…

Now that he had it, he wondered what he was going to do about it…

What he was going to do to get fucked.

He knew that the first thing he had to decide was the right bar.

Like maybe the The Ritz…

That was his kind of bar…

The The Ritz, in mid-town, was filled with young, rich executives looking for a good time…

His kind of people.

So, getting the down steps, confident that even if he ran into one of his stupid neighbors they would recognize him, he was ready to hail a cab.

One pulled up in front of his building, and now he was ready to get out of there.

"Take me to the The Ritz," he said to the driver.

They went up Fifth Avenue, and he was let out in front of the hotel.

He walked into the bar.

Just as he thought.

The place was teeming with people.

He took a seat at the bar and ordered himself a martini.

He checked the time on the wall.

Eight.

He wanted to be having sex by nine.

That was his goal.

That was what he had in mind.

And he knew that he could do it…

He could do it with no sweat, if he played his cards right…

Sure enough, before he'd finished his first drink, the fish was biting at the bait.

"Is anyone sitting here," the voice said behind him.

He turned his head and saw the guy for the first time.

Gorgeous, he told himself.

The man's gorgeous.

Tall, black hair, cute thick moustache, broad shoulders… everything a woman and Teddy could want…

He smiled and said no, the seat was up for the asking.

The man chuckled and sat down, ordering a drink for himself and another one for Teddy.

Very presumptuous, Teddy said out loud.

"Oh, I don't know… what a drink, really, when you think about it…

“Very very charming.

"A drink is a lot of things… ”

"Oh… ” "Yes… it can mean the start of a wonderful evening, for one… ” "Yes it can… ”

Eight fifteen… Forty-five minutes to go… if this kept up, he'd beat his previous record!

"Well, my friend's call me Mack… I like my name, so what's yours… ” "Teddy… ” "Teddy… I like that… I wonder if it has anything to do with the way you dress… under that nice black thing… ”

Teddy smiled. Was this guy for real? He decided to find out. He leaned over… "How would you like to see for yourself?”

Mack grinned.

"Just what I had in mind, as a matter of fact…* "Well, what are we waiting for… ” "I couldn't say… I have a nice room in this hotel, if you're interested… ” "Let's go then… ”