The Cross Dresser and The Big Fat Fuck

As soon as the door closed to her place Debbie started squeezing me tight. Before I knew it I was the one with my dress around my ankles. Soon I was being pulled down the hall to Debbie's bedroom. While I sat on her bed, Debbie went in her bathroom to freshen up.

When she came out she was wearing a sexy red night gown. If it weren't for the fact it was a size 6X you might have thought Debbie bought the thing at Victoria's Secret.


Debbie was one big fat fuck of a woman. I used to say that Debbie's tits were so big she must have to keep a window open in her apartment before she could take her bra off. Otherwise the sudden rush of air from her tits flying free might blow out all the glass in her place. Plus if she's not careful she could set off all the car alarms in her neighborhood every time she undresses. That's how massive her breasts were.

Her tits were all natural too. That meant she had a nice round ass to go with them. One time when she was wearing sweats I had to fight the urge to reach over and give her a good fisting. That's how tempting her fanny was.

Not only did Debbie have a nice body, her face was pretty as well. It wasn't bloated out the way some fat girls can get. She had just the right touch of chubbiness to her cheeks. And when you add long blonde hair cute bangs and gorgeous hazel eyes Debbie was one big beautiful woman.

But it wasn't her looks that really attracted me to her. It's that we had so much in common. We both had the same crazy eclectic taste in music. Plus we loved to argue about politics. People would yell at us to just "get a room," we'd go on so much.

The only problem was that Debbie was a coworker in my very politically correct office. To make matters worse I was my organization's trophy trans-gender. They could parade me out to show how progressive and forward thinking they were. It wasn't a problem for them to have a man wear dresses to work as long as my clothes were professional and in proper taste.

Of course the catch is allot of people still assume if you're a cross dresser you must be gay. I'm not. I'm bisexual.

But what didn't help was the fact that I had just ended a long term relationship with another man who was on the opposite side of the trans-gender spectrum. Maria said she was a woman trapped in a man's body wear as I was just a regular guy who liked to wear a dress on occasion.

Some of the gals in the office even looked forward to giving Maria a wedding shower after she fully recovered from hir sex change operation. The irony here is I was the one who talked hir out of having the operation. And soon after that we broke up. Maria said s/he needed hir space to decide what s/he really wanted.

That gave me a chance to play the victim card to the full. I even brought myself to tears.

"I don't understand, why s/he changed hir mind," I'd sob.

"There, there, Lori," everyone would say, "These things just happen."

Debbie was one of the ones who made made it allot better. The challenge was how to hide the fact that I would pop a woody every time Debbie gave me hug. That's the last thing I needed to show through a tight fitting dress when I was at work.

Meanwhile it was now six weeks later. I knew if I ever had a shot at asking Debbie out it was now. She was alone by the water cooler. This was my chance. I took a cup and poured myself a drink.

"So um Debbie," I began. "You know, I um, don't wear a dress all the time. I can be, you know, normal. "

She threw her cup away and gave me an odd look. "What are you telling me this for?" she interrupted.


"Are you coming on to me?"


"Because if you are I'm OK being with a guy who likes to wear a dress."

(Is she throwing me a lifeline?)

"In fact I think it's kind of kinky"


For our first date Debbie gave me a tour of Pleasant Town's club district. It was early evening in mid July the sun was just starting to go down. I wore a light brown sleeveless dress while Debbie had on a white blouse, black tight fitting slacks with a matching big rimmed hat.

Usually I like to watch all the guys do a double take on me. That's what makes wearing a long red wig even on a hot day worth it. But tonight, my focus was on sweet chubby Debbie. However,it was fun to catch a comment or two.

"Are they a couple?"

"Check out the lezzies!"

"Yo, I think the tall one might be a dude."

We were walking arm and arm through the trendy Regent Street neighborhood. There was stuff going on everywhere. But we finally landed at a popular gay night club called "Twisty"s." If you replaced all the Pittsburgh team logos with one's from Boston I would have thought I was back at "Slammer's" in Millingham.*

They even had a she male dancer performing just like at Slammer's. Hir name was Lucy May. She was an Asian she-male like the one I knew in New England. Billie Jean of course had a whole routine based on Michael Jackson tunes. (S/he really gave everyone a "Thriller." Hir rendition of "Beat It " burned down the house.) Lucy May on the other hand had a whole Shirley Temple thing going on. Hir act finished with a rousing crowd pleasing version of "On the Good Ship Lollipop." But the things s/he did with hir giant lollipop were way too naughty for little Miss Temple.

Meanwhile Debbie was absolutely clueless on what this was doing to horny bi sexual me. She may as well have brought me to a regular strip joint. It was hard to hide how excited I was getting.

Debbie took my hand. "Are you OK?" she asked with a concerned look on her face.

(Oh, no! Think Lori boy, THINK!)

Then it came to me. "I'm offended!" I answered.

"Offended?" replied Debbie.

"This hussy is sexualizing all of us trans-gender folk!"

Debbie started to rub my right arm with both her hands. "Lori I am so sorry. I wasn't thinking. Look I know a better place we can go."

We wound up way across town in Pleasant Town's Italian section. Nestled in this quaint little side street was a little gay bar called "The Birchwood." It was far more relaxed than "Twisty's." There were gay couples lesbian couples, straight couples even a few cross dressers here and there.

Debbie and I found a booth in a corner, ordered from the late night menu and checked out the internet jukebox. After that we danced the rest of the night away. When "Just the Way You Are," by Billy Joel came on, cupid opened up with a barrage of arrows on both of us.

Before we knew it, it was closing time. Debbie gave me a dreamy look and said, "You know my place is just up the road in New Castle."

As soon as the door closed to her place Debbie started squeezing me tight. Before I knew it I was the one with my dress around my ankles. Soon I was being pulled down the hall to Debbie's bedroom. While I sat on her bed Debbie went in her bathroom to freshen up.

When she came out she was wearing a sexy red night gown. If it weren't for the fact it was a size 6X you might have thought Debbie bought the thing at Victoria's Secret.

She got into the bed next to me and we started to snuggle. Before long it was time to untie her night gown. The glass in the place remained intact and the only alarms I heard were the ones going off in my head. But I finally got a chance to get a good look at Debbie's enormous breasts.

There was no hiding my pleasure. My eyes must have gotten really big.

"Enjoying the view Mr. Green?" teased Debbie.

"It's just you're so beautiful!"

"Well, they're all yours lover."

The next thing I remember I had gone from kneading Debbie's tits like two giant mounds of dough to fucking the living daylights out of her. The neighbors downstairs must have thought Debbie was doing a late night load of wash with the way her bed board was rocking back and forth.

It was soon time for my favorite fat fuck finishing move. I reached under Debbie's chubby ass and grabbed her big round butt cheeks with both hands and pushed upward. Meanwhile my legs were rubbing all over her big meaty thighs.

Debbie bent her head back and was moaning with pleasure as I began to empty the contents of my ball sack deep into her big box.

In my mind I was thinking, "God, you're my big fat momma!"

But out loud I said, "Oh my God, you're so beautiful!"

"You're so,


We held each other close for the longest time, and then it was Debbie who fell asl**p first. As for me My mind was spinning too much. I got up to check my E-mail.

There was something from Gail in Arizona. For a brief moment I almost deleted it. Instead I decided to send her a "Dear Jane" letter. I almost clicked "Reply" without seeing there was a file attached.

My mouse hovered over "OPEN" for a brief second, then I clicked on it. With that, Cupid's spell was broken. The file was a JPEG of Gail in the nude shoving her fist deep into her pussy.

"I miss you" it said underneath.

"Oh Shit!" I shouted.

Debbie didn't hear it.

She was snoring too loud.

*Fictional Boston Suburb
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Posted by loriannthetran
4 years ago    Views: 656
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3 years ago
ver good, continue write more
4 years ago
The first story I've read here that's made me hard and then made me laugh, out loud, properly.

You sure can write, honey. And I know how you felt... xxx