The proposal

I’d met him at the station, as I’d been hurrying from the mainline platform to the underground.

“Can you spare change for a cup of tea?” The youth sitting with his back to the tiled wall had begged.

I’d stopped and stared.

Amongst that milling crowd, those eyes had held me: those wide, innocent looking eyes.

“You’re staring mister!” He had snapped.

“Can you spare any change, or are you just taking the piss?”

I’d offered him two pound for tea and forty pence for the phone.

“Here,” I’d told him.

“If you want to earn some proper money, just phone…”


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My descent

This is the first time I’ve told my story publicly. I wrote this maybe 3 years ago, and have shared it with one person.

I used to cross dress in my hotel room while away on business trips. I’m a fat bald 46 year-old who looks ridiculous dressed up in ladies underwear. When you’re obsessed, though, appearances don’t necessarily stop you from doing something. I’m married, but my wife doesn’t know about my hobby. I never do it at home. It was something I only did when traveling. Fortunately, as a sales manager, I spent a lot of time on the road. But with airport security these days, it has become way too risky to carry a suitcase full of ladies undies and a dildo for pleasuring myself.

Even as a nine or ten-year old, I was the one who volunteered to play the girl role when we played games. Thinking back, it’s funny how sexual some of our play was even though we did nothing overt, and didn’t really know what we were actually doing.


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First meeting

The note from Dennis was short. It said, “I can’t stop looking at your profile. I’ve read your blogs, and your fantasy, and love what I see. Thanks just for being here. Very cute bottom. I’d love to play with it someday.”

Some day came three weeks later when I arranged to meet Dennis at his apartment for an afternoon of playtime. “Wear that same outfit you wore in the picture,” he said as he gave me directions to his home.

I was nervous as hell walking up the flight and a half stairway to his two bedroom apartment. How did I know that Dennis wasn’t an axe murderer? I didn’t. My nervousness at meeting someone I’d only known for three weeks, and then only through an exchange of emails, was overridden by one thing: lust.


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Friday night

After work I picked up the pictures and went home to get ready. I got the call from Wanda this afternoon at work. She first apologized for kicking me out of her house last Saturday night, Halloween, without letting me clean the cum off my face. Knowing that I would have had to walk home like that in my 4 inch pumps. That’s why she also kicked John out, so he could pick me up. “Besides,” she said, “I got so horny watching you get fucked by Peter and John on the pool table that I had to fuck Peter right away, I couldn’t wait.” She told me the reason she waited till this afternoon to call, she wants me to wear completely different clothes than what I wore on Saturday and she wanted to make sure I didn’t have time to buy any. She suspected I didn’t buy the clothes at the used clothing store like I said and figured rightly that I had a full wardrobe already, also to make sure I wear shoes with a higher heel than the 4 inch pumps I had on last Saturday night. “Since you were able to walk so well in them all night long, I know you have something with a higher heel that you can walk in, you bitch,” she giggled.


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A good fit

I didn’t want to be there. Trying on clothes in a department store doesn’t rate high on my list of entertaining activities but I needed a few more sport coats so I bit the bullet and went to the upscale store at the mall. At least I had the freedom to go on a Monday afternoon when there would be few people and abundant parking.

So here I was, in the deserted men’s department looking at jackets. Being Monday there were not any sales people on the floor that I could see. So, I piled up a few jackets and headed to the fitting rooms.

About halfway through trying on the jackets I heard someone enter the area and turned to greet an attractive brunette. She looked much like the typical department store cosmetics counter hottie and was dressed in a charcoal gray skirt reaching to just above the knee, silk white blouse and blazer. Frankly she was all-American-girl good looking and her shoulder length chestnut hair shined under the halogen lights.


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Quilty pleasures

Trevor parks the car at the far end of the large car park so we’re not seen arriving together. That’s very important. We play by my boyfriend’s rules. I have no choice in the matter.

“Come on you little slut,” he says, killing the headlights and switching off the ignition. He doesn’t smile, only puts his hand up my dress and feels my crotch. “Jesus!” he says. You can’t wait, can you?”

I’m already hard with anticipation, but this doesn’t stop a tear coming to my eye. I have an odd mixture of feelings. On the one hand I feel a naughty kind of excitement, and on the other a feeling of hurt and helplessness to be used this way.

“Come on, then… Let’s see if you can pull for us tonight,” he says.

My heartbeat is thundering in my ears and there’s that familiar fluttering in my tummy. It’s always the same.


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What a year

It was 1979 and I couldn’t stand it anymore. I was living in Chicago, surrounded by gays and transsexuals. I had begun sneaking out at night and buying copies of Blue Boy. When I would read the stories about men taking other men in their mouths, I would always get a hard on and eventually cum. I had a lot of guilt involved in the process but still I could not stop buying and reading the magazines. I never figured myself for gay, but still it was undeniable that the whole gay sex thing made me harder than women did. I was 26 at the time, just reaching my sexual prime. I was a former high school athlete and in very good shape for my age, I would spend hours dreaming about being a woman and being able to take a male cock in my mouth and swallow his cum. I began to believe I was a woman and I was meant to be a whore. I would beat off to the idea of taking one load of cum after another, swallowing and saying “Next!” I was constantly astounded by my desires, as I thought of myself as a jock and very, very heterosexual.


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One of those things

It was. Really, that’s what it was — `just one of those things.’

It’d started with one of my stories being used on nifty.org

A fella sent me an email, in response to it, as it happens, a really fit fella, with washboard stomach and impressive shoulders and pecs. That’d been sent in answer to my response to his email, saying how he liked my story. A nice thing to say.

I say all that that, as he sent me a pic of himself, albeit the face and background were obscured. But, `oh wow, that body.’

Then he’d gone on to say how much he’d like to meet: and, `where did I live?’

So anyways, I’d told him that I lived in the North West of England.


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Photo shoot

Two days ago, I was travelling to attend a panties photo shoot in California. It was the first one I did for this manufacturer, but I was led here by a referral.

The maker sent me all the panties they wanted to model, and sent me a box for my own personal wear. The size fit perfectly, and I was amazed at how sexy they looked and made me feel.

My favorite was the pink set. The fabric was mesh with pink layers, and in between the layers they had light pink and red hearts. The panties were not full panties, but rather booty shorts, and they were so cute. I adored them. I was gonna tell the director and producer when I got there that they were my absolute favorite. I wore them over and over again.

I arrived at my hotel, wearing some shorts a T-shirt with a bra. I made shirt the t-shirt was black, because I had on a pink bra, and some pink thongs. Why so much pink? Because as soon as I got unpacked, I was going to take the thongs off and put on my favorite pink panties. Oh, I just loved them.


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The cherry queen

¬†Unfortunately, for the boys, it had all started five years ago. The annual event in the small town of Cherry Tree is the Cherry Blossom Festival. For it, a queen and her court of princesses is picked from the co-eds at our high school. As a gag the boys had nominated a fellow male student and because they outnumbered the girls, the boy was actually voted “Miss Cherry Blossom.” This dismayed not only the girls but the townsfolk as well. And the boys didn’t know when to stop; for the next year they did it again, and although a boy was not picked as the queen, three out of the six princesses ended up being boys. It was a disaster and everyone was furious. It was then that special meeting of the PTA and faculty was held.

¬†The next week all the students were gathered in the auditorium for an important announcement. Mrs. Hammond the principal took the podium and announced, “The boys of Cherry Tree seem so fascinated with entering candidates in the Miss Cherry Blossom pageant that we have decided to create one just for them. A Miss Cherry Tree pageant which will crown a queen and her court of twelve princesses. This is how it will work.


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