Letter from East Hesburgh

Dear Shoeblossom

Flash loves to tease my butt-hole, she runs her long nails in and out, and then, of course makes me lick off the crud. She will use her other hand to twist my cock head about, what do they call it, the glans? like she's trying to open a bottle of baby aspirin.

I'm standing in front of Flash, who is resplendent in her little leather miniskirt and fishnet stockings...she has one hell of a set of legs.

Flash always tells me that my legs are good too, and she ensures that I shave them once a week.

I think I look a little ridiculous in the garter belt and white stockings, but it seems to make my wife hot...or at least it reduces her to giggles.

My hands are attached to the sub collar I wear around my neck. Flash has a boyfriend who created little cuffs that I can put my wrists in, so they look a little ridiculous hanging off my neck.

"Wilkie, this is the way to get you to be creative. Maybe you can use your hips to rub your dick on the wall and cum that way."

But I prefer it when Flash masturbates me, although of course she has the irritating habit of pulling her hand away all the time.

This morning, Flash and her friends rented a bobsled and had it pulled by...guess who?

The leather straps and the bit in my mouth was awful, but pulling along in the winter snow was worse, although she generously allowed me to wear boots, and otherwise I was nude.

It would have been kind of hot if it had just been her and her girlfriends in the sled, but she invited a couple of guys, including my business partner, Craig.

Craig was given the whip to urge me along (strangely, I find a bobsled with five people in it to be kind of heavy to pull)

The girls laughed when the whip's lash cut me under the butt and I screeched.

Craig got a kick out of this, as he has always endured my telling him what a wimp he is, and how he has shitty coordination, and I how I beat him at one-on-one basketball.

Then, after I finally pulled the damn bobsled back to our place, Flash and Gillian and Kairn and Marnie and Craig peppered me with snowballs as I danced naked in front of them!

I do love Flash, but I think she has a very cruel side. True, we did meet at the Hesburgh Leather Lifestyles Lounge. I was selling off my old canes and implements, and offering (Begging) attractive women to try them out on my bare ass before purchase.

Flash wasn't Flash back then-she was called Floyd. Yes, she is a transgender now. And I paid a lot to get her to be a chick, just the best surgeons.

But I'd even been attracted to "Floyd" when I met him. I'd told him as he smiled at me with his wispy moustache, that he could try a cane out on me.

"I thought you were just into chicks."

And Floyd really had a great grip on the cane, and followed it up by using a bullwhip on me, the very one that pulls the bobsled around now, eighteen months later!

But Flash is so different now. She has big, full breasts, 36 C's-and curly bright blonde hair. She decided not to have her dick cut off.

"I mean, why give up any sense or sensation, right?"

The laws in our state allow all sorts of marriages-I guess it's the law of the land now, right?

As President of the Hesburgh Young Republicans, I can't say I approve of gay marriage for all, but I am glad we got to hitch up.

And it's astonishing how feminine Flash looks, even with her big dick...

Now she is trying to get me to have the operation, too, but also have my penis removed.

"It's not a particularly big one, Wilkie," Flash tells me often. "You wouldn't miss it that much."

And how she teases!

Just this afternoon I'm standing in front of the bobsled party, all in the living room.

I've served everyone hot Irish coffees, and I'm standing naked in front of my "wife".

Flash's elegantly manicured fingers are rubbing my so frustrated cock!

She alternates quick and slow jerks, and I buckle with the intense pressure on my groin. Months of backed up cum are just boiling in there.

Kairn and Gillian keep teasing me by pulling up their tops and flashing their tits in those frilly bras, and Marnie keeps running her little pink tongue across her lips and winking at me.

Craig of course, is just looking at me contemptuously while he drinks his Irish coffee.

"Jesus, what a faggot you are now, Wilkie." He's always resented it that I saved his dad's firm when I joined. I was the smart kid in Hesburgh, and I was always teasing Craig, playing jokes on him, "Gulled again, eh?"

Craig's dad, K.C. Bullivant had been so annoyed that his son had spent much of the firm's funds on cocaine and prostitutes.

When I came in, the company became "Wilkerson and Bullivant" and we became the biggest spice-and-salad dressing sales force in the tri-state area!

How Craig Bullivant had endured his father's ribbing about wishing I'd been his kid instead, blah blah.

Of course I'd inherited a bit of money, which I'd pumped into the firm, too. And I knew a few recipes that helped, and we began making pasta sauce as well.

But when Flash learned of our competition, just the "good natured" ribbing, she had decided to let Craig know that I was really a sissy at heart.

But this afternoon was just the hardest! As I had stood, legs quivering in front of my transgender spouse, getting my dick tickled, the women-born-women had upped the ante.

Kairn and Marnie pulled off their tops and began slathering Lubriderm on their awesome tits. When Gillian joined them, she tossed her pink halter top at me, as if I was the stripper!

"So, um. Floyd-"

"Flash, not Floyd." my wife gently corrected Craig.

"Well, you know, Wilkie got a lot of girls in school, and now he sucks your dick all the time?"

"Yes, that's the way it goes. " Flash casually picked up her electric toothbrush, and put the "perv" brush in it, and snapped on the little button.

"Now I'm warning you-" Flash's voice became angry and masculine-"If you cum when I'm brushing your dick, like you did the last time, it won't go well for you."

"Right, faggot. I'll fuck you up the ass, maybe." Craig laughed.

As Flash ran her toothbrush right under my cock head, right on that sensitive little vein, the frenulum...

Marnie kicked off her shoes and began rubbing her heels on the base of my cock, and then kicked me once or twice before continuing the foot job.

At the end of the evening, I jacked off onto a hand mirror and licked it up, this as a reward for having gone down on all five of the bobsled riders.

It was a great experience!

Tomorrow though, Craig promised me he is going to whip my bare ass in his back office. He liked the way I sucked his cock, as I've had lots of practice with Flash...

But there's always improvement.

After all, I'll be locked up then, and if I get a whipping and then go on my knees for Craig, (and his Dad, who is a horny old bastard) every lunch hour...it should turn me into an expert!