The Lipstick Lumberjack

The highlight of last week's first event was dressing someone in my own outfit (again!) -- it was the trannie party.

A masculine man was wearing tight fitting black patent leather high heels, fishnets and and a fancy complicated black leather corset with four small straps looped over each pectoral muscle to create the shape of a breast. Nice!
He had a beard, no makeup and was surprisingly wearing a long sleeved flannel plaid shirt (opened to expose the corset) creating the appearance of a Mountain Man/Lumberjack, with S&M trannie leanings. Masculine, yet feminine. Sexy!

I went up and complimented him on his outfit, but said how much sexier he'd look if he took off the shirt. He said it was his first time there, and that he was shy. (Shy?! This coming from a Lumberjack in fishnets and high heels?!)
So we chatted a bit and I tried to make him feel comfortable, maybe even try on some of my clothes since he said the high heels were tight and uncomfortable. He said he was a men's size 12. I told him I was a men's size 13 and my high heeled boots were comfortable, so I suggested he try them one. Would he do that? Yes. So I took off his shoes and zipped and laced my own boots onto each leg. The whole time he was sitting on a table suspended by chains and I was sitting on a leather chair adjacent to it. He was about 12 inches higher and on my right side. Behind me on the wall read a sign: "Zero Tolerance for Drugs or Prostitution."

As I slipped my footwear onto him, it was clear that his foot would fit, but his beefy calves could barely be contained by the confines of a zippered knee-high boot. But I made them fit!

Footwear down.
What's next?
Hair! I asked if he wanted to wear my huge (five-wig-combo) brunette behemoth. He did -- it would minimize what a large man he was -- a 6'3" Lumberjack in my platform high heeled boots with the same wig given to the Israeli Giraffe. Anything to make these giant "girls" female, feminine and petite! I shamelessly took it off in public, caring less what any of the chasers thought; I wasn't doing this for them. But it was a show we were putting on and people were watching. The Lumberjack loved the wig, shaking it around, demonstrating its bounce!

But the Shirt!
How could any of this make sense with that damn shirt on?
What would it take to get it off? I had already given him my boots and wig. What needed to happen? I asked again.
"Lipstick. Could you put some lipstick on me?"
I didn't have any on hand since I (still!) only use black liquid eyeliner as my lipstick.
"Do you have any?" I asked.
"Yes!"
And there in his little bag was a stick of lipstick to be applied to his eagerly awaiting lips.
It seemed part of his trip was for me to put it on him, Not him.
So I applied it to his thin lips -- trying to avoid the whiskers of his thick mustache and beard -- and watched as he instinctively rubbed his lips together to evenly smear it around.
It reminded me of being made-over in 3rd grade at the Elementary School's carnival as the girl-who-knew-what-she-was-doing applied lipstick to my lips and I instinctively smeared my lips together to spread it around -- having watched my mother do it. "You know how to do this!" she responded in amazement at the 9 year old queer boy. I smiled proudly, "Yes I do!"

Lipstick applied, the man slowly took off the plaid flannel shirt he had been hiding behind all night! He was still shy, but feeling it -- feeling feminine and somehow complete. The lipstick gave him the power to complete the transformation. No one could see the lipstick, but he could feel it and that's all that mattered. He looked in the giant mirror and soaked in the image we had created together. And all was good in the world!

And once again, I was there to help. As is my duty and obligation.

The following day was a Bear Party and I was hoping to have the sex I never had the night before; it didn't happen. I tried fucking a friend who hasn't been fucked in over a decade and all I ended up doing was putting a couple fingers up his ass and calling it a day. Zzzz...

We spent a lot of time laying down, feeling each others' bodies and talking about reality shows and life in general. Very casual. Very friendly, but there was a strong urge to hold his hairless body next to me. (What was a hairless person doing at a Bear party?! He said by comparison, it made him feel skinny! It did the same for me! Hanging out with bigger, older men makes you feel young, skinny and desired!)

We ended up going out to dinner after the party. It was great to have someone who's company you thoroughly enjoy, but there's also a sexual impulse to wanna get-with-him. And that impulse is returned.

That was an afternoon event and by the time evening rolled around it was time for The Main Event: the LGBT Pride Party and performing (in drag) a routine that I had been rehearsing with Coat Check Kelly all week. I don't want to spoil anything because we're going to make a video of it and I want to post it here. I will tell you the audience loved it as we lipsynched to our own voices. A story was told and it was understood and totally embraced! It made me ready to perform again! But first, we have to make that video!

Feeling the rush of the performance, I was standing near the coat check area when an incredibly sexy guy came up to Kelly and was asking for me. Or rather, he was asking for "the owner of the club." He knew me by name, but he knew me as a guy and what stood before him was a giant drag queen in high-heeled boots. Kelly pointed me out.
"There he is!"
The sexy Latin just laughed and walked away.
Kelly said the guy had eaten out with us once before -- after a party.
He did look familiar. And definitely sexy. But clearly my outfit was not sustaining interest. He was not a trannie chaser!
Kelly also mentioned that the guy was a power bottom and when I saw him a little later, he was already getting fucked by an older chubby guy. Unacceptable! That ass belonged to me!

So I ran upstairs, washed off my makeup and switched into my boy clothes. Or rather, man clothes: black combat boots and a black leather-looking jock strap. (Actually it was rubber with foam lining.)
I searched around -- a man-on-a-mission -- and found him (the HOT guy looking for me) in the same area I had seen him before, sucking the guy's dick who had just been fucking him. His ass was sticking out, but the guy who's dick he was sucking had his hand on his ass, fingering his hole.

No! That hole is mine!
So I felt up the other butt cheek aggressively, prompting the bottom to turn around. And there I stood, with my newly pumped up beefy pecs asking if I could fuck him.
"Yeah."
(Yes!)
So I got hard, got a condom and started fucking him doggy-style as he sucked the guys' dick.
AND I DIDN'T STOP FUCKING HIM FOR 90 MINUTES!
I wanted to prove to him what a power top I could be and he clearly loved it.

We took a break once to clean up and start over again.
And at one point as he sucked my dick, I played with his ass and invited someone over to fuck it -- as though it belonged to me and I got to choose who fucked it and when.
Hot!

(There was also a time -- actually at two locations -- where a woman played right next to us and thanked us for fulfilling a fantasy: she had always wanted to watch a guy get fucked by another guy. She even gave me a flogger to use on either of them, but I was too busy fucking to use it properly.)

I told my bottom guy that I like to spit and slap and do some rough stuff, but all he allowed me to do was spit on his balls and ass. So I did a lot of that. I also sat on his face and ended up cumming on his chest. He used my cum as lubricant to masturbate himself and shot his own load as I fingered his hole. Perfect!

And a good time was had by all!

Sort of.
Toward the end of our play, as we were getting close to finishing and I was really pounding him, a good friend stood nearby and kept saying loudly how hot my fucking was. Great! I appreciate the good review, but don't stand by and comment on my behavior AS I'M DOING IT and NOT STOP TALKING! It's like a critic standing up in the middle of the audience during a performance and commenting on the play AS IT'S GOING ON! Rude! (No matter how positive the review might be, it's distracting and unappreciated.)

So I wrote him an email and said I appreciated the sentiment, but next time, either join in (he's very young and sexy, so that could be fun!), stand and watch quietly, or just move on. Otherwise it's too much of a distraction.

Yes, I like to (sometimes) put on a show, but a blow-by-blow account of the action?
No! Ain't gonna happen -- not in my club!