Cleaning Up is a Drag

What is it with me and drag?

I can remember being a little kid (8 or 9 years old?) and running around the front yard in a wet t-shirt with water balloons tucked underneath for boobs, loving how they bounced around like the real thing!
Then I remember my dad telling me to stop.
I also remember crouching down and often wrapping my t-shirt over my knees so it looked like I had big breasts. Did other kids do this?
Or maybe it was every Halloween when my procrastination led me to the last-minute-necessity of wearing my mom's clothes (and modest heels!) out for the night. I mean, it was Halloween, right? I was allowed!

But I never dressed up like that because I felt like a woman inside, I just liked pretending I was a girl. And really, isn't there something inherently sexy about girls? Something sexy about stereotypical femininity and softness? (Not that all girls are feminine by any means!)
Maybe for most gay guys it's not a sexual thing, but for bisexuals, trannie chasers and straight men, there's certainly an allure!
And truth be told, as written about in previous posts, the men that one can attract by dressing this way can be outstanding. And for whatever oddball reason, the more I dress like this, the more I become attracted to the same: femininity in others. Be it in a biological woman or a drag queen.
I've seen/heard of it happening to other trannies: they were gay men who transitioned into women and became lesbians! Fascinating.
So my situation is certainly not unique.

With all that in mind (and perhaps the part that is unique) was when the young-guy piss party was coming to a close and everyone was tired and not looking forward to the thorough cleanup that was about to unfold. Myself included.
So to mix things up and create some fun, I ran upstairs to my private chambers and changed into drag to clean up the mess!

The first outfit was a leopard print nightgown with slits up the front of both legs -- all the way to the navel; incredibly revealing, especially without underwear! I also wore the giant dark brown/magenta five-wig combo (worn by the Israeli Giraffe) and had scandals on for practical purposes -- with the hosing down of the entire space my feet were sure to get wet.
But alas as I bent over to pick up trash and empty out beverage bottles for recycling, my negligee kept falling onto the wet floor; I can only hope it was the wet area already hosed down. After getting wet, the garment would stick to my body. Cold and wet = really unpleasant. And who knows what that wetness really was! A change was called for.

I went back upstairs and put on something more practical: my high-heeled black patent leather platform boots, a short hot pink dress with black trim, matching hot pink full length gloves, my white flip wig and makeup (black lips and mascara).
The other cleanup boys approved -- and it only took me five minutes to transform so it's not like I was trying to get out of work!

So there I was, kneeling down in my high-heeled platform boots, picking up the sometimes-slightly-browned condoms that were stuck to the floor. Only this time, I had put latex gloves over the full length opera gloves, so as not to get cum, lube, piss, shit stains or stank on my gloriously textiled fingers...
Because I'm a girl with class!

To continue in that classy tradition on that sunny Sunday morning at 5:30am, I was out on the streets of Brooklyn, sticking out that hot pink opera gloved thumb as if hitchhiking for a ride to nowhere. There were no takers. And as the cleanup crew drove away in the promoter's SUV, I started bending over to show them my ass and lifting up the dress to show anyone looking that underneath the elaborate facade, I wasn't really a girl.

As if there was any doubt.

How I Got Fucked in Drag Live on the Internet

Was it a bad idea to pit two dueling Monsters against each other? No, I'm not referring to Godzilla, Mothra, Rodan or Ghidorah but rather the equally epic Dominican Donky Dick Lesbian vs. The Israeli Giraffe, two pivotal players in my story (this blog) so far.

Ok, so maybe it's not that epic, but I certainly wondered what would happen when two prior play partners showed on the same night for the same party -- upon my request.

I often invite more than one person to a party because its so rare to actually get someone out to Brooklyn for an event. But the last time these two showed up, enough happened that I wrote about them. And both ended up eating out from brunch with the staff after the party ended. And that's really considered being a part of the inner circle.

Dominic Donkey Dick Lesbian (D.D.D.L.) was the first to arrive. Interesting that D.L. should be part of his moniker. He still lives with his family in Jersey and is very much on the Down Low, not out to even his best friend and certainly not sharing his penchant for getting dressed as a girl and playing with the same (other guys dressed as girls -- hence the Lesbian part of the name).

I have another Jersey friend who likes to dress up for the trannie parties and D.D.D.L. used that friend's wig to complete "her" ensemble. Before D.D.D.L. arrived, I dispersed all my drag clothes, wigs, makeup and accessories across the floor in the living room, including five new dresses I bought at the nearby Salvation Army.

As soon as he stripped naked to begin the transformation, he got an erection. WOW! I remember now why he was referred to as Donkey Dick. And I loved that just getting naked surrounded by women's clothes (and me!) was enough to get him turned on. I'm sure it helps to be 19, too!
But I also know how it is with closeted people who finally get to encounter their fetish after weeks/months/years in a stifling environment: arousal is the usually first thing to appear, whether they want it to or not. The anticipation has been overwhelming.

With all the fun dresses and accoutrement I had laid out, D.D.D.L. was only interested in what he had just purchased for himself -- a long white tank top that served as a tight fitting dress and printed tights to cover his unshaven legs. Once dressed (pre-makeup and wig) he looked like a football player (a lean running back, not a linesman!) though, not a girl. And I must say, his 5'9" body was rock solid: broad muscular shoulders, beautiful pecs, a washboard stomach and narrow hips with a bubble butt, and muscular thighs that framed a dick that looked more like an infant's entire body (forget the arm!) than anything reasonably belonging to someone of his size and age. And yet, not overly sized like a body builder, but in perfect proportion: stunning!

But apart from all that, D.D.D.L. has a charming visage with full curvy lips that smile frequently and sparkling eyes that could probably get him whatever he wanted. This, as they say, is a player. A young charismatic guy that can get whatever he wants.
And on this night, he was on the prowl for "girls."

And I was there to help him with his search!
Was I being generous again, by helping another fetish freak find his kink or was I creating a girl (a la Pygmalion) and hoping she might turn her affections toward her teacher?
I could only hope I might get lucky again, but in the meantime I couldn't believe the perfectly sculpted athletic body that stood before me, wanting my help. How lucky was I? Damn. And I was allowed to kiss and fondle him too. He let me grab his dick , since it was hard and calling out my name, as much as an infant can speak English at such a young age. D.D.D.L. smiled, clearly liking the attention and validation.

Then The Israeli Giraffe arrived!
Whoa! Two potential play partners at once? My fortune had doubled! But could I really give my attention to two people?

So instead of trying to get naughty I focused on getting the girls their outfits. And truth be told, The Israeli Giraffe wasn't really into getting dressed up. Yes, it was fun the first time as part of a whole seduction when I was also in drag and I was offering him the clothes off my back, but in this scenario, with no shoes for him and a masculine face that would take a lot of work to feminize, it seemed that on this night, he would have to remain a man. And so he went downstairs in his underwear and a robe that would be removed upon his arrival.

With The Israeli Giraffe out of the picture I was able to focus on finishing D.D.D.L.'s transformation into a woman. He put some foundation on his face and I applied liquid eye liner and yellow eye shadow to lighten his darker skin tone and make his eyes stand out a bit more. Then he finished it off with a dark wavy wig and some lip gloss to that always-smiling mouth!

But I couldn't send him to the party looking like a football player!
So we found some white tights that downplayed the size of his thighs better than the busy printed ones. And he put a dress over the tank top to give his upper body more of a feminine shape. Perfect! Hair brushed out. "She" was ready to go!

As we were about to embark on another adventure downstairs, The Israeli Giraffe reappeared saying that he didn't care for what was going on downstairs: he was the only person in his underwear and no one was really doing anything.

I explained that this party was different from the LGBT one he had been at before and that most of the guys at this event stayed completely clothed, even though it's a sex party. It creates a very different ambiance. And the guys are into trannies, not guys, so if you're looking for a bisexual man into you as a man, this is not the party to be at!

That said, he returned the party with me and D.D.D.L. perhaps to play with us -- we'd have to wait and see. And if memory serves correctly, The Israeli Giraffe has a small Jewish child of his own hiding under those BVD's!

We had taken so long to get ready though, that by the time we arrived, some of the girls that had arrived earlier had already left and that put more focus on us (which would've been there already) to deliver our goods to the boys. And truth be told, that's never D.D.D.L.'s intention: she's there to play with the girls, not the men.

I, on the other hand, was open to whatever/whomever might come my way. And D.D.D.L. gave me the freedom to do that.

First on the agenda: The Israeli Giraffe. Now that we were in the club together, it was our chance to pick up where we left off before, which was my sucking his large cock very publicly (in the DJ lounge area) at the LGBT party. Was he going to fuck me now?
Wait... I want him to suck my dick first! And prove that he really was into guys and not all about being serviced and having only his needs met.
Alas, he was not into sucking dicks, which included mine.
Suddenly my interest faded. It didn't seem a fair exchange! I put all this work into my appearance and I serve his needs?
No, at a trannie party, it's girl's choice and this trannie wanted a blow job.
But The Israeli Giraffe was not having it. So I (tried to) politely move my attention elsewhere. He was clearly disappointed that I wasn't interested in playing with him anymore, but if we're not sexually compatible, well, that's the end of that -- at least when you're at a sex club.
We can be friends, but as sexual play partners, it can't be all about you and your needs, there has to be some give and take (unless one person always wants to give and the other person always wants to take.) But I'm versatile and doing the same thing over and over again can get boring.

(Side note: The Israeli Giraffe later told me he had sucked a dick once and he didn't like the taste of the guy's pre-cum. And sexually speaking, his activity is very limited. So maybe in the future he will try it again. But I know it can be tough to go there: the first cut is always the deepest, isn't it?)

Turning my attention now to D.D.D.L. I was more than happy to (try to) suck her stiff Dominican Horse Cock. She sucked mine at the last party, so I knew she was versatile -- at least where oral sex was concerned.
With regard to fucking, she was a top and things seemed to be headed in that direction at the last party. Might that happen this time? (Please?!!!)

The party was coming to an end, The Israeli Giraffe had long since left and neither myself nor D.D.D.L had gotten any play, except for my sucking her dick.
She had a long drive home, and was anxious to leave unless there was something else to keep her there.
I dangled a new option: sex on the internet!

Ever since a recent trip to California, upon the advice of a friend in Florida, I encountered a free website where people have sex on camera and broadcast it out to the world via internet. This has been going on for years, but it was new for me and it was a new play toy for me before bed. I had done one "show" of my own, but for the most part was happy to jerk off watching others play with themselves. (I didn't show my face while I did mine.)

But I had to create a profile (male, bisexual) and that's what I logged into when I brought D.D.D.L. into my bedroom. She was up for it!

We were going to broadcast a trannie sex show live to the whole world!

The thing is, my profile said I was a guy, so when we signed into the "Couples" area, people would check in, hoping to find two guys going at it.

And what did they see instead? Me sucking D.D.D.L.'s dick, with my white flip wig covering my face, pulling the flip to the side so the viewing audience could see the Dominican Horse Cock I was going down on!

The website has areas for men, women, shemales, couples and "parties" so I thought we might find some interested trannie chasers.
Nope.
Instead, we drew in guys wanting to see gay male sex and their posts were insulting to say the least: "ewww, it's two ugly drag queens!" was the one that stood out the most.

Okay, so we had a hater or two, but the more we did it, the profile image might change from a male image to the live feed, and the trannie chasers would come running. They didn't. Or if they did, they certainly weren't writing anything in the dialogue box.

Undaunted, I asked D.D.D.L. if she wanted to fuck. She did!
Yesssss! Finally! I was gonna get that beautiful infant's body inside me -- a reverse birthing, if you will, only up my ass. It had been a while since the last time I was fucked, but I was willing to give it a try and see if I could take it.

I asked what he wanted me to wear: he suggested the tutu, so he could lift it up and feel like he was fucking a girl.
So I ran into the living to find the appropriately alluring item to entice my partner.
Done!
Next?

I turned the laptop to the edge of the bed so I could bend over while standing on the floor. He said he liked to watch while he fucked, and did I have a mirror I could put across from us?
Done.

Let the games begin.
So with the laptop and mirror in their designated spots and alluring tutu in place, with a condom and lube we began our live sex webcam show.
He was stiff as a 19 year old could be and putting the condom on it was shear pleasure, but not as good as trying to take it up my ass. A true challenge, but one I took willingly! And take it I did. Slowly at first, but then to the hilt.

We had to stop briefly to apply more lube -- I was just so tight and he was so big, that my sphincter was scraping the lube off his condom!

Once he was back inside, I totally lost it -- verbally. As often happens when I get fucked, I lose my shit (verbally, not literally!) and start whimpering like I'm about to cry. It's just too much!
Too much HEAVEN!

And within minutes he shot his load.
I have to say the fucking couldn't have gone on for more than five minutes, which was fine with me. It was too overwhelming to take for much longer. And I was glad to see he was satisfied! One girl serving the needs of another. Such sisterly love!

I took some photos as he stripped naked. I had to document how fucking amazing he looked. And that dick was just. A monster! He took a shower and left when I made it clear I wasn't ready to cum yet. Besides, I knew he was in a hurry to leave.

After he was gone I watched the live male shows on the cam website and pleasured myself to completion. As I did I fantasized about the reality I had just created for myself, a reality that the whole world had the opportunity to witness. But I don't think I'll be doing it again anytime soon.

Porn on the Fourth of July

It was Fourth of July weekend and someone needed to be liberated -- first in the form of flogging, and then later in the form of running in tandem naked through Prospect Park.

I had invited a very cute young looking Latin guy (delicious caramel skin, bright blue eyes -- love that combination -- and an amazing ass) to the first-Saturday-of-the-month party.
He bursts with youthful energy and oozes sexiness. And he showed up! We have talked about it for over a year and we've always had a certain amount of sexual tension between us, but I came to believe he was just a cock tease, wanting to be desired, without any intention of ever following through.

And here he was at my party, ready for... something ... and I wasn't there. And least not downstairs in the play area.
I guess he wasn't feeling the crowd, so he left early and I caught him on his way out:

Leaving? No, you can't leave! You came all the way out to Brooklyn, you can't go already!
I invited him back into the basement with me to just hang out. No pressure! (Was he even interested in hanging out with me in a sexual environment?)

But he insisted on leaving. Or at least not going back downstairs!
I touched his ass to encourage him to stay, still he declined. Just touching his ass though gave me a hardon, so I directed his hand to my crotch. He happily grabbed it, but still didn't want to re-join the party.

How about if we go upstairs? I have something I want to do...
And there's another friend coming that you will likely be very attracted to...
He took the bait!

So I brought him to my private lair upstairs on the second floor and asked him to lay down on the couch in the living room -- on his stomach. I told him I was going to give him "a form of massage." And then I went into my bedroom and brought back The Flogger!
The Flogger is a whip of sorts, made of soft deer skin leather. The braided handle is about 8 inches long and the whip part is comprised of just over 50 strips of soft leather that are 16 inches long and a half inch wide -- each strip is black on one side and purple on the other. And incredibly soft.
The thing is, it doesn't hurt when you get hit with it (unless you're whipping as hard as you can!) It's more like a hard pillow fight, perhaps similar to monks' self flagellation creating ecstatic states or the thrashing of oak or birch leaves at a Russian Bath House.

Whatever it resembles, my young sexy cock teaser was open to trying.
As his head was face down in a pillow on the couch, I began!
I stood on the side of the over-sized moss green davenport with lots of room to swing the flogger. The first strike hit one side of his upper back.
He immediately liked the feeling. The noise it made was misleading though; it sounded worse than it felt.
After striking the upper side of his back, I dragged the strips across his body and head and then pulled back up and struck the other side of his upper back.

It wasn't long before I got a rhythm going, hitting one shoulder, dragging the whip over his body and then hitting the other shoulder. Then I decided I needed to give his amazing bubbly ass some attention! I asked first and he was eager to give it a try, so I twisted my body around and did to his ass what I was doing to his upper torso. Dragging the strips between his legs, across his body and over his head and then whipping it across his rounded ass. It was a full body experience.

After doing this for about ten minutes and really putting my guest into a relaxed state, I noticed a shadow passed by. Was someone there? Low and behold, hiding in a shadow against the wall behind us, was the Latin guy I power-topped for 90 minutes at the last LGBT party (when I performed in drag)! He was there to join in -- as planned.

I asked the Flog Boy how he felt about someone joining us.
He was into it.
Oh --- and by the way; he's already here in the room with us!
Flog Boy was startled but totally got into it once he saw how hot and muscly the Latin guy was.

So I flogged for a bit more and asked about stripping down. Before long, all three of us were naked and Latin Muscles was sucking Flog Boy's cock.

Suddenly we were interrupted and my presence was required downstairs.
Oh fuck -- that's right -- I have a party to run!
Apparently someone didn't want to take off their pants and was walking around clothed, against the rules. He said he had burn scars on his legs and was too embarassed to take his pants off. I offered him a Union Suit (underwear that covers the legs and arms, usually used during the winter.) He declined and went home, leaving his friends to fend for themselves.
Situation dealt with.
Now, back upstairs.

When I returned Latin Muscle was eating Flog Boy's ass. I was jealous!
After a while it became clear Flog Boy didn't want to fuck or get fucked or suck anyone. Latin Muscle grew bored and went downstairs to join in the party. I would be down their shortly...

Alone again with the caramel skinned blue eyed cock tease, I asked Flog Boy if I could eat his ass. He was up for it, but only if I was good(!), because we was getting tired and wanted to go home.

And so I ate his ass. And ate and ate and ate.
He said it was good, which was evident from his moaning, which turned me on even more! I went on for quite some time -- as is usual in situations like this. I was in heaven!

I have to admit, I don't even remember if he came. But something must've happened for it all to come to an end, for him to leave and for me to join Latin Muscle at the party.

Overall I was glad to eat the ass of someone I've lusted after for about two years -- when I first met him working the door at a party in the East Village. That club no longer exists but he certainly left an indelible mark! And I got to finally make a fantasy come true. Maybe next time -- if there is one -- he'll let me fuck his bubble butt.

With Flog Boy out the door, it was now time to join Latin Muscle. He was already into the party being a pig, squatting down on the floor, sucking a big dick. I watched. And on occasion interacted. But feeling I had already experienced my highlight of the night -- fulfilling a long standing fantasy, I was more than happy to be a voyeur, and I ended up shooting my load for the night all over Latin Muscle's face as he deep throated a bisexual guy's big dick.

As planned, Latin Muscle spent the night, the next day being the Fourth of July. We spent the entire day together, a large part of it just lounging and chatting, doing some more flogging and getting to know each other better. We even had a fucking session that ended with lots of bite marks and hickies on Latin Muscle's upper back. How did that happen?! :-)

After watching the Macy's Fireworks on tv (we tried to see them from our Brooklyn rooftop, but the Manhattan Skyline blocked our view) it seemed like the right time to go to Prospect Park. It was balmy out and about 10:30pm. When did the Park close? I heard there was a cruisy area called the "Vale of Cashmere," but there'd been a gay murder there in the past and in 2000 four gay men were attacked over a period of two weeks by someone dressed as a ninja!
Was it even safe to be going there at night?

Latin Muscle hadn't heard those stories, though, and there's always strength in numbers -- unless our "number two" met up with a "gang of five" teenagers out looking for trouble on the Fourth. I crossed my fingers as Latin Muscle proceeded in blissful ignorance.

He had only one thing on his mind: to be naked in nature. And dammit if he didn't strip down completely as soon as we were in a secluded area. I happily joined in, always aware of potential police cruisers on adjacent roadways or any light colored lumps in the landscape that might turn out to be people. It was that dark.

After getting rimmed aggressively by Latin Muscle on one of the many paths we traversed, we finally made it to the Park's biggest waterfall.
Were we even near the Vale of Cashmere? Who knows, but L.M. stuck out his ass and demanded to be fucked. I felt the area was too well lit and recommended a more shadowed area. He didn't want to do it at my location... or maybe I chickened out.
Point: we didn't fuck in Prospect Park. But he did eat my ass and we ran around naked a lot and encountered only one person (uneventfully) on the paths in our state of undress. We even saw a raccoon. It was an exhilarating experience. Equals parts scary and liberating!
And clearly something best done with a partner.

It was a nice way to end a holiday weekend that was full of flogging and aggressive sex: by watching fireworks in the sky and getting naked in the woods!

And I think I haven't seen the last of hombre latino del músculo!

The Halftime Report

It was six months ago when I began this blog, with the intention of writing entries for one year -- about the sex party space that I oversee.
That makes this halftime -- a chance to recap before I proceed with the second half of this year's parties.

But it seems like what's come out is more about my own sex life and less about running a space -- except for the excruciatingly detailed entries about the oft backed up sewer system (no more, I promise; I've heard the complaints!)

So, how about the highlights and low points, thus far?

The low points are really the sewer backing up. (Sorry, there I go -- mentioning it again!) It ruins everything, especially if it happens in the middle of a party. It's a lot to deal with, which is probably why I write about it in detail, a cathartic way of purging the experience, eliminating it from my system, so to speak. But being backed up is... draining to say the least.

And I have to say, we've been pretty fortunate in not having any dangerous stuff happen, which is shocking considering the level of insanity that happens behind these closed doors. Perhaps those Affirmation Circles before the parties are working! Or maybe what we're doing just isn't so dangerous after all.

Perhaps kicking four people out for barebacking in the span of 20 minutes was also a low point -- and kind of a slap in the face (Mmmm, humiliation!) -- an affront to the clearly posted rule to not bareback. And a threat to my livelihood -- FUCK YOU guys! (Nice to purge again!)

The highlights?

Bringing in the doctor who tests for HIV/STDs has been a very good thing and, along with the strict no-barebacking policy, ups the ante in our attempt to provide positive options and send a clear message of healthy responsibility to the sexually active community.

It's also been a lot of fun starting the new trannie event, getting dressed up and liberating other men to do the same. It makes me realize what an important role these parties can have in peoples' lives. This is the fringe of the fringe, so for people to find a place that accepts us and embraces our kinkiness -- yay to that.

I've even gotten more into the performing aspect with the singing on stage, some lipsynching and hosting of shows. It's something that hasn't come easy as a shy middle child from the Midwest. Sex in public is easy for me, but formally entertaining on stage? Not easy, unless I get to be the host/hostess in charge and then it's fun!
In real life I think I'm pretty animated and goofy and somewhat entertaining, so why not do it on stage? And now, after a few attempts, I've faced those fears head on and succeeded -- all accomplished amongst friends who are non-judgmental and accepting (at least on the surface)!

It's liberating. And isn't that what this is all about?

To that end, I think I'll start telling more about myself in this blog, since I've stayed pretty anonymous through the first six months. Granted, most people reading this are linked to it via my Facebook page so they already know me (perhaps too well, now)!

But there might be people who don't. And for those people, let me introduce myself, my name is Michael Wakefield and I was born in Michigan in 1962. (I may be old on the outside, but I feel very youthful on the inside.)

FYI to my NYC friends: actually I was born Michael Cash Backman, but changed my name as soon as I moved to NYC in the Spring of 1985 after getting a Bachelor's Degree in Design/Photography at the University of Michigan School of Art in Ann Arbor.

That's enough for now. Let's not get carried away! There will be more to come.

As the next six months progress, I'll let you know how I came to host sex parties and share a story that was published about being arrested at one of my own events.

Yes, I am a sexual outlaw. And I have the mugshot to prove it.
(Not that I've ever seen it, but I'd like to.)