Real Encounters : Vonda and Steven


In the past five years, I have been approached by about 3 Transmen whom have all initially asked the same question… “how do you feel about transgendered submissives?”  Now, I’ve had the same questions posed from men who like to crossdress as a way to feel submissive (CD/Sissies).  But they are radically different in many key ways.

In 1995, I went to my first gay bar and saw my first crossdresser/drag queen. I was fascinated by how good many of them were at emulating women.  But, it did nothing for me sexually.  The women I had been with were more butch than these men.  But, I still appreciated the artform that it is.  It wasn’t until I met a black submissive drag queen who went by the name Vonda, that I softened to the idea of CD’s.  She looked just like Toni Braxton when in full makeup.  Very beautiful.  And, when I lost a bet and allowed her a chance to seduce me.  When the clothes came off,  man was I surprised.  That bitch had BODY!  Athletically toned with a nice muscle ass.  Not quite a bubble butt… however, it was all firm and rounded muscle.  She was also a dancer and had done ballet (need I say more?).

I found that panties and a bra are hot on a man… with the body to pull it off.  She helped introduce her world as another facet of the Lifestyle.  Men who are bisexual and are dealing with that fact tend to appreciate the visual.  Satisfies the guilt.  Necessary in the repressive 1990’s.   Since Vonda, I have been served by three other CD’s.  One was a bodybuilder who enjoyed posing in women’s panties and stockings.  One was a politician who was in pretty good shape but enjoyed being spanked while in full drag.  He wasn’t very attractive in makeup and a wig but he had a great ass.  Spanking is also one of my fetishes so accommodating wasn’t hard since we both got what we wanted out of it.  The last was a former college athlete who failed to mention that he was into cross dressing.  He showed up in high heels and a leather skirt.  Being 6’4″, the heels made him look like a circus performer on stilts.  Thankfully, it was night and no one was around to see him or I would have had a fit.  As soon as he entered,  I made him take off all of that shit.  Dressing for me in private is one thing.  Showing up in drag without a heads up is another.

I still fucked him.  I liked what I saw underneath his armour.

And, that’s what he called it when I told him to explain himself.  He said it allowed him to be himself.  Made him submissive.  Now, I’ve always thought one knows their place instinctively but some obviously need help in getting there.

Starting in 2013, I started receiving contacts from women about to transition.  They identified as male but still had a female body (having only just started on testosterone).  But yet they were attracted to men.  Gay men in female bodies.  That was a bit too much for me at the time.  I just told them that I appreciated their courage in coming to me but that I was looking for men only.  They understood and appreciated the respect I gave them.  I respect everybody.  As long as you show me respect first.

In April 2016, I was contacted by a guy named Steven who identified himself as a transman.  I’m still getting used to the new terminologies for the Trans community so was intrigued to find out more. He sent me a photo (which I won’t share out of respect for his privacy) and all I saw was a VERY handsome and muscular guy.  No tell-tale scarring around the pecs from what I could see from the shirtless photo.  Just a slightly hairy, beefy guy.  Nice 17″ arms, bulging 45″chest.  Military standardized haircut.

I granted an interview.

He was in Colorado Springs at the time and drove the nearly 2 hours just to meet.  I didn’t know what to expect and was a bit apprehensive.  But, he updated me every 30 minutes on his progress by text.  I didn’t require him to do that but he wanted me to know he was serious and not a flake.  I appreciated that.

Arrived on time to the minute (gotta love the focus on punctuality) and when he entered, looked exactly  like his photos.  Except photos are only two dimensional and never really give a proper perspective.  Much better looking in person.  He extended his hand in a firm handshake and greeted me.  Deep, masculine voice.  He had told me that he was still pre-Op but had been taking regular injections for five years during which time he had his breasts removed.  And had been in the military for three years after that.  He is 5’10, solid 190lbs, cropped beard and mustache, with deep blue-eyes and black hair.  There was no way this guy had been a female.

As I do with anyone who claims to be submissive,  I had him strip naked in order to present for inspection.

Hot Damn… that boy was put together well.  He caught my expression as he was taking off his clothes and smirked.  I saw that smirk and once he was fully nude in front of me, I grabbed his chin and forced him to look at me.

“What the hell are you grinning about?”

“Sorry Sir,  I was nervous until I saw you checking me out with approval. Sir!”

“What makes you think I approve?”

“Sir, I don’t. Sir.  But I was worried that I wouldn’t appeal to you physically.  Sir.”

I released his chin and stepped back to begin my inspection.

He was already standing up straight with his hands behind his back and head down. Breathing rather rapidly… which made me smile.  He was nervous again.


I hadn’t looked at his crotch yet.  Mostly because that area doesn’t interest me.  AT ALL. Well, maybe for some sadistic pleasures but that’s about it.

I traced my fingers across his shoulders to his arms.  Gripping both biceps… unflexed, they are impressive.  I trail back up to his chest.  I saw a thin scar line and traced it with my fingertip.  One pec jumped in response.  Nice.

“Got some meat there.  Flex your chest for me.”

Most guys would look at me with confusion in their faces but not this one.  He smiled again and began to make his pecs flex in unison, then individually.  Nice muscle control.

“You can stop.  Very nice.  You have obviously worked hard on your chest”

“Yes Sir!  I was building up my chest even before my top surgery. Sir”

I moved down to his abs.  There was still a layer of fat there but you could see the obliques.

“Turn around”

I purposely didn’t allow my eyes to go further than his abs.

“Sir, yes Sir!”

When he turned, I saw a pair of nicely rounded glutes staring back at me.  I grabbed each one in my hand to gauge their texture and weight.  He instinctively flexed.

“Someone has been doing squats”

He chuckled,  “Yes Sir!  I know Black men love ass and I always had one before but I wanted it to be a man’s ass, Sir.  I’m all man, Sir.  And I wanted to present as one.  For you, Sir.”

He was trembling as he said that and I turned him back around to face me.  He was struggling not to show emotion.

I didn’t comment.  He had impressed me already.

“Good job soldier.  Those squats and your workouts have paid off.  Very nice.”

The trembling stopped immediately along with an emotionally whispered.  “Thank you…”

“I’m sorry, I didn’t catch that.  What did you say?”  A little more forceful than I intended.

“Sir! Thank you!  Sir!”

I grunted.  I then took a moment to check out his legs which were equally built… like tree trunks.  Always liked big legs on men.  Hell, liked them on women as well.  Usually equated to a big ass (but not always).  I purposely raised my eyes to his crotch.  There was alot of hair down there.  Very bushy.

“Somebody needs to mow their lawn”

The trembling started again.  He was trying not to laugh.  I smiled.

His clit looked like a small penis.  The testosterone and steroids (which learned later he had used in the past to bulk up) had enlarged it.

I wasn’t grossed out or anything.  I was actually fascinated.  This masculine body with a pussy. A very hairy one but still a pussy.  I have been served by eunuchs  before (castrated males) who were made that way by their Masters.  To take away someone’s dick and balls quite frankly takes balls… from both sides.  Not my cup of tea.

If any of my own subs are reading this… I would never do that to you.  Jockstraps and chastity cages hide what I want unseen quite effectively.

He served me well that night.  We talked about his experiences.  It was a world I never knew existed.  Of men and women born one way but were supposed to be another.  How the military handles transgendered personnel.  Of his fear that I would reject him as not being a biological male.

He served up til he left before Memorial Day for Hawaii.  He has an open invite to return for service if he’s back in the area or I happen to be vacationing in Hawaii.

Transmen and Transwomen just want to be given the same opportunities as everyone else. Sound familiar?  Black, Gay, Hispanic… everyone knows (or should know) what it feels like to be discriminated against.  Not saying that you have to sleep with everyone or not have personal preferences but at least acknowledge them if they are doing nothing more than trying to give proper respect.  Everyone deserves a chance if they are working their ass off to gain one.

I admit to at one time having a prejudice against something I didn’t understand.  But people like Vonda and Steven can show that as long as you give someone a chance,  you can be surprised.

This is an open invitation to Transgendered men to seek service if that’s what you feel in your heart you are destined for.  Feel no shame in being a Man.  Feel no shame in being a Woman.  Just as no one on this site should feel shame for being a submissive.

There is no better FREEDOM than being who you are.


NOTE:  The guy in the featured image is NOT Steven.  That is Aydian Dowling, a Transman once featured in Mens Health.  But their bodies are VERY similar.