Chapter 8: The Ultimate Session

I remember being fascinated by drag queens from a young (but legal) age. Transgirls were just people to me. I accepted immediately that some of us were born into the wrong gender and that these beautiful people needed our love and support, not our disdain and ridicule.

Drag queens are different. These queens are ‘over-blown, over-exaggerated caricatures of women’. Drag queens take the things women do naturally and then multiply them into comedic characters. A drag queen’s walk, talk, and body language is a woman’s multiplied to the ‘nth’ degree.

I love them and find them hilarious. I especially like the queens who aren’t making the slightest attempt to ‘pass’ as a woman; they’re just exaggeratedly mimicking them.

In Brisbane, where I live, there’s an exceptionally gifted drag queen called Mandy Moobs who creates most of the drag shows at The Sportsman Hotel in Spring Hill. If Mandy ever decides she’d like to have an affair with an overweight, almost 60-year-old, I will have to see if Vicky will allow it.

I formed a plan to expand Vicky’s and my sexual experiences further. Because I had insisted my wife try lesbian sex, I thought it was only fair she experienced me having homosexual sex.

As a male, without sexual arousal, i.e. an erect penis, sex is virtually impossible. Masculine males, as observed above, do nothing for me.

Being a cab driver for a time meant many gay men hit on me. But, for them, it’s a doomed cause because I have no attraction to the masculine. Their hitting on me never bothered me; I just didn’t feel any sexual attraction in return.

I trolled through ICQ again, but its popularity had waned by now, and I had no luck. I was looking for either a Transgirl who liked to top or a convincing transvestite or crossdresser who would do the same.

Notes:I do not pretend to be an expert in this field. The definitions and explanations following are my experiences, and I do not speak for anyone else.

Definitions:

Crossdresser:Someone who likes to wear the clothes, especially the undergarments of the sex generally recognised as opposite to them. They may or may not try to present as close to the feminine as possible if they’re male. Or as close to the masculine as they can if they’re female.

Personally, I would call men who don’t want to present as female, but get sexually aroused by wearing lingerie, fetish dressers, not crossdressers.

Transvestite:Someone trying to mimic the gender generally seen as opposite to theirs. They will go to all possible lengths to try and blend in with the sex they are portraying.

Transgender:Someone who believes that they have been into the wrong body. Even though all outer appearances suggest they’re one gender, their minds, emotions, and psyches tell them they’re the opposite of their physical sexual organs.

There are more than the three I have described above, but I’m already way above my pay grade and have no wish to go further.

Explanations:

Guys, if you’ve ever wondered why it’s almost impossible to find anyone other than a trans prostitute to fuck you in your ass, this is why.

When it comes to sex, 87% of transgirls identify as bottoms. In other words, they want to be fucked, not to fuck someone. Some 48% identify as lesbian or bisexual with a preference for women or other transgirls. Another 29% identify as queer, asexual or other. That leaves a miserly 23% that identify as heterosexual and will want to have sex with you. I.E., They’re a woman (or believe they are). You’re a man. Therefore, the sex is heterosexual.

87% of these few transwomen who will have sex with you will want you to fuck them. They’re unlikely to want to fuck you.

Let me put that into numbers so you can understand. Take a sample of 100 transgirls. On average, 87 of these girls want someone to fuck them. Only 13 want to fuck someone.

Only 23% of these 13 transwomen identify as heterosexual. I.E., they want to have sex with a male.

Doing the sums gives you a final figure of less than 3 out of 100 transwomen who will consider fucking a man in his ass.

I suggest you get off the Brazilian trans porn sites you’ve been visiting and join a site like Fetlife, where you can do some actual research.

Back to the story...

... I trolled through ICQ again, but its popularity had waned by now...

As I could not find a suitable Top in any of these categories, I changed the parameters to ‘transgirls who like couples’ and had a deluge of girls to choose from.

I approached several girls before one named Kate Coxx answered. Kate and I exchanged messages for days as we sounded each other out. I explained that as we spoke, my wife had no idea I was approaching transgirls intending to have sex with them. But, before Kate and I met, I’d inform my wife. I reassured Kate that my wife would be coming to our first face-to-face chat.

Kate is a gorgeous girl. Tall and slim, with long legs and a ready smile, Kate is one of the few trans girls that can ‘pass’ in most situations. In addition, Kate has natural ‘B’ cup breasts.

Kate is very submissive, and her desire has always been to serve a Dom/me couple. I had sent pictures to Kate of my wife and me together. Nothing even remotely risqué, as I wanted Kate to see us as people first, not sexual partners.

Note:If you choose to send nudes via the internet, do not be surprised when your account gets hacked, and those pictures are shared a gazillion times.

Back to the story...

Once Kate and I were sure the other was genuine, I brought Vicky and Anna into our conversations. My wife expressed surprise that Kate was trans. Anna thought that Kate was beautiful, but that it was obvious Kate wasn’t a ‘real’ woman.

Vicky demanded to know why I was talking to Kate. She stated she was happy with the two submissives we already had. She wondered why, if I wanted to play with a crossdresser again, didn’t we go and see caroline?

I explained that caroline was for her and that, sexually, caroline did nothing for me as she was too obviously male for me even to contemplate having sex with. I further explained that I wanted her to experience what it was like to see her spouse having same-on-same sex.

Vicky pointed out that Kate, being as gorgeous as she is, hardly counts as man-on-man.

I then brought up the one graphic pic that Kate had been kind enough to send me. This pic was of Kate standing in front of a full-length mirror with her face covered by the camera. She was dressed immaculately from head to toe, except that she had pulled her leather skirt down far enough to reveal her rampantly erect 7-inch cock.

“Wow!” Vicky exclaimed. “That looks so weird sitting on someone so feminine.”

My wife bit her bottom lip before adding, “Hot as fucking hell, though.”

“Kate likes receiving oral,” I said quietly into the silence.

“You’re going to suck that?” Vicky asked in disbelief.

Blushing, I answered, “I’m going to try. But, I don’t know if I can.”

“I think I’d like to see that,” my wife almost purred.

I could see and almost feel her arousal.

“What is my role, Master, if I may ask?” Anna queried.

“You’re part of our family now, my little natalia girl. Your role is to be informed your Mistress, and I are contemplating taking on another submissive.”

“Yes, Sir,” Anna replied.

It was Anna’s time to bite her bottom lip, “May I be allowed to play with Kate, too?”

Vicky answered before me, “Not the first time, little one. If it goes well, I may let you join us in later sessions.”

With those words, I knew Vicky was already ready to have a play session with Kate. Plus, she was considering more than one.

Note:Kate Coxx is one of the few transgirls on a complete HRT program that can still achieve and maintain a full erection. In over 95% of cases, introducing oestrogen into a biologically male body kills the ability to go hard.

That is another reason those Brazilian trans sites you’re visiting are bullshit. If the girl looks that feminine, there’s no way she is not on HRT. To be erect, that woman has taken some kind of chemical to get there.

Back to the story...

We arranged to meet Kate at The Coffee Club in West End. This coffee club hosts a regular Wednesday night meet and greet for the local Seahorse Society, so neither the staff nor the patrons are surprised at seeing transwomen.

Kate lives full-time as a woman but is still reticent about being seen in public places. She never explained why and I thought it rude to ask.

Vicky and I arrived on time for a change. The time we had agreed slipped past, and another fifteen minutes elapsed. I was about to call Kate to make sure she was okay when she called me.

Kate was suffering a panic attack and had frozen inside her car, unable to get out. Checking where she was, I walked to the downstairs parking area. When I got there, Kate timidly opened the car door and got out.

I looked her over admiringly, “Miss Coxx, you are stunning!”

Hearing and seeing me so openly smitten seemed to allow Kate to relax.

“I’ve had so many men stand me up, John. I just couldn’t go up there and face another rejection,” she explained.

For our meeting, Kate had probably gone a little over the top. Her attire was more suitable for a nightclub than a coffee club. She was wearing stockings with suspenders over stiletto heels that had to have been at least 7-inches. Above the suspenders, which were clearly visible below her skirt’s hem, she had on a clinging micro-mini skirt. Her top was backless and barely covered her tiny nippled ‘B’ cup breasts.

Kate has pierced ears, a pierced nose, and a pierced belly button.

She is glorious. Any man should have been ecstatic she was holding his arm. I was!

Note:Boys, experienced transwomen and crossdressers get that the imminent reality of a play session or meet and greet with them can become overwhelming, and you need to chicken out. But please have the decency of calling or texting them to let them know you’re not coming. Please don’t leave the poor girl sitting there, having been obviously stood up.

Back to the story...

With my arm intertwined with hers, I guided Kate up the stairs and inside the club. As we walked across to the table, Vicky stood up.

“Hello, Miss Kate. Wow, are you gorgeous! I’ll have to step my game up, or I might lose my hubby to you.”

Kate beamed before letting go of my arm and giving my wife a hug and kiss.

“Oh, I don’t know,” she said. “Maybe hubby here needs to lift his game before I take you away from him.”

Laughing, the girls sat down and then looked at me expectantly.

Internally sighing, I asked what they’d like to eat and drink before leaving them to become better acquainted as I went to order.

I sat at the bar, slowly sipping a beer while waiting to see what happened next. I’d almost finished the bottle before Vicky came and got me. When we got back to the table, Kate wasn’t there.

“Where’s Kate?” I asked, fearful the girls had decided they wouldn’t play together and I would have to start trolling for another.

To my relief, MsV answered, “In the loos.”

“And?”

“What? Oh. Yes, I think I’d like to play with Kate. One rule, though. You and Kate are never to play alone together. So if I can’t play with you, there’s no playing.”

“Of course, Chubby. I promised to bring you along for the ride and never cheat behind your back again. I mean to keep that promise.”

“And if I want to do a three-way with Kate and Anna?”

Holding my features still, I replied, “May I be in the room to record that session?”

Laughing, Vicky slapped my arm and said, “Sure. But you’re not allowed to masturbate.”

Sighing deeply, I pretended to be bitterly disappointed, “Well, what’s the point of being there to record it then?”

We were still laughing with our heads pressed together when Kate returned.

She sat opposite us, “What I like most about this is how close you two are. Most couples I’ve met, the woman is only going along with it because she thinks her husband will do it anyway if she doesn’t agree.

Sometimes the woman relaxes enough to enjoy the sex, but usually, it just feels uncomfortable because the man is the only one that’s truly getting what they want.”

“If you and Vicky don’t find each other mutually attractive, there won’t be any play, little miss kate. If we three play, your and my first priority will be to give MsV as many orgasms as possible before we look to each other’s needs.”

“So, you’re her submissive, then?”

“No. But I’m not going to do anything my wife isn’t whole-heartedly in agreement with. And nothing happens without her being there and enjoying every part of it.”

“I don’t fuck guys, Mister,” Kate averred. “If you want a girl to fuck your arse, you’ve chosen the wrong girl. I like guys fucking me, and I love fucking other women, but I don’t fuck guys. With men, I’m totally a bottom.”

Then she laughed, “I’m a bottom that loves getting fucked in the bottom!”

“I’m aware of that, miss kate. You told me that from the beginning.”

“Yeah, but guys still suddenly spring that shit on you. I’ve had so many men try and back their arseholes onto my cock. So if you try that, I’ll leave, okay?”

“Hard limit, miss kate. I respect all hard limits.”

Kate stared into my eyes for a long time before saying, “You know, I think you might be one of the few genuine ones.”

She turned to my wife, “I’d like to come and play, MsV. Or should that be ‘play and cum’? Would you like me to?”

Vicky took one of Kate’s hands in hers, “Yes, little one. You and I will get on messenger later in the week and discuss what you’d like to experience in a session. Then, as long as we’re both happy, we’ll set up a play date. Do you want to come to ours or somewhere else?”

“Don’t you have teenage boys at your place?”

“Yes, we do.”

“I’d rather have a motel room, then, please. If possible, I’d like to be able to stay there overnight after you’ve left. I’ll probably go to The Beat afterwards.”

“Sounds like a plan,” I answered. “When would you like to play?”

I wanted to get this locked in before my wife got cold feet.

“It’s Sunday today. Why don’t MsV and I chat during the week and try and set something up for next Saturday night?”

“Sounds good to me. Honey?”

“Next Saturday works for me. Assuming Kate doesn’t freak me out when we chat online.”

Kate smiled broadly, “I don’t want much from a session, MsV. Some bondage and a little bit of spanking. Oh, and if you’d tickle me until I have to use my safe word, that would be awesome.”

By the look of confusion on Vicky’s face, I’m unsure if she’d heard of a tickle fetish.

Shaking her head and shrugging her shoulders, MsV replied, “Whatever floats your boat.”

Vicky pointed at me, “What do you want from John?”

Kate blushed, “Your man is so big and manly, MsV. I’d love him to manhandle me all around the room as he sticks his cock in my holes. I want him to be quite rough with me, so I gag when he’s in my mouth and flinch when he takes my ass. His doing that will make me so vulnerable and weak, and feminine.

As you can see, I’m tall for a girl, so I can rarely find a real manly man to make me feel petite and feminine.”

Vicky laughed, “I’m sure John will just hate using you roughly, little one. He’ll probably immediately refuse.”

“Actually, wifey, I’d hate to disappoint the poor girl and leave her wanting,” I grinned back at her.

Standing, we exchanged kisses and hugs before I escorted Kate back to her car.

I was already anticipating next Saturday.

By Thursday, Vicky confirmed we’d be playing with Kate.

Kate was due at the motel at 6.00 pm. Around 4.00 pm, Vicky and I arrived to set up for our session.

Setting the ropes across the bed, I added leather handcuffs, ankle bracelets, and a leg spreader. Next to those items, I placed several types of blindfolds. I had a padded fake fluffy wool pair that would seal Kate’s eyes totally closed. A leather pair that bulged in the middle, also sealing the eyes closed, and a silk scarf that would make things opaque but allow Kate to have some sense of what was happening.

Which one I used would depend on Kate. Some people find being unable to see what is happening a terrifying experience, especially with new play partners.

Underneath these, I placed a row of floggers. We had the suede ‘cat’ and the smaller leather ‘cat’. Also, we had two different types of leather floggers. One was the studded one described above, and the second was longer and thinner, almost a belt, as opposed to a paddle.

The last of the equipment was a pingpong paddle and a couple of feather ticklers so MsV could satiate Kate’s tickle fetish.

Vicky was wearing her strap-on underneath her leather skirt, and she’d placed lube and sex toy cleaner on the bedside table.

Setting up only took about 15 minutes, so we had time to kill before Kate’s arrival. Vicky and I have always enjoyed alone time together, so sitting and chatting while waiting for Kate was no chore.

As the time passed 5.30, Vicky began getting nervous and a little fidgety. She kept getting up to look through the drawn curtains to see if Kate was there.

She turned to me, “Are you really going to suck Kate’s cock tonight?”

“No. I’m going to try and see if I can. Assuming I don’t freak out, then yes.”

“And if she cums in your mouth?”

“In for a penny, in for a pound, right?”

In disbelief, my wife asked, “You’re going to swallow it?”

“I’m going to try, then hope I don’t embarrass Kate by throwing up.”

The room suddenly filled with the smell of my wife’s arousal.

“Fuck, is that going to be hot!” She stated.

“If I can do it.”

“You’ll do it. I’ve never seen you fail at anything you’ve ever tried.”

There was a knock on the door. I opened it, and Kate rushed inside. Doing a quick pirouette, flaring the short robe she was wearing over her hips, Kate stopped facing my wife, then dropped the robe.

Under the robe, all she had on was a tight lacy bra and a tiny black thong.

“Sorry, Sir, Mistress, I had another panic attack out there. My apologies for barging in so rudely.”

Note:I only allow subs currently serving me to call me Master. I don’t really like the title, even from my submissives. I think using ‘Master’ is a bit of a pretentious wank. I prefer Sir or Mister Murray.

Conversely, I think Ma’am makes the Domme sound like a 90-year-old spinster aunt. Mistress sounds much more respectful.

Back to the story...

Kate assumed sub-position one.

Kneeling with her ass on her heels, her shoulders up and back, and her head held high, Kate said, “Sir, Mistress, I hope you find this sub worthy.”

As we agreed, I stepped to the side so MsV could begin the session. Vicky walked in front of Kate. She was so close that Kate’s nose was almost in her navel. Kate is quite tall, and my wife is tiny. By the sudden lick of her top lip, I was certain Kate was aware of how turned on my wife was. Kate had only tucked her penis back between her thighs. Unbidden, it rose into view.