Sissification, Cuckolding & Encouraged Bi Duo with Lilly Watson

Lilly Watson's regular, a sissy who loves to be feminised and teased with a strap-on, finally got up the nerve after many years to arrange a duo with a male escort.

I'm very pleased that I got the invitation for a duo with illustrious Sensual Domina Lilly to be the bull in sissy's long held fantasy.

The initial request was for cuckolding and forced bi. In the next message this had been re-worded to firmly encouraged bi. Then in a confirmation email "light on the bi". So I got the impression the bi aspect of the session should only be very gently introduced.

Not shoved down his throat, as it were.

Sissy had specified via email that the idea was to tease. A little touching and licking. Probably no real oral due to a sensitive gag reflex.

What a delicate little flower!

Subtle foreshadowing. Any guesses what the plot twist might be?

The other request was that I wear a suit and plain black underwear for an authoritative vibe.

I don't often get an opportunity to wear a suit. Always happy to dress up when the occasion arises. Suits do look amazing in my slim, toned, 6'5" frame. I got a few looks riding the tube. Looks that said they'd like to ride my tube.

The new Elizabeth line at my local Bond St is magnificent.

I entered Her Majesty's tunnel. Took the rear entrance. Prominent bulge of Bigdownunder underground. Daydreaming of Lilly's caboose. Would very much like to run a train on her. Sorry, one track mind.

Back up the exit shaft I emerged amongst the gleaming edifices of Canary Wharf. Ready to let off some steam.

Arriving fashionably early, I waited at the bar and people watched with a practiced eye assessing each solo gentleman entering the bar to determine who was most likely to be my sissy.

At the agreed time, sissy arrived and I knew at a glance that there was a man who'd be happiest in his knees with my giant cock slapping his face.

Against the unlikely possibility that I was mistaken, I sent him an email and sure enough his phone went ping. We got a table together and were soon joined by Lilly.

Radiant as always. Glamorous in vintage chic, glowing with sex appeal, her every word and mannerism a delightful tease of taboos soon to be broken.

After a delicious negroni, we adjourned to a nice suite with a view of the city. We took turns showering. Ladies first. Sissies second. Me lucky last. When I came back from my shower Lilly had sissy fully sissified, wigged and pantied, hands cuffed, on a chain connected to a collar , on her knees.

I complimented Lilly on the alacrity and finesse of the transformation. And complimented sissy on her panties. Panties she was already wearing under her clothes when she met me in the bar, she confessed, nervously.

"Excellent! That's commendable." I assured her. You came here dressed for the occasion.

As did I. Naked under a hotel bathrobe. Sissy was getting an eyeful at this point. Soon to be a mouthful.

We gently encouraged some kissing and licking of my cock.

But then plot twist sissy almost instantly lost all inhibitions and began greedily sucking without even needing to be told.

Our purportedly pristine protagonist had hidden talents. How she came by said talents was cause for speculation.

And why she was wantonly gulping down my member without following the correct protocol of awaiting Mistress' step by step instructions? Cause for chastisement.

No decorum whatsoever, some sissies.

We provided the restraint she clearly lacked via throwing her down on the bed and cuffing her akimbo.

The wig fell off. Wasn't designed to be worn whilst horizontal it seems. "She's very untidy this sissy slut of yours" "I commented. "Can't even keep her wig on straight while getting face fucked. Better send her back to finishing school."

Lilly approved of the idea and provided a bonus lesson in etymology. Did you know the original meaning of slut, was a dirty, untidy and slovenly woman?

Now you know. Every day's a school day. And extremely slovenly she was too, our sissy slut. Slobbering all over my cock. Wig on the floor. Lady parts bursting out of her panties in all directions.

Untidy as she was, she was only going to get messier with a couple of libidinous libertines using her for sex furniture.

Lilly and I have more chemistry than Heisenberg's camper van. We were more excited than electrons in a photon beam. Lilly in her lingerie was hotter, and wetter, than aqueous butyl lithium. I penetrated her like a supernova neutrino burst. We fucked with the intensity of a Carrington Event.

By the time we dismounted her, sissy looked a pretty picture. A picture I added my own artistic flourish to with what looked like a pearlescent Pollock painting on her face.

One spasming sissy clitty later, we performed our ablutions once more in the customary order, said our goodnights and Lilly and I ventured forth into the midst of the London banking sector's towering erections.

Later on I got a thank you email from Sissy.

"I just wanted to say thank you for a fantastic evening. It was something I’ve been thinking about for a long time so there was definitely a real chance that it wouldn’t live up to expectations but it both did that and exceeded them. Hopefully it will be the first of many!"

I hope so too!