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Encouraged Bi With a View of Winter Wonderland

29th November 2021
 by 
Oz Bigdownunder

Mistress Charlotte forwarded me copies of emails she'd received from a gentleman interested in an encouraged bi session with the two of us.

Let's call him Mr T.

Mr T had asked that Charlotte "Encourage, entice and gently coerce" him to submit to Oz Bigdownunder.

This was to be the realisation of a long held fantasy. One he had put a lot of thought into during the lockdowns.

It was also to mark the occasion of a recent birthday.

Mr T specified encouraged bi rather than forced as for him the fantasy was "not so much about domination or humiliation. More the willing surrender of control. To experience and be educated on what it is to be submissive and to be penetrated for the first time."

He'd had some experience with pegging but was planning to try to take a real cock in his ass and was both nervous and excited.

He wanted his Mistress to take the directors chair and "direct our activities, positions and tempo. All the while providing words of encouragement."

I read through the list of activities he was comfortable with. "Touching, giving head, receiving covered anal and CIM/swallow/facial or cum on body."

With regard to the cumshot he'd specified "You call the shots. Especially the cumshot. When, where and how I receive Oz's cum."

The idea was to help him progress from "nervous first timer to enthusiastic beginner."

All of the above gave the impression of an inexperienced but very thoughtful and considerate gentleman who had done his research and made our task of creating a perfect experience for him much easier by preparing and communicating clearly how he would like the session to go.

As arranged we met for a drink at the lobby bar. Mr T and Charlotte arrived first and as instructed I arrived 30 minutes later. Mr T was all smiles as we were introduced and was clearly delighted to meet both of us and revelling in all the naughty comments and flirtation between charlotte and I.

I told Charlotte she looked ravishing and she treated me to a little hula shimmy that made her ample bosoms jiggle most enticingly.

The bar was Polynesian themed so I erected a totem pole under the table in her honour.

We discussed difference between forced bi and encouraged bi over drinks. I like this concept. Kink is absolutely not all one flavour. Not everyone who sees a Mistress wants to be punished. Mr T chose very wisely in employing the services of Charlotte and myself. We're both experienced and flexible in our respective approaches to BDSM and kink.

Charlotte is very verbal and excels at bossing around naughty boys. Mr T and I both did exactly as we were told and Charlotte kept us on our toes with a barrage of orders and instructions delivered with the perfect tone of firm encouragement.

Mr T's very chic top floor penthouse suite overlooking Hyde Park had a spectacular view illuminated by the Winter Wonderland Fairground.

An impromptu photoshoot ensued. Mr T proved a capable photographer. He captured an emotive portrait of my cock and Charlottes strap-on illuminated by the background glow of a neon skyline.

My big dipper resplendent. Charlottes silicone schlong perched atop a Ferris Wheel.

We retired to the Master Bedroom. At length, and with ample encouragement, we had Mr T on his knees and sucking my cock like a pro. Charlotte directed the action and Mr T and I received a commendation for our efforts more rousing than any standing ovation.  ie Charlotte took out her magic wand and got herself off while clearly very much enjoying  our performance.

Our fucktastic encouraged bi fantasy scene continued anon after a brief interlude in which Charlotte strapped on her strap-on.

While Charlotte was pegging Mr T, I straddled his face on an angle allowing me to dual wield my own dick and his. There's a real science to this. It's not just handling two poles simultaneously like you're cross country skiing. There's tip to tip efficiency to consider.

Silicon Valley actually employed a team of mathematicians to help with the equations on the whiteboard as a team of software engineers react to the statement "I'll go into the auditorium and personally jerk off every guy in the audience,” by attempting to calculate how long it would take to jerk off 800 men to completion. If you're into maths (and/or wankbangs), here's the full write-up of their findings regarding the most efficient technique involving pre-sorting members by girth and length for optimal double jerking.

We switched ends and Mr T just managed to take the tip of my cock in his ass.

I'm sure next time he'll take it deep and hard after some more encouragement from Charlotte and some pegging with a bigger strap-on to open him up.

I returned to the teabag position. Dipping my balls into Mr T's mouth whilst Charlotte gently impaled him on her crotch mounted dildo. Liberal application of our respective phalluses (phalli?) to his prostate and throat soon had Mr T deep in subspace as he submitted completely to being spitroasted by us. In this suggestive state he was on the edge of orgasm. Only complete obedience to his Mistress preventing him from climaxing. Charlotte instructed me to cum on Mr T's face and I did so with a biomass akin to a Barrier Reef spawning event.  At her leisure, Charlotte withheld Mr T's instruction to cum until the exact moment beyond which he'd have been powerless to hold back a second longer and only then gave him permission.

4.8 4 votes
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Author: Oz Bigdownunder

Australian Bi male masseur and escort for men, women, threesomes with couples and duos with female or transsexual escorts.
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