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Valentines Day Cuckolding Session and Orgy

21st February 2020
 by 
Oz Bigdownunder

My Valentines day was very romantic involving a cuckolding and forced bi session with a sexy couple and an orgy with the inimitable Mr A and seven other escorts.

Mr A's sessions are always something very special. He chooses the best of the best to invite to these events. I've been lucky enough to be invited many times over the years and each one has been a star studded affair. Mr A likes party games and loves it when we put on a show. He has a brilliant imagination when it comes to inventing sexy games, shows and fantasy party themes and chooses escorts to attend his parties who share his delight in making these ideas a reality and who can add their own unique touches to the themes of the evening.

Subby Katie and I were scheduled to perform the first show of the Valentines Day Extravaganza.

Cupids Bow and Arrow Show

I came up with the idea of a cupids bow and arrow show with audience participation. The plan was to write sexy instructions on a target. Katie would hold said target over her adorable bottom and then ask guests to fire a toy bow with little suction tipped arrows at the target and act out whichever instruction they hit.

I asked Katie via twitter if she liked the idea. She loved it! So I stopped by Hamleys toy store thinking they'd surely have a cute little pink toy bow and arrows. They did not but I got directions from store staff and found the closest thing they had. A crossbow. So cupid got a weapons upgrade. I bought the crossbow and took it home, assembled it and fired a few suction tipped arrows at the target. Much more powerful than I'd intended.

I shot myself in the leg a few times to test whether it would be safe for Katie in case she took a stray shot on her bare skin. Painful but no bruises. She's a professional submissive who takes spankings and canings far more severe than the impact of the suction darts. But the crossbow is an intimidating looking beast so I made  a mental note to fire a few test shots with her before the party and make sure she was ok with it. Next I dropped by the post office and bought a white paint pen to doodle on the black sections of the target with.

valentines crossbow

Cuckolding Couple

That afternoon I had an outcall to a hotel to see a couple for a cuckolding and forced - bi session.

So I wrapped up the crossbow to take it on the tube lest constabulary arrest me for carrying an offensive weapon. The plan was to do the first outcall then go directly from there to meet Katie at a pub near Mistress Eve's place where the orgy was to take place. Katie and I would have a drink together and plan our show then arrive at Eve's together.

First stop, cuckolding couple. The lifts at their hotel were keycarded so I'd arranged with K to meet her at the bar downstairs so she could use her card to activate the lift and we'd go up to the room together. I'd arrived a bit early so I had one drink and re-read K's emails where she'd detailed how they'd like their session to play out. I'm always delighted when I can tell someone took the time to research my website in great detail to ensure my services align perfectly with their desired scenario.

K had mentioned specific blog posts in her emails and given detailed step by step instructions all of which showed that they'd discussed and planned this with loving attention to detail. They gave the impression they both cared a lot about making this session perfect. I'm a perfectionist too when it comes to all things erotic. Her email also mentioned some points they'd like to decide in the moment. This balance of planning and allowing for spontaneity had the makings of some extremely hot fetish play, fantasy and fucking 🙂

valentines cuckold

When we entered their room together, Mr K was waiting patiently. On his knees with has hands behind his back where Mrs K had left him with strict instructions not to move a muscle whilst his Mistress went to collect me.

I greeted he who's cherry I was about to take with a friendly handshake and hello nice to meet you. Seems to me it's best to meet people for the first time out of character initially to allow a sense of the real me before starting the scene just to build a basis for them to trust me.

I adjourned to the or bathroom to wash up. Only polite to at least wash one's hands and cock prior to a deflowering.

I returned anon and wasted no time in re-acquainting with the cuckold in the more conventional manner. By slapping him across the face with my semi erect member.

Deepthroating Like a Pro

K, reprimanded Mr K, where are your manners?! Return that greeting this instant. Mr K did so with aplomb. Fondling my balls and beginning to suck my cock. Timid at first but gaining in confidence and enthusiasm with every passing second. Within minutes he was deepthroating like a pro. I assured him that choking, crying, gagging etc are all more than welcome and not to be ashamed at all by his body's reaction to nine inches ramming down his tonsils.

K and I gave him a few pointers to improve his form. Several times K was obliged to throttle him and give him a good slapping about the face just to reinforce lessons learned but on the whole he was a very gifted amateur.

His lessons complete, I asked if he'd enjoyed his first cocksucking experience. Perhaps a redundant question considering his throbbing erection. Very much affirmative.

K instructed Mr K as we moved over to the bed, leaving him to watch, "you're allowed to watch but don't you dare fucking cum without my permission!"

No mean feat it seems as our show turned him on so much that I could hear him gasping and whimpering as his whole body trembled with the tension of being on the edge of the forbidden orgasm.

K's email mentioned we may or may not have sex depending on her mood but I knew the moment our eyes met as we left Mr K and approached the bed, that her mood could be best described as horny as fuck. Also, as my wandering fingers soon discovered, she was extremely wet. A veritable Punani tsunami. A Dreamtime deluge. A Biblical flood. Modesty aside, I'm taking some of the credit for that, Sex-God that I am. Smouldering good looks. Adonis-like physique. Hung like an innocent woman during the Salem witch trials.

I digress. Due credit to Mr K for being an exemplary sub. I'd got some sense from the emails that they were both having a lot of fun with their BDSM play. An assumption that became a certainty when I saw how turned on they both were by each other as they played their respective roles as domme and sub, Mistress and slave, cuckold and cuckoldress.

K and I made the bed shake, the earth move and quite possibly caused a seismic shift in the Eurasian tectonic plate.

Mr K's Turn

I was considerably more gentle with Mr K when it was his turn. I slipped a condom on two fingers, lubed it copiously. Opened him up with one then eventually two fingers. Then put a condom on my cock with more lube and very very slowly started to press the head of my cock against the outer rim of muscle of his ass.

After a few tactical retreats to re-lube, I eventually got just the head in there. Barely moved for some time. I massaged his shoulders and ass cheeks and promised I wouldn't go any deeper for now. He placed his trust in me and his body responded by unclenching his muscles. His ass was the last part of him to relax. One last splash or lube and I was able to go halfway in, get some slow movement going and after a while he was taking it like a slut.

When he'd received a pounding almost unheard of for a first timer, K rewarded him by allowing him to choose the moment at which I'd withdraw and cum on his face. He took it a while longer and when he did beg for my cum, I gave him his just desserts.

Onward Ho! To the orgy!

Katie and I had a nice catch up at the pub. Chatted about my travels over winter and recent TV and movies we'd seen. 1917 which we'd both seen and loved. Jojo rabbit which I'd just seen and Katie was planning to see asap. Recommended. Knives out. Avenue 5 etc.

We walked to Mistress Eve's place together and arrived early to get ready. I rang the buzzer and there was no immediate reply. After a while we heard Eve chastising one of her girl slaves for tardiness in letting us in. The putter patter of tiny slave girl footsteps scampered towards us.

Slave Lydia greeted us with a curtsy. I have her a good slap on the bum and greeted Mr A, the man of the hour who'd made this orgy possible with myself and seven other professionals. I said hello to our lovely hostess, Mistress Eve and to TS Alekssandra, TS Leena, Karlie Simon and Petra with cheeky kisses. And an additional squeeze of the ample tit for Morgan, Eve's other slave girl.

There were party snacks aplenty, and drinks delivered mostly promptly by slave girls. Any dallying punished immediately and mercilessly by Eve.

Our orgiastic rose petal strewn antechamber adjoining multiple themed playrooms.

Katie and I excused ourselves to change. The invitation had specified red and black leather and latex. I'd brought my black leather pants and purchased a red fishnet singlet from amazon especially. Katie duly coordinated with black latex dress and black fishnet stockings.

I fired a few test shots of the crossbow with Katie. Then showed Eve my plan for the cupids bow and arrow game and they both approved so I set to work scribbling the instructions onto the target.

Minicab Blowjob

When I was done we returned to mingle and make polite conversation. Alekssandra recounted the tale of how once upon a time I sucked her off in the back of a moving London minicab while the driver barely managed to keep his eyes on the road and off the rear view mirror which he'd adjusted for optimum perving on us in the back seat.

When it was time to begin, Mistress Eve tapped on a glass for our attention and welcomed us all. A big bravo and round of applause for Mr A for inviting us all. And introduced the first performance. Me! And my lovely assistant Katie! I explained the idea to our audience, gave Katie the target with instructions to bend over and hold it in front of her ass, handed the bow to Mr A and positioned myself behind him to help him hold his weapon steady, aim down the sight and guide his finger to the trigger.

He shot on target and hit the instruction to have oral sex with a partner of his choice. He retired to a darkroom with Karlie with a spring in his step and a boner in his pants. Everyone took a turn shooting at the target and acted on the instructions until we were all engaged in sexy fun.

Our orgy was Bacchinalian. A resounding success. Lydia fisted Petra. Alekssandra encased my head in a rimming chair. Lydia rode me like a rimming chair ensconced bronco. Karlie and Eve leasure Mr A. Alekssandra molested me alongside.

After Mr A had departed, sated and grinning ear to ear, we were all off the clock. At this point most escorts would leave immediately, but our merry crew carried on. Morgan jokingly pouted and accused me of avoiding her so I whisked her into a darkroom for a quick knee shaker.

Good times 🙂

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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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