The call from the Moneybags came four days later. Mistress R telephoned me at home late on a Tuesday night.

‘You made an impression with both of them and they liked what they saw. How soon do you think you could get out here for a session with them? It would be for the whole weekend and you’ll be staying with them the whole time. At their home – and, in their beds.’

Mistress R and I discussed my schedule as it related to my day job as well as upcoming sessions with my other clients and we soon figured out the earliest opportunity.

She then added, with some uncertainty in her voice how I would react, ‘They have already asked T, if he would join you as well, when you make your debut with them… are you okay with this? Mrs. Moneybags has a thing for watching gay men get it off together, so she thinks you and T paired up together would fit that bill nicely.’

Mistress R then added some details, new to me. ‘T has already done stuff like this before, so it all depends on if you are comfortable with performing with him, for them…’

T had never told anything substantial about his own time while working for Mistress R, nor what other men he had slept with while on the job, but once the momentary thoughts of being taken aback hearing this tantalizing new detail had passed, I agreed. With how distant and disinterested our relationship had now become, if anything else it gave me one last round of sexual action with him – and ultimately, this voyeur show for the Moneybags did end up being our last fuck together.

* * * * * * *

A couple weekends later, on my arrival in the city, Mistress R picked me up at the downtown station. We returned to her studio office where T was already there waiting and packed for our weekend. The three of us sat down over some drinks as we talked about what was ahead for me and what I should expect. Admittedly it was strange for me to be working alongside anyone else, let alone my soon to be former boyfriend T, but the excitement soon got the better of me and made me forget about any reservations or unease I may have had.

As he and Mistress R explained to me, when T had serviced them in the past, he would usually spend one night alone with Mr. Moneybags, and then the following night alone with Mrs. Moneybags, although since both of them enjoyed voyeurism, sometimes one would watch their other-half getting fucked. Mr. Moneybags really enjoyed seeing his wife with others, but she did not seem to share the same arousal watching him getting pleasured. She did enjoy seeing other men together, just not with her husband.

The three of us were unsure how the weekend would play out with both T and me there at once, so we decided we would just react to whatever transpired at the moment and pair off and play it all by ear. Mistress R figured, based on her behavior at the previous cocktail meeting, that Mrs Moneybags would be wanting to get her claws on me at first opportunity. But then she also really loved her time spent with T, so perhaps she may want to get one last session of lovemaking in with him, since he had left the business so to speak.

T then interrupted Mistress R, asking skeptically ‘Talk about this voyeur session they want.’

‘Yes, that…’ – bringing us up to speed, Mistress R explained that they ‘have asked to watch both of you perform in front of them, as in have sex for them.’

I looked over at T and said, ‘well I suppose I will take my usual bottom station, then?’ but then Mistress R interrupted, looked at T and then over at me. ‘I think she will want you both to take turns on each other.’

I had never fucked my boyfriend in his ass before – I had only ever topped another guy once, in what was my first gay experience. This would be serious uncharted and psychologically uncomfortable territory for the both of us. When I asked him, ‘Are you okay with this?’ I could tell he was not, and so too could Mistress R.

The three of us then sat in an uncomfortable silence for around a minute, thinking this out collectively in our heads. Mistress R then piped up, ‘how about you guys use a double ended dildo on each other? The sight of you two going at it with your asses slapping each other might actually be more visually erotic and interesting than simply doing anal on each other’.

I looked over at T, saying ‘of course I’m good with that’. Realizing this was probably the best of a bad situation for him, T then grudgingly agreed, ‘I suppose so’.

* * * * * * *

The evening of our session, the three of us piled into the Mistress’ black Mercedes as she drove us over to their house. It was a nasty, cold and rainy night, and as we drove along I would peer out the windows trying to figure out where we were headed, but this was a part of the city on the outskirts where I had never venture to during my previous visits.

At some point I became bored with the blackness of the rain and night, and so my attention shifted over to T, sitting next to me in the backseat, silently in thought and looking out the window just as I had been doing.  

My boyfriend had decided to accent his shapely, muscular physique by wearing some pvc-leather pants but was otherwise topless – his leather jacket would come off once we had arrived and gotten ourselves out of the rain. Besides, it was not like we would be keeping our clothes on for long.

Since Mrs. Moneybags had liked seeing me in drag, I decided to dress up feminine if nothing else for my arrival at their home. I wore my favourite short, pleated black skirt with a white shirt and black tie. For the same reasons of us soon becoming undressed on arrival, I did not bother covering my legs and I just wore some doc marten boots. To help play up Mrs. Moneybag’s apparent interest, I had made up my face with black lipstick and some face powder and Mistress R had drawn some eyeliner on for me. My now short hair I had simply gelled and slicked back. As a last girlish touch, I had opted to wear a hoop earring in my nose.

After what seemed like a longer than anticipated journey, all in silence as the three of us kept our thoughts to ourselves, the Mistress’ car turned up a long dark driveway and through a pair of stone pillars and an open gate, which then closed after us. The Mercedes pulled up in front of the house, but in the rain we made a quick run for the secondary side entrance. As I went through the welcome, open door rescuing us from the torrents of rain, I looked back at the Mistress’ automobile, and spotted a servant or some sort of staff hauling our two suitcases out of the car, before Mistress R then drove away.

T and I were greeted by someone who appeared to be their butler and T exchanged some small talk with him, while I now took in my location and became fully aware of the size and scale of their mansion they called home. It was very soon clear to me that this very stylish, old house was easily the most extravagant home I had ever been invited to. T then got my attention and took my hand. ‘Come with me, I’ll show you to the sitting room where we can store our stuff as well as change’.

After T and I had re-united with our suitcases and removed our wet coats, he explained the general rundown of the place and where to find things.

‘Like I said before, they are a really nice couple and once you and them begin to feel comfortable, it becomes very easy to take a liking to this place and feel at home, so to speak. Just relax.’

The house was massive, even though only the two of them lived there full time. T showed me where the main kitchen and pantry was, where I could get something rustled up to eat on request – they had their own in-house chef. I was amazed by this, and asked T: ‘How many people live here? How many staff do they have?’ and other such details I want to know. Along with the chef, and the butler, they had two or three others that were basically part-time assistants who maintained the grounds, cleaning, and other general labor duties – probably one of those who brought our suitcases inside.

T and I waited in the sitting room, enjoying a drink which had been brought to us, and having seen no sign yet of the husband and wife of the house.

We were then interrupted by the butler: ‘Everything is all set, when you are ready for show time, we’ll make our way down to the theatre room’.

Hearing this, I was like ‘theatre?’ – and T explained that most of the house was actually vacant and empty, and part of the basement had been covered into an arts and performance area. That was where we would put on our show.

T then stood up, looked at me, and said, ‘Well, let’s get this started…’ as he began to undress in front of me.