I have a tale to tell of how I spent my Saturday evening last week but first brief bit of background. I’m a young sub of 22 years currently tied to Mistress who is 12 years my senior. Just over six months ago I was fortunate enough to get a response from an online ad seeking an older woman to submit to. We exchanged a few emails and agreed to meet each other for the first time in a hotel close to where we both live. Since then our relationship has flourished and we have even talked about me committing to her 24/7. Never have I felt so satisfied to serve and please such a wonderful woman.
Some time before last Saturday, she mentioned that she would like to show me off to her friends and that I would spend an evening servicing both her and them. Needless to say I was somewhat hesitant, firstly out of loyalty to my Mistress but also out of worry that I may not be able to satisfy such a gaggle of women. I didn’t require any convincing, however, since it was my Mistress’s decision and I was told that I would get a nice reward if I behaved myself.
After agreeing to the evening a date was set and I spent the ensuing days growing ever more nervous but also excited that I would be waiting on five women. Eventually the day arrived and I ensured that the house was spotless and that nibbles and a meal were prepared. My Mistress teased me throughout the day, telling me I was to keep everyone happy otherwise there would be consequences; I didn’t need reminding of the pain I endured last time I stepped out of line.
At this juncture, I would like to point out that I will tell the remainder of the story in three parts as I feel the events that will be described in each one are of a discrete enough nature that I can split them up without losing any flow or details. The first, which I will describe shortly, tells of how I spent the first part of the evening as the guests arrived.
A reminder that along with my Mistress, four of her friends would be coming over. These friends were Annabel, Sarah, Rosie, and Ophelia. I had met only one of them before, Rosie, and would describe her as someone between the ages of 32-36, of slim build with small breasts, long brown hair, and perfect dainty feet. I had no idea what to expect from the others. As a point of reference, my Mistress is called Charlotte and whilst I have told you her age, I have not yet described either her character or appearance.
Charlotte is 5’7” in height, which is four inches shorter than myself. She has wonderful D-cup breasts with nipples that point slightly upwards along with wide hips and a slightly fat posterior. My favourite part of her character is her dry but playful sense of humour and while strict when required, we are never void of laughter in our relationship. Her facial features have aged as you would expect for someone who is 34 years old but she has retained a twinkle in her eye and a vim about her appearance that would require you to look more than once to guess she was that old.
I would be meeting the remaining guests throughout the night and will do my best to paint a picture of their appearance as I go. It will not be so soon, though, which I’m sure will disappoint you as I was set to spend the first part of the evening blindfolded. In fact I would be most immobile as I served as something of a conversation piece in the entrance to the house.
As you enter the building, to the right is a flight of stairs that ascends to the only other floor in the house. To the left is a door leading to the living room and straight in front is a small corridor of perfect size to put a coat stand, an umbrella holder, or in this, case a submissive young man. It had been raining most of the day outside and this had only abated in the last hour or so. As a result, it was fairly chilly in the early spring air. Each time the door opened to the corridor, a strong, stiff breeze filled the space clearing out any warmth that was generated within the house. I would be stood at the foot of the stairs facing the front door so felt the full efforts of Mother Nature to cool everything down.
We were only minutes away from the first guest arriving and my Mistress had finished preparing me for greeting everyone. My clothing was to be nothing more than a pair of black thigh high stockings held up by a suspender belt, which were topped with black lace boyshorts. My feet were adorned with six inch stiletto heels and rope was tied above my ankles and knees so retaining both my balance and posture was rather difficult. To exacerbate my predicament my hands and arms were held backwards with an armbinder and my mouth was filled with a large red ball gag. Finally a hood was placed over my head stopping me from seeing anybody enter; that didn’t of course stop me from feeling the draught every time the door opened.
The hood was not heavy enough to stop me from hearing and I could tell by my Mistress’s greeting that the first guest to arrive was Ophelia. There were giggles as I heard footsteps shuffling towards me on the carpet and I had quite a surprise as cold fingers traced their way across the front of my torso.
“What do you think of him?” Charlotte asked.
“He’s not quite what I expected, I always envisaged you going for someone a little older.” Ophelia responded, running her hand across me again. “Does he behave well?”
“He’s impeccable, I barely had to train him, which I thought would be a real chore. Six months down the line, I don’t know how I managed without him.”
They continued to discuss me for a short period and I was beginning to tire in my bondage and shoes. We had done some training for this prior to the big night so I knew that I would be able to last a fair bit longer as long as I shifted the weight between each foot regularly. Once Ophelia had had a sufficient inspection, she was led through to the living room and I used this as an opportunity to relax my posture before the next person arrived.
The next guest was Rosie, whom I recognised by accent. She echoed Ophelia’s giggles and my nipples stood on end from the cold. This was greeted with a sharp pull and twist resulting in a groan from me and an attempt to escape that got me nowhere. Rosie was taken into the living room and the exclamations from Ophelia suggested that they were old friends who hadn’t seen each other for a while.
I had to wait a while for anyone else to turn up and during this time I could hear the faint din of music, chatting, and laughter coming from the room next to me. My legs were now feeling quite tired and my jaw was hurting immensely. Each time I tried to open and flex my mouth a large amount of drool dripped out and occasionally landed on my belly or feet; I was dreading to think what the floor looked like. I was also starting to wonder how long I had spent like this when the doorbell rang again.
Mercifully the final two guests arrived together and the sound of chatter was now more prominent as it followed Charlotte into the hallway. Unlike the previous two guests, Annabel and Sarah had a much more thorough inspection of me. Again I was surprised to feel their hands upon me as I was not able to see or anticipate their gestures. I was first turned around and I hobbled in a small circle feeling pain work it’s way up from my toes to my knees. More than one pair of hands rubbed against my bum down inside my knickers and I was shocked to feel a finger push with some force against my hole. My moans were greeted with more giggles and to my relief there was no penetration yet.
I was swivelled back around to face the door again and the hands continued to feel their way around inside my panties. Given the pain I was in, I had barely mustered an erection all evening but careful caresses and touches had me engorged with barely any effort.
“I thought you said you had him well trained?” one of the voices remarked, “I wouldn’t expect him to get hard so easily.”
“Well he’s here for everyone tonight,” Charlotte responded, “if you don’t like the way he’s behaving, you’re more than welcome to put him in his place.”
And with no warning at all, my nipples were once again squeezed driving pain through my chest. My erection died away in a matter of seconds and the front of the knickers was pulled down and placed below my ballsack, presenting my goods to anyone who cared to look.
“What do you know? He does respond well, doesn’t he Annabel?” said one of the voices
“Yes. I must say, Charlotte, it looks like you’ve done a great job on this one.”
“I guess we’ll find out soon enough,” said the first voice again.
Once more, the group erupted into giggles and with that I was once again left alone in the hallway as the final two guests were taken into the living room. I began the night looking mighty pretty and welcoming for Charlotte’s friends but only 45 minutes into the night, I was already feeling a bit worn down. Fortunately I was forewarned that I wouldn’t need to suffer too much strict bondage and that I would have more fun later on. I’m not sure what that meant but I guess I was soon to find out. As it stood, I was left with cold, sore nipples, standing in what must now be a pool of my own dribble with my cock on show.
…
And so the first part of my tale comes to a close. The next part will see dinner served to the guests where I will be offered something to eat that won’t be on the menu for anyone else. I hope you have enjoyed this start to my story and that you look forward to what remains. If you wish to leave me a comment or private message, I will be most pleased to hear from you. Do look out for my next part that shall be coming soon.
Source: reddit.com/r/sexystories/comments/641rfs/a_night_with_my_mistress_and_her_friends_mfffff
More please!