First Time with a Mistress
I found a Mistress on a dating site, She was local to me, and her profile was intriguing. We chatted for a few weeks and she seemed to be keen to meet me, so we fixed up a time when I could visit her, I spent the day before shaving all my body, I was guessing that she wouldn’t want a hairy sub.
I arrived at her home slightly ahead of schedule, rang the doorbell, and this woman opened the door, slim with a great figure, I estimated her to be around 35ish. “You must be Tom”, “Yes Ma’am I replied”, “Follow me” She led me upstairs and opened the door to an upstairs back room. The room was all painted black, with spotlights everywhere, a black bed in the middle that looked like it had a black latex sheet on it, cupboards and racks around the room that had whips, canes, and paddles hanging from them, latex suits on hangers, I dreaded to think what was in the cupboards.
“Get undressed completely and lay face down on the bed, hang your clothes over the chair in the corner”, she barked, now I was beginning to feel very nervous, why did I agree to meet her? “I'll be back shortly”.
I stripped off and lay face down on the bed, I was shaking but not from cold, just sheer nervousness. It must have been ten minutes or so when I heard the door open, it closed again, and footsteps came towards me. She stood beside the bed, I could see her, black stockings, suspenders, and the tiniest of thongs, nothing else, she was naked from the waist up, except for a cane in her right hand.
“ What are you expecting boi” I didn’t know, but guessed I needed to answer promptly, “I am expecting nothing Mistress, other than to please and amuse you” …
“Good answer, what is your pain threshold boi” “I do not know Mistress, I have never been in a situation like this before”. She sat on the bed next to me, and I could smell her perfume it was amazing, she put on a pair of latex gloves, and picked up what looked like a bottle of lube, suddenly I felt her hand between my ass cheeks, I could feel her slippery finger slowly running over my hole, I groaned and writhed a little, it felt good, and my erection was growing, without warning, a finger pushed it way inside, I yelped, I could feel it moving about inside me, then two fingers, and then a third, she was stretching my asshole, it was starting to hurt, but I kept quiet, “Boi, this is a plug and you will hold it in no matter what, do you understand?”… “Yes Mistress”.. I felt this cold object probing at first, but then with the pressure I could feel her forcing it in, it was starting to hurt, then suddenly, with a plop, my ass accepted it and my sphincter muscle gripped it and the pain subsided.
Without warning, I felt a sharp pain across my ass, “First stroke of my trusty cane boi, get used to it, this was followed by another three in quick succession, I jumped, almost off the bed, “I see you need to be secured”, with that, leather cuffs with attached to both my ankles and wrists and tethered to all four corners of the bed, a ball gag was secured in my mouth and strapped round the back of my head, suddenly, two more strokes hit my backside, I struggled to avoid them, but I couldn’t move, my muffled cry came to no avail, as four more rained down, and then another four, god did it hurt, but I was helpless to do anything about it. “You did well” I heard her say, my restraints were undone from the bed, and I was told to change over and lay on my back, where the restraints were re-attached, and my full erection was now apparent, “Well it seems you are enjoying my plug in your pussy, it indicates you like things up inside you, maybe your gay, we need to explore that sometime”.
I noticed she had removed her thong, as she knelt on the bed and one leg came over my head, she lowered herself over my face, “Taste your Mistress boi, and remember in this way, now get your tongue up there.
To be continued…..
I arrived at her home slightly ahead of schedule, rang the doorbell, and this woman opened the door, slim with a great figure, I estimated her to be around 35ish. “You must be Tom”, “Yes Ma’am I replied”, “Follow me” She led me upstairs and opened the door to an upstairs back room. The room was all painted black, with spotlights everywhere, a black bed in the middle that looked like it had a black latex sheet on it, cupboards and racks around the room that had whips, canes, and paddles hanging from them, latex suits on hangers, I dreaded to think what was in the cupboards.
“Get undressed completely and lay face down on the bed, hang your clothes over the chair in the corner”, she barked, now I was beginning to feel very nervous, why did I agree to meet her? “I'll be back shortly”.
I stripped off and lay face down on the bed, I was shaking but not from cold, just sheer nervousness. It must have been ten minutes or so when I heard the door open, it closed again, and footsteps came towards me. She stood beside the bed, I could see her, black stockings, suspenders, and the tiniest of thongs, nothing else, she was naked from the waist up, except for a cane in her right hand.
“ What are you expecting boi” I didn’t know, but guessed I needed to answer promptly, “I am expecting nothing Mistress, other than to please and amuse you” …
“Good answer, what is your pain threshold boi” “I do not know Mistress, I have never been in a situation like this before”. She sat on the bed next to me, and I could smell her perfume it was amazing, she put on a pair of latex gloves, and picked up what looked like a bottle of lube, suddenly I felt her hand between my ass cheeks, I could feel her slippery finger slowly running over my hole, I groaned and writhed a little, it felt good, and my erection was growing, without warning, a finger pushed it way inside, I yelped, I could feel it moving about inside me, then two fingers, and then a third, she was stretching my asshole, it was starting to hurt, but I kept quiet, “Boi, this is a plug and you will hold it in no matter what, do you understand?”… “Yes Mistress”.. I felt this cold object probing at first, but then with the pressure I could feel her forcing it in, it was starting to hurt, then suddenly, with a plop, my ass accepted it and my sphincter muscle gripped it and the pain subsided.
Without warning, I felt a sharp pain across my ass, “First stroke of my trusty cane boi, get used to it, this was followed by another three in quick succession, I jumped, almost off the bed, “I see you need to be secured”, with that, leather cuffs with attached to both my ankles and wrists and tethered to all four corners of the bed, a ball gag was secured in my mouth and strapped round the back of my head, suddenly, two more strokes hit my backside, I struggled to avoid them, but I couldn’t move, my muffled cry came to no avail, as four more rained down, and then another four, god did it hurt, but I was helpless to do anything about it. “You did well” I heard her say, my restraints were undone from the bed, and I was told to change over and lay on my back, where the restraints were re-attached, and my full erection was now apparent, “Well it seems you are enjoying my plug in your pussy, it indicates you like things up inside you, maybe your gay, we need to explore that sometime”.
I noticed she had removed her thong, as she knelt on the bed and one leg came over my head, she lowered herself over my face, “Taste your Mistress boi, and remember in this way, now get your tongue up there.
To be continued…..
4 months ago
