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Mistress 2: First Date

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This is a true story. Other than one casual fuck, Tom and I had only met a few times (see Mistress 1 : The Pickup). We had arranged to meet at my place for a Mistress session, to be convened after our mutual sport, as it was the only night he could explain his absence to his wife. This session was our first date. And a very memorable one it was. There is a lot of preparation involved in a good Mistress session. I spend hours thinking and preparing to make sure the transitions are right, and required equipment is at hand when I need it. And then there is the costume…… I love to dress up. I have a toy box – a very big toy box – 1m long black metal tool box with all sorts of wicked things in it. The dom Mistress, other costumes and toys, have all been developed in the last 2 years – it’s been great fun. Anyway, back to the story. Tom was to come to my place at 8pm. On the black kitchen benchtop was set out the equipment required for the night. I was dressed in shiny black dom dress with lace-up back, black suspender and stockings, sheer bra and knickers, and black (real) leather knee high boots (the smell of real leather – yum), makeup, including strong eye makeup and slut-red lipstick. Shortly after 8pm, Tom knocked on the front door. “Come in, lock the door behind you, and come up stairs.” He walked up the stairs with some trepidation – he didn’t know what he was in for. As he reached the top of the stairs, he scanned the kitchen bench, and his eyes opened wide. I explained the rules: 1. You are to do what ever I tell you to do, 2. When I ask you a question, you will answer immediately with “Yes Mistress” or “No Mistress”. 3. I will be pushing boundaries, and the most important thing is trust – you need to trust me more than your wife. 4. If you find things too much, the safe word is “red” and I will stop, if you want me to back off a bit, then use “mercy”. 5. This stays between us. I asked if he was fine with that, he agreed. “Take your clothes off. Now.” Tom undressed. Yum. Tall and muscular, nice cock. I kissed him and then knelt down and sucked his cock for a bit – just a tease. Wicked smile - time for Mistress. First the collar, black leather dog collar with studs (he’s so gorgeous in collar). Then cuffs on wrists and ankles. I sit on a chair with crop in hand. “Lick me”. He kneels down and puts his face in my cunt, licking me through the sheer fabric, while I whip his arse lightly. “Now I want you to bend over so I can plug your arse”. “No” he said (I knew he was arse virgin – total yum – I love arse training). I bent down and sucked his cock briefly, he moaned. Then I picked up my riding crop, “I said bend over”. I lubed his arse and inserted a small butt plug. “Now sit on the chair”. He sat on the dining chair, the plug up his arse. I tied his ankles to the chair legs (I can do fabulous ropes). Clipped his hands together behind the chair, and used two belts to strap his torso to the chair. At this point, Tom is looking very nervous, but says nothing – how often does this happen in a lifetime. I strap on a horse bit in his mouth. Clip on nipple clamps (which I take off every now and then and suck his nipples). Then take some cord and tie up his cock and balls. Such beautiful work. I now have a man tied to my dining chair, who is totally at my mercy (how good is that). I kneel down, wrap my slut-red lips around his cock, and lick and suck that tied rock-hard purple cock while squeezing his pressurised balls. – I love cock. Later he told me that he nearly came right then and there – and this was from a man who does not cum easily. I need that cock for later. But, the rock hard cock was too good to waste, and I turned around and slightly lifted the shiny black pvc dress, and slid him into my wet cunt. Working just the tip, then sliding all the way onto his rigid cock, then starting again, until I thought he had was close to cumming, then stopped. Bitch. I sit on the dining table in front of him. Legs spread, with leather boots on his shoulders. He can look, but can’t touch. Pushing aside the sheer fabric, I finger my very wet self. “Do you want some of that?” He nods. I untie his hands from behind the chair and attach them together in front of him, undo the straps so he can lean forward, and take off the bit. I grab his head and push it to my cunt, and watch while he licks and sucks, then when I’m really wet, rub his whole face in my juices. I take off my wet knickers and shove them into his mouth, and strap a large dildo to his face using head harness. His eyes open wide and a look of “OMG” shows on his face as I strap it on, but he says nothing. “Fuck me”. He leans forward and fucks me with the dildo while he watches it go in and out from close quarters. I can tell he’s very excited by this. I need his cock - dildos are just not the same. I ask him “Do you want to fuck me”. “Yes Mistress”. I untie his ankles, and unstrap the dildo from his face. He has a desperate look in his eye, he’s so horny. He bends me over the dining table and fucks me, with the butt plug still up his arse, and his cock ties with cord. O god. It’s good. Then he says, “Please Mistress, I want to fuck your arse”. I point to the lube, he fucks my arse until he explodes in me. Yum. Nice first date. He was very brave, as there were many firsts for him, with a person he hardly knew. We both loved it, and Tom has been my horny lover these last 8 months, and we have explored much fun. Tom has also learnt to be my Master on occasion. Another story.
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Written by Mistress_Annie

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