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Meeting Mistress

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By (user no longer on site) OP   
5 weeks ago

Like many on here curiosity got the better of me. I've had my moments thinking about slipping on some tights or trying a pair of heels, see if it really is as difficult as some make it out to be. The decision to take a shot happened during a small meet one morning, being particularly horny and craving my cock being sucked I arranged said meeting. All well and good arrived on time,fairly pleasant chat and up stairs we went. He asked if I liked guys in knickers? With no hesitation "and more". From his work bag came a skimpy thong and a pair of laddered tights. He wore them as he sucked me. Laying back to enjoy it, I kept thinking what if I had the clothes on. Our meets was short but the impact it left.

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By (user no longer on site) OP   
5 weeks ago

Almost a soon as he has left, I was straight to searching online. Did I just want clothes, give them a wear see how it felt, or did I want a more full on treated like a slut experience. Deciding to think about it, I took afew days before continuing my search. The obvious finally hit me, why not talk to the "girls" in a similar situation as myself, this site has more then afew. To cut a fair bit of minor details, I began chatting to someone whose profile had alot of the same thoughts I was having. They looked amazing, they loved having a totally fem look wig, makeup,dresses,tights, stockings, sexy lingerie and the heels! Our chat started small, me completing them and all, I just explained my thoughts about wanting to give being all dressed and girly a go. They explained they had a similar start, which changed when they met a mistress.

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By (user no longer on site) OP   
5 weeks ago

The chat had lead my search in the right direction. I began searching this other site for a more local mistress. Must admit reading through some of their profiles got me rather scared again. The sizes of dildos and plugs in pictures had me questioning how that would even fit in someone. Others that seemed to love marking guys. I just want to dress up and maybe a little strap on fun, not being held upside down with breathing restrictions and my balls slapped. And then I found Mistress May x

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By *rey man hereMan
5 weeks ago

york

I thought about this on my run today

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By *igmikeswMan
5 weeks ago

Newton Abbot

Tell us about Mistress May!

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By (user no longer on site) OP   
5 weeks ago

The conversation between myself and Mistress May began simply enough, clearly this wasn't her first time at dealing with the sort of questions and reservations I would present. She tells me not to worry and we can take it slow and relaxed. Great I thought, she seems perfect for this. So we arranged a time for the following night. Gives me time to clear the house a bit and follow her instructions to clean myself out if I was wanting to do more then just wear. "Looking forward to it baby xx"

Wow with that an intense mix of horny and nerves hot me. Should I really do this?

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By *carf57Man
5 weeks ago

arctic

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By (user no longer on site) OP   
5 weeks ago

Jumping to the next day. I didn't eat that day trying my best to avoid any accidents. If this was going to happen might aswell push it. a couple hours before the meeting was to happen, I gave myself a deep cleaning. For those that haven't done it before it really can feel off putting, well maybe it was the nerves kicking into overdrive. One jet of water, then another and another. Ok I think I'm ready for this. Took my normal shower and put on some loose clothes, she had told me that might aswell make it easy for yourself since you'll be re dressed during. A text comes through " Hi love are you still going for our meeting in an hour ? "

Finally feeling a burst of calm

"Yes Mistress"

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By (user no longer on site) OP   
5 weeks ago

Time went by slowly as I waited. More more the excitement grew. Ready to play good host with a drink ready for her arrival. Final touch ups of the house, guess the rush was making me unable to sit still. Then it happened my phone went "10 minutes love x"

Ok ok just go sit down and calm yourself. Breathe deep and slowly, have a nervous piss and wash it off. Sit back down one minute has passed. This was not helping how I felt should I call it off just forget it was supposed to happen. A taxi pulls up outside my house and dose a turn fairly quick, was stunned though that was for me, must of just been turning on my street. A buzz from my phone "I'm here love".

Small knock at my front door. Before I knew it I was standing opening it.

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By (user no longer on site) OP   
5 weeks ago

I opened the door, wow she looked even better in person. I invited her in said have a seat and asked if she would like a drink. Retuning with said drink, I seen her fully in the light of the room. She had been wearing a long jacket as is was a cold night, now removed she stood hand on hip. She wore a white body suit, that really held her big tits prominently, leather leggings that showed ever curve in her legs and her ass wow it was very plump and round, could burry your face on it. Black heeled boots that she walked in so elegantly. Long black hair red lips tanned skin dark eyes. I pass her drink to her and we begin.

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By (user no longer on site) OP   
5 weeks ago

A few sips of ours drinks and we talked more about what I was after during this meeting. Almost with out warning she asked do you want to be dressed now and then we drink? Yes please

She stood up walked to her jacket moved it and revealed a fairly large black hand bag. She opened it and began pulling out clothes, dresses stockings tights knickers bras oh yes yes yes I thought. Well get your clothes off, she tells me as she sorted the clothes on my table.

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By *usiness123Man
5 weeks ago

Hamilton

OH YES YES YES - loving this keep going want to hear more about this journey

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By (user no longer on site) OP   
5 weeks ago

I removed my clothes as she decides what I will wear. First she turns holding a lovely black bra little lace trim at the top, she helps it on me adjusting the straps for my chest. Once fitted it felt odd looking down actually made it feel like I had a set of my own, she grabbed my hands and put them on the cups, making me squeeze them with her. She gave a low moan that got my cock twitching. She must of noticed turning and rubbing her leather clad ass on my cock before going back to the table and pick up several pairs of knickers. Try them all she commands. Yes Mistress. The first were dark blue lacy briefs, the least skimpy of the lot. Sliding them up my legs felt great and adjusting them around myself made me feel more feminine. No try another set clearly mistress wasn't as fond of them as I was. The next was the total opposite a tiny white g string, aside from the front you would of thought it was just string. On they went, felt great between my ass cheeks but my cock and balls kept popping out the side. Hmm she smacked my ass gently, try these and she passes me a lovely black silk thong. But the feeling in my hand I knew these would be the ones

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By *mooth FuntimeMan
5 weeks ago

Oxford

Going nicely

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By (user no longer on site) OP   
5 weeks ago

Stand in her bra and silk thong had began getting me hard clearly this was the start of what I was going to be wearing that night. She must of decided what else to add as she walked back to the table moved a something and produces a short length long sleeved near black dark blue lycra dress. Putting it on was a slight embarrassment, as with all those cuts in the dress design to show off your tits hips and back hands going one way head in a sleeve. We laughed I asked is this problem you face putting this stuff on, she laughed and answered yes as she sorts the dress over me all in place bra showing through, loved the wiggle in the skirt, yes yes sexy turn for me. I did my best sexy turn to present my ass smack smack getting a bit more firm now I thought. Sit down she commands playfully, I have more for you. Pulling the dress down as I sit to keep it in place she goes to her bag to produce a set of dark black stockings, kneeling down she helps me put them up my legs, the further up they go the horny I get they feel amazing I stand and she sorts them on me.

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By (user no longer on site) OP   
5 weeks ago

I'm settling into the clothes now seems to be effecting my movements guess I was getting into the role more I'm just looking down at myself not seen a mirror yet. The top of the stockings just poking out the dress as I'm sat waiting for her, again she's at her bag seemingly having difficulty finding something, oh I'm sorry I forgot to pack extra heels for you. I'd of loved them but I'm very happy with what I've got she walks back over and says have a drink tell me how you feel, I'm great I could go further she had brought her make up bag over then let me get you ready like a dirty bitch. That got me, I was ready for more now. She could tell I was nervous but excited as she begins dusting my face, eye shadow next i think we were just talking about silly back and forth,things like do you all learn in this kind of way. I just let her do her thing. Mascara, blush and then lips started with a pencil(who knew) going round the outside of my lips. Lipstick to follow press your lips and blow kisses with me she says as we stair as well blow kisses setting the lipstick. Before you see in the mirror she says you can try my heels as a sorry for forgetting them on your first time. They might be tight but go for it in a more firm tone of voice. Thank you mistress. She unzips the sides of her boots and slides them off passing them up to me. I forced my feet into her boots curling my toes to fit and we both pulled the zips up. Yeah they were tight lucky I've not got massive feet. That's it I'm fully dressed and wearing makeup! Go look sexy she says sitting down to her drink while watching for my reaction. I sort myself before going to the mirror carefully stepping forward in these boots. Minds racing again what am I about to see I've only seen a part of if really. You walk well in them sexy she says a relief over me I stand and stare into the mirror

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By (user no longer on site) OP   
5 weeks ago

I looked amazing for I thought anyway the outfit causing my body to have feminine curves and the heels would cause me to be all girly in walking she loved it have a drink sexy bitch smacking my ass as I walk passed her my cock bulging out the dress she ran her hand over it hmm you want, taking a sip I yeah, good she stands back to the bag pulls out two dildos one small one fair sized for someone so inexperienced. The small one first, waving it in the air walking to me. You like it? Yeah, she began rubbing my body slowly going up she kept asking if I liked it till the top of my head where it changed pulling my hair slightly yes what bitch. Yes Mistress sorry mistress, on your knees bitch ready for more then just dress like me. I lowered myself slowly head hight to her crotch she places the toy Infront. Suck it bitch she orders

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By *iswitch12Man
5 weeks ago

North

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By *inzaMan
5 weeks ago

corringham

More please

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By (user no longer on site) OP   
5 weeks ago

I start licking the tip slowly moving it around my tongue. Yes yes suck it, I put my mouth on it and slowly rock my head back and forth each stroke getting deeper down the shaft. She's giving me encouragement yes bitch oh yes so sexy gently she started pushing it down my throat. We got into a gentle rhythm, I could feel it in the back of my mouth, saliva starting to fill the rest of my mouth. I open my eyes to her smiling face saying oh your a good bitch taking that whole thing, holding in in her hand I see that the base of the toy has my spit on it more that I thought. Before I could speak she presents the second toy and press it to my lips suck it bitch !

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By (user no longer on site) OP   
5 weeks ago

I began sucking that cock with excitement. It was thicker so had to stretch my mouth.like before I started slow and worked my way up the spit I had helped lube it up. I'm half way down getting my flow, she says want to know what a dirty man would do wink if yes. I get as far as I can comfortably take about just over half look up at her and give a sexy wink and continue my sucking. Good bitch as she thrust firmly down my throat cause me to gag for the first time

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By *usan 749ukTV/TS
5 weeks ago

Bangor

Excellent

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By (user no longer on site) OP   
5 weeks ago

I pulled back but not taking the toy full your my mouth. Yes bitch they thrust deep when they are excited you need to learn how to take it. Hand placed on my head she guided me back down the cock and slowly she thrust in some of the toy slowly pushing the depth.suck hard bitch eyes closes I begin pushing the cock down my throat ignoring the minor gagging spit started dripping, she's thrusting harder now. The sounds am making are like a porn star. Eyes watering she pushes deep and holds it in place before a big gag pushes the whole toy out my mouth , yes you sexy bitch and slaps the spit covered cock over my facex

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By *carf57Man
5 weeks ago

arctic

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By *ittlesmoothoneMan
5 weeks ago

purbeck

Fuck I am so hard. I need this

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By *ecky HighheelzTV/TS
5 weeks ago

Banbury

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By *perm bank69Man
5 weeks ago

Hythe

Mmmmm

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By *inkyKnicksTV/TS
5 weeks ago

Cupar

Loving this ,,,

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By *i14Man
5 weeks ago

Rayleigh

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