?

Who would like to be Simon in this story?

  1. yes

    7 vote(s)
    100.0%
  2. no

    0 vote(s)
    0.0%
  1. sissymistressUK

    sissymistressUK Porn Surfer

    Joined:
    Oct 10, 2015
    Messages:
    10
    Nothing had prepared me for what I was to find when I came home early to find My boyfriend going through my knicker drawer. More to the point though, nothing had prepared him for the way I dealt with the situation.


    As I walked into the bedroom he was standing there with a pair of My satin panties resting against his cock.


    “What the fuck are you doing?” My words made him jump and as he turned to look at him I could see the pure panic in his eyes, his cheeks red with embarrassment.


    “Umm err well I was just um” Was all that feebly fell out of his mouth.


    In that moment My anger turned to amusement especially as I could see how aroused he obviously was and decided to see how far I could take it.


    “Does the thought of wearing my panties turn you on Sam?” I kept My tone of voice soft and calm to lull him into a false sense of security.


    “I was just curious that’s all and you do have a sexy collection or underwear, not that I want to wear them or anything, just wanted to look” He looked less embarrassed as he said this but his cock was still hard.


    “Hmm well why don’t you try a pair on, just for a laugh Sam, go on it’s just Me and you here” I have him a playful look, hoping that he would take the bait.


    Then he picked out a pair and started to put them on, I wasted no time getting out My phone and as he pulled them up and turned around I took a photo.


    “What are you doing?” The panic returned to Sam’s face and all that I could do was laugh.


    “The question is Sam what you are going to do, you see within seconds I could send this photo to everybody in My address book, now considering how many mutual friends we have I could soon turn you into a laughing stock and you really don’t want that do you.” I looked right into his eyes and he knew that I meant business and that he had no choice but to go along with My requests.


    He watched, almost helpless as I laid some items out on the bed. A bra to match the panties that he had chosen, some lacy top hold up black stockings and a little black dress.


    “I suppose that you want me to put that lot on” He seemed rather calm about it, like he had just submitted to My whim.


    “Not yet, first you need to shave”


    “Shave?? Oh you really are going too far now and I am not going to play along” He tried to sound very firm but when I held up the phone with the photo on and explained how his mates down the pub would have a fucking hay day if they saw this and once again he backed down.


    I instructed him to go to the bathroom and remove the hair from his legs, chest and genitals and not to return till he had a smooth body.


    While he was gone I gathered up a few more items from the feminisation chest reserved for the sissy sluts that serve Me and put them on the bed. When Sam returned minus the body hair I felt that familiar surge of excitable pleasure and just a hint of wetness in my panties.


    I ordered Sam to start getting dressed, stopping him only to slip the breast forms into the bra and having a grope on them. The look on his face said it all really but I knew deep down that he liked it because his cock (the cockometer) told me so and the cock never lies. I helped him into the dress and made sure that the stockings were not twisted, then told him to bend over so that I could make sure the dress was not too short, as he did this I gave his ass a cheeky slap.


    I got a pair of purple 4 inch stilettos out of a box and made him put them on and then practice walking in them. At first he looked like a drunk tart that had dropped her kebab but soon got the hang of them.


    “Well aren’t you the sexy slut then” I looked him up and down with a little smirk on my face then took him over to My dressing table and made him sit on the stool.


    “Time for hair and makeup” I don’t think that he was prepared for things to go this far and looked at me almost pleadingly, a look that I quickly dismissed and started to apply the foundation, taking My time to blend it in perfectly and dusting it off with powder and a hint of blusher on his cheekbones.


    Next I focused on his eyes, fist using black eye liner and some purple eye shadow. The finishing touch were a pair of false eyelashes. I got Sam to give me a flutter and as he did I noticed the smile on his face and knew that he was actually really getting off on this now.


    I lined his lips before using a small brush to apply the lipstick, giving Sam the opportunity to practice his pouts. The piece de resistance being the gorgeous blonde wig that seemed to instantly transform Sam into a woman. It was truly a work of art even if I do say so Myself.


    “Well who do we have here then? I think Samantha is more of an appropriate name for you now don’t you think?”


    Samantha agreed and stood in front of the mirror admiring the transformation and obviously very happy about it.


    I took another photo for the album, one that was going to grow because for Samantha this was just the beginning.
     
    • Like Like x 2
    #1
  2. sissymistressUK

    sissymistressUK Porn Surfer

    Joined:
    Oct 10, 2015
    Messages:
    10
    Since the first occasion Sam or rather Samantha has got used to dressing up for Me at my whim and it was now time to move things along to the next stage.


    I had picked out some very slutty attire, traditional black and red lingerie, tacky fishnet stockings, the shortest red skirt that I could find and a low cut black top, and a pair of 5 inch heeled red shoes. The makeup was very bimbo looking, and plenty of it. I chose a blonde wig that had the *big hair* style going on which completed the look perfectly.


    “How do you feel Samantha? “ I waited hoping that what I had chosen had put him in the mind-set that I wanted.


    “I feel like a right slapper” was the response and the correct one at that.


    I left the room for a few minutes and when I walked back in Samantha’s face was a picture.


    “Well you know what happens to slappers don’t you” I watch Samantha’s gaze fixed on the strap on cock that My hand was wrapped around.


    “What do you think you are going to do with that?” Samantha looked concerned but I saw just a hint of excitement.


    “Well I thought that you may as well find out what it is like to be a woman Samantha, now let’s see how good you are with your mouth” he just stood there, his eyes fixed on My appendage. “Well what are you waiting for? It’s not going to suck itself now is it”


    Not wanting to piss Me off he got on his knees, wrapped his hand around My 8 inch black cyberskin cock and looked up at me as if waiting for a command.


    “Tease Me, come on Samantha make me want to fuck your face” That was all the provocation that he needed and he started to work his mouth up and down My shaft like he was playing the harmonica.


    I felt My own arousal brewing as I totally connected with *My cock* and made Samantha open his mouth so that I could watch it slide in right to the back of his throat, I had My fingers around the base so that I could feel his lips touch them, smudging his lipstick in the process.


    With My other hand on the back of his head I began to fuck his face, to My surprise he took to it like a duck to water and I was able to be a little more rough with him that I originally intended to as I told him what a dirty little cock sucking slut he was.


    “Well you handled that pretty well, let’s see how you deal with being fucked” This made Samantha stop mid suck, his eyes looking up at me like a rabbit caught in a cars headlights.


    “Now that really is going too far, I am going along with this dressing up shit and have sucked your cock but fucking me, well that is not going to happen!” I was almost convinced that he meant it, if it were not for the bulge that was visible through the skirt. Samantha knew that I was looking at it and remembered what I had said the week before, the cock never lies.


    I picked up some lube and drizzled it onto My cock, Samantha’s eyes widened as I worked My hand up and down the shaft, wanking it slowly, rhythmically as if it were real.


    “Well come on bend over and show me the goods” I had an almost playful tone to my voice and Samantha laughed before getting onto all fours


    I knelt down, lifted his skirt up and pulled the knickers to one side, running my hand over his ass and giving it a little slap.

    “Pull those cheeks apart Samantha and show Me that tight fuck hole of yours” He paused for a few seconds before reluctantly doing as he was told.


    I spent a little while just looking at the tight puckered hole that I was about to take and could not resist blowing on it just to see it wink at Me. Then I rested the head of My cock against it and began to push just the head in, watching Samantha’s mancunt open up to accommodate My girth. I held onto his hips and just kept still, feeding off of his anticipation, knowing that part of him really wanted it and the other part worried that he would hate it.


    I held off as long as I could then just pulled him back, impaling him with all 8 inches. He let out a loud groan, the type of groan that I was very familiar with having fucked many sissy sluts. My clit was twitching as I began to rock Samantha back and forth, gently at first but then as My arousal got stronger I started to thrust harder until I was pounding him like a piece of meat. I felt the sweat trickle down My cleavage as I continued to use him for My pleasure.


    Samantha’s moans were getting louder which heightened My arousal and I begin to feel My orgasm approaching like a train coming down the tracks, I could not have stopped if he had begged Me, it was the point of no return and I continued to slam My cock into him until I came.

    Exhausted and out of breath I pulled his knickers back up, before reaching around to see what his cock had made of all this and what I found was a very sticky mess.


    “Well I guess I don’t need to ask you what you thought of that then” Samantha just turned to Me, an embarrassed look on his face.


    “If I am honest yes I did like it, so now you have had your wicked way with me that’s it now right?” I couldn’t quite work out if it was a question or a request and just smiled sweetly at him already knowing what the next stage was going to be.
     
    • Like Like x 4
    #2
  3. Luvagobfull

    Luvagobfull Porno Junky

    Joined:
    Jul 19, 2011
    Messages:
    313
    Good start to a transformation of a boyfriend to maybe CD-sissy.

    But who is Simon in the vote section, is that your boyfriend not Sam?
     
    #3
  4. wildthing45

    wildthing45 Amateur

    Joined:
    Nov 19, 2010
    Messages:
    91
    Can't wait to hear about what is next
     
    #4
  5. Cmlvr69

    Cmlvr69 Sex Machine

    Joined:
    Feb 1, 2018
    Messages:
    887
    Loved it I wish u was my girlfriend now
     
    #5
  6. Longforit

    Longforit Amateur

    Joined:
    May 6, 2018
    Messages:
    95
    My wife did the same thing to me but deep down I wanted her too I love being dressed up and being used by her best sex we ever have
     
    • Like Like x 1
    #6
  7. Cmlvr69

    Cmlvr69 Sex Machine

    Joined:
    Feb 1, 2018
    Messages:
    887
    Sweet mine was a stripper we would get high and play alot at first just pretending and fantasizing and play with toys then she brought outfits home that girls had left at work and heels to. She would dress me up put make up on me paint my nails lipstick to. We would play for hours to. Then one night she called me telling me to get a shower she had a suprise for me so I did as she asked me to do to. She got home and I asked what's up? I was dressed allready as 2 cars pulled in our driveway and 4 black guys got out looking at them I asked why they were there? She told me I was going to get real duck tonight they were all for me as she got the video camera out setting it up so u couldn't see it and after they came in she left the room acting like she left but was filming everything that was going on now. We all got high they brought party favors and we got started I was sitting in between 2 of them on the couch as they all dropped there pants off now. I was very horny and wantING those big black dicks in me now.
     
    • Like Like x 1
    #7