Wedding Dress-ed

Discussion in 'Member fiction' started by sissymissy, Dec 3, 2008.

  1. sissymissy
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    sissymissy MistressMichelles missy

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    Wedding Dress-ed

    An older story that doesn't contain any chastity... yet... :)

    Despite the lack of chastity, think some might enjoy...

    ----------------------------------------------------------------------

    There was the ad…

    “WEDDING DRESS – Never used, size 12, white satin, high lace collar, long sleeves, long train, all accessories included. Paid over 5000, selling for 500 or best offer. XXX-XXX”

    Now you may be wondering, why I, a divorced man of nearly 40, would would be looking at wedding gown ads in the newspaper. Well, I’ll tell you.

    I’ve been a cross dresser for half or more of those nearly 40 years…

    Of course being a cross dresser, what’s not to like about a wedding gown?

    I had often perused the ads thinking that perhaps one day it would coincide that there was an ad and it was the right size and it just so happened to be one of those rare times that I actually had the cash on hand and could make the call.

    Yes, after much internal debate, I finally decided that today was going to be the day… I figured; “What the heck, the ad does say or best offer.”

    It was with trembling fingers that I dialed the phone and when it started to ring, I began to feel faint.

    Luckily I didn’t have to wait long as it was answered before it could ring the second time by a very nice sounding female voice.

    “Hello”

    I was a little startled as I was rather expecting an answering machine and here I was about to ask this girl about her wedding in person.

    “Ah… Hello. I was calling about the ad in the paper.”

    “Which one, I have several running right now?”

    This was going from bad to worse quick… not only did I now have to come right out and ask her about her wedding dress, she had the cutest English accent.

    “Ahh… ummm the uhhhh one for the wedding dress.”

    “Oh yes, I still have it and would love to be rid of it. Damn that man!”

    Even though I could hear the anger in her voice, I still was strangely drawn to her voice and fell into some sort of daze as it took me several moments to realize the awkward silence.

    Snapping out of my haze, I work up the courage to finally ask the big question.

    “Your ad says best offer and I’m afraid I’m on a rather tight budget but would you possibly consider a hundred dollars for it.”

    Figuring this would be the end of the conversation as I hadn’t put too much stock in it anyway and wouldn’t be too upset, you could have knocked me over with a feather when I heard her reply.

    “Yes, even though I hate to do it, he helped pay for it so I’m not taking all the loss and I’ll be done with it. You or your fianc must get soon though as I’m afraid if I have to see it much longer I may rip it to shreds.”

    Already being put off guard by her wonderful voice, then being shocked and thrilled that she was going to accept my offer and take 100 for a 5000+ gown, I was already out of this world and hadn’t thought this far ahead and before I knew it wanted to hang up immediately.

    “Oh I don’t have a fianc; I’m single, well divorced actually.”

    Realizing right away I had just practically told her that I was buying a wedding dress for myself, I didn’t know what else to say and nearly did hang up as there was another long awkward silence.

    I started to feel a little queasy and had to close my eyes for a moment to calm my nerves and steady myself. When I thought I heard her giggle.

    “Well then when can you pick it up?”

    “Any time that would be convenient for you, would be fine with me.”

    “Well, I’m not sure about this now. I hadn’t really thought about it but now before I have you over to my house, I want to meet you in public first. You will meet me tonight for diner at the TGIFridays on Main Street at eight PM. DO NOT BE LATE!”

    <CLICK>

    After listening to the loud annoying buzzing in my ear for several moments, I finally snapped out of my trance.

    That was one strange conversation and it seemed that it could be the start of something very interesting. I already got a diner date with what I imagined to be a very attractive somewhat young and attractive English woman… and soon an actual wedding dress.

    Well the day could not go fast enough. I couldn’t concentrate on anything other than that conversation. Was it just me or was it odd the way she just assumed 8 was fine… maybe the battery on her phone went dead… maybe she had call waiting and I got lost in the switch, I didn’t know.

    I did know I couldn’t wait until eight came. I rushed home after worked and showered and put on my favorite pair of panties.

    Yes, I normally do wear panties and it had almost become second nature at this point. I only reached for the man drawers drawer when I had a doctors appointment or had a hot date and thought there was a chance I’d get lucky which wasn’t too often these days.

    A t-shirt, and nice button down shirt were next along with a decent pair of casual pants and sneakers and I was ready to go.

    “It’s only 4 o’clock, now what do I do til 8?”

    Well, what else could I do…

    I sat down at my computer and read some stories from fictionmania and got myself all hot and bothered.

    After reading a few stories, and with the anticipation of the evening ahead, I was nearly beside myself with nervous energy and turned on beyond belief.

    I couldn’t help myself, and as I often do while reading the stories, I had to take a break or things were gonna get messy and I didn’t want to shower again.

    Also as I often do during one of these breaks, I took the chance to “get more into the story.”

    I was at a point in the story where a wife was dressing her husband and had just told him to put on a pair of pantyhose, so I did too.

    Quickly, I pulled a pair of socks on over the hose and then put my pants and shoes back on and went back to my reading.

    Before long, I needed another break and this time I was at a point a story where the domme was having her way with her sub while wearing a strapon.

    Well, I didn’t want to go that far as once again, didn’t want to shower again as it was… oh my… it’s nearly 6… won’t be long now…

    Instead of doing any thing that would require lube, I decided what the heck, I’d add a bra. After all, I was already wearing the panties and hose. All of which were pink in color by the way.

    I put my shirt back on but thought I could see the outline of the bra too clearly and decided to add a t-shirt to mix as well.

    With the t-shirt added, I felt better and sat back down at the computer just once more before heading out.

    Time was suddenly passing too quickly and before I knew it, I was running late. I rushed out the door with my computer still on, my shirt buttoned crooked or one button off and my penis extremely hard with the head constantly rubbing against the lace at the top of my panties only making things worse.

    I must have broke all the speed limits on the way to the restaurant and someone did manage to make it at 8:02 according to the clock in my car. However, by the time I navigated through the crowd out front and made to the hostess stand and then finally managed to make my way to the table led by the hostess, I’m afraid it was even later

    The woman was even more beautiful than I had imagined from her voice. I didn’t have long to enjoy the view as I was quickly put on the defensive.

    The hostess had no more than given me a menu and quickly departed than I got my first taste of what lay ahead this evening.

    “What time is it?” She asked me rather curtly and much louder than I would have preferred.

    “Huh… uh uh… eight???” I answered rather meekly.

    “Do you even own a watch?”

    “No I just use my cell.”

    “Well use it now and tell me exactly what time it is.”

    I pulled my phone out of my pocket and was rather shocked when I looked at it and read 8:20.

    “WELL!”

    “um uh um… It’s 8:20, now 8:21 Ma’am.” I was too ashamed to look up from my phone at this point as I feebly squeaked out my reply.

    I still don’t know why in the world I called her Ma’am at that point but it just seemed to come natural.

    “Ma’am. I like that. You will continue to address me as such.”

    It was at this point that i realized that i didn’t even know her real name and it was looking like I might not get to any time soon.

    “Yes Ma’am”

    Our table was around the bar area in the smoking section and was on a raised platform in a row of booths directly across from the bar. I was just starting to take it all in and realized things had gotten quiet once again.

    I couldn’t bear the awkward silence and slowly after much debate, managed to look up from my menu which still sat unopened in front of me.

    She had been just sitting there staring at me. I had assumed she was perusing her menu and debating on what to order but no, of course not. She had already had 20 minutes or more to look at the menu and now she just sat there looking at me.

    Once she saw me looking up, she smiled and nearly put me on the floor figuratively and literally with her next statement.

    “Since it has now been over 5 minutes since we established that you were at least 20 minutes late and you have yet to offer any sort of apology or even attempted to explain, I shall have to help you with your apology. I’m afraid that since I must now help you, there will be a slight penalty involved.”

    Things were quickly going from worse to even worse yet and I didn’t see any end in sight short of standing straight up and bolting for the door. I felt both “cold and clammy” in my hands and chest and “hot and feverish” in my head and penis and thought this had to be a stroke or heart attack and perhaps my way out afterall.

    As she calmly and nonchalantly continued I went from bad to worse after hearing what would come next.

    “By way of a penalty, before you apologize for being so rudely tardy, you will rise from your seat, come over here to me and kneel before me. You will then very gently remove the shoe from the foot that is offered you and you will then kiss each of the 5 toes on said foot. After you have kissed each of my toes, you will replace my shoe and then do the same for my other foot.”

    I could not believe what I was hearing. It truly was something straight out of one of those stories that I liked to read so much but this was no story at all… this was live.

    “Now you have 5 seconds to perform this task and apologize for making me late. If you can not or will not do not do as I command, then you can leave now and you will certainly not be getting my dress.”

    I swear I hear her giggle slightly as she says. “And somehow sissy, I think we both know that you really do want that wonderful white shimmering satin wedding gown.”

    She was right and she had me. But I just couldn’t…

    “4”, “3”, “2” she counted down again louder than I would have preferred and again drawing attention.

    I quickly made the decision that it was now or never and leave or do as she said, I had to get up either way. I jumped out of my booth as she counted “1”. And…

    Quickly knelt before her and removed first one shoe and kissed all the toes on that foot and then the other shoe also kissing all the toes on that foot. After perform that rather embarrassing act, I then began to offer the demanded apology.

    “I’m so truly sorry for being late and keeping you waiting Ma’am. You are correct in that I do wish to purchase your wedding gown and I am so very very sorry that I have caused you this inconvenience and hope that you will allow me to make it up to you in any way that you would see fit.”

    She smiled and told me I could sit back down as I was creating a stir.

    I had fallen into subspace or at least I think that’s what the stories called it… was off in or own little world where the only two people there were me and this woman who’s name I didn’t even know.

    After snapping out of it, I looked around to see a small crowd had formed as there were 2 servers and a busboy going one way and the hostess seating a table for 5 coming the other and all had just stopped at me and were staring. Some where laughing others were not so amused. Some were downright shocked I think. I don’t know what they were thinking or feeling but I was wishing the earth would open up and swallow me and I was still feeling ill.

    I did begin to feel a little better once I sat back down and could pick up the menu and pretend to lose myself in but in truth just needed something to hide behind.

    She was not going to have any of that though and quickly took my menu from and announced that she had used the extra time she had to learn the menu very well and would order for us.

    Worse than the fact that she was ordering for me was that fact that I don’t think she had stopped staring at me since I had arrived. I on the other hand had only briefly glanced at her as I had spent most of my time trying to avoid looking at her.

    Now though when I did finally work up the courage to look her in the eyes again, she was smiling and suddenly the ill and queasy feelings began to fade.

    Oh what a beautiful smile. She was truly striking and melted into her eyes.

    As I was lost in yet another trance for the evening, the waitress arrive and took our order from… well “Ma’am” and departed leaving us alone again although I don’t think I even noticed.

    My trance was snapped when spoke again.

    “Now then little one, about my Wedding Dress and your desire to have it. I have to admit that at first I thought there was no way. But the fact that I just wanted to be rid of it won out then the more I thought about it, the more you intrigued me and I wanted to see what my gown would look like on a man. Yes missy that means that if you want my dress, you have to let me see you in it first.”

    With that, she broke out into a very large Cheshire cat type grin that sent a shiver up my spine.

    What more could I do but say…

    “Yes Ma’am”

    The rest of the meal was rather uneventful compared to the start. It was almost as if we were on a first date. We talked and got to know each other and exchanged stories of friends and relatives and discussed some of likes and interests and before I knew it the check was there and the meal was done. I still can’t get over how at ease I felt with this woman and still didn’t know her name. Granted I knew other things about her like she had a sister and grew up in a small village in the English countryside, etc… but not her name.

    She on the other hand seemed to know everything about me. Even though some of her questions had seemed similar, there was subtle differences and I almost felt like I was at a therapists office even though I had never been.

    After she paid the check, we left. I had tried to pay and had started to reach for but was stopped short when she merely threw a hundred dollar bill on top of the 40 dollar check.

    “That will more than take care of our bill and make up for and of the earlier inconvenience or scene you may have created with your apology.”

    That moment that I had managed to briefly forget about, came flooding back to me quickly and along with it came a red burning feeling in my face and cheeks.

    As we departed from our booths, she grabbed my hand and led me out of the restaurant at her pace. Once outside she asked where I had parked only to say that it didn’t really matter as I would ride with her to pickup my prized Wedding Dress.

    On the way to what I assumed was her house we continued our dinner conversation. Or rather she continued with it and her questions and I offered answers and honestly and openly as I could.

    It wasn’t a long drive and the time seemed to fly by before I knew it were pulling in her drive and from there, into her garage. It was then I realized that I had been so enamored with her and had been concentrating on her lovely voice and answering her questions that I had no idea where I was in addition to not knowing the name of this woman that I was with.

    At this point, I began to get very nervous and this time I was also a bit scared.

    At this point we were sitting in her garage as she pressed the button to close the garage door.

    There was another awkward silence and once again I was afraid to look at her.

    Once again, it was she who broke the silence with yet another bone jarring question.

    “Are you wearing any lingerie right now?”

    With everything that had been going on, I had completely forgotten about the bra and panties and pantyhose that I was wearing under my clothes. One of my bra straps must have been more noticeable than I thought or maybe my shirts had ridden up when I got in her car and she had seen my hose.

    Regardless, I hadn’t lied to her yet tonight and wasn’t going to start now. I somehow sensed this was something bigger than me and it would be best to go along with things a while longer and see what develops.

    “Yes Ma’am, I am wearing panties, pantyhose, and a bra.”

    “Very well then, you are to wait here until I have exited through the door you see over there and then you are to strip down to your lovely lingerie. You are to leave your man clothes here in the car and once you have opened the door to exit the car, be sure to press the lock button before closing it and sealing your man clothes along with your wallet and your keys with it. Once you have sealed your fate, you may follow through the same door.”

    With that she got out of the car and left just as she said she would.

    I on the other hand just sat there once again with butterflies in my stomach and strange look on my face almost trance like.

    She snapped me out of my trance by activating and deactivating the car alarm with her fob causing it to chirp.

    “Don’t be all day dear, I’m so looking forward to seeing you in my dress. By the way hon, you look so simply sissy in your pink undies. No do hurry.”

    And with that she was gone through the door.

    I felt a little better hearing that she was actually looking forward to seeing me in her dress but oh my, I was so very nervous still.

    It was with shaking hands that I began to remove me manly outer clothes.

    After just a few minutes, I was following her steps in my own pantyhose covered feet.

    I paused briefly at the door before turning the knob. Did I really want to do this? What were my options at this point anyway? I didn’t know where I was. I didn’t know who I was with. I had just locked my wallet and money, keys, cell phone, what change I had, a few mints, etc… all in her car… I was sunk and had no choice…

    With that I reached for the doorknob and slowly gave it a turn…
     
  2. dollyanne
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    dollyanne Sissy who loves pink frilly things!

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    Wow...sissy missy, this is terrific! Dollyanne can't wait to hear what happens next behind the door! Outstanding story!

    Huggs,
    :manga_exclaim:
    dollyanne
     
  3. subhub1
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    subhub1 Member

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    Very good story, i look forward to the next part
     
  4. crayle
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    crayle Junior Member

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    I would LOVE to see more of this!
     
  5. caged ray
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    caged ray Junior Member

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    pleasure and pain

    Missy,

    That was a fantastic beginning to a story. I am wearing my CB-6000 and I am so aroused that it hurts.....so good. Keep up the story please!!!

    Caged Ray
     
  6. caged ray
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    caged ray Junior Member

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    pleasure and pain

    Missy,

    Great beginning of a story. I am in my CB-6000 and so aroused it hurts....so good.

    Caged Ray
     
  7. felicity
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    felicity Junior Member

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    i love this story missy please please can we have a part 2 soon.

    thank you

    felicity
     
  8. Miss D
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    Miss D Expert In Femming

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    I certainly approve of the story - it is very appropriate for sissy gurls. Don't you all want to buy your very own wedding dress? Of course you do... You never know - you may need it some day...
     
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