Boo! Happy Halloween all of you panty-wearing sissies! Hoping you’re enjoying the Halloween weekend! I will be available all today and late into the evening, taking your Halloween confessions! Hope to hear your sexy voice soon!
New Halloween Sissy Bride Story!
I have another great Halloween story submitted by one of my callers. It’s long and delicious and covers the making of a sissy bride, a reverse wedding, chastity, and feminization, so sit back and enjoy this naughty tale of a Halloween sissy bride!
How Becky Spent Her Halloween
My arms ached a little, having been stretched out on the red leather bench for so long. I could feel my long nails against the heel of my hand as they were wrapped around the cold steel legs of the bench; the same legs where my wrists had been handcuffed. I had purchased the four foot by two foot bench for a place to sit down and put on my shoes in the mudroom but she had found a different use for it. Bent forward at the waist while on my knees, my chest and tummy would lie comfortably along its soft leather top and I could just reach the opposite legs along its length. The handcuffs would not allow me get up. I might have been able to shimmy around the side and free myself if it had not been for the ropes at my thighs. Each of my legs spread wide and tied just above the knee to the remaining two bench legs.
Every now and then I could hear some movement upstairs. It had been a while since the last little trick Mistress had played. She enjoyed the little stressful tortures she had planned for me. About thirty minutes ago I had heard the doorbell ring. Tied up as I was, I had panicked. Who could it be? I can’t let anyone see me dressed like this! Is it a neighbor? Or worse, one of my friends from the party! I heard the click, click of her heels coming down the oak steps. The one change she had made since coming back to my place was the stiletto heels, the rest of her costume remained the same. I yelled up for her to ignore the door and they would leave. I received no answer. Clack! The door unlocked and I heard some muffled voices. Once again I heard the click, click of high heels coming down the last half flight of the split entry stairway.
She opened the door. The bench was positioned so I couldn’t see her come in or if anyone else was with her. I felt a light slap on my panty covered ass before she kneeled beside me and softly ran her fingers along the lace of my stocking top before playing with the garter tab. “I almost forgot how cute you look, all dressed up and helpless like this,” she said. “We have a visitor.” I asked who it was but she only said that telling me wouldn’t be any fun. She stepped around to kneel behind me and ran both of her hands up my thighs to grab me by the hips. She pulled herself hard into me slapping her pelvis against my ass a few times before commenting, “Oh, this is just the perfect height, isn’t it?” She slid back a little to cup my cock and balls in her hand to rub and squeeze some life into them. It didn’t take much work on her part.
Just as I was getting hard I was jolted back to reality, “Ma’am?” said the voice of a strange man.
“Just a few more seconds, I just found my purse,” she shouted upstairs as she continued to massage my cock through my silky white panties. She stepped over to the mantle and grabbed my wallet before straddling the bench. She shimmied up so my head was nestled right in the crotch of her pants. I could barely do much more than lift my head tied up as I was.”How much should I tip the pizza boy?” she asked. “Or maybe he would prefer something besides money,” she giggled. I’m sure she read the worried look in my eyes as she pulled out a twenty and wondered aloud, “Hmmm, how long do you suppose before he gets impatient enough to come downstairs? You might be able to get the pizza for free.” Another
“Ma’am?” came from the entryway before she crawled over the top of me, gave my bottom one more playful slap and went up the stairs. I had recovered from the panic and embarrassment in the thirty minutes since then. I still don’t know if the pizza boy saw anything, it’s not too difficult to see down that half flight of stairs if you crouch down a little. This was the thought that kept running though my head; that and how I had come to be in this position in the first place.
It was another Friday night in the middle of summer. My friends and I had just finished pouring the glasses of beer at the little bar we frequent after softball. Catherine and I were recalling some of her past Halloween parties; she is always in charge of the Halloween parties. Over the past number of years I have been known to come up with some pretty good ideas and everyone now expects me to go all out for Halloween. Right in the middle of a sip of her beer, Catherine set down her glass. She suggested that I should go as a bride to this years Halloween party because she just got her veil back from the cleaners. I clapped my hands together in mock girlish delight and she did the same. The closest I have come to dressing as a girl in front of my friends was two Halloweens ago when I went as a half male/half female. Everyone thought it was a great costume, that Halloween; I even shaved one leg for the costume. I always thought that if I dressed fully as a girl, that my friends would think I did too good a job and become suspicious. None of them knew of my secret hobby. Anyways, when Catherine suggested I go as a bride, deep inside I was thinking it was a fantastic idea. Not wanting to sound overly excited I decided to play it down a little. I told her that if she could find a dress that would fit me, I am 6’4″ after all, I might think about it.
With that she announced to the table that I should go as a bride. Some people laughed and others groaned then people started shouting out other crazy ideas. Some of the suggestions were a female figure skater, a Vegas showgirl, or anything else they thought would embarrass me the most. I pretended that I thought they were crazy but with each new idea I mentally saw myself dressed in all the female finery. It was a great few minutes; I actually had my friends shouting out how I should be dressed as a girl for Halloween. Eventually the laughs died off and the conversations drifted to other topics as they always do.
A few weeks later, towards the end of August, I received an email from Catherine. She wrote that she was planning a Happy Hour for Friday after work. I wrote back that I would be able to make it and was pretty excited about it. Softball season had ended the week before and our weekly gatherings would have ended otherwise. Friday night I made it to the bar about 15 minutes late; I noticed some of my friends at a table and went over to join them. When I got situated I noticed that only the girls were there and I looked around for the guys. I asked them what was up and they told me this was a girl’s night out and they had a favor to ask me. Catherine had come up with a plan for Halloween and all the girls thought it was a great idea. They wanted me to be the bride we had discussed the other night and they were going to be my bridesmaids.
I sat there in shock for a few seconds, just enough time to gather my wits. I didn’t want to appear overanxious. So I asked why me? They said that I was the only guy who would be brave enough to do it… I told them I was too big and tall to fit in a wedding dress. They told me, that’s what alterations are for. I asked them, aren’t wedding dresses expensive? They had considered that too, between Catherine, Cathy, Suzie, Chrissie and Zeny they would put up $100 each for me if I put up $300. That totaled $800 and that should cover almost anything we would need. I reluctantly agreed.
The next few weeks went by quickly as we started to pull together the costumes. On one occasion, Zeny worked something out with the store manager at David’s Bridal. If we showed up at around 5:30 on a Saturday, we could browse until the store closed and then try on some of the dresses we thought might work out without offending any customers. I milled around the front of the store as the girls went to get their bridesmaid outfits. As the last of the patrons were leaving, they took me back and pulled out a few dresses to hold up against me to see how they might look.
In that flurry of activity before the manager had locked up for our special fitting, a very attractive woman walked up to us and excused herself for eavesdropping but she wondered if they were really here looking for a dress for me. She had long auburn hair and looked to be in her late 20’s. There was stunned silence for about five seconds and I finally said that’s pretty much what we were doing. It seemed everybody else was as embarrassed as I was before I answered. That broke the tension and some of the girls giggled. She said that she was sure I would make a beautiful bride and then asked if I was going to actually try a dress on here. She seemed very interested as we discussed my fitting before excusing herself and turning as if to leave.
She quickly turned back and asked if we would mind terribly if she could see me try one of the dresses on. The girls looked at me and I said why not. She introduced herself as Audrey. To be honest, I had known Audrey for some time. We had met online sharing the common interest of boys dressing as girls. She has her own website and has a variety of interests including a job as a phone sex operator.
We had cooked up this scheme as soon as I told her what the other girls had planned for Halloween. Audrey didn’t want to miss out on any of the fun. They had me try on several dresses but we didn’t have very much luck, nothing really seemed to be just right. It was quite a thrilling experience for me to be modeling bridal gowns for all the girls, something I never would have imagined a few months ago. Each new gown was met with a chorus of cheers, laughter and clapping. I turned bright red from embarrassment every time I came out of the changing room. I must have looked ridiculous. Without any makeup, short hair, a dress that didn’t fit me well and five o’clock shadow…I looked like a man in a dress. About an hour later we had decided to try E-Bay and would come back here if that didn’t pan out.
Audrey thanked the other girls for letting her be part of the fun. She only wished she could see if they could make me look the part after the final transformation. Naturally, Catherine invited her to come to the party and after a little more talk, and a few more hints by Audrey, it was decided that she could be the groom. The manager of the store was happy with the outcome as she sold us five bridesmaid dresses and a tux for Audrey.
I was awakened from my reverie by the riding crop tracing up and down my thigh and along my aching crotch. I was so deep in reminiscing I hadn’t heard her come down the stairs. I was particularly startled when she tapped my overly accessible balls with the crop. It took so little to get my penis hard since the chastity device was finally off. “My goodness,” she said, “I don’t think we’ll be able to get that steel tube over your cock again. Maybe this will help.” I felt her pull the crotch of my panties to the side so my cock and balls hung free. In one hand she held two pieces of ice and started to stroke my cock with the ice in her hand. With her other hand she ran another piece of ice all around my scrotum. I was writhing around trying to pull myself free but there was no chance. The cold of the ice against the heat of my throbbing penis was unbearable. It was a unique mixture of pain and pleasure that literally made my balls ache with pain yet all I could do was hump the ice in her hand to keep the sexual gratification from ending. She did this for several minutes and try as I might I could not make myself cum due to the cold ache of the ice on my scrotum. “Well that didn’t help,” she said, “it’s just gotten bigger. It looks like I will have to try something else.” Then she pulled my panties back into place, settled the remains of the ice in the crotch of the panties and went back upstairs as I awaited her return.
It was about three weeks before the party and the dress had arrived that I had found on E-Bay. The girls wanted to make sure everything had been accounted for before the Halloween party. They pulled the gown out of the box and ohhed and ahhed over all the snow white layers of tulle that made up the skirt. Some thought the off the shoulder long sleeve design of the satin bodice was pretty but laughed when someone mentioned that my A cup body had nothing to hold the dress up. They insisted I try it on so they could see if it fit properly. So once again I found myself standing in front of all the girls wearing a pretty white wedding dress. But this time it was my own pretty white wedding dress. It was bought and paid for and soon enough I would be wearing it for all my friends to see.
The dress fit well, maybe a little tight, but the girls were right about the off the shoulder gown not staying up and the zipper kept falling down. They soon discovered I had not closed the fastener at the top of the zipper and like magic everything stayed in place. Suzie thought we should get a long line bra and we could stuff the cups to fill out the bodice a little. That’s when Audrey brought out the box she had come with. She told everyone that after some quick calculations that we should have plenty of money left for some late additions to the wardrobe. The wedding dress had only been $230, that along with theother items; shoes, jewelry, etc., we still had about $400 left over. She opened the box to reveal a fully boned white over-bust corset. “This might help give her a little shape,” she said. The other girls chuckled; I’m not sure if it was over the sexy garment or Audrey’s use of the term “her”. Catherine pulled it out and held it up. She absolutely loved the four dangling garter straps hanging off of its bottom. A couple of the girls looked shocked, I don’t think they have ever thought about wearing a corset themselves much less expected me to wear one. The girls looked at me as if to ask if this was all right and I responded that if we were going to do this, we might as well go the whole nine yards.
So, a few minutes later, I was standing in front of the girls while being laced into the corset. For the sake of propriety I was also wearing a pair of gym shorts. I don’t think any of the girls wanted me to take my shorts off, except maybe Audrey. The girls were fascinated at the process of lacing me in the corset. They commented on how much a difference it made around my waist. It subtracted about 4 inches and gave me surprisingly girlish figure. Audrey suggested I try on the shoes as well just to see if I could manage to walk in them. I knew I wouldn’t have any problems since I had worn heels many times before, but the rest of the girls didn’t know that. The one problem I did have was slipping them on.
Since I was in the corset I couldn’t bend over to pull them on and I had a difficult time slipping them on to my bare feet. Audrey pulled out a pair of thigh highs and said they would make getting the shoes on a lot easier. Chrissie and Suzie helped pull them on since I still couldn’t bend over and everyone else was in stitches at my predicament. Wearing a corset, having two of the girl’s help me into stockings so I could better put on my heels was quite a funny site. Catherine was laughing so hard she was crying and I thought she was going to pee her pants. Zeny was laughing at the long, matted hair on my legs trapped under the stockings and commented on how tacky it looked. She even suggested I should wax my legs for the big day.
That brought out another huge burst of laughter. I said maybe I should, we have some money left over. To be honest, this was another plan Audrey had dreamed up. It was just happenstance that Zeny suggested it. Audrey was going to make the same suggestion and I was supposed to make like it wasn’t that big of a deal. Chrissie and Catherine tried to talk me out of it saying it would be too painful. The others thought it was a good idea. We argued a bit about it and I asked them how painful can it be really? That changed their minds; suddenly everyone thought I needed to see for myself how bad it really was. Zeny took the initiative and said she would schedule it since she worked as a receptionist at a local spa. In the end they decided a few days ahead of the party for the waxing and we could all go the day of the party for a mani-pedi and I could have my makeup done.
The girls had me walk around a bit in the shoes and were impressed with my balance on the heels. They eventually let me out of the corset and as the evening was getting late, decided to call it a night. It was about five minutes after everyone left that Audrey came back. She said she had one other surprise for me and pulled out a box labled CB3000.
“This is a chastity cage,” she said, “I know how much dressing up for us excited you and I think you might be tempted to play with your clitty over the next few weeks.” She was right of course, right after the girls left I was planning on relieving a little sexual tension. She told me to take off my shorts. It took quite a bit of coaxing to get the device on.
It was about fifteen minutes later that I heard the click of the lock imprisoning my cock and balls. “You’ll get this,” she said, referring to the key, “right before your appointment.” As she walked out the door she also told me I should get my arms and tummy waxed too while I was there. “Now don’t enjoy yourself too much,” she laughed waggling the key at me, “Oh right. I guess you can’t”.
This time I heard Audrey coming down the steps. As she walked around the side of the bench I could see the black wool pants of her tuxedo step past. Once again she straddled the bench and shimmied up close to my face. I could see a large bulge of a strap on in the crotch of her pants. “Well, my pretty little sissy bride. You’ve been good enough that I might just let you go. But you know what you have to do to earn your freedom, right?” I told her that I wanted to make my husband happy, which apparently was the right answer. She slid her crotch closer to my mouth as I had so little range of motion being tied down to the bench. I raised my head and caught the belt between my teeth; I worked hard to undo the buckle. Eventually the belt was pulled free of the pants and I started to work on the pants button and zipper. My chin kept rubbing against the hard shaft trapped in the pants.
Finally, I worked the zipper free and could see the prize waiting for me inside. I went head first into the wide open pants but couldn’t get the cock free. I was trapped along Audrey’s thigh inside the pant leg. I rooted around with my mouth trying to pull it free. I worked my tongue under the shaft and pulled back my head only to have it slip free. I worked for several minutes and was finally rewarded when it popped free and slapped me along the side of my cheek. I noticed the red of my lipstick staining the shaft of the cock where I had been working at pulling it free as I leaned in to take it in my mouth.
Flash! I heard the camera go off while I was straining forward to grab the cock with my mouth as Audrey pulled away from me….
(to be continued…)