How Becky Spent Her Halloween

How Becky spent her Halloween
by beckygirl

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; same legs where my wrists had been handcuffed.

I had purchased the four foot by two foot bench for a place to sit 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 canít 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 couldnít 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. ìI almost forgot how cute you look, all dressed up and helpless like this.î she said. ìWe have a visitor.î I asked who it was but she only said that telling me wouldnít 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, ìOh, this is just the perfect height, isnít it?î She slid back a little to cup my cock and balls in her hand to rub and squeeze some life into them. It didnít take much work on her part. Just as I was getting hard I was jolted back to reality, ìMaíam?î said the voice of a strange man.

ìJust a few more seconds, I just found my purse,î 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. ìHow much should I tip the pizza boy?î she asked. ìOr maybe he would prefer something besides money,î she giggled. Iím sure she read the worried look in my eyes as she pulled out a twenty and wondered aloud, ìHmmm, how long do you suppose before he gets impatient enough to come downstairs? You might be able to get the pizza for free.î Another ìMaíam?î 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 donít know if the pizza boy saw anything, itís 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.

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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 fantastic. I decided to play it down a little. I told her that if she could find a dress that would fit me, I am 6í4î 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 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 girlís 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 didnít 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, thatís what alterations are for. I asked them, arenít 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 Davidís 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 shoulder length auburn hair and looked to be in her late 20ís, maybe 30. There was stunned silence for about five seconds and I finally said thatís 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 Jessica.

To be honest, I had known Jessica 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 attending B&D munches, her own web site as well as a side business selling lingerie on E-Bay. I had even dressed for her on a few occasions. We had cooked up scheme as soon as I told her what the other girls had planned for Halloween. Jessica didnít want to miss out on any of the fun.

They had me try on several dresses but we didnít 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 didnít fit me well and five oíclock shadowÖI 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 didnít pan out.

Jessica 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 Jessica, 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 Jessica.


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 hadnít 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. ìMy goodness,î she said, ìI donít think weíll be able to get that steel tube over your cock again. Maybe this will help.î

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. ìWell that didnít help,î she said, ìitís just gotten bigger. It looks like I will have to try something else.î 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.

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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 Jessica 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 the other 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 Jessica'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 Jessica. 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. Jessica 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. Jessica 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 sight. Cathy 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 Jessica had dreamed up. It was just happenstance that Zeny suggested it. Jessica 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 Jessica came back. She said she had one other surprise for me and pulled out a single metal handcuff with a curved metal tube welded to it. "This is The Houdini," she said, "I know how much dressing up for us excited you and I think you might be tempted to whack off 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 as it doesn't leave much room for the scrotum. This of course, is part of the design so it doesn't come off. It was about fifteen minutes later that I heard the ratcheting sound of the cuff tightening around my now imprisoned 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".

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This time I heard Jessica 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 new 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 Jessica'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 Jessica pulled away from me. I had been involved in so many pictures during the last few days, I barely remembered what it was like not to have my picture taken.

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Of course the girls had a camera at the salon. There were pictures of me with the girls as we had our nails done. They thought it would be best if I had a full set of acrylic nails since my nails weren't long enough and then had them finished in a fancy, french manicure style. Then as the other girls were having their nails done, I was brought to the makeup station. Every now and then one of the girls would stop by and ohh and ahh over the progress that was being made. The most embarrassing part was having the other customers or a teenage girl point and giggle at me. It took at least an hour to get my face on properly. There was time spent waxing my brow, applying foundation, eye liner, eye shadow, mascara, blush, lip liner, lipstick, bronzer, yada, yada, yadaÖand the pictures. Suzy couldn't get enough pictures of me getting all made up. After that it was another thirty minutes fluffing and styling the wig so that it was just so and fitted to my head right.

As we drove back to my place I pointed out that we still had about four hours until the party. Chrissie said that would give us plenty of time to get dressed and go and take some photos for my wedding album. This was the first I had heard of this plan, but it would just give me more time to enjoy being dressed.

Cathy reached over and ran her fingers over my hairless arm and commented on how smooth it was. I didn't tell the girls, but for the last week I had been using baby oil on my arms and legs after I got out of the shower each day. It was a trick I had learned from an ex-girlfriend when I had made the same comment about her soft skin. It still was a little disconcerting about the hair there. I had even taken to wearing thigh highs under my pants for the past few days since the waxing, which, looking back, was just as painful as the girls had said it would be.

Once we were back at my place it was time to get dressed. I excused myself to go get started. I had learned through trial and error over the years to apply my press on nails after I had finished dressing because long nails made things like garter tabs and zippers much more difficult. This time my nails had been glued on before I had the opportunity to get dressed. I worked slowly so as not to break a nail and hadn't made much progress before a knock on the door came asking if everything was all right. I told the girls about my problem and their first reaction was to tell me under any circumstances, I was not to ruin my nails. Zeny asked if I was decent before coming in and I wasÖsort of. I had managed to put on the corset but not tighten it and I had pulled the garter tabs through the leg opening of my panties.

The door opened and I saw Zeny and Catherine cover their mouths as they tried to hold back their laughter. They had seen me in the corset before with a pair of shorts on but never quite this feminized. There I was in full makeup and wig, hairless as a newborn wearing nothing but a bridal corset and panties. The panties themselves were french cut so there was quite a bit of skin showing. There were ties at the sides with a big pink bow and they were covered with rows of pink and white ruffles in the front and back. They asked me where I got such a pretty pair of panties and I said they in the same box as the corset, I just assumed I was supposed to wear them. They said that was fine they were just surprised at how different I looked dressed like this. Luckily, the frilly ruffles and the fact that the panties were a snug fit helped to hide the fact that I was getting a little hard. Of course it didn't help that I had finally been able to remove the chastity device and my penis wanted to explore its recently new found freedom.

Zeny and Catherine explained that the bridesmaids were supposed to help the bride get dressed anyways, and that they could help me finish dressing if I needed it. So they sat me on the edge of the bed and pulled out a fresh pair of stockings. One at a time they slid the gossamer thin fabric up my now smooth legs. They stood me up and tightened the corset around my waist and made sure everything fit properly and I was comfortable. They were both very helpful and went about the business of getting me dressed just as if I were one of the girls. I tried to fasten the stockings to garters but with the long nails it was useless. I had a difficult time keeping my emotions and my cock under control as they finished smoothing the nylons up my legs and brushing my inner thigh and ass cheeks with their fingers as they attached the garters.

They sat me back down on the bed to help me with my shoes and I quickly jumped back to my feet. They both looked at me oddly and asked what was wrong and I turned a little red and said I was fine. I told them I had felt a little pinch from the corset boning was all. I sat back down and Catherine slid a white satin pump with a three inch heel onto my foot and started to buckle the strap. Zeny was doing the same with my right shoe and stopped to look around a little bit confused. She asked what that buzzing sound was. I stopped biting my upper lip and told her it was probably just my pager from work. The truth was Jessica had another of her little tricks planned for me.

Before the girls had come in to help me dress I had found something besides the panties in the corset box. Jessica had left a note and a small egg shaped device maybe three inches long and an inch and a half in diameter with a plastic cord connected to the end. The note said to lubricate the egg and slide it in my ass. I did just that and left the cord end out thinking it was to help remove the item later. It felt kind of sexy as I pulled up the panties and the egg was certainly a unique sensation as I walked around. The cord was actually an antenna for the remote control vibrator that was inside the egg and now in my ass. I certainly couldn't explain that to the girls and I had to keep from squirming while they finished putting on my shoes.

I was breathing heavier as they finished the shoes and I stood up on the pretense that I could breathe easier standing than sitting. That also quieted the buzzing as it didn't vibrate the mattress as I was sitting down. I asked for the hoop skirt next as I didn't know how much longer I could keep my erection from becoming too noticeable. I stepped into the slip just as the other girls were coming upstairs from getting their own dresses on. Suzie, Chrissie and Cathy relieved Catherine and Zeny as my helpers so they could go get dressed. Jessica was also waiting outside the door all dressed her tuxedo including a top hat and tails.

After a few more pictures in my lingerie, Chrissie pulled out the gown with a sense of reverence that she must have felt when she dressed for her own wedding. The dress was very formal with stitching and pearls covering the bodice, and the girls were very careful as they slipped it over my head. The long satin sleeves also had appliquÈ and pearls but not so much as the bodice, ending with a row of eight tiny satin buttons at the wrist. As they buttoned the wrists I knew it would take me a very long time to get out of the dress, my own long nails would be useless trying to manipulate the tiny buttons. I was dressed this way until somebody helped me out of the dress.

The skirt was a single layer of white nylon covered with a white layer of netting and three more layers of the softest white tulle. With the petticoat the dress stood out at least three feet wide as the girls fussed with the layers of tulle and netting to make it look just right. The girls stepped back and fussed a bit more until Zeny and Catherine were dressed. Once we were all dressed, all of the girls gave me the final approval with a number of "I can't believe how good he looks" and "That's amazing! That dress is so pretty on you" comments.

Then just as we were ready leave, the girls had one last surprise for me. Cathy slipped a choker of tiny white costume pearls around my neck that she had found at a garage sale. Zeny gave me a small bouquet of white roses that she had picked up at the flower shop earlier in the day. Chrissie and Suzie helped to pin the veil from Catherine's wedding onto my head, the very veil that started this whole thing at the bar so many weeks ago. And Jessica had me lift my shoe so she could slide a blue and white satin trimmed garter slowly up my leg. Something old, something new, something borrowed, and something blue.

The rest of the day was filled with parading around town in my wedding dress for a variety of photo opportunities. We spent some time at the Japanese Gardens, the Sculpture Gardens, and other landmarks. We even took some photos at a local church. Everywhere we went people would gather and offer to take our picture or want to have their picture taken with me, the guy in the wedding dress. Naturally, Jessica would turn on the vibrator that was deep inside my ass hidden under the layers of satin and tulle at the most inopportune times.

And then it was off to the party where everyone was amazed at the great job the girls had done. A few of the men were uncomfortable with how thorough a job had been done and they talked about how they would never dress up like that. A lot of the girls would come over and talk about all the things I had to endure. Little did any of them know just how much fun I was having.

Jessica again made a point of buzzing my ass whenever I was in the middle of a conversation or as I was being handed a glass. Eventually I started to get used to the timing of her little surprises. So in order to mix things up a little, Jessica had purposely left the remote control on the snack table in the middle of the room. No one knew exactly what it was and the curious instinct of everyone was to look at it and press the button a few times. They would turn it on and off, and on and off, and then pass it to someone else and ask what it was for. It was really quite erotic glancing over at the table and seeing a total stranger or even a good friend of fifteen years, making me feel so sexually aroused.

Being totally feminized as I was, for everyone to see and the random buzzing of the toy kept my cock at full attention for the entire party. I was so glad to have the hoop skirt so no one could see how sexually aroused I was. Eventually, the batteries gave out and I was afforded a little bit of relief from the devious toy Jessica had given me. Then, in time, the party wound down and my night of girlish bliss was almost over. But not before Jessica had just a little more fun.

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Jessica had moved around behind me since I had finally pulled the strap on free from her pants. I still could not turn to see what she was doing but I did hear her pants come off. She kneeled behind me and ran her fingers down my spine before reaching the back lacing of the corset. She once again began to tease my cock within the silky confines of my panties and play with the garter tabs holding up my silky stockings. My hard on grew quickly, not having been allowed to climax for several weeks due to the chastity device that had finally been removed earlier today.

I felt her slowly pull on the satin ribbons that held the panties on my hips. My penis quickly sprang straight out as the bows were untied and Jessica slowly slid the wispy fabric up along my exposed scrotum and over my now naked butt. I felt the cool, slick wetness of baby oil dribbling onto the top of my widespread butt cheeks and slowly trickle down the crack to my little rosebud. She found the string of the long since dead vibrator and started to pull it out. Very slowly she would pull the string and my sphincter would expand a little before she let the toy slide back into place. This went on for quite some time before she finally let the widest part of the toy slide out and the remainder followed easily.

She leaned in over the top of me and started to lubricate her strap on by running the length of the shaft up and down the crack of my ass. "Mmmmm, I bet that feels good, doesn't it Becky?" she asked, "knowing that this big cock is going to be pumping in and out of your little sissy bride ass." I moaned in agreement. She commented on how wet I was down there and how much I must want her cock inside me as she continued to slide her cock up and down. She talked about the pretty lingerie I was wearing and how helpless I was tied up like this. She could do anything she wanted to and there was nothing I could do about it. She was in total control.

Then she changed her tactics on me, as she so often does. "But that's what you want, isn't it?" she asked. She stopped, stood up and walked around to the front of the bench. She reached down and unlocked the handcuffs that had held my down for so long. Then she walked around to the other end of the bench again to untie my legs. My limbs were stiff from being stretched out all that time as I rolled over onto my back on the soft leather. "You are free now. You can go get out of your pretty lingerie."

I sat there for a second stunned at the turn of events, staring at the strap-on bouncing between Jessica's thighs.

"Mesmerizing isn't it?" she laughed as she made the dildo bounce from side to side. "You don't want me to stop." she said. No, I didn't want her to stop, I wanted to get fuckedÖand hard. "You're just a boy who likes to dress up in your lingerie, pretending to be a girl. That's sounds like a sissy to me." she chided. "And a slut too, just hoping I will stick this big, long cock deep into your ass." I begged and pleaded with her to fuck me and make me her little sissy bitch. I crawled on my hands and knees to where she was sitting on the couch saying I would do anything if she would just fuck me.

After minutes of begging she finally agreed and had me straddle her cock and sit down on its length while she sat on the couch. I reached around behind me to guide the dildo on into my waiting ass and slowly impaled myself along its length. It slid in easily from the baby oil and the fact that I hadn't shrunk too much from the vibrator being in there all day. I slowly ground my hips into her lap.

I understood that Jessica was fucking me because it was her choice, not mine. Jessica had rested her hands on my hips and set the rhythm of our fucking, she was in control of me. I though back on all the pent up sexual energy from the day last few days. Trying on wedding gowns at David's Bridal, having my legs waxed, getting my nails and makeup done in public, the erotic sensation of Zeny and Catherine sliding stockings up my hairless legs. I never realized I was such a sissy that I would do all these things so easily, especially in front of my friends. And here I was being fucked by Jessica. I was totally under the spell of being feminized.

After a little while Jessica had me back on the bench on my back as she leaned in over the top of me. My legs were spread wide and wrapped around her waist as she thrust into my ass. I lay back and let her fuck me however she saw fit. She leaned in farther over my chest and could feel my own hard cock trapped between our bellies. The friction of each thrust was intense against my penis. I arched my back and tried to meet each thrust of Jessica's.

Jessica continued to fuck me for a good twenty minutes any way she could think of, I just followed her lead. She would occasionally reach around to grab my throbbing hard cock and pump it until she though I was about to cum, teasing me right up to the edge. Then after she had had enough, she pulled the strap-on out of my abused ass.

I still had not been allowed to cum as we sat and talked for a few minutes about everything that had happened over the last few months before she got ready to leave. "Well, I bet you're going to whack off tonight," she giggled and paused "Unless...". "Unless what?" I asked, as she pulled out The Houdini chastity tube. "Unless you'd prefer to get all dolled up in some sexy lingerie for me again next weekend," she asked. Of course I gave in. That's what Jessica wanted and I was totally under the spell of being feminized.

The end

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chicago

Chicago

I was in Chicago on business and had my first experience with a professional role play Mistress this week ...
The Massage

The Massage

I started wearing panties when I reached puberty just as most TV’s before me. My very first orgasm was in my sister’s panties and it was fantastic ...
How Becky spent her Halloween

How Becky Spent Her Halloween

Something old, something new, something borrowed and something blue, but Becky wasn't blue at all, dressed to the nines in a bridal dress ...
Amy the wicked step sister

Amy the wicked step sister

Growing up with a step sibling is weird when you begin living with them full time after years of occasional weekend visits ...
Sissy In The City

Sissy In The City

An english sissy spent three months in California on a work visa program - as a waitress and sex toy of a rich businessman! ...
vickis first taste

Vicki’s First Taste

I never found out who it was who gave me so much pleasure and I still await my punishment, which no doubt, one day will come ...
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tiffany

The House has been great, this sissy feels that this is a great community with very respectable Superiors and Staff who run our House. This sissy is very grateful. The House of Sissify has helped this sissy keep in mind… Read more “tiffany”

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