Jeff slid into the seat on the airplane. He always hated traveling. It wasn’t so much the comfort factor as he was relatively small at only five foot eight. But nonetheless Jeff always seemed to attract the most undesirable people on the plane who somehow always had to be sitting next to him.
To make matter even worse was the fact that he knew just how long this trip would be. Jeff had recently moved to England from the United States and the long flight over was still fresh in his mind. And now, only a few months later, he was on his way back for business. Despite this Jeff was a little more at ease knowing he would have a week off after all of his meetings to visit with his family and friends.
As he was settling down for what he knew was going to be a long flight his eye caught the sight of one of the most beautiful woman he had ever seen. She had brunette shoulder length hair that framed a face with the most delicate features he had ever seen. However, what caught his attention the most was her shapely body. She had an astonishingly small waste that helped form the perfect hourglass image.
Jeff seemed to loose sense of reality and before he knew it he was staring as she made her way down the isle and stopped at his row. Still captivated by her image, he was finally thrust back to life when he heard her softly say “Excuse me, I need to get past you to my seat.”
Jeff did a double take looking at the empty seat next to him before looking back at the beauty. He couldn’t believe his luck. Could he really be that lucky to sit next to this beauty for the long flight? Jeff immediately stood up and let her get herself situated in her seat before taking his seat again.
It wasn’t until halfway through the trip before Jeff finally got up the nerve to talk to her. He had noticed that she was reading an article about models in her magazine and promptly asked “Sorry for being nosey but I noticed what you are reading, are you a model?”
“Oh dear no” she giggled, “I was just trying to find something to pass the time” She replied.
“Oh, well you are definitely beautiful enough to be one” Jeff weakly stated.
“Well thank you….” She trailed off.
“Oh I am Jeff”, he said picking up on her hint.
“Well Jeff, my name is Rebecca and let me tell you this body is the product of a lot of upkeep.”
“Well whatever you are doing keep it up, you look amazing! I hope you don’t think I’m being to forward or anything but you have the perfect body shape.”
She blushed and replied “Well I must confess that I have some help in that department. You see I wear corsets and that’s probably why you find my body shape in the state it is.”
“Really? Wow, I can’t say I have ever met anyone who has ever worn a corset. I have seen them in some movies and all, and I must say they have always intrigued me, but it seems like most woman don’t wear them anymore.” Then with a pause Jeff continued, “I’m sorry you must find this a little uncomfortable.”
“Oh I don’t mind really. It’s not some secret or anything. I’m comfortable with myself so I really don’t mind.”
For the remainder of the flight Rebecca and Jeff chatted back and forth swapping backgrounds and stories of their personal life. Jeff learned that she a very successful businesswoman who was going to be staying at her apartment in the city while doing business the next week or so.
Eventually the plane landed and as Rebecca stood up and began to get her carry on bag from the overhead storage.
“Well it looks like the end of the road” Jeff said. “I just wanted to let you know how much I enjoyed your company. It sure made the flight much more enjoyable.”
“It was fun, and a great way to spend the ride over.” She paused a bit and then reached into her purse and pulled out a business card and slipped it into Jeff’s hand and whispered into his ear “don’t be a stranger” before she turned and walked off the plane.
Jeff stood there several seconds before he looked down at the card she given him to see it had the address of her apartment listed on it. Jeff smiled to himself before walking off the plane.
Business went well and before Jeff knew it all his meetings were done and he had a week of vacation to spend however he wanted. Initially he had planned on spending it catching up with family and friends. However, the conversation and company of the plane trip kept playing in his mind and it was only a few hours after his last meeting before Jeff found himself standing in front of the door to Rebecca’s apartment.
Nervously, Jeff knocked on the door not knowing if she really ever expected him to take her up on her implied invitation.
It was only a few moments before the door opened and Jeff was greeted with the site of Rebecca looking just as gorgeous as he had remembered.
“I’m so glad you were able to stop by. I was beginning to think you wouldn’t” greeted Rebecca.
“Well how could I say no to such a beautiful woman who made my trip over so enjoyable” Jeff sheepishly replied.
“Well come in and have a seat. Would you like anything to drink?”
“Thanks, and I will have whatever your having.” Jeff replied as he took in Rebecca marvelous apartment.
Jeff sat down and waited for Rebecca to return. It was only moments later before she came into the room and set a glass of wine down for him.
“Thanks, and I just have to say that you look absolutely wonderful tonight” Jeff said as I took a sip of wine.
“Why thank you” she replied. “However, it probably has more to do with the stricter corset I’m wearing tonight.” She said smiling.
The two continued to chat and have drinks. Eventually the conversation turned back onto the topic of corsets.
“I find them so interesting. They make the wearer look so sexy, and I cant help but to wonder just what it would feel like to wear one” Jeff said without much thought.
Rebecca let a small laugh out at that statement. “Well would you like to see how it feels to be laced into corset?” grinned Rebecca “I mean, you did say you always wondered how it would feel…”
“Umm…well it was more an inquisitive remark than anything. Besides it’s not like I could fit into anything you have.” Jeff replied hoping to get himself out of the clear.
“Oh I don’t know about that” grinned Rebecca. “You’re only slightly taller than me. Sure you’re more muscular and solid, but I’m sure with some tugging and squeezing I would not only have you in one, but tight-laced as well!”
After a moment of silence Rebecca continued, “Oh come on it will be fun.”
Even though Jeff hadn’t verbally agreed he knew there was no getting out of it.
“I can see you have already made up your mind” Jeff laughed nervously. “One way or the other you’re going to get me into a corset tonight aren’t you?”
“You could say that, and perhaps a little more.” Rebecca teasingly replied as she sauntered down the hallway towards her room.
Jeff stood frozen watching Rebecca’s perfect figure walk down the hall, teasing him to follow. Without much thought to it Jeff began dreamlessly walking towards her room despite knowing what laid in store.
As Jeff entered, Rebecca stood in the center of the room holding a corset in each hand. She stared seductively at him as if to say she had him trapped and she knew it.
“So which one is it going to be?” Rebecca said raising the two corsets up. In her right hand she held a plain white satin corset, and in her left hand she dangled a sensuous looking black satin corset. For some reason the look of the black corset just drew Jeff in and without hesitation he replied, “I like the black one.”
“Great, I was hoping you would choose this one! This corset has so many possible additional features, and it’s just so feminine the way it looks. You are absolutely going to love this. Now strip everything off and we can get you into this sexy piece!” She said as she flung the white corset onto the bed.
“Ummm…Everything?” Jeff asked, a little nervous about getting naked in front of someone he didn’t really know all that well.
“Well we can’t very well lace you into a corset with your shirt and jeans on. And your boxers will definitely ruin the image of the corset.” Rebecca stated. “But if you’re going to be so modest then you can wear these.” She said as she walked over to her dresser and tossed Jeff a pair of black satin panties.
“Listen Rebecca, I don’t know if this is such a good idea. I mean the corset is one thing but these?” Jeff said raising the panties up.
“Oh come on Jeff, please….” She said as she came closer to him; running her hands over his body. “What’s so bad about the panties? Sure they are more feminine than your boxers, but they will look divine with that corset. And besides its only me and you here, no one will ever know.”
Jeff practically melted as Rebecca ran her hands over him. He couldn’t help but think that she had a point. With that he took the panties and slipped into them. He was amazed at how wonderful the silky material felt as they slid up is legs. Enjoying the experience, Jeff couldn’t help but think that perhaps Rebecca was right; they were not that different from his boxers. Sure they were much more smoother, felt really nice, and were cut differently, but they were actually quite pleasant to wear.
Jeff’s thoughts were quickly interrupted as he felt Rebecca’s hand reach from behind and gently massage his groin through the panties. “I can see someone is enjoying wearing those panties.” She seductively whispered in his ear.
“Now” she said as she stepped away “lets get you into that corset.”
“I think I should be able to get your waste down a good four of five inches.” She stated as she picked up the corset. “Ok, this will work better if you have something to hold onto. Why don’t you go over and hold onto the top of the door.”
Jeff walked over and grabbed onto the top of the door. Within a matter of seconds Rebecca had wrapped the corset around his waste and started to thread the laces into the corset. Jeff couldn’t help but think as to how odd it was that the corset had to open from the back and that the laces would have to be undone in order to remove it. Those thoughts were quickly thrust out of his mind as Rebecca gave a hard tug on the laces.
As the corset continued to tighten Jeff couldn’t help but notice how sensual and erotic the whole experience was. From the firm way it held him, to the way it started to mold and shape him to its shape. Just when he thought she had finished lacing Jeff felt her give the laces sharp tugs before she started to tighten the laces even further. When she was finished Jeff became aware of how the firmness and pressure the corset restricted his breathing. He immediately learned that he would have to take short shallow breaths.
“Ok sweetie, you can let go of the door!” Rebecca stated with a noticeable hint of glee to it.
As Jeff lowered his arms he felt like the corset grew even tighter. In shock he let out a tiny little gasp.
“So tell me how does it feel?” Rebecca asked.
“It’s like nothing I have ever experienced before. The tightness and pressure as it molds and shapes me feels so erotic and yet makes me feel so vulnerable and helpless.” Jeff replied.
“Really?” Rebecca said as she moved behind Jeff once again, taking two small strips that had half of a zipper on each side and attached it to either side of the corset and zipped the two strips close over the laces before finishing it with the snick of a lock securing the zipper shut. “And how does that make you feel?” she laughed.
“What did you do that for? I think this has gone far enough, now unlock me and let me out of this thing!” Jeff stated franticly.
“Oh come on sweetie. Just a minute ago you couldn’t get over how wonderful it felt, and I just wanted to show you some of the other features of this particular corset. I’ll let you out once were all through having fun. I promise.”
“I don’t know Rebecca, I thought this was all we were going to do. What else could you possibly have in mind?”
“Well, seeing you in my corset and panties really turns me on, and you look so feminine and adorable. I was thinking that perhaps you would let me finish off the transformation and see how you looked as a woman.” She said as she sauntered over to Jeff and once again began to gently stroke his groin through the satin panties. “Please sweetie?”
“I don’t know Rebecca…” Jeff didn’t know why he just didn’t say no, but as he stood there feeling the erotic pressure of the corset, and the caressing hand of Rebecca through the panties he couldn’t help but utter “Yea… ok. I guess it could be fun.”
“I promise you that you will look amazing! Luckily you don’t have much body hair so we can skip shaving your legs.” Rebecca said as she strolled over to her dresser once more and began to dig around and select things.
“Ok sweetie, why don you take a seat on the edge of the bed and we can get your legs encased in these sexy stockings I have here.”
Jeff nervously made his way over to the bed knowing that once he let her continue with his transformation that there would be no backing out until she decided she was completely finished.
Jeff sat down on the bed and tried to calm himself down as Rebecca started to roll the stockings up his legs. The cool sensation of the silk stocking being slid up his legs was much more pleasing and enjoyable than Jeff ever thought it would be. When she finally had them on each leg she lightly ran her fingers up each of Jeff’s legs and thighs before hooking the stockings to the garter straps hanging from the corset. Jeff didn’t know what struck him as he was consumed in the sensation of soft feminine lingerie.
After making sure Jeff’s stockings were on correct Rebecca stood up and grabbed the bra she has selected and held it out for him by one strap. She let it dangle teasingly off of her index finger before saying “I want you to but this on for me sweetie. I want to see you slide this bra over your shoulders and strain to hook it.”
With a shaking hand Jeff reached out and took it from her. He slowly slipped his arms through the straps and reached around and grabbed the two sides and tried to do the clasps in the back. After much fumbling around and struggling Jeff was finally able to get it hooked.
“Very good, I’m surprised you were able to get that hooked all by yourself. Are you sure you haven’t done this before?” Rebecca winked at Jeff. “There’s still something not quite right about your figure though….. I know what it is!”
Rebecca walked over to her closet and dug around in the back shelves for a few minutes before coming out with two boxes. She set them on the bed and opened them up to reveal two very real looking breasts. “These will give you just the right shape that every woman should have up top. Now this might be a little cold at first since I’m using medical adhesive, but this way they will stay in place. Don’t worry though, they should warm up fairly quick!” She said as she coated a clear liquid on the backs of the breasts. She stuck them in the cups of Jeff’s bra and pressed them up against his chest for a few minutes before she took her hands away. Jeff could immediately feel the additional weight of the breasts and was at once glad for the support the bra provided.
“Ok now lets get you dressed!” Rebecca said as she tossed Jeff a soft black skirt. He started to step into the skirt and immediately noticed how soft and intense it felt as it slid up his stocking clad legs. Much to Jeff’s surprise, Rebecca had selected a skirt that was very stylish and yet still only came to just above his knees.
Rebecca smoothed Jeff’s skirt out for him and then went back to her closet and took out a long sleeved burgundy top that had a draping neckline. As she handed it to him, Jeff couldn’t help but notice how soft and light weight it was. For a moment he thought that it wouldn’t fit, but as he began to put it on he felt it stretch. Needless to say it hugged and accentuated every feminine curve Rebecca had created.
Jeff couldn’t help but catch Rebecca’s smile as she took his hand and led him over to her vanity where she had him sit down in the chair. Then, much to his surprise Rebecca was straddling his lap and reaching onto the vanity for her makeup. “Ok sweetie tilt you head back just a bit and let me make you into the woman of your dreams.” She said as she winked at him.
Jeff did as she instructed and tilted his head back and let his eyes close. It wasn’t long before he felt the soft movements of brushes sweeping across his face, covering it in layers of makeup. Jeff couldn’t help but think of how erotic it felt as Rebecca moved the brushes and pencils along his face. To further add to his excitement Rebecca would occasionally wiggle her bottom and press up against Jeff’s member or let her soft breasts rub up against the fake breasts she had attached to him. With all of this stimulation Jeff sat there extremely turned on unable to hide the fact. While he knew Rebecca could feel his excitement she never outright acknowledged it, but seemed to wiggle her bottom in his lap to further arouse him.
In all of his life Jeff never though that he would be getting excited by a woman applying makeup to him while wearing a full set of her lingerie and two large fake breasts. With that thought Jeff felt something slide on top of his head and the sensation of hair draping over his neck. Wondering what was going on, Jeff slowly opened his eyes and tilted his head up and looked into Rebecca’s eyes as she adjusted what obviously was a wig.
“Don’t move just yet, I still have one more things to do before your all made up!” With that Rebecca grabbed Jeff’s chin and brought her other hand up holding a tub of dark red lipstick. She moved her face and hand closer to his mouth and expertly applied a nice coat over his lips. Within a second of her hand dropping down she embraced Jeff in a deep passionate kiss. He could hardly contain himself. The feeling of the clothes and the makeup along with the taste of lipstick intertwining drove Jeff absolutely insane. Rebecca finally drew away and slowly stood up giving Jeff’s panty covered crotch a squeeze.
“Go ahead sweetie, take a look at yourself while I get a few other small things.” Rebecca said as she walked over to her closet.
Jeff nervously turned to the mirror Rebecca had at her vanity, half expecting to look like nothing more than a man in drag. Much to his surprise Jeff looked somewhat convincing. The corset and false breasts did wonders to shape his body into a female form, and Rebecca had done an amazing job on his makeup. Combined with the shoulder length brown wig Jeff couldn’t help but admit to himself that Rebecca had done a pretty good job. While he knew he would never pass for a woman under close scrutiny he couldn’t help but think that he just might get by on a casual glance.
“All right sweetie, just a few more things to finish off your illusion.” Rebecca said as she sauntered back to Jeff, holding a pair of high heels. “Here slide your feet into these heels.” She said holding up a pair of high heels that must have had at least a five-inch heel! “Now these are a bit extreme, and are more of a prop than everyday wear, but they were a little bit to big on me for my Halloween costume but they are the only ones I have that you will be able to squeeze into.”
Jeff slowly rose one of his stocking clad legs and gently began to squeeze his foot into one of the heels before doing so with the other. Rebecca was definitely right; they were without doubt a tight fit. However, just as she said, Jeff would be able to fit in them.
Rebecca promptly kneeled at Jeff’s feet and began hooking the straps around his ankle. Just when he though she was done Jeff once again heard a couple little * snicks * and assumed she had clasped them shut. However, when he looked down, much to his horror, he found out that she had instead padlocked the straps shut. Jeff knew right then that there would be no way he would be able to remove his heels without her key!
“Hey, why did you lock these things on me?” Jeff cried out.
“Oh come on silly. It’s just a little bit of fun. Just go with it and enjoy yourself!” Rebecca said, completely blowing off Jeff’s complaints. “Alright sweetie, give your new shoes a twirl. Lets see how you handle those new heels!” And with a sharp slap to Jeff’s bottom she sent him off around the room.
It took Jeff awhile, but after getting accustomed to the feeling of heels, and a few shaky laps around Rebecca’s bedroom, Jeff began to feel like he was walking like a pro. However, Jeff’s pleasure was short lived as Rebecca stopped him and told him “You have your balance down, but your still not walking like a woman. Swing your hips and give yourself a sway. That’s the only way you will look like a woman in heels instead of a man.”
Jeff took her suggestions and tried to sway his hips but it wasn’t to long before Rebecca stopped him and said “Your just not getting it. Your movements are either way over the top or just look forced or unnatural. Now I could have you prance around this room all night before you got it down, but I think I know something that will give you that natural sway. Now I don’t think its necessary…” she said as she reached into her nightstand drawer “but it will most definitely get the job done. Now come and lay across my lap.”
Jeff did as she asked. It was only a matter of seconds before he felt her hand slowly make its way up his stocking clad leg and raise the hem of his skirt. “Ok sweetie, I’m going to need you to be nice and still and try and remain relaxed.” Rebecca said as she lowered his panties. “Now this may be a bit uncomfortable at first be let me assure you that it will eventually feel wonderful.” With that Jeff felt something cold and slimy, yet firm, begin to spread his butt cheeks and slide into his bottom. Despite Rebecca’s words, Jeff couldn’t help but to start squirming around from the discomfort as the object stretched his hole. However, a sharp slap on his bottom from Rebecca put him back in place. Fearing another spanking, all Jeff could do was moan as Rebecca continued to apply pressure as she slid the object further into him until suddenly when Jeff thought he was about to be split in two the remaining part of the object easily slid in. Rebecca then promptly raised Jeff’s panties back up and lowered his skirt back into place before giving him a firm pat on his now full bottom.
Jeff quickly stumbled off of Rebecca’s lap and in a panic reached back and tried to feel what was now unfamiliarly stretching his butt. Unable to reach he looked up into Rebecca devilish stare and asked, “What did you stick up there?”
“*giggle* Silly it’s a butt plug. I know it feels strange and weird right now but once you get used to it you wont feel right without one. And once you start walking around again on your heels you will see exactly why I thought a butt plug would be a good idea for you.”
Not the least bit happy Jeff immediately started to walk around the room again hoping that the sooner she was happy with him, the sooner he could get out of this. Much to his embarrassment Jeff could feel the plug shift and move inside his bottom causing him to tighten up his sphincter muscle in order to hold it in place. Much to Jeff’s surprise this caused him to add a little wiggle and sway to his walk.
“See, now your walking much more womanly and all because of the little friend I stuck up there.” smirked Rebecca. Jeff started to blush at the comments and from the erotic feeling of the plug caused.
“Alright, what now?” Jeff asked hoping she was done with him.
“Well silly, I didn’t get you all dressed up and train you to walk like a girl for nothing.” She said as she walked out of the room and into her kitchen. When Jeff finally made his way into the kitchen Rebecca handed him a sealed addressed envelope and stated “Since you look so adorable why don’t you head out and mail this envelope for me. There’s a mailbox about two blocks down. Just walk down there drop it in and come back and I will have a special surprise for you.”
She led Jeff to the door, opened it and pointed him to the direction of the mailbox, turned around walked back inside and shut the door leaving Jeff alone on her front steps.
Jeff had never felt more vulnerable and exposed than he was now as he stood outside her door dressed as woman with a butt plug buried deep in her bottom. Jeff stood on the steps for a few minutes before he finally mustered up the courage to begin his journey to the mailbox. Jeff couldn’t help but feel so self-conscious as he began the 2-block trek to the mailbox. As Jeff began walking he experienced the most foreign sensations. The cool evening air never let him forget that his legs were encased in stockings while the light wind blowing his skirt bottom made him even more aware of what he was wearing. With each step Jeff took he could feel the slight jiggle of the large breasts and hear the seemingly loud click of his heels as the sound pierced into the silent evening. All while the unfamiliar sensation of the plug brought him to a new level of excitement. Thankfully for Jeff Rebecca had insisted he tuck his male member between his legs, otherwise the smooth front of his skirt would most definitely have an obtrusion.
After what seemed like hours to Jeff he finally arrived at the mailbox and dropped the envelope into the mail and turned around to head back to Rebecca’s. On his way back the sensations and feelings soon turned to a deep pleasure. Taken by this intense pleasure Jeff slowed his walk in order to relish every moment of the sensations before he would be back in the safety of Rebecca’s apartment.
As Jeff neared Rebecca’s place he noticed she was leaning against the doorframe of her open door with a look of amusement on her face. “I see that you enjoyed yourself darling, perhaps a little to much…” Rebecca said as she reached under Jeff’s skirt and began to massage his panty-covered crotch.
With glowing smile Rebecca led Jeff back to her bedroom and flung him onto her bed. “Now for that surprise I told you about.” She said as she began to kiss him deeply while continuing to rub his panty-clad crotch. Just when Jeff thought he was going to go over the edge Rebecca stopped rubbing him and scooted herself up and straddled his face. Without any hesitation Jeff stuck his tongue out and began to orally please Rebecca. Jeff expertly worked her to several orgasms before slowing down and teasing her eventually sending her to an earth shattering orgasm.
After awhile Rebecca slid off Jeff and worked her way down to his skirt and flipped it up. She then pulled his panties to one side freeing his member. Without hesitation she took it into her mouth. After all the events of the evening it wasn’t long before Jeff was on the edge of an orgasm. Suddenly the sensation of the weight of the breasts, the clothes, the makeup, and the way his butt now clenched tightly down on the plug caused Jeff to burst into what was easily the best orgasm he had ever experienced. As Jeff lay there in post orgasmic bliss he could feel Rebecca continue to play with his member as she worked it into what felt like a plastic tube before he eventually heard a little snick and she pulled his panties back up and gave Jeff a deep kiss that had the lingering taste of cum.
Jeff lay there admiring Rebecca’s firm curvy figure clad only in her lingerie as she walked to her dresser and removed a red silk chemise and brought it back to the bed with her. She immediately got to work carefully removing Jeff’s top so as not to disturb his makeup and wig. After that she removed his skirt. As Rebecca was removing his top and skirt Jeff couldn’t help but think that perhaps his experience was coming to an end. That, however, was until she once again surprised him and had him slip on the chemise. Rebecca then slid into the bed next to Jeff and cuddled right up against his back and whispered into his ear “Good night sweetie!” After all the events of the evening Jeff drifted off to sleep.
Jeff woke up groggily, stretching out in a vain attempt to wake himself up. It didn’t take him long to realize that he wasn’t in his hotel room and that he felt different. Jeff lay there for a while with his eyes closed trying to remember everything from the previous night. All he could seem to remember was that he had worked up the courage to visit the stunning woman at her house for a few drinks. It was obvious from the strange feelings and his lack of memory that those few drinks had turned into more than a few.
Jeff stretched his hands out to either side of himself to feel if Rebecca was still here. She wasn’t in bed so he assumed that she had gotten up already. It was at that point that Jeff’s senses really started to alert him that something was different. For starters Jeff felt like he was engulfed in soft satin. He just shrugged that off as not being accustomed to the sheets Rebecca had on her bed. But not so easily explained was the weird weight he felt on his chest, the odd feeling of being full in his butt, why his waist felt stiff and constricted, and the fact that his morning hard on seemed to be obstructed and unable to get fully erect.
He slowly ran his hands up to his chest and was shocked when his hands brushed the fake breast. His eyes opened up abruptly and he threw the covers off and jumped out of bed. It wasn’t until then that the previous nights events started to filter back into his head.
Jeff looked into the mirror and suddenly started to grasp just how far everything went. The wigs hair was somewhat messed up but the makeup was still as expertly done as last night. He was still wearing the chemise, heels, corset, and the other lingerie from the previous night. Jeff nervously reached behind himself and felt the firm base of the plug confirming the reality of the still hazy evening. Jeff then began to investigate what was restraining his morning erection and placed his hands inside his panties and found that is member was encased in a small plastic shell. It was at that moment that Jeff realized that Rebecca had placed him in a chastity belt! Jeff couldn’t think of when she locked that on him but slightly remembered hearing the familiar snick of a padlock closing during his post orgasm heaven when he had thought Rebecca had still been playing with him.
Jeff couldn’t believe this and knew he had to get out of this stuff. He practically tore off the chemise and grasped to rip the corset off but couldn’t find the laces; instead just a smooth surface and two padlocks at the top and bottom. In his frustration he lost his balance in the heels and fell back onto the bed. Jeff immediately went to slip them off when he remembered that they too were padlocked on. He sat there with his head in his hands wondering why he hadn’t put up more of a fight when she was locking all of that on. Now there was no way for him to get out of this mess. He slipped his chemise back on taking some comfort in the fact that it covered the lingerie that now adorned his body.
After several minutes of sitting there in complete shock Jeff noticed a folded piece of paper on the bedside table. He took it and opened it up wondering what Rebecca had left to say to him.
I hope you like the name I gave you. I just didn’t think Jeff would be appropriate in your current state. I’m sure by now you have discovered everything that remains from last night. I cannot tell you how much I enjoyed all of it. While I know that you had several drinks and probably don’t remember a lot of last night, I still never thought you would go along with what I had planned, or for the matter as far as things went. I want you to know you make such a sexy little sissy. While I do not know if this is what you truly wanted, I do know that a small part of you couldn’t say no to this experience. I am sure you are wondering about the situation I left you in. While I know you can, and probably have, removed butt plug and whatever clothes you could, there is still the matter of the other items that you do not have the keys for. I am sure by now you have realized exactly what the locks on the corset and heels mean. I’m sure you also found the chastity belt I placed you in. I’m sure this came as a surprise to you as I sort of snuck it on you. You see when you came in and I saw you enjoyed your little stroll I couldn’t believe what a sissy you were. I was quite unable to accept this and thought of it as a little revenge for enjoying what was supposed to be slightly frightening for you. Additionally, incase you haven’t noticed last night I used long lasting makeup products on you. Your makeup shouldn’t run or fade for at least four or more days and wont be completely gone for about another week. Now I, on no certain terms, plan to keep you captive within these items; however, I do have a choice for you to make. You may or may not remember last night I said I was leaving town for business today (Friday) and would not be returning till Monday evening. Should you want to see where this relationship takes us and decide to stick around I will coming straight home on Monday and we can continue where things left off. However, if you wish to stay there are several rules you must abide by. You will keep your buttplug in at all times, and you will continue to dress in a dress or skirt and blouse at all times. Additionally, I request that you take it upon yourself to maintain the upkeep of my apartment in the meantime. If you however wish to leave, which I wont old against you, you can leave at any time. While I have disposed of the male clothes you came here in, I’m sure you can find a pair of jeans or something less feminine to wear on your way out. I however cannot give you freedom from those things locked on you so you will have to leave wearing them. You see that envelope you mailed last night was an envelope containing the keys to the padlocks on your corset, heels, and chastity belt. I made the envelope out to the address that was on your driver’s license. Since the mail wouldn’t be collected until sometime this afternoon I doubt the keys will be sent out to your address until Monday and will take at least a little over a week to reach your home in England. Although I assure you that all the keys are in that envelope and you will have your release when they arrive. Whatever you decide I wish you the best of luck, and want you to know how much I love my sweet little sissy girl.
Jeff couldn’t believe what he was reading. How could she have done this and made it sound like it was no big deal, let alone ask if he wanted to see where a relationship with her would go.
Jeff slipped off into a dazed state letting the letter drop out of his hands. It wasn’t long before the unfamiliar weight of the breasts tugging on his body, and the excruciating tightness of the corset brought him back to earth.
Jeff wondered how he had allowed himself to get into this situation? All he knew was that he had to get out of here. Rebecca was insane to think that he wanted this. He couldn’t actually believe that anyone would actually want this?
However, as Jeff reached underneath his chemise to take out the buttplug, he had still yet to remove, his hand lingered on the satin material of his panties and his mind drifted back to the enchanting words left in the note and the captivating woman who had put him in panties. Perhaps something deep down in him really did crave and want this.
Jeff couldn’t believe himself. He didn’t actually like the way these things felt and he didn’t crave this did he? Confused and emotionally drained from all the events of the past day Jeff sat down on the wooden stool at the counter. He was immediately reminded of the buttplug, he had yet again forgotten to remove, as it was crammed even further up his already unfamiliarly stretched bottom. Jeff pushed the discomfort to the back of his mind and began to think about the decision he had to make. A decision he found harder to make than he ever thought it would be.
Hi! I am Deborah, the mistress that runs Satin Submissions.