Steph Jewett's picture

Opening his eyes in the morning to no alarm was another thing Jordan enjoyed most. A day off always followed the long week when all of the Airbnb’s were booked. It was the little things Jordan began to appreciate most. He always would in bed for at least 20 minutes, gently rolling around, feeling the lace clinging to his body. He loved waking up in panties now. This was his favorite pair which he had regularly work as PJs.

As he got out of bed, he gently walked to the bathroom, up on his toes, checking out his ass in the mirror as he passed it. Brushing his teeth, he admired his plump ass and how sexy it looked, always imaging it on the body of a sexy woman when he looked in the mirror. Today he had the chance to achieve it. Today was his first day off in weeks, busy season was officially over and Jordan had the entire day to himself. Today was not just his day off either, it was also purge day. Jordan began to love and hate purge days. He loved them because he got to look like the sexy woman he always wanted to see in the mirror. The only downside was at the end of the day he made himself toss it all away, “for good” as he had said so many times. Today was unique for Jordan; a guest had finally left behind a wig, something he had been waiting a few months to happen.

Another great thing about his days off was breakfast. Andrea would cook him a delicious breakfast after he had cleaned all 19 houses. It was her way of saying thank you for his hard work. She wasn’t a bad cook either, not the best but he was not about to turn down a free meal. Jordan finished brushing his teeth, and started to get dressed, slipping a long sleeve knitted shirt on and pulling sweatpants up to just below panties. Before pulling them above his ass, he rested them gently underneath his bum, looking in the mirror. “Today’s the day I put this all behind me, I’m purging these panties, everything’s gonna go. It’s the only way to stop for good” he said to himself as he took a final look at his sexy ass before he pulled up the gray sweatpants.

“Pancakes or French toast?” asked Andrea as he walked into the kitchen.
“French toast, please” he said as he sat down at the table.
“Ok, it will just be a few minutes; there are some biscuits in the oven that are ready if you can take them out and put them on the table.”

Jordan got up from the table, pulled the biscuits out of the oven, placed them on a plate and returned to the table.

Before he was done with his first biscuit, Andrea sat down with two plates, one stacked high with French toast and the other a plate full of bacon. “Pass the syrup Hun” she said as she motioned towards it. “Thank you again for doing such an amazing job this past week. I know it can be hard, but busy season has passed and you’ll have some downtime to get back to some of that design work you’re always telling me about.”

Andrea raised her mimosa to Jordan’s, they gently touched them together, making a pinging noise, then both sipped from their champagne flutes. “Today is the start of busy season for me though. While the houses are not booked out I plan on taking advantage and trying to flip a few of them. As I’ve keep saying, it’s a sellers market!” she said with a cheery smile.

“How long will you be out of the house for today?” Jordan asked, trying to hide his excitement as he had just found out he would not only have the day off today, but the entire house to himself now.
“I’ve got appointments all day showing some of the houses.” She said as she glanced at her phone to check her calendar, “my last showing is 7 o’clock tonight.”
Hearing “7 o’clock” Jordan’s face nearly lit up before he quickly stuffed his face with French toast to hide it his excitement.
“Now I know it’s your day off, but I have one thing I need you to do before I get home today. Just fold and put away my laundry for me. I’ll leave it all in my room for you before I leave.”

He was barely listening to Andrea, his mind was running through everything he was going to do today, where he would start, how he was going to look!

“Hellooo, Jooordan… can you take care of that for me”
Snapping back to reality, “Uh, yea sure”

Andrea and Jordan finished breakfast and sat for a little sipping their mimosas, talking about the latest gossip from around the neighborhood. Jordan always had the best stories; he spent most of his days walking around, seeing everything that was happening. Jordan filled her in on a few things from the past week, nothing major had happened. Andrea went to her closet to change into more professional clothes, leaving the table to be cleared by Jordan. He cleaned up, did the dishes and headed back to his room.

As he went upstairs, Andrea was just locking up the house and heading out for the rest of the day. “Don’t forget, laundry’s in my room. Use your key to get in, I didn’t set the alarm” she yelled to him as she headed into the garage to leave.

Jordan watched as from his window as Andrea backed out and drove off to her first showing. Kneeling down at the foot of the bed, he pulled out a large cardboard box, opened it up and began laying out everything inside. First was the brunette wig, it was long and a bit wavy. Jordan liked it. Besides, even if he did, he was in no place to be picky, he was just happy someone left it behind for him to try on. Next came the matching three piece set. First were the blue sheer, thigh high stockings, then a matching bra and panties set with clips. The blue in the set matched the blue stockings. Jordan pulled a large makeup bag and carried it to the bathroom, placing it on the counter. Walking back toward the box, he grabbed the last item, a pair of five inch red stilettos.

Jordan found a few pairs of shoes over the past few months, but these were the ones that fit him best. They were the only thing to survive a purge other than the first pair of blue boyshort panties he found. He planned to purge it all this time though, even the heels.

Jordan paused, admiring his collection for a moment and thinking about where to begin. He knew he had to end with the nail polish, it needed time to dry and he couldn’t be getting dressed or applying makeup with wet polish.

“Makeup... or the matching set” he thought to himself. He opted to go with the matching set of bra, panties, and stockings. He slipped off his clothes and started with the panties. Jordan slid the panties up, fitting them into place and attaching the clips to the front and back. He had gotten better with the clips, at first it was a struggle to get the ones behind him, but now it only took a few tries.

Taking the stockings, he rolled them up so he could slide his legs slowly into them. Jordan regularly shaved his legs so when he would slid them up his legs he immediately felt the softness and sexy feeling he got when he put on stockings. Clipping all four clips to the stockings, he admired himself in the long mirror against the wall. Finally the matching bra, Jordan still had trouble with these and no matter how many times he tried, couldn’t figure out how women clipped them behind their back. He wrapped the bra around his chest, cups on his back, clipping it in front. Once he got it clipped, he spun it around and ran his arms through the straps, adjusting it into place.

He was in decent shape so his pecks kind of filled out the bra. Jordan was lucky this was a pushup bra so it constantly poked out as if he had boobs. There was no way he would be able to fill out the B cups.

Jordan headed into the bathroom and sat down in front of the mirror. He had gotten pretty good at doing his makeup, but he always needed his MacBook next to him with YouTube tutorials to help guide him so he did not mess up. He started with concealer, gently applying it to even out his blemishes, then eyeliner, heavy lines on top, but light on the bottom. Mascara, applying it just as the video showed. Eye shadow next, and this time Jordan was planning on tweezing his eyebrows to match the girl in the tutorials. He finished off his makeup with light lipgloss, nothing too noticeable, just enough to give it his lips a pop.

Once he had done the final touches and brushed the blush gently across his cheeks he grabbed the wig. Jordan had watched a few videos on how to properly put on a wig so it didn’t look like the girl was wearing a wig. This took him a few tries, but finally he checked himself out in the mirror and could barely recognize himself. He loved it, a beautiful woman, staring back at him smiling when he did, blowing kisses to him from the mirror, and sexy as hell. The girl starting back at him looked fit to be a model.

He rummaged through the bag, pulled out a few different nail polishes colors. All of them were pretty empty but the red one looked most like it had enough left in it for one last manicure. Sitting down on the couch, he put on another tutorial. Jordan barely did anything without a tutorial. He always wanted everything to look perfect, every time. As he unscrewed the top, he shot up. He had nearly forgotten his favorite heels. He slipped them on easily and strutted back to the couch, clicking his heels on the hard wood floor.

After he was done applying the red polish to each nail carefully he turned on the TV and started watching some of the shows Andrea had on the DVR. She always recorded girly reality TV and Jordan loved watching them all his days off. The day went on, Jordan making lunch for himself, wearing an apron to keep his sexy outfit clean and then continued watching Andrea’s shows. Nothing exciting, but this was how Jordan loved to spend his days off. Relaxing and constantly checking out the beautiful woman in the mirror.

Jordan must have dozed off watching one of the shows for quite some time. He was awoken by his phone buzzing. He flipped it over and saw it was a text from Andrea.

“On my way home early, no buyers today. My last two canceled so I’ll be home for dinner. I’m picking up Chinese, want anything?”
Jordan’s heart was racing after he read the text. She was on the way! No way he was going to be able to change, remove all of his makeup, nail polish and show up for dinner downstairs.
“No thanks, I ate not too long ago” Jordan lied.

He shot up and was headed straight to the bathroom to take off the makeup. Just as he was reaching to take off the stilettos, he remembered. Andrea’s laundry! He never went down and sorted it. He scampered to the door as fast as he could in five inch stilettos, carefully went downstairs and then back up once he realized he forgot the keys. Heading straight for room he folded and sorted everything as quickly as he could, probably not doing it all to Andrea’s liking. At this point he didn’t care, he had to move fast.

He rushed to put everything away in the black wardrobe. But as he was throwing away the dryer sheet from the laundry he noticed a pair of panties in the trashcan. He ignored them at first, but it was not long before he turned back and inspected at the panties again. He examined them first without touching them. Admiring the sheer pink panties, taking an interest in the very feminine lace trim.

Jordan reached in, grabbed them and was headed for the door, back to his room above the garage to get out of these clothes. Just as he was leaving the door he changed his mind, headed back to the trashcan to carefully place them just as he found them. He was purging today and did not need another pair of panties. If he was able to place them just as he had found them, Andrea would have no idea he ever even touched them in the first place.

As he was lowering them slowly back into the trash he looked up. Andrea was standing in the doorway, stunned. “I don’t know if I should be laughing or applauding your work… What the hell are you doing Jordan!!! …wait, are those MY panties?!” before Jordan could answer more questions came, “And where did you get the rest of that, how did you learn to do your makeup so perfect, and what… what the hell are you doing looking like that?!”

He did not know what to do, he just stood there stunned with Andrea’s panties in one hand, bent over the trash can like, frozen like a statue. There was silence for a minute before Andrea spoke again, Jordan still frozen in place.


“…are you trying to steal those… and wait a minute, everything you have on. I don’t own any of them, but I certainly know them.” She paused, thinking for another minute, still not a word from Jordan. “Oh. My. God. Those are the things people forgot after checking out. One woman sent me a picture of those heels, they were her favorite! I was jealous she didn’t leave them. I may have kept them for myself if they were the right size. I have to say I can see why she liked them so much, your legs look incredible!”
“Uh… Um… Thanks…” muttered Jordan.
“She speaks!” Andrea said with a laugh. “So wait a minute, you stole all of that. Everything you have on you stole from my guests. That is considered theft Missy…” there was another long pause. “Do you know what that means Jordan? Did you read the theft clause in our lease at the beginning of all this?” Jordan shook his head back and forth signaling that was not aware of it. “Stay right there, I will be right back with the lease. Don’t move a muscle either! I have an idea for you and by the looks of it you’re to be a great fit.”

Without another word, Andrea was no longer standing in the doorway; she was rummaging through her files, digging up the lease. He could hear her running back to her room, when she reappeared in the doorway a flash went off, then another, and another. “Perfect!” she yelled, “OMG this picture is going to get tons of hits.”

“Andrea, wait… you can’t…you can’t post that! Please, you can’t do this to me” pleaded Jordan.
“Actually, that is exactly what I can do. See this is the lease you signed” she said as she held up a document with his signature on the bottom. “And in this lease it states that if you violate any terms of the lease, you agree to work for me, in whatever capacity I choose” she said with a smile on her face. “And from what I’m seeing here, I know exactly what kind of work you’ll be doing. See Jordan, I run a website. It’s a very specific website that hosts fetish images. I have tons of models, but mostly freelancers, high turnover, you know” she paused. “Now thanks to you, I no longer need to hire freelancers. You get to be my full time model!”

“Andrea, you can’t be serious. I can’t do that! I have a life to get back to. Please don’t do this to me!” Jordan cried out.
“Again, I can. See it says here that if you break these terms, I can have you arrested. And since you signed it, you agreed to it.” She said as she a few more flashes went off. “So it’s either jail or model.”

Jordan slowly sank to the floor, near tears thinking about what just transpired for him. He was taking everything in, thinking about exactly what Andrea had just said to him when a word popped into his head, “fetish”.

“What do you mean by “fetish site?” Jordan asked.
“It’s probably easiest if I just show you.” She said as she pulled the site up on her phone. “See these are all my photos here” as she opened one section of the site. “The other sections are user submitted. I get a lot of photos sent to me, only can post the best. Aren’t they great!?”

Jordan was silent for a bit, scrolling through the site. It had tons of photos of girls in sexy lingerie, some naked but all drop dead gorgeous.

“What I really like to do is have a theme for each model as I’m sure you can see.”

Jordan scanned through Andrea’s site, some has of the models were shoving dildos down their throats and some up their ass. Other girls were taking strap-ons by a woman who looked a lot like Andrea. A lot of others were just posed in provocative ways, but all following some kind of theme.

“Wait, so… you expect me to be a model for this site? I… I can’t… are you insane?”
“Insane, no, and you very much will be a model for my site. You can choose either to be a model or I’ll have your ass sent to jail right now. And let me tell you, looking like that I’m sure the boys there will love you” she snapped back with a laugh. “And I have a perfect theme for you, one I’ve been able to get a model to agree to. I guess they didn’t trust me completely. But you Jordan, you have no choice” she said with a grin on her face.

As Jordan began to come to terms with what was happening he said, “I don’t think I want to know… do I?”
Andrea laughed and ignored his apprehension, “You’re going to be my bondage model. I’ve never gotten to tie my models up before. This is going to be so exciting, I have so many ideas, poses and ways to manipulate your body” she said. Jordan visibly see the excitement, her face lit up, she was talking with her hands and nearly skipping around the room. “Do you want to hear the best part?”
“…best part for me or you?” Jordan asked.
“For me, but I think in the end you will enjoy all of this too” she replied. “I’ll be able to try all of my toys with you to see which are the most popular on the site. That way I can really take my site to the next level!”

It took Jordan some time to fully come to terms with what he just heard. He was so lost in thought he didn’t even notice Andrea had walked away. When she reappeared in the doorway, this time she was holding pink nylon rope, a leather strap with an O ring, and a steel bar with two straps on each side. “All for you Hun!” she said with excitement and a wink.

At this point, Jordan did not even resist or fight as Andrea walked towards him. He was like puddy in her hands as she moved him into the desired positon. “Now typically my models are somewhat naked, but you look so perfect, I do not want to ruin all your hard work. So I am just going to tie you up with that pretty lingerie set still on” she explained to Jordan. “We’ll just have to work around some things. Maybe just the panties will have to come down a bit when its time to shoot”

She moved his hands behind his back, touching his thumbs to his butt cheeks. Then secured his hands together and tightened it to the point where he was unable to do anything with his arms other than move then up and down. Once his hands were secure, she tied his elbows together to make it a bit tighter, preventing his movement even more. Soon, she started running the rope all around his body. “This won’t be restricting, but I think it will make the photos better. Really emphasize the rope, you know?” she asked. But Jordan did not answer. He was like her little pretty doll, frozen in shock, thinking about how it all went wrong and how he ended up like this.
He felt Andrea nudging his feet apart with her foot., “wider Hun” she said. He slowly walked his feet out wider and wider until she grabbed the steel bar, strapped the one ankle on and held it across to the other. “A little wider Hun” she said. Jordan moved his left foot out a bit more until Andrea secure the other ankle strap. He looked down at his legs, they were about three or four feet apart, and the bar was there to keep it that distance.

“Just a few more things and we will be ready to shoot! Don’t you worry” she said as she stepped back to look at her newest model. “Jordan… are you getting excited over there?” She asked as she saw his dick start to grow under the panties. “Well I’ve never had a model do that before, but then again, all my models have been women“ she thought aloud.

“I’ll take care of that. It won’t doesn’t show well in the pictures.” She walked over to Jordan, pulled his panties down and began stroking his dick up and down. Jordan had a confused look on his face, he did not think for a second she would be jacking him off. “Do you want me to continue?” she asked. Jordan nodded, Andrea kept working her hands around his cock until he came. “See Jordan, I told you would like this.” She said with a smirk. “My, you really are a grower, I did not think that tiny little thing would get that big. Once it goes back down to its little bitty size, we can tuck that away so it won’t show in the photos.”

Andrea wiped the cum onto Jordan’s chest and continued to position Jordan. “Now where were we…” she said as she tapped her lip thinking. “Oh right, let me just tie this around your wrists.” She said as she wrapped a thinner rope around the pink rope at his wrists. “Just walk as best you can towards the bed now Hun.” She laughed as she told him to walk. Jordan inched his way to the bed where Andrea tossed the thin rope above the canopy bed frame and slowly pulled on it, raising his hands into the air and forcing him to bend over. “Just a little more…” She said as she placed her hand on his back, nudging him down until his chest was just above the bed. “There, perfect!” she cheered as he heard a clink on the steel bar where she locked the other side of the thin rope.

“Now for the cherry on top” she laughed. As Andrea walked towards him with the leather strap and O ring, Jordan thought of something he needed to ask Andrea. He interrupted Andrea, “wait, how long is this going to be for? Just till the end of the night right…”
There was silence for a few seconds. Interrupted by Jordan, “what did it say in the lease?”

Andrea dropped her gaze, looked Jordan right in the eyes and replied, “Indefinitely.” She secured the strap around his head, put his mouth around the O ring which prevented him from closing his mouth; keeping it wide open. Jordan was not really able to speak, he could only mumble to Andrea.. The word “Indefinitely” rang through his brain over and over. He didn’t even notice that Andrea had left the room again. Andrea’s hands brought his mind back to the bedroom as he felt his panties being pulled down again.

Jordan tried to look around to see what Andrea was doing, but he could only see the walls, Andrea was directly behind him and he could hear an unfamiliar sound. Once the noise stopped, his ass was greeted by the something cold gently touching his “boy pussy”, as Andrea came to call it. The cold object slowly pressing into his pussy, entering him deeper and deeper. At a certain point, Jordan thought to himself that the size he could take was at his limit. But he did, the object grew in size as it went further and further. After a few more seconds, it was in. It felt like someone had dropped a buoy into his ass. It was surely still inside him, hanging and bobbing as he wiggled his ass left and right. He did still feel something was sticking out the other end, holding it in place.

Jordan continued to sway his hips back and forth slowly, feeling it moving with him. He could feel Andrea’s hands grab his him. “Now if you move too much, the pictures will be bad. You need to try to be still. I need you still so the sparkly pink diamond in your ass won’t be blurry.”

He felt her fingers run from his hips to his face, she put her fingers over his eyes, “now keep them closed, I don’t want to ruin your surprise” she said in a soft but sultry tone. He obeyed, keeping them closed. “No peaking Hun” Andrea said climbing onto the bed. Jordan felt her moving around until he felt her right in front of him. “Surprise” She cheered.

Jordan slowly opened his eyes, beginning to see Andrea kneeling in front of him. He had never seen her in her this close to naked before. She was wearing a black lingerie set that barely held in her perfect tits. His eyes were fixated on them. He had never seen a pair so perfect. All he wanted to do was caress them, touch them. As he went to move his hands toward her breasts, he was reminded of his immobility. “You like them? Well Jordan, tell you what. Don’t freak out during the shoot, be a good model and I’ll make it so you can stare and enjoy tits like these whenever you want. Deal?”

Jordan nodded his head up and down, agreeing to her terms yet again. As she brought his stare down he noticed the pale colored dildo attached to her hips. His eyes went wide and he pulled his head away from her. “Jordan, you agreed you wouldn’t freak out.” She said as she lifted her breasts up. “If you can’t stay calm, no tits for you.”


Jordan took a deep breath and brought his head forward and relaxed as best he could. Andrea inched closer to him the dildo in her hand. She pressed the tip gently around the O ring, just enough for it to touch his lips, leaned forward, softly moving the dildo further into his mouth. He could feel Andrea’s hair as she leaned into his ear. She gently licked and kissed his ear. Jordan could hear the camera start snapping photos, the flash going off every few seconds. “You’re doing great Hun… And remember try to be still.” She whispered into his ear. She kissed his ear once more and as he felt her hair lifting away from his face.

Andrea started to lean back, grabbing the bed frame and slowly moving her hips forward and back. Thinking about how Jordan never even asked to read the terms of the lease made her giggle. None of that mattered now, with the pictures on that camera it didn’t matter what the lease said, Jordan was unquestionably hers, indefinitely.

Hope you enjoyed reading Jordan's story as much as I did writing it.


pink bimbo's picture
Indefinidently - Jordad Ray Stratons Story

I hope there is more to come then just three parts.

Story Rating: 
Loved it

pink bimbo Sissy to Goddess Darque

Alina123's picture
Indefinidently - Jordad Ray Stratons Story

Great start.
Hope to read more soon.

Story Rating: 
Loved it
Lisana's picture
ohmm Mistress

MY clitty startet to grow....
i had to get vibrating dilto and sit and slide on it...
as i cannot get sissygasm like woman yet...i am still without it .....

the story is awesome.....i love it..

Story Rating: 
Loved it

Lisana Sissy Dreamer
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Begging for support poor Sissy Lisana
Be the Patron, please?

Steph Jewett's picture
Jordan's Future

Right now I don't have plans to carry the story on beyond part three. I may write another part in the future. Originally I wanted to close it there, but if enough people like it maybe I will continue his story.

Thank you for reading, so glad you all enjoyed it.


Story Rating: 
Loved it
ripcurlgurly's picture
Epicly excellent

Great story, very steamy.

Story Rating: 
Loved it


Xanthe Altheia's picture
Great story . Please continue

Great story . Please continue if you can.Thanks.

Story Rating: 
Loved it


I am owned and enslaved to Lady Johanna Vendela Liv Silfverstråle.

becca.dear's picture
Great story, I hope there is

Great story, I hope there is a part four. Please please please please.

Story Rating: 
Loved it
Santacruzman's picture
Hot at the end

Could go more or end here. Most of us would like to see the two of them have some gurl on girl time.

Story Rating: 
Loved it