A Sissy Gets Hooked

Julian had found himself getting more and more into posting photos of himself in his sissy outfits. He had posted himself on sissy exposure boards and other websites, but of course being the closet sissy that he was, he made sure to keep his face hidden in his photos. While he made sure to wear sunglasses or have his wig block his face, he didn't hold back on showing off his body or how slutty he could be with it.

He loved how much attention he would get from his photos and all the dirty comments and messages letting him know how much of a whore he was. Every time he was called a whore, something deep down inside of him awakened. The more and more it awakened, he imagined himself as a whore as a hooker walking around in tall thigh boots with a shiny skimpy outfit. However, he knew it was just a fantasy, as he could never really allow himself to do it in real life, so he just decided to develop his online sissy persona into that of a hooker.

Julian really got into teasing all those who messaged him with his role play as a hooker for hire. He would let them know how they could pick him up off the street and how he would give them a front seat blowjob or let them take him into a back alley and fuck his ass for $20. The thought of being a cheap hooker enticed him even further in his role play. He had built up a pretty good online base of followers with many practically just begging to be his first real client. Of course Julian would never allow any of these online perverts to get a hold of him in real life, so he made sure to tease them just enough to have them coming back but not enough that they would be able to find him.

One day, Julian decided to get deeper into his fantasy and that he wanted to do a photo shoot in a sleazy motel. The kind that he had seen often in porn videos. He knew that a shoot in one of those motels would drive all his online followers crazy. Julian knew the perfect one too, as it had been in the news recently due to the city trying to shut it down after the increased prostitution arrests there. What better place to pretend to be a hooker than in an actual place visited by them.

Julian packed up his sissy outfit and accessories and made his way to the motel. As he pulled into the parking lot and saw a hooker coming out of one of the rooms, the realization hit him of where he was and what he was planning on doing here. As he parked, he just stared as the hooker walked away, she was dressed a bit slutty, but not too over the top. He had imagined thigh high boots, fishnet stockings, short shorts, a tube top, and a PVC jacket and even brought this exact outfit for his photo shoot, but the hooker wasn't dressed like that at all. She was just in modest heels, yoga pants, a long sleeve but tight fitting shirt. As Julian watched her walk away, he guessed maybe hookers are quite like how they are portrayed in porn or even in movies.

To Julian, it didn't really matter, he was still going to be in a place that hookers frequented and he would put on a slutty shoot in one of the rooms dressed as the ideal hooker he imagined. He made his way to the lobby and booked a room with cash for a few hours and checked into his room.

The moment Julian opened the door to his room and stepped in, he was immersed in his hooker fantasy. The hooker he saw outside may not have fit his perfect fantasy, but the room didn't disappoint. The carpet looked dodgy with stains, the walls were dirty, the decor looked like it hadn't been updated for decades, and the place smelled of cigarettes, it was perfect for a hooker motel.

Julian got dressed up in his hooker outfit, accessories, and pulled out his sex toys and went about doing his photoshoot. When he got home later that evening and pulled up the photos, he was pleasantly surprised at how well the photos came out. He was soon editing and posting his photos online with a title of "A Sissy Hooker is waiting for her clients".

The more realistic hooker shots drove his followers online crazy, they really wanted a piece of his virgin ass and mouth. Some even offered to pay him a good deal of money to be able to use him for a night. A part of Julian tingled at the thought of being used as a hooker while another part of him realized this was a fantasy and there was no way he would consider revealing himself to anyone let alone meeting up with anyone of them. Julian still basked in all the attention he was getting as the views, comments, and messages counters kept going up.

While he was enjoying his increased popularity, unbeknownst to Julian, the motel that he picked had pretty unique rooms that would be pretty recognizable to anyone who had been there. Obviously, the type of clientele the rooms attracted had unique personalities, especially considering they were usually there to be with a hooker.

One of those unique personalities was Frank. The moment Frank saw the photo set, he recognized the room as he had been to that motel more than a few times and realized this Closet Sissy lived in his city. As Frank looked over the photos he began to think. The thing with Frank, as much as he loved fucking around with hookers, his real hobby was finding closet sissies and breaking them. He loved seeing their faces as he would out them as they realized how fucked they were. He didn't care for the ones that were already looking to be outed, no he wanted the ones who didn't want to be, the ones who thought they could stay in the closet forever while being a Sissy tease from time to time.

Frank had seen this fake Sissy around online for a while and had even messaged him before, but he didn't get very far in his advances with him. He knew that this wanna be Sissy was just a tease and didn't really want to be outed but was the type that just loved the attention they were getting while being as slutty as they could to everyone. Now that he knew that this sissy tease lived in his city, he decided to see if he could hook this sissy in.

Julian sat at his computer reading all the comments and messages that were pouring in from his latest set of photos. He loved how slutty he looked in that dirty motel room. He was getting so worked up from it, that he started to stroke his cock as he read. As he continued to read, he came across an interesting message.

The message mentioned that if he wore a chastity cage he would look even better. Julian had gotten messages in the past from his online followers about how as a Sissy, he should be locked in chastity, but he mainly ignored them as he preferred the option of being able to stroke his cock. However, this particular message went into such detail as to why he should wear a chastity cage that he immersed himself in the fantasy it was portraying. He would see himself as a sissy hooker whose pimp had locked him in chastity so that he would remain all horny and ready for action for all of his clients. He could picture himself wearing a short skirt allowing his locked up clitty (as the message described it as) to peek out from the bottom as he walked in his hooker heels up and down the street. He imagined how it would look as he bent over flashing his ass as the chastity cage would then show once he bent over enough.

Julian was hooked, the message drove him into his hooker fantasy even further and he realized he needed to get a chastity cage. He was so engrossed in it that he nearly came at the thought of being forced to be locked up in a cage while whoring himself out. As Julian settled down from his thoughts, he looked at the message again and saw it was from someone who he had conversed with before. Julian thought back and realized it was a guy named Frank but couldn't remember how their past conversation went as they didn't talk too much before as he wasn't one of his regular contacts.

Julian decided that Frank was someone worth continuing to talk to if he would continue fueling Julian's fantasies. Julian, as her Jasmine sissy persona, decided to message Frank.

Jasmine: OMG, you are so right, a Sissy Hooker does need to be locked away in chastity. I am totally going to order one online now!

Frank: That's a good Sissy, you will look so much cuter with your little clitty locked up. Imagine how it would look dangling under you as your clients fuck you in your pussy.

Jasmine: Oh yes! That would be so hot to have my little clitty dangling as I am pounded back there! I can also picture it bouncing up and down as I reverse cowgirl a client!

Frank: Well, I expect to see your next set of photos with you having a chastity cage on your little clitty. It's been long overdue as you have had that nasty cock out in the open for far too long.

Jasmine: Oh, I am sorry! I guess it wasn't very Sissy like for me to have it out like that, but I like to play with it too much ;)

Frank: Once you put it on, I think it will be a very different experience for you and that you will enjoy being locked up.

Jasmine: We will see, it's been ordered, so it should hopefully arrive in a few days. You will be the first to know when it comes!

Frank: Looking forward to it you Sexy Sissy Hooker!

Frank knew once he got the first reply from Jasmine, he had her hooked. As long as he played things right, he could add another sissy to his list of conquests.

Julian waited three days before the chastity cage came in the mail. Holding it in his hands, it was smaller than he thought it would be, but he had chosen the size based on the company's sizing chart. Once he got it on, he realized it was actually a comfortable fit even with the anti-pull out measures that came with it. After fidgeting with it for a couple of minutes he got used to it and while looking in a mirror he realized it did look cuter being locked away.

Jasmine: I got my chastity cage in, here are some photos of it on.

Frank: Oh, you went with a small pink one. Your clitty looks so much better locked away.

Jasmine: I think you are right, it just looks better with it caged up. However, I already want to take it off and start stroking it.

Frank: Well keep it on for a few days and you will realize how much better it will make you feel.

Jasmine: We will have to see, I will give you an update later on how I do. Bye bye!

Julian spent most of his free time for the next couple of days continuing to read comments and messages while watching her view counts go up. It was driving him crazy not to be able to play with himself with the chastity cage on. After the first day, he decided to have more fun with it and wore a butt plug at the same time. It was pretty thrilling for him at work to have had the cage and plug underneath his clothes that it just drove his horniness to the next level.

Having to pee sitting down on the toilet at work was also bringing out the submissiveness in him as he couldn't take the risk of being at the urinal and having a coworker peek over and see his pink chastity cage. By the third day, Julian had started to wear thong panties to work, as it just felt right to.

By the fourth day, Julian had never felt this horny before as he continued to wear the chastity, butt plug, and thong out in public. It was honestly making him feel submissive as he pretended to be forced to wear these out. He even started to imagine that Frank was the one ordering him to do this.

Julian finally got so worked up that he couldn't take it anymore and by the evening he had unlocked the cage and stroked himself to an enjoyable orgasm. However, once Julian came down from his high, he realized he missed the feeling of being on edge and began to regret taking off the cage and cumming.

Jasmine: I lasted four days but finally took it off and came.

Frank: Oh, and how do you feel now?

Jasmine: I regret it, it felt so good to be horny and on edge that I began to wear a butt plug and thong panties even while in public. You were right, it did feel so good having it on that I put it back on immediately after.

Frank: Well see if you can make it even longer this time around.

As Julian read the message, a thought occurred to him.

Jasmine: Frank, could you tell me how many days I need to keep it on this time? A minimum amount of days?

Frank: I want you to go a whole week this time.

Jasmine: A week, I think I can do that....

5 days later.

Jasmine: I only made it 5 days :( I just couldn't stand it, but after I cum, I regret it as I lose the on edge feeling.

Frank: Very disappointing to hear.

Julian started to realize he didn't want to disappoint Frank, that he was beginning to feel very submissive towards him.

Jasmine: I am sorry to have disappointed you.

Frank: You seem to be a Sissy that can't control herself.

Jasmine: I know.....

Frank: I think you deserve a punishment.

Jasmine: Oh, please?

Frank: This time you will go the full 7 days and as punishment you will wear a larger butt plug and the thong, but also stockings all day and every day.

Jasmine: Yes Sir!

Frank: Now that's a good girl, you better make it through the next 7 days.

It took a day and a half before Julian managed to get used to the larger plug as he could feel it every time he walked or sat down. He could also feel the stockings as they were constantly brushing against his pants. Every time he sat down to pee, he would see his stockings, thong, and chastity cage as it drove him deeper into being a submissive sissy. He kept getting hornier and hornier as the days went by and towards the end of the week he was so tempted to unlock himself.

As Friday started, he knew that he couldn't make it to the end of the day, so he decided to take his key with him to stash it at work. If he didn't have access to it over the weekend, he would be able to make it through the next couple of days. By the end of the work day, as he placed the key in the desk drawer, he was so on edge that he felt like he was going to burst. However, Julian convinced himself that he couldn't leave his key at work because what if an emergency came about and he needed to get the cage off, but the office would be locked over the weekend.

As Julian drove home, he knew that he was trying to convince himself with the emergency excuse, but he knew that what he wanted was to keep the key with him as he was weak willed. Then the word disappointment filled his mind, he didn't want to disappoint Frank. All the way home, the word disappointment continued to fill his thoughts as his body continued to be on edge.

Halfway home, Julian realized he needed to go to the bathroom, but luckily there was a rest stop on his way home. He decided to make a pit stop there. As he stopped by the rest stop and sat in an empty stall he stared at his chastity cage as disappointment continued to fill his head, he then realized he wished he left his key at work but it was too late.

Julian then made his way to the sinks and looked at himself in the mirror and then looked down. A thought came to him as he looked around and realized he was temporarily alone in the bathroom. He pulled out the key from his pocket and bent down and looked underneath the sink. He found what he was looking for, a spot to hide the key.

Julian made the decision to leave the key at the rest stop, it was convenient as it was open 24 hours for 7 days a week. It was a place he could get to, but far enough away that he would have time to possibly resist any urges to unlock himself while he got himself back under control. He thought it was perfect.

Jasmine: Sir, I made it the full 7 days!

Frank: That's a good girl.

Jasmine: Thank you Sir! It was really hard but I managed. I am soooo horny and on edge right now though.

Frank: So be honest, did you really make it the 7 days or did you disappoint me again?

Jasmine: Sir, I really did manage this time! It was so hard, I almost gave in on Friday, but on the way home I came up with an idea that saved me!

Frank: Oh, what was the idea that saved you?

Jasmine: Sir, on my way home, I had to go to the bathroom, so I stopped by the rest stop on the way. It's one that isn't very busy, but since it's a public stop it's open all the time. I decided to stash my key underneath one of the sinks, it's hidden away a bit so I don't think anyone will find it.

Frank: That was very smart of you. What a clever girl!

Jasmine: Thank you, Sir! I am so happy I came up with that Idea. I sort of want to see how long I can go now before I give in and get the key.

Frank: How about this week, you go as long as you can, I have a number in my head of how many days I think you should last for. If you can go that long, you can escape a punishment, but I am not going to tell you the number.

Jasmine: Sir, that is so mean to not tell me the number of days!

Frank: I am mean? Just for that, make sure you wear the same plug again this week along with the stockings and thong every day.

Jasmine: Sorry Sir.....I will do as you say.

As Julian went to deal with the rest of his day, Frank realized how dumb his sissy had been in her cleverness. Frank knew that there weren't many rest stops on the way out of the city and also which one was probably the least busy. He now knew what direction the dumb sissy lived and so he set off to retrieve a key.

Julian managed to make it through 3 days before decided he had enough and went to fetch the key. As Julian searched for the key, panic struck as he couldn't find it. He thought maybe it was the wrong sink so he searched all of them, but the key was gone! His key to his chastity cage was gone. All sorts of thoughts went through his head until he finally calmed down.

He realized he always had a last resort, the hardware store. However, the thought of having to use something from the hardware store near his junk wasn't very appealing to him. It was truly a last resort he wanted to deal with. Once the panic finally subsided, he calmed down enough to realize he needed to make the best of the situation.

Julian had seen videos of Sissies having Sissygasms and read all those Sissy captions of how a Chastity Sissy could still masturbate. He has always enjoyed anal play and the plug had felt so good the last couple of weeks. In the end, there is always a way to find something to get this cage off, as unpleasant as that sounded to put some sort of tool near it to cut it off.

Jasmine: Sir, I have some bad news....

Frank: Oh, what happened? Did you give in and take your cage off?

Jasmine: No Sir, I wanted to. However, when I went to get my key, it was gone!

Frank: Oh that is terrible. I thought you said you hid it in a place where it wouldn't be found?

Jasmine: Sir, I thought I hid it carefully, but a maintenance man or something must have come around and maybe worked on the sink and found it? Now I am stuck in this cage....

Frank: It's not the end of the world, you are a Sissy aren't you? Sissies get locked in chastity all the time and they get used to it.

Jasmine: Sir, I guess so, but I am so horny and on edge right now!

Frank: Doesn't that feel good?

Jasmine. Yes, Sir, it does feel really good right now.

Frank: Now why don't you make it through the rest of the week and see how you feel?

Jasmine: Yes Sir!

As Julian made it through the rest of the week, he continued to wear the plug, stockings, and thong out. No longer having access to the key, Julian began to imagine that a pimp was holding on to the key and forcing him to wear it permanently. This drove him even crazier into his hooker fantasies. Julian began to fuck himself every night for the rest of the week pretending that a John had picked him up and was using him. However, no matter how hard he tried, he couldn't quite get to that Sissygasm yet. He got close many times, but it only left him on edge more.

Jasmine: Sir, it's been two weeks now that I have been locked up and I am so horny right now that I am leaking into my thong.

Frank: Are you enjoying yourself?