A Sissy Gets Hooked

Jasmine: Oh Yes, I have never been this horny before and it feels amazing. I have been fucking myself in the evenings with my dildo trying to get a Sissygasm and I have been so close to it, but haven't gotten to it yet. One of these days I will have one though!

Frank: That's a good girl, a locked Sissy like you will eventually learn to Sissygasm.

Jasmine: Sir, I hope so. As I fuck myself at night, I imagine I am a Cheap Sissy Hooker getting fucked by a John.

Frank: You do like that Sissy Hooker fantasy don't you?

Jasmine: Yes Sir!

Frank: You know, you haven't posted anything to your fans lately.

Jasmine: Sir, you are right, this chastity thing has kept me busy the last few weeks that I have been busy with that.

Frank: You should do another photo shoot, this time show off your chastity cage by wearing a skirt this time instead of the hotpants.

Jasmine: Sir, that sounds like a great idea!

Frank: It was really sexy how you did it in that sleazy motel last time. I imagine your fans would like to see Hooker Jasmine showing off in her motel room. It would be such a tease to them.

Jasmine: OMG Sir, that is such a great idea! I will have so many guys drooling over me, I got so many great comments and messages last time I did a photo shoot in the hotel. It really made me feel like a whore being in that hotel too.

Frank: That's a good girl, I expect a sneak preview from you before everyone else.

Jasmine: Oh yes Sir! I will snap a few pictures and send you some while I am doing my shoot. I bet it will make you so horny knowing that I am sitting in a motel room dressed as a hooker as you look over my pictures ;)

Frank: Such a tease! I look forward to the pictures. Have fun at your shoot!

Once Saturday rolled around Julian packed up this Sissy gear and headed back to the motel. As he drove towards the hotel, he saw more and more hookers on the corners, he even saw one that had more of his version of a classic hooker look. He wished that he was her standing on that corner.

Julian was given his room key and he made his way in. This time it was a different room than before, but still just as dodgy and dirty as the last. Julian got dressed again as Jasmine and as he began his photo shoot, he realized he needed to send some pictures to Frank. Once he sent them off, he went about finishing the shoot.

As the photos came in to Frank, he smiled as he looked down at what the dumb Sissy had done. He was going to find out who this Sissy was and where he lived. He hopped into his car as he only lived a few minutes away from the motel and waited in the parking lot to see what single guy would come out of his hotel without a hooker coming out first.

After about an hour and half, a door opened and it was a guy dragging luggage who fit the build of Sissy Jasmine. Most people at this hotel didn't have luggage, only a guy who had brought his Sissy outfit would.

Frank finally found what Jasmine the Sissy really looked like as male. The guy didn't disappoint, as he looked rather feminine, very cute actually, as Frank's cock stirred in his pants looking at the next Sissy he was going to break.

Julian packed up his stuff in his car and headed home. He was oblivious to the fact that someone was following him as he was focused on trying to get more glimpses of the hookers on the route from the hotel.

Frank pulled up to Julian's house and made a mental note of where he lived. He had his Sissy hooked and was slowly reeling him in. A few more steps in his plan and he would soon have his cock in that dumb Sissy.

Julian excitedly edited his newest hooker shoot and soon had it uploaded online. The messages and comments came flooding in pointing out his new accessory he had around his little clitty. Julian's caged clitty twitched as he basked in the attention he was receiving online. It didn't matter if the comments were praising him or disparaging him, either way he was excited for the attention. In fact he loved the humiliating comments the most.

Jasmine: Sir, I hope you like my new photo shoot!

Frank: Oh, I did enjoy it, especially the preview you had sent. It made my day.

Jasmine: Yay! Thank you Sir! It's been three weeks now that I have been in chastity and I am so horny that I am leaking so my panties are always damp now. I am going to fuck myself silly tonight. Hopefully, I can have my first sissygasm.

Frank: I bet you would love to have me fuck your ass pussy right now. I would be willing to pay you $20 for it.

Jasmine: OMG Sir, that is so hot! To think I would be giving up my virgin ass pussy for $20, I would feel like such a cheap hooker!

Frank: Virgin?

Jasmine: Yep Sir, no man has ever touched my ass. The only things that have been up there are the toys that I have.

Frank: Really? Hmm, a virgin. Since you lack experience, I will drop my price to $10 for your first fuck.

Jasmine: Wow, that is making my clitty twitch so hard in the cage right now. The thought of giving up my virginity for $10.

Frank: Too bad you probably don't live close, or I would come over and fuck you right now.

Jasmine: Sir, you are so bad! Are you trying to tempt me to let you find me? You know I am just an online tease. My fans love me for it, because they know that I am something that they will never have. Nice try thought ;P

Frank: Can't hurt a guy for trying.

Jasmine: Sir, speaking of my fans. They are loving the new shoot. However, I am running out of ideas on what to do next. This recent shoot was even your idea.

Frank: Hmm, I think I have an idea for your next shoot.

Jasmine: Oh what is it Sir?

Frank: I think instead of doing still you should do videos.

Jasmine: Hmm, that does seem like the next logical step up. That is a good idea Sir.

Frank: However, videos are a bit more tricky, as it's best to have the camera catch where the action is. It's almost better to have someone filming you while you do it.

Jasmine: Sir, I already said you aren't going to find where I am, stop trying to trick me :P

Frank: Hear me out, I am not asking to film you. Instead, why don't you hire a hooker to do it?

Jasmine: Hmm....

Frank: Hookers are discreet and I am sure one would love to just stand around and get paid filming you instead of having to fuck some random John. Their pussy could probably use the break even.

Jasmine: Sir, I guess that could be an idea.

Frank: Also, having a female in the room, they could do some voice overs for you in the video that way you won't even have to expose your voice. She could even moan for you, your fans would think you are the perfect sissy with such a feminine voice.

Jasmine: Oh, that would be perfect, my fans would want me even more! Sir, I love your idea!

Frank: You can probably just pick one up at the hotel, it would probably be safer than grabbing one off the corner as you don't know who may be a cop. If she is already at the hotel, she has probably already serviced someone.

Jasmine: Sir, your ideas are too perfect!

Julian and Frank continued to work out the details of her next photo shoot for the rest of the evening. Normally, Julian would have had more reservations of hiring a hooker to film him as Jasmine, but after three weeks locked in chastity, her judgment was beginning to get clouded. Plus, the thought of being near an actual hooker was driving him crazy. He had so many questions he wanted to ask of her and her lifestyle, hopefully the hooker would be receptive to it, after all he would be willing to pay her for info. He just needed to find a good one for hire.

Frank, on the other hand, knew the perfect hooker to hire. He was already calling her up to let her in on his plans. He had frequent "relations" with her in the past and she knew about his hobby of breaking sissies. She had even helped to break one in the past, as long as Frank paid, she was willing to do a lot for him.

The next weekend rolled around and Julian was shaking with excitement with the thought of meeting an actual hooker. He pulled into the motel and was disappointed to find that there wasn't any in the parking lot, so he went to the lobby to go and pay for a room.

On his way out of the lobby, he noticed a door open and a woman walking out by herself. Jackpot, he had found a hooker. He walked up to her and asked her if she was still working and she responded with an of course. Julian was a bit shy at this point, as he knew his request would be different. He mustered up the courage and told her that he didn't want to have sex and explained what he wanted instead, that he was going to do a video shoot and needed her to be the director.

To Julian's surprise, she said yes and seemed very enthusiastic about it and let him know that her name was Katrina. Julian felt he got lucky with the hooker he had found and if all goes well tonight he would have a great photo shoot for his online followers. What Julian didn't know was that before he arrived at the hotel, Katrina was fucking Frank in the room she just came out of and that they had been waiting for him to arrive.

Julian and Katrina made their way to his room and soon they discussed payment along with all the details on how the shoot should go. Julian then got dressed as Jasmine and then went to the bathroom to continue his prep. As he was in the bathroom, Katrina snagged the keys that Julian had left out and pulled off the house key and texted Frank.

Frank came by the hotel room and Katrina quickly handed over the key to him. He then made his way to Julian's house, as he had plans while Julian was distracted with his photo shoot. He was going to make his way over to Julian's place to install some software on his computer so he could take it over remotely and to plant some hidden cameras around his bedroom.

As Frank was messing around at Julian's house, Julian and Katrina started working on the video shoot. As they were about to start, Katrina stared at Julian and said something was off. Julian asked what's the problem and Katrina explained that it was the thong. It doesn't look quite right with your outfit. Why don't you try mine, as she began to strip out of her pants. Once she had her pants off, she started to peel off her thong.

Julian watched as she peeled off her thong and then he noticed that there was a string of residue clinging to it from her pussy. Julian at first thought she was really wet, but once she handed him the thong, he saw what it really was. It was cum, and a lot of it. He then remembered she was coming out of a hotel room when he met her. He was holding a hooker cumfilled used thong. He nearly came in his own thong at the thought. Are you sure he asked her?

Katrina just smiled at him and said, hope you don't mind babe, I did just fuck a guy before I ran into you, but hey, you did want to say you wanted the hooker look for your shoot. What better way to have the hooker look than authentic used hooker panties, as she winked at him.

Julian just stared back at her and said, if you say so, as he peeled his thong off. As he pulled the used thong up, he could clearly see all the cum in the crotch. Damn, he thought, her last John must be a heavy cummer. Little did Julian know that Frank had asked Katrina to give her panties to him. Frank thought it would be funny to have his cum touching Julian's clitty during the photo shoot. He also knew that it would make Julian go crazy. Once Julian pulled up the thong over his crotch, he felt the cum start to soak into his chastity cage and he felt a little bit of his own wetness squirt out of his cage to mix with the used panty cum.

Julian felt like such a whore to have a John's cum soak his crotch. He could feel the wetness run down the thong and near his asshole. If it weren't for the butt plug in place, he wasn't sure if he wouldn't have just started fucking his ass with the thong right then and their.

Katrina just stood and smirked at Julian as she watched this sissy get off on putting on the cum filled thong. After a minute, she got Julian's attention and asked him where he wanted to start. They soon began the shoot and a while later they were finished with it.

Frank in the meantime had installed everything he needed to at Julian's house and on his way back had even stopped to make a copy of the house key. After all, he would need easy access to the house to the Sissy he was about to own.

As Julian wrapped up and went to the Bathroom to clean up, Katrina texted Frank and got the key back. She was quick to put it back on Julian's key ring before he made it out of the bathroom.

Well Babe, thanks for the pay, it was fun, if you need anything else, here is my number, she told Julian. Have fun with your video that you made and keep the panties as I put yours on already and are keeping the clean pair. Don't jack off too much with it! Oh wait, you're a chastity Sissy Bitch, so I guess you won't be playing with yourself, as she winked at Julian and left the motel room.

Julian just stood there in a daze as he watched Katrina leave. Chastity Sissy Bitch flowed through his mind as he realized she was right, he couldn't even jack off right now even if he wanted to and he was still wearing the cum thong. He soon snapped out of his daze to pack up and make his way home.

Once Julian got home, he quickly went to his computer to start watching and editing the material he had just made. As he watched the video, he saw how whorish he looked and the voiceovers from Katrina were perfectly timed. It really made him sound like an effeminate Sissy. It made him even hornier to see what a whore he was.

He was a whore in the video, he even had a whore's cum filled thong on. Yes, the cum filled thong, he still had it on. He had some John's cum in his crotch right now. He was a dirty whore, he had the aftermath of a hooker and John's fuck. A dirty thought then entered his mind.

With shaking hands, he peeled off the thong and brought the crotch of the cum stained panties to his face. At first he gave them a sniff and they smelled of cum and pussy. Then he stuck his tongue out and gently licked the cum stained crotch. He could feel the cum leaking out of his chastity cage as he then licked the thong harder.

Julian's body was on fire. He was about to burst, he nearly came just by licking the cum stained thong. He decided he needed more. He grabbed one of his dildos and hopped on his bed with the thong in his other hand. He quickly pulled the butt plug out of his ass and rammed the dildo home. As he began to fuck him self, he brought the thong back up to his face. At first he sniffed it again, then licked it as he fucked himself hard. Then finally he put the crotch in his mouth and sucked hard as he exploded.

His cum shot out of the chastity cage as he sucked hard on the cumstained thong. He was in ecstasy as he had his first sissygasm and came so hard. Four weeks of stored cum went everywhere, he had made a mess of his bed. Soon he collapsed in bed with the dildo still deep inside of him and the thong still in his mouth.

After about 10 minutes, Julian started to move again. He had just had the most intense orgasm of his life, but he was still horny. It seems like it did nothing to relieve it, but rather just made him more horny being locked in the chastity cage.

Julian, as horny as he still was, then saw his cum everywhere and another dirty thought came into his mind. He pulled the dildo out of his ass, used it to scope up as much of the cum off the bed as he could and then started to suck it off. He had his first ass to mouth experience and was eating his own cum. Once he cleaned off the dildo, he used the thong to clean up as much of the remaining cum off the bed as he could and then put it back on. Julian was exhausted at this point and went to bed.

What Julian didn't know was that the whole time Frank was watching via the webcam from Julian's computer and the various cameras setup in his room. Frank used his control of Julian's computer to send him all the videos from the show Julian just put on to himself. Frank had made it look like Julian had sent the videos.

He had Julian now, the Dumb Sissy Bitch had just given him the perfect show of him sucking on a used thong, fucking his ass, and having a sissygasm while in chastity. The ass to mouth with his own cum eating was just icing on the cake. Julian had done all this looking like his normal self and not as Jasmine.

The next day, Julian was on cloud nine, he had his first sissygasm experience and it was wonderful. He also had so much slutty video of his most recent time from the motel that he knew would drive his followers crazy. Julian spent most of the day editing and uploading the videos. His followers loved the videos as all they had before were stills but they now had him "talking" in such a feminine voice too. Katrina had tried to gruff up her voice so that it would sound more manish so that it wouldn't be that obvious it was an actual female talking.

Julian basked in the attention that Jasmine was getting online. Once he had enough, he turned his attention to Frank to thank him for his ideas on this video shoot.

Jasmine: Sir, the video shoot went off without a hitch and my followers are loving it!

Frank: I saw the videos, they turned out beautifully and the hooker you chose did a good job.

Jasmine: Sir, she was great, I had found her when he was leaving one of the motel rooms after meeting with a John.

Frank: Oh so you got one just as she was finishing up with another client.

Jasmine: Yes Sir! She even gave me her thong as she thought it would look better for the shoot. It was covered in cum from the John she had just fucked!

Frank: I had seen in the video how wet and messy your thong had been. No wonder, it was really a hooker's cum soaked thong. It looked like you were having a lot of fun in the video shoot. I bet the hooker was surprised when you pulled out that dildo and fucked yourself on camera with it.

Jasmine: Very much so Sir. I loved every minute of it and she seemed to like it when I was fucking myself, I think if she didn't have to film, she probably would have tried to get herself off then and there ;)

Frank: Your most recent videos you sent out are pretty amazing. I am thinking about setting up my own site with all the stuff sissies have sent me over the years. I want to make sure that you are fine with me using your videos. I know you have posted a lot of stuff online, but I want to make sure you are still good with the stuff you sent out recently?

Jasmine: Oh Yes Sir! Any videos I send out are now the property of anybody who has them. I just love how my photos and videos are being spread around. I am such a Webslut!

Frank: I just wanted to make sure, you were pretty raunchy in the videos, playing with that used cum stained thong and fucking yourself with that dildo so hard.

Jasmine: Sir, I love being a Webslut and you have my permission to use those videos however you want!

Frank: Sounds great! I look forward to what you will be doing next. I have some ideas for you.

Jasmine: Of Course Sir! I look forward to hearing about them! Well I am going to go back to reading comments and responding to messages, I will talk to you soon about what I should do next.

Julian was on a high, as he read through the comments and messages. People were loving Jasmine's new stuff. He was looking forward to what ideas Frank could come up next, but waited a couple of days before contacting Frank again.

Jasmine: Hi Sir, I wanted to see what I should do for my next shoot.

Frank: Well, I think there is only one next step for you in your Sissy Hooker evolution.

Jasmine: Oh, Sir?

Frank: Your next shoot should be you servicing an actual John.

Jasmine: Very Funny Sir! You know that I am not going to ever be with another man. Remember, I am just an online tease ;P

Frank: I think before you turn down my idea, you should see this website that I have setup. It's private right now so you will need a password to access it. Here is the link and the password is JasminetheSissyHooker