Ben Makes a Mistake

First time I am writing a story.

Ben sat at his desk finishing paying for his new shelves. He closed down his PayPal page and sat deciding what to do for the rest of the evening.

He eventually decided to have some fun and opened up his favourite cam site. He clicked on the search bar and typed in blackmail.

He scrolled through the different models until one caught his eye, Goddess Phoenix. She looked young, early 20s, and had long blonde hair. She was wearing black PVC and looked like a stereotypical domme.

Ben liked younger dommes the best. Something about a woman younger than him dominating him and controlling him made it more fun.

Looking through her tags, she had the ones he liked--Sissy, feminization, and PayPal.

Although he might not look like it, Ben was very into the sissy and feminization fetishes. He was 6'1, short hair and a large beard. His body would be described as ample, above average but not really in the fat category. He also had hair everywhere.

He had never dared to do anything too serious when it came to changing his look. He had shaved the odd bits of hair around his genitals and ass but only a couple of times. He never shaved his legs or armpits.

Blackmail was a relatively new fetish. He'd started getting more and more daring to get his sexual kick. It had started with just dressing up a bit, then it went on to playing with his ass, then to getting cam girls to dominate him and get him to dress and play for them.

A few weeks ago while playing around, the domme on cam asked if he would like to try blackmail. He gave it a go but most of the information was made up so she didn't have anything on him. But it had stuck its claws into him from then on.

He tried to be smart about it after that. He bought a new pay-as-you-go phone to use as any numbers they asked for. It meant he could give them a number that if they did message anything to his supposed wife or girlfriend it would come to him, he wouldn't be found out and could masturbate to the thought of the message having been sent. He also made a second PayPal with that number under a fake name so when he sent money through it, it wouldn't show his name.

He didn't let his face be on camera if he could help it. Although accidents have happened once or twice. That had been scary but lucky nothing had come of it. The models hadn't sent pictures of him or actually tried to blackmail him for real.

He looked around this new dommes profile. She had a tip menu for various things but the one that got him excited was the blackmail wheel.

He typed a message into the chat asking about it and if she took other payments than the site tokens.

A few minutes later just as he was about to leave thinking she wasn't going to respond, a pm opened up from her.

It was a PayPal link and a message saying it was a minimum of £50 and he would get 4 spins of the blackmail info wheel and the 2 task wheel spins.

He clicked on the link, which opened up the PayPal. Typed £50 and clicked send. He messaged back, "Sent Goddess."

She messaged back ok slave and was then typing for a bit, seemingly checking if she had received it. She then picked up her phone and showed it to the camera. It was the blackmail wheel. She spun it 4 times and it landed on; full name, girlfriend/wife's phone number, address, and workplace.

Ben was already playing with himself and this was getting him more hot. He typed the name Bill Johnson, his blackmail phone number, an address that was near where he lived but not his actual one, and a superstore nearby for his place of work.

She messaged back, "Good slave. Now which task wheels do you want?" Ben looked through them and decided on one sissy spin and one anal play spin.

She once again showed her phone on the wheel and spun them both. They landed on full dress-up on cam and hold a dildo in your ass for 1 minute.

She messaged, "I expect your cam to be open in 5 minutes with you dressed up all slutty and your hole filled and what's your sissy name slut."

Ben was getting horny now and was nearly going over the edge. He went and got his clothes and toys. He put on some fishnet stockings, a short pink skirt, and a pink crop top with the words cumslut in pink sequins across the front. He had ordered them all online with prepaid gift cards and being sent to post lockers to avoid having any trace back to him.

He picked his smallest dildo, a 6-inch pink one, and a bottle of lube. Lubing up his hole and the dildo he slowly pushed it in. He felt his hole stretching to accommodate the dildo. He pushed in it until it was up to the base inside. He loved the feeling of having his ass full and his cock was straining and pushing the skirt out in front.

He turned his cam on and angled it so it showed his full body but not his face. He messaged Goddess Phoenix saying "My cam is on Goddess and I go by sissy Rose."

A notification then popped up saying someone was watching his cam.

"Turn around so I can all of you slut," Goddess messaged him. He complied and spun around.

"Show me your full pussy,"

He once again complied and bend over showing the dildo in his ass. It started to slowly come out of his ass so he pushed it back in and stood up.

"No slut I didn't tell you to push it back in or stand up. Bend over now and if it falls out, I expect another £50 and you to put it back in immediately. Count to 60 out loud as well so I know you keeping it in for long enough."

Ben complied and bent over showing his ass to the camera again. He started counting. The dildo was coming out again but it was just exciting him even more. He started to play with himself while bent over but it just made the problem worse as the dildo was coming out faster.

He was so close to cumming and the dildo was close to coming out. Just as he came the dildo fell out. Panicked he turned around and picked the dildo up. He stood back up and put it back inside himself. It went in easy enough and he carried on counting from where he had got to.

After he got to 60 he stood up and turned around to see Goddess smiling.

"Bad slut what did I say!"

Ben closed his camera and sat back down. He clicked her PayPal link and sent another £50. When he was about to tell her that he had sent it, he got another message.

"So "Bill Johnson" since you've been a bad slut so far, you need to make me happy or I'll be sending pictures of you to your girlfriend. How do you think she will react to finding out you're a sissy that loves her holes full of cock?"

"Please don't goddess. I'll send you more just don't send any pictures," He sent back. It was all an act and he knew it. Every time he had done blackmail they said the same thing but even when he hadn't paid they didn't do anything. Just something to get more money and excite the slaves.

He clicked the link again. But just before he sent another 50 he noticed that it wasn't his fake account. He started to panic, why was it on his normal one? Then he remembered that he had ordered the shelves before going on the cam site and must have still been logged in. He closed the PayPal page and logged out of the site. He took off all his clothes and put them all away.

Sitting back at the computer he started the reassure himself. She wouldn't do anything. It was just part of the game and she would forget about it soon enough. He decided to not go on the site for a bit and let it all be forgotten.

He relaxed for the rest of the night watching some TV before going to bed.

The next few days were normal. He had a few jobs but nothing major. Relaxed watching TV at night and he had mostly forgotten about the domme.

Then one night he was watching TV when he got a notification on his phone. He had a Facebook message. It was odd as although he had an account he didn't use it much just a bit for work advertising and messages from Friends. He looked at it and it was from an amount he didn't know.

It said, "Is this you?" With a link

He didn't click it thinking that it was some kind of virus trying to get people to click it. So he ignored it.

A few minutes later it pinged again saying

"You should open this Bill Johnson."

Ben started panicking A little. That was the name he used for blackmail. He messaged back. "Who's this?"

A message came back almost straight away.

"Sissy Rose click that link right now or you'll regret it!"

Shit that was his sissy name he thought. He clicked on the link.

It opened a new page and sent him to an escort site. It went to a new profile that was created today. He looked at it and was filled with horror.

The profile was called SissyRoseCumSlut and the description was:

Hi everyone I'm a slutty sissy that loves cum. I take it in all my holes. No condoms are allowed with me so if you want to use them find someone else I'm a bareback-only girl. My prices are as stated and you paying for my time not what you want me to do so if you have a group of friends that want to use me it will still only cost the stated price.

Ben looked at the prices. 30 minutes for £30, 1 hour for £50 and 4 hours for £150. He kept on reading the profile.

I'm a little shy on here so I only have a few pictures but you can film and take pictures with me for no cost in whatever state you want me in. I'll add more pictures the more filthy I get with clients but for now, my face picture is at a premium on my private gallery so if you want to see my slutty face before it's on your cock have a look.

He looked at the pictures on the profile and they were pictures of him from the other night. One from the front with all the clothes on, one from the back with the dildo in, and one just after the dildo had fallen out and his hole was gaping slightly. He clicked on the private gallery and there was one picture. The description was "my slutty face," and the price was £100 to be able to see it.

Ben felt sick. His phone pinged and a message popped up. The person had sent a picture. He opened the message and it was a picture of him when he bent down to pick the dildo up and it showed his full face.

Another message arrived. "Now Ben Stevenson I don't like being lied to and I don't like being left with a bad without a sissy paying her dues. I have copied all of your Facebook Friends, especially your family. Now if you don't want them to know your dirty little secret go and get dressed like the pictures and get all your dildos out. I know a slut like you had bigger ones than that. You will then go to the cam site and onto my feed (Do you know who I am or are you too dumb to figure it out). Open your cam and I want to see your full face no hiding it otherwise mummy dearest will see what a little sissy slut you are."

Ben quickly got dressed and got his dildos. He sat at his computer and opened up the site. Turing on the cam and angling to not show his face again. He opened for stream and waited. Before long he saw she had entered his room and sent him a message.

"What the fuck slut. I told you to show your face. Do it now and the consequences won't be as bad."

"Please don't make me show it I'll pay what you want," he replied

"I don't care what you want show it now or you'll regret it,"

After thinking for a moment he lifted the camera so she would see his face.

"There my slut is. Now let me look at your dildos."

He showed his dildos one at a time to the camera. There was the one he used the other day, a 10-inch pink one, and a 10-inch brown one.

"My god you are a slut having 2 big dildos. Now I want the brown one in your ass right now and the pink one on the desk in front of you. Then invite me to a private I want to talk to you."

Ben got the lube and started lubing up the brown dildo. He then lubed up his ass before sticking the dildo to his chair. He then slowly sat on it. It was a lot bigger than the one he used a few days before. It was stretching his ass a lot and only the tip was in. He pushed more and more slowly impaling himself on the dildo. Finally, his ass touched the chair as all the dildo was inside of him.

He then invited Goddess to private. She accepted and then he heard her voice for the first time.

"Well, well, well my little slut. You took that so well. Bet your pussy loves being stretched. Mmmm, I feel like something's missing. Aaah I know what it is your other hole is empty. Luckily there's a nice large dildo there for you to suck. Let's see how deep you can take it"

Ben hesitated but then started sucking on the pink dildo. Going as low as he could. After a couple of inches, he started gagging.

"O that won't do at all sissy. You need to get better at it to serve your clients."

Ben started panicking and took his mouth off the dildo to say something.

Before he could he was cut off.

"I DIDN'T SAY STOP!" Goddess shouted.

Ben quickly put the dildo back in his mouth.

"Now keep sucking that. Don't take your mouth off it while I talk. You're going to need the practice. Right where to begin. So from now on you are my little sissy slut. The new badge on my profile might make you think that I'm new to this but you are wrong. This is my 4th account. The others were all banned for what I've done to the stupid sissies that give me too much information. Now I know what you are thinking. I'll report her account and get her banned but that doesn't solve your problem. You see all the sissies that got me banned are still under my heel. They still follow my orders and send me what I want,"

Ben was still bobbing up and down on the dildo. He was terrified but at the same time, his cock was as hard as a rock. It was terrifying and exciting at the same time.

"You'll be like them. Following my orders and earning for me. Now don't worry about me forgetting about you or losing your information I could never do that to one of my sluts. Now what the future holds for you. Well, I'll be giving you some orders and some tasks to do. If you do them well that will be the end of it but if you don't do them or ignore me it's only going to get worse for you. I'll give you the first one now. You are going to fill out one of my blackmail questionnaires. I have most of the information but I want it in this form to make it easier for me. You want to make it easier for me don't you?"

Ben nodded while carrying on sucking the dildo.

"Good girl. I can see you like sucking that. Since you're being a good slut for me I'll give you a choice. You can fill out the full questionnaire or you can have a lite one. But if you do the lite one you have to do a task right now for me. Which one would you like?"

Ben carried on sucking the dildo while thinking.

"You can speak sissy. Now!"

Ben lifted his head and said, "Lite one please goddess," Hopefully it would be the right choice.

"Good choice sissy I knew you wanted to do tasks for me straight away. Give me your email and I'll send it now. Fill in the information and send it back,"

Ben typed in his sissy email address and sent it to Goddess.

"No sissy, your actual email address,"

With a look of defeat, Ben put in his email address.

"Good girl, now that's sent fill it out and send it back. Also, get a pen and some paper and your driver's license,"

Ben looked at his emails and saw a new one from sissies4sale. He opened the attachment and started filling in the form. It asked for his real name, address, phone number, and girlfriend's details. He filled them all in but when he got to the girlfriend details he said, "I don't have a girlfriend goddess what should I put,"

"I didn't think you would have sissy. With how well you took that cock in your pussy I don't think you've ever been near a girl. Just leave it blank,"

Ben wanted to defend himself, he had had girlfriends in the past just not now, but he stopped himself to avoid getting into more trouble.

Having completed the questionnaire he sent it back to Goddess.

"Good slut. Now while I look over your answers. I need you to write the date and SissyRoseCumSlut on the piece of paper."

Ben started writing it down not knowing what it was for. Once he was done he informed goddess.

"Now hold it up in front of you with your driver's license,"

Ben did just that.

After a few seconds goddess said, "You can take it down now." Seeing the worried look on his face she carried on. "Don't worry sissy it's just for your escort profile. Need to get it verified so you can earn for me,"

"What I'm not doing..." Ben started.

"Shut up sissy. I didn't give to permission to speak. Get your whore mouth back on that dildo now!" Goddess shouted

Ben wasn't sure what to do but he once again took the dildo in his mouth.

"Deeper sissy," goddess said.

Ben adjusted himself to try and go deeper making him moan as the dildo in his ass moved positions. His cock started to dribble precum as he did.

"You love sucking cock that much but you don't want to earn anything for me. What a selfish sissy you are. But don't worry I'll have you serving me with every fibre of your being when I'm done with you. Now since you are being naughty I'm going to have to punish you. Are you excited about what the punishment could be? Don't worry it's not a big one yet. For the first one, all I'm going to do is lower the cost of your lovely face picture. It's at 100 now but I think it will be better at 80. The more naughty you are the lower it will get. If you are too naught I'll have to post it for free on your page,"

Ben was scared again now but no matter how scarier he got his cock was always as hard as a rock. Was he getting off on this?

"Now I've spent enough time with you tonight already so I'll give you your task and I'll let you get back to playing with your toys. The first thing is to get rid of that awful beard. No sissy should have one. I want you to be smooth-faced next time I see you and you are to keep it that way. While you keep your face smooth I want your legs to be too. In fact, from now on the only hair you are allowed to have is on top of your head and your eyebrows but will get them fixed later. Now every night at 8 pm I want you to sit in that chair in your sissy clothes one dildo in your ass and sucking the other one. You'll stay like that for 30 minutes. I won't be watching all the time but if I open you came and your not sucking there'll be a punishment."

Ben looked at the clock in the corner of his screen and the time just ticked over to 8 pm.

"Look at the time guess your first 30 minutes are starting now. Have fun sissy."

With that, she came off private but kept his cam open. Ben sat there bobbing up and down when he uncontrollably started to spurt cum. As the orgasm went through him, he started to think what his life was going to become. Part of him was horrified but the other was excited.