Blackmailed Becky: Anal Training

"I think I have a cute little black dress that I will wear!" I told Sarah with glee.

Then 5am came round. My phone buzzed in my pocket and my heart stopped when I saw it was from Steve

No I forgot to send him a photo!!

"You seem to struggle following orders. I guess you were too distracted organising a date with that customer."

Oh no, he must have seen me on the cameras, I can't escape.

Then another text came through.

"You have 5 minutes to send me photo of you!"

Suddenly my knickers started vibrating hard! It was the hardest I had felt it go and I had to stop myself from letting out a very loud moan from the surprise.

"I need to go to the bathroom!" I almost shouted out at Sarah as I tried to limp to the bathroom as my orgasm was building up fast.

After the other night of pure teasing on my clit I was having shocks of pure pleasure coming off of me.

Reaching the bathroom, I went into a cubicle and sat down, allowing the knickers to force me into another orgasm at work.

Then my phone buzzed.

"Times up slut. As punishment you will send me a video of you cumming from my knickers!"

Oh god!

My body was trembling and my orgasm was building more and more.

Biting my lips my hands shook as I turned the camera on my phone.

Oh my god, oh fuck!

I turned the camera on and did my best to hold it pointing at me as I hit record.

I saw a message appear at the top of my phone from Steve.

"Cum for your master you fucking whore!"

"Ooohhh fuuuuuucckkkkkkk!" I moaned out louder than I intended.

"Fuuucckk yeeess!" I couldn't stop.

My body was shaking as the largest orgasm I have ever had hit me, over and over again my body was shaking from my knickers!

My breathing was loud and heavy and my legs tensed up from the never ending orgasm.

The vibrating stopped, my body slumped and I was coming down from the most amazing orgasm than I could imagine. Without having time to think about it I sent it straight to Steve and said.

"Enjoy."

Why did I say enjoy?

I re-read the text and scolded myself for giving in to this man. I wanted to see how bad the video was that I just sent to him, clicking onto it was disgusted with myself.

I had my full face and open legs on show, I was moaning like crazy and I was very clearly cumming and moaning out load as I did so.

Another text from Steve came through.

"Looks like you are enjoying yourself slut. It is time to go up a size in the butt plugs. Send me a photo when you finish your shift and have it in."

I quickly replied back.

"Yes Master." And then went back to work, trying to forget about what had just happened.

Luckily the rest of the shift went quickly and no more vibrating from the knickers.

I was back home around 7am and went to my bedroom, opening the box that Steve gave to me I picked up the next size of butt plug. Inspecting it, it was a fair bit bigger than the one I had in and I was instantly worried of how it would feel.

Carefully I removed the one I had in, cleaned it and put it back into the box. I touched my hole with my fingertips and it didn't feel any different. I was worried it would have remained stretched.

I grabbed the new plug, poured a generous amount of lube over it and around my arsehole, then bending over I slowly pushed it against my tight hole.

I was instantly met with resistance; This is going to hurt. I pushed a bit harder, feeling my hole open up and start to accept the new plug in. Bit by bit I felt my arse stretch tightly around the increasing in size of the plug, until it slipped and I knew it was fully inside of my arse.

God that is so big!

My hole felt stretched and stung around the new plug, I had realised that my breathing grew heavier whilst sliding it in.

I bend over, pulled one cheek out with one hand and took a photo of me with the new plug in and sent it to Steve. He quickly replied.

"How does it feel?"

I text him back.

"Big." To which he replied.

"Good."

That was it for the texting, I put my phone on charge and lay in my bed. Every movement was met with a new pain from the larger plug and I knew I was in for a restless sleep.

Saturday night

Standing in front of my full length mirror, I was dressed in my tight black dress which really pushed up my big boobs. My long brown hair was straightened and falling down my back and I had a full face of make up on.

Turning around I was happy with how the dress hugged my bum, I was really happy with my petite figure, then looking at my bum I remembered about the plug that was going to be inside of me the entire date with Myles.

I lifted up my skirt, pulled my knickers to one side and sent a photo of the plug in me to Steve to keep him happy. Then just as I was about to leave I had a text from Steve.

"Enjoy your date."

I scoffed at his text, he couldn't possibly think he could try and be nice to me.

I met up with Myles at a bar and I totally forgot about Steve, for a few hours I had forgotten about my problems and was happy in my own little bubbly with Myles.

He suggested we go and get food and went to a fairly nice restaurant.

He pulled my chair out for me and as I sat down I landed to hard and felt the plug push up harshly deep inside of me.

"Are you okay?" Myles asked after my painful noise.

"Yes I am fine, sorry I just sat down too fast." I told him.

He took his seat next to me and we ordered a few drinks and some food. Whilst eating he turned to me and said.

"You look absolutely beautiful tonight. I am so glad that I came into your work."

He is so amazing. I blushed, smiled towards the ground and said back.

"Thank you, you look great too."

Oh no!

The vibrating started from my knickers

No not now! Please give me this night!

"Excuse me I need to go the bathroom." I said and rushed off.

Once inside the cubicle I got my phone out and text Steve.

"Please don't do this!"

He quickly replied.

"You need to start to learn to address me properly! If you want to speak to me you call me master!"

I hastily replied.

"I am sorry Master, please don't use the knickers tonight! I am begging you!"

He was typing, finally it came through!

"I will give you two options. Admit that you belong to me and will forever be my slave and I make you cum right here, right now! Or, you agree that you will not cum until you next see me?"

I looked at his text, the choice was easy. I was never going to give this sick old man the satisfaction of accepting being his slut. I replied.

"I won't cum until I next see you."

He very quickly replied.

"Ok."

Then the vibrating stopped and I happily returned back to my date.

"Everything okay? You look a little flustered?" Myles asked on my return.

"Yes I am fine thankyou," I sat down, looked at him and said "I am having a great night."

Then the vibrating returned, but the same as the other day it was just a light vibrating. Enough to make my clit twitch but not enough to make me cum.

This sick bastard!

That was it for the rest of the date, I had to try and focus on Myles and not that my clit was throbbing from the constant tease of pleasure.

One hour later I was desperate, my mind couldn't think straight, every now and again Steve would up the vibration and then lower it again just before I came.

It got to the point where I was desperate to cum, I ran to the bathroom again and text him.

"Please just let me cum and get it over with Master!"

He just replied.

"You made your decision."

Fuck!

I tried to carry on the date as usual with the constant edging underneath my dress. I had forgotten about the plug in my ass by this stage and just took the constant tease of pleasure.

By midnight I was saying goodnight to Myles, just before he saw me into a taxi he pulled me close and kissed me.

His lips were soft and felt amazing pressed against mine, my tongue escaped into his mouth and we were making out. It was so sensual and amazing.

"Okay goodnight." I said with a smile breaking the kiss.

Once I was back home I got into my bed and I was going crazy, the vibrating had stopped by now but my body was on fire. I took off my knickers and there was a huge wet spot from my pussy. I was desperate to cum.

There is no way that he would know if I made myself cum right now.

I got onto the bed and starting rubbing my throbbing clit, my moans grew loud instantly as I thought of Myles.

"Yes.... Yes... Yes..." Was all I kept moaning out when suddenly my much needed and teased orgasm hit me.

"Fuuuuuuuuckkkkkk" I tried to whisper out my moan to not wake anyone up but my entire body trembled.

After that I was exhausted and passed out in a second.

Sunday Morning

I woke up late, my head was a little sore from the drinking and as I rose out of bed I remembered that the plug was still in my ass. It didn't hurt but I could still feel it.

I looked at my phone and strangely I saw a text from my ex-boyfriend Ken that I hadn't broken up with that long ago. Opening it I read.

"So you just dumped me to go and become a slag?"

I didn't understand, I haven't heard from him since we broke up so I text him back.

"I don't understand?"

Then he forwarded me a message that he got from an anonymous number, opening it I saw a video attached.

Oh no!

I opened the video and it was a video that was clearly me sucking on Steve's huge dick! It only lasted five seconds but I was clearly the one doing the sucking and it had me moaning!

"Please do not show that anyone!!" I text him back.

"Why should I care what you want when you clearly don't care about me." He text me back.

"Please Ken, you know how bad that would be for me!" I told him.

He eventually text me back saying.

"I won't send it to anyone. I wouldn't do that to you. I am just disappointed this is what you have become since we broke up."

I was hurt, I did still care about Ken and to know he now thought so little of me upset me. Another text popped up on my phone, it was Steve.

"You agreed not to cum. I warned you. Did you not believe that I would send your videos out?"

My shaking hands just managed to type out.

"I can't believe you actually fucking sent it! What the fuck is wrong with you! Who else did you send it to?!"

While in my head I was thinking how did he know that I made myself cum?

"I only sent it to Ken, for now. But if you don't apologise for how you just spoke to me I will send it to your parents. I got all of your contacts off your phone."

Again I learnt a new lesson of how Steve now controlled me.

"I am sorry Master, please don't send it to anyone else."

He typed back.

"I won't if you obey and stop being a bad slut!"

"Yes Master," I replied "How did you know that I came last night?"

After a while he text back.

"I installed an app onto your phone so I can hear from your microphone. I could hear you moaning and cumming from it last night."

Oh my god! He literally had eyes on me at all times. I couldn't do anything!

Then another text come through.

"Now as another punishment, put the next size plug in."

As I was texting to argue back to say I wasn't ready for that, I stopped myself. He clearly wasn't playing around with me and was happy to ruin my life. Instead I just replied.

"Yes Master."

I pulled the current plug out of my arse which made me wince as it came out. Then I got the new one, it was a lot bigger and I was afraid of what it was going to do to me.

I lay on my bed and spread my legs, lifting them up high to stretch my arse as much as possible to help slide it in. The plug was now lubed up and I was rubbing it against my arsehole to get that wet and then I started to press.

Fuck this one is a lot bigger!

I kept pushing and pushing but my arse wasn't taking it, I could feel the tip of the plug go in but the more I pushed the more it hurt. My arsehole was being stretched wider than I wanted and I was letting out little moans of pain.

I was nearly at the end, the thickest part of the plug stretching my arse. I took a deep breath and pushed the last in.

"Fuuuucckkk!" I groaned out. My arse stinging from the intrusion. I felt properly stretched right now and can't imagine being able to go about my day with this in me.

I had to lay there for five minutes, panting as I tried to control the pain in my arse.

I can't believe this is happening to me.

The next Saturday

I hadn't heard much from Steve since putting in this plug, he would occasionally turn on the vibration of my knickers and get me on the edge of cumming but then turn it off.

By Saturday I was a hot mess, I must have been edged a hundred times and I couldn't think of anything other than cumming.

After my shift ended I had a text from Steve, the first one in a while.

"How are you doing my slut? Still wishing you chose the option that would let you cum?"

I was lay in my bed and the vibrating started again, very lightly and my breathing was instantly heavy. God I needed to cum so bad.

"Please Master, Please can I cum?" I text him.

"No slut. You made your choice not to declare yourself my slave. You wanted this!" Steve replied.

I couldn't think straight, my whole body was overwhelmed with how horny I was.

"Please Master. I will be a good slut. Just please stop teasing me!"

"Good to see you are learning your place whore. Time to put the next plug in, you are nearly at the last one. How does it feel?" He told me.

I quickly replied.

"I think I have gotten used to this one now Master. Although my arsehole still feels really stretched."

"Good girl," He replied "Put the next one in and send me a photo. And no cumming!"

With a huff I did what he said, taking out the current plug which I had grown accustomed to. I bent over and started to push in the next one. I could tell it was even bigger but I just bit my lip and forced it inside of my ass, letting out a whimper as it got fully in.

I am such a mess.

Wednesday

Nothing from Steve since that night, he carried on teasing and edging me. I was just in a horny state now, every time I would feel something rub against my clit I thought I would cum which led to a lot of embarrassing situations moaning in public.

I was still sending the photos to Steve but he never replied, I didn't know if he wasn't looking at them or just wanted to leave me waiting.

God I need to cum so bad!

During my shift Myles came in. I was ecstatic to see him, we have text every day since our date but haven't had a chance to see each other yet. Our different shift patterns made it hard to organise a night we are both off.

"Hi beautiful." He said walking up to me.

"Hey you, what can I get for you?" I asked.

"Oh nothing tonight, I just wanted to see you." He said with a smile that made my heart melt.

What I would do to have him take me to the bathroom and fuck me senseless right now. Was all I could think.

"And to tell you that I managed to get Saturday off. If you are still not working, we could go on a second date?" He asked

Oh my god this is amazing!!

"Yes! Definitely! I would love to!" I said with glee.

He gave me a quick kiss and left and I couldn't stop myself from smiling.

Towards the end of my shift my phone buzzed and I looked to see it was Steve.

"Slut. I am getting back early, you are coming to mine on Saturday. I will text you the address. Put the last plug in tonight to get you ready."

No, no, no he can't do this! What about Myles

"Master. I have plans on Saturday, can I come over another night?" I asked him to try to please him.

He very quickly replied.

"Did I ask if you were free? Here is my address. Be there at 7pm."

He sent me the address and I knew I couldn't say no, who knows who he would send my videos to next. I just replied.

"Yes Master."

Then text Myles.

"Hi Myles, sorry my mum has said I have a family arrangement on Saturday so I can't go on our date. I am so sorry, I promise to make it up to you! x"

He eventually text me back to say it is okay and we will rearrange.

Saturday Night

This was it. I was sat in the taxi, the largest butt plug stretching my arse and being driven to Steve's house where I knew he was going to take my anal virginity. I wanted to cry but I thought, what is the point? There is nothing I can do and I just have to take it.

As I got closer, the vibrating knickers kicked in again and I let out a loud moan in the back on the taxi. The driver looked back weirdly at me and I just tried to laugh it off.

Fuck I am going to cum!!!

But then the vibrating ended!! Again! I was getting so sick of this shit!!

Reaching Steve's address, I anxiously knocked on the door and he quickly came to let me in.

"Slut. Glad you are here on time." He said with a grin.

He had a tan but he still looked fat as every in a t-shirt and baggy shorts!

He ushered me in and I followed him into the living room, then pointed at another door and said.

"In there."

I opened the door and was in utter shock when I saw what was inside! It was like something out of a porn movie, some kind of sex dungeon! There was a swing, chains, beds and the walls were filled with toys and objects that I didn't even know existed.

"Undress and lie over the bench." He ordered.

I looked and in the middle of the room was a leather bench at waist height, I got naked and lay over the bench as order.

Suddenly I felt his hand grip my wrist and locked handcuffs to me! I was afraid now!

"What no! Get this off me!" I tried to scream but Steve jumped and sat his fat body on top of me!

I was only small and couldn't stop him! He leant over and handcuffed my other wrist, the were attached to a metal bar on the floor and I could only move them a few inches.

Then he did the same with my ankles as I was trying to wriggle and get him off of me.

This is bad! Fuck what is he doing!!

Once I was fully locked up, I tried to shake but I could barely move, the locks were tight and I was hard against the bench.

"Let me out! Stop this! HELP!!!" I tried to scream but Steve just laughed.

"Shut up slut!" He shouted and slapped my arse harder than any before.

Tears began to fall out of my eyes and land onto the leather bench below me.

"Please Steve, not like this." I said, whimpering in fear.

WHACK!!

Another harsh slap on my arsecheek.

"How long until you only address me as master you fucking slut!"

WHACK!!

"I'm sorry, Master, Please!" I cried out to him, my arse red raw.

"Good slut! Now lets see this plug." He groaned out.

I was so afraid, I was completely helpless. I felt his fat fingers touching my arse, grabbing my cheeks and pulling them apart.

"Mmmm that looks good." He moaned out and then started to push the plug deeper in and letting it back out.

"Look at you, soaking wet. Did you get that wet knowing you were coming to your masters house?" he asked sliding a finger knuckle deep into my soaking wet pussy.

The last week or so of constant teasing had broken me, just the feel of his finger sliding inside of me sent shockwaves through my body.

"Please master." I stuttered out.

He started to slide his finger in and out of my dripping wet pussy.

"What is it slut?" He asked

"Please can I cum?" I moaned from his second finger harshly going into my pussy.

"Such a fucking whore. Begging me to make you cum." He laughed.

I was so embarrassed, I was chained up and moaning heavily from him fingering my pussy, so desperate to have any sort of relief.

"Fuck yes master." I moaned as he picked up his fingering pace, properly finger fucking my pussy.