Sissified Ch. 05

This is the fifth story in the series, please read the previous chapters so as to understand the story better.

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I woke up hearing a knock on my door, it was Mom I pulled the blanket over my transparent nightie and said, "Come in." Mom came into my room.

"Good morning Ron, I have to leave early this promotion comes with a lot of work."

"Good morning mom, no problem Mom," I replied.

Mom had been promoted a couple of days ago, so she used to leave early in the morning and come late at night. I had no problems as it gave me more time to dress up and I had to sneak to the gym too all dressed up, but now as mom left early, I didn't have that problem. After Mom left, I got up as always, I found myself leaking, took a shower and washed my used clothes and lingerie. I got back to my room and opened my wardrobe, after of week of my previous shopping Ms. Robin and I went back to the mall but this time I was dressed up all feminine, I wore a black micro skirt with bright red G-string panty under it the skirt was so short every time I walked I panty was clearly visible, on top I wore a t-shirt with a logo of big pink lips and a pair of red heels, and to top it all I had slutty makeup on, I looked like a complete slut. At first, I declined to wear this at first then Ms. Robin showed me my park video and threatened to share this and then I had no choice but to wear them. We went to the same lingerie store I got a couple of new panties, fishnet, black, red and pink stockings, thigh high socks for gym and some more nighties and baby dolls. Then we got some sports bras and semi-transparent shorts for gym. All these adventures turned me on but I couldn't do anything as I had been ordered by Ms. Robin to not masturbate.

Back to present, I took out a pink sports bra with the word 'cum' printed in bold letters, then I took an orange G-string panty and wore a semi-transparent black short over it, then I put on a white thigh high socks and the pink sneakers and started for the gym, I jogged to the gym and went inside Jessie greeted me smiling, she was my trainer. We started working out, first I did some cardio, then moved on to weighted squats and other legs and booty exercises and finished it with some abs training, I had to agree her training was working I felt better than ever, I had increased stamina, my legs and ass were getting in shape, my ass looked so round it was almost a bubble butt, I had a complete flat belly and my abs were slightly visible, I looked at myself in the mirror only if I had some boobs I would like a complete girl, but something weird had also happened my skin had started getting smooth and no hair grew over my body, my head hair grew very quickly and it looked like my penis and balls were getting smaller and my nipples were getting bigger.

I walked back to my house. Took a bath and popped my tablet. I put on a black short with red satin panty and a white crop top with slut printed over it. I felt horny as I had not been allowed to cum since the park incident It had been around 20 days, and I had to watch hypnosis about obeying my mistress, sucking dick and dressing feminine while sucking on the dildo, all this made me so horny but I wasn't allowed to cum. I finished Ms. Robin's homework and was watching T.V when I got a text from her, I had to watch sissies sucking dick till she came to my house while sucking the dildo, I put on my headphones and grabbed the dildo and played the video, by now I had become an expert in giving blow jobs I no longer had my gag reflex and could swallow the dildo till the balls, I was proud about it but it felt weird I still hadn't accepted the idea of becoming a sissy but anyway I had to do it Ms. Robin said in a couple of days I would be ready for the next stage which I guess will the point when she helps to quit these habits, the video kept playing till 6:30 P.M, then it stopped. Mistress texted me she won't be coming as she has to meet someone. I was drooling at this point at nothing made sense to me. I lied on my bed trying to sleep, I wanted to cum so bad I hadn't in 20 days, but I couldn't disobey Ms. Robin's order the hypnosis videos she sent made sure of that. My penis starts twitching I was trying to get hard, but couldn't due to the pills, I started humping the bed in desperation, I rubbed my penis against it, and suddenly I squirted hard rope after ropes of cum. I went on for some seconds these seconds were pure ecstasy I had never felt like this, I jumped down and licked it all up, I had become a cum whore I never let any cum go to waste. Just then I got a call.

"Bad sissy, I thought you were in control but, clearly you weren't," Ms. Robin said. She had seen everything through the camera she had installed.

"No, mistress I didn't intend to I didn't even touch it," I said

"But you did stimulate it humping your bed, such a slut."

"Sorry mistress, I will never do it again."

"I gave you a chance and you ruined it, I will give you one more, but you have to do something," she replied.

"I will do anything mistress."

"Good, then dress up exactly as I say put on the sleeveless fishnet crop top, put on a crotchless panty and a micro skirt with fishnet stockings under it and wear the red heels, and put on some slutty makeup."

I did it exactly as she said, it felt weird to let my penis hang out from the panties and to make it worse It was a microskirt the tip of my penis was visible, and the crop top was even worse my nipples poked out of it, I looked worse than a whore.

"Now I'm sending you an address go there and tell your name to the receptionist, she will know what to do," she said and texted me an address and then cut the call.

I knew I had no other option but to go to the location, I got out and started walking fortunately it was already 8 and not much people were on the streets, I went to the address it was a shop in the red-light district, as I got into the street, I noticed it was full of people, there were prostitutes trying to get customers, people inviting customers to their clubs, variety of sex stores, I scared I was dressed up like a sissy slut. One guy even asked me if was free tonight, I understood he thought I was a whore, it wasn't his fault even I would have thought the same, I declined went to the location Ms. Robin had sent me, it was a shop named, 'Deep desires'. I went in to the counter, a girl sat there she was around 25 she was beautiful and dressed very slutty. She looked at me.

"Hey, what are you looking for?" she asked.

"I'm Ron, Ms. Robin sent me."

"Say no more, come with me," she said and guided me towards the back of the store.

"I'm always happy to help sissies like you."

By now I had adjusted, I no longer felt weird when strange women called me sissy, I stood there, she came in with two boxes and a vernier caliper.

"Now let's first put the butt plug," she said. I was shocked did she say butt plug.

"Robin has said its your first time and she wants the biggest that you can fit," she said putting lube on the calipers.

She put rubber gloves on, and asked me to get on all fours and stick my butt up, I did then she lifted the skirt and pulled down the panties, she touched my penis.

"The next item would slide it a lot easier."

I didn't understand the next item, she applied lube on my asshole and inserted a finger in it and moved it back and forth, after sometime she inserted another, when she inserted a third finger I started to pain, I let out a soft moan.

"You like it huh sissy?" she asked.

I tried to lie but couldn't.

"Yes mistress," I said.

"Mistress? looks like you have been trained well," she said smiling.

She kept going with 3 fingers in my ass hole for some time and then inserted the fourth. I moaned again but this time I couldn't stop I moaned constantly; I liked the sensation.

"You're doing good just a little bit," she said and inserted the last finger.

Her whole fist was inside me. I was being fisted by a woman whom I had met only few minutes ago and didn't even know her name, I turned me on so much. She removed her fist after few minutes, I could feel my ass gaping, she grabbed the calipers covered them with lube and measured my gape, it felt cold when it touched my ass hole.

"Your boipussy is quite good for a first time, I think a medium will fit you perfectly," she remarked.

She grabbed a box and opened it and took out a silver butt plug with a pink diamond on top, it was quite big, she covered it in lube, and started pushing it into me, I struggled it got in little by little and then got in with a plop sound, it felt weird feeling a metal I my ass, got up and started getting ready to leave.

"Where do you think you are going, sissy?" she asked.

"What do you mean mistress?"

"We have to get you a second item," she replied.

"What?"

"Something which every sissy need, a sissy isn't complete without one."

She picked up a box and handed it to me, I opened it and was stiff with fear, it was a chastity cage, pink in color and really small not even an inch.

"Dou you like it?" she asked.

I couldn't speak.

"Look at you so excited that you're too excited to even speak, such a good sissy, now come here let's get you into this."

I walked towards her, she grabbed my penis, it got hard on her touch.

"It's so girly and cute," she said and kissed it.

I was burning with same when did it get so small in it was smaller than I remember I hadn't taken the pill till now I guessed that is the reason it got hard, it was only 2 inches even when it was hard, and her kissing made it worse, my penis started dripping pre cum. She got on her finger and asked me to lick it I did.

"We can't put the chastity when your clitty is erect, well we have some options, I could let you masturbate, or there is boring option of applying ice," she said

"Or we can try your new toy the butt plug," she said with a twinkle in her eyes.

"Yes, that is what we will do, come here sissy," she took me and made me squat.

"Now try to stimulate your prostate with your butt plug, just apply pressure on the plug by pushing it deeper and move it around with your finger."

I followed her instructions, I moved it around and got it to touch my prostate. After moving the plug in circles on my prostate, I felt something it felt new and exciting, this was a new sensation. Whenever the plug touched my prostate I felt pleasure of a different kind, I let out a moan.

"Looks like you found your G-spot now get up," she said.

She grabbed me by the hand and let met to the back door she opened it and pushed me outside, I was in a dark alley, I could see the road at the end of the alley, she closed the door.

"Use your butt-plug to cum and don't use your hands I'm watching after you cum I'll let you in, better hurry up before you get caught. If you're caught in the alley like this, the men will surely fuck you," she shouted, through the slit.

I was scared after hearing this I didn't want to get abused, I calmed myself, the only way to get inside is my cumming. I squatted and got to work, I moved the buttplug around and found my G-spot, I moved the plug in circles. I was feeling it but nothing happened, I continued massaging my prostate. I was too scared, then I noticed someone flashed a light on me, it was a man I saw him getting closer he could clearly see what I was doing, he got closer grabbed me, opened his pants, took out his dick and shoved it down my throat. He made me suck it deep, I felt breathless, I couldn't breathe, I wanted to push him but he was too strong for me, I kept sucking on it till he came in my mouth at the same time I came. I came back to reality I was imagining it, the man was still far away and I had cummed, the door opened and I rushed inside. I sat down "why did I imagine it?" I thought to myself, why did I think about sucking his dick, what was weirder was that I really wanted to suck it even now, I wanted to make him cum, drink it, why was I thinking all this.

She took the chastity cage slid a ring around my balls and then put the cage on top it slid in perfectly, she locked it with a "click" sound, I looked at it, tiny pink chastity was hanging between my legs through the crotchless panties.

"Good choice of lingerie I must say, now you may leave the only key is with Robin, she had already paid for it yesterday so, don't worry about the money," she said.

I left, then it suddenly struck me why had Ms. Robin paid her yesterday, she called me.

"How did you like your new toys sissy?"

"Mistress why did you pay her yesterday I thought you decided to punish me today when I masturbated without your permission," I asked.

"Smart sissy, you sissies are so predictable once you get them horny, they will do anything to satisfy themselves, you hadn't cum in 20 days. I kept you constantly horny and after the porn marathon today I was sure you will rub yourself. But I'm impressed you didn't touch it and cummed without touching, looks like the videos have really affected you, but I knew this would happen so I paid her in advance, and it was brilliant performance tonight, how did your first sissygasm feel?" she asked.

"Sissygasm?"

"Men and women have orgasms you sissies have sissygasms, orgasm through anal stimulation," she explained.

"It was new but it felt weird," I lied it felt great.

"Oh, silly sissy, don't worry before you know you will start loving them," she said.

I kept silent.

"Now I have complete control over when you will masturbate, I will see you tomorrow afternoon, I'll take you to a special place in the evening, Bye".

I walked back home it felt weird to walk with the butt plug and the cage, the constant stimulation form the plug, made my penis hard but it strained against the cage causing a lot of pain, I managed to reach my home, I took my pill, and it made my penis soft again but I was still horny, guess taking the pill was the only way to wear the chastity without any pain, I had dinner changed into a new nightie I had bought, it was satin and pink in color and ended just below my waist, it was so soft. I had to pee before sleeping, I went to the bathroom and tried pissing but it was difficult with the cage, my piss was spraying. I got an idea, I sat down on the toilet and tried pissing like a girl, piss came out easily, while I was peeing, I turned and saw myself in the mirror, I stared into my reflection what has happened, I'm pissing sitting down in a nightie, I looked at my reflection but couldn't get myself to believe it was me I had changed so much in a month. I got up and went to my room and got into bed. I tried sleeping but woke up in the middle of the night the pills effect had stopped and now my penis was straining again. I sat on my bed.

"Can't sleep?" Ms. Robin texted.

"No, mistress."

"I see I just finished a new video for you and was about to sleep when I saw you getting up, what happened?"

"The cage is uncomfortable, my clitty is pushing against it," I said. Mistress had instructed me to call my penis clitty and my asshole as boipussy and I didn't want to make her angry.

"This is completely normal, I'm sending you a video watch it, it will help you," she said.

I put my headphones and grabbed the dildo, and played the video. Images of small soft penises flashed. Sissies were giving blowjobs but their penis was completely soft.

"Sissies give pleasure, they must pleasure others, a sissy's clitty must be small soft and feminine, it is always limp, it never gets hard, never get hard, repeat after me," a voice said in the background.

It was hypnotic.

"I am a sissy, I don't receive pleasure I only give pleasure to others, I will never get hard, my clitty will always be soft, my clitty will be limp forever," I repeated this. When the video ended my penis was soft, I went to sleep, and found myself sucking dick in my dream again.

To be continued...