Sissified Ch. 07

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

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I got up from my bed, and rushed to the bathroom. I had no time Mom had gone on a business trip and I had to stay with Ms. Robin till she returns; she was going to pick me up at 9. I thought about skipping gym but that would make Ms. Robin angry. So, I went to the gym, quickly finished my exercise and rushed back to my house. I packed the dildo and the pills first, then I put in my lingerie, dresses, shorts, skirts, and tops. I even packed my foot wear, I looked at my boy clothes, I hadn't worn them in a long time. Ms. Robin had asked me to put on something nice, so I wore a wine-red lacy panty with a red short summer dress and wore the 6-inch red pencil heels, I put on my make-up. I got down and took out the liquid Ms. Robin had asked to mix with food. I heard her car pulling outside I grabbed my trolley and the bottles of liquid and went out. It was 9 in the morning, my neighbors were outside, I quickly rushed into the car, fortunately no one saw me.

"You look good sissy. You have learnt the skill of dressing and your make-up is perfect, but you still need something." she said.

"What mistress?" I asked.

She placed her hands on my chest and felt my nipples, they were so sensitive, my nipple erected. It had grown a lot it was in light brown color the areola had grown and the size had also grown. She circled around my nipples and then squeezed them, I moaned with pleasure. I could feel pre cum dripping through my cage, my panties were wet. She moved her other hand to my panties and felt them.

"Look at you, aroused after playing with your nipples." she said and stopped, then she cupped my small A cup boobs.

"You have some breast now. You need a bra."

Without another word she started driving and went to the mall. We got out and went to the mall. We went to Victoria's secret and met Janet. She greeted us smiling.

"How much you have grown since the last time you look so feminine now. You have become so beautiful." Janet said.

"Thank you, mistress." I replied.

"You're as cute as ever. So, what are you looking for today?" she asked

"I think it's time for her to get a bra." Ms. Robin said.

Janet groped my chest.

"Yes, she has grown a pair and needs a bra."

"Great, let's measure her up then." Ms. Robin said.

Janet got a measuring tape, and we went to the trial rooms.

"It would be better if you were naked, we could try different types and judge which one looks good other garments will only confuse us." Janet said.

"What are you waiting for, go on strip." Ms. Robin said.

I slowly removed my dress and pulled down my panties.

"Looks like you have upgraded." Janet said holding my chastity

"It looks so cute now and I bet panties fit you better now."

"Yes, mistress the panties fit way better now." I replied.

She measured my chest and waist and my hips.

"Wow!" Janet exclaimed.

"What happened?" Ms. Robin asked.

"Her measurements are 32-22-32, she has the perfect figure, just grow a pair of tits and you will have the perfect figure." She said to me smiling.

"Nice work sissy all the gym sessions have finally paid off." Ms. Robin said.

"Thank you, mistress." I said.

I was happy I had the best figure, but it also meant when I go back to being a boy it would be difficult, but I put those thoughts aside for now I was happy with my body.

"I have a record of the panties you bought, so I will just get a matching pair of bras for them and some extras too. I guess you size would be 32A." Janet said.

She returned with a bunch of them. She took out a wine-red lacy bra matching with the panties I had worn, she taught me to wear them, I put them. She asked me to put my panties on, I did.

"You look pretty, almost like a girl." Ms. Robin said. I looked at the mirror, I looked sexy I loved it.

"As she has such small breasts. They will be little loose, but I can get then padded if you want. They will fit perfectly then." Janet said.

"Please do, how much time will it take?" Ms. Robin asked.

"About 30 min, look around the store we have some new items." Janet said and left to get the bras padded.

Ms. Robin and I strolled around the store, I looked at the pantyhose they felt so soft, I wanted to try them on day.

"Sissy come here." Ms. Robin shouted. I went to her, she was standing near a rack of sleeveless oversized t-shirts, Janet was standing beside her.

"These are the latest collections, they are perfect for leisure wear our customers love them." Janet said.

"Let's try them." said Ms. Robin.

She took a pink one and we moved to the dressing room, Janet asked me to strip I did, she then handed me the t-shirt and asked me to wear it. I put it on, it was a weird t-shirt its sleeve holes were too large, the holes ended 2 inches below my chest, completely exposing my side chest, and its length was short too, I ended 2 inches below the waist, the tip of my cage was visible, I felt cold air on my balls, not even half of my butt was covered, I could almost see my butt-plug.

"These look good, makes you completely accessible." said Ms. Robin.

"I knew you would like them." Janet replied.

"We will take 14 of these and please print the words over it." Ms. Robin said.

We waited for another 15 mins and our order were ready, Ms. Robin paid.

"This will be added to your debt." she said.

We left the store and got in the car. She drove to her home, it was huge she took out a remote and pressed a button and the huge gates opened, she drove in, the house was beautiful, I had a garden, a pool, a jacuzzi. We went inside, it was modern looking it was well furnished.

"I got a huge inheritance from my grandparents, in case you are thinking how a high school teacher can afford all this." she said.

"It's beautiful mistress." I said.

"Thank you, sissy."

She took me to my room.

"I had it renovated for you." she said as she led me to my room.

I entered it was pink everywhere, pink walls, pink bedsheets and pillows, pink carpet, everything was a different shade of pink. The word 'sissy' was written in huge letters, several photos hung on the wall, they were all mine, right from my fist pic in panties that I sent to Ms. Robin to as new as the time I masturbated after getting the tattoo.

"You like it?" she asked.

"I love it, mistress."

"Good now listen, the t-shirts we got today you are to wear them only without any underwear, till I say otherwise, and we will train a little more now, there is the computer for you to watch your videos, whenever I ring this bell come find me, do you understand?"

"Yes, Mistress." I replied.

"Good, now change and meet me in my room." she said and left.

I changed into a red t-shirt, I felt so exposed with every stop my cage hit against my thighs, I could feel the air on my ass, I made my way into her room, she was sitting on her bed wearing only her panty and bra. I got near her she gestured me to kneel and I did.

"What did we learn about sissies yesterday?" she asked.

"Their clit is not their sex organ their boipussy is." I replied.

"Very good, starting today I will teach you to use you boipussy, now get into the doggy position." she ordered.

I did. There was a sharp pain on my butt cheek, I looked Ms. Robin had injected something in me.

"It will help you, trust me." she said.

I believed Ms. Robin instantly.

She put some lube over her gloved hand, pulled out my butt-plug and put some lube over my asshole, she slowly put a finger inside me, gradually she put another, then another, till all of them were inside. I moaned with pleasure, I was being fisted, with every thrust she hit my G-spot, it was so good, I drooled. She stopped and opened a packet inside was a dildo not so big, it was around 8-inches, my ass gaped, she put some lube in the dildo and pushed it inside me, this was the first time I was taking a dildo up my ass, it felt great, it hit my prostate so well, I could feel myself about the cum but nothing came out, I was too horny to think, I begged her.

"Please mistress don't stop, please. More I want more of it." I begged.

"Oh, sissy it's enough for first day. We will try again tomorrow." she said and pulled it out and put my butt-plug back.

"Please mistress, some more time please." I begged.

"Enough, it's enough for today. Go to your room I will do some more training in the evening." she ordered.

I left quietly, surprisingly I was so horny but nothing leaked out of my penis, not even precum it was weird, I went into my room, and played the videos Ms. Robin had sent them. They were about limp clitty, I watched them and then drifted to sleep, I woke up around 6 in the evening. I got ready she rang the bell, I rushed to her room, the plug stimulated my prostate keeping me aroused, I went to her room and kneeled by her bed.

"What is the aim of a sissy's life?" she asked.

"To give pleasure to others." I replied.

"Exactly, by giving blowjobs you have learnt to pleasure men, but you need to pleasure women too, I will teach you to pleasure women." she said.

"Yes, mistress." I replied.

"Lick my feet and kiss them, then suck on the toes." she ordered

I bent and licked her foot, it smelled good, I licked it and kissed it, then I started sucking on them, I slowly sucked on then using my tongue in the process.

"You are natural I must say, stop and remove my panties." Ms. Robin said.

I was excited, I was about to see Ms. Robin's pussy, it was like a dream come true my pounded so fast, I grabbed her panties from both sides and then pulled them slowly, I removed them. She spread her legs, there was her vagina in all of its glory, it was beautiful. It was my first time seeing a vagina in real life, I was filled with excitement.

"This is the clitoris, these are the lips." she said explaining the parts of vagina she continued for some time.

"A sissy like you can only give pleasure to a woman like this." she said.

She taught me how to lick her pussy. I started I first licked the clitoris, I licked it passionately. Suddenly she shot me with another syringe and removed my butt-plug, she put lube on the dildo and pushed it into my asshole, as I licked her, she fucked my asshole with the dildo, I moved down and licked her pussy, I could guess she was in pleasure by looking at her expressions this continued for some time I again felt myself cumming my sphincter tightened, but nothing came out and I was as aroused as ever, she stopped and put my buttplug back.

"You did good today we will practice twice a day, you will an expert pussy licker in no time." she said.

I went back to my room, I was so horny, every step made the plug move, it was so arousing, I looked at my reflection, my bob cut blonde hair, with the slutty t-shirt, the pink cage visible, I got even more aroused, I got into my bed and tried to sleep. I woke up hearing the bell, it was 5 in the morning, I went to Ms. Robin's room, she was wearing a gym short and pushup bra.

"Get dressed, you need to be flexible, the gym is a little far from here, so as long as you are here you will be doing yoga with me." she said.

I went to my room and got dressed in my gym clothes, a pushup bra and a short. I went back to her, we did yoga, she helped me stretch, I was exhausted after the session.

Now go to your room, and get ready for your training. I went back took a bath and slipped into a t-shirt with the word, 'slut' over it, I went to her room. I practiced pleasing her, she shot me up with a syringe and pounded my ass with the dildo, after this I went back to my room and watched the videos, she had sent me, again in the evening the training continued. This was my daily routine for the next week.

It had been week I had stayed at Ms. Robin's house, today we did yoga and I had already mastered all the basic movements and moved on to much advanced ones, I noticed my body was getting more flexible, it felt great.

I went to her room for training she pulled my butt-plug and it easily slid out all these banging from the dildo had made my asshole pretty stretchy, I got to licking her clitoris and she shot me with the syringe and got to fuck me with the dildo, I licked her slowly and sensually, I moved to her perineum and licked with too, I switched between her pussy and perineum, I licked on the exact right spots, after sometime I felt her shaking, I continued licking, she came for the first time, her juices filled my mouth and spread all over me, she took put the dildo and laid flat on the bed. Her pussy juice tasted sweet I liked it, and swallowed it.

"It was a strong orgasm, you did good sissy." she said panting.

I kneeled there. After sometime she got up and said," Be a good sissy and put your butt plug back in, you did good today and I will reward you, now go back to your room and don't change watch the videos till I return."

Like a good sissy I went back to my room and watched them. In the evening she came to my room.

"These are you gifts" she said handing me 2 boxes, I took them.

"Open them." she said.

I opened the first box it was brand new butt-plug it was completely transparent; it was 5 inches in length and 3 inches in width.

"I noticed your old butt plug had gotten too loose for you, so I got you a new one. Open the other box." she said.

There was huge black dildo inside it almost 12-inches in length and 3 inches in diameter.

"Let's try them." she said excitedly.

"Thank you, mistress." I replied and got into the doggy position.

She lubed the new dildo and my asshole and slowly started pushing it in, it pained a little at first, then it was replaced with pleasure, it was so huge, it had stretched my asshole so much. I was panting and moaning loudly, Ms. Robin shot me with another injection, I could only take 8 inches of the dildo inside me. I felt myself cumming but as usual nothing happened, she stopped and pushed the new butt-plug, it slid in quite easily.

"If you keep on progressing at this pace we will need to upgrade soon." she said tapping on my butt plug.

"Go to sleep tomorrow I will teach you something new." she said and left.

I drifted to sleep. Yoga next day was difficult with the new butt-plug but I got the hang of it. I went into her room fer training, today she sat there without panties, in a doggy pose with her ass facing me.

"You have learnt to pleasure the pussy, now you need to learn to pleasure the asshole." she taught me all about licking the ass.

I got to it, I circled the hole with my tongue, she moaned. I licked her asshole slowly, I increased the pace slowly at the same time I licked her perineum, I slid my tongue inside her ass hole and she moaned loudly, after sometime she asked me to go back to her pussy, I did and she came again.

"Twice in a day, you're really good sissy, now it's your turn." she said.

She starts fucking my ass with the new dildo and shot me up again. I was confused I had been constantly horny for a week now, how is that I felt I was about to cum and I didn't and even after being so around I didn't even drip a single drop from my penis, thought but didn't say anything to Ms. Robin. After sometime my sphincter tightened and Ms. Robin pulled out immediately, I went back to my room to watch the videos. This time the videos were different, it was titled "butt slut" I played it, the video of as sissy getting buttfucked started playing, a man was fucking her from behind and her small clitty bounced with every thrust, several such videos played.

'A sissy's boipussy is always ready to pleasure, she never says no to cock, she only squirts while taking a cock up her pussy.', a voice in the background said and I repeated them. It was evening when they ended, I went for training it was the same. This was my routine for the following week.

I had been aroused for two weeks, my brain felt broken, I could think of anything, I kept drooling almost all the time, every step I took made me more aroused, dressing sluttily was relief either. I went to Ms. Robin's room for my training. I licked her ass first then her vagina, I had become an expert now, I knew my way around a woman's parts now, this time I tried something different, I went to her foot and licked it, slowly sucked on her toes and then moved to her ass hole and dug deep into it with my tongue, I found her spot and massaged it with my tongue at the same time I fingered her pussy, I had gotten really good at pleasuring her. Kept doing this for a while, she shook continuously and came hard with such force, pussy juices I drank as much as I could get in my mouth, she lied flat on the bed, she looked completely spent. She got up after 30 mins.

"We shouldn't forget about your training." she said.

I was already in a trance, she had slept for 30 mins, I was too aroused for the last two weeks, my mind had stopped working, I kneeled there drooling.

"Are you alright?" Ms. Robin asked.

"Yes mistress."

"You don't look good, tell me what happened?"

"I haven't been able to cum for the last two weeks, and all the training had made me so horny, I'm not able to think straight, mistress I need to cum, please mistress." I begged.

"You gave me a great orgasm today, I believe you deserve one too. I will let you squirt."

"Thank you, mistress." I said happily. Finally, I will be able to cum I thought.

"But as always you have to do something in return."

"What do I have to do mistress?" I asked.

"Nothing much, it will be a little pain full but nothing permanent." she said.

If it wasn't permanent there was no problem in doing it, I agreed.

She dressed me up in a micro denim shorts and a netted crop top, with neon bra and panties underneath them. We drove to the tattoo parlor. I looked at her shocked.

"Don't worry you are getting another tattoo, come on in." she said.

We went inside I was let in with a blind fold. I heard voices.

"She is ready let's do it."

I felt a sharp pain on my right earlobe, then on my left after sometime same pain on the navel, when my blind fold was removed, I saw two small diamond studded earrings were in my earlobes, I looked down there was a golden pin with 5 diamonds shaped in a flower pattern.

"You look amazing with those, don't worry they aren't permanent If you remove those the holes will fill up, now let's go home you have your real prize waiting." Ms. Robin said.

We drove back to the house, I changed it the t- shirt and went into her room, she was sitting on the bed naked with a strap on dildo around her waist, it was the bigger one, full 12-inches of black cock.

I got excited seeing it, I crawled to her. The dildo was hanging between her legs, I kissed the tip and circled around the head with my tongue, I was starting to get more aroused and for the first time since I came to Ms. Robin's house I found my penis leaking, I took some of it and licked it, for the first time in a long time I tasted cum, I got back to the dildo I swallowed the tip for a while and then moved deeper I pushed down a little more of the dildo with every stroke, till I had them deep to the balls, I continued sucking for a while till Ms. Robin pulled it out and asked me to get on the bed and get on all fours.

"You are such a good cock sucker, you have lubed it well, but still we will use some real lube I don't want to hurt you."

She covered the dildo with some lube and put some on my asshole.

"It won't fit mistress." I said looking at the dildo.

"Don't worry it will." she said and spanked my ass.

She spread my ass cheeks, pulled out my butt-plug, it slid out with ease, and hit my hole with the dildo. Then she put her finger and started stretching it, she aimed the dildo at my hole and circled around it. It was shaking with excitement, my penis leaked non-stop. She grabbed my hips and thrust the tip in, he moved it in and out for while then she started going deeper, my sphincter had tightened around it, with every thrust she went deeper I could feel my hole tightening around it, I enjoyed every second of it, it hit my prostate perfectly and made me leak even more, it was down to 8-inches now and I had never been in more pleasure, I squirmed with every thrust.