For those of you who have read my previous story, already know about the hot strap-on session with my girlfriend who has now become my mistress. The following story is about the events that took place in the next couple of weeks after that night.

Since that night, my relationship with Aanchal has transformed a lot. She started sending me articles about sissy training, anal sex, deep throat, BDSM and also started forwarding dick pics of David.

Whenever we spoke on the phone or text, she often addressed me as a naughty sissy boy or sometimes called me a bitch and a slut. She did it so casually, that even I started accepting such names without any hesitation.

The first couple of days, the routine was the same. She would make me come over to her store. We waited till she wrapped up all her work and all her employees had left and then our sissy training session used to begin. She always wore the strap-on, made me deep-throat the dildo and then fucked my ass till I orgasmed.

By the 4th day, I was taking in almost 6″ of the black dildo in my ass. We always ended the session with me fingering and licking her cunt and making her cum on my face. I had gotten pretty good at sucking dicks by now and my ass muscles had also stretched quite a bit, so the pain had become very less.

Aanchal never let me fuck her or do anything else to her. I was only allowed to lick and finger her cunt. This routine continued for another week or so.

One day, she called me to the store in the morning. It was a public holiday, so the store was closed for business and nobody was there. She had messaged me earlier instructing me to quietly enter the store and sit in her office without uttering a word.

When I entered the store, I couldn’t see anyone. However, I could hear Aanchal moaning in the background. The moans were coming from her office. Upon entering the office, the view was pretty spectacular. She was sitting on her chair, with her legs spread wide, fully naked. However, her laptop was placed in front of her and I could see that she was on a video call with someone.

There was a guy moaning on the other side of the video call. I was shocked and turned on at the same time. She had a dildo inside her cunt which she was moving in and out screaming in pleasure with each thrust.

She saw me entering and pointed at a chair kept behind her. The chair was positioned in such a way that I could see the screen, but the man on the other side couldn’t see me. Aanchal had planned all of this.

I sat on the chair and stared at the laptop screen. There was a live stream of a naked black man stroking his huge erect penis. I recognized that dick, it was David. He seemed to be on the verge of cumming and within a few minutes he ejaculated a bucket load of sperms up in the air.

Meanwhile, Aanchal was having a strong orgasm and I could feel her body shiver with pleasure. She then shut the laptop and turned towards me and said, “What are you looking at, bitch? Come clean my pussy.”

I bent down and licked all her juices, till she was completely clean. She then got up and wore a thin silk robe. She sat across me and said, “I am planning to meet David next week. I think about his dick all the time. You have been getting fucked every day. But what about me, It’s been so long since I have been fucked.”

I replied, “If you want, I can fuck you too Aanchal.” She laughed, “Yes honey, you can fuck me with your little dick, but just like you I also want a 8″ long tool in my hole.”

I felt embarrassed and humiliated and started to tear up a bit. She saw me getting emotional and came close to me and held my hand, looked into my eyes and said, “Don’t be silly baby, I am not breaking off with you. I love you and you are my soul-mate. But don’t you realize that we both need a strong man like David in our lives. I want to share David with you baby. I want you to be a part of my affair with David.”

I looked at her with innocent eyes and asked her how that would be possible. She then smiled at me and told me to follow her to the changing room.

The changing room is big and there are multiple mannequins dressed up with different outfits. She turned towards me, held my hand and said, “It’s time we move to the next chapter of the training. I want you to embrace the sissy inside you. I want you to transform into this sexy, beautiful creature you are capable of becoming. I want you to think, walk, talk and fuck like a woman. I know your body measurements and have personally made these outfits for you. Pick whichever one you like.”

I was once again speechless. I had never cross-dressed in my life before. But the thought of it made me horny. There were 4 outfits, a sexy black cocktail dress, a traditional salwar kameez, a short casual dress, a pair of tight fitting Jeans & crop-top.

“I don’t know which one to pick Aanchal, will you decide for me please. After all you are the expert,” I said.

“I think you will look amazing in all these outfits, but let’s start with the cocktail dress first,” she said with excitement. “But first, we have to get you cleaned up. You look like Nikhil right now, we need to transform you into Niki” she laughed.

She made a phone-call to someone and checked on where they had reached. I asked her who it was, but she said it is a surprise. After 15 minutes, we heard a knock on the door, Aanchal greeted this girl who she seemed to know pretty well.

Both the girls entered the changing room and looked at me. Aanchal introduced the girl, “Nikhil, meet my very old friend Malaika. She normally assists us with our shoots for make-up. She is very good at her work. And don’t worry she is very discreet,” she winked at me.

I was shy and froze for a second. Aanchal wanted to dress me up in front of her friend. Is she mad?!! Malaika excused herself and went to use the washroom, I think she sensed the tension in her room and wanted to give us space to talk

“Aanchal, I cannot do this in front of her!!” I shouted.

“Calm down, Niki. Stop being so dramatic. I trust Malaika completely. Otherwise I wouldn’t have called her. Back in college, we used to go to clubs to pick up guys and there have been times when we have been gang-banged by 4-5 guys together. Nobody knows about these incidents but the two of us. So chill out and don’t worry so much. I have told her everything about our relationship and she is okay with it,” she said.

For a moment, I forgot about the topic we were discussing and was picturing the two of them getting gang-banged. I realized that my Girlfriend is quite a slut. Wow!!

Malaika entered the room and looked at me, “So Nikhil, sorry I mean Niki. Shall we get started.” Both the girls laughed while I stood there red cheeked and shy.

Malaika was a sexy woman. She was 5’5″ dusky, thin, petite and had small boobs. She had tattoos on both her arms. She wore jeans and a short top that exposed her pierced navel with a deep cleavage. The black Nail paint on her feet and hands. She inspected my body and told me to remove my clothes. I did as she said and striped down to my underwear.

She told me to turn around so she could see my entire body. “So, we will start with complete body waxing to remove all the hair. I need you to remove your underwear. I need to inspect your groin and asshole as well” she said very bluntly.

I looked over at Aanchal and she nodded. I removed my underwear and stood completely naked in front of these girls. Malaika asked me to turn around and spread by butt cheeks. She inspected my asshole and then commented, “You have a cute bum Niki” she spanked my ass cheek and both the girls laughed.

She made me sleep on my back first, and waxed all my hair on the chest, stomach, legs. Then she waxed all the hair around my dick. Waxing was a painful exercise and instead of being turned on by this, my dick was soft and small. Which she commented by calling it cute and flicked it with her finger playfully.

I noticed that Aanchal had left the room, she was talking to somebody on the phone. I was sure it was David.

Malaika then shaved all my facial hair as well. I was then told to turn over and sleep on my stomach. She started with my back and then my legs and then lastly my ass. Once she was done, she started slowly running her fingers around my asshole.

She asked, “So Niki, how do you maintain such a nice ass. Your hole is so nice and stretched. Tell me what is your secret.”

I replied, “Well, all the credit goes to Aanchal, she has been training me really well.” She then shared that her Boyfriend has been trying to fuck her ass but hasn’t managed to penetrate properly. Apparently his dick was really big and it hurt her when he tried.

I asked her how big it was, to which she replied 6.5″. I told her I was able to take in 6″ of a thick dick in my ass. “Woah Niki, you are quite a slut now, aren’t you?!!”

She laughed and slid one finger inside my asshole. She gasped at how easily it entered and wanted to know how much I could take in. She had small petite hands and I told her to go ahead and try for herself. Aanchal was still busy on the phone in her office.

Malaika grabbed a lotion from her make-up bag and applied it on her fingers and on my asshole. She first inserted one finger and then two. She inserted them fully inside, and stroked back and forth.

I started moaning with pleasure. “Oh Niki, your ass swallowed my two fingers so easily. I am gonna go ahead and put the other two fingers as well.”

She took her fingers out, applied more cream on her entire hand this time and started inserting all 4 fingers in me. It felt so great and I could see that Malaika was turned on as well. She moved her hand in and out of my ass vigorously.

Aanchal heard the moans and entered the room, she smiled wickedly and was very pleased with what she saw. Malaika and me both looked at her, my mouth was open with pleasure and Malaika had her hand up my ass.

“Aanchal, Niki has such an amazing ass, what kind of training have you been giving her ” Malaika spoke while moving her hand in and out. She then slipped her 5th finger in as well. I screamed loudly in pleasure. She was about to remove her hand but Aanchal told her to continue.

“Don’t stop Malaika, Niki here needs more training” She looked at me. “Next week you have to fuck a 8″ Black dick. I was just talking to David about you and I have promised him that he can insert his entire dick in your ass. He hasn’t met any girl till date who can do that.”

Malaika laughed and said, “In that case, we have to keep going. Your reputation is at stake here Niki. She continued moving her hand in and out of my ass. She then stopped for a second and in one swift movement slid all 5 fingers with the fist into my ass. I cried with pleasure. She almost had her entire fist in my ass and slowly moved it in and out.

Aanchal stood there quietly while Malaika fucked me with her fist. After a couple of minutes my body was trembling and I was sweating profusely. These girls were pushing my body to have multiple orgasms. I was so consumed by the pleasure, that I couldn’t even tell them to stop. I felt like a whore, who wanted more pleasure.

I moaned loudly with pleasure and my body trembled from head to toe. Is this what it feels like to have multiple orgasms. All I could think about now is David’s black cock fucking me and filling me up.

After a few minutes, Malaika stopped and slowly removed her fist, but my asshole was so stretched, I could still feel her fist inside me. Malaika looked at my face and said “Aanchal, it feels like she is still not satisfied. You have turned her into quite a whore yaar.”

Both the girls told me to get up and sit upright. I could sense that my sexual aura had an effect on them as well. Both of them got really horny after seeing me have multiple orgasms.

They both took turns and kissed me on my lips and neck. They took me to the washroom and cleaned all the sweat from my body, juices from my ass and cum from my dick.

They got me back to the changing room and made me stand in front of the full length mirror. I saw my body, it was absolutely smooth and beautiful with no hair at all. I had a glow on my face after all the fucking. They picked out a dark blue sexy lingerie set for me.

Malaika helped with putting it on. She had a pair of silicon boobs to insert in my bra. She tucked my penis into my panty between my legs, so that it was hidden. I wore black color stockings. Aanchal had purchased a pair of sexy heels for me to wear.

I then slipped on the cocktail dress. Malaika did some subtle make up to make me look more feminine. She then pierced both my ears.

Aanchal made me wear her set of diamond earrings which were beautiful. They picked out a wig which would suit me and help me put it on. It was long brownish-black straight hair. Maroon colored lipstick to complete the look.

I then stood in front of the mirror and could not recognize myself. I looked like an elegant and sexy woman. Both the women had tears in their eyes when they saw my complete look. Malaika said, “Niki, you look so good. You look like a complete girl. So hot and sexy babe”.

Aanchal hugged me tightly and said, “You are ready Niki. You are so fucking ready to face the world.”

She then clicked multiple pictures of me and sent it to David. Malaika hugged both of us, she gave me a peck on my lips and wished me luck with David. She left and shared her number with me and told me to call her if I ever needed any help with makeup.

After Malaika left, Aanchal couldn’t take her eyes off me. Even I kept appreciating myself in the mirror. I felt like I was reborn as a woman that day. Aanchal opened a bottle of champagne and decided to celebrate the birth of Niki.

We spent the entire day trying out some other looks as well. She was training me on how to walk in heels without tripping. We held hands all day and felt so connected and in love. Almost like we were soul sisters.

Aanchal shared a lot videos and articles on anal sex and hygiene. She told me to study all of it and become an expert in this area. She then told me to stand up and spread my legs.

She said, “I have two more surprises for you. We need to make sure your asshole remains stretched and loose. Now bend over and then don’t say a word.”

She removed something from her bag. It was a butt plug, she sanitized it, applied some lube and slid it into my ass.

“Niki, you are allowed to remove this only when you use the washroom. At all times, the butt plug should be in your ass. This will help you with your training. I want you to give David so much pleasure, that he forgets about every other woman in his life. All he shall want is your sexy asshole.”

“The second surprise is this!!” She said while handing over a Victoria secrets bag.

“I have bought you a dozen panties. From now on, you will only wear panties. No more men’s undergarments. You will also stop masturbating with your dick. Whenever you feel horny, you will use this new technique that I have come up with” she said with a wicked smile.

She unlocked her phone and opened an app. The next thing I know, I almost fell down, there was a buzzing sound and vibration I felt in my body. The Butt plug was also a vibrator! I moaned again, and hugged her.

“Niki, whenever you feel horny, you will call me and I will start this vibrator. I control this vibrator and it’s got 5 levels of speed. If you disobey my orders also, I will use this at the highest speed.” She loved to see me so vulnerable and shaken. I continued to moan, as the vibrator did its work.

Later, we video-called David and spoke to him. Aanchal introduced me as her cousin-sister. He was a very handsome, well spoken African American man and was pursuing his PHD in Pune. He was originally from South Africa.

He flirted with me a bit and said was looking forward to meeting me. Apparently, Aanchal had mentioned some very amazing things about me. I smiled slyly, I knew exactly what he was talking about. I could’nt wait to spend time with Aanchal & David next week. I had a good feeling about the three of us.

There is more to come in the adventures of Niki and Aanchal. Stay tuned. Please send your feedback on [email protected]