Previous Part: Cross-dresser substitutes as Boss’s wife – Part 1
In the previous part, I had finished giving him a blowjob. After some time, I went to the bathroom, cleaned myself up, fixed my clothes and makeup and came out. I saw that Shekhar had passed out on the sofa.
I tried to wake him up, but he was not in his senses and slurred his speech. I waited for some time, but he started snoring. So I picked up my bags and went back home.
By the time I reached home, I had sobered up. Even though I was drunk back then, I remembered everything. The thought of the incident filled me with joy, and I once again became horny.
I used a vibrating dildo to pleasure myself. I lubed it up and inserted it into my ass. I then turned on the vibrator. I imagined myself with Shekhar and began enjoying the sensation. I incrementally turned up the vibration and started jerking myself.
I once again reached climax and orgasmed. I ejaculated once again. I removed the vibrating dildo from my ass and lay on the bed.
After lying down for a few minutes, I cleaned up and went to bed. I was overjoyed with the events. This was the first time I had engaged in a sexual act with someone such as Ankita. I felt like a woman. I sent a message to Shekhar expressing my joy.
The next morning, I woke up happy and fulfilled. I checked to see if Shekhar had called. There was no call or message. I waited the whole day for him to contact me. But he never did. The weekend got over.
It was Monday the next day. I went to the office as usual. Shekhar still had not contacted me. Over the next few days, I tried to run into Shekhar at work. But I could never meet him. It was as though he was avoiding me.
On Friday, I sent him a message saying, I’m sorry about what happened. I didn’t mean to. You are a good friend. I don’t want to lose the friendship we have. Please reply if it’s okay between us.
On Sunday night, I received a reply from him saying, Okay. No problem. That’s it. I thought that was the end of it and moved on. Over the next few weeks, we met in the office once or twice. But it was strictly professional between us. On the inside, I was annoyed with him.
About 3 weeks after the night at his apartment, I received a message from Shekhar. It said, “Ankit. Would you be able to meet me for coffee after work?” He called me Ankit, indicating he wanted to speak to me as Ankit and not as Ankita. I hesitated for a few hours but later replied saying, “Okay. No problem.”
He sent me the location of a cafe in Bandra. After work, I went to the cafe and waited for him. He arrived 10 minutes later and ordered us coffee and sandwiches. I had an indifferent expression on my face. He started speaking about work and other things till our order arrived. After the waiter left, he said,
Shekhar: I know what I did was wrong. I should not have ghosted you. But please try and understand my point. I’m not gay. I have a wife and two kids.
Shekhar: I thought we were drunk. It happened by accident. I didn’t want to. But it happened. I tried very hard to forget about it. I had been lonely, and you were looking so beautiful. I slipped up.
Shekhar: But the truth is, I can’t forget about it. The memories come flashing before my eyes whenever I’m alone and thoughtless. I think I like Ankita.
Hearing that last line, my annoyance at him reduced considerably. But I didn’t show it to him. I continued with my indifferent expression, but inside I was feeling joy.
Shekhar: I know it’s not fair to you. But I am married. I love my wife. I don’t want to cheat on her. But I also have needs. So, I’m trying to say that if we decide to go ahead, it can’t be something serious.
Me: I understand. I need some time to think.
Shekhar: Of course. Take your time. We’ll meet here at the same time next week. You can let me know of your decision then. I’m once again very sorry for my recent behavior.
Neither of us spoke after this. We ate in silence, and I left.
I thought about our conversation a lot, and by Sunday evening, I had arrived at a decision. However, I didn’t contact Shekhar. On Wednesday, after lunchtime, I received a message from Shekhar asking whether we were still meeting that day. I replied with a ‘Yes.’
Just like last week, I reached the cafe after work. But this time, Shekhar had already arrived and was waiting for me. I joined him at the table. We placed our orders and waited for the orders to arrive and for the waiter to leave.
Shekhar: So, what have you decided?
Me: I’m okay with a no strings attached arrangement. But I have a few conditions.
A smile ran across Shekhar’s face.
Shekhar: Okay, what are your conditions?
Me: First, nobody else can ever find out about this. Second, our professional lives should never be affected by it. Third, I want to be your wife for 10 days.
Shekhar: (A little shocked) My wife?
Me: Yes. It’s a give-and-take arrangement. You get to enjoy the pleasures of a wife. I get to be a wife.
Shekhar: (still confused) I don’t understand.
Me: I will take a fortnight’s leave from the office saying I’m going to Patna for my cousin’s wedding. During that fortnight, you will have to marry Ankita and accept her as a wife for 10 days. Nobody will ever find out. You can continue your normal life, go to the office, meet friends, whatever.
Me: But you will stay with Ankita at my house. I have thought about it. We will have a wedding at my house followed by our first night. I will be your wife and treat you like my husband for the next 10 days. After which, we go back to our lives. If both of us agree, we can engage in any way from time to time.
Shekhar: Hmm… I don’t know
Me: It was the first time I did anything sexual with someone other than Ankita. I have always wanted to feel like a woman, and I felt it more than ever that day. I have told you how I wish to be a wife or a mother. In this way, I can fulfill at least the wife part.
Me: I didn’t think anybody would like me as Ankita after discovering that I am a man. But you are okay with it. So, this is my only opportunity to be and feel like a wife.
Shekhar: Oh, I understand. But I don’t know yet. I’ll need some time to think.
Me: Take your time. But, if anything has to happen, these are my conditions.
We finished our food and left after that conversation. I may have pushed it too far with my demands. But then I thought maybe I’ll never get such an opportunity again. Plus, it was mutual. We would both be using each other to fulfill our desires.
Two days later, I received a call from Shekhar late at night. He conveyed his acceptance of my condition but said nobody could ever find out about it. I told him that in itself was my first condition. We decided to meet the next day to figure out the logistics and hung up the phone.
I was super excited and happy that night. The thought of becoming somebody’s wife filled me with so much joy that I was on cloud 9.
The next evening, I got ready as Ankita. I wore a black chiffon saree, chose a medium-length hair wig, applied basic makeup, and wore high heels. I then went to Shekhar’s house to discuss our arrangement.
Shekhar opened the door to let me in. His eyes widened, and his jaw dropped looking at me. He said, “You’re looking so elegant and beautiful.” I blushed and entered.
He offered a beer. I declined and said, “No drinks till the wedding. I don’t want to slip up. Anything sexual between us will happen only after the wedding.” He said, “Nothing would happen with a beer.” But after seeing how adamant I was, he gave up.
I spent the next 2 hours discussing and planning everything to the last detail. After concluding our discussion, we had dinner, and I returned home. As per our plan, I applied for a 10-day leave. Of these, 7 would be work from home, and 3 would be complete leave.
Including the weekends, it was 14 days of absence from going to the office. My leave would begin on 13th September and end on 24th September. We had fixed our wedding for the night of 12th September, Sunday. So, I would have time from Friday night to prepare for it.
With only two weeks to go for the wedding, I began all the necessary preparations. First, I ordered a bridal lehenga for me and a sherwani for Shekhar online. Later, I went to an imitation jewelry store in Dadar and bought bridal jewelry.
The jewelry included bangles, necklaces, earrings, nose rings, maang tika, anklets, bracelets, and armlets. But most importantly, two wedding rings, a mangalsutra and a toe ring. Since it was imitation jewelry, the entire purchase cost me only 12k.
I then bought a box of sindoor, chooda, sehra, and other items for the wedding rituals and puja. By 9th September, Friday, everything was ready and in place. I gave my housemaid the same excuse of me going to my hometown for two weeks. I asked her not to come till I called her.
On the 9th evening, I came back home from work. This was the last time I was going to be Ankit for two weeks. I was going to get mehendi on my arms and legs. This meant I couldn’t be Ankit again till the mehendi wore off.
I looked at myself in the mirror and waved a symbolic bye to Ankit. Then got dressed as Ankita. I went to a nearby market and sat down with the mehendi artists. I chose a mehendi design that ran up to my elbow on the hands and my shins on my legs.
The next day, Saturday was spent preparing the house for the wedding and for Shekhar to stay with me later. The only thing left for Sunday was to buy garlands and flowers. I placed an order on Instamart. I would ask the delivery person to leave it at the main door and pick it up when nobody was watching.
I woke up on Sunday morning excited about my wedding. The morning was spent ensuring everything was in place. By the time I was done, it was already noon. I quickly had my lunch to get anal douche before getting ready. The flowers arrived at 2 pm.
I then started preparing the mandap for the wedding. I kept the necessary items and made a small enclosed space for the havan to be lit. I then started decorating the house with flowers and lights and prepared the bedroom for suhaagraat.
I was done by around 4 pm. I decided to go about the anal douche so my ass could be ready for sex. After douching, I inserted a butt plug into my ass to prepare it for penetration.
I had enquired with a pandit about an auspicious time. He said the time is very auspicious, between 9.30 and 10.45 pm. I had asked Shekhar to reach my house by 9 pm.
At 5 pm, I started getting ready. First, I removed all my body hair and shaved my face. Then I took a hot water shower. After which, I dried myself, lubed up the butt plug again and inserted it into my ass. Feeling fresh, I sat down to transform myself into Ankita.
First, I wore a hairnet and tucked all the hair on my head into it. I secured it with medical tape. I then put on a long black-haired wig and secured it with an adhesive solution. I combed the hair, styled it, and made it into a bun. I secured it with hair clips and pins.
Next, I moved on to my chest. I squeezed my chest together and put medical tape to hold them. This created a basic natural cleavage. I then used the magic of makeup to enhance the cleavage by contouring and highlighting. I then fixed the silicone breast forms.
I applied a finishing touch to the makeup to make them look as natural as possible. Next, I wore a new set of lingerie that I had purchased recently for the special occasion. It was a red color bridal bra and panty set. It was the 34-B size which fit perfectly over my silicone breast forms.
The panty covered and hid my male genitals. I then wore my bridal lehenga set. It was a brick red color lehenga with embroidery and beads. The blouse was backless and covered my fake boobs perfectly in the front.
Next, I moved on to my face. First, I plumped up my lips. Then I used a curler to curl up my eyelashes. I then painted my toenails with brown nail polish. For the makeup, I followed a bridal makeup tutorial I found on YouTube. After that, I applied lipstick.
I looked at the time, and it was 7.30. I still had 2 hours, so I took a 15-20 minute break. I called Shekhar for updates. He said that he would reach by 9 pm. I asked him to enter the house with the spare key I had given him and get ready. I had placed all his clothes on the sofa. I did not want him to see me before time.
After that small break, I went ahead with wearing my jewelry. I meticulously wore the maang tika and nose rings and fixed them to my wig. Next, I wore my anklets, bracelets and armlets. I put on my necklace also. I had bought clip-on teardrop earrings that I secured on my ear.
I then wore my red and white bridal ‘chudis’ on either hand. The contrast of my fair skin to my mehendi had developed a dark brown color to the jewelry looked stunning. Next, I fixed the acrylic nail extensions that were painted chocolate brown on my fingers. I then tied a mogra flower gajra to the bun in my wig.
Finally, I covered my head and shoulders with the bridal dupatta. I was ready in complete bridal attire. I stood up to check myself out in the mirror and looked spectacular. I then sat waiting for the clock to strike 9.30 pm. I was lost in thought of how my dream was coming true.
A few minutes later, I heard the main door open and close. About 15 minutes later, I called Shekhar to ask whether he was ready. He said he was ready and waiting for me. It was 9.20 pm. I asked him to wait 10 more minutes. Finally, the clock struck at 9.30 pm.
I played ‘din shagana da’ on the music system and made my bridal entry. Shekhar had worn his Black sherwani and was ready with a sehra on his head. He saw me, and his eyes almost popped out. He said, “You’re looking so beautiful.”
I blushed and made my way to the makeshift mandap. I had made everything ready. Shekhar lit the havan fire, and I played a pandit performing a wedding video on YouTube. We first exchanged garlands. Then we exchanged rings. After the recitation of shlokas, it was time for the wedding ceremony.
On the cue of the pandit in the video, Shekhar tied the mangalsutra around my neck. He then took the box of sindoor in his hand, and I lifted the dupatta over my head. He pushed the maang tika aside and applied sindoor on my maang. I became a little teary-eyed at that point.
We then tied our clothes together with a dupatta and took the saath pheras around the havan fire. On its completion, I became Shekhar’s wife. Tears of joy rolled down my eyes. Finally, he put toe rings on my toes.
I stood there as a newlywed bride, sporting all the signs of a married woman. Everything from ‘chudis,’ mangalsutra, and ‘sindoor’ to toe rings. I bent down and touched Shekhar’s feet to take the blessings of my husband. He stopped me and pulled me back up.
He said, “Your place is in my heart, not at my feet.” He then proceeded to kiss my forehead. I hugged him in delight. We then bowed down before the photos of gods to seek their blessings. With the wedding ceremony over, it was time for the next event, the suhaagraat.
I asked Shekhar to wait in the master bedroom. I decorated it with lights, candles and flowers. I had spread rose petals all over the bed. While Shekhar went into the room, I went into the kitchen. I heated the milk mixed with dry fruit powder.
I walked to the bedroom with the glass of milk in hand. I stepped into the bedroom with my right foot first. I saw that Shekhar was lighting the candles. He had dimmed the lights in the room. I coyly walked up to Shekhar as he lit the last of the candles.
I looked at him from the corner of my eye like a shy bride and handed him the glass of milk. He took the glass and kept it aside. He said, “Let the milk be. All I want is you. I have waited for weeks looking forward to this moment, Ankita.”
Hearing him call me Ankita and express his desire for me filled my heart with euphoria. He lifted the dupatta from my face and asked me to look up. I obliged. Our eyes met. And as soon as I blinked, he pulled me close and started kissing me. I let go of my inhibitions and surrendered to my husband’s will.
I joined him in a passionate make-out session. He then turned me around and started feeling my body. He squeezed my boobs from behind me. He began kissing the back of my neck. I started enjoying it. I responded by grinding my ass against his crotch.
There was heat building up inside both of us. We both were expressing our repressed feelings. Shekhar whispered, “I want to make love to you, Ankita.” Hearing this, I got excited. I turned around and said, “Me too, Shekhar.” I then moved away and started to remove all my jewelry.
It took a good 10 minutes. Other than my ‘chudis,’ mangalsutra, engagement ring and toe ring, I removed every other article of jewelry. After removing them, I untied my hair and let it free. I then started undressing. I removed my blouse and lehenga and stood in my lingerie.
I then walked over to Shekhar and started undressing him. I kissed him over his body as I removed his sherwani and pajamas. I even pulled down his underwear. I was surprised to see that this time, Shekhar had completely removed his pubic hair.
He had spent time grooming his genitals for the night. I was happy that he had put in an effort for me. All the foreplay of kissing, grinding and stripping had already excited Shekhar’s penis. I picked up his cock and started stroking it. It then started growing in my hand.
Once it became fully erect and hard, I began licking and sucking it. I was caressing his balls and sucking his dick at the same time. Shekhar got excited by this and turned completely horny. He held my face and started deep-throating his penis into my mouth.
I took it in till I started to gag. I coughed a little and looked at his penis. It was completely lubed up. I then stood up and turned around. With my back to him, I seductively removed my panty. I asked him to pick up the Durex lube on the nightstand and use it. I spread my legs. He slowly pulled out the butt plug from my ass.
He then applied some of the lube on the entrance of my ass and started to massage it. Because of anal bleaching, the area around the anus was the same fair complexion. Once I was happy with the level of lubrication, I indicated to him that I was ready.
He slowly placed the tip of his penis at the entrance of my asshole. He started to push it in slowly. Little by little, his penis slid into my asshole. Once a third of his penis slid in, he started to pull out and push in. The in-out motion further spread my asshole, and his dick went in more easily.
Initially, it was a little painful, but I am always up for a little pain for pleasure. Once he got the hang of it, he started adding his hips into the in and out motion. He started thrusting his dick in and out of my asshole. I was finally having sex as a woman, albeit anal.
I began enjoying the sensation after the initial pain subsided. I was still wearing my bra to hold the silicone breast forms in place. Shekhar held on to them from behind and started squeezing them.
Along with the noise of our bodies clapping as he fucked me, there were moans from both of us. There was also the jiggle of my ‘chudis’ and my mangalsutra bouncing around on my breasts. We were enjoying the sensation of fucking and getting fucked.
At one point, Shekhar started hitting my P-spot. It sent magical shivers all over my body. We both were moaning and screaming each other’s names. I was jerking off my penis with my hands.
We continued in doggy style till we climaxed. Shekhar offloaded his jizz inside my asshole. When he pulled out his dick, his cum started to flow out of my asshole. I collected his cum and drank it. It was the nectar of my marriage. In this way, we solemnized our marriage.
After that intense session, we took a small break. Shekhar drank half of the milk and gave me the other half. We went once again after the break. Exhausted from the double stint, we caught our breath, cleaned up and ordered dinner. It arrived half an hour later, and we ate it in bed.
Satisfied with our exploits on our suhaagraat, we cuddled and got into bed at 1.30 am. Although we didn’t want to stop, we had to as Shekhar had to go to the office in the morning as it was Monday.
Next Part: Cross-dresser substitutes as Boss’s wife – Part 3