From Straight to Sissy: A Journey of Self-Discovery – Part 4

One day, After returning from college, Mahesh handed me a bra and panty, a wig and simply said: Kritika, wear these and come for tea. I did exactly as told, even applying some makeup. After tea, he took me to his room. We sat for a while and then he asked how I felt when he had stroked my dick and made me cum. I confessed: I did not feel good. He pressed: Then how do you want to cum, Kritika? In my mind, I craved only the sissygasm, cumming solely when getting fucked, but I remained silent, full of shyness. He asked again: Tell me, Kritika. Finally, I admitted: I only want to get a sissygasm; I do not want to cum like a boy. I saw a happy smile spread across his face. At that moment, I could feel myself becoming a truly submissive sissy girl and I was completely loving this new life. He removed my dick from the cage, explaining: I am removing it because I am confident you will not be cumming like a boy anymore. You will only leak when getting fucked. When the cage came off, I saw my limp dick., it was so soft and tiny. He made me stand in front of the mirror, hugging me from behind. Look at you, Kritika, he whispered.. you have turned so sexy, just like a girl with soft, milky skin and a lovely ass. He told me to examine my entire body. He then told me to put my panty back on, so I was just in a bra and panty. He took out his mobile and started taking pictures of me in different poses, even making me kneel with my tongue out, as if waiting for a cock in my mouth. He took many pictures in that pose. Then Mahesh removed his cock, placed it on my tongue and clicked another picture. I started to suck his cock. He told me he wanted to record it and being totally horny, I agreed. This went on for about ten minutes, during which I also started sucking his balls. Later, he told me to open my mouth wide; he wanted to cum inside my mouth. His hot, thick juice started flowing into my mouth and he instructed me to show the cum in my mouth to the camera before swallowing it, which I did happily.

Days passed, and whenever my parents were at work, I would be in girl’s clothes. Mahesh continued to take my pictures in different dresses. I quickly became more comfortable in girl’s attire. Since I was not an outgoing person, I had a limited number of friends whom I spoke to only occasionally and I also avoided attending functions. This routine continued for many days.

During my Master’s degree, before the semester officially began, I had to complete an internship.. This required me to travel to Bangalore where I stayed at my aunt’s place for three weeks. During those three weeks, I missed Mahesh terribly—his humiliation and the way he used to fuck me. I did not dress as a girl during this time,, but my urges only increased.. I missed the feeling of cock in my mouth and ass and I could feel my asshole starting to tighten from not being fucked for so many days. Finally, it was time to return home after completing my internship in Bangalore. I was overjoyed because I had no classes for the next four weeks, only needing to prepare my internship report.. The day before my return, my mom called me, casually mentioning something she had forgotten to inform me about: Santosh was coming to Udupi and had called to see us. She told him that I would be reaching home that day and that they were traveling to Mumbai. I told him he could stay at our place, she added. Hearing this,,my inner self erupted with joy; I could already imagine myself sucking two cocks at the same time. The next morning, my parents left the house and my flight was also scheduled for that morning

I reached home in the afternoon and was welcomed by Mahesh and Santosh. We had a casual chat and then I headed to my room, buzzing with excitement for today’s fun. After we had lunch, Mahesh leaned in and told me he missed my ass and wanted to fuck it.. He instructed me to stay dressed as a girl until my parents returned. I took a shower, applied makeup and put on a yellow bra and panty set with a transparent yellow babydoll dress and a wig.

When I went to the hall, Mahesh was waiting. Where is Santosh, I asked. He is in the room, waiting for you, Kritika, he replied, grabbing my waist and leading me there.

As I entered, I saw Santosh engrossed in his mobile. Mahesh made me sit between them. I then noticed Santosh was looking at pictures of me in girl’s clothes and even videos of me giving a blowjob—pics Mahesh had taken long ago. Santosh looked up, his gaze intense. Seeing those pictures and videos, you have become quite the slut now, he commented, putting his phone aside and starting to touch my inner thigh. As I was sandwiched between them, Santosh began recounting how I had avoided him since he and Mahesh had first fucked my asshole, and then how I had later come begging to his room for his cock. They both laughed at me, and inside, I was enjoying every bit of it.

I began stroking both of their cocks in my hands. They pulled off my babydoll and I knelt before them. I unzipped their pants and pulled down their boxers, revealing two hard, pulsing cocks right in front of me. I took Santosh’s cock first, sensing his moan as it went deep into my mouth. Then I took Mahesh’s cock. I sucked their balls as well and it felt truly good.

After about fifteen minutes, they removed my babydoll dress, bra and panties, leaving me completely naked. Santosh could not resist my milky-smooth, soft body. Because I had gained a little fat around my waist and chest, he grabbed my ass and began to squeeze it. Mahesh hugged me from behind and Santosh embraced me from the front. I could feel Mahesh’s cock pressing against my ass cheeks and Santosh’s cock resting just above my limp dick. They both started to kiss my body all over and I could feel different sensations taking over. I was losing control. I started to stroke both of their cocks simultaneously.

They led me to the bed and made me lie down. Santosh commented on my limp dick, saying, Your dick is so soft. He then started to kiss my lips while Mahesh began sucking my nipples. I continued to suck Santosh’s cock while Mahesh applied gel to my hole and slowly pushed his cock inside. Being fucked while giving a blowjob was truly heavenly.

Mahesh then instructed me to straddle him. I began riding his cock like a sissy girl, moaning loudly with every movement. Then it was Santosh’s turn. He fucked me in missionary for about fifteen minutes; his balls slapped against my ass crack and it felt incredibly good to be fucked after so long. His tongue plunged deep into my mouth and I kissed him back, savoring the feeling of his cock burying deep inside me and his saliva coating my face, while Mahesh enjoyed watching us. Turn by turn, they both fucked me really good. It went on for hours until both burst their loads into my mouth, which I swallowed. Exhausted, I collapsed onto the bed. I remained naked all day and whenever they desired, I would give them a blowjob, fully embracing my role as their submissive sissy.. This pattern continued for two days.

The next day, Mahesh told me to get ready and dress the best I could. I assumed they were just going to fuck me as usual but they had another plan. I dressed as pretty as I could in a sexy short dress which revealed my thighs and ass cheeks, highlighting my milky-soft waist and legs. Mahesh told me to wait five minutes. He then took a call, seemingly guiding someone to our location. I wondered if some groceries were being delivered.

Are you ready for today’s fun? Santosh asked and I smiled at him like a girl. Suddenly,.. I heard a car pulling up to the house. Assuming it was a relative, I tried to rush to my room to change,, but Mahesh stopped me. Moments later, the doorbell rang. Santosh opened the door, revealing an uncle, around 50,, accompanied by a sissy girl just like me. I was utterly shocked.

Both came in. Mahesh introduced me to the uncle. This is Kritika; she is all yours today. I was stunned to hear this. The uncle was unattractive, with a big stomach and a very fat build. He smiled at me and introduced his sissy to Mahesh as Shreya, telling Shreya to go to Mahesh. She complied, and Mahesh immediately held her close like a lover,, which made me feel a pang of jealousy. Mahesh then pushed me towards the fatty uncle. He grabbed my waist tightly and murmured,. You are beautiful, Kritika. I felt uncomfortable.

Shreya then excused herself to go to the washroom. Mahesh told me to take her to my room while he and Santosh conversed in the hall. Did you know about this plan? I asked Shreya. Yes, she replied, he is my fat relative, and he turned me into his girl. She then recounted her story of how she became a sissy. It was not the first time Uncle was exchanging her for another girl; she had had sex with many men, she told me. I became very curious.

She explained that she came to Uncle’s place during her PU college days. One day, when no one else was home, Uncle took advantage. He used to show her porn videos, and one day, he made her suck his cock. It took one suck for me to get addicted, she confessed. Then I could not return to myself. I told her it was the same for me. I sucked once and then started to crave more and more for cock. After I got fucked, it was like my manhood had been washed away from me forever. I expressed that there seemed to be no return from this path, and she readily agreed.

She then asked if both Santosh and Mahesh were going to fuck her. Yes, I told her, they are both really good; they will make you happy. I then asked her about the uncle. She shuddered. He is like a wild, hungry animal. He will eat you alive today. I felt a bit scared as we headed back to the hall.

We then headed towards the living room. Seeing me and Shreya, Mahesh told me to go and sit with the uncle, while he grabbed Shreya. Santosh’s gaze was fixed on Shreya’s body. Mahesh then instructed me to show the uncle my room, and they took Shreya to their room.

I led the uncle, Kishore, to my room. As we entered, he immediately began kissing my lips, his saliva coating them. He made me sit on the bed and started to smooch me again. He was quite fat, and when he told me to lie down and came on top of me, I could barely breathe. He continued to kiss me, complimenting my lips by saying they were more juicy than a girl’s.

He then undressed, pulling off his shirt and pants, leaving him in his boxers. He moved towards me and started removing my clothes until I was just in my bra and panty. He turned me over and began to squeeze my ass, spanking it so hard that it turned red within seconds. He came back on top of me, kissing all over my body, admiring my girly waist and belly. I was moaning like a girl, Ahhh…He removed my bra and started to suck and bite my nipples, which felt really good. His saliva was all over my upper body. He moved down, removed my panty, and began kissing my inner thighs. He then turned me, spread my ass, and started to lick my asshole. I was in heaven now. This continued for a few minutes before he lay down.

I climbed on top of him, sucked his nipples, and removed his boxers. There it was: a thick, fat monster of a cock. It was not too big in length but incredibly thick. This was the fourth different cock I was about to taste. I started at the base with my tongue and worked my way to the tip, kissing the tip again. Precum stuck to my lips as I slowly took his cock into my mouth. I noticed Kishore beginning to enjoy it, so I used more saliva for his greater pleasure and sucked his balls as well. After about ten minutes of sucking his cock, he told me he wanted to fuck me.

Quickly, I raised my leg and the fun began. He slowly pushed his cock inside my hole. Ahhh, I moaned, feeling true pleasure. He started to fuck even harder and began to smooch me. He fucked me in doggy style as well, his cock hitting me deep inside while my limp dick and balls jumped back and forth with each thrust.

Suddenly, Mahesh and Santosh entered my room with Shreya. They told us to kiss each other. It was my first time kissing a sissy and it felt like a lesbian encounter. We exchanged a slow,.. deep kiss while grabbing each other’s asses. Even her dick was limp. We hugged each other tightly, like girls, while Santosh, Mahesh, and Kishore watched,..enjoying the show. They made us go to bed, where we had a little more fun, sucking each other’s nipples and smooching with a lot of tongue.

Later, they told us to kneel on the floor. All three cocks were right in front of our faces. We took turns sucking them. Soon after, they all burst their hot, copious cum loads onto both of our faces. Then they told us to lick the cum from each other’s faces and swallow it. We exchanged cum while kissing, an entirely new experience for me.

I took Shreya with me to the bathroom and we decided to shower together. I asked her how our threesome was, and she said it was “really good.” She agreed that “getting fucked while giving a blowjob is the best thing.” As we headed for the shower, I washed her breasts with body wash gel and started to squeeze them from behind. We kissed each other under the shower and she even inserted her finger inside my hole while kissing. We had quick fun in the shower, like a lesbian encounter.

Afterward, Shreya and Kishore left. I knew this wasn’t going to end here; I would be shared with many more guys. I was scared and excited at the same time..

Mahesh told me he was really proud of me and promised more happiness and surprises…Deep down, I wondered how this sissy life would continue and if I would ever be able to return to normal after all these encounters. Yet,..at the same time, I felt a deep satisfaction with everything. It was a mix of feelings, but deep down, it felt like I was meant to be a sissy.

Kritika’s life transformed as she embraced her new sissy identity, finding profound satisfaction and a sense of belonging in the submissive and shared sexual experiences that became her reality. Though initially unexpected, this path brought her an undeniable, deep-seated contentment, solidifying her feeling that she was meant to live this way.