From Straight to Sissy: A Journey of Self-Discovery – Part-1

Hi everyone, let me tell you my story. My name is Kaushik. I work remotely for an MNC in Bangalore and am currently 28 years old. This is a story from my past about an incident that happened during a vacation when I was eighteen in my hometown of Udupi. I lived with my parents and cook, Santosh, as an only child.

My parents had hired Santosh to do the cooking and cleaning because both of them had jobs. six feet one inch, Santosh was a tall, muscular man. Santosh’s age was about 39 years.

One afternoon, during my holidays, I was watching TV with the cook. My parents were at work. I was on the couch and Santosh was on the floor beside me. Santosh began to massage my leg which was not unusual as Santosh often did so. However after some time Santosh’s hand moved to my thighs—a new and unsettling sensation.

After a few minutes Santosh startlingly asked, Where did you hide your cock? I was utterly blank frozen. Santosh wanted to see it. I flatly refused but somehow Santosh convinced me promising to only touch through my pants. To my embarrassment my cock began to harden. Noting this Santosh asked if Santosh could remove my pants and see it.

First, show me yours..I blurted out, a response I still do not fully understand. Santosh askedme, If I show you mine, will you show me yours? I was confused secretly confident Santosh would not agree. Yet Santosh led me to a room and revealed Santosh. It was my first time seeing another man’s cock; it was surprisingly thick.

Shocked I hesitated when Santosh asked to see mine. Santosh pressed, As you requested, I have shown you mine, now it is your turn. Unwillingly I complied. My erection fueled by fear had subsided. Santosh then made me promise to keep it a secret between us and I agreed.

Given it was my holidays, I often stayed up late. My parents who worked, went to bed early. One evening, the cook and I were watching TV as usual. Once my parents retired to their room Santosh sat close and began massaging my legs. Santosh’s hands soon ventured towards my inner thigh and then to my cock.

It became very hard. but he insisted he would only touch inside my shorts, without removing them. I remained silent… and it continued for a few minutes. As I neared climax I told Santosh to stop and pushed Santosh’s hands away preventing myself from coming. I was surprised by Santosh’s ability to bring me to that point with just two fingers.

This pattern continued for several days. Unknowingly I began to crave it intentionally sitting next to Santosh wanting Santosh to touch me. I recognized my growing addiction. One night Santosh started with a leg massage and within two minutes Santosh’s hand was on my cock fully arousing me.

Santosh then removed Santosh’s hand and asked if Santosh could remove my shorts. I initially refused but Santosh convinced me promising greater pleasure. Santosh removed my shorts revealing my rock-hard cock and began to stroke it while I lay half-naked.

Suddenly Santosh took my cock fully into Santosh’s mouth for about thirty seconds. It was a heavenly, first-time experience. Santosh told me to allow Santosh to do whatever Santosh wanted for more pleasure. At that time my knowledge of gay sex was very limited.

Santosh then stroked my cock so intensely that I cummed in twenty seconds having to push the cum out as Santosh held me so tightly. It landed on my thighs which Santosh cleaned with a tissue. Santosh then instructed me to come closer to Santosh in the future for more pleasure and I silently agreed.

Days passed and college started keeping me busy. My opportunities for fun with Santosh became rare. One day I had a half-day at college and came home early. When Santosh saw me I sensed a hunger in Santosh’s eyes mirroring my own desire for Santosh to stroke my cock hard.

After bathing and eating lunch I approached Santosh. Santosh smiled and suggested we go to Santosh’s room. I was okay with this. To my surprise and excitement Santosh lifted me onto Santosh’s shoulder and carried me. Inside I was filled with happiness and anticipation.

Santosh placed me on the bed and locked the door. Without any protest from me Santosh removed my top and pants. It was my first time being fully naked in front of anyone and my cock was rock hard. In the next moment Santosh removed Santosh’s own shirt and pants leaving Santosh in just Santosh’s boxers.

I felt a surge of fear. Santosh hugged me tightly professed Santosh’s love and began to kiss my face which made me uncomfortable. Santosh then laid me on the bed climbed on top and kissed my lips and neck for five minutes.

Santosh then pinched and sucked my nipples intensely as if Santosh had desired it for a long time. As Santosh resumed kissing my lips I felt Santosh’s body weight and became aroused. Santosh told me to remove Santosh’s boxer.

As I did I saw Santosh’s cock—five inches but very thick with large balls. Santosh told me to play with it. Shy and nervous I began to give Santosh a handjob. Santosh was visibly happy kissing my entire body and whispering dirty talk. When Santosh asked for a blowjob I instantly refused.

I continued the handjob and Santosh cummed on my stomach; the cum was thick and abundant almost covering my entire upper body. Santosh then gave me a strong handjob and I cummed within twenty seconds.

After we cleaned up our session was over for the day and I was utterly exhausted.

As the days passed my addiction to Santosh deepened. I found myself increasingly eager for our next encounter. I started learning more about gay sex watching videos and reading extensively diving deeper into this new world.

One late night unable to control myself I went to Santosh’s room and knocked. Santosh opened the door a smile on Santosh’s face and invited me in asking if my parents were asleep. Y

es, I replied. Santosh then playfully asked, Do not you have class tomorrow? I do, I answered shyly. Knowing full well why I was there Santosh continued, Then what brings you here so late? I remained silent.

Santosh then told me to lock the door and come in which I did. Santosh began to touch my cock repeating Santosh’s question about why I was there at such an hour. My cock hardened and my face burned with shyness.

Santosh smiled gave me a soft kiss and said, I know why you are here. Santosh had me stand in front of Santosh as Santosh sat on the bed and instructed me to strip.

I removed my pants t-shirt and underwear then sat on Santosh’s lap. Santosh began to ask me dirty questions: Are you enjoying this very much? How was the last time? Was it pleasurable for you? As I told you before.. do as I say, and you will get even more pleasure. Will you agree to that? I said Okay.

Santosh then told me to kiss Santosh which I did very slowly. Next Santosh asked me to remove Santosh’s t-shirt. Obediently I knelt down as Santosh stood half-naked and I removed Santosh’s pants. I could see Santosh’s cock pressing against Santosh’s boxer briefs and I could not resist touching it. Finally I did.

Santosh told me to kiss Santosh’s cock through Santosh’s boxer and then to remove them. Santosh’s large, thick cock with its huge, hanging balls popped out towards my face. Santosh told me to kiss the tip and then I opened my mouth wide. I could not fully take Santosh’s thick cock in my mouth—it was my first time.

I gave Santosh a blowjob for two to three minutes. Santosh was clearly happy with my effort hugging me tightly kissing my lips and spanking my ass until it was red. Santosh then told me Santosh wanted to fuck me and I agreed. Santosh wanted to proceed without a condom.

Noting that my hole was very tight, Santosh got oil and began to massage my anal area. Slowly, Santosh inserted one finger and after a few minutes I felt a second finger sliding in. It started to burn intensely inside and I immediately stopped Santosh. I had not realized it would hurt so much.

Santosh did not force me but instead asked for another blowjob. As I gave it to Santosh I could feel Santosh’s pre-cum in my mouth. Santosh then told me to lie down on the bed and proceeded to face-fuck me. After about five minutes I felt a hot blast of Santosh’s thick cum erupting into my mouth. I immediately spat it out covering my body.

I was so embarrassed. After washing my mouth I lay back on the bed waiting for Santosh to stroke my cock and make me cum. Instead Santosh told me Sleep naked with me tonight. I will not make you cum today; if I do, you will just go back to your room. Sleep with me as much as possible. Santosh then cuddled me and we drifted off to sleep.

I was incredibly horny and wanted to make out. The next morning Santosh told me to wake up before my parents did but I could not find the clothes I had taken off the night before. When I asked Santosh Santosh countered, Tell me honestly, how did it feel to suck my cock? I remained silent.

If you want your clothes, then tell me, Santosh urged, pulling me to sit beside Santosh and beginning to rub my back. Santosh pressed again, Did you like my cock? Do you like the taste of cum? My cock started to harden and with class looming I just blurted out, Yes, I like sucking your cock.

Santosh laughed, then said, Give me a blowjob, and I will give you your clothes. I knelt down while Santosh sat on the edge of the bed and began the blowjob. I noticed Santosh’s cock growing in my mouth, my saliva dripping down Santosh’s balls as I tried to take Santosh fully, sucking Santosh’s balls one by one.

Santosh seemed surprised, saying, You are doing it amazingly. Now I can see your love for my cock. Santosh revealed Santosh had not stroked my cock or intended to cum, wanting to witness my lustful play. After ten minutes, Santosh released Santosh’s load onto my face and made me continue sucking for another two minutes, with Santosh’s cum still on my face.

Santosh then led me to the mirror, showing me my reflection. See, Santosh said, you are looking so beautiful with my cum. Santosh then made me promise not to masturbate, which I did, and Santosh finally gave me my clothes.

It all began with Santosh giving me handjobs, and now it had evolved into me giving Santosh blowjobs, becoming addicted to Santosh’s cock, and finding pleasure in pleasing Santosh. Since I had stopped masturbating, I was constantly horny. Santosh seemed to sense this, often giving me naughty smiles even when my parents were around.

For the next few days, I found myself slipping into Santosh’s room after my parents were asleep, solely to give Santosh pleasure. I began to discover a new kind of pleasure in pleasing Santosh. My addiction to Santosh’s cock grew so intense that while watching porn videos, I started imagining myself as a girl, sucking those cocks. It had been over two or three weeks since I had cum.

My parents had a function to attend in another city on Sunday and were leaving Saturday morning. Since I had a college fest that Saturday, I had to drop my plans to go with them. Secretly, I was also anticipating having fun with my cook. Saturday finally arrived. My parents left for the airport and I began getting ready for college.

As I was leaving, my cook told me Santosh would be waiting, suggesting we have fun tonight since tomorrow was Sunday. I was incredibly excited. The college fest ran a bit late and I reached home around 10 PM. Santosh served me dinner and then instructed me to shower, shave my entire body, and come to Santosh’s room.

I agreed without hesitation. I was incredibly horny, having not cum for weeks. After showering, I walked towards Santosh’s room and noticed Santosh had just bathed as well, dressed only in Santosh’s boxer briefs. Seeing me, Santosh told me to remove my clothes and come closer. I went to Santosh hugging Santosh tightly.

My body was completely shaven—my legs, arms, and skin felt incredibly fair and smoothly soft, like milk. Santosh began to embrace my body.. complimenting my smoothness as Santosh’s hands explored every part of me.. my inner thighs, legs, and even my chest, squeezing it hard while I, in turn, clutched Santosh’s cock inside Santosh’s boxers.

Santosh grabbed my ass pulled me onto the bed and climbed on top of me, kissing my lips fiercely. I could feel Santosh’s tongue fully exploring my mouth. Our saliva mingling, which turned me on even more. Santosh pinched my nipples and began to bite my neck as if Santosh wanted to devour it.

Santosh’s tongue then started to dig into my navel, a sensation that felt incredibly good. Santosh made me lie on Santosh’s lap and spanked my ass. Later, Santosh told me to get on top of Santosh and kiss Santosh. I started with a kiss, which deepened into a passionate smooch.

I sucked Santosh’s nipples, moved down, removed Santosh’s boxers, and began stroking Santosh’s cock while still kissing Santosh. Then I went lower and started sucking Santosh’s thick cock like a slut. After ten minutes of blowjob, Santosh turned off the light, continued to kiss me, and told me to stroke Santosh’s cock.

This continued for another fifteen minutes before Santosh asked, How bad do you want my cock? How much more slutty can you become for me? Santosh squeezed my ass. I was in pure heaven, literally moaning like a girl. Santosh then had me turn over and lie on my stomach, spreading my ass cheeks with both hands, and began licking my hole.

Santosh’s tongue went inside, a heavenly feeling that made me moan even louder. I heard Santosh open a tube, and though the light was off, I could not see what it was. Santosh applied something cool to my hole. When I asked what it was, Santosh shushed me.

Then Santosh started inserting Santosh’s finger into my hole, slowly managing to insert three fingers. This time, it did not hurt, perhaps because of the gel. After some time, Santosh removed Santosh’s fingers. I heard Santosh open the tube again, applying more to my hole. I expected Santosh’s finger, but instead, Santosh inserted Santosh’s cock.

I could feel Santosh’s cock slowly drilling into my hole, like it was about to tear. The head of Santosh’s cock finally went inside. I felt helpless; Santosh was well-built and held me tightly, reassuring me, It will be alright, just two more minutes, it will feel good for you.

Tears rolled down my face as Santosh pushed, and Santosh’s cock went fully inside me, filling my ass completely. I could feel my own dick starting to lose its erection, becoming limp and shrinking, as it was hurting. Santosh kept Santosh’s cock inside for a couple of minutes before Santosh began to pound my ass.

While kissing the back of my neck, Santosh whispered, You are not a virgin anymore. With that, Santosh started to fuck me with harder strokes. Then Santosh removed Santosh’s cock from my hole; my ass felt empty inside and ached for about five minutes.

Santosh told me to clean my ass and said we would do it again. Santosh turned on the lights, saw my limp dick, and smiled, asking, What happened to it? Maybe it is not useful anymore.

After about ten minutes, Santosh told me to get into doggy style. Santosh applied gel and slid Santosh’s cock inside my hole, then removed it again, repeating this several times. Then Santosh said, Now your hole is completely ready to be fucked like a girl. With that, Santosh started to fuck, and I began to enjoy it, moaning loudly.

Santosh’s cock went deep inside my ass. Santosh fucked me in doggy style for ten minutes. Then Santosh came on top of me and started with missionary style. With each stroke, I could feel my limp dick jumping. It was like a guy fucking a girl with a dick. My dick had shrunk so much it almost disappeared.

Santosh fucked me with different variations, and I could feel different sensations in my limp, numb dick. When Santosh increased the speed, my limp dick unexpectedly burst with orgasm. I was shocked to see it. I had not even touched my dick..yet I cummed. The cum was all over my stomach and it felt incredibly good. Santosh laughed and told me, This is why I told you not to masturbate for weeks. See how horny and slutty you have become, getting fucked like a girl. You are a girl now. You need to cum like this for me, good girl. Santosh fucked even harder, kissing me, and released Santosh’s load inside my ass. I could feel Santosh’s shots inside me. When Santosh removed Santosh’s cock, Santosh’s cum was dripping from my hole. I was truly in shock and could not accept what Santosh had just told me—that I was a girl.