My life story and how I became a sissy and how I was feminised . This story has femdom, gay, sissyfication
I am not gay, but…
When I was in college, I was studying science and preparing for the exams. It was a stressful time. The majority of the day I used to be at my coaching classes, and my whole day used to be gone studying there. I had some girls in my class, but I was never hit upon as I had many bad boys in my class who were already banging every chick. I was a virgin listening to them and getting hard.
It was very regular for me to masturbate in my class’ washroom. I usually went in and sat on the toilet masturbating and imagining about the girls in my class. It was a great feeling as if it relieved my stress and got me some peace there, but one day, one of my classmates came in, and I thought he was peeing, so I stopped rubbing hard and instead just held my dick to keep it hard till he went away. I heard him finish, and in a second, he busted open the door of the toilet I was sitting on. It was the most bizarre situation I had ever been in. He was fortunately sporty about it and just closed the door as quickly as possible. I was so embarrassed, and when he opened the door, I made the most girly noise I have ever made in my entire life.
He ran out, and I quickly pulled up my pants and went into my class as well. It just made my dick soft, and it wasn’t getting erected any time soon. I changed my seat and sat beside him. I asked him why he opened the door, and he said it wasn’t locked, so he thought it wasn’t occupied, and there was not even any noise to make him think there was someone in there.
He apologized and kind of joked about me masturbating, but I tried to turn it around and say that I was just grabbing my dick and not masturbating. It was in vain, and he revealed that anyone could see what was going on inside that toilet if you stood in the corner of the door. It had a gap about the size of my nail, and I was aware of it, but it wasn’t that big of a deal. I had no option but to accept that he had caught me.
From that day on, I had to become his friend and be a bit more fond of him. We got more comfortable around each other, and then one day we went to the toilet together. We had three urinals, but one was broken, so we were standing next to each other. I saw his 4-inch penis as he opened his pants, and I took out my 4-inch, fully-hard one. I had no control over the erection; whenever I enter that toilet, it automatically gets erected. He saw that and giggled and asked, “You like the girls in our class?” I said no, and he then said that each and every girl has a boyfriend, and if you prey on anyone, you will be in trouble. I felt like what I had done could get me into more trouble than I ever imagined. He shakes his dick after peeing, and I see it get erect. It became twice its size, 8 inches. I was in disbelief, but I knew it was possible, but not with him.
He saw my reaction to seeing him get hard, and my face said it all. He asked if it was too big, and I said yes, it kind of is. He showed me his girl, who isn’t from our coaching class. He showed me her photo and said that her GF was I kept getting shocked again and again. I am in the same college as her; she is so beautiful and lovely that she can be compared to and even become a Marathi actress. She has lighter skin, big assets, and a great face. She’s one perfect girl; she talks very cutely as well as very politely. I asked him how he got this girl, and he said it was simple: he messaged her on Instagram and she replied, so this messaging went on for some months until it was fine enough to drop some dick pics, it was enough for her to melt down and send her nudes as well, and they then met. (All are 18+, by the way.)
I was so pissed off that that girl never replied to me. I have created thousands of IDs and messaged her; I have talked to her in real life, and she has never talked to me. He asked me how is she and I rated her 90 out of 10 . It is what it is, and I can’t lie—he got a real piece of meat there. I would never have believed she even lives in the same city as me because of her beauty if I had never seen her. I was hard, and he was hard; he took his phone and then swiped some times and started masturbating by looking at the phone. I was just standing there awkwardly. I was just zipping my pants, and he asked me if I was not masturbating.
I said no, and it’s weird; he called me closer and showed me his phone; there were some nudes, and he said, “See this and masturbate.” No one comes in the washroom at this time. She was naked. But there wasn’t her face; he zoomed in so I couldn’t see. He told me it’s a secret, and if it leaks, then it will be a lot of trouble for me. I got so horny, I just pulled my 4-inch screen out, and we both were masturbating while looking at his phone. She had some tight, C-size boobs. Her pussy had bushes around it, making it hard to notice her clitoral area. The v-shaped bush made me leak.
I came all over and he was still masturbating; he laughed and saw me holding my penis. I usually masturbate with 2 fingers; I don’t get enough grip if I hold it and grab it with my full palm. He said that’s too small, bro, and laughed. He asked, “Can he take a picture of my penis?” and I said yes, I was too horny, but it wasn’t a big deal as he just took a picture of my penis; I had enough privacy there.
He showed me that he sent that picture to her, and she instantly came online and sent some laughing emoji. I was humiliated on the spot. He told me to wait until he finished and told me I could stand at the entrance. I heard him; he started a video call, and then, in about 15 minutes, he was over. He knew I could listen, so he turned the volume down. It was her only, and I was so horny because she was so free with him, and she was replying. I guess they both masturbated together on the call, and then he came and cut the call. He said just a minute. He put some water on the urinal, and then we went out. It was a very bizarre moment in my life. I never saw anyone else so dumb in my life.
After that, we usually had these masturbating sessions, about once every two weeks or so, based on his mood. Once, we had a bet that our teacher had been divorced; I said she was not, and he said she was. This was a small argument that turned into some important conversations. He said, “Agar wo divorced nikli to mai teri gand mar lunga.” (This means that if she is divorced, then he will fuck me in the ass.) It’s very common and funny to hear in Hindi or Marathi, but isn’t very practical and used as a joke. So I said if she isn’t, then I will fuck his ass. He said deal, and the next few days, he got a bit free with this teacher and had a good conversation with her when she wasn’t teaching.
He turned his face and gave a big, naughty smile. I knew I was wrong then. He came back and sat next to me and revealed that he was right and she had a divorce. He said nothing after that, and I guess he just forgot about it. That same day, we went in the washroom, and when we were peeing, he asked me to get in the toilet and take my pants off. I was shocked and asked why; he said it was a bet, and I said nope. He said, “At least show me your asshole then.” After 15 minutes of convincing, I agreed and bent over, took my pants off, and he made me get into a yoga pose.
He wanted me to bend over while standing and push my dick backwards so it was between my legs from behind, and he wanted me to join my legs and keep it like that. I did as he said, and it took me a minute, but I managed to do it right, and he took a few pictures of it. He grabbed my dick with his two fingers and then masturbated me. I told him to stop, and he asked, “Really?” I said no, and he continued, and it took me 10 seconds to finish. He saw my asshole clinching as I shot my cum on the washroom floor as well as my pants.
He licked his finger, which was clean, and tried pushing it into my asshole. I said no, and he said to please try it once, and he will give me a video of her GF getting naked, and she will know that he gave me one. I have never been so horny after just hearing her name. I stayed silent, and he spat on my asshole and asked me to stay in the same position and not move. I turned, and I was keeping an eye on the entrance. He slowly started to push his finger. It went in, and after about 1 inch, it hurt a lot. But as he pushed it deeper, it felt good.
He slowly started to finger me and fuck me, but I was about to spit, so he pushed his three fingers as deep as possible, and he said to move and get into the toilet before I spit myself. He kept his fingers in, and as soon as I squatted, he pulled them out, and then I saw that he had a glove. I don’t even remember him getting a glove on and pushing two more fingers. It all was happening, and I was enjoying it so much that I didn’t even notice it.
He saw my dick and said how much I came while getting fingered. I was in another world; I just pushed out the biggest load, and in one push, it was all out. It was the easiest break I have ever had in my life, unironically. I washed my asshole, and he was standing outside. I opened the door, and he came in and said to pull my pants down again, and this time I did it as soon as he said it. He bends me over, and then he puts his hands on my back. I knew I would be having anal sex now. I had a condom on, and he spat at my asshole again and again and tried to push it in. It went in, and all he could do was push it up against his head. It was plugged. He told me not to squeeze my asshole and just leave it loose. I let it loose and tried my best. He started to slowly push it, and I was experiencing some intense pain as well as pleasure. It was unimaginable how enjoyable it was for me. He gave a few thrusts, he fucked me, and harder and harder for it felt like infinity. I lost track of time. I don’t know about him, but I came about three times, and my back was in pain. I had some pain in my balls as well due to continuously cumulating. His bass were slapping again at my balls, and I was looking at my dick hanging in between my legs and having a long thread like cum leaking from it. I then had my legs together and pushed my dick to the back side, and this time I noticed. It looks like a pussy from the front if I push my dick behind and clinch my legs. And after he came, he pulled it out, and it made a plop sound.
He pulled his condom out and tied a knot in it. He pushed the condom in my asshole and kept the knot outside, and it acted as a plug. He was absolutely amazing at fucking; the warmth of his dick, the deep thrusts, the throbbing, and the orgasms I had were unreal. It was the experience of a lifetime. I felt like being a girl.
He helped me and pulled up my pants; he cleaned up my pants from the outside, but because of my position, I was continuously cupping in my own underwear. It was wet and sticky. He made sure I was looking normal and, mainly, if I was able to walk. It was hard; I was unable to walk. It had a high intensity, and I was suffering a lot because of it. My asshole was burning, and we told someone outside the washroom, and he made a call. He then took his bike and went and got a pill. I don’t know what pill it was, but I felt like it was a painkiller and took it. He then took me into the class; we had to be there for about an hour, and it was so long to sit with something inside our asses.
The burning almost ended, and my only problems were the condom and the wet pants. My underwear was fully drenched, and I wasn’t getting soft. My dick was hard for the whole time. My mind was constantly thinking about my hole. He helped me out while I was going out, and he told everyone that I hurt my leg and that’s why I was walking like that. He made sure I was able to drive myself home, and then I went home. I slowly walked in, and all I did was go into my room and sleep. That was my first priority, and after having a nap, I got up and almost forgot about the condom in my asshole. I woke up and changed my underwear, and I washed myself as well as the underwear. I have never done that, but I didn’t want my mom to be suspicious.
I remember my condom while washing that and feeling like it deserves to be in me for some time. I was still half-erect after that incident, and I started masturbating while playing with the condom. I was pulling it out and pushing it in, and I saw how my asshole just pulled it in automatically. It was in harmony and gave me the intended peace and pleasure. The relief of stress and the enjoyment were still on top, and I was happy that I had lost my anal virginity at least. My dick was useless, but I felt good that I had some painful sexual intercourse at that age.
That night, he sent me some links. He posted them on Reddit, and the name of the subreddit was sissyhumiliation or something similar to it. I opened it and saw my pictures. I was looking cute and very feminine. At first, there were 3 pictures: before he masturbated me, and just my asshole with my dick below it. Next was my dick leaking cum, and the third one was the picture where he masturbated me and I was cumming; it was a gif of me shooting cum. He also said that his girlfriend liked it as well. And he sent me a video of her masturbating. And the camera turns, and she is watching a video of me getting fucked in the toilet. It’s just my lower part of the body, and it was really hot to see that.
After he sent another link, it was my video on some underrated site, and he was fucking me. Most of the background was blurred, and even the back of my head and my back were all blurred and cut out.
I was still scared if someone recognized me, but he made sure I was fully hidden. From that day on, we regularly had anal sex, and he usually started to fuck me raw if I had washed it from the inside as well. If I haven’t, then he usually crawls on my asshole and never pushes or touches it. He masturbated on my asshole, cummed, and then pushed it in with a pen or anything.
Cumming on my asshole was a daily thing, and it actually kept me fresh, and I became a sissy after that. I loved to watch sissy porn after I researched what that was, and I became a sissy myself. He made me one and kept me as a sissy between us. It boosted my studies, and I was able to concentrate more as I had no use for my dick other than peeing.
All it took was the thought of him fucking me, and I was cuddling without even touching myself. I was controlling my orgasms with my thoughts. My asshole was now connected to my dick, and I was cuddling whenever he entered me. My life was filled with pleasure, and he got a job; even I got a job, and he then got promoted to a good place and post. He managed to keep me with him somehow, and we were at the same office. I was grateful as the job salary was more than that of before, and I was with him in the new job. I was meeting him daily, and we had a spot in the parking lot where he usually creampied me every day.
His girlfriend was also involved, and after a year, when they got married, I was also a part of their marriage, and I was taken on their honeymoon secretly. I told my parents that I was going on a solo trip, and we then went with him. His wife was now more feminized; she was controlling me and making me do stuff like lick his dick and drink her piss whenever she needed to pee.
And she bought a strap just to fuck me whenever she wanted; it was an inch longer than his and girthier. My daughter also had chastity at that point. I had no need of my dick at that point, and I felt like it had no point as I was not masturbating in the first place. For the first month, I was in absolute pain; it was unbearable. At night, randomly, it started to hurt whenever I got anal sex; I was getting erect and it was causing pain; whenever I was outside, while sitting, it was so painful. On the first day, I felt like throwing it, but I still kept it and made a decision to try it for at least 1 month. It was challenging because I had to fight the urge to get erect. I had to be a true sissy. I didn’t need to have my sexual thoughts in my mind. And soon enough, I was cupping without getting erected. It was magical because I haven’t experienced anything like that.
It was something that I got addicted to, and I never knew I was able to do that. His wife asked me if I wanted to remove it, and I felt like I should take it to the next level and keep it on for 3 months. And I rented out a room next to their house, and they provided me with the rent for a month, and the next month they took me into their house, and we lived together; I was their bitch. I ate food off the floor. I licked the floor; she started peeing on the floor wherever she was in the house, and she called me to lick it clean. We were on another level of bdsm, humiliation, and stared with bondage.
And in the condo, I lived with them only, and it was the most entertaining thing. We enjoyed trying something new every day, something hardcore, pushing myself to my limits, and at that point I was even ready to eat shit from their asses. I am so loyal to them, and I am grateful for the pleasure they provide.
After the covid slowly started to stop, his wife ordered thousands of rupees’ worth of sex toys. 2 vibrators, remotely controlled, one more strap on, 4 butt plugs of different sizes for me and 1 for her as well, and a new chastity cage for me It was of perfect length and all, and the last thing was clothes. She ordered so many clothes of my size, and all were female clothes with undergarments.
She spent a lot on me, and I felt grateful for that. I opened the box of chastity and felt like it was too far and would be too much. It had a pipe that went into my penis itself. I was thinking it would be harmful and could cause some problems. She gave me my phone, and I read some articles. It took me a week to finally agree, and after months, my virginity was finally unlocked. It was so fresh, but it smelled really bad. She cleaned it for me, and while she touched me, I came immediately.
She put the lube on and did all the procedures correctly; she also put lube on my dick, and my dick was fully covered with a layer of lube. She pushed the pipe slowly inside my penis hole, where I pee. As it started to go in, I felt a sudden urge to cough. I was quivering; she pushed it in, and I had a plug. Suddenly, pee started coming out; it was directly on her face, and she bit down on the bolt on it and then continued with an angry face. I wanted to laugh, but she would feel bad then. She then put the chastity, and it was done and locked. She then slid aside and opened the bolt. I started peeing again, and after I was done, she shook it and said it was done. I was now able to control my pee, but it was very difficult. She got me in doggy and fingered my ass to see if I was able to cum, and sure enough, after 10 seconds, I was in pain but I was able to cum. It was cumulating in drops and was slow, so it was creating pain and wasn’t shooting out the cum.
I cleaned the floor and thanked her for getting it and putting it on as well. I washed her in the shower. The whole lockdown was spent with that chastity, but after it was over, she changed it and gave me the older one back. I had to have a butt plug at the office. I had to take one picture daily to prove I was wearing one.
We were planning that I should get married to someone and add another girl to our group, but I feel like it’s difficult to find a girl who will see this lifestyle of mine and marry me. My parents are finding a girl, and soon, in a month, I will be getting married. I am writing this in the spare time I am getting because of the traditions and all the other things. It will be hard for her, but I guess she will love it when she finds out. I don’t feel she is sexually active or ever was. But if she is, then my friend is there to get her laid, and I will be living with them only, and I will be acting to pay rent so nobody suspects. I feel like his wife will get my wife to be the same as her, but we don’t know the future.
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