Spoiler
This is a story that I've written in Spanish, and then translated to English, probably with many mistakes, but hopely it can be understood. It's called "How I was feminized by a man":
I met Roberto at a gay night club. He was a lot bigger than me, but you could tell he was very active, and he had a well-built body, which I found attractive from the start. I was 18 years old, and I still had doubts about my sexual preferences, since at that age I had had sexual experiences with a girl and a boy. Roberto invited me to have a drink, told me about him, asked me about my life, and we had a great time talking about different topics. At one point in the conversation, he asked me if I had any fantasies. I said no, and asked him if he had any. He told me that he had the fantasy of feminizing a teenager my age and making him his lover. I think I blushed at the time, and Roberto must have noticed, because he changed the subject. Later we said goodbye, and he asked for my phone number. I preferred to give him my e-mail address, since I lived with my parents and didn't want them to answer the call.The next day I received Roberto's first email message. The title read "I would like to see you like this", and its content was a selection of photos that he had downloaded from the internet. I began to look at the photos with curiosity. They were young men between the ages of 15 and 20, with an androgynous appearance (their faces had feminine features, their bodies thin and hairless, long hair, small breasts, hip wider than waist, when the penis was visible it was small and flaccid). They were dressed as women, sometimes only in simple but very feminine underwear (pink, or floral), or with erotic lingerie (transparent babydolls, socks with garters, colaless thongs, lace gloves, tight corsets). Other times they wore a blouse and short skirt (as if they were schoolgirls or secretaries), or a sensual dress and high-heeled shoes. Their faces were made up (red lips, pink cheeks, well-marked eyelashes, fine eyebrows), and their fingernails and toenails painted red or pink. Their penises, when visible, were small and flaccid, and in some cases they used a kind of small chastity device, of a transparent plastic, which prevented erection. They were photographed in feminine poses, some more timid (kneeling, looking up, with a gesture of submission, making a childish face), and others more provocative (on four legs, arching the back, pulling out the tail and separating the buttocks with the hands, as if they were offered for penetration). I was very excited to imagine myself in that situation. I answered the message, telling him everything I had felt while looking at the photos.The title of the second message said, "I want you to do these things with me." They were also photos of young men looking like women, dressed in women's lingerie, but in each photo they were interacting with one or more men. The contrast between the men's virile bodies (muscular, body hair, broad shoulders, thick and erect penises) made the young men's femininity even more evident. In some photos, the young men were kneeling offering oral sex to a man, with a face of pleasure and desire. In others, they were being penetrated by a man in one of several positions (on four legs, leaning on a table or armchair, face up on a bed with legs open and raised). In some cases, they did both things simultaneously, with two or more men. Sometimes the photos showed what appeared to be a previous phase, in which the effeminate boy received romantic caresses, or a later phase, in which the effeminate boy had traces of semen on his buttocks, mouth, abdomen, or panties. Sometimes the effeminate boy had his hands tied or handcuffed on his back, or his feet and hands tied at the head of the bed, or a gagball in his mouth. This time, the photos excited me so much that I started masturbating, imagining that it was I who was dressed as a woman, being penetrated by a man, receiving semen in my tail or in my mouth. I wrote Roberto what had happened to me. He replied, "I'm glad you liked the pictures. I invite you for coffee. Call me on my cell phone." I felt a mixture of desire and fear. I called his cell phone, and he suggested that I meet him at a bar in Palermo. When I arrived, he was already at a table, and he greeted me.
-I'm so glad you came. I've been thinking a lot about you these days. So you liked the photos?
-Yes, I liked them very much.
-And would you like to do those things with me?
-I don't know, I'd be a little embarrassed.
-I really like your shyness, but there's no reason for you to feel ashamed. There's nothing embarrassing about being able to connect with your own feminine side. I think you could become a beautiful little girl, and I could help you, if you'll let me.
-How would you help me?
-As if I were your teacher. I propose tasks to you, and then I evaluate how you do them. If you learned well, I'll give you a gift that you like.
-What if I don't do well?
-In that case, we'd exchange the task for another. Is that all right with you?
-That's all right.
-I'm sure you'd look great as a baby. Do you already have a feminine name?
-No...
-Then we have to find one. What names do you like?
-Let me think... I like several: Paula, Laura, Natalia...
-I think Natalia would look good on you. Can I call you Natty?
-Well.
We continued talking for a while, and then we said goodbye. The next few days he emailed me several web addresses for me to look at, and some texts to read. That's how I found out about the names used in English: "sissy" (diminutive for "sister") is the name of boys who have more feminine than masculine physical and personality traits (they are shy, with delicate manners, passive, submissive, fearful), and "sissification" is the gradual process of feminization of a boy. The other texts gave recommendations on various themes of feminization: how to make up, how to hide the genitals, how to choose women's clothes, how to combine accessories (bracelets, earrings, necklaces), how to maintain the silhouette, how to achieve a feminine appearance (tighten the waist, enlarge breasts and hips), how to wear high heels, how to feminize gestures and voice, how to wear corsets. Other recommendations were specifically sexual: how to excite a man, how to suck a cock, how to prepare for anal sex, how to have orgasms by anal stimulation. I was reading them, imagining in detail each proposal. One night, I called Roberto on the phone. I told him I missed hearing his voice, he told me he missed me too. We talked for a while about different topics. He told me he really wanted to see me, and he invited me to visit his apartment on the weekend. On Saturday I gave my parents an excuse, and I went to their apartment early. I felt a mixture of anxiety and excitement. I touched the intercom, he told me to come in. I took the elevator up to his apartment. Roberto opened and greeted me smiling. We went into the living room, which was quite large. The atmosphere seemed warm and cozy. It was well lit by a window overlooking a balcony. It had several armchairs. From the living room you could enter the kitchen, bedroom and bathroom.
-Have you been reading what I sent you?
-Yes.
-Cool. I have some gifts for you. I'd like you to go to the bathroom and get ready for me. In the bathroom you'll find items to wax and makeup. You'll also find clothes to wear. And I would very much like you to wear this.He gave me a chastity device, similar to the ones you could see in the pictures he had sent me. It was transparent, in the shape of a small, flaccid penis.
-But if I put it on, I won't be able to touch myself...
-No, but you'll be able to concentrate on other sensations. I'd be very excited to see how it looks on you. Do it for me. Put it on and let's see how it turns out.
-Well, that's fine.I went into the bathroom, with a mixture of excitement, anxiety, shame, and desire...The elements were in a bag. I spent some time waxing my body, including my armpits and pubis. When I finished, my whole body was soft to the touch. I used the techniques I had learned to clean the inside of my anal orifice. I bathed, dried, and trimmed my hair. I looked for the chastity device that Robert had given me. My penis was flaccid in the bathroom, so I put it on easily. A ring was used to fix it to the testicles, and it was closed with a small padlock. When I had it on, I started to get excited, but the device prevented an erection.I found in the bag a feminine perfume, with a floral scent, and I put some on. I put a base on my face, and painted my lips an intense red, my eyelids a soft violet, and my cheeks a pink tone. I looked for the clothes in the bag. There was a colaless panties, a transparent pink silk babydoll, and medium taco sandals. I put them on, and looked in the mirror. My body is thin, white-skinned and rather androgynous in appearance. With the help of makeup and lingerie, I looked like a teenage girl whose breasts and hips haven't developed yet. I liked what I saw, and I asked myself: will Roberto like me?I came out of the bathroom, and Roberto was waiting for me on the living room couch. When he looked at me, he put on a face of desire and said:
-Natty, you look beautiful! Come, sit with me.I felt relief and pleasure. I approached the couch and sat next to him, but I preferred to wait for him to take the initiative. He approached me and caressed my leg gently. I felt a shudder of pleasure. His hand went up the crotch. Robert checked that I was wearing the chastity apparatus, and he smiled satisfied by my obedience. He took me by the waist and approached me to him. I felt the warmth of his body. He began to kiss me on the neck, and then his tongue, reaching the lobe of my ear. His right hand lowered the left strap of the babydoll, and he began to pinch my nipple. I closed my eyes to concentrate on the sensations, and began to moan with pleasure.
-I like you moaning, Natty. You look like a kitten in heat.
-Mmmhhhh, that's good, I continued.Roberto lowered the other strap, and began to suck and bite my nipples. I felt a lot of excitement, even though the device prevented me from having an erection. It was a strange and unknown sensation for me, but very pleasant.He stopped, and took me by the waist. I opened my eyes. His face was very close to mine. We looked into each other's eyes, and kissed passionately. I felt his tongue enter my mouth, while my lips caressed his. I felt very happy, and I wanted to repay him for the pleasure he was giving me.
-Can I undress you?
-Of course, Natty.
I stood up and looked at him. His face was masculine and attractive. I unbuttoned some buttons from his shirt. His chest was wide, covered with hair. I took his shirt off. I began to caress his torso, the hairs on his chest, his muscles well marked. I found it very attractive to look at him and touch him.
-I like your body," I said.
I was excited to feel the contrast between his hairy skin and my soft skin, between his big, manly body and my thin, feminine body.I unbuttoned her pants, and lowered the zipper. I had a blue slip. I began to caress him, palpating his dick through the fabric. I put my hand under the slip, and stroked it gently. I began to pull down his pants and slip, until they were completely out. I could see his dick. It wasn't quite erect, but it was still bigger than mine. I took it with my right hand. It was hot. I started to move my hand, and it started to grow quickly. The trunk became hard. It was thick and a little curved. The glans enlarged and peered out of the foreskin. I wanted to feel its smell and taste.
-Mmmm, what a rich dick you have! Can I try it?
-Of course, Natty.I knelt on the floor, between his legs. I had this beautiful dick in front of me. The aroma excited me, it was similar to the smell of sweat but softer. A few drops of pre-seminal liquid appeared on the tip. I put my tongue through the tip, and I felt a salty taste. I began to lick his dick, as if it were ice cream. I put it in my mouth and began to suck, while I looked at his pleasure face. I liked to think that I was turning him on like that. I gently ran my tongue through his testicles, and then went back to his dick. I tried to put it all in my mouth, slowly, as I moistened it with my saliva. I stopped just before I felt arcades. For a few seconds I felt her hard, hot cock inside my mouth. I slowly pulled it out until I was completely separated, and I repeated the process again. I noticed that he liked it, because he started to move to accelerate the rhythm. I adapted to his rhythm, faster and faster.
-Yes, that's right, I kept going, Natty...
I knew that if I continued, I would make him ejaculate. I felt so excited that I didn't want to stop. Suddenly, he started throwing several jets of semen into my mouth. I swallowed the semen mixed with my own saliva. I left the last jets in my mouth for a while, to taste them and feel their consistency before swallowing them. The taste was salty and pleasant. I used my tongue to wipe away the remnants of semen left on his glans. Her dick lost its erection.Roberto attracted me to his body, and we kissed. He suggested that I go to his room.We went to the bedroom. I took off my sandals and lay on the sheet. Roberto sat next to me and began to caress my legs. He took me by the hip and spun me upside down. He began to caress my tail gently. He placed a pillow under my belly, and lowered my panties to my thighs. The babydoll was short and barely covered my tail. Roberto began to run around my buttocks with his tongue. I closed my eyes and began to groan with pleasure. I felt his saliva wetting my buttocks. I felt his tongue running through the groove between my cheeks, wetting my anal orifice, trying to get in. It was very pleasant.Roberto took a lubricant from the light table, and put a squirt between my buttocks. With his finger he began to spread it. He lay on me, and started rubbing his cock between my buttocks. That made me very excited, and made me want to be penetrated. I felt his body over mine, his warmth. He began to kiss my neck and my ear. He placed the tip of his dick in my anal orifice. I lifted up my tail and separated my buttocks to open up to him. I asked him to do it carefully. It penetrated me slowly. His cock was very hard, the glans had grown considerably, and it hurt to enter. I shouted, but when the glans was inside, I felt its dick slide into me easily thanks to the lubricant, and I began to groan with pleasure. I was excited to feel his cock inside me, to feel that it was giving him pleasure like a woman would.
-Do you like Natty? Do you like to be fucked?
-Yes, I love it. I want you to make me feel like a woman.
-You're my little bitch, Natty. I'm going to make you enjoy yourself like a female in heat.
-Yes, I'm your whore. I'm yours. Go on like this, take me, cum inside me.
Roberto took me by the hips and lifted my tail, without separating. I was on all fours, with my knees apart. He kept moving my hips, making penetrations deeper and faster. I felt the shock of his body on my buttocks at each onslaught. My penis was still flaccid inside the chastity apparatus, but what Roberto had told me was true: the internal sensations were much more pleasant and intense than anything I had experienced before. I felt that if I followed that rhythm, I was going to have an orgasm. I was still groaning and screaming for pleasure.
-Do you want my cum, Natty?
-Yes, give me your cum, fill me with cum, make me yours.
-That's the way I like it. Drink my milk, my little bitch.
I felt that my body reached the maximum point of pleasure. Roberto moved fast for a few more seconds, and then gave some deeper and slower shocks to discharge his semen into me. I felt a state of complete relaxation and happiness. Roberto separated little by little, and lay on his back. I let myself fall on the bed, with loose muscles and a smile in my mouth. I felt the semen dripping between my buttocks, and I noticed that I had also discharged my semen into the chastity apparatus: it had been my first exclusively anal orgasm, without any genital stimulation. I curled up next to him and began to caress his hairy and muscular chest.
-Roberto, you made me feel things I had never felt before.
-Natty, you are very feminine, and that excites me a lot. I would like very much that you continue exploring your feminine side.
-I would also like it...
After a while, we took a shower together. We lathered each other. I was very happy.