I saw him for the first in the foyer a few months ago. A few days later I met him in the elevator. He was on the way for his apartment which happened to be just underneath mine. As I found out later, this was really convenient but in exactly that moment something else bothered my mind. I knew the boy from somewhere. It seemed that he is at least 20 years old, or at maximum 25 year old. I couldn't tell exactly. He was skinny and reasonably tall. I tried to remember why he seemed familiar but I couldn't.
Later at home I've just taken my regular shower when it hit me. I knew him from an internet forum two years ago. Back then we exchanged a few messages, he even sent me a few photos of him, but ultimately he chickened out when I told him that I have the will to help him for real with what he was asking.
A bit later that evening, I opened the old conversation I had with him. I briefly read all the messages we have exchanged and decided to contact him again. I wrote a few words and waited. Of course no one replied. Few days later I decided to check again so I opened the laptop and voila - he had replied. We chatted a few times and when it seemed appropriate I told him that I was actually his neighbor from the upper apartment. For the next two weeks there was no response - only the label "seen" after my last message. During that period I met the boy a few times in the common areas of the buildings, but he always bowed his head afraid to look at me. I have already given up on the idea when with a surprise one evening he sent me another message. It was saying "Maybe we can try".
...
The doorbell rang. When I asked who is it, his trembling voice answered "The neighbor from the apartment downstairs". His voice was trembling. Satisfied I let him in. After I closed the door behind him I took a good look. He was obviously very anxious. I decided to get straight to the question.
"You haven't been fucked by a real man's cock, right?" he seemed surprise how straight forward was the question.
"No, not really. I know I have told you otherwise, but the most daring thing I have done till now was fuck myself in front of the mirror."
"Then, we will do exactly that. You will get fucked in front of that mirror" I pointed the large mirror I had in my hallway. He gulped with anxiety and fear. "Take your jeans and pants down." I ordered.
Initially the boy hesitated, but only for a few seconds. He was determined, despite his shaky movements. His jeans and pants fell on the ground. His circumcised dick was hard and pointing at me.
"I see that you are perfectly shaven down there, just like a good and obedient cunt. Now, it would be nice to point that shiny big cock elsewhere. You are not using it this evening" I carefully forced him to face the mirror. "Lift your shirt just a little" he obeyed.
It took me a second to take my cock out. I spat on it and pressed the head against his asshole. It slid inside with ease. I didn't stop until I had all my 8 inches inside of his shitter.
"So I know your username, but what's your name in the real world?"
"Kevin" his voice was as shaky as his limbs
"And how old are you exactly?
"21"
"So, Kevin you are a 21 year old with a nice big cock shoved in your ass. How do you feel about that?"
"Like a happy sissy. Please fuck my little dirty hole"
"You will have to work a lot to become a real sissy, but let's say this is your first lesson"
Being said that, I started fucking his skinny ass. He was moaning like a little bitch and I was deliberately thrusting as rough as I can. It was obvious that his asshole was not virgin, but if what he was saying was true, my cock was his first real cock. After ten minutes of vicious fucking I emptied my balls in his welcoming hole.
"That's enough for today" I watched as my sperm leaked from his abused rear hole. "Lift your pants from the ground and come back tomorrow at 8 o'clock. Understood?" He whispered something that sounded like thank you and headed out.
...
The next day I fucked him in my spare bedroom. This time I ordered him to get completely naked before I shoved my cock in his willing asshole. As during his first time, he was crying and moaning like a good sissy slut. I didn't show any mercy. He wanted it. I filled his slutty rear two times with my sperm. The pathetic cock willing sissy lying under me had his first anal orgasm. His own cum erupted from his useless circumcised cock covering his own belly and chest with the white liquid.
I decided I have finished with his training for the evening after ejaculating in his poor anal hole for a third time. Before sending him downstairs back to his apartment I gave him a gift. His first sissy panties - a narrow leather strap with a medium size pearl beads on a strand. Kevin put them on. The beads disappeared between his ass cheeks landing tightly on his fucked and cum covered asshole. On the front the beads were supposed to go between the lips of the cunt, but in his sissy case the strand of beads was pressing against his useless and soft cock.
"You can dress. From now on, when you are coming in my apartment you are wearing these." he started dressing looking at me like a puppy. The pearl strand was really tight for him but his was on purpose. Kevin put his jeans on. "And also... I will be calling you Kiara."
...
In the next few months I made sure that he grows up to be a real sissy. More and more I was thinking about him as Kiara. She was thankful about that happy to be my anal sissy slut. For what is worth she was so eager to ride my cock with her sissy cunt that sometimes she was sending me photos of her training regime preparing for the real fuck with a plastic dildo I had bought for her.
This indeed had an impact. Her asshole transformed considerably during that period. The first time I fucked her in front of the mirror in my hallway it felt reasonably tight. Six months later this was not the fact. Her fuck hole had turned into a loose cock sleeve. On the 8th month it looked like a gaping crater if Kiara was not wearing her buttplug. On the 11th month of the sissy transformation her hole was completely ruined. Her sissy ass was farting constantly especially after I filled it with sperm. Of course I had a few other ideas, which I easily convinced her to try.
...
It took me a few days to prepare, but everything was finally ready. Kiara dressed for the occasion. She was wearing extremely high heels and... nothing else. Of course she didn't need clothes for what was about to happen.
I unpacked the enormous dildo in front of her. I used it's vacuum base to install it on a chair.
"Your task is easy. I want you to eagerly impale your ass on this beauty and fuck it for me." I told her.
Considering the fact that completely on purpose I have bought a toy which was way larger and longer than the ones she has been used to. The plastic monster was almost 15 inches of length. As for the diameter it was a bit over 2.6 inches This meant that if she manages to sit on it, her sissy ass would be permanently damaged.
I lit a cigarette. I was ready for the show. Kiara eagerly prepared herself. She was facing me, when she slightly lowered herself on the plastic dick. From this point on I was watching her struggle with the toy. Inch after inch of the black plastic disappeared in her greedy asshole, but she couldn't go further then the sixth inch. Kiara stood up and repeated the procedure, lowering herself again, this time a bit slower. Again, she was not able to go any further.
The battle took longer then I expected. She needed a lot of crying and moaning but after 45 minutes she was finally sitting on the chair with the plastic toy buried deep in her filthy shitter. Her boyish face was red and wet with tears. She was breathing heavily, but that did not mean that she had the right to take a break. I took out my erect cock and forced her head on it, making her choke on some real dick. She gave me a good blowjob or more precisely throat fuck. In fact, she had no choice. She was so tired from the self impalement that her legs were shaking. The poor sissy couldn't stand up anymore on her feet - the high heels I made her wear, were not helping at all. Kiara's only available option was to sit with the 14 inch monster buried deep in her rectal fuck canal and throat fuck my cock until I ejaculated directly in her throat.
It must have been hard for her - the plastic cock in her anus for sure was rearranging everything inside of her body. Her own sissy cock was so hard in the beginning, but almost an hour and a half later it was hanging soft in front of the chair.
"I know you are tired, but now you have to fuck your filthy hole on this beautiful toy. Would you do it for me?"
She nodded in response. Her first attempt to lift u her ass from the chair was rather pathetic, but soon she was able to establish a good pace. Kiara didn't seem comfortable with such an object in her ass, but at least she had a partial consolation - she had an anal orgasm and her own sperm started oozing from her limp soft cock on the floor. I didn't let her stop the self fucking though. I forced her to continue for another two hours. During that time she cummed two more times. I used the time to take some photos of her dancing on her new black toy in her greedy sissy ass.
When I finally ordered her to lift herself up completely. The plastic toy exited her rear hole with a loud pop followed by a long humiliating fart. Kiara seemed a bit troubled by this fact.
"Don't be shy, you did well. Turn around and spread your ass cheeks" she obeyed. I took a picture of her beautiful ruined hole with my phone and showed it to her. "See what you have done to your sissy hole bitch. Do you like it?"
"Yes" her sissy voice was low and soft
"Touch your beautiful gape, I want you to put your fingers inside"
Like a good sissy Kiara had learnt to maintain a good manicure. She fearfully touched her gaping ass, but soon she slid two fingers with red manicure inside"
"It feels so soft..." she whispered.
"Then why don't you add a few fingers?" she did not needed my suggestion though. After a minute Kiara had her entire fist inside of her own asshole. It did not took long - she started fist fucking her hole for me. Her movements were accompanied by strange fart and plop sounds created by her destroyed shit hole. She did that for a minute or two, when her ass gave up and prolapsed. Kiara was shocked and moved away her hand but the damage was done - her beautiful rosebud was shining between her ass cheeks.
"It's time for you to go home" I did not leave her any to recover from the shock. I grabbed her stuff and put them in a bag, then I gave her the bag. "You are not wearing them now. I want you to go downstairs just like that - naked and exposed. Get your prolapsing ass down there. Let's see if someone hears your heels echo in the corridor"
"But it's risky, someone will see me."
"That's why you are doing it sissy... Go now" she obeyed. I opened the door and watched her fearfully exit outside of my apartment. The echo of the heels was indeed strongly heard in the whole staircase. I knew that her heart was bumping, but she made a step forward. A few more careful steps and she grabbed the railing.
"And if someone sees me, what do I say?"
"You can tell them that you have just finished your sissy training and you are happy. It's up to you"
She moved slowly, partially because of the exhaustion, but also because of the 7 inch heels. Although it was only two flight of stairs she had to take, it took her almost 5 minutes. Luckily for Kiara it seemed that nobody noticed her. At least this time.