Sander on a Summer Vacation Ch. 01

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She laughed. "I can't do that now." She snapped at my dick head; it exploded in me, but quickly became soft. She walked over to a chest, pulled out a drawer, and rummaged around in it. She closed it and came back with a thick diaper in her hand. She unwrapped it, and I could immediately see it was a different type of diaper; it was much thicker, and I realized it was pink with princesses and unicorns! She asked me to lift my bottom so she could put the diaper under me. Wait a minute, she said. She went back to the drawer and got something else, and she smiled at me. She found a cream that she smeared around my anal hole, slowly playing with her finger outside. I was shaking a little; it was strange. I started to get stiff again! Suddenly, I felt her push something inside my anal hole. It exploded a bit before it slid into place. I understood this must be an anal toy of some kind. She pushed and got the thick pink diaper under my bottom. Slowly, she brought it up to the dick that had started to get hard again. She just pushed it down and pulled the diaper over it. She got the four tape fasteners in place.

"OK, little Sandra, now you have the right diaper on. Get up!"

I stood there, unable to keep my legs together; it was so thick.

"We're missing something; stay put; I'll go get it."

She came back; she had something pink in her hand. My eyes widened when I saw it was a pink Hello Kitty panty! She asked me to lift my legs so she could put both legs into the pink pants she had brought. She pulled it up and struggled a bit to get it over the ball that bulged out front and back, but it came into place and fit perfectly!

"Oh, how cute you are now, little baby Sandra."

I blushed red in the face. She went to the cupboard again and got a pink sweater. I could tell it was a bit special; it had a V shape with a white border. The sweater went down and between my legs. It buttoned up in the middle at the crotch. I had no pants, so I thought I could use my sweatpants. She took my arm and made me stand up straight. She bent down and asked me to lift my legs. Up came a pink skirt with two white lines. She studied me again and disappeared to the drawer to find something more.

"These are perfect! Sit on the bench."

She knelt down and lifted my foot. She pulled a sock on me, but she only pulled it further up my calf and up my thigh; it had to be stockings, and they're pink with white stripes too!

"Now you're done, little sissy. You are perfect."

She was studying me while laughing. I just looked down at the floor in shame and embarrassment. Her hand came towards mine to drag me towards a large mirror. Her hand lifted my head so I could see myself in the mirror. It was awful! I clearly saw the skirt lift up in front and behind. The bulge made the pants visible. I felt feelings that were bursting with humiliation. She was still standing behind me, and her hand still held my head in place. So I had to study myself. Her other hand moved down my pants. Slowly, she stroked my bum. Again, I got to feel the delicious breasts against my back, braless nipples poking into me. I felt myself starting to get hard and horny. It was humiliating and embarrassing, but it was so delicious. Her head rested on my shoulder. She pulled something out of her pocket. She brought it in front of the diaper. I noticed it started to vibrate; it made me extra horny. She started whispering in my ear.

"Is that good, little sissy? Come on now, little slut, show me you're a little sissy slut."

The vibrator just buzzed against the tip, which vibrated all the way to my dick, and my cock just became harder and harder. She squeezed her delicious, firm breasts against my back.

"Is it good, little slut? Is little Sandra horny? Tell me how horny you are. Little slut."

I was so horny now, I couldn't answer properly. Whispering, I got the word out.

"Yes. I'm coming now; I'm coming!"

She just kept going more and more. I come in a big orgasm! I squirted down my diaper, which was filled with warm cum.

"Mmm, was that good, little sissy?"

"Yes. Are you going to take this diaper off me now?"

She just laughed out loud.

"Why should I do that?"

I was embarrassed. "Because it is full of hot sperm".

"No. Sissy's like cum. I always knew you were a little sissy. I'm going to have fun with you all summer. So I'm not going to change your sticky diaper just because you get horny from wearing diapers and being dressed how you are, made to look like a girl, and can't hold it. No, little sissy's get to go around with nice hot cum in the diaper. Come now, little Sandra."

I followed her out to the sun. Why did she do this to me? I was so embarrassed and humiliated by the feeling that the thick diaper between my legs gave me, and yes, it was pink! I had never seen such a thick diaper before. It did not help that the thick diaper was now full of warm sperm, and I started to get hard again!

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shadow_83shadow_839 months agoAuthor

Thanks for telling, it helps when people tell a bit about what they liked and what they thought could be better or was missing. I'm very inexperienced at this writing thing, but I think it's a lot of fun. Thank you for your feedback.

SissyBoy1WarszawaSissyBoy1Warszawa9 months ago

The story starts in an interesting way and I really like Sander/Sandra as Sissy. Sander/Sandra is a boy of short height and slim build, sweet but with weak character and even submissive.

Hanna is a dominant girl who needs to have her submissive boy persona disguised as a girl Sissy to fulfill all her ideas, wishes and fetishes. And I wonder how Aunt Heidi will deal with all this? How will individual days of Sander's/Sandra's vacation (or just vacation) go and what ideas, tasks, wishes, fetishes will he have to fulfill? Will he be completely humiliated, dependent on Hanna and become the real Sissy?

Greetings from Poland SissyBoy from Warsaw. 📖🧒🏻👧🏻❤️👩🏻👱🏻‍♀️

ps. Sorry for grammatical errors and inaccuracies, but I don't speak English.

Ciekawie się zaczyna ta historia i bardzo podoba Mi się osoba Sandera/Sandry jako Sissy. Sander/Sandra to chłopiec o niskim wzroście i szczupłej budowie ciała, słodki ale o słabej sile charakteru a wręcz uległy.

Hanna jest dominującą dziewczyną która potrzebuje mieć swoją uległą osobę chłopca przebranego za dziewczynkę, za Sissy która spełni wszelkie jej pomysły, życzenia czy fetysze. A ciekawe jak do tego wszystkiego podejdzie ciocia Heidi? Jak potoczą się poszczególne dni wakacji (czy tylko wakacji) Sandera/Sandry i jakie będzie musiał spełnić pomysły, zadania, życzenia, fetysze? Czy zostanie całkowicie upokorzony, zależny od Hanny i stanie się prawdziwą Sissy?

Pozdrawiam z Polski SissyBoy z Warszawy. 📖🧒🏻👧🏻❤️👩🏻👱🏻‍♀️

ps. Przepraszam za błędy i niedokładności językowe ale nie znam języka angielskiego.

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