Sander on a Summer Vacation Ch. 06

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The boy was handsome and of the same age as Hanna. He had short, dark hair, and you could clearly see he was well trained. He was wearing shorts and a typical training sweater. His muscles made it clear that he was a person who exercised a lot, and the way his friends respected him, created a clear signal that he was someone who was the leader.

When he walked towards me, I could see he was a head taller than me. He started to check me out. He stopped next to me and took his hand to stroke my back and down my skirt. He waited and got no resistance from me; I didn't dare do anything. He looked at Hanna and smiled. He just continued before he took a firm grip on my bum outside my skirt. I made a noise, but still didn't protest. I didn't dare; the fear of being discovered was too great. I felt I had too much to lose if I started making a scene. He took his hand under and inside my skirt to take a firm hold of my smooth ass. He smiled and looked at me.

"So you like to party, Sandra? Mmm, I like your ass. It is so smooth and delicious. Is your bottom a virgin? Do you like to have a good time with boys? What a sexy little girl you are. You know, Hanna has introduced me to several girls like you, and I love to play with them."

He leaned right next to my ear. I felt his hot breath before he whispered in my ear. "Tell me, Sandra, do you like to suck cock? You look like a good cocksucker."

He ran his index finger inside the pants, played between my bottom and the other hand outside my sweater, and started squeezing my breasts. I was so embarrassed. Here I was, fully dressed like a slutty schoolgirl, being checked out by some boy Hanna knew. I didn't dare do anything but smile. It didn't make it any better that I started to get horny from the things he told me. Daniel stroked and squeezed more over my ass. He leaned closer to my ear and licked my earlobe. Completely automatically, I just raised my head to close my eyes and gave a small moan. He started to whisper.

"Are you horny, Sandra? Hanna always made the most slutty girls. I like slutty girls.

You would have liked a cock up your ass, wouldn't you?"

Daniel smiled as he looked at Hanna. "Yes, Hanna, she has potential. I would like to get to know her better. Can't you two come to my place tonight? I'm going to have some friends over. Who knows, maybe it will be like old times."

I could hear Hanna laughing. "Yes, we'll see. Can I call you later?"

Daniel let go of my bum to look at Hanna with a smile. "Of course."

Hanna let go of my hands, and we were about to leave when he spanked my ass and shouted at me. "See you later, Sandra!"

I was so embarrassed and terrified as we walked. "Why did you do that, Hanna?

Who was that boy? It wasn't kind! You made it seem like I was kind of a slutty girl!

And you held my arms! I couldn't stop him!"

Hanna suddenly stopped, looking directly into my eyes; she held me firmly by the arm.

"Now you hear me, you little sissy-bitch. I just wanted to show you how sexy you are and how hot the boys are for you. Listen, Sandra, I think you should make the most of the situation and not be so embarrassed and defensive all the time. We both know you're a sissy-bitch! Oh, we both know that it makes you horny as hell! Open yourself up and take advantage of it. I think you'll experience something you've never felt. Let it go and trust your inner slut. If you listen more to me and mom and express yourself more, we will create the perfect Sandra. We will give you feelings and desires you could never dream of.

"Daniel thought you were a sexy, hot girl. Take it in, open it up, and use it. Play with the boy's horny feelings and get a little flirty; it's so fun. To be honest, you look damn hot! They like your slutty look. I've known Daniel since I was little, and we've played together a lot over the years. I think he would be perfect for you. Oh, I'll tell you a secret-- the dildo I fucked you with, Sissy, is a true copy of Daniel's lovely cock. Now come, we'll go find a place to eat."

I was embarrassed, but I thought a bit about what Hanna said; there was a bit of truth in it. I felt the rush of hormones in my body as we walked. I felt a boost of confidence from all the looks from the boys and the whistles we got, as we walked. Hanna noticed it and smiled.

"Good, Sandra. You see, you're a natural-born sissy-slut. I saw you were missing one thing from that schoolgirl outfit, and I was lucky enough to find it for you. Come with me."

Hanna took a firm hold of my arm and dragged me into a public toilet and locked it.

"Hanna, what the hell are you doing?"

She opened her bag and pulled out one of the thick, pink, rattling plastic diapers!

"No Hanna, please!"

I tried to push her to the side to get out. But she just took a firm hold of my arm and looked me straight in the eyes with an extremely intense look.

"Now listen, you little diaper sissy! You will always obey me, no matter what! If you don't do what I ask of you, I'm screaming for help! People will think I'm being raped by a crazy boy who dresses like a girl! Think of what boys would do to you in prison!"

I was so scared. Was she serious? She unfolded the pink diaper and put it on top of the toilet. I just studied the thick, pink diaper, while Hanna rummaged through her bag. She smiled as she found a dildo in her purse. It was the same dildo she had used on me earlier, the one that was shaped like Daniel's cock! Slowly, she started to unbutton her shorts, put the dildo between two of the buttons, and buttoned the top so the dildo stuck out of her shorts like a cock.

"Get on your knees."

I didn't dare do anything but kneel down in a public toilet. I felt like a cheap whore. My eyes looked up at Hanna, who was clearly enjoying the situation.

"Suck my cock, bitch."

I moved slowly towards the dildo. My lips parted, and the dildo slowly slipped between my lips. Slowly, the dildo went in and out at a given pace.

"What a sexy, cheeky whore you are. Imagine if it were full of boys in here; would you rather suck real cocks?"

The feeling of humiliation grew stronger, but the words she used also only made me more horny. I worked more diligently, and when I kept both hands on her hips, I exploded with horniness. Suddenly, she pushed my head back to look at me, she held a bottle of lubricant in her hand, and began to jerk the dildo.

"Now bend over, bitch!"

I turned to stand, now bent over with my head over the top of the toilet. My skirt was lifted, and my pants were taken down to my knees. Gliding cream started to flow down my asshole; slowly, it was now pressing into my sissy-hole. Slowly, the dildo slid in and out, in and out, until it was all the way inside. Hanna kept a calm pace, but I was so horny; pre-cum just started flowing. She made sure the diaper was right under my cock, and then all the pre-cum flowed right into the diaper. She pressed more, and as I was about to scream, she started covering my mouth. Sperm was now leaking into my diaper--a kind of orgasm I had never felt before. She took my arm and turned me around. I bent my shoulders, so I had to sit on the diaper that was lying on the toilet, full of sperm.

No matter how embarrassed, humiliated, and full of shame I was, I couldn't resist the delicious feeling of the soft fabric on the inside of the diaper. My butt sat down on it, and Hanna squatted down. She pulled it up back and front, pulling the straps into place to make sure it was tight. She stood up with a big, wicked smile. Her arm pulled me up to a standing position, and I got my pants just above the thick diaper. It made a bulge in the back, which made the skirt shorter. Luckily, the skirt just covered the diaper, but if I bent over, everyone would see it. The legs were a bit clubbed, and it was more difficult to walk. I looked like a schoolgirl in a thick diaper if you looked closely. Hanna just smiled more.

"You're a perfect slut, Sandra. Think how delicious it would have been to suck a boy in here, while another fucked you! But you are also so cute in your diaper, Sandra. You don't have to be afraid of having an accident. Come, we'll go meet mom."

Hanna took off the dildo and took me by the arm. We went outside. I tried to walk slowly with calm movements to make as little noise as possible, but Hanna only increased her speed. I wasn't sure if she was doing it to make more noise about me or if we were running out of time. But it was so embarrassing.

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5 Comments
AnonymousAnonymous4 months ago

The diaper thing is a little strange and getting old. If he's going to be a girl, cut his nuts off, give him hormones or hypnotize him, but to think a straight guy would go through all this without World war three, doesn't fly.

AnonymousAnonymous4 months ago

Does this guy have mental issues? He doesn't seem to be able to verbalize or make a decision on his own. He's not drugged or on hormones and he's supposedly straight and he doesn't have the use of his mouth, hands or feet. Oh and he just lets people do whatever they want being incredibly slow on the uptake. He could have stolen money from his aunt or the salon and escaped.

AnonymousAnonymous6 months ago

Liked the story look for ward to next chapter

shadow_83shadow_837 months agoAuthor

@sissyboy1warszawa

Thank you very much for the nice feedback, I really appreciate it. I will continue the chapters as long as all still like them. next chapter will be finished soon ☺️

SissyBoy1WarszawaSissyBoy1Warszawa7 months ago

@shadow_83, it's great that you lead Sandra to become an increasingly submissive and humiliated Sissy, you open up the world of sex to her, and with people other than those she already knew from Mrs. Heidi's house. You let Sandra open up, feel like a real, sexy, slutty female dog.

I have become very attached to Sander/Sandra and I look forward to her further transformation and experience into Sexy Sissy with great interest. I wonder how she will handle the meeting with the boy and what the further consequences will be? What does Mrs. Heidi say about this and what will Hanna come up with next for Sandra? 🧒🏻♀️👶🏻🍼👧🏻❤️👩🏻♀️👩🏻‍🦳.

ps. Sorry for any mistakes and linguistic inaccuracies, but I don't speak English.

SissyBoy from Warsaw, Poland. 📖👩🏻‍🦳♀️❤️🧒🏻.

📖❤️.

@shadow_83, fajnie prowadzisz Sandrę do zostania coraz bardziej uległą i upokorzoną Sissy, otwierasz przed nią świat seksu i to z innymi osobami niż do tej pory znał z domu Pani Heidi. Pozwalasz aby Sandra się otworzyła, poczuła jak prawdziwa seksownie zdzirowata suczka.

Bardzo zżyłem się z osobą Sandera/Sandry i z wielkim zainteresowaniem oczekuję na dalsze przekształcenie i doświadczenia jej w Seksi Sissy. Ciekawe jak poradzi sobie na spotkaniu z chłopakiem i jakie będą tego dalsze konsekwencje? A co na to Pani Heidi oraz co dalej wymyśli Hanna dla Sandry? 🧒🏻♀️👶🏻🍼👧🏻❤️👩🏻♀️👩🏻‍🦳.

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

SissyBoy z Warszawy, Polska. 📖👩🏻‍🦳♀️❤️🧒🏻.

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