Sander on a Summer Vacation Ch. 03

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Hanna testing Sander's limits.
3.5k words
4.59
12.5k
7

Part 3 of the 8 part series

Updated 12/30/2023
Created 08/17/2023
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Introduction:

This is a short story about a 19-year-old boy called Sander. He is visiting his aunt and cousin. He has experienced that his cousin likes to humiliate him but also feminizes him.

From previous chapter:

"Hanna was visited by some friends who found out he was a sissy. They forced him to fill his diaper while he was tied to a bench, where he had to suck a dildo at the same time. It develops further with Hanna and her friends, with a little truth or dare."

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The body was completely immobilized, but the thoughts flowed wildly. My tears gently rolled down my cheek. "How could I let this happen to me? I should have known better about Hanna; she had always been like this to me before. How could I be so weak and fall for her beauty? No, something had to be done, but how could I? The door opened, and I noticed someone enter."

A hand caressed my cheek, and I saw Hanna appear in front of me.

"Looks like the little diaper sissy has filled her diaper. Well, I gotta say it was a good thing I left it on."

I tried to get some words out, but it was impossible with that gag stuck in my mouth. I tried several times to say something, but it was just mumbling.

"Are you trying to tell me something Sandra? Does my little sister need a diaper change? It's a good thing you got your sissy hole cleaned for tonight."

She just started laughing as she untied me and removed the gag that had been in my mouth for so long. She helped me onto a changing table. Carefully, she removed the filled diaper. She dried me and led me into the shower.

"Now wash yourself and clean your self sissy."

The look I sent back showed anger and contempt. Hanna saw it and was a little annoyed by it. She looked back, and her eyes sharpened. She found a small towel, rolled it up, and came towards me. Suddenly there was a slap on my bum, it came again and again before she finally stopped. She found a small towel, rolled it up, and came towards me. Suddenly there was a slap on my bum, then it came again and again before she finally stopped. She grabbed my hair and pulled my head back. Slowly, her breath met my ear. I could feel her breathing, the sound of her tongue coming out, and starting to lick my earlobe. While her hand now felt my cock. Slowly, she gently stroked it with her finger. I tried everything I could to stop the feeling of horniness that was coming, but my cock just got harder. She just kept stroking it; my breathing got heavier, and I got significantly hornier. Her hand wrapped around my cock, which was standing straight out. She slowly jerked it while her tongue played with my ear. Her hand again stroked the stiff cock before tickling my balls. Suddenly it exploded in pain. She had a firm grip and squeezed my balls. I came with a strong whimper. I tried to get a scream out, but she blocked my mouth with her other hand! She opened her voice.

"Do you think you can give me attitude? Don't you think I can't break you down? Just keep going; see how far you get, you fucking bitch. Now wash yourself; I'll find you some suitable clothes, you little bitch."

Her grip around my balls disappeared, and she left. Explosions continued to come, but it started to calm down. My mind was still working. "No! She won't be allowed to win again! Why can't I resist the temptation she gives me?"

It felt good to feel the water running down my back. It helped with the pain that was still exploding in my cock. I got out of the shower and dried myself. At the same moment, Hanna came with some clothes, which she threw on the floor. She looked at me and pointed.

"Pick it up, put it on."

I looked at the clothes and back at her. "No! I want my own clothes back! Now you have to stop Hanna; it's not fun anymore!"

She looked at me; her eyes tightened, and I could clearly see she was thinking carefully.

"You want me to stop; do you think I've been mean to you?"

"Yes, you have; now you delete the pictures and video clips you have made. Let's have a nice summer holiday together instead."

She started smiling, and slowly she started unbuttoning her blouse as she slowly came towards me. I could see her deliciously firm breasts in her bra. She stood right in front of me and stroked me along the skin. She looked me deep in the eyes and saw that she had my thoughts exactly where she wanted them. She leaned forward and whispered in my ear.

"Do you like my breasts? Do you want to feel them? You do, don't you? I can see it in your eyes. It's okay; many people want to feel them. Tell me, little sissy."

I was completely paralyzed. I wanted so much, but I couldn't. thoughts just exploded in me. At the same moment, she took my hand, slowly bringing it up her stomach while continuing to whisper in my ear how much I wanted and what a good little sissy I could be to her. Slowly, she got me inside her bra. I could feel her firm, delicious breasts. My cock just started pumping again, and it hit her thigh.

"I can tell there's someone who likes this. Good little sissy, keep feeling me."

Her hand continued to move my hand; I felt her breast nipple was stiff; it was so delicious; hot lusts of horniness just spread in me; and again, her voice whispered in my ear.

"I'm making a deal with you; if you put on the clothes that are on the floor, then you'll get to feel the inside of my pants—my wet, delicious, hot pussy. Would you like that, Sandra?"

How could she do this? My mind raced; I should stand up and say no! But my mind was elsewhere. "Yes, Hannah." I heard her laugh a little.

Slowly, she took my other hand and brought it to the inside of her shorts, down to her pants. The further down I got, I could notice it was already wet; she was clearly horny. She took my hand and used it as a toy; sounds of moans came from her mouth into my ear. I didn't do anything; she just used two fingers from my hand to play with her moist lips. She made it go in a slow but active motion, her moans becoming more intense. Again, she moved my two fingers further down, bringing them deep into her two hot, wet pussy lips. She continued regularly at the same pace in the dunes and within the hot, wet lips. She took two fingers from my hand that were held around her tit, and slowly she started squeezing her nipple with my two fingers. She became more intense, the pace increasing in her hot, wet pussy. I was completely paralyzed. I was so horny! At the same moment, she pressed her two fingers deep into the wet pussy and let out a real moan. I felt her whole body tremble; she clearly enjoyed this. Slowly, she pulled my hand out of her pussy, which had now been used to finger her. Her eyes met mine, and she smiled slyly.

"Good girl, Sandra, I knew you would be good. Now, lick your fingers clean for me. Show me what a little slut you are."

She continued to press my hand against her tit and squirted. I couldn't do anything but listen. Slowly, I brought my hand, which was full of wet pussy juice after it had been used to finger her. My mouth opened, and my tongue began to lick around my fingers. Hanna laughed a little and again answered.

"Now suck your fingers."

My lips molded to my fingers. I couldn't believe it; I was now sucking my fingers! When I was completely clean, I took them out. Hanna smiled and stroked my cheek, took the hand out of her bra, and took a step back.

"Now, you keep your part of the deal."

Reluctantly, I looked at her. I bent down and found the pants, which were slowly sliding up between my legs and into place. Something special feeling happened. I was still horny, but it created a special feeling when the dick hit the soft fabric of the pants. A warm, sparkling feeling spread, and it was embarrassing that Hanna could clearly see it.

"Well, I think it looks like someone likes this."

Embarrassment returned. But she had let me play with her, so I guess I had to keep my part of the deal. I found a bra that I got assembled and in place before I pulled on a top that covered my navel. I found a pair of short hot pants that clearly tightened well. It was not easy since my cock was still stiff but had been bent down; luckily, it helped a little to make it start to give way from stiffness.

"Now, good girl. Come with me, and we'll go relax in the sun together while my friends do some shopping for tonight."

I was embarrassed, sitting out dressed like a girl who clearly showed signs of being a slut. Imagine if her friends saw me like this. It would have been more embarrassing if my aunt came to see me like this, or maybe she would have been mad at Hanna? Yes, just hold out one more day, and Auntie will come home and get me out of this mess that Hanna has made. Yes, maybe Hanna can get back to the same feeling! I smiled to myself. Yes, I just have to make it through the weekend.

Hanna tried to be sociable and talk to me normally, but it wasn't easy compared to how I felt. It had to be said that she had not been any more mean to me; she had been kinder and made us lunch too! When it was a little late in the day, I got a push. I must have clearly fallen asleep.

"Hey Sandra, you fell asleep. Now it's time to get in and take a shower. It won't be long until my friends come back; it'll be a nice dinner, I promise. Since you were such a good sissy, I left some nice surprises on your bed."

Surprises? What is she thinking about now, and what are her thoughts on tonight? I disappeared, took my shower, and came to the room. I was surprised by what greeted me. Were there normal clothes there? sweatpants, a t-shirt. Maybe she has given in to play; she got her way when she had her orgasm. I took off my towel and was about to find a pair of pants when Hanna entered.

"Look how kind I am to let you have your normal clothes back. But there's a catch if you want them."

"Hanna, give it up! Now I think it's gone too far. Maybe I should tell Aunt everything!" I looked at her with a slightly angry look. Hanna came over to me, pushed me down on the bed, laid me on my stomach, and pulled my arm up my back! I screamed in pain, but she started spanking me again and again. I screamed in pain; I could imagine it was 15 blows on the bottom before she gave up.

"Now you little bitch, behave like this too, me! Do you really think my mother is going to believe anything you tell her? You who have had parties at home without permission, why are you with us in the first place? Think again! Now you bend those bums up; just stay on your stomach until I come back."

It stung so terribly that I didn't dare do anything but listen. She came back, lubricated my hole, and slowly pushed in a butt plug. She wiped up around the hole and pushed me to the side. I quickly noticed how quickly it pressed against the g-spot; it made me squirm. She found a pink lace panty and pulled out a flat sports bra-like thing. She looked at me.

"Perfect, this will be great for you. Put on the rest of your clothes; it's almost dinner."

She disappeared out of the room. Again, I sat with the embarrassing feeling that I had lost. At least I got to have my clothes.

There was a cozy atmosphere inside the cabin. The lights, pleasant music, and the smell of good food and chatter with laughter made it pleasant too; clearly, her friend was back. When I entered them, everyone was smiling. One of the girls looked at Hanna.

"But Hanna, isn't she a sissy anymore?"

Hanna smiled and looked at me.

"Of course she's still a sissy, Bree. I just thought I'd be a little nice to her. Of course she's got a wonderful panty underneath."

Hanna gave me some sharp eye notes while everyone just laughed. They continued with their work and asked me to set the table. The atmosphere was good—laughter, joy, and a delicious meal. I was regularly used to fetching new drinks for them. I could tell they were under the influence of alcohol. Her friends regularly spanked my bottom. It shook me every time—the feeling of the plug pressing every time. We sat down on the sofa, and I was able to enjoy the taste of alcohol too. Clearly, now I was more relaxed in my body. Lisa started talking about the good old days when they clearly had fun here. Lisa smiled.

"Why not play a game like in the old days, girls?"

The other girls laughed and replied.

"Yeah, good idea, Lisa!"

What kind of game is this? Hanna's look and smile made it a little frightening. I ask, "What kind of game is this?" Hanna smiled again.

"Nothing special; it's truth or dare."

Oh, not so bad. I thought. should be easy. They started off with easy, stupid questions you always ask when you're a little drunk. Everything from school stuff to sex questions but when Hanna looked at me with a look that made me uneasy, I became anxious, Hanna said.

"So Sandra, how long have you been turned on by wearing pants? I can see how turned on you are by them; clearly, you must have tried before."

I was so embarrassed; how could she ask such a thing? "I've never tried pants on, except when you forced me to wear them when we were little!"

"Oh well, but then I guess I'm the one who made you horny for pants then. I must say I've done a good job; if you're getting horny about pants now, it's been so long since I last did it."

All the girls just laughed. Lisa next asked if I wanted truth or dare. I was so tired of the stupid questions, so I answered quickly without thinking, "Dare."

I think about it quickly; maybe it was stupid; fast, I say "truth." In sted. Lisa said.

"Sorry, but you already said dare. So I think you should take off your t-shirt."

It wasn't that bad. The questions went again before they landed on me again. Hanna was good at coming up with annoying, humiliating questions, so I didn't want to answer any more. When Bree asked me, I said, "Dare."

Bree clapped her hands and laughed.

"Good, now get up and put on a strip show for us. Put on a good show, or you'll have to do it again."

I stood up nervously, they changed to some more strip show music, and slowly I started to move. It wasn't easy; I easily felt the butt plug start to move. It created a slightly strange but exciting ignition in me. The girls clapped and whistled. That they created such an atmosphere made it more fun for me. I put in more rhythm and more passion, but the more passion I put in, the more spark I got from the plug hitting my g-spot. I had my eyes closed but stood with my bum at them, wiggled back and forth, and the pants fell off. Everyone whistled and clapped, and I sat down on the chair, embarrassed in just my pantis and sports bra. Hanna looked at me.

"Now look how sexy the little sissy is. It looks like you're a little cold."

I didn't answer, but again, new questions came. Again, several now managed to create annoying humiliating questions, so again I could not bear to answer truthfully, so again I took "Dare."

This time it was Bree. She smiled at everyone and disappeared out of the room. She came back with some clothes.

"Now put this on."

I carefully studied the clothes. My eyes widened when I saw that it looked like a schoolgirl outfit. "You can't think I will put this on?" Bree stood with her arms crossed, looking at me.

"Listen, you little sissy, I know you like pantis; I can already see it; don't deny it. Now I'm being kind and giving you some clothes to cover it up, so put it on!"

I started to get dressed. first two white stockings, with two pink stripes at the end. A pink top that was over my navel with the word SLUT written on the front. Finally, I pulled up a short pink schoolgirl skirt with two white stripes at the end. I felt embarrassed, but it was better than sitting naked. Everyone again whistled and clapped. Again, the game went on, now slightly kinder questions but dirty with the girls. I felt myself getting horny from all the answers the girls came up with, all the words about how they liked sex and what they had tried. I felt horny but tried to hide it, but again, questions came to me that were embarrassing, irritation came again, and I answered "Dare".

Lisa smiled when she got my answer. She disappeared and came back. She sat down next to me and told me to close my eyes. She started brushing things on my face, and the thought hit me: It's makeup! I tried to move, but all the girls held me back! I pushed as hard as I could but couldn't. The last thing I noticed was lipstick getting on my lips. All the girls let out a laugh and sat down. I saw them all just grin. Hanna smiled.

"Now, look in the mirror, then, Sandra."

I looked in the mirror, and I was shocked! I looked like a completely different person. Oh, that outfit! I felt myself getting horny. I didn't know why, but horniness just spread throughout my body! Hanna came to me, caressed my cheek, and squeezed my bottom.

"Now, sissy, you're sexy as hell! Mmm, if I were a boy, I'd fuck you right away! You're dressed for the role anyway."

Everyone just laughed and agreed. Then Hanna lifted something for me, and I looked down at her hand. She was holding a dildo! She went to fix it with the vacuum on the end of the dildo. There it was, now ready on the table. Hanna came back and pointed.

"Get on your knees and suck it for us."

I just looked at them and hesitated. Hanna gave me a real slap on the bottom, put her hand inside my skirt, and felt my dick.

"Come on, do it."

Slowly, I kneeled down. I was now sitting right in front of the table, watching them. Everyone just grinned until everyone told me to suck it. Slowly head towards it, slowly my lips opened and brought down the dildo, which I now sucked. Everyone clapped and whistled. For some special reason, I became more eager and horny. I put in more passion and work, started to lick it and suck more. Everyone clapped and whistled even more. I was now on my knees, horny, and sucking a dildo!

"Go on and suck the dildo; we'll be right back."

I closed my eyes and just continued. When I opened my eyes to catch my breath, the girls were gone. I suddenly heard Hanna's voice behind me.

"Sandra, slut, we have a surprise for you. Come on, sissy, turn around."

All the girls were now standing behind me, and I carefully turned around to look. A shock settled in me; all three girls were now standing there with their strap-on attached to the front of their pants!

Everyone just laughed until Hanna broke her laughter.

"Are you ready to play with us, little sissy?"

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SissyBoy1WarszawaSissyBoy1Warszawa8 months ago

I am fascinated by the plot of this story, I have become very close to Sandra, and although I lack at least a bit of willpower in his character, he does not fight for his Self and every time he becomes submissive or even humiliatingly submissive to Hanna and her friends.

Just like Sandra, I would like to change into women's underwear or clothes. I have many imaginations, thinking how Hanna and her friends will turn Sander/Sandra into a submissive Sissy or even a sex toy for them. I even think what will happen when Sander comes home, will he be so used to and even addicted to women's underwear then. Even after Sander returns home, Hanna will dictate to him how to dress, what to do, how to behave and even have to wear a pink chastity cage or butt plug. I would like to be such a Sissy and have my Mistress or Mister. 📖❤️🧒🏻🍼💦👧🏻👩🏻‍♀️👱🏻‍♀️.

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

SissyBoy from Warsaw, Poland. 👩🏻❤️👩🏻‍🦳.

Jestem zafascynowany/a fabułą tej historii, bardzo zżyłem/am się z osobą Sandry i choć brak mi w jego charakterze choćby odrobiny siły woli, walki o swoje Ja a za każdym razem staje się uległym a nawet upokarzająco uległym wobec Hanny i jej przyjaciół.

Tak jak Sandra chciałbym się przebierać w damską bieliznę czy ubrania. Mam wiele wyobrażań, myśli jak Hanna wraz z przyjaciółmi będzie zmieniać Sandera/Sandrę w uległą Sissy a nawet wręcz seksualną zabawkę dla nich. Nawet myślę co będzie gdy Sander wróci do domu, czy wtedy już będzie tak przyzwyczajony a nawet uzależniony od damskiej bielizny. Hanna nawet po powrocie Sandera do domu będzie dyktować jemu jak ma się ubierać, co robić, jak się zachowywać a nawet będzie musiał nosić różową klatkę czystości czy korek analny. Chciał/a bym być taką Sissy i mieć swoją Panią czy Pana. 📖❤️🧒🏻🍼💦👧🏻👩🏻‍♀️👱🏻‍♀️.

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

SissyBoy z Warszawy, Polska. 👩🏻❤️👩🏻‍🦳.

jennifurzoejennifurzoe8 months ago

Loving it,this is getting better by the nice sweet chapters,and as a Ruled, Lead, and Owned sissy you know this is our dreams, wishes,desires to happen,,

Addendum; perhaps a better editor as many wrong terms and spellings, still a good theme..💜

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