Sander on a Summer Vacation Ch. 04

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Pretty Penny

My thoughts were racing, I was sitting down on my knees wearing some really slutty schoolgirl clothes, excited without being able to fully understand why. With three extremely sexy girls now standing in front of me with strapon belts and strapon dildos pointing straight at me! I was far from my comfort zone, and I was about to get up to say that the evening was over, but Hanna pushed my shoulders down. The look of evil the three girls gave me was equally terrifying, yet exciting. Hanna bent down a little and lifted my head by the chin, her intense eyes met mine with a captivating gaze.

"Now listen you little sissy, you are not going to deny us, you have no say or right here, we decide your fate for the night! How this night turns out, is up to your behavior."

I thought about it a bit but couldn't see clearly, the feeling of dread had taken control of me. Again I tried to get up, but at that moment the girls grabbed me, and together they dragged me into the forbidden room. They attached my arms and legs to the post which was shaped like an x. I was firmly locked with cuffs on both arms and legs. All three girls stood enjoying the sight of what they were admiring, the sight of me.

Bree went and found a gag ball which she forced into my mouth and attached behind my head. Lisa entered the room with a bottle of wine and three glasses. Everyone sat on the beautiful leather sofa enjoying the sight of me, completely emobilized. Bree put the glass down, and calmly came towards me. She walked around me and stroked my bottom before a hard spank came. She came forward and slowly licked my earlobe before one of her hands lifted my skirt and pulled my panty down a bit. I felt her hand reach inside the panty to start feeling my cock. It didn't take long before I started moaning. The girls just laughed as they sat enjoying their glass of wine. My now stiff cock was sticking right out, I was so horny. Bree just smiled at me, she picked up her hand and spat on it before she slowly started to stroke my cock. The feeling was heavenly. The sound of my moan was clear, I was over the top. Bree smiled at me looking down at the stiff cock.

"What a delicious dick you have, I must say it's a bit big for a sissy boy like you. Have you fucked many girls with that?"

I couldn't get a word out because there was a gag in my mouth, but I just moved my head to the side, no I haven't. Bree bent down on her knees, slowly stroking the cock that was now right in front of her. The tip of her tongue gently licked my cock, I just closed my eyes in pleasure. She stood up and whispered in my ear.

"Do you want me to suck your cock? Want my lips to take your cock in? I can do it for you if you will get down on your knees and suck my strapon on."

At the same time that she chatted in my ear, her hand was stroking my cock again. With the ball gag I couldn't speak, but just nodded my head up and down, yes.

She came in front of me and smiled as she slowly knelt down. Her finger tip stroked my cock before her tongue tip licked my cock head. I just moaned with pleasure, it was heavenly. Her lips parted and slowly they slid down the stiff cock shaft, the cock sliding deeper and deeper before she backed out. She continued at a leisurely rhythmic pace. I was so horny, I was moaning with pleasure. Suddenly she stopped, her lips gave me a kiss on the tip of my dick head and she stood up. She just smiled and loosened the gag and cuffs that held my arms and legs in place. She smiled and gave me a hot kiss before taking a step back. She looked down at her strapon which she now stood jerking.

"Get on your knees and suck my strapon."

I was so heavenly horny now, it was so delicious. I carefully knelt down, my hand cautiously grasping the strapon. I stroked it with my hand before taking one last look up at her. My lips parted and I began to suck her strapon cock. My head slowly moved back and forth at a leisurely pace. I was so horny from the sucking she had done too me, I took both my hands up behind her bottom to squeeze it while sucking her strapon. Oh it was so hot, she had such a hot ass! My hands just squeezed more and more on her delicious ass and I just sucked even more diligently. Suddenly Bree pushed my head back, I looked up and there was now Lisa with her strapon.

"Suck ME now, little sissy bitch."

She just took her hand behind my head and pushed it towards her strapon, I opened my mouth fast so I got the strapon in. Again I was on my knees sucking a new strapon. I tried to touch this lady's bottom as well, but now my hands were just pushed down. I sucked for a while until Bree took my head and led me to the bed. She laid me on my back, slowly she unbuttoned her trousers and pulled down her pants. She stood there now in her sexy panties with clear marks of wet horny pussy juice. Slowly she pulled them down and let them fall to the floor.

She came towards me, kissed my cock and continued to suck it as her ass stood up. I now noticed that Lisa came towards me without jeans and panties too! She was about to sit down on my face. Slowly she lowered her hips till the two smooth wet pussy lips were right over my mouth. My tongue came out and I could feel that her smooth and warm pussy was already wet. My tongue was just doing what it could while she moved carefully back and forth at the same time. I was struggling to breathe.

Bree continued to suck me calmly but steadily, when I suddenly noticed her lips parted and she gaped wide! Something had happened, and when Lisa got up to turn around, I saw Hanna standing behind Bree and inserting the strapon into her clearly wet pussy. Bree just moaned in pleasure. Lisa sat down again over my face and my tongue started working again. The pleasure was lovely, but Bree stopped sucking me. Lisa stood up and I saw Bree sit right over my dick, she smiled before her pussy lips met my cock, the hot powerful feeling you get when your stiff cock slides into a wet warm pussy, it's a heavenly feeling. Slowly the dick slid deep into the wet pussy lips, all the way in, and I moaned with pleasure. Again Lisa sat over my face, but with her head towards Bree. She leaned forward and I could hear them start kissing. Bree's tight smooth pussy lips continued to ride me at a steady pace, it was so delicious. I noticed she was shaking and clearly coming because she started whimpering. I wasn't far from coming myself, but she got off me just before I did. Then the girls grabbed me and turned me over onto all fours. Bree laid down on the front of the bed spreading her legs
and smiled. I heard the sound of some plastic and saw Hanna unwrap an extremely thick pink diaper in front of Bree. She put it a little under her ass and Bree fingered herself at an intense pace! Bree grabbed the front of the diaper and bent the front up towards her and she came again into a huge orgasm and she squirted pussy juice into the diaper. Bree smiled and Hanna put the diaper aside. My mind was completely different, how sexy to see a girl do this! Bree looked at me.

"Lick me sissy."

I bent my head down and my ass up. I began at once to lick her. Then suddenly Bree took my head and held it in place between her legs, at the same time Hanna and Lisa took my arms and pinned them to my back and locked them with a set of handcuffs. They lifted my bottom so it was standing straight up while my head was firmly against Bree's pussy lips.

"Lick me like you mean it sissy!"

I continued to lick her wet pussy as it was dripping with wet pussy juices. At the same time, I felt someone stroke my bottom. Slowly, someone carefully pulled out the butt plug I had been wearing all evening. I moaned a little with the pleasure of getting it out, but it didn't take long before I felt the sensation of lubricant as it began to flow down my ass towards my hole. Suddenly I felt pressure against my hole! I managed to turn around a bit to see Hanna now stood behind me and pushed in with her strapon! Again Bree took my head and held it in place. The tongue worked steadily but the feeling of the strapon dildo pressing into my anal hole was overwhelming. I now felt another hand begin to stroke my hard cock, it had to be Lisa. Hanna's hands firmly gripped my hips and squeezed the strapon in and out at a leisurely pace. She did it carefully but increased the pace a little. Lisa just continued to jerk me and my tongue worked hard for Bree's pussy lips. I was just about to come when Hanna pulled out the strapon and Lisa let go of the dick a little.

Hanna disappeared and retrieved something. I heard the sound of plastic again, it sounded like it was the diaper Bree just used! She slipped it under me and left it on the bed as Lisa continued to jerk me off. At that same moment I came in an explosion of orgasm! Sperm gushed into the diaper that Hanna held under my cock. Lisa didn't stop jerking me, she just continued more and more! "Please stop!" I just felt the pain of orgasm spread throughout me. I was so sensitive. They all just laughed. Hanna pushed the cock shaft of my dick back and moved the sticky diaper into place which was now full of both sperm and all the pussy juice from Bree! The girls got up and got dressed. Lisa gave me a hard slap on the bottom to squish the front of the diaper so that all the wet sperm and pussy juice was mashed together. Bree kissed me on the cheek and thanked me for a wonderful experience. Hanna slaped me hard also on my ass before looking at me.

"Just lay down you little diaper sissy, it almost looks a bit full, but you like sticky don't you? I know you like this, good hot pussy juice mixed with your sticky sperm that you love so much! But don't worry, that diaper can take a lot more! Sleep well sissy."

The girl's took their wine glasses and disappeared out of the room with a laugh. The door closed as I was now lying all alone. It was not good that my stomach was pressing on me and I now had to pee! I held on as long as I could but eventually gave way and the diaper filled up with warm pee mixing with all the cum and pussy juice that was in my diaper. Embarrassment and shame spread through me before I fell asleep.

I woke up to a spank on my stuffed diaper bum. My eyes opened slowly, the sight of Hanna standing and looking down at me with her arms crossed and a wide smile didn't make waking up that much better.
"I see the little diaper girl peed her diaper again, I didn't know that you were so dependent on the diaper little sissy, but it's a good thing we were kind enough to leave it on! Now get up, it's time for shower."

It was so nice to hear the water running from the shower, how it flowed down my body without anyone coming to disturb me. It was peaceful to rest. My thoughts went round and round about the night before. Had I really had sex with Hanna's friends, not the least... had Hanna really fucked me with a strapon? I could feel that I was tender in the back, it was not a dream. I must have been in that shower for a long time, because when I came out of the zone I was in, the skin on my fingers had started to turn soft and white. It was nice to dry off, I might finally be able to calm down a bit. I dried myself and inside the room were still my usual summer clothes, but of course there were red lace panties there also. I picked them up, and slowly I stroked it over my cock shaft, as a tingling pleasure came over me. At that very moment, Hanna was standing there.

"Can't you just put them on right away? You know that you want it, isn't that true little sissy?"

I held the towel in front of me again and looked at Hanna a little annoyed. "No Hanna, now it really has gone on long enough. I won't deny that there have been some good times, but this teasing stuff you do to me, it has to stop now." My look spoke volumes, as I felt tough now. At that same moment, Hanna just came straight at me, pushed me back which took me so completely by surprise that I fell onto my stomach on the bed. She took her knee and start pressing it on my back while she pushed my head down with one hand.
She started to hit me again and again on my bum. I screamed stop, but it didn't help. She just pushed my head harder down my pillow while she continued to spank me. I couldn't resist, I gave in and she noticed it. She slowly stroked my ass before she put her finger between my ass and started take it calmly in and out, inside my stretched out ass.

"Now listen you little pervert sissy. I've only been mean to you when you deserve it. Don't deny you don't like panties you fucking sissy. Now put the panties on, and I'll be nice to you for the rest of the day. But these panties are going on! Do you understand that, bitch?"

"Yes Hanna, I'll put them on." Slowly she got off me and stood by the edge of the bed. I found the panties and slowly pulled them up between my legs. I didn't want it to make tingles in me, there was that something special that just came from the feeling of them. Obviously I wasn't good enough to hide that I liked it, she just sat there and grinned. The panties were now perfectly in place, but a small bulge began to appear. Hanna just laughed and went out. While I was getting dressed, I heard Hanna shout goodbye and a car left, was it her friends who had left?

I stopped a bit when I was getting up to fetch my usual shorts and shirt. I felt like some sperm was leaking out in my panties! I grabbed my shirt and shorts and was about to go into the bathroom to dry myself when Hanna called after me and told me to come right away. I decided to check the panties later, I thought as I got dressed. I met Hanna outside, as she waved goodbye to the car that was driving away, clearly her friends.

"Why were you so slow? You could have said goodbye too. Anyway, sit down and I'll bring some breakfast out to you."

I sat enjoying the sun, with a delicious breakfast and only the sound of birds chirping. Hanna was mostly inside fixing things, clearly cleaning up after yesterday perhaps? I just enjoyed the moment and the silence with my ear buds and music from the phone. I don't know how long it lasted but I got a slap on the bottom, my body jerked and I was about to open my mouth to curse when my aunt was now standing next to me. I became more puffed up and said nothing when she looked at me with a mysterious look.

"Hello to you too, is that a grumpy boy I see here? Something wrong? I just got back, it's good to be back here. So, did you and Hanna have a nice weekend?"

I wanted to get up to start to chat with her, now I had a opportunity. "No, Hanna has been mean to me, just mean to treat me like a...." I stopped talking when I saw Hanna come out.

Auntie looked at Hanna who came over and looked at me. She looked stern and asked what I meant. I didn't know what I was going to say. I couldn't say everything, but I couldn't say any more as suddenly Hanna started talking.

"Hey mom, it's so nice to have you back, my friends have just left. Did work go well?"

Auntie still looked at both of us and asked her, "What's the matter with Sander? Why does he say he hasn't had a good time? You must have cared for him within my rules?"

Hanna looked at me sternly with angry eyes before answering.

"Of course mom, but Sander hasn't listened to any of my orders when it came to having to wear a diaper, which he clearly needed! This little diaper boy really needs a thick diaper at night, and he should be glad that I bothered to take care of him!"

Auntie started to look at me sternly, just as I was going to answer these idiotic charges from Hanna, Hanna interrupted me again.

"Sander! Have you done it again? Mom look what the little diaper boy is wearing! Are you wearing one of my panties?"

Auntie was a bit startled, she looked at me and held me by the arm and pulled down my shorts! Her eyes grew wide but tight and the arm grip she had on me became firmer. She pulled my shorts all the way down so I was just in my panties with the shorts down to my ankles, and she opened her mouth with a really sharp tone.

"Are you standing here claiming that my kind daughter has been mean to you? Here you are in one of her panties! Have you been stealing them you little pervert! Believe me, I know all about sissy boys,
since you like it so much I'll fucking treat you like one for the rest of the summer! Not only are you talking crap about my daughter, you're standing there in one of her panties that you took from her and you can't fucking deny that you clearly like it! I see you have sperm stains on her panties! Now you come with me you little diaper sissy, you can get what you deserve, but sticky panties can't you have! Come with me!"

Hanna just smiled as aunt took me by the arm. She dragged me into the forbidden room to stop at the changing table.

"Now you take those clothes off! Lay down naked on that table at once, I'm not going to hear a damn word out of that mouth of yours!"

I was completely startled and scared, she doesn't believe me? I didn't dare do anything other than lie down on the changing table. I just closed my eyes in shame, I didn't want to be here!

I kept my eyes closed, I didn't want to look her in the eyes, it was just the feeling of shame! She lifted my hips a little, I just lifted my bottom myself without protest. She put a plastic sound under me, clearly a diaper. She bent my bottom back down and wound it up between my legs. She nudged my head at me.

"Obviously you've been spanked by Hanna, you've clearly deserved it! Now get up you little sissy, stand up so I can check you out and I'll find some suitable clothes for you."

She continued to rummage around in some drawers. She found something that looked like a t-shirt, but it was something else, because she pulled the garment up my legs and up my chest and got my arms inside the garment. When it was in place I noticed it was a bodysuit. The crotch of it shaped like a panty and went between my legs and up behind where it shaped like a panty over the thick diaper. When she fastened it in the back with hooks, it tightened tightly around my hips and stomach. It created some real curves and a huge bottom with the diaper pushing out the front and back. Then she disappeared and quickly returned with a pink skirt. I put my foot inside and she pulled it up. She worked quickly and efficiently to put it in place. I noticed now that the bodysuit had a slightly wide pink collar, it so terribly embarrassing! But she didn't stop there. She found some knee-length white socks. She disappeared back into those drawers, finishing with a large pink pacifier. Now she stood calmly studying me, she smiled and took me to the mirror. I saw myself! The skirt bulged out in the front and the bulge in the back and made it hard to cover the thick diaper between my legs. She saw the fear in my eyes, but the intensity in her eyes was not gone.

"So you like to be a little sissy. I can make you a sissy. Think when my sister, your mother, finds out what a little sissy son she has! But I'll tell you a secret little sissy! I love to break down boys like you! I'm going to break every little barrier you have left in your body! You clearly enjoyed your sperm so much! Let me be kind to you and let you have it again! Little diaper sissy!
Hanna, come help me."

Hanna came in, she just started laughing when she saw me. She looked at her mother to ask.

"What do you need help with?"

Auntie looked at Hanna and smiled.

"Take his arm and I'll take the other."

Both of them grabbed my arms, I flinched but started to fight back! But it was clear, I lost easily here. They dragged me away against my will against the great cross. They took each of my arms and chained them in each arm cuffs and the same with the legs. Now I stood there tense, scared and ashamed. Both ladies stood with their arms crossed and looked at me sternly.