Boarding School Ch. 03

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Learning more every day and not about school.
1k words
4.61
9.4k
7

Part 3 of the 7 part series

Updated 06/14/2023
Created 02/07/2023
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The third night I arrived and it was the same procedure, but this time he said:

"Take off your clothes, all of them."

So after stripping down to my bra and panties.

"Those too." He ordered.

I reached behind and unhooked my bra, letting it slide off my shoulders, down my arms and drop to the floor. Then hooked my thumbs in the elastic and slid my panties over my thighs and let them drop to my ankles before stepping out of them.

The feeling standing before him naked and thoughts of being used for his pleasure were evident as my 6 inch cock was now standing at full mast. There was a grin on his face.

"I see you are enjoying this, that is good, now come here."

I moved slowly over and now stood just inches from him as he proceeded to stroke me all over again, savouring the feeling of my soft, smooth skin with his finger tips. The feelings were the same as I shivered and trembled at his touch. He stoked from my feet and ankles up the outside of my calves and thighs, then back down the inside. Then up my legs again to my hips and around to stroke and caress my ass, up my back, down my arms, up again then down my chest and stomach.

"I love the feel of you, do you like my touch?"

I mumbled a YES and I felt myself tremble and my knees get weak. He didn't touch my cock, which is what I craved for. He was in control and was going to make me wait and give me satisfaction at his pleasure.

He stood up and led me by the hand over to a table.

"Get up on the table and lie on your stomach."

He then placed a pillow under my head and got me to raise my hips to place anther one under there. I then heard the click of plastic and then felt warm liquid being poured over the small of my back, ass and thighs, a feeling that made me shiver. "Click" again, then I felt his hands.

So soft, so tender caressing the slippery liquid all over my lower back my ass cheeks and thighs. The lower back and ass cheeks felt good, but the part I liked was the inner thigh massage. His hands moved up and down with his thumbs on the inside, meant with every stroke his thumbs would part my ass cheeks.

As he continued with each stroke I felt my legs being parted ever so slightly. I am not sure if they were being forced apart or whether it was an involuntary action on my part, but it felt incredible. With each movement, his thumbs moved over my little hole, it felt like an electric shock and with every pass there was a little more pressure.

His thumbs were soon replaced by a finger, which, with every stroke, passed over my hole and each time again, a little more pressure. My hole seemed to be relaxing to his touch. Each time his finger seemed to go deeper at my opening until one pass it slipped in slightly, only for an instant and then continued. This continued until one pass his finger slipped in, only to the first knuckle, but stayed there. He then began to move it around, easily into my now relaxed hole, it felt so good. Then he pushed further to the second knuckle my relaxed ass hole accommodated it. He gently moved it in and out, slowly. Each time I could feel it going deeper with the inward push. Soon I could feel the rest of his finger against my cheeks, I knew and felt he was all the way in.

In and out he began and with every stroke came an instant of pure pleasure. Later I was to learn he was caressing my prostate. Then on one outward stroke, the first finger was joined by another. I was so relaxed my little ass accommodated it easily, my cock was rock hard against the pillow and I moved my hips rubbing it against the soft material. I had never experienced such sexual, erotic pleasure in my life.

Laying there enjoying this new sensation his fingers suddenly left my ass. "No, no," I thought, put them back they felt so good. Next I felt something hard at my hole. It wasn't a finger, it wasn't his cock (although I had never experienced what a cock would feel like down there, I knew it wasn't one.)

"Just relax." He said. "This is a plug, it is designed to make you more susceptible to opening up for pleasure."

As my hole was so relaxed from his fingers, he started to slide it in. My hole started to be stretched wider and wider as it slid in, there was no pain but there was again pleasure. Feeling my hole opening more and more until it suddenly snapped shut around the base. I felt a fullness of having a large object inside me and my hole closed around it securing it in place. It did feel natural, as if it was meant to be there and it did feel good.

I then felt a towel on me as he wiped all the oil off my body.

"Get up." He said.

I did, all wobbly on my feet, I grabbed him to steady myself. He then handed me a new black bra and satin panties.

"Put these on. You must keep that plug in all day, except when you go to the toilet of course, You will then have to replace it. Do you think you can do that?"

"Yes." I replied.

"Tomorrow I will take it out for your next lesson. Also don't you dare masturbate, as I want you highly aroused and turned on tomorrow night."

I put on the bra, he again helped me with the clasp, then slid on the panties, they felt so good against my cock, then I got dressed.

He then took me in his arms, held me tight to him and kissed my forehead.

"Good girl"

I felt a warmth of affection when he said that. I liked it very much, it felt right.

It was difficult to walk naturally as every stride I was aware of my ass being filled with a foreign object pressing against the inside of my body. So with every step my body was sensually touched from the inside.

I left wondering what could possibly happen that was better than tonight.

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SissyBoy1WarszawaSissyBoy1Warszawa12 days ago

You describe it as if you were the main character, this boy, learning to submit and accept the pleasure of becoming a sissy for the teacher. If that's the case, I sincerely envy you and I'd love to be in the sissy's position. I would love to feel those fingers on my smooth body, digging into my ass hole and then squeezing the butt plug. I imagine what will happen during the next meeting and what the sissy will experience. 🧒🏻⚧️👙👨🏻‍🎓

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

Best regards, SissyBoy from Warsaw, Poland. 👩🏻‍🦳⚧️❤️👧🏻🧒🏻

AnonymousAnonymous7 months ago

So nice. There's nothing quite like the full feeling of a large plug inside your ass, walking around, even going grocery shopping. No one knows why there's such a happy look on my face. And why I sometimes reach back and reposition the plug back inside of me if it nearly slips out.

AnonymousAnonymousabout 1 year ago

I feel like the author knows everything that has gone on in my life…nothing hotter than strutting around in a black bra and panties while feeling the constant boi pussy stimulation from a massive rigid plug

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