Boarding School Ch. 02

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The second night of my boarding school experience.
2.1k words
4.59
16.5k
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Part 2 of the 7 part series

Updated 06/14/2023
Created 02/07/2023
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As I walked back to my room I had trouble comprehending what had just happened. All those new feelings of pleasure and excitement, the feelings were indescribably beautiful. Yet from everything I have learned it was so wrong, no boy should get pleasure from another man, especially his teacher. It felt so wrong yet it felt so right, so good.

The next night I was knocking at his door at 7pm.

"Come"

I opened the door and entered, he was sitting in the same chair and said the same things.

"Close the door and lock it. Now take off all your clothes."

This time it was different though, it felt different. As I was shedding my clothes I felt a tingling, stirring in my groin. When I was naked standing before him, my cock was getting hard.

"Did you enjoy last night?" he said.

I could feel my face blushing.

"From what I can see, it looks like you did. Did you masturbate last night? Be honest."

"No Sir, I didn't," I said.

"What were you thinking about when you were in bed last night?"

"I was thinking about what happened with you." I stammered.

"Good, good, so you did like it then? Well you liked it because it felt good, it gave you pleasure and you saw it gave me pleasure. The thought that someone could use your body for their pleasure also turned you on. Is that true?"

"I g.g.guess so."

"That is good, because over the next few days I am going to teach you, train you how to give me pleasure, all the things that I like, do you understand and are you willing to learn?"

Again I stammered out a Yes.

"By letting yourself, your body, give me pleasure, you will also get pleasure."

"I have a present for you, on the table." He said.

I looked over to the table and saw a pair of white silky satin panties and matching bra.

"I want you to put them on."

I moved to the table and gingerly picked up the panties, they felt so soft and slippery as I rubbed them my hands. Then I proceeded to put them on. As I pulled them up my legs they felt so good against my skin. I tucked my rock hard cock into them then picked up the bra, slipping my arms through the straps.

"Come over here and let me do that up for you, it is a training bra so it will fit you perfectly."

I walked over and turned around so he could fasten the clips. The feeling of the restriction on my shoulders and around my back was indescribable and the soft satin made my nipple rock hard.

"Now turn around" he said.

He then began to trace his hands all over my body as he did last night, paying special attention to caressing my ass through the panties. The sensation was so over powering my legs trembled. Then he started to pay special attention to my front running his fingers across my panty encased cock. I nearly fainted from the pure pleasurable sensation.

"Now to start your training. Watch what I do next and learn because you doing this to me will give me so much pleasure. The more you do it the more you will want to do it until a stage where you will crave it."

With that he pulled the elastic of the panties out and placed it under my balls. He took my cock in his hand lowered his head and kissed the tip, the side, the shaft all the way down to my balls. Kissing, kissing, kissing, then back to the tip, where he replaced the kiss with a tongue. He licked the slit, all around the head, then underneath it and down the hard shaft. He then licked all over my balls.

My legs were shaking my cock was twitching from an overall touching sensation of pure pleasure. Moving back to the tip he opened his mouth and took the head in, swirling his tongue over and around it with his lips closed around it. As he moved his mouth further down my cock his tongue keep floating over the entire length. He then started moving up and down on it, up until just the head was in then right down to my pubic area and balls, engulfing my entire shaft. My heart was pumping, legs trembling, I had never experienced such a feeling, sensation, in my entire life, I wanted it to never end.

A tingling began in my groin, growing, getting stronger then all of a sudden I came. Shaking, trembling I had to hold on to his shoulders to prevent collapsing. Even though I had masturbated many, many times, I had never had a sensation like this.

He then replaced the elastic of the panties over my cock, which was now back encased in its silky satin enclosure.

"Did you like that?" he asked.

All I could do was mumble.

"I guess you did, thought you might. Now it is your turn to try. Kneel down between my legs and undo my trousers and slide them down."

I knelt down or more like fell down, my legs were so weak. Then fumbling with the belt, undoing the buttons and zipper, I grabbed both sides of his trousers and pulled them towards me. He lifted his ass and I slid them to his ankles. The sight in front of me was a 7" bulge encased in black sating panties.

"Touch it." He said.

With a shaky hand, I rested it on his bulge.

"Stroke it."

I ran my hands lightly over it, so warm in soft material, hard yet soft, he sighed. He was obviously enjoying the feeling, as was I. He took the back of my head and pushed it towards his crotch.

"Kiss it, rub your face and mouth over my cock, breath me in and with your warm breath, out over it."

It smelt so good and was so hot, the sensation of my cheeks on the satin encased bulge was mind blowing. I kissed up and down that shaft with a little bit of tongue at times.

"Now take it out and kiss it."

I pulled the panty elastic out and under his balls as he had with me and this beautiful hard perfectly shaped cock sprang free. I held it with one hand, it felt so soft yet hard, so warm and so good. A perfect specimen of a perfect cock. Well in my eyes anyway, I had never seen another cock like it. The other guys in the showers had nothing on this one.

I was so jealous of it, its size, shape, texture, veins. I couldn't explain the feeling that was going through me holding it, I was in love with it as I leaned forward and kissed the tip of the head. The sensation on my lips was earth shattering. Soon I was kissing it all over, up and down the shaft then down to the balls, kissing them, they felt so good on my lips too with the cock resting on my head.

"You are very eager" he said, "but you are doing well, I am pleased. Now I want you to replace your kisses with your tongue, but first take off my shoes, socks and panties. I want you to have better access."

I hurriedly took off his shoes, socks and removed his trousers, then slid his panties down and off. I couldn't wait to get back to my new prize, toy and pleasure giver.

I crawled between his legs, both his thighs resting against my arms, so warm, it felt so good, then I took that cock in both hands leant forward and licked the head. I noticed clear liquid at the slit and look up at him.

"That is called pre cum, it leaks out when I get aroused, it is very tasty, have a taste."

I ran my tongue up and down the slit and took some in my mouth for a taste. He was right it tasted a bit sweet but very pleasant. I then squeezed the head to get more to taste.

"Did you like that? There is more to come, you will love it." He said.

I could just nod as I continued my tongue exploration. I covered every inch of it before moving down to his balls and proceeded to lick all over them.

"I now want you to try my cock in your mouth, slowly at first, just take the head in your mouth. Watch your teeth, try covering them with your lips. That's it, good, now look up at me while you do this, I want to see the pleasure in your eyes."

That head felt so good in my mouth as if it were meant to be there all the time. I twirled my tongue over and around the head, mixing more pre cum with my saliva and swallowing. It did taste sweet, warm, slippery and sweet.

"Now try to take more of it in, don't rush it, just as much as is comfortable, as time goes by you will be able to take the lot, but just not yet. That's it go up and down, take as much as you can. Tickle my balls and the skin between them and my ass as you do this. That's it, oh that feels so good, you are doing well."

With one hand I was stroking that cock up and down, with the other just lightly stroking his beautiful balls and the place beneath them. My mouth was taking as much as it could before gagging, up to the head then down again, it felt so good, so hot, so right.

"Now" he said, "In a short while I am going to cum, when that happens my cum is going to pump out. I want you to take it all in your mouth, so when it happens I want you to move up so just my head is in your mouth, leaving room for my lovely hot cum, do you understand?"

I mumbled and nodded.

"I want you to keep my cock in your mouth until I have finished, I will tell you when, and then swallow it. It is an unusual taste but not unpleasant and the reason I want you to swallow is that it is full of vitamins and is good for you. The more cum you take in over time the more will be absorbed by your body and the more you absorb the more you will want, need and crave. Do you understand and will you do that for me?"

I nodded, I was so engrossed with the sensation of that cock in my mouth I would have done anything he wanted. I made love to that cock for the next 5 minutes or so, I couldn't tell as time had stood still. He was moving more and more under my touch, his hips thrusting forward, he was getting very excited and I was so turned on by the pleasure I was giving him.

"I'm getting close." He said, "Are you ready?"

I nodded.

"Here it comes, ah, ah aaaah, yes, yes, YESSSSSSSSSS."

As I was bobbing on his cock and stroking it with my hand the first thing I noticed was the head began to swell and after his warning I move up to have just the head in my mouth, but was still continually stroking the shaft. Then it happened, the first shot hit the roof of my mouth and settled on my tongue. My lips could feel the cock pulse. Then another and another, it felt so good pulsing in my mouth. I can't remember how many but my mouth was filling with warm juice from that cock. Finally he said:

"OK I have finished you may take your mouth off my cock, look into my eyes and swallow."

I did as I was instructed. It was an unusual taste, indescribable really but not unpleasant but it take a few gulps to get it all down.

"Good boy, you have down well for your first lesson, now use your mouth to clean my cock."

I leant forward and proceeded to lick any and all remaining cum from the head, there wasn't much as I had taken nearly all of it.

He stood up, patted me on the head and put a robe on.

"Now get dressed, but leave the panties and bra on. I want you to wear them all day, except in the shower of course. I want you to get used to girly things, the sensation on your body of soft, silky material. Is that understood?"

I nodded.

"Good, you have done very well for your first lesson, I am pleased and feel you got as much pleasure as I did. You will be here tomorrow at 7pm and we will start your next lesson. Good night."

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SissyBoy1WarszawaSissyBoy1Warszawa8 days ago

You do a great job of telling the story of a young boy's next steps towards becoming a sissy for his teacher. You describe beautifully how she learns to play, lick, suck real cock and swallow cum. It's nice that you said that now the boy has to wear panties and a bra and wear them every day. I would really like to be like him (that's why you're afraid to give him a name, it's so impersonal, these characters lack character). I will read with great interest the next stories and what limits this boy has to overcome and what else will the teacher come up with? 🧒🏻♀️👣🍦🍼💋💦👨🏻‍🎓

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

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

AnonymousAnonymous7 months ago

Nice build-up. i would love to run that beautiful cock all over my face: my lips, my cheeks, my nostrils......then take him in my mouth! i'm also fairly new to oral, so I would not e able to fit his whole cock in my mouth...only 4 or 5 inches. But I would be so careful and show the pleasure in my eyes!!

AnonymousAnonymousabout 1 year ago

Beyond hot…so hot to imagine having my cock kissed and sucked while wearing a pretty little white “training bra”…love that expression “training bra”, like being trained to get men’s cocks hard..can’t wait for more

AnonymousAnonymousabout 1 year ago

They should have fucked

AnonymousAnonymousabout 1 year ago

Made my dick hard I was hoping that they fucked

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