The worst / best detention ever. 2

788Report
The worst / best detention ever. 2

*there is a part one to this and once again grammer isn't perfect*



The thought of nipple torchure made me excited but I dare not tell Mr.B that. He grabbed my arm and told me to unbutton my top and take that along with my bra off and place my hand on top of my head, When I took too long he sighed shaking his head and laid some more slaps on my ass. I sped up as to not upset him anymore.

He took in my triple ds and large nipples smiling to himself as though he had hit the jack pot. I got smiles from the other boys as well. I wondered if anyone would believe this if I told them and once I realized no one would believe me I thought it best to be submissive as best as possible.

He took a step to me holding a small box of items I feared to even look at. He pulled out two nipple clamps that had small teeth on them. Oh how I prayed to myself they weren't sharp. He licked his lips and pinched my nipples making them hard before applying the clamps. My fleash seared in pain and turned bright red and I closed my eyes as if somehow that would help.

He clapped his hands in front of me, "Keep those eyes open! And keep your breasts thrusted out! I want them pointed out at all times or you'll be bent over my knee again you hear me Lilly?" He asked,

I nodded thrusting them back out and getting a hold on the pain. I looked down and seen every man in the room had a buldge. I couldn't help but feel a little proud of myself. Mr. B grabbed a few weights from his box and added them to the clamps chain that connected them. Then he grabbed a whip and started the lashings.

WHIP WHIP WHIP "Beg me for more Lilly! Be a good girl." WHIP WHIP WHIP.

Tears began to fill my eyes but I honestly wanted more. "Please sir more, make wet."

He smiled and I got over 100 more lashings but then the pain got serioiuse and I put my hands down to stop the whip. He didn't like that and motioned for the boys to stand up. He handed the whip to one while one was to hold my arms back. The third took a cane to my ass and the back of my legs.

It went on for a while and I wondered if the small things I did really deserved this. Mr. B seemed to know what I was thinking as he came up to my face, "Look Lilly you need to learn your place and I have found with young bull headed women as yourself need a proper punishment at least three times a week to do so. So you shall come here with these boys and I three times a week untill I see fit got it? And do not worry my pet sometimes it will be for a treat as well."

He reached between my legs then pinching my pussy lips and running a finger up and down my slit. I quivered in pleasure and realxed. He found my clit then and rubbed my nub over and over telling me I am never to cum without permission. I held back moaning and leaning into the boy who held my arms. Mr. B grabbed me by the neck and laid me down on his desk having a boy on each side hold my legs apart and the third was to yank the chain every few seconds.

He took a thin long wooden stick and rubbed my clit over and over making it pink and swollen again. He then lifted it and smacked my pussy . I screamed and he shook his head and pulled my skirt off shoving part of it in my mouth and slamming the stick down six times in a row. I closed my eyes letting a few excited tears fall.

Then came the clothes pins, He put 3 on each of my pussy lips making them fan out , leaving my clit out. He grabbed a vibrator and turned it on max speed and showed it to me. My eyes grew wide as he took his time going down my thigh. He smiled rubbing it around my clit being careful not to hit it. I bucked a few times hoping to get it to it my pulsing clit but he backed away farther so I held still whimpering.

He pulled it down to my ass hole and circuled and played with its entrance. I chewed on my skirt and watched as he put on a white latex glove like the doctors wear. He then poured lube there and began to slip a finger in. I wasnt sure if I liked it or not but it didnt matter because it was going to happen no matter what. He finally got it in all the way and then began on working in two. And then before I knew it he had three and was pulling a butt plug from his box with a pink jewlel at the end. He came to my ear then and began to whisper.

"I got this to match that pretty pink bow you like to wear."

My heart skipped , so he had planned it all I thought. He began to work it in and even though he had stretched me some it still hurt.

"There its in. And it looks very good." He smiled giving it a playful tap and taking off his glove.

He stood up and began to work his pants down off his athletic body. Being a teacher and football coach paid off. I shivered when I see his 8 inch cock it had to be 3 inches wide. And I knew he wanted my virginity.

"I'm going to enjoy this Lilly. You may not but it would be selfish to deny me pleasure and really denying yourself of it for later. If you fight me it will hurt worse and you will not leave this class untill I have fucked your tight cute little pussy."

He came over me then and rubbed his dick head on my clit. He yanked the clothes pins off and spit on my pussy entrance while rubbing it some more. He slid the head in finally after some pushing and stopped to grit his teeth before slamming down taking my womanhood for his own pleasure. I took the pain like a champ knowing it was a part of this no matter who did it.

His cock filled me up and stretched me untill I thought he would push me in half! I moaned and coed and breathed heavy as his strides got longer and faster. I tried to hold back from cumming but I couldnt help it and let it go,. Once he had cummed he pulled me to my feet and handed me my clothes.

"I'll see you in 2 days Lilly. . .and dont think I will easily forgive you cumming without permission. Whether there was a skirt in your mouth or not...."

Similar stories

April - Part II

Thank you, everyone, for the nice comments and generally positive ratings. I apologize that part 2 has taken so long, but I wanted to make sure it was as good as I could make it before posting. I hope you enjoy this part, and look for a part 3 in the coming weeks. Please continue rating and commenting, and if you don't like elements of my story telling, please let me know in the comments how you think I could improve. Rob and April lay in April's bed, lost in their own post-coital thoughts. They had assured one another that this...

1K Views

Likes 0

College Party Gone Right For a Change

Saturday 12:00 AM “Fuck-“ I was cut off by the wall hitting my back behind me. His hands had me by the tits, shoving me against the wall. My fingers locked on his shoulders to keep from slipping off the dresser; funny clinging to source, I thought. His breath was hot against my skin hovering above my cunt. My head leaned back as he kissed my panties, how the hell did this happen? And I remembered, Friday 5:00 PM “I still can’t believe you convinced me to go to what’s-his-face’s party, I should have asked for a better bribe.” I said...

807 Views

Likes 0

SOMETHING NEW_(0)

“You ready,” Debbie asked her friend Maureen as she stopped by her best friend’s desk, “I can’t wait another minute, I’m just about ready to burst!?!” “Me too,” Mo replied while putting the finishing touches on a report that Mr. Bently had ask her to prepare before his trip to New York later that afternoon, “just let me drop this off at the boss’s office, he’s been on my case all morning to get this done before noon!!!” “No problem,” Debbie replied as they made their way to Mr. Bently’s office, “are yours full, mine feel like they’re gonna explode!?!” Mo...

2.4K Views

Likes 0

The Boss's Daughter, Ch 1: The Beginning of the madness

I grew up in a small mountain town, to give you a clue my elementary school preschool -8th had only 58 kids in it. To say everyone knew each other is an understatement. I was an average boy, and everybody loved my for my kind heart and large since of humor. Growing up I was with my friend Collin a lot, the kid who has everything. We were always on dirt bikes, quads, boats, you name it, we did it. Always tagging along with us was his younger cousin Alexis. She was a cute girl, but much younger than I. Alexis...

1.4K Views

Likes 0

From: Bisexual Jeff?Rules For Comment On My Stories!

Bisexual Jeff…Rules For Comment On My Stories! Judging by the tens of thousands of times all my stories have been read, most of you have enjoyed them. Some haven’t and that is fine too, I’m not trying to please everyone, or really anyone, I’m writing what buzzes around in my head at times. Enjoy them, don’t enjoy them…totally up to you. But do NOT leave shitty comments about someone you know who died of AIDS, please, THIS is not the site for that. Everyone reads the stories, the titles pretty much tell you what the story is, so if you click...

1.2K Views

Likes 0

Naples, Florida & Beech Mountain ,N.C.

Naples , Florida and Beech Mountain N.C. Sandra and Debra were full of questions as she banked the plane south.. I told them of the plan Donna and I set up and how well it turned out. They were really impressed that I took on Stanley and had broken his nose, his collarbone, and a few ribs. Debra hugged and kissed me several times in gratitude.. I think she wanted to do more , but Sandra cooled her down some.. “We need to discuss what will become of you now that you can't return to Beech Mountain any time soon. I...

1.1K Views

Likes 0

SLuT9 pt 22

CHAPTER TWENTY-TWO High On Life Sunday December 23rd, Night For the next two hours the house was organized chaos as Jennifer drafted everyone into the effort to clean and prepare for the party. Dave and Emily were put to work dusting, vacuuming and cleaning the living room, Olivia and Hayley were drafted as assistant cooks for Jennifer as she prepared as much food as possible for the party tomorrow. Megan was sent to her room to get it clean while Molly swept and mopped the hardwood floors in the main hallway. Once they finished with those chores, Jenn sent Dave, Em...

1.1K Views

Likes 0

Life of a Playboy Chapter 5

CHAPTER 5 I stood in the lab, theoretically paying attention to the monitors before me and crunching numbers. But really, I was surreptitiously checking out the various women entering and leaving Mrs. Robinson's office. The posting had gone out across the college for female volunteers to participate in a biology study affecting human sexuality. It was a paid study, so there were many more girls signing up than positions needed, and Mrs. Robinson was able to select only the hottest co-eds on campus. The more the beautiful girls went in and out, wearing skimpy clothing and flashing some skin, the more...

1.1K Views

Likes 1

My Bus Journey

My Bus Journey As I stepped onto the bus, it was jam-packed full, with many people standing in the aisles. This journey was going to be a long one. I looked around the bus at the passengers, and then I saw her. I'd seen her previously, but only in passing. Her mousey brown hair was down to her shoulders, a thin button-down summer dress with nice small breasts, great legs, and an ass to die for. I decided I was going to try and enjoy this journey. I moved my way through the passengers until I was standing directly behind her...

1.2K Views

Likes 0

Jack in the Cast

Jack in the Cast The light knocking on the door caused Jack Benson to take a deep breath, grit his teeth, and finally call out. “Yeah, who’s there?” From behind the closed bedroom door came the low voice of Kathy Collett, “Jack, it’s Kathy. Can I come in?” Sighing loudly Jack answered “Ah yeah, I guess. Come on in Kathy.” “I brought you a present for Valentine’s Day.” She began as she swung the door open and waltzed into the room carrying a wrapped box, a bouquet of flowers and a card. When her eyes came to rest on the sight...

943 Views

Likes 0

Popular searches

Share
Report

Report this video here.