How I Became a Cheerleader Ch. 18

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Guy changes schools, life and sex to fit in.
5k words
4.77
36.6k
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Part 18 of the 20 part series

Updated 06/07/2023
Created 10/10/2010
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DMaster_14
DMaster_14
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Mom Jason and Heather returned home the following weekend, leaving Trent and I alone in the house. The first thing that he did was to order that his secretary report to his office for dictation.

The limo had barely left the driveway when he turned to me and said sternly, "Miss. Holcombe, be in my office in thirty minutes, we have a client due in for a meeting at two and I want to dictate a letter before he arrives."

"Yes sir, thirty minutes." I responded meekly, turning and waving goodbye before running into the house and up to the shower. A quick and thorough cleaning, inside and out and I was back in the closet, getting my clothes. I did my make up just as quickly and took my suit to the spare room my mother had just left.

The grey high heels, the smoke grey hose, teddy with garters and the skirt and jacket. I was waiting patiently outside the office, pad and pen in hand when he strolled past me, showered, shaved, and dressed in a suit, cup of coffee in his hand.

"Follow me Miss. Holcombe." He said sternly.

I kept my head down and trailed behind him into the office and saw that he had moved one of the straight back chairs from the kitchen to in front of his desk. He settled himself magnificently behind the desk and pointed to the chair before it, I seated myself on the very edge, pad and pencil poised and ready.

"Miss. Holcombe, before we begin the dictation, we have to discuss your office attire."

"What is wrong with my attire sir?" I asked surprised.

"That suit is fine, the shoes and hose are also within the office dress code, but the code also clearly calls for a blouse. Please remove your jacket and show me your blouse."

"But sir..."

"Remove your jacket Miss. Holcombe." He said sternly.

I was surprised by his request, wondering where he was taking this, but I stood and obeyed his instructions. I slipped the jacket off and draped it over the back of my chair, and turned to face the desk, my head down, clad only in my skirt and teddy.

"Where is your blouse Miss. Holcombe?" He asked.

"I'm not wearing one sir."

"I see, and about your skirt."

"My skirt sir?" I questioned.

"Yes, the dress code clearly states that skirts must come below the knees. Does you skirt come below your knees Miss. Holcombe?"

"No sir," I said meekly, not making eye contact.

"Remove it." Trent ordered.

I unzipped my skirt and let it fall to the floor. I stood before his desk, clad only in my teddy, stockings and heels.

"At least you are able to follow part of the dress code, the stockings. However, as you are obviously in violation of the rest of the dress code, I have no choice but to discharge you from this company."

Finally I saw what he was planning, I had to plead for my job, do anything it took to keep it.

"Oh please sir, don't fire me." I begged. "This is the only position I was able to get. If I get fired, I will lose everything."

"Then you should have thought of that before you came in here in clear violation of the dress code."

"But sir, I didn't know I was not following the dress code." I insisted.

"Regardless, you are in violation of it. Ignorance is no excuse. You are discharged."

"Please sir, I'll do anything to keep this job."

"Anything?" He questioned.

"Anything sir," I responded, falling to my knees before the desk.

"Then crawl over here and take care of this." He ordered sternly.

I took his tone seriously and crawled around the desk. I saw that he had his dick out. I reached for it. He was already excited and hard for me. I licked my lips and slowly climbed up his legs. I took him in my mouth and swallowed him whole. I wanted to show him that I would do anything to keep my job.

My head bobbed up and down on his shaft, my tongue never stopping and my teeth dragging slightly on the pole. He griped my head and controlled my speed. I thought he would want me to get him really horny, but he slowed down my progress, making me take each inch in separately.

I worshiped the column of flesh before me. I licked the entire length before going beneath his balls and licking there to. I wanted him nice and wet for my passage. My nose wiggled in the space beneath his scrotum and my tongue tickled his perineum. I heard his sharp intake of breath at that and did it again several more times.

He pulled me up and I dragged my tongue up the underside of his cock. My teeth gently nipped the head as he pushed me back down on him. I flicked my tongue around the crown and at the sensitive underside, enjoying the feeling of his shiver. Taking it to the next level, I dug the tip of my tongue into his slit and lapped the pre-cum that was there.

The thick salty liquid was the treat I was looking for and I hollowed my cheeks sucking for more and I hummed in my throat. Trent hissed above me and pulled me up sharply, his dick making an obscene popping sound as it slid out of my mouth.

"You are not going to get off that lightly Miss. Holcombe." He told me sternly. "Now up over the desk, face down."

"Yes sir." I said meekly, relishing my role.

I lay down on the cold desk, the soft leather inlay on the desk quickly warming to my body heat and I felt his hands caressing my flanks and ass. I wiggled slightly as he found one of my ticklish spots and a sharp crack on my butt stopped my movement.

"Hold still." He said sharply. "Your punishment is just beginning."

I felt him feel between my legs and I spread wider for him. His fingers tore at the gusset of my teddy and the snaps there popped open. He pushed the material up over my ass and onto my back. The garters were pulled even tighter and I felt his hand slowly rub my backside.

With a sudden loud slap, he spanked me again. The sound echoed in the office, but it didn't hurt all that badly. Trent was cupping his hand so that the impact was light, but the sound was really loud.

Slap, slap, slap, he spanked me, alternating first the left check, then the right. I wiggled each time he struck, and then started lifting up onto my toes to meet his hand as it came down. The slight tingle in my butt was delightful; I knew from the heat on my ass that I was turning a wonderful shade of pink, on my way to red when he stopped.

"Did that teach you a lesson Miss. Holcombe?" He asked sternly.

"Yes sir," I sniffled.

"Are you all right baby?" Trent asked suddenly concerned at my crying.

"Yeah, I'm fine," I sniffed again. "Sir, I promise that I will follow the dress code from now on. Please don't fire me," dropping right back into character.

"We will see about that after I have finished your punishment." He said, and I could hear the smile in his voice. He pulled my cheeks apart and drove his throbbingly hard dick balls deep in my pussy.

I howled in delight as he sank into me. Trent gripped my hips and banged me hard on the desk. I gripped the front of it and thrust up to meet him. He froze as soon as he was fully seated inside me and didn't move as I wiggled around on him.

"Do you promise to be a good secretary and dress accordingly Miss. Holcombe?" He asked me.

"Yes sir." I moaned still trying to get him moving inside me, but he held me pinned to the desk.

"And you will follow the dress code?"

"Yes sir." He slipped out a little and pushed back in.

"And you will report to me every day to make sure that you are dressed properly."

"Yes sir." Again slight movement, a little deeper this time. Trent was really teasing me.

"And if you don't follow the code will you accept your punishment?" His voice was starting to shake.

"Yes sir." I gasped as he slipped half his cock out and drove it back in. "You can punish me as you see fit sir."

"Good girl." He praised me as he started fucking my in earnest.

"Oh yes sir, make me a good girl." I begged, driving up to meet his ravaging dick.

Trent pounded me like never before. He had always been so loving and caring before when we had sex, but this was almost a grudge fuck. He pumped his hips forward and back at a dizzying rate of speed. Cum dribbled out of my clit and I screamed and begged him for more.

Trent pulled my hair up and leaned down over me, chewing on my neck.

"Is this what you want?"

"Yes sir," I managed to gasp.

"You wanted me to punish you like this didn't you that is why you dressed that way, isn't it?"

"Yes sir, I need you to make me a good girl."

"Fine, this should do it." He screamed, pulling up off of me, he slapped my ass for real as he shot his load into me. The burning fluid of love tripped my own switch again as his head rubbed my prostate and I screamed in delight as my eyes rolled up in my head and my lashes fluttered. My clit shot its girly load onto the floor and Trent pumped seven hard ropes deep inside me.

Finally he pulled out and fell back into his chair panting and left me gasping and sweating on his desk, his cum running out of my pussy and down my legs, where it mingled with my own.

Following the delightful hour of dictation a quick clean up of the office and a shower, we both snuggled up on a lounger together by the pool.

"That was wonderful." He sighed in my ear. "I'm gonna miss being able to do that when Candy and Kevin move in."

"I am sure that we will be able to work out a system of signals to arrange some privacy." I told him. I was wearing my silver monokini and he was in a very tight speedo.

"Yeah, we will work it out."

"I have already told her the first rule is no parties." I said.

"Oh, maybe just a little one," Trent said.

"No, there is no such thing as a little party in college." I told him firmly. "This house will get trashed and we will get kicked out of the neighbourhood. Also, your parents will kill us both."

"There is that." Trent agreed. "When are the other two due to join us?"

"Candy said that she will be here next weekend and she is bringing Kevin if he can get time off work."

"Good, we can sort the place out after they get here."

"I think this week while you are working, I will catch a train home and pack some stuff and drive back with them."

"Good thinking, you can drive my car down here for me."

"That is what I was thinking too." I agreed. "Mine is here, Candy will bring hers and Kevin doesn't have one. Perfect, everyone gets a space in the garage."

"What are you going to do all week while I am at work?" He asked.

"Work on my tan, exercise, send you dirty pictures and texts to tease you."

"Hey." He said slapping my butt. "That is not fair, you laying out here doing nothing but trying to get me all hot and bothered while I am slaving away for my father."

"It's not my fault that you have to go to work all day." I said grinning evilly. "Besides, I have to keep you away from that hot secretary of yours." Trent was drinking when I said this and he spit soda out of his nose.

"Please, Miss Carson," he gasped, then remembered what a told him in his office and he laughed. "It is hard to concentrate with her walking around in those high heels and nothing else."

I had to laugh too, the thought of his fifty plus year old little secretary wandering around his office in nothing but high heels was ridiculous, she was the most prim and proper lady I had ever met.

"Well, you just keep it in your pants until you get home mister." I warned him, squeezing his cock gently. "Oh, and by the way, this house is not going to be clothing optional. You will be dressed whenever you leave our bedroom."

"What, you think Candy will try to rape me if I walk downstairs naked?" He teased.

"Let's not give her the chance." I said firmly.

We fell into our routine in the house as soon as everyone else had left. I got up first every morning; Trent still wasn't a good morning person. I put the coffee on the night before so it was ready when we got up; all I had to do was get him out of bed. A good morning suck and he was awake and moving. I got used to doing it for him and it helped with my weight control, after he came, I didn't need breakfast.

As soon he was out the door the first Monday we were alone, I started my routine. I good solid workout, weights, yoga, riding and then a swim, I had to stay the same size if I wanted to keep my contract. After lunch I tanned and did my summer reading for school. I thought that I would have the summer off, but college was approaching and we had a list of required reading to do before classes started. I did tan naked though, I was beginning to understand why Mom and Heather liked doing it topless, but I needed an all over tan for the shoots.

I had already spoken to Ashley and she called me the instant that Trent left the office for the drive home. He had the limo, but only for that week, then he would have his own car. I rushed into the bedroom and showered quickly, getting the tanning oil off and getting ready for Trent's arrival.

I was waiting at the front door, in nothing but my heels, a soda in a frosted glass beside me when he walked in the door.

"What is this?" He demanded, slamming the door before anyone could see me.

"This is your welcome home darling." I said slinking toward him.

"I thought you said this was not a clothing optional house." He said.

"I did, for you." I told him, taking his briefcase from him and jumping up into his arms.

"That is not fair." He said between my kisses.

"You want me to go get dressed, fine." I said pouting and wiggled out of his grasp.

"Not a chance," he growled, grabbing me by my waist and pulling me back to him.

His lips met my neck and his tongue drove into the junction between my shoulder and neck and I melted.

"I hate when you do that." I panted. "You know what that does to me."

"I know that is why I do it." He said to my neck, kissing and tonguing me again.

He walked me slowly into the kitchen, his lips never stopping and bent me over the island. I squeaked at the cold marble hit my skin and then groaned in delight as Trent slid into me. He didn't even bother to remove his suit, and I could feel the roughness of his pants and the zipper dig into me.

"This will teach you to walk around naked in this house." He said plunging deep inside me.

"If this is what you are going to do, I will be naked all the time," I panted pushing back against him.

"We'll see about that," he said, driving even deeper into me.

"OOOHHHHH" I moaned, pushing back against him.

He continued to pound me, driving me harder against the island, and I loved it. The slight pain, he wasn't really hurting me, started to send a warm tingle up my back. He had my long hair in one hand and he used it like a set of reigns and he was jacking my clit with the other hand.

"This will teach you." He panted.

"Yes, yes," I screamed. "Harder, fuck me harder."

I was really turned on, my clit was leaking all over the floor and I was approaching my own release, Trent was right behind me. He thrust deep into me and let go a scalding torrent of juice as I shrieked and let go my own trickle. It actually squirted out of me and landed on the wall of the island Trent had taken me on.

He panted above me, trying to catch his breath.

"You are the best." He groaned as he slipped out of me.

"Only because you make me that way," I said, standing up and reaching for a cloth to clean up my mess. I knelt down and proceeded to clean, "Dinner will be in fifteen, go clean up."

We had finished dinner and were sitting on the covered porch as the rain beat down on the roof. Even the weather was exceptional here; it was the first rain I had seen in over three weeks. Trent and I talked about his work and what we had planned. I was just getting ready to go change for my floor show for him when my cell rang.

"Hello."

'Janie, J.D., I am soooo glad that I caught you. I need you for a shoot on Saturday afternoon."

"But you said I had another two weeks until the next one, what happened."

"Carol wanted to do some location shots and we just got approval, but it has to be this weekend or it is off." J.D. explained. "Tell me you can be there."

"What time?" I asked.

"Two."

I thought for a long moment, it would take some rescheduling of the road trip, but I could do it.

"Can do boss." I said cheerfully. "Just send me the address and let me know what to wear and I'll be there with bells on."

"Bells might not be a bad idea." She laughed. "I email you all the info. You are the best. Bye."

"What was that all about?"

"J.D. has an emergency shoot for Saturday." I explained. "It just means that I will have to leave a little earlier than I planned to make it back here."

"No, reschedule everything for the day before." Trent said firmly. "I don't want you rushing on the road to make a deadline. You have time to go Thursday and drive back Friday."

"You just don't want me to ding your car." I accused.

"Of course I don't." He said, and then laughed as I hit him. "Seriously, I don't want anything to happen to you. I will get your ticket changed, call Candy and let her know about it."

I picked up my cell and speed-dialed her number, but expected to leave a message as she was probably at work.

"Hey Janie, how you doing sweetie? Did Trent like his lap dance?" Candy's voice spilled from my phone.

"I thought you would be at work." I responded, trying to change the subject.

"No, they canned me when I said that I was leaving in August."

"That sucks." I responded. "You can't let them do that."

"Who cares," she replied. "I hated that job anyway. It just gives me more time to spend packing and looking for a job in LA online."

"Well, I have to do a shoot on Saturday afternoon, so I have to drive back Friday, can you and Kevin find your way yourselves?"

"Naw," she came back quickly. "We'll come down with you on Friday. Kevin's office told him he can work anywhere there is an internet connection. Since it was my work that was messing things up we can just follow you down and stay for awhile while I look for work."

"That's doable." I said. "I have to drive Trent's car down so he has wheels here. I would prefer it if you followed me."

"No problem hon. We can do that. I will call Kevin now and get him on the stick. Now tell me how was the lap dance?"

"I'll call you Thursday when I get in and we can finalize the trip. Bye Candy." I hung up quickly before she could start on me again.

"All set, they are coming with me on Friday." I told Trent.

"Good, I will feel better if my baby has some protection during the drive and you too."

"You creep." I said hitting him with the pillow from the wicker sofa we were on. "Just for that you don't get the surprise I got for you."

"Oh baby, you know I don't mean it." He wheedled at me.

"No chance, you just want your surprise." I told him firmly.

"Damn right, now give or the tickle monster will get you." He curved his hands into claws and reached for my side.

"Okay, okay." I said quickly. He knew I hated being tickled, but he did it to me often. He said that he liked the way I giggled when he did it. I think he just liked to torture me.

"Stay here, I will call you when it is ready." I told him sternly. "And no peeking."

"Yes dear." He said wearily, earning himself another swat with the pillow.

I ran upstairs and straight into the closet. I dug out the school girl outfit, the white thigh high stockings and the white platform heels and went to do my makeup. I went all out on that one. The mascara was so thick I could see it on my lashes without the mirror. My eye shadow was heavy and sparkly green. My lipstick was thick and dark, the outline so dark it looked almost black.

I slipped downstairs to the media room and checked the CD player. My music was still in there and I set up my mix for my dance set. I had three songs ready and I wanted to do it right. I went into the recreation room and changed into my outfit. I wanted to appear already dressed.

DMaster_14
DMaster_14
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