Freshman Dorms Ch. 01

The following is chapter 1 in a multi-part series. For background on Dean Bobby and WorthingtonUniversity, please read Chapter 0.

Chapter 1 – First week of school

I was thrilled that the hidden cameras I had installed in each room in the Freshman dorms were working perfectly. I was able to watch everything the students did in crystal clear video from the security of my own private room in that very same dormitory. My only regret was that I couldn't find nearly enough time to devote to my new favorite hobby.

As both Senior Resident and Dean of Students for Worthington University, the first week of school is always the most hectic of the year. I spent most of each day getting the students acclimated to their new environment while ensuring that everyone had places to live and the correct schedules of classes. True to my earlier promise, I also devoted several hours each afternoon and early evening conducting random room checks. I would knock on a student's door and announce "This is Dean Bobby, please open your door." The students knew they had until the count of 10 to open up, at which point I would use my master key and let myself in. Not once during that first week did I ever find anything that required further attention. I would chat and joke with the student so that by the time I left, they didn't feel like the visit had been an intrusion. By the end of the first week, I had visited with each student at least twice, getting to know them each a little better. These checks went on until dinner, at which point I would join the freshmen in the student cafeteria, sitting with a different group each night. I would finally return to my room, mentally exhausted but thrilled by what I knew was waiting for me on my computer.

I worked until well past midnight each evening watching and then tagging every video on my private server. My computer was setup with two large flat panel displays, so I was able to observe eight movies at once. I soon had a routine established that let me quickly delete the useless videos, archive the semi-interesting ones, and mark as favorites the ones I wanted to view again and be able to access quickly.

My first task was to build a digital catalog of every student, complete with their important information. With over 200 new freshmen residents, I decided to begin with the girls. For each student, I started by listing their name, birthdate and home town. I next made a copy of my favorite images of each - one of their face, one fully clothed, one full-body shot naked, and then close-ups of their asses, breasts and pussies. Next to each image, I would add a category type. Body types included "Athletic", "petite" and "busty". Pussies could be "Bushy" or "Shaved." For tits, I tried to guess the cup size and whether they were natural or enhanced. After several days, my personal female student database was complete. It was time to find my first "project."

*******

Cassidy Jennings had come to Worthington from a small prep school in Connecticut. She had a cute round face with pouty lips and long blonde hair. My favorite parts of Cassidy were her medium-sized perky breasts which she proudly put on display with each outfit she wore. I figured she was enjoying the freedom of college as I watched her sleep with three different guys her first two days at school. It appeared that she had picked one favorite though, as she had hooked up with Jimmy Franklin each of the last three nights in her room at exactly 10 PM. If they had thoughts about making tonight four in a row, I would be paying Cassidy a little visit.

At around 9 that night I pulled up the live video images of Cassidy and Jimmy side by side on my monitors to see if I could determine if they were getting ready to meet up. Cassidy spent the hour showering, shaving, and applying twelve different bottles of lotions and perfumes to every part of her body. Jimmy sprayed his armpits with deodorant and put on clean underwear. It seemed like I was in luck.

At exactly 10 PM Jimmy hurried out of the elevator and almost ran me right over. "Hello Mr. Franklin," I said cheerily. "Where are you off to in such a hurry this evening?"

"Dean Bobby? Um, er, nowhere important," he stammered as he shot a quick glance in the direction of Cassidy's room. "Just going to visit a friend."

"It's kind of late for a visit, isn't it? I hope everything is OK?" I asked.

"No! I mean, Yes! I mean, everything's just fine. Nothing serious at all." He continued to babble and he shot another look past me to the door down the hall.

"Great! Then perhaps you wouldn't mind helping me out this evening?" I asked.

"Me?"

"Why not? The Worthington chapter of the Abstinence Society is having their first meeting next week. I told them I'd be happy to go door to door explaining the goals of the club and personally inviting every freshman student. How about I give you some literature to hand out? You take this side of the hall, I'll take the other. Shouldn't take us more than a few hours to finish."

Jimmy's face scrunched up and paled noticeably as he tried desperately to think up an escape plan. "You know Dean Bobby, I just realized that I forgot I had something super important to do tonight. And now that I think about it, my friend isn't even on this floor. I'm supposed to be one floor down. You don't mind if I take a rain check on the abstinence thing, do you?"

"But of course not. Go do your super important thing. But just in case you change your mind, I'll be on this floor for the next few hours if you'd like to join me."

"Thanks Dean Bobby. I'll keep that in mind, but...uh, right now I gotta go!" He skipped the elevator and practically sprinted down the stairs, back towards his own room.

I almost felt sorry for the dumb lug, it was just too easy. I made a mental note that I'd make this up to him at a later date. But right now, someone else was requiring my attention.

I walked over to Cassidy's door and knocked firmly. Before I could even announce myself, from inside the room I heard "Get your ass inside and fuck me! Hurry the hell up, you're late so I started without you."

I entered the room and cheerfully said "Hello Miss Jennings. How are you this evening?" Cassidy's eyes got huge and she grabbed for the blanket next to her, but not before I got a look at her completely naked, one hand fingering her clit, the other holding onto the vibrator shoved deep inside of her. "Oh my God! Dean Bobby! What are you doing here?" She asked frantically.

"You told me to come in Miss Jennings. Surely you remember." I turned around and locked her door, then grabbed a chair and sat down right in front of her. "So please tell me, why do you seem so surprised?"

"I thought you were someone else. I don't know what to say, I'm so embarrassed." This last point was evident by the deep shade of red she had turned.

"You have nothing to be embarrassed about, I can promise you that. But do you a hear buzzing sound?" I asked.

Her eyes got wide once again as she realized the humming we could both clearly hear was coming from the instrument still turned on inside her pussy. She sheepishly looked away from me and slowly moved her hand to remove the offending vibrator.

"Don't TOUCH that!" I commanded her loudly. She pulled her hands away immediately as if she'd been shocked. I stood up and moved so that I was standing directly above her. "You see Miss Jennings, I believe that I've found you in what's known as a 'compromising position'. You know what that is, right?" She nodded. "And I'm guessing you wouldn't want this reported to anyone, say the University or your parents?" She shook her head no. "So until I tell you otherwise, you're going to doing exactly what I say, you understand?" She nodded again. "What was that? I couldn't hear you."

"Yes," she said softly.

"Yes, what?" I asked.

"Yes, Dean Bobby."

"Excellent! I'm glad we've reached this understanding," I said as I smiled broadly. I reached over and yanked the blanket off of her, and sat back down.

She moved move to cover her body, but stopped as she remembered what I told her. "Please remove your vibrator, " I asked her. "I don't you want you too desensitized down there." She gave me a quizzical look, but removed the vibrator and turned it off. "May I?" I asked her and held out my hand. She paused briefly before handing it over. I held it up to my nose and took a deep whiff, before putting it into my pants pocket. "Thank you for that." I told her.

"A few minutes ago, you told me to come into your room, which I've done. You also told me to fuck you, and to be quick about it, remember?"

"Yes, Dean Bobby."

"Well, then I've got good news and bad news. The good news is that you're about to be nice and fucked. The bad news is that there is going to be nothing quick about it." She finally lost the shocked look that had been plastered to her face since I first walked in and I thought I glimpsed the beginning of a sly little grin. "However," I continued "It's certainly not fair that you are completely naked, while I'm fully clothed. I think some changes are in order." I stood up and put my arms up over my head, waiting for her next move.

She stood up quickly, getting the message right away. Walking right up to me she pulled the t-shirt up over my head and threw it aside. She stepped back to get a better look at my chest and arms. I kept myself in excellent shape by working out with the teams that I coached, and was quite proud of my body. Cassidy seemed to like it too as she stood there just staring at me.

I pointed my head down and looked right at my crotch, giving her the signal to keep going. From her knees, she grabbed my waistband and pulled my jeans down with one quick jerk. Freed from its confines, my semi-hard cock jumped out, just inches from her face. Cassidy just stared at my cock for a minute and then looked up at me waiting for my next order.

"Lie down, Miss Jennings. On your back, facing me." She did as commanded, never breaking eye contact with me. I could tell she was starting to get into this and I wasn't about to ease up on her. "When I came in her, you were pleasuring yourself, is that right?"

"Yes, Dean Bobby." She answered.

"Were you close to cumming?"

"No, Dean Bobby"

"Why not?" I asked.

"Well, I like masturbating and all, but I really prefer a big hard cock inside me." As she said this last part, she looked directly at dick, which was slowly growing to full size.

I had spent much of the last few days watching videos of Cassidy Jennings having sex, and I knew she was telling the truth. Her favorite position was on her hands and knees getting fucked from behind. I hadn't seen her cum once from having her pussy eaten. That could have been partially due to the guys she'd been with having no idea what they were doing, but whatever the reason, I saw this as a personal challenge.

"Hmmm...Very interesting," I said as I lowered myself directly over her completely shaved pussy. With my finger, I started rubbing her slit up and down, applying pressure to her clit. "Your clit is still swollen, seems like you got yourself at least a little turned on. Still wet?"

Instead of answering, she just shrugged her shoulders, daring me to find out for myself. I was liking this girl more and more.

I shoved a finger deep inside her, happy to find out that her pussy was in fact still moist. She moaned slightly as I slowly moved my finger in and out. When I suddenly shoved two fingers deep inside of her she groaned even louder.

"Well Miss Jennings, if there's one thing I can't stand, it's a job that's only halfway done." With that, I bent down and started working on her pussy. I spent some time tonguing her clit before licking the folds of her pussy lips up and down. By now, she had her eyes closed and was squeezing her tits hard. Without removing my mouth from her mound, I reached behind me and pulled her dildo out of my pants pocket, hiding it from her view. As I went back to licking her clit, I positioned the vibrator directly over her throbbing pussy. "Miss Jennings, it appears as if you are enjoying this, am I correct?"

"Oh fuck yes, don't stop!"

"I'm sorry, what was that?" I asked sternly.

Again, she quickly recalled how this game was being played. "Yes, Dean Bobby. It feels amazing. Please don't stop."

"Miss Jennings...we're just getting started." With that, I pushed hard on her clit with my tongue and shoved the vibrator deep inside her. She yelped aloud at the sudden simultaneous hits of pleasure and shock. With my right hand holding the dildo, I slowly moved my left hand up her chest. I massaged each wonderfully large breast and gently rubbed her nipples in turn, pleased by the fact that they were fully hard. I put my hand over her throat, giving a very slight squeeze, before sticking my finger into her mouth, allowing her to suck it in and out.

"Look at me, Miss Jennings. NOW." When she lifted her head to watch what I was doing, I lifted my mouth from her pussy and stared her directly in the eyes, not moving for a good 30 seconds. Then, without notice, I turned the vibrator on and pushed it further inside her as deep as it would go. At the same time, I grabbed her nipple and pinched it hard. When she gasped loudly, I went back to work on her clit, licking it hard and fast before grabbing it with my lips and biting it gently. The three-tiered attack pushed Cassidy over the edge and she came hard and loud. I keep up the pressure on her clit, feeling her entire body spasm, five, six seven times. It wasn't until her body went completely limp that I finally relaxed my assault on her body.

Wiping my face with a towel from her night stand, I sat back down on the chair to give her a few moments to recover. When she finally sat up, she looked at me with awe. "That was unbelievable! I've never, EVER had anyone do that to me before." I sat still on the chair, unmoving and not saying a word. "Please Dean Bobby, tell me what I can do for you."

"For starters, you will ask my permission before you cum the next time, understand?"

"Next time?" She stammered. "I mean, yes Dean Bobby."

"Good. On your hands and knees," I commanded. "I want you to crawl over to me...slowly." On all fours, she crept towards my chair until she was between my legs, her face over my cock. I put my hand on the back of her head, applying slight pressure but not pushing down. "Miss Jennings, you're now going to suck my cock. And if you do it well, you'll be rewarded. Do you understand?"

"Yes Dean Bobby."

I quickly shoved her head down as I drove my cock deep down her throat. I held it in that position until I felt she couldn't take it any longer, then let her up. After that, I stood up and allowed her to work on me at her pace. She was doing a pretty good job, alternating between long slow strokes with her hand, and working just the tip with her tongue. At one point I took my cock out of her mouth and pulled it back, giving her easy access to my balls. She went right to work, licking the underside of my sack, and taking each of my balls into her mouth and sucking them gently.

I grabbed the back of her head again and shoved my cock as far down her throat as it would go. "Enjoying yourself Miss Jennings?"

Her answer sounded something like "hrmmmfff hrmmmrrrfff", but I didn't really care about her actual response. She was giving me exactly what I wanted and it was time to give her something in return. I pulled my cock out gave it a few slow strokes, holding it just in front of her face. "Miss Jennings, please put your hands behind your back." She did as I asked and waited patiently as I started to stroke faster and faster.

Without a word, I began shooting long ropes of cum all over her face. To her credit, Cassidy barely flinched and even moved her face slowly side to side to provide me with a better target. Quickly, seven or eight solid spurts decorated her forehead, cheeks and chin. Quite pleased with myself, I took a deep breath and stepped back to admire my work.

"Miss Jennings, that was most pleasurable. But it seems I still have some cum on the end on my penis. I'd like you to clean it off."

While still on her knees, Cassidy leaned forward and looked up into my eyes, her face covered with my sticky goodness. She very slowly extended her tongue, and licked a large drop of semen from the tip of my semi-hard cock. She kept working my cock and in just a few minutes, I was very clean and once again fully erect.

I strolled over to her bed and sat down, my dick still wet and sticking straight up. I beckoned her over with a motion of my finger. She stood up and walked to the bed, stopping directly in front of me, her tits directly at my eye level. I completely looked over her naked body and was pleased to find that her pussy was still noticeably wet.

I reached out and grabbed her by the ass, picked her up and then gently lowered her onto my waiting cock. She gave a moan as her pussy was slowly filled up, and I didn't stop until I couldn't penetrate her any further. I held myself deep inside her, not moving, just letting her enjoy the sensations provided by my fully hard cock. After a few minutes, I started to bounce her on my lap, letting her know it was OK to start grinding on me. When she got into the rhythm and started riding me on her own, I move my mouth to her nipples, very deliberately sucking each one, enjoying the feeling of them getting hard in my mouth. Every so often, I would peer up at her still cum-covered face and get even harder looking at the evidence of the massive facial I had just bestowed upon her.

When I sensed she was close to climaxing, I pulled her off my lap and spun her around. Facing the chair still in the middle of the room, I bent her over roughly, her hands grasping the chair and her ass pointing right at me. I walked right up and jammed my cock into her pussy and didn't hesitate before fucking her as hard and fast as I could. Knowing that this was her preferred position, I made sure to jam myself deep inside of her with every thrust. I guessed her orgasm was approaching quickly and I said "Miss Jennings, you now have my permission to cum." And I smacked her ass as hard as I could.

Another wave of orgasm hit her and she cried out, grabbing the arms of the chair in a death grip. I could feel her pussy clenching onto my cock, pulsating as she climaxed. Looking up at the ceiling of the dorm, I stared directly at the place where I knew the hidden camera was placed, filming every moment of our tryst. Unable to help myself, I smiled and winked for the recording that only I knew existed.

When Cassidy finally finished, I pulled out of her. "Have a seat, Miss Jennings. There's one thing left to do before I leave you for the evening." I walked over to her, picked up her hand and placed it around my still throbbing penis. "I did a great job plastering your face with my cum – with your help of course. But I completely missed your tits. Let's remedy that right now, shall we?"

This time, I put my own hands behind my back to see what Cassidy would do. She grabbed my balls with one hand and gave my cock long slow strokes with the other. At one point, she mashed her tits together and slid my cock between them, never stopping the stroking motion. Once again without a word, I started unloading my cum in thick spurts. She milked my cock nicely spraying her right breast then left, unleashing long white streams of sticky cum, although far less than the first time. When there seemed to be no ammo left in my gun, I removed her hand from my body. I took a step back to catch my breath.

"Dean Bobby", she said. "It looks like there's still something leftover on your cock. Would you like me to take care of it?"

"No Miss Jennings. You've done quite enough for the evening." I started to gather my clothes and began dressing.