Jenny and Henry Pt. 01

This story has humiliation in the beginning which takes a turn for sexy humour.

(This story has elements of non consent and humiliation and meant for mature audiences.. All the characters are above 18)

I blame my roommate Alex for all the shit I am in.

As I stood wringing my hands in the principal's office, I just wished that I could turn back time and say a simple "no" and be far far away from this terrible predicament.

Let me start at the beginning.

My name is Jennifer or Jenny and I am a small town girl, first time in the big city for college.

My parents back home are rough and uneducated but supported my ambition of becoming a lawyer. My father even mortgaged his farm to send me here. So, I have been focusing on my studies and keeping my head down since I came here two months ago.

The blasted roommate Alex I mentioned above is not a bad person perse but we had totally different upbringing and goals. So we were cordial but aloof.

Then last night as I was about to get into bed, she walked in and asked if I could do her a huge favour. I asked her what was the favour.

"I am going to this frat mixer and I am afraid I am going to to drink too much and lose myself. So I want you to be my sober buddy and look out for me at the party." She said.

I protested saying that I had never been to a frat party and wasn't invited.

Now she pleaded "Please Jenny, at the last party I got drunk and some guy groped me. Please I need you to protect me."

With that, she wore down my resistance - you simply don't ditch a sister in need, especially in the metoo era.

"So, what are you wearing?"

I picked up one of my jeans and shrugged my shoulders.

Alex was indignant "Don't be silly. You will borrow one of my dresses and please ditch the granny panties. We are almost the same size."

I was actually delighted, not at the prospect of wearing her fabulously expensive clothes but about having a friend in this far away place. I was so lonely away from my home.

Even though we were almost the same size, her clothes were a little tight on me but nothing too uncomfortable.

Alex picked a black and short sequinned sleeveless dress. Although it had a jewel neckline and no cleavage was visible, the dress was semi transparent and when the light hit it, the swell of breasts and their movements could easily be seen.

The dress was short, ended just below my crotch. As I wore one of Alex's lingerie set complete with stockings it was not a major problem. I paired it with my own black boots and we went to the party.

Although I was dressed like a sexy woman on the outside, I couldn't behave like one at all. So I sat in the corner sipping my beer and looked on in apprehension as Alex kept knocking back vodka shots and smoking rolled joints. I actually dozed off a little.

Suddenly I heard shouting and screaming and woke up with a start. The campus police were here and they were rounding everyone up.

They confiscated the booze and the drugs. They took our names, checked out IDs and locked us in to the rooms in the frathouse. By now Alex had passed out and I sat cursing her for landing me in this fix.

In another hour or so, the door opened and the policeman called my name, taut with tension and shaking in panic, I went with him and he escorted me to the Dean's office.

To my consternation, my school counselor was waiting there for me. I despised this lecherous man known as Tucker the fucker among the students because he was a habitual groper.

Before he could say or do anything, I hurried into the Dean's office and stood in front of him. The Dean sat with an expression like he was at a mourning. Old man in his 70s he had no patience for our antics and spoke -

"Jenny, you have been caught at a party that violated 20 of this college's rules. You should be handed over to a judge but when we checked your ID I came to know that your local guardian is Henry. He is a reputed banker and a personal friend to me. His niece going to jail would cause him major embarassment."

At this I felt totally dejected and scared. First of all I had hoped for a suspension of a week or community service not the expulsion. And I groaned as I heard the dean speak about uncle Harry.

Henry is my father's elder brother in his 50s. He is a 6 foot giant and a super successful banker. Both my father and mother are in awe of him and he had even arranged for the latest mortgage. I had met him once or twice a long time ago but had heard plenty about his brains and his ruthlessness.

As my thoughts were getting scarier by the minute, the door swung and uncle Henry walked in with Tucker. As Tucker locked the door behind me, Henry ran his eyes over me and his face had an expression bordering on disgust.

I shivered in fear, if he was anything like my father, I could expect a good hiding and I would have deserved it.

The Dean walked forward and led him to the seat as Henry expressed his regrets about the behaviour of his niece. The Dean assured him that I would be dealt with internally and there would be no backlash for my uncle.

Then the Dean spoke to me as I stood white and shaking "Young lady, considering your Uncle's predicament I have decided to put you on probation for next 6 months."

I started to protest "But I did not even take the drugs, I was there as a sober buddy."

The Dean raised a hand and silences me "I will now list out the conditions of your probation and as long as you follow them you will have no trouble. If you put a little toe out of line during his time, you will be expelled and you should remember that your fees are non refundable. Am I clear?"

I nodded my agreement because I had no other option.

The Dean listed out the conditions

"You will voluntarily submit to a search and drug test. Your room will be searched for drugs and sealed. So you will stay with your Uncle until we get the results of your drug test and as the guardian he will guide you and help you stay sober. After that you will be under probation for next six months and you should agree to random drug tests."

I was shaking quite noticeably and said "Why do I have to stay with him? Just change my room and please let me stay on campus."

The Dean was a bit angry now "You don't realise what a slap on the wrist you are getting young lady. If not for your uncle, you would be in jail and what firm would hire a convicted druggie?"

"So, either agree to my conditions and co operate fully or refuse and go to jail. I just want you to follow orders without protests or tears. Am I making myself clear."

I knew when I held a losing hand and accepted my fate. 6 months of misery or a lifetime being a failure, it was not a contest at all.

Then the Dean gave me some forms to sign. I just wanted to get out of there and signed them fast. Then he sat back and announced "Time for the search." And Tucker started walking towards me.

I was in shock and wild panic as I imagined his lusty hands searching me. So I backed into the wall "Can't a woman search me?"

The Dean looked exasperated now "You moron, we can't let this become general knowledge for your own sake. Someone might gossip about this and things would get complicated. Moreover Tucker is trained, so you can relax."

I understood that I was out of options and alone. Just had to get through this humiliation.

Tucker motioned me forward. I walked in and stood nearer to the Dean's table as Him and Henry sat on either side of the table and Tucker was behind me.

Uncle Henry ran his angry gaze from my disshellved hair to high heeled boots and snorted "So, you have been spending my brother's hard earned money on looking like a stripper."

The disgust in his voice irritated me I started to say that the dress belonged to my roommate but the Dean silenced me and asked Tucker to take charge.

I braced myself for a patdown like at the airport but Tucker barked "Take of your dress, this is a strip search."

I clutched my dress and shook my head unable to speak. By now Dean had run out of patience "This is the last insolence I am permitting. You will do as we say and stop speaking at once."

"At least send him out he is my uncle." I begged.

Tucker snapped "What kind of a lawyer are you? A parent or a guardian must be present for any type of interrogation. It is the law. Stop yapping and take off that excuse of a dress."

All the protest slowly drained out of me as I stood in misery and shock for a couple of minutes. Then I grabbed the hem of my dress, pulled it off over my head and handed it to Tucker.

At the sight of my ripe body clad only in underwear I could see Henry and Dean take in a sharp breath and exchange a look.

I wore a black satin bra that was Underwired and lifted my already firm triple D breasts up and together invitingly. As I was panicked and breathing hard, my creamy curves rose and fell rapidly and a flush was spreading over them.

I wore black see through stockings which clearly showed my blonde bush peeping by the sides of my thong.

Uncle Henry spoke "Too busy partying to shave, I see." I blushed brick red at this crude comment.

The Dean motioned me to continue. But I now protested that Tucker could easily Pat me down now. The Dean was now properly angry "This is my final warning. If you defy me once more, I will call the police, no more warnings."

Now even Henry spoke up "Why are you being so ungrateful Jenny? If you haven't got any drugs why the hesitation? It's already 2 am, please Co operate and let us get moving asap."

My defenses destroyed and my humiliation growing, I was about to remove my stockings but Tucker moved suddenly and in a smooth motion unclipped my bra and removed it.

As my breasts swung free, flushed and heaving, topped by dark coral nipples I was mortified and started to move my hands to cover but Tucker barked at me to stop and I was paralized in fear as I let my hands hang by my sides.

The Dean and Henry were looking at my perky boobs in open lust. I could even see the Dean rubbing his crotch as he pointed to my crotch.

I slowly bent and pulled down my thong and stockings exposing my golden bush and long legs.

Tucker walked around me in a frank appraisal and commented "Her boobs are quite large for her body don't you think? Is it genetic? Does her mom have large boobs?"

I blushed hotly at these coarse words and spluttered in protest the insult to my mother.

Uncle Harry spoke up " Even larger with breastfeeding her brats but I am sure they are not as firm as Jenny's."

The casualness of this was unbearable. I spoke " Can I have my clothes back? As you can see I have no drugs on me."

Tucker spoke "Don't be silly Jenny these are evidence, moreover your search will begin now."

As I stood in horror and the other two guys looked on lasciviously, Tucker started to grope me.

First, he ran a hand through my blonde shoulder length hair and searched behind my ears. As he slid his hands down I bent my head in humiliation.

Next he cupped and lifted my breasts. Caressed them and grazed his palm against my nipples and pinched them almost painfully. To my aggravation, my nipples instantly became taut and my boobs were throbbing. As he continued to press and squeeze my breasts, I could also feel my pussy getting wet.

Then Tucker trailed his hand down my navel and cupped my pussy. By now I was breathing hard both in anxiety and a little bit of arousal. I tried to look at Tucker's ugly mug and calm my body now. But my harmones were out of control.

Tucker rubbed my hairy bush "It is so rare to find an unshaved pussy nowadays. Look at how curly and soft this is."

The words were dirty but the tone was casual like discussing weather. I felt my body stiffen as his fingers parted my bush and found my vagina opening.

In panic I grabbed his hand and sobbed "what are you doing?"

Tucker swatted my hand away roughly "Just my duty. If you have no drugs why are you worried?"

I looked at uncle Henry and the Dean hoping that they would stop this madness. But they were too busy ogling my heaving breasts and paid no attention.

Tucker pushed a finger in and it easily slipped in as my pussy was already leaking its juices. He chuckled in amusement as he felt the wetness and inserted another finger and started to probe my pussy. Then his thumb started to caress my clitoris.

I was losing control fast and soon my breathing got heavier and my boobs bounced and swayed topped by rock hard nipples. Involuntarily I started to push my crotch against Tucker's hand and started to squirm my hips.

Tucker squeezed my boob with the other hand and laughed aloud "Look at your niece Henry, a proper whore, if only we had waited another hour we would have caught her sucking some frat bro's dick."

Both Henry and the Dean slapped their thighs and laughed as if it was a huge joke.

I started to try to calm myself and hoped that my first orgasm with a man would not be by Tucker the fucker. Thankfully in a couple of minutes he withdrew his hand and moved to my back.

I took a breath of relief. But it was short lived.

Tucker asked me to bend over and hold my knees. As I bent forward, My boobs swung heavily and I blushed at the expression of Dean who was now pressing and adjusting his crotch.

Tucker once again inserted a finger into my pussy and I settled for another grope but he quickly pulled it out and inserted it roughly into my asshole.

Even though the finger was coated liberally in my pussy juice, my asshole was too tight and he had to push with force. I screamed in agony and swayed in place. But Tucker continued his unhurried abuse of my ass.

After five minutes, he snapped at me to stand up straight and turned to the Dean "We are done with the search sir. She has no contraband on her person. Now I will collect the sample for drug test."

Tucker ordered me to squat. Ashamed with awareness of how vulgarly my pussy and boobs were exposed to the men, I squatted and swallowed my objections.

Tucker handed me a small cup "Pee into it.'

I was mortified and begged desperately "Can't I do it in the bathroom? Please please."

Tucker shook his head "That would contaminate the sample. Please be fast and also 5 ml is enough."

I held the cup but just couldn't go. Henry spoke "The sooner you give the sample the sooner this will be over."

I shut my eyes and forced myself to pee. At first it was a trickle and fell into the cup. But suddenly I lost control and warm piss gushed out of me in a thick stream.

The cup was filled but I couldn't stop and like a dog peed on the floor. Soon my heels were dipped in the pool of my urine. I shuddered in disgust at myself.

Tucker was smirking and handed me the mat by the door and asked me to clean up after me. I was too ashamed to even look at my uncle and the Dean.

But as I stood, I realized that my ordeal was over at last.

Dean spoke "I hope this search has been traumatic enough for you never to abuse drugs again. It will take a week for the results of your drug test. We will meet and talk once again after the results are in."

Then he turned to Henry "You can take her home. Sorry for the inconvenience."

Henry thanked the Dean and the counselor profusely and said "I should thank you for not sending her to jail. Don't worry I will keep an eye on her. Let's go Jenny."

I was panicking again "But how can I go across the campus like this, at least give me back my dress."

But Tucker was already placing the dress and underwear in a clear plastic bag and said "Sorry can't do. It is evidence. Let me find you something in lost and found."

Now I covered my pussy with one hand and even though not much effective drew the other hand across my breast.

Soon Tucker came back with a cropped jacket that reached just below my boobs but had no zip of buttons. So I had to clutch it together.

"That's all?" I questioned indignantly and Tucker shrugged his shoulders.

Then the Dean spoke "Don't worry Jenny, I can understand your reservation. I will help you."

Then to my horror the shameless old lecher unbuckled and removed his pants. I stood, my mouth gaping in shock. Even Tucker and Henry were shocked now.

Then the Dean slid down his tighty whities and his droopy dick and hairy balls sprang free. I was so disgusted, I threw up in my mouth.

He extended his dirty underwear and suggested that I wear it for modesty "and don't trouble returning it, you can keep it." I was furious and screamed inside "I will burn it, hopefully when you are wearing it."

The underwear smelled strongly of sweat and it had a wet spot in the front. My whole body shivered in disgust as I realized that the bastard must have cum into his pants while Tucker was fingering my pussy.

Then as Henry hurried me some more, I gingerly put on the dirty underwear. I felt like scratching myself all over with frustration.

Then Henry made me walk all the way across the campus clutching the jacket to my chest and wearing cum soaked whities. Thankfully the campus was deserted.

We went to the parking outside and I craned my neck for his car. But he walked to a sports bike and took the spare helmet and extended it towards me.

I had to let go of the jacket and strap it on. As soon as the jacket gaped open, my boobs jutted out - creamy and heavy.

I quickly grabbed the jacket and closed it.

Henry gave me a mocking smile. After the degradation in Dean's office, my modesty was comedic.

I got up behind Henry and sat as far back as possible. But the bike had a sleek design and I had nothing to hold on to. Henry was sleepless and exasperated by now "Hold me tightly and sit, I just want to get home. Some of us have to earn our living tomorrow you know."

Cringing I slid forward and put my hand around his hard torso. Now my jacket was flapping but I could move my arms and control it. Moreover the roads were empty even if my boobs were hanging out.

Henry turned realising that even though I held him, my hands were pulled back, and I sat as far back as possible and, I gave him a smug smile. He shook his head in exasperation and started the bike.

The moment he started the bike and accelerated, I slid sharply on the incline of the raised pillion seat, my jacket gaped open and I slammed hard into Henry's back. While I sucked in a quick breath in shock, Henry's shoulders were shaking in quiet laughter as now my bare boobs were pressed into his back.

As the speed increased and my boobs were crushed to his back and they rubbed softly onto his rough leather jacket. Soon my nipples were taut and I felt my pussy getting wet.

We rode for half an hour and reached his apartment. Henry parked his bike and I almost jumped off it and stood clutching the jacket to my chest. Shaking his head he guided me to the private elevator, into his apartment and into a bedroom.

Henry pointed towards the bathroom and handed me a towel and a garbage bag. Grateful I murmured my thanks and went in.

I peeled off the jacket and the dean's underwear and stuffed them into the garbage bag. I stepped into the shower and felt myself relax after the terrible day.

I consoled myself that the worst was over.

When I walked out, Henry had kept one of his white T-shirts for me. Of course it drowned me and looked like a maternity dress.

As I heard him coming towards the room, I jumped under the covers and drew them up to my chin.

He came into the room wearing a robe and to my horror stood on the other side of the bed and removed it.

My mouth opened in shock when I looked at the sight of Henry wearing a pair of red silk boxers and preparing to slip into bed.

I almost screamed "Leave me alone."

Henry looked amused "so that you can sneak out and do some drugs with your degenerate friends? I don't think so."

He noticed my gaze on his hairy chest and toned navel and the trail of hair disappearing into his boxers.