Chapter 4 of Anna's Education.

Chapter 4 of Anna's Education.

Anna's Educational Journey: Four

High-class clients emerge and dilemmas arise

Written by Aoife

Attention Dear Readers, welcome to this next installment of Anna's journey. She is transitioning into a distinctive university student. Expect many more turns and detours as she is tugged deeper into her newfound life. She will keep evolving, growing and maturing as she acclimates to her diverse circumstances.

I must express my gratitude to LadyMichelle for her feedback, affection, and assistance on this series. This story is explicitly written for and dedicated to a treasured and adored lover.

I heard a door close. I felt like sobbing but discarded the mask from my face. I allowed my eyes to acclimate. I perceived the water of a shower activating. I knew I needed to prepare and leave.

I stood, finding my shorts, blouse, and sandals. I dressed rapidly. I felt like sobbing, I was remorseful for what I did. I wondered what I did to earn this. I looked at the dresser and an envelope surfaced. I seized it and exited the room, descending the steps and departing the dwelling.

I got in my car, ignited it and accessed the maps app, returning to Miss Liz and Miss Susan's house. I departed their driveway adhering to the directions. On the primary road outside of the residence complex, I teared up, undeniably more than in yonks.

End of Chapter Three

Anna

I arrived at Miss Liz and Miss Susan's driveway. I attempted to stop raging but I could not. My consciousness was swirling with feelings of indignation, despair and trepidation, overwhelming me. I collected my mobile phone and the envelope; I shut off my car and marched to their door.

I vowed to hand them the envelope and stroll back to my car. I was done with them. Uncertainly, I had let myself be trapped in this scenario.

I rang the doorbell and waited for them to open the entrance. When the door opened, Susan beamed at me with a euphoric grin.

"Anna! You're gorgeous. Your anklet glimmers superbly in this evening illumination. Step inside Anna." I presented the envelope and intended to leave but stopped. I sincerely enjoyed my anklet. It made me feel sensual. Regrettably, I ceased to sob.

I heard Liz murmur in my ear and then she stated, "Anna dearest, please enter. And enter you should."

Liz embraced me, caressing me tenderly. She confided in my ear about my beauty and how impressive my job was.

"She veiled me. She had me climax for her. Then she climbed atop my face." I galvanized into tears. "She vanished to the washroom then disregarded me. I feel violated."

"She relished you and although devoid of the affection we'd prefer, she did deliver a phenomenal orgasm, correct?"

Indeed Miss, it was bewildering and rather unnerving."

Liz kissed my lips and ceased our embrace. She directed me to the shower and turned it on. The room blurred with steam. She unfastened my blouse and lowered my shorts, removing my attire.

"Enter the shower, my darling."

I heeded her and stepped into the vast shower. Liz stood alongside me and turned me beneath the water. She washed my visage, facilitating my eyes to open, visualizing the windows and the loofah washed my body, removing the tension. The alluring scent of lavender invigorated my senses. Her hands meandered across my still supple and gradually enlarging nether lips. She tenderly touched my gateway to orgasm.

She coaxed my lips over her luscious lips. She breathed in my ear and mentioned she loved me. My head swirled, I felt consumed by pleasure.

"Miss! Let me cum! Permit your whore to experience ecstasy!"

"Now whore!" Liz clenched her mouth over my clitoris, orally gratifying me.

I galloped to escape the chokehold of my pleasure. I grasped what I could and uttered sensual frenzy. I heard the door open and felt the draft.

The curtain convened partially. Susan peered through, observing me climaxing. She reached out a palm and facilitated me stepping out of the shower. She wrapped me in a plush towel.

She cradled me in the towel and started drying my body. When I was dry, she aided me donning the nightgown and then guided me to a secondary bedroom. The bedding was smoothened and calm instrumental music sounded in the backdrop.

"Hey Anna, it's time to chat in the morning."

A few days after that, I chanced upon the ladies having breakfast together. We all discussed how well our secret partnership was going and how much we could potentially expand it.

Liz broke the silence, "You know, Anna, you'll definitely find someone as striking as you who might need a little financial assistance."

"Don't you think it's time for you to stand on your own two feet and not rely on your parents' help?" she continued, placing her hand on mine.

Then, Susan added, "If you manage to bring someone as captivating as yourself, we'll give you 20% of whatever she earns. Plus, you'll get the first pick of our clients."

Susan paused for a moment, deep in thought. "Why not think about one of your friends who might need some pocket money? Nursing school can be pretty expensive."

After that, they offered me extra money, similar to what the mystery woman had left behind for me. They walked me to the door and mentioned that if I felt like stopping by for a casual evening with the two of them, I was always welcome.

A few days later, my phone rang while I was at the library. I answered it right away.

"Anna, there's a delivery request for tonight. Could you come to my place for dinner?" Liz said.

I kept quiet, absorbing what she had told me.

I chose a red mini-skirt and a white top for my outfit. It looked great with my hair, which was growing longer and longer. I decided not to cut it yet but needed it to be tended to. The outfit, along with an anklet I wore, reminded me of my dream to one day shine in the nursing world.

I put on the anklet, and it felt great on my skin, making me feel confident and sexy.

I was nearly ready when Miss Liz called, saying she had a special delivery for me.

"It's all sorts of kinky," she said, describing the client. "Any questions?"

I shook my head.

I arrived at Miss Liz's place and entered the hall. She remained in the foyer while I headed to the living room.

"Is Miss Susan here?"

"Nope, she's running some errands."

Liz took my hand and held it, whispers in my ear, "Which one's that little dick?" She let go of my hand, and I headed out the door, towards the client. I followed the directions on my phone.

I stopped at a house located in a luxury neighborhood. The place looked incredible, like something straight out of a magazine.

As I walked towards the front door, my client appeared. He was quite handsome, with a formal dressing manner. I happily complied with his instructions, undressing in front of him.

I watched his expression as he saw me standing naked in front of him. He led me through the house to a spacious living room. It was nothing short of spectacular.

When I stood in the middle of it, I saw Miss Liz standing not far away, dressed in a simple brown dress. They seemed to be waiting for something. I wondered what was going on, but decided to stay silent.

"My friend here wants you to observe her. You won't take part unless you agree," the client informed me.

A beautiful blonde woman, who I assumed was Liz, stood before me. Naked like me, she stood proudly in front of him.

"This is a special situation, Anna," the client said.

"Undress," he commanded, watching me attentively.

I followed his instructions, wrapping my skirt around my waist.

Liz remained by my side. She took over, picking up the garment after I discarded it.

"This man has some kinks you should know about," she whispered, gently touching my hands.

Before I knew it, Liz had us both standing in the living room, both nude.

"All right. It's your call."

"Will she be okay with that?"

"She doesn't mind, we were assured it won't be an issue."

I paused, feeling restricted by my lack of words.

"I need you to strip for him, Anna. You won't take part, just watch her as she does it for him."

"And why should I do that?"

"You don't want your little video being shared with our mutual friends, do you?"

I stood there completely naked, anticipating. His eyes assessed me, leaving me feeling exposed. His hand moved to my right hip. With his left hand, he grasped mine, guiding me to turn. I turned slowly, my body feeling his warmth as I rotated. When I stopped back in front of him, only his four fingers remained on my hip.

My confidence soared – I was the center of attention. I heard him humming as his fingers left my hip. His shirt started to come off, unbuttoning it step by step. His muscular chest and shoulders were revealed, exuding the look of a mature and attractive man.

He passed his shirt to me, who stepped forward to take it. His hands delved into his waistband, unbuckling and unfastening his pants with deliberate action. They fell to the floor, leaving only his dark blue boxer shorts.

I stared at his exposed penis, a rather sizable cock for an older gentleman. He stepped out of his pants and boxers and turned around, bending down to pick them up. I admired his properly-shaven groin area.

With my eyes still on his genitals, his hands grabbed my shoulders, gently pressing me down. He placed his hands on his hips, cleared his throat, and waited. I moved with caution as I descended.

"She will observe and learn while you perform oral sex on me. If you accidentally release any of my reward, she'll be punished," he said.

I gazed at him, my eyes searching for answers. "But she did nothing wrong," I replied.

He stepped closer and his hand circled my neck. "Then you better swallow my cock properly, whore."

I looked into his eyes, apprehensive about my own actions. He stood up straight, his hands back on his hips. I knelt in front of him and proceeded to give him the deep blowjob that he demanded. My tongue and mouth lavished his cock, swirling around his head, licking it thoroughly, and greedily sucking his member as deep as it would go.

My clitoris grew more sensitive, almost aching for his large cock. I felt his hand on my shoulders, urging me faster. I didn't resist. I just thought of the young woman who might be punished if I couldn't satisfy him.

Saliva dripped from my jawline all the way down to my tits, creating a mess on my body.

I pulled away, allowing a trickle of my saliva to flow from my mouth.

"Cum for this slut. Fill my mouth with your essence. Pay me in spunk and she'll be spared," I pleaded.

He moved his hands to my sides, guiding me to suck him harder. He held close, waiting for me to deep throat him.

"Double," he grunted. "Double my payment if you cum on my face, and she licks it clean."

"Double my reward for cumming on my face and her tongue cleans you," I repeated. I continued sucking him with greater fervor.

I started stroking his cock with my left hand, setting the tempo faster with each pass. He started moving his hips – I recognized the pattern, knowing he was about to climax.

"Triple," he shouted. "Triple my payment for cumming on your face and cleaning it off with her tongue, followed by a passionate kiss between you two."

I sucked harder and my right hand caressed his balls lightly, rubbing intently and increasing the pressure.

"I want to cum on your face," he ordered. "Cum for this whore."

I continued blowing him, trying my best to fulfill his demands. He jerked his hips quicker and tighter, holding my head steady, and so close that I sensed his cum was about to be released.

A sudden spurt slammed on my nose and face, blinding me right away. A second and a third spray followed, coating my cheeks. I felt his cock jerk, emptying his semen down my throat.

I stroked his cock in my hand, coaxing the last of his cum out by aiming it at my face. Without hesitation, another stream of precum flowed into my lap.

"Clean the whore's face," he ordered.

His payment was still dripping from his cock. I gestured to the young lady. I felt her hands on my shoulders; her tongue licked my cheek and wound up on my lips. The way she cleaned his spunk off my face felt like an act of kindness and compassion.

After her task was completed, she released my shoulders, standing up. We kissed softly – gentle, loving, and slow. I could feel her tongue on my lips. I closed my eyes, feeling like she sensually caressed me. I was sure I heard her quietly whimper as she touched my neck.

She placed a final kiss on my lips and stepped back. She touched my face, gently wiping off the remaining semen. My hands traced down her legs, moving them closer. "Let's reward the woman that spared you," I muttered in her ear.

She'll guide you to the shower and clean you up. Don't lust after my servant; don't sexually touch my servant. I'll get your package and have it ready when you arrive downstairs. I glanced up at him as he made his exit.

She walked me over to the shower, washing my body in silence. Once I was dressed, she led me downstairs. He stood in the foyer, fresh from his bath. He handed me an envelope and mentioned the next time he wanted to make love to me, while she observed. He explained that she needed to learn how to satisfy a partner. He threatened that if I were a poor lover, she'd face punishment, and be allowed to cleanse my crotch with her mouth, either my pussy or my backside.

I nearly jumped in my vehicle to tell was with Miss Liz about this domineering man. Yet, I held no desire to see him again. I couldn't help but pity the woman who was being controlled.

Miss Liz chastened me, reminding me that my role was to please our clients or risk facing retribution — both to my rear and my future prospects. When I considered questioning her, she sternly pulled at my hair, bringing me to my knees.

I found myself before her as she reiterated that by obeying her, I'd become a successful woman without the stress of being a mother of three, nearly destitute, living in a trailer park. She handed me my envelope and dismissed me.

The subsequent two coffee deliveries were profitable. I left each residence with a sizeable envelope in tow. One client requested intercourse, taking over twenty minutes for a blue pill to kick in. The man's face seemed familiar from campus, but I couldn't recall where.

I inquired with Miss Susan, who told me not to worry. The bonus cash I earned permitting him to finish on my face before immediately vacating his residence was well worth such humiliation. She awarded me an envelope with $500.

The second individual kept me blindfolded, just like the first, but my blindfold wasn't applied until I was maneuvered into a sleazy motel room. She remained motionless throughout, simply lying there. This one concerned me. Who was she? And would I be abused by the client again?

Upon completing deliveries to my fifth client, I decided to splurge on a little treat. I awoke mid-morning on a Tuesday, had a quick breakfast, and perused my phone's review site. The top-rated tattoo shop was thirty minutes from my location.

I wanted something distinctive and private on my own body.

I showered and smoothly ran a razor across my skin to ensure I was completely smooth. The memory of her fucking my pussy from behind while pinching my nipples put a spring in my step. I yearned to climax again, but couldn't find the time.

I was struggling with Calculus, a core nursing class. I set the directions on my phone and ventured forth, driving the winding roads in my open-topped Z-4. What a pleasure to have the wind tussling in my tresses while my skirt fluttered and my top exposed my chest.

I was less than two miles into my journey when my thong was soaked and my nipples stiff from desire.

I pulled into the shop's parking lot. There were few cars about. I shut my car and stepped inside. A stunning woman greeted me, sporting long hair with a purple streak on the left side. chestnut-brown-hair-with-purple-streak

I was eager to obtain a tattoo. I wanted the world to appreciate me for my bravery. It would consist of two Chinese characters, 'fearless', inscribed on my left forearm. The other would have a personal and private meaning to myself. Finally, I desired a star between my left ankle's top and the tip. This would symbolize myself as a star, with two in each leg's inner side. My bracer, which I never removed, and the star would signify who I truly was.

I arrived at the tattoo parlor. The spot wasn't bustling, with only a few cars occupying its lot. tattoo-shop-parking-lot

I locked my car and entered the store. A magnificent brunette with a pronounced purplish tint to her locks greeted me warmly. long-haired-beauty

I gave a smile as my eyes fixed on the elaborate design of vines and roses that started from her wrist and extended up her arm until it reached her shoulder. They were stunningly detailed and realistic.

"Excuse me, how can I help you?" She inquired with certainty.

I couldn't avert my gaze from her arm; it was hypnotizing me.

"I'm sorry, please forgive me, but I'm looking for Daria," I managed to say finally.

She extended her hand, bringing my focus back to the present. "I'm Darla, darling. What can I do for you?"

After a moment of hesitation, I clarified and showed her a photo of the 'fearless' symbol. She informed me it would be easy. Then I attempted to contract obscenities about the water drops near my genitals.

"What's that dearest?" Daria asked.

"I'd like water drops tattooed on my inner thigh... umm... near my... kitty." I eventually uttered.

Darla smiled. "Okay, let's deal with the star and the symbol first. Then we'll address the other issue." She took my hand and guided me to a chair in the store.

We discussed various star designs as she showed me images. I settled on the one I wanted. Darla then set me up, even wearing her gloves when she touched me, causing me to shiver.

"Can we remove this bracelet? It'll make things easier."

I immediately replied, "No! Miss has the clasp permanently closed, I can't."

Darla nodded in understanding and proceeded. It took only a short while, but it was extremely painful. I was satisfied, though, when Darla displayed my completed ankle.

Next, she started on 'fearless'. It wasn't as painful, but when she finished I glanced at the clock and realized I had less than two hours to make it to class. The other would have to be postponed. I made my way back to campus feeling happy and proud of myself.

I spent the entire class struggling to focus due to lack of sleep. That night, I accompanied two companions to a fraternity party. I put on a shorter skirt and a blouse that matched, as well as my preferred sandals.

I ensured my wrist and ankle tattoos were hidden for safety.

As Angel, a slender girl from western Pennsylvania, undertook a conversation about financial concerns, I crept up to her. After a while, I noticed her friends conversing with these men, and I approached Angel.

Angie was a slim girl with small breasts, fitting the runner stereotype. Her hair reached her shoulders and was chestnut brown. She had the most mesmerizing green eyes. While chatting, I suggested we head outside to discuss a possible source of income.

Her eyes widened, and she grabbed my hand, claiming she needed a smoke. We walked outside to a secluded location. She opened her purse, pulling out a cigarette and lit it.

I started to talk about being a coffee delivery person, relaying how much I'd earned so far. Angel appeared confused. I then mentioned that one of my jobs involved a woman, causing her to break into a louder voice.

"SHE?!"

I jumped up, covering her mouth. "Yes, a woman."

I resumed my seat while Angie opened her purse again. She extracted the cigarettes and showed me the pack.

"Do you want to have a smoke with me?" She asked, reaching for a cigarette.

She lit it and took a deep puff, then passed it to me. I inhaled deeply, then leaned close to her and blew smoke into her mouth.

I had surprised Angie, as she made himsing noises. She stood up and retrieved her purse again. The pack contained illegal drugs.

"We need to go," Angie said rapidly.

We exited the party's property, and she handed me a cigarette, taking one for herself. I lit it and engaged in a more passionate kiss.

As the cigarette became shorter, our embrace intensified, and we became more intoxicated. Eventually, she took one last hit and passed the joint to me. She pulled me close again and kissed me passionately. I inhaled deeply, surprised by her move.

My mind was spinning, my body was tingling, and my arousal was heightened. I breathed deeply, turned, and held Angie close, kissing her passionately. She didn't resist, opening her mouth to accept my kiss as our tongues danced together, igniting my desire even more.

We broke the kiss, and as I stood up, I took her hands, leading her through the back entrance and away from the crowd. I had a plan in mind: to make love to my newest companion.

I switched on the side lamp in my dorm room, illuminating the room and setting the mood. I still hadn't released her hand, and she didn't protest. I wrapped my arms around her again and kissed her deeply. Then, I lifted her shirt and bra off her body, separating our lips for only a moment.

I removed her jeans and sneakers as well, then stood tall. "Dearest Angie, your body is so enticing, and I will cherish every moment we spend together."

She smiled and moved towards my bed as I shed my own clothing pieces - a skirt, thong, and blouse.

As our kisses became passionate and our pussies ground together, Angie exclaimed louder. I nibbled dangerously close to her neck, whispering promises of providing coffee and financial security.

She wrapped her legs around me and pressed herself against me forcefully.

"Please, make love to me, but please be gentle. I get bruised easily."

I stopped nibbling and softly kissed her lips, then her cheek, and finally her forehead, tracing my path back to her lips.

"I'll go slow, dear Angie," I murmured. "When you reach your climax, you'll know how much I'm enjoying this. I'll adore you."

I separated from her and left the room, turning off the light before returning to bed. I snuggled up to Angie. We kissed delicately as I slipped my dildo into my dripping and swollen pussy. I rubbed her back and kissed her again.

"I promise to take care of you, my love. You won't have to worry about money ever again."

With her legs now spread wide, I entered her still tight pussy, relishing her heat and sensitivity.

I didn't fuck Angie heavily at all. I made love to her slowly, our lips meeting in soft partnership as her kisses filled with affection and passion. Her kisses became firmer, her breathing intensified, and her hips followed every thrust.

She encircled her legs around me and shoved her tongue into my mouth, biting down on my shoulder.

"Harder, Anna. I need you."

I respected her wishes and hastened my pace slightly. As I felt her body shake, she bit down harder on my shoulder, then uttered loud, high-pitched sounds as she soaked my sheets with squirted orgasms.

It was a new experience for me. I had never had a woman squirt before, but it was incredible.

I gently slid to the side, prompting Angie to position herself on top of me. She understood and joined me, sliding back onto my dildo.

"Here to love and care for you, my dear," I whispered in her ear.

Her kisses were passionate and romantic as she ground her hips against me, making love. Her second climax was powerful, her entire body shaking and her breath heavy.

I carefully extricated myself from the bed and cleaned my dildo before putting it away. I then returned to bed, clutching Angie tightly.

"Stay with me, Angie. We will make love like this countless times once you begin your new job with me," I whispered into her ear.

She looked up at me and thanked me for my protection, commitment, and kindness.

"And so, my Angie, I will love you unconditionally." Angie nestled her head back down on my chest as we kissed and fell asleep.

In the morning, she awoke gentle and sensual. I burdened her with cleaning my dildo in the dorm bathroom. When she returned, we made love once more.

It was early afternoon when my phone rang, but I let it reach voicemail as we continued to embrace.

Angie agreed to work because she urgently needed the money. Her mother, an employee at the bank for twenty-three years, had surprisingly found herself jobless after a recent merger.

I pledged to shield her from the too intense deliveries coming in. We stayed on campus during Thanksgiving, working as hard as we could. I concluded a meeting and was on my way back to the dorms. I was still a bit aroused from the guy who filled me then tossed me out without any time to clean up.

My phone rang, it was Angie and she was sobbing. I rushed over to meet her, telling her to head to my room while I'd join her there.

I hurriedly got to my room and opened the door to discover Angie curled up on my bed, crying hard. I just embraced her tightly, rocking her in my arms. Once I managed to pry her hands away from her face, I saw her reddened skin; I saw the lingering impression of his hand on her face.

As she cried out how this client didn't like how she sucked his dick, after she swallowed his cum he smacked her when she refused to let him pee on her in the shower.

I was livid! I promised her I'd handle this and apologized for not being there to defend her. In our first obvious and bold act of lesbian affection, I led her to the shower and took care of my feline. I cleaned her after the shower and caressed her as tenderly as I could. When I ended, I returned her to my room and cuddled in bed with her, consoling the pain and humiliation she felt; as well as I could.

As she dozed off in my grasp, I vowed I'd speak with Liz and Susan.

It was the week prior to exams. I was barely managing to squeak by in this Calc class; I was literally on the brink of failing. I left my class and received a text from Liz. We had another delivery lined up, my sixteenth now.

Liz swore if I finished my sixteenth, I'd get another toe ring to place beside my existing one on my second toe. I was really stoked. Little did I know this one would be one for the books and it'd be quirky as hell.

I arrived at their place and was led to the living room. Liz shared I must be prepared for anything and helped me insert my biggest purple jeweled plug. It was the widest of the three I possessed.

This was a fancy delivery, a well-to-do client. I could tell this from the address. At 6pm I arrived and rang the doorbell as instructed. As the door opened, I was greeted by a man in what seemed like a dinner jacket on top of a t-shirt. His trousers matched the jacket in color.

He navigated me into the formal dining room where I came face to face with an acquainted face. She was dressed in a formal gown. The jewelry decorating her ears and the necklace sparkled and captivated my attention.

"Professor Deemer emphasized your absolute discretion," she stated. "If it's not kept, you'll be dismissed from this academic establishment. Do you grasp?"

I hung my head a bit, "Yes, yes definitely."

She tapped my chin with her finger and lifted it, staring into my eyes. "Good now Richard, dinner's ready. And you, Elizabeth, can call me Olive or Miss this evening and only this evening."

"Yes Miss Olive."

Olive maneuvered to the chair at the head of the table and was aided in her seat by Richard. He then drew out my seat and aided in my seating. A salad was served to Olive and me, and as we finished, our dinner was brought in. I noticed, Richard, who'd taken off his dinner jacket, was now totally naked.

Richard knelt and began chomping on his food like a dog, utilizing hands.

Olive started a normal conversation with me about my childhood and my modeling career. I was flabbergasted by how much she knew about me. As she finished her meal, she commanded Richard to clear our plates and continue in his duties.

Coffee was served to both of us, then I felt the warm hands of Richard slipping off my sandals and adorning my feet with delicious oils. The massage was wonderful. Olive commented she liked a foot massage after her dinner combined with her coffee.

"If Richard does an adequate job, I'll service him later, and I anticipate you joining us, sharing his sperm with him only once I've had my way with your delectable and saucy body. That's what I'm paying for."

The Vice Chancellor rose to her feet. "It's time for the fun to begin, slut." She commenced walking forward, "Richard, strip her first. I want her bare when she enters my bedroom."

"Yes, my dear Olive." For the first time, I heard Richard's voice. It was one that felt familiar, but I couldn't quite pinpoint from where.

Before I climbed the steps, I was disrobed and wiped clean of any nervous perspiration. He explained that Miss didn't enjoy too much moisture when she fucked me. As I ascended the stairs, Richard walked behind me. I felt his touch upon my hip.

"Miss, we'll need to remove that before seeing her, she'll punish us both if you're still wearing that."

I nodded, and when we reached the top of the stairs, he guided me into the smaller bathroom and bent me forward, prying out the plug from my ass. I groaned in ecstasy as it was removed. I felt so empty yet excited for what was to come.

And fucked by the Vice Chancellor I was. As Richard guided me into the room, which was more a playroom than a bedroom, Olive kissed my cheek while forcing a ball gag into my mouth, fastening it tightly. While Richard secured my ankles, calves, and thighs to the table, I was bent forward. My bare breasts pressed against the leather-covered bench.

I couldn't see what was being prepared but soon felt the girth of a rubber cock pressing against my pussy. I felt Olive's breasts against my back as she bit my shoulder and thusted hard into me.

I moaned loudly through the gag, feeling this cock spread me open wide. Miss Olive began fucking me with a force I hadn't yet felt. I bit down hard on the rubber ball gag to stifle my screams, not wanting to beg her to stop.

I lost track of time, nearing a climax as I felt the first slap. The resounding sound echoed in the room. There was a pause as I heard Richard gagging on the cock.

I heard her comment on her small dildo, explaining she wanted to now fuck my "pretty little ass."

She was forceful, yet gentle, bringing me to a powerful orgasm, one of the hardest I'd ever experienced. As she slowed her assault on my ass, she stated that Richard would clean me and then she'd milk him as his reward.

The gag was removed, and Richard led me to the shower, washing me and soothing my spanked ass. After drying me with the softest towel possible, he led me out to the room where Miss Olive stood, wearing a silk robe that gave glimpses of her hairy pussy and slightly sagging breasts. Her nipples remained pert and erect.

Richard assisted me in kneeling on a pillow. He knelt beside me, then lowered himself to the floor, his hands flat on the carpet.

I watched in awe as Miss Olive unlocked Richard's penis cage, and his small, four-inch cock sprang free. It was hard, with a purple, eager head.

Miss Olive drizzled lube on his ass and her gloved left hand. She smeared some lube on her right hand too. With her left two fingers, she pressed into his ass, twisting and fucking him. I watched as she then reached around with her right hand, massaging his balls.

"Look, darling. Watch as he takes a third and then a fourth finger into his ass."

I was captivated, seeing his ass open and her fingers move in and out. Richard was now pleading, coaching her, asking for her to touch his cock, which she refused.

He began groaning louder and she smiled wider. "Bring the small bottle, darling." She pointed with her right hand. "Hold the opening over his little cock head, so we both can enjoy his cum."

I did as instructed and was astonished as semen oozed from his cock, then a squirt of thick fluid. Richard exhaled and moaned as a third squirt splashed inside the bottle. His still swollen cock head dripped a little more fluid into the bottle.

"Good boy, Richard. You are a very good cuckold." She patted his ass as she removed her fingers. She stood up and said again, "I'll return to watch you both drink my cuck's milking."

She moved away, Richard rose from his position and knelt before me. "When she returns, you should take a sip but don't swallow. I'll kiss you, and we will share. That should please her."

The Vice Chancellor returned, smiling. She sat in a chair and lit a pipe I hadn't noticed until now. As she smoked her pipe, a delightful scent of apple and wood filled the air.

"Drink and share." She exhaled, watching intently. I obeyed and shared his cum with Richard by kissing him. I'd never experienced this before. He broke the kiss, took the bottle from my hand.

"May I, dearest Olive?" She nodded and then stood, bending forward, taking my hand.

Under her guidance, I regained my feet. She kissed me passionately prior to informing me that I had to dress. Richard would accompany me out. Walking down the hallway, she disappeared, concealed for the remainder of the night.

Richard directed me outside and handed me an envelope with a thick texture. He wished me good fortune for next month when he required his milking.

Entering my vehicle, I contacted Miss Liz, notifying her of my impending arrival at her residence.

Angie and I navigated through the holiday season. She spent a brief duration with her mother and youthful sister, Jeannie. As the latter was only two years younger, she resembled her father more closely. Aspiring to pursue a career as a physician in the northern part, she yearned to follow in his footsteps.

I celebrated Christmas at Dad's. His girlfriend, who likely was about five years older, was present for dinner. This woman sullied the ambiance considerably. I heard them engaging in sexual acts in the morning. I could hardly wait to depart, despite reaching Mom's residence in ample time for the scheduled 3:30 meal.

Despite her initial annoyance, Mom understood my difficulty with mathematics and my decisiveness to pursue nursing. Consequently, she identified it as crucial for me to address my academic struggles. Although not furious, she expressed concerns and emphasized the need for me to improve.

Visiting me on New Year's Eve, Angie appeared unexpectedly. Accepting my invitation, we acknowledged the profound kiss as the clock transitioned to midnight.

My mother retired around 12:30. When Angie required a cigarette, I resisted but eventually conceded. Stepping outside, we retreated to the lengthy grass beside the in-ground pool. She adopted a seated position next to me and retrieved a premium cigarette.

Upon breaking the kiss, Angie informed me she needed me, having missed me during the holidays. We inhaled another joint and engaged in coitus under the twinkling stars.

Primed for adventure when high, I struggled to urinate as the beer distended my bladder. Pushing past my embarrasement, I traipsed over to the back shed, relieving myself in the grass.

Angie commenced giggling, deriding me. Nonetheless, it wasn't long before she squatted and voided her bladder. Afterward, we ventured inside and snuggled compatibly within our nudity. My attraction for a satisfactory penis remained, yet Angie suited me well.

I maneuvered my car into the parking lot and advanced towards the studio. The personnel greeted me pleasantly. They echoed that Liz had reappeared in her office. With steely resolve, I journeyed to her domain and knocked on the door.

Remaining patient, I listened as noises emanated from within. The silence that ensued prompted her to instruct me to enter.

Stepping inside, I observed Liz standing behind her desk. The typical chair I sat on had been relocated to the side. In its stead, a camelback sofa occupied the center, facing her desk.

"Are you cognizant of the feats Miss Sue needed to perform on your behalf?" she inquired. "Are you cognizant of the actions necessitated by the tenured professor from the Psychology department?"

I paused before addressing her, mindful of the appropriate response. "I apologize, Ma'am. I am genuinely remorseful and will do anything you require of me."

Liz paced her office. "I am teetering on the brink of dismissing you and distributing the recordings to my associates! Now, beg for the privilege to retain your anklet and toe adornments."

Remaining immobile, I maintained my posture, not daring to utter another word. I unzipped my skirt, allowing it to fall to the floor. Bending forward, I formed a triangle with my legs and positioned my head as low as possible on the camel back.

"Please, Miss, I implore you to lend me the courtesy of retaining my anklet and toe rings. I humbly offer to tender my body for any necessary torment."

Maintaining my stance, silent and motionless, I hoped my truthful sorrow and embarrassment would pacify her. She traversed the room and relocated herself, presumably taking her seat.

"Dress yourself and depart. Our client roster is expanding rapidly. You are to deliver two specific clients without being compensated."

I put on my clothes as instructed. I handed my phone to her, and she entered something into my maps app. "Make sure you clean your bottom for your first customer. It'll be a straightforward experience. You'll be going to meet him for anal sex. He's an older man who wants to live out what his wife never provided for him."

After I left, she informed me that after the first client, I would come to her house. She would be dressing me for this person she was close to. "But, be aware, by the time he's done, you'll be gagged and thoroughly fucked."

I made my way to the first customer. He was forthcoming, admitting he hadn't had anal sex before. This encounter only lasted about ten strokes before he came inside me.

Several hours passed, and Liz had me dressed in a leather skirt, a leather strap bra, and a leather jacket. My feet were adorned with black platform boots that raised my height to over six feet. She made sure that my ass was clean, commenting it would need to be cleaned again soon.

I drove to the given address where I was brought into a sitting room where I met three men. They all told me how happy they were to have me as a "cum dumpster" for the next two hours.

These men filled each of my orifices twice. The halter bra was used as they held on to me. They were often harsh with me, but thankfully, none were large or very girthy.

After that, I headed to Liz's house where Susan greeted me at the door. She took the envelope from me. "It looks like your ass belongs to my department now." She closed the door, and sent me to my dorm room.

***

The registration process was complete, and the new semester had begun in psychology class. I managed to get through Professor Deemer's class. As students filed out, she asked me to wait. "A moment, please Anna?"

I paused, and waited till everyone else had left. "Ensure your exams go well this semester. If they don't, I'd rather have control over you and Angie."

"What? Miss?" I questioned.

"Don't be naive. Doesn't your wife really run all this? I'd hate to take over this entire operation. If you're a source of embarrassment this semester, your girlfriend will be under my control, not yours."

I swallowed hard. "Yes, Miss. I'll make sure not to fail you or Liz."

***

I woke up to Angie licking my kitty on Valentine's Day morning. I whispered, "There's cum in there from last night, sweetheart."

This only amplified her desire. My kitten loved the taste of cum on my skin. I opened my legs, hugging her to me, and started thrusting towards her mouth. I came hard, soaking her face with my fluids.

I pulled my pillow over my face to muffle the sound of my orgasm. When it subsided, I removed the pillow, unwrapping my legs. I asked Angie to kiss me, pressing my lips against hers.

"Kiss your lover, my kitten," she whispered.

Our lips met in a passionate, sexual embrace. My arms wrapped around her, and I whispered sweet things in her ear. "Until eternity ends, my kitten."

As we parted, we both received a text message. I checked mine - it was a delivery service requesting a double driver.

We shared a kiss, me proclaiming that I was looking forward to a wonderful dinner. We both replied to Liz agreeing to the delivery for that evening.

***End of Chapter Four***

Enjoyed your ride? More to come - chapter five is in the works. Anna discovers her and Angie's influence. A fresh face joins the team. Anna supports her too.

What do you think? Lots of love,

Aoife

Read also:

• Slim, Youthful, and Well-Endowed in Part 2
• Who's More Skilled at Taunting?
• Recruiter Chapter 5: Engaging Storylines
• North Hillside Chapter 2

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