The Virgin Servant

*A new series I’m starting. I’m going to explore sexual situations that will involve humiliations, slavery, bondage, and taboo subjects. I hope you all enjoy this part of this min-series of stories. More to come. Please leave comments and feedback. Your responses help shape my stories and my abilities as a writer. *

The Virgin Servant

            Dean Marsh was looking at his college bill. His expenses were amassing. His financial aid was not going to cover all his school expenses. He owed money for his dorm room for both semesters, his books, and some of his college courses. Fear of debt began to sink in for Dean. What was he going to do?

            “I can always be a stripper!” Dean said sarcastically to his friend Ben, as they were drinking coffee at the school cafeteria.

“Yeah but there are no guy strip clubs nearby. You’d have to travel out of town. Also, nobody would hire you, you’re ugly.” Ben joked as he laughed at Deans reaction.

            “Fuck you dude. I’m serious though. What the hell am I going to do? I don’t make enough waiting tables. My parents are broke so I can’t ask them for money. I’m fucked.”

“Check the newspaper bro or craigslist. There’s always funky jobs on there.” Ben patted Dean’s back and he went on his way. Dean sat down in the cafeteria pondering on his current financial situation.

            Later that evening Dean went back to his dorm room. He decided to listen to Ben’s advice and got onto craigslist. He spent hours and hours looking for jobs that would pay good or immediately, but it was to no avail. Dean sat in his computer chair and began to stress out. He took a quick glance at the monitor and decided to take a chance and searched for higher paying jobs. He inputted $10,000 for the minimum wage and hit search. Only one job opening popped up.

            The listing stated: “Looking for male only employees. Job requires an in-person interview and extensive background check. Job pays cash only. If interested call this number and set up an interview.”

            Dean called the number and was met on the other line by a female voice who spoke in a polish accent.

“Hi, I saw your ad on the internet, are you still hiring?”

            “We are always looking for new prospects. I need your name, age, and orientation.” Dean thought the last part was weird but he obliged.

“Dean, I’m 20, and I’m straight.”

            “Sure you are. Meet me tomorrow at the Tea Leaves diner around noon. Dress nice, but not formal. See you soon Dean.” Click. She hung up the phone. Dean was a little nervous but he had no choice. He needed the money.

*The interview process*

            Dean arrived at the Tea Leaves diner around noon and nobody showed. He looked at his cell phone and checked the time. It was almost 1pm. He ordered him a drink and looked around at the diner, nobody was looking for him. Dean finally got his drink and had given up all hope, until.

“Dean I presume?” asked a tall pale lady, with blood red hair.

            “Yes, that’s me.” Dean said as he took a gulp of his hot tea.

“Name is Olga. I was the one you talked to yesterday about the job. May I have a seat?” she gestured to chair across from him. Dean nodded.

            “I thought I was being set-up. I didn’t think anyone was going to show.”

“How adorable. Too be so young and have such worries. I was running a bit late, had an issue with one of my clients but we sorted it out. Should we get straight into business?”

            “Sure!” Dean said with eagerness. Olga smiled at her prey.

“I run an exclusive service for certain high end clients. My clients pay high dollar for escorts, services, or pleasure. I’m not a pimp and this is not prostitution per say, but my clients get what they want.”

            “Oh. What kind of clientele do you have?”

“Men Dean. My clientele is all older rich men.” Olga gave Dean a serious face.

            “I’m straight though.” Olga laughed.

“Orientation has nothing to do with anything. My clients don’t care about if you are straight or gay. They want good looking men to help them or be their ever-living fantasy. Would you like to have a trial?”

            “What kind of trial?”

“First I need to inspect you from head to toe. I will then write an extensive report about you and send it to my clients. If you are picked my client will call me and I will call you. Then you go to your job. I will detail everything out for you before the job. You have the choice to accept or refuse it. Shall we go to my house?” Dean, desperate for money, shook his head in agreement and the two left for her house.

            Olga lived in small house outside of town. The house was empty except for a few couches and chairs. Olga made some tea and poured a cup for Dean. Dean wandered around the house and saw nothing but red walls, and black trim.

            “My house is quiet no? Do you like it?” Olga looked at Dean.

“It’s simple.”

            “I wish most things were. Please come here.” Olga waved at Dean to come towards her. Dean stood right in the center of the room.

“What do I do now?” Dean asked as he saw Olga circle him.

            “I’m going to start my report on you. First things first though, take off your shirt.”

            Dean, shocked by her request, did as she asked. He thought to himself this was crazy, but he needed the money. Olga began to circle around him slowly, eyeing every piece of him. Then she spoke.

“Dean, his age is 20. He has short brown hair. His eyes are green, emerald almost. He is 5’8”. His waist size is 32 inches. His torso is smooth with minor hair around his nipples. His nipples are a light beige color; his skin is tan. His stomach is toned; he has a four-pack abdominal area. He has no hair on his stomach. His belly button is inward not outward.”

            Dean began to blush. He had never heard anyone describe him in such detail. Olga still circling him, motioned to him to drop his pants. Dean removed his blue jeans, and stood in his blue checkered boxers. Olga continued with her examination.

“His legs are toned, hairy. He has a small freckle on his left foot. His toes are neat and do not look broken. Dean, can you remove the boxer please?” Olga asked politely. Dean slipped off his boxers and stood still in the nude.

“His pubic region is shaved. His balls are average, do not look like low hangers. His cock size flaccid is 6 inches. His cock is meaty and he is circumcised. He has a fairly round bottom. His bottom his hairless except for hair around the anus region. He is also a virgin.”

            “Wait, what makes you think that?” Dean asked in defense of the comment.

“You keep getting shy when I talk about your private areas. Also, you have done nothing but stare at my breasts since we met. Am I wrong?”

Dean lowered his head. “No.”  he replied.

            “Do not be ashamed. Being a virgin will make you more money. The only issue we are going to have is your cock not being uncircumcised.  Most of my clients like an uncut cock. Your virginity will make you a hot commodity. You did fine, now get dressed and head home. I’ll get in contact with you when I find a client.” Dean gathered his belongings and got dressed. He walked out of the door and made his way back to his dorm.

*The Job*

            Dean spent the next two days staring at his phone. He was hoping Olga would call soon. He needed the money bad. School fees were almost due. He had one week left. Dean was giving up hope. He was ready to succumb to his financial woes.

            Ring!Ring! Dean’s phone had finally rung. Olga was calling. Dean picked up the phone and answered with haste.

“Hello! Hello!” Dean said with excitement.

            “Hi Dean. I have a client that is interested in you. Get a pen and paper just in case you decide to takt the job.” Dean ran to his desk and grabbed some old scratch paper and a pen.

“Got it!” Dean said.

            “Good. No this is a job for being a servant at a dinner party. The guest is having a retirement party. He will have 8 guests, all old men, at the venue. You will pour drinks only for the guests. You must also perform when asked to.”

“What do you mean by perform?”

            “If the client asks you to dance, sing, masturbate, simulate sex, or milk the other guests you must do what is asked of you.”

“I..uh..I don’t think I can do that.” Dean said nervously.

            “You will not be penetrated by anyone but yourself. That much I can promise you. The job pays $35,000 for the 3 hours you are there. Are you willing to put your orientation aside for one night?” Dean pondered her question over and over. Could he try to expand past his own safety zone? Could he put aside being straight for one night?

“What’s the address?”

            Dean made it to a small country club estate just 15 minutes outside of town. When he arrived, he was greeted by another woman, who clearly worked at the club.

            “You must be the wine bearer?” asked the woman in sweet soft voice.

“That’s me!” Dean replied

            “Great! You are much cuter than what you were detailed as. Let me show you to your station.” The lady walked him around the estate and he saw lush green gardens, fountains of marble statues, and a full table full of foods from all over. The lady walked him over to his area, which included his own bathroom and drink station. He also noticed a small box that was gift wrapped with his name on it.

“So What do I need to do?” Dean asked the lady.

            “Your job is to pour drinks for the guests. We are serving two wines tonight and water. Make sure each guest gets a drink and is happy. You also needed to change into your outfit for tonight. After dinner, you will go to the lounge area upstairs and pour drinks up there. After that you are done. If you need to clean yourself up I put an enema in the bathroom for you.”

“Thanks.” Dean replied, not knowing what an enema was for.

            “You are very cute. You will make the master very happy! Don’t forget to clean yourself okay?” With that she walked away from him and began setting up for the party.

            Dean grabbed the box and walked into the bathroom. He noticed the enema in the corner. He looked at it with interest but had no idea of how to use it. He decided to poem up the gift box and saw his attire for the event. He was going to wear a cock ring around his package, white briefs with the slit in the ass area, a collar around his neck, and body glitter. Dean began to freak out a bit.

            After a few moments Dean regained his composure and remembered this was about the money. He removed all his clothes and put them aside. First he rubbed the glitter all over his naked body, highlighting his chest the most. Next he snapped on the cock ring around his cock and balls. Finally, he slipped on the tight white briefs and noticed his bulge was pretty big. He didn’t mind the slit in the back. Dean took a deep breath. The party was about to begin.

*Enema and a party*

            The party was small but elegant. The guests were all older men around their 60s. The variety of races were nice, but to Dean he was not aroused by them. Throughout the event he got plenty of stares. The men watched him as we poured drinks and lit some cigars for the guests. He was a lamb and they were eying him like they were wolves.

            About an hour into the party he finally met the client. The man was not bad looking for being 62. He had white hair, a goatee, and looked like he took care of himself regularly. He approached Dean with sense of desire.

            “Well you are a cute little thing aren’t you.” The client retorted.

“Thank you sir!” Dean replied.

            “Please call me Daddy.” The client smirked at him.

“Thank you daddy.” Dean said with hesitation.

            “That’s better.  I see the cock ring fits snug. Your bulge is pretty massive. I could see it from half way across the room.”

“Yes, it fits very well.” Dean said shyly.

            “Fits very well…..” the client replied.

“Daddy. It fits very well, daddy.” Dean said.

            “Good boy. You are learning some manners. Do you mind if I smell your ass?”

            But before he could answer his “daddy” was sniffing the slit area of the underwear. Dean was embarrassed. The guests gazed over and stared, mouths watering.

“Did you use the enema?” the client said with a venomous tone.

            “I didn’t know how to use it daddy.” Dead replied apologetically. The client patted him on the shoulder.

“You poor boy. Well now I know what to do when we go upstairs. Go grab the enema from your bathroom and meet us upstairs. We are going to help you clean yourself.” The client gave him a slap on the butt and motioned his guests upstairs. Dean walked to his bathroom and grabbed the enema. He realized this is what he was supposed to do with it.

            Dean made it upstairs and saw all the men seated in chairs in a circle. He took a big gulp and walked into the room. He made his way into the center of the circle and them men just glared at him.

“This is my new servant fellas. He forgot to clean up before the party. He needs us to help him.” The client said as the men giggled.

            “Well he can’t get clean with those undies on.” Said one of the oldest men sitting across from the client.

“You are so right daddy. Here let me take those off you first.” The client yanked the undies straight down Dean’s body. The men gasped in excitement at the naked specimen before them.

            “I should take off that cock ring daddy!” said another old man sitting with his hand down his pants.

“Go ahead!” said the client. He shoved Dean right to the man playing with himself. The man looked at the dangling cock in front of him. He grabbed the cock ring and unsnapped it. Dean’s cock rocked back and forth from the vibration of the ring removal. The man held out his tongue and licked the tip of Dean’s cock head.

“Uh.” Dean said in fear but his cock was starting to grow.

            “We have a grower daddy!” said the man who licked Dean’s cock.

“Show me!” The client yelled. The man turned Dean around and Dean began to sprout wood. His cock grew and grew from fear and excitement.

            “What a baby maker man!” “It’s a monster!” “Look at the veins on that fucker!” all the men began to shout out loud.

“Men, first things first. We need to clean his hole, then we will watch him jerk.” With those words Dean stood in terror as his cock finally grew to its huge length.

            The client grabbed Dean and bent him over with his hair hole sticking straight up in the air.

“This is how you use an enema boy. You stick this part inside of your hole like this!” The man thrust the lubricated tip inside of Deans ass hole.

            “Aggh!” Dean screamed. The men all laughed.

“Now since you have a tight boy pussy it will hurt the first few times. Next we squirt the water deep inside of your ass.” Dean could feel the could solution deep inside of him. The men all laughed.

“Finally once you’ve taken it all in, you will leave it in for a bit and jack off. Once you cum you can squirt out the solution.”

            The client removed the lubed tip from Dean’s ass and rolled him back over. Dean sat with his cock fully erect. The men all leaned in and watched Dean like a Hawk.

“Stroke!” the men yelled in unison.

            Dean could feel the water inside of him but he did what he was told. He grabbed his cock and began to stroke his meat. His cock was erect and veiny. He also realizing a bit of pre-cum. One of the men touched the tip of the penis and tasted the pre-cum.

“Sweet and salty.” The man sated.

            Dean, with embarrassment kept stroking. He could feel his balls getting tighter and his cock getting harder. He needed to cum soon. The water was also beginning to squirt out of his hole.

“Cum first then you can squirt!” the client yelled.

            Dean began to stroke with more motion. Faster and faster, he pulled on his meat till he was going full speed. He could feel his cock beginning to twitch. He was about to cum.

            “I’m going to shoot!” Dean said as he neared orgasm.

“Squirt and shoot now!” commanded the client.

            Dean without even thinking it squirting the solution out of his ass and his seed shot straight out of his cock. The cum covered Dean’s face and his chest. The solution spread all over the floor. The men all clapped with amusement.

“What a whore!”      “He’s a squirter!” “That load looks yummy!” “Virgin!”

            Dean heard the remarks but he could not care. He was exhausted. The men all left and headed towards the exit. The client came over and bent by Dean.

“You did good boy. Now clean up your mess and then you are done. Hope to see you soon.” The client winked at Dean and he left the room.

            Dean spent 20 minutes cleaning up his mess from the floor and the cum off his body. Finally, Dean went to the bathroom and changed back into his street clothes. As Dean left the estate he got a text message on his phone. It said from Olga: “Check your bank account.” Dean checked his bank account he made way more than what he was promised. Dean walked away with $50,000 for his services.

            Dean drove home that night with excitement. He had enough money to pay off his debt, and some of his student loans. Dean fell on to his bed and began to fall asleep. Beep!Beep!

            Dean received another text message. It was from Olga again: “I have another job for you. Are you interested. Text me back asap.”  Dean, still unsure of how he felt about the last job, messaged her back. His response……… “Yes!”