The Interview
by sheepisheyes » Wed Mar 19, 2025 12:10 pm
Billy showed up at his interview early. Brenda was waiting for him and introduced herself. Brenda was knock out gorgeous. She had big firm tits behind a white blouse where the buttons barely contained them. She had on a business skirt that came just above the knee. Billy found her very intimidating. “Have a seat Billy” she said as Billy sat down in front of her desk. Billy’s eyes immediately went to her cleavage and Brenda noticed. She had Billy’s resume and was reading it and asking him questions. Billy was very nervous because he was fired from his last job because he was caught masturbation in his office.
His old boss Michelle was also very attractive, and the office was full of young attractive women as well. Billy had a constant hard on and ogled the women. This made them uncomfortable at times, but they also were aware of the fact that Billy might be a little creepy, but he was harmless. Billy was pretty scrawny and obviously had no experience with women. It was also abundantly clear that he was a compulsive masturbator. The women would tease Billy about being a virgin and watch as he snuck into the bathroom. The sounds of masturbation were pretty obvious. Billy found humiliation was a huge turn on for him and he could not help but play with himself when they teased and humiliated him.
One day one of the girls in the office really let in to poor Billy. She was in a nasty mood and Billy was trying to see up her skirt as she went up the stairs. She scolded him and started questioning the size of his penis. Billy turned red and hung his head and skulked away to the bathroom, except it was occupied. The humiliation made him so horny that when he got to his office he unbuttoned his pants and reached into his underwear to play with himself. The young woman had gone to Michelle to complain that he was trying to look up her skirt. Michelle showed up at Billy’s office and caught him with his hand in his pants. Poor Billy looked up and realized there was no getting out of this. His face turned beet red, and the humiliation washed over him as he ejaculated in his pants. Michelle just stood there watching as wetness spread across his crotch. “You’re fired Billy. Pack up your things and leave right now” was all she said.
So, Billy sat there at this interview hoping that word of his termination did not reach his new potential boss Brenda. They talked about Billy’s work experience and what his interests were. Then Brenda said, “So Billy, I spoke with your old boss Michelle” and let it hang there. Billy turned 8 shades of red and hung his head. He knew he was done for. “From you reaction, I think you know what I am going to ask?” she said. “Um. Maybe” he shrugged. “Well Michelle told me how when the girls in the office humiliated you, you would run to the bathroom and masturbate. An then you got bold enough to masturbate in your office until you were caught. Isn’t that right Billy”. Billy couldn’t speak. The humiliation washed over him, and his small penis began to stiffen in his pants. Brenda could tell he was becoming weak and helpless.
“Billy I cannot have you masturbating in your office. The women here are very aggressive and given your small stature and beta manner, they are definitely going to humiliate you. Do you think you can control yourself in this environment?” she asked. Billy really needed a job but was helplessly submissive right now. “I’m sure I can Ms. Brenda” he squeaked. Brenda liked being called Ms. Brenda. “Well Billy I am going to test you then” she said as she reached into her desk drawer and pulled out a travel size jar of Vaseline. Billy just starred. “I am going to humiliated you. You are welcome to masturbate in front of me without consequences, but I need to know where we stand with you. Do you understand?” Billy just gulped and turned even more red.
Brenda unbuttoned one of the buttons on her blouse spilling out even more cleavage and gave a view of her white lace brazier. “You are a pathetic boy. You were caught masturbating by a bunch of women. How humiliating. You don’t have any control. I bet you are going to play with yourself right now in front of me.” She kept taunting Billy. He lost control, and stood up pulling is pants down, lubed up and started stroking right in front of his potential boss Brenda. She started laughing “You don’t even have a man’s penis! Look at you! How pathetic. I cannot believe you are actually playing with yourself in front of me right now.” Poor Billy came all over himself. He was so humiliated. She handed him some tissues.
“Well, you failed that test. Billy I like your qualifications, but I cannot have a masturbator in my office. I will hire you under one condition” she stated as she pulled a pink chastity cage out of her desk. “You will come to my office each morning and I will lock your penis up for the day. At the end of the day, I will unlock you and you can go home and masturbate as much as you desire.” Billy was stunned as he wiped up his cum and zipped up his pants. “I really need a job and I will do anything Ms. Brenda” he replied. “Very well. I will see you in the morning.”
Billy showed up a little early and tentatively knocked on Brenda’s office door. “Come in. Oh, Billy right on time. I like that. Obedience is very important when you work for me. Now let’s get this on you. Drop you pants and underwear” she ordered. Billy complied as embarrassment washed over him. His little penis was sticking straight out. “My my Billy you are not very big, but you seem to be very hard. Fortunately, I think this cage will fit you even in your excited state.” She exclaimed as she lifted his balls and penis and settled them in the chastity cage, encasing his manhood (or maybe boyhood) and locking it shut, placing the key in her desk drawer. “Now pull up your pants and run along, you have a lot of work to do today. Come by my office at the end of the day and I will unlock you.”
Billy found it difficult to concentrate with his semi hard penis confined in his cage. It was a little painful and he needed to try to get his mind off of it, but the humiliation of this morning was too strong. As promised Brenda released him at the end of the day and Billy had to play with himself in his car instead of waiting until he got home. Day after day went on and poor Billy was in a constant state of arousal but could do nothing about it at work, causing him to actually be more productive once he got used to his cage.
One day Billy knocked on Brenda’s door at the end of the day. There was no answer and one of the office girls said she went on vacation for a week. “What? What do you mean? She’s gone?” he asked. “Well duh. Yeah she’s gone. She’ll be back in a week”. Billy tried her door, but the office was locked. He started to panic. What am I going to do he thought. No, I can’t be locked up for a week!
Meanwhile Brande lay topless on a recliner in the Caribbean soaking up the sun. A smile spread across her face as she realized poor Billy’s predicament. “Oh well” she thought to herself and rubbed more lotion into her big breasts.
It was one of the longest weeks of Billy’s life. Not being able to play with himself was torture. He masturbates multiple times a day. Finally, Brenda returned from vacation and Billy was at her office door. “Hello Billy. How are you?” Brenda asked. “Can you please release me?” he begged. “Oh, Billy its morning and you still have the whole day to work. I will unlock you as usual this evening” Now run along I have a lot of catching up to do.”
Finally quitting time arrived and Billy almost ran to her office. Brenda let him in. She didn’t even apologize for leaving him locked up for the week, but Billy didn’t care as long we she let him free. “Ok Billy let’s get you out of that cage.” She teased. Billy dropped his pants without hesitation as Brenda knelt in front of him to unlock his cage. Billy looked down and saw her beautifully tanned breasts and felt his cum start to boil in his little balls. She fumbled with his cage and Billy thought “Oh know I’m not going to last”. She pulled of his cage and gently stoked his little penis as she looked up at him. Billy trembled and started to ejaculate. Brenda did not see it coming as ropes of pent up cum came shooting out of his little penis and splashed on her chest and cleavage. Brenda aimed his little penis at the floor as the rest of his sperm puddled at her feet.
“Oh, my goodness Billy I wasn’t expecting that. I guess you are also a premature ejaculator too. My, you are a pathic little boy. You should be ashamed. Now clean up the mess you made.” She scolded. Billy started wiping up his cum as he looked up and watched as Brenda unbuttoned her blouse exposing her bra encased breasts and started wiping up the cum dripping down her chest. “Goodness Billy you made mess. Don’t get all excited but I need to clean my chest and breasts”. She then unhooked the front of her bra and her tanned breasts tumbled out right in front of Billy’s eyes. His little penis went fully erect as he watched her wipe the cum off. She had no tan lines, and her breast were so big and firm. She finished and stuffed them back into her bra and buttoned up her blouse as she looked over at Billy with his mouth hanging open and a little tent in his pants. She laughed and shook her head “I guess you’ll have something to think about tonight when you play with yourself.”
Brenda thought about Billy shooting his hot cum all over her chest. Not that she found Billy attractive but the thought of his little balls being denied release for a week, and then just the slightest touch triggering a huge orgasm. It definitely made her pussy tingle. It was a feeling of power over this pathetic little masturbator that made her hot.
Brenda decided she wanted to share this power with her friend Lynne. Lynne would get a huge kick out of seeing a whimpering wanker shooting his little load. It would be like high school all over again. She smiled to herself.
Monday evening Billy came to her office to have his cage removed. Brenda smiled at him and said “Billy I am going to leave you locked up until Friday. I want you to come to my apartment and met my friend. I think it will be better if you are very obedient” “Please No! Please let me out” Billy pleaded. He got on his knees and begged. “I will do anything please unlock me! I can’t go that long without playing with myself!”. “Billy you will obey me. You have my answer, and you will do as you are told. Now go home”.
It was a long week for Billy. Brenda would not even allow him in her office at the end of the day because she did not want to hear his groveling. Billy kept thinking about going to Brenda’s apartment with Lynne there on Friday and the fact that she was keeping him locked up. He remembered prematurely ejaculating after a week of no masturbation. Is that what they wanted to see? He felt himself getting stiff inside his cage. He just didn’t want to wait all week to be set free.
Friday rolled around and Billy showed up at Brenda’s apartment right on time. Lynne was already there and the two of them were sitting on the couch drinking glasses of wine. Brenda had her feet tucked under herself while Lynne sat with her legs crossed. They both had above the knee skirts on which instantly made Billy stiffen inside his cage. “Well Billy it is nice of you to arrive on time. We were hoping you could be our entertainment for tonight”. Brenda said. “Um sure anything you want. Can I please be let out of my cage?” he pleaded. “It doesn’t sound like you really want that. I expect a little more pleading”. “Oh please Ms. Brenda. Please! I will do anything you want” Billy begged. “Remove your pants and underwear.” Brenda commanded. Lynne smiled and sipped her wine watching as Billy stood there in front of them with his pink cage and now very red face.
“Would you like to free him?” Brenda asked Lynne “Be careful because he might ejaculate at the slightest touch.” Billy stood in front of Lynne in total shame but didn’t care as long as it meant being set free. He was visibly shaking as Lynne very gingerly unlocked his chastity cage and removed it. Billy’s little penis shot straight up and was at full attention. He had to concentrate very hard not to cum. They both started laughing as they watched his little penis bobbing up and down. “Can I please play with myself?” Billy asked, “I want to cum so bad, it’s been so long”. “Do not touch yourself Billy! We have plans for you” Brenda admonished. Poor Billy hung his head in shame.
Billy stood there in front of them feeling totally vulnerable. His penis was rock hard. Lynne uncrossed her legs and Billy caught a glimpse of her raspberry colored red panties. Lynne watched his eyes go straight to her crotch. “Do you like my panties Billy?” she asked him and opened her legs a little wider. Billy’s penis literally twitched as he stammered “Yes”. She reached under her skirt and removed her panties. She handed them to Billy and said, “Then put them on.” They both watched Billy’s reaction. He was so embarrassed, but they could also tell he was turned on. His stiff little penis was giving him away.
Billy took the panty and pulled it up his legs and over his stiff little cock. He was small enough that the panties could contain his balls and cock completely. The feeling of the warm satin panty caressing him was becoming too much. He sheepishly looked at the two women as Brenda laughed and said “Oh my not only are you pathetic but now you are a sissy too. Billy the pathetic sissy. Look at you in Lynne’s panties with your little tent in the front. I guess you have officially lost your man card for good” They both broke out laughing.
Humiliation washed over poor Billy as he rocked his hips. “He’s going to cream his panties! Without touching himself!” Lynne cried out. That was too much Billy’s legs started to shake as he began filling his panties. His cock exploded into the satin fabric. Brenda and Lynne starred as a wet spot formed and a white cum puddle pulsed thru the fabric. Billy’s penis twitched in the panty as more and more cum flooded it. Soon they were soaking wet with his sticky cum. The women could not stop laughing. They both watched as Billy’s penis finally subsided into his sticky wet panties. They sipped their wine watching as he became more and more uncomfortable. Lynne had to admit the power they had over him was making her horny. She was not attracted to him in the least, but the power was an aphrodisiac.
“Have you ever eaten a pussy Billy?” Lynne asked and opened her legs so he could she her bare shaved pussy. Billy stared and stammered “No I haven’t”. They watch the tent in his panty start to reappear. “Oh, my it looks like you like that thought”. As his little penis grew he could feel the sticky mess which made it grow even faster. “Get on your knees and crawl to me” Lynne ordered.
He crawled in between her legs and could smell the musky smell of her excited pussy. She opened her legs wider and scooched forward. She maneuvered his head, so his mouth was covering her vagina. “Now lick me Billy as I guide your mouth”. Billy obliged and began licking her in earnest. Lynne leaned back and started chatting with Brenda as she sipped her wine. Both ignored Billy while Lynne occasionally repositioned his mouth for her pleasure. They chatted for maybe a half hour until Brenda could see that Lynne was losing focus. Lynne had to put her head back as she started to climax. She pulled Billy’s head into her pussy and rotated her hips, so her pussy was grinding up and down his nose and mouth. Brenda reached over touched Lynne’s shoulder as her pussy started to gush into Billy’s face and mouth. Billy felt her nectar flooding his mouth as he swallowed what he could, and the rest coated his face and dripped down his chin and neck. Satisfied Lynne pushed Billy away as he fell back onto his panty covered ass.
He sat there in his sticky panties with Lynne’s juices coating his face. He could smell and taste her pussy. He looked up at the women watching him. He felt so humiliated sitting there in a pair of panties, wet with thick sticky cum. He knew what he had to do. He spread his legs and reached into his sticky panty and started stroking his little cock. Both women shook their heads and laughed at how pathic he was as he quickly added another load of cum to his already creamy panties.