Weekend Retreat

Rob had never been more ready for a weekend. Ever.

To celebrate the forthcoming holidays, in addition to the great results the company had delivered this year, they were going away for the weekend.

And everyone was in on it. They were staying at a spa hotel. The mood was jubilant as the bus slowly made its way out towards the coastal retreat where they would be staying.

They had already started drinking. The guys had popped some beers, while the ladies at the back were toasting in prosecco.

They were talking about who they wanted to fuck at work. Rob listened as Harry, Patrick and Morgan shared their fantasies.

"I'd bang Mary all day every day, guys. Have you seen those boobs," said Harry.

Rob could hear her voice from the back of the bus. And he knew exactly what Harry meant.

Mary was the quintessential MILF. If he had been told she was a pornstar in her spare time, he wouldn't have been surprised.

At over 50 years, she concealed her age cleverly. With a wide smile and dumb questions, she always got the attention she wanted. She had this habit of leaning in over your desk and barely touch you with her gigantic boobs. Everyone wanted that treatment from the stocky little blonde secretary.

Patrick chimed in.

"Nah. She's too old for me. I want them younger and fresher. I would have picked Holly."

Holly was young, sexy and big-chested. And she knew it. Everyone always wanted her to come in with today's mail. Her pink-colored hair went down to her waist.

She always dressed a little bit more slutty than appropriate, but never crossed the line. We were talking low necklines, short skirts and very tall high-heeled boots.

"I'll tell you what.."

Morgan had started speaking.

"Nothing beats a little bit of ginger fun, does it?"

He meant Tracy. A well-trained young woman with ginger hair. Her body looked like that of an Olympian. But she never made any fuss about it. She always wore plain clothes: T-shirts, sneakers and denim jeans.

"What about you, Rob? Are you there?"

He had zoomed out, but was now back in the conversation.

"It's Hannah for me. Nothing very fussy about her. She is just an ordinary good-looking woman. And she is very nice, too."

Hannah was Bob's boss, and took good care of him. They used to have lunch together. She always had a smile and a good word for him when he talked about his misses in his personal life. No girls to talk about for him

Lately, Bob had noticed a flirty tone in their conversations. She winked and smiled. It was definitely flirting.

This weekend he had plans to do something with it. A bit of alcohol, and he was sure that their relationship could be taken to new heights.

Then the bus stopped at the spa resort. They got off the vehicle and grabbed their suitcases.

The guys were sprinting to get in the pool as quickly as possible, while the girls were talking about which treatments they would get, and in which order.

Rob checked in, got his room key, and bumped into Hannah, waiting for the elevator. They got in and Rob pushed the button for the sixth floor.

"Nice. I'm there as well. Which room," Hannah asked him.

"I think it was number 60."

"Oh, great! I'm staying next door."

They got out of the elevator and walked down the hall. Rob opened the door to his room and peaked inside. Just a normal-sized hotel room, this. Nothing special.

Then he heard Hannah calling on him through the open doors.

"Yes, Hannah! Coming."

He was used to orders from her, and this one he was going to answer.

Rob walked into her room, which wasn't a room at all. It looked like an apartment. It was a big suite, with a separate bedroom and sitting room.

"Ah, yeah. I had some extra points, so I upgraded. Nevermind. I just need some help from you. My suitcase is very heavy. Would you mind lifting it up and putting it on the table over there?"

"No worries, Hannah. I'll do it."

It really was heavy, indeed, but his tall and skinny frame just about managed to do it. Being kind to Hannah would never hurt his chances.

"So. What are you doing now," Rob asked.

As Hannah pondered her thoughts for some seconds, he managed to take in the sight of her body in front of him.

Long, dark hair. Glasses which highlighted her big, blue eyes. A big bust and juicy ass hidden beneath a tight red turtleneck sweater, a black pleated skirt and dark pantyhose.

"Hmm. I think I'll have a nap before dinner. What about you?"

Rob tried to hide his disappointment.

"Yeah, I feel you on that. Me too. It's been a long fall, hasn't it? See you for dinner, then?"

"Sure will do, Rob. See ya."

Rob walked disappointingly out and back into his room, where he did as he said and took a nap.

When he woke up, he had gotten a message from Hannah.

"Can't wait for after dinner," it read.

Attached was a selfie of her, toasting with a champagne glass. She appeared to be naked, but the image was cropped at her neck.

He grabbed a beer and took a picture of it, sending it to her. The message read:

"Me too."

He finished with a kissing emoji.

He looked at his watch and realized he needed to change into his suit quickly. Before leaving the room, he drowned the beer in one gulp and smiled at the thought of squeezing Hannah's tits while she rode him into orgasm.

The dinner was dreadful. Speech after speech from dry and boring executives was made funnier by every glass of champagne he drank. The guys talked about gaming and football, but Rob didn't pay attention. He was thinking of what was next.

When they got up to leave the table, he told them a white lie.

"Just taking a piss first, lads. See you afterwards."

He headed to the restroom, as he had said, but had no intention to return to the bar with the guys.

Neither had Hannah, it seemed.

The text from her was short and simple.

"See you in my room. Be quick."

Rob hurried out, but bumped into the giggling trinity of Mary, Holly and Tracy outside.

"Hiiii, Rob!"

They giggled, and Mary gave him a hug with her huge boobs. The alcohol had made its impact. They never even used to talk to him.

"Coming to the bar?"

Rob lied again.

"Ehh. Soon. I just need to grab my phone, I forgot it in my room."

"Sure, darling. See you soon."

They giggled and walked away, their high heels clacking against the floor and their hips swaying underneath their tight dresses.

When they disappeared, Rob suddenly realized he had been holding his phone in his hand while saying it. Damn it.

They must be too drunk to understand, he reasoned.

Anyways.

Rob got up to the sixth floor as fast as he could. As he stood outside the door to Hannah's room, he braced himself. He breathed slowly and gathered his thoughts.

Be cool now. Be thoughtful. Be handsome. And you will be rewarded.

Hannah answered his knock with her voice:

"Just come in! It's open!"

He stepped inside, and could see that Hannah was ready. Sitting in a black leather chair, only wearing a pink silk robe.

She had a champagne glass in her hand and another one filled up and waiting for him at the table.

"Hi there, sexy. Come grab a seat."

She pointed at the other chair beside her.

He sat down and took a sip of the glass.

She leaned in towards him and started to whisper in his ear.

"I've been looking forward to this for a very long time, Rob. Every day for the last few weeks I have been thinking about you and what I am going to do with you. Are you ready?"

Rob nodded and whispered back.

"Yes, Hannah."

She took the glass out of his hand.

"Close your eyes and do as I tell you."

He closed his eyes and felt her standing up beside him. She walked over to the suitcase and opened it. He could hear approaching him again.

His dick had grown in his pants, and he was sure she could see the large bulge.

She sat down on him and started to grind against his pants.

"Come on, you sexy bull. Show me what you've got."

Rob still had his eyes closed. He started to get excited and inpatient.

Then something unexpected happened.

With quick motions and a metallic sound, Rob felt his wrists getting cuffed to the metal arms of the chair.

Before he could protest, she stuffed a pair of panties in his mouth. He could only make gurgling noises which no one could decipher.

He disobeyed her and opened his eyes.

Hannah had jumped off him and was bending down, cuffing his ankles to the legs of the chair.

The cuffs who held him in place were girly, in pink leather with golden chains.

He was completely unable to move. He didn't understand what had happened.

Hannah looked at him with a sinister smile. She hadn't said a word yet. She took off his clothes and shoes, and threw them in the corner.

He soon sat completely naked in the chair.

Rob looked down at his dick, which had so eagerly been waiting for this. He even had shaved himself this morning, to be ready for Hannah.

Now he was shivering a little bit, from both the cold and the unexpected situation.

His dick had shrunk to almost nothing.

"I know you had great hopes for this evening, Rob. But your dreams were never to be realized. And I never promised anything, did I? I just said I was ready for you. And I have been for a while."

She laughed whole-heartedly. It sounded evil.

"Ever since you started working with me, I have seen your horny eyes. They way you have looked at all of us. Mary, Holly, Tracy and myself. Listening to you talking during the lunches, I have understood one important thing. You're a pathetic excuse of a man. You will never get real pussy. But you will get something else. Let's see what I have in my suitcase, shall we?"

Hannah returned with a small item in pink plastic.

She took out a ring and pulled it over his shaft before she tucked his balls on the inside of it. Then she put a small restraining device on top of it, and locked it with a key.

Rob could feel his small dick trying to escape from the cage it was captured in. It bounced and twitched against the inside, before understanding the edges of the prison it now inhabited.

Then it slowly faded and went limp again.

She held the key in her hand.

"This is the only key to the cage. If you don't do as I say, I will flush it down the toilet and you will be locked up forever. Is that understood?"

Rob couldn't speak, but nodded hastily to make sure she knew he had understood the stern threat.

She attached the key to her necklace before she continued to speak:

"That little dick of yours is of no use for anybody. It's better to keep it locked up and hidden, so it doesn't scare girls who were thinking about real cock. You see? But I am not mean: I promise you pleasure, albeit in a different way, if you do as I say."

She grabbed her phone and snapped a few pictures of him.

"If you disobey me, not only will I throw away the key. I will send these pictures to the lads we both know so very well. And I don't think you want that, do you?"

"But first, we need to fix you up. You look quite silly now, don't you think?"

Hannah unlocked the cuffs. Rob stood up.

Desperate, and without thinking about the consequences, he made for a run.

He didn't get very far before she tripped him up and he fell on his face.

The groaning noises he made was a mixture of anger, desperation and just pure pain from the fall.

She sat down on top of him. She was angry.

"I told you to not disobey me. I will send the pictures."

Rob protested heavily with his muffled voice.

"But not to the lads. The girls know of my plan, and I bet they will want to see this. There! Sent."

She giggled as she sat on top of him on the floor.

Sooun Rob heard girly laughter and high heels walking down the hallway outside the room. The door opened, and they all entered: Mary, Holly and Tracy.

"Quite a catch you have got there, Hannah? Is the cage on yet?"

Mary's words were silent killers. They had known about it all the time. Suddenly their reactions outside the restrooms made perfect sense.

The lie was pathetic.

The last hug was a solemn goodbye.

Hannah got off him and four pairs of hands lifted him up and dragged him back to his chair. There he was yet again cuffed, and unable to move.

This time it was Holly who spoke.

"You pathetic loser. You thought you had any chance of fucking a gorgeous woman like Hannah? No way, bitch."

Tracy put small wireless earbuds in his ears. She picked up her phone, and soon white noise filled his ears. He could see her lips move, but didn't hear a thing of what she said.

Then he felt a hood tugged over his head from behind. He couldn't see anything. He started to breathe fast, but soon understood that it contained holes for his nose. His breathing slowed and he relaxed a bit.

His thoughts raced through his mind. Those damn girls. Tricking him into this! How could he escape? Could he even escape at all?

He couldn't see any way to get out of here. And in addition, Hannah had the pictures as well. And all the girls knew.

He could never return to work after this humiliation.

As the realization hit him and the girls started to plan his future without him knowing, tears started to stream down his cheeks.

No one saw them, but Rob knew: He was never to return to his old self.

Rob must have fallen asleep, because it felt like hours later when the hood was removed and he looked straight into Holly's big boobs.

She removed the earbuds and the panties from his mouth.

Rob understood that this was a chance:

"HEE..."

He couldn't finish screaming for help before Holly squeezed his balls so hard he started to cough.

"Don't you try anything stupid now, bitch. You promise me?"

"Yes.. Yes.. Yes.. Holly. I am sorry."

"Well. You can start addressing me and all the other girls as Mistress. We're in charge here, you understand?"

"Yes.."

She squeezed hard again.

"Yes what?"

"Yes, Mistress Holly. I am sorry, Mistress Holly."

She smiled.

"Good girl! You don't look very sexy now, do you? We have to do something about it."

Holly uncuffed him and dragged him up.

"Stand very still now. You understand? I don't want you to say anything or move an inch."

Rob didn't dare to do anything but answer accordingly.

"Yes, Mistress Holly."

As the other girls sat and watched, giggled and sipped champagne, Holly went to work.

First, it was the fake silicone boobs. Judging by Rob's eyes, it looked like G-cups, which she strapped around his bust. Now he couldn't even see his chastity cage, so big were they.

She took out a lacy lingerie set in pink. First the bra, then the garter belt and then the smooth-feeling panties. She dragged them up as long and hard as she could, and Rob felt them almost dividing his butt in two.

She made him sit down as she pulled on the stockings and attached them to the garter belt. The smooth feeling of silk made him shiver.

Actually, this felt quite good, Rob admitted to himself.

But he didn't dare to say that to the girls.

While sitting, Holly had taken out a pair of shoes from the suitcase. And they were not just any pair. The pink high-heeled platform shoes had heels seven inches long.

She tightened the ankle straps, before locking them in place with tiny heart-shaped locks.

"Stand up and walk, slut."

Holly's order was not meant to be misunderstood.

As Rob stood up, he could hear small bells jingling inside the locks.

He tried to walk gingerly forward, but felt like Bambi on ice. Managing the heels and balancing out his added chest weight didn't go well.

He fell over, but the landing was cushioned by his new chest.

The girls roared with laughter.

"You stupid slut! You're such a sissy," Mary shouted!

"You're not fit to fuck anyone in that state. But you are fit to be fucked, that's for sure," Tracy calmly said.

Rob brushed off the embarrassment and stood up. Almost automatically, his hand went to his hips.

Holly intervened.

"You want to say something, sissy?"

Rob had learned his lesson, and didn't respond.

"Come back here, sissy."

Rob hobbled back towards her, where she put on him a pleated pink micro skirt and a pink tank top.

The writing was embarrassing.

"I am Daddy's girl" it said in white capital letters. The font was girly as well.

"We're soon finished, bitch. Come to the bathroom, and Tracy will make you look wonderful."

They walked together into the bathroom, where Tracy opened a purse. She attached fake eyelashes and long fake pink nails, before adding mascara, rogue and a pink lipstick.

She finished off the job with a wig of long, blonde curly hair. It went down to his waist.

When Rob saw himself in the mirror, he couldn't see a trace of himself.

He could see what looked like a young man's version of a bimbo porn star in front of him.

And he liked it.

His small cock twitched inside his cage. Tracy noticed it as well.

She shouted to the other girls:

"He likes it! It moved!"

Hannah's voice emerged.

"I knew it! Well done, girls!"

They got up and they walked back into the sitting room.

The girls gasped at the sight of him.

"WOW. What a sexy slut," said Mary.

Now Hannah stood up and took control. She was clearly the woman behind all of this as well as the leader of the girls.

"After all this work, I bet you want a reward. Is that true, sissy?"

Rob didn't know if he really wanted this, but he knew one thing: He didn't dare to say no.

"Yes, Mistress Hannah. I really want a reward."

"Good girl! But first we need a girly name for you. Rob isn't that sexy, is it? What do you reckon, girls?"

The other girls put their heads together and started whispering. Rob couldn't hear what they said.

Finally, Holly started speaking.

"We think this is a Rachel."

"Good choice, girls. It very much is, " affirmed Hannah.

Hannah walked over to the suitcase again, and took out two items: A large strap-on which she attached around her waist. And a large vibrator.

Hannah walked towards him and pushed him onto the bed.

She stuffed the vibrator into his panties, directly against his cage. With the garter belt on the outside, it was secured.

She pushed a button and it started vibrating heavily.

Rob started to moan and became unable to control his movements as his whole body pulsated in the same rhythm.

"I see you like it, sissy. Turn around."

Rob did as Hannah told him.

"This will be painful. Popping your cherry is just that. But I promise you it will be unlike everything else you have experienced."

Rob felt a lubed-up rod trying to enter his ass.

He resisted. He wasn't used to this.

"Relax, Rachel. Relax to get your reward."

Rob breathed out heavily, and felt it glide in. Deep.

He felt like he was filled with some gigantic monster he couldn't control. It felt weird and hurt a little bit. He could feel that every millimeter of the inside of his ass was active.

Then Hannah started moving. Slowly at first, but after a while she picked up her speed.

The pain subsided and was substituted with relief. And a delightful feeling.

The combination of the vibrator and the strap-on made him shake with pleasure. He couldn't control his body. And neither his mouth, as he soon heard himself moaning in pleasure-filled horniness and happiness.

As Hannah picked up the pace even further, Rob felt he was close to orgasm. A long outdrawn "aaaah" escaped him and he felt tiny drops of cum squeeze out of his dick and started dripping.

Hannah pulled out at the same time as she stopped the vibrator. Rob collapsed onto the bed, his head filled with pleasure-contained thoughts and a sense of sensual sexiness.

"Welcome to our world, Rachel. This is how it feels to be a slut like us. You'll never be as good as us, as you are a sissy and not a real woman, but who would notice the difference? Not anyone at all when they enter you from behind."