Dr. Lilith's Retreat Part 7: Orientation (Patreon)

Jeff pulled the SUV into an empty space and surveyed the layout of the grounds.  A series of about four identical buildings were directly in front of him.  To his right was a circle with an intricate landscaped space around a fountain in the center.  It was surrounded by a set of long low buildings that seemed to stretch out from the circle like spokes on a wheel.

“Jeffry!” Carol nagged “I think you’re supposed to use the valet!”

Jeff rolled his eyes. “The valet will just park it right here.”

“It’s the rules Jeffery!” She insisted.

Jeff sighed.  The whole point of this retreat was to make peace and save his marriage.  Fighting over parking would be pointless.  He put the SUV in reverse and pulled it round the circle to the uniformed woman standing by the valet desk.

“Mr. and Mrs. Harris, welcome!” The woman announced as she handed Carol a claim tag while Jeff climbed out of the driver’s side leaving the engine running and the door open.

The woman came around the vehicle and thanked Jeff as she shut the door once she got inside.

“Say,” Jeff got her attention before she pulled away. “In case I need to get anything out of it later, where will you park it?”

“Oh we will manage your luggage sir, no problem.”  The valet said.

“Ok, great!” Jeff replied. “But if I need my car for some reason, where will it be?”

“Oh, just over there, sir.” The woman stated, pointing at the row of spaces where Jeff had parked only moments before.  As she pulled away, Jeff rolled his eyes, looked at Carol and then inclined his head down the lane as the valet pulled into the exact spot Jeff had vacated moments before.

“That’s not the point!  Rules are rules.” Carol said and turned her back on Jeff, walking down the steps towards an open door.

Jeff worked his jaw in irritation but couldn’t help but smile.   Her stubborn streak was something he loved about her, as annoying as it was.  He caught up to her and took her hand in his as he walked beside her.  Her hand was cold but it returned his grip.

Through the double open doors, they came to a long table.  An attractive woman in her 20s with wavy brown hair smiled at them.  “The Harris family!  Welcome to the retreat!”  She picked up 2 hard plastic name tags on lanyards and handed them over. The back of each tag held a QR code and they seemed thicker than they needed to be.  
Carol slipped hers over her head with a smile and Jeff did the same.  He noticed that rather than having his name printed directly on the card the way Carol’s was, it was printed on a stick-on label, he assumed someone had made a typo.

He glanced down at the other tags on the table, a lot of them had printed labels on them.  Someone made a lot of errors.  Jeff wondered if there had been an import issue in the software.  His musing was cut off however as another beautiful woman in her 20s with red hair approached them.

“Are you the Harris family?”  She asked.  “I’m June and I will be getting you both settled!”

Jeff introduced himself and Carol with a smile.  He wondered if they had recruited their staff from a local college sorority, all of the staff he had seen except for the Valet had been young women of the same age.

June began walking down a long hallway with windows on the left and wood paneled walls on the right, divided by the odd closed door.  She went into her spiel “You are lucky to be among the first guests of this retreat, well this retreat was centered on Dr. Lilith’s program.  The property itself has been a retreat compound since the 1970s.  It was used primarily for religious and corporate retreats as it changed hands several times over the last 50 years or so.  Finally, several years ago, the owner of the property was convicted of securities fraud and this property was among the government’s seized assets.  Dr. Lilith saw the potential of the property and purchased it early last year.  Since then we have been working around the clock to restore a truly unique location and get it ready for you all today!”  She stopped outside an open door.

“Carol, this is you.” June said

“Uh, Excuse me?” Jeff interjected as Carol let go of his hand.  “I thought this was marriage therapy.  Shouldn’t we be together?”

June smiled. “Sir, Dr. Lilith’s program is very detailed.  A marriage is made up of individual people and we work with them individually to make sure that they best fit.  At this stage, Carol has her sessions and you have yours.”

“Jeffery,” Carol said with an edge in her voice. “I am sure they know what they are doing.”

Jeff looked through the open door into the dim room.  He could see a comfortable couch, some soft chairs and smell aromatherapy oils.  It was exactly what he would expect from a therapist space.  “Okay, Honey.  I’ll see you later.”  He said.  
Carol walked past him and into the room ignoring his lean in for a goodbye kiss.

“Love you!” He said.

“Okay!” Carol said.  “Now go!”

Somewhat disappointed, Jeff turned to June and shrugged.  “Where to?”  
June smiled.  “Right this way Mr. Harris!”  She led Jeff out through a pair of double doors and across a concrete sidewalk into an adjacent building.  This building was not as well restored.  It had a linoleum floor and simple textured wallpaper on the walls, it smelled of antiseptic. June led him left, to the end of the building facing the circle.  A pair of large men in suits stood by the door outside and watched Jeff closely. June ignored them as she went to an open door.  Inside was what looked like a classroom.  Heavy tables were set in rows with 2 chairs behind each one all facing the front which had a whiteboard partially covered by a pull down projection screen.

Do not open your box until instructed

Was written in large letters on the exposed portion of the whiteboard.  Four other men stood around the room chatting quietly with each other.

“Group therapy?” Jeff asked of June.

“It seems best for your program” June responded.  She motioned into the room.

Jeff sighed and walked in.  He could see that there were rectangular white boxes on the table,  each one had a name on it.  Jeff found his box on the same table as a man named Daniel.  He looked at the younger square jawed man and smiled.

Daniel returned the smile.

“Kinda unfair how the wives get a cushy room and we get sent to class” He said.

“I’m sorry?” Daniel asked.

“Oh.” Jeff paused. “Maybe it’s individualized, but it looked like my wife had a relaxing aromatherapy session ahead of her when I left her a minute ago.”
“You came with your wife?” Daniel asked.

The classroom door clicked shut as June left.

“Well, yea '' Jeff responded. “Marriage counseling and all.”
“I’m here for mandatory sensitivity training.” Daniel said. “My company sent me”

“Sensitivity… No.  No this is a couples therapy retreat!” Jeff was getting very confused.  He turned to the young man with a crew cut and tattoos in the next row over.  “Excuse me!”  The man was in an animated conversation with an emaciated long haired man and ignored him.  Jeff looked down at the box at the man’s place.  “Timmy!” He called again.

The crew cut man stopped talking and his muscles seemed to ripple across his body.

“Don’t fucking call me Timmy you bitch!” He said in slow deliberate words.

“I’m sorry,” Jeff stammered.  “It’s what’s on the box”

“Yeah, but it aint my name!  It’s just what my bitch grandmother calls me” He said.  “What the fuck do you want?” Tim turned toward Jeff revealing that his right eye and much of his face on that side was swollen, black and blue.

“OH!” Jeff was startled.  “What happened to you?”
Tim put his hand up to his face.  “I had to throwdown with some faggots at the State penn.  Make sure they knew I wouldn’t be their bitch!”  Tim was all swagger.

“Did it work?” Daniel asked.

“WHAT?” Tim couldn’t believe the question.

“Did you dissuade them or did they make you their bitch?” Daniel asked while staring dead eyed into Tim’s eyes.

“Fuck you!” Tim replied.

“Cause, a beating like that, and the lack of injuries on your hands.” Tim went on. “Tell me that rather than fight back, you gave in soon after the violence began.  So, like I asked, are you their little bitch?”

Tim sprang up on the table attempting to vault over it.  Jeff grabbed the man by his shoulders and slammed him down on the slate surface boxes flew everywhere.

“Thats ENOUGH!” He shouted authoritatively.

Tim tried to pull free of Jeff’s grip, but the other man Tim had been talking to had thrown his weight into holding Tim down too.

“Let me go!” Tim cried out, all the bluster gone from his voice.

“Are you going to answer my question?” Jeff asked.  
“Let go!”  Tim cried out again.

“Not until you tell me why you are here!”

“Plea Bargain!” Tim said.  “Judge got me out of prison as long as I do this program!”

Jeff let go and stood back.  Something was very wrong.  “What about you?” He pointed to the scrawny long-haired man.

“Detox and Rehab” The man replied.  He pulled his long-sleeve up to reveal a collection of needle marks.  “Heroin”

“You?” Jeff pointed across to two more men standing at the next table.

“Same as him!” a blond man said, pointing at the man with his sleeves up.  
“This isn’t an alcohol program” The black haired man beside him asked.

Something was very wrong.  Jeff moved toward the door when it opened.

A Young woman with long brown hair pulled back into a low ponytail walked in.  She wore a white sweater and a plaid pleated skirt.  The door closed behind her with a click. She walked to the front of the room and clicked a button on the remote in her hand.  A close-range projector came on showing the image of a muscular young man standing on the deck of a boat.

“Welcome to Dr. Lilith’s retreat” the woman said.  “I am called Miss May and I will be one of your instructors for this week!  Would you all please move to your places as indicated by the boxes on the…” She looked down at the boxes scattered on the floor.  “Timmy, Nate, you each lose a point.  Please pick these up.”

“What do you mean lose a point?” Jeff asked.  
Miss May glared at Jeff. “If you let me finish, I will explain it Jeffery.  Minus one point from you for interrupting!  I cannot understate how much you want to have as many points as possible by the end of this week!  So please, pick up these boxes, get to your places and pay attention or I will deduct five points from the entire class!”

Jeff sighed, bent down and picked up the box marked ‘Nate’ from the floor and handed it to the man.

Tim picked up his box himself and went back to his place.

The room hung in silence while Miss. May looked from man to man before continuing.  “By now, you have all discovered that you came here for different reasons.   It may seem strange that Addiction rehab, Violence intervention, and marriage counseling are all in the same room.  Let me make it very clear, every single one of you has the exact same problem that Martin in this picture once had. Toxic levels of masculinity.”

“What is this woke bullshit!” Tim exclaimed.

“Another point loss!” May snapped.  “Keep this up Timmy and you will wash out of this program faster than you thought possible!”

This threat seemed to settle Tim.  He said nothing and lowered his head.  The idea of going back to wherever he had come from seemed to terrify him.

“Timmy,” May kept on.  “Be honest with yourself, how much of the trouble you have faced in life is a direct result of you doing everything you can to prove your manhood?”

Tim looked down at his desk.

“The fighting, the sexual assault, the firearms, all about being a big man.  What has it gained you? In and out of Juvie since you were eleven?  Constant disciplinary issues before that, and now, now you have a taste of the kind of time a grown man faces.  Do you think you can do twenty years of that? Do you think you can survive?”  She paused and stared directly at Tim.   “Do you?  You are required to answer.”

“No.” Tim muttered down at his desk.

“No.” May repeated. “Which means you need to set aside the idea of being the ‘big man’ don’t you?”

Tim squinted his eyes.  His fists tightened.

“Timmy.” May’s voice was soft but reproachful.  “This is the moment of truth.”  She walked over and stood by him.  Jeff could smell her perfume.  “Tell me you don’t want to be a big man.  Tell me you are not a man or you will wash out right now.”

Tim looked at her “What?  I can’t say that!”

“You will renounce your manhood or you will walk out that door right now.  The guards are waiting!”  May demanded.

“Renounce my manhood?”  Tim was sweating.

“The pursuit of masculinity is the source of your problems Timmy.  Give up that pursuit.  Tell me you are a sissy girl or you are done!”  May demanded.

Tim gritted his teeth and shook his head.

“Fine.  Get out!” May said pointing at the door.

“You can’t make me say that!”  Tim demanded.

“You’re right! So don’t say it and leave!”  May insisted.

Tim looked at the door and then back at May.

“Or, do I need to get the guards in here to drag you out?  Maybe rough you up too?”  She asked as she held up the remote with her thumb over a button.

The two stared at each other for a tense moment.

She pressed the button.

The door to the classroom swung open and the two guards from outside came through the door looking at May.  May nodded to Tim and the guards walked over.   They seized him by the arms and forced him to walk toward the door.

“I’m a sissy girl!” Tim yelled out.

“Stop!” May said.

The guards halted and turned Tim around to face May who was walking over.  She got right in his face. “Say it again, loudly so everyone can hear.”

“I’m a sissy girl,” Tim whispered.

“LOUDLY!” May insisted.

Tim took a deep breath.  He locked eyes with Jeff for an instant and then looked away.  “I AM A SISSY GIRL!” he yelled.

“Very good, Tabitha.” May said.  She looked up at the guards.  “You may let HER go.”  
The guards released the humiliated man who seemed to slump in place.

“Class, for the rest of your stay, you will refer to her as Tabitha, with She/Her pronouns!  Is that understood?” May said.

Jeff just blinked in disbelief at what was going on.

“Tabitha, return to your seat.”  May said.

‘Tabitha’ lowered his head and went back to the spot behind the box marked “Timmy”

The guards smirked to each other and walked out the door, closing it behind them.

May returned to the front.

“Toxic Masculinity.  Each of you suffers from it, each of you will learn to let it go as Tabitha has done. Each of you will fail this program if you do not do as you are told!”  She walked up to the black haired man.  “Barry, never able to prove yourself to your father so you crawled into a bottle instead. “

“Yeah, I get it.” Barry said.  “I suck, and I’m a sissy girl now!”  He shrugged.

“When we are done, you will actually believe it, Britta. Everyone, this is Britta, She/Her.”

She then worked her way to the two junkies. “Josh, you told us you first tried Heroin on a dare to impress a girl.  Have you ever slept with her?”

“Yeah” Josh replied.

“And, where is she now?” May asked.

Josh hung his head. “She OD’d two weeks ago.”

“Did you prove you were man enough for her before she shot up the heroin YOU got for her?” May asked.

Josh had tears pouring from his eyes and was shaking his head.  “Stop it!”

“Yet, her family was generous enough to fund your recovery here.” She went on.  “You took their baby girl from them and they STILL want you to get clean!   Are you Man enough for that?”

Josh’s knees buckled and he folded over onto the floor sobbing.  “No!  No no no no no.”

“You cry like a sissy girl.  Just accept that as what you are.  No man would let that happen to the girl who depended on him to protect her. Give up the illusion.  Tell me what you are.”  May was directly over him.

“I’m a sissy girl,” Josh sobbed.

“Very good Josie.”  She spoke to the room.  “Everyone meet Josie, you will refer to her with she/her pronouns from now on too.”

She turned to Nate who was rolling his eyes.  “This is sick!” He said.

“Did you earn your coin two weeks ago?” May asked.

“You know I didn’t” Nate said.

“Using again?  Did you use this morning?  Are you high now?” May’s tone was harsh and accusatory.

Nate worked his jaw and rubbed the inside of his elbow.

“You are.” There was no question in May’s voice.  “You’ve been around the block a few times, you know what happens now.”  
Nate lowered his head.

“Don’t you want to get clean?” She asked

Nate’s face grew contorted with anger. “I interviewed with that woman for hours!  I told her it got me bad, I told her I just can’t fucking help myself!  I told her I needed this!  I’m done!  If I can’t clean up, you may as well put a bullet in my brain right now!”

“You can stay, but you know what I want to hear.”

Nate shook his head.  “Fine!”  He took a deep breath.  “I’m a sissy girl.”

“Class, meet Natalie.” May said.  She stepped around Tim. “Excuse me Tabitha.” She came to Daniel and Jeff.

“Daniel here is quite the office Romeo!” May announced. “Had two of his employees paying him ‘under the table’ to keep their jobs if you know what I mean.”

Daniel shook his head.  “It was a setup!  I never did anything to those women”

“Except fill their mouths with your spunk every morning!” May replied. “Not man enough to get a woman on your own?”

“It's a lie!” Daniel protested.

“Tell that to the unemployment clerk when you are denied a check after being fired for cause!” May retorted.  “Or you can tell me what I want to hear.”

Daniel rolled his eyes.  “Yeah, I’m a sissy girl.  Ok”

“Ok, Daisy!” May replied and turned to Jeff. “Lastly, Mr. Jeffery Harris.  So addicted to the masculine myth that infidelity soon followed.”  She said,

Jeff shook his head.  “Look!  I know what Carol thinks, but I have never touched another woman.”

May looked at Jeff for a long time and tilted her head.  “Another innocent victim?  You and Daisy should have coordinated before we talked.  Do you think Carol will accept that answer?”

“It’s the truth,”  Jeff replied.

“Well, then you have a problem Jeffry.” May said. “Cause there are three possible ways this can go.  One, you are lying to me, you did sleep with that woman from work and you lied about it to your wife, and to me when you swore you would do what was needed to save your marriage.  In which case you are no kind of man.

Or two, You are telling the truth, you never touched that woman, and you refuse to cooperate with me.  You wash out, and Carol signs those divorce papers.

Or option three, true or false, you choose to honor your promise to Carol and do what is needed to save your marriage.” She looked at Jeff and licked her lips.  “And what is needed right now, to save your marriage is for you to tell me what a sissy girl you are.”

This was going too far.  Jeff wondered for a moment if his marriage was worth this.  He looked at the door.  He could walk out right now, end his marriage and start rebuilding his life.  He thought about that life.  He had thought he knew how it would go.  He thought he and Carol would grow old together, raise a family together, spoil grandkids together.  He still wanted that.  His pride was not worth more than that.  If he had to swallow his pride to preserve that future, so be it.

He looked May in the eyes.  “I am a sissy girl,” he said.

“Good girl, Jessica” She walked to the front.  “You are all good girls, or have the potential to be.  Now take off your clothes, and place them on the table.”

Defeated, the men looked at each other and then began unbuttoning or pulling at t-shirts.

“All your clothes!” May interjected as they got down to their underwear.

Pretty soon the five men stood taken behind piles of their clothes and the mysterious boxes.  May pressed a button.

June and another woman, just as young and just as beautiful came into the room and swept the clothes into large black garbage bags with no regard to what got mixed together.  They were in and out in less than a minute.

“You may now open your boxes and put on what is inside.”  May said.

Jeff had a bad feeling about this as he pulled the tab clear and lifted the lid on the box.  Inside was a small pink cock-cage with the name “Jessica” engraved on a plate along the top of the anchor ring.  The cage was resting on a folded sheet of paper that held instructions on how to put it on.  Under the paper was  a folded set of silk panties, a bra, and clothes folded under it.

“Oh fuck!” Jeff heard someone say

“Minus one point Natalie!” May said. “Put on your cages in silence.   Once you have it on, stop and wait for me to inspect and collect your key before you proceed with the rest of your uniform.”

Jeff gritted his teeth in suppressed anger as he pulled his testicles one by one through the rear ring and then sheathed his cock in the small hood that then locked to the ring.  After he heard it click into place he looked up to see a few of the other men had finished with theirs.  Not knowing what to do, he left the key in the lock and then crossed his arms to wait.

May waited till everyone was done before walking the room.  As she came to Jeff she brushed her breasts against his arm and then knelt in front of him.  She cupped his testicles in her hand and he could feel his cock straining against its restraint as it tried to get hard.  He grimaced as her fingers crawled over his cage and her thumb traced the exposed skin at the tip of the hood.   “You’re a good girl now Jessica and girls don’t have cocks to play with.” She pulled the key out of the lock and moved on to Steven.

She took her time to cruelly tease every man in the room before returning to the front.  “Ok, sissies, time to put your schoolgirl outfits on now!”  She clapped her hands.

Jeff and the others bitterly pulled the lacy panties up over their locked cages.  He was relieved to see that the bra snapped in front.  He was less happy to find the silicone prosthetic breast forms under it in the box complete with instructions on how to properly align it before peeling off the plastic protecting the adhesive and sticking it onto his chest.  Once he had them glued in place, the weight was a constant reminder of their presence and he took time adjusting the shoulder straps of his bra to reduce the effect before putting on the white blouse with the peter pan collar.  Buttoning the blouse backwards was harder than it should have been. Under the blouse was a green vest that he buttoned below his false breasts.  The dark color framed and highlighted his expanded chest.  Lastly he pulled on the plaid skirt.  It didn’t even come down to his knees.

“Tsk tsk tsk.” May said as she walked around them.  “Hairy legs, no makeup, and that hair is just all wrong for my girls!”  She sighed.  “This is going to take a lot more work!  You sissy girls all look like men!”

Jeff bit his tongue.

May opened the classroom door.  June was standing outside with the guards behind her.  “Follow June to your dorms!  When you get there, you will shower and remove every bit of hair below your eyebrows!  Each room is fully stocked with makeup, We will teach you how to do it right as the week progresses but do what you can.  When we meet for lunch, the prettiest sissy girl will win five points! Tabitha, you lead, single file behind her!”

Tim rolled his eyes as he walked past the others.  Everyone else followed behind him as June led them barefoot into the hall.  She walked straight to the double doors and went through them.  Jeff could feel the cold air blow up his skirt as he walked outside.  The concrete was freezing against his feet.  As they made their way up the stairs to be level with the traffic circle Jeff heard someone say “FUCK” in front of him.  At the top of the stairs he saw why.  
The walkway was lined with people, mostly women all smirking at them as they walked by.  Carol was one of them.  She waved and winked at Jeff as he passed, saying “looking good Jessica!”  At that moment, Jeff knew that this had all been set up by her.  He followed the line for now, but as he walked across the retreat grounds he decided that the woman who had cruelly set up this humiliation was not the woman he had married.  He was done.

June led them to a low, long building.  Each dorm room opened to the outside.  “You girls are lucky!  As the first class, you each get a double to yourself until the next class arrives.”  June announced as she pointed out each person’s room.

Jeff waited till everyone else closed their door before he went back over to June.  “Listen, This isn’t worth it.  I thought I could make it work with Carol, but.. I can’t do this.”

“Get in your dorm, and get ready Jessica” June said.

“No.  I just need my street clothes back.  I’m not staying”  Jeff clarified.

“Minus two points!  Dorm, now!”  June insisted.

Jeff shook his head.  “The Points don’t matter!  I am leaving!”

June took out a remote like the one May had and pressed a button.

Jeff doubled over in agony as his cock and balls exploded in pain. Electric shocks surged from the cock cage through him.  He fell to the ground trying to scream but the sound was caught in his throat.  When he was aware of the world again, June was kneeling over him with her hand up his skirt gripping his balls.  She squeezed tight, causing him to moan.  “You don’t get it sissy!  You signed up for involuntary hold!  You don’t get out of here until your sponsor, Mrs Harris, signs you out and the lower your score, the longer she will keep you here.”

“That’s insane!” Jeff moaned.

She twisted and he almost vomited from the pain.  “We have you by the balls, sissy!  So get in your room, get pretty and do what we say!”  She let go and stood up over him.

Jeff tried to climb back to his feet, but she pushed him over.  “Crawl to your room like the bitch you are!”

Jeff was about to object when he saw the remote in her hand.  He turned and crawled through the grass to the concrete slab outside his door.  His knees burned on the concrete and his balls still throbbed.  He crawled through the door and pushed it shut.  He was trapped.