“Very interesting” Jasmine muttered sarcastically as her pen sailed across the page. Normally she’d be taking notes, but that was no longer necessary with her current client. She had this young man figured out. In cases like his, she would often doodle while the subject was under hypnosis. Her questions would occasionally spark a new point of interest, but at this stage, they mostly confirmed her suspicions.

She knew exactly what treatment he needed. Now it was just a matter of talking him into it. Sometimes, it helped to visualize these things; to create a portrait of the future you would make manifest. Her pen came to a stop as she completed her drawing. It was a crude representation of the alternative therapy she would conduct with the cock-sure client resting comfortably on her couch, if all went according to plan.

“Alright, Trevor. I think we’re done for now. I’m going to count to three and snap my fingers. When I snap my fingers, you will re-emerge feeling completely refreshed. Ready? One. Two. Three.”

snap

Trevor’s light gray eyes opened. He stared at the ceiling as his mental fogginess cleared. It felt like he’d been sleeping for days. It wasn’t sleep in the traditional sense, of course, but he felt well rested. He sat up and turned, his feet finding the floor. Trevor ran a hand through his short, blonde locks. When he looked up, the gorgeous therapist with the gleaming glasses and luscious black hair was smiling at him.

“How long was I out?”

“Quite a while. We’re almost out of time.”

“Did you learn what you needed to?”

“Oh, yes. I’d say we’re done with hypnotherapy for now.”

“Good, because I’m not paying a hundred bucks to take another nap.”

That wasn’t fair. She’d done more than just the hypno stuff. Still, he was starting to question why he continued coming here. She wasn’t even a licensed therapist. Her business card read: Sex Therapist & Relationship Counselor, but the only credential on her wall was a bachelor’s in psychology.

A month ago, her advertisement had called out to him like a shining beacon in the night. It came along at just the right time in his life. A picture of her, one hand on her hip and the other lowering her rimmed glasses down her nose while she stared at the reader. ’Relationship trouble? Can’t find a match? Be man enough to admit you need the help of a woman.’

From the bullet points listed below that opener Trevor got the impression she specialized in treating long time loners, incels, guys who’d fallen into pick-up artist culture and other clueless dorks. He wasn’t a member of any of those groups, but something about her had grabbed Trevor. Maybe it was her eyes; dark orbs brimming with confidence that spoke wordlessly: ’Only I can help you.’

And that wasn’t her only impressive feature. Jasmine had the body of an Olympic athlete and a beauty mark to go with it. Her tight suit-coat and heavy skirt couldn’t hide the muscle in her arms and thighs. Yet her skin was flawless and her features purely feminine. Her black hair flowed in sultry waves that extended well down past her shoulders.

No wonder Trevor was going to therapy for the first time in his life. If reeling guys in with sex appeal was her shtick, she probably had lots of clients. It seemed to have worked on him. That, combined with Trevor’s long dry spell, is why he found himself on Ms. Jasmine Walker’s couch for the third time.

“You’ve been patient up to this point, and I appreciate that” she replied, ignoring his petulance. “I assure you, we’re going to do something more concrete next. Although, it’s going to cost more than a hundred if you want my most effective treatment.”

“More?!?” he asked incredulously. “What kind of treatment are we talking about?”

The counselor chuckled as she flipped her notepad closed and set it aside. Jasmine brought the tip of her pen to her mouth and bit on it as she studied Trevor up and down.

His simple t-shirt and jeans betrayed a lack of fashion sense, but he was handsome enough. Trevor was fit and his figure filled out his clothes nicely. He would’ve done fine with the ladies if he wasn’t such a typical dude-bro. Unfortunately, her trips into his psyche had revealed he was lacking in several areas other than fashion. Chief among them were empathy, communication and a modern understanding of the fairer sex.

Trevor had some outdated notions about relationships. This had resulted in disaster with his previous girlfriends. Without Jasmine’s help, his kind were doomed in the new world. She would have to be strict with him. It would all be for the best in the end. Perhaps he’d even thank her, later, when he was a new man.

“Have you ever been to the Antilles?”

“The Antilles?”

“The archipelago in the Caribbean.”

Trevor still looked flummoxed.

“Do they not teach geography in school anymore?”

“Not much” he admitted.

“Jamaica. Cuba. The Dominican Republic. Haiti. The Cayman Islands ... etc. They make up the Antilles.”

“Oh! No, can’t say I have” he answered with a shake of his head.

“It’s gorgeous. I go there frequently for work and play. In fact, an organization I’m affiliated with hold retreats there regularly. We often bring clients who can benefit from more hands on experience.”

Trevor chuckled. “Hands on, huh? What does that mean?”

“Workshops. Role play. Deep hypnosis. Intense sensitivity training that requires a sort of ... simulated relationship. It’s much more intimate than what can be achieved in an office environment. I think you’re an excellent candidate for this form of therapy.”

Jasmine’s grin was as mischievous as Trevor’s eyes were wide. The implications were clear. The only question was if they were genuine or if this was a smooth sales pitch to get him to some horribly dull, overpriced, new age, personal growth seminar.

“That does sound interesting. Tell me more.”

“If you were to come along, our sessions, outside of the workshops, would be mostly one on one. However, I should mention all of the other counselors in this group are women and we do help each other out. Sometimes its necessary to dial up the intensity. Things can get very interesting when multiple women are involved.”

Trevor’s body temperature rose steadily. He felt like a thermometer that was about to pop and gush mercury all over the floor. He almost never sweat outside the gym, but his skin was close to breaking out in a wet sheen.

“Wow! Yeah, that does sound ... intense.”

At first, Trevor thought he was going crazy when he noticed the busty counselor being more flirty with him. Jasmine had put her hands on him during this session, guiding him to the sofa and getting him in the position she wanted. She’d taken his pulse and given him a light massage, something she hadn’t done in previous sessions. She was smiling and making eye contact more often. And now she was asking him to a tropical retreat.

No, he wasn’t imagining things. She was into him. Jasmine likely reserved these offers for her favorite clients. Trevor had heard of sex therapists who did more than just therapy and, in truth, he’d hoped Jasmine was one of those women. Now, it seemed his patience was being rewarded. He may have hit the jackpot.

“You have no idea, but I hope to show you first hand. Our next retreat is in three weeks. These events typically run four days. I’d love to take you, assuming you’re prepared.”

“Prepared?”

“Well, assuming you have a passport, you can get the time off and you can pay the entry fee.”

Trevor leaned back into the couch. “The passport is no problem. I had to get one so I could go on my senior trip to Europe. I have vacation time saved up and I should be able to get the time off if I put in for it soon. That just leaves the fee. How much are we talking?”

“Two thousand dollars.”

Trevor’s eyes practically bugged from his skull. “TWO THOUSAND?!? For four days?”

“And three nights” she said matter-of-factly.

“Where are we staying, the Ritz Carlton???”

Jasmine laughed. “Nothing that fancy. Though, our group does require some special accommodations to put on our training. That’s why it’s a little pricey. And we therapists need to be paid for our time, too, of course.”

Trevor encountered his first hint of trepidation. For that kind of money, he could go to Vegas and have one hell of a weekend. He could gamble, see a number of fantastic shows and pay for the company of several women. Of course, he would feel like a loser by the end of it. That was the easy path and it wasn’t going to help him with the ladies in the future.

His beautiful counselor, on the other hand, was offering a trip to the Caribbean, some kind of next-level sex and relationship therapy and she was hinting at naughty fun. It had just the right aura of mystery and class to make it more appealing than splurging on booze and hookers.

“Come now, Trevor” she spoke, interrupting his musings. “Does spending three nights with me really sound so bad?”

“No, of course not. It’s just the-”

“It will be the wisest investment and the most exciting four days of your life. That’s my guarantee.”

Trevor studied the sultry woman as she crossed her legs gracefully. Her breasts seemed like they were about to burst from her suit jacket. Her strong legs flexed, leading down to commanding heels. She lowered her glasses and looked at him directly, their eyes meeting like lonely strangers in the night. She’d already won.

“When you put it that way, I suppose I can’t say no.”

“That’s the perfect attitude” she replied, pointing at him and flashing a smile. “You’ll need to cover your own air fare as well, but everything else is included. You won’t have to worry about meals and such.”

“Alright. Are we having another session before the trip?”

“No, that won’t be necessary. I’ll be heading down early to help setup the training, so I won’t see you again until then. I’ll text you the details tomorrow so you can book your flight.”

“Great. Anything else I should know?”

“Yes, one thing. I’d ask that you not masturbate between now and the trip. That’s very important.”

Trevor looked like he’d just been smacked in the face. “What?!?”

Three weeks without jerking it? For a guy in his late twenties? He felt like he’d just been assigned to some hellish purgatory.

Jasmine’s impish chuckle reinforced the prospect of naughty fun to come. “It’s crucial that you enter this with the right mindset. Follow my instructions and you’ll be attracting the right kind of women in no time. Trust me.”

Trevor sat in the airport lobby, shifting uncomfortably in the rigid seat as he waited for his flight to begin boarding. It had been several long weeks of blue-balled anticipation, but the day had come and he would soon be taking his first trip to the Caribbean.

He lamented that he couldn’t put in his ear buds and ignore the noise around him, but he didn’t want to miss an important announcement and get caught with his pants down. Trevor scrolled through his socials leisurely, barely paying attention to the usual stream of bullshit news and mediocre memes. It was mostly to give his hands something to do. His mind was fixated on the next four days.

Would this trip be a massive disappointment and a total waste of time and money? The best long weekend of his life? Something in between?

A series of futuristic beeps blared through his phone’s speakers, letting Trevor know he had an incoming call. The pop-up notification read: Jasmine Walker. He smiled and hit the accept button.

“Hello, Miss Walker.”

“Heya! I caught you before the flight, huh?”

“Yeah, I’m waiting for it right now. Should be boarding soon.”

“Awesome! I’ve been here for a couple days. The weather is perfect and the hotel is prepped. This is going to be a great event!”

“Sweet. I’m looking forward to it.”

“I bet you are. I’m glad you picked up on my hints and agreed to come.”

“You were laying it on pretty thick. Only a total idiot wouldn’t have caught on.”

“Yes, well, I don’t like to be too obvious, but some guys can be pretty oblivious. Not you, though. You’re clearly ready for some advanced training. By the time I’m done, you’ll have to fight the ladies off with a stick.”

“I have no interest in fighting them off. There’s plenty of me to go around.”

“Oh-ho! Bold words. We’ll see if you can live up to them. Have a good flight, lover boy. And check your email. I just sent a pic.”

’Whoa! ‘Lover boy.’ It’s on for sure! Don’t overreact ... Play it cool.’

“Will do. See you soon, pretty lady.”

He heard Jasmine giggle before hanging up. Trevor quickly banished his phone app and switched to his email. Sure enough, there was a message awaiting him from the sultry counselor.

The picture loaded and he barely recognized the woman who’d been his therapist for two months. Her dark hair was done up in a high ponytail. Her makeup was much more pronounced with dark shadow, prominent eyeliner and ample blush adding color to her cheeks. Her blue eyes sparkled as she gazed into the camera.

She’d posed for the selfie with one hand on her wide hips, just like in the ad. Jasmine wore a sleeveless leather top that molded to her curves wonderfully. In stark contrast to her conservative persona at the office, she looked wild and ready to head to a nightclub.

Jasmine smiled and held up two fingers in the classic peace sign. That was the most common association, though Trevor knew in many parts of the world it instead meant ‘V for victory.’ It had formerly been a post World War II gesture of celebration, but now was used more as a statement of cute playfulness.

’Goddamn, she looks amazing! And she obviously wants in my pants. I definitely made the right call.’

He gawked at the photo until a woman announced his flight over the intercom. The plane was boarding. It was time to takeoff for paradise.

After disembarking and a long cab ride, Trevor found himself in the hallway of a swanky hotel. It wasn’t a five-star establishment by any means, but it seemed pretty upscale for the relatively small island nation he found himself in. The natives spoke an odd version of broken English in which you’d be lucky to catch every other word. Their language and culture was a hodge-podge influenced by a dozen different nations from colonial times.

Jasmine met him in the lobby and he followed her, watching her body flex in the same leather top she’d sported in the photo. She wore a long, matching midi skirt below, it’s glossy black rippling as her legs pumped. The pattern held as Trevor followed her legs down into black leather boots with stiletto heels. Her dark hair bobbed in the tall pony tail; the luxurious locks trailing down past her shoulders even from its up-tied source.

Trevor wondered if she was really a fan of leather or if she’d worn something more provocative to get him psyched up for the first day of ‘therapy.’ He wouldn’t think anyone would choose to wear leather this close to the equator, but the hotel air conditioning was on full blast, which probably made it tolerable.

In fact, unless you were very warm blooded, you would want to wear something heavier to avoid getting cold. Luckily for him, that had never been an issue. He felt fine in his button down shirt and chinos. The cool air felt nice on his skin.

“Why aren’t the bell hops following with my luggage?” he inquired.

“They’ll bring it up shortly. They’re pretty busy right now. Lots of guests checking in.”

Trevor nodded. The lobby had been pretty packed. At least he didn’t have to lug the heavy bags around by himself any more.

“Do we have an orientation tonight?”

“Nope” she answered over her shoulder. “Not until tomorrow. Tonight you can rest up up from your flight and we can get to know each other a little better.”

“Awesome” Trevor replied with an encouraged grin. He was pleasantly surprised. The last thing he wanted after passing through two airports was to listen to some woman yammer on for an hour or two. Also, he knew what getting to know each other was code for. It seemed this mini vacation was about to kick off in grand fashion.

They continued on until Jasmine slowed to a stop in front of room 237. She turned and smiled at Trevor before pulling a key card from her pocket and swiping it over the door’s magnetic panel. The portal opened with a metallic clunk and Jasmine waved him in. Trevor stepped through first and was immediately blown away. The room was massive, immaculately furnished and well stocked with booze, snacks, toiletries and other complimentary gifts.

“This is my room?!?”

“No, this is our room.”

Trevor turned back to her as the door swung shut behind them. “Wait, you mean we’re staying in the same room? All weekend?”

“Mmmhmmm” she answered with raised eyebrows. “I wasn’t kidding when I said simulated relationship.”

He couldn’t believe it. This was getting better by the minute.

Jasmine clasped her hands behind her back, which caused her ample bosom to stick out even more in the shiny leather bodice. She strolled forward slowly, growing closer by the second as the anticipation built.

“Maybe, if things go well, it won’t be a simulation for long” she spoke evocatively. Her smokey eyes and full, red lips betrayed lustful intent.

Her breasts pushed into the top of his chest and he realized just how much taller she was in her high heeled boots. She was already tall for a woman, but now she had at least an inch on him. Jasmine stared at him for a few moments, breathing softly as her scent wafted over him. The tip of her tongue poked out, gliding across her top lip suggestively.

In a surge of primal desire, she dove on him. Jasmine’s hands groped him all over as they started to kiss. Her tongue invaded his mouth aggressively. Trevor took hold of her curvy frame, tracing it up and down several times before giving her fulsome ass a hungry squeeze.

“I think-- You’re fucking hot” Jasmine spoke breathlessly around sucking kisses. “And I want you right now.”

“I’m all yours-- Miss Walker” he answered between wet smacks and pleasurable murmurs.

They made out at length until their passion was interrupted by a knock at the door. Jasmine broke the kiss. She pointed down the hallway past the kitchen.

“Bedroom is that way. Get out of those clothes. I’ll collect your things and be right there.”

“Yes, Ma’am” Trevor answered, his cheeks filled with rosy red. He turned and strode off to find the bedroom. In the background he could hear Jasmine open the door and speak to the staff in their weird dialect as he went deeper into the luxury suite.

The bedroom had a nice view, a giant bed and a TV almost as big as the one in the living room. Trevor couldn’t stop smiling as he disrobed. For once in his life, he’d taken a chance and it had paid off. Thank fuck he hadn’t gone to shitty-ass, disgusting Vegas.

He’d stripped down to his boxer briefs by the time the dark-haired beauty returned. He didn’t lift heavy weights, like he was pretty sure Jasmine did, but his body was well toned. He liked to spend his nights at the gym running laps and shooting hoops in between a round or two on the weight machines.

“I know how it is after a flight” Jasmine noted. She lifted her arms and untied the band holding her hair up. Her lovely locks glided down in waves of silky jet black. “You look like you could use a massage. Get on the bed, face down.”

Trevor wasn’t going to argue with that. “Wow! You know, you could’ve sold this to me as ‘the perfect girlfriend experience’ and it would’ve been a much easier sell” he quipped as he stretched out flat on the bed and settled into the soft covers.

“Oh, it won’t all be peaches and cream” Jasmine admitted as she grabbed a bottle of lotion from the dresser and squirted it into her hands. “But by the end, I think you’re going to have a whole new perspective on life.”

The mattress shifted as the weighty amazon slid onto the bed and crawled over Trevor’s body. She planted her strong legs on either side of him, her knees digging down around his waist. Trevor felt something firm press down on the small of his back, but he figured it was just her leather skirt, bunched up below her. He moaned as Jasmine sank her strong hands into his shoulders and began kneading away.

She traced his arms and back up and down, groping him with an impressive grip. Where her hands flowed, tension and stress exited his body. He spoke muffled gibberish into the duvet as she put him at the greatest ease he could remember in his life. Trevor didn’t even notice the light metal clinking when Jasmine reached over and grabbed something from under the pillows.

“Give me your arm” she commanded. Trevor let her pull it behind him.

CRRRRICK-CRICK

He felt a metal cuff tighten around his left wrist.

“Wait- What?!?”

“Shhhhhhhhh” Jasmine leaned down and hissed into his ear. “Just go with it” she implored as she seized his right wrist and pulled his other arm behind his back. “Let me take you places you’ve never been before” she added in her most sultry tone.

“Haha ... Alright...” Trevor replied meekly. He yielded to her as she secured the other cuff around his right wrist. Given how strong she was, it’s not like he could stop her in his current position.

CRRRRICK-CRICK

“There we go. Almost ready to party!”

“Why, what else do we have to-”

Before he could finish the question, it was answered for him. Jasmine’s hands reached over his head and lowered a bright, red, rubber ball gag into view. She pulled it to his lips, mashing it against his face as Trevor closed his mouth just in time.

“Mmmmm!”

“Open.”

“Mmmphhhmmmrrrrrmm!”

“I said open, Trevor! From here on out, you’re going to do what you’re told, or there will be consequences.”

“Wait, I--”

His words made it just wide enough for Jasmine to pull the smooth, thick ball past his lips. She tugged it with all her strength and Trevor opened his mouth wider, if only to spare his teeth. His eyes bulged as his entire mouth was filled with unforgiving, spherical rubber and his jaw was forced open permanently. Jasmine secured the device behind his head with a web of leather straps that dug into his hair and flesh tightly.

’Oh fuck! What the fuck did I walk into?!?’

Jasmine’s hands left him momentarily, but were back on his body in seconds. She wrapped another thick piece of leather around his throat and he quickly realized it was some kind of collar. It clinked and jangled as she moved it into place. She worked intently, tightening it snugly around his neck as she secured its many metal buckles and fasteners.

“It should come as no surprise that you’ll be calling me Mistress Jasmine from now on. That is, when I give you back the ability to speak. That won’t be for a while. On the first night, good little slave boys should be seen and not heard as they learn proper decorum.”

“Mmmppphhgglllmmm! MMPPHHHRRRRRMMM!!!”

“Shutup!” she shouted, grabbing his head harness sternly. She dug one knee into his back, pushing him deep into the bed to cement the point that she was in full control. “Unless you have something damn important to say, you speak only when spoken to! Two oinks for yes, one oink for no! Understand, piggy?”

Trevor was overwhelmed by shame, but he didn’t want to piss her off. The full gravity of his situation was descending on him like an array of ominous storm clouds.

“Ommph! Ommph!”

It was the best approximation of an ‘oink’ he could do with a mouth full of wet rubber.

“Better” she said with a playful smack to the side of his face.

She slid off the bed again, but was back in no time. Trevor felt her hands all over his lower body. She held something cool against the skin of his thigh.

snip snip snip snip

“We won’t be needing these anymore.”

His boxers were shredded and their remnants pulled off with a combination of metallic slices and stretched ripping sounds. Soon, his buttocks were exposed to the frosty hotel air.

“Mmmmm, not bad Trevor!” Jasmine cooed as she groped his bare ass cheeks. “Your ass might be your best feature! I’ll be making frequent use of it.”

“NNNRRGGGHHH! NNNNPPHHHH!!!” His body shook in her grasp as her intentions grew more clear.

“Oh, forgetting the rules already? That’s going to cost you.”

Jasmine rose and walked to the dresser filled with toys, fetish clothing and restraints. She retrieved a long, sturdy paddle before making her way back to the bed.

“Ten strokes to help you remember, bitch boy.”

WACK WACK WACK WACK WACK

She brought the flat end of the paddle down fiercely across the center of both cheeks. Each one grew more painful than the last as she put every bit of her considerable strength into each massive swat. His ass jiggled and grew more red with each crack. The final five broke his silence as Trevor groaned painfully into the increasingly sloppy gag.

WACK WACK WACK WACK WACK

“Up on your knees, unless you want ten more” Jasmine ordered as she tossed the paddle aside casually.

Trevor hurried to obey, shimmying his legs up the bed. Jasmine helped him into position, guiding him until his backside was in the air and his knees pressed down into the duvet. His limp cock and scrotum hung below, free for the twisted Domme to do whatever she pleased with them. Trevor quivered with his face pressed into the bed as he dreaded what she’d do next.

Jasmine examined his bottom, running one hand all over his balls before seizing his half limp cock and stroking it up and down. She masturbated him until it grew to a full erection. He was responding to her sexual aggression in spite of the bondage and his own fears. Trevor’s body was betraying him.

“Damn! A nice ass and an impressive cock! Seven inches, I think? You’d have no trouble finding a girlfriend if you weren’t such a fucking asshole.”

She released his cock and reached for something else below the pillows. It was the final piece she needed before the festivities could really get into full swing.

“That’s what this weekend is all about, Trevor. You learning what life has been like for women for most of human history. You were close, about this being the ultimate girlfriend experience. It’s actually the ultimate boyfriend experience, and you’re mine for the next four days! I’m going to train you into a proper submissive boy toy.”

As she spoke, Trevor felt Jasmine guide something past the tip of his penis and ease it up the full length of his shaft. Once at the base of his cock, she pulled the straps tight, sealing it to his pelvis. He felt something small, but weighty, pulled up into the back of his scrotum. Two short, cool metal prongs pressed into his balls.

“There! Now we can have some real fun!”

She disappeared just long enough to collect some more toys. When Jasmine returned, she grabbed hold of his body and rolled him over. Trevor lay with his bound arms behind him, staring up at the grinning temptress. She wasted no time fastening gleaming, spiked metal clamps to Trevor’s nipples. As the cool metal bit into his sensitive bits, Trevor yelled into his gag. He yelped again when Jasmine tugged on the thin metal chain connecting the two clamps.

“MMMRRRGGGGGHHHHHHHHH!!!”

“Oh, stop it! You think they hurt now? Wait till we take them off. That’s when the real pain kicks in.”

As Jasmine stepped back and admired her work, Trevor noticed something that multiplied his growing anxiety. The thick leather skirt could no longer hide Jasmine’s weighty appendage. Not at the long, fat size it had grown to, feeding on Trevor’s fear and pain. With horrific clarity, he realized she wasn’t just a con artist and sadist. She was a Futanari to boot.

“Oh, whoops!” she exclaimed, following his startled gaze downward. “Guess that spoils the surprise!”

She undid her skirt, stepping out of the glossy leather and tossing it aside. Revealed in its totality was her humongous club of flesh jutting through her silky nylons. She pulled them down, freeing her cock, so Trevor could get an eyeful of her massive weapon at full mast. He stared at it in shock. Her erection was more than a foot long and at least twice his own girth. A giant pair of fleshy cantaloupes hung below it, carrying the promise of more seed than any male could ever hope to conjure.

As he gawked at the powerful Futa in horror, Jasmine unburdened herself further. Her leather top was unzipped, unlaced and cast aside, freeing her sizable breasts. They were equally impressive as her cock, jutting out enticingly and glistening with a thin sheen of sweat. The mighty woman oozed pure dominance and unrestrained eroticism. This was only magnified when she reached to the dresser and lifted a black and gold Venetian mask to her face. Jasmine tied it behind her head, completing her image as a Dominatrix in full bloom.