Cornered during the Action
Introduction
Meet Jane, a thriving young businesswoman in her prime, who lives next to Simon, an adolescent college student. After leaving college, Jane founded a talent agency involving acrobatic performers. With effort and a modicum of good fortune, she expanded her business swiftly. One of her burlesque shows became a Las Vegas mainstay. Other gifted performers also thrived in the sexual arts as a result of her guidance and patronage. Consequently, Jane procured a property five years ago.
This dwelling, in a quaint secluded neighborhood, is the sole house on a cul-de-sac adjacent to a park. The region is particularly discrete, bracketed by woods at the rear of the houses and slender traffic. The other house, on the aforementioned cul-de-sac, is owned by Simon's parents. When Jane moved in five years ago, Simon, a 15-year-old, was preoccupied with comic books and video games. It was only when he turned 18 that he fell in love with Jane. He was spellbound by her charm, in the middle of her youth, plump but not flabby, celebrity-esque. However, he did not crave to sleep with Jane - like many hormone-charged university boys her age - he yearned to emulate her or at the very least adore her. Simon had always avoided sports and his current round body was the subject of disparagement.
He yearned for Jane's bewitching curves. The hypnotic hips and breasts that magnetized him when he saw her in one of her successful corporate attires, going away on one of her frequent business trips. Since he became aware of Jane two years ago, Simon frequently fantasized about becoming a woman. He had even purchased female garments for himself. He invariably disposed of them due to fear that his devout Christian parents would interrogate him about his baffling behavior.
That autumal season, two years ago, he left for college in another state. While becoming a university student, he suffered through a dismal predicament. Nonetheless, he managed to chuck some lingerie into his bags for his roommate's absence. This fiscal year, he intended to unveil his intentions to his parents. He had not mustered the bravery to disclose to his parents his chosen major in Fashion Design. He perceived that they wouldn't comprehend.
Prologue - Simon's Return
Upon returning home for his summer holiday, Simon was astonished to discover that his parents had conveniently forgotten to inform him about their intentions to renovate their house.
His parents divulged, "What's your plan?"
They exclaimed, "Ah, we've arranged everything. You probably recognise the kind-hearted woman next door, Jane? She's an itinerant professional and, fascinately, she embarked on a two-month business excursion this week. She entreats you to reside in her house and tend to her cats while we're renovating. We'll spend the ensuing month of summer deliberating your future course of action. With your scholarship, our finances are not strained regarding your tuition, boarding and sheltering expenses."
Simon's jaw slacked at the news, a medley of emotions assailing him. Would he live in Jane's home? Alone? For rudimentary months? How could he broach the subject to his parents that he had resigned and forsaken his scholarship? He was coy and his brain whirred as they carried on:
"The constructor commences work in three days, on Monday, we leave tomorrow to avoid a Sunday flight, and Jane has already rambled off to her errand. We've always wondered what she accomplishes in that posh automobile of hers! She disclosed to us that she acquired her residence five years ago."
Simon nodded, inhaling a relieved respiration. The footlocker his parents had "forgotten" contained whatever leftovers of feminine apparel he had conserved, as well as tools he had utilized to abstain from losing control. The other items - the bosom prosthetics to made his chest akin to Jane's proportions, the little chastity gadget for his petite penis - went with him to college and were crammed in his lone suitcase.
During the car ride home from the airport, an interesting conversation unfolded. When they reached their house, they found out their parents had already left for a hotel by the airport because their flight was early the next day. They gave their son, Simon, an envelope containing house keys, instructions, and hugged him goodbye with the assurance of staying in touch despite limited service in the rural areas they'd be in.
Simon found himself standing at Jane's door, undeniably nervous as he had never been inside her house despite years of maintaining her lawn and shoveling her driveway. After a pause, he entered the impeccably decorated home and opened the envelope. A brief note from Jane awaited him:
"Simon, thanks for looking after my house and cats while I'm away. I supplied enough food and litter for your stay. Feel free to make yourself comfortable! The guest room is yours for the duration of my trip. Since you don't drive, I stocked up on food and you can order more if needed. I'll be home on August 1st. Here's my email address and phone number if you ever need them. Let me know you've arrived. Cheers, Jane"
Simon immediately sent an email to Jane, expressing his gratitude for letting him stay and adding some sarcasm about his parents for forgetting to inform him about their trip.
After exploring the living room, dining room, kitchen, then the master bedroom with an attached bathroom, guest bedroom, bathrooms, office, and basement, Simon weighed his options. Although Jane had given him permission to stay in the guest room, he couldn't resist checking out her personal space. He peeked into her bedroom, marveling at the full-length mirror and luxurious en suite bathroom with a jetted tub. He smirked, "I'll stay here for part of the time. How will she ever know?"
Conveniently, he unpacked his belongings in the guest room, leaving plenty of space in the closet and drawers. After eating a small meal and having a shower, he contemplated his next move. He knew he wouldn't last long without rummaging through Jane's drawers. As a meticulously-groomed man, he was confident in his shaved legs and body hair. He planned to lock the bedroom door and keep his chastity device on while going out for essentials.
When Simon emerged from the shower, he put on the restrictive chastity lock known as the "inverted" or "negative" chastity device. This unique device was originally designed for larger men but worked well for him. It consists of a ring, a metal cup on a short post, and a metal plate. The metal ring was already around Simon's scrotum, and his cocklet barely reacted to this. The inverted part was a cup atop a post attached to the metal plate. A hole at the top of the cup was meant for his pee hole, and he carefully slipped his cocklet into place. He inserted his fingers, the metal cup and post, ensuring perfect alignment, and secured it with a wrench. The result was a small, flat plate with a hole above his scrotum, securely locking his balls in place.
Analysing his progressive attachment to the device, Simon realized it had caused a decrease in erections during his last accidental week-long use, and his cocklet occasionally retreated even when he pulled down his underwear. This made him feel like his body instinctively accepted and even desired this level of restriction. Additionally, he wore a "kitchen safe" with a timer lock, planning to spend a week locked away, then free himself for cleaning. The clear plastic safe was durable, but he hesitated replacing it due to the cost.
As the timer counted down from 5 and the lock engaged, Simon reached for his silicone breast forms, his favorite. These realistically-shaped breasts came in two black lace bras and one nude "sleeping" bra. Opting for ease, he donned the strapless bras for a more comfortable experience. In anticipation of his future, he considered utilizing the chastity lock and kitchen safe simultaneously. This would entail spending a week in complete submission before regaining his agency. The safety of the latter somewhat reassured him but pondered whether he should test his bodily reactions for a week.
He inhaled deeply, sealing his destiny, and headed to Jane's lavish bedroom. With jittery hands, he approached her dressing table, opening the drawer presumed to contain her lingerie. He was granted a mesmerizing spectacle, a variety of colors of coordinating bras and panties, some lace, some satin, some cotton, and even garters and hose. His mouth turned to cotton, he selected a green lacy bra and brief set. He awakened the undergarments, pulling them up his legs, then effectively took off the form's straps from the replica bosoms, putting on the complementary bra, placidly placing her breasts into the cups. Shutting the drawer, he... or potentially she... examined the view.
As he moved to the closet, he opened it cautiously, viewing a myriad of dresses and skirts, some businesslike that he had witnessed, some informal, some alluring. He located a green midi dress that corresponded with the bra and panty set he was donning, and took it out. He smoothed it over his body and removed it from the hanger, hands still trembling. Placing the hanger aside, he draped it over his head, settling it on his hips, and adjusted his breasts. He confronted the mirror. He, in reality, had transitioned into her. It was definitive, Simon had to partake in at least part of summer attending to his sassy counterpart. He returned the hanger and prepared to make some food.
Exposure 1: Jane
"That little prick certainly didn't wait long," said Jane, glancing at the video stream. Unbeknownst to Simone, the house harbored cameras in numerous strategic locations, all distant accessible. "He even went for one of my preferred lingerie sets. I wonder if he intends to carry on with this while I'm missing?" Jane monitored Simon--she had not yet communicated with Simone, unaware of her moniker--around the house as he cooked food and settled down to watch a film.
"I'll observe him occasionally. I'll let him have his fun, and afterwards, I'll have mine when I return. I'll have a fabulous last month before he departs for school!" It sent a ravishing arousal between her legs, her general area becoming soaked from her already cautious business attire. Despite her desire to rub her genitals to pleasure, she persisted in attentiveness to the meeting.
"I can't wait to sway this narrow ass; he has to be an innocent." While she eagerly desired to slip her fingers into her mounting excitement, she instead aimed to remain attentive to the discussion on hand.
Summer Self Sating: Both
Simone proved steadfast to her promise. Each week, she liberated herself, cleansing her gonial gland, letting it aerate, and then locking it up once more. For two months, she sported Jane's outfits, attending to them diligently, washing them as needed, progressively moving through the wardrobe. As Jane watched, she expressed, "He doesn't seem unattractive, honestly. Yet, he will experience punishment in some way. Golly, I can't wait to deflower that inexperienced ass."
Simone had unveiled that she could utilize a Hitachi magic wand to reach climax although it was ultimately unfulfilling. The gush would leak through the door in the cocklet lock, leaving her ravenous for more. Jane occasionally observed such instances, at times live, running her fingers across her clitoris as she longed with intensity about what she would undertake when she returned in a few weeks.
Exposure 2
Simone was drawn into idle musings, daydreaming, and enkindled arousal on July 31. She was sprawled on Jane's bed, aware it could be her final chance to do so. Decorated in a sultry red lace bra and brief set, having also tried out all of Jane's shoes due to their similar solesize. She was viewing a video on an alluring pop streaming site, featuring a man transformed into a woman by an actress differing only slightly from Jane. She never conjectured it could be Jane, only slightly divergent from when she lived in the area.
The video portrayed a man hub transformed into a sissy wife who gets effed by the star--Jane--once caught wearing lingerie. Oh, how Simone hoped for this to be genuine and also was dreadfully petrified about getting caught.
As she watched, Simone utilized the Hitachi on her secured cocklet beneath her lacy underwear. Her noise-cancelling headphones were on, thus she didn't hear Jane return to the home and navigate to the bedroom. Jane had a general idea of what was happening because she had been observing the stream via the concealed security camera. When Jane anticipated the peak--intended sexual innuendo--of the video, she entered the room silently and stood quietly.
From the depths of her sexual bliss, Simone was unaware until she glanced at the door and saw Jane. She jerked back, kicking the laptop, which turned around to face Jane. Jane, wearing jeans and a T-shirt, strolled into the room with a seething expression, saying, "What the hell are you doing? Wearing my clothes? In my room, Simon?"
Simone hesitated, "I... I... I can explain, Jane."
"And I see that you uncovered my other income stream."
Taken aback, Simone exclaimed, "That's really you?"
Jane nodding, "Yes, from about 7 or 8 years ago. When your parents asked what I did, I told them 'talent management.' Knowing their opinions, I didn't add 'erotic' to that explanation. And when I started, I thought that I should understand what it was like. I ended up liking it and thus did it for a few years."
From the hospital bed, Simone was confused, "So, you're actually behind this?"
Jane, now closer and looking somewhat annoyed, chuckled, "Yes, it's me. The one filmed here."
Simone was still in disbelief, "This is really you?"
Jane, still wearing jeans and a T-shirt, lifted her T-shirt, displaying the tattoo on her chest.
"Oh my god, I... I don't..." Simone stammered.
"And yes, I see you discovered my side job," Jane said with a hint of annoyance.
Simone seemed lost, stuttering, "I... I didn't know."
"You should be sorry, not because of being a sissy, but for using my belongings without my authorization. I would have preferred we'd sorted this out differently, but the cat's out of the bag, isn't it?"
The wand buzzed in Simone's hand as Jane inquired, "Don't stop due to me. You're likely already leaking into those panties. I hope you've done a decent job with my laundry, Simon."
Simone murmured, "........"
"What's that, say something!"
"Simone," Jane chided, "when I'm in this state, I use Simone."
"I... I don't know, I..." Simone's eyes flicked towards the door.
Sternly, Jane remarked, "Stay here, Simone. Let's just enjoy this for a while."
Simone closed her eyes and complied, slipping off her panties and lying on her back. Jane knelt at the edge of the bed and examined the cock lock, "This is something I want to see. Perhaps I may assist." Simone began to circle her wand over her pubic mound and the device, sometimes wandering down to her balls. She moaned, realizing that she was fully engaged in this fantasy. Her hand strayed up to her breast, nuzzling the C-cups.
Jane stood up and removed her bra, still wearing her jeans. She grinned, "So these are rather like yours, aren't they? I would have guessed you had them before you knew they'd fit so well into my clothes."
Simone nodded, her arousal escalating.
Jane smirked, "Pussy's stolen your tongue, Simone? I guess we'll have to determine what you can call me for the next month. I'm Jane for now."
Simone gasped, her arousal nearing its peak, groping, "Yes, J-Jane. U-um... I was w-withdrawing from... high school."
"Shhhh, Simone. We'll discuss that later." Jane reached behind her, unclasping her bra, though nonetheless maintaining it resting on her breasts, seductively. She slid her hands over her pussy, through her jeans, moaning softly, "That's right, good girl, get close." She slid her bra off her breasts, setting it aside and then caressed her nipples with her fingers, licking them.
Simone was unable to take her eyes off Jane, her face and breasts. Her body shuddered as she neared a climax, "Please, Jane, can I cum?"
Jane replied calmly, "Yes, baby, let it happen."
Jane grinned as she said, "What a good girl you are. You can only cum when I say you can. Stay right on the edge of it." She climbed onto the bed, sitting next to Simone, running her hand over her own bosom while simultaneously touching Simone's breasts. Simone twitched with pleasure, nearly unable to hold back, but managed to control herself with the wand. "Tsk tsk tsk, no cheating, Simone. You must obey me and control yourself. She leaned towards Simone's ear, whispering, "Believe me, it's worth the wait."
Simone moaned, resuming stroking her "intimate area" with the wand, bringing herself as close as possible to the edge. Jane leaned back and Simone fixed her gaze on her eyes, "Please, Jane, please. I can't handle it anymore!"
Jane smiled, "Not yet, Simone, not yet. I'm curious, would you like to become my little sister?"
Simone nodded vigorously, saying, "Yes, please, Jane, please make me your little sister."
Jane smiled, "Make you? I think you're almost there already, sweetheart."
"I... I am a... vir... virgin, Jane. I've played with my fingers, though never a man."
"I KNEW it! I'm so excited – I get to take your sisterly virginity. I'm so excited! I can't wait to tell my friend Mary. You'll love her." She bounced excitedly, her breasts almost hypnotizing Simone. "Okay, I give in. Ten... Nine... Eight." She began pinching and pulling her own nipples, rolling them in her fingers. "Seven... Six... Five... Four" She spread Simone's legs close together and sat on her thighs, pressing the crotch of her pants against the other side of the vibrating head of the wand. "Three," she thrust her hips, "Two," pressing her clothed pussy against the Hitachi, driving Simone closer, "One," staring deeply into Simone's eyes, saying, "Will I say it? Hmmmm? Do you deserve it? CUM!"
Simone immediately began jerking and moving about, pushing against the Hitachi, and Jane was thrusting back – both pushing hard. Spurt after spurt of cum exited the hole in the cage, Simone continuing to move until she was spent, flopping back onto the pillows, suddenly turning off the magic wand.
Jane reached down and scooped up as much of the spurt as she could, offering it to Simone's lips. The little sister eagerly licked it up and licked Jane's fingers with great enthusiasm. "Good job, my little sissy," Jane said. "Now, close your eyes, wait here." Simone heard movement and other noises, possibly pants being removed. She felt her hand being led away, down to her knees.
"Open your eyes and mouth, Simone!" Simone obeyed and saw a large dildo hovering in front of her mouth. "Now, make it wet and nice!" Jane entangled her fingers in Simone's hair and slowly shifted Simone's lips to the dildo, filling her mouth and then pulling back, rhythmically thrusting again, with more force each time. Simone submitted and went with the flow of the moment, recalling every cock-sucking video she'd seen and emulating them as best she could.
"Hmmmm, you're a hungry little sister, aren't you?" Jane asked.
Simone groaned and drove the dildo as far back into her throat as it would go until she gagged, her eyes watery from the effort. She sucked and licked, using both hands to massage the fake dildo, licking the balls, and plunged it even further back into her throat, leaking saliva down her chin. She looked up in bliss, gazing upon Jane's satisfied face past her breasts.
After a while, Jane pushed Simone back down onto her back, standing over her with the dripping dildo and a view of her slick pussy. "On your back or on your knees? How should I take your virginity?" Jane mused, stroking her dildo as if to keep it hard. "I want to see your face when I do it. Front and center!"
Jane moved from standing between Simone's legs, pushing her up and onto the bed. She grabbed Simone's legs, pulling them up to her shoulders. She positioned the tip of the dildo at Simone's sissy's entrance, rocking her hips, stretching Simone open. She spit on the dildo and gathered her juices to lube the toy and Simone's vaginal opening. She continued to poke and push, Simone groaned and Jane made eye contact.
Prepared? Simone confirmed with a slight nod, feeling her heartbeat hasten. Jane persistently pushed Simone's transgender pussy until the tip penetrated her. She paused, relocating her hands to her breasts, teasing her nipples before bending over to grip Simone's hips. She shoved the strap-on into her as Simone bent her back to meet it.
Simone grunted, "Oh, Jane, I am eternally grateful that you're accepting me." She braced herself against the strap-on, Jane enhancing the depth of her thrusts. Simone shuddered and twitched at this initial intercourse, wrapping her legs around Jane's waist and ass, urging Jane tighter with each movement. "J-Jane, I'm about to... orgasm once more!"
Jane neglected to count this moment, she simply persisted fucking Simone without cease until Simone shrieked, "May I CUM!?"
Jane grinned, "Yes, have your orgasm, sissy Simone, join mine."
Simone's bottom contracted on Jane's strap-on so strenuously that Jane grunted from the experience. Spray dribbled out of Simone's pee catcher once more until the contractions eventually subsided. Jane extracted the prosthetic, leaving Simone pausing for air and gasping. As usual, she collected Simone's discharge and painted Simone's lips with it, Simone dearly indulging in it.
"Hmmm, this is going to be delightful," Simone panted out, settling down after the intense coupling.
Of course, taking off the strap-on harness and boosting Simone into bed, hugging her. "You're a well-behaved girl, aren't you? Once you've caught your breath, detail your school experiences." Simone remained in Jane's embrace for a spell, her heart and breathing levels decreasing.
"I really wasn't ecstatic about where I was enrolled after two years. I mastered all the essentials and yearned for a new program. That school didn't have my desired curriculum."
Jane tilted her head and raised an eyebrow.
Simone mumbled, "My parents would be very furious. I want to pause school and work in fashion, then return to college."
Jane gasped, "Oh, Simone, that's splendid."
"Thank you, I yearn to take a year off to function in fashion design, then return to school."
"Thus... you'll be lingering in town?" Simone nodded, "Long for remaining here, with me, and be my sissy?"
"Oh, Jane, I would adore that!"
"I discovered you were utilizing a lockbox for the cock lock, when will it unlock."
"Depending on the time, it should free you now."
"OK, let's eliminate it from your body and wash ourselves up. We can ponder the upcoming action."
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