CAUGHT IN THE ACT

Prologue

Jane, a successful young businesswoman, lives next to Simon, an almost 20 year old college student. Right out of college, Jane created a talent agency working with exotic performers, and through hard work and a bit of luck, was able to grow her agency very quickly. One of her burlesque shows took off and established a residency in Las Vegas. Other talented performers that she worked with were able to establish successful careers in the erotic arts. This, combined with some shrewd investments, led to Jane being able to buy her own home 5 years ago.

This home, in a quiet residential area, is one of two on a cul-de-sac flanking the entrance to a park. The area is particularly secluded, with woods backing the houses and little to no traffic. The other home, across the cul-de-sac, is owned by Simon’s parents. When Jane moved in five years around, young 15 year old Simon barely noticed her. His head was buried in comics and video games.

Only when he turned 18 did he become enraptured. That fateful summer, he realized that he found Jane stunning, in the bloom of her youth, curvy but not overly so, MILFy though likely too young for that label. But it was not that Simon wanted to fuck Jane, like most of the hormonal college boys his age, he wanted to *be* her or at least like her. Simon had never liked sports and he even now he had soft curves for which he was teased.

He longed for a body like Jane’s. The wonderfully rounded bottom and breasts that mesmerized him when he saw her in one of her smart business suits, leaving for one of the many business trips what she took. Since discovering Jane almost two years ago, Simon often fantasized about being a woman and had bought some lingerie for himself. He always got rid of it for fear of his Conservative Christian parents finding it and wondering what was wrong with him.

That fall, two years ago, he went off to college in another state and had something of a miserable time of it, not fitting in with anyone. He did manage to bring some lingerie to college and to have some fun when his roommate was not around. This year, he planned to tell his parents that he was going to take a year off to figure out what he wanted to do. He had not had the nerve to tell his parents that he wanted to declare a major in Fashion Design. He knew that they would not understand.

Arrival: Simon

When he came home for summer break this year, he was shocked that his parents had seemed to forget to tell him that the house was going to be renovated and they were going to travel for a year as missionaries.

Simon asked, “What will I do?”

They answered, “Oh, we took care of it. Do you know that nice young woman next door, Jane? She travels a lot for work and, in fact, she has a two month business trip that started yesterday. She said that you can house sit while you are away and care for her cats. During that time, we can figure what you will do for the last month of summer before returning to school. We have the bank accounts set up to give you an allowance and, since you are on a scholarship, we don’t have to worry about paying your tuition, room, and board.”

Simon swallowed at this news, a mix of feelings cascading over him. He was going to live in Jane’s house? Alone? For two months? How could he tell his parents that he had already withdrawn and given up his scholarship? He was tongue tied and his head was swimming as they continued.

“Construction starts in three days, on Monday, we leave tomorrow so we don’t have to fly on the Lord’s day, and Jane has already left for her business trip. We do wonder what she does! She told us that she bought that house five years ago and that fancy car of hers. We guess that the Lord has his eye on her!”

Simon nodded and said, “Where is my stuff?”

“Oh, we packed it away. There was one footlocker, probably from when you went to camp, that was locked, we hope you didn’t need anything from it. We figured that you could use whatever you brought back from college.”

Simon nodded and took a relieved breath. That footlocker contained whatever remnants of lingerie he had kept, some things he had used to restrain himself, plus porn and erotica that he did not want to bring to college. The other items that he used more often–the breast forms so that his chest was more like Jane’s, the tiny chastity device for his tiny cocklet–had gone to school with him and were packed in his one large bag.

This conversation had taken place in the car on the way home from the airport. Indeed, when they got home, the house was completely empty. His parents told him that they were going to leave the car in the garage since they knew he didn’t have a license and would not need it.

They were going to stay in a hotel by the airport because their flight the next day ways going to early in the morning. They walked him to Jane’s door, gave him the envelope with the keys and the instructions, hugged him goodbye, letting him know that they would keep in touch though might not always have service in the rural areas they would be in and left in their taxi for the airport.

Simon stood at Jane’s door for a long moment, finally opening the door with trembling hands. He had never been in her house the five years that she had lived here though he had cut her lawn from time to time and shoveled snow in the winter. He entered the tastefully appointment house, not knowing what to expect, and was pleasantly surprised. Opening the envelope, he read the short note from Jane.

“Simon, thank you so much for taking care of my house and my cats while I am gone. There should be enough food and cat litter for the duration of my trip. Make yourself at home! There is a guest bedroom that you can use. Your parents told me that you don’t drive so I stocked up on some food items and you can order more food otherwise. I should be home on August 1st. Here is my email address and phone number. Send me an email when you arrive so I know that you are there. Cheers, Jane”

He sent Jane a quick email letting know that I had arrived and thanking her for letting me stay since his parents had neglected to tell him about their trip. It was hard to hide his snark.

He took a tour of the house–living and dining room, kitchen, master bedroom with en suite bathroom, guest bedroom, other bathroom, office, basement. Though Jane said he could stay in the guest bedroom, he could not help but peek into her bedroom. He walked around, touching all of the surfaces, eyeing the full length mirror, checking out the en suite with its huge jetted tub. He bit his lip and then smiled, thinking, ‘I’ll stay here, at least for part of the time. How will she know?’

That being said, he did unpack his things into the guest bedroom, not nearly filling the closet or drawers. He had a bite to eat, showered off in “his” bathroom, then thought about what to do. He knew he would not be able to last long without peeking through Jane’s drawers. He kept his legs and pubes shaved smooth and he had very little and very fine body hair. No time like the present, he thought!

When he got out of the shower, he first put on his chastity device. It was the latest and most restrictive that he had tried, an inverted or negative chastity lock it was called. The usual metal ring settled behind his scrotum. He had had so much practice that his cocklet barely stirred. The inverted part consisted of a metal cup on a short post attached to a metal plate.

There was a hole in the cup and the post was hollow. He pushed the head of his cocklet down inside his short shaft and pushed everything up into his body, first using his fingers, then the metal cup and post, doing his best to line up his pee hole with the hole in the cup. When it was pushed all the way in, he used the custom wrench to secure the two screws holding the plate to the ring. The end result was a small flat plate with a hole in it above his scrotum, his balls secured in place.

He took a few deep breaths and admired the chastity lock. He had once worn it for a week, by accident, because he came home for break and forgot the wrench. In time, two things have happened–he got fewer erections and, often, when he pulled down his undies, the head of his cocklet had already retreated part way into his shaft. It was almost like his body not only expected but also wanted to receive the restrictive device.

Besides the device and his breast forms, he also had a small “kitchen safe” with a timer lock. His idea was to set the timer for a week, leaving him locked away, then free himself for cleaning. He would try it one week and see how it went. The safe was clear plastic though he could break it open if needed but the company charged a steep price for a replacement box so he was disinclined to do so.

As the lock counted down from 5 and he heard the mechanism engage, he fetched his breast forms. They were the best he had found that he could afford. They were like a bra that could be worn with our without straps. Nude it was easier to use the straps though with a bra he would just use the band and let the bra support the lifelike breasts. He bit his lip, looking at his small collection–two black lace bras and one nude “sleeping bra.”

He took a deep breath, unknowingly sealing his fate, and walked to Jane’s master bedroom. With trembling hands, he walked to her dresser, opening what he correctly guessed was her lingerie drawer. He was treated with a glorious site, so many colors of matching sets of bras and panties, some lace, some satin, some cotton, plus garters and hose. His mouth dry, he chose a green lacy bra and panty set. He pulled the panties up his legs and then, removing the straps from the breast form, he put on the matching bra, settling the breasts in the cups. Closing the drawer, he… or perhaps she… took in the sight.

Moving to the closet, he opened it slowly, seeing quite the collection of dresses and skirts, some businesslike that he had seen, some casual, some sexy. He found a green midi dress that somewhat matched the bra and panty set he was wearing and took it out. He smoothed it over his body and took it off the hanger, hands still trembling. Setting the hanger aside, he pulled it over his head, settling it on his hips and adjusting his breasts. He looked into the mirror. He for the most part had become she. It was settled, Simon would spend at least part of the summer as Simone. She put the hanger back and went to make some lunch.

Discovery I: Jane

“That little fucker sure didn’t wait long,” said Jane, as she watched the video stream. Unbeknownst to Simone, there were cameras in a number of strategic places in the house, all remote accessible. “And he went right for one my favorite lingerie sets. I wonder if he is planning to do this the whole time while I am gone.” She followed Simon–she had not yet “met” Simone and did not know she used that name–around the house while he made some food and settled in to watch a movie.

“I bet he’ll be in for shock when I get home a day earlier than I put in the note,” Jane chuckled to herself, going back to the meeting she was sitting in on. While she did want to know when Simon had arrived, she had really wanted to know when she could start watching the cameras. She had had her suspicions about Simon for the last two years. He could not hide the looks he gave her though she found them less like the lustful leering that she might get from the typical late teen and more like… envy. Her suspicions were confirmed.

“I will watch him from time to time. I will let him have his fun then I will have my fun when I get home. I will make that last month before he goes back to school one to remember!” She felt some tingling between her legs and her nipples stiffen in the modest business clothes she was wearing. Though not obvious to the outside world, if she glanced down, she could see the tattoo between her breasts. “Oh, yes, this will be fun.” Though she really wanted to slip her fingers between her legs to her now soaking pussy, she forced herself to focus on the meeting.

Summer Self Loving: Both

Simone was true to her word. Each week, she released herself, cleaning her cocklet, letting it air out, then locking it up again. For two months, she wore Jane’s clothes, taking great care with them, washing them as needed, working her way through the wardrobe. As Jane watched, she remarked, “He doesn’t look half bad, to be honest. But, still, he will pay for this in some way. Gawd, I can’t wait to fuck that tight ass, he has to be a virgin.”

Simone had learned that she could use a Hitachi magic wand to get off though it was ultimately unsatisfying. The spurt would ooze out the hole in the cocklet lock, and she would just be hungry for more. Jane would watch some of these sessions, sometimes in real time, getting herself off watching the show while dreaming of what she would do when she got home in a few weeks.

Discovery II

Simone was lost deep in thought and lust on July 31. She was sprawled on Jane’s bed, mindful it was likely her last chance–little did she know–to do so. She was decked out in a red lace bra and panty set with matching garters and hose as well as some low pumps. She had figured out that she and Jane also had about the same shoe size a few weeks into the summer so had also worked her way through Jane’s shoe collection.

She was watching a video on a popular erotic streaming site that featured a woman that looked almost exactly like Jane, though not quite. It has never occurred to her that it could be Jane, though from before she moved into the neighborhood, her appearance was different enough. The video featured a husband turned sissy wife who gets caught wearing lingerie by the star–Jane–who takes the sissy’s ass virginity. Oh how Simone both longed for this to happen and was also terrified of the prospect of getting caught.

While she watched, she used the Hitachi on her locked cocklet over the lacy panties. She had her noise canceling headphones on so did not hear Jane enter the house and find her way to the bedroom. Jane somewhat knew what was going on because she had been watching the stream on the hidden security camera. When she thought the climax–pun intended–of the video was approaching, she opened the door and stood quietly.

Lost in the throes of the approaching sissy-gasm, Simone was oblivious until she glanced at the door and saw Jane. She jumped such that she kicked the laptop which flipped around to face Jane, now walking into the room, looking somewhat angry, “What. Are. You. Doing? In my clothes? In my room, Simon?”

Simone stammered, “I… I… I can ex-explain, Jane.”

“And I see that you discovered my other income stream.”

Simone looked shocked, still stammering, “This… this is… you? For real?”

Jane nodded, “Yes, from, oh, 7 or 8 years ago. When your parents asked what I did, I told them ‘talent management.’ Knowing their beliefs, I didn’t add ‘erotic’ to that explanation. And when I started, I figured that I was going to manage erotic talent, I should understand what it was like. It turned out that I liked it so I did it for a few years.

Still in disbelief, Simone said, “That’s really you?”

Jane, in jeans and t-shirt, lifted the t-shirt to reveal the tattoo between her breasts.

“Oh my god, I… I don’t… I don’t what to say, Jane. I’m sorry.”

“You should be, you will be. Not for being a sissy but for using my things without my permission. I wish we could have figured this out in a different way, but the… pussy… is out of the bag, isn’t it.”

The wand still buzzing in Simone’s hand, Jane said, “Don’t stop on my account. I bet you are already leaking into those panties. I hope you have done a good job with my laundry, Simon.”

Simone mumbled, “……..”

“What’s that, speak up!”

“Simone, when I am like this, I use Simone.”

“I could have guessed! OK, Simone, have at it. I also want to see that cock cage, I have not had a chance to see it clearly on the security cameras. Slip off those panties–I see you know about the panties over garters trick–and lay back, give me a show.”

“I… I don’t know, I…”

Jane looked at Simone sternly, though a smile.

Simone closed her eyes and did as she was told, slipping off the panties and lying back. Jane knelt at the foot of the bed and inspected the cock lock, “Wow, this I have to see, but don’t let me delay you. Perhaps I can help.” Simone began to run the wand over her pubis mons and over the lock, sometimes straying down to her trapped sack. She moaned, knowing that she was now all-in with this fantasy. One hand strayed up to her breast, caressing the c-cup forms though feeling it as though she were touching herself.

Jane raised onto her knees, leaving her jeans on though slowly peeling up the t-shirt again, not quite bearing her breasts, watching Simone stimulate herself. “Those are a lot like these,” she lifted her shirt and peeled it over her head, “aren’t they? I bet that was on purpose, wasn’t it. It looks like you had them before you knew that they would fit well into my clothes.”

Simone nodded, caught up in her own ecstasy.

Jane laughed, “Pussy got your tongue, Simone? I guess we will need to figure out what you can call me for the next month. Call me Jane for now”

Simone groaned, her arousal ramping up again, stammering out, “Yes, J-Jane. A-about t-that. I… ugh, ahh… I with… withdrew from… sch-school.”

“Shhhh, Simone, we can talk about that later.” She reached behind her to unclasp her bra, though continuing to let it rest on her breasts, teasing Simone with seeing them. She ran her hand over her own pussy, over her jeans, letting out a low moan, “That’s right, good girl, get yourself close.” She used her hands to slip the bra down her breasts, her nipples erect. Setting the bra aside, she skimmed her fingers on her nipples, sensuously licking her fingers first.

Simone could not take her eyes off of Jane, her face, her breasts. Her whole body shuddered as her arousal came close to cresting, “Pl-please, Jane, please, can I cum?”

Jane smiled, saying, “Such a good girl. You can cum when I am ready for you to cum. Keep yourself right on the edge.” She crawled up the bed, sitting next to Simone, skimming one hand over her own breasts while skimming the other over Simone’s breasts. Simone jerked with pleasure, almost unable to hold back, though easing off with the wand. “Tsk tsk tsk, no cheating, Simone. You will just need to control yourself and obey me. She leaned close to Simone’s ear, “Trust me, it’s worth the wait.”

Simone groaned, resuming stroking her “pussy” with the wand, bringing herself as close as possible to the edge. Jane leaned back and Simone looked her in the eyes, “Pl-please, Jane, please. I can’t handle it anymore!”

Jane smiled, “In time, Simone, in time. Now, I know you might be a bit distracted, but I would like to know if you would like to be my sissy?”

Simone nodded vigorously, saying, “Yes, please, Jane, please make me your sissy.”

Jane smiled, “Make you? I think that you are most of the way there, sweetie.”

“I… I am a… vir… virgin, Jane. I’ve pl-played with my fin-fingers, though ne-never a c-c-c-cock.”

“I KNEW it! I am so excited, I get to take your sissy virginity. I am so excited! Have I said that? I can’t wait to tell my friend Mary. You will love her.” She bounced in glee, her breasts practically hypnotizing Simone. “OK, I give in. Ten… Nine… Eight.” She begins to tug and pull her own nipples, rolling them in her fingers. “Seven… Six… Five… Four” She pushes Simone’s legs close together and sits on Simone’s thighs, pressing the crotch of her jeans against the other side of the vibrating head of the wand.

“Three,” hip thrust, “Two,” pressing her clothed pussy against the Hitachi, driving Simone closer, “One,” looking Simone right in the eyes, saying, “Will I say it? Hmmmm? Do you deserve it? CUM!”

Simone immediately began jerking and bucking against the Hitachi, pushing against Jane’s crotch, who was grinding back. Spurt after spurt of cum oozed out of the hole in the cage, Simone continuing to thrust until she was spent, falling back onto the pillows, somehow managing to turn off the magic wand.

Jane reached down, gathered as much of the spurt as she could and offered it to Simone’s lips, the sissy gobbling it up, licking Jane’s fingers with abandon. “Good girl, very good girl.” Jumping off of Simone’s legs, she continued, “close your eyes, wait here.” Simone heard shuffling and other noises, perhaps pants being removed. She felt her hand tugged by Jane, off the bed, pushed down to her knees.

“Open up, eyes and mouth, Simone!” Simone did and saw a strap-on looming in front of her face, “Now, make it nice and wet!” Lacing her fingers in Simone’s hair, Jane slowly and gently drew Simone’s lips to the strap-on, slowly filling up the sissy’s mouth before pulling back to slowly thrust gently again, with more vigor. Simone yielded and went with the flow of the moment, remembering every cock sucking video she had seen, always wishing she was the cock sucker, and did her best to please Jane.

“Hmmmm, you are hungry, aren’t you? Such a good sissy cocksucker!”

Simone groaned and plunged the strap-on as far into her throat as it would go until she gagged, her eyes wet from the effort. She sucked and licked, using her hands to wring the fake cock, licking the balls, so close to Jane’s bare pussy, before sucking the cock more, drool running down her chin. She looked up in bliss, seeing Jane’s smile past her breasts.

After a while, Jane pushed Simone down onto her back, standing over her with the dripping strap-on and a further glimpse of her juicy pussy. “On your back or on your knees? Hmmm. How do I want to take your virginity. Hmmm.” She stroked her cock as though to keep it hard. “I want to see your face when I take you, Simone. Back on the bed!”

Jane moved from straddling Simone, tugging her up and pushing her onto the bed playfully, Simone’s bottom ended up on the edge of the bed. Jane grabbed Simone’s legs, pulling them up to her own shoulders. She pressed the tip of the strap-on to Simone’s sissy pussy, rocking her hips, opening Simone up. She spit on the cock and gathered the juices from her pussy to slick the cock and Simone’s hole. She continued to poke poke poke as Simone groaned and Jane made eye contact.

“Ready?” Simone nodded her head, breath quickening. Jane steadily pressed against Simone’s sissy pussy until the head passed into Simone. She paused, bringing her hands to her breasts, toying with the nipples before leaning over to take Simone by the hips. She pushed the strap-on into her as Simone arched her back to meet it.

Simone groaned, “Oh, Jane, thank you for taking me.” She pressed herself to the strap-on, Jane increasing the depth of her thrusts. Simone shuddered and shook at her first fucking, wrapping her legs around Jane’s back and bottom, pulling Jane to her with each thrust. “J-Jane, I am going… to… c-cum again!”

Jane didn’t bother counting this time, she just continued to fuck Simone without stopping until Simone cried out, “Can I CUM!?”

Jane smiled, “Yes, cum for me, sissy Simone, be mine.”

Simone’s bottom clenched on Jane’s strap-on so strongly that Jane groaned from the sensation. Spurt burbled out of Simone’s cage again until the clenching finally stopped. Jane withdrew the cock, leaving Simone gasping and gaping. Again, she gathered the spurt from Simone’s release and painted the sissy’s lips with it, Simone eagerly slurping it down.

“Hmmmm, this is going to be fun,” gasped out Jane, calming down after the vigorous fucking.

Slipping off the strap-on harness and pulling the spent Simone up the bed, wrapping her arms around Simone. “You are a good girl, aren’t you? When you catch your breath, tell me about school.” Simone rested in Jane’s arms for a while, heart and breathing rates coming down.

“I didn’t really like where I was going after two years. I took a lot of the basics and I want to transfer. That school didn’t have the program I wanted.”

Jane cocked her head and raised her eyebrows.

Simone murmured, “My parents would be so angry. I want to do Fashion Design.”

Jane says, “Oh, Simone, that’s delightful.”

“Thank you, I want to take year off to work in fashion, then go back to school.”

“So… you’ll be here, in town?” Simone nods, “Want to stay here, with me, and be my sissy?”

“Oh Jane, I would love that!”

“I saw you were using a lockbox for the cock lock, when does it open.”

“Depending on what time it is, it should be open now.”

“OK, let’s get it off of you and get us cleaned up and we can talk about the near future. I am still mad that you wore my clothes without my permission though I have to admit that you look good in them.”

“Thank you, Jane, thank you,” said Jane with tears of joy in her eyes.