Brian Winger was just your ordinary guy. He had a wife, a job, and a house in the suburbs. He worked as an accountant, and his wife, Wendy, was a lawyer for a big law firm. Nothing about him seemed amiss. Oh yeah, except that he had a sissy kink.
Nobody knew about this kink, not even his wife. The only evidence he had of it was a secret stash of erotica on his phone, along with a discreet vibrator he kept hidden somewhere that Wendy would never be able to find. Luckily, due to her work schedule, Wendy was gone a lot, so Brian could indulge in his kink while she was away. He’d just get the vibrator, pull out a juicy piece of fiction, and it’d be over in like 5 minutes (that’s all it took for him to cum).
Well, this tale begins on a Friday night. It was 6:00 PM, and Brian had just gotten home. Wendy wasn’t expected to get home until around 8, so Brian figured that he might get a quick little session before he prepared dinner. On his phone, he pulled up one of his favorite stories, “Becoming Sissy Lauren”, a short work about a man being transformed into a proper sissy. Brian then took the vibrator, set it to the highest setting, and put it right up against his cock. As he read the story, he let out small moans here and there while he enjoyed the sensation of the vibrator.
A couple minutes into his session, he’s on the edge of cumming when Wendy opens the door to their bedroom and catches him in the act. She must have entered the house without Brian hearing her.
“What the hell is going on here?” Wendy yelled, stunned at what she saw her husband doing.
“I was, um…” Brian muttered, not being able to comprehend what was occurring.
“Honey, I don’t care that you masterbate,” she explained. “In fact, I encourage it. But I never knew you liked using toys!”
Brian still sat there, not sure what to say. “Well, I, uh…”
“I told you, this is nothing to worry about, sweetie.” She then sees that he’s holding his phone, and that something is on it. She quickly swipes it out of his hands and says, “Hey, I just want to take a look at what you get off to.” Brian looked a little frightened. “Don’t worry, I won’t get offended if the woman is hotter than me,” she said, stifling a laugh.
Wendy skims over what he had been reading, and surprisingly doesn’t look shocked at all. “Ooh, you’re into some kinky stuff. I learn something new about you every day.” Before handing back the phone, she quickly sends the link to the story to herself. “Now, come on, get dressed, and let’s get dinner ready together.” Brian does as such quietly, and follows her into the kitchen.
As they prepare their dinner, Wendy explains why she got home early. Apparently, the case that she was handling ended up getting finished quicker than expected. She didn’t text or anything because she thought that coming home without warning would be a fun little surprise. Brian just stood there in silence, still embarrassed by what happened before. They finished making their dinner and sat down to eat.
While they ate, Brian was able to relax a little more. Wendy seemed to be completely okay with his secret, so he told himself that he needed to chill out. But he still couldn’t help but feel stressed out about it. He saw her send the story he had been reading to herself, and he had no idea why she did that. She might end up reading the entire thing and think he’s weird for liking it. He was just hoping that it would all blow over soon enough.
Once they finished dinner, they decided to watch a movie in the living room. Brian just let Wendy pick the movie, as he figured that would keep her on his good side. She chose to watch a rom-com she had heard about recently. They found the movie on one of their streaming services and started playing it. They snuggled up on the couch under a blanket as they watched the movie.
After a couple hours, the movie ends, and they are both still cuddling together. Wendy begins to kiss Brian deeply. She knew that her coming home had ruined his masterbation session, and she wanted to make it up to him. They moved to the bedroom and had passionate sex for a while. When they finished, Brian collapsed on the bed, feeling his sexual needs having been satisfied. He decided that he was ready to go to sleep. Wendy chose to stay up a little longer and use her phone before she also fell asleep.
It was about 7:00 AM, and Brian woke up to hearing Wendy turning on the shower. He wondered why she was getting ready this early, but didn’t think too much about it. She showered for about 15 minutes before she turned the water off. She wrapped herself in a towel and came into the bedroom to get Brian out of bed.
“Come on, honey,” she said, poking him. “Time to get up. We’ve got a long day today.”
“Huh?” Brian muttered, kind of puzzled. “I didn’t think there was anything to do this weekend.”
“There are some stores I want to hit that are closing early today. Plus I made last-minute reservations at a couple of places. I figured that we could spend a little quality time together.”
Not really questioning anything, he got up at her request and took a shower. Since he was tired, he spent about 20 minutes in the shower, which was almost twice as long as normal. When he got out of the shower, he got himself dressed into his normal clothes: jeans and a t-shirt. He then brushed his hair a little bit and considered himself ready.
As Brian walked into the kitchen, he was surprised to see that Wendy was already ready herself and had finished cooking them breakfast. She kissed him on the forehead, and they started eating. He asked about what specifically they would be doing today, but she said that it would be better as a surprise (which is usually true, Brian loves surprises). They finish eating their food and clean off their plates. They then fix themselves up a little more before heading out.
Wendy took to driving because she knew of all the places they’d be going. After about 10 minutes of driving, they arrive to the first stop of their journey. Brian looks at the name of the place, which is called “Smooth and Spectacular”. He becomes confused, and looks over at Wendy, who is smiling.
“What?” she questioned, seeing his face. “This is just a waxing salon. You always compliment me on how smooth my skin is, and this is how I do it. Now I want you to experience this with me. I have couple’s waxing appointments setup for us.”
“But why?” Brian responds. “I already know you get waxed, and I’ve even see you do it once before. Also, this isn’t exactly a thing for men to do.”
“Hey, beauty is pain sometimes, so I think it will be good for you to truly understand what I’ve been doing for years. And besides, it’s 2024, so I think we are past gender stereotypes.”
Brian reluctantly agreed, and so, they walked into the salon together. Wendy told the receptionist that they had a reservation for 2 under Winger. The receptionist checked the appointments and confirmed their reservation. She led them into one of the treatment rooms, instructed them to take off all of their clothes, and said that someone would be with them shortly. Brian was hesitant at first, but then began to strip; Wendy did the same. They both then laid on the tables that were the room with them.
After a few minutes, there was a knock on the door, and two women entered. They began to prepare all of the waxing equipment, which mostly involved warming up the wax. Once the wax was ready, they used the wooden applicator sticks to spread the wax across every inch of the couple’s bodies. Then, one by one, they quickly tore off each of the wax strips. Brian let out many yelps throughout the process, his eyes watering almost the entire time. Wendy took pleasure in this, and barely even flinched after having done this so many times.
It wasn’t long before their entire bodies were completely smooth; they even had their facial hair removed and eyebrows trimmed. The women working on them rubbed some scented lotion on to help relieve the pain and make their skin softer. While Brian would have enjoyed this part under normal circumstances, his penis wasn’t even getting hard, probably because he was still too shocked from the experience. The women quickly finish up, and the couple is told that they can put their clothes back on and may leave.
As they walked to the car, Wendy didn’t even have to ask what Brian thought about what just happened. She could tell that he was still in pain, but also that he was mesmerized by the new smoothness of his skin. He kept touching different parts of his body and observed how it felt. He was both embarrassed and excited about this. He thought to himself, “I always fantasized about this, but never thought it would actually happen.”
They got into the car and drove to their next destination: the mall. Brian figured that Wendy just wanted to do some regular shopping, which she often did on the weekends. He followed her into the building and right into Victoria’s Secret. She told him to wait at the entrance for a second, and she went to talk to the cashier. After a minute or two, another woman came out to talk to Wendy, and she gestured for Brian to follow.
They entered into a room towards the back of the store that had a curtain for privacy. The woman told Brian that he should probably strip to his underwear now. He looked towards Wendy confused, who said, “We’re just going to get some measurements before you try on some new clothes. Don’t worry, honey, this room is completely private. Nobody but us will see.” Warily, he took off his clothes and stood on the stage-like platform in the middle of the room. The worker used a measuring tape to take a bunch of measurements of his body, writing each one down on a piece of paper. Once she’s finished, she hands the paper to Wendy and leaves the room. Wendy then says that she’ll be back and also leaves.
After a few minutes of Brian standing there in just his underwear, shivering due to the lack of body hair, Wendy comes back with a pile of clothes. She makes him take off his underwear and hands him a matching red bra and panty pair. Inside, he was actually curious about doing this, but on the outside, tried to act hesitant about it. Eventually, he began to slide the panties up his legs, but before he finished, Wendy showed him how to tuck his penis so that there was no bulge. With the panties (and penis) in place, he tries to put on the bra with some struggle, and eventually figures it out. He then looks at the mirror and is stunned. He never knew that he had such a feminine body. The hairless skin, women’s underwear, and lack of a bulge didn’t help with this, but it was clear that his body was not normal for a man.
Once Wendy had him show off the bra and panties, she had him change into a different pair. Over the course of a half hour, Brian tried on a variety of panties, bras, sleepwear, and even lingerie, all in different colors and styles. Towards the end, it became clear that the couple actually enjoyed doing this together. When they got through all of the clothes, Wendy chose her favorites for them to buy. She took the tags off of a pair and gave that pair to Brian, as she wanted him to wear it out of the store but also needed a way to pay for it. Figuring that nobody would notice it, he agreed and put the bra and panties on, putting his male clothes on over it all. They then go to the cashier, pay for the clothes, and leave the store.
The next store they go into is JCPenney. Brian begins to see a pattern with the places they’re going to. He remembers from his “Becoming Sissy Lauren” story that the main character starts out getting waxed, then gets measured for women’s underwear, followed up by him hitting a department store for some female clothing. He now knows why they are doing all of this today: Wendy read the entire story and wants him to experience the exact same thing. He was kind of nervous now, knowing that he’d be completely turned into a woman. He tried to think about what happens in the story after the department store, but for the life of him, he couldn’t remember. He’s not even sure if he’s read the entire story; at best, he’s just had a glance over it all, but that was a while ago.
In JCPenney, Wendy went around picking clothes for Brian to try on. This included tops, skirts, dresses, and leggings. They then went into one of the dressing rooms and essentially did the same thing that they did at Victoria’s Secret. He tried on pretty much everything that Wendy handed to him. Although he felt as though she was kind of tricking him, he was still having a good time.
Once Brian had tried everything on, Wendy again gathered what she wanted to purchase. He was about to put his male clothes back on, but she stopped him. She gave him a black skirt and purple tank top, and said that he should wear this. He felt a pit in his stomach.
“Wait, you want me to wear this?” he exclaimed. “I get the whole ‘no gender stereotypes’ thing, but I’m not sure if I’m comfortable with this. Everyone will see a man in women’s clothing and make fun of me.”
“Sweetie, I completely understand your concerns.” says Wendy. “However, I do have to disagree with you. You don’t look like a man in women’s clothing. Just put that on and take a look in the mirror.”
Brian did as such and realized that she was right. Despite having a male hairstyle and no additional female products on him, he did look like a woman. Due to his feminine body (which he had noticed earlier), the clothes made everything below his neck look like a woman. He also had a few feminine facial features that he never noticed before, and the completely hairless body was doing him no favors. He barely looked like a man.
Although he was still as nervous as he could be, Brian agreed with Wendy. She stuck the stuff that was in his pockets into a new purse that she liked, and handed it over to him to carry. They carefully walked out of the dressing room as to not draw suspicion. Before they could reach the cashier, Wendy had them make another pit stop to the makeup section of the store. She brought him over to one of the makeup chairs and found a worker there who could give him an official makeover. The worker didn’t seem to know that Brian was a man (or at least, she didn’t say anything), and so, she started working on him. She did foundation, eyeliner, mascara, and lipstick on him, while explaining every step and making a little bit of chitchat. Once she finished, he saw himself in the mirror, and he could only see a woman staring back.
The worker gave them all of the products she used so that they could purchase them, and she also was nice enough to scan the clothes they were purchasing at the same counter. They thanked her and left the store.
As they walked outside, Brian assumed that they were done, but he was wrong. They walked over to the hair salon that was in the same plaza as the mall. Wendy confirmed the appointment she had made, and Brian was led over to one of the salon chairs. Wendy whispered to the stylist what she wanted done to him, and the stylist began to work on his hair. She added extensions to make his hair longer and cut it into a more feminine style. Brian started to question if this was a little permanent, but was assured that it could easily be put back to normal. Looking in the mirror, he looked completely like a woman now.
When they finished in the hair salon, they went into nail salon that was right next door. This time, Wendy had an appointment for the both of them. They were brought over to chairs that sat next to each other, and were instructed to put their bare feet into the water in front of those chairs. Two beauticians came over and started working on their feet. As the pedicure was done, Brian was actually feeling relaxed for once, and Wendy was happy about that. The beauticians took the time to shape, clean, and buff their toenails. Once it came to the polish, Wendy picked out a neon pink for both of them so that they could match. The beauticians then polished their toenails, starting with a base coat, doing two coats of the pink polish, and finally adding a top coat. The polish made Brian’s feet look undoubtedly feminine, which he actually liked. They then stuck their feet into a machine so that the polish could dry.
Brian thought they were finished at this point, but the beauticians began to bring over tables to do manicures on them, too. They pretty much did the same thing that they did with their toenails, but on their fingernails instead. However, before they did any polishing, they used a bit of acrylic to make their fingernails a little longer than normal. Before they added the polish, Brian questioned if this might be too obvious, but Wendy argued that polish is easily removable, and he agreed. Soon enough, their nails sported the same neon pink as their toes. They put their hands into a machine similar to their feet in order for their nails to dry.
When everything had dried, the couple was given complimentary flip-flops to wear, and they left the salon. Brian couldn’t help but keep looking at his new nails, and Wendy definitely noticed him doing that. They ended up going back into the mall, and Brian tried to think of what else happened in the story. It seems like everything they’ve done today was in the story (in the exact same order), but he still couldn’t remember what else may be in store for him.
They ended up walking into Famous Footwear. Wendy had Brian use the foot-measuring device to get his shoe size in women’s measurements. She then took her time in finding a bunch of pairs of shoes for him to try on, including multiple kinds of open-toed sandals and heels, along with a pair of high-heeled boots. She had him try on all of the shoes and walk in them. He initially struggled with the ones that had heels, but eventually got the hang of it. Wendy chose at least 5 different pairs that she liked on him and purchased them. She gave him a pair of open-toed sandals to wear out of the store.
Brian figured that there would be more in store for him, but Wendy said that they were practically done. However, she needed to go to another store by herself to pick up a couple of surprises for him, so he was told to go back to the car. He took all of the bags they’d accrued throughout the day and headed outside. As he walked out of the mall, a man held the door open for him. Brian thanked him in the best feminine voice he could do. He went to the car, stuck all of the bags in the trunk, then sat in the passenger seat.
While he waited, he decided to take his phone out of his new purse. Typing was definitely a little harder with his new nails. He thought about looking back at the “Becoming Sissy Lauren” story to see if anything else will happen, but since he liked surprises, he eventually chose not to. Instead, he went to his camera and took a few selfies of the new version of himself. He then stored them in a hidden folder on his phone just in case.
Wendy came back to the car with a bag of unknown items and also sticks them in the trunk. She gets into the driver’s seat and they begin the trip back home. Brian thanks her for the day they’ve had, and that it was such a great experience. She smiles, as she is glad to see him this happy. Then she says, “Well, the day isn’t over yet. I’ve got a couple more things in store for you.” Brian gets excited at the thought of this.
They eventually pull into the driveway of their home and exit the car with their bags. They barely get inside before they are making out with each other. They both kick off their shoes and rush to the bedroom. They throw themselves onto the bed and continue to make out. Brian takes off Wendy’s skirt and top, while she does the same to him, leaving both of them in just a bra and panties. Brian took his polished fingertips, reached into Wendy’s panties, and began to finger her. She moaned with pleasure as he teased her pussy. If someone had caught a look at them right now, they’d assume it was 2 lesbians having sex.
After a few minutes of fingering, Wendy let out a big moan and orgasmed. To return the favor, she pulls down Brian’s panties, and his penis springs to life after being tucked for so long. She positions herself so that she has one hand on his penis, and a finger inside his asshole. She teases his prostate as she gives him a handjob, and Brian begins to moan like a girl. Wendy then puts his whole penis in her mouth, using her tongue to tease it while still teasing his prostate with her finger. It doesn’t take long for him to orgasm after this. Wendy milks him out of all the cum she can as his penis shrinks to practically nothing. To top it off, she kissed him to let him get a taste of his own product.
Brian laid there in a complete daze, feeling a euphoria like he never had before. Wendy quickly slipped to the living room to grab something while he stayed this way. She comes back and starts to mess with his groin area again. He thought that she was going for round 2, but he hears a “click” sound and looks at what she is doing. He sees that his penis is in a chastity device, and she had just locked it. His eyes widened.
“Oh, honey, are you really that surprised?” Wendy asked. “Look, I’m sure you realized that today was almost exactly like that little piece of erotica I caught you with. So, you should know that it ends with the main character getting locked up. And from what I understand, sissies aren’t supposed to use their penises, so this will be best for you.”
Wendy sticks the key to the chastity cage in a locked drawer on her dresser and continues. “Now, come on, we should get ready. We’ve got dinner reservations to get to.” Brian just sits there shocked. He had completely forgot about the ending of the story, and he was now living it. He was a mix of confused and turned on. But knowing that he couldn’t do much else, he decides to get out of bed and start getting ready.
Wendy brings all of the bags into the bedroom. She chooses his outfit for him: a red, slim-fitting dress. He changes into this, and she hands him the makeup so that he can fix it up. Looking in the mirror, he mostly just sees that his eyeliner and lipstick got smudged from the sex session. Although he’s never applied makeup before, he fixes it as best as he can, and does a pretty decent job. He brushes his hair back into his new feminine style and uses a bit of hairspray to keep it in place. As he questioned if there was anything else he needed to do, Wendy comes in and gives him some perfume to make him even smell feminine.
After slipping into a pair of 2-inch high heels that Wendy picked out, Brian was done and the couple was ready to head out. As Brian crossed the threshold of his front door, he sighed. “I guess this is my reality now.”
The End?
