Stepping Out With Stepmother
As his bus finally reached its stop, Steve made a mental note to get here early next year. Mother's Day weekend had caused the traffic to be backed up, doubtlessly due to all the people taking their mothers out that year. It would take another hour until he reached his stepmother's house.
Fortunately for him, Steve got there before dark. Unfortunately, he arrived late in the evening. After he knocked several times, his stepmother, Monica, finally answered.
"Steve," Monica said, smiling widely. "Please, come in."
Steve entered the house and the two made their way to the living room.
"This is a surprise," Monica said. "What brings you here?"
"Well, I had been planning to take you out for Mother's Day dinner, but the traffic was terrible," Steve explained.
"Oh, you didn't have to," Monica said. "After all, I'm not your real mother, and your father and I divorced last year."
"All the more reason for me to be here today," Steve said. "You shouldn't be alone the first Mother's Day without Dad."
"You're so sweet," Monica said. "Tell you what. You can stay here overnight and tomorrow we'll have a day out, just the two of us."
"As long as you're okay with that," Steve said.
"More than okay," Monica said. "I'm looking forward to it."
The two talked for awhile after that, before Monica made up the guest room and Steve went to bed.
As he slept, Steve dreamt of when he first met Monica. He had seen her around town before, but he'd been quite shocked when his father brought her home to meet his son. Steve himself had recently turned 18 and was finishing up high school. Monica had actually been closer to his age than his father's.
The two were engaged in no time, and Steve's friends were quick to mock him for it. His father was marrying a smoking hot babe, and Steve wouldn't even be around long enough to take in his stepmother's beauty.
The divorce last year hadn't been that surprising. Again, Monica was closer to Steve's age, so plenty of people knew his father would be tossed to the wayside after a time. Some even guessed that she was a gold digger who'd been out for money. While Steve's father wasn't rich, Monica had gotten a large amount of money from the divorce, which showed in her new life.
Steve woke up later than expected the next day. He had left his house early the previous day, hoping to get to Monica's house by noon, but the world had different plans for him. Thankfully, it was still fairly early when Monica knocked on his door.
"Steve, wake up," she called from the other side of the door. "It's time to get ready. We'll be going to breakfast soon."
"Yes, ma'am," Steve said.
Steve quickly washed up in the shower. Monica only had soap and shampoo meant for women, but he could put up with smelling a little feminine. At least for today.
Once he was finished, Steve went to the living room, where Monica was waiting for him.
"Whoa!" Steve said, stunned.
Monica was standing in front of him in a red, double-breasted suit with matching skirt and heels. Her hair had been combed to perfection and swept over her one shoulder. Her red lips, matching her suit, complimented her beauty.
"Why, thank you," Monica said, flashing a smile which sent Steve's heart fluttering.
"Now I feel underdressed," Steve admitted.
"I'm actually glad you bring that up, darling," Monica said. "I was hoping I could ask a little favor."
Monica's smile went from somewhat seductive to mischievous at the response.
An hour later and Steve was now staring at himself in the mirror. He had a wig placed on him and was in a fuchsia version of Monica's suit. Monica had done his makeup, which surprisingly worked in making him look like a woman. The open toe shoes helped create the image of a woman.
"I've always wanted my own daughter," Monica confessed. "And now, I get to see what it would be like."
"I know I said I'd do anything, but..." Steve started, only to be silenced by Monica's finger on his lips.
"You sound too much like a man," Monica said. "You said you'd do anything, so please, let me have this Mommy-Daughter Day."
Steve sighed and said, in his best feminine voice, "Yes, Mother."
"Good girl," Monica said, giving Steve a pat on the head. "Now first, we'll go to get your makeup professionally done. After that, we'll have a little breakfast at this cafe I know and then we can head to the spa."
The beauty parlor had been fairly humiliating for Steve. Monica was complimented for how perfect she already looked, but Steve was told "her" makeup needed work. For whatever it was worth, he did think the beautician had done an even better job than Monica had.
The two had arrived at a small, quaint little cafe and sat down for a small meal. The waitress, when bringing their food, noticed the hair on Steve's chest and wrists.
"She's been a touch under the weather recently," Monica said. "The medicine threw her hormones out of order. We're going to the spa after this to get her taken care of."
Steve blushed and looked down. The waitress was cute. If he hadn't been dressed as a woman, he would've asked her out.
"I'm so sorry," the waitress said. "Good luck at the spa. I hope it makes you feel better."
Steve looked down further.
"Say 'thank you', dear," Monica ordered.
The waitress smiled and walked off.
"And thank you, sweetie," Monica said, as she sipped her tea. "I always wondered how it would feel to embarrass my daughter."
"You're... You're welcome," Steve said, blushing deeper.
Once done, the two had arrived at a spa where Monica fed the same lie to the staff about why her "daughter" needed a waxing. Monica sat by as Steve had his legs, arms and chest waxed, almost enjoying the pained expression on his face as the hair was ripped out of him.
"It's okay," Monica said, cradling Steve in her arms. "I've booked us a mud bath. That should help the pain."
"Thank you again, Mother," Steve said, his voice now sounding more feminine.
Monica lifted his face so he could stare into her eyes, awestruck, as she said, "Now you know the pain women go through to look beautiful."
"You're right," Steve said in a stunned monotone. "You are so strong."
"As long as you realize that," Monica said, before smiling. "After our mud bath, I'll order us both massages. And since you're being such an amazing daughter, i might even request a lovely young lady for you."
The mud bath, as it turned out, was exactly what Steve needed. He wasn't sure if it was actually helping his pain or if it was mind over matter, but he would believe anything Monica told him.
As he stared at his stepmother, who was lifting one of her long legs out of the mud to run her hands down it, Steve couldn't lie to himself anymore. He was attracted to her.
When he was younger, he would always steal glimpses of her as she walked past his room, and he'd fantasize about her slipping into his room and seducing him, but he had hid those feelings away once she married his father. But now? He would at least enjoy the sight while he was here.
Monica noticed him staring and asked, "Where's wrong?"
"Oh, uh, I'm just wondering if there's anything I'm supposed to be doing," Steve replies, embarrassed.
"Just let the bath do it's job," Monica said. "When you're done, you'll feel completely transformed. Like a whole new you has taken over."
"Yes, ma'am," Steve said.
Steve truly did feel refreshed after the bath, and now was laying across a massage table across from Monica. As a man and woman, the masseurs, walked in, Monica's eyes lit up. She licked her lips hungrily as she eyed the man.
"Mama like," Monica whispered under her breath.
Steve took a look at the man. He was around the same age as Steve himself, but that's where the similarities ended. He was far more masculine than Steve was, even if he wasn't being treated as a woman currently.
His attention them turned to the woman. She was absolutely beautiful. Steve swallowed hard as he tried not to let his body betray his appearance.
Steve couldn't help but feel ashamed as the massage started. As the male masseur worked on Monica, she was moaning in pleasure. He knew that he could never make a woman feel that good. Not only that, but the beautiful masseuse working in his back would laugh if she knew he was a guy asked by his stepmother to pretend to be her daughter for a day.
"This feels so niiiiiice," Monica sighed, looking to Steve with a satisfied smile. "Don't you agree, baby?"
"Yes, Mother," Steve said.
"You feel really tight," the masseuse said. "You must not get to relax much, ma'am."
"Oh, uh, yes," Steve said.
After he two enjoyed their massages, or, rather, Monica enjoyed her massage while Steve tried enjoying it, they were now laying back in chairs.
"What should we do next, Mother?" Steve asked.
"Hmm, give me a couple minutes to scope things out," Monica said. "I very much enjoyed that young man rubbing me across my body. The only thing that would've made it better would be if I got my hands on him. Mmmm."
Steve blushed as Monica bit her finger, until she noticed the look on her "daughter's" face.
"What's the matter, darling?" She asked, before realization struck. "Oh, don't worry. I know you were attracted to that lovely young lady massaging you. I know you think she probably isn't into you either, but don't be so hard on yourself. You're quite the catch yourself."
"You think so?" Steve asked.
"Oh, yes, dear!" Monica said. "The only problem is, she might not be into women."
Steve's face sunk, causing Monica to smile mischievously.
"But if she doesn't, I could introduce her to this handsome young man I know named Steve," Monica said.
Steve's face lit back up.
"Thank you, Mother," Steve said. "I'm so grateful for you."
"Of course you are, sweetheart," Monica said. "Most going ladies wish they could have a mother like me."
The next few hours were spent with Monica and Steve getting pampered however Monica wished. Mani-Pedis, facials, hair care. By the time the two left, Steve saw himself in a body mirror and smiled. He looked like a truly beautiful woman. It was odd, but he was a little attracted to himself.
However, as men and women stared at the beautiful young lady in the purple suit out with her mother in an identical red suit, Steve found himself blush ing in embarrassment.
"Don't be so shy," Monica said. "You're a lovely young woman. You should own it."
"You really think?" Steve asked.
"Of course," Monica said. "I'd never lie to my daughter."
To finish their day, Monica and Steve picked up for, before heading back to Monica's house.
Once the two had finished, they sat on a couch together, staring out at Monica's backyard.
"This day has been absolutely fantastic," Monica said with a sigh of contentment. "You've truly made me feel like a mother being spoiled by her daughter for Mother's Day."
"I actually had a good time myself," Steve admitted. "Even if I was dressed as a girl the entire time."
Monica smirked in an almost perverted way and asked, "How did you enjoy wearing my clothes? Could you feel the heat from my body when you first put my suit on?"
"Oh, don't act all embarrassed," Monica said. "I know you enjoyed it, and enjoyed dressing like a fine young lady for me."
Steve couldn't answer, only gulp as Monica grabbed him and pushed him onto the couch, positioning herself above him.
"I always knew you were attracted to me," Monica confessed. "That's the real reason you stopped by, isn't it? You wanted to come and see your old crush."
"I- I-" Steve lost the feminine voice he'd been using and reverted to his team voice. "But you're my dad's..."
"Ex," Monica said bluntly. "I only married him to be spoiled before I took him for everything he had. There's no reason for you to be against this."
Before Steve could admit she was right, Monica saw it in his eyes, he had agreed with her, and held his head as she began kissing him. Steve laid there, mentally melting for Monica as her lips pressed hard against his and her hands held him in her grasp.
"I was never physically attracted to your father," Monica said after her lips parted from Steve's. "But you? You had this cute look to you. The only problem was you didn't make a handsome guy. But as a young lady? You're beautiful."
"Thank you, I'm honored," Steve said, slipping back into his feminine voice.
"I want you to stay here with me, as my good little girl, doing everything I tell you to," Monica commanded. "I'll teach you to be a fine young lady, maybe introduce you to some of my girl friends, and when I bring a guy home, you can please him too."
"Why that last part?" Steve asked hesitantly.
"You don't think you can satisfy me, do you?" Monica asked, a seductively cruel smile dancing on her lips. "But I do want you as eye candy. After all, isn't that fair, with how many times you and your friends ogled me?"
"Do... Do you want me to give you their numbers?" Steve asked, his tone making it clear he was ready to do so.
"Perhaps one of these days," Monica said. "But I've got my eyes on a couple other guys first. And after I seduce them, I'll bring them back from our date, and you'll give them whatever they want."
As Steve imagined what that would be like, Monica leaned closer to Steve's ear and whispered, "Because of you make me very happy, I might let you help me have a real daughter, and you don't want one of those guys to do it first, do you?"
"No, ma'am," Steve said, shaking his head obediently.
"Good," Monica said, grabbing Steve's head again. "I have so much to teach you. I imagine it'll feel like a real mother, bringing her daughter into the world of womanhood. I can't wait to get to feminizing you."
"I thought I already was," Steve said.
"Oh, sweetie," Monica said in a flirtatious tone. "This is just the start. This is a rough draft. Wait until you see the final version of yourself."
As his body reminded him of his manhood, Steve smiled, eagerly waiting for Monica to feminize him so he could please and satisfy her any way she asked. Steve moved in with Monica the next day.
Weeks passed. Weeks filled with many changes for the sissy who'd once been Monica's stepson. But after all the teaching, training, cosmetic work and shopping, Monica felt she had earned the date she just went on.
As she and her date, the masseur from the spa, entered her house, Monica stared into his eyes.
"I had a wonderful night tonight," Monica said.
"Me too, ma'am," the masseur said. "How about we keep it going in the bedroom?"
Monica smiled a truly lustful smile and said, "You know exactly how to charm a lady. But would you be opposed to someone joining us?"
"A friend of yours?" The masseur asked.
"Someone like that," Monica said. "She's the daughter of a friend of mine, but she's living with me now."
"As long as she's okay with it," the masseur, who'd been completely seduced by Monica, said.
"Stacy, come here, darling!" Monica called.
A young woman walked down the stairs in a stylish blouse and shiny leather pants.
"Yes, Mommy?" Stacy asked.
"My date, this handsome young man here, was hoping for some fun," Monica explained.
The masseur stared in shock at the young woman in front of him.
"A beauty, isn't she?" Monica asked, walking over to Stacy. "I've put a lot of work into her. Finding a top that fit her while still looking refined. Pants that perfectly hug that tight tush of hers."
Monica turned Stacy to get and gave her a kiss, before turning the young woman to the masseur. Monica grabbed Stacy's face and pointed her fingernails at her lips.
"And we can't forget these lovely, plump lips," Monica said. "I can't begin to tell you how good they feel when you kiss them. One of the reasons she calls me Mommy is because of how I basically remade her from the ground up. Of course, that's not the only reason."
Stacy couldn't be bothered to listen as Monica talked about how she dominated the young woman. Instead, she could only stare absently and drool at the thoughts running through her head.
Thanks to Monica's training, Stacy now liked the thought of pleasing the men Monica brought back, and Monica herself, naturally. The kiss Monica had planted on her was enough to make her shudder in lust even after all these weeks. But the thought that most captivated her was the thought of one day having a daughter with Monica.
"Stacy, darling, what do you say you give my date a taste of what he's in for and..." Monica stopped briefly to chuckle. "...get a taste of him too?"
"Yes, ma'am!" Stacy cried happily, getting on her knees.
- SISSIFIED BY SUITS, MAY 2024
[Sorry this is a couple weeks after Mother's Day. I wanted to submit it sooner, but couldn't get it done until now.]
