Oliver drove up to Lizzy's Boutique-Intimates for Everyone with great apprehension. Was he finally ready to dive into his greatest desires? He had done this so many times before and stopped. However, today felt different. Today felt right.

Lizzy saw the car pull up to Lizzy's Boutique-Intimates for Everyone. Given the time of day and the cold weather, there wasn’t much activity in the plaza. The man in the car sat for a few minutes before getting out and heading towards her store. She knew right away that he had reservations about going in. He pulled the door, paused a second, entered the shop, and looked around. A beautiful woman greeted him.

“Hi, come on in. I’m Lizzy. Welcome to Lizzy's Boutique-Intimates for Everyone.”

Oliver saw a stunningly beautiful young woman looking at him. His heart immediately pumped adrenaline into his system. His nervousness multiplied tenfold. He had hoped to find some frumpy middle-aged retail lady who might have dealt with guys like him in the past.

Someone with a secret desire. Someone who would be nervous, etc. He hadn’t thought the clerk might be young and super hot. He froze up and just looked at Lizzy.

Her long ebony hair cascaded down past her shoulders. Lizzy's eyes were a mesmerizing cat-like green, and her high cheekbones were soft pink. Lizzy’s glistening lips were a deep burgundy. Her face was radiant and her smile was infectious. She wore a pearl-colored satin button-down blouse.

A generous amount of her ample cleavage showed, enough to be enticing without being overtly sexual. The blouse was tucked into a mid-thigh-length, black pencil skirt. Her long, sculptured legs were encased in fine, nude-colored stockings, and time appeared to sit still for Oliver. Fear and anxiety overcame him.

“What now?” he thought. “This wasn’t the plan… think of something quick."

Lizzy’s voice broke his trance. “Is this your first time shopping with us?”

His vision came back to him, and Lizzy smiled pleasantly at him.

“God, she is beautiful,” he thought.

“Umm, yeah… I mean, yes, it is,” Oliver replied.

Lizzy asked, "Do you have something particular in mind?”

Oliver said, “Uh, uh, not really."

Lizzy thoughtfully stated, “Well, I’ll give you a minute to look around. Feel free to ask me any questions.”

Nervously, Oliver replied, “Okay, thanks."

Lizzy knew precisely what was going on. He was shopping for himself but was scared to admit it. He had probably had a thing for panties and lingerie for a long time and had never told anyone. He would say he was buying it for someone else. She got excited. A newbie! This was her favorite part of the job. She loved making guys like him comfortable for two reasons: One, she felt bad for guys who had to hide their desires. Two, they usually spent good money and became repeat customers.

She busied herself folding items while he browsed. Lizzy knew giving them a little more time before going to work was best and watched him. Consequently, Oliver soon stopped before a display of satin rompers. Lizzy glided over to a table closer.

“I see you like the rompers.”

“Umm, yeah,” he stammered. “They’re pretty.”

“I love them; they're one of my favorites,” she said as she came up next to him. “Which one did you have in mind?”

“I, I don’t know. They’re all beautiful…I am not sure I know the difference and stuff,” Oliver stammered.

Lizzy could see he was still very nervous. It was time to break the ice.

“Yes, I know, but I can help with that. What’s your name?” Lizzy asked.

Oliver gazed into Lizzy’s green eyes and said, “My name is Oliver.”

“Nice to meet you, Oliver. Do you know what size you’re looking for?”

“I don’t. This is embarrassing, but it’s for me, and I’ve never shopped for something for myself.”

He was looking down the whole time. Lizzy had had this situation many times before. She knew exactly how to handle it. She reached out and put a hand on his arm.

Rubbing it gently, she said, “Don’t be embarrassed, sweetheart. It’s no big deal.”

Oliver looked up and took comfort in her warm, sincere smile. He let out a sigh of relief as his shoulder relaxed. Lizzy noticed it all.

“Now that’s out of the way, let’s see what we can find. Do you like anyone in particular?”

“I, I, I’m not sure. I don’t know what kind would work best. They’re not designed for, um, well, guys,” Oliver said as he stammered again, looking around. He hoped this wasn't a big mistake.

But then Lizzy replied with a sparkle in her eye, “Well, that’s what I’m here for, honey. Try to relax,” she said as she rubbed his arm again. “Helping new clients was my favorite part about opening Lizzy's Boutique. That was why I named it ‘Intimates for Everyone’. I had always thought it unfair that there was a stigma about guys wearing lingerie. Women wore men’s stuff all the time, right?”

She could feel the tension ease from his arm.

“Wow, um, that’s cool. It's just that, I mean…” Oliver stammered. He was still looking down.

“Relax, Oliver. Look at me,” Lizzy said.

Oliver looked into her deep green eyes.

Compassionately, she told him, “I get it. And I can help you. Just trust me. Can you do that?”

He sighed again.

“Yes, Lizzy, I think I can. Thank you for not making this awkward,” he said shyly.

“Good, I’m glad. So, it’s almost closing time. I’m going to lock the door so we don’t get interrupted. Is that okay?”

Oliver sighed in relief and said, “Sure. That’s great.”

Lizzy smiled knowingly.

“You’re in good hands here.”

Lizzy walked up front, locked the door, and turned off the sign. As she walked back to him, she saw he was much more at ease but still apprehensive.

“So, Oliver, now that we won't be interrupted, let’s get started. Let’s pick a few things and go to the dressing area."

Oliver was caught off guard and replied, “Dressing area?”

“Of course, honey, how else will we know your right fit? There are lots of variables to consider. I pride myself on helping men like you find the perfect fit. We have to consider your height, frame size, and of course, your cock and balls. That’s the tricky part. But also the fun part,” she said with a naughty smile and a twinkle in her eye.

“I don’t know?” he replied.

Lizzy stood before him, reaching out to place her hands on his shoulders for reassurance. She looked him in the eye and explained, “Oliver, I’ve been doing this for a while, so you don’t have to be shy or embarrassed. Most guys like you who come in have only worn the panties of their mother or sister, maybe their wives. Perhaps they bought something that didn’t fit right and never had a woman to help them, or they get frustrated and stop exploring their burning desire.

"They are often insecure about the size of their dick. They are afraid and embarrassed. I can change all that if you let me. Not every woman has big tits like me, so why should every guy have a big dick? Right? I can get you to release those fears and show you the pleasure you seek.”

Her tone was so compassionate and understanding that he could not say no.

“Okay, why not?” Oliver said.

Lizzy grabbed a few things and led him to a door at the back of the boutique.

“This is our dressing suite. It gives us more space to work with,” she said with a smile.

Oliver followed her to find a very comfortable room with a loveseat, a couple of chairs, a few mirrors, and a vanity with a large mirror. As he looked around, Lizzy continued.

“I built this room, especially for men like you. It gives us plenty of room, unlike those cramped fitting rooms. Plus, we offer various services like makeovers, pampering sessions, bridal events, etc. I’ll give you a minute to get undressed while I grab a few more things.”

When she returned, Oliver sat in a chair, still in his boxers.

“So, you’re one of the shy ones, aren’t you?” Lizzy said as she approached him.

She placed some things on the side table and had him stand.

“Let's get these boxers off and see what we are working with.”

She slid his boxers down to find, as suspected, a pretty small, semi-hard cock.

“Okay, we can work with this. You know, smaller works better in most lingerie,” she said as she moved in close, brushing her tits against his arm.

As she did so, she noticed his cock twitch.

“Well, well, someone is getting excited, I see.”

Pressing herself tighter to him, she gently ran her fingers up his hardening shaft. He flinched. She could tell he was unsure what was happening.

“Don’t be nervous,” she said seductively. “Proper fittings require lots of touching and arranging. Of course, you are going to get excited. That’s the whole point now. I bet a nice pair of satin cheekies will do the job. Here, step into these.”

He did as he was told, and Lizzy slowly slid the panties up over his cock, adjusting it and gently rubbing it.

“That’s it, get good and hard. Feel that satin on your cock and balls,” Lizzy commanded.

She rubbed her nails up and down his shaft. Oliver reached down and caressed his balls.

“Go ahead, let yourself feel the sensations of the soft satin against you. Spin for me so I can check the back. Oh yes, honey, these are perfect for your cute little ass.”

Lizzy slid her hand up and down the panties. She glided her nails under the sides to straighten them.

“Oh yeah, now that’s sexy,” she said.

Lizzy came back in front of him and continued to rub his cock and balls.

Lizzy continued, “Go ahead and touch yourself. Feel your cock under that soft satin. Feel the way the panties hug your tight balls. Let yourself experience feeling sexy and looking sexy. Embrace that feminine side every man feels and allow yourself to enjoy it. Think about all the possibilities.”

Oliver relaxed a bit and let his mind wander. He rubbed his cock through the satin panties while Lizzy watched admiringly. His senses seemed to be on high. The feeling of the panties, the atmosphere, the fact that he was experiencing his fantasy, and, of course, the beautiful Lizzy standing before him was almost overwhelming yet intense. Lizzy allowed him to relish in this new sensation.

She circled him slowly and gently, gliding her nails over his chest, arms, and his cute little ass. Snuggling up against him, she pressed her big-nippled tits into his back. Lizzy then nestled her head against his ear and breathed softly, letting her tongue lick his earlobe.

“I think you are enjoying this, aren’t you, Oliver?” she softly said.

All Oliver could do was nod in agreement like a schoolboy.

“I was so glad you came in when you did. I loved being unrushed with my clients—especially new ones like you. There was so much to explore and show you. It was such a turn-on to guide someone into a whole new world. Were you ready to explore a new world with me, Oliver? Were you willing to open your mind to new experiences? To push your boundaries? To enter a world without limitations? A world where old-fashioned morals and expectations didn’t exist. A world where you could be free sexually?”

Lizzy questioned Oliver as she stared at him with her piercing green eyes.

“Oh my God, Lizzy, I’d never thought such a place existed. Can you take me to that place?” he asked.

“There is, Oliver,” she replied with a wry smile. “It’s right here. Right now. But it would help if you accepted that this world has no rules. No societal roles, norms, acceptable or unacceptable feelings or behaviors. Can you grasp that concept?"

Lizzy smiled as she cocked her head to one side, waiting for Oliver's response.

Oliver thought for a moment. His mind waffled between nervousness and excitement. What did all this mean? he thought. How should he respond?

“I think so? I don’t know. It sounds so enticing. I don’t know. Is being willing to try a good answer?” Oliver replied.

“That was a perfect answer. It was half the battle. I thought once you began trying, it would come easy enough. I knew it did for me. You see, Oliver, we're more alike than you thought,” she said with a wicked glimmer in her eyes.

The last comment concerned Oliver, who soon forgot when Lizzy picked up a short, red silk robe.

“Put this on and come sit here,” she said, pointing to the loveseat.

Oliver put on the robe, luxuriating in the light, soft feeling on his shoulders and chest. He tied the sash and sat as instructed.

Lizzy sat next to him and crossed her legs. Oliver’s eyes darted at her long, smooth, stocking-covered legs.

“I see you like the stockings. Go ahead and take a feel. We will have to get you into some soon. You’ll love the feeling,” she said reassuringly.

Lizzy continued, “You’re probably wondering how I know so much about how you feel and what you’re thinking. It’s simple, actually; I used to be you until I decided to make some changes. Big changes,” she giggled as she thrust her voluptuous chest forward.

Oliver’s reaction was as she expected. His eyes opened wide and popped open. He was dazed.

“You seem surprised,” she said in a comforting manner. “You’ve spent so much time admiring my tits and ass that you didn’t notice this little lump in my throat,” she giggled. “Don’t worry. I won’t try to push you into anything or suggest you make the changes I did. I can help you find what fits you best, or I can help you explore experiences you’ve only fantasized about. Remember, what happens in this room stays here. We both appreciate discretion, I imagine.”

“Um, I don’t know what to say. I would have never guessed. I was looking for some lingerie and never expected this.”

Oliver paused.

“But much of what you’ve said makes sense and is intriguing.”

Lizzy replied, “I get it. You said earlier you trust me. Do you still?”

Oliver nodded in agreement.

“That’s wonderful,” she said, touching his knee. “Just relax a minute while I get more comfortable. It seems unfair that you are the only one half-naked. I think you’ll be more at ease if we are both half-naked,” she said with a twinkle in her green eyes.

Lizzy stood in front of him, slowly unbuttoned and removed her blouse. Underneath, she wore a beautiful black satin, embroidered shelf bra. She saw his look of approval and smiled. She turned around, looked over her shoulder, and asked, “Are you sure you want to see all of me?”

Oliver gushed and replied, “I do, Lizzy. God, you are so fucking sexy.”

Oliver looked on with anticipation as she lowered the rear zipper. She slowly shimmied it down, exposing an incredibly sexy, round ass covered chiefly in black satin. She intentionally bent down, dramatically thrusting her ass out.

Gathering the skirt, she looked back at him and asked, “Are you ready?”

“I am. I can't wait, actually,” he sighed deeply.

Lizzy turned to face him. His eyes darted directly to her crotch, where he saw a noticeable but not overtly colossal bulge. He stared, not knowing what to do or say.

Finally, he looked up and told Lizzy. “I didn’t think you could be any sexier until now….I mean, wow!” he said with a nervous smile.

Lizzy stepped forward and reached out for his hand. Oliver took her hand and stood inches from the sexiest vision he had ever seen. Lizzy reached down and untied the sash of his robe, slid it off his shoulders, and let it drop to the floor. Her hand slid to the small of his back and pulled him in tight to her body.

She looked at him profoundly and planted her moist lips on his. Her mouth opened slightly as her tongue caressed his lips. They opened instantly and engaged in the most passionate kiss Oliver could have imagined.

Suddenly, her hand slid further to grasp his ass to pull the crotches together firmly. The kissing intensified. Oliver’s hands began to wander and caress Lizzy’s ass and back. Time seemed to stand still for Oliver. His eyes closed as he relished the feeling of their panty-covered cocks rubbing together. The fire was lit, and his inhibitions were melting.

Lizzy broke the embrace and looked at Oliver lustfully. She took his hand, brought it to her, and placed it on her upper thigh. Their eyes locked. She sensed his hesitance, but experience told her he was ready.

“Go on, honey, it won't bite,” she said as she led his hand to her semi-hard cock. His resistance slid away as he felt her throbbing dick. They kissed again as he explored her panty-covered cock and balls.

Again, Lizzy broke the embrace. “Come sit again.” Once seated, she straddled his lap and sat on his knees, leaving enough room that he would have access to her crotch.

She reached down and straightened her cock in the panties. She took his hand and placed it there. Lizzy lovingly said, “See, honey, not everyone is hung like a porn star."

She continued, "You don’t need to be concerned with that anymore, at least not here with me. I want you to be comfortable. I’m sure you’ve never touched another cock before, so take your time. Explore my body. Please tell me what you’re thinking. I want to know your secrets. Open up completely. There are no taboos here. Let me guide you in this new world.”

“Right now, I’m thinking this can't be real," Oliver replied. "I’m dreaming. But this,” he said, squeezing her cock, “sure isn’t my imagination.”

Oliver took a deep breath and continued, “You know, I’ve just recently started watching trans porn, but I never thought I would experience something like this. Can I take it out?”

Lizzy replied to Oliver, “Of course, honey. You’re free to explore all of me. Ask me anything you like. Tell me anything."

Lizzy stood again, reaching out for him to stand also. “Let's go over to the mirror. I love watching ourselves in the mirror.” She led him to a large, full-length tailor's mirror, the kind with three panes so you can see different angles. They stood shoulder to shoulder, admiring each other. Lizzy’s hand gently caressed his ass over the satin panties.

Lizzy entranced Oliver. He was in a state of ecstasy and said, “Ohh, that feels so good, Lizzy.”

Lizzy smiled at him and said, “I think I know something that will feel even better. Take off my panties."

Oliver slid the panties down over her stockinged legs. Bending at the waist to pick them up, his face was inches from her hard cock. He looked to see Lizzy’s approving smile. He smiled back and placed a soft kiss on the head of her cock, and stood back up.

“I see someone likes my hard clitty,” Lizzy whispered in his ear. She maneuvered herself behind him, took hold of his hips, and pressed her hard cock against his ass.

She found the groove between his cheeks and began to grind against him. She felt him push back against her. Her hand gently took hold of his balls.

Lizzy pressed her bra-covered tits against his back and whispered in his ear, “Feels good. You always wondered what this would be like. Let yourself go. Let all your guards and worries slip away.”

“Oh my God, Lizzy, this feels so amazing. I’ve never been so turned on!” He turned to face her and said, “Lizzy, I need to cum so badly, and I want to make you cum with me.”

His hand gripped Lizzy's cock and started jerking her. They kissed passionately as Lizzy led them back to the couch. She pushed Oliver down and straddled his legs again.

Yet this time, their cocks were touching. She grabbed some lube from the end table and began rubbing it on their cocks together.

Oliver’s head fell back, eyes closed. She began furiously jerking their cocks together until Oliver let out a moan and began shooting his load. Her rhythm and excitement continued until she was beyond control and erupted with him.

Lizzy thrust her hips as wave after orgasmic wave swept through her. They collapsed into each other’s arms and remained silent as the euphoria lingered.

Lizzy broke the silence first. “So, I trust you plan on paying for those panties now that you’ve stained them!” They both broke into laughter as they held each other tight in the afterglow of their euphoria.