First Time Escort (Part 2)

As the door slowly opened, Kimmie began getting second thoughts. Could she really go through with it? Did she have what it takes to be an escort? Either way, there was no turning back. She would just have to get through the next hour or so, and that would be it. This was something she would never do again.

Kimmie felt a sense of relief when Mike came into view. She was half-expecting a man who wouldn’t be capable of capturing a woman’s interest; she couldn’t have been more wrong. He was about six feet tall with brown hair that just started graying at the temples. He had an average build and wasn’t the least bit overweight. It was clear that he worked out, because his arms were nicely toned. And, to top it off, he was good-looking with a strong jaw and a well-groomed goatee.

She may have had reservations about being an escort for a night, but she figured there were worse things in the world than fucking Mike.

Unsure of what exactly to do, she simply smiled, before slowly getting off the bed to greet him.

“I’m Kimmie, and I’ve been looking forward to meeting you,” she said, while putting her hands on his shoulders and kissing him gently on the cheek. She tried her best to remember everything Brooke had told her.

“I’ve been looking forward to meeting you, as well. I’m Mike.”

“I’d rather call you daddy, if that’s OK,” she whispered into his ear.

He couldn’t help but smile after hearing those words, and said, “I’d like that.”

“I hope you like my outfit. I thought of you when I bought it today.”

“You look wonderful, and so much better than I dared hope.”

Not sure of what to say or do next, she took his hand and led him to the queen-sized bed.

What comes next? Should she start taking his clothes off? Give him a blowjob? That all seemed abrupt. Well, he liked being called daddy, so she figured she couldn’t go wrong playing his little girl.

She laid down next to him with her head on his shoulder and her hand rubbing his chest.

“Brooke was holding back on me. She didn’t tell me you were this good-looking.”

“Thank you, Kimmie. That’s very kind of you.”

She began undoing the buttons on his shirt. “You don’t mind, do you?”

Of course he didn’t mind. He was there for that and more–much more–but he liked being asked, and it felt sexy to get his permission.

“No, not at all.”

If there was one thing she learned as a stripper, it was how to take clothes off seductively. She undid one of his buttons and slowly let her hand slide under his shirt and lightly glide over his flesh. She felt him shudder, which told her she was off to a good start.

“Brooke tells me you’re new at this.”

“Yes. In fact, you’re my very first. I hope that’s OK.”

“I’m actually proud to be your first.”

She smiled as she started undoing the rest of the buttons on his shirt, which allowed her hand to roam over his entire chest. After a couple of minutes, Kimmie’s hand stopped. She hated admitting it to herself, but she wasn’t exactly sure what to do next? Should she ask Mike what he wanted? But, since she was a high-priced escort, she should know. What if she made a move that turned him off? With the money he’s spending, he’s certainly entitled to a memorable encounter.

Mike sensed her unease and asked, “Would it help if I guided you a little.”

She nodded. In a way, they would both be taking care of each other at the same time. She liked that idea.

“Why don’t you slide my pants off? I think it’s time we got more comfortable.”

She undid his pants slowly to build his anticipation, as well as her own. He raised his hips, making it easier for Kimmie to slide his pants and briefs down his legs and drop them on the floor. Her eyes widened as Mike’s semi-hard cock sprang into view. He was large, and she knew he’d be getting much larger in no time.

“It’s beautiful, Mike. So much more than I hoped for.”

Those weren’t mere words. His cock was both long and wide with a large, pink head. And it was shaved clean. No hair at all. She had never had a bare cock before, and for the first time, she was excited about having sex with Mike.

“Can I have a kiss?”

Those words surprised her. For some reason, Kimmie thought this would only be about sucking and fucking.  Their lips met lightly–then again and again, each time leading to a deeper kiss, until their tongues were passionately exploring each other’s mouths.

She could have stayed that way for the rest of their time together, but she wanted more–much more–and began kissing her way down his chest.

Mike’s cock twitched as she kissed his inner thighs and the soft flesh near the base of his shaft. She couldn’t hold back any longer. And if he wanted to cum twice during their session, she had better take care of business now.

“Can I have a taste? Would that be okay, daddy?”

“I’d like nothing more, Kimmie.”

Teasing him ever so slightly, she slowly licked up the length of the shaft–once, twice, three times– before letting the head of his cock slowly disappear between her full lips. She enjoyed the smooth flesh and musky scent, and she craved more. Kimmie went deeper and deeper, feeling him grow all the more in her warm, wet mouth. She loved making a cock harden, knowing that it was her doing and no one else’s. And she loved knowing that a man wanted her desperately.

She kissed and licked his cock, then rubbed it along her cheek and lips as if she couldn’t get enough. Then, once again, she took him deep into her mouth, getting to about an inch from the base. She gagged slightly while trying to take more, but his cock filled her mouth, and she could go no deeper. For a moment, she wondered how it would fit when they fucked, but that concern would have to wait.

She sucked as her tongue played with his shaft, and her lips caressed his skin. Mike squirmed under her touch and his cock throbbed, which let her know it wouldn’t be much longer. She quickened her pace and embraced him all the more with her lips. His rock-hard flesh pulsed again and again, unleashing a stream of cum into her waiting mouth. It was warm,  salty, and sticky, and she couldn’t get enough.

Kimmie had tried swallowing once before, but couldn’t go through with it. But this was different. Maybe it was because of Mike or the circumstances. Whatever the reason, she loved the feel and taste of his cum. It was pure sex, and she wanted the experience to last.

She looked up at him while she slowly backed off his cock. Her lips lingered around the head before she pulled away and swallowed, letting every drop slide down her throat. She  then licked her lips and smiled, locking her eyes on his.

A small bead formed at the head of his cock. Kimmie bent down to catch it, wanting one more taste and to show Mike how much she enjoyed taking care of him. Moving down to the bottom of his shaft, Kimmie licked up every side, making sure nothing went to waste. And again, she put his cock back into her mouth to savor the moment.

Kimmie wasn’t just willing to fuck Mike; she wanted to. Very much.

Knowing that Mike needed a little time to recover before they fucked, she snuggled up next to him. But he had other things in mind.

His hands began caressing her–first her hair, then her back, ass, and thighs. He was tender, something she didn’t quite expect. He pushed himself up and gently positioned her onto her back so that he could explore the rest of her. Starting with her full breasts, Mike slowly kissed her warm, soft flesh, spending plenty of time on her erect nipples. He worked his way down her body until he found himself between her welcoming thighs.

Kimmie closed her eyes and felt his soft kisses all along her opening, followed by the warmth of his tongue slowly caressing her pussy lips, again and again. She let out a soft moan as his tongue penetrated her opening and licked her insides. Sure, Kimmie thought she’d enjoy being fucked, but little did she expect this amount of attention–or pleasure.

Mike turned his attention to her clit, running his tongue over its hardness before taking it between his lips. His gentle sucking, followed by a finger inside, pushed her to new heights. He sucked, licked, and probed until her body yielded to a wave of passion that began between her legs. Kimmie’s body shook and convulsed, as she cried out, pushing her pussy into Mike’s face. She lay back as the shudders subsided and her breathing slowed.

No one had made her feel that way before. And now she wanted more.

“Oh, thank you, Daddy,” she whispered. “But now I need to feel you inside me. Please fuck me. Fuck me now.”

Mike didn’t respond, but simply knelt before her, stroking his cock to get it hard. She took him back into her mouth to complete the task. His cock was big and wide and stiff. He was ready.

As she reached for the condoms on the side table, Kimmie paused and looked up at him. She wanted his cock now, but she wanted it in all its glory.

“You always use protection, don’t you, Daddy?”

He nodded.

“And this is the first time I’ve done something like this. You  can take me raw, if you want. Would you like that?”

A big part of her knew she shouldn’t go without protection, but she felt it would be OK under the circumstances. And if she was going to have one experience as an escort, she wanted to make the most of it.

Plus, Mike’s cock was gorgeous–and big. She wanted to feel it all.

She looked up at his face and found a look of unadulterated desire, unlike anything she had seen before. He not only wanted her, he craved her. To see a man want her–to need her–that strongly gave her both a thrill and a sense of power.

Kimmie’s own anticipation was building as she felt his warm thighs touching hers and his hardness pressing against her very wet slit. His shaft pressed against her, and their eyes met.

Slowly his tip pushed the lips apart and entered her. She moved her hips forward to welcome his penetrating cock and gasped as her pussy was filled with his very hard flesh.

He began pulling out of her, then thrust his dick back into her–again and again. Not fast, not hard, but very sensually.  He wasn’t so much fucking her, as he was loving her and her body. As much as she wanted that cock to fill her and take her to new heights, she was more turned on by the desire she found on his face. He may have wanted to be called daddy, but Kimmie now realized that she was the one in control. She loved the idea of having that power and, for the first time, wondered if she could give it up.

Kimmie started moving her hips faster, and the sound of flesh slapping against flesh filled the room. She clutched his sides tightly and cried out, as her body convulsed in waves of pleasure. It was then that Mike’s cock pulsed over and over, filling her pussy with his hot cum.

After a minute passed, Mike lowered himself onto Kimmie.

“Hold me, daddy,” she said.

She knew he’d like the sound of that.

She also knew there was no turning back for her. This was only the beginning.

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First Time Escort (Part 1)

Kimmie held up the white two-piece outfit, admiring the halter top with the plunging, scoop neckline and tight bottoms that were a cross between shorts and panties. She stood a little over five feet and had a firm 34C chest, small waist, and round butt. She knew the outfit would provide a nice contrast to her long black hair, as well as show off her ample cleavage and cling to her ass like a second skin.

“Oh, good choice,” said a woman shopping in the same aisle. “I think you’d look great in that–much better than I ever would.”

“Thank you,” said Kimmie. “I want to leave a little to the imagination, but not too much.”

She let out a small giggle as she looked over her fellow-shopper–a beautiful blonde with shoulder-length blonde hair.

“I’m Brooke, by the way.”

“I’m Kimmie.”

“Are you a dancer or just spicing up your personal life?”

Kimmie smiled, knowing that it was pretty obvious. The Adult Boutique was the best place in town for sex videos, toys, and stripper clothes.

“Yeah, I just got a job dancing, and I figured I had better come up with more outfits.”

“You’ll do well here. This is where I got most of my clothes when I danced.”

Kimmie was not surprised that Brooke had been a stripper. She has the perfect spinner’s body with firm B-cups, a cute ass, thick blonde hair, and beautiful blue eyes. She looked like a model straight out of a magazine.

“You don’t dance anymore? I bet you were popular with the guys.” Kimmie said those words as her eyes took in all of Brooke’s body.

“Yeah, I did pretty well. But, let’s just say, I got into something that fit my schedule better and made me more money. A lot more.”

Kimmie didn’t want to push too hard, but thought it was safe to ask, “What did you wind up doing?”

Brooke wasn’t going to beat around the bush. “I became an escort.”

There was a silence. Kimmie had never met a hooker before. She didn’t know how to respond.

Brooke was happy to fill in the gap.

“The guys at the club wanted some extras from me during the private dances, and I was happy to oblige, especially since they were tipping me nicely. It didn’t take long to realize I could do better on my own. I could set my own hours, and I wouldn’t have to share the money with the club.”

“Do you still work as an escort?” Kimmie was intrigued.

“Sometimes. But what I mostly do is run my own agency. I have ladies working for me. It’s all high-end. I screen the ladies, I screen the clients, and everyone’s happy.”

“I’m impressed. It sounds like you have a very good thing going.” Kimmie opened her mouth to say more, but just smiled instead.

Brooke was sizing up Kimmie’s reaction and decided to make her move.

“Is this something that you might be interested in?”

Brooke looked directly at Kimmie and smiled, waiting for her answer.

“I don’t know. I mean, it’s a big step just being a dancer.”

“How old are you?”

“18. I dance at a nude club, where’s there’s no alcohol, so the girls can be under 21.”

“Guys love girls who are 18. You’d be very popular with my clients.”

Kimmie liked the thought of guys–a lot of guys–wanting her in that way. And she loved sex–a lot. But she considered herself a late-bloomer, having only discovered sex a year ago. She still had a lot to learn, and if a guy is paying for sex, he pretty much wants a professional. The idea of being an escort excited her, but she wasn’t ready for it, at least not yet.

“I’ll give it some thought and get back to you.” It was a half-lie. While Kimmie would think about it, she had no intention of accepting Brooke’s offer.

“Sounds fair. Why don’t you give me your number, and I’ll call you in a couple of weeks. Would that be OK?”

Kimmie was flattered–too flattered to say no, so she shared it with Brooke, who immediately put it into her phone.

Kimmie thanked Brooke, said bye, and went to the counter to pay for her new outfit. There was just enough time to run home and get ready for work.

After a few days, Kimmie started to feel she was fitting in as a stripper. She got her share of compliments, as well as tips, and the men were taking her up on the private dances in the back rooms. While the money wasn’t bad, it wasn’t as good as she hoped it would be. But she had only been dancing for a week and was assured it would only get better.

She let out a sigh and heard a ping from her phone, which surprised her because all her friends knew she seldom got up before noon.

Brooke: Hi Kimmie. It’s Brooke. We met at The Adult Boutique a few days ago. How r u?

Kimmie: All good. And u?

Brooke: Same here. I have an offer.

Kimmie thought she’d have a little more time to think things over, even though she’d eventually just say no.

Kimmie: No thanks. I don’t think it’s for me.

Brooke chose to ignore Kimmie’s text.

Brooke: I have an important client from out of town who wants to visit with a young lady. 18 or 19. Long hair. Big tits. You’re perfect.

Kimmie started feeling excited at the thought, but she knew she wasn’t escort material.

Kimmie: I’ve never done this before. Have to say no.

Then she admitted: I haven’t even had sex very much.

There was a long pause, making her think that Brooke gave up. Kimmie was heading to the kitchen when she heard another ping.

Brooke: I checked with the client. He’s OK with that. In fact, it turns him on.

Kimmie: No thanks.

Brooke: $300.

That was more than she was taking home from the club, but Kimmie held firm.

Kimmie: I can’t. Really.

Another pause. Maybe she was texting the client again. Or maybe she finally did give up.

Then came a ping.

Brooke: He’ll pay extra. And I’ll give you a bigger cut. I want to keep him happy.

Kimmie wasn’t sure what that meant, but she was a little more than curious.

Brooke: $600.

Kimmie just stared at her screen. That was a lot of money for an hour–or however long an appointment takes. And it would be for sex–something she liked.

Kimmie: Where should I go? And when?

Brooke: Meet me at Adult Boutique. 8pm. Bring something cute & sexy. No stripper clothes.

Kimmie had a little over eight hours to buy something appropriate for her escorting debut. She was thinking of a sheer babydoll with a matching thong, black stockings, garter belt, and heels. Her heart was racing. Sure, the money would be great, but the idea of someone paying her good money for sex was exciting. She was looking forward to it more than she could have imagined. Much more.

When the time came, Kimmie pulled into the parking lot of the Adult Boutique, followed shortly by Brooke, who told her to hop in. Barely five minutes later, they arrived at an upscale apartment complex and made their way to a spacious, well-furnished suite. It was not at all what Kimmie expected.

“I thought your place would be nice, but this is amazing,” said Kimmie.

“It has to be. I cater to a special clientele.”

Kimmie nodded as her eyes scanned the apartment. There was a luxurious furniture, two bedrooms, a large kitchen, and artwork all along the walls.

“Why don’t you put on the clothes you brought? You can use the room straight down the hallway. Afterwards, I’ll give you a little pep talk.”

Kimmie took her bag and headed to the bedroom. She was excited to show Brooke what she chose, and more than a a little nervous over whether it was something the client would like. She came out ten minutes later wearing a dark purple, sheer babydoll and matching g-string. The flared skirt and the satin bow between her breasts gave it a cute, almost little girl look. But with her nipples and g-string clearly visible through the material, there was no doubt that she was all about sex and was there for the taking.

To complete her outfit, she wore a pair of four-inch heels that emphasized the curve of her ass and made her legs look all the longer.

She waited for a reaction. Was the outfit cute enough? Was it sexy enough? And most importantly, was it something her client would find appealing. Kimmie felt a flood of relief when Brooke’s face broke into a smile.

“Perfect. You’re absolutely perfect. It’s the right combination of cute and sexy that Mike adores.”

Mike. She now knew his name, which made everything all the more real.

“Have a seat, Kimmie. He’ll be here in about half-an-hour. Since this is your first time, I want to tell you what to expect and answer any questions you might have.”

Kimmie sat down next to Brooke, eager to soak in all that she could in the short time she had.

“The appointment is technically for an hour, but considering what he’s paying, I’d like to give him at least an hour-and-a-half. Is that OK?”

Kimmie nodded.

Mike likes to be called daddy. And it turns him on when a girl asks permission to do things. It makes him feel that it’s something she wants as much as he does.”

So far, so good.

“Did you shave your pussy? My girls are either bare or neatly trimmed. Mike likes it smooth.”

“It’s all bare. I started shaving regularly after getting the job as a stripper.”

“Do you swallow?”

Kimmie hesitated. She’s had a few guys cum in her mouth, but she always spit. She did try to swallow once, but wasn’t very successful. She shook her head.

“You need to swallow. And act like you enjoy it. Can you manage that. It’s important.”

Kimmie nodded, but not with a lot of confidence.

“If he cums in your mouth, keep your lips locked on his dick, and don’t make any strange faces. When he’s done, suck and lick some more. Make him believe you can’t get enough.”

“I can do that.”

“Another thing. Don’t just stick his cock in your mouth. Make love to it. Enjoy it. Savor it. You want Mike to think there’s nothing else you’d rather be doing.”

That would easy. Kimmie enjoyed feeling a cock become hard in her mouth. She loved the smell and feel of a man’s erect flesh. And she always felt proud when it exploded. Yeah, making love to a cock would be easy.

“Finally, it’s not over when a client cums. Clients pay for the entire time, and we always offer multiple shots. Mike likes to cum in the mouth before fucking. It’s twice the pleasure, plus it makes him last longer when he does fuck you. Are you good with that?”

Kimmie was more than fine with that. If he could cum a third time, that would be even better.

“Do you have any questions for me?”

“How do I start? I have no idea how to begin.”

“You’ll be in the bedroom waiting for him. Mike will knock lightly on the door, then let himself in. I suggest kneeling on the bed, then getting up to give him a hug and a little kiss on the cheek. After that, your instincts will kick in. Are you ready?”

Kimmie didn’t know how to answer. She didn’t feel quite ready, but she understood everything Brooke told her. She would just do her best and make sure Mike was taken care of.

They went to the bedroom, and Kimmie took her place on the bed–heels on, feet tucked under her butt, and her back nicely arched. A buzzer sounded and Brooke turned to wish her good luck. With that, the door closed and Kimmie’s heart raced faster and faster.

Just when Kimmie thought she couldn’t handle the anticipation any longer, she heard a gentle rap, and the door slowly opened.

Nickie & the Shoe Clerk

Nickie paused one last time to check herself in the store window. Her top was on the modest side. Deep red with a scooped neckline that gave only a hint of her breasts. And there was no cleavage since she had it buttoned all the way. But the material draped beautifully over her bust, leaving no doubt about the full breasts that lie beneath.  She wanted a modest top so there was no visual competition for the skirt.  The black skirt was definitely tight and short–following the curves of her hips and ending just two inches below the tops of her legs.

Her shoes, meanwhile, were basic black pumps with barely a heel. Mundane, to say the least. But that was the whole point.

She smiled at her reflection and walked two more store fronts down the mall until she came to a shoe store.

Nickie was ready.

The clerk was alone, which was to be expected 8:30 at night on a Monday.

“Good evening. Is there anything I can help you with?”

Nickie paused for a moment and smiled.

“Not yet. I think I’ll just look for a bit.”

“Let me know if there’s anything I can do.”

Nickie slowly walked to the nearest shelves and looked out the corner of her eye to make sure the clerk was watching.  Bending over, she reached for a shoe on the lower shelf, letting the skirt ride up to the bottom of her ass cheeks. She felt the air against the upper part of her legs and swore she could feel his gaze taking it all in. Standing up, she pretended to adjust her skirt, letting her hand smooth out any wrinkles on her ass.

After putting the shoe down, she turned around to find the clerk staring her way, not even bothering to hide his obvious interest.

“I think I could use your help, after all.”

“Wh-what can I do for you,” he said as he quickly moved from behind the counter.

Nickie glanced at his name tag, then looked straight into his eyes.

“I’d like a pair of boots, Joe. Something sexy.”

“What exactly are you looking for. There’s a lot to choose from.”

“Since I’m hoping for something that a man would find appealing, I’d like to see what you come up with.”

With that, Nickie backed up, turned slightly, put her hands on her hips, and gave him the warmest smile she could conjure up.

“What boots would complete this picture, Joe?”

After taking in the view from top to bottom, he nodded, then headed to the stock room.

“I wear a size 7,” Nickie called out.

Joe turned back with a grin, more than a little embarrassed that he neglected to get that crucial bit of information. And Nickie couldn’t help grinning herself, knowing that she already had him flustered.

She took a seat and waited to see what he came up with. After about five minutes, Joe came her way carrying two boxes and sat on a small bench in front of her.

“I’ve got something you may like,” Joe said as he handed her a short, black boot with a four-inch heel.

“Would you mind putting it on for me, Joe? It’d be a lot easier for me.”

Joe gladly removed the black pump from her right foot and replaced it with a boot that went just over her ankle. As he started tying the laces, Nickie moved her left leg, which pulled up her tight skirt an inch or two, calling attention to her thighs and more.

As she did so, Joe couldn’t resist following the softness of her legs to the hem of her extremely short skirt, wondering if she meant to give him such a view, or if it was an accident.

Could he tell that Nickie failed to wear any panties? Probably not. At least, not yet.

After tying the laces, he sat back on his heels and looked up at her, waiting for a reaction.

“They’re very cute, but I was hoping for something more than cute.”

“Well, I think I have something,” he said as he opened up another box and showed her a black, mid-calf boot with four-inch heels and a wrap-around leather tie.

Nickie loved what she saw and couldn’t wait to try it on.

Joe undid the boot on her right foot and slowly took it off. Instinctively, he reached out and rubbed her heel, but stopped when he realized what he had done.  He quickly looked up to see her smiling broadly at him. Relieved–and more than a little turned on–Joe gently pulled the other boot on her foot.

“I like it, Joe. Would you mind putting the other boot on for me?”

“Not at all,” he said, hoping his eagerness wasn’t too obvious.

As Joe took off her left shoe and started putting on the boot, Nickie moved forward on the seat, bringing the hem of her skirt to the very tops of her legs. At the same time, she undid two of the buttons on her blouse. It was time to give Joe a real show.

He sat back and stared directly up her skirt till his eyes rested squarely on her shaved pussy. Stunned, he felt paralyzed as he continued to soak up the view before him, not caring that she saw exactly what he was doing. His pulse raced and his cock grew hard as he tried to make sense of what was taking place.

This had to be deliberate, but Joe needed to be careful. One wrong  comment, one wrong move, and his boss would likely hear about it.

Nickie bent over, letting her hand run along her right leg, down to the black leather boot that adorned her lower leg. As she did so, Joe could see straight down her blouse. He looked at her, hoping to find a clue to help him understand, but Nickie was admiring and caressing the boots.

Finally, she looked into Joe’s face. “I love the boots, Joe, but they’re not quite what I wanted.”

All he could do was stare.

“You’ve heard of fuck-me pumps, haven’t you?”

Joe’s face momentarily betrayed his surprise at her choice of words. He nodded.

“I’d like a pair of fuck-me boots–something that will make a man notice me, maybe even want me. A second skin.”

No words came to Joe, because he knew men already noticed her, and, if they were like him, they wanted her, as well.

“Do you have anything like that?”

Without even answering, Joe got up and went to the back room, coming out two minutes later with a long box. Sitting in front of her once again, he took out a pair of black thigh-thigh boots that came with seven-inch heels and zippers that ran up the back.

They were perfect.

After removing the pair on her feet, Joe slipped on the right boot, followed by the left one. He then asked Nickie to stand so he could more easily zip up the thigh-high boots–and he did so slowly–almost lovingly–savoring the moment.

“These feel wonderful. But I want them to look like another layer of my skin. Would you mind making sure that there are no bumps or ripples? You can just run your hands along the boots to see if they’re perfectly smooth.”

Joe was speechless as he simply stared at her legs.

“Then check the tops, where they meet my thighs.  That way you can tell if there’s any kind of gap. Would that be OK?”

“Sure. Whatever you like.”

Joe started at the toes of her right foot and gently caressed her foot through the boot–then her ankle and calf–working his way slowly up her leg past her knee to her thigh, until he reached the top of the boot, just inches below the hem of her skirt. His warm hands moved from the boot to her thigh and lingered for a moment on her soft flesh.

Nickie felt her leg tingle, and she let out a soft moan.

Joe shifted his attention to her other left leg and again moved his hands carefully around and up the boot, feeling every inch as he worked his way up toward her thigh. Once again, he moved over the boot to her warm flesh–only this time he boldly caressed her thigh until her felt the hem of her skit. And he moved further up her leg until his hands were under her skirt, inches from the bare opening of her pussy.

While he couldn’t be sure how far Nickie was willing to go, Joe knew she was well aware of what she was doing.

Nickie jumped ever so slightly. She didn’t expect to have that reaction with her little episode–but she did. His hands–his touch–started a current that ran from her thighs to her pussy, before spreading upward throughout her body.

Joe was pushing the boundaries, and why not–Nickie certainly did. He looked to her face for a clue, but found it in her legs, which moved further apart, inviting him to go further.

And he accepted that invitation, sliding his hands further until he could feel her slit. She was wet–very wet–and Joe easily pushed a finger into her opening. With that, Nickie sat down again to keep out-of-view of anyone passing by the store window.

Nickie moaned softly, surprised at how excited she became. She loved seducing men and making them want her, but never thought her own desire would build so strongly. It was clear he wanted her, and she wanted him just as badly.

Nickie’s moaning became louder as she felt him caress the inside of her pussy with a finger from his right hand, while his other hand moved up to clit. There were no other customers in the store, but that was the furthest thing from her mind. All she cared about was the mounting pleasure from his touch and his probing.

Joe slid another finger insider her and began moving the two inside and out, faster and faster. Unable to resist any longer, he came in closer, replacing his left hand with his mouth–running his tongue along her clit, then enveloping it with his lips so that he could taste her and suck on her as his fingers thrust faster and faster.

Nickie tilted her head back and waited for the waves of ecstasy that began in her pussy and spread throughout her body over and over. When the feeling subsided, she closed her eyes and savored the moment. Looking down, she locked eyes with Joe and traded smiles.

Without saying a word, Nickie gathered herself, stood in front of Joe. “I’ll take the boots, and I’d like to wear them now.”

She followed Joe to the counter, paid for her new footwear, kissed him on the cheek, and whispered into his ear, “Thank you, Joe. Maybe I’ll see you again sometime.”

Turning around, Nickie walked slowly out the doorway and around the corner, with Joe watching her every move.

Nickie stopped in front of a nearby store window and studied her reflection, straightening her hair and admiring her new boots. After a couple of minutes, she could hear one gate after another coming down as employees began locking down their stores. She turned, and began walking back from where she came, till she approached a young man from behind.

“I want to tell you how much I appreciated your service tonight.”

Joe turned toward Nickie, unable to hide his surprise at seeing her again so soon.

“Now that it’s after-hours for you, how about I help you this time.” Nickie said those words as her eyes settled on the obvious bulge in his pants.

Taking his arm in hers, Nickie led him toward the exit. This time, Joe had no doubt about her intentions.

Welcome to The Dirty Scribe

I’m glad you found my new and evolving site. What you read here is my work, unless otherwise noted. I was previously a contributing author for The Sex Writer, which, sadly, is no  longer around. The time I have for writing my stories varies, which partly explains why I post irregularly. I’m currently working on several ideas and expect to have a burst of productivity before too long. I hope you like what you see and come back periodically to see my latest fantasies come to life.

Babysitter Makes Her Move

Ashley chose her outfit carefully. She wore a simple white blouse with buttons. It was tight, but Mr. Brenner couldn’t tell since she kept her sweater on till after he left. Her skirt was loose and short–well above the knees. She decided against a plaid, thinking it was cliché and, instead, went for bright blue. She completed the outfit with a pair of pink ankle socks. She was going for a look that was both innocent and sexy–just short of slutty.

And she succeeded beautifully.

At the same time, Ashley was more nervous than she had ever been in her life–and she was starting to get second thoughts. Sure, Mr. Brenner was good-looking and friendly, and they got along very well–but she’d known him for years and didn’t want to risk hurting their relationship. He was a father figure, and not once did she think of him sexually–that is, until four weeks earlier. That was when she used his computer to look up something online and stumbled across his collection of porn videos. Ashley didn’t think a lot about it until she realized most of the videos had to do with babysitters–and most of the girls were blonde, just like her!

That changed everything. From then on, she couldn’t stop thinking of Mr. Brenner in a sexual way. The discovery of his porn videos came at a time when she was already thinking of having sex for the first time–of finally getting fucked–but the idea of doing it with a boy from her school didn’t appeal to her. She didn’t want to lose her virginity to someone who didn’t know what he was doing; she wanted an experience that she would always treasure. She wanted a man.

Ashley didn’t think that would ever be possible–that is, until she discovered a different side to Mr. Brenner. What started as an innocent fantasy turned into an obsession. Did he think of her sexually? Could she really be the object of his fantasies? Ashley’s urges kept growing stronger, and she couldn’t pass up the opportunity to find out–but she was going to tread carefully, just in case she misread the signs.

Ashley wasn’t sure how to go about seducing Mr. Brenner–or just letting him know she was sexually available. She found some guidance in his video collection. Even if they didn’t show real-life scenarios, Ashley figured anything that reflected his sexually fantasies would help.

It was almost 10:30, and she heard a car pull up in the driveway. Ready or not, it was time to find out if Mr. Richmond thought of her as more than a babysitter.

Ashley quickly took her place on the sofa with her face turned  away. She brought up her knees which let her ass stick out. Then she pulled up her small skirt till it showed off most of her left hip, just barely covering her lace panties. Finally, she undid the top three buttons of her blouse. She was ready.

Her heart pounded, and she waited.

After what felt like half-an-hour, the door to the kitchen opened, and Mr. Brenner called out, “Ashley. I’m home.”

As hard as it was, she resisted the urge to respond, wanting him to think she was sound asleep.

She heard him walk into the living room and then just stop. There was no movement, no sound. He must have been looking at her, and Ashley hoped–even prayed–that he liked what he saw. Maybe his eyes were following the curves from her feet, all along her smooth legs, up to the roundness of her hip and her half-exposed ass.

He wasn’t moving–and that had to be a good sign.

Finally, Mr. Brenner half whispered her name.

“Ashley? Are you awake?”

She moved her head with her eyes half-closed and looked his way.

“Oh, Mr. Brenner. I didn’t hear you come in. Sorry.”

She slowly turned around on the sofa, letting the skirt ride up to the tops of her thighs and sat down facing him.

“No problem, Ashley. You must be very tired. I hope everything went well with the baby.”

“Absolutely. He was easy, as always.”

Ashley bent down to rub her ankle, knowing he could easily see down her blouse.

“How was your night, Mr. Brenner?”

There was a noticeable silence that prompted Ashely to look up. That’s when she saw him staring at her half-bare tits being held by a red lacy bra. Maybe he was starting to think of her as more than a babysitter, after all.

“My night? It was fine, but frankly, I’m just glad to be home after a long day.”

She was glad, too–and started feeling confident that she was on the right track.

“Did you get a lot of homework done?”

She saw an opening. In one of the videos, the babysitter turned the topic of discussion to sex to help create the right mood. Ashley would do the same.

“Not really. I just wasn’t up to it tonight.”

“Why not? Are you OK?”

“Something’s been bothering me a little, but I’m not sure if I should talk about it.”

Ashley knew Mr. Brenner couldn’t ignore that opening. He had a sensitive side and was sure to find out if she needed someone to talk or not.

“We’ve known each other for years. You can talk to me about anything, Ash.”

She loved it when he called her Ash. It somehow made her feel closer to him.

“This is different, Mr. Brenner. It’s…well…it’s about sex.”

Mr. Brenner paused for just a moment. He wasn’t expecting that response.

“I don’t want to interfere in something that’s maybe best left to your parents, but we can talk if you want.”

“That’s OK. It’s not something I can talk to my parents about, and I don’t know if I can talk to anyone about it. I’m sorry I mentioned it.”

Mr. Brenner sat down on the sofa to be more reassuring.

“But you can talk to me. Please tell me what’s bothering you.”

Ashley looked at him, took a deep breath, and got herself ready to take the next step.”

“I want to have sex. I mean, real sex. I’m a virgin right now, but I decided it’s time for me to have sex with a guy. I just don’t want to do it with a boy who doesn’t know anything about it.”

Mr. Brenner opened his mouth to say something, but just stopped.

“I mean, shouldn’t the first time be special–something to enjoy and remember fondly? I don’t want my first time to be something to just get out of the way. Can you understand that?”

“Yes, that makes perfect sense, Ashley. But are you really ready for sex?”

“This is a little embarrassing, but, I am horny a lot. Sometimes, all I can think about is sex. And I have gone on the pill. So, yes, I am ready.”

Mr. Brenner looked at Ashley. For the first time, he didn’t see her as just a babysitter; she was all grown up–she was a woman.

“I think I’m making you uncomfortable, Mr. Brenner. We should talk about something else. Or maybe I should just leave.”

“No, Ashley. I’m just not sure how much I should tell you. I mean, you’re my babysitter.”

“I know, Mr. Brenner, but I’m 18 now and not a kid anymore.”

Mr. Brenner paused, then said “You’re right, Ashley. And please call me Steve from now on. Like you said–you’re not a kid.”

Ashley smiled at those words, instantly feeling closer to him, now that that he was Steve, and no longer Mr. Brenner.

“What was your first time like, Mr. Brenner…I mean, Steve? Did you enjoy it?”

“No, not really. I had no idea what I was doing. And I really didn’t take care of the girl I was with. I wish I could do it all over.”

“That’s why I want to lose my virginity to someone who knows what he’s’ doing. I want it be memorable for all the right reasons. I want it to be pleasurable. Isn’t that what it’s all about?”

“Yes. Yes, it is, Ashley. Just don’t rush into anything. Make sure he’s the right guy, and please make sure you’re ready.”

“I’m definitely ready, and I’ve made up my mind that I’m going to have sex. The only question is who the guy will be. I’m thinking I should look for a college guy–or maybe someone older. I think an older guy would be good. He’d be more mature and have all that college mentality out of his system. Yeah, that’s what I’d like–someone who’s done with college.”

Ashley looked straight at Steve as she said those last words. His face turned slightly red and his breathing stopped for just a moment. She wanted him more than ever, and she started to think that he wanted her, too.  All she needed was to find a way for them to touch. And thanks to his video collection, she knew exactly what to do.

Ashley hung her head and sighed. “You must think I’m a silly girl, and maybe I am. But this is so hard to sort out, and it’s embarrassing. I should leave.”

Ashley hid her face in her hands and let out a sob. Steve quickly slid closer on the sofa and put his arm around her. Ashley immediately curled up into him and put her hand on his chest. With that, he put his other arm around Ashley and pulled her closer.

“Thank you, Steve. Sometimes a girl just needs to be held.”

The encouragement worked, as Steve instinctively began rubbing her back.

Ashley cooed. “That feels nice. You’ve always known just what to say and do.”

Steve rubbed her back, starting at the shoulder blades and gradually moved his hand lower and lower. Ashley snuggled up closer and began gently caressing his chest. She pressed her head against him and felt his breathing quicken, which she took as a very good sign.

“You don’t look very comfortable, Steve. Wouldn’t you rather lean back a little?”

Steve took her suggestion, but since the arm of the sofa was far enough away, he wound up lying flat on the sofa with Ashley on top of him. He didn’t mind at all–and neither did she.

“Isn’t that better?”

“Yes. Yes it is.”

“I have a question, if you don’t mind. You said your first sexual experience wasn’t very good and that you didn’t take care of the girl you were with. What do you wish you did differently?”

“It’s a little embarrassing to talk about, but it’s a fair question. I should have taken care of her better. Teenage boys sometimes cum too quickly, and I certainly did that day. I wished I made sure she came that night.”

“And that’s my point, Steve. You did nothing wrong. You were both just brand new at it. Wouldn’t it make more sense if one person knew what he or she was doing?”

“That’s a little hard for boys. To be honest, guys like to think they’re in charge and know what they’re doing.”

“Well, maybe I can find a man with some experience for my first time.” Ashley looked at him as she finished that sentence.

Steve squirmed a little at what he just heard. “Be careful, Ash. You want to make sure you’re with someone nice who won’t take advantage of you.”

“That’s easy, Steve. I’ll look for someone like you.”

She wondered for a moment if she went too far. She looked up to see Steve smiling as he looked right at her. Ashley smiled back and caressed him along his belly, letting her elbow “accidently” run up against his now-hard cock.

“I think I’m making you uncomfortable. I’m sorry.”

“Don’t be sorry.”

“I just needed to talk to someone I trust. Maybe I should leave now. ”

“Don’t leave, Ash. Please stay.” There was a near urgency in his voice, making Ashley think she could get away with pushing things a little further.

“But what about this,” she said, moving her hand lower until she was gently rubbing his cock. “Doesn’t this mean I’m causing you some…difficulty?”

“In a way, yes.”  Steve chuckled ever-so-slightly.  “I just can’t help my reaction. I hope you don’t mind.”

“No, I don’t mind at all. I like the idea that you find me appealing. At least I hope you do.”

Ashley looked at his face for some reassurance.

“You’re definitely appealing, Ashley,” Steve said, squirming a little as she continued to rub his cock. “But maybe we’re taking this a little too far.”

“But why is that? We’re both enjoying each other’s company. And, as you said, we can’t help how we react.”

Steve closed his eyes for a moment and enjoyed the feeling of her touch.

“Plus, I was hoping you can explain things to me a little more. In case I don’t find the right man soon, I could use some help on what to do.”

Ashley paused for a moment, then said, “Or maybe you can show me. Will you, Steve?”

Steve’s eyes popped open, and he looked straight at her in disbelief at what he just heard. Of course, he wanted her. But he was older, and she was still his babysitter. Part of him insisted he should ask her to leave, but he simply couldn’t find the will to do that.

“Can I take a look? I’ve never seen a cock up close before.”

It was a lie, but one she knew would appeal to his ego.

“Sure, Ashley. I’d like that.”

She looked up at him and smiled broadly as she undid his belt buckle, unsnapped his jeans, and slowly lowered his zipper.

Ashley was done being coy and put her hands on the waistband of his pants. Steve took the hint and raised his hips off the sofa. allowing her to pull down his jeans and shorts. After one final tug past his hips, Steve’s cock sprung from the confines of his clothing. Ashley assumed it wouldn’t be small, but she was not at all prepared for the size and hardness of what appeared before her. She said nothing as she stared at his beautiful, firm cock–and she smiled, knowing it would soon be inside her.

“Do you mind if I touch it? ” Ashley didn’t bother waiting for an answer, knowing full well that he very much wanted her hands–and more–on his cock.

She reached out and grabbed his hardness with both hands and massaged his cock repeatedly from the base to the head. Her body tingled with anticipation as she wondered how it would fit inside her virgin cunt. Looking up, she saw Steve close his eyes and tilt his head back in pleasure and–she hoped–his own anticipation.

There was no turning back for either of them. She wanted more and leaned forward to give his cock a brief kiss–then another and a third–each time letting her mouth linger all the longer. Remembering what she saw on Steve’s videos, she  caressed the head of his cock with her lips, then opened her mouth, allowing the tip to slide inside. Ashley savored the feel of his rigid penis and the taste–and she felt herself become increasingly wet.

She took him deeper, as far as her young mouth could take him, and began stroking him with her hand. She loved feeling his cock throb and grow harder–loved it so much more than she ever imagined.

Ashley released him from her mouth so she could look at his beautiful, erect penis. Leaning down, she simply kissed his shaft–first once, then again and again–before placing a final, lingering kiss on the head of his cock.

“Steve?”

“Yes, Ashley?”

“Would you like to lick my pussy? No one’s done that before, and I want you to be the first.”

Steve was stunned by those words, and could only muster a soft, “Of course.”

With that, Ashley motioned for Steve to lie down on the sofa so she could straddle his face, just like she’d seen it done in his videos. Slowly, she lowered herself until she could feel his mouth pressing against her cunt. A spark shot up her spine as his lips began massaging her wetness. She had guys–more like boys–touch her and finger her before, but never did she feel anything like this. Steve’s tongue licked at the outside of her slit, then pushed through her opening. As he probed the inside of her pussy, Ashley threw her head back and moaned, louder and louder, praying the moment would never end.

But she wanted something else . The evening was about losing her virginity to Steve, and Ashely needed that to happen now.

She lowered herself from Steve’s mouth and leaned forward to whisper in his ear.

“Please fuck me. Steve. Fuck me now.”

Steve lifted her by the waist and positioned her on the sofa, where she spread her legs beckoning him to take her. Unable to bear the anticipation any longer, Ashley held him by the hips to pull him closer. She watched as he bent over to kiss her gently before locking his lips onto hers with his tongue finding hers. She could taste herself in their deep kiss, which took her to new heights. She was now more than ready for his cock. Though this was her first time, Ashley instinctively knew what to do, as she reached down, found his rock-hard penis, and placed it at the opening of her pussy. She held his hips as Steve slowly, gently pushed his way into her.

Ashley wondered how her virgin pussy could take all of Steve’s cock. She held her breath as he went deeper into her, letting out only the smallest grimace when he broke through. Ashley trembled with pleasure as his cock filled her. It was then that Steve pulled out till his cock was just inside her opening, then slowly thrust it back in. He did this again and again, moving faster and pushing harder each time. Ashley pushed back with her hips to match his rhythm and felt wave after wave of pleasure starting at her pussy and spreading over her entire body.

“Steve, Steve,” she cried out. “I can’t believe how good your cock feels in me. Please, don’t stop!”

The tightness of Ashley’s young pussy and her cries of pleasure drove him to thrust harder and harder into her. With each push, the excitement coursed through every fiber, every inch of her body till she it reached a fever pitch. Her fingers dug into his hips, and she stopped pushing back as her body began to convulse repeatedly. Ashley let out a soft moan, then a louder one, releasing any inhibitions that may have been lingering.

Knowing  that Ashley had already cum, Steve continued his thrusting, feeling that rush of excitement build to the point of no return until his cock exploded with an intensity he had never felt before. Stream after stream of cum erupted inside Ashley, who threw her head back as she let out a soft moan.

Then there was silence. The two stopped and looked at each other, each trying to savor the moment and fully grasp what had just happened. Ashley was no longer a virgin–and she couldn’t have been happier. Steve, in turn, saw the look of contentment on her face and was pleased that her first sexual experience turned out well.

He began to push himself off of her, but Ashley stopped him.

“Please don’t. I want to feel you inside me as long as possible.”

With that, he lowered himself back onto Ashley, kissing her softly and stroking her hair.

“That was wonderful, Steve–and so much better than I ever hoped it would be. Thank you.”

“I should be thanking you, Ashley. Being with you tonight was a true gift.”

“I’m glad you feel that way. But I still have so much to learn.”

Ashley let those words linger in the air before going on.

“I want to learn more. I’m not even sure how to give a proper blowjob–and to swallow. Would you teach me?”

Steve looked at her in silence, unable to fully process what he just heard. He had assumed that fucking Ashley was a one-time opportunity, and he was fine with that. But she was asking to continue their sexual activities, perhaps indefinitely.

“I promise to be good to you, Steve. I’ll do whatever you tell me. I just want you to teach me what I need to know about sex.”

“I’d love nothing more, Ashley. And I’ve got a feeling you’ll be able to show me a thing or two yourself.”

They held each other tightly, each re-living the experience they just shared and looking forward to the encounters yet to come.