Babysitter No More Pt. 02

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Eyl 2, 2023 // By:analsex // No Comment

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Part II: How Did We Get Here Anyway?


A short multi-part story of how a man meets a figure from his past and how it impacts every aspect of his life. Part II gets more adult.


Catching up and a Few Sparks

I easily found the coffee shop Amber had texted me she would meet me at. It was a typical Starbucks, and Amber looked like a typical twenty-something customer. She had on a long-sleeved skin-tight top, that showed off her slender body and cute breasts very nicely.

Of course, the seemingly mandatory yoga pants and a pair of cute pink running shoes completed the College student look. I had to admit her ass and legs in those legging type pants would probably stop traffic. It was hard to believe that she had been rocking it in a strip club less than twelve hours ago.

And with her blondish hair tied back in a loose pony tail, much more the cute coed than hot stripper today. We found a table and I bought the first round of skinny lattes. Amber looked sweet, and her perfume was frankly, almost bewitching. Even without meeting in that strip club, this was a hot woman, not my cute young babysitter anymore.

We talked for almost four hours, but it didn’t seem nearly that long. Amber gave me her story on how she went totally off the rails and then managed to get herself back right again. It was a mix of sadness, craziness, and recovery.

She had in fact started five years ago at ASU here in Tempe, but hadn’t lasted. It turned out she wasn’t really ready to act like an adult. She partied really hard and flunked out after her freshman year.

It was a lot of drinking, but more importantly a habit of all-night Raves with copious amounts of E. When she tried to return home, her father let her back but read her the riot act. Clearly her parents had not expected Amber to turn into a drug loving party girl!

But Amber wasn’t ready to change yet, and after a week and three more Raves and wildness around the house, her dad kicked her out. She told him to fuck off and pawned a bunch of his stuff to get the money to return to Phoenix.

Over the next two years she got herself under control, with a lot of two steps forward and several steps backward. She also made the transition to a full-time dancing career. What else was a girl with no degree and no skills to do, she asked me. The best paying work was in the strip clubs, it wasn’t even a matter for discussion.

She told me she could take on any of five or six personas, depending on the crowd in the club. That focus, and ability to transform herself into personas that customers adored allowed her to clear around 90K a year. She told me she was the top earner most weeks at her club.

To partly explain it, she also recounted how, encouraged by the club owner she went full on blonde and then made sure she was always sporting a dark tan. She had refused a boob job, but as she matured her nice pert 34B at least grew to the beautiful 34Cs I had seen last night. Amber laughed, she called that tanned blonde look the Phoenix stripper standard.

But her ability to almost shape-shift she said was what set her apart. Of course, her tight hot body didn’t hurt her. In fact, she told me, that depending on the time of the month, she actually found her C cup bras a bit tight.

But still she was never going to be that stereotypical stripper with big fake DDs with big hair and standing well over six feet in her stripper heels. Amber told me she had to establish another approach to make sure she made the money she needed.

She was of course still thin as I remembered, but after five years it wasn’t a teenage thinness, but something Amber called ‘dancer-thin’. She also said she worked out during her days. That gave her that hard, hot body, but also helped to keep that deep golden tan.

Last year she had felt she was finally in control again. She applied and had been readmitted to the University, in a probationary status. She was moving slowly, this was all on her dime now, but was up to two or three courses a term. Amber was very proud that in two semesters she had only As this time.

I of course had to give her my story. I had to tell her how my marriage had exploded and that I was now a single guy again. We talked and I showed pictures of the twins she had babysat for from the time they were only six months old.

She was amazed they both were in Kindergarten. She was sympathetic, but smartly didn’t pick hard at the scabs that were still healing from my failed marriage. For the first time though I was talking about it without feeling this big void inside.

It was amazing that we didn’t even know the afternoon was gone and were sitting almost on top of each other, very much inside each other’s personal space, but not feeling awkward at all. I had the feeling that we weren’t done when we finally Tekirdağ Escort got done with our coffee.

I also didn’t push hard about her parents; they were more in Janet’s circle than mine. Amber said she had not heard from them in the last four years. She laughed and said pawning a bunch of her mom’s jewelry and her dad’s electronics probably hadn’t made them too happy.

As the sun was setting, we agreed to meet for dinner in a nice place in Scottsdale, my treat, Amber didn’t have to work tonight for once. I wasn’t sure where this was going, but Amber was funny, and smart, and of course totally hot.

I got cleaned up and dressed for a smart-casual dinner look. Phoenix was clearly a lot more casual than Chicago. And even nicer, in the winter you didn’t have to dress up like an Eskimo, or worry about freezing to death in the walk to your car in a parking lot.

The restaurant, a kind of Asian Fusion place that Yelp liked, was actually in a big fancy mall. I guess in the summer that made it easier here. I agreed to meet Amber there, I wanted to not be too pushy. After the afternoon I was pretty sure she would show up, and figured I’d get an idea where we were at when I saw how she looked and acted at dinner.

I saw her as I came down the hall from the parking structure. She was looking down towards an escalator, as she faced the restaurant. Wow, she cleaned up nicely. She wasn’t dressed like a student, and not like a stripper, this was more simply a super-hot twenty-something woman.

She went with a look that was sexy and fashionable at the same time. It was a simple but effective combo, with a skin-tight spandex looking red minidress grabbing your attention. If she’d had an ounce of fat it would have shown, but of course there was none of that to show.

The dress stopped about six inches down from her hips. Her curves looked amazing in that skin-tight dress. But the nicest part was the effect of her thigh high suede boots. Not sure if it was the suede or the four-inch heels, but Amber was simply riveting, at least to me.

Tasteful makeup to go with her long free-flowing blonde hair completed the look. The entire look of course screamed hotness to me. Amber had made quite an effort to look hot, I was already thinking that was a really good sign!

Dinner was as much fun as the afternoon in the coffee shop. We talked non-stop, but that wasn’t the best part. By the end of the dinner and all through our dessert and coffee Amber had been very touchy. Her body language was very open and she didn’t go more than a minute or two without contact with me.

She had been reaching out and was holding one of my hands or forearms nearly the whole time. Her hand was soft and elegant, all the way to her dagger like nails that matched the red of her dress.

As I paid and we were walking out, Amber told me she wanted to show me her new townhouse. I thought that would be interesting. I was so naïve. Later Amber admitted she had one goal in mind, and showing off her furniture and decorating style was not it.

Taking things Further

We got inside, a nice little townhouse type condo, that Amber was very proud to say she had bought about a year ago. She wasn’t kidding about doing well as a dancer. Then again looking at her in the red dress and stylish heels, she would have made a dead man get hard at his wake.

We took a quick tour of the downstairs, and Amber poured us another glass of some wine that had been open in the fridge. I was going with the flow, just not sure if my hopes of something more intimate were foolish and forlorn. But the signs at dinner and now more wine was getting not just my hopes up.

She then pulled me close, gave me a quick, intense kiss. We sat together on her couch and she made sure she was very, very close to me. God, she smelled good. Amber continued to be the aggressor, her tongue deep in my mouth, when she wasn’t kissing my neck and giving me little bites too.

I mean I was nearly thirty and she was probably seven years younger, but I hadn’t felt this in sync with someone ever, not even with the cheating slut I had married. Amber was pretty touchy, to go with the super-sexy kissing.

But she suddenly broke it all off and stood up. I was taken aback, had I done something? I got ready to make my goodbyes, figuring maybe I was just foolishly hopeful. But Amber stopped me.

She told me to get comfortable till she called me. Maybe we were going a relatively traditional path. After all we were clearly really into each other. I was hoping she was going upstairs and was going to call me up after she put on some slinky negligee.

But to my surprise, Amber said she was going to prove that she was every bit the chameleon I had laughingly called her after she described how she changed her act to match the club’s clientele every evening. She told Tekirdağ Escort Bayan me that I got to decide if it was both different and as sexy as she had claimed, but she said, she was sure she was going to convince me.

She giggled as she disappeared up the stairs moving like a young gazelle. I looked around, checking out her books and flat-screen TV. Late night TV was boring as always, and I was distracted by the music and sounds coming down the stairs. This was really pretty curious.

After at least 30 minutes, I heard Amber call me to come upstairs. Like all women, she took her time to get her look right I guessed. I filled up my glass, she had taken hers with her, and climbed up to the second floor, with the rest of the bottle of white wine.

There was light spilling down the hall and jazzy music coming from the back of the unit, so I headed there. Somehow, I was sure I would like what she had changed into, I just had no idea what that would be.

However, even with all that had occurred since last night, I don’t think I could have been more shocked. There on small padded stool, in front of some satin drapes, was Amber, it had to be, but what a radical change. Maybe I should just call this creature Jezebel.

It was her but there was a totally different, very sexy and dangerous effect. This creature was sexy and dangerous, literally the total opposite of the cute girl from Starbucks or the fashionable woman from dinner

She no longer sported the loose, casual blonde hair. This look started with gelled hair that was braided tightly against her scalp. That did showcase Amber’s dramatic and elaborate makeup. She had gone with much stronger makeup, surrounding her eyes with very dark pencil and eyeshadow.

To match the war paint, she had added really long lashes above very bold cheekbones. Not a big surprise she had bright red lips that of course matched her blood red talons. This girl was hot. But that was only a small portion of the look, her hair and face were nothing compared to her clothing.

She had drawn attention to her body with a wild corset type of latex item, that nearly showed her nipples and simultaneously totally pushed up her cute tits, making them look huge. Below the display of her chest the corset narrowed dramatically, showing off Amber’s very sexy midsection.

The corset ended at her hips, and I saw no sign of any panties. But in an amazing final piece I took in Amber’s legs. She had finished off her outfit with some stripper platform boots. They looked to be at least seven inches tall and were in shiny black latex to go with the black and red corset.

Most disquieting of all was the still leather collar covering most of her neck. On the black leather was the word ‘mistress’ in bright silver embossing. All this girl needed was a whip to encourage a customer to worship at her feet.

She really had been right, if I hadn’t eaten dinner with her and come back to her condo there is no possible way, I would have thought this sexual animal was Amber the girl I knew from Chicago. She somehow now also had a bright full sleeve tattoo all down her left arm, where had that come from and how come I hadn’t seen it earlier?

At first thought it was from her lost years, when she turned into a party animal. Amber saw my look of amazement and laughed at my shocked looking expression.

“Baby, it’s not permanent, I use this temp tattoo to bring the whole together. Even I wasn’t willing to go that far.”

Relieved I looked her up and down,

“Ok Jezebel, you win, but I have to ask, this outfit, this persona, is totally hot…and if I didn’t know for sure this was you, I would never ever guess. Did all this effort pay off at work? And what do I owe you for my lack of faith?”

Amber, pulled herself upright and got right in my face, smiling ear to ear. I immediately noticed her perfume was different, heavy and musky. My heart seemed to beat even faster. I was drawn to the everyday Amber, but this Amber was making me a little crazy.

She was now eye to eye with me, seven-inch boots helped with that. Amber pulled back to look me in the eye, after kissing me fiercely for a minute, and pouted at me,

“I’ve decided you owe me a whole night of doing everything I want you to do. I have wanted you since I was eighteen and you were twenty-five, and now I am getting what I wanted.

She boldly rubbed my painfully hard erection through my slacks,

“Nothing is off the table, and I so badly want to have you more ways than you can imagine.”

She paused again and then added,

“and as to your first question, I never made less than a grand, and sometimes nearly two when I took the time to go all Jezebel on the customers, so yes, it was a really good return on investment. But look baby, I’m all about consent, let me know if you want to go still!”

I Escort Tekirdağ cracked up at her second answer and thought about the first statement for about a Nano-second. We were both single, both adults, and both connecting on so many levels,

“Amber honey, just don’t kill me. And with that outfit my death looks distinctly possible.”

The rest of the night was beyond my wildest imaginings. It wasn’t’ just that the sex was rawer and the orgasms stronger than I had ever had with Janet. We simply seemed, over and over, to be more emotionally and personally engaged with each other than I had ever been with anyone.

Amber’s racy outfit, except for the boots was ditched after she sucked me dry the first time, licked me back erect and then pulled me on top of her. That led to at least five minutes of kissing and vigorous fucking before I exploded deep inside her super-tight, wet, bald pussy.

But the feeling after we got our energy back, draining that bottle of wine, as she licked me from my balls to my tip, was beyond words. Of course, that was only one of her techniques. Amber was able to suck on my head like it was a lollipop, and then sink down to engulf all of me inside her mouth and throat, all the while licking my shaft with her tongue. She was an oral diva.

Of course, the first time, to finish it all with aplomb, Amber ignored my moaning and groaning that I was about to cum, she just looked up and batted her eyelashes and sucked even harder. Then as I exploded in her mouth, she swallowed every drop of my orgasm, licking her lips at the end.

Once again, when I regained the ability to think, I thought that this was not who I thought our babysitter would ever have become. But this woman was totally hot, seemingly insatiable, and I realized I was falling for her on the first night we were together.

After I had cum the third time, we needed another break. We cuddled and relaxed for a while, talking on silly topics while Amber lay across me, head on my shoulder. For a first time together, having only found each other a day before, we were as comfortable naked in bed together as if we had been together the whole last five years.

But I wasn’t ready to just receive that night. In just a few minutes I roused myself and attacked her awesome breasts, leaving them wet and with very hard nipples. Then I worked my way south, playing with her bellybutton piercing before moving further down. I wanted to return her oral efforts for Amber. I figured it was the least I could do, and would give me a chance to recover.

She asked if I wanted to do this, after I had cum inside her. I looked up, smiled and continued to her beautiful bald lips. I tried every trick I knew, licking and sucking and adding in a vigorous finger fucking. Amber noisily came as I sucked on her clit while I also did the come to me motion on her G-spot. She clearly was ok with my technique; my face was soaked.

After we cooled down for a while, finishing off a second bottle of wine, I thought we might be done for the night. We had been saying silly things to each other, and I had been playing with her nipples, she was laughing at me, totally comfortable sprawled together hours into our sex marathon.

But her nipples were getting really erect, and her chest had started to redden again, a sure sign she was starting to get aroused again. This girl was not kidding about having fun all night long. I wasn’t sure what was next, but I wanted to make her cum one last time.

Suddenly Amber roused herself and got aggressive again. First, she began to stroke me, and she got the reaction she wanted almost immediately. After I was hard, she kissed me hard for a minute or so, then pulled away and moved herself away.

She had finally decided to be somewhat traditional. She mounted me and started to bounce up and down in a very rapid fashion, reaching down to stroke herself on a regular basis. I was just enjoying the sensations and staring up at an amazingly hot chick ride me.

Amber was not a silent partner, she was moaning and making small mewing sounds. Every so often she would open her eyes and look down at me,

“Jim baby, I’ve dreamed of your dick inside me for so long. Baby don’t ever stop fucking me.”

I was all about keeping Amber happy, and with my three prior orgasms over the last two hours, was able to fuck her for nearly fifteen minutes. At the end I heard myself make a series of odd sounds and arched up, cumming with all I had left into her tight, wet passage.

We collapsed together and slipped off to a lazy, sleepy embrace. I had so not expected this when I agreed to attend the conference in Phoenix to escape the cold Chicago winter.

On Friday morning I knew I wasn’t going to get any rounds of golf in, and also knew that was a pretty sweet situation. I had to let Amber go to her two classes but she was done by one PM.

I agreed to pick her up at the townhouse for an afternoon together, then some dinner. I went back to my hotel to catch up on work so my boss didn’t think I was a total slug. I had no idea what lay ahead, I just was sure I wasn’t going to let Amber slip away.

…next: the conclusion

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