I had been dating Sherry for a while and knew her to be a gorgeous, fun, and very sexual woman. She had long red hair, deep green eyes, and a petite, gymnast type body with proportional breasts to fit her size and a sweet little bottom. I knew she had a very colorful past as far as men and sex was concerned and had gotten bits and pieces of her story over time and a lot of it when she was drinking.

So one night we were gonna be at my place chilling and watching movies. I decided to try real hard to get her secrets out and thought up a plan. I have a rather wild and crazy sexual past myself, having spent a lot of time in many Pacific Rim countries while in the Marines. I was single and women were hot, cheap and up for anything, and to say I indulged was a huge understatement!

The plan was simple, get her drinking and play a game where we tell our tell things about ourselves. Of course, we all know where I was heading on this one, but it sounded like a good plan. I bought Sherry’s favorite Tequila and my Whiskey and some beer, and we were set. She came over and the night began. After we were both loosened up, we got to telling stories and the longer we went, the more we drank, the wilder the stories got. I knew I had some really crazy stories from my own past and was winning pretty handily, as her stories were fairly tame in comparison.

I was starting to think it wasn’t gonna work and needed a change of tactics. We were really lit by this time and I told her to tell me something that she would never want anyone else to know, especially me. I reminded her how much I had revealed and that I knew she had some really crazy stories. Well, she finally told me her deepest, darkest secret and it was even wilder than I could’ve imagined!

Apparently some years earlier toward the end of her senior year in high school, she had started stripping for private parties. Pretty much high-end stuff and specialized in Asian businessmen. Apparently real redheads were highly prized by Asian men and with her petite body and long red hair, she fit the bill perfectly. Taking one more big swig of tequila, she told me the story.

She said she was approached by what she later found out was a recruiter at a store in the big mall about 30 miles away in the city who asked her if she liked to dance. She was puzzled by the question but assured him she did indeed like to dance, but why was he asking? He was good-looking and maybe 30ish? He had such a disarming personality that she felt comfortable with him right away. Upon further reflection, she realized that she was looking at some pretty risque thong bikinis and that’s probably what drew him to her, that and her obvious good looks.

The man asked her if she was eighteen and she said that she had just turned the month before. The man then turned and picked up the bikini she was looking at and told her he would like to see it on her. She was nervous as it was a very revealing bikini with small triangles just barely covering her goodies with basically string in between and up her ass crack. She didn’t know what came over her but she agreed and went into a dressing room to change. She began wondering what the hell she was doing, showing off her almost nude body to a strange man and simply because he asked!

She gathered her courage and stepped out of the dressing room, relieved to see no one else around. The man smiled as he observed her firm, B-C cup breasts, flat stomach, and well-toned arms and legs. He told her to turn around and was greeted with her small firm ass, which also pleased him greatly. He then asked her if she was a natural redhead. The question caught her off guard and she wasn’t sure how to respond. Sure, guys had joked with her about whether or not she was a “real” redhead but the way he asked was a bit more than joking or idle curiosity. She responded warily that yes she was.

The next thing he said floored her, he told her to prove it! There she was, a barely eighteen-year-old high school girl from a small town in the Midwest, and a strange man had convinced her to show more of her body than most guys would ever see and now he wanted proof that she was a real redhead? To this day she said she had no idea what came over her, but she pulled down the front of her thong and showed him about an inch of her blazing red pubic hair! Thank goodness she had just had it groomed she thought to herself.

The man smiled and told her to get dressed because he had a business proposition for her. As she got changed she wondered just what this proposition could be. When she got out of the dressing room he was at the counter with two bags. He handed her one of the bags and she saw that it was the bikini she had just worn. He asked her if she had a job, she said that she didn’t as she couldn’t find a decent one that would fit in her schedule. Then he asked if she was interested in making $1,500 to $3,000 in only two days and only a couple of hours each day.

Sherry was dumbfounded and couldn’t comprehend what he was talking about, but an idea dawned on her. She told him she wasn’t gonna be a porn star if that’s what he was talking about! She also said she wasn’t going to be a prostitute either! He chuckled a little as he told her he wasn’t surprised that she guessed those two jobs, but that wasn’t what he was talking about. He asked if he could buy her lunch and they could talk about it. She readily agreed as she was hungry anyway and a free meal is a free meal, so what the hell.

The man introduced himself as Tony and they went to get some food. While they were eating, Tony explained what the job would entail. Basically, he worked for a company that supplied dancers for private parties. “Like strippers you mean” she asked. He said yes but in her case, it would be for a certain clientele, namely Asian businessmen. They were apparently infatuated with redheads and they were highly prized. They also command top dollar for their services. Well, at least now she understood why he wanted to be sure she was a real redhead, also why he wanted to see her in a bikini.

He went on to tell her that she was one of the best-looking redheads he had ever met and if she wanted, she could really make some serious cash. She was obviously flattered and wanted to know more, even though she doubted she would actually do it. He explained that she would be hired for small private parties mainly in hotel rooms for eight to ten guys. He also mentioned that he was glad she had pubic hair as they loved to see that also, which made her blush just a little.

Tony explained that if all she did was go and dance she would make five hundred dollars an hour plus tips. And these wealthy men were good tippers he added. He told her she would be booked out of a large city in a neighboring state, requiring her to stay for two nights. She would typically book one party for Friday and one for Saturday evenings and then she could travel home on Sunday. She liked the idea of doing something like this out of her state so she would not run into anyone she knew.

She then realized that something wasn’t right, even if they were good tippers and admittedly she had no idea what kind of tips a stripper made, it still probably wouldn’t reach the $3,000 mark. So she asked him about it. He asked if she had ever given a blowjob. She was only a little surprised by the question as she was a smart girl and knew there was a catch, and this was it. She said that she had, not telling him that she had actually been giving them for years and liked doing it. Tony said that if she would give blowjobs to the men after she danced, she would make a lot more money.

He told her a couple of reasons why it wasn’t as bad as it sounded. 1: Asian men typically had smaller penises so it wouldn’t be difficult to perform oral sex on. 2: They would be highly excited and probably cum very quickly, so it wouldn’t require a lot of time or effort. 3: They had a lot of money and the tips would be awesome if she did well. So in her mind, she was thinking, I go and dance naked for a group of eight to ten strange men per night, then blow all the men, meaning she would suck sixteen to twenty men per weekend. It sounded like a lot and was pretty overwhelming for her.

After lunch, Sherry had not committed to the proposition but Tony gave her his card and told him to call if she decided to do it. She said “OK”, thinking that it would never happen and they parted ways. Over the next week, she could not get the idea out of her mind and she had a list of the positives. 1: There was no way anyone would ever know. 2: She wasn’t opposed to the idea of showing off her body to a group of men, she knew she looked good. 3: She was fairly certain she could suck that many dicks at one time although obviously not positive. 4: The money would really be nice and she wouldn’t have to worry about a regular job because even if she only did one weekend a month (which is all she thought she could get away with living with her parents). 5: The idea was growing on her and she found herself getting rather excited about it.

She called Tony about a week later and told him she would like to do one weekend of parties just to see how it went and she would decide afterward if she wanted to continue. He said that sounded fair and she needed to come to his office to take a few photos to show prospective clients. She agreed to come down the next day and was told to wear the bikini he bought her for the pictures. She wouldn’t be posing nude he told her, much to her relief, as they wanted to not let them see her nude without paying. And besides, they would be more than ready to book her from some bikini pictures.

Only a few days after her photos had been taken, Tony called her with two parties lined up for the following weekend. He told her to tell her parents that she got a job hosting for conventions and would require her to stay in the city for the weekend. He also gave her a phone number to give them in case they wanted to check up on the job and that he would cover for her and explain her pretend job to them.

The rest, as they say, is history she said finishing her story. But I had so many questions! First, would they line up for her or would she just go around the room and service each guy where he was? She said it varied and it was probably a 50/50 ratio. Did they use condoms or did you swallow for them? She gave me one of those ‘Are you stupid?’ looks and said no man likes a blowjob with a rubber on! How much money did she make? Right around $3,000 for the weekend, turns out they were good tippers! How long did each party last? 2-3 hours she replied, depending on how much money was coming in and how long they lasted. Which made me ask just how long did they last? Some, less than a minute others five minutes, most were between 5 and 10 minutes.

My mind was completely blown and I had so many more questions, but she said she was getting turned on and told me I needed to take her to the bedroom right away! Who was I to argue? I ended up marrying her and with my approval, she really let her Freak Flag fly! Stay tuned for more, good readers...