The Insurance Salesman Ch. 03

"Breaking in Brittany"

It had been several months since I first met Jessica, and we have had many good dates during that time. We found that we seem to have many things in common while trying to get to know each other. We played around a few times, but not to the full extent that we did on the day we met. I think subconsciously we both didn't want to risk ruining this thing we were starting, so we both seemed to take it a bit slower. We talked about family, friends, old partners, and even some of our craziest sexual acts. This is when I found out that she and her ex have experimented a few times with swinging. Needless to say I was ecstatic about finding out that she actually enjoyed it. I even explained to her that my ex and I also experimented a few times with some mixed reviews.

She explained that they both enjoyed it, and that was one of the reasons her ex didn't want to have children. This is so weird I thought to myself while realizing we had yet another thing in common. Could this be the perfect woman for me? I pondered while staring at her beautiful face. I almost fell off of my chair when she told me she was a twin, and that she should have been the one to get with her ex. Jennifer, her identical twin sisters' name, was into many of the same things as Jessica. However Jennifer did not want children, which is why Jessica thought that she should have been the one to hook up with her ex husband. Twin sister? Likes many of the same things? Does she fuck like Jessica? Do they both enjoy swinging? How can I get to have both of these women at the same time? All of these things went racing through my head, and I think she sort of knew what I was thinking.

"Are you okay Jack?" She teasingly asked me snapping me back to reality.

"Um..Yeah I am okay, I Uh was just thinking of....." blushing a bit as I started to answer her question.

"I know what you were thinking, and get it out of your head. There is no way you are going to fuck my sister." She said smiling sexily at me while she spoke. "Not just yet, anyway."

"Oh my god, how could you know what I was thinking. What makes you think I want to fuck your sister?" Continuing to blush and smiling greedily at her.

"Are you kidding me? You are a MAN, right? Christ I fucked you on the first day we met, and I know you are thinking if I fucked you on the first day, what would my sister do?"

We were both smiling a bit excitedly at each other at that moment we started getting closer to each other. I pulled her into my lap and began to kiss her passionately. We made out like a couple of school kids for nearly an hour when her doorbell rang. It was her parents dropping off her son Justin after spending the day with them. The three of us had some dinner and watched a movie. It was getting late and I told her that I had to get up early to pick up a new trainee I was charged with teaching this business to.

"Don't worry Jackie; we will talk more about my sister very soon. She and I have shared many things and I have already told her about you. She is very excited to meet you." Jessica said whispering in my ear as she walked me to my car. "I just want to make sure you and I have a future before I let you play with Jennifer, if that is okay with you?"

"We can take it as slow or as fast as you like. I really like you Jessica, and I think you like me. So whatever I can do to make you happy and keep this thing between us going for a long time I will do."

The next day I got up a bit earlier than normal and got myself ready for work. I had this new trainee starting today, but unlike most new trainees' I knew this one very well. Brittany is the 22 year old daughter of the best friend of one of my sisters. I have known this girl all of her life as her mom and my sister have been best friends since high school. I remember actually having a crush on her mom when I was a young teenager. How ironic that had I been a bit braver back then perhaps this would have been my daughter I was getting ready to train in this business. Of course very few 15yo boys are lucky enough to fuck a 19yo hottie, but hey kids can dream can't they.

I had offered Brittany this job a few weeks back because she was struggling to make money at the department store sales counter. She had the personality for the business, but perhaps just lacked some confidence in herself to be more successful. I offered to take her under my wing and show her how to be more confident with herself. This would give her a solid foundation for a future she could be proud of. I arrived at Brittany's door just after 8 am to pick her up, as I told her I would drive for a while so she could save money. As she opened the door to let me in I think she thought I was over dressed, however she soon realized that she was underdressed.

"Wow, you look way different. I have only ever seen you in jeans or shorts and stuff. I hadn't realized you had to dress up so nice for this job." She seemed a bit depressed or saddened that she wasn't dressed nicely enough for her new job.

"Hey Chic, you have to look the part. If you want to make money you should dress like you already have it." I put my hand on her shoulder to try and comfort her and cheer her up a bit. "Just go put something else on and we can get on our way, I will just wait here for you to change."

"That's just it. I don't think I have anything that nice to change into. You didn't tell me I had to dress that nicely for this job. Forget it, I cannot do this. I don't have the clothes or the money to get new ones, thanks for the chance though, Uncle Jackie." Getting more saddened and depressed as she spoke to me.

Even though I wasn't really her uncle, she called me that all the time. I mean I am pretty close with my sister and we have known each other her entire life. We treated each other as if we were family.

"Don't worry Britt, I am not going to let you quit before you get started. This is partially my fault because I thought you dressed this way for your old job. I will take you shopping for a few new suits and outfits today, and then we can get you started making some money."

"I can't let you do that! That is not fair to you, besides that will probably cost a small fortune."

"Don't even think of it, I have made plenty of money in this business and don't plan on stopping now. Besides I wasn't taking you shopping as a gift, silly. You are gonna have to pay me back at some point." I exclaimed sarcastically back to her while smiling.

"REALLY? You don't mind taking me shopping? I will absolutely pay you back; I will do anything you want. I am just glad you gave me this opportunity to start a new lucrative career. Thank you so much Uncle Jackie, you're the best." Brittany lunged at me giving me a big hug.

Brittany and I were headed to the mall to get some new clothes for her career when my phone rang. It was Jessica calling to ask me if I wanted to go to this benefit she forgot about for a few of her clients. How could I refuse any chance to see my new girlfriend wear something sexy and hopefully very revealing?

"Absolutely, I would love to go with you. Just let me know when I need to pick you up." I excitedly responded to her query.

"How is your training going? Are they learning anything yet?" Jessica asked curiously.

"Yeah, she is doing fine. I haven't actually taught anything just yet, I have to take her shopping for some new clothes. I think we are going to Macy's or something." I said kind of un-emphatically.

"HER? You didn't say you were training a girl. I hope you don't try to get her to do the same things you got me to do on our first meeting, DEAR." Jessica said with a somewhat sarcastic tone in her voice.

"You're not jealous already are you?" Chuckling a bit as I fired back at her sarcasm.

"Why are you laughing at me? I can be a little jealous if I want to be, that big cock of yours is all mine right now. So if I don't want to share it then I don't have to."

"I am laughing at you silly girl, because my new female trainee is my niece. Well not actually my niece, but I have known her since she was born. Her mother and my sister have been best friends since high school."

"OH MY GOD, I am SO embarrassed right now. Let me call you tonight after I come to my senses."

I could hear from her tone that she was indeed embarrassed at what she was thinking. Never the less I was happy to hear that she cared that much for me. We said our goodbyes and hung up on each other. I just continued to chuckle a bit under my breath at what just happened.

"Who was that?" Brittany stated inquisitively.

"That was my new girlfriend, Jessica. I guess she thought I was going to try and seduce my new trainee the way I kind of seduced her when we first met."

"Really? You have to tell me about that. How did you seduce her? Where did you meet? Come on Uncle Jackie you have to tell me."

"I am NOT going to talk to you about my sex life young lady. Those are details that you don't need to know." I somewhat scolded her.

"I am not a little girl anymore, Jack! Besides I am not really your niece so if we talk about sex with each other then it is just that, talk. Also like you said she is your new girlfriend and we wouldn't want to mess that up, right?" Brittany barked back with a wicked little sneer on her pretty young face.

I sat silent for a short time while pondering what she was saying, and taking into consideration that she is only a couple years younger than Jessica. I have always thought Brittany was a very beautiful young woman, but until now I have never thought of anything past that point. There I was now thinking of this gorgeous young lady sitting next to me in the car in a different light. Brittany is about 5'5" tall, with a very slender and lean body. Very nice bubble butt that sticks out just enough help accentuate her curves. Her breasts are fabulous, sitting up high and a very full C cup. Finally pulling into the mall parking lot I parked the car and just stared at Brittany for a few minutes.

"I tell you what, let's see how you do today and maybe I will tell you a little something of what we did together. How does that sound?" I continued to stare at her pretty face.

"That's a deal. I want to hear all about it so I am going to work extra hard just to hear some of these stories." She stated with a huge grin and wide eyes returning my gaze.

Brittany and I were now shopping for new suits and such for her to get her looking like she needed to. We grabbed many things and mix matched items to build up a bit of a wardrobe for her. She tried all of them on and we decided on many of them. I then took her over to the shoe department to get several pairs of shoes. She got five or six pairs that ranged from the rather plan three inch pumps to a very high strappy stiletto. The next area I started to really want to take her is the lingerie and pantyhose department. I picked out a bunch of really high end sexy and sheer pantyhose.

"Uncle Jackie, I had no idea you had such great taste in clothing. Your sense of style is magnificent, even your choice for nylons. Where did you get such a sense of fashion? And where on earth did you learn how to pick out pantyhose? Now that is the real question?" Brittany was smiling and staring at me while speaking.

"Ahh... you will have to be really good today for me to answer that last question." I said grinning from ear to ear. "As far as the other stuff, well I have to wear nice things for this job. And you just end up learning what things work and what things don't work. Besides you know I have three older sisters, right?"

I think Brittany thought she was on an episode of "what not to wear" when we went to check out and pay for all this stuff we just picked up for her. The bill was a bit over $800 for her new wardrobe, but she really did need these new clothes to help her make money. That didn't make me think twice before paying the cashier and grabbing bags to head out.

"I cannot believe you just spent that much money on me unc. You really didn't have to spend that much, I mean that is really a whole lot of money to spend. I just hope I can really make money to pay you back for this." Brittany now had this demeanor about her as we walked out to my car that was sort of submissive.

"Look kiddo; let's take all this stuff back to your house. You can change into one of you new suits and I can go show you how to make some money." I said playfully while holding the door open at the car.

"Absolutely, I know I am gonna have to work hard to pay of this new debt. I am just glad it's you and not someone else." Smiling and giggling as she spoke back to me.

On the ride back Brittany started to ask me again about how I seduced Jessica, my new girlfriend. She kept prying to try and get me to talk, and finally I started to give in when she shocked the hell out of me.

"So Jackie, what did Jessica do when she found out you have a huge cock?" Brittany snickered and gave me a very sexy grin.

"HOW ON EARTH DO YOU KNOW WHAT SIZE COCK I HAVE?" I said completely shocked as the car swerved into the next lane.

"Please! All of those cookouts, swimming at your house, parties at the beach over the years. I noticed many times that you had a huge bulge in you swim shorts. And to be honest with you I have always secretly hoped I could see it someday, but because of you being like an uncle it was always sort of weird." She explained with a wanting look on her face.

I was absolutely speechless for the next several minutes it took to get back to her house with her new clothes. We both carried her bags of lute into her house and into her bedroom.

"Go ahead and get changed so we can actually get to work sometime today. I will be waiting in the living room till you get done." I said quickly in the hopes we could just get the rest of the day finally started.

As I went back into the living room and sat down, I could not get what she said out of my head. I tried to read a magazine she had on the table, as well as try to think about work to get this off my mind. I couldn't believe how aroused I was and my cock was starting to wake up inside my pantyhose. After a few minutes Brittany came into the room wearing one of her new outfits and carrying another on the hanger.

"Which one do you think I should wear first? This one I am wearing or this one on the hanger?" She asked as she kind of gave me a quick once over with her eyes.

"I think that one you are holding looks good, and it is a bit warm today and you don't want to be overheated." I retorted quickly with as little visible emotion as possible.

A few minutes later she returned to the living room wearing the other outfit. A medium blue pleated skirt that fell a few inches above her knees. I nice silk camisole top that was lined enough to not show her bra, and a short three button jacket style low cut shirt with long sleeves. This entire outfit really accentuated her figure and she looked like a million bucks. I could tell she was carrying something in one hand, but couldn't make out what it was.

Sitting down beside me Brittany asked. "What pair of pantyhose should I wear? The nude or tan color or the black sheer style? I am thinking the black ones should go well with the blue skirt. What do you think?"

"I think the tan ones will look best myself, but make sure you wear the simple black pumps with them. That should bring everything together." I said pointing at the package of pantyhose she was holding.

She began to open the package right there and proceed to put on her pantyhose. I wasn't sure what to do or say, so I said nothing and just watched. She had one leg up to her right knee and then brought the other up to her left knee. Brittany stood up and began to work her new pantyhose up her firm toned thighs pulling her skirt up a bit as she did. She continued to pull her new pantyhose up her thighs raising her skirt further and further up her legs. She then did something completely unexpected, but quite enjoyable.

Brittany leaned her head down and stopped pulling on her pantyhose. She grabbed the sides of her skirt and pulled it all the way up her waist turning it inside out. She put the hem of her skirt in between her teeth to hold it and returned to pulling on her pantyhose. I was pleasantly stunned when I immediately noticed she wasn't wearing panties, which started to put a twinge in my cock. She finally pulled her pantyhose all the way up and fussed with the seams to get them just right at her crotch. I could do nothing but stare at her luxurious pussy displayed a mere foot from my face. She let her skirt fall from her teeth and then plopped back down on the couch next to me.

Turning to look at my blushing and shocked face, she spoke. "Well the least I could do is giving you a little show for buying me all of these wonderful new clothes. If you are not that bothered by seeing me this way, I could get dressed in front of you every day as partial payment for all these clothes.

I mean if you are comfortable enough with seeing me this way that is." She continued after a slight pause while I remained stunned.

Dumbfounded and almost in a trance I just sat there and stared at her. She put her hand on my knee kind of just petting my thigh a bit as she attempted to calm me down. At the same time with her other hand she was stroking her thigh admiring the sheerness of her pantyhose she was wearing.

"Uncle Jackie? I wonder if my pantyhose feel as sexy and soft as your pantyhose do. Here tell me what you think." Then she pulled my hand from my lap and placing it on her thigh just above her knee.

Realizing she noticed my pantyhose covered ankles and shins, I figured at that point it didn't make sense to act like I didn't wear them. I just went with it and started to pull up my pant leg when I asked her.

"Don't know? Why don't you tell me what you think?" I grabbed her hand and placed it on my lower leg covered in my black sheer elegance Legg's pantyhose.

"Wow, they are really nice, but I think mine are softer and probably sexier than yours." She giggled while still stroking my leg.

"So is this how you seduced Jessica? Or did you just whip out that big cock in front of her? Can I see it? PLEASEEE!!! Uncle Jackie. Let me see your cock just once." She begged me while bouncing up and down on her butt just like a little girl would do when asking for something sweet.

"I don't know if that is such a good idea. I mean if I let you see it, next you will want to touch it. Then you will want to suck it, and then I will want to fuck the hell out of you. I now have a girlfriend and you are kind of like family and that is weird."

"You know I am not actual family, and I understand about it seeming that way. I also understand about the new girlfriend thing, you really don't want to mess that up. However I really have to know why you are wearing pantyhose, and how long have you been doing so. Does Jessica know? What does she think?"

I decided to explain to Brittany what happened the day I met Jessica. How she noticed my pantyhose leg similar to the way she had. How she teased me the same way she is teasing me today, but how I made sure she went through with her intentions. I then explained that we both have many things in common, like the fact that we both have tried swinging on several occasions. I also mentioned to her that I wasn't sure whether or not she was bisexual or even bi-curious, but how that would make things truly wonderful. I could share my sexy new girlfriend with someone.

"Uncle Jackie, did you know that I am bisexual? If you let me see your huge cock, I could find out for you if she is or isn't. Who knows, if she is then the three of us can play together. How does that sound?" She said with a seductive smile on her face.

Pondering her offer for a minute or so and that is when the wrong head won the decision making battle. "Okay, here is the deal. If I pull out my big dick to show you, then I get to use it anyway or anywhere I want. Also I will be taking you up on your previous offer of watching you dress every morning when I come pick you up. If after you find out if Jessica is interested in playing together then we tell her about today. If she gets upset then we have to stop if she wants me too. If that isn't okay with you then we forget about the last couple hours." I stated with a determined tone in my voice.