Uncle Jim & Jenny's Secret Ch. 01

Over dinner, he explained that he had an important business dinner in a couple of days and it helped if he had an attractive woman as a companion. I had a puzzled look on my face because I didn't know why he was telling me this until he explained it further.

"I was wondering if you'd like to accompany me to the dinner."

"Why me?"

"You may not realize it, Jenny, but you are a very attractive young lady. I saw your prom pictures and when you get all dressed up, you look older, and to be honest, you're sexy."

"Gee, I don't know, Uncle Jim. You must know other women that are more beautiful than me."

"Trust me, Jenny. You'll do fine."

"I might have to work that night."

"If you agree to do this for me, I'll buy you a new outfit, pay for your makeup and hair to be done, and give you five hundred dollars."

"What? Why would you do that?"

"To be honest, when I'm cutting a business deal, having a young, attractive woman there helps distract my client and they seem to be more agreeable. It breaks the tension of making a deal. Trust me, it works. I'll take you shopping tomorrow and set up an appointment at a salon for the afternoon of the dinner."

I wasn't sure about this but what college student would turn down that offer? I was still skeptical.

"That's all I have to do is go to dinner with you?"

"You have to kind of pretend that we are dating. That's all."

"I'm not having sex with anyone."

Uncle Jim chuckled, "I know I have a bad reputation but I'm not going to expect that from my niece."

I was relieved but I needed to know for sure what I was getting myself into so I agreed to help him out. I could always use some new clothes and cash. I was still a bit skeptical of my uncle's motives but I liked getting all dressed up and eating in fancy restaurants.

The next day, Uncle Jim took me shopping in some very exclusive dress shops where I tried on several dresses. I think my uncle enjoyed seeing me model various outfits that, quite frankly, were very sexy. It felt a little weird but I agreed to help him out and this was the compensation for my assistance. I chose a short but elegant and sexy purple halter dress with a scoop neck along with and matching handbag and a pair of open-toed four-inch pumps. He bought me a nice pearl necklace, and matching bracelet, to complete my outfit. He also told me to quit calling him Uncle Jim. I'd have to remember to call him Jim which might be challenging after all these years.

I told him it might look funny for me to get all dressed up in my dorm room because no one could afford the clothes and jewelry he picked out for me and I didn't want all that attention so he suggested that after I go to the salon I get dressed in his hotel room. I got a little suspicious but that seemed to be the only reasonable alternative.

The next afternoon, I got my hair styled and makeup done professionally and headed over to Uncle Jim's hotel room, which turned out to be a small suite, where he greeted me by saying, "Wow, you look fabulous. I can't wait to see you in your new dress."

I shyly responded, "Thank you."

He told me I could get dressed in the bedroom and I went to get changed. I knew I wouldn't be able to wear a bra with my dress and I brought along a white seamless thong so there wouldn't be any visible panty lines in my dress. As I stood there in my thong, I couldn't believe I was going through with this charade but I'd end the evening with a new dress, accessories, and five hundred dollars in cash along with a spectacular meal. I took my time getting dressed even though there wasn't much left to do.

When I was done, I took a deep breath, and before I opened the door, I called out to Uncle Jim, "Are you ready for me?"

"I can't wait, Jenny."

I took another deep breath and turned the doorknob and walked out into the sitting area. Uncle Jim's eyes widened and he got a huge smile on his face as his eyes traced the length of my body from my head down my bare shoulders to my cleavage, over my torso to my hip, down my legs to my toes, and back up again.

"Holy shit, you look absolutely stunning. Jenny, you are a beautiful and sexy young lady."

I shyly looked at the floor and said, "Thank you, Uncle Jim."

"Remember, I'm just Jim tonight."

"Okay, thank you, Jim."

He then had me slowly turn around and I could feel his eyes scanning my body. I felt beautiful and sexy. Jim told me that I had to act confident, that men liked a confident woman. He said that he'd be talking about a business deal with Art and hoped to come out of the dinner with an agreement on a contract. All I had to do was help keep the casual conversation going, and compliment Art on his appearance and knowledge.

Uncle Jim had a car service pick us up in a huge black SUV and took us to the restaurant. It was very difficult to get into the car in my short dress and I'm sure Uncle Jim and the driver got a nice view of my legs and panties as I got in and out of the car. I held onto Jim's arm as we walked into the restaurant under the watchful eyes of many of the other patrons. I'm sure they thought I was a paid escort but, in a way, I guess I was. I felt proud that I was attracting admiring stares from the men and some of the women. Art and his lawyer arrived shortly after we sat down at our table. When we were introduced, both of them glared and gave an appreciative smile.

Art asked Jim, "Who is this very attractive young woman?"

"Art, Sam, this is Jenny. She is a protege of mine who is in college majoring in business. I hope you don't mind that I brought her along to learn some of the tricks of the trade."

"Oh no, Jim. We don't mind at all. You're very beautiful, Jenny."

"Thank you, Art. You're quite handsome yourself. Older men are so much more mature and confident than the boys at school."

Everyone ordered a round of drinks as the men chatted about the stock market and various business trends. Things got serious once they brought us our dinners and it seemed to be going well. Whenever Art or Sam would glance my way, I made sure to smile at them and even uncross and cross my legs again. My skirt had ridden up my legs and I was showing off plenty of my thighs and most likely, my panties too. When I looked down, I could see my nipples poking through my top just a bit. That explained them staring at my chest. Uncle Jim made sure to put his arm around me or stroke my bare shoulders at times and took the liberty of placing his hand on my knee and rubbing my legs. I understood that he was trying to silently brag about him having a young lady as his date but I couldn't help but feel a slight tingle in my pussy when he touched me.

Every so often, Jim would explain to me what was going on. The men negotiated over dinner and seemed to come to an agreement just before dessert arrived. Uncle Jim looked over at me and gave me a wink so I figured things were going well.

After dessert and coffee, the three men shook hands with Sam saying he'd draw up the appropriate contract and send them over to Jim for signature. Both Art and Sam kissed me on the cheek and hugged me before they left. We exchanged pleasantries about how it was nice to meet one another.

When his two clients left, Uncle Jim then told me, "That was perfect, Jenny. You were wonderful."

"But I didn't do anything."

"You did more than you think, honey. I can't thank you enough."

Uncle Jim was ecstatic in the car on the way back to his hotel. He asked me if I wanted to have a drink with him at the hotel bar but gratefully declined. I knew what he was like but I had an early class anyway. When we got to his hotel room, he stood in front of me holding my hands, scanning my body once again. I could feel him undressing me with his eyes. I hate to admit it but I found it exciting to have a few older men find me attractive that night and it was obvious Uncle Jim was taking a mental picture of me at that moment.

Before I went into the bedroom to change, he mumbled, "You know, if you weren't my niece....oh, never mind."

I knew exactly what he meant because I was thinking, "If he weren't my uncle...."

As I stripped off my dress to change back into my casual clothes before returning to campus, I posed in front of the mirror. I took a good look at my nude body and thought, "Maybe I'm sexier than I thought," as I twisted and turned looking at my firm, pert breasts, slender legs, and shapely ass.

I put the dress and accessories that Uncle Jim bought for me in a bag and I did something a little naughty. I purposely left my other pair of pink bikini panties on the floor on in the bedroom knowing Uncle Jim would find them.

I stepped out of the bedroom and thanked him for a pleasant evening, "Tonight was fun. I had a good time."

"We can do this again sometime if you're willing, Jenny."

"Call me when you're in town."

"Okay, honey."

We kissed each other on the cheek and he gave me a big long hug. I could feel his growing manhood pressing against my thigh but I knew I had to go. I thought about the evening on the car ride back to the dorms. My pussy was itching and my nipples were hard. When I got back to the dorms, a few of the male students were wandering the hallways obviously drunk or high and they noticed my makeup and hair and made some comments about how good I looked and wanted me to go back to their room. I shook them off but it only reinforced the thought that maybe I really was attractive to men.

When I got to my room, I hung up my new dress and put the accessories away, trying hard not to wake up my roommate Ally. I then went to the lady's room to wash off my makeup and returned to try and get some sleep. My pussy was itching and I was tossing and turning with the thoughts of everything that happened that evening. I put myself on display for my uncle and his business associates and I know all of them wanted to fuck me, especially my uncle. I kept fantasizing about what I would do with Uncle Jim as my hand drifted down between my legs. I masturbated to the thought of a wild love-making session with my uncle. I tried to muffle my moans as I brought myself to an orgasm.

My effort to be quiet as I came was unsuccessful because Ally commented, "Are you done now because I need to get some sleep."

I demurely replied, "Uh, sorry."

As I drifted off to sleep, I had a dream of my uncle coming into the bedroom when I was changing at the end of the night, throwing me onto his bed, and letting him fuck me all night long. I was rudely awakened by the sound of my alarm just before I came.

The next day after class, I sent a text message to a boy that had been trying to date me and asked him what he was doing later. We ended up going to a cheap restaurant for dinner and then going back to his dorm room. I was still horny from the night before so it didn't take much for him to talk me out of my clothes. He ate my pussy to a nice orgasm before he fucked me hard. The good thing about being young is that he was able to fuck me twice before we called it a night. The entire time I was sucking his dick or when he was fucking me, I was pretending it was my Uncle Jim that I was with. I know it was wrong to fantasize about a relative like that but I couldn't control my nasty thoughts, especially when I was so horny. Damn, it felt good to finally have a hard cock in my mouth and pussy.

I kept in contact with my uncle through social media and text messages. He thanked me for the present I left him, meaning my panties, reminding me that pink was his favorite color. I pretended not to know what he was talking about. He said he didn't know when he'd be back in town but he was hoping we could get together again soon. I told him it sounded like fun. We would text message each other several times a week and I would send him pictures of me before I went out on a date and he would always tell me how beautiful I was and how lucky the guy was to be going out with me.

The day after one of my dates who I had been seeing for a couple of weeks, my uncle asked me in a text, "How lucky did he get last night?"

I thought it was a very strange text to be getting from my uncle so I thought about it and sent him this text a few hours later, "Oh, he got really lucky."

He responded, "I hope he appreciates his luck."

"Oh, I'm sure he does."

Apparently, he didn't because he started dating someone else a week later. He swore they were just friends but I wasn't falling for it. That was the end of that short-term relationship.

When I told my uncle what happened, he replied, "That jerk didn't appreciate a beautiful woman when he had one. He'll never have a woman as beautiful and sexy as you."

Sometimes, I would take a picture of me wearing the dress he bought me and he would always tell me he will never forget how lovely I looked that night and how he was looking forward to doing it again soon. I told him that would be fun.

A couple of days later, he sent me a text saying he'd be in town again on business and wondered if I could accompany him to dinner with a client again. He said we go shopping just like before. I couldn't help to quickly agree to join him. I told him I was looking forward to seeing him again. He said he couldn't wait to see me too. Deep down I knew I was going down a dangerous road but the intrigue of it all made me want to see him. He was a villain in my mother's eye and I was suspicious of his motives but that's what made it fun. I was playing with fire but I convinced myself it was all innocent. Nothing would happen, we were an uncle and niece going out for dinner.

I was anxious and excited over the next couple of days in anticipation of seeing my uncle again, as friends, of course. He picked me up in a rental car to take me shopping and I made sure to wear a short jean skirt and halter top with no bra. I kissed him on the cheek when I got in the car. He once again told me how gorgeous I was. It's flattering to have someone tell you that because not many men take the time to compliment women.

Uncle Jim took me to an exclusive dress shop again where I tried on several dresses for him. I made sure to pick out some very, very sexy dresses to show him. I know he liked me modeling for him and to be honest, I was enjoying it too. The sales clerk that was helping must have thought I was his young girlfriend but I didn't care what she thought, we were having fun. After modeling several dresses, including some very sexy ones, I picked out a red mini slip dress with spaghetti straps. It was low cut and without a bra, my breasts bounced freely

We also picked out matching shoes and handbag, along with a necklace and bracelet again. I was surprised when he asked me to go into a lingerie store to help pick out some stockings and underwear to go with the outfit. It was an odd request but he was being so generous, that I agreed.

We looked at several pairs of underwear when he held up a tiny g-string and said, "How about this?"

I shrugged my shoulder and said, "Okay."

We picked out some stockings and left. Uncle Jim took me to a chain restaurant nearby and we talked about school, his divorce, and how well his business was doing. He told me how everyone in the family made him out to be the bad guy during the divorce but they didn't know that my aunt never wanted to have sex, she was a compulsive shopper, and they barely talked to each other. He stayed faithful as long as he could but said a man had needs. He said his business colleague who we were going to have dinner with was bringing along his trophy wife but she wasn't nearly as pretty as me. I got a little nervous seeing there'd be another woman there who might be more attractive than me but he told me not to worry.

On the day of the dinner, I met him at his hotel again to get dressed. I didn't have time to get my nails, hair, and makeup done professionally again so I got ready in his hotel suite bathroom. It was naturally taking longer this time and in the middle of me getting ready, Uncle Jim told me he had to use the bathroom. I was annoyed but understood. A girl doesn't like to be interrupted when getting ready for a big dinner. I was only wearing my panties so I wrapped a towel around me and opened the door.

Uncle Jim stood there staring at me and said, "Wow, you look great in just a towel. A guy could only hope that it would fall off."

I playfully responded, "Oh stop, all you guys are alike."

"Hey, you can't blame me for looking when there is a sexy young lady standing in front of me."

I blushed and told him to hurry up. It took me a while to finish getting dressed and when I was done, I came out of the bathroom. He heard the door open and quickly turned his head and gave my body a slow up and down look.

"I wish I were young again. You look stunning. You are so sexy."

"Why thank you, Jim. What would you do if you were young again?"

"Baby, I'd treat you like a queen."

"But you already are."

"Oh no, Jenny, this is nothing."

I did a slow turn for him so he could see me from every angle. The dress hugged every curve of my body from my boobs to my hourglass waist and round butt cheeks. I still had to put on my stockings so I pulled them out of the package and sat down on the sofa in the sitting area. I rolled the first one into my hand and placed it over my painted toes then slowly pulled them over my heel. I straightened my leg and pointed my toes as I pulled them up over my calf. Uncle Jim was watching closely while I pulled the stocking past my knee, and up my thigh. I knew he could see my g-string and I made no effort to conceal it from his view. I repeated the process on the other leg, and stood up, lifting my dress slightly, to even them up on my thighs. I sat down and crossed my legs with my ankle over my knee to put my shoes on knowing full well my uncle was feasting on the sight of my stockinged feet, legs, and g-string.

When I stood up, Uncle Jim told me, "Damn you've got great legs. You looked lovely, Jenny. You're a beautiful young lady. You've come a long way from being a tomboy."

"Thank you, Uncle Jim. You look quite handsome yourself. I love a good-looking man in a suit."

"So you think I"m good-looking."

"I always have, Uncle Jim."

I blushed as my uncle took my arm and guided us out of the hotel room and to our dinner. I felt so sexy being all dressed up again and having an older man tell me how beautiful I was. My dates in college rarely complimented me or would say I looked great in a way that felt forced. I could tell that Uncle Jim was sincere and I liked dressing up for him. He had his hand on my leg as we rode to the restaurant, feeling the silky material of my stockings. When I got out of the SUV at the restaurant, my uncle held my hand as I placed my right leg on the ground. My dress rode up, exposing the bare skin above my stockings and my g-string. My uncle smirked as he stared.

I enjoyed going out with my uncle because other than my prom, no one ever treated me like a lady before. My dates in college were okay but Uncle Jim went the extra mile. I didn't expect to have my dates buy me clothing and jewelry but they never treated me like I was someone special and they didn't know me when I was a tomboy to appreciate the transformation in my actions and appearance.

We went into the restaurant and met Chuck and his trophy wife Lana who was in her mid to late 30s and about half of her husband's age. Lana had bleach-blonde hair, big fake tits, and botox lips. Chuck kept looking at me all night which got Lana a little annoyed but it didn't bother me one bit. I was now 19 but told them I was 21.

When Lana and I went to the restroom, she advised me, "Use your good looks and get as much as you can while you're young dear."

I told her, "Oh, Jim and I are just friends. It's nothing serious."

"Sure he is, darling. Make it worth your while is all I'm telling you."