I was in my early 20s and had met a married man who traveled to Chicago on business on a monthly basis. He was introduced to me by my boss at the time who told his friend Tony "I would help him with whatever he needed". Fresh out of college, I wanted to make a good impression on my boss and a guy who was a big deal when he came to our hotel. Three or four months passed and there were a few meaningless things I had done for him but his glowing review to my boss was all I cared about.

One afternoon I get a call from him that he needs a gift picked up from a store and delivered to his room. I get the details including that it was in the lingerie department ready for pick up after 4pm. There was a slight delay in getting the order ready but it gave me a few minutes to browse. These weren't the bra and panties I had bought for myself. I peaked at a few of the price tags and couldn't believe of expensive some of the items were. The woman brought me the package with the message that if something didn't fit right to bring it back and she'd take care of it.

I got to his hotel room, package in hand, a little after 6pm. He was on the phone but told me to come in. He opened the package and took out a very cute white lace bra and panties. I pretended not to look but couldn't help think how I'd love to have them. He hung up his call and asked what I thought of his gift? I told him they were nice, very cute. He walked over and handed them to me.

He explained there was one occasion before he thought I was wearing a bra. He confirmed it when he saw a bra strap marks one day when we were changing to play golf. In face, he said he was pretty sure I was wearing a bra at that moment and he was right. So there I was, holding very expensive lingerie in a hotel suite being outed as a crossdresser by a seemingly understanding guy who is a good friend to my boss. Needless to say I was speechless. I could feel my cheeks turning red.

He asked me if his assumption was correct? I sheepishly told him he was. He told me not to worry and not to be embarrassed. He said to go try them on come out and show him how it looked. He poured himself a drink and pointed to the bathroom to go change. Part of me was scared shitless while the other part, sinfully aroused. I stripped down, taking off the cheap bra I was wearing, and slid on the panties first then put on the bra. Both fit perfect. I reached for the door handle and thought I'm either getting a raise or getting fired for this. I walked out into the suite and walked toward Tony. He looked up from his file and gave a nod of approval and motioned for me to come closer. Standing next to him, his hand rubbed the lace material over my ass and then gave it a light slap.

He told me I looked great and that we would build on this. He asked me how far I was willing to take this. I wasn't sure what "this" was but I told him I was willing to try anything (thinking to myself, I'm so fired or ready for a promotion). He had a dinner meeting at 7pm. He said I could go and that the bra and panties were mine to keep. I needed to be back at his room at 3pm sharp tomorrow.

I had been crossdressing for a few years and had some fun experiences. College was a little on again off again but now graduated, in my own apartment, with a job, I was starting to buy some things, experiment w make up, and had been with a few guys as well. Tony was a completely different league though. Successful. Good looking. He was what I wanted to be. Right now, my goal was to please him.

I showed up the next day and let myself into his room. There was a black dress, lingerie, shoes, and a few other items laid out on the bed. I was looking for a note or some kind of direction from Tony. There was nothing. A few minutes later there was a knock on the door. It was a woman from the spa. She recognized me and identified me as Tony's "special fiend." She told me my secret was safe with her, Tony had taken care of her.

She had what look like a tackle box that ended up being her traveling make up kit. WTF had I got myself into? I flashed back to being made up as a teenager but here I was a 20 something professional, playing "girlfriend" to some rich businessman. Confused, scared and highly intoxicated at the prospect of what was going to happen, I was ready to get started.

Debbie had specific instructions from Tony for me to follow, making sure I was shaved and as perfect for him as possible. Then it was into Debbie's makeshift makeup chair. She had produced two separate wigs as well. She said it was time to work her magic. I've never done my make up like she did. We tried both wigs, settling for a shorter sandy blond. By the time she had walked me through dressing, put on a cute pair of heeled booties, I was amazed at the transition.

She said she was certain Tony would like it. She put a few items in a small purse for me in case I needed to freshen up as the evening progressed. I asked if she knew where I was heading but she produced a bottle of Champaign and told me Tony would be there shortly. She poured a glass for me, told me to act natural and have fun. And off she went.

I was a few sips in when Tony arrived. His silent head nodding followed by a "you look amazing" was all I needed to hear. I walked over and gave him a kiss on the cheek and thanked him. I told him I've never felt so amazing and it was because of him. He held my hand and pulled me back toward him, paused and then kissed me on my lips. He started to pull away but I wanted more. I kissed him again but this time neither of us stopped.

Tony stopped us after a minute. We had plans. He had to change and I fixed my lipstick. About 10 minutes later we were heading out the door and then it hit me. I was walking through the hotel I worked at, in a public area for everyone to see. We made are way down the elevator, the lobby and to the waiting car and I realized that all anyone saw was a rich dude and his girlfriend. My heart stopped racing once the limo started to pull away. Tony said I looked amazing.

We ended up at an art show. Neither of us really wanted to be there but it was a friend of Tony's so he was obligated. No one looked twice at me in a suspicious way at all. My confidence grew by the minute, sipping Champaign and walking with him. We ended up having a great time. We stayed for a few hours and then headed back. The car ride back resulted in giving my first limo blowjob, getting a chance to taste all of him. I was in love.

We got back to the hotel and were enjoying each other in the room. Tony was a great kisser and had an amazing cock. It wasn't long before he was stripped naked and me down to my bra and panties, in bed. After a good amount of touching, kissing and cock worship, i felt his cock rubbing against my ass. Then his finger slid in with a little lube.

I remember the head of his cock slowly moving inside me and the feeling of him slowly filling me up. And then, when I felt his hips again my ass, he stopped. I could feel him swelling inside me. All of him. Slowly he began to slide himself in and out of me. We were in perfect rhythm and about ten minutes of his cock fucking me, I felt him cum in me, shot after shot filling me up. The most amazing feeling knowing he was truly inside me in every way possible.

We had sex twice more that night and it was the start of an incredible two year relationship. Those were two of the best years of my life getting to be Tony's girl, Jenni. Our story only started with that night. But all great things did come to an end. Tony sold his business at one point, retired and we broke things off. Some heartbreak. No regrets. An amazing time that easily was my most memorable time Getting to be Jenni.