I have always had a fetish for nylons. I loved the way a ladies legs looked when they wore them. I used to go to my friends house for visits and after a while, excuse myself to the bathroom area where I can go through his mom's laundry and try on her nylons. They felt so great and looked so good on my legs. As I grew older, my passion for nylon stockings only increased, but so did the risk of getting caught.

When was sixteen years of age, I used to visit my aunt regularly. I used to lock myself in the bathroom when I took a bath, and would go through her walk-in closet and try on her stockings, heels, dresses and wigs. Although it was time-consuming, the best times were in the summer when I would do chores and she would be showing homes since she was a real estate agent.

Just as I turned eighteen, I was still trying her clothing on. She seemed to have a penchant for dressing very classy and sexy at times. I'm sure that's why I enjoyed doing chores for her as a teen. It allowed me the opportunity to indulge in my fetish also. By now, she had a different house and her clothing would eventually be closeted in her own room, where I had limited access.

One day, my mom asked if I would stop by my aunts to drop off some flower bulbs for her. I happily obliged, knowing my aunt would be out showing homes and I knew where the spare key was. It would be a perfect time for me to look through her closet for new, or old things, to try on.

As I entered the empty home, I went straight for the bedroom. I had to be careful as to not disturb too much. I opened drawers and found that she still adored stockings, but a classier brand. He lingerie preferences was still as sexy as always and she eventually upgraded her heels to sluttier styles. By now, my cock was starting to drip. I figured I had plenty of time so I picked what I felt she would not suspect as being 'disturbed' and started to dress up. I loved the smell of her clothing also. Very girlish.

Once I was dressed, I would pause to admire myself in the mirror. I looked like a classy, yet very sexy, housewife. The stockings had a seam in the back which were an extra special touch.

My erection was at full sail by now and I wanted to jerk out a load so I looked around her bedroom for magazines that may have some nice lingerie shots. I opened her nightstand and was staring at a huge dildo and a vibrator. Whoa! That's new.

I removed the dress and kept her garter belt, stockings and wig on with a nice pair of 5" heels. I took a towel from the bathroom and laid it on the bed. Me and the dildo were going to become good friends.

I started to massage my penis with the vibrator and worked my way around my hairless balls. It felt great! I would come close to shooting a load, but make myself stop to avoid blasting too early. I was sucking on the dildo, (knowing full well that my aunt used it), and I marveled at my ability to deep throat the mushroom headed friend.

I was lost in my own perverted universe when I was suddenly brought back to Earth with a smashing blow when I heard the sound of "huh hmmm", in a familiar tone, which turned out to be my aunt. She was standing in the doorway with a concerned, yet disappointed look on her face. "I always suspected that you were 'gay' but I never thought you were a crossdresser," she said.

"I-I, I'm not gay," I managed to mutter. "I just like to wear things like this." I was so red with embarrassment by now. My penis had shriveled to a limp shrimp as I scurried to cover myself and gather my clothing. "Please, don't be angry. Don't tell my mom and dad." I was in panic mode.

"I was curious and I thought I would..." my voice trailed off. No way I was talking myself out of this.

She walked into the room while I still moved about, trying to put her dildo and vibrator away without cleaning them. "I can't be angry at you if you agree not to say anything either," she said, as she sauntered to the closet.

"Huh? What do you mean? I'm really sorry about all of this..." I stammered.

"Hush!" she said as she placed a finger over her lips. She opened the closet door and pulled out a leather riding crop.

'Oh no!' I thought to myself.

She smiled, "I have no reason to share your secrets with your parents or anyone else. But I think we may be able to work out an arrangement to secure a little confidentiality for both of us."

"Anything to keep my parents from finding out." I gave in so easily.

As she approached me, she placed the riding crop under my ball sack. "Those are a little small aren't they?" She asked.

"They work for me." Was all I could come back with.

"You would make a pretty girl, though. Maybe I should give you a few lessons on how to apply makeup, and we'll work our way up from there. I need a personal assistant. This would allow you to earn a little extra cash while you go to college."

"I don't think it would be a good idea for me to dress up as a girl and work for you with my parents around," I pleaded with her.

"Look, we can avoid the parental issues if you just let me handle this. I need a personal assistant in more ways than just business," she said with a sly smile while running her finger up from her private area to her breast. "You see? There's a reason I'm not married. But I still have desires and you will do perfect to help me fulfill those desires."

"S-so you're a lesbian?" I asked quietly.

"Of course not," she shot back. "I have no time for commitments and drama with a man. But a 'boy-toy' like yourself would suit me just fine." She stepped closer to me. "You and I can have a nice arrangement. You provide a service and I provide an opportunity for you to indulge in your little pleasures." She smiled and winked.

"As long as my parents and friends don't find out," I agreed.

"Look!" she said, "I have no intention of telling anyone even if you don't agree. This is as much of an embarrassment for me as it is for you."

"I understand." I mustered up the courage to finally open up to her. "I've always found you so beautiful. But your clothing was so sexy and inviting. I liked the way they felt and the way they looked," I continued, "You inspired me to want to crossdress because I wanted the same beauty and the confidence you have." I blushed... I finally admitted what I had been doing all those years.

"You're sweet," she said as she held the riding crop under my chin... "Perhaps too sweet. But I'm about to share a part of me that you have never known. Something your parents aren't aware of." She sat me on the bed now and sat down beside me. As she brushed my hair, she looked into my face and gave a sly smile. "I'm a dominatrix," she whispered.

I wasn't shocked. There was always something about her clothing style. She had things I never saw her wear in public, but even when she dressed up for some occasion, she was always so sexy and classy. Never trashy.

That day, we shared our deepest secrets. It was the beginning of a new relationship between me and my aunt. I would never betray her trust, and I would gladly spill blood for her. The great times that came after that day are fondly remembered and saved in detail in my diary.