This is posted in the reader fiction but it's an experience that actually happened to me....
I dated a woman some time ago that tapped into something that drove me nuts. For this story I'll call her Sarah. One day, while we were having sex, she reached for a lipstick and put it on. Then she teased me with it. I came instantly when she touched it to my lips and she knew I was open to more. We talked about it through the weekend and each time we did my erection told her I was all in. She said she wanted to dress me as a woman and have sex with me. I wasn't about to argue with her.
She had it all planned out. She asked me to wear her panties while we went shopping for a few things. Her panties were dark blue, tight, silky and they struggled to hold in my cock. It's head was purple and I was doing my best to not stroke it as she touched the silky fabric. Eventually it subsided slightly and I pulled on my jeans. She smiled as we drove the store. I was enjoying the feeling of the satin against my skin. I felt so naughty.. and completely out of my element. We went to a local store and bought makeup. I was instantly hard again as we picked out base, powder, blush, mascara and various other cosmetics. I had to hide the bulge in my pants using the basket! Next.. the perfume counter. Again the same thing. She smelled numerous scents before she picked one out for me. We made many stops that afternoon and when we returned home we had heels, pantyhose.. a dress, bra and a long brunette wig and had even found shoes in my size.
She returned home and she stripped to her bra and panties.
Next she asked me to shave. I shaved my face, twice. She then insisted I shave my legs. This took some doing but eventually I was smooth and bare. She took care of shaving my balls and cock. She teased me as she shaved me. Soon I was bare and smooth. I wanted to *censored* her so badly but I knew she wanted me made up first.. I was dying to see where this went. Makeup first. She showed me how to put base on. It evened my skin tone.. the powder helped even more. The feminine smells of the powder made me ache for a release. Blush next. Then my eyes.. she did this for me and also applied the mascara. The the lipstick. I nearly came as she put the soft pink pigment on my lips. It felt smooth and had a slight taste. I was aching to stroke my cock. I'd remember this taste and scent for a very long time, as it turns out. I had long admired the colorful ads and pictures of women wearing lipstick. To me it represented such power. I don't know if women really see it that way or not.
She moved on to my clothing. The soft nylon of the pantyhose slid over my legs. It was tight, sexy and so foreign to me. The bulge in the front made it clear I was enjoying the process. Next a short white slip and then my bra. She stuffed the bra with pantyhose. Suddenly I was a 'c' cup. She teased me by running her lips and tongue against my nylon encased cock. It strained for relief. My dress was next. It was a sundress. The soft fabric stretched slightly and I felt my own ass. It slid in my hands.. it felt good. My false breasts suddenly looked even more real when covered with the fabric. I can still remember the taste and feel of the lipstick.
She placed the wig on my head and settled it into place. I was grinding against the nylon and she insisted I stop. It was probably wise she did that as I was very close to cumming and it would have spoiled all her work. The perfume was next. It's scent filled my nose and she leaned in to smell for herself.. she leaned against me and her breasts rubbed against my stuffed bra. She was very turned on. I was far more turned on.
Next she insisted on nail polish. A deep dark red covered my nails. They were not long but they helped disguise my masculine hands slightly. She then put some jewelry on me. A necklass and bracelets. Then I slid into my heels. We had managed to find heels in my size (size 11) but they were only about 2 inches or so. It was a good thing as they were more difficult to walk in than I had imagined.
Sarah lay back on the bed and insisted I walk back and forth. She slowly touched herself as I struggled to walk in the shoes. Soon she had pulled her panties to the side and was touching herself freely. She looked at me and motioned for me to crawl to her. Her hands found the back of my head as my tongue found her pussy. Her warm juices were not new to me but this was a new experience for me. She came after a short period. She pushed me back on the bed and pulled up my dress and teased my cock. She started with her fingernails.. slowly touching my shaft. Using her nails she finally opened up the nylon on my pantyhose and my cock sprang out. Her mouth wrapped around my shaft and she slowly sucked on me. Well before I came she pulled back and lay back on the bed, legs wide inviting me to enter her. I pulled up my dress and my cock entered her slowly.... the warmth of her body surrounding my cock caused me to explode immediately.
It was one of the most memorable experiences of my life...