It had been many years since my time in Florida and my transformation to Melissa to please my lover, Lydia, and also my own inner desires. She soon grew out of her desire to see me dress up and wanted a normal lifestyle and to date other men.
It seemed that our time together had come to an end. I gave up my apartment and I moved back North.
As I still had a sizable amount of money left from my settlement. I didn't need full time employment and I took a job as a part time job as a bartender in an upscale establishment. It was at the suggestion of a regular customer that I soon joined and became active with the Junior Chamber of Commerce.
I met Darlene at one of the regular Friday night gatherings. She was a few years older than most of the other females but did not look, dress or act it. I saw her a lot at the numerous functions and the civic events we worked together. She was constantly hit on by almost every male member in attendance, but I never saw her leave with anyone..
I attempted to start a conversation with her many times, and though she responded she never really said much. So I was surprised when she invited me to join her for a drink at a local pub after one of monthly meetings.
The place she chose was a quiet place compared of the other clubs. It catered to an older crowd that relished conversation rather than ear splitting music. We took a seat at a corner table and ordered drinks and we chatted about our likes and dislikes, there was an interest on her part but it was guarded.
"You dress like one of them, but you're nothing like them," she stated.
"Yes, you. You show up in a muscle car while the rest of the men drive little foreign sport cars."
"I refuse to be like everyone else. You have to be yourself."
"Don't you want to fit in?"
"To a point, but I refuse to be boring."
"You should see the looks you get when you show up on your motorcycle.Isn't riding a motorcycle dangerous?" she continued.
"Life to too short not to live a little dangerously," I repied.
We continued to and drink and make polite conversation. It was after her return from a powder room break that she slid in closer to me. Then without warning she leaned into me and placed her lips on mine and let her tongue gently entered my mouth.
I was surprised and pleased at the same time. I placed my arm around her waist and pulled her in even closer to me and responded in suite. One of her small hands made its way to my crotch and began to gently rub the increasing budge.
"So you are not afraid to take a risk?" she asked as she broke the kiss.
"No I am not."
She continued to gently rub my cock through my dress slacks while we talked. I allowed my hand to slowly slide up and down her silk covered legs. Each time it went further under her skirt until my hand discovered the tops of thigh high stockings and the warm silky flesh where they ended. She was not wearing pantyhose but thigh high nylons.
"You like?" she asked.
"Lets see how risky you really are."
She then asked me to unzip and allow my prisoner some air. So with minimal movement I unzipped my trousers and allowed my now fully rigid cock to escape. As soon as I did her hand circled to and she began to gently stroke it. I slowly slid my hand under her skirt where I began to gently rub the crotch of her very wet panties.
I had been without a lover for quite a while and it didn't take long before I was ready to shoot my load. I told her so as I reached for the cocktail napkin. She stopped me from sliding in under the tablecloth.
"That will be too rough a texture for him," she said in low voice.
She let go of my cock and excused herself to visit the powder room. Before she departed she asked me not to put him away as she would be right back. She returned in less than a minute and slid in close to me again.
"These will work much better," she said and cast her eye downwards.
I looked down and there in her hand was the prettiest pair of white satin thong panties I had seen in a long time. She then gently wrapped them around member which in her absence had began to shrink. As soon as the buttery soft silk touched my flaccid cock it sprang to life again and she resumed her gentle stroking.
She softly whispered in my ear urging me toward my finish and I exploded in the sexy garment. We returned to our drinks and we lit a smoke. She smiled and kissed me numerous times and shortly afterward announced that it was late and that she was getting tired. I slid the panties back toward her.
"So just how adventurous are you?" she asked.
"Good, because I want you to take them home with you," she replied and slid her cum soaked panties back in my direction.
"I want you to take them home and clean them. Then I expect you to wear them tomorrow under your suit for the art gallery opening."
I looked at her and didn't say anything as I slipped the panties into my coat pocket. Once assured they would not visible when I stood up and we rose to leave. I walked her to her car where we stood and kissed good night for a long time before she got in her car and departed.
My mind was racing as I drove home and I was looking forward to tomorrow night and whatever surprises it would bring.
This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than Lushstories.com
with this note attached, it has been posted without my permission.
<a href="https://www.lushstories.com/stories/crossdressing/once-again-in-silk-part-1.aspx">Once Again in Silk - Part 1</a>