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 grew out of her desire to see me dress up, wished for a more normal life and to date other men. I sensed that our time together was coming to an end, so 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 restaurant manager. 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 working numerous civic events and she never 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.
This was a quiet place compared of the other clubs as 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 and there was an interest on her part but it was guarded.
"You are a bit of a rebel aren't you?" she stated.
"Yes, you. You show up in a muscle car while the rest of the men drive boring little foreign sport cars."
"I refuse to be boring."
"Those cars are dangerous."
"Life is too short not to take risks."
We continued to talk and drink and make polite conversation. It was after her return from a powder room break that she slid closer in closer to me. Then, without warning, she leaned in and placed her lips on mine and let her tongue gently entered my mouth. I embraced her and responded in suite. One of her small hand made it 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 and my cock through my dress slacks and I began to slid my hand 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 for a powder room visit and 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 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.
"Just how adventurous are you?" she asked.
"I want you to take them home with you."
"I want you to clean them and wear them tomorrow under your suit for the art gallery opening."
I looked at her and didn't say anything. I slipped the panties into my coat pocket ensuring 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.
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<a href="https://www.lushstories.com/stories/crossdressing/once-again-in-silk-part-1.aspx">Once Again in Silk - Part 1</a>