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Saturday, July 30, 2022

Upcoming date (guest caption by TheInsomniac)


 

3 comments:

  1. Every success begins with a single small step, go for it!

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  2. When I got back from my date, I went straight to my room and threw myself on my bed. I buried my face in my pillow and began to cry.

    My mother knocked on my door and stepped in and sat on my bed next to me, putting her hand on my shoulder. I rolled over and looked at her, tears running down my face.

    "What happened honey, didn't you have a good time?" she asked.

    "I did, I thought we were having a great time. He made me laugh and he was a gentleman, just like I thought he would be. Then in the car, he had his hand resting on the seat between us and I put my hand on top of his and gave it a little squeeze. Just a kind of a thank you for being so nice. He looked at me and smiled, he has a great smile. Then he suddenly jerked his hand away and drove me home. When we got here, he walked me to the door, shook my hand and said goodnight then left. What did I do wrong? I liked being out with him, I was looking forward to going on more dates with him Mom." She wiped tears from my face with her thumb and shook her head.

    "I don't know. Maybe your father can talk to him and see what happened."

    An hour later my father came in and explained. He said Steve told my father that he had started to see me as a young attractive woman, which I am now, but when he looked in my eyes after I touched his hand, he saw me as the teenage boy he had watched grow up. It really shook him and he couldn't handle it. He said he was sorry.

    "I'm not sure what to say. I can see his point, maybe you can too. It's hard to make such an adjustment so suddenly. He just isn't comfortable dating you right now." My father left me alone and I lay on my back and looked at the ceiling, wondering if there was anything I could do. Then I got an idea.

    "When it was clear that I would be a woman for the rest of my life, my mother took me shopping. Bras, panties, sleepwear, a couple of dresses and skirts, different tops and several pairs of jeans. I wore jeans on the date tonight with a green button-up blouse and sneakers. No makeup, no scent, no manicure although my mother offered to go with me to get a mani and a pedi. She had to explain what that meant.

    I talked with my mother about a plan I had, I needed her help. She liked the idea and said even if it didn't work, it would be good for me.

    The next day we went for the mani and pedi and I got my hair cut and styled. She helped me with makeup and getting dressed. I took the selfies but she was there with suggestions on posing my facial expressions. We treated it as a modeling session, that's what she said anyway. We avoided anything that was even mildly suggestive. I was aiming for feminine, tasteful and refined. We both agreed that we achieved that. I was wearing lingerie but only because it accented my figure. I wore a purple dress that she told me would bring out the color in my eyes. I also had on a pair of black heels and pantyhose for the first time. I took photos of myself in a dress, heels, and makeup. including a close-up of my face I sent them in a text to Steve with a simple caption.

    "I really enjoyed our first date. If we had another one, I would like to go somewhere where this outfit might be appropriate."

    Steve called me and apologized which I accepted. We went out to dinner and a movie on Saturday night. We walked around the lake after dinner and Steve held my hand the entire way.
    Back at the car, Steve walked me to the passenger door and opened it for me. I looked up into his face and put my hands on his shoulders.

    "Thank you for a wonderful time Steve," I said then I gave him a light peck on the cheek. He smiled and gave me a hug. He drove me home and walked me to the door where I gave him a quick kiss on the lips and quickly stepped inside the house, hoping I had not pushed it too far.

    Steve and I will be going out again next Friday. Before I was depressed about having to date an older man, but now I am looking forward to it.

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  3. Wait, Insomniac is still around?

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