Caught My Best Friend (part 2)
What do you do when your best friend since high school turns out to be a cross-dresser? Is your friendship strong enough to survive this? I hope you enjoy this work of fiction.
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The next day I arrived at Ginnie's for our date. She was dressed in a lovely blue dress, sexy heels with an ankle strap. I'm not much of a shoe enthusiast, but found that the ankle straps looked wonderfully sexy.
We agreed to take Ginnies car, so we could just drive out of the garage without the neighbors seeing us. Knowing how self-conscious she was, I agreed.
We drove to the next city to put some miles behind us, to a popular seafood restaurant. Ginnie had little to say during the drive, which bothered me. I really wanted our relationship to go to a new and better level. Being best friends was great, but I hoped for something even better.
We discussed the menu and I ordered for both of us because Ginnie was uncomfortable about her voice being so deep. Once I had ordered, I decided to address my concerns head-on, and said, "You have been very silent, Ginnie – please tell me what is on your mind."
"Despite your assurances," Ginnie said, "I feel that I am here at your insistence."
"Ginnie dear," I replied, "I invited you on a date – I wanted to take you out, but only if you want to be with me. If you don't, I'll take you home – I have no interest in coercing you in any way."
"I'm sorry Bill," Ginnie said, "I'm just feeling so vulnerable from being caught – despite your assurances I can't seem to get over my fears. Please don't take me home – let's make the most of our time together."
I took reached across the table and took Ginnie's hands in mind and squeezed them. "Even though we have been best friends for many years," I said, "I understand your apprehension, and will work with you to get over it."
"What are your expectations of me tonight?" Ginnie asked.
"Very simple," I replied, "Just enjoy a night out with me – nothing more."
"That's good to hear," said Ginnie, "but what would YOU like to happen?"
"I don't want you to feel any obligation," I said, "but what I would like would be some nice shared time together back at your place, but only if that is something you want."
"Anything else?" Ginnie asked.
"No, nothing else," I said, "I don't know where it may lead, but I'm okay just letting things happen."
"Okay Bill," Ginnie continued, "but I'm still nervous about it – in fact still scared to death – but I trust you."
I kissed Ginnie's hand and smiled at her.
We enjoyed our dinner together and the conversation became more like a normal date. I was glad Ginnie was becoming more comfortable with the situation.
We walked out to the car and I opened Ginnie's door, but stopped her before she got into the car. I took her in my arms and she stiffened. I released her and said, "you aren't comfortable with my advances, so I'll back off."
"I'm so sorry Bill," she said, "You have been so good to me, I'm sorry I'm just not ready for this."
"Ginnie dear," I said, "I'm sorry to push – you know how guys are – but I'll back off, at least for tonight. I care about you and just want this to improve our relationship."
I helped Ginnie get into the car and we went to the movie theater, selected a movie and bought tickets.
As we watched the movie I kept to myself for the first half. After that Ginnie reached over and took my hand in her's. I look at her and she turned to me and leaned over to me. I kissed her on the lips and she kissed back. It was a closed mouth kiss, but it was a start. We kissed a few more times and she placed my hand on her knee.
That seemed like a green light to me, but I moved cautiously. I slowly moved my hand between her legs and her knees moved apart. I kissed her again and this time I felt her tongue part my lips and we kissed deeply. I was sure I had a green light now and moved my hand up her legs and felt her soft panties. I could feel her arousal grow as I touched her panties and her kisses became more passionate.
"Ginnie dear," I whispered, "If you are willing, I would love to take this further, but we are kind of limited here. Perhaps we can go further back at your place."
Ginnie smiled and me and whispered, "wait a moment," and she moved around in her seat. The next moment she handed me something, which I quickly realized was her panties. A green light can't get greener than that!
I leaned over and kissed her, reaching back up her dress. She was very obviously aroused and I took her in my hand and squeezed gently. She wiggled around in her seat and she said, "Do you mind if we skip the rest of the movie so we could go back home and continue there?"
I quickly agreed, and helped Ginnie put her coat back on, and we left the theater. At the car we kissed more before she got in.
On the drive home Ginnie said, "I'm surprised that you paid so much attention to me – the few other men I was with wanted me to attend to them, but you didn't."
"I'm not like other men," I explained, "but I don't expect you just take my word – you need to know it's true."
"I'm still nervous, but not because of you," she confessed, "you have been wonderful to me."
"Now Ginnie dear, I need you to be brutally honest with me," I said, "are you a woman or a man right now?"
"It's complicated," said Ginnie.
"I know," I returned, "but please tell me what you feel in your heart."
"I feel like I'm a woman," admitted Ginnie.
–––––––––––––––––––– To be continued ...
Feel free to contact me with your comments or requests. –Bill (oral_guy_2000@yahoo.com)
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