Caught My Best Friend (part 5)
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.
––––––––––––––––––––
After our shower we dried off and got dressed. I said, "You didn't have your wig on in the shower, and it was okay."
"I was already wet when I thought about that, and it was too late by then," said Ginnie.
"I think you are prettier with the wig on, but you are still Ginnie with or without it," I said.
Ginnie reached for her wig, but I stopped her. I embraced her and kissed her just as I would have with the wig on, saying, "the wig is nice, but it isn't what makes you a woman – now go put your wig on."
We made breakfast together and got to know each other all over. As Bill and Jim, we knew each other well, but as Bill and Ginnie there was suddenly much more to learn.
"Are you gay?" Ginnie asked.
"I don't really know," I said, "that label can be rather restrictive. I'm not really attracted to men, but I am to girls like you."
"Have you ever been with a man – other than girls like me?" asked Ginnie.
"Yes, before I discovered girls like you," I replied.
"Did you suck them," she asked.
"Yes," I said "I did, but much prefer sucking you."
"How is sucking a man different from sucking me?" Ginnie asked.
"The mechanical part is pretty much the same," I replied, "but the emotional part is completely different. Sucking a man is simply a way for the guy to climax, but sucking you is going down on my lady, and showing her how much I care."
"I hadn't thought of it that way," confessed Ginnie, "so you think of yourself as straight?"
"I don't know that there is a correct label," I said, "but I don't think I could really be considered as straight – maybe bisexual, but that doesn't seem to fit exactly."
"Well," she replied, "it doesn't really matter to me."
"I like to think about our relationship being a straight one," I said, "except during intimacy, we are pretty much like any other boy-girl couple."
Ginnie smiled broadly and replied, "I really like that – I thought for a long time that there would be nothing 'normal' in my life."
"I will do my very best to make your life as a woman as genuine as possible," I said.
"That is a tall order, Bill, but I certainly welcome it," she replied.
"How do see your sexual orientation?" I asked.
"I suppose straight. I am attracted to men (especially you) when I am a woman," she said, "but I suppose others might disagree."
"The agreement of others is irrelevant," I said, "society is a harsh judge, so we'll just remain discrete."
"You said my wig was not what made me a woman," Ginnie said, "what exactly did you mean by that?"
"What makes you a woman is what is between your ears," I explained, "not what is between or legs, or anything you may wear."
"When you are in boy mode," I continued, "do you really feel like a very different person?"
"No, not really," said Ginnie, "but I feel more feminine when dressed."
The clothing is simply the window dressing," I said, "very nice window dressing, but it gives you confidence. When you are in boy mode I think you are still a woman, but undercover – your boy self protects the woman inside from a very harsh society."
"That makes some sense," admitted Ginnie, "I'll have to think about it."
"I want you to learn to feel completely femme when you are naked," I said, "when you have achieved that, I want you to feel femme when you are in boy mode, though you will not act like a woman."
"Wow!" responded Ginnie, "Can that really happen?"
"Let's give it a try," I said.
We agreed to go out to a nearby shopping mall. I'm not big on shopping, but the mall is a great place for Ginnie to walk around in public. I wanted to help her grow her confidence, while being with me, affording a measure of safety that will further help her confidence.
We finished breakfast and Ginnie took me to the bedroom, wanting me to help her pick out something to wear.
"Let's try something first," said Ginnie, "undress me, Bill."
I didn't need to be told twice, so I removed her clothing with great interest.
Ginnie stood there naked before me, with her eyes closed. "What are you doing?" I asked.
"Just feeling," she said, "please hold me."
I took her in my arms and held her close to me, gently massaging her back. One of my hands rested on one of her soft, round buns – it felt wonderful to me and I couldn't resist kissing her again.
"You were right!" she said, "I am a woman, even when naked!"
She wrapped her arms around me and we continued kissing.
I helped her choose a nice blouse and skirt for the mall. She agonized over dozens of pairs of shoes before selecting a nice pair. They all looked fine to me, but the choice seemed really important to Ginnie.
We walked around the mall, and of course looked at lady's apparel. It would have been horribly boring to me, but as I looked at various items I pictured them on Ginnie. She held a pretty red dress up to her and asked, "What do you think?"
"I'm not so good at this," I said, smiling, "but I could judge this much better if you were wearing it."
"You want me to try this on for you?" she asked.
I nodded and Ginnie smiled and handed me her purse and went to the changing room.
I waited while she changed. Under any other circumstances I might have felt awkward standing there holding a purse, but I felt a sense of excitement knowing that Ginnie was trying on a dress just for me.
Soon she emerged, and modeled the dress for me, turning slowly so I could see it from all angles. "You like?" she asked.
"It looks wonderful on you, dear," I said.
She returned to the changing room and changed back into her other clothes. As we walked to the checkout counter she said, "Oh my gosh! I can't pay for this!"
"What do you mean?" I asked.
"My credit cards are all in Jim's name – I can't use them now," she said.
"I'll take care of this," I said, "just stay with me – I don't want them to think I'm buying it for me."
Ginnie giggled and accompanied me to the checkout. I paid for the dress while Ginnie smiled the entire time. We left the store and walked to the Food Court area, where we had a light lunch.
Ginnie thanked me for liberating her and making her feel so wonderful.
"I love the clothes," she said, "but am thrilled that I can still feel femme even without them, but I'm not sure I can feel that way in boy mode."
"Want to try tonight?" I asked.
"What do you mean?" she asked.
"I really like you, but I haven't seen Jim in awhile," I explained, "Why don't Jim and I go to Jake's bar tonight to watch the game over a few beers?"
"This is all happening so fast, Bill," Ginnie protested, "I don't know if I can handle it."
"I'll be there with you," I said, "we can leave any time you want."
Ginnie reluctantly agreed and we drove back to her place. I left for my house to get a change of clothes, pick up my mail and attend to some other things.
–––––––––––––––––––– To be continued ...
Feel free to contact me with your comments or requests. –Bill (oral_guy_2000@yahoo.com)
Please support this website by donating to nifty.org