Bob Returns To Crossdressing With Unexpected Results – Chapter Two

I left Jane’s house feeling exhilarated. I was fairly confident that I passed as a woman, but I only had Jane and Jim telling me that. Maybe they told every client that.

As I drove, I thought about what I had done. I not only dressed fully as a woman, and received lengthy instructions on how to act like one, but I had made out with a man and sucked his cock until he came in my mouth. I felt guilty. But not for the reason one might think. It was not because of what I had done. I felt good about my feminization. It was because I was doing it without Joann’s knowledge. I knew if this was to continue, I had an obligation to tell her. I hoped she would have some level of acceptance. Even if she only allowed me to do it in private, I would be content so long as she knew.

It was early evening as I drove home. At stop lights, men glanced over and smiled. I smiled back.

I didn’t want this day to end. I wanted affirmation that I was truly passable.

I decided to take a small risk. I pulled into the parking lot of a shopping mall not far from our house. I got out and walked around, pretending to window shop. Men stared at me. Women looked at me. I didn’t sense that anyone thought I wasn’t a woman.

My confidence rising, I went into a Kohl’s Department Store. I headed to the women’s clothing department. I was enjoying myself browsing through some bras when a middle-aged saleswoman asked if I needed assistance. I told her I wanted a fancy black bra. “What size are you?” she asked.

“36D,” I replied.

“I assume you want an underwired one?” she inquired.

“Yes, please. Something lacy.”

She showed me three lovely bras and I picked the laciest one. “You should get the matching panties,” she suggested.

“Sure,” I said.

It suddenly occurred to me that I didn’t have enough cash. I handed my credit card to her, hoping she wouldn’t notice the name. She did.

“I assume this is your husband?”

“Yes. Is that okay? He told me to buy something sexy,” I smiled.

“Aha,” she responded with a broad smile. “Since he’s paying, and I assume he’ll want to see you in these, may I suggest something?”

“Of course.”

“Hold on.” She left for a minute. When she returned, she asked, “Here is a matching garter belt, and a pair of lace top stockings. With your body, you’ll look fabulous, and he’ll love it!”

“I think he will, and I’m sure he won’t mind paying for it,” I said.

“One more item, if I may suggest?”

She went away again. “A semi-sheer black robe?”

I smiled. “He will love it.”

“Pair all this up with a pair of 4-inch spike heels, and you’ll have him in the palm of his hand.” She smiled like the Cheshire Cat.

“I love it,” I responded.

“I could help you with the shoes if you like. I’m authorized in that department, and it would be a nice commission.”

“Let’s do it” I responded.

We walked over to the shoe department. I took a seat and she measured my foot. “You’re a size ten, but I think we have that size in the pair I’m considering.”

She returned in a few minutes with a box. She opened it and pulled out two black patent leather shoes with pointed toes and four-inch stiletto heels. I gulped. I had three-inch pumps I could walk in, but I wasn’t sure about these.

“I’ve never worn heels that high,” I said.

“You will with a little practice. You’ve got the legs for wearing these. And your husband will go nuts.”

I slipped them on and stood up. I was a little wobbly, but I managed to take a few steps.

“I’ll take them. I’m sure hubby will love them.”

They were expensive but what the heck, my husband was paying for them.

“You must come back and tell me his reaction. I’d be happy to assist you anytime.”

“I will,” I said.

I was loving my first day in public as a woman. It brought back wonderful memories of shopping as a girl with my sister. I received a few stares from men, but they seemed to be admiring ones. I walked across the parking lot, making sure I swayed my hips and kept my shoulders back, as Jane had instructed.

My confidence was growing. I decided to stop at a bar that Joann and I went to occasionally. I pulled into the parking lot, took a deep breath, and went in. It wasn’t crowded, with only a few men and some couples scattered about. I took a seat at the bar I had sat at many times, but obviously never as a woman.

A bartender I knew came over. “Good evening ma’am. What can I get you?” He didn’t recognize me.

“A glass of Chardonnay,” I nervously said in my best feminine voice.

He poured a glass and set it before me. I took a sip and looked around. I noticed a nice-looking guy sitting down at the bar. He smiled at me. I smiled back.

He took my smile as an invitation. He got up with his drink and walked towards me. “Oh god,” I’m thinking. “What have I gotten myself into?” But I was excited.

“Good evening. Mind a little company?” he said, smiling at me.


“Sure,” I said. Still working on my feminine voice.

“My name is John,” he said as he took the stool next to mine.

“Elizabeth,” I responded.

John explained that he occasionally stopped in after work for a glass of wine before going home nearby. “I haven’t seen you here before.”

I told him I lived nearby, but usually didn’t hang out at a bar. We laughed. “I had a meeting and just felt like a glass of wine before going home,” I explained.

John bought me another glass of wine, and we had a nice chat about the neighborhood.

After finishing the second glass of wine, John asked if I had had dinner. I realized I hadn’t and was hungry. “I haven’t,” I said, feeling more confident about my voice.

“There’s a nice little pizza place two blocks from here. Would you join me?”

I hesitated. In one day, was I going to be with two men? But I didn’t want this to end. I said “Sure, that would be nice. I’m starved.”

We decided to go in his Mercedes. We arrived, got a table, and ordered a pizza. I had two more glasses of wine and was feeling great. John was funny and charming. We talked for quite a while while downing the pizza.

At one point, he said, “Do you know of the actress Lauren Bacall?”

“Of course. She was married to Humphrey Bogart.”

“Your voice is like hers. Deep and sultry,” he said.

I loved that. Confirmation that I sounded like a woman. I smiled.

I had to go to the bathroom. I realized I was going to, of course, use the Ladies’ Room. “Another new experience for Elizabeth,” I thought. I excused myself. I went into a stall and sat. I lifted my skirt and struggled to pull down the gaff. I peed, pulled out toilet tissue, and wiped a drop off the tip of my penis. Because other women were in the bathroom, I knew pulling out tissue would be a necessary sound. I exited the stall and saw an attractive, middle-aged woman putting on lipstick at the mirror. I opened my purse, took out my lipstick, and did the same. We smiled at each other.

“Lovely jacket,” she commented.

“Oh thank you,” I replied. “It was a gift from a friend.”

I exited the bathroom and rejoined John. We chatted and he told me how pretty I was. I loved it.

We finished and John paid the bill. We headed to the car. He grabbed my hand on the way. He had parked in a dark spot behind the restaurant.

We got in but he didn’t start the car. He reached over and pulled me towards him. I didn’t resist. He kissed me and I willingly kissed back.

I was enjoying it. I felt it was affirmation of my increasing femininity. I was absorbed in being treated like a woman. I glanced down at John’s crotch area. He had a raging hard-on trying to burst out of his pants. I thought to myself, “He bought me drinks and dinner. I kind of owe him. It wouldn’t be fair to just leave.”

I reached down and rubbed his crotch. Yes indeed. He was hard as a rock. I started opening his pants while we kissed. He willingly helped. Out sprung a nice-sized, very stiff penis. “Well, here you go again, you slut,” I thought.

I lowered my head and took the second cock of the day into my mouth. I took my time, sucking a little and then just licking up and down his lengthy rod as I daintily held his mushroom head. I found myself wanting to explore.

I wrapped my tongue around his large head, allowing my tongue to explore the opening at the tip. He let out a soft squeal. “I’m good,” I thought.

Next, I lowered my mouth and started licking his balls. He pushed his pants down and spread his legs to give me better access. He had a large, hanging sac and I lifted it into my mouth. I softly juggled both testicles in my mouth while I stroked him. “Oh Elizabeth,” he whispered.

I returned to sucking, sliding my feminine lips up and down his wet shaft.

I sped up. He started to raise his hips, forcing his cock further into my mouth. I sucked hard. He let out a loud grunt. My mouth started to fill it’s the now-familiar taste of cum. With a few more thrusts between my girly lips, he was finished. I sloshed the warm, salty cream around in my mouth for a few seconds, then I swallowed. I carefully licked him clean and sat up.

“You’re amazing Elizabeth.”

I opened my purse, took out my lipstick, and applied it while looking in the mirror in the visor. Luckily my wig had stayed in place. I told him I had better get home. He drove to my car at the bar and stopped the engine. He pulled me to him and we kissed a bit more.

He asked if he could see me again. I had assumed this was coming. Of course, he’d want to see the woman who had just given him a great blow-job. I had a response ready that would neatly get me out of this situation.

“I’d love to John, but there is something I need to tell you.”

“What’s that?”

“I’m married and I don’t think my husband would approve,” I said as I smiled at him.

He sat stunned. I kissed him again, said good night, and went to my car. I smiled all the way home.

When I got home I knew that I had to tell Joann about Elizabeth. I knew I had to break it to her slowly. Certainly, I wouldn’t tell her about the two men I had been with; at least not now. I liked being a woman. I could only hope she would understand.