I steered into the driveway that I had pulled into hundreds of times. This was the first time dressed as a woman. I knew I couldn’t stop what I started. I wasn’t controlling the overwhelming desire to be feminine. It seemed to control me. As a couple walked by, I pressed the remote and pulled into the garage.
I watched TV for a while. Though it was late, I decided to try on the lingerie and heels I purchased. After dawning the bra, panties, garter belt, and stockings, I sat to put on the stilettos. Although the sales lady said they were four inches, they were probably more like four-and-a-half-inch heels. I stood up unsteadily. I carefully walked to our full-length mirror. My legs did look great.
I walked around. I needed practice. I put on the new robe and moved through the entire house, improving with each step. I had a newfound appreciation for women who strutted easily in these heels. I opened the patio door and walked around our large patio, my heels clicking on the pavers. It was a beautiful, warm night. I was safe. There was a six-foot privacy fence on each side. Suddenly I heard a male voice from the other side.
“Joann, is that you?”
It was our neighbor, Frank. He and his wife were friendly. Frank and I occasionally had a beer together. He is a big, muscular former football player who wouldn’t understand my current outfit.
I responded in Bob’s voice. “No Frank, it’s me, Bob.”
“Oh, I thought I heard the sound of women’s heels on the patio and assumed it was Joann. “I’m sorry. I suppose it’s too late for a beer, huh?”
“Yeah, I’ve had a long day. I’m going to turn it in.”
“Okay, good night Bob.” I heard him close the door.
“Well that was close,” I thought.
I lay on a chaise and rubbed my lacy panties, thinking about what could have happened had Frank walked in the gate. I got aroused and pulled off my panties. I stroked my stiffening cock. Within a short time, I released a number of arcing spurts onto the patio. I drifted off to sleep.
Suddenly the gate to our yard banged open. It was Frank. I jumped up, standing there in the dim light in my black bra, garter belt attached to my lace top stockings, shaking in my stilettos. “Oh my god,” I thought. “I’m trapped.”
“What the fuck,” Frank muttered. “Bob, is that you?”
I just stood there. There was no escape. I didn’t have panties on. To complicate the situation, I was getting aroused.
Frank walked slowly towards me. “Well, aren’t you a pretty lady? I always thought you were a little girly. But wow, you do make a striking figure. And I see you’re excited to see me,” Frank mused as he looked down at my cock now pointing up at him.
“I don’t know what to say, Frank,” I whimpered like a girl. “Can we somehow just keep this between us?” I begged.
“God, you even sound like a girl. You don’t have to say anything. I’m not going to tell anyone.”
“Oh thank you, Frank,” I murmured.
“On one condition,” Frank smiled.
With that, he unzipped his pants and pulled out a hardening cock. Come here and get on your knees.
I did as instructed. My knees hurt on the brick patio. I was inches from his now completely stiff, long, and thick member. My girl cock was stiff and throbbing.
“You want this, don’t you? Answer me!”
“Yes Frank, I do.”
“Tell me what you want to do with my big cock. Tell me,” he commanded.
“I want to suck it, Frank.”
“You’ve always wanted to blow me, haven’t you?
“Yes Frank, I have.”
“Good girl. Open your mouth.”
He shoved his cock into my waiting mouth. I gagged. Frank didn’t care. He started pumping the massive rod furiously between my lips. He slowed down, falling into a smooth rhythm while he clasped the sides of my head. He kept this motion going for at least ten minutes. He let go of my head, but I didn’t release him. I was enjoying pleasing my neighbor. I allowed him to continue his rhythm without pulling away. My arms dropped to my sides.
He stopped thrusting. But when he did, I took over, moving my head back and forth, Frank just stood there, letting me please him. I increased my speed as I simultaneously sucked harder. I reached up and massaged his large balls. Frank started to moan loudly.
I stopped and let his cock fall out of my mouth. I looked up from my subservient position. “Shush Frank. Your wife will wake up. Let me finish.”
I placed his huge cock back in my mouth. I went back to work, sucking hard. His body stiffened, and I began to taste the now-familiar flavor of semen. My mouth filled. I sucked until he finished squirting. Even after he finished, I kept my lips attached. He pulled back, and his flaccid dick slipped out of my mouth.
“I’ll keep this between us Bob. You’re an excellent cock sucker. We will do this again. Just make sure you tell me when Joann is going to be out of town, okay.?”
“I will Frank. Thank you for not telling anyone.”
Frank smiled at me kneeling in front of him, cum dripping from my mouth. He zipped his pants. “Let’s have a beer tomorrow.” He snickered, turned, and went out the gate.
Suddenly, I heard the pleasant song of a Robin. “What? What’s going on?” I thought. I realized I was lying on the chaise lounge. I wasn’t on my knees. Then I noticed it was getting light. It was a Robin. “Oh god! I was dreaming.”
I had laid there all night in my lingerie, without panties. I looked around. Was it possible a someone saw me from the second-story window next door? Probably not,” I thought. “It’s barely light.”
I glanced at my panties lying on the patio. I got hard reliving the dream. I couldn’t resist. I gripped my girl pole and stroked it. It took a while, but I launched a creamy load.
I picked up my panties, sat back down, and slipped them on. I walked inside.
I made coffee, and decided to change into a skirt and blouse. I had time. Joann’s plane was due at noon.
She called from the airport to tell me she was on her way. I reluctantly took off the skirt and blouse and removed my makeup. I put on jeans and a sweatshirt. “Men’s clothes are so dull,” I thought. I stowed my girly things in a locked tool cabinet in my downstairs shop.
I had to wait for the right moment to tell her about, well, Elizabeth.
We made love that night. We kept changing positions. Missionary, cowgirl, finishing with doggie. She commented on how passionate I was. Because I had masturbated twice, I lasted. “I don’t know what’s gotten into you, but I hope it stays. I haven’t had three orgasms in a while,” Joann giggled.
We went about our normal business. A week passed. The time never seemed quite right to bring it up. I found myself dressing every time she was out for a few hours. This went on for weeks. I didn’t like it. I felt guilty I was still hiding it.
Four weeks after my big day out, we were relaxing after dinner on a Friday evening. Joann was channel surfing and she landed on“Tootsie.” We watched and laughed.
“It’s amazing how passable Dustin Hoffman was as a woman, wasn’t it? You would never think he could pull that off,” She commented.
“Really amazing,” I responded. It’s Karma, I thought.
“Honey, do you remember when I told you how I crossdressed when I was a teenager?” I said calmly. “I was very passable, so I know it can be done.”
“Sure I do. You told me how your sister dressed you for a Halloween party, and everyone thought you were a girl. And that the two of you would go shopping together with you dressed as a girl. I always thought it was so cute because, with your build and height, you must have passed,” Joann responded. “I always wondered how you’d look dressed as a woman.”
I was surprised by that response. Joann went on, “Why do you ask? Have you thought about doing it again?”
I didn’t immediately answer. Joann had a sly smile. “You have, haven’t you?” she asked.
This hadn’t gone at all as expected. I squirmed. I started to speak, but she cut me off.
“Listen, honey. I never told you, but after you disclosed your experiences, I went on the internet and did some research on cross-dressing. It was enlightening. I learned it’s more common than people think. I also learned that most crossdressers, especially married ones, frequently feel guilty and try to quit. However, the urge almost always returns.”
“I thought about that a lot. Honestly, I always expected you would have a desire to do it again. I decided that if you did, I would be open to it. So please be honest. “Do you want to? Or have perhaps I should ask if you have been crossdressing again?”
I looked her in the eyes and said “Yes I have. It’s a very recent development. I have hated hiding it from you, so I’m glad the cat is out of the bag.”
She sighed a sigh of apparent relief. “I am glad too. I didn’t tell you, but I found a tissue with lipstick on it. I thought you might be having an affair. I’m so relieved it was yours. Now that didn’t sound right.” She laughed out loud.
She went on. “From what I read, it’s undoubtedly part of who you are. It certainly seems to have had a positive effect on your love-making. You have been so passionate lately.” Joann laughed again.
“We definitely need to talk about it. I’m assuming you wouldn’t bring it up if you didn’t want to dress around the house?” she inquired.
I admitted that I did, but only if she could somehow come to terms with it.
“You don’t have to see me or be involved. I just don’t want to do it behind your back,” I said.
“I truly appreciate that Bob. I don’t want you to feel like you must hide it. I just need to prepare myself to see you in a dress.” She giggled. “I’m worried you might look better than me,” We both laughed. “Let’s talk about it more tomorrow.”
We went to bed and, once again, had incredible sex.
After breakfast, Joann asked me if she could ask me some questions.
I prefaced her questions by telling her again that this had come on only recently. “The urge to do so is intense. I don’t know why, but I can’t seem to resist it.”
“Tell me what you wear. Do you wear a bra, panties, dresses?” she asked.
“Yes, I have dresses, skirts, and blouses. I have a few bras, panties, and other lingerie.”
“Do you wear a wig, heels, makeup?”
“Yes I do”, I answered.
“Do you act feminine when you are dressed?” she inquired.
“I try to,” I smiled.
“Let me just jump ahead here,” I said “Remember when you were out of town a few weeks ago?”
“Of course,” she responded.
“That Saturday, I met with a very nice, slightly older woman, who has a small business helping crossdressers with clothing, lingerie, makeup, etcetera. She even teaches how to act and talk like a woman. Her name is Jane and she calls it Transformations by Jane.”
“Ah, I see”, she responded.
“So Jane dressed you, and instructed you about looking and acting like a woman?”
“Yes she did,” I answered.
“Have you dressed completely as a woman?” she asked.
“Yes, with Jane’s help. When she was finished, she told me that I was the most passable client she had ever had. She told me no one would ever guess I was a male.
Jo went on. “Wow. Somehow I’m not surprised though. You are so thin and fair. Have you been out in public as a woman?”
“Yes, but only that night. I drove home from Jane’s fully dressed. I wanted to see if what she said was true. I stopped at the mall and walked around. No one appeared to think I wasn’t just another woman shopping at a mall. I even bought some lingerie. The sales lady clearly thought I was a woman. I have to admit, it was fun.”
“I was feeling confident and decided to stop at The Bungalow Bar for a glass of wine. A man even came over and bought me a glass of wine. I felt I passed the test. Jane was right.” I smiled broadly.
“That’s so cool that you went there. How did that feel?” Joann asked.
“I enjoyed it,” I responded. I decided it was way too soon, or if I would ever, tell her about the blow-job.
“Well honey, you certainly have piqued my interest. I’m still processing this. Let me think about it and perhaps tomorrow you could dress for me.”
“Really?” I blurted.
“I think so. But let me sleep on it. I definitely don’t want you to hide it,” Joann said.
That night, we again had very passionate sex. I had mounted her and we were furiously going at it. Suddenly, she told me to stop. “Fuck my mouth, honey.” She slid down and had me insert my hard cock in her mouth. I pumped it between her lips. I realized she was fingering herself while I fucked her mouth. It was very erotic. While she sucked away, I wondered if I was as good as her. I filled her mouth and, like me, she swallowed.
In the morning, Joann smiled at me and said, “I must say, if the result of your crossdressing is that you become a more passionate lover, how can I not encourage it?” We laughed.
“I assume you are hiding your things somewhere, so why don’t you get them and get dressed,” Joann suggested.
“Are you sure honey?” I asked. “I’m not pushing it.”
“I am. But don’t get completely dressed. I’d like to take this in stages. I think it would help me to adjust if I see each step, so after you have a bra and panties on, come and show me.”
“Okay, sweetie. I will.”.
I got some of my things and went to our bedroom. I took off my clothes and put on a white lace bra and matching panties. I slipped the forms into the bra.
I shouted that I was ready. I walked into the living room.
Joann stared for a moment. “Okay. You have lovely lingerie, and bigger tits than me.” She giggled.
Joann felt my boobs. “Wow, those feel very real. But so far, you’re just Bob wearing a bra and panties.”
Joann told me to put on makeup and come back with a wig on.
I did as told. I wanted to look good, so I took my time. When I finished, I slipped my wig on, pinned it, and brushed it a little.
“I’m ready hon,” I shouted.
I walked out.
“Well now you are starting to look like a woman,” Joann said. “Very nice job on the makeup dear. Jane taught you well. I’m okay with this so far, so what’s next?”
“A girdle with hip and butt padding, a waist-cincher with garters, and stockings,” I told her.
“That sounds intriguing. Let me see.”
I returned to the bedroom. I was excited. Joann seemed to be accepting everything so far.
I slipped on my padded girdle, as well as the waist-cincher, then my stockings. “Okay hon, here I come.”
“Oh my,” she giggled. “You’re really taking shape, shall I say.” We both laughed.
“I think it’s time for the final steps. Will I see you in a dress or skirt and top? She asked.
“Your choice,” I smiled.
“How about a sexy dress? Might as well go full girl.” Joann giggled.
I turned and went to the bedroom.
I selected a mauve dress with long sleeves. I slipped it over my head. I looked in the mirror. It certainly showed my curves. I finished with a pair of black pumps with a two-and-a-half-inch heel…
“Are you ready dear?” I shouted to her.
“Yes, I am.”
I confidently walked into the living room. Joann stared at me for a few moments. She smiled. “I knew it,” she said. “You have a better build and are prettier than me.” She laughed.
“Bob, Jane was right. Even as your wife, if you walked past on the street, I wouldn’t know it’s you. That padded girdle and bra give you a very feminine figure. This is weird, but you are so convincing that I feel I shouldn’t call you Bob. Do you have a female name?”
I smiled. “Jane and I discussed this and came up with Elizabeth.”
Joann smiled. “That’s a nice name. Do you want me to call you Elizabeth, at least when you’re dressed?”
“If it is okay with you,” I answered.
“Why not? You look like a woman, not Bob. And I’m amazed at how feminine you suddenly are. Your mannerisms have changed. Even your voice. Do you like being feminine?”
“I imagine no wife wants to hear this from her husband, but I love being feminine,” I said. “I can’t really explain it, but I hope you can somehow understand.”
“Honey, I will do all I can to understand. I assume it’s okay to say this now, but many of your mannerisms have always been somewhat effeminate. It’s never bothered me. I didn’t marry you because you were some macho guy.”
“Let’s be girlfriends when you’re dressed. Would you like that?” Jo asked.
“I think I would,” I responded.
I made another pot of coffee. We sat and talked for hours. Joann asked many questions. I explained that this didn’t change my feelings for her. “I think it’s just part of who I am.”
“This is weird, but I feel like I’m talking to a woman I just met. I guess I am.”
“I have to ask this. Since you like looking and acting like a woman, do you think you might be bisexual?”
I hadn’t really thought about it like that. Even though I had kissed men, and sucked their cocks, in my mind, I did it as a woman.
“I don’t think so, Jo. As a man, I have had no interest in another man. As a woman, I suppose the attention of a man has the effect of making me feel more feminine. I do like the feeling. Does that make any sense?”
“Kind of. I’m realizing you don’t just want to dress, but you want to basically be a woman, at least when you look like this. It’s like an actor becoming completely absorbed in a role. Am I getting it?” she asked in an earnest tone.
“I think so. I feel transformed.”
“Actually, this could be fun,” she said. “I can’t get over how convincing you are. It certainly helps that you are so thin. No one would know you’re a male.”
“That’s so sweet of you to say,” I said. “That doesn’t sound right,” I laughed.
“I think you should stay dressed all day. Let me get accustomed to being around Elizabeth.”
We spent that day cleaning and working around the house. It was like a normal Saturday, with the exception that I was wearing a dress. We even went out on the patio and did some planting. It was approaching dinner time and Jo said, “Let’s get a pizza for dinner. I’ll order our regular.”
Twenty minutes later, the doorbell rang.
“Elizabeth, would you get that?” Joann asked as she smiled and walked into the kitchen.
I looked in the mirror and went and opened the door. A young man looked at me and said “Good evening ma’am. Here’s the pizza you ordered. It’s already paid.”
“Wait. Let me get your tip,” I said in my feminine voice.
I obtained a ten and handed it to him. “Thanks, ma’am. That’s nice of you.”
Joann came out of the kitchen with plates. “I bet you loved being called ma’am. And I’m impressed with your voice. You sound like a woman.”
We had dinner. By bedtime, Joann said, “While I’m getting used to Elizabeth, I’m not quite ready to go to bed with her.”
“No problem hon.”
I changed and removed my makeup. Once again, the sex was great.
On Sunday morning, Joann told me she was fine with me getting dressed again. “I know you want to.”
I did. I put on a red pleated skirt and a pink blouse.
When I appeared, she said, “I’m going to have to get accustomed to you having a better figure than me,” she giggled.
I spent the entire day dressed. We even went out for a drive and stopped at a park to go for a walk.
I told Jo how much I appreciated her understanding.
“I’m getting used to it. It’s still you, just in feminine form.”