I connected with Jim online. Although married, I enjoyed having occasional one-night flings. I’d usually connect with a married guy who came to town on business. I wasn’t interested in anyone local. It was important to get to know the guy before I met him though. The process took a while but always resulted in meeting a nice guy. Over the last couple of years, I’d fucked fifteen very nice and appreciative married men. All but a couple were one-nighters. It had become my hobby.

Jim was married and told me he came to town often on business. Perfect! We flirted. He was fun. That led to the private sharing of some personal information. We began messaging daily. There were exchanges of emails. This is what I usually did. If a guy wasn’t willing to do this, he wasn’t going to do me.

As time went on, I realized that i had more in common with this guy than the others. We both longed for romance, passion, something new and exciting. The more we exchanged information, the more I liked him. I started thinking that maybe I’d meet this guy more than once.

I live in a small city that Jim traveled to regularly as part of his job. I am a nurse and work nights at the university hospital. I like working nights. It allowed me to have my sexual encounters on the way to work. I’d just tell my husband I had a meeting before my shift.

I never sent a photo, but I described myself. I told Jim I was attractive, had a little extra weight, and full breasts. I am blond and fairly tall. He described himself as medium height, very fit, thin, and attractive. He told me he had long blond hair which he usually wore in a pulled-back ponytail.

Clearly, it was worth meeting him. He clicked all the boxes and I knew we’d have a good evening of sex. We decided to meet the next time he was in town. It turned out he always stayed at the nicest motel in town, which happened to be on the way to the hospital. How convenient. That evening, I told my husband, Tom, that I had to get to a meeting before my shift. This was common.

I arrived at his room just after five. When the door opened, I was pleasantly surprised. He was very attractive. Not so much handsome, as cute. His facial features were almost feminine.

We didn’t hesitate and immediately kissed. It didn’t take him long to undo my bra and softly caress my large breasts.

In no time, we were naked in bed. He fingered me while I stroked his cock. Then he mounted me. He took his time. Most guys couldn’t wait to cum. But not him. It was wonderful. He has a nice cock - about seven inches with a big mushroom head. He took his time and allowed me to have more than one orgasm before he came. We got partially dressed and talked some more. We ended up back in bed before I had to leave for work. I was happy when he asked, “Nora, may I lick your pussy?” He was good at it. After eating me for quite a while, he fucked me from the rear. I thought, “This is great. Maybe we should meet again.”

He was different than my other flings. He was kind and sensitive; nothing like my husband. He took his time and made sure to please me.

Jim was in town often. He was a lawyer and had a major client here. I decided to meet him again two weeks later. The sex was even better. He seemed to love eating my pussy. I really liked this guy. I decided that this was a good situation. I can get fucked regularly without having to find a new guy all the time. I started seeing him at least every two weeks. Whatever I asked him to do, he did. If I said “lick me until I have an orgasm,” he did. If I said “fuck me in the ass, in my ass went his stiff cock. He was intent on pleasing me. I admitted I enjoyed being dominant. I asked if he minded. “Not at all. I think I like being submissive.”

We explored our desires. He asked me if I liked masturbating. No one had ever asked me that. In fact, I love to masturbate. I admitted I did. I told him I had a big, double dildo I used. Then I played with it while he watched.

“How about you?” I asked. Next thing, we were watching each other masturbate. It was so erotic. I loved watching him squirt his cum. Once, when he came in his hand, I told him to eat it. He did. I found that so erotic.

We wanted to discover more about each other. One night, after I got on top and fucked him hard, he asked me if I had any secret desires. I shyly admitted I liked watching male sex. “You’ll think I’m weird. For some reason seeing a man suck or fuck another guy turns me on,” I said. He didn’t care. He said he found that “fascinating.”

“What about you?” I asked, smiling. For some reason, he turned red and squirmed. “Well, I have something that I’ve never told anyone I know. I’m not sure I’m ready to tell you. You’ll think I’m really weird.”

“Come on. Tell me,” I insisted.

“I don’t think so.” He said.

“If you want to fuck me again, you have to tell me,” I said, smiling.

“Okay. But please don’t laugh.” He hesitated.

“I like to wear women’s clothes,” he finally said.

I was a bit shocked but also intrigued. That wasn’t something I expected. “Do you mean, an occasional item, like panties? Or do you dress up completely?

Jim squirmed again. I assured him that it didn’t matter. I had fallen in love with this person.

“I dress completely. I’m what is known as a crossdresser,” he quietly said.

I sat for a minute. Here I was, in love with this wonderful guy, and now learning he likes to wear women’s clothes.

“Why don’t you fuck me again, and then we can discuss this further?”

We made love. It was fantastic. “Well,” I thought, “he’s still a great fuck.”

I learned that Jim had been cross-dressing since he was a teenager. He admitted that he had never told anyone close to him. I asked if he was gay, or bi. He shyly admitted that he had met married men, but only when dressed.

“What do you do when you meet them?”

He squirmed again. I assured him it was okay. In fact, I was getting turned on.

“I usually suck their cocks,” he admitted.

“Do they cum in your mouth?”

“Usually, Yes. I’m pretty good at it.” He smiled.

“Oh my god,” I thought. “Why is this getting met wet? Well, I did tell him I like gay sex.”

“So, before you met me, you would be here, dressed as a woman, and meet married men and blow them?”

“Well, yes,” he admitted.

“Wait a minute. On the nights you’re here, and I can’t make it, do you dress?”

Jim smiled and admitted he did.

“You sneak you. You certainly have my attention. Now you have to dress for me. Would you do that?”

He smiled and told me that he would if I really wanted him to.

The next week, Jim was in town for a few days. I told him that I wasn’t quite ready to just show up and see him in a dress. I told him I wanted to watch him dress, one step at a time, so I could adjust to it. I asked what he was going to wear. “I will end up in a dark pink pencil dress if that’s okay,” he replied shyly.

“Okay, let’s get started,” I said. “I want you to go in the bathroom and come out in panties. Then you can keep adding, one thing at a time.”

I could tell he was more submissive than usual. I was enjoying this.

In a minute, he walked out wearing only a pair of black lace panties. He stood before me.

“Those are darling. Okay, I assume a bra is next?”

He smiled and turned to go to the bathroom.”

He soon returned wearing a matching black lace bra.”

“You have sexier lingerie than me,” I laughed. “Wow, you have nice tits. What size do you wear?”

Bob responded, “I wear a 36C, and these are silicone breast forms in the cups.”

“Well, at least I have bigger tits,” I laughed.

“Okay, what’s next?”

He went back and a few minutes later came out wearing what he described as a waist clincher with garters. The garters were attached to black opaque stockings. He was also wearing black pumps with what looked like three-inch heels. It was obvious he was accustomed to wearing them.

“Very sexy,” I smiled. “Okay, I’m adjusting to this well. Keep going. I assume you wear makeup?”

“Of course. And it will take some time to do my makeup and hair. Do you want to go get a bottle of wine? Hopefully, I’ll be done when you return.”

I left to get the wine. He gave me a key card. I took my time. I figured, like any woman, he’d need time to get ready. I was anxious to see him. When I returned, he was still getting ready in the bathroom.

After another fifteen minutes, he said, “Okay, Nora. I’m ready. Are you ready?”

“Yes, hon. Let’s see what kind of girl you have become.”

He walked out. “Oh my god,” I thought. I was staring at a woman. This wasn’t a guy in women’s clothes. It was a very attractive woman. Perfect makeup. Pretty, feminine hair. He even walked in heels like a woman. He was wearing a perfectly fitting dark pink sweater dress. I sat and stared for a minute. It was a complete transformation. I was fascinated, and, surprisingly, turned on.

“Nora, please say something. Are you going to dump me? What do you think?” He said in a surprisingly feminine voice.

“I’m amazed. I would never know you’re not a woman.” I giggled.

“Really?”

“Yes. You completely pass as a woman. Shit, you’re prettier than me. Your hair looks so feminine. Do you travel with a curling iron? It’s amazing what you’ve done to it.”

“Yes, I do. Sometimes, if I have time, I use curlers.”

I smiled. “I see why you have long hair. I’m impressed.”

“So, are you okay with me like this, or are we finished?”

“I think so,” I said. “I need a little time to adjust. I honestly didn’t expect you to look like an actual female. I thought you’d just be a guy in women’s clothes. But it appears I have a new girlfriend, as well as a boyfriend.”

We both giggled. “Oh my, you giggle like a girl,” I said.

Our relationship changed, but not in a bad way. I researched crossdressing and learned that it was much more common than I’d ever thought. I realized it was simply an aspect of the complex person I’d fallen in love with. We still had great sex. But I also encouraged Jim to dress when he wanted to and to enjoy his feminine side.

I decided I couldn’t call him Jim when he was dressed. We agreed on a name - Elizabeth. Now, when he came to town, we’d have a great evening of wild sex, but then I’d get to see my new girlfriend. With some coaxing, I convinced her (If he was dressed, it was she/her) that we should go out. “Obviously, I won’t have to worry about being seen with another woman in public.”

First, we went for a walk downtown. While we got some looks, it was apparent that it was because we were two attractive women. We went to a bar for a drink, and two men bought us drinks. We flirted with them. We were both having fun. We worked on her voice and I fine-tuned her mannerisms. I was turning my boyfriend into a girl.

We started a routine. The first night he was in town, he was Jim. We’d fuck, do sixty-nine, anal. The sex was great. But the second night, if I was available, I’d get together with Elizabeth. I liked my girlfriend. I began to think of him as a woman. We’d talk about girl things. We’d go shopping. We bought jewelry and tried on dresses together. I bought her a purse. I was truly enjoying her. She became more and more confident in her ability to pass as a woman. The more confident she became, the more willing to be feminine she was.

Jim was going to be in town for three days one week. We had an evening of our usual great sex. The next day, I told my husband I was going to dinner with an old friend who was in town. I assumed he wouldn’t care. But for some reason he asked, “Is it a guy?”

“No, silly. An old girlfriend. She’s in town on business.”

“What’s her name?” He inquired.

“Elizabeth,” I replied.

He was obviously suspicious. Maybe I had been out with Jim too many times. Was I getting careless? It occurred to me that he might think that I was having an affair.

“Don’t you believe me?” I asked.

“Sure. But how about I join you two for a drink before I meet the guys for bowling? Then the two of you can catch up over dinner.”

“Oh god,” I thought. My mind raced. “If I say no, he’ll be more suspicious. It’ll make seeing Jim more difficult. On the other hand, if I say yes, he’d be meeting the man I’m having an affair with, but he’d be dressed as a woman. That’s insane.” I had to think.

“I have to go to the bathroom. Be right back.” I bought some time.

I tried to think this through. “Was it crazy to introduce my husband to the man I was having an affair with? Was it even crazier that he could convince my husband he was a she? But I knew she was quite passable. Everywhere we went, everyone thought he was a woman. And if he did meet Elizabeth, and she told him she came here regularly, maybe it was a good idea. He’d have no problem with me meeting a girlfriend.” I left the bathroom.

“Let me call her. Okay?” I blurted.

“Sure. Go ahead.”

I dialed Jim’s number. He answered.

“Hi, Elizabeth.”

“Hi, Nora. I'm not quite Elizabeth yet. I’m just doing my makeup. Are we still on for drinks and dinner?”

“Well, yes. But a slight change in plans. My husband, Tom, is here, and he would like to join us for a drink. Is that okay?”

“Oh my,” Jim responded. “Are you kidding?”

“Not at all. It’ll be fine. You’ll like him. I’ll pick you up at five.” I hung up.

Bob messaged me shortly. “I hope that was a joke.”

I replied - “Unfortunately not. It’ll be okay. It will make things easier for us. I’ll explain when I see you. What are you wearing?

Jim replied - “I was going to wear a black pencil skirt with a ribbed beige sweater and the mauve jacket we bought last week.”

“That’s perfect. Finish your makeup and hair, and I’ll see you in a bit. I’ll explain more.”

Half an hour later I knocked on the door to her room. The person who opened the door was a beautiful woman.

“Oh, Elizabeth. You look lovely.”

“Thanks, Nora. But please explain. I’m terrified.”

“My goodness,” I thought. “He really sounds like a woman.”

“I think Tom started suspecting I was having an affair. He clearly didn’t believe I was meeting a woman tonight. So, he kind of forced the issue. But, this will make it easier for us in future. He’ll have no problem with me meeting you once he meets you.”

“Are you sure he won’t suspect?”

“It will be fine. Face it. You’re a woman. Hell, you’re my most feminine girlfriend.”

We both laughed. “By the way, you look great in that outfit. I bet Tom thinks you’re beautiful.”

We drove to the bar, parked, and walked to the front door.

I looked at Elizabeth and told her to relax. But I was thinking, “I can’t believe I’m about to introduce the guy I’ve been fucking to my husband.”

We walked in. Tom was at the bar and waved.

He got up. “Hi, you must be Elizabeth. Nora didn’t tell me how pretty you are.”

I smiled and thanked him.

We talked. It was actually fun seeing my husband flirt with Elizabeth. Tom asked her about her work. She said she was a lawyer and she had a major client in town and she had to travel here often.

“It’s nice to be able to get together with an old girlfriend after being with clients all day. I hope you don’t mind me stealing your wife for an occasional evening,” she said as she smiled at me.

“Of course not,” Tom responded. “Nora, we should have Elizabeth over for dinner sometime.”

I suggested we go to the Ladies' room.

I was excited. I kissed her deeply. “You pulled it off, girl. Tom seems charmed by you. I’m proud of the woman you have become.” Another woman came in. I’d forgotten my purse, but Elizabeth had hers. We fixed our lipstick and exited.

Soon after, Tom excused himself. “It was a pleasure meeting you, Elizabeth. Hope to see you again. I’ll let you girls have dinner.” He gave Elizabeth a hug and a kiss on the cheek and left.

When Tom left, we looked at each other. Then we both started laughing.

“We did it,” I exclaimed. “You were incredible.”

“Thanks, Nora. It was fun. How crazy is it that your husband kissed me?”

From then on, it was easy to meet. I’d just tell Tom that Elizabeth was in town.

I became more and more comfortable with her. It may seem odd, but I thought of her as a woman.

We would have sex, but I looked forward to seeing my girlfriend.

One evening, Elizabeth and I went out to a bar. I asked her if she missed being with a man occasionally. “I think what I liked about it, is it made me feel more like a woman. I can’t believe I just told my girlfriend I suck men’s cocks to feel more like a woman.”

We both giggled. “It’s even crazier that you telling me that turns me on,” I replied.

“If you want to meet a man, it’s fine with me. In fact, I find it very erotic. So, since we can’t get together tomorrow evening, I think you should arrange a date. But under one condition.”

“What’s that?” She asked.

“You have to tell me all about it,” I giggled.

I had to work early the next day. I stopped by to see Jim on the way to work, but I found Elizabeth getting ready. She was so cute with her curlers in her hair. She told me that she had arranged to meet a guy.

“He’s married. Seems very distinguished. Says his wife is no fun and he loves girls like me”

“Does he have a big dick? I asked.

“They usually lie, but he says he is seven inches and thick,” Elizabeth replied.

“Do you usually kiss the guys? I asked matter-of-factly.

“Sometimes. Depends on the guy. Some like to make out before I go down on them.”

“Well, have fun, and I can’t wait to hear all about it.”

The next morning I stopped by. Jim had to leave soon, but we managed to get a good fuck in. Then I made him tell me about his evening.

He said that the guy did want to make out. “We kissed for a while. He was a good kisser. He didn’t have a lot of time, so I took his cock out while we were kissing. He wasn’t lying. It was very thick.”

I was getting wet hearing this. What a strange relationship we had.

“Go on,” I said.

“I got on my knees and took my time licking his cock. He asked me to suck on his balls.”

“Did you?” I asked.

“What do you think?” He smiled.

“I sucked on his big balls while I stroked his rod. Then I started sucking. I don’t think he had cum in a while.”

He kept saying, “Oh Elizabeth. You are such a good cock-sucker.”

“Oh god, this is getting me so aroused. Do you mind if I finger myself?”

“Of course not. I’m glad you enjoy it.”

“Anyway, he grabbed my head and started face-fucking me. He stood up so he could more easily push his cock in and out of my mouth. He’d pull it all the way out occasionally, and slap my face with it. After a few minutes of me sucking really hard, he started cumming. Nora, I’d never had so much cum.”

I was furiously fingering myself. “Did you swallow it?” I asked.

He smiled. “Well, first he had me show him my mouthful of his semen. Then I swallowed it all.” With that I orgasmed.

“This sounds crazy, but now I want to watch sometime?”

“You mean watch me, or Elizabeth, suck a cock? Really?” He said.

“Yes. It’s so erotic.”

“Of course. You know I’ll do anything for you. But how about we find a guy and both suck him?”

“You want to see me suck another guy’s cock?” I asked.

“I think it would be erotic. Two girls playing with a guy’s cock.”

“Let’s think about it. Maybe see if we can find a guy who’d be interested.”

Jim was back the next week. He had been chatting with a guy who was very excited with the prospect of being sucked by the two of us. Jim asked if I was up for it right after he finished fucking me.

“First of all, tell me about him. I don’t want some guy I know, or a friend of Tom’s, walking in.”

“I thought of that. He’s from out of town and staying at a hotel down the street. He’s tall, good-looking, and married. Married guys are safer and more discrete. And he has an eight-inch cock.” Jim smiled.

“Oh, he’s probably lying,” I replied.

“I don’t think so. We exchanged photos. He thinks Elizabeth is a doll. Here, look on my phone.”

Jim pulled up a photo. He was tall, naked, and had a huge boner.

“Let’s do it,” I replied, giggling.

The following evening I came over early. I told Tom Elizabeth was in town and we were getting together for dinner. When I arrived, Elizabeth was in a pink satin robe. She was in a bra and panties, had her hair in curlers, and was doing her makeup.

“Well, this is certainly different than the night we met,” I thought to myself.

I had worn a short black dress. “What are you wearing?” I asked.

She went to her closet and brought out a lovely burgundy pencil dress. “Oh, you’ll look great in that,” I said.

She finished getting ready. We had a glass of wine and Elizabeth messaged the guy. He said he’d be there in ten minutes.

On schedule, there was a knock on the door. Elizabeth opened it and this very good-looking man walked in.

We introduced ourselves. “I’m John. it’s nice to meet you both. Elizabeth, if you hadn’t told me, I’d think I was meeting two genetic women. You’re both beautiful.”

We had a glass of wine, and after an awkward pause, Elizabeth asked him if she could kiss him. He smiled and said yes. She went over and gave him a big kiss. Then they started making out. She deftly reached down and unzipped his pants. She reached in and pulled out a semi-erect cock. I watched her stroke it until it was fully erect. “Wow. She knows what she’s doing,” I thought. I was getting aroused. He wasn’t lying about his size.

Then Elizabeth bent over and started licking his cock. I moved over to the other side and started making out with him while she started sucking him. It was exciting. He played with my tits as my boyfriend sucked his cock! Okay, it was my turn. I pushed Elizabeth gently aside and took John’s big cock in my mouth. Elizabeth sat up and went back to making out with him while I sucked his cock. After a bit, she knelt down and we took turns. We ran our lips up the side of his rod and kissed at the top.

John started moaning. At that point, he was in my mouth while Elizabeth was licking his large hanging testicles.

“I’m going to cum,” he warned. I felt his warm semen hit the back of my throat. Elizabeth nudged me aside and she took the rest.

“Wow. You girls are incredible. I hope we can get together again.”

I said, “Maybe. That was fun.”

We said our goodbyes. After he left, we just looked at each other and giggled.

“What a couple of sluts we are,” I said.

We were going to go out to dinner. But I was now horny as hell. “Honey, I can’t believe how turned on I got seeing you suck his big cock. How about you?”

“Same for me. I am so aroused now. Seeing you suck his cock was amazing.”

“I think we should fuck before we go out. Would you mind fucking me?”

“Like this?” She asked.

“Yep. Elizabeth can stick her big clit in me. Pull down your panties and do me from behind.”

“Yes mistress,” she said in her most feminine tone.

“Mistress. I like that. My little sissy girl.”

Elizabeth was as turned on as I was. She fucked me hard.

“Good girl,” I told her as she shot her load in me. It crossed my mind that maybe we should just be girlfriends. It was so much easier.

We freshened our lipstick, brushed our hair, and went to dinner.

We talked about what a fun night it was. “You know, Hon, I am fine with you being Elizabeth whenever you’re here. I know you love it. And I can just be your lesbian girlfriend. Or your mistress.” I smiled at her.

“Are you sure? She asked.

“Yes. I don’t have to worry about being seen with you in public. We can go out and do whatever we want. We can still have sex. From now on, you’re just Elizabeth. Okay?”

“Oh, Nora. Are you sure? I must say, the idea is exciting.”

“Yes, I’m sure. I’m crazy about Elizabeth.”

We giggled.

“Let’s plan our next adventure.” I was loving my new girlfriend.