Mike Meets Arianna!

Most of my stories are from the point of view of the crossdresser. This one just popped into my head and comes from the other side. I hope I do Mike justice.

"What the fuck am I doing sitting here?" I asked myself. Even though I had freely come inside, I was having second thoughts and wondering if I'd made the right choice. Yet, here I was, sitting at the bar of the most popular alternative lifestyle club in the city. How did I wind up here??!!!!

My name is Michael Josephs. I'd taken early retirement and hadn't been retired that long. I've been married twice. I'm newly single, a widower, and in my late fifties. Both of my wives had something in common besides being married to me. They also quit having sex with me shortly after we got married. You might think that since I'm the one thing they have in common, that it's all my fault. I'll let you decide.

My first wife and I got married too quickly. She became pregnant three months after we met so we didn't really have much time to establish any kind of sex life. After our son was born, we slowly began to explore sex together again. It became abundantly clear she didn't enjoy sex at all. Something happened to her when she was much younger; she would never talk about it and refused to go to counseling. By the time my son was in eighth grade, she had stopped sleeping with me altogether. The day after we dropped him off at college, I asked for a divorce.

I moved out of state to be with a woman I had met online. Our sex life was great at first. She was an enthusiastic and willing partner. We had two children together. Then my wife had an affair. With one of my relatives. I'll skip the gory details but even she admitted it was all her fault. She never apologized, she refused to talk about it when we went for marriage counselling, and because of her guilt, also refused to sleep with anyone else, including me, ever again. Not verbally, she never talked about it, just rebuffed all my efforts until eventually I quit trying.

My sex life turned to masturbation. I love looking at women in sexy lingerie, stockings, and high heels. Those types of pictures are available in abundance on the internet; I could fantasize about making love to all kinds of women. The one thing they all had in common was what I made sure they were wearing.

Then one day as I was surfing the net, a link came up which I followed. The woman was beautiful and dressed sexier than most women like to dress nowadays. As I continued to look at her pictures, I masturbated and had an earth-shattering orgasm. I did a deep dive into her background; I wanted to make sure I could find her again. It was then that I discovered 'she' wasn't a woman at all but a crossdresser. I had just masturbated while looking at another guy. I slammed my tablet shut, disgusted with myself.

I didn't masturbate for four days afterwards. I wouldn't even pick up my tablet. Eventually, my dick did my thinking for me, and I started masturbating again. And soon after that my curiosity got the better of me. I began to search for crossdressers on the internet. I realized there are as many kinds of crossdressers as there are people. Most of them aren't passable which is absolutely OK but not what I was looking for.

Some of the most beautiful 'women' in the world are passable crossdressers. Their makeup skills, use of prosthetics and wigs, are to the point of being artistic. And they themselves are the canvas they use to create the feminine images they portray. Eventually, I found myself masturbating to the most beautiful, sexiest of crossdressers. It was as if they were speaking directly to me. "You know you want to be with one of us. One of us can make you happier in bed than you've ever been in your life." These were the thoughts running through my brain as I masturbated looking at them. Eventually, I stopped looking at pictures of genetic women, the orgasms I had while masturbating looking at crossdressers were way more exciting and satisfying.

And then my second wife died. It took a while to get all of our monetary affairs in order and for me to assess my life. I was in great shape financially. Our house was completely paid for. We had both taken out a lot of insurance on ourselves. Not only did I have the money from her insurance policies, but I also got all the money from the various 401-K, stock, and retirement plans from her jobs. I sold one of our two cars to pay for the funeral. I was set for life as long as I didn't spend that money foolishly.

As I continued to masturbate to pictures and videos of crossdressers, I also began to communicate with some of them. I created a special email account that I only used to correspond with crossdressers. I got a burner phone, again, only used to text and call crossdressers. There were a lot more misses than hits, I wasn't the kind of guy many of them were looking to meet. I was too 'old' or too straight for most of them.

I was more than OK with that. I didn't want to meet anyone who didn't want to be with me. I've done that twice in my life already. I wasn't looking for that third strike. I started to narrow my search to gurls in my city. I found a very attractive CD in her early forties. We'd exchanged emails, texted and even talked on the phone a few times. I told her my history; she said she understood my curiosity.

Eventually we agreed to meet at the club where I was now sitting at the bar. I was nursing my drink when there was a tap on my shoulder. I turned and looked into the hazel eyes of Arianna. She smiled at me. "You're Michael, I recognize you from the pictures you've sent to me. I have to say, you don't look anywhere close to your age." I had always prided myself on my appearance. I was just under 6' tall and weighed 175 lbs., all of it lean muscle. I had been an athlete growing up and continued to work out, even long after my athletic career was over.

Arianna was more beautiful in person than any of the pictures she sent to me. She was wearing a camel colored, figure-hugging sweater dress that was about 6" above the knees along with dark brown knee-high boots with 4" stiletto heels. In her heels, Arianna was probably about 5' 9" tall which would have put her at about 5' 5" in her stocking feet.

She'd chosen the name 'Arianna' because of her Italian heritage. She was dark complected, had raven-black hair and was absolutely beautiful. She didn't look anywhere close to being in her early 40's either. Had I just seen her on the street, I would never have thought she was a crossdresser, and I would have guessed her to be in her late 20's or early 30's. I stood up and pulled out a bar stool for her. "Please, sit down and let me get you a drink."

Her musical laughter sounded like the pinging of a crystal glass. "A gentleman I see. I like that. Most men nowadays don't know how to treat a lady." She smiled at me, and I just stared. Her smile was warm, genuine and made her even more beautiful.

We chatted and Ariana opened up about herself way more than she had done electronically. She knew at a young age she was gay. She loved making love to men and had never been with a woman in her life. She still had gay relationships, but she said her crossdressing allowed her to make love to men who would otherwise never have been attracted to her male persona. I guess I fell into that category.

The bar was right next to the dance floor and just then a slow song started playing. Ariana looked at me and asked, "Dance with me?"

"How can I say no to the most beautiful woman in this club?" I stood up, pulled out her stool, held out my hand, and led her to the dance floor. No one would ever confuse me for Fred Astaire but because of my athletic ability, I had always been able to do more than hold my own on the dance floor. We seemed to glide as I led Arianna around. She snuggled into me tighter and I pulled her to me.

The song ended and she looked up at me with longing and desire in her eyes. This was the moment. Either I kissed her now or walked out of the club knowing this had all been an unrealistic fantasy on my part. She laid her head back down on my chest. "I'm sorry; I'm not being fair to you. You're just so handsome, and dancing with you was so arousing that I couldn't help myself. I know I need to go slower with you. I'm so turned on right now. I want to be your first; I don't want to do anything to drive you away."

"No, I'm the one who should apologize. I'm the one who's intruded into your world. You've been kind and patient and thoughtful with me." I put my finger under her chin and lifted her face. I bent down and kissed her gently. She kissed me back just as gently. Her lips were moist and warm, she smelled so feminine, and her body was soft and curvy. My passion grew and I kissed her with a hunger for something more. Moaning sexily, she answered the intensity of my kiss.

People passing by were laughing and making comments. "PDA!" "Get a room!"

Ariana and I looked at each other, blushing simultaneously. I held her hand as I led her back to where we were sitting. I ordered another round of drinks as we continued to talk. "I'm sure this is going to be a clumsy question but I'm curious. You have an amazingly sexy body and you felt wonderful when we were dancing. How do you do it?"

"Michael, I don't mind at all. If this relationship goes where I would like it to go, you have to be completely comfortable with me. I have a silicone prosthetic bodysuit. The breasts are lifelike as is the vagina. I tuck my penis into a pouch behind the vagina. The bottom is open, so my lovers have access to my rosebud. At some point before you commit to going all the way, I'll model it for you. If you don't feel it's realistic enough, if it turns you off in any way, I'll understand. I'll be very sad, but I'll understand."

We continued to laugh and chat when suddenly the alarm on my phone went off. We both looked at it at the same time. "Ariana, we both agreed before we ever met up that no matter how things were going, when that alarm went off, I would leave. I didn't want us to feel pressured; I wanted to give us a chance to see how things were working out without feeling hurried. I'm going to leave as promised. But I also promise you I will see you again."

I stood up, leaned in and kissed her. She kissed me back and sighed. "I know this is what we agreed to do but I don't want you to go. I wish you would stay."

"I want to stay too but I also want to show you I can keep my word. If you would have felt uncomfortable with me in any way, you'd want me to be going. Again, I promise we will see each other soon."

I left and drove home. When I got inside, my phone chimed. Ariana had sent me a text message. This was all it said. "💋"

I texted her back. "😘 👫"

"Do you mean it? Do you really mean it?"

"Of course I mean it. You're beautiful, funny, smart, confident, and intelligent. What man wouldn't want to be with a woman like you. Say you'll go out with me tomorrow, please?"

"Well, I don't know. You just left me here all alone by myself at the bar. What if you walk away from me again tomorrow?"

I called her immediately. "Ariana! That is so unfair, we agreed no matter...."

"I'm teasing silly! Yes, I'll go out with you again tomorrow. Where would you like to go?"

"Would you go to the bookstore with me? They have a coffee shop inside so we can sit there, rest, and drink coffee whenever we're not browsing?"

Ariana giggled. "I love that idea! I'd love to go to the bookstore with you. What are you going to wear?"

"Honestly, I hadn't really thought about it. Probably just dress-slacks and a nice polo shirt. Why do you ask?"

"Because I want us to look like a couple. I don't want to be wearing jeans if you're not. I don't want to wear a business skirt suit if you're more casual. I want us to match. Is that OK with you?"

"Of course, I was just curious. Can I ask a favor?"

"Certainly silly, what is it?"

"Would you wear garter stockings and at least 3" heels? It's a fetish of mine. Even though I won't be able to see them, just knowing you're wearing them will be such a turn on for me."

"Mmmmm, I like the thought of you being turned on. I absolutely will wear them for you!"

"You're amazing. I'll see you tomorrow at 11:00 am at the bookstore."

"Don't be late! I want to spend every minute with you that I can!"

I fell asleep dreaming of Ariana. It had been a long time since I had been with a woman who wanted to be with me the way Ariana did. And the fact that she eagerly wanted to wear garter stockings and high heels just for me? I thought I'd died and gone to sexual heaven! I woke up the next morning with a puddle of cum on my stomach. Clearly, my dream about Ariana had gone to the next level.

I showered and shaved. I wanted to be clean and well-groomed for my date with Ariana. I selected my nicest pair of slacks and dress shoes and a polo shirt by Calvin Klein. I thought I looked good, not overdressed but not too casual by any means. I deliberately arrived at the store early at 10:45 am. I wanted to look around, get a quick idea where everything was located, and most importantly, not be late for my date with Ariana.

Ariana arrived at exactly 11:00 am. She looked amazing. She was wearing a pine green silk circle skirt that was cut 2" above her knees. She had on a pastel green satin blouse with cap sleeves. The wide black patent leather belt that cinched her waist matched her black patent leather stilettos with 4" heels and open toes. She was wearing dark suntan-colored stockings, only I knew they were garter stockings. Somehow, the thought that I was the only one who knew was even more exciting. She wore minimal jewelry, just gold dot earrings, a delicate princess necklace, a couple of bangle bracelets on her left wrist and two gold rings on the pinky and index fingers of her right hand.

I rushed to greet her and taking both of her hands in mine, I kissed her on both cheeks, European style. "You look fabulous. I don't know if I'm going to be able to browse the books at all; I'm going to have a hard time tearing my eyes away from you!"

She giggled appreciatively. "You truly are a sweet man. I love your compliments, they're thoughtful and witty."

"Books or coffee first?" I asked.

"Coffee, please. I didn't drink as much coffee as I usually do in the morning. I wanted to make sure I was on time for you."

We walked to the coffee bar hand-in-hand and placed our orders with the barista. We found a small table in the corner and when our order was ready, I picked it up and brought it to our table. Ariana had chosen to sit with her back to the rest of the coffee shop; I was sitting facing out. We were enjoying our first sips of coffee.

Ariana looked over her shoulder. We were the only two sitting there. She reached down with one hand and slowly slid her skirt up her leg until her stocking tops being held up by garter tabs were clearly visible.

I almost spit my coffee out. Ariana smiled mischievously around her next sip of coffee. "You asked, I just wanted to show you I keep my promises."

"That is so unfair. I'm not going to be able to think about anything else for the rest of the day."

"Mmmmm, that's good. I'm glad you're not going to be able to keep me out of your mind."

We finished our coffee in silence, just enjoying each other's company. We couldn't keep our eyes off one another, looking into Ariana's eyes was like talking to her. I felt as if she could read every thought in my head, and I didn't mind at all. We were in sync.

We finished our coffee and stood up simultaneously. Linking hands, we walked out into the store to browse the shelves. I let Ariana take the lead; I wanted to see what topics interested her. When she squatted down onto her haunches to look at titles on the lowest shelf, she would hike her skirt up again, flashing her stocking tops at me.

"You're just looking at the lowest shelves so you can tease me."

"Of course I am, darling. I can stop if you'd like?"

"Actually, I was hoping I could talk you into only looking at books on the lowest shelf!"

"You're such a naughty boy. Sometimes I really like bad boys." She winked at me coyly when she said this.

We continued to wander around the store, I picked up a copy of 'Dune.' I had lost mine somewhere along the way. Arriana picked up a copy of 'The Seven Habits of Highly Effective People.' She was a team lead where she worked and was constantly reading self-help books. We took our prizes back to the coffee shop area, ordered a second round of coffee, and began reading (re-reading for me) our books.

It was nice being with someone who enjoyed the same things I did and didn't feel pressured to do anything else. Occasionally, she would look up from her book and catch me looking at her. It never seemed to bother her, and she always gave me that magnificent smile. Ariana was truly beautiful, she seemed to remind me of someone which was why I kept looking at her.

"Min-Min-Minetti! That's it, Nicola Minetti!" I mumbled to myself. Ariana peered over the top of her book.

"What's that? I couldn't hear you."

I blushed when I told her, "I've been trying to think of who you look like, who you remind me of. It's Nicola Minetti!"

Now Ariana blushed. "Wow, she's off the charts gorgeous! That's quite a compliment."

She grabbed both of my hands in hers and gently pulled me to her across the table. She kissed me slowly, tenderly. I returned her kiss the same way. "You are such a dear, sweet man. You always say the kindest things. Thank you!"

"Thank you for wanting to be with a crusty old codger like me!" I smiled when I said that.

"I'll bet you're not a crusty old codger in bed!" she replied as she licked her lips seductively.

I blushed again. "What are you doing tonight?"

"I haven't really made any plans. I was hoping our afternoon out might turn into an evening together."

"Would you come to my house? Let me make dinner for you?"

Her eyes sparkled. "I'd love that!"

"Do you like seafood, spicy food? I make Cajun Shrimp that is scrumptious. It's a Paul Prudhomme recipe, it's melt-in-your-mouth delicious."

"Yes, I adore spicy food and I love shrimp. The pairing sounds incredible."

"I have to warn you! It uses lots of butter so it's high in calories. Add in the baguette you use to dip in the sauce and it's a day's worth of calories in one meal."

She pouted. "Oh, are you worried about me gaining weight?"

"No, no, it's not that at all. I always want people to know so they can adjust their diets if they want to. I really watch what I eat the next couple of days after eating it."

She winked. "I know, silly. I was just teasing." She sighed. "You really are a nice man. So thoughtful. Most people wouldn't even think about sharing that kind of information."

"Then it's settled. What time do you want to come over?"

"How about now?"

"I have to stop at the store on the way home to pick up the shrimp, bread, and a couple of other ingredients. I also want to get a couple bottles of wine to go with it."

"Even more calories. You ARE trying to turn me into the stereotypical, Italian momma." She smiled that smile I'd already come to love to let me know she was still teasing.

Ariana followed me in her car to the grocery store. We got a cart and went inside. Pushing it through the store, side-by-side, holding the handle together like an old married couple. We picked up two pounds of shrimp, a pack of unsalted butter, two baguettes and some spices I thought might be close to being out.

We went to the wine section and selected two bottles of Chenin Blanc from the cooler. Ariana bent over to put them in the cart and her skirt rode up to her hips giving me an eyeful of her gorgeous nylon-clad legs and a partial view of her panty covered ass. I started to get an erection, right then and there.