Josh Meets Carmen Pt. 01

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Straight widower meets transgender woman.
2.3k words
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10.6k
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Part 1 of the 6 part series

Updated 06/18/2023
Created 06/02/2023
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My name is Joshua Michaels. I'm retired and a recent widower. I had taken a leave of absence to help take care of my wife and be with her as much as possible when she was diagnosed with incurable cancer. My wife was a fighter; she hung on for nine months. Eventually the cancer won out and it ate away most of her internal organs. We didn't have any children, so it was a small funeral.

The house was paid off and we had purchased good sized insurance policies for both of us. Not only would I not have to go back to work, but I would also never have to work another day in my life. I spent the next few weeks in a mental fog as I went through my wife's belongings and cleared them out of the house. She'd made a list of what charities she wanted things donated to and I made sure to honor those wishes.

Finished with that task, even though it was just a small ranch-style, the house seemed a lot emptier. I updated my will. I began to go through my things and clear them out too. I didn't want some stranger making those decisions for me. Unless it was of great value, either sentimentally or economically, I let it go. I found an unopened bottle of Viagra; I'd gotten it filled just before my wife's diagnosis.

I've always had a healthy libido. Like many men in their late 40's, I dealt with the occasional bout of ED. My wife's sex drive didn't match mine, but we found a middle ground like so many other things you have to compromise on in a marriage. She was also gracious enough to accommodate my preference for women wearing fine lingerie, stockings, and high heels. She knew how much this turned me on and was happy to make me happy! It had been more than a year since we had made love.

I smiled ruefully at the bottle. I had occasionally looked at porn on the internet, targeting pictures of scantily dressed women. I stumbled across pictures of crossdressers, obviously the links were similar. I remembered seeing one picture of a crossdresser sitting on a bed, with an older gentleman looking out the window of the hotel room behind her. She was all dressed up; she was adjusting the garter stockings under her dress. There was just something about that picture I found so erotic.

I started surfing the net again specifically targeting pictures of passable crossdressers. Not just passable, but sexy and enticing. I would take half a tab of Viagra beforehand and masturbate for hours looking at these gurls who clearly loved dressing up for the sake of dressing up. You rarely, if ever, saw GG's dress that way. They were into yoga pants, sports bras, and sneakers.

I came across a link to a nightclub in my city that catered to crossdressers and their admirers. I decided to visit that club. It was called the Alpha / Omega Club. I did as much research as possible; I didn't want to stick out like a sore thumb or look like some desperate pervert. I decided to go on a 'retro dance' night, hoping I might be familiar with at least some of the music.

I groomed carefully and wore dress slacks, an open collar dress shirt and a blazer. I didn't want to be overdressed; I also didn't want to look like some slob. I was in pretty decent shape for a man my age; I wasn't overweight, had all my hair and people always told me I looked at least ten years younger than my actual age.

I arrived thirty minutes later than the doors opened; I didn't want to appear desperate. The club was already starting to fill up. I found a seat near the end of the bar, close to the dance floor. I ordered one of the local micro-brews and discreetly looked around. The clientele ran the spectrum, from one end to the other. From drag queens to guys in dresses, from transgender to passable crossdressers, from guys dressed like me to out-of-shape guys who looked like they were in desperate need of a shower, everyone was there, all looking to have a good time.

I smiled to myself when a voice over my shoulder said, "Hey stranger, new in town? Wanna buy a girl a drink?"

I looked and was stunned. An absolutely gorgeous Latina was smiling at me. "I'm always willing to buy a beautiful woman like you a drink. Whether I'm willing to buy you a second one depends on if you're as witty and charming as you are beautiful."

She laughed. It was musical, like the tones from a bell choir. "Well said, el guapo, well said."

"I'm Joshua Michaels, my friends call me Josh." I said as I pulled out the bar stool next to me for her to sit down.

"I'm Carmen Arroyo, my friends call me 'Bonita'." she said laughing again in those musical tones as she sat down.

"Ay, que' linda!" I replied.

"Oh, nicely played, gringo. Tu' hablas Espanol?"

I shrugged my shoulders. "Un poquito, un poquito. What can I get you to drink?"

"I'll have a Tequila Sunrise."

I signaled the bartender and ordered her drink. I looked at her closely and she looked at me just as closely in return. Carmen was dark complected, with sparkling brown eyes, jet black hair and full, luscious lips. She wasn't just pretty; she was a knockout. "So, I have to ask. Why does the most beautiful woman in the club decide to ask a plain old man like me to buy her a drink?"

She laughed. I could have listened to her laugh all night. It was music to my ears. "Well, Josh, I know you're new here. I've never seen you before. I've seen lots of newcomers to this club either being awkward or just plain rude. You're neither. You've been quiet and respectful as you've tried to get your bearings here. I like that. Quiet, respectful men are sexy. And it doesn't hurt a damn bit that you're cute too!" She laughed in those musical tones again.

"Wow! First, you call me el guapo. Then you tell me I'm cute. I'm starting to really like talking with you!" I smiled; she smiled back.

Just then, the club's DJ began to play '(Da Le) Yaleo' by Santana. I stood up and held out my hand to Carmen. She took it and I led her onto the dance floor. My wife and I had taken dance lessons for decades. I loved salsa. My wife humored me. The dance instructor always said I was a natural. Dancing was another one of those things I loved, and my wife was kind enough to meet me halfway.

Carmen seemed surprised by the smoothness with which I led her through our dance, but her surprise quickly gave way to joy, and she let loose. Carmen was amazing, there is no other way to describe it. She was a natural dancer whose body seemed completely in sync with the rhythm of the song. I did my absolute best to stay with her and complement her but there was no doubt Carmen was the star of the dance floor.

The DJ slowed things down by playing 'Europa' next. It was Santana with Gato Barbieri which is my favorite version. I held out my arms to Carmen and she molded herself to me. I held her right hand and placed my left hand respectfully on the small of her back. It was as if we had been dance partners for years! Carmen followed my lead instinctively, whether it was taking her through a spin or leaning her way back on a layout. There was no hesitation on her part, and I made sure to complete all the moves smoothly.

The dance ended while I had Carmen in a layout move. We stayed like that as the last notes of the song echoed in the club. We were staring into each other's eyes. Finally, Carmen giggled and said, "Are you going to help me up gringo or are we going to pose like this until the next dance starts?"

I laughed too and helped her up. Carmen intertwined her fingers with mine and led me to a small alcove in the club. It had tables for two, and no speakers, so the music from the dance floor wasn't playing there. It was perfect for a quieter, more intimate conversation. I ordered drinks for both of us, and they soon appeared. We were content to enjoy the silence and just study one another until our drinks arrived. Then the conversation began in earnest.

"Josh, you're an incredible dancer. It's been a long time since I've enjoyed myself that much on the dance floor. So, tell me, what brings you to the Alpha / Omega?"

"Do you want me to beat around the bush or get straight to the point?"

"I always appreciate honesty and directness from any man I'm talking to."

I poured out my life story to Carmen. She was an incredible listener, only asking the occasional question for clarification. From the absolute most important parts of my life such as my more than 20+ years of marriage and the way it ended to the less than serious things such as my love of women in lingerie, stockings, and stilettos, I shared it all.

When I finished, Carmen asked. "Josh, when your wife was sick, why didn't you have an affair or seek out a professional? I'm sure your wife wouldn't have minded."

"Carmen, even if my wife wouldn't have minded, I would have. It may be old fashioned but when I promised 'in sickness and in health,' I meant it."

A single tear rolled down Carmen's olive-skinned cheek. I reached out and caught it on the tip of my finger and brought it to my lips. Carmen just stared, wide-eyed.

"Mi amor!" Carmen whispered breathlessly.

"My turn. What brings you here? What brings an incredibly beautiful woman like you to a trans club? And please don't misunderstand me, I'm not judging, just curious. I really want to know."

Carmen stared at me. Finally, she asked, "You don't know, you really don't know?"

"Know what?"

"I'm not a genetic girl. I'm two plus years into my transition. I haven't had my final surgery yet. I still have my male parts between my legs although two years of hormones have caused them to shrink greatly. But they're still there."

I didn't blink. I was surprised at my own stupidity. Meeting someone like Carmen had been the reason I came to Alpha / Omega. Carmen was gorgeous, funny, intelligent, open-minded and empathetic. I'm not sure I'd ever had a more pleasant first meeting with a woman in my life. "Carmen, I hope I'm not being too forward, but I'd love to take you out on a date. Dinner, dancing, a movie, your choice of places, it's up to you."

Another lone tear rolled down Carmen's cheek. "You don't mind, you really don't mind?"

I reached out again, caught that tear and also brought it to my lips.

"Mi amor!" Carmen said as she slid her hands across the table to cover mine.

Just then, a very good looking but very inebriated young man came up to our table.

"Been looking for you, Carmen. Why you make it so hard to find you?" he slurred heavily.

"Obviously I didn't make it difficult enough, James. Like I've told you so many times before, it's over between us. It didn't work out. Please leave me alone. Please stop stalking me."

James slammed his hand down on the table. It echoed in the alcove. All eyes turned to our table. "It's not over, I won't let it be over."

Just then two very large security guards came up, each of them gently putting a hand on a shoulder, and asked James to leave. As he let them lead him away, he looked over his shoulder and again said, "I won't let it be over."

I could feel Carmen trembling through the fingertips on top of my hands.

"Carmen, look at me. I don't know what that was all about, but I promise you, while you're with me I-will-not-let-anything-bad-happen-to-you."

She looked at me and smiled wistfully as if to say, "Sure, OK."

"Carmen! Look-at-me!" She did, a little surprised by the force in my voice. "You might not believe what I'm saying but you are safe with me, and I will not let anyone hurt you while I'm around."

"I think I really believe you; I think I will always be safe with you. I've never felt this way about a man before; how did you do this gringo; how did you make me feel this way so quickly?"

"I hope by being honest with you. I hope by pouring my heart out to you. I hope by sharing myself with a woman more completely than I ever have the first time I've met her. I hope by letting you know through my actions, more than my words, how attracted I am to you in such a short period of time. I'm going to ask you again; please say you'll go out with me. I will treat you like the goddess you are; I will treat you with more respect than any man you've ever been with before."

"I will go out with you but not until you've met my mama, not until mi mamita has given you her stamp of approval."

I nodded. I thought it was somewhat of an odd request but perhaps Carmen just wanted to see if I really wanted to go out with her. We exchanged phone numbers. "Can I walk you to your car? Just in case that asshole, James, is lurking around outside."

"No need, thank you. I don't own a car. And security will make sure I get safely into my Uber."

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9 Comments
MaryFrancis36MaryFrancis363 months ago

Read the whole thing in record time. Great story!!!

AnonymousAnonymous11 months ago

My panties are wet just thinking about where you’re going to take this story. I love Josh and Carmen already! I can’t wait for Part 2!

Michell408Michell40811 months ago

You got a great story going and absolutely loved the beginning hope for more

Danielle_CD58Danielle_CD5811 months ago

Wow, I love this story. Please keep it up. Keep them both so real too.

nutcase666nutcase66611 months ago

Love this good start looking forward to more

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