The Letter

This one was a request. I had a fan mention that all my stories had transgender women falling for men which plays into my personal fantasies, so I usually just go there. Her request was for a story about a cross dresser that found a loving supporting female partner and I accepted the challenge.

I hope you enjoy the story and as always, everybody's 18, only happy endings, etc., etc.

Please leave me a comment with your thoughts and suggestions.

***

Carla waved when the bell above the door to her shop chimed, giving me a big smile and motioning me to the couches off to the side. I had met her ten years ago when she walked through the bar I was in, slipping a ponytail tie and her business card on my table as I wrestled with my unruly mop of shoulder-length blonde hair; she hadn't said a word and two days later; I was in her chair.

I had always been meticulous about my hair, getting it cut every six or eight months whether it needed it or not. On the day she had slipped me her card, it had been thirteen months. From then on, I had an appointment the fourth Thursday of every month at 12:30. If I missed, she let me know about it.

I sat in her chair and she did her magic with my hair and we talked about our lives; we talked about our jobs, our hobbies, and our families, she heard everything about my kids and my wife and ultimately my divorce and I heard about her husband, her kids and then her divorce, for people that only saw each other for about an hour once a month, I felt like she knew me better than anyone else I knew; it was therapy with a haircut.

Four years ago, that changed. I showed up and the first thing I noticed was her beautiful waist length auburn hair was a short bob cut, "My god Carla, what did you do?"

She handed me a pamphlet, 'WigsforKids', somewhere out there was a little girl fighting cancer with a beautiful head of auburn hair courtesy of Carla.

"Um, can guys do this? I mean, what an amazing cause." I handed the pamphlet back to her.

"Your hair? As fast as it grows, absolutely. It will still take about two years to grow it out to the length they like, and you'd still need to come in for trims, but sure," she smiled and winked at me in the mirror.

"Well, just a trim today then, ok?"

She used a different shampoo and conditioner than she usually used, making sure I stocked up with her before I left; If I was going to donate my hair, she wanted to make sure I kept it perfect.

Today would be the second time she had cut my hair for a donation. It was almost to the middle of my back, and I had to admit, I was going to miss it.

Carla called me over, sweeping up around her chair from her previous customer, "So, you ready to do this?"

I just smiled and nodded, settling into her chair. She spun me around and laid me back so she could wash my hair before she cut it. I laid back and closed my eyes as the warm water flowed over my head and she rubbed the fragrant shampoo in and work it into my scalp. There is very little more relaxing or more seductive than having someone else wash your hair. When they're a gorgeous redhead and their breasts are pressing into your chest, it's even better.

Conditioner was next and then the blow dry, after which, she tied it off into a tight ponytail at the base of my skull, put a second tie a little lower and made the cut. I had cringed last time, and this time was no different.

"Sixteen inches. You are a beast. They will love you for this." Carla leaned down and kissed me on the cheek.

She spent the next forty minutes making my remaining hair look outstanding, I got an update on her youngest Emily, and how she was doing in College Station, and I shared the latest on my job, I had finally proved myself or kissed the right ass and received a promotion to regional sales manager; no more travel unless it was necessary.

"So, Derailers at the Spoke tomorrow and Saturday, you up for a celebration?" Carla was checking my hair one last time.

"Carla, after all these years, are you asking one of your customers out on a date? I thought that was the one line you wouldn't cross," I laughed at her.

"I still have scissors back here, so you better watch it," she laughed with me, "Seriously, Emily is off to school, and it would just be nice to have something to do, and like I said, celebrate your promotion, and it's not like you've been filling my ear with girlfriend stories since you and Liz divorced."

"Fair enough, and I guess I have heard little on that front since Rob...," I didn't finish the sentence, I knew it was still a sore subject, her ex had run off with her business partner, her gay business partner.

"I'll take that as a yes. Now give me your phone and I'll add my personal info to your contact list for you. You can pick me up at seven."

I headed back to work, and our receptionist Roselyn won the office pool on how many inches I would donate, guessing exactly 16. There was much gnashing of teeth and beating of chests and much laughter before Greg told us all to get back to work. He had guessed 15.5.

Friday afternoon came, and I headed home to get ready, I was more nervous than I remembered being on my wedding day, sure, Carla and I had known each other for ten years, sure there were lots of things we didn't know, but I knew about her kids and she knew about mine, I knew about her ex and she knew about mine, I had watched her business flourish and then almost fail as she struggled to rebuild it after her partner ran off with her then husband, and she had weathered the stress of all the travel I had been doing as well as the degeneration of my marriage, it had just been one hour at a time, once a month, now I was going to be spending the entire evening with her; I hadn't been on a date in over twenty years.

We were going dancing, that I could do, in fact, I was actually pretty good, it had been the one thing that Liz and I did well together, and I love The Derailers, a staple of the Austin music scene, mostly cover music, but they always drew a crowd.

"Ok, I can do this," I checked myself over, nice blue paisley button down, clean Wranglers, ostrich boots. I was ready. I reached up and knocked on the door.

"Doors open, be down in a minute," I heard Carla shout from inside.

"Good evening ma'am, I'd like to talk to you about your relationship with our savior," I laid on a thick southern accent as I opened the door.

"Dammit Mike, not funny," she stuck her head around the corner at the top of the stairs and glared at me, her mascara in her hand.

"I know a good stylist if you need some help," I laughed again.

"Just shut up, ok, I'll be down in a couple of minutes. I had a client run long."

It was worth the wait, skintight jeans, camisole top with no evidence of a bra. Her hair flowed around her face, framing it perfectly. I had known her for ten years and had never seen her. My god, she was gorgeous. Rob had to be gay to leave a woman this beautiful. She floated down the stairs and all I could do was stare. Carla waltzed right up to me, wrapping her arms around my neck. She kissed me, "I have wanted to do that for so long, you have no idea," she smiled as our lips parted.

"Wow." I shook my head and took a couple of deep breaths.

"Besides, it takes the pressure off, don't you think?"

"Depends on what kind of pressure you're talking about." I made an exaggerated move to adjust my crotch.

"Stop it, let's go," she grinned and grabbed my hand, leading me out the door.

We danced every dance, taking a break only when the band did. Liz and I had danced together for years and weren't as smooth as Carla and me. It was almost like dancing with myself, except I got to watch Carla's smile and gaze into her big green eyes. The last dance was a waltz. When it finished, I spun her out and then back in, pulling her close and finding her lips with my own. We were still in the middle of the dancefloor when the lights came on.

"Come on guys," it was the bouncer. Carla and I laughed and headed out to my car, holding hands and acting like teenagers. Breakfast at Kirby Lane and then back to her house. It was almost four when I got Carla home.

Without a word, she unlocked her door, and biting her lip, turned to face me. "Stay?"

Words failed me, so I just nodded. Following Carla inside and up to her bedroom, I could feel the anxiety radiating from her, the eagerness, the fear, and the lust that went with it shone from her eyes.

There was no hesitation. Carla pushed me onto the bed, pulling my boots off and scrambling at my pants while I unbuttoned my shirt. Her camisole was next, holy shit she had perfect breasts, she kicked her boots off as I worked at the button and zipper on her jeans, it took both of us to get them off, she gave me a dirty look when I giggled, I was just wondering how she got them on.

My boxers flew across the room, and I froze, watching mesmerized as Carla turned her back to me and slowly slid her panties down her long legs, stepping out of the small pool of soft fabric and turning slowly. I couldn't move, the look in her eyes, that amazing body, the way she slowly crawled up from the foot of the bed, like a big cat on the hunt, slowly up my body, stopping to kiss my chest and then my chin, and then my lips, I wrapped my arms around her, my lips meeting hers, our tongues continuing our dance, there were no two-steps, no waltzes, this was a dance born of the gods, primal, raw, a dance begun before time, a dance of eternity.

My lips left hers as I pushed her onto her back, sliding my kisses along her cheek to her ear and then down the side of her neck, taking my time, teasing, and playing with each spot, trying to convince her it was the most perfect, the most erotic spot on her body.

Carla moaned, her hands roaming over my body as hers moved beneath me, her soft moans drifting to the heavens.

Slowly down her collar bone to the valley between her perfect breasts, my hand finding one globe as my lips found the other, massaging and drawing tender circles around her nipple with my fingers as my tongue flicked the other and I sucked it into my mouth, biting it gently as I released it only to repeat the process as I shifted my kisses to her other breast.

Carla's hands were in my hair, massaging my scalp as she arched her back and continued to moan, my tongue leaving a sloppy wet trail from her breasts down the center of her abdomen to her navel. Driving my tongue deep inside, I sucked hard, eliciting a gasp, "My god Mike," I smiled to myself as I continued my journey.

Carla's scent filled my head as I made my way to her prize, kissing the inside of her thighs and her perineum before I gently drew my tongue between her lips and flicked her swollen nib, pulling it into my mouth and sucking hard as small tremors spread through her body.

I buried my face in her pleasure, spelling every word I could think of with my tongue as her hands gripped my hair and held me in place, her moans growing louder and louder her breath shorter and shorter until there was nothing but guttural noises left, "My gaaaaaaawd Mike," she screamed as her body clenched, her back arched and spasms ripped through her arms and legs, laughing she collapsed and pulled me up to her eager lips, kissing me deeply.

"Can you please just fuck me now?"

There was no passion in what came next, it was base, it was animalistic, it was something she and I both needed badly, something neither of us had experienced for a long time, driving inside her I showed no mercy, pounding as hard as I could, making her feel every thrust while she clawed at my back and bit into my shoulder. When I finally exploded inside her, something inside me broke. It felt as if chains that had been binding my soul shattered. I collapsed next to her, pulling her close. The last thing I remember was her sweet voice, "Thank you Mike."

I woke up alone in Carla's bed. I could smell the coffee from downstairs, so I got up, grabbed a satin robe from the bedpost, and went downstairs to find her. There was coffee and a note, but no Carla,

Mike,

Thank you for last night. Sorry to run off, but I have clients early today.

Make yourself at home.

See you tonight at seven...

Carla

XOXO

I poured a cup of coffee and went out onto her back porch to enjoy it. No matter what I did, the smile on my face wouldn't go away.

Carla's yard was small and private, the hedges along the fence were in full bloom. I think it was honeysuckle, and full of bees. A pair of blue jays chased Squirrels through the trees. I could have sat here all day, but after enjoying the last of the coffee, decided against it.

Hanging the robe back where I found it, I made my way to the bathroom and stepped into the shower. Carla used the same products she sold me, so I had everything I needed. The shower felt good, and the aroma of the body wash reminded me of Carla.

I found my clothes scattered all over the room along with Carla's, noticing that her bra and panties were not only very sexy, but they also matched, a powerful indicator that she had planned the whole thing. I got the feeling I was in trouble, but it was a trouble I decided I wanted.

Picking up the panties, I couldn't resist, I lifted them to my nose and took a deep breath, the smell of her sex filled my head, and I just did it, it was one thing that had caused problems with me and Liz, other than her being bat shit crazy, she had caught me stealing her panties from the laundry and wearing them.

The satin and lace of Carla's panties felt nice as they slid up my legs, they were a little too soiled for me to wear and the reason they were in that condition made me smile, but the feeling was still there, that tinge of excitement mixed with a sense of comfort, that feeling I knew so well. Taking a deep breath and letting it out slowly, I pulled them off and tossed them in her hamper along with the rest of her clothes, picking mine up and getting dressed.

I left Carla a note like the one she left me, pocketed hers and headed out the door, smiling about what a wonderful night it had been.

Lunch was a leisurely stop at one of my favorites, a little sandwich shop with outdoor seating and a good selection of beer, I spent a few hours thinking about Carla and the possibilities she represented and just watching people as they walked past before I headed home to get ready for round two, I had hit forty a few months ago and two nights in a row like last night was going to be a challenge, yup, a nap was definitely in order.

6:59, I knocked on her door, clean jeans, a light blue chambray button down, and, of course, my ostrich boots. The smell of something wonderful filled my head when she opened the door, her smile filled my heart, and the kiss she gave me, well, it filled something too.

The something wonderful was shrimp in an alfredo sauce with a nice salad and an excellent glass of wine. We sat and ate and talked about last night, both a little embarrassed by our enthusiasm, and neither of us unhappy with where it had led. I helped with the dishes, and we took the rest of the wine out on her back porch.

"Can I ask you something?" Carla put her hand on my arm. "You and Liz, what happened? You're such a good guy, nice, smart, funny, handsome, and last night, oh shit, how did she let you go?"

"She filed, I just said yes, gave her everything she asked for and did my best to move on."

I really didn't like to talk about it and did my best to not badmouth my kid's mom and when people pressed about my divorce. It was difficult to not bring up the time she kicked me in the stomach while I was giving eight-week-old David a bath, or the rocking horse I had hand made for him she destroyed on Christmas eve or the broken finger that had forced me to remove my wedding ring for the one and only time I ever took it off; I would never put it back on.

"We should never have gotten married, I knew it and so did my brother and a couple of friends, but I was 'in love'," I did the air quotes thing, "And then she got pregnant with David, and I did the right thing, we lasted fifteen years, when she filed, I jumped at the chance to get out."

I took a sip of my wine and sighed heavily. "There's a book called 'Stop Walking on Eggshells' you can read if you want to understand what it was like." I left it there.

I almost got up to leave. Suddenly, all the crap, all the baggage with Liz came rushing into my mind. Here I was enjoying an excellent glass of wine with a beautiful woman and all I could think about was my ex, my ex and what I had done to deal with the stress of living with her.

It had started when I was five or six. I had discovered the wonders of my mother's lingerie drawer, especially her slips and stockings. As I got older, I started stealing my sister's panties from the laundry and wearing them, then a few of her dresses. It wasn't until I went to college that my interest in pretty things waned. Occasionally, something would get mixed in my laundry at my dorm or my apartment and I would relapse. When I married Liz, it had been years since I had fully dressed as a girl.

It started innocently enough, Liz and I had gone to our favorite condo at the beach and actually had a nice time, until it was time to leave and she got the idea that the manager should give us a discount for their moving us from the third floor to the second because the owners of the condo we thought we were going to be staying in had the audacity to use their own room. All the way home, it was my fault, If I weren't such a loser, they would have never moved us, if I were more of a man, they would have given us a discount for the nonexistent inconvenience, on and on, for four hours.

When we got home, I unpacked the car and got ready for the business trip I was leaving on the first thing in the morning. Of course, Liz couldn't let it go. Her nagging distracted me while I packed, so somehow, some of her things got into my travel bag. I alternated the two pairs of panties all week. It grew from there. Before long, I was stealing Liz's panties to wear under my clothes and had a small bag at my office full of frilly things to take with me on business trips; I always made sure I had the time to stop by the office to pick it up when I travelled.

"I'm sorry, Carla, it just makes me crazy to even think about her. How about we catch a movie or something? There has to be something out that neither of us have seen."

"Or we could stay here. I have another bottle of wine and Netflix," she smiled.

I couldn't even tell you what the movie we chose was. We were naked on the couch before the opening credits finished, picking up where we had left off early this morning. I don't know how I did it. With Carla, I was eighteen again. I lost two buttons on my shirt when she undressed me and broke a vase on her end table when I kicked my boots off.

Carla swallowed me whole and then did things to my cock with her lips and tongue that I had only read about in some online porn I read now and then, refusing to let me finish. She tortured me forever, and I loved every minute.

When I finally pushed her onto her side and started returning the favor, she got even more aggressive. Ultimately, yeah, that's the right word. Ultimately, we exploded together, her juices covering my face, my seed pulsing down her throat; I think she even squirted into my mouth.

We found ourselves covered in sweat and wine, as both of our glasses had fallen off the coffee table when we rolled onto the floor in the heat of our passion.

"I think I need a shower." Carla gave me a devilish smile. "Or maybe a bath. My tubs huge and it's a jacuzzi."

"Bath, I'm thinking," I smiled as I picked up the wine glasses from the floor and the bottle we had just opened, from the coffee table, following Carla up the stairs watching as her butt swished back and forth on the stairs in front of me. Without a word, we had agreed we could clean up the mess in the morning.