Finding Evelynn

Just a quick short story to hold you over while I tie up some details on a longer story I've been dying to finish. I hope you enjoy Carla and Dave's journey, well Evelynn's too. All standard caveats apply. Please leave me a comment when you're finished. Your feedback keeps me going.

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"Carla, we need to talk." I collapsed onto the sofa and took a deep breath.

"Dave, what's the matter?" Carla sat on the sofa next to me and handed me a cold beer.

"Maybe nothing." I smiled at her. "At least until you get sick and tired of me. The RNG deal went through today. I sold the company."

"What does that mean, exactly?" I could see the confusion mixed with excitement in her face.

"It means that you and I are going to Europe for two months and then figuring out how to be together all the time without killing each other. It means no more sacrificing our lives for the employees when things get tight. We are finally free to do what we want to do. They offered three times what I was going to ask, and I got them to agree to four. Baby, We. Are. Set." I said the last three words in a deliberate staccato to emphasize them.

We truly were. The deal we finally agreed on added an eighth zero to the price they paid me for my small software company. More accurately, they paid for the clever little application I owned the patent for. The one that had the unique quality of enhancing transaction processing time by a significant factor for the tech stack they used. It would save RNG a lot more than it cost them and would give them access to my short and rather lucrative customer list, but I didn't care. My twenty employees would all receive nice signing bonuses. RNG guaranteed all their jobs for at least two years.

The millions they paid me were more than enough for Carla and me to do whatever we wanted. Right now, what I wanted was to hear my beautiful red-haired vixen scream my name as I drove her from one orgasm to the next.

I set my beer down and dove onto the couch, tackling Carla and sucking her tonsils from her throat before carrying her upstairs to our room. Practically ripping her clothes off, I dove between her legs for the first act in the most carnal opera she and I had enjoyed since our wedding night.

My jaw was sore, and I looked like a glazed doughnut when we finally stopped. Carla had cum four times and my small cock had erupted twice across my stomach from her massaging my prostate. I came a third time from her amazing skill with her tongue and lips.

We didn't have what most people would consider a traditional sex life, but we made up for it with technique and enthusiasm. Carla and I often joked that I was the best lesbian lover any girl could ever ask for. I had what my doctor called a micro penis. It was about the size of my little finger, but not as long. It also meant I missed out on a lot of traditionally masculine traits, like height, body hair or anything resembling a beard, a broad chest, or muscular build. Stuff like that. None of that mattered to Carla, and her acceptance had given me the confidence to create a company around my clever invention.

What I was lacking in manhood, I made up for with a rapier wit, above average intelligence, and a willingness to do whatever it took to make Carla happy. Carla had an adventurous streak a mile wide. The two of us together were almost perfect. It didn't hurt that I could touch my nose with my tongue.

Europe was amazing. Italy, Spain, France, Switzerland, Germany, and England. We felt like we had seen everything there was to see, but knew we hadn't even come close. Our last night in Berlin was probably the highlight of the entire trip. It certainly changed me in ways I never expected.

We had been doing the traditional touristy things for a few days and Carla asked the desk clerk at our hotel for something different. "We want something fun to do before we headed for London." She had told him. He recommended a cabaret not too far from the hotel. It offered an amateur night of sorts, promising it was always fun and decidedly different, noting that if we left now, we could get dinner before the show started.

We had no sooner walked in the cabaret's door when an elaborately dressed and very attractive and a bit overdone woman accosted me, asking if I had a song I could sing. "We always need new talent for our amateur night."

"You could do 'The Rose'" Carla practically shouted. "You almost sound like Bette Midler when you do it at karaoke. And it is my favorite song. Go on, sign up honey. It would be so much fun."

"I guess I'm in." I shrugged. "What do I need to do?"

"Just come backstage in about an hour." She pointed to the left of the stage at the back of the cabaret. "We have people that will help you get ready. And there's a 500 Euro prize for the crowd favorite."

What did I have to lose? I knew I could kill the song, and I was a tenor, so my range and Bette's were similar. Mostly, I knew it would get Carla all worked up and the sex when we got back to the hotel would be amazing.

We grabbed a quick bite, and I made my way to the backstage door they had pointed out to me. Before I could protest, the lady I had met at the front door grabbed me and started undressing me right there.

"Wait, what...?"

"It's a drag show, honey. I thought you knew that. Now come on, we need to get you made up and dressed before the show starts."

I looked around and a dozen other 'girls' were in various stages of undress. A few were in chairs in front of huge lighted mirrors, with someone working on their makeup. Evening gowns and wigs flew everywhere. Except for mine, there was no modesty in the room. Before I knew it, I was completely naked, stepping into a lacey pair of bright red panties.

"Girl, you are so lucky. You don't even need to tuck." The girl dressing me patted my little erection as it disappeared into the soft satin and lace.

A garter and stockings were next, followed by an impressive pair of fake tits which she glued to my chest before covering in a delicate lace bra. Of course it matched the panties and garter.

"You'll need to get used to these. Try not to break your ankle." She laughed and handed me a pair of shoes that had to have at least a five-inch heel. I was well past complaining about what they were doing to me. Besides, I thought it would be fun to see if Carla even recognized me before I started singing, so I stepped into the shoes and did my best to not fall on my face.

"Go easy on her, girls. She's a virgin." They put me in one of the makeup chairs and two women started on my face. I watched in the mirror as the transformation took place. Several of the girls that had gone before me had elaborate, almost garish makeup. From what I could gather, I didn't need as much help and, while it was still stage makeup, mine was a lot more subdued. Bright red press on nails, some clip-on earrings, and they gave me a short, skin-tight, red cocktail dress to slip into. As a finishing touch, they set a long, wavey red wig on my head and stepped back, letting me take in the finished product. Shit, I would fuck me - or try, anyway.

"We need a name, honey. How do you want us to introduce you?" I looked at her, dumbfounded.

"Um, Evelynn. It's my wife's middle name." What I had gotten myself into was sinking in. I was just about ready to back out when the host for the evening started her introduction. The show was starting. She was hilarious and had the crowd ready to go before she introduced the first contestant.

I was going last and spent my time pacing, trying to get used to the ridiculously high heels I was wearing and hoping that Carla didn't take this the wrong way. I was sure she didn't have a clue either when I said I'd sign up. By the time Evelynn took the stage, there would be no doubt that I was going to be dressed as a woman when it was my turn.

"Please welcome our final contestant, Evelynn. I am told this is her first time tonight. Not only to compete but to dress as a woman, so be generous and let her know how much you love her."

I walked out onto the stage, trying not to fall off my heels, and took the microphone, searching for Carla in the crowd. When I found her, I saw the love in her eyes. I locked onto her.

The simple piano intro started. When it was time, I took a deep breath and sang to Carla, "Some say love, it is a river..." I was in my moment. I poured all the love I had for my lovely wife into every word, completely forgetting where I was or what I was wearing.

"...Lies the seed that with the sun's love in the spring becomes the rose." Carla was crying her eyes out. I closed my eyes and curtsied as the entire room erupted in applause.

The other contestants surrounded me, hugging me, kissing my cheeks. I didn't understand the words most of them were using, but I knew what they were saying. Several of them were crying, too.

The MC recognized the top three finalists. When she announced me as the winner, I felt as giddy as a schoolgirl. It was Carla that started shouting for me to sing another song. The rest of the crowd quickly joined in.

"Well, Evelynn?" The MC offered me the microphone. I told her what I wanted to sing.

Pointing at Carla, I beckoned her to join me on the stage. They gave her a chair, and I absolutely destroyed her with a rendition of 'Wind Beneath My Wings.' Bette Midler is her favorite, after all.

Anika, it turns out that was my handler's name, took Carla and me backstage, where they fixed our makeup. It was part of the deal that the winner had to hang around and schmooze with her fans for a while after the contest. Another thing I didn't know before the competition, but why would they tell me that? Who thought some strange guy off the street would do what I had done?

While they were putting the finishing touches on my ruined mascara, I noticed Carla and Anika chatting animatedly in the corner. Carla smiled as Anika nodded and handed her a shopping bag, giving her a big hug and kissing her on the cheek.

The three of us made our way out to the club, where people inundated me with comments about what a wonderful job I had done using various levels of English. Carla tried to stay with me but was getting jostled and ignored, so she made her way back to our table to wait for me.

Anika finally rescued me and led me to join Carla, where a bottle of wine was waiting with two glasses, a nice regional Riesling.

"You were amazing. You never sing like that at karaoke." Carla beamed.

"I'm usually a little tipsy and a lot less motivated to make an impression at karaoke." I laughed.

We sat and sipped our wine in silence for a few minutes. I could tell Carla wanted to say something and, not sure what it was, wanted to give her time to put her words in the exact order she wanted.

"You look beautiful." She smiled and blushed at me.

"It surprised me, too." I took a sip of my wine and smiled at her.

"I made a deal with Anika. You can keep the clothes, the wig, shoes, everything. She will accept your prize money as payment. I have your boy clothes in the bag next to me."

"Carla, boy clothes, what...?" I set my wine down and leaned on the table closer to her.

"You're so beautiful and you looked so happy when you were singing. I just thought maybe Evelynn might like to stay around for a little while. That's all." She bit her lip. I could tell there was more to it than just that, but years of experience told me she wasn't ready to tell me yet.

"And maybe Carla wants to see what it's really like to have a lesbian lover?" I gave her my most devilish grin.

"Maybe." She said coyly.

I was close to the truth, but could tell it went deeper.

We sat and drank our wine. I told her about getting ready and how Anika never gave me a chance to protest or back out, admitting that when it was all over, I had had a blast.

People drifted by and congratulated me, and I even posed for pictures. Anika joined us as it got closer to closing time, slipping an envelope discretely to me under the table and winking. Where she thought I was going to hide it in the skimpy dress she had put me in was anybody's guess. I had a powerful impression Carla didn't want me to change before we headed back to the hotel.

I gave the envelope to Carla, and she put it in her purse. It was a little perplexing that Anika had reneged on their deal by paying me the winner's prize and letting Evelynn keep the outfit. She also offered an open invitation to come back anytime and perform again.

We finally said our goodbyes and walked the few blocks back to the hotel. I had figured out walking in the five-inch heels and never once thought about someone calling me out for being a guy in a dress. Most of the people we passed saw exactly what they wanted to see, two beautiful women walking together.

The desk clerk did a double take as we made our way toward the elevators. "So, you had fun?"

"She won." Carla beamed back at him. "Now I'm going to fuck her brains out, if you will forgive the language."

I just grinned as the click of my heels echoed through the lobby.

"Well, you girls have fun and try not to disturb the other guests. I'll put you down for a late checkout." We all laughed.

The sex was amazing. Carla let me take off was my dress and the tight panties that had hidden my little friend. The rest, the makeup, wig, bra and forms, the garter, stocking and even the heels; I had to wear. I dove into her pussy, and she swallowed my small cock whole. Using her finger to tease and probe my ass as she sucked my little soldier.

She was teasing me, toying with me, dragging my orgasm out longer and longer. I sucked and licked her clit, nibbling softly and pulling on her nether lips, driving her from her first orgasm to her second.

Carla's hand disappeared for a minute, only to return covered in cool, slick liquid. She slathered around my hole before slipping her middle finger inside me all the way to the knuckle. I moaned loudly as the invader slipped in and out of my ass, moving faster and faster while her tongue and lips continued to torture my cock and balls.

A second finger joined the first and then a third as she led me to the precipice again and again, only to deny me with a gentle squeeze at the base of my cock.

"Do you trust me?" She whispered in my ear after she left a trail of soft kisses from my cock to my neck.

"You know I do and, as worked up as you have me, I'd let you do anything." I moaned as she drove all three fingers as deep as they would go.

"Good. Close your eyes and I'll be right back." I felt the bed shift as she got up, her soft footfalls fading across the room.

"Are you ready for your surprise?" She whispered softly when she crawled back onto the bed.

"Yes, please?" I moaned again, expecting a small vibrator on my prostate to bring me to my climax. What I got was nothing I ever expected. She slipped her slick fingers inside me again, thrusting a few times before she pulled them free.

She moved between my legs and lifted my ankles, resting them on her shoulders. I could feel her press something different against my ass.

"Oh shit. Carla, are you doing what I think you're doing?"

"I told the desk clerk I was going to fuck your brains out. Are you ready?" She didn't wait for an answer as she shoved the dildo she was wearing into my ass, taking me all the way to its base. I screamed. It hurt, but it felt so good.

Leaning down to kiss me, her hands massaging my fake tits, she fucked me. Not tender and loving, but like a fiend possessed. I hadn't opened my eyes until she made me scream, so I didn't have a clue how big the dildo she was fucking me with was. It felt like it was in my throat and If I'd had to guess, I'd have said you could park a Buick in the opening it was going to leave when she was done with me.

"Anika gave it to me when I told her what I was going to do to you. Does it feel good?"

All I could manage was a loud moan, as the searing pain subsided, and an intense pleasure took its place.

The dildo ravaged my hole while it massaged my prostate, clear pre-cum dripping from my cock as intense feelings radiated from inside me. Running down through my crotch, into my thighs and legs, up through my torso and out my arms, I felt like someone had plugged me into an electrical outlet. It wasn't just the quick intense burst of pleasure I normally experienced; it was longer, deeper, fuller. My whole body shook as it tore through me, and I erupted all over my stomach. I trembled and shook as it waned, only to build again as Carla started thrusting more and more furiously.

A second wave and then a third. I was exhausted when she finally collapsed on top of me, leaving the thick hard shaft she had fucked me with embedded inside me as she nestled on my chest.

"Evelynn, I want you so bad." Carla moaned softly as she finally pulled the massive cock from my aching hole, going to the bathroom to clean it up. It had to be eight inches long and so thick. I just laid there, unable to move.

Carla brought a warm washcloth back with her and gently cleaned the mess from my stomach, kissing my little cock sweetly when she finished. I collapsed into an exhausted sleep, waking up with Carla spooning behind me, her hand cupped on my fake boob.

It took some creative packing, but we got all of Evelynn's things in our suitcases. The flight to London was almost too uneventful. Carla was unusually quiet, and I was a little tired and sore from last night, so I took a nap while she made plans to change my life in ways I never expected.

We did all the standard tourist stuff, changing of the guards, Tower of London, castle tours in Scotland, over to Ireland, and back through Wales. We even saw a performance of 'Two Gentlemen of Verona' in The Globe. As we traveled around the United Kingdom, Evelynn's things filtered to the bottom of my suitcase as she became a fond memory, at least for me. Carla had other plans, and, of course, the massive strap-on dildo made a few cameo appearances. I quickly decided I enjoyed it almost as much as Carla seemed to.

By the time we boarded our flight back to the States, we were both so exhausted we slept the entire flight.

I expected the moderate chaos I would come home to. Anytime one company buys another, there are transition issues. I had signed a consulting contract for the next six months to help smooth out the rough edges. I hadn't expected it to be two weeks of twelve-hour days. To be fair, if I hadn't run off to Europe with Carla for two months, it would have been less of a mess. There were some questions that needed to be answered and a few expectations that needed to be massaged to make the integration work like RNG had expected.

While I focused on making RNG happy, Carla focused on other things, little things, subtle things, things like replacing my shampoo and body wash. She even replaced my deodorant with a lavender scented stick of Secret.

"I love the way you smell now, and your skin is just so soft I could touch you like this all day." Carla was nestled next to me after an epic session of lovemaking, celebrating the end of my long days as the strap-on poked me in my side. I clenched my butt in response to the emptiness it had left behind.

"It would be even softer if we did something about all this hair." She ran her fingers through the small tuft of hair on my chest and her foot up and down my leg. "You like how soft and smooth I am, don't you?"

"You know I do." I moaned and rolled over to kiss her. "Do you want me to shave?"

"I was thinking maybe you'd like to come to my spa with me the next time I go. They can do laser, so you don't have to worry about it anymore. That's what I did to my legs, and it's so nice not to have to shave and they are so smooth." She ran her leg over mine. She was right. Her legs were so smooth, just like the rest of her body, and I loved touching her. It only seemed fair that she gets to enjoy the same thing.