Wilma Ann & Friends - The Audition

This story was inspired by a collection of homemade videos posted on various porn sites by a transvestite called Wilma Ann. The videos of Wilma Ann, her wife, and their crossdressing friends are very sexy and I've watched them many times. If Wilma Ann ever reads this story, I hope she understands that it's a tribute to her and her friends.

I was a closet crossdresser. Nobody knew that I secretly bought lingerie, heels, dresses, wigs, and cosmetics online. Nobody knew that I watched hours of YouTube videos to learn how to apply make-up. And nobody knew that I enjoyed getting dolled up and prancing around my apartment. After getting dressed, I would watch crossdresser porn and fantasize about dressing for lovers, especially other crossdressers. I got so turned on thinking of their hands sliding up my stocking-covered legs to the smooth skin of my thighs and then the satin covered bulge between my legs. In the fantasy, of course, I was doing the same to my lover while we kissed. I dreamed of sucking cock and having my sissy cock sucked too. And I fantasized about getting fucked and then thrusting my cock into my lover's ass.

I often had these fantasies while scrolling through crossdresser porn. Inevitably, I ended up watching videos posted by a transvestite named Wilma Ann. Wilma Ann records herself, her wife, and their crossdressing friends playing together. Those videos never failed to get me off. I often fantasized about being with Wilma Ann and her friends even when I wasn't watching them online.

Eventually my loneliness and desires compelled me to contact Wilma Ann. At first, I only wanted to thank her and compliment her for the videos. I hoped to maybe strike up a correspondence. I never could have imagined what actually happened.

I sent Wilma Ann an email using an address I found on a porn site that hosted her videos. I figured it would increase my odds of a reply if I enclosed a photo, so I shaved my legs, slipped into black crotchless panties, and pulled my cock through the opening. I pulled on black thigh-highs and slid my feet into black pumps with ankle straps. Then I laid on the bed with my legs and stiff cock posed and took a selfie from the waist down. I attached the photo to the email and hit send.

To my surprise, Wilma Ann responded. She thanked me for my comments on her videos and she complimented my photo in return. But she said that I needed to show her more if I wanted to hear from her again. I assumed that meant a face pic. I was going to have to risk revealing my identity if I wanted to continue communicating with her. Did I want to go further? Did I want to risk it? Did I want to continue jacking off alone?

It didn't take long before I was fully dressed in a slinky red minidress, black fishnet stockings, and red patent leather pumps with four-inch heels. I wore a dark brunette bob and carefully-applied make-up with smokey eyes and dark red lips. I set up my phone on a tripod and programmed it to take photos every 30 seconds. Then I began posing and doing my best to look feminine and sexy. I pulled up the skirt to reveal my stocking tops. I took off the dress to show my matching bra, thong and garter belt -- all red satin and black lace trim. I turned around and bent over to show my ass. I got on my hands and knees, arched my back, and pushed my ass toward the lens. I laid back against a pile of pillows, spread my legs, and stroked my cock through the panties. Then I slid the thong down my legs and draped them around one ankle while I spread my legs. I photographed my hand and red polished nails stroking my cock. I got back on my hands and knees and photographed myself from behind, including with my red fingertip poking into my ass. I lubed up a dildo and took pics as I fucked myself in the ass. Finally, I got my realistic dildo and took closeups of myself giving it a blowjob. When I was done I jacked off to an explosive orgasm.

Over the next week, I went through all the photos and sent a collection of the best to Wilma Ann. To my shock, she responded with an invitation along with an address and a weekend when I should visit. She explained that I should arrive at her home on Thursday evening to meet with her and her wife, Suzanne. Whether I was invited back for the rest of that weekend would depend on how Thursday went. It was to be an audition of sorts.

I stared at the email for a long time. I never imagined this would happen, that Wilma Ann would invite me and offer the possibility of joining her sexy parties. It was literally beyond my wildest fantasies. But there was significant risk. I assumed that everything at Wilma Ann's was recorded and ended up online. That meant I would be online. In lingerie. And make-up. Having group sex. With crossdressers and trannies. What if somebody recognized me? What if my boss found out? My family? My friends? The life I knew would surely be over.

But then I realized that I was reading this email while wearing a purple lace teddy, black thigh-highs, purple patent leather pumps, and a purple wig. My nails and lips were purple. And my cock was rock hard and throbbing. Of course I was going to risk it all. This is who I was. So I confirmed with Wilma Ann. I bought airline tickets, reserved a rental car, and booked a hotel room near Wilma Ann. In the next weeks, I packed everything I thought I might need. On the Wednesday before my appointed weekend with Wilma Ann, I flew down, drove the rental car to the hotel, and checked in. I spent the evening preparing my body by shaving carefully, applying lotion, and painting my nails. I was willing to risk the nails in public because I assumed nobody would see me long enough or look that closely. The next morning I packed a duffel bag with a blond wig, cosmetics, and the pink frilly outfit I planned to wear. I climbed in the rental car and followed the GPS to Wilma Ann's. I parked out front and sat nervously for a few minutes. It was my last chance to back out, but I wanted this too badly. I took a deep breath, collected my bag, walked to the front door, and rang the bell.

Wilma Ann opened the door. She was wearing a red basque with garters holding up opaque white stockings. Her red thong was over the garter straps. Her feet were in red strappy high-heeled sandals. She seemed perfectly at ease in lingerie while standing in her open doorway in the middle of a residential neighborhood. I was fully clothed and shaking in my oxfords.

Wilma Ann took a long look at me and said, "I thought you were serious about this."

"I... I am," I stammered.

"Clearly not," she said. She gestured at the duffel bag and continued, "Did you seriously think you could slink in here in your man clothes and then change."

Even though Wilma Ann was in lingerie in full view of the neighborhood, I actually asked, "You wanted me to come over here already dressed?"

In a no-nonsense voice, Wilma Ann said, "I play with people who are willing to be all in. When you're ready to demonstrate that you're 100% willing, then you can come back and maybe I'll let you in." Then she shut the door in my face.

I stood there staring at the door. All the mental build-up came crashing down. I felt deflated. My dick was definitely deflated. In fact, I think it was trying to crawl inside me in shame. I turned and trudged back to the car. I got in and stared out the window at nothing in particular. The car must've driven itself back to the hotel because I don't remember the trip. In my room I dumped the contents of the duffel bag on the bed, slumped in a chair, and stared at the jumble of satin, lace, nylon, leather, and cosmetics.

Willing. That was the word Wilma Ann used. Willing. Willing for what? Willing to do what? I started thinking about Wilma Ann. She was a transvestite, not just a crossdresser. She had gone under the knife to get D-sized breasts. There was no hiding that part of her anatomy now. She had sold out and crossed a threshold from which she could not easily return. Some of her playmates were crossdressers, so gender reassignment surgery was not required. I'd been invited, after all. No, what Wilma Ann expected was a sort of mental gender reassignment. A willingness to not just dress like a sexy woman or even have sex while dressed like a sexy woman, but to actually become that sexy woman. How would that sexy woman arrive at Wilma Ann's for a party? Would she dress like a man and change after she arrived? No, she would own it proudly and loudly.

I stood up and stripped naked. I untangled the pink satin bra with white lace trim from the pile, wrapped the band around my chest, connected the clasp, and slipped the straps over my shoulders. I found the C-cup breast forms and fitted them in the cups. I sifted through the pile, pulled out the matching garter belt, and clasped it around my waist. I carefully untangled the sheer white stockings with lace tops and carefully pulled them up my smooth shaved legs. I attached the garters and smoothed everything out. I found the thong that matched the bra and garter belt and I stepped into it and pulled it into place, nestling my cock in the gusset. I picked up the "dress" if you could call it that. It was a Bo-Peep-style number in pink satin with frilly lace. The skirt barely covered my ass so it had no chance of hiding the garters or stocking tops. I slipped into it and zipped it up. I picked up the long blond wig, faced the mirror, and got it situated on my head. I brushed the hair smooth. I took my time with the make-up; a nice pink blush, some pink eye shadow, and glossy pink lip gloss. I slipped my feet into pink patent pumps with three-inch heels. I took a long look in the full-length mirror. I adjusted the dress slightly, hoping that I could make it slightly less scandalous before going out in public. I packed the rest of my belongings and put the suitcase by the door.

I peeked through the security lens in the door, but I couldn't see anybody. My car was just outside the door. I cracked the door, but still couldn't see anybody. I stuck my head out and looked again. Nobody. From the room, I unlocked the rental car with the key fob. I took a deep breath, grabbed the suitcase, and scurried to the car. I panicked and fumbled the latch momentarily before jerking the door open, throwing in the suitcase, and practically jumping into the seat. I slammed the door shut and realized my heart was racing and my lungs were heaving. I'd gone only about 10 feet. Calm down. Nobody saw. You're good. I started the car, sped out of the parking lot, and headed back to Wilma Ann's. My pulse and breathing calmed as I drove, though my nervousness never left me completely.

Panic returned when I parked at Wilma Ann's house because I had to get from the car to her door and then wait to be let in. But this was part of being willing. Willing to become the woman I wanted to be. I scanned the area. No one around. I took a deep breath and got out of the car. I steadied my legs, not because of the heels but because my legs were practically shaking in fear. Then I straightened my back, thrust out my tits, and strode more confidently than I felt to the door. I pressed the doorbell firmly and waited. I was scared to death but I held my ground. It seemed like an eternity until Wilma Ann opened the door. She looked me up and down, smiled approvingly, stepped aside, and welcomed me in. Wilma Ann led me through the house to the living room. Suzanne was sitting on the sofa but she got up to greet me.

"Welcome," Suzanne said sweetly. "We enjoyed the photos you sent. It's a pleasure to meet you in person. What's your name, hon?"

"T...T... um...well," I stammered. "I... well, I never really..." The truth was I could never decide on a name so I changed what I called myself from week to week.

Suzanne saved me. "It's alright, dear. Let us get to know you and we'll pick one together. Have a seat here. I'll get us some drinks."

Wilma Ann sat on one end of the sofa and gestured for me to sit next to her. I did and she draped an arm around my shoulders. I started to relax in the safety of her home. Suzanne returned with glasses of white wine and we all took sips. She was wearing all black: thigh-highs, pumps, thong, and baby doll nightie. Her long blond hair hung loose around her shoulders. Despite my lingering nervousness I really wanted to kiss her red lips.

Suzanne complimented my outfit and make-up. She turned out to be a bit of a chatterbox and soon we were talking like old friends about clothes, shoes, and makeup. I didn't register at first that Wilma Ann had placed a hand on my knee. I noticed when it slid up to my thigh. It was all I could think of when her fingertips touched my bare skin above the stocking top. I turned and looked at her. Wilma Ann leaned in and kissed me. The hand on my shoulder came to the back of my head and she held me while her tongue entered my mouth. Her other hand began stroking the inside of my thigh.

Suzanne brushed my hair back off my shoulder and started kissing my neck. I felt her hand on my knee and she gently pulled my legs apart. They seemed to be working together. As Suzanne spread my legs, Wilma Ann's hand crept higher. I gasped when her fingertips touched the bulge in my panties. With the kiss broken, I turned to look at Suzanne. She kissed me and our tongues danced. My legs were spread wide by now and Wilma Ann was stroking my rigid cock through my panties.

When Suzanne released the kiss, I looked back to Wilma Ann. She leaned back, displaying her body to me. Her big boobs had fallen out of the flimsy cups of the basque. Her legs were spread and her cock bulged in her panties. The pose was an invitation, an invitation for me to continue proving that I was willing. As much as I wanted to continue being the focus of their attention, I knew that's not what tonight was about. Tonight was about me giving, not receiving. If I proved my willingness to give, then there would be plenty of receiving later.

I knelt between Wilma Ann's spread legs. I leaned forward and flicked my tongue at her fleshy nipple. I teased the tip and then licked around the nipple before taking it in my mouth. As I sucked one breast, I caressed the other with my hand. Once the nipple in my mouth was hard, I switched and gave the other the same treatment. When both nipples were hard, I kissed down across the red satin of the basque, lingering momentarily on the bare skin between it and the top of her thong. Then I licked and kissed the bulge growing behind the red satin there. I gently reached for the thong waistband and Wilma Ann lifted her ass off the sofa. I tugged the thong down her legs and off. Wilma Ann's cock stood stiff in front of me. Looking her in the eyes, I placed my tongue at the base of her cock and slowly licked its full length to the head. I repeated the tongue stroke but this time I lingered and teased the soft, sensitive skin under the head. From there I licked around the ridge of her cockhead. I opened my mouth and took her in.

"That's a girl," Wilma Ann murmured.

It was intoxicating to be here in lingerie, on my knees, with a cock in my mouth, and to be called a girl. I wanted to be a good girl and give a good blowjob. I pushed more of Wilma Ann's shaft in my mouth, keeping tight contact with my lips and tongue. My head began bobbing steadily on her cock. My hands caressed her tits and played with her nipples.

"Balls," Wilma Ann murmured, "suck my balls."

I released her cock and moved my mouth down to her balls. I stroked her cock with one hand and caressed her breast with the other. I gently took one ball into my mouth, lovingly swishing it in my mouth. Then I did the same to the other before taking both in my mouth.

As I sucked Wilma Ann's balls, I felt Suzanne move behind me. She knelt and snuggled against my back. I could feel her hard cock against my ass. She swept my hair to one side and began kissing the nape of my neck. I felt her hands on my thighs, which were together, and I sensed she wanted me to spread them. I did so while continuing to suck Wilma Ann's balls. Suzanne's hands moved up my thighs under the dress and began stroking my raging cock through my pink panties.

"Suck me," Wilma Ann breathed.

I released her balls and wrapped my lips around her cock again. I sucked harder this time, sensing that she wasn't far from climax. I tweaked her nipples as my head bobbed more rapidly on her cock. I felt her hand on the back of my head guiding the pace she wanted. I followed her lead, keeping continuous contact between my mouth and her cock. I soon felt the telltale throbbing and knew she was close.

"I'm cumming," Wilma Ann gasped just before her cum flooded my mouth. I swallowed as rapidly as I could as her balls emptied. Suzanne was whispering in my ear what I sexy cocksucker I was. When Wilma Ann started to relax and her cock began softening, I released it and swallowed the cum still in my mouth. I milked her cock gently and licked the remaining cum from the slit.

Suzanne moved next to me and we kissed deeply as she tasted Wilma Ann's cum in my mouth. Suzanne pushed me onto my back on the floor and climbed on top of me. As we kissed, she moved between my legs and ground her cock against mine through our panties. I put my hands on her ass and pulled her tighter against me. After kissing for a while, Suzanne raised up and straddled my chest. She pulled her thong to the side and released her stiff cock which bobbed right in my face. I opened my mouth and she fed it to me, fucking my mouth. I reached up and played with her nipples through her black satin nighty.

While Suzanne fucked my mouth, I felt Wilma Ann get on the floor with us. I felt her pulling down my thong. I lifted my ass to help her and she pulled it down my legs and off. She lifted my legs and told Suzanne to hold them. Suzanne paused fucking briefly to grab my ankles and put my legs under her arms. Then she resumed fucking my mouth. Wilma Ann began licking my ass, probing it with her tongue. I felt her fingers next as they rubbed lube around my tight hole. A lubed finger pressed into me and then a second. She began finger-fucking my ass while Suzanne fucked my mouth. Wilma Ann was twisting her fingers inside me to stretch my anus open. Just about the time my ass started to relax and adjust to the invasion, she withdrew her fingers and replaced them with her cock. Unbelievably, she was hard again and forcing her stiff cock into my virgin ass.

Suzanne was breathing heavily and repeating "yes, yes, god yes" as she fucked my mouth faster and faster. Soon she let out a little squeal and thrust her cock nearly down my throat. Her cock exploded and another load of cum filled my mouth. When she was done she rolled off me. Wilma Ann was fucking my ass now. She put her hands on the backs of my thighs, pressing them against my chest. She leaned over me with my legs over her shoulders. She fucked my upturned ass steadily, burying her full length inside me over and over.

"You're a tight little whore. You're going to be very popular with the girls," Wilma Ann said. It was so dirty but I loved it, partly because I wanted to be a slutty whore and partly because it meant I was passing the audition. "Roll over you little slut," Wilma Ann said as she pulled out of me. I immediately got on my hands and knees and she plunged her cock back into my ass. She grabbed my hips and began fucking me with a furious pace. Suzanne reached under me and stroked my raging cock. I was in a state of ecstasy and knew I wouldn't last long. Wilma Ann didn't either. With a grunt she slammed her cock deep in my ass and filled it with her cum. Almost immediately I came and pumped my load into Suzanne's waiting hand. When I stopped cumming, Suzanne brought her hand to my face and offered it to me. While they both watched, I licked my cum from the palm of Suzanne's hand. I really was a crossdressing slut and I loved it.