Outed as a Crossdresser

One evening I overheard Mistress Sharon talking on the phone to her friend Chantelle.

"William is a cross-dresser," she told Chantelle. "He's had a life-long fetish with women's clothing. His previous girlfriends weren't supportive, so he never had a chance to explore it until he met me."

I couldn't hear the other side of the conversation, but it seemed that Chantelle was intrigued. I was kind of embarrassed about being outed like that, but also excited. I wondered what might come of this.

"Why don't you come over for dinner tomorrow", Mistress Sharon continued. "We can have some fun."

Later, Mistress Sharon informed me that she had invited Chantelle over for dinner. "You will be dressed as a girl."

So that was it. I'd been outed as a cross-dresser to one of Sharon's girlfriends. I didn't really know if I was more embarrassed or excited. Chantelle already knew that I painted my toenails and wore toe rings and ankle bracelets, so this was just the next step.

The following afternoon, while Mistress Sharon was preparing dinner, I had a shower. I thoroughly shaved, from my face down to my toes, so I was completely hairless, and then presented myself to Mistress Sharon for inspection.

"You missed a few spots", she informed me. "Bring me a razor and I'll finish the job for you."

I went to the bathroom and returned with a fresh razor. Mistress Sharon shaved a few spots on my legs and my scrotum, and then had me bend over so she could shave around my anus.

"You know what happens when you don't shave properly," she said.

I dutifully lay across her lap with my buttocks raised and submitted to a spanking. Mistress Sharon delivered several sharp blows to each cheek with a bamboo paddle until my buttocks flushed a bright pink.

"Now go and get dressed for dinner," she ordered. "Put on your purple bra and panties and purple dress, and then I'll do your makeup."

I selected the requested items from my lingerie wardrobe. A purple push-up bra with the La Senza logo band gave me a D-cup. The matching purple panties also had a La Senza logo waistband. The sleeveless purple dress hung to about mid-thigh. I also wore several toe rings and a bracelet on each ankle, and bracelets on both wrists.

Mistress Sharon came to the bedroom to check on my progress. "That looks great," she informed me. "Sit down at the vanity and I'll do your makeup."

First, she removed my existing pink nail polish with nail polish remover. Then she applied a base coat and gave that a few minutes to dry. She selected a purple nail polish to match my dress and underwear. She painted my toenails and fingernails, and then proceeded to do my face while the nail polish dried. She applied foundation and blush, and then a light purple eyeshadow. Next she applied eyeliner and mascara and finished off with a light purple lipstick. The final touch was a blonde wig with purple highlights. I inspected myself in the mirror. I made a fairly passable girl.

Chantelle arrived not long after. She knocked once, and opened the door. Mistress Sharon greeted her with a hug and a kiss, while I took her jacket and hung it in the hall closet.

"Look at you!" she exclaimed in her sweet Quebecois accent as she looked me up and down. "Tres joli!"

She took me by both hands and kissed me on the lips.

The two women sat on the couch in the living room while I went to the kitchen to pour some wine. I returned to the living room with a glass of Pinot Noir for Chantelle, and Sauvignon Blanc for Mistress Sharon and myself.

Mistress Sharon had been telling Chantelle about my cross-dressing habits. "I'm so happy that he feels able to share this aspect of himself with me," she said. "His previous girlfriends didn't understand at all, and he had to hide it. You're much happier being open about it, aren't you, Babe?"

I agreed with her assessment. "I'm glad I don't have to hide it anymore."

"He seems very much in touch with the feminine side of his personality," Chantelle suggested.

"I think you're right about that," Mistress Sharon agreed.

Dinner was ready so we moved to the kitchen. Mistress Sharon had made baked lasagna and Caesar salad. The two women sat with their wine while I served dinner. I topped up our wine glasses and joined them.

When we finished dinner, Mistress Sharon and Chantelle moved to the living room with their wine. I loaded the dishwasher and tidied up the kitchen and then joined them.

"You've got a spot of grease on your dress, dear," Mistress Sharon informed me. "Take it off and throw it in the laundry."

I wasn't sure if she wanted me to go to the bedroom and change or take it off right there in front of Chantelle. A Blues tune was playing on the radio, so I made up a bump-and-grind routine to stall for time. The two women seemed to appreciate the dance, so I kept going, and peeled the dress off over my head. I threw the dress on the back of a chair and continued to dance. My penis stiffened and popped out of my panties.

"Oh, he's really enjoying this!" Chantelle laughed.

Mistress Sharon held out her arms. "Come here, Babe," she requested. "You deserve a spanking for messing your dress."

She pulled down my panties and I lay across her lap with my buttocks in the air. Mistress Sharon picked up the bamboo paddle from the coffee table and delivered several sharp smacks across my cheeks.

"Would you like to spank him, Chantelle?" she asked.

"I'd love to do that," she responded, and Mistress Sharon handed her the paddle. Chantelle smacked me several times on the buttocks.

"His face is as red as his cheeks," she laughed.

"He loves the humiliation, though." Mistress Sharon informed her. "Why don't you get the dildo and lube, dear? We'll put on a show for Chantelle."

I went to the bedroom and got the strapon dildo and lube from the bedside drawer and returned to the living room. Mistress Sharon stood up, and I fastened the straps of the dildo around her waist. Chantelle sat with her eyes wide in amazement.

"Wow!" she exclaimed. "Your sex life just keeps getting wilder and wilder! Tabarnac!"

I leaned over the armrest of the couch with my buttocks in the air. Mistress Sharon dropped my panties to my ankles and I stepped out of them. She squeezed some lube onto her fingers and inserted two fingers in my anus and massaged me to relax the sphincter. She slid the dildo into me bit by bit and then thrust it home. She worked in and out of me while I masturbated.

"Would you like to fuck him, too," she asked Chantelle. "You're my best friend, so I don't mind if you fuck my boyfriend."

"I'd love to," Chantelle replied. "I've never done this before!"

Mistress Sharon unstrapped the dildo and placed it around Chantelle's waist. Chantelle penetrated me, but didn't have the experience. She popped out of me repeatedly and Mistress Sharon guided her back in.

"That was fun!" she declared. "I'd love to do that again!"

"I'm sure there will be many opportunities," Mistress Sharon assured her. I wiped my anus clean with a handful of tissues and then lay back in Mistress Sharon's arms and masturbated. I was so aroused by this point I soon squirted sperm all my belly. Mistress Sharon scooped up my sperm on her fingers and held them to my mouth. I sucked my sperm from her fingers and swallowed it.

You clean yourself up and bring us some more wine, Babe," Mistress Sharon requested.

I went to the bathroom and wiped myself clean. I checked my makeup in the mirror and freshened up my lipstick. I grabbed a short, see-through negligee and pulled it over my head. I went to the kitchen and opened some more wine and topped up all the glasses and then joined the women on the couch.

The two women had been chatting in the meantime.

"Have you ever taken him out in public dressed as a girl?"

"I have," Sharon replied. "There's a gay bar downtown where a lot of drag queens hang out. We went there for Halloween last year."

"Oh, that would be so much fun!" Chantelle exclaimed. "I'd love to see that!"

Sharon picked up her phone and began to scroll through the photos until she found the photos from Twisted Element on Halloween. She showed Chantelle the photos of me in a push-up bra and pink dress with a dog collar around my neck.

"I was wearing my motorcycle leathers, with a pair of handcuffs on my belt, and leading him by a dog leash," she elaborated. "We actually won 50 bucks for best costume."

"I really liked the way women would come up and talk to Mistress Sharon," I interjected. "They would ignore me, and talk to her because they knew she was the domme and I was the sub."

"We should go there sometime," Chantelle replied. "Two mistresses and our slave. That would be a lot of fun!"

And so a new plan was made...