An Evening of Crossdressing

"I've invited my friend Denise over for dinner tonight," Mistress Sharon informed me. "We used to work together at a bridal salon many years ago."

"OK, sounds good to me," I replied.

"I haven't seen her in a long time. You'll really like her."

Later in the day, when it came time to start the dinner preparations, I made the salad and set the table. Mistress Sharon had just got the dinner in the oven when the doorbell rang to announce Denise's arrival.

Mistress Sharon opened the door and Denise stepped in. The two women exchanged hugs and greetings.

"It's great to see you again, Denise!" Mistress Sharon exclaimed.

"It's been way too long," Denise replied.

"This is my boyfriend, William," Mistress Sharon introduced me. "We've been together for a couple of years now."

"Nice to meet you, Denise," I said as I held out my hand.

"Oh no," Mistress Sharon said. "Denise and I are old friends. You can give her a hug."

Denise and I embraced, and then I went to the kitchen to pour some wine.

"White or red?" I asked.

"Oh, I'll have white, please," she replied.

"Sauvignon Blanc OK?" I asked.

"Oh, that's one of my favourites," Denise replied as she slipped off her shoes.

The two women retired to the living room, and when I joined them with the wine, they were sharing stories of the days working in the bridal salon.

"Remember the time that young guy came in and wanted to be fitted with a wedding dress?" Denise asked.

"Oh, that was hilarious," Mistress Sharon laughed.

Denise started to retell the story for my benefit.

"Just before closing time, a young guy about 25, very nervous, came in and asked for a private fitting of a wedding dress. I suggested he stick around until we closed up shop, and we would do it. We locked the doors and took him into the back room. To get a proper fitting, you have to be almost naked, so I asked him to strip down to his underwear. He was wearing lacy women's panties. First, I had to fit him with a bra, so I asked if he would like a padded bra, and what size breasts would he like? Large, he said, so I fitted him with a D-cup, hooking it behind his back and adjusting the straps for a good fit. Meanwhile, Sharon was measuring him and selecting samples from the rack."

"His package slipped out of his panties, so I tucked him back in," Mistress Sharon interjected. "His penis began to stiffen, so I thought, OK, enough of that!"

"He tried on two or three dresses and admired himself in the mirror," Denise continued.

"He became more relaxed as he realized we weren't laughing at him," Mistress Sharon added. "He asked about the prices of the dresses. Wedding dresses are expensive because a lot of expensive fabric and a lot of labour goes into them. "I wish I could afford it," he told us. We undressed him and he put on his street clothes and away he went."

"I still don't know what that was all about!'" Denise pondered. "A gay guy, I've always assumed."

"William might have some insight into that," Mistress Sharon suggested.

"He wasn't actually interested in buying a wedding dress," I began. "He probably wasn't even gay. He was a straight guy with a fetish for women's underwear. He was looking for an erotic experience, but he didn't have a girlfriend, or didn't feel he could share his fantasy with his girlfriend. There was probably a bridal fantasy in there too, but the heart of it was he wanted two women to strip him naked and dress him as a girl. He probably went home and masturbated furiously."

"Oh, I see," Denise responded. "Somehow I get the feeling you would enjoy that yourself."

"Well, yeah..." I mumbled as I looked at the floor.

The two women exchanged knowing glances.

"Show Denise your toenails, dear," Mistress Sharon ordered.

I leaned over and pulled off my socks to reveal my bright red toenails and toe rings.

"Stand up, babe," Mistress Sharon ordered.

I stood, and Mistress Sharon undid my jeans and slid them to my ankles. I stepped out of them and then Mistress Sharon peeled my t-shirt off over my head. I stood there wearing only my red Hanky Panky thong panties.

"Let's go to the bedroom, and I'll show you his lingerie collection," Mistress Sharon suggested.

I followed the two women into the bedroom where Mistress Sharon opened drawers and closets to display my wardrobe of bras and panties and dresses and negligees.

"How shall we dress him for dinner?" Mistress Sharon asked.

The two women selected a bright red push up bra with a D cup to match my panties. Denise looped the padded bra around my shoulders and hooked it behind my back. She adjusted the straps to get a proper fit. My penis began to stiffen.

"You love this, don't you babe?" Mistress Sharon asked as she stroked my penis through the lacy fabric.

"Oh my god," was all I could murmur.

The two women looked at my dresses on the hangers and chose one of my little black dresses, a sleeveless, thigh length, flouncy thing. I don't have any breasts of my own, so I can't do low cut or backless. All it shows is bra straps. Denise pulled the dress on over my head and smoothed everything out.

They stood back to admire their handiwork, then led me to the mirror so I could see for myself.

"We should paint his fingernails to match his toenails," Denise suggested.

"Would you like to do that?" Mistress Sharon asked, as she handed her friend the bottle of red nail polish from the bathroom.

I held out my hands, nails up, and Denise applied a coat of polish to each fingernail.

"I think he'll need a second coat," she said.

We sat in the living room and had a glass of wine while my nail polish dried. After a few minutes, she applied a second coat.

Mistress Sharon had been puttering in the kitchen, and after a few minutes, she announced that dinner was ready. Denise sat at the table while I poured some more wine and then helped Mistress Sharon serve the meal.

We enjoyed an excellent meal of broiled trout and white wine; the two women, and me in my little black dress with large breasts and bright red nails. After dinner, we retired to the living room. Mistress Sharon and I drank some more wine, but Denise had to drive, so she passed on the wine. Talk returned to the young guy in the bridal salon.

"Are you sure he wasn't gay?" Denise asked me.

"If he was gay, why would he want two women to participate in his fantasy?" I replied. "He'd find a couple of guys to do it with instead."

"What do you mean by a 'bridal fantasy'?" Denise asked.

"That's the ultimate in femininity," I replied. "He wants to be dressed as a girl, and there's nothing more feminine than a bride."

"I see," Denise responded. "That makes sense. I finally understand what was going on there."

After a while, Denise announced that it was time for her to head home.

"Thank you for a wonderful evening, Sharon," she said. "It's so great to see you again and meet your boyfriend."

"Thank you for joining us," Mistress Sharon replied. "Let's do it again soon!"

The women hugged and kissed, and then Denise turned her attention to me. She put her arms around me, and I returned the embrace. I didn't want her to feel my erection, but she put her hands on my buttocks and pulled me close so she couldn't help but feel my erect penis against her stomach. She smiled and kissed me on the lips.

"It was so nice to meet you," she told me. "Thank you for your insight into the young man in the bridal shop."

"It was great to meet you, Denise," I replied. "I really enjoyed the evening."

I helped her put on her coat, and she headed out the door with more farewells.

Mistress Sharon took me by the hand and led me to the couch. I snuggled in her embrace and we cuddled and kissed.

"Did you enjoy that, babe?" she asked.

"That was awesome!" I replied.

Mistress Sharon slipped her hand into my panties and began to massage my stiff penis.

"I can tell you enjoyed it!" she said. "You should go to the bedroom and get the dildo and the lube. You deserve a good fucking."

I trotted off to the bedroom and came back with the requested equipment. Mistress Sharon stood, and I fastened the straps around her waist. The dildo stood at attention.

I braced myself against the armrest of the couch with my buttocks in the air. Mistress Sharon hitched up my dress and pulled my panties down to my ankles and I stepped out of them. She squeezed some lube onto my anus and slipped a couple of fingers inside me. She massaged my sphincter to relax me, and then slid the dildo into me slowly, inch by inch, until she was completely inside me. She worked back and forth, slipping in and out, teasing my sphincter, and then driving deep inside. She knows exactly how to drive me wild! I masturbated while she penetrated me and soon, I shot my load on the living room floor.

Mistress Sharon pulled out of me. "OK, you can clean up the mess now," she said.

I went to the kitchen to get some paper towel and spray cleaner to wipe up the mess. I threw the paper towel in the garbage and went to the bathroom to wipe my anus clean. When I returned to the living room, Mistress Sharon had taken off her panties and was lying back on the couch with her legs spread. I ducked under her dress and buried my face in her vagina. I spread her labia and probed her with my tongue. I licked her labia and sucked on her clitoris the way she likes it. I sucked the middle finger of my left hand to lubricate it and slipped it inside her. I found the little ridged area that represents the G-spot. I gently pressed on it and then began rubbing her clitoris with my other hand. I soon had her moaning and writhing. I kept this up for about 10 minutes, and then she arched her back. She moaned and went limp, and I knew she had had an orgasm. I continued kissing her vagina and gently licking her until she said, "Come here, babe."

I slid upwards into her embrace, and she said, "You can fuck me now, you've earned it."

I slid my penis into her vagina and fucked her until I came again. After my orgasm, we cuddled on the couch with my penis inside her. Eventually, I softened and slipped out, so I went to the bathroom to get some toilet paper to clean us up. I wiped Mistress Sharon clean first, and then wiped myself.

"That was a wonderful evening, babe but I think it's bedtime now. Let's finish our wine and go to bed."