The Bet
Chapter 2

Copyright© 2006 by jomar

Erotica Sex Story: Chapter 2 - Ch.1-Wifey wins bet and hubby must comply. Ch.2-Wifey won the bet and dresses hubby up. Ch.3-Wifey won the bet and pretty hubby takes her strapon. Ch.4-Wifey won and hubby has more crossdressing strapon fun.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Consensual   CrossDressing   FemaleDom   Oral Sex   Anal Sex   Masturbation   Sex Toys  

We bet big. To the winner, anything goes for the weekend and the loser must comply. I thought I had it in the bag, but she won. And now I had no hair, the hard way. Except for my head, she waxed me stem to stern Friday night. She had plans.

"Wake up, huggie bear, we have a lot to do-oo," Lilla said playfully.

"Morning, baby," I croaked as I grabbed her for a hug.

She hugged me back, squirmed away and said excitedly, "Come on, let's get going."

Lilla could barely contain herself during breakfast. She was so beautiful, so open and full of life. I loved her so much.

After breakfast she ran upstairs while I finished my coffee and read the paper.

"Oh, poo-kums," she trilled down to me, "come on u-up."

"Dag," I thought as I slowly climbed the stairs. I knew what was coming.

More supplies and a towel spread out on the bed which she had me lay on. Lilla cleaned me, ran a damp washcloth over cock, balls and rear. Then she fluffed me, stroked and sucked me, toyed with my rear opening with finger and tongue, maybe getting me harder than I'd ever been. At my hardest she slapped some goo on me and made a mold of my cock.

"Surprise, stud muffin. I miss your wiener sometimes when you're not around. Aren't you glad?" she smirked.

Lilla did her thing while I showered and shaved my face shiny. I had to admit it felt sensuous having no hair, my hands sliding effortlessly across my skin. I got hard. I couldn't help it.

I emerged from the bathroom in my cotton gym shorts, pulling on my t-shirt. "Okay sweetie pie, I have some underfrillies for you on the bed," Lilla said with a gleam in her eye, hands clasped under her chin, torso twisting slightly back and forth.

"Lilla, are you sure you want this?"

She cozied up to me with a serious face, lay her palm gently on my cheek, looked adoringly up at me with those amazing green eyes framed by her blazing red shoulder length hair, said emphatically, "Fuckin' A, dude. Now get naked!" and slapped my ass.

I laughed and I took my shorts and shirt off, stared at the items on the bed.

Lilla noted my apprehension and said, "Ooh, isn't this awesome, baby? It's the stretch lace garter belt from Frederick's. And those are scalloped lace-top stockings, also from Frederick's I might add. I think black is sooo sexy, don't you?"

"Ugh," I uttered as I dropped my chin to my chest.

"Come on, baby, get dressed, get dressed," she said excitedly.

Resigned, I picked up the garter and pulled it on. It was pretty wide, maybe five or six inches. I sat on the edge of the bed. As I pulled the first stocking up my incredibly smooth leg, my cock twitched. As I pulled up the second stocking it stiffened a little more.

"See, see, you're getting a boner! I told you this would be fun," Lilla squealed with delight and waggled a pointed finger.

"The only reason I'm gettin' any wood at all is because you're standing there naked rubbing your twat," I shot back.

"Uh uh-h, can't fool me-e," she singsonged.

Finished clipping the stockings to the straps, I stood up. The base of my semi-hard cock was just beneath the edge of the garter, smoothness all around. Lilla handed me a lacy luminescent green long sleeved v-necked top, sleeves flared at the wrist, saying, "Okay, this is from VS. Velly sexy, hmm?"

"Maybe on you," I pouted, putting it on.

Next I put on a flippy, swishy black miniskirt that barely covered the band at the top of my stockings.

Lilla came up, hugged me, kissed me while stroking my cock under my skirt, said in a husky voice, "God, that's so hot. You're gonna look amazing when I'm done. Put these on and come with me," She handed me a black lace thong and 3 inch black pumps.

With considerable effort I put them on and wobbled into the bathroom after her. She motioned me to sit down next to her at the vanity, which I did.

Sitting on a stool in her blue silk robe, Lilla had an array of girl stuff spread out on the counter in front of her. She tapped her lips with an index finger, found what she wanted and dove in. She made me up. She put fake fingernails on me and painted them a light burgundy; colored, not natural so I'd know they were there, she said. Applied to my face whatever it is that women apply. When she was done she pulled out a dazzling, dark purple wig and secured it to my head as I closed my eyes and thought, "I must be nuts."

With a final touch here and there Lilla beamed, spun my stool to the mirror and exclaimed with a flourish, "Ta daa!"

Astounding. From the mirror, a woman stared back. I was speechless. I have somewhat androgynous features and Lilla's deft hand with makeup camouflaged masculinity and accentuated femininity, eyelids, lashes, eyebrows, cheekbones, lips. A delicate black lace choker to hide my Adam's apple. Tasteful dangly earrings. Rich, dark plum colored shoulder length hair, feathered bangs parted stylishly. I gently shook my head and my silky hair swayed easily with my movements, the highlights dancing in the bright vanity light. I felt the wavering tug of the earrings. I was dumbfounded.

Lilla spoke reverently, "Oh my god baby, you're prettier than I ever imagined you'd be. This is amazing. You're beautiful. Stand up, let me look at you."

I stood up and looked in the mirror not believing what I saw. A slender, flat chested, decent looking, if not leaning toward hot, babe. My cock stiffened some.

"Fuck yeah, baby, that's what I'm talkin' 'bout!" Lilla crowed, rubbed my cock, kissed me long and hard.

 
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