The Bet - Cover

The Bet

Copyright© 2006 by jomar

Chapter 3

Erotica Sex Story: Chapter 3 - 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. This morning, she dressed me in sexy lingerie and gave me a world class handjob. Lilla had plans.

After an early dinner Lilla called me upstairs. A pretty woman briefly caught my eye as I passed the foyer mirror and strutted up the stairs in my 3 inch pumps, sexy green lacy top, deep plum hair and dangly earrings swaying with my movements, the hem of my flippy black dress snapping smartly with my steps.

I entered the bedroom and Lilla said, "Hey love bug, let me get this wig off you, then I want you to take a shower and shave real good. Oh, and make sure you use those Fleet thingies I left out for you. Chop, chop, lambkins."

I did all that, got squeaky clean, inside and out. When I came back into the bedroom Lilla pointed at the bed. "Okay, tootsie, I have some more dainties for you. You're gonna love these," she gushed. "Look, baby, here's a lace half jacket and half slip from Frederick's, your new favorite store. I love the lace bra with the sheer sleeves. Ooh, and the lace half slip. Don't you love the wide solid border on the bottom?"

"Sure," I muttered.

"Oh, I know you do-oo. So put it on, sweets. And put on these scalloped topped thigh highs. I got 'em long 'cause I wanted 'em way up there on you. Maybe the boys'll rub against them. Wouldn't that feel great?" she teased. "And you're really gonna love these, baby. Put them on and follow me."

Besides the lingerie, Lilla left me black 5 inch fuck me pumps. Very pointy closed toe, no sides, stiletto heels, ankle straps. I put them on, held onto whatever I could grab and wobbled my way to the bathroom vanity.

In the mirror I saw myself wearing a black sheer half-jacket attached to a black lacy bra. The "jacket" sat a couple of inches over the tops of my shoulders and the sheer sleeves flared at mid-forearm where the material changed to lace. I had to admit it was sexy. Bare skin below the bra, the black half slip, skirt-like, about a foot in length, half lace, half microfibre, set low on my hips just above my cock. Long, sexy legs with sheer black thigh highs rising up to my crotch. I was slim and in pretty good shape so, surprisingly, the look wasn't bad.

"Okay, honey bunny, quit admiring your sexy self and turn this way. She sat me down and made me up. Again. All the subtle shades and touches she had used before on my already androgynous looks, hiding masculinity and emphasizing femininity. Lilla did something with my eyebrows and eyelashes, a light touch with smoky eye shadow, lipstick then other magic to bring out my cheekbones. The tasteful dangly earrings that twinkled. A black lace choker. And that dazzling deep plum wig with highlights that simply sparkled in the light.

I looked at myself in the mirror, slender, flat tummy, skimpy lingerie, actually attractive, and thought, "How can I look like this. I'm a man for cryin' out loud."

Lilla gaped at me, softly said, "Frickin' unbelievable. Tomorrow's gonna be outfuckinstanding."

"What do you mean?"

"Nothing, baby. How about you go downstairs and get some more champagne for us."

When I finally, unsteadily, got back to the bedroom, dressed in my skimpy black lingerie, 5 inch fuck me pumps and sporting a semi-hardon, from the friction I told myself, Lilla was on the bed reclining against the headboard in her blue silk robe, black sheer stockings and shoes similar to mine.

"Hey baby, welcome back," she said in a sultry voice, patted the bed.

"Cheers baby," She said as I stretched out next to her. She put her arm around me, smiled warmly at me in my sexy outfit and dazzling purple hair. We clinked glasses and sipped champagne. "You look absolutely fabulous, baby. I'm amazed. What's it feel like to be such a hot little number?"

"I don't know, Lilla, kind of weird. At first I didn't want to, but here with you it's okay, I guess. I mean, if this does it for you, then I'll do it."

"Oh, it do. But don't you feel sexy, baby? Doesn't it turn you on, tent your skirt a little, hmm?

"I guess, some. I didn't expect that. Brings out different feelings, you know? And when I passed the mirror downstairs I did a double take. It's weird."

"Mmm, you're gorgeous, baby. I'm gonna bring out all kinds of feelings in you, pumpkin."

I sipped champagne and Lilla took my glass, put both on the bedside table. She put her arm back around me and pulled me to her for a kiss. Softly, lips brushing, she nibbled and bit my lips. She pulled away slightly and looked at me, smiled sweetly and kissed me again, lips parted and tongues caressed.

Breathing a little heavier when we broke, Lilla said, "Baby, you know how I love your mouth. Are you gonna be good to me, use your mouth on me?"

"Mmm, yeah baby, I'll use my mouth on you," I said and leaned in for another kiss.

"Take off my robe, sugar lips," Lilla said with a small smile.

I untied the front and slipped the robe down her shoulders. She leaned forward slightly to let me pull it away from her. She had on the wide garter belt I wore earlier today, a matching black lace bra, and something else.

"Surprise, baby. How do you like our new toy? I love this thing! It's got a wire inside so I can adjust the angle of the dangle. Isn't that what you guys say? It also has a curvy part that goes inside of me and it fits perfectly along my little pleasure zone. Ooh, and get this, it comes apart so I can just use the fucky end on you," she said and snuggled against me. "It's awesome, peanut butter. It's a win-win strap-on, baby. Here, touch it."

Lilla pulled my hand to her strap-on and I gently touched it, causing her to squirm slightly. It was flesh toned and felt silky soft. The thin outer cover moved slightly over whatever firm spongy material was underneath. It was both soft and hard. It was a state of the art dick.

"Wow, that's pretty realistic. Where'd you get it?"

"That's right, baby, it's very realistic. I got it from Fake-Me-A-Man.com, lover. They have all kinds of cool stuff," Lilla said with a gleam in her eye. "Okay dollface, you know what to do, you promised, remember?"

Sighing with resignation, I moved to my side, on my elbow, leaned down took her into my mouth. I moved my head up and down some, tried not to scrape her with my teeth.

"Mmm, that's nice lover. I can feel it. This is gonna be good, baby. You're doing great."

I continued my efforts, taking a little more of her in, my plum colored hair and dangly earrings flowing and swaying some. I felt so feminine. As I sucked Lilla, she talked.

"Mmm, So nice, baby, don't stop. That's good. Does my cock seem familiar, baby? Do you recognize it?"

"What?" I wondered.

"You should, you're sucking your own cock, baby, the one I made from you this morning. Isn't that horny?"

A vague anxiety surfaced. I felt my cock move slightly.

"Sucking your own cock because you can. Isn't that the punchline, baby? Mmm, now you know why I like your cock so much, why I like to suck it. Doesn't it feel good in your mouth, baby? Makes you stretch wide for it, doesn't it. But not too much. Not too big, not too little, it's just right. Oh! That felt nice, baby, keep going."

"I'm gonna teach you to deep throat our cock, baby. Just like I do. Are you ready? Are you ready to learn to take me all the way? To feel what I feel?" She stroked the back of my pretty purple hair as I rose and fell on her stiff spongy cock.

I moaned with a perverse pleasure.

Lilla slid down and lay flat on the bed. "Here, move around this way." She moved me so I was sort of lying across her stomach, facing her cock. Okay baby, tilt your head back a bit to straighten your neck some. Now extend your tongue just past your lower lip. That's right, sexy. Flatten the back of your tongue like you have a tongue depressor back there. Okay, baby, now force your throat open like you're yawning. That'll help counter that nasty gag reflex."

I did as she said, feeling the dildo penetrate deeper into my mouth. I got a little anxious.

"That's right, baby, you're doing fine," she said gently. "Oh, that feels good. Take a deep breath and slowly slide me in."

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