The Bet Ch. 04

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Wifey won and hubby has more crossdressing strapon fun.
4.4k words
4.69
121.3k
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Part 4 of the 8 part series

Updated 10/28/2022
Created 12/01/2006
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jomar
jomar
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*****

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. On Saturday, she dressed me in sexy lingerie and gave me a world class handjob during halftime. Saturday night she dressed me in sexy lingerie and did me with a very special strap-on. Lilla had plans.

Sleeping on my side I woke to a cold pressure at my rear. As I drifted into awareness I arched my back some so she could take me more easily. She slipped in gently and set a leisurely Sunday morning pace. The immense fullness in my rear was wonderful, welcome. She reached around to my hardening cock and stroked me. Her hand felt like silk on me.

"Good morning, baby," I heard close to my ear. "I saw your sweet little ass there and just couldn't resist. I hope you don't mind," Lilla said softly as she stroked me faster until, with a small moan, I came. "Here, baby," she said as she brought her fingers to my mouth for cleaning.

"Mmm, you sure are enjoying all of this, baby doll. You sure you've never been a backdoor man before?" she teased.

"Your backdoor," I laughed. "And good morning to you, too," I said as I reached back and squeezed her.

We had a light breakfast, drank coffee, read the paper. Finally Lilla came over, worked off my beautiful plum wig and said, "Okay sugar, you know the drill by now. Get up there and do the triple S, use those Fleet thingies, and I'll meet you in the bedroom."

I did all that and came out of the bathroom naked. Lilla said, "Not so fast, eager beaver, let's get you dolled up before you put on the goodies this time."

So she did it again. Lilla worked her makeup magic on me and used subtle shades of girl stuff to downplay masculinity and enhance femininity on my fairly androgynous features. Then the dangly earrings that caught the light. The black lace choker to hide my Adam's apple. And the spectacular almost shoulder length deep purple wig with sexily parted bangs, the highlightsshimmering in the light. She also put several thin silver metal bracelets on both of my wrists that made dainty clinks whenever my arms moved.

"There. Not bad if I say so myself. C'mon, back to the bedroom, sweets." Standing, I was amazed yet again to see a decent looking babe staring back at me from the mirror. I closed my eyes, shook my head slightly and felt the graceful sway of my beautiful dark plum colored hair, felt its delicate caress on my face and the tug of earrings on my lobes. My cock twitched. I stood and walked into the bedroom.

On the bed were the goodies. The scalloped top sheer black thigh highs that came up almost to my crotch. She was right, it did feel nice when my boys rubbed against them. The pointy five inch fuck me pumps, no sides, stiletto heels, ankle straps. A black lace thong. A black long sleeved lace dress, sleeves flared at the forearm. I figured that she was dressing me in all these flared long sleeved outfits for the same reason she painted my long fake nails a light burgundy, so I'd be more conscious of the femininity, feel more feminine. There was something else on the bed that didn't register at first.

"Lilla, what are those?"

"Aren't they awesome? Those are your new tits, baby. I got them from this website. You wouldn't belive the stuff they have, they've got everything! You're a C cup, baby, hefty three inchers, how about that. It was a really hard decision, baby, there wereso many great models to choose from. The Kirsten Dunsts, the Diane Lanes and Drew Barrymores were outstanding. And the Teri Hatchers were spectacular! I finally narrowed it down and went back and forth between the Halle Berrys and Elizabeth Hurleys, but in the end I went with the Hurleys. They're classics. What do you think?" she asked, beaming proudly.

"Why are they shaped like that?" The breast and base was wide and only slighlty rounded on the top, and the sides and bottom of the base followed the shape of the breast.

"They're wider at the top than regular breast forms to look more realistic. That way they hang naturally and don't look plopped on. Here, take a look," Lilla said as she handed me one.

I held a flesh colored boob. The cover felt like skin, and it was soft and jiggled like the real thing. The areola sized somewhere between a quarter and a fifty cent coin, with nipples mid-way between soft and erect.

"What's it made of?"

"Who knows, pumpkin, some hi-tech stuff and space age materials. The website went on and on about their 'breast density matrix' and 'breast fluid viscosity.' Pff, whatever. All I know is they feel real. Did you notice? The base side is a little bit firmer."

I turned it over. "What's that?"

"That, baby cakes, is the optional clamp. Isn't it brilliant?" she gushed. "It's a teensy clamp that attaches to your nipple with a little adhesive to help it stay put. Then, and this is the best, cupcake, then when the fake nipple is pulled you feel a tug on yours. Isn't that wild? I mean, who thinksup this shit?" Lilla said as she smiled brilliantly, leaned slightly at the waist for emphasis, then clapped her hands and bounced up and down on her toes a few times.

"How's it do that?"

"Who cares? I think it has a little string thingy attached to the nipple and the clamp somehow. Oh, and the harder you pull the nipple the more the clamp digs in. Ha! You're gonnalove it, you'll see. C'mon, let's get these babies on you."

"Ugh." I let my head drop, chin against chest, again.

Lilla put adhesive on the back of the breast and on the clamp. She pulled the clamp out a little from its recessed position and I noticed the nipple sucked in some. I stood silently while she put the clamp on my nipple, eyed me like she was hanging a picture on the wall and, presto, I had a boob. The clamp wasn't pinching, but resting comfortably until called into action. As Lilla put the other one on me I asked her how to get them off. She said I wouldn't want them off, but a hot shower would do it.

The color of my breasts was almost exactly the shade of my skin. The edges of the base glued to my skin tapered to a thin sharp point and blended so smoothly you could hardly tell where they ended. Lilla marched me back into the bathroom and my new tits swayed naturally. I could feel the clamps presence, but no pinch. It was weird. It was surprisingly erotic. My cock twitched.

Lilla used some more makeup to really blend in the edges and when she was done stood behind me looking at me in the mirror.

"Ohmigod, baby. I don't think God or even Industrial Light and Magic could have done a much better job."

We stared at my shapely C cup breasts, the inside edges curving gracefully up towards each other, blending naturally onto my chest about an inch apart. The outside edges rounding out a bit past my slim torso, out and up and also blending smoothly and naturally at the top. From the top my breasts sloped down, out, back in, where the bottoms curved slightly back up to meet the base. I stared at my natural looking tits. My cutting edge Hurleys.

I twisted side to side, leaned side to side, bounced on my toes and my lifelike breasts swayed and jiggled and settled naturally. Amazing. And they were only the barest hint lighter than my own skin. I figured that depending on the light you probably couldn't tell the difference. I stood there staring at myself, pulled a towel around my waist and was astounded. A good looking woman with a killer body.

"Oh,hell yeah," whooped Lilla. "Let's get you dressed!"

I pulled on the sheer black stockings and they almost floated up by bare legs by themselves. I carefully pulled the lace dress over my head and down. It was a slightly snug from the neck to the hips and stretched easily. The neck was a wide oval, almost to my shoulders and dropping down my back a few inches and more in front, showing some cleavage. From the hips down it flared, undulated easily around me and ended about mid thigh. It had a lot of swish to it. Black lace thong. And the five inch fuck me pumps.

Lilla told me to go downstairs and make up some mimosas. As I did, carefully in my five inch fuck me pumps, I was startled at the sight of the beautiful woman who met my eye in the foyer mirror. I stared, turned this way and that. "I could actually pass in public," I marveled. Almost in a daze, I continued on and made us a pitcher of mimosas.

"Wow. Nice rack there, Liz," Lilla teased as she entered the kitchen and I handed her a drink. She moved in tight, caressed my breast, and as it moved under her hand I felt shifting weight and the promise of the clamp. "Cheers, baby. Amazing, isn't it? God, you're tits are perfect." We drank a toast and as I raised my glass my arm grazed my breast and again I felt the subtle weight shift. It felt sensuous, erotic.

Lilla went with a lipstick lesbian theme today. Except for the shoes she wore the outfit I had on yesterday. A sexy, florescent green lace top with long flared sleeves. A wide garter belt and sheer black stockings. A sexy, flippy, swishy black miniskirt. And five inch black fuck me pumps. Subtle makeup. Her stunning red hair in careful disarray. A lump under the skirt told me she had on the strap-on, bent down from the looks of it. She was spectacular.

We went into the den. Lilla didn't waste any time today. She took my drink, set it on the coffee table, put her hand on my neck and kissed me. She rubbed my front. She'd worked her makeup and lingerie magic on me and I felt so feminine, so receptive. I loved that she wanted me, that she desired me. I wanted her to show me how much she wanted me. I wanted to please her. She kissed me, and I was hers.

"Down girl," Lilla said softly as she pushed me over the high, wide, round arm of our brown leather couch. "I'll be good to you, sweets, nothing but goodness."

I let her push me over, settled on my waist and put my arms out, palm down, to support me, my deep plum colored hair fell around my face. I felt the tugging swing of my dangly earrings, heard the bracelets light tinkling. I saw my lacey sleeves leading down to my long, light burgundy nails. I felt the weight of my breasts pulling down and settling, the shape changing to perfectly fit my position. It surprised me to realize that I wanted Lilla, wanted her in me, back there. I closed my eyes, arched my back a little, raising my rear to her.

Lilla caressed my rear. Said, "Mmm, baby, I do love that ass. You know I love you to fuck my ass, hon, love to feel your cock back there. It's always open for you, isn't it, baby. You love it too, don't you. You weren't sure you would, but you do. Like my cock in your ass, that is. Your cock. Isn't that wild, doll, a kit to make a dildo from a mold of your dick. What's it like to get fucked with your own cock, baby. I can't even imagine whatthat does to your head."

I moaned softly as she caressed my rear, rubbed across my front. She flipped my skirt up and pulled off my thong. I felt cool slickness on my opening. I felt a thin pressure. I reached back and spread my ass for her and heard my bracelets clink, felt my breasts shift.

"Ooh, very good, hot cakes, very good. What is it that you want, baby, tell me what you want," Lilla said as she rubbed my cock.

"Please," I said.

She kept the pressure at my opening steady, didn't push into me. I tried rocking my hips back up to her, but she moved with me, denying me. "Please," I said again.

"You have to tell me, baby, like I tell you."

"Oh god. Please Lilla, put it in."

"Uh uh, baby, you know what I want. Good for the goose, good for the gander," she said lovingly as she continued to rub me. She snaked a thin finger up my rear and pressed my prostate. She caressed my back and around to my breast.

"Oh god, fuck me Lilla, please fuck me," I gasped.

"That's my little whore. Okay, baby, since you asked I'll fuck you real good." Lilla gently pressed her cock into me and slid deep. She stayed there, swayed and twisted side to side some.

"Like it? You like our cock in your ass? Mmm, baby, I'm fucking your ass with your cock. You're feeling what I feel when you fuck me. When you fuck my ass. So thick and full back there. Yeah, baby, you like it, your cock is hard. Are you ready? Can you picture me? Behind you. Against your ass in a sexy green lace top, black miniskirt, sheer black stockings held up by that sexy wide garter belt. And five inch fuck me pumps. Looking down at my cock in your ass. Hold that image while I fuck you, baby. Are you ready? It's okay baby, let me know when you're ready."

"Yes," I husked, and put out my hands and arms to support me.

And she began. Lilla gave me long, deep, slow stokes. The wide head of our cock slipped back and forth across that special place and I loved her for finding it again and again.

A new sensation. My breasts moved with Lilla's thrusts and I felt the weight of them pull on my skin. Forward then back. No twist from the clamp, but I felt its presence and the light sensation reminded me of a nipple rubbing across fabric. Sensual. I moaned and relaxed back there as much as I could so she could take me. Oh god, my breasts, hair and earrings swaying while she fucked me. I loved it. On and on she went, and the pressure built inside me and I wanted that release. Lilla grunted behind me. She stabbed into me relentlessly. I sensed her building need and wanted her to use me to get there. I wanted that. I wanted her to use me for her pleasure.

She rocked against me and it felt wonderful. On and on she went. Lilla took me from behind and finally groaned and yelled. She eased out of me and slumped over my back, her cock between my legs, nestled against me. I'd felt my own growing need, but I couldn't get there. Instead, I glowed knowing she found her release through me.

My nipples throbbed lightly and as I stood up, my lacey dress slid over my rear. My breasts settled back in to place and I liked the feel of the shifting mass.

"Thank you, baby. That was nice. This dildo is awesome. I'm just using the fuckey part today, but it sure did hit the sweet spot. Was it good for you, baby? I hope so, I hate to say it, but I almost forgot about your pleasure. Do guys do that? Work their cock in and out trying to come and forget about everything else? Do you do that? Sometimes, baby, I'm happy just to feel you ride me. I don't always come, but love your cock in me and making you come."

I smiled with understanding.

"Cheers, baby," I said and kissed her.

"C'mon girlfriend, we got some football to watch."

"I thought you said femmes only watched girly shows."

"Nah, you can be fem and watch sports. Besides, big game today, Barbie."

"I know."

"Okay, so you go get the fixings, make another pitcher of mimosas and hurry your sexy ass back in here."

In the kitchen I prepared the snacks. I was aroused the whole time. My bracelets tinkling, my flared sleeves and dress flowing, my dangly earrings and brilliant hair swinging, My breasts swaying. High heels altering my step. I registered all of these feminine sensations as I moved about the kitchen.

My arms brushed against my breasts as I reached for things. My nipples brushed against my lace dress. No, my fake nipples brushed against my lace dress and the clamp moving slightly on my nipple made it feel so real.

We sat on the coach in front of the television, sipping mimosas and watching the game. Lilla liked football, but it seemed to me an odd sight: Two chicks in sexy lingerie watching the game. Me in my sexy long sleeve lace dress that snuggled lightly against my C cup breasts then flared at the hips, sheer stockings, five inch stiletto fuck me pumps, tinkly bracelets, dangly earrings and dazzling deep purple wig. Lilla in her florescent green lace top with long flared sleeves, wide garter and sheer black stockings, sexy swishy black miniskirt, and her own pair of black five inch fuck me pumps. I was aroused the whole game.

After the game, I looked over at Lilla. So gorgeous. She gave me a dazzling smile and I wanted to make her happy. I reached under her skirt, bent the strap-on upright and made sure it was seated in the right spot. I still had lubrication in me from before but put a little more on the tip. I swung a leg over her and, looking into her loving, stunning eyes, settled down on her, all the way until I felt her thighs against me. She spread her legs a little and pushed up some. She was huge in me.

With my feet hooked over Lillas' spread knees, I rocked my hips, slid forward and back, moving the base against her. My cock grew hard as I ground against her. I worked the base of the strap-on against her and she leaned back, closed her eyes and smiled.

"That's nice, baby. Feels real good," Lilla softly said.

I felt so full back there as I rocked my hips on her. I leaned forward and pressed my lips to hers, my tongue parted her soft full lips and pushed in with love. My hair cascaded around us creating our special, private world where only the two of us existed while we kissed and kissed and kissed.

When we finally broke away Lilla cupped my breast, massaged me and fondled me. I felt weight shift, the tug of the clamp, not hard, but slightly pulling this way and that. Lilla bent forward and took licked my nipple through the lace. She pulled my dress off my shoulder and down below my breasts. I shrugged off the sleeves and my dress folded downward under my breasts. Lilla fondled and played with my breasts and I closed my eyes and enjoyed her touch. She took my nipple between her teeth and leaned back. My breast stretched after her. The string grew taught and the clamp bit. She pinched my nipple and I moaned. I ground against her and she played with my breasts and nipples. Lilla scooped my precum with two fingers, put them in my mouth and I sucked them as our eyes locked.

After a time, I leaned back, supported by my arms, my hands on the coffee table while I ground against her, her thick cock deep inside of me. Looking down between my naked breasts, I watched Lilla stroke my cock with her small hand, smile, lean forward, and take me into her mouth.

She sucked me and used her hand on me as I rocked my pelvis against her, looked down between my shapely bare breasts and watched her gorgeous red hair sway. The feeling was overwhelming, so much pleasure front and back. She sucked me and I pulled my nipple and felt the sting of the clamp as I came. Lilla reached up, put a hand behind my neck and pulled me to her. As our tongues collided I tasted salty come and I moaned while she swirled her tongue around mine. As we kissed I couldn't help it, I had to feel it, and rose up and down on her cock, felt that wonderful thickness slide over and over that spot. I moaned into her mouth.

I settled and ground against her on and on, watching her breath faster and harder until she grabbed my hips and peaked and came and came and came.

I stayed on her, hugged her, my face nuzzled in her gorgeous red locks, covered now by my dazzling deep purple hair. I finally eased off of her and said, "That was nice, sweety, that was lovely," kissed her and went to freshen up a little in my five inch stiletto fuck me pumps and swaying feminine things.

And the day wore on. We sipped mimosas, watched television, read, and lounged about in our lacy girly clothes. She made me practice walking in my five inch fuck me pumps. She had me deep throat her some and I was a bit stunned to find I could do it with ease now. Before our romantic candlelight dinner she had me lean over the kitchen island on my elbows, flipped up my lacey skirt and took me one more time. I loved feeling my dangly earrings tugging, my fabulous hair swishing, and especially my breasts swaying with Lilla's powerful thrusts that caressed that sweet spot inside of me. That pressure built a bit, but we groaned and laughed and had to stop when the oven timer went off.

jomar
jomar
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