Wifey wins bet and wants more frilly fun

I hope you enjoy the kink.


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 was fucked. Literally. She had plans and the day was due.

Lilla popped up in bed bright and early and pumped her fists in the air. "Yay! Come on, dude! Wake up!"

I pulled a pillow over my head and moaned. I was a little hungover. Lilla had waxed me from top to bottom and stem to stern last night and I drank white wine to shield the pain of having all the hair on my body below my neck ripped off by a strip of wax. She would only let me drink white wine, saying it was a proper ladies drink.

"Honey! Get up! We have a big day ahead of us. I need to get started on your hair."


"Your hair, silly. I need to do your hair. No self respecting woman is going to be seen in public with that mop you have."


Lilla laughed. "Surprise! We're going on a road trip, sweets. I have hotel reservations a few hours away. It'll be a blast!" Lilla threw the sheet off, popped onto her knees and straddled me. She leaned down, her glorious red hair framing my face. She wiggled her crotch on me and said, "Okay, sport. Today's the day. Ooh, you feel so soft and silky. I bet it's weird with no body hair, huh. I like it. I bet you do too. Now get up and let's get going!"

I was hard and tried to maneuver Lilla so I could fuck her, but she laughed and squirmed away saying, "I don't think you'll be fucking me this weekend," and skipped into the bathroom.

"Oh, man," I said and rolled out of bed.

We had a light breakfast then Lilla shooed me to the bathroom to "shit, shower and shave that face to the bone," and to use one of those "fleet thingys," as she called it. I did all that needed doing and called for Lilla.

Lilla was a master of makeup and hair and all things girly. She took off the rubber band that held my hair in a small ponytail and fluffed me. "I'm so glad you grew your hair out for me. You didn't even balk just once. I'm sure you were hoping I'd win another bet so you could be a girl again. I'm sorry, I mean a woman," she said "a woman" in a deeper, husky voice and giggled and went to work.

She gathered my hair and snipped it and clipped it here and there, stood back to look and worked on me some more. She put shiny things in my hair and plastered it with goop. After awhile she undid everything, made me rinse it and then she blew it dry wielding a brush and moving my head this way and that.

"Your dick is hard."

"You're naked and you've been flashing your tits in my face. Of course my dick is hard."

"Nuh uh. You're thinking of how beautiful you're gonna look and how I'm gonna fuck your sweet little bum. See! You twitched!"

"Ugh. Just get on with it."

"And...there." Lilla spun me around and it wasn't me in the mirror. Rather, it was and it wasn't. My shoulder length light brown hair was now blond with highlights and was parted in a line starting above the middle of my eyebrow and the bangs flowed naturally across my forehead to end just below my eye. The ends about my shoulders and neck were feathered and curled and the look was utterly feminine and sublimely sexy. Like I'd just been fucked and wanted to be fucked again.

I shook my head and my hair flowed lightly across my shoulders and settled. I couldn't believe it. "Jesus, that's amazing, Lilla."

"Isn't it! Fucking A, hon. I know you have more than a bit of that androgynous look to you, drew me to you and all, but shit! I had no idea it would turn out this good. And we're not even done yet! I can't wait to see you made up. Here."

Lilla turned me back around and went to work doing that makeup magic she does so well. "Just a little light day makeup. We'll get you all slutty tonight," she said and giggled. She plucked and shaped my eyebrows and did a little of this and a little of that with a small brush and a pad. Lipstick.

"I can't believe I'm letting you do this," I said.

"Oh hush," Lilla said and scooped some precum off the end of my hard cock and fed it to me. "You might not believe it but your wiener does and I think he likes it." She deftly worked on my eyes until she was satisfied.

She looked at me and gave a low whistle. "Damn. If you look this good now you're gonna be stunning when you get decked out, doll. A mankiller."

"What." I started to turn and look at myself in the mirror.

Lilla stopped me. "No, no, not yet, sweets. I want you to get the full effect." Lilla gave me a pedicure and painted my toenails a light cinnamon color, her favorite. She gave me a manicure, put on very high quality fake nails on me and painted them the same shade as my toenails saying, "This color is just fabulous. Goes with anything, babe."

She wagged a finger at me. "Promise me you won't look in the mirror. I have to get something from the bedroom."


Lilla padded out and I was tempted to sneak a glance. As I started to turn Lilla yelled, "No looking!" I didn't and she was back with a box.

"What's in the box?"


"The Hurley's," I said with resignation.

"Bingo, baby! And not just the Hurley's but the new, improved Hurley's. Ooh, there were so many new ones on that website. I was sorely tempted by the Madonna's, the Thora Birche's, the Tyra Banks's. And the Angelina Jolie's, oh my god, to die for! But in the end, once again, I just had to go with the Hurley's. Thirty-six C funbags, cupcake. Do you know I read somewhere they did a poll and hers were considered the best boobs ever. Or something like that."

"Do tell."

"Yes! And now you have them! Isn't that brilliant? Get it? Brilliant? Because that's how they talk in England and Liz is..."

"I get it."

Lilla laughed. "This is so awesome. Here, have a boob." She took one out of the box and handed it to me.

It was shaped as I remembered. The base extended beyond the breast form. The sides and bottom of the base followed the shape of the breast until at the widest point, moving toward the top, or shoulder edge, it tapered only slightly and the base edge was only slightly rounded at the top. As Lilla had explained to me before the base was wider at the top than regular breast forms were to look more realistic and hang more naturally, even if the wearer stood on his head, for whatever odd reason that might happen.

I held it. It was flesh colored, of course, and the cover felt almost exactly like skin. It was soft and jiggled like the real thing. The areola was sized somewhere between a quarter and a fifty cent coin and the nipple mid-way between soft and erect.

"This thing is amazing. What makes it new and improved?"

"Fuck all if I know. According to the website it has a significantly improved breast fluid viscosity and density matrix interaction leading to a far more realistic experience. They did a blind comparison, you know, real versus fake and guess what?" She said "Guess what," again when I didn't say anything.


"People couldn't tell the difference!" Her eyes were wide and she was leaning toward me, her heels off the ground. "I mean, isn't that insane!"

"What do you mean they couldn't tell a difference? That doesn't make sense."

"They said there's a huge range in titty shapes and tata feel. Like some big ones are firm, some are medium and some are even hangers."

"What's a hanger?"

"You know, ones that are mostly skin it seems. You know, hangers."

"If you say so."

"I do. Okay, babycakes, let's get these puppies on you."

I turned it over and saw a pad and remembered the clamp's subtle caress and its bite. "They improved the clamp system too. See, no clamp anymore. It's held there by adhesive. You can tell me if it's improved or not," she teased. "Amazing shit, truly amazing."

"Whatever." My heart was beating a little faster.

Lilla cleaned my chest with alcohol, dried it, put adhesive on the back of the breast and on the small pad that would be attached to my nipple and areola. She pulled the pad out a little from its recessed position and I noticed the nipple sucked in some as the connecting string tugged it from behind. As before, I stood silently while she glued the pad to my nipple and areola. She eyed me, getting it level, and voila! I had a boobage.

As Lilla put the other one on me I asked, "Do they come off the same? With a shower?"

"Oh! That's the best part, sweetie. They have a new adhesive, a breathing adhesive, they call it, and your tits can stay on up to a week without having to take them off. All part of the new matiterial. Crap, that joke sucked. Anyway, all part of the new design."

"Sooo, how does it come off?" I said.

She held up a bottle labeled 'Breast Remover.' "Great. Just as long as it doesn't take my skin off."

"Not to worry. Okay, let me blend the edges." Lilla went back to work on my new tits. "Jesus, this is way better than before. These edges are tapered so sharp and thin it hardly needs touch-up. Especially since they're feathered a bit, too. Man-o-man."

"Here, put these on. Then you can look." Lilla handed me a pair of lacy, rose colored tanga panties.

I took them and looked at her. She was standing there naked in the brightly lit bathroom, smiling, bouncing on her toes, her hands clasped together under her chin.

I oriented them and leaned over slightly and my hair flowed sensuously over my skin. My breasts swayed naturally with my movement and my arms grazed them as I reached down and my cock twitched. I stepped into the panties and pulled them up my long, smooth legs, the beginnings of a feminine wriggle already surfacing. I tucked myself down.

Lilla was staring at me. Silent. Eyes wide, a look of amazement on her face.


Lilla put her hands on my shoulders and turned me around to face the mirror. My jaw dropped. A pretty blonde was staring back at me. Me, but not me. Me as a woman. Not a guy with makeup on, but...a woman. The person in the mirror could walk into any room and no one would think twice about gender. I took measure of myself.

Lilla's makeup wizardry had actually made my face pretty. Sexy, feminine blond hair with highlights. Slender, toned body. And killer tits. My shapely thirty-six C breasts. I looked them over carefully, caressed them. Unlike last time, the color of my breasts was exactly the shade of my skin. I couldn't tell where the edges of the base ended and my skin began. The inside edges curved gracefully up towards each other near the top. The outside edges rounding out a bit past my slim torso, out and up and back in. From the top my breasts sloped down, out, back in, where the bottoms curved slightly back up to meet the base. My new and improved Hurley's.

And then we remembered to breathe.

"Holy shitski, hon. Who the hell is that hot blond?"

"How'd you get the Hurley's to match my skin?"

"I sent a digital photo."

"Oh, that's what that was for."

"Yeah. They couldn't guarantee, but..."


"Yeah. Who'd'a thunk."

I just stared at the lovely woman in the rose colored tanga panties. I turned to the left, to the right. I got a mirror and looked at myself from the rear. I was attractive. I liked the panties and how my bottom looked in them.

Lilla snapped out of it first. "Got-damn!" She poked one of my boobs and it wobbled then settled like a real one.


"C'mon, girlfriend! Let's get you dolled up and get on the road. She took me by the hand and led me into the bedroom. On the foot of the bed were clothes.

"Okay, okay," Lilla bounced up and down on her toes. "Put these on while I get dressed."

"Stockings? During the day?"

"Oh yes, dearest. They're the sheerest of the sheer. Very lightweight. Not that you really need them, of course, but it's a feminine touch and I don't want you to forget for even a moment."

"Like that's gonna happen."

"So don't just stand there. Put them on."

I sat on the edge of the bed and picked one up. It was so very sheer there was really no color to it. I found the opening and quickly gathered it up with my fingers, surprised at how quickly the skill came back.

"Sweet," Lilla commented.

I reached down, my arms grazing my breasts, a slight tingle on my nipple and I loved the feel. It felt so delightfully feminine to feel my breasts on my arms. I pointed my toes with the cinnamon colored toenails and wrapped my foot in nylon. I pulled it up and the stocking flowed up and up and up my smooth leg. My cock thickened. And when I let go of the second stocking, pulling it up almost to my groin, I was straining against my pretty, lacy rose colored tanga panties.

"Hmm, Houston, we have a problem. Tell you what, dear," Lilla said as she stood me up and peeled off my lacy panties, "lean back against the headboard and I'll rub one out for you. Can't have you tenting those pretty panties all day now, can we."

I leaned back on a pillow as she suggested and Lilla settled in next me and I put my arm around her. She stroked my stiff cock, ran her palm over the head and I shivered at the intense pleasure. Lilla stroked me and rubbed me and she talked.

"You have such a nice cock, hon. Look. It's so big in my tiny, delicate hand. A big cock that fills me up. Fills up all my holes, hon." Her hand felt like velvet, her touch soft and hard. "A perfect cock for me. And for you. Are you remembering what it feels like? In your mouth? Your lips wrapped around your cock. Sucking it. Giving me pleasure." She stroked me faster and I moaned. "And in your ass? Filling you all up over and over? Again and again and again?" Lilla stroked me and when I said, "I'm there," she dove down and put the head of my cock in her mouth and jacked me and I came. She rose up and we kissed long after my love was gone.

"Mmm. That was nice, Lilla."

"It was, wasn't it. No sense wasting perfectly good man juice, I always say. Besides, I didn't want to mess your tummy all up. Alright, let's get this show on the road."

I got out of bed, put my panties back on and picked up the dress Lilla had chosen for me.

"It's a ribbed v-neck tee dress. Do you like it?"

"I guess."

"Well, silly, put it on."

"No bra?"

"Oooh, you are getting into this. You want to wear a bra-a," she sing-songed

"I...no...I...I mean, isn't a bra standard? You want me in all this other stuff. Aren't you going to have me in a bra too?"

One fist on a hip, her other finger wagging at me. "Can't fool me, missy. You want to wear a bra. But here's the thing, she bounced to her knees on the bed and said, "I did think about it. But then I thought, 'Well, why not just go braless and let the girls fly free.' How can you get anymore feminine than that, really. Feeling them shift and shake, drawing all that attention. So I skipped braland."

"Oh shit," I said.

"Here. Trade those pretty panties for this," Lilla said and handed me a delicate lacy thong that matched my nails.


"I want you to wear this thong on the ride."


"Do it and I'll tell you."

I peeled off the lacy tanga panties and slipped on the thong, working it up my legs. I tucked myself in and held out my hands and cocked a leg like, tada!

"Smoking," she said and approached me. She reached behind me and yanked the thong up some, seating it firmly against me. "You feel it, muffin? Deep in the crack of your ass, on your little hole back there?" I nodded. "See, I want you thinking about that back door. The one that I'm gonna tap tonight." I gulped. "Okay, so put on that dress, dude!" she said and slapped my ass.

I slid it over my head, got my arms in the holes and pulled it down, shimmied my hips and straightened it. It was a chocolate color. Three inch wide shoulder straps. Deep cleavage and came to mid-thigh. Cotton.

"Wow. Gotta say, cupcake. You're a looker. Go check yourself. Wait! Here, put these on first." Lilla pointed to the nightstand.

I walked over, enjoying the feel and flow of the dress on my skin. I couldn't help but feel pretty, sexy even. I picked up the thin, silver, bangly bracelets and put them on. I dipped my head to one side and clipped on one dangly earring, then did the other side and saw Lilla smile at me. I put on a silver necklace, the thickest part hung just above my cleavage. "Rings?"

"Yes. And that one goes on your ring finger. It keeps most of the men from flirting with you."

"Lilla, I'm not sure..."

"Ah, ah, ah, now. Don't worry your pretty little head off. It'll be just fine. Trust me," she said and began to dress herself in khaki shorts, a white sleeveless blouse and sandals. "Here's your sandals." She held up a pair of simple, strappy sandals that complimented my dress. "I don't think we'll need heels for the ride." I put them on and she said, "Now let's go see."

In the mirror I saw a perfectly lovely woman. I turned from side to side and was amazed to see the image turn with me. I felt my hair sway and caress my neck and shoulders, the earrings tug on my lobes, my breasts shift and settle, the delicate tinkle of my bracelets. So feminine, so sensual. I flicked my hair back in that way women do and said, "I cannot believe that's me."

"Me either," Lilla said quietly, then she whooped, pumped her fists in the air and yelled, "Fuckin' A, hoss, saddle up!"

In the garage we put our bags in the car and Lilla tossed me the keys to the Audi convertible and said, "Shotgun!"

I snatched the keys out of the air, my breasts swaying with a delicious tug on my nipples and my cock twitched and I said, "Uh uh. No way. I am not driving out of here looking like this."

"But sugar bun, you look fantastic!" she smirked.

"Give me a break!" I said and tucked my hair behind an ear, noting the delicate tinkle of my bracelet and the sway of my earrings. "I am not driving through the neighborhood. If anybody sees me I'd just die!" I blushed.

Lilla smiled and said, "Spoken like a true woman, dearest. Tell you what, I'll drive out, top up, and we'll swap when we get out of town. Fair enough?"

"I guess."

Lilla backed out of the garage and hit the button to close the door. She laughed when I bent over and put my head on my lap and tried to disappear as we drove out of the neighborhood. Lilla stopped outside of town and we exchanged places. She gave me a pair of feminine sunglasses to put on. I put the top down and we were off and on our way. The wind in our hair, the music blaring, riding toward who knows what.

My skirt rose high on my thighs and I felt the thong against my rear. My breasts jiggled as we drove and the constant gentle tug on my nipples was akin them brushing against the fabric of my dress and it aroused me. My arm pushed against my breast as I held the wheel with a manicured hand. I felt so feminine and alluring as the men who passed us looked us over and the wind swirled up my dress and caressed my thighs with a faint promise of things to come.

"You know, honey bun, there are so many combinations of girl clothes I really wasn't sure what to go with." Lilla turned in her seat toward me. "Skirt and blouse combinations are fun. Corsets and jeans. And bras are tres sexy, especially taking them off. I simply adore bra and panty combos and saw the cutest things for you. But I decided to keep it simple for our first foray." I glance sideways at her and she giggled.

We arrived without fanfare and I was a nervous wreck walking toward the clerk at the check-in desk. A few of people were milling around. Or coming and going and I felt pretty and feminine and tossed my hair back. Without thinking I walked differently, more gracefully, more poised somehow. The clerk didn't bat an eye when as he handed us the key card to our room with a single king-sized bed, but I could feel his eyes on my firm rear shifting under my clinging dress as we walked to the elevators.
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