The Bet reLoaded Ch. 03

I hope you enjoy the kink.

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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 was fucked. Literally. Thursday night she waxed me stem to stern leaving me with no body hair save the fetching shoulder length blond hair with highlights on my head. Friday, Lilla dolled me up complete with state of the art fakes tits and took me out of town for a girls weekend away. We met new friends, saw a drag show and then Lilla had her way with me.

The bed shifted and I woke up in the morning to see Lilla climbing back in, the strapon jutting from her mound. She got between my legs, hooked her arms under my knees and dragged me to her. Her legs were folded beneath her and my legs were draped over hers. She applied lubrication to our cock. I felt her put some on my rear and my cock thickened.

I closed my eyes as she pressed against me and after a momentary resistance she slid in easily and I swooned, the bliss was so intense. My hips were cocked, my ass was in her lap, and she loomed over me.

"Morning, sunshine," Lila said with a broad smile. "After the fireworks last night I thought I'd throw you a leisurely morning fuck. Well, it's gonna be mostly for me, but I expect you'll have a little fun." She smiled and winked and ground against me. "Hmm, on second thought, tell you what, sweets," she said. She gently withdrew and I hitched as the head of her cock left me, "Scoot on over." I did and Lilla lay down.

"Alrighty, hop on board and show me what you got, toots." I threw a leg over Lilla and positioned myself and slowly dropped down on her thick cock, letting the blunt head spread me and spear me and I was thrilled as it penetrated and filled me. An earring had fallen off in the night and Lilla noticed and handed it to me. I settled on her, the pressure thick and deep and welcome, tilted my head in that feminine way and put on the earring, my bracelets gently clinking. A stocking had slid down a thigh so I pulled it back up as best I could. I sat erect and ran my hands through my shoulder length blond hair with highlights and my breasts perked up.

"God, you look amazing," Lilla said.

I stayed seated and rotated my hips. I ground against Lilla and was rewarded with a moan. I ground the cock against her mound and swiveled and snapped my hips so it would work her insides. Lilla's breathing got faster, she took short choppy breaths, then she was there and I mauled her breasts and nipples and ground against her as hard as I could until her back arched and she cried out and came and collapsed. My cock was hard.

I let her rest a minute, let her get her breath back, then slowly raised until the tip of her cock was barely in me. I lowered myself, relishing the thickness, the pressure, the slide over and against my prostate. God, it felt glorious. I put my hands on Lilla's chest and raised and lowered myself on her cock, fucking her cock. She began to thrust up against me, she punched in and out of me and she jacked my cock and my breasts bounced wildly sending bolts of pleasure to my nipples. She circled the head of my cock with her palm I shuddered with the exquisite, almost painful bliss. Harder and harder I raised and dropped and harder and harder Lilla thrust up against me and harder and harder she rubbed and stroked and pulled on my cock and I came and clenched and spasmed and spurted.

I collapsed to my elbows, breathing heavily, raggedly, my hair enveloped my face and my dangly earrings swayed and tugged. "Mmm. Very nice, darling. You rock," she giggled at her joke.

I eased off of Lilla, released the straps and when wriggled the strapon off of her. I bent and licked her stomach and cleaned my cum, working my way up her slender, toned body until I reached her lips and kissed her gently. "What a wake up call that was," I said. My rear throbbed deliciously.

"Yeah, nothing like a little shake and bake to start the day," she said and squealed when I pinched a nipple. "Okay, you know the drill, get in there and take care of business.

I rose and tended to things in the bathroom. I showered and shaved and my cock thickened when I washed my breasts. I called Lilla when I was dry and she came and did her magic with the makeup. Light makeup for daytime. She blended the edges of the Hurley's to perfection, styled my hair to a tee and handed me a pair of yellow, lacy sweet cheeks.

"Sweet cheeks?" I asked.

"Aren't they darling? More than a thong, but less than a tanga. You'll love them."

"If you say so." I straightened them out and bent to put them on. Again, my arms grazed my breasts and my nipples tingled and my cock twitched.

"Already? Am I going to have wank you already?"

I shrugged.

"Girl, you are one horny little filly."

I pulled the panties up, cocking my hips from side to side and got myself adjusted. A three inch band around the back, a thicker than usual thong splitting my cheeks and making its presence known back there.

On the bed lay a taupe dress. "Hurry, hurry, hurry, put it on. I want to see it on you."

Another microfiber dress that flowed like liquid, slippery as mercury, seductive and sensual and ever so feminine. I put it on and looked down at myself. It was empire waist inspired with about a one inch band below my breasts, gathered below the band and flaring out. Mid-thigh length. The hem of he sleeves and dress a little bit ruffley. The material rose from the empire waist up and around my neck. Lots of cleavage as the material had about in inch gap where it met the empire inspired waist band just below my breasts. A lining kept the nipples on my thirty-six C funbags, as Lilla called them, from being too obvious.

Lilla whistled. "Man, you make that dress look good. It's a flutter sleeve dress from VS. Isn't it precious?"

"It really fits me well. It flows nice." I turned side to side and felt the sexy material caress my skin and settle." She handed me some pretty sandals and I strapped them on. "No stockings?"

"You really are getting into this. First wanting a bra, now stockings."

"No...you...ugh, same thing. You want me in this stuff, you had me wear stockings on the drive here, I just thought...."

"I know what you thought. You wanted to wear stockings and be a sexy little vixen today. Well, we can be kind of casual. You can just enjoy the swish and swirl of the dress on your bare thighs. And the wind blowing up your skirt, though you just better hope it's not too windy out," she said and smiled and cocked her head. "Get your jewelry on and let's go, pard."

I put on the bangly bracelets on both wrists, the dangly earrings, the silver necklace, a few rings on my fingers, one on my ring finger to keep most of the men from flirting and a toe ring that Lilla handed me. My burgundy finger and toe nails looked absolutely divine with my dress.

We left the room and headed out on our adventure. Lilla, striking in a simple yellow sundress that matched my pretty sweet cheeks panties, and which set off her brilliant shoulder length red hair, and me in my sassy sexy taupe flutter sleeve dress. We passed the lobby mirror and I was once again stunned at the image that followed my movements in the mirror. A woman, a beautiful, alluring woman who walked with more grace and poise and confidence than I felt.

The hotel was in the middle of a retail district with higher end stores of all kinds lining the long, wide shopping avenue that was closed to vehicles. We exited that side of the building and looked around. Street vendors were out, artists putting on shows, families and kids and women wandered about, some with purpose, some just enjoying the day. And men. Not as many men as women, but a goodly number.

The men made me nervous. As we walked by them, or they us, I watched their eyes from behind my dark, feminine sunglasses. The men's eyes soaked in my body. They appraised my legs, zeroed in on my cleavage and strained to see my nipples. I'm sure they tried to imagine what I looked like naked. I'm sure they wondered what kind of panties I had on and if I shaved down there.

Lilla was beaming as we walked and passed the men. "Oooh, the lookie loos are out today. Girl, the men are just drooling over you. They can barely take their eyes off your tits."

"Shut up."

"I noticed some of them even turning around to check out your ass even though you got a dress on."

"Stop."

"Maybe you should put a little more bounce in your step and get the girls going. See if you can develop a following." She laughed.

"You're terrible. I want to sit down."

Lilla hooked an arm through mine. "Aww. Did the stares of a few men get you all hot and bothered? Did their probing eyes get you a little wet, I mean hard?" She giggled. "Come on, pumpkin, let's have brunch over there."

We crossed the street and the gentle breeze caressed my hair and nipped at my dress and flowed delightfully across my hairless arms and legs. The feel of the microfiber swishing across my rear was sensuous and served to highlight the band of my lacy yellow sweet cheeks panties riding high back there. We took an outdoor table at a small café and as I sat I felt the pull of my thong on my rear opening and my cock twitched. We ordered vegetable omelets and mimosas and enjoyed the view.

Much to my chagrin Lilla pointed out this handsome man and that, asking me if I'd drop my panties for this one or swallow for that one. She scanned the pretty women, speculating which ones had a surprise under their skirts. It was at once embarrassing and exciting and, I hated to admit, just plain fun.

We ate at leisure and ordered another round. It might have been the mimosas, but I became less alarmed about the men looking at me. In fact, I began to welcome their stares and made eye contact and smiled at the men. I even leaned forward a little and pressed my breasts together some with the inside edges of my arms so the waiter could have a better look down my dress and when he took the opportunity my cock thickened and Lilla's eyebrows raised, her eyes twinkled and she smiled brightly in the morning sun.

Lilla and I finished brunch and strolled the plaza. I demurely cut my eyes and lowered my head with a small smile and tucked my hair behind an ear when certain men looked my way. It was thrilling and I was aghast to find myself behaving in such a manner and enjoying it.

My actions were not lost on Lilla. "Slut."

"Am not."

"You would be if I turned you loose. Goodness, sweets, why I think you'd buy new shoes with round heels and hope for a slight breeze to blow you on your back." She laughed.

"This is so weird. I can't believe how sexy and desirable I feel out here. Just dressing like this brings out...I don't know...something."

"Yeah, like your inner slut."

"Ha."

"Come on, sugar, let's go in here," Lilla grabbed my hand and dragged me into a movie theater. She bought two tickets for the new Sex in the City movie and I groaned. I hated the movie but couldn't help but notice and admire and be fascinated by all the jewelry and clothes and how they draped and fit and flowed on the silly women as they cavorted through what, to me, seemed to be just a cash run.

After the movie Lilla and I strolled around some more, window shopping, feeling the eyes on us linger and probe and move on. She wanted to try on clothes, especially for us to look at lingerie, but I resisted her teasing efforts.

In the late afternoon we had a couple of more cocktails, colorful girly drinks we sipped through straws. We had a light dinner consisting of a salad and a wonderful seasoned fish at another outdoor café while we watched the men watch us.

Back at the hotel Lilla gave me some white wine and sent me to do the bathroom ritual again. I reluctantly took off my brilliant taupe flutter sleeve dress. I loved the way it felt and made me feel. I peeled off my lacy yellow thong and my cock pulsed as the thick thread made its way from between my cheeks. I stepped in the shower and spent ample time making sure my breasts and cock and rear were squeaky clean. We were to meet Marion and Joanna for cocktails and I was anxious about it for some reason. We'd had a great time at the drag club, but wasn't sure what to expect tonight or even how to act.

When I was out and dry I called to Lilla. She poured me some more wine and got to work on my hair and makeup. She painted my finger and toe nails a blood red color and applied lipstick to match. When she turned me to the mirror and there I was again. A beautiful woman. My heart fluttered.

On the bed were sheer black thigh highs, a scalloped fishnet lace thong the color of my nails and lips, and a dark blue dress. I sat on the bed and gathered a stocking. I closed my eyes and shivered as I pulled the silky stocking up my long, smooth leg and felt its whispery caress. My cock twitched. I pulled on the other stocking, feeling my arms brush against the side of my breasts and my nipples tingled. I stood. Lilla admired me. She lovingly caressed my face and I smiled and leaned into the softness of her hand.

I picked up the pretty red thong and shimmied into it. I picked up the blue dress, another silky slippery microfiber material.

"Isn't it lovely?" Lilla said. "It's a sassy little curvy jersey knot front halter dress. You'll adore it."

I slipped it over my head and Lilla adjusted the halter for me. A tad longer than the other dress, but not by much. And the halter was positively scandalous! You could see bare skin all the way down to where the cloth covering my breasts met the waist wrap just above my belly button. It swished and swirled and was absolutely marvelous. I liked the way it moved on me and the way it felt on my toned, hairless body.

"It's nice," I said, and moved to put on my jewelry and earrings. I put on my four inch high heels with an ankle strap, thinking about what Lilla had told me, that the strap was so they wouldn't fly off while sluts were getting fucked hard.

Lilla wore a sexy little black dress, black stockings, gold jewelry and four inch heels. We looked spectacular together. Two beautiful women, one of whom had a cock.

We met Marion and Joanna in the hotel bar, which was elegant and subdued and glistened with silver and green. Marion had on a sexy, billowy rust colored skirt and blouse combo and Joanna had on a clingy white tank dress and bangly jewelry. We sat down and said hello's with smiles and air kisses all around and Marion said, "You two are drop dead gorgeous."

"You too! I love that tank dress, Joanna."

"Thank you," she said and took a sip of her girly drink.

"Did you ladies have fun last night?" Marion said with a hint of a smirk.

"Yes! We had a blast! The show was a fucking hoot," Lilla practically bounced in her seat with enthusiasm.

"Wasn't it?" Marion touched Lilla's wrist, "And all those lovely ladies in the club and then the cab ride back here where the four of us were pressed so tightly together in the back seat? Oh my god, I was so horny that when we got back in the room I was all over Joanna, wasn't I, baby." She glanced at Joanna. "To be honest I was surprised she could even walk this morning the way I hit it." She winked at Lilla.

"Marion!"

"Oh hush," then to Lilla, "She loved it. Oh my god, she was begging and pleading for me to fuck her harder and faster. Weren't you, baby."

"Marion! You're embarrassing me again," Joanna said and widened her eyes at Marion then folded her arms across her flat chest. Marion smiled.

"Yes! Me too! I practically attacked Liz," Lilla said.

"Did she wear you out?" Marion addressed me and I blushed. "Oh my, are you a shy girl in bed, Liz? Or do you let it all hang out, as they say." I gulped and took a sip of wine.

Marion laughed. "So how about it, Lilla. What's she like in bed?"

"She's a freak," Lilla said and giggled.

"Lilla!" I stared at her. Marion laughed. "Jesus. I have to go to the bathroom," I said and got up to go.

"I'll go with you," Joanna said.

"Make sure you use the right one, ladies," Lilla said and giggled.

"Aw, man," I said as Joann and I turned to walk toward the ladies room in our high heels and feminine attire.

Lilla and Marion were huddled in conversation as we returned from across the room and I saw Lilla wink at Marion as we sat down. "What's up?" I said.

"Later, I want to propose a toast." Lilla held up her girly drink and said, "To new friends and frillies."

I groaned and we all laughed and reflected the toast back to Lilla and clinked glasses. We chatted and laughed comfortably over another round or two and eventually said so longs and we'll see you laters.

Back in our room Lilla said, "I really like them."

"Me too. I'm glad we met them. I kind of feel more comfortable knowing Joanna is around, you know?"

"You're not alone, pumpkin, lot's of men love dressing up like women."

"I don't love it. I lost a bet."

"Mmm hmm. You can't fool me. Now slip out of that lovely dress and put these on," she said pointing to the bed where some frilly's lay.

I picked up the flimsy black material and said, "What is this?"

"Isn't it fantastic! So sexy. It's a little half slip. And see, it has a ruffled back with a pretty little bow at the back and lace trim at the waist. Ooh, and it has a matching lacy bra."

"Bra?"

"All for you, sweets. I know you've been dying to get the Hurley's in one."

"Lilla..."

She giggled and bounced on her toes and said, "Put it on, put it on, put it on."

I wriggled into the half slip and settled it over my red scalloped fishnet lace thong. It rode low on my hips and barely covered my ass cheeks. It flowed enticingly despite its dainty size. I put the bra on and had some difficulty with the back closure, but I got it done. I liked the feel of the bra. It felt so powerfully feminine and alluring.

I toe-heeled it to the mirror in my four inch fuck me's and saw a sex kitten staring back at me. A very pretty sex kitten with a slender, toned body, shoulder length blonde hair with highlights, bangly bracelets, dangly earrings, a black lacy bra, a tarty black half slip, thigh highs up to there and four inch fuck me's with ankle straps. Blood red nails and lipstick. I was devastating.

"Baby, you are all that and a bag of chips, a box of chocolates, a butt full of plugs, a...."

"A what?" I laughed.

"You are out of this world stunning. Here, put on your chocolate ribbed v-neck tee dress."

I smiled. "You just want to see me in it so you can have the pleasure of getting out of it, don't you."

"Oh, not me, honey bun. You're paying Marion a visit."

"What?"

Lilla nodded.

"No fucking way!"

"Oh, definitely fucking way, dearest. We talked while you girls were in the ladies room and we decided to trade."

"Lilla, you can't do that," I whined.

"Of course I can sugar, I won the bet and you have to do what I say."

"But, Lilla..."

"Right?"

"Yeah, but..."

"Then it's settled."

"But I don't want to be with anybody else."

"Oh really? You mean like you didn't want to be with my old college roommate and me when you won the bet and found out I experimented a little back then with that French hottie?"

"But that was different."

"Pish posh and poppycock." Her eyes widened, her eyebrows raised. "That was fun, though, wasn't it, honey bun. I forgot how good dining at the Y could be," Lilla said and licked her lips and beamed and laughed and I couldn't help but smile at the memory of the three of us all jumbled together in all possible combinations.

"Yeah, but Lilla..."

"Listen, we've talked about this, right?"

I was silent.

"Right?" she said quietly.

I nodded, my heart was pounding.

"Talked about it, fantasized about it, and had great sex while doing so, remember?"