The Bet
Copyright© 2006 by jomar
Chapter 4
Erotica Sex Story: Chapter 4 - 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. 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 highlights shimmering 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 Fake-Me-A-Woman.com. Outstanding site, they've got everything! You're a C cup, baby, hefty three inchers, how about that. It was a really hard decision, baby, there were so 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 straight on the top, the base's corners rounded, 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 thinks up 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 gonna love 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 what that 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.