You know the drill, if under 21, don't go any further. If it is illegal in your area. Stop right now. This story contains sex, crossdresing, between consenting adults.
The Bet
Part One of Seven
by
Stephanie Tranned
It started out as a bet, who would win the Superbowl, and I lost. The bet was for a week, during our vacation, the loser would do whatever the winner wanted. My wife, being a bit reservative, surprised and shocked me when she told me what I had to to.
We arrived home and my wife told me that I had thirty minutes to enjoy my manly ways all that I could. I sat and lounged in the recliner drinking a few beers thinking of the following week. I had mixed feelings about it. part of me was dreading it, the other was looking forward to it. I glanced at the clock as my wife entered the room. My time was up.
"Follow me," she said.
I followed her down the hall and into the bathroom. She had drawn a hot bath for me and I could smell a faint flowery scent coming from the water. I looked at her and she smiled at me. Nothing was said as I stripped and climbed into the tub. The water was very hot and my skin turned pink instantly.
She washed me from head to toe and proceeded top shave all my body hair off, even on my scrotum, I definately did not like that. When the bath was done, she rubbed my body with baby oil mixed with a violet smelling cologne. I definately smelled like a woman.
"What's this?" Grabbing my throbbing cock in her hand.
I didn't even realize I had a hard-on until then. My wife got on her knees and slid her full luscious lips around my shaft. I was so horny that as I felt her hot moist mouth around my cock, I came instantly. She took all my cum into her mouth, stood up and kissed me, feeding me my own cum. We kissed for several minutes, with Brenda holding my head, savoring the taste. The taste of the sperm didn't surprise me as much as the act did. I had eaten her out after having intercourse before on a few occasions. She was starting to turn into a sex fiend after these years of marriage.
Next, she led me by the hand into the living room, where she sat me down into a chair from the kitchen table and styled my hair. She then applied make-up on my face. Explaining everything she was using. When my face was done she told me to get dressed into the outfit that layed out on the couch. She told me in what order to put on the clothes.
I started with the white lacy garter belt, adjusted it on my waist. Next came the sheer white stockings, Brenda explained how to pull them up without tearing them. Then the white silk thongs, pulling them up at the sides till the back slid up the crack of my ass. I was starting to get turned on again. the bra came next, a silky push up that hooked in the front. she told me it was a "B" cup. The perfect size for my five foot elevan inch, one hundred and forty pound body. After she helped me adjust it she slipped a silicon breast form into each side, equipped with their own nipples. Brenda adjusted them as well. I then slid a slip over my head and had another hard on by the time it settled down into place. The ivory colored dress came next, it had a low cut front, showing my cleavage off nicely. The hem settled a couple of inches above my knees, and was accented by a narrow belt that matched the dress. Brenda finished the ensemble with a pearl necklace and matching screw on earings. I then slipped on a pair of ivory shoes with one inch high heels.
When we were done I walked into our bedroom and looked into our full length mirror. I couldn't believe the reflection, I was a gorgeous woman. I walked back into the bedroom and gave my wife one of the most sensuous kiss I could give.
"Tonight your a virgin, so I want you to act like one. I'm gonna take a shower, so you can watch this while I'm busy." With that, she handed me a VCR tape and left the room. I put the tape in and sat down to watch the tape. The first part of the tape was Brenda explaining how to sit, walk stand, and talk like a woman. The second, had me copying her as she went through the procedures. The video lasted forty-five minutes and when it was over, my wife walked in.
She was wearing a white satin blouse with a black velvety skirt that ended about two inches above her knees. Brenda wore black stockings with black shoes, her long brown hair hung loosely down around her shoulders. She had diamond studded earrings with a matching necklace. Man was she hot.
"Well Steph,"my name for the week,"What do you think?"
"You look absolutely beautiful." I replied. My hard cock straining at the panties I was wearing.I couldn't wait to see what she had in store for me. She put a cassette tape into the stereo that she had made for tonight. . She had me light several long candles while she turned all the lights off. Brenda stood in the middle of the floor. She had me push play on the tape player. The first song was the ballad 'Waiting for a girl like you' by the group Foreignor. Then she held her hand out and had me walk over to her. I melted into her arms as she wrapped them around me I layed my head onto her shoulder, delving into the part I was to play tonight. Steve did not exist, and wouldn't for a week.
I lifted my head and looked into eyes falling under some type of spell as she brought her face to mine and we shared a slow long kiss that took my breath away. I felt just like a virgin as I was falling deeper into the role. We danced for a couple more songs then sat on the couch talking 'girl' talk, and kissing. We drank wine as we continued to kiss and lightly fondle each other.
When the sixth song came on, we went back to the mddle of the room and danced some more. I was getting real uncomfortable in the shoes so I took them off. Brenda was now as tall as I was and it was even easier to fall into the part of her new woman. We continued to love each other slow and softly like only two women can. We continued to do this until the tape ended, and I flipped it over to play the other side. We walked hand in hand to the couch, I tucked my feet up under me and sat facing her, melting even further in the love I felt for her. I picked my up my wine glass and took a swallow of the semi-sweet fluid.
Brenda's eyes looked as if they were on fire with love and passion as I knew mine were.
"I didn't think you would do this, but I'm glad you did." She told me.
"I would've done this or anything you asked, even without a bet," I replied, "I love you and no matter what I'll do anything you ever ask of me, without hesitation. I want you to always know that."
Brenda then leaned forward and put her hand on the back of my head, pulled my face to hers. As soon as our mouths touched, our lips parted and she slid her tong into my mouth. I sucked and swallowed on it, revelling in the feel of her tongue sliding in and out of my mouth. Her left hand came up and cupped my right breast, I swear I could feel her hand through the breastform. My breathing became faster as I returned the favor with my left hand. We stood while still kissing, as she slowly undid the belt, letting it fall onto the couch. Brenda then slid her arms around me unzipping the dress. I lowered my arms, letting it fall effortlessly to the floor. I was guided slowly backward to the center of the room and gently lowered onto my back, our mouths still attached.
Brenda straddled my waist, leaning forward and ever so softly, began trailing her nails down my abdomen. I was so turned on that I came the momoment her nails reached my groin. My girlcock shooting more cum than I thought any man could, filling my panties with the hot sticky fluid. Brenda lowered her face to my crotch, licking and sucking all of the semen into her mouth. Raising back up, she brought her mouth to mine, and without any hesitation, I eagerly opened mine to except the gift that she held for me. We kissed for several minutes, my tongue searching her mouth for any remaining sperm. I couldn't believe how turned on I was. When she was sure I had all of it, we broke our kiss. My wife raised her head slightly, looked lovingly into my eyes and I fell even deeper into her trance. I tentatively raised my hands and began to slowly undo her blouse, I then slid it off her shoulders. Her breasts trapped into the bra, only inches from my face. I lifted my head buriing my face into her perfumed cleavage, licking and kissing and sucking on her deep sweet valley. My arms reached around her and found the clasp that held her breast trapped. Undoing it, the bra slid down her arms, freeing her breasts. I sucked the left nipple into my mouth rolling my tongue around it. Feeling it become hard and erect between my teeth as I lightly nibble at it. Switching to the other one, I hear a soft moan escape her lips. Rolling the nipple between my teeth, I hear her moan louder as she has an orgasm. I roll her over so she's on her back and I slowly work my way down her body. kissing and licking every sguare inch of her body. Another shudder and moan escapes her as I give her left armpit a slow lick, bringing her to another orgasm. Trailing my tongue down her luscious body, I feel her skin trembling toward yet another orgasm. My mouth continues to explore her body till I reach her pubic area, then I lift my head. I slide down to her feet and slip the left shoe off, licking her feet all over, enjoying the feel of her nylons against my face. I suck her little toe into my mouth, I suck each one for several seconds, moving toward her big toe. The big toe slides into my mouth as I suck on it, moving my head back and forth as if I was sucking a hard cock.
"Suck it," Brenda whispers. I suck it even harder, moving my head faster. A loud moan comes from her, Brenda's whole body shakes, sweet honey runs out of her flower, down her ass and onto the floor. I can't wait to taste it, but move to the other foot instead. Lickiing and sucking, bringing her to another orgasm. I proceed to lick my way up each leg until I reach her thighs, I stop to slide up for a kiss, rubbing my nails ever so slightly across her mound. She grabs my head and plants her tongue deep into my mouth, bucking her hips into my hand, She whimpers as she reaches down to push my hand hard against her clit.
My head gets pushed down and shoved against her pussy, fingers entwining my hair. I suck her pussy into my mouth to drink all of the juice that I can. Her whole body racks as she pulls my head even harder against her pussy. She face fucks me to yet another orgasm, screaming out and bucking wildly. She then gently guides me back up till I'm laying next to her, planting her mouth to mine, drinking what nectar I didn't swallow. My whole body tightened up as I shot a load onto her belly, without any clue from her, I bend my head down and lick her clean. I lay back down next to her, putting my head on her shoulder, dozing off for about an hour.
I wake up to feel her rubbing my back, we kiss slowly.
"Thank you," I whisper, looking deep into her eyes. We then get up and walk into the bathroom to clean up. I strip out of the bra and stockings, already missing the feel of the silky material against my bare skin. I go into the bedroom and see a white silky nightgown laying out for me. My nipples get hard and erect as the silky material slides down my body, I slide into bed and cuddle up next to my 'lesbian' lover. With my back to her, she wraps her arms around me, making me feel secure in her loving arms. I fall asleep, knowing that Stephanie will be safe.
The Bet part II by Stepanie Tranned
The following morning I woke to the feeling of soft silky material against my body. The previous night rushing into my head. I immediately became aroused, I looked over to where my wife was and noticed she was already up. I climbed out of bed, put on a satiny light blue housecoat over my nighty and walked out to the kitchen. Brenda was sitting at the table reading the morning paper with a cup of coffee in her right hand.
"Good morning," she said looking up at me and smiling. "I didn't think you'd continue with your payment. But I'm extremely happy to see that you are."
"Morning," I replied. "I enjoyed last night so much that I'm actually looking forward to the rest of the week." I leaned down to give her a kiss.
"Remember, you're a supposed to be a girl just learning to explore your sexuality. Not to mention that your still a virgin.
I didn't know what she meant but I knew it would mean that the following days would be extremely enjoyable. I poured myself some coffee and refilled her cup then sat down to drink. Crossing my legs and sitting somewhat sideways like the video showed. When we finished our coffees, I was told to follow her to the bedroom. Brenda sat on the bed and took my raging hard-on into her mouth and proceeded to suck me off. She pulled her mouth off my cock to have me jerk off into her hands. My cock grew harder at what I suspected she would do. I came hard and long, shooting my hot white cum into her cupped hand. After I was done cumming, Brenda lifted her hands without spilling a drop, and told me to lick them clean. That taste was saltier than last night and not as thick as it normally was, but I had orgasmed several times the previous night. The sperm was still hot and gooey, I loved every bit of it.
When her hands were licked clean, I was told to use the cream that was setting on the bathroom sink. Following the directions closely, I smeared the cream onto my body. When I finished, I was covered from neck to toes with a pink cream. My skin started to feel as if it was on fire, but I left it there for the full fifteen minutes. When it was time, I climbed into the shower and washed it off. My skin was pink from the burning, but Brenda reasured me that the burning was only temporary, not to worry.
I was then told to put on the outfit that was laid out on the back of the couch. I started with the soft beige thigh highs, with elastic bands at the top. Then slipped on a pair of baby blue high cut panties, they had lace on each side of the front. Next came the bra, it was another padded "B" cup, the color matched the panties. I had no trouble hooking it up, even though it was a back snap. After I adjusted the breast forms into them, I slid the slip over my head, watching it slide down my body in the mirror that brenda put in the living room for me. The skirt came next, a velvety purple that stopped midway down my thighs. Lastly came the blouse, it was a satiny pink, which buttoned in the front and ties in the back to so off my curves. I slipped a pair of light pink one inch heeled pumps onto my feet. Looking into the mirror, I couldn't help but get turned on by the woman in the mirror.
Brenda had me do my own make-up, explaing each step to accent my face to the fullest. Light purple eye shadow with a antique autumn colored lipstick. The shoulder length wig finished the job, turning me from Steve to Stephanie once again. I loved the way I felt and couldn't understand why women didn't dress like this all the time. I know it's alot of work, but the finished product looked and felt great.
"Today, you're gonna practice walking, talking and sitting like a woman. I don't mean like a 'sissy' but the way a real woman does."
I didn't think it would be too hard, but man, was I wrong. I sat, got up and walked around, then say down again. The whole time triing to talk with a high pitched voice, it wasn't working too well. My feet started to hurt just after a half hour, and my throat was killing me. Brenda let me switch to slippers so that I could be alittle more comfortable.
At lunch time, I had the sitting and walking down pretty well, but I would occasionally slip up and act too feminine. I didn't know it was possible, but she went to the video store and came back with a camcorder that she rented. She taped me for fifteen minutes, then had me watch it, I could tell immediately that it wasn't really a woman. Just a man that tried to pass as one. I looked like one but deffinately didn't act like one.
However, by dinnertime I walked, sat, stood, ate and drank just like a woman. My heels were returned to me and I was walking just like a woman with them in no time. The voice was another thing altogether. I drank alot of tea with lemon to keep my throat from getting too sore. I listened to Brenda and repeated what she said, I talked like her, but it didn't sound like her. I was more than discouraged. We ate supper with candle light that we prepared together, and shared a bottle of white zinfedel together. I sat down on the couch with my legs crossed, watching tv while Brenda took her shower andf got ready for another hot and heavy night. She returned into the living room carrying a small plastic bag. She was dressed in a black sweat suit that hid her curves a little too well, she smiled as she came into the room and lit five candles around the room. I turned the tv off as she got the lights. I sat back down while Brenda went into the kitchen and returned with two glasses and a another bottle of wine.
She sat down on my left, filled the glasses, and gently pulled me back against her shoulder. I felt more like a woman than even last night, and I loved it. I had never felt secure like this except maybe when my mother would hold me or kiss an injury away. I could easily get hooked on this. I was handed a glass and watched tv, sipping our wine. My glass seemed to get filled more often than hers, so I knew she had something even kinkier than last night in mind. I couldn't wait.
The last of the wine dripped into my glass, and a toast was raised to Stephanie, celebrating on how far she had come. I turned the tv off and started the slow song casssette. My lover got up and took me into her arms pressing her mouth to mine. I slid my tongue out only to find hers meeting me halfway, kissing sensuously. My breath taken away by the gentleness of it.
We began to dance, swaying slowly to the music, our hands roaming softly over each other. I wanted to know what was in the bag, but she kept telling me to wait. After about the third song, I lost count in my delirium, we stopped and my wife stepped back. She raised her hands to the front of my blouse, slowly unbuttoning it. When the last button was released, She slid the blouse off my shoulders, letting it fall silently to the floor.
I stepped back reaching behind me and undoing the skirt. Stepping out of it I stood up against my lover , sliding my hands up the front of her shirt. Pressing our mouths together again, this kiss was a bit more hurried, our tongues pushing deep into the other's mouths. Guiding me gently to the floor, her hands sliding the slip off of my shoulders and down my body. The silky material sliding across my stockings sent waves of pleasure through my body. I couldn't take much more, my cock was so hard that I thought it was going to rip through my panties. Brenda lowered her head and began to lick my entire body, bathing me with her hot mouth. I started to explode just as her lips reached my 'womanhood'. Wrapping her lips tightly around the head of my shaft, she caught every precious drop. Reaching down and wrapping my hands around her head, I pulled her mouth up to mine. I was beginning to really enjoy the taste of my cum, and couldn't wait to get my desert. Sharing the sticky fluid as we passed it back and forth between us, our throats contracting, each one trying to swallow more than the other.
Pulling the front of my panties back over my 'girlcock', brenda reached her hand up and I immediately took her index finger into my mouth, sucking it as if it was her cock. The act of me sucking her finger brought her to an orgasm, moans escaping from her mouth as the juice soaked her pants. Brenda stood up and stripped her clothes off, revealing her body inthe candle light. She walked over to the couch, grabbing the bag, and came back to where I was laying.
Her hand went into the bag and withdrew holding a black scarf, she wrapped that aound my head. Covering my eyes, she made sure I couldn't see, then tied a knot in the back, adjusting it so that the only thing I could see was total blackness. I could hear her rustling the bag and then her hands took my arms and tied them securly at the wrists, I was feeling helpless. The bag rustled again as I lay there at her mercy, a little scared, but mostly turned on by this game.
Out of the silence I heard a small humming sound, as the sound grew louder I felt a tingling sensation on my neck. I moaned with pleasure as she slowly worked the vibrater over me, not missing a square inch of my body. It traveled down then up each arm, sending waves of desire through my entire being. The vibrater moved ever so slowly across my breasts, sending it's wonderfull effects through the breasts to my erect and hardened nipples, my passion making me arch my shoulders to raise my breasts against this mercilfull feeling. I groaned with disapproval when she removed it from my sensitive breasts. Only to have it start at the soles of my feet. I began to writhe on the floor as she slowly and teasingly moved it up my left leg. When she finally reached my upper thigh, Brenda then began working on my right, this time licking and kissing my foot. Following the magical toy up my leg, till she reached my groin. I could hear her moaning with desire as she began to lick and suck my balls through the panties.
Untiing my arms and removing the blind fold, she layed on her back and had me climb on top of her in the sixty-nine position. Handing me the vibrater, she adjusted her arms behind my knees, I didn't even notice that this was a different variation of this position as I slipped the vibrating phalus into her smouldering pussy. Her hips bucked up into my face as she came to a screaming orgasm. Pressing my mouth to her vagina, I lick and sucked every drop of honey that I could. I snapped my head up as I felt her hot tongue slip into my asshole. At first I started to object, bot before I could even get a word out, I succumbed to the waves of desire that it sent throughout my whole body, ending at my cock. I came instantly as her tongue worked in and out of my ass. My mind gone now, I shot the hot sticky liquid onto her chest and ground my groin into it, revelling in the wonderfull sensation that it gave me.
We continued to eat each other's 'pussies' as I gave her several more orgasms, I began to grind my ass into her face as her tongue continued to sen waves of ecstacy through me. After a short time, Brenda reached down and pulled my head back and pushed my hand away telling me she couldn't take anymore. I sat up, continuing to rock on her face, until her tongue couldn't take anymore, then very hesitantly, I got up off from her. as soon as I rolled onto the floor, I had already missed her tongue and would've done anything to have her tongue fuck me some more.
That night, I wore a silky medium blue nighty with matching panties. Climbing into bed i rolled over and layed my head on her shoulder, closed my eyes and slept like a baby.
This is the end of part II, if you like it, send me comments at havnfun41@hotmail.com. I would love to hear from you.