Truth or Dare Ch. 01

I had eagerly anticipated this evening for many weeks. Thought about how I wished for events to unfold. Planned, indeed plotted as I thought of ways to set the scene for the series of events to unfold as I had dreamed of for a year or two now.

We would have the house to ourselves for not only the evening but for the whole weekend. That's if I could encourage him to stay. I hoped I could.

Tom and I have been best of friends for years. I think I know most there is to know about him and he thinks that he knows all there is to know about me. I prey that this evening will change that assumption. That tonight he will meet a part of me that I have kept secret from him, from my family, from the world until now.

I can no longer hide the way I am and have a knowing, an understanding that now is the time for me to reveal my true inner self. For Tom to meet Rebecca.

The refrigerator is stocked with his favourite beer. Tonight, perhaps alcohol will indeed be my friend. To lessen his inhibitions, to increase his sense of adventure, perhaps to open his mind, allow him to see new opportunities, a different path. The music has been chosen carefully. The open fire is roaring, radiating it's heat and casting its glow into the large lounge of the Villa of my Family home.

The fireplace is an essential part of my careful plan. Thank goodness for the cold winter night. Perhaps the snowdrifts will help my cause, perhaps Tom will not be able to drive home even if he wished. It is up to me to ensure that his wish is to stay, to spend the night. To explore a new side of a friendship. The curtains are pulled, I expect, I hope for a knock on the door within an hour.

My afternoon of dress up fun has been as fulfilling as always. Yet another afternoon of secret feminisation, playtime where I am able to become Rebecca, to express the girl that has been a part of me for as long as I can remember.

The thrill of stripping from my male clothes, the excitement of seeing the dress, the lingerie laid out on the bed as i stand before the mirror, naked, applying lipstick, makeup. Pouting and pretending to secretly kiss as i look at my image in the mirror as i clip on the earrings, clasp the pearl necklace.

My ever present erection standing proud as i become Her, that part of me that now longs to be set free . Stepping into the panties, fastening the bra, slipping in the silicon inserts, rolling on the stockings. I am now rather accomplished at fastening bras behind my back, clipping stockings to suspender belts. I feel rather pleased with myself.

Stepping into a little dress and zipping myself up, i gaze at the mirror, admire the transformation, i slip into the heels and then rather nervously leave the room to set up the props needed to assist in my devious little plan.

Setting up the portable clothes stand I move it a little closer to the fireplace. Wet clothes will dry quickly from the heat of the flames. As part of my plan I have washed clothes of my family members. I have chosen the clothes of my sister very carefully. They are to play an integral part in the adventures that I foresee for this evening.

A simple yet pretty white lace bra, matching panties, stockings and a skirt and white blouse. I feel nervous, scared that perhaps I should have not washed the skirt. I prey that it has not shrunk at all in the wash. She will still be away for several days.

They are carefully placed in a prominent position on the clothes rack amongst various shirts, pants and men's socks. Blending in discretely. No one would ever guess the deliberate way that they have been placed, the thought that has gone into their selection.

After my man trap is set, I reluctantly change from my Rebecca attire back into that of a somewhat reluctant guy to greet my friend. Seems that he transformation was perhaps just in time as I notice the headlights of the jeep pull into the driveway. He knows the door will be unlocked. I plan to lock it later after my little game.

"Hey, Hi" something smells good as he gives me a playful punch on the arm. I open his first can of beer and hand it to him as he then makes himself comfortable on the couch in front of the fire. He is in jeans, black shirt and boots. Tanned, toned and looking sensational. I turn away so as to not risk him noticing my erection. To this day he has no idea that he has been the object of my sexual fantasies for months and now years.

Yes, I have had girlfriends, he still does , but my most intimate fantasies have involved he and I in a passionate embrace. In my mind, in my fantasies I am always dressed as Rebecca during my encounters with Tom. Will my plan succeed. Is he to see me dressed as Rebecca this evening. How will he react I am nervous, scared, excited.

Dinner brings with it small talk. I am distracted. It is near impossible to talk about world events and the ever popular sports. My mind is elsewhere. We sit together on the ouch as we dine. In front of the roaring fire. Beside the drying clothes. I glance at the bra, imagining how it's strap will feel around my back.

The evening progresses. Laughter, fooling around and more beers for my Tom. Time to make the suggestion. Taking a deck of cards, I suggest we combine cards with truth or dare. Throwing his head back, he laughs . "Yeah, why not". I pour myself a glass of red wine and begin the questions after my successful hand of cards. The truths seem to revolve around ex girlfriends, the dares revolve around drinking the beer and wines at an ever increasing pace.

Nervously I sow the seed for my plan. Holding up my older sisters pink sweater I suggest that maybe he should put it on. As he laughs out loud he hands me the bra, suggesting that I should put it on. My heart races. I am beside myself with excitement. Appearing to look shocked, I hold it up in front of me over the top of my t shirt.

Tom informs me that holding it up in such a manner is not good enough and dares me to put it on properly.. Looking shocked I remove my T Shirt and slip on the bra.

It does not go un noticed by Tom that I am proficient at fastening it in back. He throws me two socks, gesturing for me to stuff them in the cups. In turn I dare him to give me the keys to his beloved jeep, to let me use it for a day. He jokes that instead of me using it that perhaps he should take me for a drive in the bra. I blush, my heart races with excitement at the thought. I am soon back on the couch, in the bra, thrilled, apprehensive. I catch him stealing glimpses of me.

I subconsciously move a little closer to him. Gently removing the panties from the rack he hands them to me along with the stockings with a simple. Not a word is said.

I stand in front of him, turning my back to him to shield my erect cock, I slip out of my jeans, briefs and slip the panties on. The stockings roll on easily. I look back over my shoulder playfully , giving him an exaggerated bat of the eyelids. He laughs out loud and instructs me to turn around. I do do, hands over my crotch, covering my hard cock in the panties. He holds each of my wrists and moves my hands apart.

He stands in front of me. Taller, stronger. He places his hand on my panties, feeling my erection before taking my hand and placing it on his own crotch encouraging me to stroke him.

The cards now seem irrelevant, the game has grown a life of its own. He kisses me gently. Hands around my waist as he pulls me near. I slowly unbutton his shirt as the kissing becomes more intense. Gently unzipping his jeans I take his erect cock in my hand and stroke. So many times I have dreamed of this moment.

Cupping his balls, stroking his shaft as he kisses me. The feel of another mans cock in my hand almost too much to bear. I must hold on, I can not cum in my sisters panties..... Yet.

I slowly lower myself to my knees to position myself in front of him. Gazing at his delicious erect cock. I unzip him totally , stroking him. Eager to take him in my mouth. Looking up into his eyes, I lick my lips, his hand on the back of my head, guiding me to his rigid shaft. I look up again, straight into his eyes . Almost as if I am asking if I may suck him.

Looking down at me, he simply dares me to.

... To be continued.