Truth or Dare Ch. 02

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Rebecca and Tom on a wild winter night.
1.5k words
4.48
36.5k
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Part 2 of the 3 part series

Updated 10/29/2022
Created 08/01/2014
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As I kneel in the bra, panties, stockings looking up into his eyes I am overwhelmed with excitement. With lust, with desire. Having been drawn to him for years, I cannot believe that at last I am on my knees, dressed as a girl for the object of my desire, for my Tom.

He smiles as he looks down at me, I gaze up into his eyes. The feel of his hand on the back of my head is heavenly. I wish to wear a wig for him later. I wish for him to see me with my shoulder length blonde hair. For now he moves his fingers through my short boyish hair. Perhaps I need a simple pink ribbon in my hair for an added touch of femininity.

My cock now as hard as a rock in the little panties. I adore the feel of them. I always have. The tip of my cock protrudes out over the little bow embroidered on the front. The bra is fitted tightly. I always fasten my bras tighter than required to heighten the sensation of wearing my pretty feminine lingerie. The restriction of the bra adding to my feelings of fragility, of helplessness, of femininity.

The stockings firmly in place. The lace tops holding them up without the need of a suspender belt.

I lower my gaze. Looking away from Tom's eyes. His erect cock standing proud before me. I see a glisten of pre cum. A touch of moisture at the tip. It is magnificent. Slightly larger than my own, beautifully formed. I move ever closer, licking the tip as he runs his fingers through my hair. My tongue moves in circular motions. My left hand gently caressing his beautiful balls as my right hand slips into my own panties.

I lick the shaft. After having received so many blow jobs over the years from my previous girlfriends it seems too good to be true to realize that today that I am to be the girl, that at long last I am to give rather than to receive. It seems so right. It is so right. This is how it is meant to be. Tonight Tom is the man. Tonight I am the girl.

The moment of truth. The moment I have thought about for years. I take him in my mouth. I hear a slight moan of delight from his lips as I move forward slightly to receive him. I feel the pressure on the back of my head as he guides me into position. At long last a cock in my mouth. I am surprised at how far I have to open my mouth to receive him, at just how big an erect cock can be. I move my tongue gently around him as he slips into me.

I can barely contain my excitement. The panties can barely contain my excitement. I long to explode. I am on the edge. I have never felt so aroused. I must not. I must hold on. I gaze up into his eyes. He looks down at me. I have never felt so wanted, so desired. This is perfect in every way. He pulls me forward. I take him in my mouth completely. It is huge. He is huge. My mouth wide open. He thrusts gently, both his hands now holding my head.

The feelings of feminity overwhelm me. The sensations of the bra, the panties, the stockings. The sound of the rain on the roof. The smell of his musk, his aftershave. His moans of delight as he gently thrusts.

I bob my head back and forward. Taking his cock right out of my mouth and then back in. It seems larger. He is harder. Every time it slips past my lips is a dream come true. I have never felt so much like a girl. I am Rebecca at last. Never before have I felt so validated in my feminity.

He is close. I feel him twitch , I feel him pulse slightly in my mouth. He withdraws, He tells me that it is too soon, that the night is young. "Stand up young lady" he instructs. I do as I am told and stand in front of him. We kiss. Pushing me against the wall I feel his hardness against my panties. Our kiss grows urgent, passionate.

He instructs me to raise my hands above my head. With one hand he pins my hands to the wall. He holds both my wrists in his one large, strong hand. His other hand wanders, explores. He slips it into my panties, stroking me slightly. He slips his hard cock up the leg of my little lace panties. Both our erect cocks now covered by the lace. Cocks touching. He takes both of them in his other hand. Stroking the two as if they were one as our passionate kiss grows increasingly more frantic.

His left hand holds my wrists so tight. I would not be able to move them even if I wished. His strength arouses me further. Despite the deliberate way that I have orchestrated the events of the evening, it is now almost as if he is in charge. He seems dominant, masterful.

An image flashes through my mind of my wrists being bound by rope. Of him tying me up. Of Tom taking control and removing my choice in the matter. I know that even if I were to change my mind and wish to step back, that he would not take "No" for an answer. The image of helplessness feels right to me.

The storm grows more and more wild, lightning now and crashes of thunder. As he kisses me I imagine myself as his captive on this wild winter night. I am glad he can not read my mind as I imagine myself gagged and tied to his bed in a little Babydoll nightie. I blush at the image. Trying with every little bit of willpower to ensure that I don't cum in his hand.

He whispers in my ear that he needs to see me play a little bit of dress up. I nod when he asks me if I want to put on a dress for him. Without saying a word I take him by the hand and lead him upstairs. I have often worn my sisters Lemon bridesmaid dress when home alone, I know this is the one. Carefully removing it from the wardrobe I hold it up in front of me with my left hand, with my right I hold the hem and pull it out to emphasize the shape. He nods approvingly.

As Tom lays back on the bed naked, hard, stroking, I step into the dress as I have done so many times before. I turn to face him as I slowly button it up. I have always been thrilled by the helplessness of fastening bras behind my back and I love the sensations of trying to fasten the six buttons behind my back. Success at last. I slip into the Lemon high heels and give him a twirl. The sound of the high heels on the wooden floor, the sound of the fabric rustling as I move thrills me. The skirt flares out as I spin in front of him.

I step towards the bed. As I move I almost subconsciously place my hands behind my back. Once again the image of my hands bound flashes through my mind. Perhaps my hands tied behind my back in this pretty dress as I suck my man, my captor. I blush again at the thought, glad that he can not see how hard I am under the full skirt and the layers of petticoat.

Stealing a glance in the mirror I see the need to add the finishing touches. He strokes himself gently as he lays back watching the process. The lipstick, the foundation, the blusher and mascara. I contemplate the wig but choose a simple cream hair clip with a pretty bow in my short boy hair to complete the transformation.

I kneel on the bed in between his now open legs. I can't take my eyes off his balls, his gorgeous cock pointing skyward. My moves now more feminine than ever, almost forced to move as a girl by the constraints of the dress, the stockings, the bra, the heels. I bathe in the delight of the moment. I look up at him. Our eyes meet. We gaze into each others eyes as i brush my hand over his balls. I stroke his cock gently. It is magnificent.

Cupping his beautiful balls, I move them around in their sacks. His cock twitches with excitement as does mine under the layers of feminity. With my free hand I stroke his shaft.

I admire his beautiful, toned body. He is as I had always dreamed. Tanned, strong, toned. Short dark hair. A dream of a man. My dream, my fantasy.

I reposition. Time to suck my man. Time to suck Tom' s cock dressed as his girl. I glance in the full length mirror at the perfect scene. At last I am Rebecca. At last I am Rebecca with my Tom. Taking him in my mouth again my mind turns to the possibility of the night ahead. How will he take me. How does Tom intend to ravish his girl...

To be continued...

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9 Comments
RebeccaCherieRebeccaCherieover 9 years agoAuthor
Jill, Thank You

Xxxxxx

Thanks for the feedback. Tom and Rebecca will be continuing their voyage of discovery in a couple of days. Xxxxxxx

Rebecca.

AnonymousAnonymousover 9 years ago
wow!

you capture the feelings so well, you paint a beautiful picture! keep going! XO,XO,!!!, Jill

BrendaNWBrendaNWover 9 years ago
oh yes

more please.. I definitely identify with Rebecca.. I need a big strong man to make me a woman.. his woman, fully in every way..

RebeccaCherieRebeccaCherieover 9 years agoAuthor
Thank You.

:-) I appreciate the feedback. I am so new to this writing. I will try to write longer chapters and improve my style as best I can. This is one of many fantasies that I have had throughout my life. This story is based upon a guy I fancied some years ago. Fast forward to present day and I now have another man that is the object of my desires. Geography and circumstance have not allowed us to meet as yet however we are in regular contact. Yes, his name is Tom and he is now aware that I have posted these stories. I am glad that many of you can relate to the feelings that I share within this story. "Gurls" isn't it just heavenly to express, celebrate our femininity. :-) Xxxxxxx

Rebecca.

AnonymousAnonymousover 9 years ago
Wonderful piece!

I am enjoying this story very much. The picture you are painting is highly erotic, and the atmosphere very charged. My only problem is choosing which character to identify with!

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