Truth or Dare Ch. 03: Take Me Tom

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Rebecca becomes a woman for Tom.
1.9k words
4.57
36.4k
18

Part 3 of the 3 part series

Updated 10/29/2022
Created 08/01/2014
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Cupping his balls in my left hand I move position to take my man in my mouth. My Mother always told my older sister that it is a woman's role, her duty to please her man, to be there for him as needed, when needed. I wonder if my sister is as compliant, as obliging with her Husband of 6 months as I wish to be for Tom. I could be a very obliging young lady indeed. My mind has been filled with fantasies over the years of being the submissive girlfriend, and wife. If only.

Tom's legs now spread wide, his hands above his head holding onto the headboard. An image flashes through my mind of his hands tied. A strong sexy man, hands bound. My cock drips a little in my panties at the thought. I dismiss the fleeting image from my mind. It is we, the girls that should be bound by the strong forceful, dominant man. My mind is a whirl with contradicting, thrilling thoughts.

I lick my lovers balls. Each in turn. I gaze at his magnificent cock. Larger than mine, of course, a mans cock should be bigger than his little girlfriends'. It is cut as am I ,he is trimmed he is tidy, he is perfect. My mind drifts back to earlier in the day prior to my dress up when I showered shaved and then waxed. I hope Tom will appreciate the effort I have gone to in ensuring I am smooth, for him.

I hope my little cock and my balls look as they did when i was a boy . I have a little pink ribbon I tie around my cock at times. Perhaps tonight might be a special night. Should I let Tom tie the pink lace in a bow or should I. My mind is wandering all over the place. I need to focus if I am to be a good girl and fulfil my man.

"Oh my god, that's it, suck me," whispers Tom as I take him in my mouth.

His cock fills me once again. My mouth wide as I lower myself onto him. I feel no hand on my head. Perhaps his hands are still above his head. The image of him tied flashes through my mischievous mind again as I make my first attempt to deep throat. He is so huge, I can not possibly take his all, I suckle gently amidst his moans. I kiss the tip, my tongue dancing at the slit.

The little drops of clear precious precum excite me. I know I must continue to kneel in the dress, kneel between his legs. I fear that if I were to lay down, face down on the bed, to feel pressure, that I would surely be unable to hold on. I would surely fill my sister's pretty panties. I would surely fill them with cream. My sissy Girly cream.

While I suckle, lick, suck, stroke, I picture our two naked cocks together. Matching cocks, His and Hers cocks. His the strong dominant potent cock, hers the pretty little submissive cock to be treated as the man sees appropriate. In my mind a little lace pink bow around mine, as if we need to be reminded who is the girl tonight. I quietly giggle to myself as I imagine our cocks as little people all dressed up, mine as a bride, his as the groom.

"Oh God, that's incredible," he whispers, "what do I call you when you are dressed like this?" he asks.

Lifting my head and looking him straight in the eye I reply "Rebecca, call me Rebecca Tom".

"Come up here baby, I want to kiss Rebecca." he says. I reposition, moving up. I sit astride my god of a man. As I move over his cock, I pause to imagine the sensation of lowering myself on him. I fantasise about how it is to feel to have him enter me. He raises his hips slowly. I lower myself just a little. I feel the tip of his cock push against the rear of my panties. We smile, we both know.

I lean forward to kiss my man. My dress now covering his chest, his cock still easing against the fabric of the panties. Part of me longs to hear the fabric rip and to feel him enter me. I know I must wait. I can be a good girl. I have waited all these years. What's another hour or two.

I move further up, leaning forward I position to kiss him. Another images races through my over active imagination. An image of me as a woman, my breasts swaying as I lean forward to kiss my lover.

Back to the here and now. We kiss. His hands wandering over my dress, he runs his fingers over my bra strap. As I lean a little further forward I feel my padded bra rest on his chest. My feelings of femininity heightened moment by moment. He repositions slightly , he raises his hips slightly.

I feel his cock hard against the back of my panties again. I push back into him, I long to feel them rip, long for him to perhaps move them aside. I long to feel a potent erect cock slip inside me.

He now thrusts gently as we kiss, he slowly unbuttons my dress, he plays with my bra strap. Our kiss is intimate, exciting, passionate. Our kisses are growing more urgent. The wind strengthening, the crashes of thunder seem to heighten my growing feelings of urgency, of excitement. The rustling of the fabric, the feel of the net petticoat driving me wild. I fear an explosion in my panties. I long for his explosion up me.

Tom instructs me to sit up straight. I do as I am told as all good girls must. He is a magnificent sight laying on his back. Strong, rugged, handsome. His strength, his masculinity heightens my feelings of femininity in a way I have never previously experienced.

I sit on his erect cock. The feelings of his manhood tapping at the rear of my little panties feels superb. He pulls the top of my dress forward, removing it. I am now sitting up straight, rocking gently backwards and forwards on him as he gazes at my padded lace bra. He cups them in his hands. Fondling me as he would a woman amongst my moans of delight.

The feel of a man caressing my imaginary breasts is a dream. I close my eyes and savour the feeling. In my mind my phantom breasts have been a part of me all my life.

Again, I am glad he can not read my mind as an image forms in my mind of the many times as a teen that I have sat in a chair beside a mirror in bra, panties, stockings, heels with my sisters life sized baby doll at my breast as I gaze at the reflection of Rebecca breast feeding. But one of many moments throughout my life that I become a woman.

Tom sits up straight, he begins to reposition. "On your knees Rebecca," he instructs.

Again I eagerly comply. I kneel on the bed. The top half of my dress hanging loose the bottom half for now neatly in position. I feel frustrated that the kissing must stop but excited about what may come next.

Tom kneels behind me, his strong hands around my waist as he pulls me back. His cock is still outside the many layers of the dress. He is teasing me, maybe we are teasing each other. He pulls me back against him. Even through the layers I feel how hard he is. His erect cock must be pointing straight forward. I need him.

At last I feel him lift the dress. He lifts it high, folding both the skirt and the petticoats up onto my back. I feel the cool air. He reaches forward and strokes me through the panties, gently, delicately. His hand moves back and briefly cups my little LadyBalls.

He unfasten the stockings from the belt, the straps hang free as he starts to remove my panties. I fear I will explode over the bed as he gently removes them and casts them aside. I prey I have not stretched them too much. Has my sister ever felt such excitement with a guy while wearing them.

I have never felt so exquisitely exposed as I kneel there on all fours. He refastens the garter straps to my stockings before taking my hard little sissy cock in his hand again and gently strokes me. He moves forward slightly. I feel his erect manhood against my bare skin for the first time.

I am no longer protected by the delicate lace of the panties. If Tom were to want me now all he would have to do is thrust forward and I would be his. I long for the moment. He pushes forward. He teases me. His erect cock is neatly positioned to enter me. To fuck me. I am tantalizingly close to being screwed as a girl. His hand moves from my cock. Both his hands now around my waist.

He pulls me back onto his shaft. The tip rests at my entrance. I long to feel him fill me though we both know that I cannot take him like this. Not just yet. His precum lubricates the tip. He eases forward.

The tip slips in. I push back. We are both eager, desperate. We both know that it will not work this way. Not just yet.

"God you are a sexy little bitch Rebecca", Tom says, "On your back, now."

Eagerly I roll over. He lifts my dress, my little cock pointing for the sky amidst the petticoats and chiffon. I gaze at his dripping cock. We both know that it will still not fit.

"In my bedroom, down the hall, third on the left," I instruct.

"Under the bed, cardboard box, go and get it."

He looks confused but he leaves me on my sisters bed and proceeds to my room as instructed. I know I need lubrication. I have fucked myself with my vibrator hundreds of times and I know that Tom is bigger...much bigger.

Returning, he empties the entire contents on the floor. I instruct him to open the KY lubricant. As he does so, much to my embarrassment he looks at my three vibrators, my stockings, my bras, panties, my maid costume, my princess dress and my numerous other secret dress up playthings. He jokingly points the plastic imitation gun at me. I blush.

Kneeling between my legs he hands me a condom. Eagerly ripping it open I carefully roll it on him. I can not believe that at long last I am the girl, putting a condom on her man.

Taking the lubricant he looks perplexed. Smiling, I take it from him. I unfasten the lid. I place a pillow under the base of my back then lay back. I pour a little onto myself and it trickles down towards my ass. I take his middle finger and show him where to position it. The oil builds up behind the dam that is his middle finger.

"Massage it in baby," I instruct "Then Take me, I am yours."

As he finger fucks me with his ample digit I try with every ounce of self control to hold on.

I am ready, we are ready.

As he lays on top of me gazing into my eyes I whisper "Take me Tom"

To be continued.

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Riki1942Riki1942over 3 years ago
Dressing

I don't think that dressing up would be be anywhere near as sexually arousing for a girl as it is for a boy.

I'm dressed and made up at least as much as I am not and always when having sex with my boyfriend. I could have naked sex with another guy, but becoming a girl and still having sex be gay is the best of both worlds!

NellaBarely2NellaBarely2almost 9 years ago
It's a shame life isn't this simple

Life happens while we think we're trying to control what might be. How often do we try to plan every minute of a future event only to look back on the actual situation to realize the reality was better than the fantasy. These two were both READY to make a play for each other; for the first time they were on the same track heading in the same direction. The story could have been better, longer, more detailed prelude ... but it wasn't necessary. Rebecca knew both were ready and didn't need to waste time. Even if it could have had more colorful detail, it was complete as it is. Good story.

griffin57griffin57about 9 years ago
Very good.

Needs more and longer chapters Rebecca.

Boo96Boo96over 9 years ago

My darling Rebecca.....You've really outshone yourself this time. This is EXACTLY how we have always imagined it will be..... Great story, darling.....

RebeccaCherieRebeccaCherieover 9 years agoAuthor
Thank you

Josie, BlueSky, thank you.

Josie, yes, I feel totally fem. Always have always will. I am sure many readers relate to this feeling, yourself included seemingly. I know the gun was a little naughty. I do have a little plastic one in case a man ever needs to take me at gunpoint !!! :-)

Xxxxx

Rebecca

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