Dressing Up with Filly

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

He kissed me again, passionately, earnestly, and I could not resist his soft lips and wet tongue. Then he rubbed his manly face across mine. I moaned again with pleasure. It felt wonderful.

"Do that again Phil," I pleaded, but instead he ran his sticky wet tongue across my lips over and over again. Oh God, how I loved that!

He told me to stand up and reach to him, the white, suspender belt that lay on the bed to his right. I leaned across him to do his bidding, when he seized my waist with one arm and held me tightly. I was trapped and exposed, the white panties still below my buttocks. I thought he was going to spank my bare bottom but he didn't. Instead, he used his free hand to caress my bum with gentle, tender touches. This I had dreamed about and it was even better than I had imagined. He pressed his hand into the valley between my cheeks and I parted my legs to give him better access. He ran his fingertips smoothly up and down the crack of my ass and drew little circles around my rosebud. I squealed with pleasure as my cock hardened.

"Such a beautiful round bum!" he exclaimed.

I let him do what he wanted to me. Something clicked inside my head the instant he started to tease my virgin rosebud. I knew this man wanted me and I felt myself become the girl in my fantasies. He was bringing out my alter-ego and it gave me the confidence that I lacked in everyday life. I was in heaven.

"Cock teaser," he said, mockingly, sliding one hand across my firm buttocks. "That's what you are, Don, a dirty, little cock teaser. Teasing all the men in the changing room with your cute, soft body and your lily-white, bum. Bending over to put on your socks and undies, wiggling this little bum deliberately, provocatively. You just love tempting all the daddy dicks, don't you, now?"

Phil flipped me over on to my back and ran his hand through the soft down of my pubic hair. I realized we were playing a sex game and all the talk was to increase our arousal. I had played out such scenes in my mind with the daddies and Mrs Jones or the daddies with me.

"Your pubic hair is so soft and fluffy," he said smiling. "That's it! I shall call you Fluffy from now on. Little Miss Fluffy, the cock teaser, and I want you to call me Filly. That's what I call myself when I dress up like this. Now let me dress you like the dirty, little, cock teaser you are. Stand up now."

Wanting to play his little game and holding the suspender belt in my right hand I raised it to my mouth and sucked my index finger, provocatively. I stood with my legs crossed at the ankle and on my tiptoes. Then, placing my finger on my lower lip, feigning innocence and all wide eyed, I spoke in a soft sexy voice...

"Cock teaser? Me? You think I am a cock teaser, Filly? Is that because you want me to be a dirty, cock teaser and tease your cock for you? Do you want me to tease your cock just like this, Filly?"

Then I leaned down and tickled his balls lightly through his sheer, black, nylon panties before running my finger and thumb ever so gently, up and down the length of his rock-hard shaft several times, before pausing at the top, to scrape a nail lightly down the sensitive cock head, which responded by emitting yet more precum to add to the sizable stain at the top of his beautiful panties. On an impulse, I dropped to my knees and placed my finger and thumb on either side of the base of his cock. I jiggled it from side to side, then ran my mouth, tenderly, all along his lovely cock, dampening his panties. When my mouth reached his flaming, purple knob, I flicked my tongue across it several times. As I got my first hint of Filly's sweet precum, I heard him moan with pleasure. I felt so proud of myself.

My little cock was oh so hard but I had not cum again. I pressed my face against his hardness and breathed a sigh of contentment. He smelled delicious. This was the smell of a real man. I wanted to stay there with my face pressed against his lovely, hard cock. I felt his cock throb against my soft cheek every time I lightly tickled his big balls. I just could have done this all day, but Filly told me to stand up. He had a bid smile on his face.

"Does my Filly not like that? Alright then, I won't do it again." I said and stood up.

Filly took my hands in his.

"Oh Fluffy, you are just the best cock teasing, little sissy bitch, aren't you? I knew when I saw you admiring my cock in the changing rooms that's what you were. And when I saw your slim, smooth body, your sexy slender legs and your little bum this morning, I knew that I was going to take you home, dress you up and that we were both going to have the time of our lives, playing together, in panties and stockings."

His words filled me with joy and self-belief. I could not have admired him any more than I did at that moment. I knew I would let him do whatever he wanted to me and that I would be able to do to him whatever I wanted.

Filly took the suspender belt off me, then he reached around me and while he was attaching the suspender belt around my waist, his bristly chin tickled my tummy and I liked it. He picked up the white stockings from behind him and with great care and attention, one at a time, he rolled each stocking down and once more, I held on to him as he placed them carefully on each foot, to draw them lovingly up my legs. He made sure his hands caressed my thighs tenderly. He took the garters, one by one, and pulled them under my panties to attach them to the stockings. He was just as excited as I was. He then adjusted my panties to his liking. He blew his warm breath on my cock. I was so turned on by what he was doing, by his touch, by the whole experience. All these wonderful, new sensations.

"Try on those heels by the wardrobe," he said " I want to see you in heels too."

I tried them on and Filly whistled. I did not expect his reaction to be so strong.

"Get the fuck over here right now and let me look at you. Fuck me! You really are Miss Fluffy now. Look at your legs and ass in those heels. You were born to dress like this. I mean... Fuck! Keep the heels on and get on that bed before I spank you."

"You wouldn't dare spank me," I said defiantly with my hands on my hips, hoping he was going to put me over his knees like a helpless little girl. In my mind I was screaming... please, let him spank me.

In one quick movement Filly pulled me down between his legs and over one knee, trapping me. I pretended to not want him to do this. I begged him not to do it. He pulled my panties down and begin to caress my buttocks. My mock protests stopped as I began to enjoy the sensations his clever hand movements were giving me. I was helpless, humiliated, but being pleasured like never before. He must have felt my hardness on his thigh.

"So I wouldn't dare spank you," he said, laughing, and slapped my cheeks sharply. I yelped, but then he ran his hand down the crevice of my bum cheeks. We both gasped in unison. "Fuck! You are as smooth as a girl! As smooth as a girl!"

I could only whimper as his hand gently massaged my bum and his fingertips tickled me up and down the crack of my ass and all around the tops of the back of my thighs. It was deliciously dirty and sexual. I wanted more.

"Oh my, I gotta get this oiled up. Does my little baby girl like daddy's fingers here? He asked, mockingly as he ran them lightly up and down my perineum. "Of course you do baby don't you? Go on, tell me you like it or else..." He gave me another sharp slap on my bum.

"Oh God, yes I love it, I love it. Please don't stop, don't ever stop.""

"Not yet Fluffy, not yet".

He produced a bottle of baby oil from under the bed and I felt it oozing down between my bum cheeks as he poured generous amounts all over my bum. He set the bottle down and picked up something else from the same place. I heard a humming sound.

"What is that noise Filly?"

"Something for your pleasure pet. A silver humming dildo. Just relax."

The humming continued and I felt something metallic at the entrance to my bum hole. I was full of trepidation but Filly told me to relax and enjoy the sensations. He started to slide the implement gently along my crevice, back and forth, back and forth. It felt so good, so tingly, so absolutely dirty, that my anxiety vanished. Without being asked to do so, I opened my legs a little bit to accommodate Filly's pleasurable movements. No one had ever played with my bum hole before, I told him. Filly corrected me and told me it was my pussy. I nearly came when he said that.

The dildo was no longer cold but warm. I pictured it glistening with oil as my cute bum must have been. Every few seconds Filly told me how much I was going to love it and the truth was that lying helpless across his knee, and totally at his mercy, I was in heaven. Every time he maneuvered the dildo close to my pink rosebud, he applied a little bit of pressure causing me to moan with pleasure. It was so sensitive and tingly.

Then he reached for something else from below the bed. He told me it was lube, lovely lube, lickable, lush, lube. He squirted it directly on to my hole and all around the entrance. Our cocks were so hard now. I could feel his crowbar like erection pressing and pulsing against my body and I was rubbing mine into his leg.

"What are you going to do to me Filly?" I asked.

"You know exactly what I am going to do pet and you want me to do it. Relax now it's going to go in. Don't resist. Good boy! Good boy! Push out against it now. That's it! You are loving this, aren't you? I just know from your hard cock you are loving this as much as I am."

Then, just like that, my resistance ceased and the head slipped in. It felt wonderful.

"Oh Filly! Oh Filly!" was all I could say.

Then he slid the silver toy all the way inside me and I could feel it gently vibrate and hum deep in the very core of my body which had offered no resistance to the metallic intruder. My sphincter muscle was twitching and I felt wonderfully full but I was still a little bit nervous. Filly had inserted a humming vibrator up my bum and was holding it in my hole. He kept telling me to relax, to breathe deeply and accept it, as I would soon feel something delicious. His soothing words helped me regain my composure and just as I was starting to feel comfortable, Filly twirled the vibrator around and it hit my prostate again and again. A string of "ooh's" and "aah's" came out of me and all I could do was whimper with uncontrollable delight. I thought my cock was about to explode.

Filly pulled my panties up to hold my new silver toy in place. He pulled me up on to the bed after him as my hand reached around to my ass. I did not want to lose the source of this new pleasure. Lying face to face he put one arm under me and one arm around me. I felt his hands squeeze my bum continuously and our cocks pressed urgently against each other. I put my arms around his neck and looked into his eyes. For the second time that day I cried out to him that I was going to cum.

"Cum for me Don, cum in you little white panties just for me", he whispered. "Cum for Filly."

He watched me as my eyes rolled back in my head. I started to moan loudly, uncontrollably. He licked me across the lips again. My senses were overloaded with pleasure on the inside and pleasure on the outside. I thought I was going to black out. For the second time that day my sissy cum poured out and flooded my panties as I succumbed to my orgasm. I heard myself screaming in ecstasy. This proved too much for the equally aroused Filly, who unbeknownst to me was also crying out and a massive load of his creamy, white cum, soaked into his panties as we orgasm-ed together, uncontrollably.

It took a moment or two for us to regain our composure. We were still in each other's arms and we held on to each other tightly, squeezing, touching, cheek to cheek. Filly slid my panties to the side, removed my silver friend and switched it off. Then our mouths found each other and our kisses were desperate and eager. We whispered each other's names and neither of us wanted to lose this moment, this most precious, best moment of our lives. Filly's cum laden panties were sticking to mine but neither of us cared. The feeling was blissful.

12
Please rate this story
The author would appreciate your feedback.
Share this Story

Similar Stories

A Slut is Born Young man forced to be a womanin Transgender & Crossdressers
Neighbors Sissy Son Training the boy nextdoor to be a fucktoy cumslut!in Transgender & Crossdressers
My Feminine Side Guy becomes a beautiful sexy girl.in Transgender & Crossdressers
A Harmless Favor A young wife assists her young husband to become a sissy.in Transgender & Crossdressers
Daddy's CD Waitress Young crossdresser learns to love living as a woman.in Transgender & Crossdressers
More Stories