A Femboy's First Encounter

This is a continuation of A Femboy's First Encounter. I hope those who commented on the previous story enjoy the tale I have crafted. Although based in fantasy, I tried to keep the story as realistic as possible. Enjoy!

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It had been a week since I last had Jason's long cock down my throat. He usually came over on Saturday and we hung out in the garage. My girlfriend never bothered us, thinking we were making fishing baits or some other activity she had no interest in, but in reality it was hours of me pleasuring his manhood and swallowing the cum treat he made for me every time.

Today was going to be special, though. Deborah, my girlfriend, was leaving on a weekend business retreat. Her boss had ordered all the employees to attend as a way to build teamwork and trust in a series of motivational (and mindless) activities. She had already left and wouldn't be back until late Sunday night.

Jason was due any time now, and I was beyond ready for his arrival. I had gone all out to impress and pleasure him, and I hoped dearly he wouldn't be disappointed. I heard the knock at the back door and ran to it, fixing my hair before opening the door. There he stood, wearing his best jeans and a button down blue T-Shirt. He had some vodka and a bouquet of flowers for me.

He stood there, mouth open, once he realized what he was seeing. I was wearing a tight red bodycon dress which hugged my feminine curves in all the right places. Underneath that, and invisible to him for the time being, I wore a tight black thong that held my 3 inch cock and balls tight against my body.

My hair was styled in a short, but very feminine, pixie cut and I had put on deep red lipstick. Eyeliner accented my natural blue eyes, and the subtle blush and eye shadow gave me the appearance of a real girl in her twenties. My nipples were hard, showing through the dress as I took his hand and pulled him inside.

Taking the flowers and vodka to the table, I hurried back to him and wrapped my arms around his waist. He lifted my face towards him, drinking in the aesthetic I had achieved.

"Wow... You are seriously fucking hot..." I felt his long cock hardening beneath his jeans, pressing against my restrained sissy clit. I stepped back from him, giving him a spin so he could see how amazing my ass and hips looked in the dress.

"I'm glad you like it, Jason. I wanted you to be impressed with me so very badly..."

He took my hands in his, pulling me close again. Looking into my eyes, he traced his fingers up my neck, over my small adam's apple, and up behind my head. Pulling me close, he pressed his lips to mine and kissed me deeply. He wanted me badly, and I him, so before long we had made our way upstairs to the master bedroom.

I had drawn a bath, with plenty of bubbles, and had lit candles around the room. The master bathroom was partially open to the bedroom, and his eyes wandered over the scene I had set.

"Mmmm, I am so ready for this. I've been looking forward to it since last Saturday. I haven't masturbated, saving up a big load for you to enjoy. Does that excite you, Gary?"

I nodded, shyly, "I want to make you happy. Whatever that takes, I will do it. All you have to do is tell me exactly what you want, and I will do it for you.... anything, Jason... anything."

I let the word hang, slowly pulling the dress down my body. His eyes drank me in as the tight red fabric clung to me until it was on the floor. He knelt in front of me, his face right in front of my sissy clit, and kissed me softly through my panties. I was on fire, growing to my fully erect 3 inches, and was beyond surprised. Jason had never done this before, and I was loving it.

He stood, turning me around to look at my smooth ass, before leaning in and whispering in my ear, "I'm going to sit on the bed, and I want you to lay across my legs. Do you understand?"

Nodding, I did as he commanded. He sat, and I lay down across his legs and allowed my full weight to settle on him. He gently forced my shaved legs apart, petting across my ass and balls. I screamed out as his hand connected with my bottom, the smack so unexpected that I couldn't contain myself. He was fully hard under me, and I could feel his cock running down his pants leg. I could feel the heat coming off of it, and as I turned to look back at him he smacked me again.

The pain exploded through my body, but the pain was accompanied with an intense arousal. I wanted more. I wanted Jason to use me any way he wanted. He smacked again, this time on the other cheek, and then ran his hand between my legs and rubbed my sissy clit through my thong. My eyes rolled back, and I was breathing heavily. I ground my hips against him, the sensations so amazing that I was losing myself in them.

I felt his hand move away, and the final smack came, hard enough to bring tears to my eyes as the sharp pain spread. He had smacked me on the asshole, hard, and had caught the bottom of my balls with his fingers. I felt a little sick, but savored the pain in a way I never knew I could.

"Up."

I followed the command, and he stood in front of me. He unbuttoned his shirt, his chest hairy from a week of not shaving. I wanted to run my fingers through it, but Jason was moving over to a small bag he had carried in. I wanted him so badly that I hadn't even noticed it, and I watched in curiosity as he rummaged through it. He came back with two clear cylinders with corkscrews on the back.

"These are nipple suckers. I want you to put them on every day. I want those useless little nipples big enough for me to suck on. Do you understand?"

I nodded, taking the cylinders. They were simple to use, and after Jason's tongue had lubed my nipples up I placed one over each. I turned the corkscrew and felt the suction; it was intense, drawing not only the nipple but the entire areola up into the device. Jason watched my nipples being stretched, and pulled his jeans off.

He was wearing boxer briefs which clung tightly to him. I was so turned on it was ridiculous, and the nipple suckers were making me feel like such a dirty girl. I wanted to touch myself, but I had been waiting for this day. I took Jason's hand and led him into the bathroom. I sat him on the edge of the tub and moved in front of him.

I danced for him, moving my body as sexily as I could, like that epic scene from True Lies where Jamie Lee Curtis unknowingly dances for her husband. To finish I slowly pulled my thong down, showing him my tiny little cock. I turned around, pushing my ass towards his face, so that he could see my boy pussy.

Jason leaned in, smelling me deeply. I had cleaned myself, inside and out, and he knew it. I felt his tongue press against me, eating my asshole like a pussy, and I knew in that moment how lucky a girl his girlfriend was. His tongue was strong, tracing circles around my eager hole before thrusting into me. He wriggled his tongue, and I involuntarily tensed up. He laughed, smacking my ass cheeks with both hands.

As much as I was enjoying the attention, I was here for one reason. I wanted his cum, but not to eat. I wanted to feel his hot jizz as far up in my body as I could get it. I wanted Jason to fuck me and blow his load inside of my ass.

"Please, Daddy, I want you to fuck me today. We can do it in the bubble bath if you want. I want to feel your cum fill me up. It's all I want in the entire world!"

He took off his underwear and socks and then slid down into the tub. He looked up at me, "Well, then get in here beautiful."

I stepped into the tub, facing him with a foot on each side of his body, and sat down slowly on top of him. As the warm water made contact with the goosebumps running up my thighs I gasped, and finally my hips were in the water. I felt Jason's raging hard cock below me, and the small amount of pubic hair he's grown since our last encounter. It was soft, and in truth I loved my man a little hairy.

I had a bottle of silicone lubricant by the shampoo, and taking some on my fingers I lubed up my asshole and his cock. The water didn't bother the lube; I had done my research. Putting the bottle back on the tile shelf, I settled my weight down, feeling his massive cock head press against my boy pussy. I was ready, had practiced for weeks, but still the feeling of Jason popping into my asshole made me lean forward and rest against him.

Jason's arms wrapped around me, hugging me tightly, as he slowly thrust the rest of the way into me. There was pain, obviously, but the intense feeling of fullness so deeply inside of me coupled with his girth pressing against my prostate made me shiver. I felt my insides stretching to their limit, a slight burning, but despite all that the pleasure was overpowering.

I breathed in shakily, "I'm ready. Just please go slow at first. Once I'm stretched a little we can pick up the speed. Jason nodded, and unscrewed the nipple suckers. He took one of my sore nipples into his mouth; it was swollen, and felt cold until he began to suckle me. He moved to the other, sucking my sissy breasts like he was trying to get milk. If only I could, I thought. There were hormone pills, of course, and maybe one day I would commit. For now, his mouth on me was heaven.

He was thrusting now, slowly, and my well lubed and clean rectum accepted every inch of him. The feeling of finally being fucked caused me to leak a small bead of precum from my soft sissy clit, which Jason eyed before saying, "Enjoying this, are we?"

My face was planted against his chest, licking his hairy nipples. I nodded, moving my hips in rhythm with him, getting into the motion. Jason picked up speed, and his sheer size was causing my sphincter to move back and forth, in and out, with his cock as he pumped into me.

I was going to be sore later, but I no longer cared. I rode him faster, taking him to his final depth before sliding up his long shaft and back down again. He was grinding into my special spot, causing me to shiver, as the sissygasm built. I sat straight up, pinching my nipples and rolling my head back, waiting for the sweet release that I could feel coming.

Jason's hands were on my hips, and by then he was fucking me furiously from underneath. The water in the tub was sloshing everywhere, and my hands were in my hair, working my hips down onto him, as the feeling of needing to piss overcame me. I let go, feeling the warmth pass through my clit in a small stream. Jason held his mouth open, tasting it before spitting it back down onto his chest.

I was so very close, needing my own orgasm in a way I had never known before. His cock, so long and hard, hitting me just right inside my boy pussy; my asshole, gripping his cock with every ounce of strength that I had. I came, shooting a watery load of precum and cum onto Jason's chest. I yelled loudly, growling, as the orgasm reached it's peak.

Jason was there too, grunting as his orgasm began. I felt his cock twitching inside of me, and felt the hot, runny sensation of an ass filled with cum. I breathed heavily, moving my had down enough to lick my cum off of his body. Jason collapsed back against the tub, sweat covering his head, and his cock growing soft inside of me.

We lay there together for a while before I slid his cock the rest of the way from my ass, sealing my gaped hole with my fingers. I crawled from the tub, sitting upright over the tile floor, and let Jason's cum ooze and bubble out of me. I coughed, trying my best to mask the noise of the air escaping me, and looked over to see Jason watching me intently.

"Do it, baby. Shit out my cum and lick it up off the floor like a good little dog."

I pushed the last of his cum out, and then got down on all fours. I dragged my tongue across the tile, sucking up the mess I had made on the floor, rolling the cum around in my mouth for a few moments before swallowing. I stayed down there, raising my eyes to meet his, "Like that, Daddy?"

Jason nodded emphatically, wiping a wet hand across his face. "That was fucking amazing! You didn't mind the rough spanking, did you?"

I licked the floor again, hoping to find another little puddle of cum but not finding any. I sat up, rubbing my sore nipples for a moment, "Not at all. I told you, I want you to use me any way that you like. I want your cum, Jason. I love the way you taste to the point where I'm craving it all week. I was hoping you would jack off during the week and save it up for me. I was wanting to put it into ice cube trays so I could have little treats throughout the week without Deborah knowing."

Jason stood, the water running off his perfect body. I wanted that cock again, even just to suck on it while it was soft. Jason dried off and gave me my wish. We lay in my bed, the bed I shared with my girlfriend, and now the bed in which I was another man's girlfriend. My head rested on his lap, and I suckled on his soft cock while he rested.

Despite the nature of our relationship, in which he believed to have control over me, I knew who really had the power. I controlled this cock now, ate it's cum whenever I craved it, as long as the girls weren't around. I sneaked a picture, no flash, of Jason's cock in my mouth. Another with his balls in my mouth. I would stroke my cock or toy my asshole later to the pictures, and as Jason slept I thought about a life where he came home to use me, not that slut he was dating.

Could I really have a life like that? I lay back down, suckling on his cock until I felt it grow hard again in my mouth. I stretched my neck and back, and leaned over his sleeping body to take his hardening cock into my mouth. No matter what the future held, his cock was mine tonight, and I was going to milk him of every last drop.