GF Walks in on Femboy Toying Ass

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My girlfriend walks in while I'm toying my asshole.
1.8k words
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I was bent over on the floor of my bathroom, a soft fuzzy rug beneath my knees, as I massaged my prostate with my favorite glass dildo. Every press against my prostate brought waves of pleasure, and as I looked between my legs at my soft little cock I was overcome with impatience. I wanted to see that little drop of precum that meant I would get my daily feeding.

My girly big ass was pushed as far out as I could get it, which made sliding the dildo across my p-spot that much more pleasurable, and my black thong was pulled aside just enough to allow entry into my boy pussy. Just thinking about those femboy terms always turned me on even more, and before I knew it a small drop of delicious precum formed on the tip of my pitiful little cock.

I used a finger to gather up that precious first drop and quickly got it into my mouth. The subtle flavor, and the thought of eating a massive load of cum from my big balls was pushing me closer and closer to sissygasm. I wanted so badly to take a mouthful of cum straight from another man's hard dick, or even better to be used in a gangbang and have multiple loads shot onto my face and into my eager mouth.

I focused on that thought; all of those men stroking their cocks at me, looking at my girly body and jacking off with the desire to cover me int their cum. I moved the dildo faster, pressing it harder against my prostate, and was rewarded by a dribble of more precum, which I caught in my palm and licked up. The flavor, the sensation, imagining all of the precum I could eat from those men's cocks.

I was working my asshole furiously at that point, my hand positioned below my sissy clit, when my girlfriend walked in. She knew that I did things like this, and she had seen me in my girly clothes many times, but she left me alone while I came. She saw me, waiting to catch my cum, and with a little precum glistening on my lips.

Instantly she unzipped her jeans, pulling them down enough to rub her pussy through her cotton panties. Her hand moved up under her shirt, squeezing one of her breasts as she nodded for me to keep going. I looked up at her, happy that she would watch me finally eat a load of my cum, and positioned myself so that she could watch me toy my boy pussy.

"You like watching me get fucked baby? You like watching my little sissy asshole get used rough?"

She was leaned against the wall now, her shirt pulled up and her bra pulled down enough for me to see her F-cup breasts. She was a full figured woman, but in a remarkably sexy way. She had the smallest of tummies above her extra wide hips; a stark contrast to my skinny waist and hips. She often remarked how good I looked in thigh highs, or how much my ass popped out after a workout, but I could tell she was enjoying seeing me work my asshole more than any of that.

"I'm going to cum soon, baby, and when I do I'm going to catch it in my palm and eat every damn drop of it. I'm sorry, it's all for me."

She smiled and began rubbing her pussy through her now-wet panties again, "It's okay, honey. Maybe I'll just invite some friends over to work your asshole for you." She winked, but the thought of her bringing guys over to use me pushed me over the edge. I dribbled cum out of my sissy clit, filling my palm up, and rode the wave of pleasure until I was finished. This type of orgasm for me wasn't as strong as a normal one, but I could have them over and over again.

She got down on her knees, and guided me up off the floor. I was careful not to spill any of my cum from my hand on the way up, and we kissed long and hard once our faces were close. She dipped her fingers into my tasty treat and began feeding me cum 2 soaked fingers at a time. I could taste her pussy mixed with my own flavor. She spread some across her nipples, and I greedily sucked on them as I cleaned them off.

I put my hands between her legs, sliding my fingers into her warm, wet pussy. She rode my fingers as I worked them in and out around her G-spot, playing with her clit with my thumb. She returned the favor by reaching around me and taking hold of the glass dildo still in my ass. She fucked me hard, rougher than I ever would have, and before long I was cumming again, which gathered between my closed legs and covered my balls and cock.

She used her fingers to scoop it up, eating some herself as I whined. She was using my boy pussy hard, so I began ramming my fingers into her. She wanted more, I could tell, so I started pressing other fingers into her fat pussy until finally I had nearly my whole hand in her. We had never done that before, so I looked into her eyes. She just nodded, riding my fingers, and her consent was magical. I pressed slowly, but forcefully, until I popped my entire hand into her. I made a fist, using my thumb to press against her G-spot.

She squirted hard, and with her positioning it covered my entire body. I greedily lapped it up, and as she collapsed back onto her butt she begged me to come to her. I crawled across the floor, the glass dildo looking like a tail as it stuck out of my ass. She pulled me to her, kissing and licking her cum off my face.

"Are you done?" she asked, to which I shook my head no. I turned around, removed the dildo, and got as close to her as I could.

"Fist me too...."

There was no hesitation on her part; she used the cum dripping from my balls as lube on her hand, and then pressed it into me until she was completely inside. She closed her hand into a fist as well, but instead of being gentle she just started punching straight into my boy pussy. I let out a loud yell, but begged her to keep going. My reaction to her hand in my ass only worked her up more. She was being so rough with me, and I fucking loved it.

She grabbed my cock and balls in one hand and aimed them back at her. "You are going to cum for me, you little bitch. You aren't going to dribble it out' you are going to shoot a hot fucking load of cum all over these fucking titties. You are then going to clean it off of me, do you understand?"

I nodded my head, unable to say much as I edged closer and closer to orgasm. She was moving my entire body with her arm, which was much deeper than I had realized. I could nearly feel her elbow. It was too much, and I could feel a warm sensation growing in my crotch. The urge to pee overcame me,and before I could say anything about it I began pissing all over her.

She didn't stop fisting me; instead, she just yelled out loudly "Oh fuck yes, Baby! You just squirted all over me! Fuck that was hot!"

I couldn't contain myself anymore and came hard. My entire body pulsed as I felt the thick ropes of cum fly out of my cock. She squeezed my balls hard, adding to my pleasure, and as I looked back at her I felt the sensation of her pulling her hand out of my asshole. I turned around, as she had instructed me too, and saw that her shirt was soaking wet. Her breasts glistened with my piss, and lines of white cum covered her from head to tummy.

I dove in, running my tongue across her anywhere I could find cum. She was breathing heavy, sweat forming on her brow, and she giggled as my tongue tickled her. I loved her intensely, and when I was done eating my cum I sat in front of her. We stared into each other's eyes for a few moments before I broke the silence.

"Thank you so much baby, that was amazing. I didn't think you would be that into this or I would have asked you to join me earlier."

She gave me our standard post sex high five, and took off her piss covered shirt, "It's fine. I had a lot of fun, even if I did get soaking wet. I need to shower."

I was still on my knees when I looked up at her and asked, "Do you think you can do like you said earlier? Like, maybe bring some of your guy friends home?" She turned on the shower and sat on the toilet. She thought hard for a few moments, and I waited in anticipation.

"If I were to bring guys over, you wouldn't stop at sucking their dicks. You would let them fuck you, wouldn't you?"

I lowered my gaze to the floor, shoulders slumping, "Yes... I would. I want them to fuck me. I want them to fill me up with their cum... Is that okay, baby?" I looked back up at her, unsure if I had made a mistake by asking for a fantasy to be a reality. She had her chin in her hands as she looked at me. I loved this woman, and I didn't want her to ever feel betrayed or not good enough.

She took my hand in hers, and breathing out a sigh she asked, "Are you ever going to leave me for someone else? Do you truly love me?"

I was shocked by her question; we had been together for 10 years, through good and bad times, "Of course I love you baby, and no I would never leave you. I just have these crazy desires that I can't help."

She smiled, "Then yes, of course, I will bring other guys over to fill you up with cum, and feed it to you. I even have 2 or 3 in mind right now. I just want you to be happy, and have no regrets in life." She stood, climbing into the shower, and I saw her hand peek out from behind the shower curtain. She curled her finger in a 'come here' gesture. "Now get in here, you little sissy slut. I want to play with your asshole some more."

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7 Comments
AnonymousAnonymousover 2 years ago

honestly this is really cute and almost wholesome

AnonymousAnonymousover 2 years ago

I got SO HARD thinking about his girlfriend bringing over some of her guy friends for him to suck and get fucked by. I'm about ready to cum in my hand so I can lick it uo like he did. Guy on guy fucking with a woman watching is SO hot. I've only had that opportunity once when my favorite masseuse lined up another guy at the same time as me for a massage so she could watch us fucking. He had such a long cock and filled me to overflowing with cum. She let me fuck her ass after he was done with me. dale

AnonymousAnonymousover 2 years ago

Not into the fisting but that is just me! It, in no way, detracts from how hot this scene is! Love the precum play/eating, it is my favorite treat as I work my sissypussy with my toys, feeling the leak start and lusting over the taste as the strings grow longer and longer! 5 stars, baby, wish I knew you IRL!

TNsourdoughTNsourdoughover 2 years ago

A good first story, but just an average read. I PM'd you with more details. Keep on writing!

NMsissyCuck69NMsissyCuck69over 2 years ago

Fun but not as arousing as I expected. Perhaps another 1000 additional words describing ¹the things you can expect the first time you have been fucked bi a cock big enough to hit your special place and make you cum

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