Tail Butt Plug, Costume Party, and [M]y [F]irst Anal Fuck

My dad is a CEO, but his motto is that money is fleeting, skills are not. He and my mom made sure I could take care of myself in any way necessary. Sure, he is comfortable monetarily, but we’ve always lived below our means. Status never meant anything. Except for meek, socially anxious Wren in high school.

One skill I was taught when growing up was how to sew. And I’m pretty good at it, if I do say so myself. To this day, I wish there was a picture of the costume I made for the Halloween party we attended senior year. Rather than buying one, I chose to create one. And I was fox. In costume and look. We were both 21.

The only thing was that it required a little modification. I already had the white thigh highs and arm compression sleeves, the black gloves, and black shoes. I only had to buy the orange leotard, ears, and the tail. The latter of which is where the modification comes in. It wasn’t any tail, but a Fox tail butt plug. But with the skills I had learned, I was able to fit it through the clothes easily and to look like it was part of the get up.

All eyes were on me as we arrived. Sure, it was mostly the leotard clinging to my big tits, but it also excited me that no one, not even the man beside me knew that the tail was attached to a plug in my virgin asshole. My ass had full control of the tail, which was fun. But not as fun as the lubed flare sliding into the tight hole, and not even close to the feeling of it in me in public.

Honestly, I had to be careful how much I thought about. A wet spot would likely be very obvious in the simple costume. The cool, fall air already had my nipples at attention. Steven couldn’t keep his eyes off me. Which of course complicated things. Especially when he gave me a playful slap on the ass and the tail wagged.

“I’m so horny, babe.” I whispered to him. “Let’s get out of here. Take me home.”

As I brushed against him, I could feel his dick was a little engorged. He wasn’t hard but wasn’t complete flaccid. It was clear my costume was working, and we left without hesitation.

That night was not spur of the moment. I had been plotting, planning, training for that night’s finale. The Fox tail butt plug was just the final piece. Steven didn’t know, but I had been training my ass to take his dick. I allowed the thoughts and visions to flow as we walked home, feeling the crotch of my leotard grow damp with anticipation.

The sleeves and gloves were off before we even got back to the apartment we shared with friends senior year. The leotard was slid under my tits before his key was in the door. As soon as he locked it behind us, we kissed passionately and he effortlessly picked me up and carried me to the bedroom.

Steven threw me on the bed and immediately began kissing all over my tits and rubbed my pussy through the wet spot that had formed. My hips bucked and I moaned at his touch. I used my flexibility to contort myself in such a way that I could start removing his clothes while he stroked my clit.

Begrudgingly, Steven got up to remove his clothes completely and began to tug at the stretchy fabric below my bosom.

“Just pull the crotch to the side. You can’t pull it off. You’ll see. Just fuck me. Fuck me now baby.”

I began to remove the ears.

“Leave them.” He said.

Steven slid the leotard aside and pressed his cock into my tiny pussy. I sighed as he entered and slowly filled me up. He slowly removed himself and after a few pumps began to fuck me hard, bracing himself with my tits.

“Mmmmm…fuck yes. Your dick is amazing. Fuck me hard baby! Mmmmmmmm”

Never one to disappoint, Steven squeeze my tits as he pounded into me. He tried to move a hand to my clit, but brushed it away and told him to keep gripping my tits while I rubbed circles on my sensitive button.

“Yes baby. Faster. I’m going…mmmmm…aaaaaaahhhhh…I’m going to cum all over your dick. Aaaaaaaaggggggghhhhhhhhh!”

Pushing Steven away from me, I repositioned myself to stroke his wet cock.

“Grab those scissors off the table. You’ll have to take them right beside the tail and cut a big hole around it. You’ll see what I mean.”

Steven did as instructed as I positioned myself with my ass in the air, shaking it so the tail would move. I could feel him poking around and pulling the fabric away from me. I heard the scissors cut through and my ass becoming exposed.

“Wren?!” Steven gasped. Before cutting the entire leotard in two.

I sat up wordlessly and removed the bottom over the tail. And slid the top around my breasts and my head. He looked at me for a moment, taking in the Fox ears, tail, white thigh highs, and shoes I never removed. I got on all fours again.

“I want you to fuck me in the ass. Pop my anal cherry baby. The lube is on the table.”

He reached over me and grabbed the lube. I could hear the cap open and the contents sputter out as he coated his dick. As he pulled the tail from me, I moaned slightly then shrieked when the coldness of the lube hit my asshole.

“Are you sure, Wren?” He said with his tip pressed against my Virgin opening.”

I responded by pushing against him. Slowly his cock entered me, filling me in a new way. Steven listened to my body and vocals and continued to slowly pull in and out, occasionally replenishing the lube until everything felt smooth and I began to moan and push against him. He thrusts sped up and I quickly came to an orgasm, falling face first into the bed.

With a wicked grin, I rolled over. Using the flexibility known to cheerleaders and dancers, I pulled my legs above my head so I could watch as he fucked my ass. He slid in more easily this time as we both moaned from the new sensation. He kept hitting a sensitive spot as he pounded himself hard into me, looking down as my body tightened and convulsed on his dick.

“Goddamn babe.” I panted. “You keep making me cum. Mmmmmmmm…fuck that feels good. I can’t wait until you fill my ass with cum.”

Steven pushed himself deeper into me. Squeezing and rubbing my breasts in his hands as his body crashed into mine. Through the tightness, I felt him tensing up and breathing hard.

“Fuck!”

My ass began to fill with his warm, white goo as his thrusts slowed and he pulled out of me. His cum dripped down to my pussy as he stroked the last bit out.

Though we’re older now, like my cheerleading uniform, [the tail](https://www.reddit.com/user/bent-my-wookie/comments/xad83h/fox_tail/?utm_source=share&utm_medium=ios_app&utm_name=iossmf) remains part of our collection and still comes out at times.

Source: reddit.com/r/gonewildstories/comments/xad9q5/tail_butt_plug_costume_party_and_my_first_anal