One Shot

This is it. This is my one shot to get everything I ever wanted. To finally be who I really am inside. One final look in the mirror to steel my resolve and take one last breath before it's past the point of no return. Wavy long red wig, tight and flowing sultry like. Smooth waxed body glistening and sheerly covered in red toned lace corset. Small natural pseudo breasts filling out the cups. Garter attached to red sheer pantyhose, not to draw away from the hot pink chastity cage concealing my tiny penis and keeping it locked and submissive, like it should be. Maybe I should have put on the tall peg red high heels after I inserted the fluffy long fox into my butthole. I knew I should've practiced more in heels before today.

Lubing up the butt plug on the tail was making my heart race. While I have practiced and trained playing with my butt with my various dildos and sex toys this was more symbolic nervousness. As I squat down and insert the plug into my still tight virgin butthole I told myself that this will only come out when I am made into a real woman. Once inserted I breathed once more and stood up to look at myself in the bathroom mirror.

This is it. It's not too late to back out now. Put away all this silly stuff and walk back to my dorm room as my unassuming and meek self. But I had to be strong. This was my only chance to show everything who I really am. I've been planning this for months. As I put on the last touch to my pink shade lip gloss and touched up my makeup one last time I procrastinated.

What if everyone laughs at me? What if a teacher gets called or worse is out in the hall? All this work will be for nothing if I only make it one step out of the door and I'm wiped away. No. This is going to work. I've planned this out. I just need to go out there and present myself. Present myself to my peers and bullies and nearly strangers. This is my one shot, I can do this. I can't do this.

Just as I was about to break, there was a loud bang on the door.

"Come on dude hurry up!" a voice called from outside.

Jumping in startelement I clutched my chest and took some deep breaths. Then I realized I forgot something. Feverishly looking around I couldn't find it. It was kind of quintessential to this whole thing. I can't believe I would have forgotten to bring it on this retreat. I swear I packed it first thing when I was getting everything together for the last away retreat of senior year. Just as I was about to panic I saw it. It had fallen to the floor. I picked it up and stood up and stared at myself as I brought it up and wrapped it around my neck. As I buckled it up I made sure it was tight but not too tight, just right. A thick leather collar with the bedazzled word in bold. SISSY. With that it was time.

I swung open the door and felt the cold air hit my near naked skin. Goosebumps ran up and down my spine. I could feel my nipple getting hard and my penis jumping to get released from its tight pink confinement. I met the eye of the boy who must've been the one knocking on the door. The look of utter shock and bewilderment plastered his face. I saw him look me up and down. As I passed by him I ran a soft gentle hand under his chin to close his gaping mouth.

I stared down the hall and saw fewer and fewer people milling about and more and more eyes locked on me. I inhaled deeply and took my first real step into a new world. My heart was pounding so hard I thought I was going to pass out. I was doing it, I was actually doing it. I prided myself down the hall like I was a model at a runway. I made sure to swing my hips as naturally as I could to get the tail to swing nicely.

As much as I tried to keep my eyes ahead of me, focused on getting to my room, I couldn't help but look at some of the shocked faces that I passed. I shot a wink and a smile. I could hear murmuring and whispering but I couldn't focus on any of it to hear anything. Just a lot of murmuring and pointing. At least no one was laughing. It was dead silent except for the clicking of my tall heels.

A made it to my door and just before I opened the door I looked back down the hall and for a second I saw everyone still staring at me but in unison all 30 or so bodies shamefully and quickly and conveniently remember they had something very important they should be doing. With a wry smile I looked down to insert the key into the lock and opened my door to step inside. Closing the door with both hands I just stood there at the door trying to realize what I just did.

I just publicly outed myself as a crossdressing sissy faggot to nearly half my class and im sure the rest will hear about it shortly. My life will never be the same again. I turned to lean my back against the door and I looked around my temporary dorm room for this weekend trip. I had candles lit all around the room and I left some soft jazz playing in the room.

I dont know how long i was just pacing my room for when i heard a knock on my door. Gluping, I walked to the door and just as I was about to grab the knob, I hesitated. I knew if I opened this door now everything's about to change. But that was the point. I grabbed the knob and swung the door open. Standing at the door were 3 guys, Mark, Jason, and Jared. Jared. Captain of the wrestling team Jared. Tall, dark and handsome Jared. Bully Jared.

"Uh oh the goon squad." I chuckled while still holding the door.

Mark and Jason were speechless, but then again they never were good with wordy words. It was Jared that did all the talking.

"I always knew you were a faggot Jensen, never thought youd have the stones to embrace it though." Jared said as he took a step into my room.

I put a hand on his chest to stop him and said, "I didn't say you could come in."

My heart was pounding. I really hoped he knew how much I was bluffing.

Jared pulled my hand away and said, "I wasn't asking."

As he entered his two cronies followed. Behind them the door closed and I heard the lock being set.

Jared, without warning, ran a hand up the back of my head and I felt his long strong fingers weave into my wig and tighten. The wig wouldn't come off easily. I made sure to really set it in place.

"Hmm, nice hair. Surprised it doesn't just fall right off." Jared mocked.

"Well...what's the point of long hair if it can't be pulled.'' I challenged looking deeply into his eyes.

I tried to look for anything in his expression but he was hard to read. So it caught me by surprise when he brought his other hand to my throat and with both hands wrestled me down to the cold hard floor. My knees hit the floor and I gasped for air. A slight moan might have escaped as well. Jared was pulling my hair back forcing my look up at him and I saw he was struggling to undo his belt and zipper.

Not really knowing what I was doing I saw my own hands raise and gently start undoing his belt and pants and slid his bottom down. Out jumped an enviously big, hard, dark cock. I bit my bottom lip and slowly wrapped my fingers around it. It jumped once which made me jump. I chuckled and really grasped it this time. It was so warm and hard. I started to stroke it as I looked from it up to jared. His hands had dropped from me.

"I'm so glad it was you that knocked on my door." I said in a low sultry voice.

"Let's see how glad you were once we were done with you." Jared said and I saw him wave to his two companions.

Quickly it felt like the walls were closing in around me as the two guys surrounded me and down dropped their pants. Pointing at me were now 2 more hard cocks, one white one black but both large and in charge. I brought my free left hand up to grasp his and then looking to my right I grasped his and started stroking both. I looked back to center and Jared's unattended cock. Looking up at him I smiled and opened my mouth invitingly.

Jared stepped forward and with a hand on my head guided his cock into my mouth. I moaned and rolled my eyes as the thick, warm cock slid past my lips and over my tongue. This was it. I had not one but 3 real, hard, big cocks right here right now. It was finally happening.

I sucked jared's cock vigorously and hungrily. This was so much better than my dildos. I sucked hard as I popped Jared's cock out of my mouth. Looking up at him I could tell that he liked how I was doing. I then looked at Mark and Jason's cocks and took one into my mouth and brought that hand to Jared's cock to stroke. After sucking one i moved to the other and then back to Jared and round and round i went sucking and gagging and spitting. I could feel a drool dripping down my chin and onto my chest.

At some point jared stopped me and pulled me up. My knees were so sore it hurt to relieve the pressure. I stood on wobbly heels as I felt my head spinning. Just this was already a dream come true. Then Jared kissed me. It was strange at first but it really did feel like fireworks, like everyone says. Jared broke the kiss and I just stood there in his arms, our foreheads touching.

"Jared, i...i....i want you to fuck me." I managed to stammer out.

Jared didn't say anything but he spun me around and pulled me tight against him as he kissed up and down my neck. I felt shivers running down my spine. I was in ecstasy trying to keep my knees from giving out on me as I heard noise around the room. Mark and Jason were clearing the floor and putting the single twin mattress down on the floor. Once it was in place, Jared pushed me onto it.

I yelped in surprise but chuckled when I hit the mattress. Pushing myself up with my arms I felt a mass straddle my butt and push me back down. Jared slapped his cock against my butt several times. My arms were tucked underneath me and I looked to one side as it dawned on me. I had an actual real man naked and real cock straddling me like a real girl.

I waved my hips around seductively and I felt a hard smack landing on one cheek and then the other. I yelped and moaned. I really moaned when I felt Jared pulling my fox tail. He tugged on it several times causing me to moan and grid my hard shell chastity cage into the thin mattress. When he really started to pull it out I froze and tried to relax. Eventually it popped out. I sighed into the mattress at the release pressure but then I felt something cold and wet dripping on my buttcrack. I raised up to look over my shoulder and saw Jared squeezing a bottle of lube over me and lathering his stiff pole of a cock. He looked at me and smiled devilishly.

I looked away as I felt his hand spread to my cheeks. I felt the head of his cock pressing into me. I can't believe this is happening! I'm about to reach the point of no return and I don't want to stop. It's finally happening. Oh fuck oh fuck! His cock is so big! Why did it have to be so big?! OH MY GOD!

Jared's cock entered into me and slowly plunged deeper and deeper into me. I hadn't realized I was holding my breath this whole time that I was actually starting to get light headed. It wasn't until Jared pressed down on top of me and he was deep inside of me that I exhaled. He just held there and let me grip his cock, I was pulsing uncontrollably. I felt his breath on the back of my neck and he began to nibble my ear. I moaned.

"Ive been wanting to fuck you for so long bitch," Jared whispered in my ear. "Im going to fuck you for the entirety of this trip, you are going to go home limping. I'm going to breed your ass so much you are going to think you actually are pregnant."

With one last hard bite he pushed himself up and pulled my hips with him so that I was on all fours. Never once did his cock leave my body. He pulled my hair back too hard. I really did think that it was going to come off. Then he started to pump into me. It hurt at first but as he began to pick up the pace, sawing in and out of me, I could feel the pleasure I desired.

"Oh yes jared! Fuck me! Fuck my ass!" I begged and moaned.

I had completely forgotten about the other too until one of them stuffed his cock into my mouth. I didnt really have to do anything to suck them but keep my mouth open since jared was fucking me so hard. It didn't take long though for one of them to get impatient and a new cock was stuffed into my mouth. I was helplessly rocking between a hard cock on both ends.

When the first of them began to cum I was not prepared. Just all of a sudden a torrent of semen erupted into the back of my throat. I gagged and coughed at first. Most of the cum flowed out of my mouth. Before I could even catalog that I had just taken my first cumshot another cock was stuffed into my mouth. Jared was pulsing between fast and hard and slow and deep thrusts.

I didn't even notice when my mouth was empty until I felt something wet hit my face. I moaned as I watched the cock in my face spray thick ropes of sticky cum all over my face. I really didn't know what to do. I had cum on my lips and cum dripping down my nose. This whole time I needed to keep both my hands firmly on the mattress because Jared was pounding so hard into me the whole time.

The salt on my tongue and my heavy panting was drying my mouth out. Every time I swallowed I tasted cum scratching down my throat. My tunnel vision and whirly mind was interrupted when I felt Jared's hand on the back of my head, clearly trying to point me in a certain direction. Once I blinked several times and focused, I saw something that instantly made me panic.

Mark was kneeling down to me and he had his phone pointing in my face, my cum covered flushed face.

"Are you filming this??" I questioned.

Jared smacked my ass before saying, "it's your audition, tell me who you are."

My head bouncing all over the place made everything blurry but I was able to look directly into the camera and in steely resolve I declared myself.

"Im jennifer and i love getting fucked in the ass by real men."

Jared leaned closer to hold my head tightly as he pressed his thick cock as deep as he could physically go. My mouth gapped and my eyes rolled back.

"I'm a dirty sissy cumslut and I serve cock. Please give me more cock!" I pleaded.

I moaned loudly as i Jared fucked me hard and fast and i heard him grunting. I knew what was going to happen. Jared was going to cum. He was going to cum inside of me. I was about to let another man cum inside of me like a real girl.

As Jared's shutters bucked into me I swear I could feel his hose of a cock spray his load in my insides. With his last spurt he plunged as deep as he could and we both just held there holding our breaths.

After several heartbeats we both relaxed and he shoved me off and I collapsed onto the mattress. I curled up into the fetal position and just painted like a bitch in heat. My asshole was gaping and spasming. Cum was already drying out my face.

I heard what could've been high fives slapping and then I heard the lock on the door being fiddled with.

"Don't you worry bitch, we'll make sure everyone knows you are open for business." Jared said as he swung open the door.

I felt the rush of cold air washing over my, apparently, sweaty form. While I was too exhausted to move I could see the flashing of pictures being taken. I guess this would be considered 'mission accomplished' except that this was only going to be the start.