The Barn

Story Info
A casual crossdresser gets more than he antcipated.
2.1k words
4.25
7.3k
6
0
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
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

After back and forth messages they had agreed to meet. Neither could host, both were married and horny.

He had agreed to dress as provocatively as possible under the circumstances- which was in an abandoned barn well off the main roads and he had never even known it existed though he had lived in the area for many years.

He pulled up at the dead ends road and noted a pickup truck already partially hidden in the shade just off the rutted track.

He proceeded to the barn and entered through the rear by squeezing under a loose board which he'd never have found without instruction. Once inside he saw a tall figure standing in the shadows with a small knapsack at his feet.

"Philly"? I asked.

"Yes Jana, get ready and let's get it on."

I told him to turn around and I stripped off my pants and shirt. I already had the pink mesh tube dress around my middle as well as the black thong and the inflatable butt plug was in place. The black thigh highs slid down a bit as my jeans came off but I pulled them back into place and put on my 3 inch black heels.. I was not a passable CD but I had a nice ass & legs and I enjoyed the feel plus he had requested it.

I said "ready "and he turned around and whistled.

"Wow" he said "turn around so that I can see that ass!" I did and heard him approach. He grabbed both my cheeks and squeezed, followed by a swat and he ran his hands up & down my thighs and reached around and tweaked my nipples hard.

Many barns had the remnants of mangers and poles running throughout to separate crops etc. This one had a short wall about 4 feet tall with a beam at the top. Scattered on the wooden plank floor were hoops of used baler twine.

He pushed me forward and bent me over the rail. He picked up a loop of twine and made a lasso knot over my right hand and stretched it out to the side along the rail and I heard the whine of a cordless drill as he screwed the twine to the top of the rail. He did the same with my left hand and I was stretched out. My mind was numb. I think they call it 'sub space.' I was waiting to be taken.

He lifted up the hem of the mesh dress and slid my thong down my legs and over my heels. The bulb of the inflatable plug hung between my legs and he squeezed it several times, expanding it to what I hoped was the limit. I danced a bit in my heels as the pressure stretched my rectum. I could not help but groan.

Then he looped a piece of twine over my left ankle pulled it far out to the side and I heard the drill, followed by my right foot stretched out and screwed down. Bondage really turned me on and if not for the cage I wore I would be long and hard. I was stretched out wide and helpless with my ass filled and pulsing. Totally at his mercy- I hoped I had not misjudged his character.

"OK slut, I am gonna fuck that ass that I've been dreaming about and if you don't like it that's too bad because your ass is mine now! I heard his belt unbuckle and heard his pants hit the wooden floor.

He came around the beam naked from the waist down and fed me his cock which I sucked with enthusiasm, he smelled clean and tasted good. I used my tongue and lips on him until he pulled out of me.

"I'll come in your face later, he said but I want a piece of that man pussy you've been showing off."

I had been sending him photos by email and he told me that he had printed them & jerked off on them.

I guess it was true. He moved behind me and I felt his fingers around the flange of the inflatable plug and he began to pull. I squealed and squirmed- it was too big inside to fit through my hole. He stopped part way and deflated the plug, then puled it out some more and then re-- inflated it while it was till partly in me, thus stretching my poor little hole to the max. He pushed it back in and then pulled it out to the widest part and left it there for a minute while he whacked my ass and pulled on my balls.

He abruptly yanked it out which made me scream- no other word for it.

He said "Relax bitch it's just like taking off a band aid" he inserted first one and then 2 fingers with lube on them and started to finger fuck me. God it felt good. A good thing I had coated the plug with desensitizing lube before I put it in me.

"Ok slut time to get what you came for". He lined up his hard cock with my hole and slid all the way in with one slow continuous thrust. I could feel the hair of his pubes in the crack of my ass and he began to thrust in and out while griping my thighs and calling me names. I didn't care, his cock felt hot and filled me nicely. I was glad that he wasn't too big.

Wait! Was he wearing a condom? He promised to wear a condom. I asked him if he was using one and he said " Damn, I knew I forgot something!" But he did not slow down and didn't take his cock out of me. I started to protest and tried to wiggle away but that was clearly impossible. He put his hands around my throat and squeezed. I understood the message and stopped trying to get away. In no time at all he was shooting come inside me.

He laid over my back while he rested and after some minutes he shrank out of me and I felt his come sliding down the inside of my thighs. He came around in front and told me to clean his cock off, which I did.

He went out of sight behind me and I felt him re insert the inflatable plug and pump it up to its full size inside my ass.

I heard rustling and eventually he walked in front of me fully dressed.

"Hey Philly, you've had your fun and gotten your rocks off now please let me go" I said.

"No can do slut of mine, I have an appointment in town. I am going to hide your truck deeper in the bush and then go to my meeting. " He managed to push a huge ball gag behind my teeth and buckled it tightly behind my head. My jaws were stretched to the limit.

He walked all around me taking pictures with his phone- something he had agreed not to do.

He slapped me once on each side of my face-hard. It snapped my head left and then right and stung before it started to burn and my eyes teared up..

"I'll be back in an hour or two you fucking faggot cum dump slut. Maybe I'll come alone and maybe I won't. Maybe I'll get delayed and won't be back until tomorrow. You can spend the night here alone unless I decide to post a bang gang party on a certain facebook page. Then you'll be happy to do anything to get released, won't you?"

He laughed and the last thing I saw was him wriggling through the loose board and then the sound of his cordless drill screwing the loose board back in place. Faintly in the distance I hear a truck engine start and fade away.

All the times I had fantasized about this happening came no where close to the fear I felt now. It was beginning to get cooler in the barn but that was not the cause of the chill that enveloped me. In spite of my plight I rested the side of my face on the beam in front of me and somehow dozed off.

I woke suddenly to sounds and the light of a Coleman lantern. I saw 'Philly squeeze through the barn board, followed by 3 other guys and a girl.

"Guess what Bitch, that gang bang you've been fantasizing about is going to happen!"

One of the men pulled out a pocket knife and cut off what remained of my clothes leaving only the nylons and my high heels. The woman climbed up on some pallets and started to record with her phone.

Philly got in front of me, removed the ball gag and shoved his cock in my mouth while someone behind me pulled out the plug, nearly tearing my ass wide open and immediately shoved his cock into me. The two of them set up a rhythm and fucked me hard from both ends. Tied spread open there was absolutely nothing I could do about it. I stood there and got spit roasted.

Neither of them took very long to come which was fine with me. I was already thinking ahead to what was going to happen with me when they were done.

The girl who was videoing the entire thing must have been getting horny because she climbed down and after dragging a bale of hay in front of me, climbed on it and dropped her pants. She spread her legs and ordered me to eat her. The angle was all wrong but I did the best I could while I felt another hard cock against my hole. It was of course bigger than the others I had had there but because of the stretching and lube it was not too bad. The girl decided I needed to hit some new spots with my tongue and turned her back to me and pushed her ass in my face. I licked everything I could reach because I knew what would happen if she was not satisfied. She reached behind and grabbed the back of my head and pulled my face deep into her. I could hardly breathe but I kept going while the fellow in back jack hammered into me and swatted my ass when he wasn't holding my thighs for extra leverage.

The girl in front tensed and came on my face while wriggling like crazy. I was soaking wet. Meanwhile my caged cock streamed pre come and then the guy in back rammed his cock into me right to the balls and came in long streams. He immediately pulled out and came around to have me lick him off.

The fourth man took his place and began a slow methodical fuck. All the way in and all the way out again and again. It felt like he was rubbing my hole raw. When he came he just stood still and pulsed inside me. Then he too came to my face for a cleaning, but before he did he put the inflatable plug back into me and squeezed it full.

They all sat on the bale in front of me and opened beers while I stood tied and panting in front of them.

"Hey guys I'd really like to come and my legs won't hold me up much longer. Can you release me now please."

"Well he did say please" said one guy "and it was a great fuck."

"I liked it too" said the girl. "Let's let him go."

Philly said " No I think we should leave him here and anytime one of us wants an ass fuck or a blow job we just come back and help ourselves. Or maybe rent him out- see how much cash we can make."

It turned out it was just teasing and they got dressed and left. Philly unscrewed one wrist and threw my keys in the hay in front of me.

"Thanks Jana, hell of a ride, eh? Be careful what you wish for. Hope those photos don't show up where they shouldn't!"

After they left it took me a good 20 minutes to get free, remove the plug and take off the cock cage. I was soaking wet. I squatted and pushed and the 4 loads of come squirted out of me on the floor. I wouldn't jerk off here- I still had to find the truck in the dark and get home.

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

Similar Stories

The Predicament A predicament that could lead to self destruction.in Transgender & Crossdressers
Down on the Farm Ch. 01 Nicole plans evening of self-bondage games in abandoned barn.in BDSM
Road Dog Boy is trapped by truck driver and turned into a sissy slave.in Erotic Horror
The Deal Freddy's wife convinces him to dress up and go clubbing.in Transgender & Crossdressers
Bookstore Bound Sub tgirl is bound & ring gagged, then left in a bookstore.in Transgender & Crossdressers
More Stories