Pretty Boy

"Aren't you a pretty boy?" He said with a leering grin.

I was on my second day of my new job and I had been tasked to drive the van to an industrial estate in the rougher end of town to collect some items and drop them off to the customer. I had walked through into the warehouse where I was confronted by a man in his late 40's with a strong accent, tattoos, a few days of stubble growth. He put down the box he was holding while maintaining an uncomfortable eye contact. I couldn't help but notice the was the muscles in his arms flexed and his massive, calloused hands...

"Errm I have this order to pick up." I stammered. Producing the order note from my pocket and walking toward him to hand it over. Regarding it he smiled another wicked smile and said,

"We don't do dildo's for your sissy arse here, pretty boy."

I was shocked, what had I just handed him? Had the guys at my new work set me up to look stupid?

He saw my look and leaned into me and in a lowered tone,

"I have plenty you would enjoy at my house though, pretty boy."

I blushed. Deeply.

I have known for a long time I was bi-sexual. I have enjoyed a finger or three rubbing my prostate. At the age of 22 I had bought a dildo for home use and although I had fooled around drunkenly with an older man, I had more experience with girls. I did know however, that I was well and truly a bottom. A submissive. And this man could somehow tell and had made me incredibly turned on.

He had walked off to collect my order and left my mind swimming.

"I've left it by you van pretty boy, I just need you to sign here."

I walked over to the desk and picked up the pen to sign my name.

"You would look so cute with you trousers and panties down, bent over my knee getting a good spanking. What do you think pretty boy?"

I found my voice. "Yes, Sir."

"SIR?!" He laughed "I knew it! Give me your phone number pretty boy and we'll see if we can have some fun. But bear in mind I have had quite a few pretty bitch boys leave my house in tears, so be sure."

I scribbled my number, felt brave and signed it "Your Pretty Boy" and drew a love heart. Handed it to him, he grinned and I left.

I couldn't concentrate for the rest of the day, perhaps because the blood was elsewhere. I kept checking my phone but no text came. That night I masturbated twice before bed imagining all the things this man was capable of. The next morning a Friday a text alert came through and read;

Pretty Boy come to mine tonight at 9pm. Sherebourne Road.

First make sure you are shaven all over, armpits, legs, balls. Wear your biggest buttplug, a Chastity cage and some sexy panties, if you don't have these items, there is a sex shop just off the high street. Don't disappoint me.

It is safe to say the rest of the day was a blur of arousal.

I got home from work and ran a bath, shaved and gave myself an enema. Left for the sex shop. It was a dreadfully seedy establishment in the rough end of town. Thankfully there was no-one else there and I picked out a large metal buttplug and the smallest cage I could find. Cock cages had always turned me on, as had crossdressing. Once back in my car I tried to put the cage on but could not get my dick soft enough. I sat there for nearly 20 mins looking at the clock, I was going to be late which surely meant a punishment, which made my dick hard. It was a vicious cycle. I managed to squeeze myself in. Let me just be clear here, I have a small dick but the cage I bought turned it into a nub. I hadn't bought any lube so I spat on the plug and worked that in, got into my panties and drove the 10 mins to the house. Heart in my mouth I knocked on the door.

He opened the door and turned and walked away.

"Strip, then follow me." He ordered.

I practically ripped my shirt and trousers off and followed him into his front room, leaving my clothes by the front door.

He sat on his sofa with a can of cheap larger smoking a rolled cigarette. The room needed a deep clean it was obvious he lived by himself and didn't mind some mess.

I stood and he regarded me, I saw that same evil smile flicker across is mouth.

"Give me the key to your little clit then turn, pull your panties to one side and spread your cheeks, good, pretty boy I see you can follow instructions."

He stood and grabbed me roughly, turned me around to face him, held my wrists and cuffed them. Not with your classic bedroom bondage plastic fluffy cuffs, these seemed like police issue. Grabbing my hair he pulled me over his lap. With out any warning he started spanking. Hard. His strong hand rising and falling on my bubble bum. I cried out after 10. He increased his strong grip and I realised that even if I want to get away I would not be able to. I was being over powered and now being used. I loved it. My dick in its little cage loved it.

He pushed my off his lap and I fell on to the dirty floor, gasping. Ass stinging. He placed his foot on my balls and pushed down.

"Who owns this now?"

"You do."

"You do what..." he said pressing harder

"You do Sir." I squealed trying my hardest to stay still while he crushed my balls against the cage.

"Take my socks off with you mouth pretty boy."

I complied.

"I haven't washed these in a while." he laughed and I could taste his sweaty feet. He took his socks and rammed them into my mouth then used a roll of duct tape applied a long strip all the way round my head. He grabbed my by the hair again and pulled me back over his lap but this time he spanked me with a leather belt. It was the most intense pain I have ever felt and I realised later he was drawing blood. This time I did try and get away but he held me down a laughed and moved his whipping to more sensitive areas down the back of my legs.

He rolled me over so I was on my back across his strong legs and unlocked my cage. Stroking me he bought me to the edge then slapped my balls with the back of his hand. My little dick was leaking pre-cum and the head of my penis was incredibly sensitive, as he slapped my balls again I tried to get free but he just smacked me again.

"Stay still now pretty boy." As I looked up at him laying on his lap. He started wanking me again using his thumb on the head of my dick.

"Look at this little cock of yours, I bet you don't please many people with this worthless thing." I nearly came but he pulled his hand back and slapped a large open hand on my balls. He laughed and rolled me back onto my front, reached between my legs pulling my sore balls down with one hand and spanking them with the other.

I had stopped resisting and tears had formed in my eyes when he stopped, rubbing his rough hands over my beaten bottom. He started playing with plug before ripping it out of me then forcing it back in, I regretted not lubing myself up before hand.

"mmm I told you to get the largest plug, this is tiny... in comparison to what will be in there soon."

He stood and I rolled off his lap onto the floor he picked up a chain and a pad lock and attached the cuffs to something behind the sofa so that I was on my knees with the sofa under my chest and arms pulled infront and above me making moving very painful for my shoulders and my red ass exposed.

I was then blindfolded and he put some large headphones over my ears playing some heavy metal. Duct tape was the wrapped around my head to secure these. Deaf and blind I felt completely exposed but christ did my dick love it. It felt like 30 minutes passed before I was aware of him again.

I felt a probing finger inside me and found my prostate which felt the size of a basketball. Intense feelings ran through my body as I tried to move my body onto his finger but as soon as I started it finished and was replaced by a much much larger object. My hole was being stretched and I felt it burning as the object was slowly moved in. I was then fucked with it, rough and hard I was screaming with the pain and pleasure into the gag. I was roughly tugged and came within 2 minuets, it was the most powerfully orgasm I've ever had shooting cum all over the floor, but it didn't stop. The assault on my ass was harder if anything and the rough calloused hand kept stroking my dick as it tried to go limp. I was wriggling trying to get away from the torture but it was no use.

Soon enough my dick was hard again and the dildo was removed, it was strange it hurt while it was in but I felt empty without it and craved to be filled again. The duct tape was removed in one painful rip from my head and the headphones and blindfold removed. It was then I saw the two other men in the room stoking their rock hard erections and laughing at my expression.

Not only was this the most humiliating this I had ever done but now I find that I had be entertainment for other men, I then saw the camera with a red light indicating it was recording.

"Now we've broken you. We're going to fuck you." my original tormentor said. The rest of the duct tape was removed and the socks taken from my mouth. The chain was released I and was dragged across the room towards the two men. I had no fight left, my mouth was dry, my ass was on fire and my cock was hard. I could smell the sweat and the arousal of the three men using me. The guy on the left took me by my hair and pushed his average sized dick into my mouth and down my throat. I was broken, he was right, because I didn't everything I could to satisfy this stranger.

"Woah, look at him go, you got a good one here Smithy." he gasped.

The other man, with the larger member had moved behind me and started fucking my abused hole. My hole was open to the penetration and I was grateful for the large dildo that had been in there before, as this man slammed into me. I could feel his length pressing against my prostate and bladder. He would then pull out all the way to admire the gape he made, spit into it, then force his whole length back in.

I moaned with the pleasure, and opened my throat to take the man at my front deeper. Feeling this pubic hair on my nose. Trying to use my tongue on the head of his throbbing cock, although he was roughly face-fucking me, I found his rhythm. I felt the belt again on my ass and back and was taken into a deep state of submission and joy. They swapped placed and I sucked the dick that had just been in my ass. The taste and the smell of my submission filled my senses. I could not get enough. He controlled my head with my hair and came in my mouth the a grunt. Salty delicious cum ran out of my mouth and I used my tongue on the head of his penis.

It was soon replaced my my Sirs dick, he slapped my face while face-fucking me as the guy at my ass finished deep inside me.

Sir picked me up by my hair and pushed me onto my back on the sofa. He started fucking me in my cummy asshole while stroking my dick roughly. I came for the second time the night within moments and my asshole clenching on his dick as he fucked me. Again he didn't stop wanking me off and I was begging for a break. He finally gave me the all of his seed in my ass. We locked eyes as he came and I felt strong feelings of lust in my chest.

Once again he dragged me by my hair, my legs where not working and took me outside to the garden, they took in turns pissing on me laughing as they did. Sir held me by my hair told me to keep my mouth open and swallow as much as possible. They then left me on the floor, went inside and locked the door. I led on the floor thinking of escape, but I couldn't just walk out of his back garden gate naked, covered in piss and cum could I? So I stayed and tried to stay warm.

I couldn't tell how much time had passed, I think I fell asleep when Sir came out and picked me up in his strong arms. My whole body hurt and I gave myself into him leaning my head against his chest. He took me upstairs and placed my gently into a warm bath and washed me. After I was still in a daze he dressed me in one of his t-shirts and put me into his bed where I slept.

Morning light spilled through the curtains.

"Aren't you a Pretty Boy." He said looking at me from his pillow.