An English Boy Gets Turned Out Ch. 03

Mr Tobias picked up a bottle of lube. He poured a little on to his fingers and with his other hand he pulled my ass cheeks apart. "Oh how cute a little virgin ass hole. Have you ever played with ass before? Have you ever put a finger in your ass?"

"No of course not, that's disgusting. My bottom is one way traffic. My big jobs (For some reason I was using the word for shit that I used at the same age I was using willy.) come out of there."

Mr Tobias just smiled. He moved his hand to my crack and very gently he started to caress the inside of my buttocks. His fingers moved effortlessly over my skin thanks to the lube. Before this moment the only thing that had been this close to my anus was loo paper. His fingers got closer and closer to my bottom hole until finally his index finger was slowly rubbing around my rosebud.

"You like that don't you Sammi?" I groaned in response.

"Sammi you know how to answer questions. You like me playing with your ass don't you?"

"Yes your finger feels really good Sir."

"Where does my finger feel good Sammi?"

I hesitated to respond because this was really gay. As gay as it can possibly be. "Your finger feels good on my bottom, Sir"

All the time Mr Tobias was still moving his finger slowly round and round my virgin hole. He was so gentle I did not notice when he increased the pressure his finger was exerting. Before I knew it his finger was no longer just going round and round but was beginning to penetrate my ass hole. Not much just a few millimetres.

Slowly he continued until his finger stopped going round and round and now it was just slipping into my hole. The slow caressing and the lube had loosened me up and the finger slipped in with no resistance.

When I realised what had happened I tried to move away and jerked my ass. His finger slipped out. It was not really a conscious decision on my part it was just a natural reaction. Whack I was jolted as the same hand that had been so gently caressing my ass swung down and gave me a really hard slap on my buttocks. I grunted in surprise.

In a stern tone Mr Tobias said. "Never move my hand from your ass. You are a submissive little bottom. You do not have the right or even the will to move away. If I want to play with your ass you are going to let me."

"Stand up!" I did so and I moved to pull up the shorts which were halfway down my thighs. "Leave them there. Pick up the smaller Trainer plug and bring it back to me."

I did as I was told though I wasn't very elegant as it was hard walking with the shorts around my thighs. It was even worse as I walked back as the shorts started to fall down my legs. I tripped as I reached the sofa and landed in a heap.

"Your little willy was enjoying my ass play. You are still rock hard. Don't deny it Sammi. We have been through this. Your mind might lie to you but when it comes to sex your dick never lies. Look how hard it is. You've just had a man playing with your anus and it's hard. Your holding a big ass toy and you're still hard. Sammi you are gay, you are a little submissive bottom. Your cock knows this and as you work here your head will know it too."

"Lie back on the sofa. Put your ass on the edge. Give me the rubber toy and start playing with your little boy's willy."

I handed the large rubber toy to Mr Tobias and started playing with myself. My willy had not softened at all and it was leaking pre-cum. I smeared it all over my cock.

"Sammi you got one question wrong this morning. You know what that means don't you, you are going to take the first knob of this toy in your ass."

"You said you were going to give me a break today."

His brow furrowed and he looked angry, his fingers went straight for my aching nipple and squeezed it. "You will always address me a Sir! Don't forget it." He pulled the nipple away from my chest and stretched it by about an inch. "I said I would give you a break and not test you any more today. I said nothing about forgoing your punishment for giving the wrong answer to the single question I asked you this morning. Don't question me anymore or you'll take this baby with no lube." To emphasis his point he pushed the dildo against my anus and pushed. It felt like a fucking baseball bat was assaulting my ass hole. Excuse my language but it hurt.

"Ask me to push the first knob into your ass as we agreed this morning."

He was still holding the toy hard against me. There was no way I was going to disagree with Mr Tobias.

"Please sir please penetrate my bottom with the first bobble."

He smiled and paradoxically he eased up on the dildo.

"Good boy Sammi. Do you still think you are not gay? Lying back with a stiff dick asking another man to push a dildo up your ass. It does not get any gayer than that. Carry on playing with yourself but don't cum until I tell you."

My hand went back to stroking my cock.

Mr Tobias' hand went back to playing with my ass. He lubed it up again and this time when he slipped his finger inside me I remained still. He started to push it in and out, and twisting it around putting pressure on my sphincter to loosen its tight grip. It felt weird having something inside me but there was no pain.

He added a second finger and I could feel the stretch as both digits entered me. With two fingers he was able to spread my ass from inside. I could feel my hole stretch as he spread his fingers and twisted them around. He was loosening me up nicely I hardly felt the difference when a third finger entered me.

He chose this moment to press my prostate. I gasped the feeling was so unexpected, It made my ass tingle, it made my cock tingle and it forced more precum out of my leaking penis.

"Sammi you're a natural. Look at that your ass is swallowing my fingers. You are a bottom and no mistake." He moved the toy up beside my taily. "Put some of your pre-cum on the toy. That's it spread it around. Can you feel how big that feels in your hand. Imagine that's going up your ass." He spread his fingers wide as he said the last part and I could feel my sphincter giving way as it was eased open.

He moved the toy up to my face. "Lick it taste your pre—cum. Use lots of saliva. The more you wet it' the easier it's going to slip unto your ass."

I licked the toy. The strongest taste was rubber but underneath I could taste something musky which I assume was my emission. I had never tasted my cum or pre-cum when I wanked so it was an unknown flavour.

He removed his fingers from ass and the toy from my face. He poured some lube directly on the toy and spread it around the rubber plug. He then poured some lube directly on my ass and used the same hand to smear it around my hole and then his fingers to lube my insides.

"Keep playing with yourself. You are about to have the most amazing orgasm of your life my little bottom buddy." He used both hands as he lined the dildo up with my hole. I felt the tip of the toy grazing my rosebud. This time when he pushed the tip of the plug against my ass hole it entered part way. I could feel it spreading my hole wider than ever before. Then slowly he pulled it back out, Mr Tobias spread a little more lube around my hole and replaced the plug with his fingers. He was intent on opening me up but he wanted to do it with as little pain as possible.

When he was satisfied there was enough lube and my hole was open he pushed the plug back in, it entered a little further than before and he released the pressure and eased it out. He pushed it back in forcing the round bulb up my tight little anus. He pulled it back out and then repeated this piston motion steadily. With each inward thrust my hole was expanding and little by little more of this enormous tool was entering my body.

My ass was virgin territory until this moment. Never before had anything entered it. It had been an exit only. I could feel the plug entering me, I could feel it stretching my sphincter which under Mr Tobias' ministrations had become quite elastic. The feeling was intense as the pressure needed to force the tool into my ass was high.

Mr Tobias was talking to me continuously. "Keep playing with yourself... Enjoy the feeling as you open your ass... It will become the focus of all your pleasure... Remember this moment because you can say good bye to a tight little ass hole... This hole is made for big cocks..."

My mind was in a whirl. I could feel my little dick was getting ready to spurt, I was more excited sexually than I had ever been. Suddenly I yelled out as Mr Tobias gave a heavy push and the first bulb was in my ass.

"Well done boy. Look at you with a big cock up your ass for the first time. Stop playing! I don't want you to come just yet. Take hold of the toy and hold it in place we need to take a picture of this moment. You need to be able to see the first time you became a submissive little bottom."

He stood up and got my phone and started to take pictures of this object half inside my ass and half protruding obscenely from it. "You're a sexy boy. Look at what you're doing to me." He unfastened his trousers and pulled them down. His big fat cock sprung up from between his legs. As I was to learn Mr Tobias always went commando. I had seen it before but seeing it as it thrust out from his body mesmerised me. My eyes were locked on it and without me realising he took pictures of me staring at his crotch.

He sat down beside me once again. He took my left hand and placed it on his cock. He then poured lube over my hand and his cock. With his other hand he started to move mine up and down his enormous member. The cock was smooth but it felt uneven as my hand rose and fell along its length. I could feel the ridges and veins under his soft skin.

My hand continued to move of its own accord and he started to play with the dildo in my ass. He twisted it around and he pushed it in slightly and then pulled it out a little so the widest part of the first bubble was really stretching my hole. I was loving all these sensations and it felt right, my inhibitions had fled and I had become a sexual being for the first time in my life.

"Sammi start playing with your cock, make yourself cum." Mr Tobias whispered in my ear.

"Wank your little dick, feel your ass stretching wider by the second."

My right hand was racing up and down my little cock and my left hand was steadily waning the giant pole of Mr Tobias. The contrast between the two cocks could not have been greater. My little boy dick and Mr Tobias' giant man's cock. The difference made me feel inferior and humiliated but the humiliation turned me on all the more.

Mr Tobias was watching me carefully. He was thrusting the first ripple of the plug in and out of my ass. He was removing it totally and forcing it back into my slackening hole. I was being fucked for the first time.

The sensations from my ass, Mr Tobias' cock and my willy were all combining to send me over the edge. I started to groan and the first spurt of semen shot from my dick. At that moment Mr Tobias thrust the dildo hard up my ass to force the second bubble inside me. My sphincter was clenching tight as I came but the rippled plug bust it wide open.

I came and came. Normally I have a weak spurt and a dribble but this time I had 6 spurts each one a little weaker than the one before. The first hit me on the chin the last made it to my belly button and in between my belly and chest were covered in spunk.

Mr Tobias got up once again to take more pictures of my just fucked look. The toy was wedged firmly in my ass and was not going to be dislodged easily. I was breathing heavily and slowly I recovered and gathered my wits. As I came down from the sexual high my inhibitions returned. I could not believe what had just happened. I could not believe I had let Mr Tobias fuck me with a rubber plug and even worse I had enjoyed it. I groaned with shame.

Just seconds before I had felt on top of the world but as reality set in I was disgusted with myself and angry with Mr Tobias for taking advantage of me.

I reached down, grabbed hold of the base of the plug and pulled it out of my ass in one hard pull. I screamed as the widest part stretched my ass hole and without the sexual high the pain was acute.

I stood up and pulled up my girly shorts. I looked around looking for something to wipe myself with. "Have you got any tissues?" I asked Mr Tobias.

"Sammi use your fingers to clean yourself."

"But I will need something to wipe my fingers with."

"Sammi scoop up the come with your fingers and clean your fingers with your mouth. That's how submissive little bottoms clean up come."

What a disgusting thought. I've never touched my own cum let alone tasted it. I stood still as I continued to look around for a cloth or a towel to clean up the mess.

Mr Tobias was not having any of it he walked over to me. He used his own fingers to scoop up some cum. He pressed his fingers to my mouth and forced them inside. "Suck them clean little boy."

The fingers were already in my mouth so it seemed simple to suck them. Cum tasted ok. It did not have a strong taste, just a hint of salt. But the texture was pretty disgusting. Slimy like a disgusting sago pudding. Mr Tobias' fingers were hard at work and were moving swiftly from my chest to my mouth and back again. Each time they deposited more spunk for me to clean.

"Swallow Sammi!"

I did so and I nearly gagged as the slimy substance went down my throat and met the shame rising up my gullet.

I looked around for my clothes but I could not see them.

"Sit down Sammi." Mr Tobias poured me another shot of whiskey. "In time you will love the taste of cum but tonight you can wash it away with some good Scottish whiskey."

He brought over another glass of whiskey, that made it 5 for the shift and I drunk. But after the evening I'd had I needed something to lessen the guilt and the shame I was feeling. He pulled out my phone and started to show me the pictures he had taken. My willy had softened a little after my orgasm but as I looked at the pictures of me it got rock hard again.

"Your little dick knows you are gay Sammi. You are looking at some real gay porno pictures of yourself and you get a hardon less than 5 minutes after you've just cum. You already know you are a faggot but I understand it will take some time for you to admit to yourself. Three shifts and three orgasms from working in a gay store."

"Just wait a moment I will get you your pay for the last three shifts."

He sat down at his desk, he tapped at his keyboard and looked at the computer screen. He then took out a cash box and gave me $100. That was a lot more than I was expecting.

Mr Tobias said "It pays well this job. It's not bad when you get to play with yourself and I still pay you. You are the highest paid wanker on campus."

I blushed. "Where are my clothes Sir?"

"I've arranged for a new outfit for you Sammi." He reached behind him and pulled up a small bag.

He passed it across his desk. Inside were a pair of shorts and crop top. The shorts were a pastel blue and the top was a pastel pink. Both were very girly.

"You'll need to take your panty shorts off you don't want to have a visible panty line under your clothes.

I knew better than to argue. I also knew I would never get any other clothes.

I tuned my back on Mr Tobias and took my shorts off. I could hear him laughing. I guess it was pretty stupid as he had seen me naked covered in cum and he had been playing with my ass hole. As I said my inhibitions had returned.

I put on the shorts first and the material was very clingy. My little willy was outlined clearly by the material. It was obvious I was aroused. You could clearly see one nipple through the material. The top ended midway down my chest. My belly button was on display to the world.

"Sammi, you can have the weekend off. I will see you at the usual time on Monday. You can expect to work a full shift so don't expect to leave here before midnight." He gave me another USB. "Remember to watch both videos and you will get tested on Monday when you get in. Having said that I think you enjoyed the punishment for getting the answers wrong."

I put my money in my back pack and left the office. I climbed on my bike and winced as my bottom touched the saddle. Even though Mr Tobias had been gentle with me, my ass was still sore.

Mr Tobias was feeling very pleased with himself. He knew he had great video from this afternoon and the website was going to be buzzing over the weekend. He would talk to Mike on Monday morning to discuss what they would do to Sammi next week.

He had not come with Sammi and was in need of relief. He picked up the phone and spoke to Tony. "Is Jamie around this evening?"

"No Mr Tobias you gave him a few days off, you didn't want him to scare Sam."

"Who is in the video arcade? I need to get my cock sucked urgently. Sammi left me high and dry."

"There's a young lad in booth 2. He's been here before and he likes to get on his knees for a big cock."

"Thanks Tony." Mr Tobias stood and walked into the store and then video arcade.