An English Boy Gets Turned Out Ch. 02

Story Info
Sam's gay book store training continues.
14.1k words
4.64
57.9k
59

Part 2 of the 6 part series

Updated 06/08/2023
Created 12/12/2016
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
RustyRover
RustyRover
181 Followers

Sam woke up the next morning with his usual morning hard on. As he put his hand on his erection yesterday's events suddenly leapt to the forefront of his mind. He felt himself blushing as he was submerged with a wave of humiliation. He remembered he was going to be working in a gay porn shop for the foreseeable future, he remembered picking up an enormous dildo, but worst of all he remembered watching the video in Mr Tobias' office and another man playing with his penis and making him cum.

He shot out of bed muttering to himself "I am not gay. I'm not a pooftah."

Luckily he was alone, his roommate had not come back last night. He decided he was going to prove he was not gay. He went to his laptop and went to his favourite porn site. It featured older women bossing younger men and telling them how to bring the older women pleasure. He liked to tell himself he liked this site because it was educational and he would have a better knowledge of how to please a girl when the opportunity arose. But deep down he knew he liked this particular site because he was submissive.

Anyway he went to his favourite scene and started to watch. He became erect instantly and it featured a woman having sex with a boy. Phew he was not gay. He felt he had something to prove and he whacked off harder and quicker than normal.

Afterwards he cleaned up and showered. Relieved he was a normal heterosexual male.

He had a lecture at 10 and then went to the library for an hour or so. Had some lunch with a class mate and then went back to his dorm to chill out.

He did not want to go back to the store tonight and see Mr Tobias. But he knew he had to. He was worried by the connection between Mr Tobias and the Dean of his college. But he decided he had to make it clear he was not gay, he was not going to take part in any more sexual activities in the store.

He then remembered how he had been hard all the time in the shop. Time was running out but he had an idea. He would have another wank now, so he would not be hard when he went to work. There was no time to set up his laptop so he started using one of his favourite fantasies. This dark haired 40 year old woman was telling him to crawl towards her and worship her pussy with his mouth and tongue. His hand was working furiously on his little dick and he felt himself getting closer to orgasm. Just as he shot his load he thought of Mr Tobias' hand stroking his cock.

Ugh! Why did I think about that disgusting man as I was coming? Did it mean I liked him touching me? Did it mean I was gay? No of course not I started to rationalise, it was my fantasy of the older woman that turned me on and got me excited and Mr Tobias' hand job only came to mind because I had worried about it all day. Having reached a conclusion, I quickly got dressed. I wore the same clothes as yesterday and thought I won't get a hard on this evening, so it won't matter what I am wearing. I climbed on to my bike and rode without enthusiasm to my job. As I rode I fantasised that I was riding to a proper book shop and I could talk to the customers about the latest New York Times best seller, or whether Shakespeare was a sexist or a feminist?

I arrived at work and went straight to Mr Tobias's office. He was seated behind his desk and waved me in.

"Good to see you Sam. I'm very glad we haven't scared you off and you've come back for more fun at the store. Did you enjoy yourself last night?"

I'm quite clever and you would have thought I would have prepared an answer for such a question. It was obvious he would ask it. But I hadn't. All I managed to say was "I'm not gay."

"Sam, I know you enjoyed it. I've got your pictures to prove it."

"You said you would delete them."

"I am going to show them to you in a minute and you can delete them yourself. First I'm going to give myself a whiskey as it's after 5 and I don't like drinking by myself so I'm going to give you one too,"

With that he stood up and turned away. I could hear him pouring the drinks but could not see it.

Mr Tobias grinned to himself as he stirred in some blue powder into Sam's drink. He thought that psychiatrist, Pavlov, was right. Ring a bell when you give a dog a bone and the dog will always think it's going to eat a bone when he hears the bell. Give a boy a boner every time he goes into a gay shop he's going to think he's gay and he's going to want to suck on a bone.

Yesterday had gone well, Sam had his first orgasm at the hands of another man and he had come back for more. In his conscious mind he might not think so but the Pavlovian reaction was already working and in his subconscious Sam knew he was going to get another orgasm today.

Mr Tobias handed me my drink, I took a sip and did not grimace today. He sat beside me on the sofa and handed me his phone. "Have a look at the pictures and tell me you were not in post orgasmic heaven. When you've had a good look delete them off the phone, understand I keep my word." Mr Tobias smiled to himself as he said that knowing he had HD video of the whole session. He did not need the pictures on the phone.

He picked up the office phone and I heard him say. "Tony, Sam is wearing the same clothes as yesterday. Can you dig out something more appropriate? PAUSE. Yes something that won't scare the customers away. PAUSE... No I don't think Sam would feel comfortable in shorts. PAUSE.... Yes perfect, I'll send him out in about 5 minutes to get them."

He turned to me. "I told you yesterday you could not wear those clothes again in my store. Tony is going to get you something more appropriate to wear."

I stood up to go and get them. "No rush, give Tony a chance to get them. Actually what size are you?"

I sat back down and said I am small to medium in most things.

"I can see that." Mr Tobias asked me a few more questions about the uni all the while encouraging me to drink my whiskey. He wanted to delay Sam in his office for about 10 minutes so that when he was looking at the pictures on his phone or putting on the new clothes his hard on would kick in.

After a few minutes he told me to go to Tony and pick up the clothes and come back to the office.

Sam went out into the store over to the cashier's desk. Tony was all smiles as he said Hi and handed me over a small package in a brown bag. "Tell Mr Tobias if he doesn't like the colour I can change it or if the clothes don't fit I can get another size."

Sam just nodded and went back to the office. Mr Tobias held out his hand and he gave him the package.

"Pale blue." He said as he handed me some pale blue fabric. I held it up and saw a very small pale blue stretchy shirt. He then reached into the bag and pulled out some matching yoga trousers.

"I think you'll look good in those. Get changed."

I looked around wondering where he expected me to get changed.

"Hurry up! You're on the clock. Just get changed over there." Pointing to the middle of the room.

I hesitated, I did not want to get changed in front of him.

He raised his voice. "Sam, don't be so stupid. I have already seen your little dick, you've got nothing to hide. It's not as if I don't see a hundred cocks a day and they are all bigger than yours. So get changed before I lose my temper."

My face was burning with humiliation. I walked over to the centre of the room. I took off my shirt and tie. I picked up the stretchy shirt and slid it over my head, as I pulled it down my chest and put my arms in the sleeves I could feel it clinging to me. I pulled it down and it reached just below my navel. As I looked at myself it seemed as if my skin had turned blue. Every contour of my body was on display.

I turned my back to Mr Tobias and pulled down my trousers. I left on my boxer shorts and stepped in to the yoga pants. I pulled them up and turned to face Mr Tobias. He was busy looking at his computer and it took a while for him to notice I was changed.

"Turn round! I want to get a look at you and make sure you are displaying our clothes in the best way."

I got half way round and I heard him laughing. "You've got a bad case of visible panty line. You need to take off your underwear."

I turned to face him. "I always wear boxers. Haven't you got something else I can wear?"

"Sam! You need to read your contract. It clearly states you will be required to wear a uniform as needed by me and in addition you may at times be asked to model and or demonstrate any item we sell in this store." I wanted to complain that as yet I had not had a proper look at my contract. Instead I just looked at the floor and kept quiet.

He continued in a quieter tone "If you really want to wear underwear, I'll get Tony to bring you some that won't show under your pants."

He picked up the phone and called Tony. When he finished speaking he told me to strip and to stop wasting time.

I slipped down the yoga pants and stepped out of my boxers. I was now naked except for a skin tight pale blue lycra top. Everything below my waste was on display. I put my hands in front of my privates trying to hide as much as I could.

Just then Tony walked into the room. He went straight to Mr Tobias and handed him something.

Mr Tobias laughed and said perfect.

Sam come here and get your underwear. I walked over to the desk keeping my hands in front. Tony was staring at me. I was so embarrassed to be bare-assed in front of 2 men, 2 men I worked for.

I reached over and Mr Tobias handed me the merest scrap of material. It was pink and tiny.

"That's a thong. They won't show under your yoga pants and leave your cute little ass on display."

"I can't wear these, they are for girls." I replied.

"Boy, you are beginning to piss me off. Every time we tell you to do something you complain and argue. Now just put them on before I lose my temper and punish you. You won't like that."

The situation reminded me of a favourite video that turned me on. The older woman ordered the boy to put on girl panties just like these and it always gave me an erection. But that was a woman and this was a man and I didn't have an erection.

I reached out and took the thong. I moved back to the centre of the room and stepped into it. When I pulled it up over my dick I noticed it had a small bow on the front. It felt strange as the rear fabric pulled right up my ass crack. I could feel it resting on my anus.

Horror of horrors. I could feel my cock beginning to get hard. How the fuck could that happen? I had wanked less than hour ago and here I was half naked in front of 2 men wearing girl's knickers getting a hard on.

I quickly reached down and pulled up the yoga pants, hoping they would help to hide my growing penis from the eyes of Mr Tobias and Tony.

I was barefoot and Mr Tobias asked Tony to get me some suitable shoes.

He then turned to me and said. "Sit down on the sofa. Let's look at the pictures from yesterday and then you can delete them."

I sat down and Mr Tobias joined me on the sofa, he was sitting up close. I was very aware this was how we were sitting when he game a hand job.

He lifted up his phone and pulled up the pictures. There I was lying in a post orgasmic haze. There was spunk all over me from around my zip, up my shirt and even on my face.

He held the phone towards me. "Delete it." I did so and the next one appeared it showed the same thing but from a different angle.

Just then Tony came in holding a pair of pale blue sneakers. "Tony, look at the straight boy enjoying some gay fun. Doesn't he look as if he had a good time at the hands of another man?"

He walked around and Mr Tobias handed the phone to Tony. He smirked as he looked at the picture. "He sure looks good covered in come. He would look even better if he had more"

Mr Tobias replied. "We'll see if he wants to play again after his shift."

Tony was staring at my crotch. "He definitely will, he's getting turned on just looking at those pictures, or it might be, he's excited by wearing girl's panties. But he's got an erection again."

"Oh yes, so he has. It's a little hard to see. Even with tight clothes his penis is so small it's hard to see when erect." Said Mr Tobias.

These 2 men talking about me and my small dick was embarrassing me. But at the same time my penis was not showing any signs of softening. If anything this talk was making it harder.

Mr Tobias was feeling very pleased with himself. He had got the timing with the Viagra just right. It was perfect that Sam got an erection just as he put on the thong.

"Look at the little boy. He has put on a girly thong and he gets hard. Despite all his protestations about Pooftahs and their unspeakable acts, he is definitely a faggot. I think he's going to turn out to be a sissy boi. Are you a sissy, Boi?" He asked.

I kept looking at the floor and did not answer him.

"Well Tony he's not denying it so let's all agree he's a sissy boi. In the next couple of days we'll need to dig out some more clothes that a sissy will feel comfortable in."

I wanted to tell them to shut up. I wanted to shout I'm not a sissy. But I was struck dumb. My mind was still processing that I am standing here in skin tight clothes, a girl's thong and an erection.

"Sam, stand up and come over here. I'm going to take some pictures so you can see what you look like. Tony, I think I need to get a mirror in here so Sami can use it when he wants to dress up." With that he held up his phone and started clicking away.

"Turn to the side. Now let's get a view of your butt in a thong and yoga pants. That's perfect. Face me again." I don't know why but I followed his instructions without question. It was as if I had lost all control, but at the same time I felt what I was doing was wrong, perverted and disgusting. Trying to reconcile all these emotions was doing my head in and leaving me confused. Every time I thought, no I'm a man I would remember Mr Tobias saying the cock does not lie. And there was my little dick standing up proudly saying I'm a sissy. Looking back at it, I think this confusion was what made it so easy to manipulate me.

When he finished he sat down again and asked me to sit beside him. "Here have a look at yourself and tell me you're a real man." He laughed as he handed me the phone.

I burnt with humiliation when I looked at the pictures. There was a small boy in skin tight clothes. He had no muscle, he was short, he was skinny and he definitely had a small erection. From behind it was even worse because my butt looked kind of full and feminine. One thing for sure, my butt was smooth and there was no sign of underwear. That was definitely not a man's ass.

"Now you've seen them you can delete them. I know you don't want these pictures getting out." I did as he suggested and deleted all the pics.

"Sam, I hope you are beginning to trust me a little bit. I'm letting you delete the pics after you have seen them. I want you to see how others see you. With the best will in the world you don't look like a man, at best you look like a little boy but today you look like a sissy boy."

At that I finally spoke. "I am only looking like a sissy because you are making me wear these girly clothes. When I wear my normal clothes I look fine."

"Sam you only have yourself to blame. I told you to wear something more suitable for the store and you turned up in the same middle aged clothes as yesterday. I would also say it's not the clothes that make you look like a sissy but the little boy inside them. Tony go and put on the same clothes and show Sam how a real man looks."

Tony walked out of the office. Mr Tobias took the opportunity to refill our glasses. He handed my second whiskey of the afternoon I started to feel a bit fuzzy around the edges.

"Today Sam you are going to have the same training as yesterday. Once we have compared your manliness to Tony you'll join him out on the shop floor. He'll show you some more stock and let you look around the store. I also want you to start interacting with the customers. Remember the saying, the customer is always right. So if a customer asks you to do something you need to do it. I won't be happy if I hear complaints and you'll be punished."

"What do you mean Punished?" I asked in a quivering, slightly slurred voice.

"I'll make sure Tony teaches you about our stock items designed to cause pain. So you'll know what to expect."

"You can't do that it's against the law to hurt people."

"Sam you're right of course, it is normally against the law to hurt someone. But if someone gives their consent then it's perfectly acceptable and legal. If someone signed a contract that had a whole section agreeing that their boss was allowed to punish them, then the punishments will be within the law."

I could see where this was going. I felt my face burning and I realised I had probably signed such a contract. Oddly my dick stayed stubbornly hard. What was wrong with me? My boss was talking about hurting me and my cock was excited.

"I see you already understand." Mr Tobias reached down to his drawer and took out a folder. He pulled out some papers and turned the relevant page towards me. "Here's your contract." I could see the words ACCEPTABLE PUNISHMENTS. Mr Tobias moved his finger to my initials at the bottom of the page.

"There we have it Sam. You have already consented that I can punish you in a variety of ways. As I told you before you need to read a contract before signing it. I'm sure this is a lesson that will hold you in good stead in the future. Don't even think about saying you were rushed into signing it. You signed it and that's all that matters."

Just then Tony walked back into the room, wearing the identical clothes. More accurately he strode masterfully into the office. He seemed taller than before. I could see every muscle on his body was outlined. His chest, his abs, his biceps were all straining the fabric to breaking point. His six pack was fully on display. There was no mistaking him for a sissy.

I looked lower and his cock and balls were totally on display in the yoga pants. The cock though soft looked bigger than mine. It was thrust forward by the big set of balls below it. I did not know it at the time but he had a bit of help from cock ring which pushed everything to the front.

"Go and stand next to Tony!" Mr Tobias commanded.

I stood up and slowly made my way beside him. No one said anything, they didn't need to. I felt small and puny beside him.

Mr Tobias stood up and started taking some pictures with his phone.

"Tony show some muscle."

Tony struck a body builder pose and curled his right bicep.

"Sam you do the same."

I didn't move.

"Sam you don't want me to punish you before you start work. Now copy Tony's pose."

I tried but even as I did it I knew I just looked stupid. Where Tony's bicep bulged under the stretchy lycra, mine just stayed flat.

The phone was still in Mr Tobias' hand recording my humiliation.

"Go into the shop with Tony. Remember the customer is always right. You are on the verge of being punished so don't step out of line. The smallest problem and your ass will be red."

Tony and I walked into the store. We both went to the counter and sat down. There was no one in the store and so Tony stood up and took me quite roughly by the arm. He marched to a section I had not been in before. It was marked THE DUNGEON.

We went through a fake arch into a dimly lit room. On one wall there were shelves and hooks holding all manner of strange looking things. On another a large cross. The centre of the room was dominated some leather hanging from a metal frame. I was later to learn it was called a sling. One other wall had shelves with lots of smaller items, they glinted in the lights but I had no idea what they were.

"If you fuck up badly then you will be punished in here. If it's less severe you will be punished in the office and sometimes in the store itself. So it's best to do as you are told and to follow instructions immediately and accurately.'"

RustyRover
RustyRover
181 Followers