Steve's First Adventure Pt. 02

Total fantasy. Do not read if not into gay sex, domination and forced fem.

*****

After that first experience, things didn't get too crazy like I was afraid they might. I did meet with Daddy several more times in the next couple months. There were more spankings as he taught me it was better to do as told, that if I resisted things would just get worse. He always made me dress up fem and insisted that I learn to put on makeup properly. He had a way of making me feel that I deserved to be treated like he treated me. If I tried to act at all masculine around him he made sure I knew that wasn't acceptable. He hadn't made me go out in public again and I really appreciated that. To have others see me as a fem boy was my biggest fear and so humiliating.

My job changed somewhat and I ended up working less and less from home. I was a legal assistant to a lawyer with his own practice in the downtown area. He was very successful. Daddy made me tell him about my job, my boss and how things were going. My boss, Mr. Manning, was 52, six foot, two and reminded me of the executives you would see pictured on business magazines. He was divorced and I didn't know much about his private life. He was not the easiest man to get to know or feel very comfortable around.

There were two other guys working for him. They were both a couple years older than I was and had worked for him for over three years. I was with the firm for just over a year. We prepared legal briefs and other paperwork, answered the phones and did whatever he needed us to do. I got along with them ok but we didn't hang out together at all.

Working in the office was not nearly as relaxing as it was when I could do most of my work at home. I found Mr. Manning rather intimidating and when he called me into his office, I had the fight the nervousness I felt and that sometimes led me to make mistakes I shouldn't have made and he didn't hesitate to let me know when he was displeased. The job was very important to me since it paid well and I didn't want to blow it which just made me even more nervous around him. I just couldn't loss this job. I explained this all to Daddy and he told me not to worry, that he would make sure I didn't lose my job. I didn't know how he could guarantee that.

One day, I got an email from Daddy. It read: Stevie you will check into the Sheraton Hotel downtown on Saturday night at seven o'clock. The room will be paid for, just go to the front desk, give them your name and they will give you the key. I have sent the following email to your boss. Send me an email Sunday evening with a picture of yourself dressed waiting for your boss to show up. Don't worry Stevie, if you get fired, I know you will make a good fag whore.

"Mr. Manning, this is Steve from work. I know that my job performance has not been up to par and I was hoping that I could do something to show you how much I need my job and enjoy working for you. I have to admit that I can't get you off my mind. You are the man I wish I could be but I know I could never be a man like you. When we are alone in your office, it's hard for me to even feel very manly at all. It's so hard to admit that but it's true.

I'm going to be in a hotel room at the Sheraton my Saturday night. I was hoping you might come to my room around nine o'clock that night. I know I don't deserve to spend time with you but I have to ask. I'm afraid of losing my job and want to show you I will do ANYTHING to keep that from happening. If you don't want to do this, I totally understand and realize that asking will probably lead to me being fired but I can't stop thinking about you. I want you to see what I'm really like and how badly I need to spend time with a real man like you. Please come show me what you really think of a boy like me. Stevie"

Oh god, how could he do this to me. Mr. Manning will fire me for sure. How can I go to work tomorrow? This is too much. What will I do if I lose my job? Fuck, Fuck. At least tomorrow is Friday so I only have to endure one day. I wonder if he will fire me when I come into the office.

Friday morning and I go into the office dreading every minute of it. I go to my desk and try to settle down but it's so hard. Then I get the call from Mr. Manning wanting me to come to his office. I can feel my face turning red but I know I have to do it. I go knock on his door and he tells me to come in so I do and close the door behind me. I can't look up at him.

'Do you have the Thomas brief completed Steve?'

'Yes Sir, I didn't bring it in with me though.'

'Why don't you be a good boy and go get it for me Steve.'

'Yes Sir,' I answer still not making eye contact. I leave and go get it and bring it to him and set it on his desk.

'Hopefully, you haven't screwed this one up.'

'No Sir, everything is in there.'

'Are you alright Steve? You seem more nervous than normal.'

'I hope everything is ok Sir. Is there anything else?'

'No that will be all,' he says and I turn to walk out. 'You be a good boy Stevie.'

Oh fuck, I shut the door behind me. That left no doubt that he got the email. I feel a little relief that he didn't fire me but he made sure I knew that he had gotten the email. I'm shaking as I sit down at my desk. I barely get anything done the rest of the day but thankfully didn't see Mr. Manning again the rest of the day. I stop on the way home and have a couple drinks trying to calm down then smoke a big joint when I get home. I can't get the thought of tomorrow night off my mind and only sleep a couple hours that night.

Saturday morning and I'm a wreck. Maybe he won't show up. Then I think if he wasn't going to show up, he would have probably been pissed and fired me and that makes me think that he will show up. Oh fuck. How can Daddy do this to me? I stay high all day trying to relax but I can't get it off my mind. It's finally time to leave.

I check in at the Sheraton and go to my room. It's a nice suite and when I go into the bedroom, I see the clothes laid out on the bed. There is a note on the dresser that reads: You better be a good sissy bitch for your boss if you want to keep your job. I'm sure I will get a chance to talk to him in the future to see how well you behaved. I wanted your first time to be special and what can be more special than losing your virginity to your boss. You will do everything and anything he asks of you. Now go take a bath, use the bubble bath and the fem body lotion. Make sure you are totally smooth, I left you some razors. Get dressed and put on your makeup and the perfume. I left some lube by the bed. No condoms for you sweetie. You need to feel his cum in your cunt. Have fun sissy boy. Daddy.

The nightmare continues but I do as I have been told. After showering, I go put on my makeup and by now I'm pretty good at it. A few hard spankings help you learn in a hurry. I go back to the bed and see the white corset and the white nylons. I put the nylons on and pull them up high then put on the corset and tie it as tight as I can like I've been taught then hook the garters from the corset to the nylons. I put on the panties on the bed. They are pink with several rows of white laces running across the ass, definitely sissy panties. There is a pair of pink pumps with three inch spiked heels for me and I put them on. Lastly, there is the sheer pink negligee which comes down to mid thigh.

I go look at myself in the mirror. I look so different. It's not hard to tell I'm a boy but I look like a really pretty sissy boy. The heels make my legs and ass look so different and the corset makes my waist look small. I reach down and tuck my cock back between my legs giving the panties a flat look in the front. I can't stop looking at myself and if it wasn't for the fact that my boss might show up, I would kind of like the way I look.

I go back to the living room of the suite and sit down and smoke the joint I brought with me and I look at the clock. It fifteen till nine. Oh god, how can I do this? Then I remember that I'm supposed to take a picture for Daddy so grab my phone and stand in front of the full length mirror and take several pictures of myself. I'm sure one will come out alright. I sit back down trying to relax.

I jump as I hear a knock on the door. I get up and go to the door and open it a little way and see him standing there in his fancy suit. I open the door standing behind it as much as I can and he comes in and shuts the door behind him.

'My, my. Not what I was expecting Stevie boy.'

'Please call me Steffie,' I tell him, knowing that is what Daddy expects of me.

'Steffie, that's great. I always thought you were gay but I had no idea that you were a sissy. Sit down and try to relax. I've got to think about this.'

I sit down in one of the soft chairs across from him and cross my legs like I have been taught by Daddy. 'Mr. Manning, I'm so sorry about all of this. I know how this has to look but I'm really not even gay. I'm being forced to do this by a man I met online.'

'Really, not gay? Excuse me if that's a little hard to believe. Look at you.'

'I met this guy online and just wanted to try one thing and it all got out of control. Now he has pictures of me and if I don't do as I'm told, he will expose me to my family and everyone.'

'What did you want to try?'

It's so embarrassing to admit this but can it be worse than sitting here dressed up like a sissy boy? 'I wanted to see what it was like to be spanked.' He laughs at me, shaking his head.

'Did you find out Steve, oops Steffie?' he says a smirk on his face.

'Yes Sir.'

'Did you like it?'

'Not really. It hurt a lot more than I was expecting and to get him to stop I had to do other things for him.'

'Like what, dressing up like a fucking girl?'

'Yes Sir,' I answer keeping my eyes down, so humiliated.

'That wasn't all you had to do, was it?'

'No Sir.'

'Tell me sissy boy. Tell me what you had to do.'

'I had to suck his cock Sir.'

'Did he fuck you?'

'No Sir, nothing like that.'

'Fucking amazing,' he says as he is interrupted by the phone in the room ringing. He hesitates and picks it up. 'Hello.'

'Hello, my name is Mike and I arranged this meeting with Steffie for you. I hope you like what you see.'

'Well Mike, it isn't quite what I was expecting. I always thought Steve was a fag but I had no idea that he was a sissy too.'

Laughing, 'I taught that might surprise you. I bet he has been telling you that he's not gay and being forced to do all this.'

'Yes he has been telling me that very thing.'

'Well, it's true. What I do Thomas, is find good looking straight boys and turn them into sissy boys. It's so much more rewarding then working with gay boys. To watch them try to resist and then finally submit is so rewarding. Once they are properly trained, I find men for them to serve. I think a boy like this might interest you.'

'And why do you think I might be interested Mike?'

'Divorced, middle age man, very successful, a real alpha man, this kind of man often enjoys special kind of toys. Toys like Steffie.'

'I have to admit, it is kind of intriguing. I have never really thought about something like this but it's something to think about.'

'Absolute control of another. The feeling of power can be quite intoxicating. And that doesn't even factor into the financial gains a situation like this presents. A sissy like Steffie can be a virtual ATM. You would be surprised how much demand there is for a pretty sissy like Steffie.'

I'm so nervous, sitting there listening to the conversation, knowing it must be Daddy on the other end of the line.

'Really?'

'Yes Thomas. If a man desires to turn his sissy out, they can be very valuable. I mean big money. One boy I sold last year earned well into six figures for his Master. It's time to talk business. I will sell you Steffie for $10,000 and trust me, that's a bargain price.'

'Sell him.'

'Yes, he will belong to you and you can make sure he does as he is told. I will include a portfolio of pictures of him and a thirty day money back guarantee. Also, I will provide supplemental training of him free of charge if you don't think he is performing up to the standard you are expecting.'

'Fuck, that's crazy. You really sell boys like Steve?'

'Yes and I have many very satisfied customers.'

'I don't know Mike. It all seems rather unreal.'

'Let me send you a couple pictures Thomas.'

I see Mr. Manning take his cell phone from his pocket. When he looks he sees a picture of me, standing in a corner, nothing on but a corset with my panties pulled down below my ass cheeks. My ass is a bright red and my face is turned back towards the camera and you can tell I have been crying. The second picture shows me with cum all over my face. My tongue is out trying to lick up any cum it can reach. I sit there wondering what he is looking at on his phone, thinking it could be pictures Daddy has taken of me.

'Interesting Mike.'

'Yes Thomas. You will be surprised the feeling you will have the first time you have a boy crying like a little sissy, begging you to stop, offering to do anything if you will stop spanking them,' he says laughing. 'Giving me a hard on just thinking about it.'

'I don't know Mike. It's a lot of money and I don't know how it would really work.'

'I will call you tomorrow night for your answer. Now please let me talk to Steffie.'

Mr. Manning hands me the phone. 'Hello.'

'Hello Steffie. I have offered you to Mr. Manning. It is up to you to make sure that he wants to buy you from me. If he decides he doesn't want you and sends you back to me I will realize that my training wasn't successful and further measures are needed. The first thing I will do is remove your balls. Then you will be sold to a man in either Africa or the Middle East. American white boys are in high demand over there. I like you and wanted to give you a chance to be with a man such as your boss. It's up to you to make sure he wants to buy you from me,' he tells me and hangs up. He smiles to himself knowing he would never do that but the boy doesn't know that.

I can't believe what just happened. I thought things were out of control before but I never expected something like this. Sell me? How can he do this? I think about what he said if Mr. Manning didn't buy me. I can't let that happen. It's all I can do to not start crying. I look over at Mr. Manning and see his staring at me. I know what I must do. I stand up and go over and kneel in front of him.

'I can't stop thinking about you Sir. I am so happy Daddy is offering me a chance to be with a man like you. I promise I will do anything you want me to do and I will be a good boy, or girl, whatever you want Sir. You can punish me if I disappoint you. Please Sir. Do you want me to suck your cock? I really want to,' I tell him, knowing how my begging must sound. He just looks at me then suddenly he slaps me so hard I almost fall over.

'I've been wanting to do that for a long time Steve. Now thank me and ask me to slap you other cheek even harder.'

Tears start to flow but I just think about what Daddy said he would do to me so I straighten up and look up at him. 'Thank you Sir, will you slap me again even harder, I know I deserve it.' He just looks at me then slaps my other cheek even harder. I fall to the side, tears flowing, it really hurt. I look up at him. 'Thank you Sir.' He stands up in front of me.

'Suck my cock faggot.'

I reach up and unfasten his pants and pull them down. I can see his cock outlined in the silk jockeys he has on. It looks big. I lean over and start licking it through the material and can feel it getting harder. I lick his cock head through his jockeys getting them all wet then pull his jockeys down and let his cock hit my cheeks. I run my tongue all over the head of his cock and then suck it into my mouth. I take it deeper and deeper till I feel it slide into my throat. I don't stop till my nose is pressed into his pubic hair. Daddy has trained me to be a good cocksucker and I heard Mr. Manning moan when his cock entered my throat.

Then I start sucking him. I suck as I pull my mouth back almost taking his cock out of my mouth then slowly suck him all the way in again. I do this several times and then feel his hands take my head and he starts controlling the action. It's not long till he's face fucking me hard. I hear him moaning then feel his cock harden as he pulls my face hard into his crotch and feel his cum shoot into my throat. He pulls back and shoots the rest of his cum into my mouth.

'Don't swallow faggot. I want to see your mouthful of my cum.'

My eyes watering hard from the face fucking and when he pulls his cock from my mouth, I lean my head back, open my mouth wide and show him my mouthful of cum.

'Stir it around with your tongue bitch. Taste my cum you fucking sissy fag.'

I do as he says and look up at him. The look on his face leaves no doubt that he enjoyed treating me like he did.

'Ok bitch, swallow.'

I swallow the big mouthful of cum and look down at the floor. The tears flow as I just kneel there in front of him.

'You are a very talented cocksucker Stevie. I hope your boy pussy is just as satisfying. Get your ass up and go fix me a drink. We need to talk.'

I go over to the bar in the suite and fix him a scotch and water and bring it back hand it to him and then I kneel down in front of him, lower my head and stay quiet. He has fastened his pants back up.

'You know what is happening here don't you Steve?'

'Yes, he is trying to sell me to you.'

'Yes, he is and I have to decide if that is something I want.'

'Please Sir. I will try really hard to please you. I will do anything you want me to do. I will dress anyway you want me to dress and if you want me to be a sissy for you, I will do it and try to act very feminine for you. Please Sir, I won't disappoint you.'

'And if I decide I want you to please others?'

'I will do it Sir and make sure to please them.'

'No more hiding at work that you are a fag Stevie. I would expect you to leave no doubt from your mannerism that you are gay. Not just gay but I'm sure you have watched enough videos to see how the flaming fag boys act. That is what I would expect of you.'

'Yes Sir, I would do that for you.' How did it get to this? One email online and see where it has led me. I feel I no longer have any control of my life. I can't keep from crying and I can feel him looking down at me, not saying anything. Finally, he stands up.

'Follow me.'

I start to get up to follow him but he tells me to crawl so I crawl behind him as he goes into the bathroom.

'Take me cock out faggot. I have to piss.'

I take his cock out and wait for him to move to the commode.

'Do you think I should have to piss in the toilet boy? I thought you said you would do anything to please me. Watching you drink my piss would please me faggot.'

Oh fuck. How can I do that? Is he testing me? What if I refuse? Can I take that chance? I move in front of him and take his cock in my hand and bring it to my lips and open my mouth. 'Please piss in my mouth Sir.'

'Are you sure Stevie? I mean what kind of boy does that?'

'A faggot boy like me Sir. I really want to drink your piss.'

'Then drink bitch,' he says as he pisses in my mouth then moves to where his piss is sprayed all over my face. Then he pulls my head till his cock is in my mouth and continues pissing. I try to drink it but he is pissing so fast a lot flows out of my mouth and down onto the floor. He finally stops pissing and tucks his cock away.

'Lick up the piss you spilled on the floor. Wash out your mouth and come back into the living room.'

He stands there for a minute watching me lean down and I start licking up his piss.

'Absolutely amazing. What a fucking fag bitch,' he says walking away.