Stevie's Journey

I remember being so excited landing a position as a legal assistant at such a good law firm. My boss Mike Maddox seemed to be a great guy and I was looking forward to learning from him. I never imagined what it would be that I would learn from him. This job has changed so much and I can't even decide if I regret what has happened or if it was where my life was destined to lead.

My name is Steve. I'm 23, 5'8" and 140 pounds with longish brown hair and blue eyes. I work out three times a week at the local health club not really to get muscular but to stay firm and slender. I have to admit I'm not the most macho kind of guy but usually had a steady girl living with me or at least seeing a lot of each other. Right now I'm rather involved with this girl that is a waitress at a bar I go to. She is not a ten but is quite attractive and likes to get it on in the bedroom. What more can a guy want?

At first work was going great. I didn't have a lot of interaction with my boss but at least a couple times a day he would call me in to get him some information or some other task. If you have ever seen pictures of high level executives on magazine covers, you will have an idea what my boss looks like. He has to be at least 6'3" and had a slender build but it all looked to be totally toned. He keeps his black hair combed back and dresses in expensive suits. I have to admit that I am rather intimidated by him but hope that he doesn't see that. Let me tell you what has happened in our relationship.

Things changed at work once I had been there a couple months. It started when Mr. Maddox started asking more of me. First, it started when he started making me bring him coffee whenever he wanted it. Really didn't think that should have been expected of me. I was there to learn from him and not be his gofer but I always did it. Then there were more errands, getting his cleaning, picking up something from some store for him.

I think he could tell that doing these chores for him wasn't something that I wanted to do but whenever he called me in and told me to do something for him I never told him no. We made eye contact a couple times and, I tell you, it made me uncomfortable, the way he was tempting me to say something against what was happening. It wouldn't take long for me to have to break eye contact and look down and agree to do it for him.

I couldn't believe it when he told me to go Victoria Secrets to buy some lingerie for one of his female friends. I was to get a matching pink set of bra and panties, something lacy and very feminine. Then I was to buy her a pink camisole that would just come to the bottom of her ass cheeks. Then he tells me he doesn't know her sizes, just to tell the lady helping him that she is about the same size as you. The way he looked at me standing in front of his desk as he told me all this was rather intimidating and that just got worse when he told me to repeat his instructions.

'I'm to go to Victoria Secrets and buy pink bra and panties and a pink camisole. I'm supposed to tell the clerk that I'm buying them for a girl about my size.'

'Good boy.'

I couldn't believe he just called me boy. It's bad enough having to do this crap for him but now he wants to call me boy. Fuck him. I just look down at the floor pissed.

'Is there a problem Steve?'

'I didn't appreciate you calling me boy and I don't know why I should have to do your shopping for you.'

'You like working here Steve?'

'Of course, the pays great, love this firm but sometimes I feel like I'm being taken advantage of.'

'I expect more from the boys...men that I hire here. Maybe you are the kind of guy that doesn't appreciates a job like yours, right out of college, maybe I'm asking too much of you and it might be best if you start looking at other opportunities.'

Fuck, fuck. I can't let that happen. 'No Sir, please I like working here and I like working for you. It was wrong of me react like I did. I'm sorry. I should feel like doing these things for you is almost like rewarding me, letting me further into your life. Please Sir. I'm sorry I was so disrespectable.' I hated saying that to him but I can't lose this job, I just can't. I felt like such a suck up.

'Let me see if I understand things now Steve. You don't have a problem doing personal tasks for me, in fact, you like doing things for me. Things like buying feminine items when told to do so. Are you going to have a problem with the clerk thinking you are buying these things for yourself and not because you have been told to purchase them? How are you going to feel when she looks at you, those thoughts in her mind?'

'Sir, I will be embarrassed and even though I know they aren't for me, I know what she will think and that will be very humiliating for me. Doing something like this is hard for me. I know when I can't look her in the eye it will confirm to her that I am buying them for myself. It will be hard but I will do it because you asked me to and I want to show you how much I like this opportunity with you and know I can learn a lot from you.'

'That's a good boy. Now you take off from work right now. You have one hour till closing time. You be back here fifteen minutes after we close. I will be waiting for you and wanting to see the pretty lingerie you bought. Do you understand how things are now Stevie? I expect more.'

I just stand there stunned thinking about what has just happened. I can't blow this job. Where did this come from? I felt so humiliated that he sees me like he must. Why does he think he can treat me like this? Why does he want to treat me like this and assume that I will just do as told?

'Yes Sir, I understand,' I tell him understanding that he actually threatened to fire me if I wasn't willing to do as told.

'Good, now run off and go do your thing. I can't wait to see what you have bought.'

I turn and walk away realizing even the way he said that was rather insulting, telling me to run away and go be humiliated. I leave work and drive to the mall. Fuck, I hate this, it's so embarrassing. I force myself to walk into Victoria Secrets and start looking around.

'May I help you?'

When I turn and look, I see a very attractive woman, probably around forty. Her makeup is perfect, her black hair pulled back in a bun. I realize I'm staring and answer, 'I'm supposed to buy a matching pink set of bra and panties and a pink camisole for my boss.'

'My, that must be quite a boss, sending you out to buy lingerie for her.'

'No, my boss is a man...'

'That makes is even stranger doesn't it?' she states as she stares at me.

'No, it's not for him. It's for a friend of his.'

'Ah, I see. Sorry, I jumped there but we do have many men come in here buying lingerie for themselves. I'm sure you are aware of that.'

'Can you just help me find the things? I'm rather in a hurry.'

'Sure, do you have her sizes?'

'My boss told me to tell you that his friend was about my size.'

'Really, so your boss has you buying lingerie for a friend of his that just happens to be your size. I'm thinking I like your boss. Let's go find you some lingerie sweetie.'

'Really, they aren't for me, really.'

'You protest too much sweetie. It's ok. We will find some things you will really like.'

Twenty minutes later, I'm leaving with the items needed wondering if my face is still red from my encounter with that sales clerk. It was obvious that she liked making it embarrassing for me, leaving no doubt that she thought they were for me and one time telling me how my boss was going to love the way I look. Fuck, fuck.

I get back to the office and knock on Mr. Maddox's door and I'm told to enter. He is sitting behind his desk, leaning back in his chair, his hands behind his head.

'It took you long enough. Did you get everything?'

'Yes Sir,' I hold up the pink bag.

'Show me that you bought.'

I take the bra out and hold it out to him.

'No, hold it up in front of you so I can see what it would look like on someone.'

It just doesn't stop. I hold the bra in front of my chest. Pink with lots of white lacy, very feminine.

'Nice Stevie, now show me the panties. Show me the same way.'

I take the panties out and hold them in front of me as he stands and looks at them.

'Turn them around. Let me see the back.'

I turn them and know he can see all the rows of white lace. I thought they were too much but the clerk told me he would love them and made sure I bought them.

'Perfect. I think they call panties like those sissy panties, don't they Stevie?'

'I don't know, the clerk just told me you would like them.'

'Oh, you told her that you were getting them for me?'

'Yes, I told her that I was buying them for you to give to your girlfriend.'

'Did she believe you?'

'No, she made sure I understood that she thinks the lingerie is for me.'

'Let me see the camisole now Stevie.'

'Could you call me Steve Sir?'

'Yes I could but I think I prefer Stevie. That's ok isn't it Stevie?' he says as he walks around his desk to stand beside me just a little too close.

'I guess it's no biggie Sir.'

'No, tell me you like it that I call you Stevie. I need to know Stevie.'

What the fuck is happening today. I know things were a little strange for awhile and I had seen how he looked at me. But where did this come from, his need to humiliate me? Looking down at the floor, I tell him what he wants to hear. 'I like it when you call me Stevie Sir.'

'I like it when you call me Sir Stevie. I think we are going to get along fine now that we have experienced things today. What are you thinking about Stevie, I know it's been quite a day for you today but I felt it was time to take our relationship further? I know it must be tough for you but I know what is best Stevie.'

'I don't know what to think Sir. I didn't know you looked at me that way as someone you could treat like you have treated me today Sir. I was humiliated by a clerk at Victoria Secrets then I come back here and feel like I either do as told or I could go find another job.'

'That is exactly what it is Stevie. I have already made some transactions under your name that aren't exactly legal and I don't think there is any doubt what time in jail would be like for a pretty boy like you.'

'Why are you doing this to me Sir?'

'I have been watching you for awhile Stevie and you are very enticing. You are a handsome young man who tries his best to be a man but when I look at you I see very little manly about you. I know you have a girlfriend but a lot of gay men have girlfriends covering up what they really are. Are you gay Stevie?'

'No, I'm not gay.'

'I thought you probably were. Most pretty boys like you end up being gay, giving it up to some real man.'

'Well I'm not.'

'I need you to understand how things are now Stevie. I have faked transaction in your name that could lead to you getting jail time. As long as you do as you are told no one will ever see those transactions. Do you understand what is happening here boy?'

'Why are you doing this to me? Why?'

'I need to own a pretty boy, an obedient pretty boy? And you are such a pretty boy. Now Stevie, I want you to go home and think about today. I know this is going to be hard for you but you need to realize you only have one choice. You will be my fag boy. Fortunately for you, each month that I keep you under my control, I will put $5,000 into a saving account set up for you. This money will be yours once I tire of you and let you go.

'In the meantime, things will change now. You will come into my office in the morning. You will shut the door, move to the front of my desk, go down on your knees, head down and you will tell me you will do as told. That the thought of being my boy excites you so.'

How can he do this to me but I don't think he is lying about making up evidence on things that could land me into a lot of trouble. I know he is going to treat me like a fag but what can I do? I just stand there not knowing what to think or do.

'You can go now boy. Hang your lingerie in the closet. I want to save seeing the camisole till the time is just right. I will see you in my office, eight o'clock sharp. You will come in and you will do as you've been told. Now go.'

I leave the office and don't remember anything till I'm pulling into my garage. I plop down in my soft chair and try to get my mind around this. This guy wants to take control of me. The way he is always telling me I'm pretty says a lot about what he thinks about me and what he might want me to do. Can I take a chance that he is bluffing with the action he spoke of? I can't, what if he actually did it and I couldn't prove his shit was wrong. I can't chance going to jail.

I think about the way he looks at me. It makes me uncomfortable, it's like, he looks at me and that look lets me know that he is thinking about what he would like to do to me. I never can keep eye contact with him. I close my eyes and can picture myself on my knees, in my suit in front of his desk. I have to do it. Fuck, fuck. I can see the look on his face thinking about what fun he is going to have with me.

I get a big joint and smoke the whole damn thing. Laying back in my recliner I could keep from thinking about what had happened today. What the fuck, I have to give myself to this guy. I know he thinks I will be there on my knees in front of him in the morning. He knows and I know. What choice is there?

Then I started thinking about the clerk at Victoria Secrets. She was so sure of herself and took such control of our encounter. I remember how she looked at me when she was letting me know she thinks the panties are for me. She was so overwhelming. She had that look that let you know, she was the one in control and that I better do as told. Her tight black dress highlighted just how attractive she was and her 4" pumps just made everything perfect. And I bought lingerie from this fantastic woman, fuck, I didn't think I could ever do that. It was so scary, but still, such an erotic encounter. My cock gets hard just thinking about how she looked and thinking about the way she talked to me like I was a sissy. God, my cock is so hard that I have to stroke it as I close my eyes picturing her again.

I try to keep him from my thoughts but can't keep Mr. Maddox off my mind. I'm going to have to do what he tells me to do and I think he is going to make me his gay boyfriend. What if he lets other people know what happening between us and they think that it's something I desire.

Stroking slowly, it feels so good. I imagine Mr. Maddox standing in front of me as I'm on my knees jacking off. His face has that look of superiority and he moves one foot right in front of my cock. "Cum on my shoe,' I hear him say. I can't imagine what it would be like to have something like this happening for real. Just the thought of having to jack off in front of him is enough to make me panic but I don't stop stroking my cock. How can I still be hard thinking about having to do something like this? What if he actually did this? I know he wouldn't clean the cum off his shoe himself and when I think about what he might make me do to clean his shoe, it's too much and I cum hard.

I look at the cum all over my hand. Now I just feel like a pervert. How could I cum thinking about being made to do something like this? The situation I am in really hits me. I wish I could just quit and run away but what if he did what he threatened. I clean the cum from my hand and go to bed. Maybe I will wake up and this has all been a nightmare but I know that isn't going to happen.

I wake up the next morning and think about the day I have in front of me. This morning everything just seems worse and I can't think of any way to avoid this mess. Just the thought of kneeling in front of him seems like such a surrender. This isn't something a man should let happen to him. And I know it's going to get worse. I can hardly eat and I have to force myself to leave for work.

When I get to the office, there is another guy sitting at my desk. He looks about my age and my size but he has long blonde hair which looks great on him. Kind of reminds me of pictures of guys I have seen on magazines catering to guys and girls my age. Very attractive but almost too perfect.

'Hello,' he says as I walk up to my desk. 'I'm Taylor.'

'Hello, I'm Steve. What are you doing at my desk?'

'Oh, about that. Mike told me to send you to his office as soon as you got in.'

Taylor calling Mr. Maddox Mike catches me off guard. I have never called him Mike and I don't think he would appreciate it if I did. 'OK,' I answer looking at the door to his office and just staring at it.

'You better go Steve. You don't want him to have to wait on you, do you? And he told me to make sure you bring him his coffee.'

I go get his coffee, making it just like he likes it with a little cream in it. I go knock on his door and I hear him tell me to come in. I walk up to his desk and hand him his coffee. He doesn't say anything, just looks at me. I back up a couple steps then slowly sink to my knees. I look down and can feel my face turning red. 'Sir, I want to be a good boy for you. The thought of being your boy really excites me.'

'Look up at me. Did you masturbate last night after you went home Stevie?'

I look up and we make eye contact and his look says it all. He is not kidding about this and expects obedience from me. 'Yes Sir, I did.'

'What were you thinking about when you stroked your little cock Stevie?'

Not really wanting to discuss this but things could be worse so I tell him. 'I was thinking about the clerk at Victoria Secrets. She was so hot.'

'You like the fact she treated you like a little sissy boy, didn't you?'

'Not really Sir. It was so weird. The way she talked to me was very embarrassing and I know she liked humiliating me but at the same time, everything about her was turning me on. I know my cock got hard but I don't think she noticed. I can't imagine what it would be like to have to dress up like a sissy. It's nothing I have even considered.'

'That's rather hard to believe. You really don't come off as very manly. I know that sounds mean but it's not. There is nothing wrong with being more feminine than most other guys. Most pretty boys like you have had numerous occasions to wear panties and see what they felt like. Have you ever worn panties Stevie?'

'No, definitely not.'

'That's too bad. Your ass would look so hot in the right pair of panties. Stand up in front of me Stevie.'

I stand up in front of his desk.

'Did you meet Taylor?'

'Yes, he was sitting at my desk.'

'That is his desk now Stevie. I have turned your projects over to him. You are going to be my personal secretary. I will have a desk set up right outside my office. I know you want to be close to take care of my every need, don't you Stevie?'

Fuck, this just gets worse and worse but he has me and he knows it. 'Yes Sir, I do.'

'This job requires a different mindset than your job as a legal assistant. For that job you needed aggression which I feel you lacked. You new job requires more passive behavior. Clients that you will greet need to see my secretary as a very subservient type personality. Your mannerism shouldn't try to project masculinity since you aren't very good at that anyway. Show them your softer side including how you talk and interact with me and my clients.'

'No more suits at work. Find some nice black slacks and buy some long sleeved shirts in pastel colors. You know, pinks, yellows, baby blue and make sure they are made from a material like a shiny polyester. I want you looking nice for my clients. Also, black loafers, no socks.'

I feel like I'm about to cry. Everything is so out of control I just stand there not saying anything.

'Since you don't have a desk, you might as well take the day off. One little chore for you Stevie. I have been thinking about your favorite clerk and I want you to go back to Victoria Secrets and find her. Tell her you forgot to get a pair of white thigh high nylons, the one with the seam up the back. You will tell her that I would love to speak with her and you will get her name and phone number. Stop and tell Taylor that you are so glad he is here, that you were having trouble keeping up and that you feel being my personal secretary is going to be better.'