Stevie's Journey

'Yes Sir,' I say starting to walk away.

'Stop boy, come stand in front of me and unfasten your slacks. I want to see something.'

Nervously, I do as told and he tells me to push my slacks down enough he can see the white jockeys I have on.

'That's unacceptable. You will wear panties to work from now on. Have the clerk at Victoria Secret help you find at least ten pair of panties, different styles. You can charge them to my account like you did the other lingerie. You will come to my office each morning and show me the panties you are wearing that day. Now, before you go, thank me for buying you panties to wear, that you can't wait to get some sexy panties to wear for me.'

I feel so humiliated and he knows that making me thank him just makes it worse but what can I do. 'Thank you Sir for buying panties for me to wear and I hope you like what I buy.'

'Good boy, Stevie. Don't forget to stop and see Taylor. I think you two will become best of friends.'

I leave thinking about how he gave my job to another and the thought of being his secretary is so humiliating. I see Taylor look at me when I leave Mr. Maddox's office and I walk over to him.

'I hope you don't hate me for the changes he made Steve. I have known Mike for a while and I just couldn't say no when he offered me the job.'

As much as I hate to say it, I do. 'No, it's ok Taylor. I was having trouble keeping up and think being his secretary will be ok.' He smiles at me and comes over and gives me a hug. I didn't notice it before, but his mannerisms are rather gay. When I look closer, I see that his ears are pierced and he has little diamond studs in both ears. He sees me looking at them.

'Don't you just love them? Mike got them for me. You should get your ears pierced. I know a great place. Maybe we can go out together some day and get them done. You will love it.'

'I don't know Taylor. Not really my thing.'

'I know Steve. It wasn't mine either when I first met Mike but now I'm so glad I did it. Sometimes it can be kind of hard but Mike does know what best for us. We just need to do as told.'

Fuck. Does Mr. Maddox control this guy too? It sure seems like he might. The more I look at Taylor the more gay he seems to be. 'He gave me the day off. I will talk to you later.'

'Come give me another hug. I hope we can become best of buddies.'

I hesitate but he moves to me and gives me a hug, a hug that lasts a little too long. I hurry away once he lets loose of me. This just gets fucking worse and worse. I don't want to hang around with a fag especially one that is so obviously gay. I just get to my car and sit there feeling helpless.

I dread the thought of having to go back to Victoria Secrets and seeing that lady again. This time will be even harder, having to buy all those panties. I might as well get it over with and head to the mall. I walk in and see her staring at me. I walk over to her.

'I knew you would be back sweetie. Did your boss like what you bought.'

'Yes I think so.'

'I knew he would like the sissy panties. They are one of our best sellers for boys like you.'

I look down embarrassed. 'I'm really not like that. He is forcing me to come here and buy the panties and other things. I'm not a sissy, really.'

'Aren't you the cutest little boy? Your face gets so red, I just love it. Now what can I interest you in today sweetie?'

I hate it when she calls me sweetie. I tell her what I'm there to buy and she just smiles. She heads over to the area with all kind of panties. I follow behind checking her out. She looks even hotter than the previous day. She has a white silk blouse with a tight black skirt but what really gets me are the black boots with the spiked high heels. The sound of the heels on the tile floor is enough to make me start to get hard again. She turns and looks at me when she arrives at the panty area. She just looks at me then down at my crotch and smiles.

'Looks like you are glad to see me again. I should be flattered making a boy like you hard just being with me. You better adjust that so it isn't so obvious unless, of course, you want the others here to see your little hard on.'

I reach down and adjust myself so it isn't so obvious. Then the humiliation continues. She selects panties and holds them up in front of me. Her voice loud enough that I know some of the other clerks and customers can hear her. It's not long till I'm holding ten pair of panties, all different colors and styles. Then she gets a pair of white thigh highs for me.

'Will that be all sweetie?'

'Yes but my boss would like to talk to you. He wanted me to ask for your name and phone number.' She hands me her card and tells me to tell him she can't wait to hear from him.

'What is your name sweetie?'

'It's Steve.'

'Sure, sweetie, whatever you say.' She rings up all the sales, handing me the bright pink bag. 'Till next time sweetie.'

I rush from the store but know I'm not done. By the time I leave the mall, I have purchased several shirts like he described and a couple pair of black slacks. I already have a pair of loafers that should work. How did everything get so out of control? I drive home and get high. Fuck, fuck. I go into the bedroom and see all the panties scattered out on the bed. The thought of wearing them to work and having to show them to Mr. Maddox is so fucked. I put the panties away in a drawer and try to forget all this shit for the rest of the day.

I get up the next morning and get cleaned up and ready to get dressed. I go to the drawer and look at the panties. I chose a pair of baby blue panties that fit high on the hips. I slide them on and try to tuck my cock away in them but the only way I can keep it contained is to tuck it back between my legs. If I pull the panties up tight, it stays in place. Grab the baby blue shirt and finish getting dressed. It feels so weird to wear the loafers with no socks. I head off to work. When I get to work, I don't see Taylor anywhere but know what I must do. I go knock on Mr. Maddox's door.

'One minute,' I hear through the door. I stand there several minutes till the door opens and Taylor comes out of his office. His hair is a little messed and he seems almost out of breath. He just smiles at me.

'Your turn Stevie.'

I can't believe he just called me Stevie. What did Mr. Maddox tell him about me? I go into his office. He is sitting at his desk, a smile on his face.

'Hello boy, did you have a good time shopping yesterday?'

'I got what you told me to get Sir.'

'But did you have a good time?'

'Not really. It was so embarrassing.'

'Maybe next time I will have Taylor go with you. He loves shopping. Did you get her name and number?'

'Yes Sir,' I answer handing him her card.

'Good boy, now show me your panties.'

I unfasten my slacks and lower them enough that he can see the baby blue panties. It was so humiliating.

'Interesting boy. It doesn't look like you have a cock. I figured it would be small but your crotch is flat like a girls.'

'I had to tuck it between my legs to keep it in the panties Sir.'

'I like that look Stevie, you keep that little cock of yours tucked back like that at all times at work. Ok, you may pull your slacks back up. Go see if you can get anything for Taylor.'

I leave his office. That was so humiliating. I go ask Taylor if he needs anything. He tells me he wants coffee also and he smiles at me when he tells me he likes lots of cream in his coffee. I start to walk away when I notice a couple spots on Taylor's shirt and I instantly know what they are. They are cum spots. Oh fuck, Taylor must have been sucking Mr. Maddox off in his office when I knocked. This is all so fucked up.

I go over to the desk in front of Mr. Maddox's office. It has a nameplate that reads, 'Stevie'. That is probably what Taylor saw. I sit down but there's nothing for me to do but answer the phone and once in a while Mr. Maddox has me get paperwork from Taylor. His first client, Mr. Walker, shows up at two in the afternoon. I let Mr. Maddox know that he has shown up and he tells me to escort him into the office. When we get into his office, they shake hands and I start to leave.

'One minute Stevie. I want to introduce you to Mr. Walker. Jim, this is Stevie. He is my new personal secretary.'

'Hello Stevie,' he says, his eyes checking me out. 'I don't know how you do it Mike, but you find the prettiest boys to work for you. Taylor is such a sweetheart and Stevie is just as attractive.'

'Yes, he was working as my assistant but that was a little too much for him. I think he will work out very well as my secretary. It will be nice to have someone to travel with and take care of all the details when we do travel.'

Jim smiles at him then looks at me. 'I'm sure that will make your trips much more memorable. I'm jealous.'

'Don't be, maybe we will be coming to see you. I know you enjoyed it when I brought Taylor along with me.'

'Oh yes, definitely.'

'That will be all Stevie. Run along like a good little boy.'

I hear them both laugh as I'm closing his door. I'm sure Mr. Walker understands what is going on between us. I go sit down at my desk and think about all this and how it doesn't ever stop. Thank god, it's about closing time and I can get out of this nightmare. I see Taylor walking over to me.

'I'm having some friends over for a small party tonight. I want you to come. Please. Please.'

I think about the friends Taylor probably has. I'm sure most of them are gay. I don't need to a party with those kinds of people. 'I'm sorry Taylor but I'm tired and just want to take it easy tonight.'

'Oh darn, I wanted to introduce you to some of my friends. I'm sure you would like them and I'm really sure they would like you,' he gives me a little smile. 'I wish you would change your mind.'

'Maybe next time Taylor,' I tell him and he walks away. A few minutes later my phone rings and it's Mr. Maddox.

'You will go to Taylor's party tonight. You will stop him before he leaves and tell him you changed your mind. You will tell him that you are usually reserved and like to keep my private life private but the thought of meeting his friends sounds so exciting and that you want to step up your social life. You will wear panties of course. I will be stopping by to say hi and I will check Stevie. Now you go be a good boy and go to that party full of gay and sissy boys.

He hangs up. He just doesn't let up on me pushing me further and further. I look over and see Taylor heading for the door.

'Wait Taylor, wait.' I rush over to him. 'I changed my mind. It's not something I usually do but I need to get out more and meet new people. When I thought about what exciting friends you must have I had to change my mind.'

Taylor quickly gave me a hug and held onto me. 'You will love my friends Stevie. I know you will. They are such exciting people.' I feel his cheek on mine and move my head away. 'I can't wait to show you off to some of my friends. They will love you,' he says as he lets me go and turns and leaves.

Does Taylor think I'm gay? He acts like he thinks I am. I know what is going to be at that party and Taylor will want to introduce me to everyone. I wonder what it will be like interacting with these people. I have never been around the gay scene at all. Will they look at me in such a way that I will know they want to be with me. What if they come onto me, strong? Will they see me like Mr. Maddox sees me? I know he likes letting me know that he is going to turn me into a sissy fag and there's nothing I can do about it.

I get home and try to relax. Fuck, I have to go out to this party tonight and I will have to stay at least until Mr. Maddox leaves. I light one up and lay back and think about what it's going to be like. What will I feel like to have others looking at me and thinking I'm gay. I got to be high when I get there or I don't know if I could do this. Finally get dressed, nice slacks, the yellow shirt I bought at the mall. For some reason, it only seemed right to wear the loafers with no socks. I head over to Taylor's place.

I knock on the door and Taylor opens it and smiles and gives me a hug and I feel a light kiss on one cheek. I look over his shoulder and see there are around twenty people in the room, several watching us, others involved with others. He breaks the hug and grabs my hand. I try to pull my hand away but he moves closer.

'Don't be like that Stevie. I don't want to tell Mike you've been misbehaving. Now hold my hand Stevie boy.'

I'm high but still understand what this means. Taylor and Mr. Maddox are both involved in this. It's easy to see Taylor wanting to please Mr. Maddox by helping him control me. I hold his hand but can't meet his eyes. He pulls me to the middle of the floor and gets everyone's attention.

'Friends, this is my new friend Stevie. Isn't he cute? Stevie works with me and for Mr. Maddox. Mr. Maddox wanted me to introduce Stevie to you all and hope you find Stevie to be someone you find to be as enticing as he does. Stevie wants to meet new people and discover things about himself that he has never considered. Say hello Stevie.'

I feel overwhelmed that he just put that out there for everyone. It was like an invitation to everyone to introduce yourself and your lifestyle to him. I look at his guests. There are several men in suits. I'm sure they are probably bosses in some firm. Men like them carry themselves differently. Then there are the gay boys running from pretty boys to really what I would consider flaming fags. There were half a dozen women there but I was sure at least half of them were not females. All of the girls or whatever they were all very beautiful and so very sexy.

Feel like I can't get my breath but I weekly get out, 'Hello everyone.' Taylor releases my hand. 'Go mingle Stevie. Mr. Maddox wants to make sure that you behave properly so I will be watching. You better look like you are enjoying it.' Several of his guests return my greeting then I feel a tap on my shoulder. When I turn around it's the lady from Victoria Secrets. She has a skin tight black leather cat suit on with ankle boots with five inch heels. She grabs my forearm and tells me to come with her.

'One minute Anne. He has taken his pill yet. Here Stevie,' he says as he hands me a pill. This is an ecstasy party Stevie. Everyone is taking it. If you just accept that you are going to feel different but ok, then everything can become very exciting. Ecstasy can raise the level of experiences, things seem more intense, colors brighter, music nicer, just let yourself relax and enjoy it.' He watches as I take the pill.

'Good boy now go with Anne. She has been waiting for you.'

She literally dragged me through the crowd as they separated for us to pass. I could feel their looks and imagine what everyone must think of me now. She pushes me into one of the bedrooms and closed the door. She pushes me into a soft chair and stands right in front of me glaring down at me.

'Your boss and I had a long talk Stevie boy. He told me how he's forcing you to serve him. I find that so hot. He has some nasty plans for you boy. I got the impression that it's probably not a good thing to disappoint Mr. Maddox. He isn't sure you really understand how things are now and asked for my help. I told him he would be disappointed if he were to see the way you would look when you got to the party. I told him the boy would be wearing the most masculine thing he can find so everyone didn't think he was a faggot. I asked your boss if he wanted my help. He does, so here we are Stevie. Do you want to disappoint him?' she asks and I know she is referring to Mr. Maddox.

'No Ms...'

'You will call me Anne in public, when we are alone like this or with friends I have invited to join us, you will call me Mistress Anne. Do you understand Stevie? Your boss told me you weren't exactly the smartest guy on the block.'

Well, that was insulting. 'Yes Mistress Anne, I understand.'

'Then undress, you look ridiculous, like some fucking pretty boy nerd. That is not what your boss desires. He likes his boys pretty and also, very sensual. Now get undressed.'

I start undressing knowing how it's just going to add to my humiliation when she sees the shiny white panties I have on. I get undressed down to the panties and stop.

'Very nice Stevie. Very appropriate for a gathering like this. Here put these on,' she says hand me a short pair of white pants.

'I could never get into those. They are way to small.'

'They stretch silly boy. Good thing you aren't blonde or I would probably start thinking you were one of those silly bimbo bitches men seem to like. Now get them on.'

I step into them and start pulling them up. They fit pretty much skin tight and by the time I'm finished they just go down to just below my knees.

'They are called Capri pants Stevie. Very popular and very sexy. Turn around, let me see your ass.' When I turn she can see that the pants have pulled up into my ass crack highlighting my nice round ass. They ride kind of low on my hips.

'I can't wear these out there Mistress Anne. Please don't make me do this.'

'You need to try harder Stevie. You knew you were invited to a gay party. You should have gone shopping and bought yourself an appropriate outfit. But no, no effort from you. You made no effort, so I have to put forth extra effort to make things even more humiliating for you. That's why you are going to walk out there looking like one of those pretty fag boys.'

She hands me a bright pink blouse and makes me put it on. It has long fluffy sleeves and big lapels. I try to button it up but no buttons. She comes around in front of me and takes the two shirt tails and ties them together. They ride above my waist leaving about three inches of bare midriff. Also the lapels of the blouse lay back, exposing a lot of my smooth chest almost opening up to where my nipples show. The blouse screams sissy faggot.

Then she brings out these pink ankle boots with pointed toe and a three inch block heel and a pair of white ankle socks with pink lace tops and makes me put them on. The socks stick out a couple inches above the boots. Thankfully, the block heels make walking a little easier but I still have to concentrate and take small steps. She leads me over to a full length mirror and makes me look at myself. I look so gay and rather feminine.

She comes up behind me and put several gold chains around my neck that hang down my bare chest. When I look closer I see a small gold figure of cock and balls hanging on one of the chains. I just stand there not knowing where to turn. Then she brushes my hair, using the hair spray she brought, hair tucked behind my ear and I much more feminine style. Then I feel her rub something on my cheeks turning them a little pink.

'Do you think Mr. Maddox will be disappointed with the way you look now Stevie?'

'No, I think he will like the way I look.'

'Then shouldn't you try harder to dress and act in the manner you know he expects of you. Don't be a cunt with him or it won't be pleasant for you.'

'I guess but I didn't want this...'

'You must understand what you want is not important. What others expect from you is what is important. How you live up to others expectations will decide many things about your new life. I know Mr. Maddox is here now and he is probably looking for you. I want you to walk out there alone, find him and slowly walk up to him, keeping eye contact the whole time and put your arms around his neck and lift your head up letting him know you want him to kiss you.'

I can't imagine walking out there looking like this. And then I'm expected to throw myself at my boss letting him know I want him to kiss me. Everyone will be watching. How can I do this? Mistress Anne reaches in front of me showing me her phone. On the phone is a picture of me dressed as I'm currently dressed.