Training.

So, this opening part is just mean. I felt pretty bad writing it. However, I think it’s important to the ending of the story. If it’s too much please stop reading at any point and let me know. I’ll can either replace portions or just explain what I was trying to set up for the later parts.

The Bar:

/Then five of us are seated around a table at Patrick’s favorite bar. God, why he loves crowded bars I will never understand/

/Boisterously and slightly drunk Jamie points to you and laughs, saying/

Jamie: Ha, what the fuck are you doing, fag. Who crosses their legs like that you might as well give up your balls if you are gonna cross your legs like that.

/Not to be outdone by his best friend, Derek joins in on mocking me/

Derek: Like, really dude. We uh, we are going to have to work on this if we are going to be hanging out in public. Also, who the fuck orders a sex on the beach when they are with their guy friends… Might as just say “Look here! I like boys and taking it up the butt!”

/Always the most moderate of the three roommates he still has to get an insult in while trying to defuse the situation/

Patrick: Common guys we all know he’s a little fagish but let’s just move on and get back to drinking.

/Alright, not just slightly drunk…/

Derek: Pff, says you. You aren’t the one sitting right next to him. I think the waitress thought we were gay. At least I would clearly
be the one on top because, lets me honest, I would definitely be giving it in that case.

/no longer making fun of just me/

Jamie: WHAT! Ha, how the fuck, haha, does that make it any better? Even if you are the one plowing a dude you are both definitely fags! There is like, no way it’s any better.

/Derek is being defensive and tries to explain himself in that self righteous way only drunk people can manage/

Derek: NO, there is a huge difference! If I am plowing him in the ass it makes me far less gay then taking it in the ass. See, if I pay for this losers sex on the beach then, while still gay, I would still, in fact, be less gay then this little fag.

/Jamie is trying to bring his jokes back to the main, agreed upon, target/

Jamie: Whatever floats your boat, dude. Taking or giving, If it’s in the butt and there are two dicks, I’m pretty sure it’s gay. But, let’s just be clear here I think we can all agree that Derek’s date for the night is the gayest, most feminine and faggiest.

/Oh shit, Patrick just noticed the boner I got from all this talk… he is no longer trying to defuse the situation. A few of the other table are starting to notice now, Fuck this is embarrassing. He is laughing his head off and pointing at your erection as he says/

Patrick: Uh, dude. Do you have a boner right now! No, no, no, I can see it through your pants. What the fuck! That is the faggiest shit I have ever seen. Aw, Derek. He’s getting a boner from the thought of you plowing his asshole.

/Fuck, fuck, fuck people are really looking now. God, why am I getting even harder?/

Jordon: Guys, shut the fuck up and just let it go. People are starting to look at us weird.

/Wait, what? Jordon is coming to my defense? I don’t even know him that well…/

Derek: Yeah, I guess we don’t want everyone knowing what a little bitch we are drinking with. Just, for fucks sake, order a beer or something next round. But for real, can we agree that he would be the bitch in a gay relationship? He’s got a tiny waist, wimpey arms, we all know about the daddy issues, and as Patrick has pointed out apparently has a boner.

Jordon: Guys, fuck off. Let’s just get back to drinking…

Patrick: Ha, of course Jordon would jump in in defense of the gay relationship. We knew he was experimental but, fuck, I didn’t know you were that experimental.

Jamie: Yeah guys, let’s move on. So, how is the new job going, Patrick?

/Do I really look that feminine? Would I make a better girl? huh, I guess I should try and get rid of this boner and get back to the conversation, at least it is moving on… But, why are Jordon and Derek now looking at me./

/It is the end of the night and everyone is leaving. I see Jordon approach me. Derek and Patrick are smashed and Jamie is heling them into a Uber./

Jordon: So, I did notice your boner earlier. No, you don’t have to be embarrassed about it. Here, just let me have your number and we can talk later. I’ll text tomorrow. It was a fun night, and have a safe trip home.

Sunday morning:

/I wake up later than normal, around 11. Thankfully I don’t have a hangover and start my day normally. The whole time I keep checking my phone to see if Jordon has texted me./

/Ding! Oh shit here’s a message/

Jordon: Hey, so that was pretty fun last night. This may seem forward as I don’t have definitive knowledge, but are you seeing anyone?
/No, no I am not…/

Me: Hey, no I’m not now and uh yeah, your intuition is right.

Jordon: :) yeah, I thought as much. This might also seem a little forward but you are very feminine, and seem excited by the idea of being feminine. Do you think of yourself as a girl?

/damn, he figured that out too? Uh, how much do I say? I’ve fantasied about that for years, I’ve felt like that for years. But, I don’t even know him. Eh, fuck it. It seems like my friends already know, and he is pretty cute…/

Me: Well, you seem to have figured me out pretty quickly. Yes, it’s something I’ve fantasized about for a long time. I’ve thought about that a ton and it’s something I want to try, I want to learn how to be a girl.

Jordon: Then I will teach you. Do you want to learn?

/Oh god, is this happening? Am I about to have sex, with a man!/

Me: yes, I want to learn

Jordon: Good. Here is what you will do.

Jordon: you will go shopping, buy a wig, make-up, dress, stockings, shoes, pantie, and bra. You will then spend the rest of the day learning how to do your make-up, shaving and preparing your body, and practicing your new voice.  You will not pretend to get the materials for anyone else. If you are asked what they are for you will be honest. You will tell them that you are becoming feminine.

Jordon: You are going to make a very pretty girl.

/Wait, what? God, is this… is this happening? Am I ok with this? Well at the very least I’m excited by it… I already have an erection just from that text. I need to respond. What do I say? “oh, sure thing lets become a girl just for you”, “sounds good, I’ll see you tomorrow.”, “yes, sir”? What am I doing!/

Me: Ok, I will do it. I will do everything you told me to do.

Jordon: Perfect. What is your new name?

Me: Karen, My new name is Karen.

Jordon: Karen, that is a pretty name. I will see you tomorrow, Karen.

/Shopping was not as bad as I thought. Only a few people asked questions about the items I bought but the few that did I answered like I was ordered. I told them they were for me. The wig was for me, the make-up, all of it. It was embarrassing, for both of us. But apart from the humiliation nothing bad happened. After shopping I spent the rest of the afternoon and evening practicing make-up. It is way harder than it looks. Thankfully there are a ton of tutorials and I think I managed to get it done right in the end. Hopefully I look good for Jordon tomorrow.  /

Date Night:

/God, I cannot believe I am about to do this. I just spent most of the afternoon getting dressed up. I hope I look good. Well, here it goes. I have to leave sometime. I hope no one sees me…/

/You sneak out of your apartment, hoping against hope that no one sees or recognizes you. You feel so different. The make-up feels heavy on your face while the dress you are wearing, a light blue dress that is cut just above your knees, feels light… it feels wonderful, it feels right. You get to Jordon’s apartment without anyone recognizing you. You knock once on his door/

Jordon: Hello! It’s great to see you. You look wonderful, come in, come in.

/What a nice smile he has. Maybe this will be worth it, maybe I look good. Judging by the grin Jordon seems to like it/

Jordon: Would you like a drink? I think we should talk for a bit. We have some things to figure out before we start.

/Yeah, I’m pretty sure I will need a drink tonight…/

Jordon: Sit down. Did you enjoy shopping and dressing up for me?

Me: Yes, yes I did.

Jordon: Good, do you like these parts of being a girl? Because let’s be honest. You are shit at being a boy. So, do you want to try being a girl for the rest of the night, Karen? Do you want to be Karen for the whole night? I will teach you. I will train you but only
if you promise to listen, if you follow my orders, and only if you will be my little boy slave, the little boy that I turn into a girl.

/Wait, what, Slave!?!?... I want to say no but… I always wanted to try this. I love this stuff in porn /

Me: Yes, Sir. I understand and I want this. I’ll be yours tonight, to train, to be your girl. But, I’ve never really done any of this before…

Jordon: Perfect and don’t worry, I am more than happy to teach you. I love teaching new subs.

Jordon: Now there are a few ground rules. This whole situation is about our pleasure. If you don’t like something you must communicate with me. If we are in a role playing situation you should use a safe word. The safe word I normally use is Bob Ross. Yeah, yeah, yeah, I know it’s funny. But, that’s kinda the point. Can you think of a situation where you would use Bob Ross in a sexual way. No, that’s what I thought, you can’t. The other thing is that you are to refer to me as Master or Sir tonight. Remember, if for any reason you are unconfutable use the safe word. It doesn’t have to mean the end of the night or even the end of a particular… activity, so use it.

Jordon: Now I need to know you understand. Repeat the safe word, tell me my titles for the night, and that you want this.

Me: Yes, Sir. I am to only call you sir or master, I am to use the safe word if I want something to stop, to get out of a situation, or because I don’t like something, and, the safe word is Bob Ross.

/I can’t help but let out a little snigger as I say Bob Ross. Jordon smiles as well, a warm caring smile at my reaction to the name. Then, he changes. He sits up straighter, his smile vanishes, and he speaks to me firmly/

Jordon: Now, stand up and turn. I want to see you, all of you.

Jordon: Very nice. Now take the dress off and come on my lap.

/As I turn you start to become excited, nervous, aroused. Well, I must be doing something right, as I feels Jordon’s erection as I sit on his lap. His hand start to grope and run his hands over my body/

Jordon: You feel wonderful. Close your eyes.

/I feel his lips press against my own and feel his tongue forced into my mouth. I feel his left hand grip into my neck pressing on either side. He continues to kiss me and moves to kiss behind my neck, my cheek, and move to my breast. The pressure is building in my head; I can feel the blood pounding as Jordon keeps his hand wrapped fully around my neck. /

/I almost feel high from this breath play. Jordon places his other hand around my neck and physically lifts me and pushes me against the wall. Pinned with one hand still pressed against my neck/

/Jordon reaches into my panties and starts to massage my little cock. I am so excited that I am already leaking pre-cum. As soon as I feel his rough hands touch me my eyes burst open. I… I am about to cum already/

/Softly but with an amount of authority I had not heard yet. Jordon says/

Jordon: I told you to shut your eyes. Keep. Them. Shut.

Jordon: Are you really this impatient? Now you will have to wait. Good sluts suck cock and remember, you are a slut tonight so get on your knees

Jordon: Very good. Now, be a good slut and put your hands behind your back. No touching, you obviously cannot be trusted to control yourself. Now please your master and suck. Not so quickly, take your time. This is going to be a long night for you.

/He’s right. I am to excited and want to cum already. I want his cock so bad. I want to see how far I can take it in my mouth. I want to feel it in my ass. I want him to make me a whore, his whore/

/I take my time and warm my throat. I take my time and soon I am taking his cock deeper and deeper into my throat/

Jordon: You can open your eyes now. Look at me. You really do make a much better girl. You make a great whore.

Jordon: Are you ready to be fucked?

/Fucked? Of course I am. I want it so bad. Maybe I will be allowed to touch myself them. I already want to cum so badly…/

Me: Yes, I want to be fucked. How do you want me?

Jordon: Follow me.

/He takes my hand and leads me upstairs to his bedroom. The room is spacious, its walls are painted a light grey, the king size bed is center to the room and the headboard is a dark leather. But my eyes are drawn to the leather St. Andrews cross on the left wall. Jordon can see me staring at the cross /

Jordon: Not tonight. If you are girl for me you will get to play with all my toys. Tonight, you learn the basics. Now, take off the rest of your clothes and lie on the bed.

/As I take off the rest of my cloths I see Jordon open his walk in closet. Inside there is every toy imaginable. Flogs, whips, gags, restraints, ropes, dildos, handcuffs, vibrators… everything and anything I could have thought of is there. Unfortunately for me all he brings out is a bottle of lube and a small dildo./

Jordon: Lie back, we need to make sure you are relaxed. I can see that you wearing the butt plug like you were instructed. Good.

/Jordon gets on his knees in front of me and I feel a small amount of lube flow down me and my butt plug moved in and out. It feels so good that I try and stroke myself…/

Jordon: Hands aside! You do not have permission. You can play with yourself as soon as you can fit my cock inside you.

/Master takes his hard cock in one hand and slowly presses it against my hole. Slowly it pushes inside of me. Master begins to move in and out of me faster and faster… fuck it feels good/

Jordon: You may stroke yourself now. But, you cannot cum yet. Good toys cum from being fucked, not from playing with themselves. You must stop when I tell you, and… do not cum unless I give you permission.

/Well shit, he better give me permission soon because I have been waiting for thirty minutes to cum…/

Jordon: Take your hands away.

Jordon: Good, now you may cum but, keep your hands away.

/Master grips my hips and pulls me to the end of the bed. Oh god, he is pushing his cock even deeper into me… I cum all over my stomach and chest as Jordon, I mean Master fucks me even harder. Master pulls his cock out and shoots rope after rope of his cum over me. I can feel his warm cum hit me/

/He leans over me and once again grips my neck. As he squeezes he kisses me, once. Then he growls into my ear/

Jordon: Good little slut, good whore, good girl. You get to do this again. You’ve been good.

/He stands up and looks down at me. Almost all the lust, the emotion, all of it is gone… That’s him, that’s my… Master?/

Jordon: The shower is this way, follow me.

A New Type of Party:
/Jordon texted me the next day asking if I was ok, if I enjoyed it, if I wanted to keep doing it. Of course I want to keep doing it. I have never felt so sexually pleased then I did after last night. I want to do it all again. I want to do so much more, I want to work through that whole closet/
Jordon: Hey, so there is a life style party this weekend. A good friend is hosting it. Would you like to go?
Me: Sounds fun. But, what exactly is going to happen is I go? What happens there?
Jordon: Well, a ton of different stuff. Some people like to be watched, some people like to watch, some people like to play with different people. Some people like to show off their slaves, share their partners, or just use other people’s nice toys. I know the host and they always host respectful, safe parties. We could discuss doing whatever you want. If you want, I know several other guys and or girls that would love to play with us.
Me: Wow, that’s a ton of stuff….
Me: I mean, yeah it sounds amazing. I’m not really into girls, btw, but you should “play” with whoever you want. Would you really let me play with other guys at the same time?
Jordon: Gotcha, that is not problem and of course I would. As long as you are being good and following my orders I love to share. Is there anything in particular you would like to try? The party is Saturday evening, starts around 9.
Me: Yes Master, I will be good and follow all your orders. I want to try having sex in front of everyone and, are you sure you would share me? I want to try that most of all…
Jordon: Then, we will make sure both of those fantasizes come true. Prepare like you did last time and I’ll pick you up at your place on Saturday. Also, make sure you get a new dress evening dress. I’ll pay for it you just need to pick it out.
Me: Any preferences?
Jordon: Yeah, one that will make me horny. Let’s be honest you are not going to be wearing it for long. Once you find the dress, send me a few pictures of you in it.
Me: ok… why do you need pictures?
Jordon: Well, first of all your answer should have been “yes, master” but I’ll forgive the laxness over text. Secondly, I am going to masturbate to them then I will be sending them to some friends. They will want to know what you look like before the lifestyle party.
|As you pull up in Jordon’s car you see a huge house with at least forty parked cars|
/Well, Jordon’s friends are doing well for themselves. This place is basically a mansion. No, it actually is a mansion…/
Jordon: Now, do you still remember the safe word and our rules? You are going in as my submissive again.
Me: Wow, this house is amazing and yeah, Jordan I understand that.
Jordon: Good, well understand that there are a large range of activities going on tonight. We can try the ones that interest you, watch those that you want to see and avoid those you don’t like.  In other words, we are going to be in a new… different place so, communicate with me.
Jordon: Oh, and your pictures made quite an impression. Almost everyone has already seen you and there are more than a few volunteers.
Me: Already? You, you sent my pictures to other people and what, offered me to them?
Jordon: Yes, I did. Remember, you asked for this and anyway, you belong to me tonight. I can share you however I see fit. Now, a good submissive would thank me for organizing this for her. So, thank me. Thank me for sharing you with my friends.
/Wow, this is really, uh, going fast but, I do trust Master and I’ve always wanted this…/
Me: Yes, Master. You do own me tonight and I have wanted this. I just, I didn’t this it would come so fast.
Jordon: You’re welcome.
/As we get to the front door Jordon knocks and the front door immediately flies open. A couple is standing there and both are beaming. Their smiles and warm greetings starkly contrast with the black leather suits they are both wearing. The woman also has a collar, leash around her neck, and ears. Both give Jordon a hug and I am introduced/
Jordon: This is Elizabeth and James. They are our host for the evening. This is Karen.
James: Hello, Karen. Jordon did not tells us just how pretty you were. We are so glad you came. The festivities have not started just yet. So come in and have some food or a drink before we start.
/As I enter the house it is not what I expected. Its bright, open, and friendly. It’s not at all a sex dungeon. Then I see the people in the main room. It is a ton of people… some of whom seem to have started the party/
Elizabeth: Well, sir I guess we the party has started.
James: Yes it has kitty, now get on all fours and follow me.
/I slip my hand into Jordon’s in the hope that there is some normality there and thankfully, there is. Master leads me into the middle of a large group of people and tells me to sit on