How Far Would He Go

This story was inspired by a Domme that wanted me to write a story about being with a man. It was at first just a few paragraphs. She then wanted more and suggested I add various elements. She knew it embarrassed the hell out of me to write it. But then she knew how much I was a victim of my own sensuality and more would follow. She knew she just need to give a little push and gravity would take over from there. I appreciate any and all comments.

A message showed up at my email;

Unknown:

I've been reading your profile Burglvr, and your posts to different groups. So you like having women control you? Sniffing panties, kissing ass; you don't have to tell me but I bet you sucked on a few strap-ons and had a few butt plugs in your ass? Are you a really sissy?

Burglvr:

Well not really, I'm a masculine guy and it is just for fun. I don't recognize the name. Did I write you Mistress?

Unknown:

Forget who I am for a moment. I think your lying to yourself. I think I know you better than you know yourself. I believe you need to be taught a lesson. Anyone that likes women's panties in their face, kissing their ass, tonguing their ass, spanking and ... dare I say it...sucking on their strap--on is not just playing. I bet your getting hard right now as I repeat it, aren't you?

Burglvr:

what kind of lesson do you want to teach me? I'm not into pain or anything like that. Are you a Mistress? Do I know you? What do you want me to do? Where are you? I do have limits.

Unknown:

Oh, I understand. You won't do anything you don't want to. I know something you want. Do you want someone to suck on your cock? Hmmm.

Burglvr:

Yes Ma'am, who wouldn't?

Unknown:

that is what I thought. Would you like to reciprocate? Have you learned enough on a strap-on? Hands off that cock, I will own it when I am done with you. I have a pair of panties; I will make you sniff and taste. I also have an ass you will kiss. But you will have to ask for it. Now tell me you're a sissy or this is the last you will hear from me. Now cocksucker!

Burglvr:

(I was quiet, I didn't know what to say. Who was it? My heart was racing. ) "Ok, don't go; I'm a sissy, but it is just for role-play. What do you want me to do?

Unknown:

See I know that deep down all sissies are little sluts. They don't like to admit it to themselves. I like to teach that lesson. A little pussy is dangled I front of their face and they will do all kinds of nasty things. Now from the ads I read about you, that you are willing to serve and to service sexually is that correct? Hmmmm....Well I know lots of women and I will have them call you to confirm the validity of what I say. Pass my little test and they will be available to you. It seems like you have a fondness for women sitting on your face. How far would you go for that?

Burglvr:

so it isn't you that I service but one of your lady friends? i would do just about anything for that. How do we proceed?

Unknown:

Well you will have only one requirement, sissy boy. I am a man and you will suck a real cock until you can make me cum. I will show you how. Since you think you're

Not really a sissy, and just a "role-play" I will teach you how to suck, but you will not be allowed to cum. That's right big fella, you're a real man, and you wouldn't cum with another man would you? I agree, unless, that is you are a real cocksucker? Now if along the way If you decide to do so do so without my permission you will owe me three big blow jobs. So be careful or your going to have lots of work to do. Now do a good job, learn how to suck a cock, and don't shoot your wad, and you go home with a shameful little experience; but I'll recommend you to some beautiful mistresses that love a guy comfortable with his

Masculinity. OK. These ladies would love to sit on your face and have the sweetest pussy. A real man can't turn it down. How about you sissy? As for the panties and the ass kissing I will allow you to do that to me only if you ask, lets even say beg for it. Oh I've known a few boys that once they get are a little teased they can't say no to very much. Those might be my sweaty jockey shorts or a pair some cum slut left here because he was embarrassed to go home after he shot a load in his shorts, when I grabbed his crotch; but only if you ask for them slut! Oh I bet you'll sniff them and be hard. How about another side bet? Oh yeah I read how you begged to suck some mistresses ass. i will let you beg to spread my cheeks, I'll bet you you'll be moaning with your tongue buried in my ass. Maybe you will owe me some more cock sucking if you blow your load with your tongue in my ass. Now maybe you're laughing, thinking this guy is a nut. But I bet you're going to ask to kiss my ass and you're going to be moaning when you do. I know you better than you know yourself. Your hard as a rock now, aren't you?

If you are a sissy slut you will need even more and I will teach you what you are. I need a new suck slut. Now call this number, soon--- he disconnected.

Burglvr:

Holy shit. I was just about to kick him off my IM but I was in shock. I would never. No way. i caught my hand scratching at my crotch. I pulled my hand away, a little pissed at myself for my reaction, and I walked away from my computer. I got a beer and sat back. i couldn't ignore it and it didn't go away.

Ahh, I was just horny. I was going to go surf the net. I needed to look at some women and get this guy off my mind. Hey, maybe it was a Domme. One of them that wanted to play with my mind. Maybe i should call, what could it hurt. I could always hang up if it wasn't a Domme.

It was probably the Mistress Sarah that had so much fun and laughed at my embarrassment when she had me suck that strap-on. God I loved it when she sat on my face. She probably put that guy up to it. No one else knows I did that. It was nasty and I'm not sure I ever want to do it again.

I called the number and a women answered. Ahh, I was right.

This is Burglvr. I believe that maybe we were on the computer about a half hour ago.

I said to myself, see you got yourself worked up over nothing. You need to go with the flow and quit being so reserved. But it didn't sound like Mistress Sarah and it wasn't her phone number so maybe there was more to this game. But she had to be behind it. Maybe she just had a friend looking for someone with my kinks.

Mistress:

Oh you called back, good boy. Say can I call you back in 5 minutes, honey.

Sure. I gave her the number. The phone rang 10 minutes later. Hello Again Burglvr, she answered, I wasn't the one you were talking to online. You see there is a real man, and i do mean a REAL man that takes care of us here. He screens out men for us if they are real men they can play with us or we dominate them as they please. I believe you would love to meet us but you have to get screened out first. So hold on and Sir will be with you in a minute.

Is this real or is this a game. It sounds too good to be true on one hand, but again an elaborate game and test. Even if it was some guy, she said ladies, as in plural.

Unknown:

Sissy boy you called back. Not many do. Only the real men that get the key to the ladies, or the sissy boys call back. You know where I think you stand. Are you ready or are you going to wet your pants and hang up?

Again my mind was spinning. Do I actually go forward? I guess I could pull back. I still bet that this guy is just part of their game. What did I tell myself a few minutes ago? Go with the flow. "OK, what are the rules again?"

I'll send you package. There will be instructions, maybe a little treat the ladies and I can put together, and more information meeting instructions. The rules are as I told you. I'll show you how to suck cock; don't blow your load, or else you have some more work to do. Then you open your mouth. I'll feed you the bone. If you learned your lesson, its over quick, you have a nasty taste in your mouth until you brush your teeth and the ladies are open to you. Blow your load and you load and you have more work to do. When we are even you are free to go and the ladies are yours. My guess is that by that time you'll want more time on your knees in front of me, and they it will get interesting. Everything else you want and get you ask you ask for.

Burglvr:

So worst case scenario, I can't hold it, I have to do some more; are the ladies open to me when we are done?

Unknown:

Sure, we can do that. As soon as you get caught up on your obligations you're free to go. But I'm still betting you're a little sissy cum slut when we are done. Now Mistress Rose that spoke to you a minute ago thinks otherwise and we have a little bet on it. She has as a cute round ass I'd love to fuck, so if she loses you can polish her ass clean with your tongue after you lick me clean. Do I send the package? You can always cancel?

Burglvr:

ok. I whispered.

Unknown:

what was that, I didn't hear you? How about Yes sir?

Burglvr:

Yes sir

A few days later I received the package. I can't believe they now had my phone number and address. I received the package and it contained more than some instructions.

slut,

Enclosed is a little outfit for your adventure. A few frilly things I'm sure you will enjoy. Don't worry it will fit. Mistress drove by the house the other day to check you out. At 8 o'clock each night, for the next week, I want you scrub your ass and cock clean. Your ass is probably not used to this so, put a dab of Vaseline on you asshole so it doesn't chap. I bet you're the shy type when it comes to your asshole! Put on your outfit. Pile some pillows, at least three, and get over them on your stomach ass high. Have this other envelope with you and call Mistress Rose.

Sir

The frilly stuff fit and I am a big guy. This clearly is someone that knows me. I felt like such a...., heck I don't know, but I was in the privacy of my own place. I called Mistress Rose.

Burglvr:

Mistress, this is burglvr

Mistress Rose:

oh hi are you dressed? Ass up over the pillows. Ready to start?

Burglvr:

yes ma'am.

Mistress Rose:

Does the outfit fit. If I was there I would be inspecting you and pulling it down or up to best expose you, I'd give you a few swats on your ass so you would remember. I want you think of me having you wear it. It will make it easier for you. Are you lying over the pillows with your ass high in the air? Oh, I bet it feels a bit naughty. I should have sent a picture of my nice round ass. But I figured it would only make it worse with you having a hard cock wearing all that stuff. Ready to begin?

Burglvr:

Yes Ma'am

Mistress Rose:

Open the envelope.

I gasped as I saw a man's jockstrap. Whew it was sweaty pungent.

Mistress Rose:

We will meet next week. You have the location and i will pick you up in my new Porsche, so I'll be easy to recognize. Now here is one more rule. You can't cum this week. Now, Sir sent you a jockstrap. I want you to think that you are behind me doggie style pounding away. Pretend you're a real man, rather than some sissy sniffing a sweaty jock that has been go d knows where. (Pretend?) So give those pillows a little hump for me. No Cumming or staining the underwear, sir will spank for that. Now give that jock a big sniff, come on let me hear you. Now wouldn't you prefer to be rubbing your little thing up against my bottom rather than sniffing that stinky old jock?

Burglvr:

yes Ma'am

Was I imagining things? Did she say Pretend to be a real man? My little thing? Where had that jock been? Okay I'm just getting sensitive.

Mistress Rose:

Good now stay like that and I'll call you back in twenty minutes. Give me one more sniff and a nice little hump. Keep sniffing and humping, but no cumming. She hung up.

She called back 20 minutes later and told me to be ready the next night. I was in the same position when I called. She asked if I was sniffing the jock and humping the pillows. I said yes. She asked if I had scrubbed my ass clean. I said I had washed. She asked had I used the Vaseline. I said no there was no problems chapping. Listen to me closely and obey me, go get a warm wash cloth and the Vaseline, then back over the pillows. I did and was back in position. Now you're going to need both hands, she said, so slide the jock over your head. Now reach back and slide down the panties. Good now scrub your bottom, harder, I want to hear you working it. Good now put a good dab or that Vaseline on your anus. Rub it in good.

I am going to call you back in twenty minutes. When she did she said she had me do this because Sir would inspect me. So she wanted to be sure I passed inspection and knew how to clean myself before I met him. She said she would call me the next night, but wanted me to have a few things ready. She said, I want you to have q-tip, a banana and some rubbers. I think you will find the best deal on a twelve pack. I want you washed clean, panties down when I call. She hung up. She called and asked me to explain what i had done getting ready and my position. She asked me to wet the q-tip and inset it in my bottom about an inch or two. She had me twirl it and run it in and out a few times. When told to pull it out she asked if it was clean. When I hesitated she said 'you're not washing properly. Soapy finger at least two knuckles deep. She told me to put the dirty q-tip in a baggie she wanted to see I was doing it when we met. If you can't prove that you are doing as I say I will call it off. Next she had me take out a rubber and put it in my mouth. Ok bill both hands on the banana. Now put the rubber on the banana using just your mouth. Ok I'll call back, tell me how much you can fit in your mouth.

Twenty minutes later the phone rang; how much she asked as I answered the phone. I don't know exactly a mouthful for sure. Put it in your mouth and moan a bit as you do it so I can hear. William, take it deeper, unless you're experienced I would expect some gagging at his point. I'm disappointed with your effort. Did sir tell you about our bet? I don't want him fucking my ass so you better do a good job. Now I will let you fuck me if he loses the bet. Now hump those pillows and think of my nice round ass. While you're doing it practice sucking tonight. Tomorrow same position practicing on the banana. i want you with the q-tip in your ass when you answer. Are you sniffing the jock? Good boy now hump those pillows for me with the cock in your mouth. Good we'll show sir you're no cum slut.

Oh, bill have a big cucumber tomorrow. I don't want you intimidated by Sir's size. You will see why I am taking this time to train you. You can only guess how the week went. My jaws where sore as she had me keep it in my mouth.

Finally, the day had come. I was so fucking horny that when the time came I got dressed in the panties and bra provided and met with Mistress Rose. I still was sure Mistress Sarah was behind this. Then I threw on some jeans and a shirt over it. I was ready.

She had me bring some humiliating items, the q-tip from the inspection during the week. The banana and cucumber. She stopped on a back road to give me last minute pointers. Her hand on my thigh was driving me crazy. She dropped me off at his house.

I guess I got so caught up with Mistress Rose that I sought of forget in a scene about what was about to happen. While the thought was lingering in my mind, I still thought this to be a hoax by Mistress Sarah. I was almost positive she would be who I was going to meet. I mean who knew about my sucking on the strap-on and such?

When I showed up it seemed like a regular house. He answered the door. Oh shit. He seemed OK so I went in. I was nervous. What the fuck was I doing? How did I get myself into this mess? Oh shit.

Take off your clothes he said, as he sat back and watched. I was standing in the frilly things. He walked off with my outer clothes. He reminded me of the rules. He would show me how. I was not allowed to cum or I owed him three more. I agreed. I was nervous. He laughed at the outfit and grabbed at my crotch. These things are wet, he said. You are one hot little bitch. It didn't help with all the teasing I got from Mistress Rose before I showed up. He slid his pants down and told me to get to my knees. He began to stroke me. Then he put his mouth on my cock.

No please don't do that. I cried out. I'm sorry I need to leave.

He grabbed my balls and held them firmly. You better pay attention. i told you I would teach you. If you leave you going to leave like that, and not get your pants back. Because you owe me.

I was torn in that I thought I would never do this. Being sucked seemed as humiliating as the thought of doing it. Way was I so hard? i couldn't get hard with a man sucking me. Oh no... He was going to need to slow down, or I was going to cum.

Please that is enough! I'm too close!

You don't get to tell me how much to suck on you. It is my job to show you how to do it properly. If you think you know how, I will let you suck my cock right now. So when you are ready you will tell me that; "Sir, I need to suck cock".

His mouth was down upon me again. I easily tried to push his head away, but head his hand on either side of my ass cheeks. Oh I was close. "I need to suck cock."

He continued.

"Sir, I need to suck cock NOW" He stood and told me to sit on the couch. He took out

His cock and put it in my face. I think you need to be taught a lot more before you're ready to suck cock; but let's see.

Oh shit, I can't do this. I looked at it in front of my face. I was never this close to a cock like this. God it was too humiliating. I tried to do it and get it over with but i couldn't.

Get on it sissy, or I'm back on you. I opened my mouth expecting him to put it in. He just slapped my face with it. Beg for it and take it.

I put it in my mouth and tentatively sucked. After a short period he pulled it out and said that I was a lousy cocksucker and really needed to be shown how to do it. Again he was on me. I was still quite excited from his previous sucking and was at the edge again.

My efforts to tell him to go easier or stop had no effect. I need to suck cock. I said again.

You told me that earlier he said, but you did not really want to suck it. He went back at it.

Sir I really need to suck cock. i was almost hopping from foot to foot trying to not cum.

Ask me to spank your ass and teach you how to suck cock.

With a bit of hesitation, I almost came, I yelled it out. What, he said? Please, spank my ass and tech me how to suck cock. I could feel that my face was red with shame, so hot I felt like I was sun burned. Standing there with my cock bobbing and just moments from cumming.

He took me over his lap and playfully spanked my ass. It wasn't meant to hurt but to continue to tease. Between his slaps he stroked my cock. He kept me on edge by stroking me and slapping my ass. I was close again. He kept me there for a while. I could feel the warmth of my ass and the need to cum badly. But I really didn't want to keep going. Or did I?

Ok slut your mouth needs to be taught a lesson in humility. Rather than asking to suck cock tell me you want to tongue my ass.

No, I definitely can't. I won't, that isn't part of our deal.

He laughed, oh your right sissy. His hand was on my cock stroking and I was soon begging.