Meeting the LadybyOldGrower©
(All events loosely based on an actual first meeting with a professional dominatrix. Some events are strictly fictional, as most pro dommes won't do anything that could legally be considered prostitution, e.g. sucking, fucking, hand jobs, and the punishments are exaggerated.)
I had dabbled in BDSM a few years ago, visiting a pro domme a few times, but then got away from it. Recently I decided that I wanted to see if I was still into the scene. Previously, I had some cupping, a little flogging with a wide leather flogger, and some mild CBT (weights on my balls and some light penis whipping). This time, I wanted to first see if I still wanted to continue in the scene and if so, how far my limits could go. After scanning the web, I found a professional that I thought would be perfect for me, willing to go soft if necessary but would take me as far as I would want to even fantasize about. I made the appointment for as quickly as I could arrange to get to the city where she lives.
I got prepared as best I could that morning, clean in and out, well groomed, shaved up and down, fresh breath, and was definitely on time. As I walked in, I found a very petite long red haired beauty, with a smile that lit up the dimly illuminated interview room. She had on a low cut black bustier with garters, long see-through stockings, a small black g-string, and tall spike high heeled shoes. She also wore long elbow length red vinyl gloves. A sight that was both alluring and intimidating. Wire framed glasses perched on a delicate nose magnified a pair of striking green eyes and a large welcoming smile set off very white teeth. The bustier pushed up her moderately sized breasts to a point that threatened to overflow the top, drawing my eyes to her enhanced cleavage. I started to harden at the sight and in anticipation despite my nervousness, and quietly followed behind her into a nice sitting area with a couch and a chair, watching her naked cheeks framed by the garters jiggle slightly as she walked, as beautiful a bubble butt as you would ever want to see. I was starting to fantasize that maybe she would forget her rules and I would be getting some sex as well.
As we sat, we talked for a while and I repeated what I had told her on the phone, for this first time I wanted to see whether I was still interested and so I wanted her to try a variety of things. We talked a little longer for her to see what kind of experience I did have and come up with a plan. She was so calm and sweet while we were talking that I wasn't sure if she could be harsh enough. I found later to both my delight and extreme discomfort how well she could do her job. She told me that I was to honestly respond to any questions but I was not to whine and ask for lessening of any activity. She would stop anything at any time but no whining. Grunts, groans, moans, screams or just plain stop was alright, but no whining unless I was specifically asked. When all the talking was done she told me to go to the bathroom, get naked, and not come out until she called me. Once I came out, there would be no more negotiation, just obedience.
I couldn't get over how nervous I was while I was undressing. I stood there shivering from anticipation and lost the semi-hard on I had developed during our time in the interview room. When she called me I came out and stood in front of her devilishly smiling form.
"Put your hands at your side away from your crotch and stand still," she ordered me. "I need to see what I am working with!" slowly walking around me rubbing all along my naked body. "Ah, nipple rings, you didn't tell me about those. That will make for some fun as well as an excuse to punish you a little for not telling all."
Her hand moved slowly down to my cock and shaven balls. At her touch, my cock began to slowly rise as she fondled my balls lifting them in her small hand. "I like the fact that you shaved, it makes it easier to bind without hair in the way. Well, it is not a really big cock, but it doesn't need to be for what I have in mind, and nice balls. A little tight but I will have a lot of fun changing that," she said as she made a ring with her thumb and forefinger around the top of my scrotum pulling it down away from my cock and body, tightening the balls in my sac, while her other hand traveled down exploring the my ass crack. "You did tell me you had an enema before coming here, didn't you? In that case, I can have some fun here then too," she said as her index finger and middle finger played around my ass hole making me shiver
"Oh you react easily, don't you? This could be more fun than I thought." With both hands at my crotch, her face was close to my body and though short, the shoes raised her chin almost up to my shoulder and when she spoke, her breath gently washed over my cheek.
"Uuuunnggggg," I grunted painfully as she suddenly pulled down hard on my balls causing me to bend at the knees.
"Stand up straight!" she demanded. I did but that just caused a dull ache in the pit of my stomach since she kept her grip and only followed me up part way, keeping quite a bit of tension on my ball sack.
"Good, that is much better. Now follow me." I did so as she released my balls and led me into the next room, a concrete room containing a St. Andrew's cross, an ottoman, an overhead winch, chains, a structure I learned in a later session was a whipping bench, and various whips, canes, and floggers.
"Come over here and give me your hands," motioning me to stand in front of the St. Andrews cross with a mirror off to my left side. She then proceeded to buckle my wrists in wide leather shackles with D rings on them that she then attached to a spreader bar that was hooked up to a chain dangling from the overhead block and tackle. Similarly she shackled my ankles to a different spreader bar so that I couldn't close my legs. Walking over to a motor control, she started the motor and the winch pulled my arms over my head to a point where I was just barely standing fully on my feet. Any more, and I would have to rise up on my toes. There I was, standing spread eagled, unable to close my legs or lower my arms. By now, I was starting not only to feel exposed and vulnerable but helpless as well. Even though I was scared, I was still disappointed that I had lost my erection.
"Not hard yet?" she asked. "We can't have that." Putting a little lube over right hand, she moved up behind me, pressed her breasts to my back, reached around, grabbed my dick in her vinyl clad right hand and started slowly masturbating me. I looked down in amazement as my cock inflated despite my nervousness.
Once I was hard enough for her, she moved around to my front with a roll of what looked like baling twine. "I like to bind up men's cocks, they look so pretty that way." First, a few loops around the base of both my cock and balls, a few around just the balls both separating them from each other and my cock, then a weaving pattern around the shaft, culminating in a coil just behind the head. Surprisingly, I didn't get soft.
"The way I trussed you up, you won't be getting soft any time soon."
There was left over string at the bottom of my balls and the head of my cock. Soon, I learned what use she had for them. First she pulled the string holding my balls back between my legs and down tying it off to an eyebolt in the floor behind me, and then she pulled my cock forward and tied it off to the St. Andrews cross. Soon, I felt the twine on my balls being pulled back and I tried to shuffle back but that just tightened the string around my cock until it stood straight out and was painfully biting all along the shaft and head. If I pulled back anymore, I was afraid it would cut and bleed, yet she still pulled on the string around my balls until they were pulled down and back behind me, also painfully cutting into my scrotum. If I moved, back, I would increase the pain in my dick, if I moved forward, my balls.
"Please, Lady...." I began to plead but was cut off quickly.
"Please pull the strings tighter? Good idea," she lightly laughed as she increased the tension until I was sure that I was going to be cut, but I understood then, that any unsolicited comment would get me in more trouble. Once she was done, more sting through my nipple rings pulling them straight out tightly towards the St. Andrews cross, more tension, until I was afraid that much more and the string would pull them right through splitting my nipples in two. I wouldn't be leaning back anytime soon.
Quite gleefully she said, "Look what your nasty cock has gotten you into now."
Around me she went, plucking away at the strings like a guitar, every pluck causing me to moan in pain and fear of cutting myself. Soon my balls were starting to throb, my dick ache, and my nipples sting, my mind concentrating on not moving to add to my pain. Still, because of how tight the string was around my shaft, my erection never subsided.
Suddenly, I stupidly moved forward as I was surprised by the flogger first being applied to my back. God, my balls felt on fire as they were simultaneously pulled further back and down, cut off from my body, and cut apart from each other. I moved backward, to relieve the pain, only to apply more pain to my cock. I was stuck.
"Surprised you, didn't I? Now, I am going to beat you with my flogger for a while, you better not move, unless you want your balls or cock cut up." So there I was, trying my best not to move while stroke after stroke rained upon my back, ass and upper thighs.
Stroke---the pain wasn't all that intense, I was just surprised by the first one. A few more like that and my back started to get a little tender, though painful, it was still no big deal.
"Aaaggghh!" What the hell was that? My back just erupted into a wide band of pain making me almost jump forward pulling the hell out of my ball sack. I moaned loudly. I was sure I must be bleeding but I was determined to stick it out. I moved back, again tightening the string cutting into my dick, it never seemed to loosen just tighten. My cock now stung constantly like it had new paper cuts all over it and I was starting to get a low ache in my stomach from my balls, making me want to try to curl up but I couldn't, strung up like I was. Then more strokes, quicker softer, but they seemed to spread the pain all over my back, but no way was I going to move again. I was wrong. In quick, succession, two, three, four, five, very hard strokes and I was moving again. More pain in my balls, more pain on my cock. I wasn't sure how much more I could take and by now I was groaning and moaning constantly, but I wasn't going to complain, not and risk worse. I was getting ready for more strokes when I felt cool hands running all up and down my back soothing the pain out. But that feeling just increased my pain, as my cock responded by getting more engorged tightening the string woven around it even more. My cock was a constant source of low grade pain now.
"How are you doing?" she asked.
"I am really worried about my cock and balls. I feel like they are already being cut off."
"No they are fine, still a healthy red color, not purple at all. There is some minor swelling. Can you try to handle more?"
I badly wanted to ask her to release my cock and balls but if there was no real damage yet, I steeled myself. "I'll try to continue, Lady."
Expecting a verbal response from the Lady, I was unprepared for the series of hard impacts that landed on my ass instead of my back. My breath whooshed out of me and this time I almost screamed. Her blows came so fast and hard that between the pain and actual physical impetus of the blows, I couldn't keep still and was in a constant dance backward and forward constantly aggravating the pain in my balls, cock, and my nipples as the rings were also being pulled further out now, threatening to pull them completely through the tissue, something I had been able to avoid up to now. All the time she was flogging my ass, she was teasing me.
"I love to turn an ass red. You are only just a little pink so far, you need to be a lot redder before I quit. I do like my handiwork on your back. The pattern reminds me of a quilt I used to have. Your balls are pulled back far enough that I can see them hanging. I wasn't sure if I could get them pulled that far at first as tight as they were to begin with. If I am not careful, I might just hit them by accident. They do make an inviting target."
Occasionally, when she hit low on my ass cheeks, one of the strands from the flogger would lightly slap my sack but other than scaring me, those didn't really hurt my balls, anyway not enough to register through the pain of the pulling and cutting string. Soon I had trouble catching my breath from constantly moaning. Just as I was readying to yell stop, the blows suddenly ended, my ass on fire. Taking a chance, I looked in the mirror to my left just as I felt cool flesh contacting my whole ass to see the Lady pressing her exposed ass cheeks to mine.
"That is pleasantly unexpected," I was able to finally express.
She lightly giggled. "I love to feel the hot fire of a whipped butt." It didn't help me all that much. It soothed my butt, but the feel of her soft cool cheeks rubbing against mine prevented my dick from softening and relieving the pain there.
I heard her footsteps walk away from me and I strained to watch her in the mirror but she went out of vision. Soon I heard her returning and as she approached me I could see an open jar in one hand and some sort of a stand with the other.
"Since you were good enough to clean out your ass, I might as well take advantage of it," she said.
Checking in the mirror, I saw her kneel behind me rubbing some lubricant on her right hand glove. Roughly grabbing my left cheek, she spread me open as much as she could with her left hand and then started working the fingers of her right hand into my ass hole. First she pushed one finger into me, moving it in and out and around lubricating my hole, then after again lubricating her hand again, two fingers. I have played around with inserting smaller butt plugs in my ass before (I had told her so) and so had no trouble as she proceeded to sink both fingers into me as far as she could. She fucked me with those two fingers for a while, occasionally massaging my prostate sending minor waves of pleasure right to my dick keeping it hard, keeping it hurting from the string, causing me to moan in both pain and pleasure. I was to get no pure pleasure from her it seemed, every pleasure would come with its painful companion.
"Yes, your hole has possibilities, loose enough but not so much that we can't use it for some pain in the future. For now though, I will just use it to hold you in place a little better." With that she laughed is such a sweet little girl way, that you would have thought she was a child playing in the back yard with her friends.
This was no childhood game however, no indeed. With as much pain as I was in, I wasn't quite sure what I was seeing in the mirror when she pulled the stand into view. It had a wide, flat, rectangular metal base with an adjustable metal pole standing out of the center and a device I later found out was a Vac-U-Lock attachment that allows different sized dildos and plugs to be attached on top. She picked up a medium sized butt plug, one I was sure I could handle without too much trouble, liberally lubricated it, and attached it to the stand. Scooping up another glob of lube, she again lubricated my anus. I was sweating liberally from all that had happened to me, and trembling from anxiety about what she had planned next. Watching in the mirror, I saw her position the stand under my ass, loosen a knob that allowed her to raise the pole in the center, raise the plug into position with an inch or two of the widening tip just inside my anus. She then stood up, putting her feet on each side or the base while still holding on to the pole. I wasn't sure what she was planning.
"I am getting a little tired of all your moving around, so I am putting an end to it now," she chuckled.
I wasn't sure what she meant since I hadn't been able to move much at all and when I did it just increased my pain, but she had that little girl smile on her face. How can such a sweet smile feel so evil? Without any other warning, she suddenly pulled up on the pole. Since she was standing on the base, the pole moved up freely, shoving the whole plug into my ass in one swift movement until it was buried in my rectum all the way to the base.
"NOOOOOOOOOO," I screamed at the intense burning sensation caused by the abrupt stretching of my sphincter ring and the increased cutting sensation in my ball sack when I reacted to the anal intrusion by rising up on my tiptoes and then coming back to rest on my feet. I was sure I had castrated myself, the cutting pain was so intense and for the first time that session, tears were streaming down my face, and I just yelled over and over for what seemed a long time but must have been only a few seconds.
Before I could get the breath to yell stop, she soothingly said, "It's alright; your balls are fine, just a moment and I will untie them. Can you go on after that?"
It took a little while for me to regain enough mental sense to respond. "I am not sure Lady; I will tell you after you release my testicles."
Quickly and efficiently she cut the string pulling on my balls and unwound it. Removed too quickly perhaps, because my tears just kept streaming from the pain involved in the blood returning to all the tissue constrained by the twine. The cutting pain had gone, but the sharp pain from the returning blood wasn't much better. Surprisingly, my erection had only slightly subsided which did alleviate some of the pain radiating from my cock but not much.
"Poor balls, they must surely have been screaming, but you know it is all your cock's fault. I could see how you looked at my ass, how excited your cock was getting as we talked, and its reaction to my touch every time I handled it or your balls in any way. Even now, your dick is standing at attention, just hoping to get in my pussy. I just can't have it think that without punishment, but I will be merciful for a little bit and give these poor fellows a little rest." As she said this, she softly massaged my balls, bringing them back to life without the constant cutting pain, even though they still throbbed lightly and stung. Again, I moaned in pleasure from that little bit of relief. Of course, this just brought my cock ball to full life, the twine cutting into it again. Like I said, I couldn't get any pure pleasure, what pleasure I would get would have some pain associated with it, but I was getting used to what my cock was radiating. It still hurt like hell but I could stand it a lot better than earlier.
"I think I can go on now Lady."
"If you are sure, I will proceed. Just remember, don't say anything unless I ask you a question, except to stop everything, or I will be even more harsh thinking you are playing games with me. However, if you can't go on, say so at any time."
The Lady went back around behind me but at first I didn't watch her in the mirror being content to close my eyes and try to enjoy the fact that my balls weren't under stress anymore. All of a sudden I felt the plug pushing against my anal ring. Since, it was in as far as it would go, the only thing I could do was go up on my tiptoes as best I could with my legs spread the way they were. I looked in the mirror and I could see the Lady pumping up the pole like it was a car jack and she was trying to raise me up like a car with a flat tire. It only took a couple of pumps and I was as far on my toes as I could go. Still a couple of more pumps forced me to tilt forward a little and induced pain from my anus as the base of the plug was forced harder against my opening.