by John Rivers
She looked at me with the most puzzled expression I’ve seen in a while. I thought she was going to tell me I was crazy, but after a few moments, she nodded her head.
Opening the lubricant, I smeared it on the end of the device before rolling my chair out to set the object about three feet from my desk.
“Now, if you’ll come over here and bend over for me, I’ll put a little lubricant on you.” Once she did as I asked, I instructed her to spread her cheeks. I lubricated her well. I even managed to get the tip of my finger in her butthole.
“Ok, I want you to hold onto my desk for support and squat. Once you’re almost down, I’ll be behind you and align it.”
If anyone were to wonder why the few women I’ve handle so far have been so cooperative, they need to remind themselves that women don’t come to places like mind to acquire dignity. I’m sure Gina was also aware she’d have to suffer a little indignity. This was probably the most humiliating thing I had yet subjected a woman to.
I rolled my chair behind her. As she brought her small butt near the floor, I position the object as near as I could. Even at that, Gina had to release the desk with one hand and center the tip with her rectum.
“You don’t have to take a lot, just enough to get a hold with your sphincter.” I watch as the shaft entered her small puckered hole. When I saw she had taken about three inches, I said, “That should be enough, now get a good grip with your sphincter. Make sure you’ve got a good grip before you raise yourself up.”
I almost felt bad about having her do this when the poor girl raised up and it immediately slipped out of her butt. I wondered if anyone could have picked this thing up like this. I was certain she wouldn’t have any success no matter how many times she tried, but I was going to have her do it a few more time simple for my amusement.
“Ok, Gina, we’ll go on to the next phase,” I told her after she tried three more times without success. I had decided to use the examination table. With my paraphernalia in hand, I headed across the room. It took a while to get the top section secured in place and the stirrups pulled out. By the time I had completed that task, Gina was waiting. I patted the area of the table where she needed to take a seat. Once she was on the table and placing her feet in the stirrups, I went to retrieve the wooden stool I’d left at the table with the upright posts. I had considered using that table for this procedure, but I felt her anal area would be more exposed on the medical table.
Once I was seated and pulled on a pair of gloves, I placed a hand on each side of Gina’s small, but cute butt to slide her down as far as possible. I then did a complete examination of her butthole. It was still covered with the lubricant I’d applied earlier. It was indeed small. It was also hairless. Like around her small, but cute vagina it was totally void of hair.
“This isn’t very dignified, is it?” she stated timidly as I applied another liberal coat of Vaseline. When I didn’t immediately answer, she went on. “But you know what, it’s sort of fun.”
“I’m glad to hear that, honey,” I assured her. “I’d hate to make you uncomfortable. By the way, did you have a Brazilian?” I was referring to the absence of hair in her nether region.
She laughed. I watched as her belly giggled. “I started to ask a stupid question: how did you know, but you can pretty much see for yourself, can’t you?”
“Yes, ma’am. Pretty much.” I had started to massage her butthole. It might have loosened a tiny bit more. I don’t think the test did anything to dilate it. I massaged a little firmer. I heard her moan.
“Oh, that feels so good.” I looked up to see her eyes were closed. There was also moisture forming in the crevice of her vagina.
After a couple additional minutes of rubbing, I decided it was time to attempt inserting the first joint of my index finger. I managed to insert the tip, but there was a lot of resistant. I had my job cut out for me. At this rate, it would be a while before I could even think about inserting the inflatable butt plug.
I glanced up to see that Gina now had a breast in each hand, massaging them. Her eyes were closed and her breathing heavy.
I came up with an idea. I placed a hand on her inner thigh a couple of inches from her pubic area and shook it to get her attention. “Gina, I think if your bottom was warmed a little, your butthole would loosen. I’m going to spank you gently for a while.”
“Please,” was all she said through her heavy breathing.
I stood. Being right handed, I stood on her left side. I had already positioned her so her bottom was four inches or so over the edge of the table. I could spank it without my hand also striking the table. After spanking her for a while and hearing no objections, I spanked a little harder. After a couple of minutes of this, I reclaimed my seat and began inserting my finger for the second time. This time it was looser, but pulsated against my finger. She had stopped rubbing her breast and was looking at me questioningly.
It was then I chose to be a “dirty old man.”
“Gina, why don’t you step down and lay across my lap so I can spank properly. I think that will work better.” I didn’t know whether it would make an iota of difference. I simple wanted to lay this little naked doll across my lap and spank her cute little butt.
To my surprise, before I knew it, Gina was down and had positioned herself across my lap. Alright!
I spanked her for a good five minutes before I tested the waters again. This time, although it was snug, she took my entire finger. It was time to insert the inflatable plug.
“Gina, honey, why don’t you get back on the table and we’ll go to the next step.” Once she was back in place, I scooted her bottom down again. This time it was pink from the spanking. Taking the forefinger and thumb of my left hand, I spread the anus enough to insert the plug into her rectum. I should have known, but I was soon made aware the device was not going to stay in place at the opening. To remain in place and inflate, it would have to be past the sphincter. Left with no other option, I push it past that critical point and inflated it just a little. I then pulled it out, dilating her as it passed through the opening. I reinserted it again and inflated it a little more. I pulled it out with no great problem. With the object coming from the other direction, her anus was momentarily expanded to a diameter of approximately two inches.
“Hey, guess what, I think we’re having some success.”
“I can feel it when you pull it out. It feels good. I wasn’t sure how it would feel. I’ve never had anything up my butt before.” She chuckled and her belly jiggled.
I inflated the plug considerably more and started to extract it. It wasn’t coming out without exerting some force. I didn’t want to do that. I released some of the air and pulled it through this time. The bulb must have been at least three inches in diameter but it passed through her anus with no great problem. I decided I probably shouldn’t push my luck. I certainly didn’t want to hurt this young lady.
Laying the device aside, I inserted my finger and made wide circles. I had no idea I would have ever dilated it this much. On the other hand, in an hour or so, it would be back to normal. I had one more idea.
“Little Bit,” I said, “why don’t you come over here with me. I want to take something about the size of a penis and see if I can insert it, ok?”
She offered no argument as I helped her down. I took her hand and led her over to the horse. I instructed her to mount. She offered no argument and once she was positioned with her butt pointed upward, I patted her on one buttock and told her I would be right back. Taking my keys from my pocket, I went to the locked cabinet. There I found a good size butt plug. Going back and standing behind the tiny woman, I began to insert the devise. Although it took a while, I was finally able to insert it. I was proud of myself, I had done what I set out to do.
“It’s in, Gina. Congratulations.”
“Don’t take it out just yet, it feels so good. I wish Bill was here to fuck me right now.”
I didn’t say anything. I just let her enjoy the mome
nt. I placed a hand on her butt and rubbed it. Her pussy was dripping.
“Sir,” she said after a couple of minutes, “I know I shouldn’t do this, but could you fuck me in the ass?”
“I’ll try, honey, but we’ll have to remove the plug first.”
She laughed. “I know that.”
I removed the butt plug and damn if I didn’t drop it on the flood close to where I’d dropped Savannah’s. I then helped Gina off the horse.
“Gina, I want you to bend over and grasp your ankles, ok?”
Once she was position to my satisfaction, I dropped my pants and placed my throbbing erection against the same orifice I had just spent an hour dilating. No matter how hard I tried, I simply could not penetrate it. I tried and tried to no avail.
“Gina, I’m pretty large and I can’t get it in. I’m sorry, but I’m going to have to put it in your pussy. Just keep holding your ankles.”
With the petite woman still in this position, I grasped her about the hips and lifted her a foot off the floor and simply slid her onto my erection. Rather than thrush myself, I pulled her back and forth until we both reached a climax.
Chapter Eight
Gina left feeling quite proud of her new butthole. I didn’t have the heart to tell her that it would return to its original size tomorrow. At least now she wouldn’t be afraid to use it. I went back to check the phone again. It was flashing. I glanced at the clock to note the time before answering. I don’t know why; I didn’t have any place to go.
It was another woman wanting me to call her back. As always, I did. She answered on the third ring. Her name was Della and she wanted to know if I could take her this afternoon. I could, I told her, but I’d like to have a general idea what she was expecting.
“You are the expert, sir. I’ll just leave it to you. I just feel I need putting through my paces, if you know what I mean.”
No, I didn’t know what she meant; that was why I asked. However, I didn’t push the issue. She wanted to know if she come over in about an hour.
I said sure, gave her my address, and went to fix me a bite to eat. Other than toast, I hadn’t eaten today. True to her word, Della was ringing my door bell in approximately an hour.
Della was a little different besides the fact she was black. Well, not extremely black, but enough you could call her that. She was somewhat attractive, despite the fact she was well over six feet tall and weigh somewhere around two hundred pounds. She might have been a little fat, but mostly, she was just big. Again, I asked her what she would like. I got much the same answer. Ok, so I started quizzing her.
“Do you want a spanking, Della?” I asked. I certainly wouldn’t be able to put her over my lap as I had Gina.
“If that’s what you’d like to give me, sir.”
I hadn’t been called sir in the last five years as much as I had in the last five days. That still wasn’t an answer. “Would you like to be humiliated, Delta?” I thought I saw a flicker in her eye. I decided I would put Della through her paces, as she had said. I’d also try doing it the way John said Burt would. Have them undress upstairs.
“Ok, Della. I want you to go into the middle bedroom and remove all your clothes. When you’re naked come back in here and we’ll discuss this some more.”
Five minutes later, Della was back, as naked as she was ever going to be. I had never seen an Amazon naked before. I was going to enjoy putting her through her paces. “Della, since you haven’t told me what you like, we’re going to do what I like. First, I want you to get down on your knees and crawl. Crawl to the kitchen and back.” I watched her big butt jiggle as she made her way to the kitchen on her knees.
“Okay, Della, let me think. I’ll tell you one thing I going to do before we’re through: I’m going to take you down to the dungeon and hang you by your feet. While you’re there, I’m going to use a ping pong paddle on your big butt. What about that? Wouldn’t that be humiliating?”
“Yes sir,” was all I got out of her. I was into it now; here was a submissive if ever there was one.
“I tell you what would be humiliating, Della. That would be to call my friend and let him come over here and see you naked and hanging upside down. While he was here, I’d let him put a big plug up your ass and then let him whip you. Would you like that?”
“Yes sir.”
“Speaking of putting a big butt plug up your ass, stand up and turn around and show me your asshole.”
As instructed, Della stood, turned around, bent over and spread her cheeks. It was so hairy up in there, I couldn’t actually see the hole. I racked my brain for something else to make her do. For the moment, nothing came to mind. To stall, I motioned her over to where I sat. I had her turn around and I began slapping her oversize butt cheeks. I slapped them several times before I could think of anything else to humiliate her. I came up with one more idea. After this, I would have to take her to the dungeon.
“Della, I want you to go back to where you were. I want you to lie down with your bottom towards me. I want you to draw up your legs as well as spread them. I want to get a good look at that pussy. Stay that way until I tell you to move.”
As she was instructed, Della lay on her back, drew up her legs and exposed herself to me. Spreading her legs, she split herself to the point her labia was separated. With the light at a different angle, I could now see her anus.
“I can see your asshole now, Della.”
“Yes sir.”
After a couple of minutes, I stood and fumbled in my pocket for my keys. “Ok, Della, you can get up now. We’re going to the dungeon and I’m going to beat your big ass.”
After I had Della suspended by her heels, true to my words, I inserted a butt plug up her ass after spanking her for several minutes with the paddle. Once assured the plug was going to stay in place, I commenced to spanking her again. I stopped long enough to tell her I was going to continue spanking her until she told me what she really liked. She never did.
Chapter Nine
I didn’t know it at the time, but I was going to get a lesson in hardcore BDSM. Yes, I had suspended two of my clients so far. Any way you look at it, that was somewhat drastic. More so considering I had hung they by the heels. The same ones I had suspended, I had thoroughly whipped as well. I use the term “whip” to denote any strikes to the body with the numerous objects one can use to do so. The bare hand can be used. I would think the next step up from that would be the paddle. My favorite was the ping pong type device. It would sting like the devil, but left no serious damage. Of course, there were larger paddles. I supposed some people used them. I didn’t intend to use any of these. In fact, I was intending to remove some of the objects that were placed on the wall during my departed uncle’s tenure. The large paddles were going to disappear simple because I didn’t want anyone hurt during the Saturday night events.
There were riding crops in various lengths. They were all but innocuous except in the hands of a nut case. Believe it or not, there are nut cases in the world. There were the whips. I thought of a whip as a device with a handle and flexible leather strips. There could be multiple strips as on the shorter ones or there could be a single large strip as found on the “bull whip.” I didn’t like the presence of the “bull whip” because it could cut if not administered correctly, but I would leave it out for a while. Several of last Saturday night’s clientele had used it. I made a mental note to ask John if anyone had ever been seriously hurt with the device.
As I said, I was about to get a lesson in this business. Monday morning, John called me. He asked if my schedule was open this afternoon. I told him that so far it was. In fact, at the present, I had nothing on the agenda. He chuckled and said that would change. Once most of Burt’s old clientele became aware that I was continuing the public service offed by my uncle, the phone would be constantly ringing.
I said I hoped so although I had been somewhat busy as it was.
He went on to say the reason he called was because he had a couple from out
of town that would be here this afternoon. Every time they were in town, they called him for a session. However, he had always given the session in Burt’s dungeon. I recalled him telling me that he had a small dungeon of his own in his garage where he catered to a small number of people. The session this couple, or least this woman, received required more than he could provide. She was extremely submissive and the husband liked to watch. John wanted to use my dungeon.
There was no problem there. After all, John was my newest best friend.
A little after one o’clock, John rang my doorbell. Along with him was a distinguished looking couple dress quite expensively. The man wore what could have been an Armani suit. (Of course, I doubt I would recognize an Armani suit as such.) The woman’s red business type skirt and white blouse had not come from Sears. I stepped back for them to enter.
The man could have been forty. He was rather dark skin with black hair. The woman was a few years younger and a blond. Whether the hair color came from a bottle or not, she was a knock-out and built like the old proverbial brick edifice. John introduce them as Bob and Marsha. I doubted that was their actual names.
They wasted no time. Within a couple of minutes of entering, John removed a collar and leash from his back pocket. Today he was wearing jeans as opposed to the leather of Saturday night. He fastened the collar around the woman’s neck and grasp the lease. He looked at me.
“If there’s no one else in the house, we’ll let her undress right here.”
“Just me,” I confirmed.
“Ok, pussy cat, let’s get you get naked.”
The husband had stepped back and taken a seat in a living room chair. He pointed at another chair. “Have a seat,” he told me. I did. I guess that was his way of telling me it was alright if I watched.
I guess I should have known by now that thigh-high stocking and high heel shoes were an accoutrement of BDSM. If not, I was reminded again. Pussy cat, or Marsha, removed her skirt first to reveal that was indeed the proper attire. Her thigh-highs came almost to her butt.