Wednesday finally arrived. I kept myself busy in the morning, but made sure to arrive punctually at 1:00 PM at Samantha Smith’s door.
“Why, Joseph, you’re right on time. Good boy,” she said.
I felt like a dog. I fully expected Samantha to be dressed provocatively in some outfit designed to titillate, but instead she was dressed very conservatively. She wore slacks and a sweater. She actually looked very preppy, and this I found disappointing.
She again had a list of items she wanted to cover on the computer. First on the list was organizing her “Favorites” in Internet Explorer. I took her through the menus and showed her how to create folders and group her bookmarks. Then she wanted some instruction on streaming video. Before I knew it the hour was up, and I was standing at the door ready to leave.
“You look disappointed, Joseph. Is something wrong,” Samantha asked.
“No, Mrs. Smith, nothing at all. I’ll see you next week,” I replied.
I tried hard not to think. I didn’t want her reading my thoughts. I didn’t want her to know just how disappointed I was because in reality I was extremely frustrated. I expected to see her breasts again today. I thought we might progress to a new level.
“Were you expecting more today?” she asked.
“I don’t really know what I expected, Mrs. Smith. All of this has been very… different,” I said cautiously.
“I see. Well, here’s something for you to consider for next week. I would like you to give this a great deal of thought. How far are you willing to go to get what you want?” she said coyly.
“I don’t understand,” I said.
“Just think about it, Joseph. I’ll see you next week,” she said with finality as she closed the door.
I was totally obsessed with Samantha Smith. Why had this voluptuous woman taken such an interest in me? Maybe it was because she could read my mind which gave her a distinct advantage over me.
I pondered the question she put to me before I left on Wednesday. ‘How far are you willing to go to get what you want?’ I had done her bidding up to now. I was willing to involve myself in her kinks in order to see her magnificent tits. God, I did so much already, and that was only for the privilege of seeing her tits. What would I have to do in order to touch them? Would she even allow me the opportunity to touch them? I think she would, or she wouldn’t have posed the question. She wanted me to think about it. She wanted me to consider my own limits. Was there a point where I would draw the line and say no? Was there something she would request that I would absolutely refuse to do?
Of course, I had limits. I wouldn’t do anything that involved another man. If she even hinted at something like that, I would be out of there. I would not fuck her. That was reserved for my wife only even though we were going through some rough times right now. That was my fault because of my obsession with Samantha Smith.
I lived for Wednesdays and that day had finally arrived. At 1:00 PM sharp I was ringing Samantha Smith’s door bell. Would she be all business today? Would she be dressed like a school teacher? I waited in anticipation for her to open the door.
“Hello, Joseph, you’re right on time,” she said, standing in the doorway.
My jaw dropped open. I must have looked like a fool. I never expected to see her dressed like this. It revealed a whole different side of her. This was beyond kinky as I knew it. After all, I was just a small town boy who never strayed from the normal conventions of society. This was stuff I read about in erotic literature.
Samantha Smith stood there in black leather over the knee boots with what looked like six or seven inch heels. I mean she was practically standing on her toes. On top, she wore a leather corset that pushed her breasts up and in, displaying a considerable amount of cleavage. Her nipples peaked over the top of her corset. She looked so hot.
“Today we won’t be working on computers, Joseph,” she stated.
“Oh, but I thought…”
“Please don’t interrupt me,” she said, cutting me off.
“I’m sorry,” I replied.
“Let’s retire to my bedroom, and I’ll explain what’s going to happen today. Our session today might be more than an hour. Actually that will depend on you,” she stated.
I followed the gorgeous red head into her bedroom, watching her succulent ass sway back and forth.
“I gave you a question to consider before you left last week. Do you remember the question, Joseph?” she asked.
“Yes, Mrs. Smith, I do,” I replied.
“Good! What was the question?” she asked.
“You asked me to consider how far I was willing to go to get what I wanted,” I replied.
“Yes, precisely, and did you consider how far you would go?”
“Well, yes, I did toss the question around in my mind for a bit,” I said.
“Fine, that’s all I asked you to do, Joseph,” she said.
She paced back and forth for several minutes. She looked as if she was in deep thought.
“I’m not receiving any of your thoughts today. That’s strange. I usually can pick up something,” she said more to herself than to me.
She then walked up and turned with her back to me.
“Joseph, undo the stays on this corset. They’re much too tight. Besides it’s too hot to be wearing this damn thing anyway,” she said.
I quickly loosened and removed the leather stays as she directed. She was going to remove her corset! This was better than I expected. My cock grew hard at the thought that she might expose her magnificent tits again.”
“I don’t like you to refer to my breasts as tits! That’s crude. Do I make myself clear?” she hissed.
“I’m so sorry. It won’t happen again,” I muttered. There was no sense in fighting her on this. So much for not being able to read my thoughts.
“Damn, the first thought I pick up from you today, and it has to be you using that word,” she complained as she removed the leather corset. She then turned around facing me, wearing only her over the knee boots.
My jaw dropped open at the vision standing before me. As she paced back and forth, her breasts bounced up and down on her chest. It was truly a magnificent and arousing sight. My cock grew harder, and I thought I might cum in my pants.
“Now, Joseph, what do you want?” she asked.
“Well, I could use a new car,” I said.
“No! No! No! Other than looking at my breasts, what else do you want from me?” she said irritated.
“Well, I would like to touch your breasts,” I replied.
“Is that all?”
“No, I would like to squeeze them and pull on your nipples,” I said.
“Well, yes, I would like to kiss your breasts all over and take your nipples in my mouth and suck on them,” I added.
“And maybe bite lightly on your nipples as long as it brought you pleasure, of course,” I said.
“Is there anything you would like to do even if it was something I didn’t want done to me?” she asked.
“Are you serious?”
“Of course, I’m serious, Joseph. I wouldn’t be asking you if I wasn’t serious,” she retorted.
“OK, fine! I’d like to tie your hands behind your back, and then bind your arms at your elbows so that your breasts stuck out even more. Then I would have you spread your legs wide so your pussy so exposed. I would then rub your breasts to get you aroused, and then I would pull on your nipples. I would increase the pressure as you got more aroused. I would tease your hot pussy by rubbing my cock all over your clit. Then I would smack your breasts and watch them knock into each other. Is that enough, Mrs. Smith?” I asked, irritated by her superior attitude.
“Yes, I think that’s quite enough, Joseph,” she replied.
She walked up to me and let her breasts brush against my chest. My knees went weak at the contact.
“I will allow you to fondle and kiss my breasts, but no rough stuff, yet,” she said. “However, I do want something in return. Would you like to kiss and fondle my breasts, Joseph?”
“Yes, of course, I would,” I replied.
“Would you be willing to let me do something to you in return,” she asked.
“You mean like what I did last time?” I asked.
There was a moment of silence as she considered. She looked me straight in the eyes as I stole glances of her breasts rising and falling on her chest.
“No, this would be something new. It’s what you would call moving to another level. After all, you’re moving to a new level by kissing and fondling my breasts.”
“And what might that be?” I asked.
“I want to... sodomize you?” she said.
She laughed at me.
“Are you that naďve? Do you not know what sodomy is?” she asked.
“Of course, I do,” I said, irritated.
“Have you ever been sodomized?”
“Of course, not!”
“Listen carefully, Joseph. What I am proposing is this. If you want to get your hands on my breasts, then you must let me take your virgin asshole with my strap-on dildo,” she said.
She put her arms around my neck, pressed her luscious tits against me. I could feel their warmth and their fullness. She then brushed her lips across my ear.
“It’s all a matter of how far you’re willing to go to get what you want,” she whispered. “You want something, and I want something in return. Am I worth it?”
My legs were shaking. My cock was so hard that my balls were aching. What was happening to me? This had turned out to be much more than a computer call, and I’d managed to dig myself a deep hole. How could I say no and walk away from this woman? How could I say yes? It would destroy me.
“If I agree, how much time do I get?” I asked, trying to stall her.
Mrs. Smith laughed.
“As long as it is pleasing to me, you get as much time as you want,” she said.
“And what if it isn’t pleasing to you? What if after a minute or two you decide that you’re simply not enjoying it?” I asked.
“Then you will stop, and you will leave,” she answered with a smug look on her face.
“In other words, I have to take all the risks, Mrs. Smith,” I stated.
“That is correct! How much faith do you have in your ability to turn me on?” she smiled. “Allowing me to sodomize you only gives you the opportunity to touch my breasts. The rest is up to you. I mean, think about it. Why would I let you fondle my breasts if it brought me no pleasure?”
It was quite obvious that the world revolved around Samantha Smith. It was all about her. I could walk out right now, and it would be over. I’d seen her. She was half naked right now and leaving nothing to the imagination. I would have the last laugh. I could leave here with my dignity in tact. I would have won. I could return to my wife with a clear conscience and get on with my life. Well, maybe not with a clear conscience, but at least with the knowledge that I resisted temptation and won.
On the other hand, I could stay and let her sodomize me. Oh my God, what a degrading act, but then I could get my hands on those monstrous breasts that I so desperately wanted to touch and hold. I could bury my face in her mountain of flesh. I could suck and lick and bite those massive mounds.
What should I do? God, I wish there was an easy answer. I really wanted her. It was like taking a child into a candy store, but then telling him that he couldn’t have any candy. He could only look but not taste.
I couldn’t walk away. I wanted to taste her. I wanted to possess her.
“All right, I agree to your proposition,” I said.
Mrs. Smith became animated, and was visibly pleased by my answer.
“You have made a wise decision, Joseph. My breasts are my pride and joy, and not many men have had the opportunity to caress them. Now, take all your clothes off so we can get started,” she ordered.
I removed my clothes and stood naked before her for the first time. My cock was hard and sticking straight out from my body. I felt so self-conscious standing there naked in this woman’s presence. It wasn’t that I was in poor physically condition because I wasn’t. It was just that not many women had seen me in the nude.
“Now put these leather cuffs on your wrists and ankles, Joseph,” she ordered.
The cuffs were made of fine leather and lined with a soft material. They buckled close and had a D-ring attached to them. I quickly attached the cuffs to my wrists and ankles. I then stood there waiting for further instructions.
“Follow me,” she ordered.
Mrs. Smith led me to an open area of her bedroom that contained a raised, carpeted platform. This platform was approximately three feet wide by five feet long.
“Now get down on your hands and knees on that platform.”
I lowered myself to my knees and assumed the position she demanded. She kneeled in front of me and attached my wrist cuffs to rings concealed in the floor of the platform. She then moved behind me and did the same to my ankles, spreading my legs further apart. Samantha certainly had everything planned out well.
My stomach was queasy. I felt so helpless, and, at the same time, I knew that I had made a mistake. I should have left when I had the opportunity. I could have put all of this behind me. I may have had some regrets, but I could have held my head high rather than end up shackled to the floor at the mercy of this woman.
She placed a full length mirror in front of me. I looked in the mirror and say how pathetic I looked shackled to her floor on all fours. She then approached me from behind with a riding crop in hand. I could now see the reason for the platform. With her strap-on in place, she would be at the perfect height to sodomize me.
“This mirror will give you a better view of the proceedings, Joseph,” she said as the riding crop came down on my left ass cheek. “I’m so glad you opted to participate in my little adventure.” My right cheek then felt the sting of the crop.
“Hey, wait a minute. You said nothing about using a riding crop on me!” I protested.
“Joseph, I need to get you into the mood,” she replied.
“Oh no, I want none of this. I’ve changed my mind. Let me go!” I protested.
Mrs. Smith without saying a word released me.
“Get dressed and get out!” she said dismissing me.
I felt awkward as I quickly gathered up my clothes, got dressed, and left.
My stomach was in knots as I drove home. I couldn’t believe that she actually intended to whip me and then take me up the ass with her strap-on dildo. I thought she was miss prim and proper when in reality she was a very kinky lady.
What was most upsetting was that in this whole scenario, there was no sexual gratification for me. She would use me to get off, and then she would allow me to give her more pleasure by having the honor of touching her tits. There was something wrong with this picture. I was making all the sacrifices and even risking my marriage while she was the only one who was really benefitting.
I figured I’d wait a couple of days and then call her to see if she wanted to keep our appointment for the following Wednesday.
I called her on Friday, but there was no answer. I tried again on Saturday with no success. In the meantime, she was constantly on my mind. I couldn’t get the image of her standing there in only her over-the-knee boots out of my head. The more I thought about her, the more I wanted her.