Sandra's Fantasy Ch. 02byTappy_McWidestance©
BY Sandra and Tappy McWidestance
Author's Note: Please read chapter 01 before reading chapter 02 or you will be pretty lost. Like chapter 01, chapter 02 will be told from multiple points of view.
*** Sandra's POV ***
After Nicole left I masturbated for 2 hours straight before finally peeling myself off the couch. I walked back to the kitchen and poured myself a cold drink of water. I wanted to shower, but I knew I had to write my journal to Mistress D. While I wrote every detail and every feeling I had during my encounter with Nicole, my arousal began to build back to where I'd been when she arrived. I didn't understand why the two women had that affect on me, but soon I had a very real need to cum again.
Finally Mistress D appeared in the chat room and we immediately went into private where I confessed all the sordid details of my sins to her. She continued to press me for details about my life, which concerned me, although I was very forthcoming with her and never once considered lying. She had me tell her my typical schedule for a work day, where I worked, when I was in the office and she had me describe myself.
"I have blonde hair. I am 5 foot 6 inches tall. I weigh 121 pounds and my measurements are 36C-27-37. I told her I was a little softer than I was as a young woman (I already told you my daughter is the hard body in the family now) but that I still have an hourglass figure which can draw attention."
I told her my entire sexual history. How many partners I had in my life? (12 give or take) Did I suck my lover's cock? (Yes sometimes if I was hot enough) Did I have anal sex? (No never) Did I have group sex? (No, but I thought about it) Was Nicole my first woman? (Yes) The interrogation went on and on.
She pressed me to send her a picture which I reluctantly did. I felt like she was getting all the information she needed to stalk me. I questioned her after I sent the picture. That was probably not the best time to do it but she told me not to worry. She told me that wasn't the case. She said she wanted to know what I looked like and my personal habits because she was going to train me to be an obedient slave she needed to know everything about me to do so. I wasn't reassured.
I was expecting her to have me perform for her that night, but she said it was late and she had to get up early. I was disappointed. She told me to expect a package at work on Monday and that Monday night we would chat again. That meant I had two days upcoming without her. I knew I would be spending the weekend in front of the computer. My Friday night only plan would be coming to an end.
*** Rose's POV ***
I was in shock after Jeannie sent me the links and passwords to my mother's favorite websites. I'd never seen such filth and couldn't imagine my mother reading and watching what these sites provided. Still, as I looked at the sites trying to figure out why she would find these lurid stories and dirty videos exciting, I found myself strangely compelled to continue exploring.
In fact at night in my bed, I found my mind wandering back to some of the characters and fantasies I read about. The next night found me back exploring these sites and it soon became a habit. I had to assume that was how it started for my mother. I didn't find myself reading about the lesbian domination stories she did. Instead I found myself reading group sex stories and found I began to fantasize about being with two or more men at the same time. I even found myself thinking about a three-way with another woman. Maybe someday instead of splitting up with Jeannie at the bar we could pick the same guy and have some fun. I made a mental note to talk to her about it the next time I saw her.
*** Nicole's POV ***
Everything was going to plan with Sandra. I was going to use Mistress D to learn everything about her so I could use that information to snare her deeper into my web. I knew she would be masturbating as soon as I left the chat late Friday night. From what she said in her journal, I knew she craved being told what to do by a powerful woman. The picture she sent me showed her wearing a modest outfit. I knew I could exploit her feelings about covering herself. I knew from seeing her naked at her house that she had beautiful breasts. But she didn't like to accentuate them either in the picture she sent me or in the ones I noticed on the walls in her house. I also knew her nipples were very sensitive and that her ass was made for spanking. I had to figure out how to make use of that information.
Saturday morning I sat down to scheme how best to take this lovely creature Jeannie had handed me and make her my own. My plan came together fairly quickly, but I would need help. I knew Jeannie would be in. That was a given. But I'd need more help. I had a friend who worked at a local upscale hotel. She'd been able to get me a deal on a suite before. It is a business hotel so on the weekends it is pretty empty. I'd have to give her a call. I also had to figure out how Mistress D would play into the scene. I didn't want Sandra to find out just yet that we were the same people. I also didn't want her to know Jeannie was in on the plan. I'd have to think about that a little more. One thing I did know was I wanted Sandra conflicted about serving me and Mistress D. After some deliberation I decided that I would write a note and drop it off at her house. It would tell her we would be going out on Friday. It would also tell her I expected her to be a good girl and not masturbate until we were together. Then as Mistress D, I would give her exactly the opposite instructions and see what she does. Oh how I enjoy tormenting a new partner.
*** Sandra's POV ***
I woke to a beautiful sunny day on Saturday. My life had been turned upside down but I felt great. The world seemed right as I sat down to read the paper and eat breakfast. Thinking back to last night, I felt my arousal begin to creep back into my body. I was tempted to reach between my legs but I wanted to wait. The anticipation of delaying my orgasm was exciting to me. This world was still new to me and I wanted to keep it special as long as I could. I decided to go for a run, something I rarely did. But the day was too nice to waste indoors. I put on some shorts, a t-shirt and a jogging bra and headed out. The local park was teeming with activity as everyone seemed to have the same idea I did about enjoying the day.
Every time I passed a woman who was the right age for how I perceived Mistress D I would think about her. Of course there were more girls around Nicole's age on the jogging trail. I thought about them too. Although I was outside with people, my thoughts were completely focused and contained on my desires. I'm sure if I asked my daughter for her opinion about what I was doing she would say I was crazy. But I didn't care. Some basic animal need had been tapped and there was no going back now.
When I got tired of running, which was pretty quick, I found a bench and decided to people watch. Everyone looked so normal and I found myself wondering who was secretly kinky like I discovered myself to be. It was a wonderful distraction although I could feel the moisture building in my shorts. I decided it was time to head home for a shower.
As I walked up to my front door I noticed an envelope taped to it. Somebody had left me a message. It was from Nicole. It was a simple note. "Sandra," it began. "You are a very passionate woman. Next Friday I intend to find out just how passionate you really are. We will be going out. I will make all the arrangements. I will send you instructions Friday morning. Until then, don't masturbate. I want you hotter than you were last night." It was signed XXX-Nicole and there was a bright red lipstick kiss on the bottom. If I had touched myself I would have cum on my front stoop in an instant.
*** Jeannie's POV ***
I had talked to Nicole that morning. She had stopped by to show me the note. I thought her plan was devilishly clever. Rose had been emailing me questions about her mom. I could tell she was coming around to the thought that what her mom was doing on the Internet was exciting. Of course she didn't know what Nicole had done to her last night and she certainly didn't know what we had planned for the two of them. Rose had told me we should go out and pick up a guy together. She didn't know it, but that would work just fine with my plan to seduce her. I told her I couldn't make it this Friday, but the Friday after was open. By then Sandra would be where Nicole needed her to be and that would give Rose an extra week to get excited.
*** Sandra's POV ***
After reading the note I got inside as quick as I could. The order from Nicole not to masturbate was going to be impossible to follow. I barely made it inside before I pulled my shorts down and furiously frigged my clit. I had a little orgasm. It wasn't great. I was a bit surprised because my arousal level was very high, but the release was minor. I sprinted up to my bedroom to get my trusty vibrator. I turned it on full and started to fuck myself. It felt great, but I still couldn't have the nice juicy release like I had last night. I came again, but it was another little one almost not worth the effort. Then I realized my mind was rebelling against Nicole's wishes and that must be what was holding back my passions. Dejected I pulled the vibrator out of my pussy and curled up into a ball.
I didn't sleep. I was thinking too much for that to happen. Why was I so enthralled by this girl that she could now apparently control my orgasms? That thought scared me. I decided to get up and take a shower. Refreshed I tried to go about the rest of the weekend without thinking of Nicole or Mistress D. It was a losing battle and a constant struggle to keep my hands outside my panties, but I made it. Once I got back to work on Monday, it would be easier as I could concentrate on my job.
I had not slept well Saturday or Sunday night, but I had managed to stay off the Internet. The temptation to disobey Nicole would have been too great and I feared unsatisfying as well. Monday morning flew by as I was back to my regular bitchy self treating my subordinates like dirt. In fact I had not thought of sex at all until my admin assistant knock on my office door at 11:45. She was holding a flower box.
"These just arrived for you Sandra," she said. "A new suitor we should know about?"
I had completely forgotten Mistress D said she would be sending me something today. I had not expected flowers. I was at a loss on how I could explain a woman I'd never met but chatted with on the Internet was sending me gifts. I mumbled something about nobody special and asked her to place the box on the corner of the desk. My assistant wanted to open the box and get some water, but I told her I would take care of it. I didn't want her seeing who they were from. As it turns out, that was a very good decision on my part.
My assistant left with a disappointed look on her face. I quickly dropped what I was working on and opened the box. Inside were a dozen red roses. The flower of passion I remember thinking. My own passion instantly returned. In the bottom of the box was another small box. It was good that my assistant had not seen that. I opened it up and there was a piece of ornate glass. At first I didn't recognize the shape, but once I unfolded the piece of paper with it, I knew what it was.
"Sandra," the note began. "Whatever mistress you ultimately serve will want your ass prepared for her. From our conversation you said you were an anal virgin. That must be rectified. A woman's ass is a source of great pleasure as you have many nerve endings. From now on when we chat I expect this starter plug to be inserted in your backside. I have included a small tube of lube in the box. You will need to buy more. I also want you to buy a larger plug. You will struggle with this one tonight, but soon it will become second nature and you will feel empty without it. You will want something larger then. Be online tonight at 9pm."
I couldn't believe she had sent me that. I also couldn't believe the tone of her instructions like I would just ram a piece of glass up my butt because she said so. I quickly tossed the small box into my purse and found a vase for the flowers. I knew my assistant would want to see them.
As I sat working that afternoon, I found myself more and more distracted by the box in my purse. My initial negative reaction was starting to give way to intrigue as to what it would be like. Many of the videos I watched had women taking huge cocks and dildos up their asses. I suppose it could have been trick photography, but they seemed to enjoy it. Maybe it wasn't so back after all. I was sitting at my desk trying to work, but I could feel my asshole twitching. It was puckering and releasing all by itself as if to say "try me." My assistant and the other women under my management had all come in to see the flowers and press me about who sent them. That only served to heighten the naughty feeling from knowing what was in my purse.
I had a chat schedule with Mistress D and I knew I'd have the plug inserted before we started. The more I thought about it, however, the more I felt compelled to try it right now. I knew that was wrong. Playing with myself in the office was a line I was not going to cross, but the plug kept calling me. It was telling me everything was alright and that I would enjoy it. Over and over my thoughts left my work and focused on my twitching asshole and the relief (or so I imagined) waiting for me in my purse. I struggled to come up with an excuse why I shouldn't try it right then, although getting caught doing that should have been enough of a reason. Finally at 3pm I gave up. I told my assistant I wasn't feeling good and was going home early. It was the safe play.
My arousal continued to build as I drove home. I remembered Nicole's order not to masturbate, but she didn't say anything about no using a butt plug. Still I knew Mistress D would order me to do much more than just insert it. I didn't know what I was going to do at that time. I'd have to tell her about Nicole's order and then just do what she commanded. I decided honesty was the best policy.
Safely in my living room I pulled the shades shut and fired up my computer. My first stop was some research on anal sex. I really didn't know the ins and outs of it, as it were. Through Google I found many women talking about loving it, some women who tried and hated it and other who didn't try it and said they never would. I found several articles on how to do it right and most suggested using a plug first to accommodate your body to the feeling. Even though it was still many hours before the chat, I decided to try the plug now.
The consensus I had read online was to first use your finger to spread plenty of lube into your butt. I had never even allowed anyone to finger me there so even that was a mental hurdle I had to cross. That wasn't quite true, my doctor had done a probe before but that was for medical reasons not pleasure. I looked at the small vial of lube Mistress D had sent me. It was probably just enough for tonight. She was going to make me go shopping for it tomorrow. I didn't even know where to start looking
My finger with the aid of the lube actually went in easier than I imagined it would. Looking at the plug itself, however, I thought there was no way I could take it. Although Mistress D claimed this was the "small" one, I didn't believe her. The plug came to a point and then tapered out to about an inch and a quarter wide before tapering back down and then finally back out to a wide flat top. From what I read online the shape was designed to stretch your sphincter which would then snap shut around it holding it in. I did find it strangely erotic pushing the plug into my body. I would have never done this for myself, but because Mistress D had ordered it I was actually a little excited to try.
Not surprisingly the plug did not go in an easy as my finger, but with a little strain, pain and a couple of grunts, my ass snapped around it and the deed was done. Once it was in, the pain subsided. I felt full and I knew it was there, but there was no sexual pleasure like I had been expecting. Still I felt a sense of accomplishment at following the instructions Mistress D had given to me. Of course I wanted to masturbate to celebrate my accomplishment, but I also wanted to follow Nicole's instructions. It was a challenge, but I decided to try and buy some lube online so I could avoid having to go to a store in person.
It turns out finding lube was easy. It was also easy to find larger plugs like Mistress D said I would need. The plugs all followed the basic design of the one she sent me. The glass ones were very expensive. I had a sense of pride that she felt I was worthy of such an investment instead of sending me a cheap one. As I had said, money isn't much of an object for me so I quickly picked out two different sized glass plugs and two large vials of lube. I also found a thin anal "teaser" which looked like a narrow ribbed dildo. I decided to give that a try too. The website I chose was several time zones behind me which worked well. I was able to get overnight shipping and a promise to deliver tomorrow. Now all I had to do was wait for the chat.
I quickly learned the first rule of wearing a plug is to go to the bathroom before you start. I didn't have enough lube to take out the plug and put it back in at 9pm so I had to hold back my growing desire to go to the bathroom. I hoped Mistress D would understand and let me remove the plug after I told her I'd already worn it for three hours.
When I finally got back online with her first question was whether I was wearing the plug. I told her I was and how long it had been in. I told her my dilemma and she told me I couldn't remove it just yet. I was secretly thrilled as my need to go to the bathroom was a constant reminder of my submission to her. I asked what she wanted me to do.
"Sandra, I am pleased that you are using my plug. Following your mistress' instructions exactly and without question is very important. The plug is also about your pleasure and I want to be sure you enjoy it."
I could tell she was going to have me masturbate, probably in some strange way. I knew I had to confess my order from Nicole not to masturbate so I told her about the note.
"You need to decide whether you serve me or her?" was the response.
I paused only briefly. "You mistress."
"Good," was the reply. "From our previous conversations I know you are still shy about your sexuality. A good mistress will always have your best intentions at heart. Right now I want to begin breaking down your shyness. You are a beautiful woman and should not be afraid to express yourself as a sexual being."
I didn't like the sound of that. But of course I didn't voice an objection. My pussy apparently didn't understand my internal conflict as it was leaking like a faucet.
"I want you to strip down to nothing but the plug," was the first instruction. That was easy enough.
"Now get your vibrator if you don't have it already." Again that was easy since I already had it. Mistress D asked which room I was in and I told her the living room. She told me that was good. I was to turn on the lights, open the shades and open the windows. I balked and didn't type a response.
"Is everything alright slave?" she typed. My hands were shaking as I finally typed, "yes."
Mistress D was right about me, of course. I was a bit shy about my body. I knew my reluctance about how I look was unfounded. Even at my age I get plenty of positive feedback and can still turn heads. But that didn't make it any easier to open my blinds and stand naked in the living room for anybody walking or driving by to see.