Sandra's Fantasy - Chapter 02 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.
"Did you do it?" she asked.
I was still struggling. "No not yet."
"You need this if you are going to grow as a sub," she said.
Finally I summoned up enough courage and followed her instructions. I then slumped back down on the couch in shame. I knew the top of my head was visible through the window, but at least my nudity was hidden by the back of the couch.
"It is done mistress."
"Good. Now I want you to get yourself off. Use the vibrator as a dildo and finger your clit and nipples as you like. Think about the follow scenario. Picture your biggest female rival at work. Overcome by passion you have been masturbating like a naughty girl. You are in the bathroom or some unused office. She catches you and drags you back to your office. Your clothes are disheveled and your co-works see her doing this to you. She pulls your skirt down and pulls your blouse open. She then bends you over your own desk and spanks you. Eventually she flips you over and has you masturbate. As you begin to cum she opens your office door and everyone can see you."
I was horrified by both the scene she laid before me and by having the windows and blinds open. But I did what she asked. Later she would tell me this was an exercise to see if I could keep my sounds to a minimum while I came. Slumped onto the couch I really couldn't be seen, but I certainly could be heard. In fact I thought I heard sounds from outside my windows. But I was too far gone to care. The vibrator was working its magic. The thin tissue between my vagina and anal cavity transferred all the vibrations to the plug which buzzed quite wonderfully against my newly discovered nerve endings. It didn't take long for me to realize my inability to have a decent orgasm since Nicole had ordered me not to masturbate was going to be gloriously absent tonight. After all Mistress D had commanded me to cum so I was just following orders.
I didn't think about the consequences of disobeying Nicole. I only thought about pleasing Mistress D. I did my best to be quiet, but I don't think I was too successful. Just as I was letting go, I was sure I heard a noise right outside my window. But the thrill of being caught took center stage and I came. I came hard. I came tensing my body and rolling off the couch onto the floor. By the time I recovered and could carefully peak out the window, I couldn't see anything. The lights reflecting off the glass would have prevented me seeing anybody even if they were there. I looked at the chat log. Mistress D had left shortly after she lay out the scenario. I was crestfallen that I couldn't tell her about my success. I sat down and wrote her a long journal entry before shutting down the computer. I sat a couple more minutes in my post orgasm glow before standing up and shutting the windows and then the blinds. I wasn't so shy any more about exposing myself to whoever happens to come by. Finally I removed the plug. It was pretty nasty so I washed it and then relieved myself. Finally I crawled into bed my lust satisfied for the time being.
Tuesday at the office I managed to get some work done and not think about what happened the night before. I realized I had subconsciously dressed in a shorter skirt than I normal wear to the office. This came as a bit of a shock to me. I kept checking my personal email hoping to have a message from Mistress D or Nicole, but the only thing I got was a tracking number from my shopping the night before.
Since I would not be home when FedEx usually delivers, I had sent the package to the office. I received packages all the time and I knew this would not cause any suspicion like the flowers had. I found myself watching the tracking number waiting for my package. I didn't expect it until late in the day so I tried to stay focused on my work. Thankfully the shipping package was wonderfully generic and nobody had any clue what the contents were. I was still skeptical that I'd ever need the larger size, but I had followed orders and that was the important part.
I didn't know if I'd be chatting with Mistress D that night, but just in case, as soon as I got home I inserted the small plug. I kept the computer on waiting for her, but she didn't show up. Without her order to masturbate, I refrained trying to remain true to Nicole. It was very difficult. Now that I knew how good the plug would feel with my vibrator, it took all my willpower not to diddle myself. The plug was easier to put in this time. I remembered to relieve myself first and it started to feel less foreign.
The next night I tried the medium size plug when I got home. It wasn't that much wider, but the strain of inserting it reminded me of the first time I used the small one. I forced myself to relax and an extra plop of lube helped as I finally snapped around to the base. I took a deep breath. I'd never felt so full. I hoped and prayed Mistress D would appear online so I could tell her of my progress. She finally did about 10pm. I'd had the plug in for about 4 hours at that point and I was ready for action. She told me she had been very proud of my journal entry. Tonight's exercise was to watch someone else while I masturbate. I worried this meant doing it in public but she said it did not. At least not yet.
Her plan was simple although it made me feel dirty. I had told her my bedroom overlooked Jeannie's bedroom. I'd already told Mistress D about my daughter's best friend who lived next door. I had confessed I found Jeannie attractive. Although I had known her almost her whole life, it was only recently I'd begun to feel a sexual attraction.
Mistress D told me to go into the bedroom and move a chair to the window. I could leave the lights off this time, but I was to strip down and wait for Jeannie to appear in her bedroom. I was instructed to watch her and play with myself. Once again I should use my vibrator and fingers as I wanted. I told Mistress D I had no idea when she would be home and was told to just sit and wait. I'd seen her lights on usually around 11pm and I hoped she would not get home late tonight. As always I was instructed to write about my experience when I was done.
I had a chair in my bedroom so that was not a problem. I was glad I could have the lights off. If Jeannie could have seen me sitting in my chair with my legs spread and ass plugged waiting for her I think I would have died. As it were, alone in the dark with just my thoughts, a plug and a vibrator to keep me busy, I felt like the biggest pervert in the world. The silent but relentless parade of my digital clock reminded me of just how long I had waited. My pussy was screaming for attention, but I was determined to wait. Why did she have to be late tonight? Finally at 11:22, I saw her bedroom light turn on.
I wasted no time. I didn't know how long she would be visible. I had hours of mental foreplay that night and knew I could come very quickly. I didn't really need Jeannie to do anything for me to get off, but she did provide an unknown service by beginning to undress for bed. I pretended she was doing a sensual striptease just for me. The larger plug was even more efficient at transferring the vibrations from the vibrator around my entire sexual core. I knew it wouldn't take long. Jeannie was down to her bra and panties. For the first time I wondered if she slept naked, but I didn't get the chance to find out.
My orgasm hit me like a freight train from out of nowhere. I had felt it building, but usually my body stays on the edge for at least a few moments before crashing over. That didn't happen this time. I went directly from strong build up to loud, screaming orgasm. Like Monday night, I was completely unaware of my surroundings. With the knowledge of the windows being shut, I made no effort to quiet myself and I allowed my cum to wash over me like a warm blanket. I looked up when I finally calmed down and Jeannie was staring out of her window. I knew she couldn't see into my room because the window would just reflect her lights since my light was off, but I instantly flushed with embarrassment. She must have heard me and looked to investigate. In shame I slide to the floor and crawled out of the room. I then wrote my journal and took out the plug. I went to bed wondering what Mistress D had planned for me next and then remembered that Friday was fast approaching too. I didn't know what Nicole would do when she found out I masturbated several times against her order. But I was ready to find out.
Friday couldn't come fast enough. My pussy was wet all morning at work in anticipation of seeing Nicole. I could hardly concentrate. My chats with Mistress D had me primed for action and I was ready to submit. Nicole had told me to keep tonight open although I had little more than that promise of seeing her. I wondered just what we were going to do and where we would be doing it.
At 10am a FedEx letter arrived for me. I didn't recognize the sender's address, but I assumed it was from her. The address was several towns away. Was this where I was going tonight? I tore open envelope. There was a single typed page with no signature or identifying marks. It said, "Dear Sandra. Tonight we are going out. However, I am not taking you to a club or some kind of sleazy motel. I want you to dress elegantly as befits a mature educated woman such as yourself. I want you to take your time and make yourself pretty for me. Alluring not slutty. I already know you're a slut and will bring your true self out of you later, but to begin, I want you spectacular for me. Sometime today I want you to go shopping for new lingerie. I want you to come to me fresh in clothes you've never shown a lover before. A new bra (black demi push up), thong, garter belt, stockings and a black choker to match. I will text you with further instructions tonight, but not before 8pm so you will have time to go home and prepare. Take a nice long hot bath to relax your mind and body. Then put on your new lingerie and do your makeup. I do not want you using too much makeup and looking like a tart. At least I don't want that tonight. Make yourself up like you would for a first date. In addition to the lingerie wear a sheer white button down blouse. Make sure the black bra is clearly visible through it. Leave the top three buttons open. You should have just a hint of cleavage. Also wear a black skirt. It should come no longer than three inches above your knee and be slit high up the side so when you sit and cross your legs, the garter snap will show. Remember no masturbating or you will be punished." I was shaking in my seat by the time I finished reading it.
Shopping was not a problem. There is a fancy lingerie shop near the office and that is where I spent lunch. I left my purchases in my car so I would not be tempted to put them on in the office. I already owned a suitable skirt, blouse and shoes, but I'd never worn a choker before and when I tried on a simple black one in the store I felt deliciously naughty.
All day had been a struggle not to masturbate. I wanted to give myself a release so bad, but I knew waiting would make it better. I followed Nicole's instructions to the T. I took a long hot bath and then took my time getting ready. I didn't rush in the least. I setup my Friday night mood candles in my bedroom and slowly put my new lingerie on. Dressing as somebody had ordered me to dress was a new thrill. I'd worn clothes like these before, but always on my terms in order to seduce a lover. I'd never dressed specifically as somebody had ordered. In the end I achieved the Nicole's desired effect. I was stunning, if I do say so myself. Staring at myself in the mirror I looked like the executive I am with just a hint of naughty thrown in. With three buttons open, I was showing a little more cleavage than I would at the office where two buttons would have been the rule. My skirt was shorter than an office skirt too, but not by much and especially in high heels, I have the legs to carry it off. I twirled and saw my calves were tight and right and so was my butt.
As I twirled I noticed the slit of the skirt flip up slightly. I took hold of the opening and pulled it up exposing a generous expanse of my thigh, the top of my stocking and the garter snap. This look was definitely not office issue, but I must confess I was excited by the thought of other people knowing I was wearing the garter belt. My heart was racing at this point. I looked at the clock and it was only 7:30. I had some time to kill.
I sat like a school girl watching my email and holding on to my cell phone. I didn't know if Nicole would contact me via text message, voice or email so I had to be ready for anything. I didn't want to start another activity until I knew what was going on so like a dunce I sat and waited. 8pm came and went. My pussy had begun to throb in anticipation. By 8:30 I was starting to wonder if this was just a test. Maybe we were not going out and she was going to arrive at my door. My pussy continued to demand attention. By 9 my willpower to not play with myself was deteriorating. If she did not contact me soon I was going to be in trouble. By 9:30 I was going out of my mind with lust. Finally I felt my phone vibrate.
"Sandra my Elegant Submissive," it began. "Go to the Cyndmark hotel and ask for Erin at the front desk. She has an envelope for you. Follow the instructions."
That was it. Nicole's orders were clear, concise and to the point. I grabbed my purse, coat and car keys and headed out to my first public adventure. The drive to the hotel was uneventful. I didn't waste any time in the parking lot. My mind and body were primed to see this through and even though I was scared and nervous, I was determined to complete whatever Nicole had planned for me. I walked confidently into the hotel lobby. It was a fancy business hotel I'd never been to before. Being a Friday night, the lobby was almost deserted. I was guessing that Sunday through Thursday things were much busier. There were two women working at the front desk. Both were blondes and attractive. One had long hair and one short. I tried to scan their nametags without looking to conspicuous. The short haired woman was Erin.
I felt very subconscious standing waiting to talk to Erin. I wondered if she knew the contents of the envelope I was to pick up. If she didn't, why did Nicole tell me to ask for her? I stood patiently while both women handled other people checking in. I could feel my weight shifting from foot to foot as I tried to mask my nervousness. I worried that the other desk clerk would finish first and I would have to come up with an excuse why I needed to wait for Erin. Fortunately that did not happen and Erin asked me if I was checking in.
"No. My name is Sandra. I was told you are holding an envelope for me," was my reply trying to sound confident.
"Let's have a look," she said before turning to a bin which held several different sized envelopes and cards. I watched as she thumbed through them looking for my name.
"Here it is," she said handing me a large brown envelope which had a tie clasp at the top. It looked like the kind of envelope we use for interoffice mail. "Is there anything else I can do for you?"
I took the envelope and told her no. I thanked her for her help, turned and made a hasty retreat from the front desk. There was a secluded sitting area where you would wait in the lobby and I made my way there out of eyesight of Erin and the other woman. Taking a deep breath I unwound the string holding the clasp shut. Inside were a couple of other letter sized envelopes and a piece of paper. I pulled the paper out and read my next message from Nicole.
"Sandra, inside you have probably already noticed the envelopes. Each is numbered. You are to complete the instructions from the envelopes in order. Finish each BEFORE opening the next envelope. I will see you soon."
I had expected the note to read "come to room xyz so I can fuck your brains out." Apparently I had more tasks to complete before I'd get my satisfaction. I looked around to see if anybody was watching me and opened envelope number one.
"Begin by finding the ladies room. Choose a stall and open the second envelope." I quickly looked for a sign to the nearest bathroom. I didn't want to ask at the desk. I probably looked a little lost. I saw a sign indicating where the meeting rooms were. Certainly there would be a bathroom near those so I headed off. There probably was a closer bathroom as the meeting rooms were down a long hall, but I realized a very important side benefit was that area of the hotel was empty. I found the bathroom and locked myself in the first stall. I took another deep breath and opened envelope number two.
"Hike up your skirt. If you're not sitting down, do so now. Spread your legs and masturbate through your thong. Don't cum. Get your thong good and wet if it's not already. Bring yourself to the brink of orgasm and then stop. Then open envelope three." Nicole was right to assume my thong was already wet. It also wasn't particularly absorbent so my thighs were equally moist. I didn't need to be told twice to start pleasuring myself. I was desperate to cum and wondered how she would know if I did, but since she always seemed to know what I was thinking, I was determined to follow her instructions to the letter.
It took all of my willpower to pull my hand off my thong without going over the edge. I literally left myself panting on the edge of a massive climax. I almost didn't stop in time as the vision of me spread in a strange bathroom flashed through my mind just as I was pulling my hand away and that was enough to almost take me over the edge even though I had stopped touching myself. My orgasm teetered back and forth as I hung on the edge of climax trying to will myself to calm down but the eroticism of the moment pushing me further into my lustful desires. I held my breath and strained to force myself to calm down. The thong was positively saturated with my fluids and my pussy was pulsating to my heartbeat as my body refused to calm itself. I actually worried that I'd pushed myself too far. I'd always managed to calm down if I stopped rubbing myself, but my body didn't react that way this time. I started thinking about work, my daughter, my few friends, anything to get my mind of sex.
Finally I felt my arousal peak begin to ebb. God Nicole made me hot. I wondered how much longer I would last under her tutelage. I pulled envelope three out and tore it open.
"Pull envelopes four and five out and then put your thong in the large envelope and seal it. Write Erin on the delivery route."
If Erin didn't know what was going on she soon would, I mused to myself. I wondered what I would think if a strange woman handed me an envelope with a wet sticky thong in it. Still it felt good to get the messy underwear off my body. I hesitated before putting the thong in the envelope. I could just touch my clit, cum and go home. But I could feel my arousal starting to peak again and knew I couldn't stop now. I had to see this night through. I put the thong in the envelope and tied the clasp before I lost my nerve. I also looked down at my clit. It was puffy, pulsating and angry looking. One direct touch and I was a goner. Nicole had to know the state I'd be in. Certainly she was going to let me cum before leaving the bathroom. I opened envelope 4. I could tell it contained more than a letter. There was a note, but also a small thin belt.
"Sandra, I doubt it would not take much to make you cum right now, but I need you to hold off just a little longer. Leave everything in the stall and go turn on the cold water. Chill a paper towel with the cold water and hold it on your clit long enough to break your need to cum. Repeat if necessary but failure to control your climax will lead to serious consequences. When you are done, return to the stall and slip on the belt."
I didn't even look at the belt yet or worry about somebody else coming into the bathroom. I swung open the stall door and walked out. My skirt dropped back into place hiding my exposed pussy, but getting wet in the process. I didn't care that I was dripping. I only wanted to please Nicole at that moment. I don't know if it was good or bad that the water temperature at that hotel was exceptionally cold. It was good because it put an instant halt to any eminent climax. It was bad because it hurt like hell when I pushed my makeshift ice pack onto my overheated clit. I gasped as the cold temperature took my breath away. Wanting to be sure I was ready, I chilled another towel and repeated the process. All thoughts of sex were temporarily vanquished. I returned to the stall, hiked up my skirt, sat down and picked up the belt.
There were thin straps which obviously went around the waist and through the legs. There was also a small metallic heart just larger than a watch battery. Its position was adjustable on the front strap. At first I wasn't sure how to wear it, but when I read the engraving on the front it said "heart on" and I figured it was designed to fit over my clit. Weird. I slipped my legs through and then stood up to position the belt where I thought it went. I didn't understand what it would do except rub me when I walked. Oh well, there has to be a purpose. I opened envelope five. Thankfully it was the last one.
"You are doing well and I am proud of you," the last note began. I felt a warm feeling of euphoria wash over me at the simple complement Nicole just gave me. "Tap the heart on and it should turn on." I did and it began to buzz. It was not strong at all. In fact I considered it annoying. It could never make me cum on its own. Then I realized that was not its job. I realized the diabolical nature of it. It was too quiet to hear and too weak to make me cum. But what it would do was obvious and I wasn't happy about it. The note continued, "Throw the envelopes into the trash except the large one with your thong. Return that one to Erin and then go to the hotel bar. It will not be crowded on a Friday except probably a few businessmen stuck in town and maybe a few tourist couples. Sit at the bar and order a white wine. You will be observed and I will text message your phone with additional instructions."
I read the note again. I did not like the sound of what she was ordering me to do. Who was going to be observing me? If Nicole was going to text me instructions it probably wouldn't be her. Did she mean for me to give one of the businessmen stuck over the weekend a special thrill? Or maybe one of the couples knew her and she'd be sending me to their room. I took several deep breaths and headed out of the bathroom. I stopped to throw away the envelopes and straighten my skirt so it didn't look out of place. I couldn't see a bulge where the Heart On was pressed against my clit nor could I hear it. But I could definitely feel it. Summoning my courage I began to walk toward the lobby. Each step was an adventure as my skirt pressed gently against the tiny vibrator. Once again I was aroused, but clearly not to the point I'd not be able to control myself. I hoped whatever was going to happen was going to happen quickly and that Nicole would not let me marinate in my own juices too long.
When I reached the front desk both women were once again with new people checking in. Both were young couples apparently in town for a holiday. I looked at both couples intently. Either one could be in my intimate future tonight. As luck would have it, Erin was not the first clerk to become available. The other woman asked if she could help. I was at another decision point. To me, my thong must reek of my musk and my wetness would soon be soaking through the envelope. I should have run and never talk to Nicole again. Or I could stay and hopefully one of these couples would take me to their room. I hesitated. The woman asked again. I decided.
I held the envelope forward. "Can you please give this to Erin when she's done?" I asked. "Of course", was the reply accompanied by a smile. I wondered if she knew what was inside. I handed her the envelope before I could change my mind. "Which way is the bar?" I then asked. "Just follow that hallway," the woman said pointing in the opposite direction from the meeting rooms. "It's the second door on the right." I thanked her and walked away shaking.
I had to focus on every step I took to prevent myself from wobbling back and forth down the hall. Each step brought the emotions I felt in the bathroom into sharper focus. Even though the Heart On was barely moving, my arousal was building as the next part of this adventure drew closer with each step. I stopped at the entrance to the bar. I couldn't see anybody inside. I took a deep breath and I opened the door.
It took all of my courage to walk the 15 feet from the door to the corner of the bar. Nicole was correct. There were only a couple of single guys dressed in suits in the bar plus a woman bartender. She looked bored silly and I knew I was going to stick out like a sore thumb. I definitely didn't belong here. But I had my instructions. I took the corner stool and ordered a white wine. The bartender brought it to me without much fanfare. She gave me a quick once over glance probably trying to figure out what I was doing there and much as I was trying to figure that out. She then walked back to the other end of the bar. Almost immediately I felt my phone vibrate. It was a message from Nicole.
"Sandra, you look beautiful. But instead of sitting on the end of the bar you should sit in the middle. And you should also turn so your back is to the bar so the guys can get a good look at your legs."
I stared at the message. How did she know where I was sitting and how could she send that message so fast? I looked around the bar but I couldn't see her. The bartender was not paying attention to me. Could one of the guys have tipped her off? I moved around the corner of the bar to the center. The bartender seemed amused. I sat as I had been instructed. Very ladylike with my legs crossed.
Of course the slit of my skirt did its job and the top of my stocking was exposed. I felt very naughty. I wondered what the guys were thinking. Actually I knew what the guys were thinking. I was more concerned with what Nicole was thinking and what she would order me to do next. The phone buzzed again.
"Good girl."
That was it. No instructions. What was I supposed to do now? Another buzz.
"More people coming. Hang tight. Act natural."
No more than 10 seconds later the door opened and the two couples I saw at check-in when I left Erin my thong entered. Did they know why I was here? Had they seen my thong? I tried to act natural, but it was impossible. Both guys from the couples were staring at me. One of the women was giving me a dirty look as if it was my fault her man was ogling with me. The other one was taking a different tact. She was looking at me like a predator looks at a meal. Clearly she knew what was up, I thought.
The couple with the confident woman walked over and asked if they could buy me a drink. Nicole had said I could talk to people but didn't say how much I should drink. Given my current nervous state, I figured another glass of wine was appropriate so I agreed.
The woman asked if I would join them at their table, but I said I preferred to sit at the bar. Her man was staring at my thigh and the garter snap. He certainly didn't mind. The woman seemed not to mind either and we spent the next 10 minutes or so chatting. They were in town for the weekend along with the other couple and looking for fun things to do. I gave them a few suggestions but the woman interrupted and said she was thinking more along the lines that I would be their fun thing to do. Obviously I was putting out a bi vibe and I wasn't about to discount her offer out of hand. I felt my phone buzz again. I still didn't know how Nicole was watching me. She probably got a signal from the woman that she had just made her pass at me. I looked at the screen.
"Go into the bathroom." Immediately my mind assumed the woman would be coming with me and that Nicole had set the whole thing up. Then I continued reading.
"The stall next to the handicapped stall has an out of order sign on the door. Inside is a bag. Follow the instructions."
I excused myself saying the wine was going through me. I wondered if the woman would follow me. I was a little surprised when she didn't. I found the out-of-order stall just like Nicole promised and went inside. I sat down to try and get a handle on my emotions. I was an emotional wreck. There was a bag hanging on the stall door. Inside I found the note she promised and a scissors.
"Sandra, this toilet is working so if you need to go, please do. Remember though, no masturbation and don't turn the Heart-On off."
I'd almost forgotten I was wearing that devilish little buzzer. It was keeping be very aroused but as I was flirting with the couple I forgot about it. All of a sudden I remembered just how horny I was getting. I continued reading.
"Take the scissors and cut holes for your nipples in your bra. Leave the scissors in the bag and return to the bar."
I hated ruining my new bra I had purchased just 9 hours ago, but I'd come this far. I wasn't going to give up now. A couple of quick snips and the guys were about to see just how excited I was to be at the bar. I walked back to the bar. Another full glass of wine was waiting for me as was the woman. The man had returned to the table with their friends. I didn't have the courage to look the bartender in the eyes. I could sense everyone was looking at my newly on display nipples. I took my seat again at the bar, still facing out and crossing my legs. My phone buzzed almost immediately.
"It's tough for me to see, but I can tell you did it. Good job."
The door to the bar opened again and another man came in. He didn't know what was going on. All he saw was two women at the bar and one of us was exposing the top of her thigh, a hint of her breasts and two very hard nipples. Needless to say I got his attention.
But I was sure the woman was Nicole's plan for me so I deftly deflected his fumbled pick-up line. My phone buzzed again.
"Sorry, I forgot to put on the bathroom instructions to cut the top 4 buttons off your blouse. Do it when you can."
Shit. The three buttons I had open now were not too bad. But the fourth was just below the line of my nipples. My black bra would clearly be on display. I was starting to feel exposed and not in control of the situation. I quickly downed my glass of wine. I was trying to figure out how I could make an excuse to go to the bathroom again so quickly. Fortunately my new companion solved that problem by announcing she had to go now. Thanks to the lady's code of never going to the bathroom alone I was able to join her without raising suspicion. While she took the first stall I quickly retrieved the scissors and snipped off the buttons. I wait by the sink for her to finish. I know she noticed my new found expanse of exposed breasts because she commented on them.
"I believe in being direct," she said. "My husband and I would both like a shot at you tonight."
I just smiled. "We'll see," I told her.
As we walked back to the bar we noticed a few more people had arrived. The woman continued to stand next to me as I sat at the bar. I felt a bit protected by her. Every guy hit on me. That was to be expected the way I was dressed. Usually I could deflect them easy enough but she would help me when I needed it. Within about 10 minutes every guy knew I was committed to her for the evening and to leave me alone. Then my phone buzzed again.
"You're doing very well. You're almost done. One last task. Go back to the bathroom. Leave your bra in the bag."
If I felt exposed before I was mortified by the last instruction. I have nice breasts, but at my age they do need a little support. I'm not a perky 20-something. Still I felt liberated returning from what I assumed would be my last bathroom visit. My breasts were swaying free under my blouse. My nipples continued to try and poke holes in the blouse and the four missing buttons guaranteed anyone looking an eyeful. I was feeling dizzy from the combination of wine and arousal. I hoped Nicole would be there soon as I doubt I could have resisted any further advances from the assembled crowd. I was sure the woman would now whisk me upstairs to their room. I would have joyfully taken her back into the bathroom and licked her pussy. I was ready for anything at that point. Of course my phone buzzed. At least I would not have to wait much longer.
"Sandra, you're doing great. Say good night to your fans. Tell the woman maybe you will see her later but your mistress requires you now. Give her a nice kiss. Then give the bartender a tip. She wants to see your boobs. She'll give you your next instructions."
I was frozen in fear. Up to this point I could pretend I wasn't exposing myself on purpose. How would this woman react? Nicole said she wanted me, though. As soon as I finished here, I would be with her. At least that was my assumption. I stood up and looked at the woman. I think she could tell the text message didn't bode well for her. I just nodded. I didn't say a word but took her head in my hands and gave her a deep passionate kiss. She didn't seem surprised and kissed me back with a fiery intensity. I felt myself swooning. I said a little prayer hoping that is was all a setup and that she would be coming with me.
The bartender was waiting for us to break our kiss. She was holding a cocktail napkin in her hand. I turned from the boys who had enjoyed watching the kiss, unbuttoned two more buttons and pulled my shirt open. The bartender never said a word. She just handed me the napkin. I quickly buttoned up the two buttons and headed for the door. I prayed nobody would follow me but I was sure Nicole had planned for that if it happened. I tried to read the napkin as I moved. It had a number. 606. That must be Nicole's room.
I hustled back toward the lobby elevators. My breasts were flopping wildly but I didn't care. Erin and the other woman were still behind the counter. They got an eyeful as I past them. I didn't care. They already knew why I was here. I impatiently pressed the elevator button five or six times. Finally it opened.
I jumped in and pressed six. The elevator seemed to be taking its sweet time going to that floor, but I'm sure it was just my impatience. I was into the hallway and looking at the signs for room 606. An arrow led the way. I was going to see her soon. The Heart-On and my exposure had done the trick. I was desperate to cum and would do anything she asked to achieve that outcome. I found the door. I knocked. I waited. I knocked. There was no answer. I pounded on the door. Nothing. I started to cry. Had everything been one big joke to her? I threw the napkin on the floor.
It was almost surreal as the napkin floated to the carpet. It looked almost slow motion as I watched it twist and curl on its way down. It landed face up and I saw my problem. The napkin now showed 909. I was at the wrong room.
Back to the elevator I went. It seemed like everything was in slow motion now. I was tapping my heel trying to make the elevator come faster. The doors finally opened and the woman and her husband were inside.
"Done so soon?" she asked coyly.
"Wrong room," I sheepishly admitted.
"What floor?" she asked.
"Nine," I said.
"If it doesn't work out, we're in 1024," she told me. I nodded.
The doors opened again and I sprinted out of the elevator. I didn't care what I looked like or trying to hide why I was there. They knew already anyway. I quickly found room 909. It was at the end of the hallway. There was a bag hanging on the doorknob. I picked it up. One last set of instructions I hoped. I looked in the bag. There was a single piece of paper and what looked like a leather blindfold. I grabbed the paper.
"Sandra, welcome to my lair," the instructions began. "Soon you will experience pleasure like you've never experienced before. You have proved yourself worthy of my attention. Follow just a few easy instructions and you soon will me mine."
I think my heart stopped beating for a moment while I read the letter.
"First, knock twice on the door."
That was easy and I did.
"Now step back to the middle of the hall, remove your blouse and skirt and fold them neatly in front of the door."
I should not have been surprised by that command. Nicole had already told me I would be coming to her dressed in clothes no other lover had seen me in. The blouse and skirt were old. The stockings and garters were new. I didn't expect the blindfold, but it really wasn't a surprise. The third instruction was to put on the blindfold, knock again and then step back.
How long did she make me wait nearly naked in the hallway? I don't know. I was beyond rational thought by that point. My inner thighs were plastered with my juices and I'd reached the point of being so aroused any touch would have sent me over the edge. Did anybody else see me? I don't have a clue. Finally I heard the door opening.
"Come in my pet. Come in," I heard Nicole say. I felt her take my hand in hers. Her touch was electric.