Cyber Sissy Ch. 05

I slipped into a frothy mint green nighty while she put on her red satin gown and we joined each other in bed. As I dozed off, I felt her finger insinuate themselves into my panties. That is how I went to sleep, with my Mistress's fingers around my cock. I can't begin to describe the feeling of contentment I felt at that moment.

The alarm went off at 6:30 and we both dressed for the day. My lingerie was a pretty pair of eggshell panties with built in garters. Of course the camisole matched with lavish lace at the shoulders and bodice. By the time I had my suit on, Megan was already waiting for me in the kitchen. We wolfed down a quick breakfast and drove to the office, again in separate cars. The day was not that busy, sort of a welcome lull after the hectic two weeks getting ready for the prior days meeting. I was just settling in to read one of the trade journals when Megan came in with my morning mail. She had a very determined look on her face as she handed me one piece in particular.

"The bitch didn't waste any time," she said ominously. "This is from Lydia Comstock and its addressed personal and confidential, as though that would stop me. Open it, let's see what that conniving shrew has in mind."

I opened the envelope and read the note inside. It read:

Dear Jim, (or should I say Jamie?)

I was quite pleasantly surprised at my discovery yesterday. Who would of thought our macho executive had a penchant for panties. You were wearing panties with the garter belt weren't you? I wonder what color you chose for that meeting. Was it a power color like red or something more soft and feminine?

I don't think the President of the company or any of your peers would understand if they knew. For that matter, what would your pretty little secretary think if she knew her boss wore panties to work? I propose we set up a quiet rendezvous to discuss what I will require of you if you want me to keep our little secret.

You will get a motel room for two tonight, registering under the name James Comstock. You will wear white panties, bra and garterbelt. If you don't have a set like this, you are to purchase one. It is important to me that the first time we are together, you be in something virginal and pretty. Once you are in the room and settled, you are to strip off all your boy clothes and call 555-1234 at exactly 8:00. You will give the motel address and room number. I will join you and tell you what it is I expect from you. Don't worry, you might even learn to enjoy it. I'm sure I don't have to elaborate about what will happen if I don't receive your call.

Lydia Comstock

"We will have to take care of this sooner than I thought," Megan commented. "I have an idea as to how we can get her off our backs and have a little fun at the same time. I'm going to take the rest of the day off. I'm going to be busy preparing a few surprises for our Ms Comstock. I will call you and let you know where to go to after work. Be sure and bring several change of lingerie with you."

The rest of the day seemed to drag as I waited for Megan's call. On my way back from the coffee machine, I ran into Ms Comstock. She stopped and looked me up and down, pausing perceptibly at my crotch. She caught my eye and gave me a smile as though we shared a secret. I said nothing averting my eyes from her gaze. She came closer and whispered, "I can't wait to get my hands on you tonight. You are going to be there aren't you?"

Mutely, I nodded my acceptance and we both continued back to our offices. When I reached my desk, I had no sooner sat down than my private line rang.

Megan's voice was at the other end with my instructions. "I have taken two connecting rooms at the Starlight motel. You will be in 132 and I will be next door in 131. You will find a bottle of wine in a bucket of ice on the dresser. Next to the ice you will find two pills. I want you to take both of them as soon as you get there. The wine is drugged and will put her to sleep within 5 minutes of drinking it. The pills are the antidote, allowing you to drink with her without any effect. When she gets there, you will find an excuse to pour a glass for both yourself and the bitch. Go along with whatever she wants until the sedative takes effect, then open the connecting door to my room. I have several surprises waiting for the bitch in there. This will be a night she won't soon forget, but not for the reasons she's thinking." With that last ominous statement, she hung up, leaving me to wonder what sort of diabolical plan she had in mind.

I left work a few minutes early so I could shower and change into my white lingerie. When I came out of the shower, I went to my dresser and because I now had several white ensembles, chose my favorite. It comprised of a satin half cup bra, French cut panties with lot of lace at the sides and leg openings and lace trimmed garter belt. The stockings were of course seamed and ultra sheer. Following Megan's instructions, I packed a small bag with several more changes of lingerie including some crotchless panties as well as my black and my pink baby doll nighties. I also put my white mules with the marabou trim in for good measure. I didn't know what Ms Comstock had in mind for the evening, but I knew my Mistress would approve of the extra lingerie. Noticing my time running short, I threw the bag in my car and drove to the motel for my meeting with Sylvia.

The desk clerk gave me my key and I went to the room. Just as Megan had said, the wine and pills were there. I wasted no time, hurrying to take the pills before calling Sylvia. I dialed her number and she answered on the first ring. "Sylvia, this is Jim," I announced.

"Good, you're on time," she replied. "I like that in a man. Are you dressed as I told you?" "Yes, just as you said, white panties, bra and garter belt."

"Give me the address and room number, I cant' wait to see the big executive in his panties."

I gave her the requested information and she hung up, telling me to wait for her arrival. She further instructed that I was to answer to motel room door dressed only in my lingerie, that she didnМt want to waste any time removing my male clothes. I paced nervously, wondering just what I had gotten myself into. Just as I reconciled myself to trust Megan to take care of everything, there was a knock at the door. I looked through the peephole to see Sylvia there. I opened the door and stood behind it, blocking any casual observers from seeing me in my lingerie. Sylvia swept into the room, turning to face me as I closed the door. "Be sure and lock the door Jim, I don't want anyone to disturb us," she ordered. "When you've done that come over here, I want a better look at you."

Once I had complied, she ran a fingertip over the bulge in my panties. "Would you look at this?" she commented. "A nice big cock all wrapped in satin and lace. I think I'm going to enjoy this a lot."

"Would you mind if we had a glass of wine first?" I asked. "I have to admit I'm a little nervous and it might help me relax a little."

"Of course, that's a wonderful idea. You may pour us both a glass."

I poured the wine and turned to see Lydia shrugging her blouse from her shoulders. She said nothing, but continued to undress until she was left with nothing but her black lacy bra and panties. "Do you like what you see?" she asked, taking the glass of wine. "Don't bother answering, it really doesn't matter what you think. I know your secret and that's all the control I need to turn you into my boy toy. Because I am so devoted to my career, I don't have time for a conventional relationship. I do have my needs however and you will be the one to satisfy my requirements in that area. As long as you go along with my little games, your secret will remain between the two of us. If you should disappoint me in any way, I will make sure everyone at the office knows that their hotshot sales director is a panty boy." By now, She was beginning to slur her words and sway a little. "This wine is really going to my head. I don't understand this. Normally, I can have several glasses before I start to get light headed." She sat on the bed and just after putting her glass on the night stand, fell back on the bed with her legs splayed.

I gave it a couple of minutes to make sure she was completely out before going to the door that connected to Megan's room. I knocked twice to and called her name, wanting to make sure that it really was Megan in there.

"Is the bitch sleeping now?" she asked as she opened her door.

"Yes, it only took a couple of minutes after she drank the wine."

"Good, I was worried that I might not have gotten the dosage right. I trust you are feeling no ill effects, that the antidote worked as it was supposed to?"

"No problem at all," I replied. "Actually, I didn't have to take more than a sip. She was too busy telling me how she owned me and wasn't paying attention to whether or not I was drinking with her."

"Then everything is ready. Help me carry her into my room. I've made some special preparations for tonight's fun. Trust me, she won't forget the lesson she's going to get tonight. I doubt she'll be playing any more blackmail games ever again, certainly not with you my pet."

"I was really worried that something might go wrong and I'd have been left at her mercy. You have no idea how glad I am that everything went as you planned," I said as I picked Lydia up. I carried the sleeping body to Megan's room and laid her on the bed.

Megan went to a suitcase and pulled out a box from the adult toy store she patronized. "Take a look at this my pet. This little toy is called The Scorpion," she said as she took it out of the box and handed it to me. It was made of a jelly like material with a battery box at the end of a pair of wires. There was also a harness designed to go around the tops of the legs and around the waist. "As you can see," Megan continued while grinning devilishly, "There is a long tail at one end and a pair of pincers at the other. The pincers will go around her clit and the tail will be inserted in her ass. I can assure you that as soon as I turn on the power, both her clit and her ass will be assaulted with incredible stimulation. She came here expecting some sexual stimulation and I'd be the last person to deny a girl a good time. Pull her panties down a little and I'll get her ready for the surprise of her life."

I did as Megan instructed. She then had me roll Lydia onto her side and after lubricating the tail of the Scorpion, slid it into her ass. Satisfied that the tail was now in place, she parted her labia and placed the pincers on either side of Lydia's clit. "Hold this in place while I fasten the straps," she ordered. I did what she said and soon the toy was securely fastened to Lydia's sleeping body.

"Now I want you to put her in the chair next to the dresser," she continued. After pulling her silky panties back in place, I again picked Lydia up and carried her to the chair. As soon as I had placed her in it, Megan attached leather cuffs to her wrists, ankles and thighs. Each of these in turn was attached to the chair with lengths of nylon rope. "We have to hurry, the sedative is due to wear off soon, Megan said as she fastened a leather collar around Lydia's neck. This was tied to the back of the chair with yet another length of rope. As a final touch, she opened Lydia's mouth and inserted a penis shaped gag. It was attached to a harness with straps under the chin and around her head. Once the straps were fastened, I could see that there was no way the gag could be expelled. As a finishing touch Megan added a blindfold. Lydia was now completely helpless, her legs spread wide apart. She was unable to move, to see who her captor was or call for help. "There, now all we have to do is wait for the bitch to wake up," Megan said as she stood back admiring her handiwork. "There is a fresh bottle of wine in my bag, be a pet and pour us each a glass while we wait for our new toy to wake up."

I poured the wine and as I was about to hand Megan her glass she asked, "Did you bring any crotchless panties with you?"

"Yes, several pair. Would you like me to slip into any particular ones?"

"If you brought the naughty purple set with you, put that on. You know, the one with the half cup bra and crotchless thong panties. Don't forget to put on the matching garter belt. I intend to take several pictures, so I want the full effect."

I retrieved my bag from the other room and stripped off my white lingerie. The lingerie Megan had referred to was not entirely purple, but also trimmed in black lace. I slipped the panties, bra and garter belt on before selecting a pair of black stockings to complete everything. When I was done, my clit was at full attention, sticking straight out of the lace trimmed slit in the panties.

Megan laughed and caressed it, "I just love the way it sways back and forth when you move. As soon as the bitch wakes up, I think you may have to use this replace the gag she has now. I'm sure she'd much rather have the real thing."

Any chance I might have had to reply was interrupted by Lydia's soft moan as she began to come out of the drug induced sleep. We watched with amusement as she regained consciousness, only to discover that she couldn't move, see, or make a sound other than a muffled moan.

Megan walked the chair holding her prisoner and whispered in her ear. "This is not quite what you had in mind, is it? I'm sure you had all sorts of plans for Jim, but I'm afraid I'm not willing to share him unless I can be here to direct the fun. Would you like a little preview of what you will experience tonight? Oh wait, you can't answer with that penis gag in your mouth. How thoughtless of me! I will just have to assume that you want it." She reached down and turned the Scorpion on, using the lowest setting. The effect on Lydia was immediate. The instant the toy began to vibrate, she bucked against her restraints in a vain attempt to escape. Megan's response was to turn the toy up to it's highest setting. Lydia now began to moan and writhe in the chair as the toy assaulted both her ass and her clit at the same time. It was quite clear that her orgasm was only seconds away when Megan pulled down the lacy cups of her bra, motioning me to come closer. The instant her orgasm began, Megan pushed my head to her nipple. I knew what was expected and quickly sucked it into my mouth and lashed at it with the tip of my tongue. I could smell her musk now, the unmistakable aroma of a woman in heat. The front of her panties were becoming wetter by the second as her body responded to the ministration of both the toy and my mouth. Her entire body began to quiver, every muscle taut as her climax overtook her. By the time the last spasm had subsided, her panties were completely soaked with her juices. Megan turned the toy off and leaned next to Lydia's ear. "You came here to get some jollies and I'm just the girl to see that you're not disappointed. You are going to cum again and again. You see, this falls under the heading of watch out what you ask for, you might just get it. Are you ready dear? "I'm going to allow you more pleasure now."

Megan went to her bag and came back with a pair of scissors which she used to cut away Lydia's panties. Lydia jumped a little at the feel of cold steel against her skin, but relaxed once she figured out that it was just her dainties that were to be put to the scissors. As she felt the cool air against her totally exposed private place, Lydia began to shake her head violently back and forth, straining against the collar and rope holding her head back. She might as well have saved what little strength she had left.

Megan's response to all this was to just smile a little and once again turn the toy on. To make matters worse for our captive, she bent over next to her and whispered seductively, "Were you going to make Jim go down on you tonight? I'll wager you had something like that in mind. Well, far be it for me to deny a girl her fun. I'm going to loan you his very talented tongue for a moment or two. I'm so sure you'll enjoy what he can do for a girl I'll make a bargain with you. If you can last more than five minutes without having an orgasm, you will be set free. You have my word on that." She then turned to me and simply nodded her head, giving me all the instructions I would need with just that one gesture.

After Megan handed me the remote control for the Scorpion, I knelt between Lydia's wide spread thighs. At first, I turned the toy off, wanting to build her slowly to a climax. Because I knew she had to be a little tender after what she had been put through, I began very gently, licking my way up her labia until I found her clit. It was in the tight embrace of the Scorpion's pincers, a hard nubbin of nerve endings. I touched just the tip of my tongue to it, before giving it several quick flicks. I sucked it between my lips and rolled my tongue over it until she began to mew and whimper. As her body betrayed her, her hips tried to thrust her pussy against my mouth. She was now a complete slave to the lust of the moment, not knowing or caring what was happening to her. Her brain was being flooded with messages of pleasure and her body complied with the involuntary commands it sent. I could sense the onset of another climax and at just the right moment I pressed down with my lips and turned the toy to it's highest setting.

Lydia gave out a scream of pleasure as the second of her climaxes hit. Only because of the gag was it somewhat muted. At just this moment, I heard the sound of Megan's Polaroid as she documented the moment with several shots of her lingerie clad lover between Lydia's legs. I couldn't help but smile as I thought about what would happen if they ever became public. Lydia's climax was now at it's peak. I didn't stop what I was doing, in fact I intensified my efforts until she gave out a final scream and sagged against her bonds. Her body was completely slack. I couldn't believe it! She had actually passed out from the intensity of it all. I pulled away from her and wiped the juices from my face. I went to the dresser and took a sip of wine before turning to Megan. "How did the pictures turn out?" I asked.

"Here take a look for yourself," she said grinning. "Her face is somewhat obscured by the gag and mask, but we have all night to take care of that." She removed the gag and blindfold from Lydia and motioned me closer. Because of the activities of the evening, my cock was fully erect, waving from the slit in my panties. Megan grinned a the sight and said, "I think she would appreciate a real penis gag now. Come here and we'll give her something to think about when she comes to."

Megan opened her mouth and after stroking it a couple of times guided my cock into her mouth. "Don't move," she commanded. "This will make a great shot." She took several pictures before she was satisfied that we had enough for the moment. When they developed I could see what a powerful club they would be. Lydia's face was clearly visible, her lips wrapped around a cock sticking out of a pair of lacy panties. Even the fact that her eyes were closed enhanced the overall effect. It looked for all the world like she was really enjoying the moment. After a few more seconds, she began to regain consciousness. As her eyes opened, the first thing she saw was my cock just inches away.

Megan came around the chair and stood silently with an ominous expression. Lydia gasped when she recognized her captor. "Oh my God! You're Jim's secretary. Why are you here doing this to me?" she asked plaintively.

"Because Jim is also my husband. I was hired under my maiden name so no one would make the connection. I don't like to share my possessions with anyone," Megan replied. This whole evening was my idea. I wanted to be sure that you would never again bother him at the office." Take a look at the pictures I've taken of you," she added handing Lydia the Polaroid's. I will keep these in a safe place as long as you behave. If you step out of line with Jim just once, I think I know where these would do the most good. You really can't complain you know. You wanted to get into his panties and I have arranged for just that.