Cyber Sissy Ch. 05

A fantasy by Miss Vicky

Part 5 (The Last One)

The rest of the evening passed with the two of us cuddling on the couch, each with a glass of wine. Megan had changed into a black floor length nightgown with a lace inset running diagonally across the front. This meant that with each movement of her body, I would catch a glimpse of various parts of her body. The sole intent of the gown was to tease and tantalize, never showing everything, yet never concealing it all either. I was still wearing the white bridal peignoir she had given me in celebration of my first complete experience as a woman. Even the most subtle movement caused the slippery fold of my gown to caress my body with the predictable effect on my privates. My hand was resting on her satin covered breast, the heat from her body warming my palm. At random intervals, I would run my fingers around her nipples. Obviously, her body responded to my ministrations, her nipples growing to their full distended length. At one point, she purred her approval and shifted her position to give me better access. I reveled in the knowledge that I was giving her pleasure, surely that was the reason I was put on this earth.

l felt so happy and content with Megan. This wonderful woman had taken me away from my vanilla lifestyle and indoctrinated me into the love of lace and satin. Where before all I could do was fantasize about what it would be like to wear all those lacy garments, now I was going to be able to live my dream.

As I lay next to her on the couch, I had to ask, "Megan, how did you know that I would respond so well to being put in panties?"

"It was obvious from the sites I found in the computer that you had an interest in being feminized. I have to tell you, the more I explored the idea of putting you in panties, the more excited I became. My only concern was that it was just a fantasy and that you would not want to live it. I suppose you could call it woman's intuition. Somehow I just knew that you would be susceptible to what I had in mind. When I was a teen, my brother used to look at my panties hanging on the line with the same look on his face as you had every time I gave you a glimpse of my bra or garter strap. I came home unexpectedly once to find him with a pair of my panties on, masturbating himself. He was so engrossed, I was able to watch until he filled my panties with his cum. That was the beginning of a wonderful summer for the both of us. I discovered my secret desires to dominate men with lingerie and he learned to accept his penchant for panties. When he got married, I took his bride to be aside and explained how she could enhance both her marriage and her sex life at the same time. Poor Ron didn't know what hit him on their wedding night. Pam had packed two peignoirs, one for her and one for him. She told me afterwards how shocked he had been when she let him know that she was privy to his secret. He tried to deny it, but I had given Pam a picture of him during one of our dress up sessions. There was nothing he could do but submit to her and wear his frillies for her. She said that he had never stayed so hard for so long before. We still write to each other and she has him in panties all the time now. He couldn't be happier and neither could she."

All the while she was relating this story, she had begun her own explorations of my body, stroking my cock through the slippery fabric of my nightgown. When I began to evidence the predictable effect, she teased, "I don't know which is exciting you more, the feeling of satin against your body or my fingers stroking you. Actually, I think itМs the combination of the two. You now have the best of both worlds."

She continued her manipulation of my cock, wrapping the folds of my gown around and slowly stroking it up and down while she continued, "I have it all planned out you know. You will continue as before, working your way up the corporate ladder. There will be just one difference. Since youМve been using a temp since your last secretary got married, you are going to hire me as your secretary, starting tomorrow. Now, instead of just having an administrative assistant, you will have a true partner in your efforts, one that will take a personal interest in your success. Imagine how good it will feel to sit there in your business suit with the lingerie I've selected for you under it. Every time you move, the satiny panties will give the mildest stroking, reminding you of our secret. You will begin to look forward to five o'clock, when you can come home with me and slip out of your boy clothes and into some sexy lounge wear."

My breathing began to grow deeper as she reached down with her other hand and cupped my balls while continuing to stroke my cock. "We will begin tomorrow", she went on. You will be allowed to keep one set of male underwear for those times that you must wear them. For example, your doctor would get quite a shock if you slipped off your pants to reveal a pair of frilly lace panties under them."

By now, the effects of her teasing had become quite evident and I knew that if she continued, I would have an orgasm right there. I kissed her gently and whispered in her ear, "It sounds wonderful, but for now if you don't stop what you're doing, I'm going to cum in my nightie."

"Don't be silly my pet," she chided. This is what I want for you. It excites me to know that no matter how hard you try, you can't resist the effects of your lingerie and my attentions." She increased both the tempo and the pressure against my cock, while gently squeezing and massaging my balls. "I can tell you're ready," she giggled. "Your balls are getting very full aren't they? That's all right my pet, I want you to cum."

By now her hand was a blur as she stroked my faster and faster. As she sensed the onset of my climax, she licked the inside of my ear and whispered in it, "Now, come for me my pet. Squirt your juices into your satiny nightie. Think how good this feels and admit that you can't help yourself."

"Oh Megan, please don't stop! I'm going to cum," I gasped. \"That's it, my pet," she cooed. "Empty yourself into your nightie. Surrender yourself to the silkiness that surrounds your very essence. Reward your Mistress for her efforts." Despite having climaxed only an hour before, my cock erupted with another tremendous amount of jism. When I was apparently finished, she wrapped her fingers tightly around the base of my shaft and milked the remaining drops from my trembling body.

When I had recovered enough to take a sip of the wine, Megan shifted her position on the couch, leaning back with her legs spread. She pulled up the hem of her black nightgown to her waist, revealing her mound. "Look at what that has done to me," she said as she slipped her index finger inside her slit. "Getting you excited had the same effect on me. I'm all wet and hot inside." Gently she pushed my head to her lap.

As I approached her pussy, I could smell her musk. It was the distinct aroma of overheated woman. I knew what was expected of me and to tell the truth, needed no further urging in setting about my task. I slipped to the floor, kneeling between her legs. As I began to nibble and lick my way up the insides of her thighs, she raised herself off the couch and pulled the hem of her nightie down over my head, trapping me inside. It was like being inside a tent of black satin. The gown was sheer enough to allow ambient light inside, while being opaque enough to shut out outside distractions. As I neared her muff I extended my tongue as far as it would go. I wanted it to be the first thing she felt against her vaginal lips. Just before making contact, I began to flick it rapidly back and forth. The instant my quivering tongue made contact, it was as though her body had been assaulted with a cattle prod. She jerked convulsively, thrusting her hips toward my eager mouth. I pursed my lips and sucked her clit into my mouth before lashing it with my tongue. Her body jumped again and I could feel the onset of her climax. It seemed to build and build until with a scream that would wake the dead, she grabbed my head with both hands and pulled it tight against her pussy while her climax continued with wave after wave of ecstasy. I don't know how long it lasted, only that when she finally relented and released my head, her body was coated with a fine sheen of sweat. Her exertions had momentarily sapped her of all strength and she sagged back against the cushions of the couch.

I pulled myself up nest to her and laid my head on her shoulder. "That was just for you Megan," I whispered. You have given me so much pleasure, I had to try and repay you in some small way."

"I don't know if I could survive your repaying me with anything more intense than what you just did to me," she said ruefully. "That is the most intense climax I can remember. No one has ever eaten my pussy that way before. I don't think it was just the physical stimulation though. All I could think about was that my man was eager to please me, that all he wanted was for me to be happy. I've never had that before in a relationship and I find it to be quite arousing. Let's go to bed, we have a lot to do tomorrow."

I followed her up the stairs and went to my room to change out of my soiled nightie. I selected a pink babydoll nightie from my closet and was just pulling the matching ruffled panties into place when Megan called to me from her room. "When you've finished in there come to bed with me. From now on, you will once again sleep with me. That room will be reserved for those special times when I want to get a little dominant."

I went immediately to the bedroom and as I walked into the room, Megan pulled back the covers on my side and patted the bed next to her. "Get into bed my pet. I want you next to me while I sleep. I'm sure my subconscious will supply me with some delicious dreams tonight and I want you there next to me when I wake up."

I slipped in next to her and leaned over to give her a kiss. She pulled me hungrily down to her mouth and drove her tongue into me. "This is more perfect than I dreamed," she said softly. "I have my man just the way I always fantasized of, in bed with me and wearing his lacies. Now we had better get some sleep. We have a full day tomorrow."

I rolled to my side and did as she said. I must have been tired, I fell immediately to sleep. I was awakened the next morning by the delicious feeling of Megan's fingers inside my panties, caressing and stroking me until I came fully awake.

"Wow, what a way to get a wake up call," I murmured. "If I thought you'd do this every morning, I'd throw away the alarm clock"

"I just couldn't resist," she answered. There's something about a penis inside a pair of frilly panties that turns me on. Its too bad we don't have time to take advantage of it. I'm afraid you'll just have to look forward to what will happen the moment I get you home tonight. Come along my pet, we have to get ready to face the world." She got out of bed and went to the bathroom. I joined her and together we quickly showered and came back to the bedroom to get dressed.

Megan went to her dresser and came back with yet another package from her favorite lingerie store. Handing it to me she said, "Put these things on. I bought them especially for your first day at the office in your panties. As you will see they are quite special."

I opened the package to find a complete set of black lingerie. They were as Megan had said, quite unusual. The panties were black with lavender lace trim. They had been custom embroidered with the words "Megan's Panty Boy". Also in the package was a pair of black stockings with a lavender back seam along with a garter belt and camisole, both in black with trim to match the panties.

Megan watched with an amused smile as I examined my new treasures. "As you can see, IМve been planning this for sometime. You can imagine the look on the salesgirls face when I told her what I wanted embroidered on the panties. I thought she would explode, she was trying so hard to hide her astonishment. She did quite well though and after a while she asked me why I was doing this to my man. I explained the advantages to keeping a man in panties to her and she showed considerable interest in the idea. She went so far as to suggest that next time, I bring you in for a custom fitting."

My face must have shown my consternation at that idea, because Megan immediately added, "I don't know how comfortable I would be with the idea of giving another woman a chance to see how desirable you look in your panties. Well anyway, that's a matter for future discussion, we have to hurry if we don't want to be late."

I put on my new lingerie and then covered it with my normal business attire. I reflected on how fortunate it was that my socks were calf length, allowing me to easily hide the pretty stockings Megan had bought. We quickly ate a bowl of cereal and coffee and each taking our own car, drove to the office.

My schedule that day was quite hectic. There was a meeting of the department heads that I had to attend. I sat at my usual place in the meeting room and waited my turn to present my proposals for our upcoming fiscal year. There was only one problem. All through the day, every move I made caused my cock to be stroked and teased inside my new panties. The lacy camisole rubbed my nipples as well, keeping them erect with an unrelenting teasing of the slippery fabric.

Megan hadn't made it any easier either, taking every opportunity to lean over my desk, exposing the lacy top of the lavender bra she wore. Her other little trick was to go to the file cabinets and pretend to look in the top drawer. She would look over at me and pull the hem of her skirt up, exposing her garter strap and give me a lewd wink Not satisfied with just that, she would occasionally come behind my chair and then speak in a soft tone, telling me what would happen to me when we got home.

The person next to me was Lydia Comstock, the head of Human Resources. On several occasions, I thought I saw her glancing at my crotch. I looked down to see that my slacks had a distinct bulge in them. There was nothing I could do but sit there and cross my legs, hoping that would hide my erection.

My turn came and I gave my report, emphasizing my departments higher goals for the coming year. The president of the company complimented me for the job we had done the previous year and the objectives we had set for the coming one. When I was finished, Lydia turned and congratulated me, "Nice presentation Jim, I'm sure you made a big impression on the president. I know you made one on me." This last statement was made with a definite look a my crotch. She reached out and gave me a congratulatory pat on the thigh. I could see her eyes change as she realized that there was a garter strap under my slacks. "My, but aren't we full of surprises," she said with a slightly ominous tone. I said nothing, merely averting my eyes. "Don't worry, as long as you play ball, your secret is safe with me," she continued. "Perhaps we might have lunch someday. You can tell me how you came to your choice of undergarments. I'll be expecting your secretary to call with a date and time. Don't make me wait too long or I'll have to make you sorry." Mercifully at this point, the President adjourned the meeting. I didn't say a word to Lydia. I just joined the group as we all trooped out to our respective offices.

Megan met me as I came through the outer office. "How did the presentation go?," she asked.

"I have good news and bad news," I replied. "First, the good news, the presentation went very well. The president was obviously impressed."

"I assumed that would be the case," she replied. "Come on, don't keep me waiting. What's the bad news?"

I told her about Lydia Comstock's apparent discovery of our secret and her veiled hint about exposing me.

"That is something we will have to deal with in an appropriate manner. She strikes me as the type of bitch that is always looking for a way to embarrass others. Don't worry my pet, when the time comes, I will think of a suitable way to make sure she won't meddle or humiliate either of us. I haven't gone to all this trouble and expense to have her obstruct our future together."

She patted me on the cheek to reassure me that all was well and Mistress would take care of everything. The rest of the day passed quickly and before I knew it, I was on my way home. Megan showed me where she had hidden my male underwear and together we threw it in the trash. True to her word, I was allowed to keep only one set of briefs for those times I would be at the doctor's office. "You will never have to wear these nasty boring undies again," she proclaimed. "You are mine now and I will keep you forever in lacy panties and lingerie. You have to admit, you have a much wider variety of things to wear. You can match your undergarments to either your mood or mine. I can put you in something slutty or chaste, depending on what I want to do to you that night." Megan took my hand and led me to the bedroom. "Don't move a muscle," she ordered. "I want you to just stand there while I remove our clothes." She removed our clothes in corresponding pieces, first my shirt, then her blouse until we were both left with nothing on but our panties. Saying nothing, she took me again by the hand and led me to the bathroom where she quickly stripped us both of our remaining clothes. She used a fleet enema on me to ensure I was nice and clean inside and then we showered together. When we were dried off, instead of going to her room, she took me to what had been mine. I knew from our earlier conversation that this meant she was in a dominant mood. She ordered me onto the bed, placing me on my hands and knees. I meekly complied, secretly relishing the idea of being "forced" to serve my beautiful Mistress. She next slipped a black satin sleep mask over my eyes adding, "Don't peek now and hold that position. I have a surprise for you." I heard her rummaging in her night stand and shortly, I felt my wrists and ankles being cuffed and tied tightly to the corners of the bed. To make sure I couldn't resist whatever she had in mind, she ran an additional pair of ropes to my thighs, just above my knees. When she was finished my legs were spread wide apart, giving her complete access to my privates. I was now helpless to stop her from doing whatever she wanted to me. I wondered to myself how a woman could be so feminine and caring one moment and so demanding and strong the next.

My reverie was cut short my her next statement.

"Its time to give your Mistress a reward for all her efforts," she intoned. "Open your mouth my pet, you are going to learn how to suck my cock. I want to watch as it slides into your sissy mouth. You are going to get the full length of it all nice and wet before I use it on your sissy pussy." She grasped me by the ears and place the head of the dildo at my lips.

I obediently opened my mouth allowing it to slip between my lips. She fed it to me an inch at a time, chiding me for my inability to take it all deep in my throat. "Relax your throat my pet, let your Mistress bury her cock in your sissy mouth." I did as she said, and before long the entire length of it was being pumped in and out of my mouth. I could hear the tempo of her breathing increase as she continued. Oh my precious slut, you should see the vision you make. Your sissy lips wrapped around my cock as it slides in and out. You want this don't you? You want me to make you my sissy. Alright then, you are going to get the fucking of your life. I can't wait any longer. I have to take you like a girl before I explode."

She pulled the cock from my mouth and went behind me. I felt her coating my pussy with lube just moments before she entered me. This time she had not spent any time preparing me, so I was tighter than the last time. The pressure needed to penetrate me was transmitted back down the length of her cock to her clit. I was just beginning to relax and enjoy myself when I felt her hands on my shoulders. Using them as leverage, she thrust herself deep inside me. Her nails dug holes in my shoulders as she gave in to the overwhelming climax shaking her body. "Oh my God!," she screamed. "I can't stop cumming!" I took this as my clue to thrust myself backwards, increasing the pressure against her clit even more. "Yeeeeesssssss," she screamed. "That's my sissy. Make your Mistress cum again!" Once again, I felt her nails penetrate my skin as yet another wave of pleasure coursed through her body. At last, she let go and collapsed against me, the dildo still buried deep inside me. It seemed as though it took forever for her to regain her composure enough to pull the dildo from my ass. She didn't say a word as she untied me and took me back to the bathroom for a quick shower to rinse the sweat from our bodies. Not until we were back in her room did she speak, "You have certainly lived up to my expectations my pet. I think you were born to be a sissy slave. Find yourself a nightie and lets go to bed. Your Mistress is tired and needs some rest.