The Unsuspecting Candidate Ch. 03

Story Info
Mike is bound in his new lingerie and used by two women.
5.1k words
4.68
82.3k
29

Part 3 of the 3 part series

Updated 10/31/2022
Created 08/06/2009
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I awoke at 6:00 A.M. and set about preparing for my sissy's surprise. I opened the door to see him there on the bed, his ankles and wrists still cuffed to the four corners of the bed. His head was still encased in the bondage hood and he lifted it as I shut the door and approached the bed.

"I trust my sissy slept well," I cooed as I began to release him from the cuffs holding him prisoner.

"You have a big day ahead of you, so I want you to quickly get out of your maid's dress and use the bathroom. When you finish with that, you may come back and join me in a light breakfast. Then it will be time to begin preparing you for your surprise."

As soon as the last cuff was undone, I unsnapped the blindfold from the bondage hood, leaving the gag holding my panties in place where it was. You will leave the hood where it is, you can see well enough for what you have to do. Obviously, he couldn't say a word, but he nodded and moved quickly to the bathroom. I'm sure the poor dear needed the facilities there, since he'd been tied up for more than eight hours.

"I will be selecting your attire for today," I told him through the closed bathroom door. "I want you to get completely undressed. I don't think a shower is possible with the hood in place, so I want you to use a washcloth to quickly clean up a little, then present yourself to me in the bedroom.

I quickly dialed Jessica's number and when she answered, I said, "You can come over in about 15 minutes, don't bother knocking, the front door will be unlocked. When you get here, don't make a sound, just take your shoes off and come as quietly as you can up to the bedroom. I'll be there and so will your new sissy slave."

"I can't wait," was her response. "I'll be on my way presently."

"Good," I replied. "Be sure and bring the toys you purchased for today's little party."

"Don't worry, they're already in my overnight case, bye for now, I'll be there soon."

I heard the water running as he followed my instructions while I set about laying his lingerie for the day. I chose a filmy white babydoll style peignoir set with sheer ruffled panties. To this I added a lacy garterbelt and seamed lace top stockings, also in virginal white.

I heard the bathroom door opening and as he came back into the bedroom I chided him, "Hurry up sissy, we have a lot to do." I handed him the frilly garterbelt and without being told, he fastened it around his waist. "Now sit on the bed sissy, I will put your new stockings on," I commanded. "I don't want you to get a run in them."

He sat there and extended each leg in turn as I slowly rolled the stockings up and into place. I noticed that as my hands brushed his inner thighs while I attached the garter clips, his sissy parts began to get hard. This was not unexpected, the poor thing had not had any chance for relief since last night's milking.

"Now for your panties," I teased. Holding them up in front of his eyes, I continued to tease him. "Would you look at all the ruffles on these panties?! They're called sissy panties, the perfect name for them I think. After all, that is what you are, a sissy, my pantyslave. Now, lift your feet so Mistress can slip these on you. "He did as he was told and I began to pull them up his legs. As I got them to his knees, he stood to allow me to pull them the rest of the way up until his sissy clit and balls were snugly held by the filmy ruffled panties.

I took his clit through the sheer fabric and stoked it several times, making it grow and make a tent out of his panties. "Mmm," I cooed. "My sissy is certainly excited this morning! Soon you will be even more excited and aching to cum for your Mistress. But for now, we need to get you into your lacy nightie and restrained again. I don't want you to have any chance to resist the sweet torments I have in mind for you. I think it's time for the blindfold again, hold still while I put it on."

He stood meekly as I reattached the blindfold, sending him back into darkness. I picked up the babydoll top and slipped it over his head. Without being told, he slipped his arms through the armholes, a shiver going through him as it cascaded softly down his body.

"Now, the peignoir coat," I said as I slipped it on over the nightie. I stepped back to survey the results. "Oh my," I exclaimed. "Don't you look pretty in your lacy lingerie, just like a bride on her wedding night." Now it's time for the rest of your preparations.

"Turn for me sissy and face the headboard please" I said as I guided him into place. Once he was positioned properly, I attached a cuff to each ankle. "Now spread your legs for me sissy." When his legs were about three feet apart, I tied a rope to each cuff, leaving him unable to put his legs together. I then fastened a cuff to each wrist and positioned him face down on the bed. I took all the slack from the attached ropes, leaving him with his arms extended fully to the corners of the headboard.

I reached from behind and stroked his panty trapped clitty, teasing him until he began to writhe and wriggle as the pleasure my fingers provided him drove him wild with lust, aching to cum. "Not yet, little sissy, you will cum but only when I allow it," I teased as I stopped my ministrations. "I have to get dressed for our fun today, so don't go anywhere." All he could do was moan his frustration into the panties still gagging him.

I went to the dresser and selected my attire for the day, a black lace garterbelt and stockings. To this I added a black lacy bra with openings for my nipples. I didn't bother with panties, they would just get in the way of what I had in mind for my activities. Once I had my lingerie on, I moved to the bed, positioning myself with my legs under his outstretched arms my pussy inches away from his gagged mouth.

"Would my sissy like Mistress to remove that nasty gag from his mouth?" I teased. All he could do was nod. "All right then, but you will have to repay my kindness," I said as I removed the articles from his mouth. I pressed my pussy against his face and without further instructions, he began to lap at my lips, probing with his tongue into their silky folds.

My body began to tremble as all the pent up passion overtook me. At this point, I heard a car door slam. I knew Jessica was here now. To muffle the sounds of her coming into the house, I grabbed his head with my hands over his ears and pulled him even more tightly against my now sopping pussy. In a loud voice I let him know he was pleasing me. "Yes that's it sissy, lick my pussy, make me cum all over you sissy mouth. Mmm, yes that's it run your sissy tongue over my clit, feel it grow as you pleasure your Mistress."

At this point Jessica came silently into the room, a look of shocked amusement on her face. I'm sure we made quite a sight, her boyfriend helplessly bound in lacy lingerie, eagerly lapping at my pussy. I held a finger to my lips to indicate she should remain silent while I continued to let my sissy know he was pleasuring me.

Jessica was wearing a knee length coat. She undid the buttons and shrugged it from her shoulders, leaving her in nothing but a fire engine red set of lingerie. The bra was a half cup style, leaving her nipples exposed and the panties were crotchless, giving me a good view of her honey blonde muff. I looked at her overnight case and nodded at her to indicate she should get the special toy we had purchased in place.

Silently, she opened the case and removed a latex panty from within. Attached to the panty was a six-inch latex dildo! That was not the only extra feature though. Inside the panty was another dildo, one meant to be inside her pussy. In addition to that, there were controls for the vibrators buried in each of the dildos!

I continued to exhort Mike to greater efforts as Jessica came to within my reach. She carried the toy to the bed where I licked a finger and slipped into her, getting her nice and wet for the dildo. Without making a sound, she pulled the panty-dildo into place, a look of pleasure coming over her as the toy inside the latex panties slipped inside her.

All the while my sissy had been lapping at my clit like a kitten at a bowl of cream and I knew what would only be the first of many climaxes shook me. "YES, sissy make me cum! Lick me! Suck my clit! " I exhorted as wave after wave shook me. As the tremors subsided, I teased him further. "You've been such a talented little lesbian sissy. I have a treat for you. You're going to have a special experience, one most sissys dream about but never realize in anything but their nasty fantasies."

As I was speaking, Jessica had moved behind him. I held his head as she reached out to stroke him through his panties. As soon as she did this, he stiffened, realizing there was another person in the room with us. "Relax sissy," I said softly. "I invited a long time girlfriend of mine to enjoy your submission. As much as I wanted to keep you all to myself, you are just too precious and talented not to share."

By this time, Jessica had her hand in his panties, gently massaging his balls and clit with her soft hand. "It's time for my sissy to get a special treat," I continued. "You're about to feel what it's like for a girl on her first time."

"Pull his panties down and put an examining glove on dear," I instructed Jessica. Once that was done, I continued my lesson. "Now lube your index finger and put it inside his pussy, finger fuck him just like a boy does when he's trying to get a woman hot and wet, trying to get her to spread her legs for him."

Jessica complied with a vengeance, and as she slipped a finger in his ass, he began to writhe and buck as his pussy was invaded by her probing finger. Before long, I could tell he was enjoying it, moving his hips back and forth to facilitate deeper penetration.

Without being coaxed, she lubed the dildo protruding from the front of her panties and using both hands to spread his cheeks she began to press into him. As the head of her latex cock slipped past his sphincter muscle, he gasped aloud. Giving him no chance to adjust, Jessica thrust forward, burying her cock inside his sissy pussy. A look of intense pleasure came over her face as she began to stroke it in and out. I knew she was being pleasured from two directions at once, the base of one dildo pressing against her clit while the other one moved inside her as she fucked him.

She began to increase the tempo, faster and faster, burying her plastic cock in Mike's sissy pussy. His body had adjusted to the invading cock now and his hips moved back and forth, meeting her thrusts. I knew it would soon be time for her to have the first climax of her life with a cock in her sissy.

"It's time dear," I said. "Turn on the vibes now and let our sissy slut feel his pussy being fucked by a woman in complete control." As soon as the words escaped my mouth, Jessica turned both vibes on.

As Mike began to buck and writhe from the sensations filling his body, Jessica's expression was one of complete bliss. I could see her legs starting to tremble as her climax neared. "That's it dear, let yourself go, give in to the pleasure, knowing this will only be the first of many orgasms you'll have today. Don't worry about the sissy, he is here solely for your pleasure and we will use him for quite a while before he's allowed to cum.

As I was saying this, her body began to shake and tremble as her climax overtook her. A look of complete rapture came over her face and she actually began to drool as her climax shook her. Her hips continued to thrust for a few seconds more, almost as though her body had taken control, until finally she stopped and withdrew from inside our sissy.

She sat heavily on the bed then, as though her legs could no longer support her. As she did, I got off the bed and said, "Once you've had a chance to recover, we're going to reposition our sissy for further play. I got so horny watching the two of you. I want to use him some more."

Jessica had recovered sufficiently from her climax to pull the dildo out. After releasing the ropes on his arms, I moved to the foot of the bed warning him, "Don't even think of using this as a chance to resist. The two of us could easily overpower you and then you'd really regret it."

He just laid there as I untied his ankles. "Now lie on the bed, face up," I commanded. He immediately complied, and without being told extended his legs and arms to the four corners of the bed.

"Be a dear and restrain his wrists, while I get his ankles," I instructed Jessica. Be sure he is spread wide and completely helpless." She soon had his wrists in the cuffs and attached to the headboard with a short length of rope. I had been busy with his ankles, attaching them in a similar manner to the foot of the bed. We both stood back for a moment to admire our handiwork. Our sissy was once again completely helpless and vulnerable. His body formed a perfect "X" his hard clitty aching for release.

"That looks good, now why don't you remove his hood and let our sissy pet see who just took his cherry? I'm sure he's dying to know which of my girlfriends was just buried in his hot tight sissy pussy."

"It will be my pleasure." She cooed, speaking for the first time since entering the room. Mike's body actually jumped as he recognized her voice. She reached behind his head, loosening the laces of the hood.

As she pulled it from his head, she continued her teasing. "Look at my macho boyfriend now! All dressed in slutty lingerie and tied down! I was the one to call Helen and tell her my suspicions about you. I wondered how my lingerie kept getting disturbed when you were left alone. The only answer had to be my boyfriend was fondling my lacy things. Helen and I worked together for a short period of time and we had lots of nice chats. It was then that she told me of her "hobby" transforming males into sissy pantypets. Her number was the first that popped into my head when I decided to test you and see if you really were a suitable candidate for panty training and feminization."

"He or should I say she looks so good," Jessica continued. "But the name is wrong! No one named Mike would be found in slutty lingerie after meekly allowing herself to be tied down.

We need to come up with a more appropriate name for her. I have it, Missy......yes Missy the Sissy! That is perfect!" She strode around the bed, repeating the name in a lilting voice. "Missy is my Sissy, Missy is my Sissy, oh my!" She bent over his bound form, her face just inches from his. "Now, what is your name? Come on you naughty girl, tell Mistress Jessica what you are called."

He mumbled the answer in such a low voice, only Jessica could hear him.

"That will not do! You must speak loudly and clearly, telling us your new name and your acceptance of it," she exclaimed. "Now one more time, what is your name slut?"

"My name is Missy," he replied.

"Not good enough," she said. "I want your full name."

"I am Missy the Sissy," he said choking the words out, but in a clear and discernible voice.

Jessica bent further and gave her a peck on the cheek. "You are learning my pet. Now that you've been taught to be a sissy for me, I'm going to take full advantage of the situation."

Turning to me, she said, "I really enjoyed those dildo panties while I fucked my slut, but I think I'm going to avail myself of the real thing this time."

I thought for a moment and replied, "Before you do, let me make a little addition to her clitty. I think it would be nice if she was not able to climax until we allow it. I have just the things to take care of that problem," I said heading once again to my toy box.

I came back with the rubber O-rings and set about once again binding our slave's naughty parts. As you may recall from the first time I employed these rings, there are six used. One around the base of her balls, one around each ball individually, and three on her sissy clitty.

Turning to Jessica, I showed her the advantages of using them. "Once they are in place, the poor thing can't lose her erection or climax. Her clitty however, remains available for a woman's pleasure. I think you will find them to be quite an improvement, as her clitty now has distinct ridges on it"

Jessica looked at her sissy's bound clitty and gave a Cheshire cat grin. "It looks like a French tickler on steroids," she joked. "I can't wait to straddle her and take that deep inside me. But first, I want to make sure she's properly aroused." With that, she bent over and while fondling her sissy's balls took just the head of his clit into her mouth. I could see her cheeks pursing as she sucked gently. Her fingers were dancing ever so softly over her sissy's balls. In very little time the sissy was writhing and bucking, straining against her bonds.

"Hand me a pair of your silkiest panties," she asked. "I have a feeling I know just how to drive my sissy wild."

I rummaged in my panty drawer, finally finding a pair of satin panties, the most slippery ones I owned.

"Watch this!" she said, as she began to pull the panties up and down the length of his clit and down over his swollen balls. With each stroke, his body bucked and his hips thrust upwards, tying to intensify the contact with the panties. Jessica stopped and wrapped them around his shaft and began to lightly stroke him.

"Does this feel good sissy girl?" she teased. "I bet you'd love it if I were to tighten my grip and milk you into these slippery satiny panties, wouldn't you?"

He didn't utter a word, but his hips began to move up and down, trying in vain to get the release he was being denied. Jessica stopped all motion and cooed softly. "Well, that's not about to happen. You are going to be kept right at the edge for hours. By the time I'm finished with you, you'll be aching to cum. And who knows? Perhaps I'll allow it, but no time soon sissy."

She straddled his waist, and looked at me. "Helen, would you enjoy using her slutty mouth while I use her clitty?", she asked ever so politely. It was so funny, her tone was one used by ladies at their teas, ever so prim and proper.

"Thank you for asking Jessica. I would love to." I replied, equally primly. I took only a moment to straddle his head, my pussy just inches from his waiting mouth.

Jessica moved down his body and grasping his bound clitty, began to rub just the head up and down the length of her slit. "Mmmm," she exclaimed. "This sissy clit is getting my pussy all wet and creamy, I do believe I'll avail myself of it." She began to lower herself onto the sissy clit. As the lips closed around the rings, she gave a gasp as first one, then two, then the final ring rubbed her clit as she took the full length inside her.

"Mmmm, sissy, your clit feels so good inside me! Are you enjoying the sensations to be had from my pussy devouring your sissy clit? Of course you are. But that is actually of little consequence. Your sole purpose tonight and for the foreseeable future is to provide pleasure to me and whomever else I may designate."

All this time, I had remained just inches from that lovely sissy mouth. Jessica saw that and spoke. "Go ahead Helen, let the sissy pleasure you with his hot wet tongue. He really is quite talented in that area, but I suppose most sissy girls are."

I lowered myself to his sissy lips and she immediately began to lap at my inner lips. It felt incredible. Seated as we were, Jessica and I were facing each other. I looked and her and smiled. "I hope you don't think me forward, but I'd love to play with your breasts while your sissy licks me to climax."

"You read my mind!" she replied. "But only if I can reciprocate. I've been looking at your nipples poking out of that naughty black lace bra the whole time I've been here."

"Mmmm," I replied, "let's not wait then." Using both hands, I began to caress and tease her nipples. Tracing around them with just a fingertip, I watched as they began to swell and distend. Jessica had not been idle either as I felt my nipples being similarly teased. Each of us was being serviced by our sissy girl while we played and teased each other in our naughty bras.

12