What are the Odds?

Sandy caressed my ass and up my back, bringing goosebumps to my skin and a chuckle from her. She spoke to me, "You won the race so get a reward... what do you think you would like, slut?"

I responded with the truth, using a well memorized formula, "My reward is to give you the pleasure of torturing my worthless cock and balls, and turning my ass nice and red, just the way you like it, Mistress... before you... well, you know..."

Sandy laughed and responded, "Yes, I know... but Carol doesn't... so why not tell her? Come on, a slut like you isn't that shy..." Of course Carol knew exactly what I meant, but Sandy wanted to make me say it out loud as a further humiliation in front of Carol and Bob. The fact that both of the woman were wearing cocks in harnesses and had been for much of that evening was irrelevant.

But I was that shy, and it took every ounce of strength for me to finally reply, "To... to fuck this slut... until Mistress cums..."

"Very good, slut... and what about our host Carol?" Sandy inquired.

Unsure of how eager I should appear, I replied cautiously, "As her property, Mistress is free to give her slut to Carol to use in whatever way pleases her."

Sandy got serious, "Well, then, now that that is all settled, let's get started. Carol, would you please pick up the two hairbrushes? Excellent, now turn them so the bristles are facing out and the wood is against your palm. That's perfect. Now place them on either side of Michelle's balls, and squeeze them together lightly." She did hesitantly, unsure of how much was appropriate, and I moaned.

Sandy continued, "Now a little harder." She did again and I moaned again. "What do you say to Carol, slut?"

"Thank you Carol... it feels so good... I hope you are enjoying this... you can do it harder if it pleases you... much harder."

Carol responded as she squeezed a little harder, "Actually I am... enjoying this, more than I expected. Barbi is a little sissy and can't take pain like this, but I think we might try some training in the future. Looks like we can both learn from each other!"

I groaned at that comment, thinking about the cock cage, as did Bob, who was watching his wife get aroused from squeezing a pair of balls between the prickly bristles of two hairbrushes and thinking it will be himself one day, probably sooner than later. I looked over at him and gave a look like 'sorry', but he just sat there and watched with trepidation. Carol saw this interchange and squeezed even tighter, eliciting an even louder groan from me. While Carol continued to squeeze my balls, Sandy reached in and pulled my cock back to point towards Carol, which had the effect of pinning it against the arm of the sofa between my legs, which Sandy had me spread apart.

It also had the effect of pushing my ball sac into a tight ball. Sandy gently took hold of Carol's hands and pressed one brush's bristles on to the length of my cock and the other on my balls, bringing a loud moan from me. She then took one hand and moved it face up under my cock, already tensioned downward from being pulled back, so the bristles were against the top of my cock, that was actually then on the bottom, and brought the other hand to press bristle side down on the bottom of my cock, that was now on top. My cock was squeezed between the two brushes.

Sandy had her hands over Carol's and began to press them together, giving Carol an idea of how much I could take. But even that was much less than I had experienced with Sandy over the years. The moans and groans required a lot of effort on her part to become the louder cries of real pain, and Carol was not there yet, or even close. But of course she didn't know that and was astounded at what pain I was already taking.

Sandy released her hands and left Carol to experiment with the brushes on my cock and balls as she pleased. She began to find out what kinds of pressure and areas of special sensitivity brought a response, and Sandy told her she was going to paddle my ass, so she should hold on, and Carol brought her hands to the top and bottom of my cock and squeezed tightly.

Sandy picked up the paddle and without any delay brought the first smack to my ass, and Carol felt as I was pressed down from the blow. She understood she didn't have to do anything, that the paddling would torture my cock with each strike, so just held on. The blows came down on my ass one after another, each causing the immediate pain in my ass as the paddle made contact, but also the pain in my cock from the brushes. Soon I was moaning and crying out loudly, and thanking Sandy and Carol for punishing me so good, which only increased the severity of Sandy's ministrations to my ass and the pressure Carol applied with her hands.

It was not long before my ass was flaming red, and I was pleading with Sandy to stop. As usual she ignored my pleas, and Carol continued to press the bristles into my cock. It continued for about fifteen minutes, which felt like forever, before she finally stopped and lightly caressed my ass cheeks, feeling the warmth generated by the spanking. At her direction Carol pulled the brushes away from my cock, and for the first time in a while I was able to relax, letting go of the tension that had built up in all my muscles as I collapsed into the sofa. I still had not cum, but edging me for hours was standard procedure for Sandy.

She had me get up, laughing as I flinched when my ass inadvertently touched the cushion. Carol had refilled all our wine glasses and with a clink of our glasses the girls took a sip, while again both Bob and I took a bigger swig, needing extra liquid courage. Carol had us all move over to the dining table and we all sat down; both Bob and I sat down gingerly on our sore asses, mine I was sure much more so than his. We talked, drank more wine and ate some of the fruits and vegetables Bob had prepared earlier.

It was nice to relax after the intensity of our spankings, and after a while it seemed almost normal for Bob and I to be crossdressed and the otherwise naked ladies wearing their cocks as we sat and talked about various matters of interest. After a while the conversation lagged and Carol announced it was time we got back to our play. She ordered Bob and I to go to the guest bedroom and put on the clothes that she had laid out for both of us. When she had the time to put out the outfits we found there I didn't know, but with all the distractions of the past few hours, that wasn't surprising.

On the bed were two dresses, satiny and frilly, with puffy sleeves and a low cut, lace edged neckline, and the short dress flared out with lots of crinoline folds of cloth underneath. One was a rose color and the other was a light blue. They were the type of dress a proper young girl might wear to a party, except not quite long enough for us. Think a sexy Shirley Temple. With them were a pair of panties covered in rows of lace, giving them more bulk than a regular pair, and I was sure would make our asses more prominent. A cotton padded training bra, a pair of white stockings and black patent leather Mary Jane shoes completed the outfit. I didn't think the shoes would fit but looked at Bob's feet and was no longer sure of that.

As we started to undress from the things we currently had on, I asked him if these were all his things, and he told me that Carol liked to make him into a young girl, and then shyly admitted he liked it too. They had a pretty large collection of lingerie, dresses and other women's clothing, including the shoes, all in Bob's size. I was jealous to say the least.

Once again fate was kind and we both wore close enough to wear the same size. Since he was a little stockier and shorter than I was, the dress would cover even less of my ass, but given the circumstances that was not really of importance. I told him I only had a few items to dress up in, some of which he was seeing now, but only bras, panties, garters and stockings, plus a few nighties and a French maid's outfit. Soon we were both naked, except for Bob's cock cage that he still wore, and I began to get dressed.

Bob, who had remained silent for the most part suddenly spoke up, although it was in a whisper I could barely hear, "Mommy says nice little girls don't have big tits. They have little boobies." Not quite understanding, I asked him to repeat it, so he said little louder, "Mommy says nice little girls don't have big tits. They have little boobies."

It was a little weird since it was said almost like it was a fact drilled into him with much repetition (as it was), but I simply replied, "OK... so we should take these off?" He nodded and I asked, "So how do we do that?" He came over and held the top edge and pulled, and it slowly but surely peeled away from my body. It was a little uncomfortable but not too painful. I couldn't help but be aware of the weight being lifted off my chest and shoulders, and realized I had become used to it in even that short period of time.

Bob stood in front of me and I peeled his breasts off as he had done mine. He took a bottle of a clear liquid and squirted a little on a cloth, and wiped the residue adhesive off both our chests. When done we began to get dressed. To make it go faster and easier we agreed to help each other. Bob sat on the bed and I knelt in front of him and rolled the stockings up his legs. I couldn't help but notice the metal cage still confining his cock, and couldn't help but ask, "Do you mind wearing that cage?"

Bob hesitated and looked at me as if the question was irrelevant, which it probably was to him, but replied, "Mommy says little girls need their clitties confined or they get in trouble."

It was said in that absolute fact way that once again indicated long training and repetition, and I was intrigued by it, but just left it alone and again said nothing. Once both stockings were on, I put the Mary Jane shoes on his feet and he stood up. I picked up the panties and he lifted one foot and then the other as I slipped them up to cover his cock cage and ass. I stood up and held out the bra and he slipped it up his arms and turned so I could clasp it in the back. It was a padded training bra that fit his real breasts.

I picked up the rose colored dress, and lifted it up and over his head as he threaded his arms through the sleeves, then down until it was settled on his body. He turned around and I buttoned the hook clasps up the back like a corset, which it had instead of a zipper. With a few tugs and adjustments it fit him well. He then went over to the mirror and checked his wig and makeup.

He then had me sit on the bed and proceeded to kneel down and put on my stockings and the shoes, which were a little tight but manageable. I stood up and he put a padded training bra on me, and it also seemed tight since I was used to Sandy's DD's, but also felt nice on my nipples. He then helped put my panties on me, followed by the dress. The dress was a little loose on me in the body, and also shorter in the front and rear than his due to my height, but in the end as he closed the clasps in the back it fit me pretty well too.

I checked myself out in the full length mirror and was surprised at my reflection, the ensemble giving the look of a young girl ready to go to her first formal party. Bob brought over a black wig, cut in a bobbed style in front with the sides and back about shoulder length, and told me he thought Carol might prefer me to wear one too, so I let him attach it to my real hair underneath, and even with my facial hair it made a decided improvement in my overall look.

We both looked each other over to make sure all was right and proper, took a deep breath and went out of the room towards the living room. I was surprised when Bob took my hand in his and squeezed a little bit, and I returned the squeeze and did not release his as we entered the living room. Sandy and Carol were sitting on the sofa side by side, each with a glass of wine in hand, and smiled broadly as we came into view.

Carol got up and gushed, "Oh my God, you two are adorable! Come on, turn around so we can see it all!" She then held Bob by the shoulders and gave him a peck on the lips, then moved over and did the same to me, except she lingered a little longer with hers pressed into my lips. I looked over nervously at Sandy but she just shrugged and smiled. Carol picked up two glasses of wine and handed them to me and Bob, and Sandy got up to join us. Carol proposed a toast, "To Barbi and Michelle... and sharing..."

We all repeated the toast and clinked glasses, then took a sip, and as before Bob and I took a little more substantial sip than the ladies.

We stood there silently for a moment, sipping more wine until Sandy broke the quiet, "You two girls are adorable, but your sweet looks are not going to get you by in this difficult world. You will need skills... skills to satisfy a man... and keep him... as women have been doing since time immemorial. We know you have some experience, but are now ready to become real women. You both want to become a woman and leave your little girl life behind... yes?"

I stood there astounded, as Sandy elucidated the fantasy and now reality we were playing out so wonderfully, and I could only feel more and more like the young girl I was dressed up as, wondering what adult pleasures would come from both my wife and Carol.

Bob seemed a little less astounded, as this was apparently a common role-play for him and Carol, so without much hesitation answered her, "Oh, yes mommy! Please teach us what we need to know... we want to be good girls!" After a hesitation he added, "But mommy, you know I'm a virgin... I heard it will hurt, and I'm afraid..."

Sandy giggled at that, but Carol took a more serious attitude and replied, "That's perfectly understandable... yes it may hurt the first time, but lie mommy told you, it is just for a little while and then you get to enjoy it. Mommy was a young girl once too so knows how you feel, so just be a big girl and accept with gratitude whatever you feel, good or bad."

She turned to me and asked, "And what about you, Michelle. Do you want to learn to be a big girl too? And are you also a virgin?"

I looked over at Sandy and back to Carol and replied, "I thank you for taking the time to help my mistress. I will be as good a big girl as I can. But no I am not a virgin... Mistress raped.. I mean deflowered me on our wedding night, a long time ago."

Carol delighted in that image, hoping to remember to get all the details later from Sandy, clapped her hands and declared, "Well, there is no time like now to get started! But before we do we have a little matter to attend to. Michelle, please come over here." I moved over closer to her, with Sandy next to me, and she leaned over and pulled down my panties, freeing my cock that was partially erect. Carol took hold of my cock and declared, "I'm afraid this clitty will be a distraction if we don't do something about it. What do you think, Sandy?"

Sandy already knew where this was going and replied, "It's always been a problem and heartily agree that something needs to be done. Tell me, you don't have another one of those cages we could use, do you?" My heart sank at the thought, but my cock responded otherwise, stiffening further. Looking down at my cock, Sandy commented slyly, "You might want to get that down, tiger..." I closed my eyes and thought of multiplication tables to try and reduce my arousal, to only minimal effect.

Carol smiled, "Of course... I'll be right back," left to the bedroom and returned promptly with the two sections of metal in her hand.

"OK, Michelle, let's get you situated. Sit over here and lift your legs up and apart." I moved as directed and was soon exposed, but with the fluffy dress I could not see that area of myself. But I could surely feel the fingers of Carol and Sandy and they manipulated the back section in a circle behind my balls and over the top of my cock. This cage also had a sounding device built in; it was thinner but longer than the one I saw go into Bob's penis. Since Sandy and I had done some sounding and similar penis play was occasionally part of her cock and ball torture sessions, I actually looked forward to it.

So when I felt the sound press into my hole and down my urethra, I moaned in pleasure. But when it came to attaching the front to the back section it was much less pleasurable as they pushed and squeezed my cock until they finally could clasp the two parts together and insert the padlock to secure it all in place. I could feel Sandy holding it and moving the entire package around, inspecting it from all viewpoints, and for good measure she gave my balls, distended into a firm ball by the cage, a few good smacks with her hand.

Not too hard, or at least not as hard as she's done sometimes in the past, but still hard enough to evoke a reaction from me as I groaned. Sandy and Carol stood up again and lifted me up as well. Sandy bent down to pull my panties back up and over my new cock cage, supporting it in place, which seemed more comfortable than when hanging free.

Bob had stood by and watched the entire time I was being caged, and now the attention of Carol was directed at him. "I think the first order of business is this young ladies cock sucking skills. We all know that is critical to every woman's panoply of skills to please a man... every guy loves a good blowjob, and it can be pleasurable for the woman as well... well, at least I enjoy it. The feel of the head in your mouth and feeling it swell as you take it in deeper, until you get that tasty treat of cum... well anyway, you get the idea, so let's get started. Barbi, get down on your knees."

Bob got on his knees and Sandy and Carol stood facing him side by side, their cocks now at close to eye level for Bob. I remained standing off to the side, but had a good view of the three of them. "OK, now suck Sandy's cock... let's see what you can do without any help."

Bob took her cock in his mouth and began to bob back and forth on it, moving a little deeper each time, until he reach a point where it hit the back of his mouth pressing into his throat and he gagged on it, and had to pull back and recover. He kept trying and soon tears were falling down his cheeks as he gagged over and over, giving it a good try.

In character, Carol said, "Mommy is not happy with you, Barbi... I'll just have to give you some encouragement to try harder. Bend over the table here." Already on his knees, Bob shuffled over a few feet and bent over the coffee table. Carol unceremoniously pulled down his panties and began to smack his ass cheeks with a hairbrush she had left there before.

Bob squealed and cried out like a little girl, and begged her, "Mommy, no! Please no! I promise... I'll do better... Mommy please..." His words trailed off as he soon could only cry out from the pain and words became garbled. He obviously had a much lower pain threshold than I did, but that was no consolation to either of us, knowing what might come sooner than later. Starting out a little pink from the earlier spanking, his ass was quickly a nice shade of red before she stopped and pulled him up by the neck and turned him to face Sandy again.

Without being told he took Sandy's cock in his mouth and started to take as much as he could, then pulled back and tried again, actually making some progress towards the finish line, which I assumed from experience was his nose touching the leather harness holding the cock, proving it was taken completely in the cocksucker's mouth.

As Bob continued to work on Sandy's cock, Carol motioned me over to her and soon I was on my knees sucking her cock. It did not take long before I was able to take it all, and once I did that Carol took hold of my head and began to fuck my mouth and throat with her cock. Gargled sounds came from my saliva drooling mouth as she violated me, as Sandy looked on smiling at both my torment and the efforts of Bob on her own cock.