What are the Odds?

I was still kneeling next to him and saw Bob freeze at the question, but soon recovered and, still playing his role, removed his mouth from the cock and pleaded, "Please mommy, no... it's too big for a little girl like me... mommy's cock is not so big, but Miss Sandy's...", she trailed off not wanting to say the obvious, changing the subject somewhat, "...and I like mommy's cock... and don't want anyone else's in me!... Only mommy!"

Carol had advised Sandy of their mommy/little girl role play in more detail when alone earlier so she just took it in stride, while I was somewhat surprised at the tantrum but in no position to do much about it, just watched it play out. I supposed the private play I had with Sandy surprised them as much, particularly the severe paddling and cock and ball torture Sandy enjoyed giving me, that I was sure had shocked Bob. Anyway, it was definitely fun to be a part of it, even if only as a voyeur for the moment.

Carol quickly replied, "There, there... don't worry, my precious little girl... but don't be a brat in front of company or I'll have to spank you again!" she warned, which got a reaction of submissive silence and fear from Bob. She then continued more softly, "Don't worry, baby girl, only mommy will take your virgin pussy... when the time is right..."

I noticed the look between Carol and Sandy as she said that, and I wondered what they were up to now, but said nothing and maintained my kneeling pose next to them. Once again I thought I had it all figured out, but was soon to be surprised again.

Bob looked up at her in relief, and went back to licking and sucking on Sandy's cock again, maybe with a little extra enthusiasm. Carol stood up and took hold of my head and soon I was sucking on her cock again, but this time it was of my own volition as she released control of my head, and I bobbed back and forth on it with a sense of pride at my oral skills. Wearing a wig and dressed like a girl with make up and breasts, I just hoped I was pleasing to Carol and Sandy, and actually worried what they thought of me, like any teenaged girl about some boy she liked at school.

When Sandy and I played alone together I lived out my role in the relationship as best I could, but here with a like-minded couple with their own dynamic that somehow weirdly complemented ours, the wine and food combined with a night swim dressed in skimpy bikinis, and sucking cock of both Sandy and her new friend Carol, I was able to take it all to another level, living the role that I had previously only played at. Immersed as I was, it was already the most erotic day in my life, and I was no youngster anymore. But that was even before what came next.

While our attention was occupied with the cocks in front of us, Carol and Sandy were talking quietly in each other's ears, occasionally nodding in agreement, until they gently pulled us off their cocks, to both our dismay.

Carol couldn't resist, "Don't worry, my dears, they will be back inside you before you know it! Sandy and I are going to take a little break, so you get one too. Take the time to pee if you feel the need, but make sure and clean up properly... help each other if you must. Other than that, have some wine or whatever you want, and just relax for a while."

Without any further explanation they left into the master bedroom and closed the door. Neither of us dared to open it so we went to the guest bathroom and took turns peeing and cleaning ourselves, something Bob was much more used to with the cage on than I was, so I followed his lead. We returned to the living room and I filled a glass of wine for each of us. We sat on the sofa, our frilly dresses piled up around us, our knees together like good girls. While our glasses were held in our outside hands, we held each other's with the other, getting some comfort from the contact. That is how our wives found us when they returned to the living room.

I felt Bob squeeze my hand as they came into view, the change in appearance and demeanor apparent at first glance, and more so once in full view. Both women were naked from the waist up, their breasts declaring without question their inherent femininity. It even looked as if they had rouged their nipples, to make them even more prominent than they were naturally.

Their hair was brushed out and make up that enhanced their eyes and lips had been added. Both ladies wore a black garter belt, and attached straps extended down across hips and ass cheeks to hold up black thigh high stockings. Lower down each wore pair of black boots that went up almost to their knees, both with a two or three inch heel, the entire ensemble making our short wives look much taller than normal.

I figured, later confirmed correct, that Sandy must have borrowed these from Carol, since we hadn't brought any that I knew of with us. Once again fate gave them close enough shoe sizes for that to work out so well. It was a pleasant surprise for me, since I often asked Sandy to wear her boots when we played, a minor fetish of mine. The additional height not only gave her a sense of increased power but also actually made it easier for her to peg me due to our height differences.

Anyway, the boots were just the icing on the cake seeing these two beautiful, sexy women coming towards us side by side to play with me and my new companion in crossdressing. But the ultimate change in appearance was what was sticking out from their crotches. Both still wore the black leather harness that held their cocks earlier, but now Carol's held the large flesh colored dildo that Sandy had worn earlier, while Sandy's held a new black one I had not seen before, that was not quite as long but definitely had more girth.

Bob was shocked once again, understanding the implications of Carol wearing the bigger cock- the days of playing with little girl toys was over. And it was happening in front of Sandy and Michelle, which was both embarrassing and arousing. When he looked at the monster cock Sandy wore, he got really scared, but I quietly assured him that was only for me.

He visibly relaxed, even knowing he would be fucked with a much larger one than ever before. I had seen that black cock before, but did not know Sandy had brought it with us on vacation, and conveniently never laid it out on the bed for Carol (and therefore me) to see when we were in our room.

I had bought it a while ago on her orders, but so far it was too big to penetrate me, although she had surely tried several times. It may not seem like it mattered, but the extra half inch or so in diameter made a big, big difference. That it was shorter made no difference when the even thicker mushroom head attempted to stretch your tight hole wide open. Those were the only times I ever safe worded, and I wondered if this would be the first time for success.

Like I knew Bob wanted to please Carol, I wanted to try and please Sandy, and having the other couple there going through their own test, pushing the limits for the sissy, helped more than hindered my own immersion in the situation. I was aroused and terrified, and looking at me looking at her huge cock, Sandy knew it and smiled.

Carol began by pulling Bob off the sofa to kneel once again on the floor to one side facing us. We both thought he was going to be forced to suck her cock, but it quickly went in another direction. She turned to me and flipped me over, now kneeling on the floor face down on the sofa cushion.

Sandy sat down next to me and leaned over to press her body into mine. I could feel her large breasts and erect nipples pressed into my back, a feeling I always treasured, as she held me down. She pulled my dress out of the way and I felt Carol pull my panties down to my knees, and with a few tugs completely off.

Face down I could not see but felt Sandy pass something to Carol, and soon I felt someone's gel covered finger press into my asshole, first one and then two fingers. They were removed and reinserted several times, adding more gel each time, for which I knew I should be grateful, and sincerely moaned in pleasure at the feeling.

From above me I heard Carol order Bob, "Get over here and lube up my cock... no, not with your mouth, with the lube!" She apparently handed him the tube, and I assumed he was coating her cock with it. I felt her move forward and she said to Bob, "Ok now Barbi, hold her ass cheeks apart and line up the tip of my cock with her tight little hole... yes, like that... now watch carefully..."

I felt Bob's fingers pull apart my ass cheeks around my asshole, and the tip of the cock touched lightly just above my hole. I lifted my ass up and wiggled it a few times to help line up the cock with my hole, and realized what I was doing in front of Bob and Carol, which is inviting her to penetrate me with her cock, but first she had a little fun of her own. Carol laughed and pushed her hips forward slightly, enough for me to feel it but not enough to penetrate my tight ass hole.

"So I see this little girl, so good at sucking cock, also likes a cock in her pussy... tell me what you want, young lady... come on, don't be shy..." Carol cajoled, and I hesitated until Sandy smacked my ass hard and ordered me to answer!

So I responded, "Oh, Carol... please fuck my boi pussy... I know I am just a dirty slut whore, here for your pleasure... please let me pretend I'm a good girl... make it hurt like a virgin, with your big cock when you stretch me open... and then you can use your big cock on me for as long as you need to... until you cum..."

As I spoke Carol began to get aroused at the scenario I had detailed out, and it was enough for her to reply, with a growl in her voice, "You see, Barbi, what a slut she is... someday you'll be begging for this cock too!... but for now... unngggh!!!!" As she held on to my hips with both hands, she pressed forward and the tip of the cock easily penetrated the outer starburst of my ass hole, and the head stretched it further until it popped inside. Next the head met with the tight barrier of my anal sphincter muscles, surrounding the opening like a ring of steel, and that is when the sharp pain started as it stretched open more than normal, and eventually almost more than possible.

I felt Sandy's body like a comfort blanket on top of me as I trembled and moaned in pain, "Oh God.. so big... owwww.... ohhhhh.... too big..." as commentary to my ordeal, not that it would or should in any way stop Carol. She did stop pushing for a moment after the head had penetrated beyond the sphincter to let me get used to it, but when I wiggled my ass and actually pushed myself back on to her cock, she laughed, held tight to my hips and pushed hard to penetrate me until it was fully embedded, her abdomen pressing against my still sore spanked red ass. Mercifully she held herself there for quite a while, letting me get used to the feeling of fullness her cock provided.

After a long pause Carol slowly pulled the cock out so only the head was inside me, and had Bob add more lube along its' length before she slid it all the way back in in a single thrust, eliciting a groan from me that began to combine pain and pleasure. She began to fuck me at good pace, not too slow or fast, pulling almost all the way out before sliding it back in, and as she did she spoke conversationally to Bob, "Now Barbi... as you can see a boi pussy is made to take a cock, no matter how big... didn't you see how it stretched so nicely as it was penetrated... and I know it hurts at first, but that's part of being a good girl... and it feels so, so good after that," then addressing me "Isn't that right, Michelle?"

I barely heard her question in my position with my face in the sofa cushions and blocked by Sandy's body, but luckily did and replied, "Yes! yes!... it feels sooo good... please don't stop... harder... faster... yessss...."

With no more encouragement Carol moved Bob back a little to watch and began to fuck me harder and faster. She held my hips tightly except when she let go to give me a good smack on the ass, pounding into my ass with her abdomen each time the cock bottomed out deep in my bowels.

She kept up that pace for a long while, until she began to slow down and pull all the way out, so it was just barely still inside by the tip of the head, and held it there interminably before she pressed it all the way in in one hard thrust that brought a cry from my lips and the breath from my lungs. After holding it there for a while she once again slowly pulled it all the way out, making me wait in fearful anticipation of the next violation of my boi pussy.

She played this game with me over and over with great enjoyment at my distress, combined with my begging for more each time she pulled out and held it there, until the final time she just held the tip of the cock at my asshole and ordered me to fuck myself on her cock, to pleasure her cock like the whore I was. I began to press back on to the cock and felt it slide all the way in until we were once again touching. I began to bounce my body back and forth, causing the cock to slide in and out of my ass a few inches each time, and each time I pressed back I made sure my ass pressed hard into her groin and I wiggled it back and forth, to Carol's delight.

From long experience with Sandy I was pretty sure the back of the dildo was pressing into her vulva and engorged clit, surprising her at the arousal it created in her loins. Like many women wearing a strap-on that I saw in pegging porn, Carol had always placed it too high, above her pubic bone and not her pussy, so she gave Barbi was she needed but did not receive for herself.

Sandy had adjusted it for her when they were alone, after telling Carol that she always had an orgasm from fucking me, and I would give her one too later that night. While she fucked me she breathlessly teased Bob, "You see how a good girl pleases her man... if she keeps this up, I might even cum in her ass... don't you want to be a good girl like Michelle here?"

I was too preoccupied to hear Bob's reply as Carol began to fuck me hard again, and I knew it would continue unless and until I could make her cum, so began to cry out, "Yes! Yes! Cum for me! Cum in my slut pussy!" and pressed myself back into her in time with each of her thrusts forward, and wiggled my ass to vibrate the back of the dildo over her own mounds as it pressed into me. Her juices were flowing copiously and a wet slap sounded with each thrust forward.

It did not take long before she was pounding into me with great ferocity, relishing the counteracting pressure on her own pussy and clit, and her own voice rose above mine, calling out, "I'm cumming! I'm cumming!!!... Ahhhhhh...", and she pressed it deep into me for the last time and collapsed forward to lay on my back. She held herself there for a long pause, and whispered in my ear, "That was fantastic, my dear little girl... I've never cum like that before... you have such a sweet tight ass..."

I could only lay there, her body holding me down. Sandy had sat up as Carol came and now was petting my head, helping me calm down from the brutal violation. I wondered if this was a false calm, given she still wore the huge black cock I had never been able to take before. Eventually Carol pulled back and the cock slipped out of my ass, and I was sure my hole was gaping to her and Bob's view.

Exhausted, she plopped down on the sofa and I heard her say to Bob, "You see Barbi, the boi pussy stretches so nicely, and so will yours when the time comes, so to speak," and she giggled at her own double entendre. I could hear Bob mumble a nervous thank you.

That Carol and I needed a break was obvious, but it seemed Sandy and Bob also needed a break to recover from the intensity of the scene that played out so intimately before them. So slowly we all got up and, after a group hug, went back outside and sat at the table, quietly eating some of the fruits and sipping more of the wine. Still without my panties, before I sat down Carol gave me a small towel to put down on the seat, for obvious reasons. She took her leave and went to the bathroom, we later found out to clean her cock, but soon returned to join us still wearing it.

Bob and I were still in our little girl dresses, wigs on our heads, while Sandy still wore the ominous black cock and was naked from the waist up, as was Carol. Both our bottoms were sore from the spanking and mine more so from the fucking I had received, so we both fidgeted in our seats quite a bit. Sitting together like this with another couple as if it were all quite natural was all highly arousing, as my cock still restrained in its' cage reminded me.

The funny thing is the more we sat and talked, and drank, the more normal it all became. Much of the conversation was steered by Carol and Sandy to deliberately embarrass us in front of the other guy, revealing several secret desires and perversions, which was no small thing after all we had done and revealed already.

Eventually the conversation petered out, and we sat in silence for a while. I noted the sexy physical contrast between Carol and Sandy, enjoying the view of Carol's small breasts with their long erect nipples, sitting across from Sandy's fulsome round breasts capped by large coral hued areoles and eraser sized nipples. I had to admit Bob looked quite sexy too in his wig, make up, dress and stockings, and could see how he could be considered an attractive woman, and was jealous that I could not pass like that.

I wondered if Sandy had thought about that by now, and if shaving both my facial and genital hair was in my future. Anyway, once again my daydreams were cut short. Carol stood up and announced, "I think it is time to adjourn to the bedroom. Don't we all agree?"

Sandy affirmed her agreement, while Bob and I just nodded, and we all got up. Carol took Bob by the hand and led him back inside and through the bedroom door. Sandy took me by the hand and we followed behind.

When we were all in the bedroom, Carol asked me to help Barbi out of her dress, so I undid all the clasps in the back and helped to carefully pull it over his head and off, leaving Bob in a bra, panties, stockings and shoes.

Carol led Bob directly to the end on the bed and pushed him down so he was laying on his back, his legs bent down so his feet still touched the floor. Carol pushed his legs up and back, bent at the knees and had Bob hold them there, exposing his asshole, balls and cage covered cock. Carol stood between his legs and, holding the large, flesh colored cock in one hand, touched the tip to Bob's asshole, eliciting a cry of fear, "Please, mommy... I'm too small and you are too big... do you have to? I'll be a good little girl for you... I promise..."

Carol just smiled and soothingly replied, "Didn't mommy show her how nice a boi pussy stretches to take mommy's cock... didn't Michelle love it once she got used to it? Yes, it does and yes, she did... and so will you, my dear... you will be a good grown up girl for me, won't you?"

Bob replied, "I'll try, mommy..."

Carol called Sandy over to sit on the bed next to Bob, her arm around his shoulders to give him some comfort, and hold him in place if he struggled too much. I was moved to kneel on the floor next to Carol, who handed me the tube of lube. I didn't need any instruction as I took the lube and generously coated Carol's cock with it, and at an indication from Carol added more lube to my fingers and applied it to the outside and inside of Bob's asshole.

I had lubed up my own asshole many times for Sandy, but never another person's, so I just did what I thought I'd want him to do for me, to make the inevitable easier. I started with one finger, added some lube and inserted two fingers, then three, moving them slowly in and out and feeling him relax to the digital massage. Carol let this go on for quite a while, making sure Bob was truly ready, trying to avoid as much pain as possible for her sissy girl, but eventually had me stop.