What are the Odds?

For the next fifteen minutes Sandy sat in the chair with her legs spread apart, Bob's face directly on her pussy. He licked and sucked at her pussy and clit as best he could while still bound, and when she had a nice orgasm and coated his face with her juices, she got up, leaving Bob happy with the taste of Sandy's sex on his tongue.

He expected Carol to follow but they came over to me, led me back into the center of the living room and had me stand bent over the back of a chair Sandy had placed perpendicular directly in front of Bob, giving him a ringside view. I had been in this position before and knew the requirements for this punishment.

I didn't have to hear or see Sandy pick up the cane, but knew implicitly she was doing so. I did hear the swish of the cane as she swung it through the air, always seemingly benign but actually a warning to any exposed ass that was near. Then she brought it down across my ass cheeks, causing a searing slice of pain, and a cry emerged from my mouth unbidden.

However, I regained what composure I could and quietly announced "One, thank you ma'am...may I have another?" Sandy did not reply and brought the cane down across my ass again, a little above the last stroke. I moaned and continued "Two, thank you ma'am, may I have another?" This went on in her steady practiced way, Sandy giving me time to recover in between strokes when needed, until I had counted out ten strokes, and a ladder of red lines and welts ran parallel to each other across my ass cheeks.

While I was mostly concerned for my own situation, as I was being caned I could overhear to the side the sounds of Bob licking at Carol's pussy as she stood with legs apart in front of him. I hadn't noticed but she had removed her harness so he could access her pussy, and was now naked with her back to me. She did have a nice ass, but I was too preoccupied to think about any future there. It was my ass I needed to be concerned with, and was brought back to the present with the final tenth stoke of the cane to my defenseless ass.

Once I had pronounced "Ten, thank you, ma'am" Carol pulled away from Bob and came over to Sandy and me. I could see the copious moisture coating her pubic hair, outer mounds and even running down her thighs, the result of Bob's oral efforts.

Sandy handed Carol the cane and went over to stand in front of Bob's face, her huge black cock sticking out menacingly. Sandy saw the anxiety on Bob's face and laughed as she peeled the side straps of her harness off her hips and the entire harness pulled away from her body and fell to her feet, "Don't worry... sweet young girls like you are not ready for that... yet... but they are good for some lesbian pussy licking, which your mommy says you are pretty good at, little girl. Show me, or do you need an incentive?"

Bob knew that 'incentive' was mommy-talk for punishment, and he quickly nodded his head yes, and called out "No, ma'am... I mean, yes, ma'am... I mean, I'll do my best..." and tilted his head back as Sandy moved forward to bring her pussy in contact with his mouth, and soon his tongue was working up and down in her slit, touching her clit when she bent down slightly to give him access, her juices rapidly coating his mouth and face, and I could hear the moans from Sandy as he touched her most sensitive spots.

She just enjoyed the pleasure he gave her, not allowing it to build up to achieve an orgasm. She preferred to hold that back for me later, so pulled away from Bob's face, who wound up licking at the air for a long moment before he caught himself, embarrassed when he realized both Sandy and Carol had seen him and were giggling at this new little humiliation.

While Sandy was being serviced by Bob, I assumed Carol was also going to use the cane on me, with the fact that she held it in her hand and was swishing it about it a strong clue. She did caress the welts and red lines that Sandy had so expertly created on my ass cheeks, feeling the bumps and warm glow the spankings and caning had produced. She was gentle about it so it felt very nice and I appreciated the break.

Carol had not yet put back on the harness, and surprised me by laying on her back on the sofa and pulled me down to kneel at her feet, my face in between her spread legs and her pussy open and inviting to me. I didn't need a formal invite and bent forward and was soon licking at her folds and into her slit, from her asshole to her clit, working to build the arousal to a peak of pleasure, holding her there for as long as possible before thrashing at her clit to bring her crashing over the edge.

Her orgasm was fierce and loud, and she shook and bucked under me as I worked hard to maintain contact with that delicious moving object. It continued with her body convulsing in waves and sharp spasms erupting when I flicked my tongue across her engorged clit, slowly receding in intensity until she was laying back into the cushion of the sofa, breathing hard with a wry smile on her face. I just remained kneeling between her legs, softly kissing her inner thighs and licking lightly at her swollen mounds.

When she had caught her breath, she called over to Sandy, who remained standing with her pussy in Bob's face, "Wow, I could get used to this... you are one lucky lady!"

Sandy smiled and called back to her "Yes, she is a good pussy licker, isn't she? Barbi here isn't so bad either... but I think they both will need lots and lots of practice!" and laughed with Carol who heartily agreed. Sandy continued "But that is not all they are good for, is it my slutty girl" On that she pulled away from Bob and began to put the harness with its' big black cock back on, and Carol pulled herself out from under me, stood up and was soon wearing hers, with the beige flesh colored cock somewhat smaller than Sandy's.

Everyone in the room knew that I had taken that one from Sandy many times and from Carol the night before, but the black one was a new experience, and there was little doubt it might be as painful as a girl losing her virginity to a very well endowed man, his cock breaking through her barriers and stretching her pussy to its' limits. But that looming violation was not all our devious wives had planned for me, or us. Sandy had me kneel on the floor with my upper body on the sofa facing the back, and I just stayed there while she and Carol untied Bob from the ottoman. From the sounds I heard it seemed in addition to his rope ties they were removing his cock cage, confirmed from his loud sigh of relief as it was removed.

Carol escorted Bob over behind me, gently forcing him down to his knees. I'm sure Bob thought he was going to be forced to rim my asshole, as did I, but instead she handed him the base of the other cock cage used on me the prior night, which he clasped shut around the base of my cock. From Bob's handling of my cock and the general atmosphere of sex in the room, I was partially erect, so was quite nervous when Sandy had me turn around and lay on my back with my sore ass on the edge of the sofa.

Carol helped and held my legs apart while Sandy held my cock and slowly but surely penetrated my pee hole with the two inch long hollow sound attached to the cage. I moaned but stoically refused to complain as the sound slid deeper inside and the cage slipped with difficulty over the mushroom head and with even more difficulty compressed it tighter until it met the base, causing me some distress. My cock was partially hard but could not compete with the strength of Sandy's hands, so soon she was locking it closed.

She tugged at it and slapped my distended balls a few times, making sure it was on good and tight. No doubt it was not going anywhere, and Sandy was clearly enjoying this new addition to our play. I might have worried more about the long term future but the present situation required all my attention.

Sandy got up and moved over to hold Bob by his cock, which was as erect as it ever got, and pulled him over to the sofa, and I could see Carol had replaced the rope that had tied him to the ottoman with the metal ring around the base of Bob's cock, which of course concerned me. I was concerned for good reason as Carol slid Bob to sit on the sofa in front of me, my face in his crotch where his little cock stuck up like a thumb, a dribble of pre-cum emerging from the tip.

With Sandy on one side and Carol on the other, in a few quick motions a leather strap was snapped shut to the ring on my collar and pulled forward until I had no choice but to open my mouth and take Bob's cock inside, and Sandy snapped it closed at the other end under Bob's balls. I realized I hadn't even protested or resisted at all taking a real cock in my mouth and Sandy and Carol knew it too, which was confirmed when Sandy bent down and kissed me on the cheek, saying "Now that was easy, peasy... such a good sissy, she loves to suck other sissy's clitties..."

To emphasize my situation, Carol brought her fingers to squeeze on my cheeks, and massaged Bob's cock inside my mouth, causing him to moan softly before she stopped. She got up and took hold of both Bob's hands and placed them on my head, instructing him "Now hold the sissy's head firmly, like all the boys do when they get their cock sucked... now what is going to happen next is going to be difficult to watch for a sensitive sissy like you, but I promise it is for your own good. After all someday you'll be a big girl like Michelle here, and it will be your time."

From my position I could not see much, but sensed both fear in Bob at the prospect someday it would be his turn, and relief it was not today. I could also feel his cock grow to its' full length as I held it in my mouth, unable to refrain from sucking periodically to clear the saliva that accumulated too quickly, and the natural action of a tongue on a foreign object in the mouth. While I wasn't giving him a full effort blow job, I was sure it felt pretty good for him, which perversely made me proud. From his vantage point above me he saw a blonde woman with too much makeup that had smeared somewhat, her red lips surrounding his cock, a sexy sight for sure to any man. That he was also still dressed in his party dress, stockings and wig only made the scene more erotic.

Sandy and Carol had disappeared behind me and I could hear them milling about, pouring themselves more wine and talking softly. I was pretty sure they even went out to the patio to enjoy a little evening air before proceeding with me, knowing that anticipation was a powerful aphrodisiac. After a few minutes I heard Carol come back into the room and without any warning she was smacking my ass with the paddle fast and hard, and of course I tried to cry out in pain but it was muffled by Bob's cock in my mouth.

As if I didn't have enough to worry about I had to make a conscious effort not to bite down, an automatic reflex response to the pain, fully aware of Bob's involuntary role in my punishment, and from the feel of his hands on my head I felt his concern at first as he tightened his grip, but soon relaxed it once again when he realized I had it under control.

We quickly gained a mutual understanding as to our best interests under the circumstances. Carol must have smacked me twenty times in less than a minute, and it ended as abruptly as it started, and she was gone from the room, having returned to the patio. When I began to regain my composure, I realized that Bob was getting pleasure from my discomfort, even if indirectly. I could taste the pre-cum flowing copiously from his slit.

It was a while before anything else occurred, when I heard the footsteps and quickly felt the slice of pain from the cane in Sandy's hand as it swished through the air and landed over and over on my already reddened and sore ass. I could not help but scream, muffled as it was, around Bob's cock, and I knew it was giving even more pleasure to Bob. After ten swift strokes Sandy simply stopped and left for the patio.

Then I waited again, which was almost worse than the spankings. Almost. I could hear the ladies talking and giggling as they sat at the patio table and sipped wine and ate some snacks, unconcerned with their two sissy's joined together so obscenely in the living room, available to provide whatever pleasure they might desire to extract from us. Both were highly aroused after having been given oral, then the eroticism of talking to someone who understood and enjoyed the similar way their husbands found pleasure, and each was willing to share some of their own particular proclivities with her new friend.

Even after the past two evenings they were learning about each other. The large cocks jutting out from their crotches, and neither could avoid the natural act of holding it and stroking it, the act of which was highly arousing in itself.

At one point Sandy observed, referencing her big black cock "You know, I understand why guys like to play with this thing, and always want to stick it somewhere tight and warm. It just... I don't know... makes you feel powerful and dominant just by its' size and how it seems to want to penetrate something, or someone. I don't know about you, but as a woman I know I am made for this thing to find its' natural place, which is deep inside me. And as much as I love playing with Michelle, I also love getting banged good and hard, and luckily Michael is quite as proficient at that as he is with his tongue, as you found out last night."

Carol thoughtfully responded "Yeah, there is no doubt from the first time I put on a strap-on, at Barbi's request by the way, I felt the urge to stick it in and fuck someone. You are 100% on track with that! I also love getting fucked and I really appreciated you letting Michael fuck me last night... I sure needed it, since it's been a long time since I had anything besides Bob.

"And while I love him dearly, he knows he is small down there and has let me find a bigger partner to play with occasionally over the years when I get the urge, but like I said it's been a while. You are sure lucky to have it available any time... he is quite talented with both his tongue and cock. To be honest, we were at the casino on the prowl to pick up another guy to come back and fuck me. I never expected to find not only that big cock, but a lovely sissy and her owner to play with my own sissy, and hopefully friends for the future. Isn't it amazing how kismet works... you just never know when you wake up in the morning what is going to happen before you go to sleep that night!"

Sandy smiled and nodded in silent agreement, and the two ladies sat and sipped at their glass of wine enjoying the evening air, deliberately delaying returning to us, knowing every minute of waiting would seem like hours to me as I still held Bob's cock in my mouth. Periodically I could taste the dribble of pre-cum from his pee slit, but luckily so far he had resisted the urge to cum.

Over the next half hour or so they talked and drank, and each took a trip to use the bathroom and pee. Carol went first and as she passed through the living room went over to Bob, stood up on the sofa and brought her pussy to his mouth, and he licked her clean, lapping up all the drops of pee that remained on her pussy lips and inner folds.

I could only look up and watch this as Carol looked down at me and smiled, and when she pulled away from Bob and got down off the sofa she knelt down with her face near mine, and whispered "You are such a good sissy... you know it's almost time... I hope you enjoy it as much as your partner will... she told me I get 'sloppy seconds'... I can't wait..." She laughed, got up, gave Bob a kiss on the cheek and went back to the patio.

During the interim between Carol leaving and Sandy going to the bathroom about fifteen minutes later, the imagined fear this generated in my mind was slowly replaced by resignation and then a sense of anticipation as we pushed our limits farther than ever before. I assumed Carol had told Sandy what she had done after using the toilet, because she also stood up on the sofa and had Bob lick her pussy clean of all residue from urinating.

She did not say anything or even acknowledge me before she left to the patio again. Once again I was forced to wait in this humiliation position, not knowing when or how the evening would continue.

It was another fifteen minutes or so before I could hear the footsteps of both ladies coming into the living room behind me, and soon they came into view on either side of my head. Both were naked except for the leather harness, but had added a pair of knee high leather boots as well. Sandy wore the black cock that was at least two inches in diameter and six inches long, while Carol wore the flesh colored one, about one and a half inches thick but longer at eight inches.

I knew it was the thickness that mattered most, not so much the length. Sandy knew the boots were another fetish of mine, and she admitted she found herself feeling more dominant when wearing them, so I appreciated her sharing that and including Carol in my fantasy once again, but wondered for a moment where Sandy had gotten hers from since she didn't bring them on vacation as far as I knew.

Apparently Carol had a pair that fit Sandy, another coincidence in this chance meeting. Their made up faces, coiffed hair, feminine curves and exposed breasts contrasted with the large cocks, declaring that it was women in charge this day, and they were going to take their pleasures where they found it.

They both held their massive phallus's in one hand and brought it to near my face, and began to slap my cheeks on both sides with their cocks, laughing at me as they did so as I closed my eyes and scrunched up my face in response, unable to move or prevent this new humiliation.

Carol teased me "We know you'd love to suck these nice cocks down your throat, but it seems you already have a nice cock in that sissy mouth of yours. Are you enjoying that cock, sissy?" I could only nod yes and mumble "mmhmm..." as she continued "... and does my little sissy like her clitty in Michelle's mouth?" Looking up as best possible I saw Bob smile and nod yes.

Carol and Sandy stopped smacking my face with their cocks, and Carol reached over and picked up a tube of lube, and handed it to Bob. Meanwhile Sandy moved so her cock was over my head, in front of Bob. Carol continued to direct, moving her own cock so the head was pressing against Bob's lips, and he quickly opened his mouth and took it in, the head stretching his mouth open wide and filling his mouth.

He was relieved when she just held it there and made no effort to press it into his throat or fuck his mouth. But then while he still held the head in his mouth she made clear Bob was to apply the lube to Sandy's cock. It was a little awkward at first but

Bob quickly was able to coordinate his hands, squeezing out the lube and applying it to the massive black cock. Knowing full well what the intent was, and actually hoping to reduce my pain, Bob repeated the application of more lube several times, until it was almost dripping off and the entire black cock glistened with lube. When he handed the tube back to Carol, who discarded it to the side, she gave him a small towel to clean the lube off his hands, and once done Carol gently placed them back to hold my head as before.

Sandy had disappeared behind me, and Carol pulled her cock out of Bob's mouth and sat next to me, watching Sandy intently. I felt Sandy take hold of my ass cheeks with both hands and pull them apart, exposing my asshole. She positioned the tip of the cock at the hole, holding it there as I tensed up and moaned in anticipation around Bob's cock, which he obviously enjoyed.

Sandy caressed my ass cheeks and up my back, trying to soothe my nerves, while Carol added her touch to my shoulders and arms. Sandy spoke in a calm, knowing voice "They say it is best for it to be fast and over quickly... to get to the good part... are you ready, my good little sissy girl... do you really want it... your boi pussy says it does...?"