What are the Odds?

I hesitated for a moment, but realized I was nodding my head up and down as best possible while bound to Bob's cock, and mumbled "Ysstthh... plsssh...", as close to 'Yes please' as I could manage under the circumstances. I felt the pressure build from the head of the cock as it pressed against the reluctant hole it was trying to enter, but nothing could stop it from beginning to stretch the puckered entrance, and again I moaned.

A little more pressure by Sandy and the first half inch of the head was inside, and she held it there for a moment as I waited for the inevitable. Bob held my head a little tighter in his hands, the tension of the moment affecting him as well, and somehow that was soothing. When Sandy sensed me relax a little she took a firm grip on my hips and pressed forward with her own. It took me a moment to register what was happening as the head continued to stretch the hole apart to accommodate it's girth, quickly followed by it encountering and defeating the anal sphincter muscle, causing intense pain, then sliding it's full length into me in one thrust until there was no more, her leather harness pressed firmly against my ass.

It took barely more than two seconds for this to occur, and I don't know at what point during that time the pain and violation in my bowels registered in my brain, or at what point I began screaming incoherently as I was pressed even harder onto Bob's cock as I tried in vain to be rid of the massive cock. It took a while but eventually I was able to calm down enough to stop screaming, left to just moan and groan around Bob's cock, which once again reacted positively to my involuntary mouth and tongue in reaction to the severe distress I endured.

I could hear him occasionally mutter "Oh, God... oh, god... yes...", which only confirmed he was enjoying it. At least someone was.

Sandy gave me a long minute to accommodate the fat cock shoved deep in my ass, stretching my hole to the limit with that special feeling of fullness only known under these circumstances. Sandy had fucked me many times before, but this new cock was so much larger it was like the first time, and I knew it was not over.

Suddenly Sandy began to pull back slightly on the cock and it began to slide out, but she stopped about half way before pressing it deep inside me again. I could feel the mushroom head sliding inside me and had a jolt of pleasure when it passed over and stimulated my prostate, before the leather harness pressed against my ass when she bottomed out. She began a sawing motion, pulling out slightly and pressing back in, each time a little farther out, until only the head was still in me when she pulled out, followed by a firm thrust to impale my ass completely.

She took her time, alternating slow and easy with harder and faster to keep me off guard and retaining her strength to continue longer, all the time teasing me with comments like "Such a tight boi pussy... she loves it, doesn't she?... such a good sissy." Carol joined in and teased me as well, saying I was not just a good sissy cock sucker and pussy licker, but I was made to be fucked. But I also knew it was all really about Sandy's pleasure, with mine being incidental, so it did not surprise me when she began to hold my hips tighter and fuck me harder and faster. I knew this would press the back of the cock against her pussy and clit, and if she fucked me hard enough she would orgasm, and so for the next ten minutes she pounded her cock in and out of my ass, slowly but surely building up her own arousal until it broke over her in a wave of full body spasms emanating from her pussy as she pressed the cock as deep and hard into my ass as she could, obtaining every measure of sensation she could to achieve her release.

At the same time my mouth was working wonders on Bob's cock and he soon could no longer hold back, held my head firmly in his hands and began to cum, filling my mouth. I managed to swallow enough to not choke, but the creamy remains coated my mouth and tongue, adding to the complete perversion and degradation I was subjected to, and of course Bob's cock remained in my mouth, although it had shrunk a little.

When Sandy's orgasm subsided, she collapsed forward, her breasts pressed against my back, an erotic feeling I always loved, silently declaring that my violation was over. She hugged me from behind, holding herself in that position for a while. Carol meanwhile sat up and kissed Bob, then stood up and went out of my sight, going to the patio to retrieve the wine glasses for herself and Sandy.

When she returned Sandy lifted herself up, her cock still embedded deep in my ass, and she took the glass of wine handed to her by Carol. The two clinked the glasses together and Carol proposed a toast "To hot chicks and losing your virginity."

Sandy smiled and replied "To losing your virginity." She took sip and slowly pulled the cock out of my ass, until it fell out with a plop, and I moaned at the empty feeling it left me with, and the air tickled my gaping ass hole, and I involuntarily wiggled my ass, inviting Sandy to put it back in.

Sandy laughed and teased me "Poor baby girl... got used to the big cock in her boi pussy, did she? But you wore me out dearie and besides, I came... and I need to rest for a bit."

I sensed her move away from me and she was quickly replaced by Carol's hands on my butt, roughly spreading my cheeks apart. She lined up her cock and penetrated me fully in one hard thrust forward. Given how much I had been stretched by Sandy's cock, this one slid in with hardy any resistance, and soon Carol was pumping her cock in and out of my ass, smacking into my still red and sore ass with her leather harness with each thrust forward, which she added to by spanking my ass with her hand periodically.

She showed no mercy and took her pleasure as she pleased, enjoying the added benefit of her sissy husband being sucked in front of her by the sissy she was fucking. She kept fucking me for a long time, slowing down occasionally to help her catch her breath, but each time resumed her attack on my ass. By then there was almost no pain and the movement of her cock in my bowels and across my prostate was a constant source of pleasure, and I moaned accordingly around Bob's cock, my own cock straining in its' confines.

She was able to keep this up for quite a long time, and I knew at some point Sandy had gone to use the bathroom and came back with refilled glasses of wine, which Carol nonchalantly sipped at while she continued to fuck me at a steady, relentless pace. Sandy sat next to Bob and me, and began to play with Bob's nipples through his training bra, and he moaned at her touch.

She teased him "Mommy's little girl has such sensitive titties..." and also reached down with one hand to play with the base of his cock and his balls, caressing and stroking them where they met my lips, increasing my humiliation. Carol redoubled her efforts and began to pound me even harder than before, which caused me to moan and be pressed forward into Bob's crotch. The combination of my mouth, Sandy's manipulation of his cock, balls and nipples, and watching his wife fuck another sissy aroused Bob beyond any ability to withstand release, and soon he was spurting cum in my mouth again. It was much less than last time, since he hadn't had much time to recover, so I easily accommodated it in my mouth and swallowed it down.

Meanwhile my ass was being pounded by Carol's cock and she was building up her own arousal from the pressure against her pussy each time she pressed forward, and she finally thrust hard particularly brutally several times in a row before holding herself hard and fast against my ass, the back of the cock taking her over the edge and she began to orgasm just as Bob was coming in my mouth.

Unlike Sandy Carol did not stop as her orgasm coursed through her body, but rather used it as a force to maximize her own pleasure. She pounded me wildly, almost uncontrollably, which only served to make it last longer, grabbing hard to the flesh on my hips to maintain control, until the orgasm eventually subsided and she began to slow down, then finally stop when on an out stroke the head of her cock slipped out of my ass. She laughed breathlessly as she came back to her senses, and fell on top of my back to rest, and I once again had the pleasure of a satiated woman's breasts pressing into my back.

It was blissful in a way, and the only thing that brought me back to reality was the insistence of my cock to try and break free from its' metal cage. Everyone had had an orgasm but me, and each used my body to achieve theirs, and I wondered if the wives would give me that release tonight, or if I was to remain caged.

I was happy about one thing when Sandy began to unsnap the leather strap that joined my collar to Bob's cock, and soon my mouth was free and I was opening and closing my jaw to regain some movement after being held open for so long. Bob slid out from under me and got up and left to use the bathroom. I remained bent over the edge of the sofa, not having been told to move.

As he left Sandy came up behind me and with no warning slipped her cock into my ass, and I grunted more from the surprise than pain, although it's larger size still made a difference and it did hurt much more than the one Carol now wore. I soon found Carol had removed her harness and promptly sat on the sofa and slid under me, so her pussy was in my face. I did not hesitate and began to lick lightly at her mons, then swiping my tongue through her wet slit several times, causing her to moan in appreciation and take hold of my head in her hands.

Now that I was free of Bob's cock, the steady penetration of my ass by Sandy allowed somewhat more movement of my body, and I was able to use that to stimulate Carol's pussy and clit with my tongue. I also began to press myself back into Sandy's cock as she thrust forward, increasing the pleasure she received. Sandy urged me on "That's it slut... show me how much you want this big cock... come on, take it deep... that's it... what a whore...", and Carol clearly understood when I lost contact with her pussy as I pulled back away from her before Sandy sent me back into her with a thrust forward.

We developed a rhythm of me bucking back onto Sandy's cock then my face being pressed into Carol's pussy, where I attempted to lick at her as best I could, and that is what Bob saw when he returned to the living room. Carol called him over "Barbi dear, come join us... sit next to me... you need to see what is expected of sissy girls... and how much fun you will have..." Bob sat down at the end of the sofa next to Carol, and anxiously watched what seemed to be his own future play out before his eyes.

Sandy had continued fucking me as I bucked back into her the entire time, but I sensed she was holding back to last longer, and last longer she did. In all our years she never went on longer, and I was doing everything I could to bring her to an orgasm so she might stop.

I was pressing my ass hard into her to increase the pressure on her pussy, I was calling out, now that my mouth was no longer gagged on Bob's cock, for her to fuck me harder, calling myself a slut and whore, and any other filthy, degrading thing I could think of to arouse her, including how good her big cock felt in my tight boi pussy. After what seemed like forever, she must have finally been ready to finish herself off, pressing my body face down into the sofa with her hands she began to fuck me even harder, if that was possible, until she either came or gave up, I couldn't tell which or if it mattered. She unceremoniously pulled out and gave me a smack on the ass with her hand. My body finally relaxed, exhausted, into the sofa, hoping it was over.

But before I could really relax Carol was up and behind me, her cock impaling me in one thrust forward. Without any hesitation she was fucking me in long slow stokes, and it felt so good I moaned in pleasure, causing Sandy who stood nearly, to laugh at me. She took Bob by the hand and pulled him up, and without a word led him out of the room into the bedroom. Carol didn't stop or go faster, just continued to fuck me in long slow strokes.

Several minutes later Sandy and Bob returned, but Bob was now dressed in the light flannel pajamas he wore the previous night. When they sat on the sofa next to me Carol stopped and pulled out, then turned me over so I was on my back, my legs spread and pushed wide apart by Carol, who made clear I should hold them that way, with my ass extended just past the edge of the sofa. My cage covered cock sat on my stomach, with my distended balls below it. Carol knelt in front of me and quickly pushed her cock back into my ass and held it there, pressed fully inside me.

I was surprised and elated when she began to unlock the lock and unhinge the top from the bottom, slowly relieving the pressure on my cock as the sound slid out of my pee hole, causing me to moan loudly. I could not help but notice how interested Sandy was in that particular aspect of the cage, but had no time to dwell on it as she pulled it off and placed it to my side on the sofa, and soon had removed the bottom section from below my balls and it joined its' mate on the sofa. She rubbed my balls and stoked my cock softly, and it quickly responded to its' full length and girth, to Carol's obvious delight.

Meanwhile Sandy manhandled Bob to lay across her lap face down, his hips over her thighs, which placed his head on my stomach turned to face my cock and his wife. He looked up at his wife, questions in his eyes, and she nodded yes, and without any protest or hesitation he took the head of my cock in his mouth. Carol held him there with her hands, so he could not take it any deeper without serious effort.

As he did so Sandy was unbuttoning the flap on the rear of his pajamas, and began to spank him, softly but with a regular cadence. I could feel the effect of each smack in the pressure of his mouth and tongue on my cock head, and it felt amazing, but I worked hard to control my inclination to ejaculate immediately, and once under control I was able to concentrate on other aspects of my situation.

It was highly erotic for me, with Sandy sitting naked to my right with Bob in his sissy pajamas over her lap, ass exposed, the sight and sound of his spanking, and of course the sliding of Carol's cock in and out of my ass, which had begun again as Bob took me in his mouth. I was moaning at all the stimulation and begging Carol to fuck me harder and faster, which slowly and surely she finally did, and I looked down over the large breasts on my chest, the nipples like little erasers, as I watched at the top of Bob's wig clad head bob up and down on my cock, and Carol's body moving in and out of my ass hole, providing constant friction to my prostate.

I held out as long as possible but I admit it did not take very long for the climax to this cacophony of erotic pleasure to overwhelm me, and I began to try and push my cock deeper in Bob's mouth as I called out "I'mmmm cummmiiinnnggg...." and began to spurt my cum in his mouth. I felt his tongue laving the head as each rope filled his mouth and he choked slightly as some went down his throat, otherwise apparently enjoying the taste and satisfied at his own efforts. In fact Carol was complementing him as she slowed her penetration of my ass "That's it, my sweet little girl... take all that juice from her clitty... mmmm, good, right dear?"

Bob lifted his head and replied "Yes, mommy... thank you mommy..." Sandy had stopped spanking him and he turned his head to face her and added "And thank you, Miss Sandy..."

Sandy smiled and patted him softly on the ass and began to button up the flap again. Carol had pulled out of me and stood up, removing the harness. She had Bob pick up his head and had me stand up. She took me by the hand and out of the living room into the bedroom. Once there she had me go in the bathroom and clean up, then remove the garter and stockings, and put on the flannel pajamas I wore the night before.

I still wore the wig and breasts. Carol brought me to the dressing table and touched up my make up, and when I looked in the mirror saw a young girl with somewhat larger than average breasts, stretching the material across the chest of the pajamas. Carol reinforced this as she took one in her hand and squeezed, leaned in and kissed me, her dominance apparent as her tongue overwhelmed mine in my mouth, and I submitted to her assault just I had submitted to her cock.

She kissed me until she stopped as abruptly as she had begun, and I had to catch my breath afterwards, like a breathless teenage girl. She smiled and took my hand and we returned to the living room, where Sandy and Bob were sitting side by side on the sofa, with Bob's legs curled up under him on the sofa and Sandy's arm around his shoulders. They looked cute, like a teen girl nestled in her mother's side, but with his head nestled in Sandy's large naked breasts it retained an incongruous erotic feel.

Carol announced she was tired and it was soon time for bed, and Sandy agreed. Bob and I looked at each other, wondering the sleeping arrangements for tonight, and hoping it was less stringent than the night before. Sandy suggested a nightcap before bed, and at Carol's suggestion we all went out to sit at the patio table. Carol got the glasses and the bottle of wine and poured us all a short round that finished the bottle.

It was a little strange with Bob and I in pajamas and the ladies naked, but after all that had occurred no one said anything and we just sat and drank our wine, conversing quietly about plans for the rest of our vacation and beyond. When we had drained the last of the wine, we got up and the ladies escorted Bob and I back into the living room.

Carol advised Bob he could pick up and clean the dishes tomorrow. She then ordered the two of us off the sleep in the guest bedroom, declaring that the 'grown-ups' would sleep in the big girls bedroom. Relieved we were not bound together with cocks in mouths, and were not punished before bed, we took the opportunity, thanked them, kissed each in turn goodnight, and padded our pajama clad feet to the guest bathroom to brush our teeth and pee, then off to the guest bedroom.

It had a queen sized bed so we had enough room without touching but could obviously feel the other's presence in the bed, and somehow within a few tosses and turns I was snuggled in behind him, spooning in the comfort of the intimacy between two similar souls, and soon we were both fast asleep. Neither of us knew that our wives had come by to look in on us and smiled in delight to see us so contented in our sleep. As they stood there Carol took Sandy's hand as she said "I'm so glad we went to the casino, and had to go to the bathroom!"

Sandy chided her "Quiet or you'll wake them up... and it took so much effort to get them down...", and they both giggled as they closed the door. Sandy continued, "But in answer to your statement, you better believe it, me too!"

With that the two naked ladies walked back down the hall to the living room and beyond to the bedroom. They both used the bathroom and washed up as usual, and went to bed. Sandy was always cryptic about what happened between them in bed that night, so it was left to my imagination, but it seemed inferred by Sandy in her evasive reply to my inquiries that Carol had enjoyed playing with my wife's large, soft breasts, and Sandy loved having them played with, so that seemed a good bet at the least. Beyond that only they knew, but it wouldn't surprise me if all they did was say good night and go to sleep, enjoying the chance for rest after a quite energetic evening for all of us.

So sleep came easily to all of us, and we slept soundly until the early morning. I think I was the first to wake up, getting out of bed to go to the bathroom while Bob still slept. As I finished and left the bathroom Bob came in and began to do his morning ablutions, coming out a few minutes later.