What are the Odds?

Bob and I got the umbrella up and chairs unfolded while the ladies watched, and they took off their wraps and sat down facing the ocean. Without a word Bob got out a bottle of suntan lotion and began to apply it generously to Carol's entire body until it glistened in the sun. When he was done he handed it to me and I had the pleasure of coating my wife's exposed areas, and taking liberties with a few that were not, to which she did not object since the few other people there were well distant away from us, and the combination of chair and umbrella helped conceal my intimacy.

When they were satisfied at our efforts I announced I wanted to take a swim in the ocean, which had only relatively small waves that afternoon due to the light offshore wind. It was in the nineties so a swim in the cool water seemed a great option just then, and Bob agreed.

The ladies just wanted to sunbathe for a while, so off we went and for the next half hour of so swam, floated and otherwise enjoyed the salt water. Eventually we tired and went back to join our wives, and had some drinks and snacks. Later the ladies joined us in the ocean, and after a while returned to continue sunbathing.

As the afternoon progressed, Sandy and I took a long walk down the beach, enjoying the sun, wind, waves and the often scantily clad people on the beach, which drew speculative comments on their sexual preferences from one or both of us, a game we often played. One common question from Sandy when we saw another older couple like ourselves was if I thought the man was a sissy like me and liked to get fucked by the woman, or pain slut for her, or a toilet slave, and if I would like to get fucked by her. It was a trick question because if I said no she would know I was lying and punished me later, and if I said yes I would probably be punished later for wanting another woman.

A perfect Catch-22, but we both loved the devious nature of the trap she had laid, and knew it was an excuse for her to punish me, as if she needed one. Eventually we return to Bob and Carol and sat and enjoyed the drinks, food and company, taking a few trips to cool off in the ocean. When the sun was beginning to get lower in the afternoon sky, we decided to return to the house to shower and get ready for dinner.

The next few hours were relatively uneventful and almost seemed normal, except Carol and Sandy had Bob and I take a shower together, including soaping and rinsing each other's bodies as they watched, and then after drying off applied a scented lotion to each other's bodies. They told us our clothes were laid out in the bedrooms and to leave them in private to take their showers.

Whether they shared a shower or did so separately I do not know, since I went to the guest bedroom as ordered. On the bed was a pair of plain cotton girl's panties and a training bra, and a pair of khaki slacks and a collared polo shirt, and black socks. My loafers were on the floor to the side of the bed. Without delay I put on the items laid out for me, panties and bra underneath and my regular clothes on top. Unless I had a mishap like earlier in the day in the elevator, no one but Bob and our wives would know. I wondered if Bob was to be similarly attired, fairly sure he would be as well.

When I arrived out in the living room Bob was already there, dressed similarly to me, and we figured it would be a while for the wives to get ready so we poured ourselves a glass of wine. I poured two more glasses and brought them to Carol and Sandy to sip as they did their hair and make-up.

A half hour or so later they came out dressed beautifully in knee length flowery dresses, both with low cut necklines and bare shoulders. While Carol's slim figure and small breasts was quite sexy in her form fitting dress, it was Sandy's bounteous cleavage that was the center of attention. It was obvious to me she was wearing a push-up half bra, and feeling more adventurous than usual given she must know exactly how it looked. Both women wore flats on their feet, as we would be walking on the Boardwalk later, and had a light sweater for the night chill.

We looked for all purposes as just two perfectly normal retired couples going out to dinner together, except for the panties and bra Bob and I wore. We drove to the restaurant, which was in a nearby beach town and overlooked the beach and ocean, and had a fantastic meal of freshly caught fish, vegetables and potatoes with freshly baked rolls, and of course a bottle of wine we brought to accompany the meal. We finished it off with desserts, which we ordered four different ones and shared. During the meal the conversation ebbed and flowed, on topics small and large, as we shared more about ourselves. When done we used the bathrooms and paid the bill, with a generous tip, and left to drive to the Boardwalk.

Once at the Boardwalk we parked and decided to go for a walk before anything else, so began to stroll up to the north end. We went past the small shops and restaurants, the amusement piers, and the big casinos, with the lights and music playing through loudspeakers into the night, enjoying the night air and cacophony of people and sounds around us as we made our way.

Soon we had exchanged partners, so Carol and I, and Bob and Sandy, were walking together arm in arm. It was not long before we had shared the game we played observing the people that passed by, evaluating their sexual preferences, perversions and proclivities. While Sandy played with Bob I found Carol to be quite devious and shocking in some of her evaluations. We walked slowly up to the end at the inlet, and then turned and strolled back towards our car.

We went into a casino for a while and Bob and I watched as our wives played blackjack and later slots. But playing casino games was not really the type of games on their minds, so after less than a half hour they cashed in their modest winnings and we exited and walked back to our car. We drove back in silence, each preparing mentally for what was to come next.

When we arrived Bob and I were told to get a glass of wine and wait in the living room while they got our clothes ready. As we left, obviously excited at the prospects of being allowed to dress up again for our wives, Sandy teased us that she knew we couldn't wait to get into some nice sissy clothes and become the sluts we are.

Neither of us could disagree, but were also embarrassed to admit it to each other so just stayed silent, prepared the glasses of wine and waited. When the ladies came out to join us we handed them each a glass of wine, and we toasted to another fun night with new friends.

They sat down and dismissed Bob and I to go to the bedroom and put on the clothes laid out for us. When we were dressed, we were to call for Carol, who would come and help with our make-up. When we got to the bedroom two sets of clothes were laid out, and in case we didn't figure it out one had a note paper on it that read "Barbi" and the other "Michelle".

Once again we had to become sissy's together, so Bob and I removed our clothes. Bob saw I was now shaved down below as well as on my face, and commented that Carol was going to like that a lot. Also on the bed were the two pairs of breasts we had worn the prior night, Bob's modest 34C's and the impressive 40DD's for me. We helped each other put on the garter belt, stockings, bra, panties and flat shoes, it all being much easier when assisted.

Bob's outfit was composed of white cotton panties, a white silk garter belt attached to thigh high stockings, a soft cup padded bra, an empire cut dress cinched under his breasts with short puffy sleeves and a very short hemline. Before he began to get dressed he applied the adhesive to the breasts was with some assistance from me attached them to his chest. Once set in place he was obviously proud of his new assets.

The dress could have been worn by any stylish teenage girl on her way to a party, except that it only covered about half his ass and the bulge in his panties front was quite visible, as were the garter straps and skin above the tops of the stockings. He added a red haired wig with two long ponytails so that with the dress he was transformed into a young girl. Bob then helped me put on the large breasts, followed by a black garter belt and stockings, a black thong type panties, and a sheath type dress that was too short on top leaving my breasts mostly exposed, and on bottom leaving most of my ass open with the thong string wedged in the crack of my ass.

What was obviously missing was a bra, and the nipples on my breasts stuck out through the thin material that barely covered them. This time Bob put on me a blonde wig that had bangs and shoulder length soft curls. Once he had settled it in place he turned me to look in the mirror and I was pleasantly surprised at what I saw. The outfit was somewhat slutty, but I felt good about what I looked like so far with my clean shaven face. After a quick mutual examination to assure straight stocking seams and proper fit of the rest, Bob called out to Carol that we were ready.

Carol arrived a few moments later and was dressed in a pair of men's slacks and a dress shirt. There was a prominent bulge in the crotch of her pants. Sitting Bob on the stool in front of her dressing mirror, she put on his make up, which was minimal as befitted a young teen girl. No eyeshadow or liner, with just a touch of foundation and rouge to his cheeks, and a light pink lipstick. When done she kissed him lightly on the cheek, and had him move to sit on the bed while I took his place.

She turned me away from the mirror and began to work on my face. Eyeliner and eyeshadow, fake lashes for length, shaping for my eyebrows, foundation and blush, and a deep red lipstick were all added in turn. When I was finally turned to face the mirror I almost didn't recognize myself, which was not surprising given my own transformation.

And I was transformed, but not into a pretty young girl like Bob, but rather into an experienced woman looking to hook up. While I sat there in shock Carol put a leather strap around my neck, and once more I wore her collar with the metal ring in the center. She got up and quickly attached a leash to my collar, and indicating Bob should follow, led me out of the bedroom and into the living room.

Sandy was sitting on the sofa holding her glass of wine and looked me over casually as she took a sip, dressed similarly to Carol in khaki slacks and a men's dress shirt. Even though the four top buttons were left undone, the shirt was stretched to the limit to accommodate her bounteous breasts, which I noticed were not contained by a bra.

I stopped to stand in front of Sandy, and Carol who stood next to me removed the leash, with Bob standing behind us and off to one side. Carol turned me around so Sandy could see me from all sides, and I could hear her snicker at my discomfort from being put on display like that, and I submissively looked down at the floor as I stood there, hands hanging loose at my sides.

For all intents and purposes there were two men and two women in the room, but it was not as it was earlier to based on biology, as our roles had exchanged. I waited nervously as Carol sat down on the sofa next to Sandy and called Bob over. She produced the two sections of the cock cage and Bob pouted and protested mildly, knowing anything more would result in punishment and he would still wind up in the cage.

Sandy held the top part for Carol as she attached the back around the base of his cock, then handed it to her and I watched as Carol slid the sound into his pee hole, resulting in a clear moan of distress lasting until the top section met the base, and it was locked securely shut. After checking her work she cooed approvingly and patted Bob's ass with a few light swats, indicating for him to return to his prior place behind me. I wondered if I was also to be caged tonight.

Carol got up and went over to Bob and had him kneel down and lay over an ottoman off to one side of the sofa, and efficiently tied his knees and wrists to the legs, and an extra length of rope attached to a hidden hook pulled on his cock and balls from below if he tried to rise up. A pillow was placed under his chest to raise up his head so he could watch whatever was to happen in this room. He also knew he was helpless if either woman wanted to use or abuse his mouth or ass. As it turned out they used but did not abuse him that night. Such treatment was reserved for me.

Once Bob was secure, Carol returned to sit on the sofa next to Sandy. I waited and waited as they sat and sipped at their wine, giggling and whispering between each other as they looked at me like a sex object to be used, implementing their plot on how to do exactly that.

Sandy spoke to me first, "So where do you think you are going dressed like that, young lady? Don't you know Barbi looks up to her older sister, and you need to set a good example!"

I took a moment to process what she had said, but then sputtered "But... but... but all my friends dress like this...", adding more quietly "...and the boys like it..."

Carol interjected "Michelle, dear... we're only trying to protect you. I think the boys will like you way too much... and you don't really understand what boys are like."

I just stood there as Sandy continued "With tits like those you sure bet they will! And no, she doesn't know... or do you, slut?"

I stammered innocently "No... no... I never... not really..."

Sandy glared at me and called me over to stand closer, and with a grab of my wrist and a pull had me face down over her lap, putting my face in Carol crotch. It was easy for her to pull the bottom of my dress up over my back to uncover the rest of my ass, and the string of the thong I wore covered nothing.

I could feel the bulge of the thick cock Sandy wore under her slacks, and a similar bulge pressed into my face from Carol's crotch. Carol put her arm over my upper back, holding me in place, while Sandy lifted one of hers and brought it down with a loud smack on my bare ass. I grunted from surprise.

Sandy began to smack me in a regular cadence, in between grilling me with questions, "So, slut... do you give the boys hand jobs?", to which I hesitantly replied I had. Sandy continued "...and do you suck their little boy cocks, like a whore?", and I simply nodded, unable to admit it out loud. Sandy sneered "Yes you do... and I bet you love that nasty cream in your mouth, and swallow it all down... don't you?" I could only nod again in humiliation, recalling the taste of my own and Bob's cum in my mouth not long before.

Sandy continued "And I bet you like it when the boys put their little cocks in your tight boi pussy, don't you slut?" The spanking continued.

That was when and where I decided to push back, so to speak, and called out, my voice muffled in Carol's pants, "Nooo! I promise... I know I'm a slut but I've been a good girl and didn't let them! Please... I'm saving myself..."

Sandy interrupted me and laughed as she replied "Saving yourself! Who knows what else you'll say..." Turning to Carol, she grinned and added "You hear that... she's been saving herself... but there's a time for every girl, and I think this little piece of ass is old enough and perfectly ready. And after all she needs to show her little sister what to expect when she grows up- no need for surprises!"

They laughed again at that. Sandy was still spanking me slowly but surely with her hand as all this occurred, and turned to Carol and asked if she would like to help, to which of course she was amenable. I was turned around so my face was in Sandy's crotch and my ass was face up centered over Carol's lap.

Without delay Carol began to spank me with a similar cadence to Sandy, but more often spent time on one cheek for many more smacks in a row before moving to the other one. From this direction I could see Bob bound to the ottoman nearby, and his face showed some commiseration with my situation, but also understandable relief it was me and not himself. Carol's spanking went on for about fifteen minutes before she suggested they use the hairbrush to avoid any more discomfort to their hands. Discomfort to my ass was not a consideration.

Carol got up and disappeared into the bedroom, returning a few moments later with a hairbrush, a paddle and a cane, setting the paddle and cane off to one side on the sofa. With Sandy's concurrence she took her position on the sofa with my ass over her lap, and resumed the spanking with the hairbrush. While the hand spanking can hurt and the pain accumulates, the unforgiving wood of the brush does not yield to flesh, and it stings and burns like the dickens.

On the first smack I was calling out in pain, struggling to keep any sort of composure, and it was not long before I was crying out loudly with each smack. It seemed like forever when she finally seemed to tire and slowed and then stopped.

She wiped at her own forehead from the exertion, and stated "Whew. That was nice, but hard work! And I'm hot!" She handed Sandy the brush and began to unbutton her shirt, pulling it out of her slacks and removing it, baring her arms and breasts.

Sandy smiled and chided back "You sure are hot!" and Carol blushed at the compliment. Sandy continued "I think you've had enough of the hairbrush... Carol, very well done, indeed! But I'm not sure you've learned your lessons yet. Michelle, get up and stand in front of Carol. No, bend over and put your hands on her thighs. That's right, now look up at her."

In this position my ass was jutting out, and I was so mesmerized by Carol's pert breasts in front of my face that I didn't notice Sandy picking up the paddle, her favorite implement. But of course I noticed immediately as she swung it forward and it connected with the fleshy cheeks of my ass, and I hissed in air to contain my scream as Carol watched me try and maintain my position.

After several more smacks such control was impossible and I began to cry out louder and louder, until it was almost continuous. Sandy had used the paddle on me many, many, many times in the past, but it seemed she found a new ferocity in her arm, or maybe it was just the audience that watched and participated in my debasement.

I felt lucky when after only about five minutes she stopped since I knew she could go much longer if she chose, although my ass was definitely on fire and quite well reddened. The paddle on top of the hairbrush on top of the hand spanking definitely provided an incentive to learn any lesson they wanted to impart on me.

But of course they were not done and had me stand up straight, then led me to an open corner of the room and had me stand there facing the corner, my hands up behind my head and my red ass exposed to the room. I knew from long experience it was best to only look at the corner and not try and see anything going on around me, so all I could do was hear as Carol got up and began to remove her slacks, and Sandy was removing her shirt and slacks.

Both were still wearing their harnesses and the cocks now stuck straight out, no longer confined by the slacks. The two ladies came up to each side of me, caressing my body with their hands and Sandy pressing her breasts into my back, but I remained in position facing the corner, although it was arousing as can be imagined. They each took their cock in their hand and slapped them on my hips and ass, then made rude comments about the size of my cock compared to theirs. Of course even at a decent six inches and fairly thick, I was no match for their porn star cocks.

After a while of teasing me they left me to stand there and contemplate my situation, and the immediate future as anything beyond that was irrelevant at this point in time. I could sort of hear and barely see them both remove the harnesses and moved the entire ottoman with Bob on it to face a chair they brought over.