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Roberta and Patrick's Next Bet - The Ending

Roberta and Patrick's bet is decided, and the loser pays off.
….A jack!!

That gave me a full house, beating Patrick’s straight!

A whoop of triumph left my lips. What an incredible rush! I mean, it’s sweet to win, but when victory drops into your hands after escaping from the clutches of almost certain defeat it has the saccharine scent of honey and the unbearably, indescribably delicious taste of a preposterously decedent dessert. Although I’d won in February, this was so much better than that first adventure, and it was a rush I knew I would just had to have from time to time.

Patrick got just the gloomiest look on his face, poor dear, now that he was a career 0 for 2 in our little erotic bets.

But I’ll turn this over to Patrick now.


In the NFL an official would have thrown a flag at Roberta’s egregious touchdown dance. But here in our living room there was nothing I could do about it. Man, this sucked! I was really hoping to win this time after having to surrender to her after our last bet. And when I saw that 8 on my last card and completed my straight I knew it was in the bag. So much for sure things.

It took a little while for Roberta to finally settle down, but when she did she was quite direct.

“Looks like a full house. And that beats your straight,” she observed. “So, strip. And make it snappy.”

There’s really not too much to a guy stripping, is there? I mean, I love to read descriptions of women stripping. Very hot. But, well, I just took my clothes off. Do you really need to know any more than that?

Roberta moved to the couch and sat back, crossed her legs, smiled, and adopted an expectant and impatient air. When my boxers came down my dick was half hard. Shit! That certainly sent the wrong message!

When I was done she told me to move the coffee table and stand in front of her. After I’d done so, she scooted forward on the cushions. She reached out and gave my dick a few pushes back and forth, wrapped her hand around my member and brought herself closer until her mouth was within an inch of it. Now, there is no way Roberta’s mouth can be an inch from my dick and have it not stand up and take notice. I was fully hard in seconds. Then she laughed, stood, and moved toward the bedroom, calling over her shoulder that she would be right back and that I wasn’t to move.

I stood there feeling exposed and a little ridiculous. I mean, there wasn’t really much else to do. My boner was doing a great imitation of a telescope, pointing toward the constellations.

Roberta was back after a few moments, several items in her hands. She handed me the leather ankle cuffs and wrist cuffs that she so often models and told me to put them on. This was a first for me. I’d never had these on, but Roberta clearly felt that what was good for the goose…..

When all the leather was buckled in place, she had me get on my hands and knees on the coffee table. It’s a big, round one: the heavily lacquered cross-section of an immense tree trunk. Roberta directed me into the position she wanted and soon my shins and ass were hanging out over the edge. Then, as I expected, she pulled first my right and then my left wrist back to the corresponding ankle and clipped the cuffs together. When she pulled my second hand back my head did a barely controlled face plant, my forehead clunking into the surface of the table none too gently.

“Ow,” I complained.

“Oh, shut up. You did the same to Ellen. Serves you right.”

However, after my cuffs were secured she was kind enough to place a pillow under my head. Then she put the blindfold she so often graces over my eyes.

I was now ass up on the table and with no sight. I’d never experienced this, and it was not a comfortable position or feeling. My knees and back, I knew, would soon be complaining, and I felt dramatically vulnerable. I suppose this was a good experience for me to have. Roberta spends time like this on occasion for my benefit, and maybe it’s best that I experience at least once the emotions and perceptions involved. Roberta never speaks a word of complaint, but this was going to get just plain uncomfortable. Not having a choice about staying in the position made it worse. I pinned a post-it note to my frontal lobe to check in with her about this.

I thought about Ellen and, in the position I now found myself, my heart went out to her. I felt helpless and on display enough here in my own living room and with only my loving wife in attendance. How must Ellen have felt? She’d been as naked as I was, bound like me, but in a strange house and with people she’d barely met!

Roberta had been away for some minutes, longer than I was comfortable with in this position. I was beginning to feel some rising tension as I anxiously awaited her return. Then again, though, what experience was in store for me when she got back? Maybe postponing that wasn’t such a bad thing after all.

Then I heard the swish of her feet on the carpet. I turned my head as best as I could in her direction even though I was sightless.

I sensed her behind me, and had known this was coming. She spread my ass cheeks and I felt her paint lube all up and down my ass crack and onto me. Shortly after, I felt something finding its way toward my back portal.

Well, shit , I thought (no pun intended), and waited for my ass to be pried opened. This was the first of the forfeits the loser of tonight’s game faced: something large up their butt.

Clearly, it was a dildo of some kind, how big I did not yet know. Roberta was apparently holding it in her hand and pushing it into me. It was an invasion, my hole spreading wider, my breathing becoming shallower, sounds indicating vulnerability and anxiety involuntarily escaped my lips.

There is nothing, I was now finding out for the first time, that can make you feel more defenseless and exposed than being bound as I was and taking something large up your ass.

But then the stretching stopped and my sphincter settled back around a shaft narrower than what had just gone past it. That got my attention. A butt plug? But, no, the narrower part was continuing to push into me. Had it been a butt plug, the advance would be done and it would be seated motionless until pulled out.

Obviously, it was a realistic, penis-like dildo, the head having now slipped past my sphincter and the shaft advancing. But to my knowledge we don’t have a toy like that. All of ours are smooth, not anatomically correct. Where had this one come from?

I felt the shaft of this artificial penis continue to slide into me. There was no more pain, just discomfort as my ass was filled more and more.

Then I heard an electric buzzing, but the object up my ass was not vibrating. What was going on?

Then another bit of sensory input I couldn’t quite reconcile. As the phallus went farther and farther into me I had expected to feel Roberta’s hand gripping the outside end, pushing. Instead, I felt growing warmth, and then Roberta’s thighs were flat up against the backs of my thighs, her abdomen against my ass cheeks.

Realization dawned. She didn’t have a strap-on. Did she? I didn’t think she did. I’ve never seen one around here. Had she made a special trip to the adult store? Got one specifically for this occasion? I had some questions that wanted answering.

But right at the moment I was a little preoccupied with a big piece of molded rubber deep in my ass. I guessed that the questions might need to wait.

Then another piece of sensory input. This one I knew well and loved. It was the sound of Roberta moaning in pleasure. The dildo began to move faster, increasing its depth in my ass until Roberta’ hips were pressed tight against me and grinding. A moment later I heard crying and was so glad to hear it. When Roberta comes very hard she makes a sound that anyone but me would mistake for crying. And that sound was now coming from her in spades.

When her orgasm had passed she rested her forearms on my back, panting. But the dildo only pulled slightly out of me.

She gave the side of my thigh a healthy slap. “Not bad, Lover Boy,” she said.

“This is a little uncomfortable.”

“Too bad. You had Ellen like this for a lot longer. If she could take it so can you. And I’m not done yet.” She gave my thigh another smack.

That seemed to inspire her, and I felt the dildo moving in me again. After being so well fucked my ass now had no major complaints. It was stretched and could accommodate the dildo with relative ease. Roberta fucked me again, this time taking much longer to build to her orgasm, the vibe’s sound reaching several notches higher in pitch as she proceeded. Often Roberta doesn’t come a second time in one session, but when she has an orgasm as massive as her last she usually has little trouble taking advantage of seconds. She eventually climaxed, this time in a more controlled way, a way that involved ‘ohhhh’-ing rather than her simulated crying.

Roberta moved back and away from me, the dildo coming out of me suddenly and unceremoniously. Then she was releasing the clips holding my ankle cuffs to my wrist cuffs, and I sighed with relief. I immediately came to my feet, my knees sore and my muscles badly in need of a stretch. But I ripped off the blindfold. Before me was my beautiful Roberta, in only a top, loosening a harness strapped around her hips, the phallus that had been up my ass moments previous jutting from her crotch.

“What do you think?” she asked, waving the intruder at me.

“Um,” I said.

“Get used to it, Big Boy,” she said, “I enjoyed that too much.”

When we had agreed to the three forfeits for the loser of our bet one of them, this one, had been relatively general in nature: just that the loser would have to take something up their ass. I had assumed that if I lost it would be a dildo for me. I never imagined it would be attached to her and that her clit would be responding to delicious vibrations that would have her bucking, fucking me.

I watched as the harness dropped from around her hips and she slowly disengaged from a piece of molded plastic nestled between her legs. The front was a little bulky, a wire emerging from it: the clit vibe I had heard. And as the plastic came away from her I saw a larger vaginal dildo and a smaller anal dildo emerge from her body.

I don’t know diddle, speaking strictly personally, about the physical stimulation that produces an orgasm in women in general, but I was certain I was looking at one sure-fire possibility.

My boner, in spite of the ignoble manner in which I’d just been used, had not subsided at all. Roberta took a few steps over to me, put her arms around me and kissed me hard and deep. This did not help the boner situation at all. But after a few moments she began to slide down my body ending on her knees. Without any working up to it at all both her hands encircled my boner and she had it in her mouth. And she was working hard on it, forcefully sucking and running her mouth over it, in and out with great enthusiasm. One hand moved to my balls, cupping and squeezing them the way I like. Patience and surrender apparently have their rewards

She began moaning, the pace of her mouth on my boner picking up, me deep in her each time. Much faster than it usually happens I could feel those first sensations deep in my body and brain that lead to orgasm.

Roberta flinched, like she had just remembered something. In an instant her mouth and hands were off me and she was standing.

“Oh, gosh, Patrick, I’m so sorry,” she said. “Wow, I completely forgot that you’re going to need all that cum tomorrow afternoon. Gee, I’m so sorry to have gotten you so worked up.” The smile on her face and the laugh that escaped her mouth left no doubt that she had known exactly what she had been doing.

Then she turned and walked away, leaving me standing there with a boner that might have been sculpted from marble.

Roberta turned as she went. “I’m going to take a nice bath, and you can come with me to the bathroom. You have another little task that needs doing to pay off your bet, don’t you?” She was smiling and laughing again as she turned and walked toward the bathroom.

I followed her, and as she turned on the water to fill the tub I reached into the chest above the sink and took out some small scissors and a razor. With Roberta smiling at me, I sat on the toilet and began using the scissors to cut away my pubic hair.

I had not been engaged in this activity for more than a few seconds when Roberta said, “Let me have that razor. You know what the advice columnists all say: set some boundaries.”

She proceeded to use the razor to shave away a band of hair across my thighs about half way to my knee. She then shaved the hair from another strip that had its upper edge at my navel, all the way across my body.

“There,” she said. “You can just get rid of all the hair inside those borders.”

“Why so much?” I asked, an absurd question.

“Because that’s what I want,” she said, an obvious answer. “You bet your pubes on this game, and that’s how I want them shaved. Or I could just decide everything below your neck is a pube - I mean they really are when you come right down to it - and decide you’re shaving from your armpits to your ankles.”

I suppose I could object, but there was court of appeals, so I continued to chop with the scissors through the densest of my pubes, finally leaving nothing but stubble. Then I slathered on some shaving cream, wet the razor, and began shaving the stubble off to leave only bare skin. This really did not take more than several minutes. Although I think it took a bit longer than it really had to because I had a raging boner to work around, and I couldn’t help but indulge myself: while Roberta’s eyes were closed I stroked my shaft a bit every now and then, giving myself little jolts of pleasure.

When I had finished I was shocked at how stark and defenseless my genitals looked. All the hair was gone from the front of my body from my navel to mid-thigh on both sides.

“Okay?” I asked Roberta.

She had reclined in the tub, her eyes closed, relaxing. She opened her eyes. They focused on me standing a few feet away. Her eyes got wide and she burst out laughing, a loud, robust belly laugh I’d not heard from her in a long time.

“Oh, my good heavens!” she exclaimed through her laughter. “Oh, my God! I knew this would be entertaining, but I had no idea.” And she began into another loud round of laughter.

I turned to look in the mirror, and was more shocked at the full-length sight than I had been just looking down while seated on the john. My skin for more than a foot was white and smooth, a huge patch of clear cut in the middle of my forest of body hair. My dick, still as hard as ever, was totally hairless and jutting out. It looked defenseless and even I thought a bit ridiculous totally bald. I had never seen myself naked of pubes since before puberty. Task two was complete.

I calculated that I might just as well go to bed. That would allow me to deprive Roberta, at least for now, of her entertainment. And I could try to get unconscious so I didn’t have to think about my unremitting boner and the desire to come that Roberta had sparked in me.

This night had brought two firsts for me. Tomorrow afternoon would also be a new experience. But at least my bet would then be paid in full afterward.

When we had negotiated the terms of our bet we had determined that the last task to pay off the bet would be to come in public. But the details were left to the winner.


Sunday afternoon we sat in the local high school’s auditorium. One of the local drama companies rents the facility for their productions. This afternoon a matinee performance of Ira Levin’s Deathtrap was playing to a full house. It is wonderful entertainment: no especially deep meanings or symbolism to decipher; just suspense, humor, interesting characters, and a nicely constructed plot.

I wasn’t quite as involved and entertained as I might otherwise have been, anticipating with dread paying off the last part of the bet I had lost.

Finally, Clifford back from the dead and Myra dead of a heart attack (talk about reversals!), the curtain came down and the lights up signaling the end of Act One and intermission.

I felt the tip of Roberta’s forefinger under my chin, turning my head and attention from the stage to her eyes.

“Well?” was all she said.

I stood and headed for the men’s room, patting the outside right pocket of my sports jacket to make sure the items I required were still there.

The high school’s auditorium is located near the main entrance. Because of that location the men’s room is large, boasting about ten stalls. This being the men’s room, many of the stalls were empty. Most of the male drama enthusiasts just needed to piss. However, all four of the stalls that were occupied were at the farthest end, and had likely filled from farthest forward. So I had to take a stall about in the middle of the row. I would have paid hard cash for that last stall at the end.

I did not have the luxury of waiting for a stall that would provide the illusion of more privacy and isolation. My task had to be completed, and I back in my seat, before the curtain went up for Act Two.

I hung my sports jacket on the hook on the door, dropped my trousers and boxers, and sat on the toilet. I could see a little bit of the shoe of the man in the stall to my right. Then the door of the stall on my left opened, and I was soon looking at another piece of shoe. I was surrounded. Other men continuously went by outside the door on their way to and from the urinals.

Precious moments ticked by. I stood halfway up and reached into the pocket of my sports jacket, removing a bottle of liquid lube. I sat back down and squirted a bit on my right hand. I didn’t want too much because I wanted to avoid any juicy noises as I did this, wanted just enough to allow my hand to slide over my dick. I put the bottle in my shirt pocket in case I needed more.

I looked down at my dick and its surrounds: as hairless as a xoloitzcuintle. It was limp and slightly shriveled: didn’t seem interested in a compulsory jerk-off in a stall of a busy men’s room during intermission. But I began stroking it. What else could I do?

To my surprise, Admiral Winky began to rise to the task almost immediately, growing at a very encouraging pace. This looked like it might be easier than I had thought. Then for who knows what reason a name flashed through my mind: Larry Craig. Who? I didn’t know anyone by that name. I returned my attention the business at hand, as discretely as possible quickening my pace.

Then the pieces of the puzzle began to assemble themselves.

Larry Craig.

Senator Larry Craig, that is.

Republican Senator from Idaho.

The Minneapolis-St.Paul International Airport men’s room.

Playing footsy with the undercover vice cop in the next stall.

Mug shots.


Plea bargains.

In a Minneapolis minute my dick was doing a convincing imitation of overcooked pasta.

Damn ! I thought. Clear your mind. Associate. Make a connection. Something hot.

House. Our house. A room. Living room. Coffee Table. Ellen. A bra coming off. E cup tits. Tits doing a fetching little sway. Nipples erect.

Oh, Mister Chubby liked this. He was again finding his footing in a very bold way indeed.

“Oh, my gosh! Would you look at that!” The voice was right outside the door of my stall. Loud.

Peter the Great deflated like one of those really long inflatables they make the balloon animals out of after the fingers pinching it shut are loosed. I expected to hear air spluttering from my dick and see it going flying in great looping circles right out of the stall.

“Isn’t that just the cutest picture you’ve ever seen?” the voice observed. “Three weeks old? This is your second grandkid or your third?”

I tried to reassure myself by remembering that the incidence of heart attack in men in their thirties is not that great. But the knowledge didn’t help slow my racing heart.

Damn it. Why couldn’t some of that blood racing through my body make a detour again into my dick?

I closed my eyes; tried to associate again.

Ellen. Up.

Naked. Up.

Coffee table. Up.

Right where I had been last evening with Roberta fucking my ass with a dildo. Down.


Start over.

Ellen. Up.

Tied to the guest room bed. Up.

E cup tits. Up.

E cup tits cradling and encircling my dick. Up. Up.

The head of my hard dick poking in and out at the top of Ellen’s amazing cleavage. Up. Up.

That first spurt of cum shooting from my crotch cannon onto Ellen’s face. Oh, man! Up! Up! And away!

I stood halfway up again; reached into my sports jacket pocket and found the little flat packet.

The lights in the lavatory dimmed and brightened, dimmed and brightened, dimmed and brightened: the traditional signal for ‘The performance is about to resume, so pinch it off and get in here.’

Not giving up the grip I had on Pink Floyd, keeping the stimulation going, my cum boiling and ready to burst out in seconds, I brought the packet to my mouth with my left hand, ripped it open with my teeth, and pulled the rubber out, letting the foil wrapper fall into the boxers around my ankles. Quickly, I rolled the rubber down my shaft. I was just in time. In seconds cum was spurting, filling the reservoir and leaking down the sides. I squeezed the bottom tight against the shaft of my erection to prevent any of the cum, now swelling the crimped condom, from leaking out.

I kept my mouth and throat wide open, the better to let my breath in and out without engaging my tongue or vocal cords in the process.

But I knew. Somehow I just knew.

I could see the piece of shoe on the other side of the divider to my right. It was the third shoe to present itself there since I had sat down. And somehow I knew that whoever was wearing that shoe had twigged to what was going on over here.

The toilet over there flushed, the occupant now on his feet. The door of that stall opened and the occupant emerged into the bathroom at large. For just the shortest time his progress slowed as he passed the little gap between my stall’s door and the door frame. But by then I was sitting with my forearms over my thighs, an expression of boredom on my face, my shrinking, condom-covered hard-on concealed behind my arms.

He proceeded to the sinks and I heard water running, then paper towels being pulled from the dispenser. There were only a few men left in the room at this point, and I knew which footsteps were his, heard them recede toward the door and out.

I pulled the condom from my dick and twisted the end. Again I reached into my sports jacket pocket and this time pulled from it the tiny plastic food storage container. I dropped the condom into it and pressed on the air-tight lid. Good, now my cum was less likely to grow mold and would be fresh for weeks and weeks, and freezer-safe too, at least if the Tupperwear salespeople are to be believed.

I was on my feet in a second, grabbed the condom wrapper, pulled my boxers and trousers up, zipped, buttoned, and flushed the toilet just for effect. I left the stall and made a perfunctory pass of my hands under the faucet of one of the sinks. I dried my hands on the way to the door and tossed the paper towel, with the condom wrapper inside, in the trash as I exited.

As I scurried toward the auditorium I sensed something. There were less than half a dozen people still in the lobby. Had I noticed with my peripheral vision a man standing off to the side, motionless, his eyes on the portal to the men’s room? Fuck him.

I was soon down the wide aisle, the lights inside the auditorium already dimmed. Then I was excusing myself down the row of seats in which we were seated. My ass hit the seat just as the curtain went up, and I handed Roberta the little plastic container. She stowed it in her purse.

The theater was now silent in anticipation of Act Two. Roberta directed a whisper at me, but a loud one, audible for at least a couple rows. “Isn’t this just the most fun we’ve had in a long while?” she asked.


“What? Do you think I actually stood at the sink and squirted liquid soap from the dispenser into a condom in the middle of a crowded men’s room?” I asked.

“Well, I suppose you’re right,” Roberta said. We were in the familiar confines of our kitchen. Roberta was holding the condom up to the light, holding it by the opening, swinging it back and forth, the weight of its contents turning it into a little pendulum.

“Okay, Sweety. Bet paid. I’m sure it’s what it’s supposed to be,” she said.

“Yeah, and there’s more where that came from,” I said. I took the condom from her, tossed it in the trash, and pulled her by the hand toward the bedroom.

Our little romp in the bedroom was fun, but I found myself distracted by a thought I hoped would not grow into too much of an obsession: when was I going to manage to win one of these bets?

# # # END # # #

The last story in this series will be submitted as soon as this one is posted.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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