1

This story is presented in a total of five parts. There will be a second part of this chapter 2A, and there is a two part chapter 2B. I think the story hangs together fine on its own, but I think having read the stories

Roberta & Patrick's Bet

and

Roberta's Bet

will increase your enjoyment of this story. The story is complete and all installments have been submitted so hopefully you should be able to begin reading the story and have an installment to read each day to the story's conclusion. As always your comments and observations are very welcome.

Roberta & Patrick's Next Bet – Chapter 2A, Part 1

A queen!!!

That gave me a full house, beating Patrick's straight.

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.

Roberta is completely right. 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 3 on my last card and completed my straight I knew it was in the bag. Well, so much for sure things.

She was very direct about the whole thing, telling me immediately, "Looks like a full house. And that beats your straight. Strip."

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 was certainly enjoying the situation. When my boxers came down my dick was half hard. Shit! That certainly gave the wrong impression! She told me to stand in front of her. She was still cross-legged on the floor. She reached up and gave my dick a few pushes back and forth, wrapped her hand around it, brought herself up a bit 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 an instant. Then she got up and left for the bedroom, calling over her shoulder that she would be right back.

I just kind of stood there. I mean, there wasn't really much else to do. My boner was doing a great imitation of a telescope, pointing to the sky.

Roberta was back after a few moments, several items in her hands. She handed me the leather ankle cuffs and wrist cuffs that so often adorn her and told me to put them on.

I think if you know the

Ellen's Bet

story you can imagine perhaps what was going to happen to me next.

She had me get on my hands and knees on the coffee table. 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 left 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," Roberta said, "you did the same to Ellen. Serves you right."

However, after my cuffs were secured she got me a pillow and placed it 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.

She went away then. I had some minutes, actually longer than I was very comfortable with, in this position. This was a first for me, although I enjoy Roberta in this position, restrained in this way and in this place, every once in a while. But I have to think about this some. Roberta never says a word of complaint, but this was 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 was beginning to feel some rising tension after some minutes without her return. But then I heard the swish of her feet on the carpet as she entered the room. 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 my asshole. Shortly after I felt something finding its way to being seated there, moving up and down as it began to find and push into my ass.

'Well, shit,' I thought (no pun intended), and waited for my ass to be pried widely opened.

Clearly it was a dildo of some kind, how big I did not yet know. Roberta was holding it in her hand and pushing it into me. And it was an invasion, my asshole spreading farther and farther, my breathing becoming more shallow and little vulnerable-sounding 'ah, ah's leaving my lips.

There is nothing, I was now experiencing, that can make you feel more vulnerable 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 of the smooth shape, 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, clearly from some sort of vibrator. 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.

As the expression goes, the clear white light of stupidity illuminated my brain. Realization dawned on me. She didn't have a strap-on, did she? I didn't think she did. I've never seen one around here anywhere. 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 was right up against me, her hips pressed tight against me and grinding. A moment later I heard crying and was so glad to hear it. When Roberta cums and cums 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 hard slap. "Not bad, Lover Boy," she said.

"This is a little uncomfortable," I said to Roberta.

"Too bad. You had Ellen like this using her for a lot longer than this," Roberta said. "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 complaints. It was stretched and could accommodate the dildo easily. And 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.

She seemingly took her time but eventually came, this time in a more controlled and orderly 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, nude, just 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, but never imagined it would be attached to her and that she would end up bucking her hips back and forth fucking me with it.

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 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.

She began moaning, the pace of her mouth on my boner picking up, me deep in her mouth 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 started a little 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 little laugh that escaped her mouth leaving 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.