An Evening Out Ch. 02

I heard the “pop” sound of a bottle being open, and then a few seconds later felt the cool sensation of liquid dripping down from the top of my crack. From the consistency I could tell that Sarah had gotten a bottle of lube that I know she always carried in her purse. She was evidently dripping it quite slowly, as it took a number of seconds to slide down from the top of my crack, over my asshole, and then down my balls. She then began to trace a path down my crack, working the lube around all parts, focusing her attention particularly on the pucker of my asshole. She worked a good amount of the lube in there, which confirmed for me what her next step was going to be.

She let me stay like that for about a minute, finally saying, “Isn’t he quite a sight like that Jill? All spread wide open for his Mistress, his ass thrust up in the air, just begging for us to do something about it.”

Jill replied in a throaty voice, “Yes Mistress, it is quite a sight.” I didn’t know if Jill had ever experienced anything like this before, seeing a man being dominated by another woman, but from the sound of her voice it was arousing her quite a bit. I thought I also sensed the smell of one or both of the women’s pussies beginning to get wet; no doubt the closing off of my visual sense was heightening my others.

“Come here, pet, you can help me with this part,” Sarah said to Jill. I felt Jill kneel a little closer to my body, and then felt the sensation of what I knew could only be a butt plug being pushed against my pucker. She was gently turning and twisting it, slowly working it into my ass. My humiliation was only mounting, and yet I found myself getting more and more turned on. No other woman had ever done this to me, and yet I couldn’t control the reaction of my body. I heard Jill’s breathing getting heavier, and I could tell that she too was enjoying this.

Finally, with a pop, I felt and heard the butt plug placed all the way into my ass. I then felt a slight pressure against it, followed by a buzzing sound and a low rumbling feeling emanating from the plug and working its way up and down my ass. I knew that Sarah must have inserted the bullet vibrator into the bottom of the hollowed-out butt plug, and the sensations of the vibrations in my ass were incredible.

“So what do you think of our little pet, here, Jill,” Sarah asked her. “You like what you see? This getting you all hot and bothered again?” she asked with another little chuckle.

“Yes Mistress, I do like it,” Jill replied. It was getting hard for me to listen, given the sensations emanating from my backside.

“Well, maybe we should let you have your orgasm finally, my little pet,” Sarah said, though it wasn’t clear at that point which of us she was talking to. “You’ve waited a long time, haven’t you sweetie?”

Before I could open my mouth, I heard Jill say, “Yes, Mistress, I would like that.” I now realized Sarah had been talking to her, not me.

Sarah said, “Well, I hope you don’t expect me to take care of that. That is not the role of a Mistress. But fortunately, I do have this little tied up subbie boy here, and maybe we can put him to good use for that purpose. What do you think, Bob? Think you could help out Jill here?”

I quickly replied, “Yes Mistress,” thinking that having something else to concentrate on would take my mind off of the sensations in my ass. I knew that I couldn’t come without Sarah’s permission, and I also knew that she was very experienced at bringing me to the brink.

Sarah said, “Okay, Bob, scoot yourself down here toward the bottom of the bed, but be sure to keep that butt plug up your cute little ass – don’t want that popping out now,” she laughed. I did as she said, which wasn’t easy with the spreader bar between my knees, but after a few attempts I scooted my knees backwards one at a time. “Now lift your head and get back up on your arms.”

I did as she instructed, and then felt Jill moving around the bed. I could hear her arranging herself in front of me on the bed, and then felt her legs squeezing between my arms.

“Okay, Bob, lower your head and let’s see if you can help out my poor little pet here,” Sarah instructed. I did as she was told, guiding my head down until I was directly on top of Sarah’s pussy. I began to lick her, starting with her lips and then alternating her lips with her clit. Her wetness was overwhelming; even after all that she had leaked earlier in the evening, she was still generating incredible amounts.

The sensations I was feeling were incredible. The vibrating butt plug continued massaging my ass, while I smelled and tasted Jill’s sweet pussy as I ran my tongue up and down her lips and around and over her clit. After a few minutes I heard Sarah say, “Lower, Bob. You’re missing some important parts.” With this, I felt Jill’s hips raise up a bit, providing me with easier access to her perineum and down her crack to her puckered little asshole. I began using my tongue to make long strokes, from the top – paying great attention to her clit – all the way to the bottom, stiffening up my tongue to thrust it into her anus.

After a few more minutes of this, I could tell that Jill was getting close to an orgasm. I didn’t know whether Sarah was just teasing her again, or whether she would let her come this time. Finally, as I could sense Jill was reaching the point of no return, I heard Sarah say, “Go ahead, my pet, go ahead and come for your mommy.”

No sooner were the words out of Sarah’s mouth before Jill erupted in a huge orgasm, her body jerking and twitching around, and loud moans coming out of her mouth. Even if I had tried, I would have been unable to keep my mouth fastened to her pussy and ass, she was shaking and moving around so much. I picked my head up as Jill writhed on the bed, slowly coming to a halt after a minute or so. I could hear her breathing, ragged at first, then eventually working its way back to a normal pace.

“Thank you Mistress, that was wonderful,” Jill finally said. Sarah replied, “You’re welcome, my pet. You were a very good submissive tonight and you deserved that release. But what about Bob? What are we going to do with him?”

I heard Jill giggle and say, “I don’t know Mistress. What do you think we should do?”

Sarah said, “Well, he’s been a very good boy tonight too, so I think he deserves to come also. But I guess the question is, how? So many choices, I just don’t know what to do. Maybe you and I should discuss this?”

I had no idea where Sarah was going with this, but had little choice but to play along. I felt the two women get up from the bed and walk away, then heard the sound of the bathroom door closing. I heard faint sounds of them talking, then giggling, and then the door opened and the two of them walked back to the bed, but did not get on it.

“Well Bob,” Sarah started, “we’ve figured out what we’re going to do. We’re going to give you a little test. Being a college professor, we know that you’re very good at giving tests, so we thought we’d turn the tables on you for a change. If you pass the test, you’re going to get to have sex with both of us until you orgasm. But if you fail the test, you’re going to have to make yourself come.”

“What kind of test?” I blurted out.

I felt a sharp smack on my ass as Sarah said, “Is that a proper response from a submissive little pet?”

“No Mistress,” I replied, as the sting of her spanking dissipated.

“Here’s what we’re going to do, my little sub boy,” Sarah started. “There are five questions on the test. We’re going to give you various parts of our body to touch or taste, and you’re going to have to guess which one of us it is. But this test doesn’t have a very high standard – you only have to get three out of the five correct, only 60 percent. That shouldn’t be too hard, should it, pet?”

“No Mistress, I think I can do that,” I replied.

“Good, let’s get started,” Sarah said. “Remember – no trying to peek through that blindfold, or you’ll automatically fail the test.”

I felt movement on the bed, and could sense that both women had gotten on it on either side of me. “Okay, open your mouth nice and wide,” Sarah said.

I did as instructed and quickly felt something pushed up against my face. I realized it was a breast, and I closed my mouth and began to tongue the nipple attached to it. Right away, I knew it was Sarah’s, from the distinctive texture. I had noticed when Jill first disrobed in the living room some hours earlier that her nipples are about the same size as Sarah’s, but are much smoother.

As the breast was removed from my mouth, the nipple making a popping sound as it squeezed between my lips, I said, “It’s Mistress Sarah,” secure in my answer.

“Very good, pet, you’re right,” said Sarah. “That’s one right for you. Okay, open up again.”

I did as she said, and this time was greeted with a finger in my mouth. As I closed my mouth, I could taste that it was a finger that had been placed into one of the women’s pussies, for it was covered in the sticky wetness that signaled where it had just been. It was quite wet and pungent, so my first thought was that it must have been Jill’s. Given the mind-blowing orgasm I had just given her, I thought that her pussy would have been much more aroused and secreting much more wetness than was Sarah’s.

I was about to say, “It’s Jill,” when I quickly caught myself. What if they had fooled me by dipping Sarah’s finger into Jill’s pussy, I thought. I ran my tongue around the finger, checking for any jewelry, but didn’t find anyway. I then concentrated on the fingernail, trying to figure out if I could sense a difference from that. But hard as I tried, I could not remember whether Jill had long nails or short nails, or whether they were tapered or more squared off. With all the time I had spent so close to her body, I had not taken notice of her fingers.

At that point I decided I had no choice but to guess, and remembering some advice given to me by a high school teacher, decided to stick with my first reaction. “It’s Jill’s finger, Mistress Sarah,” I finally said.

I heard a clap, and Sarah said, “Well done, subbie. You’re right again, that’s two for you.” I allowed myself a slight smile, now feeling that I was on the path toward an orgasm through the pleasure of these two women.

“Okay, here’s number three,” Sarah said. I opened my mouth in anticipation again, but it was left hanging open. Instead, I felt something stroking up and down my erect cock, which by this point needed no further stimulation. It kept stroking up and down, but it didn’t feel like fingers.

Sarah said, “Better answer soon, Bob. I can see from your reaction that you’re enjoying this, and I wouldn’t want to see you come right in the middle of the test. That would be very, very bad.”

I replied, “Yes Mistress,” and tried to concentrate on what I felt. I realized finally that it wasn’t fingers, but somebody’s toes that I was feeling stroking up and down my shaft. If I had taken very little notice of Jill’s fingers, I had discerned even less about her toes. On this one I had no choice but to guess and hope for the best.

As I was thinking about this, Sarah started humming the theme song from the Jeopardy show, and then giggled. “C’mon Bob, what’s your answer?”, and then the stroking stopped.

“It’s Mistress Sarah,” I guessed, hoping that I was right and bringing the test to an end.

“Oh, I’m sorry, Bob, but you’re wrong. It was Jill’s toes,” Sarah said. “That’s two right, and one wrong. Let’s move on to number four.”

I felt more shifting on the bed, and then felt something rubbing against my left ass cheek. I realized right away it was one of the women’s pussies, and again, the amount of wet, sticky secretions that were being spread all over my ass made me think it must have been Jill. But before blurting out the answer, I hesitated for a second. I knew that all of this domination was a great turn on for Sarah, so she would have been quite wet herself. I tried to concentrate as the pussy rubbed up and down my ass, but it was getting harder and harder to focus on that as I continued to feel the sensations of the vibrator in the same area of my body. Both women were shaved, and were around the same size, so it was difficult to tell them apart.

Since it worked before, I decided once again to go with my first reaction. “It’s Jill, Mistress Sarah,” I said.

“Wrong again, Bob, said Sarah. “It was your dear wife and Mistress, and I’m so disappointed that you couldn’t tell our pussies apart. Tsk, tsk, what kind of a good submissive are you when you can’t even tell your own Mistress’s pussy?”

I said meekly, “Sorry, Mistress,” and kept my fingers crossed that the last question would allow me a more definitive sense of which woman it was.

Sarah said, “Guess it’s going to come down to this last one, huh pet? Well, here it goes, good luck. I want you to stick your little subbie tongue out as far as it can go.”

I did as she commanded, waiting nervously for the final question of the test. I so badly wanted to be able to have sex with these two women, and yet I knew that Sarah would stick with the rules. We had played games like this before, and no matter how hard I begged, if I didn’t pass the “test,” I would not be given my reward.

I again felt movement around the bed, and then had the sensation of something approaching the front of my face. Just as I smelled the musky scent, I felt a woman’s ass being placed against my tongue, and pressed back against my face. My tongue was lodged right on the pucker of the woman’s asshole, and I began to move it around to try to figure out which of those two beautiful asses I was tasting.

I rolled my tongue around the pucker, stuck it in, and then moved it around the region surrounding the asshole. I did this a few times, and knew that I had the right answer. It was all so familiar – the feel, the scent, the taste – that I knew it had to have been Sarah. I pulled my head back a few inches and confidently answered, “It is your lovely ass, Mistress Sarah, that I have been allowed to taste.”

For a few seconds, there was no answer. A bit of doubt crept into my mind, but I thought that Sarah was just playing with me. And then the answer came.

“Sorry, Bob, you’re wrong again,” Sarah said. “It was Jill’s ass, and I am EXTREMELY disappointed that you don’t even know your own Mistress’s ass, that ass that I have allowed you to worship so many times. You have failed your test as a good submissive, and your penalty, as you know, is that you will be forced to come on your own.”

I was shocked, and crestfallen. I was so sure that it was Sarah, and yet I was wrong. I had been looking forward so much to being able to have sex with these two beautiful women, and now I was not only going to be denied that pleasure, I was going to be forced to humiliate myself by masturbating in front of them.

“Okay, pet, you know the routine. Stick out your hand,” Sarah said. “And Jill, come on over here so you can get a good view of the little submissive boy touching himself.” I felt Jill move around the bed, and I put my hand out as Sarah had commanded.

I felt some lube drip into the palm of my outstretched hand. As I started to close it so as not to spill it, I felt a hand removing the blindfold from my head. It was Sarah’s, and she said to me, “I want you to be able to see your humiliation, pet. I want you to see the two of us watching you as you whack yourself off with your pitiful little hand. Here will be these two beautiful women, right within your reach, but you instead will be touching your little cock until it spurts.”

I was unprepared for this. Upon failing the test, I had taken solace in the fact that at least I was blindfolded, and I wouldn’t have to see them as I touched myself. But now I would have to see their faces, their smiles, knowing how they were enjoying my shame.

“Go ahead, get started, and make sure you keep looking at both of us,” Sarah commanded. I braced myself on my one arm, and gently began stroking my cock with my other hand. Jill and Sarah were both right in front of me, where I could not avoid their piercing stares as my hand moved up and down my shaft.

As humiliated as I was, I tried not to let the sensations get to me, but I was fighting a losing battle. I was already in a high state of arousal, spurred on by the vibrator in my ass that had been working there for half an hour or so already. I quickly was approaching the point where I was craving the release of the orgasm and the wonderful feeling that it would bring to my entire body.

As I continued to stroke up and down, I felt as if I was on the brink, so I said to Sarah, “Please Mistress, may I come?”

She replied, “Yes, my little submissive pet, you may come for your Mistress.”

It only took a few more strokes before I started spurting, having reached the orgasm that had been denied me all night. I continued to stroke, gasping for air, as the orgasm wracked my body, heightened by the sensation of the butt plug filling my ass and vibrating away. Finally, I collapsed on the bed, unable to support my own weight on my one arm, and closed my eyes as I attempted to catch my breath.

I felt a hand stroking my head and the back of my neck, and Sarah’s soft voice filled my ears. “That’s a good little boy, you did just what your Mistress ordered, didn’t you? You’re so good at following your Mistress’s orders.” I felt the vibrator in my ass turned off, and felt the butt plug slowly twisted and pulled out of my ass.

I opened my eyes, and saw Sarah lying down next to me, followed by Jill on the other side. The two women laid their arms over my back, and snuggled up next to me. Within minutes we were all asleep, and I’m sure the two women were enjoying the same types of dreams that filled my head.

The next morning, as sunlight filled the windows of Jill’s bedroom through the big picture window, we awoke amid a tangle of arms, legs, and torsos. We straggled into the shower, and spent half an hour scrubbing each other’s bodies with soap, and shampooing each other’s hair. After toweling off, Jill grabbed some clothes for herself while Sarah and I headed downstairs to retrieve ours from last night.

Jill came down, and prepared a wonderful breakfast for the three of us. As we chatted away at the breakfast table, I said to Sarah, “I’m so upset that I failed that test,” and laughed. “I was so sure on that last one that I had it correct, that it was your ass I was enjoying. I must have been so distracted by everything that was going on that I just spaced out. I can’t believe it was Jill’s ass.”

A devilish grin crossed Sarah’s face, and she turned toward Jill. As I looked at Jill, I noticed exactly the same look on her face. The two of them turned toward me.

“What?” I asked. “Why are the two of you looking like the cats that swallowed the canaries?”

It was Jill that spoke up first. “Welllll,” she said, dragging out the word, “we hate to tell you this Bob, but you were right. It wasn’t my ass you were tasting, it was Sarah’s!” With this, the two of them burst out laughing.

I spoke out with mock horror in my voice. “You mean you two lied to me, just to make me fail the test?”

The two of them could barely get the words out they were laughing so hard. “Yes, sweetie, we cheated, but it wasn’t so awful, was it?” Sarah said.

I couldn’t do anything but laugh myself. “No,” I said, “I’ve experienced worse, I guess. But I’m going to get back at the two of you.”

Sarah replied, “Oh, we’ll see about that. Don’t forget who your Mistress is, now,” as she lightly patted me on the head.

Sarah then turned to Jill and said, “And I’ve got something to say to you, my other little pet. That was the first time you’ve ever done anything like that, wasn’t it sweetie?”

Jill, who had still been laughing at my embarrassment over how I was duped, dropped her fork, and said, “My god, how did you know?”