Seducing Jennifer

After I held her for a few minutes, she underwent another personality change, hopping off my lap and strutting around, showing me the plug in her ass, and asking me what I was going to make her for breakfast. It was really quite disconcerting and a little spooky. Jennifer had occasionally insinuated that her mother was crazy, but I figured, what the hell, everybody gets pissed at their parents sometimes. I was really about convinced that the 'crazy' diagnosis was an understatement. On the other hand...there's that thing about hard dicks and consciences. And then I couldn't really just walk out of here and try to hitch-hike home with a plug in my ass. I would wonder for the rest of my life what else she had planned.

We threw on a couple of robes from the huge walnut armoire and went downstairs, both giggling about the other's bow-legged walks. Anna was suddenly in a chatty mood. "Tell you what, Jacky, I was walking almost this bow-legged after that last time – on the couch at my house – my pussy hadn't been reamed like that for years. Actually that's not true – it's NEVER been reamed that way before" She stood on her toes and stroked my long black hair, running her fingers through it and kissing me wantonly. My cock had wilted from walking down the stairs with the fat plug dilating my asshole, but it responded enthusiastically, popping out of the front of my robe. It apparently distinctly remembered being fully embedded in Mrs. C's tight pussy, bumping against her cervix as she ground her pubic bone against mine.

She grabbed my rod and massaged the head, lubricating it with my leaking pre-come. "You're a very naughty boy, Jacky. I can read your mind like a book. Right now, you're thinking about bending me over that granite counter and fucking my brains out." Actually, at the moment I had been thinking about ham and eggs, but I started thinking about bending her over just as she mentioned it. Coincidence, no doubt.

I pulled open one of the refrigerator doors and was surprised to see that it was fully stocked with all manner of goodies. "Hey!" I said, "There's a lot of food in here." I opened the other side and the freezer and everything was full. "Are you sure nobody is going to show up here? Because it kind of looks like someone is planning to do a lot of eating."

"I know someone who is thinking about doing a lot of eating," she grinned. "As in eating out my PUSSY!" There was a manic glint in her eyes that made me extremely nervous.

"No, seriously Sweetie, the little pervert keeps this place all ready for company all the time. In case he need to organize a slut party for some of his scumbag friends. Politicians, mostly. Cops sometimes. A couple of Arab guys once, and they were CREEEEEEEEPY. He actually has a service that comes in once a week and takes away all the food and replaces it with fresh stuff. Wish they would give me the stuff they throw out every week. But that's somebody else's rice bowl, I guess. Oh, yeah, we also get Japs sometimes. And then they order special delivery sushi, which most of the girls like, but nobody really likes some of the extremely kinky stuff they want to do."

"Uh huh," I said absently, pulling food out of the refrigerator. A dozen cage-free eggs, a slice of smoked ham, a little can of...Beluga Caviar? I wondered if that would go with breakfast. It was supposedly fish eggs, which are a kind of egg....suddenly I wondered how Anna was privy to all these details. I wouldn't think that a secretary/receptionist would be in on those kinds of parties.

"And you should see the booze they put away! And dope too, but I stay away from that and I hope you do too because that shit can really –"

"So do you come here often?" I asked, cracking eggs into a crystal mixing bowl.

She batted her eyes at me, vamping. "Why no, sailor, this is my very first time and I'm a little scared so I hope I can find a big strong man to take care of tiny little me."

I laughed but my heart was in my throat. Was she playing another game? Or was she really hinting that she was some kind of a...whore? "So tell me about your job," I said, beating the eggs with a whisk.

"Oh, officially I'm personal secretary to Dr. Hyman Hershkowitz, J.D., L.L.D., Ph.D. and total A.S.S.H.O.L.E. The little pervert. I think his mommy finally pulled him off the tit when he was 12 and he's been lost ever since. But anyway, what I am in fact is his substitute mommy. Except that he used to fuck me. Before his little pee-pee went limber on him. Now I mostly just go places with him, hang on his arm and look pretty, and suck his little weenie about once a week. I shouldn't complain. At least he keeps me for himself and doesn't pass me around. Mostly."

I squinted at the can of caviar. What the hell. I opened it and dumped the contents in with the scrambled eggs. "So you're kind of like his escort when he goes out?"

"Yeah, we have to show up at the parties here once a month or so, help entertain, all that. It was fun once," she said wistfully, "but I'm getting damned sick of it. I've been kissing his ass for nearly 18 years now. It's about time to make a change."

"How did you ever end up with a job like that?"

"Well, it was like this: I had Jennifer at 15. And I was out on my ass with nothing, because my bible-thumping parents could not allow a filthy little slut like me to live in their house. So my options were limited. I only had one thing to sell, and I did it with class, didn't I?"

She embraced me from behind, leaning her head against my back. "Hey, let's not talk about sad things. I'm hungry, so get cooking, Wife."

Wife? I shivered, anticipating another personality change.

I served her breakfast on the couch by the fireplace where we had made love the night before. "Ooooh, looks good!" she said, bouncing on the couch and clapping her hands. "But before you sit down, Sweetie, why don't you just trot upstairs and turn on the Jacuzzi so it will be nice and hot for us later?"

Obediently I trotted up the stairs, very aware of the plug flexing in my ass, located the controls for the Jacuzzi and turned it on. It gurgled to life and I went back downstairs to join Anna for breakfast.

She took a bite of scrambled eggs, paused in mid-chew: "What? These lumps? Is that caviar?"

I nodded. "Do you like it? I was kind of experimenting."

She swallowed and laughed with her hand over her mouth. "Oh Sweetie! You really know how to hit the little pervert in the wallet. Did you know this stuff costs over a hundred dollars an ounce?"

My neck flushed with heat. I had no idea. "I hope you really really like it then." I took a bite. Fishy. Not bad though. But I wouldn't pay any hundred dollars an ounce for it.

"It's perfect, Honey. One more piece of a perfect memory. Me and my lover sharing the most expensive breakfast in town after a full night of hot sex. Well, maybe not a FULL night, but we aren't done yet either. Hey, we should be having champagne with this. Mimosa cocktails. You know how to do that? Half champagne and half orange juice."

I waddled back to the kitchen, found some fresh-squeezed OJ and a bottle of something called Dom Perignon, and mixed some tall drinks. They were quite good, and we finished off the bottle of champagne, getting giggly toward the end.

Upstairs again we shed our robes and stepped into the steaming Jacuzzi. I sat down on a ledge so I was submerged only to my waistline, reluctant to plunge all the way in. The hot water did relieve some of the pain in my tortured rectum, however. Anna plopped right into the middle, submerging completely before floating over to rest her arms on my knees. Her luscious apple-sized tits bobbed on the surface of the water.

My cock popped up out of the water like a lighthouse. "Oh my, what is this?" Anna teased. "Is my little Wifey horny?" She sucked my knob into her mouth and polished it with her tongue. I obligingly thrust upward to give her more of it, but she pulled away. "Now don't be a naughty little slut. First you have to scrub me all over with a loofah. And then..." she pulled herself up to present her stiff nipples for my kisses, "then we're going to go back to bed and fuck ourselves silly."

We were glowing as we stepped out of the tub. "Now Jacky, I'm going to go into this bathroom and get ready. And I want you to go to the one in the next bedroom and do the same. It's time to pull the plugs." She winked at me lasciviously. "Oh, wait; you'll want to use this before you come out. Unless you want me to do it for you." She handed me a slender cardboard box. "Now shoo. And don't waste a lot of time primping. I have a BIG surprise for my Sweetie."

The next bedroom was not as ornate as ours but it was plenty fancy. I let myself into the bathroom and tried to pee. It just kind of drizzled out, probably due to the increasingly uncomfortable butt-plug. I sat on the open toilet and looked at the cardboard box in my hand. It said, "Disposable enema." O-kayyyy. Wouldn't be needing that until I got the plug out of my ass. I reached down between my legs and found a plastic ring on the outside of the plug. I yanked at it experimentally and squealed when the plug slid out a little and popped right back in. I yanked harder and got it past the biggest ridge. After that it was no problem, until a gush of foul liquid splattered into the pot and splashed on my thighs. Ugh. I could see why Anna wanted us to do this in private. Cramps racked my stomach and another gush of hot liquid spurted into the bowl. I began to feel light-headed. When my bowels seemed to be completely emptied I waddled to the shower and washed off with cool water. I washed my hair too. Nice assortment of hair products in there. My hair was coarse and thick and I needed a lot of conditioner.

I dried off and read the instructions on the disposable enema. Seemed easy enough. I knelt on the bath mat and squirted the enema up my ass. It felt pretty good, actually. My asshole was burning like fire and the cool liquid helped. When my guts started to rumble I got back on the pot and let go. It was crystal-clear this time.

I carefully scrubbed the butt-plug with soap and hot water before going back to the master bedroom. I cracked open the door and looked in, not sure what to expect. Anna was standing in front of a cheval glass arranging her hair. She was wearing something that looked kind of like a leather garter belt from the back. There were no garters, though, and some sort of straps wound around her thighs. She caught a glimpse of me in the mirror and turned to confront me. "So my naughty little slut was peeping at Daddy, wasn't she?" She placed her hands on her hips sternly, and that's when I shifted my gaze from her sweet titties to her...big, fat, COCK? I thought my jaw would hit the floor.

I gulped loudly and Anna laughed. "I think my little wifey-slut is scared of Daddy's big dick, isn't she?"

I nodded, still stunned speechless. Okay; she had a strap-on dildo. Surely she couldn't really be planning to use it on me?

"I think my little slut needs to get over here and suck Daddy's hard dick before he gets mad and gives her a good spanking." She picked something up off the night-stand and slapped it against her hand. It was a thin leather paddle.

"On your knees, slut," she ordered, strutting toward my with the rubber cock swinging menacingly. "Suck that cock like you mean it. And maybe I won't spank your saucy brown ass until you cry."

Uh oh. I had a feeling I was about to pay for the spanking I gave naughty little Anna earlier. I dropped to my knees, which was easy to do because they were shaking like palm trees in a hurricane. I crawled toward her. She took the rubber cock in her hand and rubbed it across my lips. "You have exactly thirty seconds to make me come. If you don't, you're going to get a spanking you will never forget. And then you're going to get fucked in your tight little ass."

I knew I wasn't likely to be able to suck off a fake dick, but I did try. I took the knob in my mouth, and it was quite realistic; a jelly-like substance rather than hard rubber as I had feared. I reached for the cock to stroke it with my hand and she swatted me on top of the head with the paddle. "No hands! Keep them behind your back and suck!" I took as much as I could into my mouth, which wasn't much. She grabbed a handful of my hair and drove it in further, until it hit the back of my throat. I gagged, and she held my head there until I thought I would suffocate.

When she finally let me spit it out I gasped for breath. "Time's running out," she warned. "My little slut is about to get her ass blistered and fucked for being so lazy." I bobbed up and down on the fake cock awkwardly a few times before she yanked it out of my mouth and slapped me in the face with it. "Time's up," she snarled. "Lay across the edge of that bed, and keep your hands out of the way or I will cuff you."

I flopped down on the edge of the bed and presented my ass for abuse. It wasn't long in coming. The first stinging swat was a surprise.. "That was for sneaking and peeking," Anna said. "And this is for playing with yourself in the shower. The second swat hurt like hell, and I yelped indignantly, about to protest that I hadn't played with myself – much – but thought better of it. "And this is for not knowing how to suck cock!" She whacked me again and my eyes began to water. It really stung.

"I'm sorry," I sobbed. "I'll never do it again!"

Her cool hand caressed my glowing ass. "Oh Sweetie," she purred. "Daddy hates to punish his little slut, but how else will she learn?" Another stinging swat came out of nowhere and I wailed with pain. "And that was just for being a horny little slut!"

She kissed my burning ass-cheeks tenderly and pushed one knee between my thighs. "Now I suggest that you get those legs apart, because you are going to get fucked." I heard the squirt of KY jelly and then felt her finger smearing it around and into my sore asshole. She lubed me thoroughly and I then I heard a different squishy sound; she was greasing her rubber cock. Before I had time to panic it was nudging at my hole, stretching me slowly until the head popped in. I was panting like a racehorse. My cock had wilted during the spanking, but was once again showing signs of interest. Anna reached around me and took my dick in her tiny fist. "So little slutty likes a big cock in her ass, doesn't she?" I moaned. I didn't like it all that much, but I wasn't about to say so and provoke another spanking.

She pushed the dildo into my ass a little further. I groaned and she slapped my still-stinging ass with her free hand. "Slutty should be telling Daddy how much she loves having his cock in her instead of complaining."

"I love it, Daddy," I sniffled. "Please fuck me." She stroked my shaft, penetrating a little deeper into my ass with each thrust. Pre-come began to drizzle from my pee-hole, and she rubbed it into the head of my dick. Time stood still. I was pouring sweat from every pore and hot and cold flashes racked my body. I was glad my bowels were empty. She continued to pump my meat but it wasn't going anywhere. It felt good, but my cock was nowhere near hard enough to shoot a load.

She hesitated and I had a fleeting hope that she was in all the way. No such luck. "Now you've got half of it, Jacky," she said in her Mrs. C. voice. "But I think you need to feel it all in you. Just for future reference. To help you become more considerate of others."

"Oh God!" I moaned. "I can't possibly take all that! No one could!"

"Funny you should say that," Mrs. C. purred. "I chose this one because it's almost exactly the same size as yours. Maybe not quite as thick as the base..." She grabbed my hips and pulled me back against the invading monster. "Maybe this will help." I heard a click and a gentle buzzing vibration started somewhere deep in my tortured bowels. "I got the built-in remote control vibrator option, just for my little virgin lover."

It did help. But getting fucked in the ass was still not high on my list of favorite things to do. But she was determined to get it all into me, and after an eternity during which I almost passed out twice, I felt her silky pubes against my sensitized ass. I was surprised at the amount of pre-come that was streaming from my semi-hard prick. She started to draw back. "Now, Jacky," she lectured, "what I want you to learn here is this: ass-fucking can feel good if you go about it the right way. But it's not the same as pussy-fucking. Except maybe for a girl's first time. They can both hurt like hell the first time...and if it's really bad some girls never want to do it a second time. So when you're with a virgin, like my daughter for example, you want to take it very very slowly." As she spoke she eased the rubber dick back out of me an inch or maybe two. It felt like she was pulling my insides out with it. "If she says it hurts, stop and give her time to get used to having you in her." She thrust back in gently, and it didn't hurt at all. "And even when she gets used to that, no long-dicking her until she asks for it." She began slowly fucking me, back and forth, lengthening her stroke a little each time. "You need to get it in your head that Jennifer will probably only be able to take half your cock in her pussy for quite a while." She began fucking me faster and my cock spewed pre-cum at every stroke. "It might be months before she can take it all comfortably." Anna's breathing had become ragged as she plowed my ass. It sounded suspiciously like she was approaching orgasm. The vibrations in my ass intensified and suddenly seemed to be coming in waves. "You should also know," Anna gasped, "that this vibrator is also pushing directly against my clit, and I'm...Oh God...I'm coming!" She rammed the rubber cock fully into me and I convulsed with pain as she shuddered through her orgasm. When she caught her breath she eased the fake dick slowly out of my ravaged asshole. When the head finally popped out of me cold air rushed into my abused anal passage and I felt terribly empty. And extremely frustrated. It felt like I had been held on the edge of coming for hours.

She flopped down on the bed next to me, still gasping for breath. I wanted to climb on with her, but my legs seemed to be paralyzed and I remained half on and half off. She combed her fingers through my sweat-soaked hair. "When you can move again, we'll hit the shower. Then maybe a little nap? Or if you can't wait...my back door is open for you."