The Last Time Is the Best Time

It was nearly closing time. Hilary didn't even announce herself through the intercom as she easily could have, from the front office, where she held the fort, but knocked at the door, asking if she could come in. The firm was down to three, the two warring partners, and to one person who doubled as girl and boy Friday. Hilary was a bit "born yesterday", even more so than I, who had some notion that she was a bit daft. Almost at once on entering, Hilary announced that she had to stop fucking me; her boyfriend didn't like the news getting about that Hilary was fucking me. -- Actually -- the thought ran through my mind - I had fucked H. only twice, the first time when we had met at a bar when she had come for a job interview that her non-identical twin-sister had suggested, and then the second time when I gave her her job as a secretary. "Do you still a want to fuck me?" had been her reply to the good news.

"Yes."

"When"

"Right now." And she had come right over. But I had not fucked her since she started to work at the office, some months ago. For the simple reason that I made it a point not to fuck any of my employees, it might create complications. Before and afterwards, I came to realize, was an entirely different matter. And I had not given her the job because Hilary was a wonderfully eager fuck, I gave her the job because she had a bit of the street girl about her, she could hold the fort, the front office, she could handle a bit of gaff, we had never had anyone like that. I had not fucked Hilary in all these months, not since I actually saw her extremely enticing figure at the office, for the good reason that I made it a habit to keep work and pleasure separate. Short sexy tight skirt, tight blouse, good ass, the love of sex written all over her, "Born Yesterday" as it were, but not a bimbo. Straight in a way, but street enough to be hip to the man-woman thing, and to like it. The second time we had fucked she indicated that she really really liked ass fucking but that someone, instead of easing into that deeper darker mode of pleasure, had taken her, had raped her, and that she was vulnerable there, and thus reluctant, though sometimes her desire for ass fucking got so strong she did it despite the pain. I had not taken her up on that invitation. I did not look forward to a possible blood bath on my mattress. Unintentionally I had injured a girl once that way who had indicated how much she liked it in the ass, without giving thought to proper relaxing anal foreplay. - So I was just a tad surprised when Hilary, in her ultra short tight little skirt, fine ass, made that blunt announcement. I might have said: "But we aren't fucking, are we?" Or: "Who gives your boyfriend the idea that we are fucking."

I guessed, to account for the skewed time, that she must have told him only the other day. However, I, who liked "last times" was just horny enough to reply to her by saying: "What about a last time..."

"When," Hilary said, in about the same tone of voice that she had used when I had said yes I wanted to fuck her again when I had given her the job as secretary and she had come right over, in the morning, and we had a very nice morning fuck indeed, during which she confessed, without the least prodding on my part that she really really liked ass-fucking but that someone had raped her and that now it hurt, nonetheless occasionally when she wanted it real bad that way, she did it, pain or no pain...which mention of pain made me who hated pain and inflicting it desist. Her half-twin Heather, with whom I would have a fling later on, loved ass fucking too, turned out to be the best ass fucker of them all the way she knew how to bend over obligingly over the arm rest of a lounge chair, sticking her ass into the air, and had not been raped and so her anus and its erotic possibilities were deeply sensually intact, who even liked to play "pampers", that is to put on a pair of pampers and poop as she was slowly ever so slowly fucked into a behind that knew how to expand and to contract during the oozing to give itself and me all the pleasure, a pleasure until then unexperienced. But that experience still lay several years ahead, and I had not the least inkling of its eventuality at that moment as I said "Why don't you sit on my lap." I pulled Hilary towards me and slowly slipped my hand up between her silk stockings, of her thighs, and her skirt up so that she could straddle my legs on the chair on which I was sitting. Very moist silky panties at once. Panties wet with desire, and I was nearly crazed with desire myself when it occurred to me to ask whether H. had locked up the front office.

She had not.

"Why don't you put everything in order and then buzz me on the intercom and we can tell each other all the things we like to do and then we do them and we fuck our horny hearts out."

Hilary was so obliging, she stood up, straightened her mussed up skirt, I got up, pulled her to me, and finger fucked her to the point that we simply couldn't wait and descended onto the Persian carpet and I started to fuck her through her panties. But then backed off. At least the door to the front office and my office had to be locked. "No, you have to lock up first."

Within minutes Hilary was on the intercom. "Done," she said.

"I want you to sit down on your chair and touch yourself...

"I am sitting."

"Are you wet?"

"I'm creaming."

"Tell me all the things you like to do, and like me to do to you. Tell me your favorite fantasy when you masturbate. No, tell me when you fucked the first time."

"At sixteen."

"Who was the guy?"

"Allessandro, you know him."

"Allessandro." Did I know Allessandro. Not only did I know Allessandro, I knew about a half dozen girls who had been devirginated by him, all at sixteen, a painter he seemed to run a serial devirgination operation out of his studio on the island. "Did he fuck Heather,too?"

"First her, then me."

"At the same time."

"Not at first."

"How many of the same men have you and Heather fucked, either at the same time or sequentially."

"Six I think, but I wouldn't fuck Jeff [Heather's then boyfriend]. He's just too weird."

Well, I would not have fucked Jeff either as a woman, however a lot of men, men who were not gay, had some kind of strange crush on Jeff, were smitten, found him charming in his Junkydom and all, emaciated, nervous, so junked-up that he could barely breathe. Weird indeed. Perhaps it was the male mother instinct coming out in these guys. Heather was a fox, but was entirely straight. Mad for Jeff, a junky couple, adhering to each other as to their addiction.

"I like going down on each other best."

"D'accord. But there has to be a bit of foreplay."

"No sometimes you just diver for each other."

"Tell me the sequence. You are horny, you start to touch yourself, detail by sexy lewd little detail."

"I just can't wait, I'm coming over now."

"No! Play the game!"

"I'll do anything."

"I know, that's not the point."

"And you?"

"I like to see you lie down on the couch, pull up your skirt and start touching yourself, first just the crotch of your panties, then to slip your hand under the panties...that gets me crazed. If you do that I'll be on top of you and start to fuck you at once."

"I'd love that."

"I love to play first time."

"You mean make believe I'm a virgin?"

"No. We tell each other the first time we fucked in complete detail, but can't fuck until we are both finished describing, then we combine the two into our perfect first times. Because first times generally are anything but perfect,

"Oh what a mess I made."

"They tend to be perfect fumblings, unless you are introduced into fucking by an experienced elder lover."

"Allessandro was great, so experienced. Still, what a mess."

Even before we were done painting the most exquisite and crude pornographic images into our imaginations, Hilary exclaimed: "I can't wait" and went off-line, I could hear the door being locked and her running down the corridor, she rushed in, locked the door and lay down on the green Nougahyde couch that had decades upon decades of fucking tales to tell if it could talk, all the way back to its origins in the Nickelodeon wars in the 20s of St. Louis, pulled up her skirt, and, one leg dangling over the side of the couch, spread her legs wide and started to finger her pink cunt half of which was visible beside narrow crotch of her ultra slim panties. I instantly kneeled down by the couch and dove for her pussy, pulling her fingers away and the panties to the side I did what Hilary had said she liked most: a man going down on her and making her come with his mouth before she got fucked good and hard. Indeed, that was the way to fuck Hilary. She came quickly and with me looking across the mound the beaver dam I saw the most delicious expression suffuse her face. Ah, how I envied women their orgasms! I then pulled her off the couch onto the carpet and, after giving a couple of spanks on her bottom, that she said she, a Catholic girl, liked so that she would be completely loose, punished ahead of time as it were, holding her ass with one hand,and diddling her clit with the other started to fuck her methodically through her panties, before I let loose and just fucked straight and hard ahead, until we both came near simultaneously. Then I went into both our favorite 69 position, and we both came once more that way.

As we both put ourselves back together, Hilary to leave, I said: "I guess we can play last time, as often as we like." And we did then, quite a few times, each of them preceded by a long or not so long intercom talk, during which we would describe in detail what game to play that day, or preferably sexy things we had done with someone else: Hilary as a school girl - the day she had come dressed as one; Hilary as the sluts of sluts - the day she had come dressed like that; Hilary as a Catholic girl who had to be introduced into fucking by a Priest [her actual second time, which from what she said, could not have been lovelier, on the altar, that is on my altar, my desk, a Catholic Priest who had fucked twins, lovingly fucked both eager hot seductive squealing laughing twins on the altar so that they swore that if anyone ever accused the priest of molestation they would come to his defense and of altar fucking. Their altar was fucking and that is where they worshiped and that is why I worshiped them, the darling Catholic Irish school girl lassies]; Hilary as as my whore; Hilary as the naughty 16 year old who introduced a 12 year old me into sex, a role reversal that she, or rather Hilary's mouth got off on, and her pussy with which she rubbed herself sitting on top of my mouth until she came.

So we kept playing last time many times over until there actually was a last time when the office was closed down. It had been a wonderful way to end a hard day's work, for Hilary to go home, for me prior to my afternoon snooze.

Did she tell her boyfriend?

Yes, she told him each and every time, saying that she just couldn't bear not fucking me, but that it really was the very last time, and he was fucking other people too, wasn't he. So without breaking up with her, or his getting her to quit her job, which supported his endeavors as a would-be downtown film auteur, there was little that he could do. Except that it kept turning him on, and he would fuck Hilary too, so for every time Hilary fucked me, she got fucked a second time when she got home, and the color in her face and all of Hilary kept blooming into the most wonderful Irish rose-cheeked lassdom.

Altogether we played maybe a dozen "Last Times" over a 12 months period.

That is until the time that I started to fuck her twin Heather and Heather arranged it so that both she and Hilary would fuck the same man, a big big turn on for them both since that is how they had started to fuck at age 16.

Heather and I fucked the nite after a date during which she told me how her boyfriend had died in a car crash... the kind of talk that really required the intimacy of bed. I myself had come far too quickly that nite, since there was a lot of emotion involved, Heather said she didn't mind. Heather was incredibly obliging. Nonetheless I felt that we were by no means even in sexual satisfaction and relief, so that upon coming, just a release of emotional tension more than a hugely satisfying orgasm, just a squirt really, I put my head between her Heather's ultra sexy thighs and we proceeded immediately to go around the world, as Heather's head started to bob piston-like as soon as my tongue accessed her anus and one our fingers probed each other's behinds she started to reach the verge of coming she turned around, draped herself over a corner of the bed that bed that stood about two feet off the ground and stuck out her behind. Having already licked and fingered this sweet asshole I knew that Heather, like her sister, was an uninhibited anal erotic, I placed both hands onto her left and right groin, held her to me, and entered her from behind, her vagina from behind which elicited a positive little yelp of joy, I seemed to be hitting the spot, her hand urging me to go to the orifice just above, the real deep dark orifice..."Both" was all she said and of course I knew what she meant, alternately.

"Very slow when you do it in the ass.

"How did you get into ass fucking?"

"Right away."

"And you liked it right away?"

"I used a finger in my ass even before I started to fuck."

"Just like Hilary."

"Oh you fucked Hilary in the ass too?"

I was delighted to hear a tinge of jealousy, but decided not to prevaricate. It appeared that, though Hilary had called Heather at once the morning after we had first fucked, she had not told her that we had not ass fucked; but I was not going to pretend that we had.

"No, Hilary said she had been raped, and that now it hurt. And I like pain free experiences."

"That's nice. I hate pain, pain sucks."

"Have you ever ass-fucked at the same time that you pooped?"

"No, but I love pooping very slowly, sometimes I nearly have a come when I poop, and I diddle myself at the same time, I have the sweetest feeling deep inside my ass when I poop and when you fuck me real real slow, withdrawing, coming back out, that's pretty much the same feeling, but knowing that it is a cock and that you are holding me and mastering me..."

But there was no poop to be had that day, it just made for the slowest ever ass fuck during which Heather proceeded to give deeper and louder little moans of pleasure, so that when the time came one morning that Heather actually was able to poop onto my cock and put a warm load in the pampers she had brought it was nearly anti-climactic. But that, either not pooping but trying to, and occasionally ass fucking while there was some poop to be had is how Heather and I fucked until I raised the ante and asked her if she had ever gone down on a woman.

She had not. As a matter of fact, aside having been kissed by a sexy girl who had petted her below the waist, while she had been high, Heather had been entirely straight, she loved cock inside too much, cock in mouth cock in every orifice that would hold cock.

But would she for my sake if she liked the girl maybe? No, she wouldn't, even Heather's being obliging knew certain bounds, even thought Heather was even more obliging than Hilary, and cleverer, also with the underwear that she knew turned me on, and since I can be just as obliging, and since both of us could also be competitive we got into a competition who could be more obliging than giving the other pleasure. It was inevitable that Heather, somewhat petite Heather but with enough broad in her hips, with her firm thighs, fine breast, Irish lasses spirit and black hair, and a lot of instant leaping fish left in her well fucked thighs would fall in love and with making love ... until we nearly died of fucking and the devouring of each other's genitalia... And when I found myself, who knew he had to remain unattached, found myself falling in love with her, I had to withdraw. Under different circumstances, since there was a lot more to Heather than wonderful fucking, it would have been as good if not a better partnership than she had had with her dead Junky boy friend, she had gotten off junk, I had never tried more than one line that put me to sleep. Heather awake, we could have gone places, she was the rare girl that you can steal horses with. As long as you don't have her non-identical twin "Born Yesterday" Hilary to slow you down.

Of course, we had a three some with Hilary, several as a matter of fact. It proved very difficult for me who is as easily infected by laughter as by the clap to keep a hard-on what with the sisters cheering each other on to ever lewder acts while laughing their heads off.

FINI