Judy Ch. 01: Work Experience

It was no surprise to me by now that I discovered two things; first, that Judy absolutely loved her ass being violated like this and second, why I've seen so many people refer to a woman's asshole as a 'rosebud' - that's exactly what it looked like as her anus opened up to accept my digit. I watched, mesmerised, as her dark hole opened up and swallowed my thumb easily, my invasion stopping only when the pad of my thumb was resting on the inside of the stretched flesh of her buttock.

This was enough to bring Judy to yet another climax, this one the biggest she'd had so far as evidenced by the loud shriek which erupted from her throat and the vicelike clamping of her vaginal muscles around my still thrusting manhood. I paused for a few seconds with my prick buried deep inside her clenching pussy and my thumb inserted fully in her rear entrance. Then I started to pull out of her cunt, while leaving my thumb in place. When the head of my penis was still just inside her I thrust forward, withdrawing my thumb at the same time. After a few strokes I had got into a nice rhythm where as one organ was entering her the other was withdrawing, giving Judy a kind of double-penetration which was sending her to the moon and back every few seconds.

She was now in an almost constant state of orgasm, her juices flooding out between her thighs and covering both of us in her sticky cum. I decided, as much for my own enjoyment as Judy's, to replace my thumb with my first two fingers, which were already covered in juices and needed no further lubrication. I managed to do this with no disruption to my rhythm, and Judy seemed to find the extra thickness of two fingers even more arousing.

The one drawback to fucking this way was I could no longer see Judy's breasts, though my minds eye could see them swinging back and forth as we continued our mutual thrusting. I reached round in front of her, but couldn't quite reach her breasts due to our rapid movements; however I could reach the pearl of her clitoris, and I placed my finger directly on her button and began to rub gently in a circular motion, sending Judy over the edge yet again. I needed a bit of a 'rest' then, and stopped moving my hips to give my cock a brief respite, though I kept probing Judy's ass with my fingers, spreading them wider now to open her rosebud even more. Then my cock, which was rock hard and slippery as hell, popped out of Judy's squeezing pussy landing with a thump on her butt cheek right next to my probing fingers.

The thought which flashed into my head then was quite automatic, given the circumstances, and before Judy could open her mouth to complain at the loss of my member in her suddenly bereft cunt, I removed my fingers from her ass and used them to place the head of my pulsating shaft at the entrance to her dilated hole. Judy moaned at the feel, and spoke for the first time in what seemed like hours,

"God Tom, I don't know if I can take you there. You're so much bigger than anyone else I've ever had - just go easy, OK?"

So much bigger than anyone else? Fuck - I'd never had her down for someone who'd even tried anal sex, never mind wanted it, in all the fantasies I'd ever had about her! Still, I'd think about that later. Now, heeding Judy's request, I pushed gently against the opening to her anus, the head of my penis beginning to part the flower of her opening. As the ridge at widest part of my cock-head neared the widening ring of Judy's sphincter, I heard a slight gasp from her and immediately stopped, allowing her all the time she needed to get used to the thickness that was about to invade her. I felt her pushing outwards with her anal muscles and, sooner than I expected, my glans was fully inside Judy's tight ring and on it's way to filling her completely. I eased further in with tiny, almost imperceptible strokes, until over half of my rampant eight-inch penis was buried inside her forbidden hole. I replaced my finger on its earlier spot, directly onto her swollen clitoris, and resumed the firm, gentle circular rubbing I had been doing before. This seemed to make things a bit easier for Judy; the remaining length disappeared inside her easily as she pushed back against me.

Now I was fully inside my boss's ass, she underneath me with her hands firmly pushing against the wall, encouraging me to begin fucking her ass the way I'd been fucking her cunt only minutes before. Never one to disappoint a lady, I did just that, sliding back until only the head of my penis remained inside her then sliding forward to impale her again on my loving cock. Very soon I was pounding her ass as hard as I'd been doing in her pussy, my balls battering the backs of my fingers where I was now forcefully rubbing Judy's erect love button.

As much as I was loving this, I was still missing my view of Judy's tits; selfish of me, I knew, but symptomatic of my wanting everything I'd ever dreamed of about this woman all at once. After a dozen more strokes, I decided I wanted to have my cake and eat it too, as the saying goes, so on my next out-stroke, when only the head remained inside, I bent over and grasped Judy firmly round her chest and legs. Exerting every ounce of strength I possessed, I managed to lift her bodily and swivel her round my dick, still within the confines of her seductive ass, and place her on the edge of the desk, flat on her back, before lifting her legs up and wide apart, pushing them back against her and thrusting deep into her hole to complete my move.

Judy had not uttered a word during this manoeuvre, but now she looked up at me from half-closed eyes and said,

"Wow, lover. I don't know how you did that, but it felt wonderful! Now, give me that cock!"

She lowered her spread legs until the back of her calves were resting on my shoulders, knees bent and my cock filling her ass so far that my balls were in danger of being crushed between her and the desk! Now I could see all of Judy's heavenly body, from her flushed, beautiful face, down over her shaking, heaving breasts with their dusky tips, across the plateau of her slightly rounded stomach to her wet, gaping pussy. I slammed my thick shaft in and out of her stretched, abused anus, burying my thumb inside her pussy with the heel of my hand stimulating her love pearl, feeling my shaft through the thin wall separating her ass from her canal. My other hand went to her breast, squeezing it hard and rolling her nipple between finger and thumb, the other breast just reachable with my mouth, my tongue revelling in the sensation of her stiff nipple and succulent breast flesh against my oral cavity.

All this stimulation caused Judy to writhe uncontrollably beneath me, shouting and screaming her lust as she climaxed continuously now, her juices flooding out of her all over her skirt and soaking through to the desk beneath.

"Slam that big thing into me, you fucker!" she screamed at me, "fill my ass full of your spunk!"

Once more, I did as she asked, abandoning her tits and cunt to grasp her legs at the knees, pushing them up and pumping into her ass like there was no tomorrow. Judy had her hands pressed hard against the wall again, her beautiful tits stretched almost flat but still shaking up and down as the force of my thrusts shook her whole body. I had never fucked anyone so hard before, let alone in the ass, so Judy's stamina and ability to take everything I had to offer was astounding me. Very soon I felt the telltale tingling in my testicles that heralded my own orgasm, delayed so long only because of Judy's earlier expert blow job. Judy obviously felt it too, and she exhorted me to fuck her even harder, to fill her bowels full of my cream. I gave two or three last deep thrusts before a geyser of sperm erupted from my cock; no jets this time, just a continual flood of spunk filling every last crevice of Judy's bowels.

As the ejaculation emptied my sac into her, Judy too was experiencing her own stupendous orgasm, the flush of her exertions covering her face, neck and chest, her breasts a deepening shade of pink as she came and came, the nipples now a dark red colour and swollen almost beyond belief. Finally my flow slowed and trickled to completion, Judy's anal muscles milking every drop of my juice until I was completely spent. When she could feel there was no more to come, her own orgasm began to subside until she had regained a more normal rate of breathing and was able to speak.

"Tom , that was... just so fucking AMAZING!" she whispered, "the feel of you cumming in my ass was just so... horny. No-one has ever made me cum like that, never ever. You're pretty terrific, d'you know that?"

I couldn't answer her right then, I was too shocked at her words. I couldn't believe I had just fucked my boss in every hole she had, and more than that, had given her the best sexual experience of her life. I was on cloud nine for a few minutes then, as my hard-worked member softened sufficiently to slip out of Judy's tight asshole, I realised this was probably the only time I'd ever experience her superb body and skills, and I felt extremely sad both for myself, and for her. I stood up and looked at Judy spread out over the desk, her legs still wide apart and my sperm beginning to leak from her slowly closing anus. Eventually, I roused myself to say,

"I really enjoyed this, Judy, but I know we'll never do it again. I just want you to know that was the single most exciting and erotic experience of my life, and I think you're the terrific one, not me".

Judy just looked at me for a minute, saying nothing. Then she reached down between her legs and spread buttocks, scooping up a handful of my sperm and bringing it to her lips. As she licked it off, she replied,

"Tom, you've reminded me just how much fun sex can be," lick, "and how much I've missed having a proper cock in me," lick, "and what a useless bastard I'm married to," slurp. "So, if you want to that is," suuck, "I want us to do this again... only in more comfortable surroundings, if that's OK with you".

I could only nod my acquiescence to her vocalising of my secret desires. No doubt we would encounter problems along the way, and it wouldn't last - but I was going to enjoy it for as long as it did!

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This is quite wordy, as most of my stories seem to be! Nevertheless, I hope you have enjoyed it, and welcome any comments/feedback.