Molesting Ms. Cullum Ch. 03

The thought again of Gloria, asking her to pass the yellow one, as she stood there with her eyes wide at what he was doing.

Oiled and shiny, Kelvin pushed the yellow plastic at the orifice in the middle of her bottom. Just so fascinating to see it stretch to receive the rounded yellow end. In and in it went as he pushed, way past where his finger had reached. It was a lot less difficult than he had expected. His fingers had done the preparation well... and there was quite a bit of oil right there.

Ms. Cullum was panting.

"Is that OK, not hurting?"

"No, just strange. Sort of like, only the wrong place!"

"Would you like another - in the right place?" Tempting of course to put a real one in the 'right place.

"I don't know."

The idea too good not to try. Kelvin selected the red dildo, the one closest to her boyfriend's size. He brought it to bear, a little way below where the yellow dildo stuck out from her bottom. Well-oiled it too slid into Ms. Cullum alongside its companion.

"How does that feel?"

"Full, very full."

"Nice?"

"I don't know."

Slowly Kelvin slid the yellow dildo from Ms. Cullum's bottom - not to leave her less full for long. Hardly, when straightway he reached and oiled up the slightly thicker green dildo.

"Oh, no!" The twin bottom cheeks jiggled as she tried to escape the green invader: but it was already lodged. Bent in two over his knee, the young businesswoman was not in a position to resist. Kelvin slid the green plastic inwards.

Kelvin's thoughts returned to the idea of Gloria seeing her boss like that - with a dildo deep in her bottom. What would she have thought? Kelvin rather liked the idea of Gloria standing there naked but with a strap on rising from her thighs, waiting to use it as a practice penis upon Ms. Cullum. A practice before the real thing. Perhaps other colleagues, male colleagues, lining up with real penises at the ready for a 'once only' opportunity to penetrate Ms. Cullum's oiled and open bottom hole and leave that very male 'calling card.' Perhaps he, no better to watch Gloria do the task, lining the men up in order of size.

Perhaps the men taking her two at once, one in her bottom, one in her vagina. Why not pose like that for formal photographs, perhaps another man's penis in her mouth. Perhaps either side the other men standing, in penis size order, erections in the air, naked and smiling at the camera.

"I feel so stretched." Certainly, the anal ring looked pretty stretched around the green plastic, but Kelvin knew there were two more to go in. He moved both dildos in and out, imagining two penises working. His being one, of course. Whether having one going in and the other going out - an alternating cycle - was feasible he was not sure: probably the cocks working in series, pushing in and out together was the more likely. He would ponder upon that!

Could Ms. Cullum take the white dildo? There was only one way to find out. Slowly Kelvin withdrew the green dildo from her bottom. Most enjoyable just to hold it one end and pull with a light touch and watch it slide all oily from her anus. It closed as the rounded end came out, but not that tightly. Within her vagina the red dildo. If the white was successfully inserted, then it would be the turn of the red to leave one channel and enter the tighter one.

Kelvin picked up the white dildo, squirted oil and, with his hand, liberally coated it. He licked his lips. He was really enjoying what he was doing to the almost helpless Ms. Cullum. Such a fun thing to be doing - testing her bottom for size - a sort of mock technical exercise. His penis felt as hard as the plastic dildo in his hand. He was looking forward to oiling the real thing.

Was that a whimper as he touched the white dildo to Ms. Cullum's anus.

"Not another, Kelvin."

"Yes, Ms. Cullum, two more if we are to get to Joe's size. It has to be done." He pushed and to his surprise the white dildo opened the passage. A bit of resistance and then, the resistance of the sphincter no doubt overcome, it just slid three inches in.

"Eeek!"

"Does it hurt?"

"No, but... so much. I think, really, you should be doing this to Joe too, so he knows just what it's like."

Kelvin bit his lip and thought. Difficult to imagine both Miranda and Joe across his knee, probably better to have them on their hands and knees with bottoms raised. Certainly, he could do it, no more difficult pushing a dildo into Joe's bum than Miranda's: but would he at all want to? Certainly, he was enjoying what he was doing to the female half of the couple: might it be amusing to take a dildo from Miranda Cullum's bottom and slide it into Joe's? It would give him a great feeling of power. He could be all techie professional about it, oiling their two anuses and relaxing them. But what about Joe's cock and balls hanging there between his thighs. The penis might erect as he touched Joe's bottom or pushed a dildo in - a sexual reaction to Kelvin's hands and fingers. Of course, Joe would have the added stimulation of Miranda beside him and the thought that at the end of it all he would be penetrating Miranda's female anus.

What would it be like holding a plastic dildo in each hand and alternating their movement in the two rectums, pushing one into Miranda as he pulled the other out of Joe. In out, in out, very much like steam pistons working.

It might be enjoyable hearing Joe protest a dildo was too big and Kelvin saying reassuringly that Miranda had already taken it within her bottom, indeed it was nice and warm from her rectum. What a feeling of power it would be over the man to push the coloured plastic slowly, ever so slowly, into his bottom. Would his cock be extended, would it be bobbing up and down in excitement, perhaps surprised excitement at what was happening? Even better if Joe suddenly came, his cock spurting in front of him across the table or carpet - wherever he was kneeling. Unable to help himself.

"Oh dear. I'd better take over." Take over the performance of the final act. Penile penetration of Miranda. All with Joe watching, perhaps still with a dildo up his bottom, with limp penis as Kelvin's erection, stiff and bigger than his own, pushed into his girlfriend's bottom.

But Joe might be man enough to take them all, right up to the red one, and not come. Perhaps his eyes tight shut and his teeth clenches as it was pushed into his bottom. Perhaps Miranda might like to do that - perhaps with a grin on her face as she pushed the red dildo in.

And then it would be time for the real bottom fucking. A real penis in Miranda Cullum's bottom. Would Kelvin try it out first? Show Joe how it was done. The man watching as Kelvin's erection touched, pushed and then slowly disappeared into his girlfriend's bottom. Would that be the cue for his own penis to strengthen and rise at the sight, knowing he would follow on?

Of course, Miranda might want Kelvin to fuck her boyfriend as well. Get him to see what a penis felt like there before trying himself on her. Would Joe accept that? Would he be prepared to submit to that so as to enter his girlfriend's bottom? Would she be insistent, would her boyfriend be submissive as she issued instructions to her technician? Would actually her technician be prepared to do that? Kelvin imagined pulling out of Miranda's bottom, perhaps with a pop, and then moving across to the hairy bottom of her boyfriend. Not perhaps that different, albeit with hanging penis and balls. Could he do it? Slide the red dildo out and push in himself? The sexuality of it for Kelvin not in the act with the man but in the encouragement of the woman. Might she then feel or might she direct the insertion herself? That would be a lot easier to accept for Kelvin! Her hand then holding his balls and feeling around where his cock was fully embedded in her boyfriend. Might she move to fondle Joe's balls and then his penis, perhaps suck it - nice to see. Might she then offer her bottom to Joe and say he could enter where Kelvin had been moments before but only if Kelvin stayed in his bottom.

Amusing to think of Joe, moving across to his girlfriend with his own bottom embedded, make the entrance to her rectum whilst feeling a cock in his own bottom, thrusting away at Miranda whilst at the same time pulling and pushing at the other cock embedded in his bottom. Kelvin, though, even if encouraged to do all that by Miranda, would want to come in her bottom not Joe's. He could imagine pulling out - perhaps again with a 'pop' - and pushing the red dildo back into Joe. He would stand and wait, once Joe had finished and extracted himself, Kelvin would re-enter Ms. Cullum and add his ejaculation to Joe's.

Joe, though, was not there. It was just Miranda and Kelvin, she over his knee and with the white dildo sticking out of her bottom. He had not even taken his clothes off. Gently he pushed and pulled the white dildo, sliding it along in her bottom - the lovely motion of sexual intercourse albeit in the wrong place.

"How is that Miranda? Do you like that? I am sure Joe will. Are you ready for the next size - Joe's size?"

"So full, Kelvin, so stretched. Like it? I don't know."

The white dildo was well inserted. Kelvin's fingers went to the red dildo inserted in her vagina. He rotated it and then slowly withdrew it. His hand returned to her now vacated vagina. It felt wet and supple. His fingers moved, and he felt her clitoris all engorged. It was clear to the technician that Ms. Cullum's body was responding well - sexually - to his insertions. There was no need to re-oil the red dildo. Her rectum was already well oiled, and it was already well lubricated not just with oil but her sexual lubricant.

To insert the red, he first needed to extract the white. Out it slid as he pulled. This time the corrugations of Ms. Cullum's anal ring did not fully pucker and did not fully close. The careful manipulation and training had made it compliant in grasping substantial objects. It was waiting to grasp another and hold it.

"Are you ready Miranda? Imagine this is Joe I am inserting."

The idea somewhat amusing. He, the sexual technician, lifting not the red plastic dildo but Joe's flesh, all firm and ready, testing its rigidity and then applying it to the waiting anus. It was not, of course, that but the red dildo. Perhaps not having a dildo in her vagina made it easier, perhaps she was simply relaxed and accepting but, again, the resistance was not too great, the muscular ring was overcome, and Kelvin slid the dildo inwards. Ms. Cullum's fists clenched but he did not think in pain only sensation.

"Well, how is that?" His fingers moved again to Ms. Cullum's sex, gently frigging her as with his other hand he pushed and pulled at the red dildo.

"It's... fine. Yes, I've done it haven't I?"

"Yes, Miranda, you've done very well. Joe is going to be pleased. Only I think we should try one more thing."

Still in the case, the purple and black dildos. He did not plan to subject Ms. Cullum to those.

"Yes, I think you're right. A real penis - yours."

"Just to make sure, you see, I think it'll be easier. Hard but not so hard, more pliable and accommodating."

"Would you?"

"Of course. Would you like me to try and make you come first?"

The wriggling on his lap rather suggested Ms. Cullum was very 'worked up.' He very much liked the way her bottom cheeks kept clenching around the plastic dildo.

"Please, Kelvin."

He brought her to orgasm with his fingers, playing her hard, little upstanding clitoris. He doubted she had ever come like that before, bent over a man's knees. It had something of the bad great uncle about it, chastising a young girl with her knickers around her knees, perhaps not with a dildo sticking out of her bottom, but certainly with reddened cheeks from rigorous punishment and then him soothing the chastised girl, stroking her abused buttocks and the bad great uncle unable to resist delving between her legs and, perhaps, bringing her to her first orgasm by another's hand. Easy to imagine Great-uncle Jasper then saying there was something she could do for him... as well.

Kelvin bade Ms. Cullum rise, still with the dildo poking from her bottom. It made it a little awkward for her. He liked that.

"How would you like my cock up your bottom?" He did not mean how far but what position should she be in. "On all fours, holding onto the table, with pillows under you on the bed? What would Joe want?"

"The bedroom, I think, pillows."

Kelvin had rather been hoping for Miranda to adopt her earlier bent over pose but following her to the bedroom and seeing the red dildo sticking out between her cheeks rather pleased him. He got the bed ready, moving all four pillows from the top of the double bed into a pile for her to place her hips upon. Undignified? Very. Sexual? Very much so! Again, the woman, the rising executive, so exposed and vulnerable. Perhaps she would have looked even better in work clothes, a pin striped skirt up around her hips, a white blouse open and dishevelled under a neat jacket. He looked at her as he undressed and she in turn watched him. Very soon he was as naked as she, as naked as Joe would no doubt be when Ms. Cullum sprung her surprise invitation upon him to bottom fuck her. And no doubt Joe's cock would be no less extended than Kelvin's.

"Do you want to check my penis for firmness. Miranda?" No need at all, really, a visual inspection would more than have sufficed, but she moved and touched. After having been stuck inside his jeans during the dildo practice it was lovely to feel her fingers upon it.

"Mmmm, big and firm for my bottom, Kelvin, but it needs to be wet and slippery."

It was unexpected but lovely. She moved her head and took him into her mouth. Bliss! So lovely to feel the warmth and the wetness and a moving tongue. Lovely too to see her lips clasped around him. He would have to make sure she gave him a complete blow job in the not distant future - one culminating in him ejaculating in her mouth. Perhaps in the office. Did he dare?

Kelvin got up on the bed behind her, his now wet penis ready for the task. The red dildo was, of course in the way, it had come half way out, but he pushed it back in. So erotic, so exciting to know he was about to replace that with himself but... should he? Should he feel what it, the hard dildo, felt like if he was to slip into Miranda's vagina for a few strokes. Of course, he had seen double penetration videos and pictures - and, of course, he had wondered.

"I'll just get a bit wetter and slipperier." Her bottom was right up in the air, both occupied anus and unoccupied vagina so there, so ready for the male. One and a half inches of protruding dildo did not get in his way. Kelvin lined himself up by hand, not wanting to miss his aim, and pushed. A gasp from Miranda and he was in, feeling not just her wonderful warmth and wetness but the hardness of the dildo running along the top of his cock,.

"Kelvin! What are you doing? You are meant to be in my bottom. Get out of there!"

Four strokes and he pulled out. He reached and pulled the dildo. As Ms. Cullum's suddenly invaded vagina closed the dildo came out of her bottom. It made her gasp. It was time to re-enter Ms. Cullum but just above where he had been before. Not a great distance really, but a quite different place. He had felt the resistance before when pushing the plastic dildos with his fingers but now he felt it on his cock. It though was firm, as hard as it ever was with excitement; he pushed and then Miranda Cullum yielded, and Kelvin's knob was travelling up her back passage.

"Oh!"

Oh indeed! What would Gloria have said? And very much what would Joe have said? Miranda Cullum with a technician's penis right up her bum, the two of them lying upon the bed like spoons nested. Kelvin was very much nested albeit in the 'wrong hole.'

He did not hurry. Why should he hurry? He had her pinned to the bed. He did not need to worry about her coming, he had already seen to that. He had completed his technical demonstration, showing Ms. Miranda Cullum, as requested, that anal intercourse with her boyfriend was possible. Of course, with the penetration of his cock, a full penetration, he had completed his demonstration. He had inserted the real thing not just plastic. The moving of his penis, stroking it within her as her anal ring held him, was not needed and nor was ejaculation. But he did rather want to do both things.

So enjoyable to lie upon Ms. Cullum's soft body, moulded to her and with his penis inside her bottom and feeling both cheeks against his thighs. He raised his own bottom, drawing his erection somewhat out of her and then sank down again. Up in the air and then letting his weight sink his penis into her again and again.

The culmination, when it came, did not draw any protest from Ms. Cullum. Indeed, she seemed simply to have accepted the long bottom fuck after the technical test had been completed, as a necessary experience, perhaps as practice as to what Joe might do. She lay passive as her bottom was used. Kelvin had certainly not hurried. He had no other plans for the evening and it was a very pleasant way to spend the time. And, finally, he did indeed spend - he released his pent-up excitement, pumping it into her bottom as he stroked quite fast.

Kelvin lay upon her, resting and feeling his penis subside. Ms. Cullum was no doubt feeling the penis return to its resting state. A feeling of lessening fullness, a creeping feeling as it shortened, retreating towards the entrance to her rectum. And then, that was all it was, a soft, floppy penis in her bottom. Impossible to insert like that but until withdrawn, there it was, just nestling inside. Kelvin felt Ms. Cullum tighten her muscle around him.

"I wonder how long I can hold you, stop you leaving my bottom."

Kelvin pulled, his penis stretched. He really was held - imprisoned.

"You liked, then, being fucked in the bottom?"

"I don't say liked but I won't mind Joe doing that."

He tried pulling again, feeling his flaccid penis stretch. She seemed to really have him.

Ms. Cullum giggled. It was uncharacteristic of her. "Got you!"

Another pull and this time he managed it - and it did come out with a pop!

Kelvin looked down at the closing muscle. So small, it was surprising it could accommodate what it had. It was almost difficult to believe he had been fully inside her bottom.

"I hope all goes well with Joe. Do let me know if there are any problems or any adjustments need to be made." It was, perhaps, difficult to imagine what kind of 'adjustments' might need to be made, but it sounded very much the technician talking about IT equipment rather than what it really was: Kelvin taking his pleasure with the duped, and of course programmed - hypnotised actually - Ms. Miranda Cullum.