Molesting Ms. Cullum Ch. 04

The evening of sodomy at Ms. Cullum's apartment with her boyfriend Joe was, apparently, a great success. Ms. Cullum called Kelvin up to her office on the Monday and described it in considerable detail. "Did I do that all correctly?"

To Kelvin it seemed Ms. Cullum had not put a foot wrong (though feet had nothing to do with the activities). Her report of Joe's surprise and his manifest delight in being offered the chance to place his penis inside Ms. Cullum's rectum came very much over to Kelvin in the description. It certainly made him very hard in his jeans.

"The practice was helpful?"

"Absolutely. I am so grateful for your help. It was much easier than with you, what with Joe's penis being so much smaller – unfortunately. I do wish his was as big as yours."

The reality was there was not a lot of difference. The measurements had been done confirming a difference in size, but really 145mm length and 140mm circumference compared to Joe's reported 137/137mm was only a difference of 8mm in length and 3mm in circumference. The difference could even be down to measurement or operator error. They had not both been measured by the same person and at the same time. His programming, though, had given quite a different thought in her head.

"My boyfriend's cock is too small, Kelvin, I hardly feel it when it's inside me – properly, not in my bottom I mean. I wish it could be made bigger, like yours."

Her eyes were on his jeans as he stood beside her. He was not trying to hide the bulge.

"May I, just feel it?"

He nodded, and her hand touched his jeans – where the zip was – moulding what was inside. A tug, and the zip came down and her hand slipped within.

"Oh yes, so big, so strong."

"Gloria – she might... come in." The touch of the female executive's hand inside his jeans, touching his erection through the thin material of his boxer shorts and searching for the opening was very pleasing.

Ms. Cullum stood and went to the door, leaving Kelvin with his fly open.

"Gloria. Bit of an IT problem." He heard. "I'm not to be disturbed for ten minutes whilst Kelvin shows me what to do." The door closed.

Kelvin thought Ms. Cullum looked gorgeous in her chalk striped suit. A skirted one with the hem just above her knee. Knees clad in black nylon. A white blouse with buttons running the female way and a string of pearls around her neck. The perfect dress for the aspiring and confident female senior executive. A trouser suit would not have had anything like the same impact.

She smiled at him, "Well, go on, get it out. Let me see."

A surprising thing to be doing but nonetheless exciting to expose himself like that to the young female executive. He reached and pulled. Out it came almost with a 'boing' sound!

"So big!"

Miranda Cullum came around the desk to sit in her chair, her eyes not leaving Kelvin's penis for one moment.

"Doesn't it stand!" Her hands reached for his belt. He was clearly going to be fully exposed.

And he was. His jeans and boxers tugged down, and his penis revealed in all its glory with its accompanying dangling balls. One of her hands went to his shaft, the other to cup his balls. She drew up the foreskin.

"So long. Oh, I so wish Joe's..."

"We could, just possibly do something about that."

Her fingers moved a little faster at the thought. "How?"

"You can get a sort of dildo, one that fits over a penis increasing both its length and girth."

"Oh, really! You do have such a knowledge. A real expert in your field. Can you get..."

"There are different types. They are in the sex shop. We could go and choose."

"I haven't time this lunchtime but..."

"They open late."

"I could after work. Won't make it real like yours, though. Can I make it come? Would you mind? You haven't anything... someone else to use it on this afternoon?"

As it happened. He did not. It was rather unlikely Diane Meechin in the IT room would suddenly announce she had need. He doubted such things occupied much of her thoughts. Perhaps he should use his program on her?

Ms. Cullum was being effective in her wanking. Nice regular strokes. It was not just the feeling which was good but seeing her staring at what she was doing, coupled with the knowledge of just what was happening. He was being wanked in her private office and with her having every intention of bringing it to a conclusion. Would it be in her hand? She would need to move it from where she was fondling his balls!

The tongue running around her lips rather indicated Ms. Cullum had another thought in mind. She pulled the foreskin right back, squeezing the shaft to push more blood into the head to make it even fatter, even more like a plum and then she moved in upon it. Lovely! Hot, wet and all so mobile; stroking, tickling and sucking.

"Ms. Cullum, I'm going to come."

"Mmmm." A deep throaty sound he felt vibrating on his penis as he found he was unable to hold back any more. Such a lovely thing, fellation, and the more so if the man can come inside the mouth. The feeling coupled with the visual appeal of Ms. Cullum's lips around his cock as he poured his semen into her mouth.

And she did not let him go, was still toying with the so sensitive thing even as it softened, drawing the whole thing into her mouth so his balls were on her chin.

"I think the ten minutes are up."

Kelvin pulled, stretching his flaccid penis but Ms. Cullum was not letting go. It was like her bottom all over again, but instead of the rubbery ring of her anus holding him tight it was the ring of her lips. He pulled the harder, really stretching himself. She was not letting go.

A knock to the door. That did it. Kelvin came away and hurriedly bent forward his hands going to Ms. Cullum's keyboard as if he was typing. It was not a moment too soon. The door opened, and Gloria poked her head around. "Mr. James Sandman is here to see you, Miranda."

"Give me a minute. Kelvin's done what he came for. Ask James if he'd like a coffee."

The door closed, and Kelvin stood. His trousers and pants were still around his ankles. He hoped Gloria had merely seen him bent over the screen: not his dangling cock. He hurriedly pulled up his trousers.

"Thank you, Kelvin, I needed that. I'll see you tonight then. Seven-thirty in reception."

"Yeah, um, you've got a bit... on your lips... my cum."

"Oops!" She licked. "Tasty!"

Gloria did not look up when he left. A very business-like Mr. James Sandman was looking at papers on an easy chair near her. He looked up, but the tee shirt and jeans clad techie did not really register. He was not the rather lovely Ms. Miranda Cullum. James Sandman had thoughts about her. Rather private thoughts. He would very much have liked to have done what Kelvin had just done. It would have made the forthcoming meeting very satisfactory.

It was unbelievable, it felt unreal that evening, standing in a sex shop looking at mock penises and particularly at penis extenders with the so well dressed and so confident Ms. Cullum. Did the shop assistant really think he was 'with' her? It was so evident how his program had worked upon her. Ms. Cullum was clearly fascinated, indeed aroused, by the various coloured mock penises. The way she picked up and handled them was arousing in itself. Kelvin was hard in his jeans.

She chose, though he had encouraged her towards it, an extender in transparent plastic. The penis went inside the 'tube' of the extender and there was an additional stretchable 'ring' to go around the scrotum so the balls both hung free and yet the flexible ring secured the extender in place, so it could not come away. It would act as a male 'strap-on,' extending and thickening the wearer's penis to the benefit of his chosen partner. The very realistically moulded penis, albeit transparent, would do all the penetrating and rubbing. The plastic was soft and pliable to an extent, so a degree of sensation would reach the enclosed or trapped real penis but nothing like it would if free and un-encased. It would not even matter if the penis lost its rigidity or ejaculated, the transparent casing would still do 'the business' for the woman. Visually, the penis could still be seen, or rather, trapped as Kelvin saw it, within.

There was room enough for Kelvin inside the extender, but Ms. Cullum had no intention of trying it upon him. "You are so big anyway, it would squash and hurt you." It was for her boyfriend and his 'too small' penis.

It was wonderful, simply so enjoyable, to watch the scene play out. Not actually present in their bedroom but, instead, sitting in his bedsit looking at his computer and watching the whole event unfold. Ms. Cullum had left her laptop open and with the camera transmitting. He had seen and heard Ms. Cullum telling her Joe she had a 'surprise' for him when he returned to her bedroom from his shower. Wonderful seeing him come back in the room wrapped in a towel and to see his face when Ms. Cullum lifted the transparent extender from her lap and showed him what she had bought. A somewhat different surprise from when she had offered her bottom to him – not that Kelvin had seen, only heard about, that. He was certainly nonplussed.

Exciting to see her unwrap the towel exposing him and lifting his penis, as she had lifted Kelvin's own before, and slide it into the casing and pull his balls gently through the ring.

After his initial shock Joe had got well into the whole thing. No doubt pleased his girlfriend was getting more adventurous sexually, even getting a bit kinky – or quite a lot actually! Seemingly delighted with how big it made him, presenting himself to the mirror to see what he looked like with a much bigger, but transparent, erection. Kelvin very much liked the way the real pink erection showed through as he watched the bedroom scene through the laptop's silent eye. He much more he liked the way Ms. Cullum pulled her boyfriend towards her as she sat on the edge of the bed and took the transparent knob into her mouth. Very erotic to Kelvin, lovely to see her lips slide over the realistic but transparent shape, probably really good for Ms. Cullum to feel the big thing in her mouth, perhaps quite erotic for Joe to see, but it amused Kelvin to know he was not getting the sensation of a wet mouth working upon his cock. It was there, certainly, but encased – trapped - in transparent plastic. It was not as if all his flesh was divorced from immediate touch, his balls hung free and Ms. Cullum was certainly fondling those.

Kelvin liked his balls being touched, stroked and fondled by Ms. Cullum. He was sure Joe did too. It was good seeing Joe standing there, up in the air with his sheathed penis released from her mouth and she gently massaging his scrotum. Kelvin supposed it was possible to excite a man enough that way and thought how amusing it would be to see sudden white splashing within the transparency or the extender, it filling up beyond the penis and knowing Joe had come too soon and then having to fuck Ms. Cullum, because she would want it, with his extension gave him the capability despite his penis being all soft, flaccid and spent. Kelvin wanked happily away at the thought.

Joe, though, did not come. His penis remained solid within its transparent cage. Miranda settled herself back on the bed with her thighs open. It was an invitation and Joe reached and played for a while before getting up on the bed above her. It was very enjoyable for Kelvin to watch the big transparent penis lining up on Ms. Cullum and pushing in. He liked the way her eyes widened. She was clearly appreciating the added girth.

He watched the fucking, his own private porn channel with just him and the couple. And it was a long bout. Ms. Cullum was well seen to! Desensitised, Joe could keep going for a long time and if he lost enthusiasm and rigidity or simply came it would not matter to her – the fucking would go on! A change of position with Ms. Cullum on her hands and knees – which gave Kelvin a better view, both of the thing being pushed in and it moving in and out.

Kelvin wondered what it was like for Joe. Fucking away with very little sensation, the sensitive flesh of his penis removed from Ms. Cullum's wetness, yet his balls were free, swinging away as he fucked. And, every so often, she reached and fondled them.

Ms. Cullum was vocal when she came but still the fucking went on.

"Enough, enough, too sensitive!" Miranda pulled herself forward and off the penis extension, so her face disappeared into a pillow.

Kelvin leant forward towards his screen, trying to see if Joe had come. Was he still erect, had the extender denied it him much pleasure from the whole session? It was so amusing seeing his 'rival' encased in the transparent plastic, the more so to see that not only had he not come but he was not that hard either. Kelvin smiled, it gave him a strange thrill to be spoiling Joe's sexual experience. The upstanding extension was most impressive as Joe stood up: the penis within was not.

"It rather spoils it for me," Kelvin heard Joe say.

"Not for me!" Miranda Cullum turned over with a big smile, "That was so good. And it makes you so big!"

"I've lost my... can I take it off now?

"Oh no!" She reached and held one hand to Joe's balls, the other to the shaft squeezing the malleable plastic and therefore doing the same to the penis within, a squeezing and rolling motion. Perhaps a little like working dough.

It was deliberate. Miranda Cullum had pulled Joe right in front of the laptop, right in view of its camera. She was showing Kelvin how big he had made her boyfriend. It was likely she would be showing him coming too. Kelvin could see the encased penis filling out and growing as she squeezed and fondled the soft clear plastic. Undoubtedly, he was receiving considerable sensation but only his balls had skin to skin contact. It was perhaps like Ms. Cullum was wearing really thick rubber gloves as that was how Joe would be feeling it. Not the same as being touched by her hand – or lips or sex. Or as if he was wearing a very thick condom. She was being very attentive to his balls; his scrotum being so pronounced due to the restraining ring of the extender behind them, and the way they were exposed.

It was lovely to watch Ms. Cullum's hands at work, rather good to see just how slippery the transparent sleeve was fresh from her vagina, and good to see her breasts jiggling away as she worked. Kelvin wanked away as he watched. His naked hand touching his own penis, squeezing the shaft as he pushed and pulled his foreskin over the edge of his knob.

All of a sudden within the transparent sleeve there was movement, a spurting of white cum. One spurt, two spurts and it began to fill. Miranda turned to the laptop and grinned. In his bedsit a very similar spurting occurred, a free spurting from the end of Kelvin's penis up into the air.

The boyfriend was away for a whole week, indeed ten days, on business abroad. It was mentioned in passing by Ms. Cullum and, apparently, was not an unusual event. Kelvin took full advantage via his program. He had formed a desire to stay overnight with Ms. Cullum. He had never slept with a woman and wished to sleep with her and awake in the morning with his penis in her mouth before getting up. Another experience, another learning experience for the curious techie.

By the third day of her boyfriend's departure, Ms. Cullum was positively squirming from a lack of sex. It was probably not at all how she normally was. Kelvin rather thought she got more 'kick' from her work than sex, would not normally have been so desperate but his program had been at work again, playing with her mind. He was duly summoned by Gloria mid-afternoon.

"Ms. Cullum wants to see you, again."

The high-flying young executive was indeed squirming in her leather chair when he knocked at her door.

"Ah, Kelvin, a problem for you."

"What's gone wrong with your PC?" He knew very well what the real problem was. He saw the squirming and knew what his program had instructed.

"Not my PC, my sex organs. So embarrassing."

He looked puzzled.

"I'm just so wet, so aroused. I've, I'm desperate for..." Her look was imploring.

"May I?"

It was as if he was asking to use her keyboard and mouse, but it was not that at all. He bent towards the seated woman and placed his hand between her knees and then slipped it right up inside her skirt and touched her knickers. They were completely soaked, not just a bit wet but as if they were fresh from a 'hand wash' and in need of wringing out, as if they had just been in rather hot water. He curled his index finger and slid easily under the elastic and to the wet gooey flesh beneath. It really brought home the contrast between the male and female genitalia. The male hard and dry, the female soft and wet. Kelvin was hard and dry. He would very much have liked to have wetted his penis in Ms. Cullum's soaked flesh but with Gloria a mere opening door away, it was not the time.

"Have you, have you got your equipment with you?" She was licking her lips at the thought.

"My coloured dildos?" He tickled her hard clitoris with his finger.

"Yes..." her voice quavered, "the black one."

"It's too big for you, it really is."

"I know but I just want to feel it, feel it's shape." Her hand was making grasping motions. "Have it in my hand to stroke, so big, just to toy with. I wish it looked like... was shaped. I want one which looks like a cock, really looks like one. And then another to..."

"I'm sorry..." The set was back in the bedsit. The idea, though, of leaving Ms. Cullum playing with a so realistic, big, black plastic dildo as she worked, was a rather pleasing image. What would Gloria think of coming in and finding a most unusual executive toy on her boss' desk. Perhaps listening to instructions whilst Miranda Cullum's fingers stroked up and down the black plastic as if masturbating a real erection.

"Oh no, what am I to do?"

"Have you any more meetings today?"

"No."

"I think you should go straight home. In effect you are not well. A late afternoon and evening spent masturbating will help. Wouldn't it?"

Her eyes lit up, "Yes! Would you, would you come and help?"

"I'll want to fuck." He pushed two fingers into her as emphasis.

"Yes, yes, of course. I don't mind. It's only semen, after all. I'd love it if you got your cock out now and fucked me here on my desk. I could tell Gloria we are not to be disturbed. I..."

Kelvin did not think that would really be a good idea. Gloria might wonder what was going on. Too many 'do not disturb' visits might arouse suspicion. Better to enjoy Ms. Cullum at leisure at her home rather than a quickie upon her desk.

"I'll meet you in the car park in fifteen minutes." Kelvin withdrew his fingers and offered them to Ms. Cullum. How exciting to see her lips close and suck her own wetness from his fingers. He had some difficulty pulling them from her mouth.

Kelvin hoped his erection was not too obvious to Gloria as he walked past her towards the lift.

It was not Kelvin waiting in the car park this time, but Ms. Cullum. He got in beside her.

"I can't go another night without..." she was actually blushing, "a penis, a real one."

Her left hand was stroking the phallic roundness of the gear stick. She was certainly worked up.

"I have mine with me."

"So big." She started the engine. She looked at him. I'll want to use it more than once."

"I can stay the night. You can use it as much as you like."

He was a little worried Ms. Cullum might jump on him and make him come too soon once inside her house. He would have to slow her down. She might be able to multiple orgasm all evening, but he was not built the same way! He might manage three but with a gap of time to get his enthusiasm back. He did not want to come the first time too quickly, he wanted to savour the sex, enjoy the stimulation but not too much stimulation for a time.