Pocket Money Pt. 03

Nice to just start undressing as she stood there. Undressing in a young girl's bedroom, getting naked with her. He could even imagine getting into bed with her - not that he was going to.

Nice, also, to expose himself to the girl and pleasing when she did a mock look of astonishment when his erection sprang from his pants,

Jim's eyes settled on a large picture on Jess' chest of drawers. A whole group of girls smiling at the camera. Thirty or so in colour. Beside it a similar one but of the same group rather younger in maroon uniforms.

"That's the catalogue I mentioned," said Jess.

Jim smiled. "Ah your classmates."

"Yes. See we do have larger sizes, different shapes – different colours even! Which would you like to fuck, Jim? Which would be your choice?"

It was rather nice looking down the rows of smiling schoolgirls and picking out a favourite. Perhaps it was like that at a brothel, choosing from photographs. He would not know!

"Which one Jim?" Her hand had crept under him and as he leant against the chest of drawers examining the photograph she was gently stroking his penis.

His eye paused at the image of Jess. She was certainly one of the best but, if he had to choose another, then...

"You, of course, Jess." He turned to her pulling his penis from her grasp and lifted her skirt and pushed himself up against her maroon knickers, sliding on the smooth cotton right between her legs so his knob was in just the right place had it not been protected by a thick layer of cotton. He crushed her to him, his arm around her back. She squeaked.

"I'd love to fuck you, Jess, love to have my cock up inside you but I'm not going to. I'm going to spank you some more, then I'm going to undress you and rub your boobs with oil and slide my cock between them until I make a really big mess there. That's what I've paid for and that's what I'm going to do."

He let go and was amused to see Jess looking a little flustered. He knew that was the closest she had been to intercourse, he had got his cock closer than any man had done before to her sex - had rather 'copped a free feel' and he knew she had very much felt his hardness there too. Perhaps he had even left a little damp spot on her knickers! It was a good time to sit on her bed and pull her over his knee.

He sat, and he pulled, and over she came right over his knees, his erection up against the side of her skirt. Once again, he lifted the skirt up exposing her thighs and knickers. A tug and down the knickers came. So nice to see a clenching of bottom cheeks - in anticipation of a slap no doubt. Instead he stroked, letting his finger tips slip over the smooth skin. At first that did not stop the clenching or tension but gradually the cheeks relaxed. Tempting to slip a finger between those cheeks and tickle her sensitive little bum hole. He had never been a great one for anal and certainly his ex wife had simply said 'no' when he suggested it, but there was something about young Jess' bottom cheeks that made the idea strangely attractive - pushing between them and opening her.

The cheeks looked relaxed enough for the spanking to start. "Thwack! Thwack! Thwack!"

Wonderful seeing the flesh quiver and feel Jess pull away, pushing against his bare knees and thighs. Again he stroked, relaxing her once more. Her thighs were a little parted and he slid his hand up the soft flesh and touched her sex. It was wet.

"Interesting," he said, "So you like being spanked?"

The girl giggled, "Seems I do and I do rather like that."

Jess was referring to his stroking fingers, moving around her wet sex. He had brought her off in the shower before. He was not averse to doing that again.

"It hurts, though, Mr Jones. Your hand."

Was that an invitation to spank or a request not to do it again? Jim though removed his fingers and spanked again but not before he had sniffed and sucked on his fingers. Jess could not see what he was doing - seeing him perhaps doing something he had not paid for!

Three slaps and his fingers returned to work the girl. Of course there was no let-up in his erection. He thought of touching himself - indeed thought of coming right across those bottom cheeks but he resisted. He was going to come between Jess' breasts. That was the plan and he was sticking to it.

He had her breathing a little faster now. Again, his fingers worked and again his hand came down.

"When are you going to stop spanking me?"

"When you come!"

"Oh!"

This time Jim slid his left hand under the girl. Lovely to touch her curls before curling his fingers upwards into her sex. It left his right hand free to spank - or stroke - soft buttocks. He knew what he was going to do - spank her as she came.

It did not take as long as he had expected and he did not at all think Jess was faking it. There was an extra quivering, a pushing of her sex against his fingers and a certain gasping moan. Down came his right hand. Spank, spank, spank as the girl gasped and wriggled before going completely limp. Jim's hand paused.

"I've come, I've come. Stop, stop!"

Gently he lifted Jess and set her down on the bed. Her skirt had fallen back over her thighs, but he was not having that, and lifted it right up revealing her curls. He parted her legs and looked down on her wet and swollen sex. Wonderful to just think of pushing into that and releasing. Wonderfully young, fresh and virginal. Just standing above her, looking so defenceless, and thinking - thinking with his erection looming over her. The thought of lying atop her and pushing in. He was revelling in his male desire – his controlled male desire!

Jim reached, leaning over her, and began undoing the buttons of Jess' blouse. She did nothing but look up at him. He parted the blouse and looked at her exposed tummy and white brassiere. He could see the money tucked between her breasts.

"Have you any massage oil, Jess, I want to massage your breasts?"

"Olive oil?"

He let her get up and go and fetch the oil. Strange to be in Jess' room naked and with his erection so prominent - so visible in the mirror on her wall. He looked at himself for a few moments and then stood looking out of her bedroom window across at his own house.

"Here you are."

Jess had taken her brassiere off and was naked from the waist up. A bare breasted schoolgirl in pleated skirt. A bare breasted schoolgirl with generous boobs and puffy brown areolae. Fantastic.

"Shall I or do you want to?"

He let her. Just so erotic to see Jess pouring the oil into her hands and massaging her own breasts. So good standing looking with his erection so strong. He got the best of both ideas, of course, because he took over.

"Sit on the bed, Jess."

She sat down and he stepped up to the mark. Hard penis between oily big boobs. Jim squeezed and fondled and then pushed them together, around himself, and slid happily up and down between them. Like a vagina? Similar but different. Nice to see his knob appearing and disappearing into Jess' cleavage and sliding so well.

He stepped back - almost, almost. So lovely to bring himself to the edge – but not quite.

"Nice?"

"Very nice, Jess, you have lovely boobs."

Her hands went to them and stroked. "Thanks Jim, and you have a lovely cock. Shall I make you cum?"

She leant forward and pushed her breasts around his erection and began sliding it between them. She grinned, "Nice?"

Well, yes! What man could resist a tit fuck from a young girl, half-dressed in school uniform, with really big breasts pressed all warm and oiled around his cock? It should be made compulsory twice a week!

Jim saw it happen, one moment the stretched, oiled skin of his knob simply appearing and then disappearing down between her breasts, the downwards pull actually stretching open his urethral opening each time: the next white stuff shooting from it up to catch Jess under her chin as she moved the smooth skin of her breasts, holding and stroking him. Plentiful semen. It was a good one!

Jim sat at his computer. He had really enjoyed the spanking and coming between Jess' breasts. but Jess had asked to see some photographs. Not just pleasant scenes or even of bikini clad girls but real pornography. He did not just want to find simply any old hardcore photos but thought he had better find some 'nice' ones that a girl might like. Did girls actually like pictures of copulation, fellation and cunnilingus? Did girls like seeing pictures of erections or splayed female thighs? Some things he came across were rather stronger. BDSM, water sports and more. How would she take to photos of 'facials?' He had real, but possibly rather odd, worries about corrupting her!

It took him the whole evening sitting there in his tee shirt and nothing else. A pleasant evening somewhat one handed searching and storing photographs. His cock and balls were aching from being erect too long and not coming. Eventually he let himself slip over looking at a particularly nice picture of a blond girl with an ejaculation running all the way up from her wispy pubic hair to her little breasts. The man was in the picture or at least his cock was. It had clearly done the deed.

It was quite a good collection, if you liked that sort of thing. Jim hoped Jess would be happy with the photographs.

It was a couple of days later when she came around to see him. Nice to see her in a quite short denim skirt and a nice little white top with a jacket. Pleasant to sit in his kitchen drinking coffee with her and taking the occasional glance at one shapely knee crossed over the other as they sat on stools. They talked away about all sorts of things.

"I've done you a set of pictures, Jess."

"Oh, yes, good, um, pictures of, you know?"

"Well, yes."

"How do you look at them? With your cock in hand?"

"Jess!"

"Penis, then?"

"Yes, I do tend to."

"Shall we look? What should I do?"

"I suppose you do the same sort of thing."

It had to be said the sight of a young girl reaching up into her skirt and pulling down her knickers was rather pleasing. Having Jess walking across his lounge to his computer in that short blue denim skirt knowing she was now knickerless beneath it did something for Jim. They sat side by side on chairs as Jim booted up the machine and found the folder.

The first few were of copulation. Good looking young people engaged in sex, their bodies coupled. The next was rather more graphic. A freckled redhead being taken from behind with the young man's penis almost out of her very visible opening. His buttocks were tensing as if he was about to really push home.

"I like that!" Jess turned to Jim, "Don't you?"

Jim had really liked the picture when he had found it a few days before. He had wanked quite a bit as he had looked at it, zooming in on the particularly interesting connection.

"Yes, Jess."

"Aren't you going to... let me see how much you like the photo?"

They had done things together before. Quite sexual things but, even so, getting his cock out with Jess sitting beside him felt a funny thing to be doing. He was unsurprisingly hard and knew Jess expected him to start wanking.

Jess smiled as she watched him. "He's got a nice penis hasn't he? Funny them both having red hair."

"You'd like to be the girl then?"

"Um, yes." She giggled, "And I see you like the idea too. Your hand went faster!"

Jim shrugged his shoulders, "Yeah, OK, be nice to watch. Two girls on the bed with him taking turns. I'd like being the photographer."

"And then?"

Jim was distracted by Jess' hand slipping under her skirt. Fascinating to see a young girl clearly touching herself. Doing her equivalent of what he was doing. "Another picture?"

It was the same couple but this time the boy's penis had been removed and was in the act of ejaculation across her bottom. A fine quick shutter speed shot with the stuff in the air as well as already landing on the redhead's skin.

"Jim! That's a bit... well sexy, actually. Gives me a funny tingle. Nice penis and nice to see it in action!"

Jim smiled at Jess. He was rather pleased with the favourable reaction.

"It makes me want to fondle it, Jim. I'd love to make it get all hard and stand up. Hasn't he got thick red hair! Another picture."

He had not been sure about the next photo but had put it in the album all the same. It was the same cock but taken before it got really excited. Swollen but not erect with its knob still covered but its shape visible through the foreskin. The thick red hair Jess had liked so visible. The bloke's balls dangling and low slung.

"Oh yes! Makes you want to pet it, doesn't it Jim?"

He shrugged his shoulders. He would be happy to watch Jess' petting, watch it all the way through to a conclusion. A lovely idea, seeing her stroke it like a cat – or a dog! 'There's a good boy, stand up and beg!'

Another photograph and then another. His choices had moved into oral play. First cunnilingus, and Jess had said how much she liked the thought of that, and then into blowjob territory. Not just sucking but then a really impressive shot. Such a pretty girl and such a fine photograph. Not one of those 'splattering across face' shots - facials - but a very real in the mouth ejaculation. You could see 'it' was happening because of the seepage around the sucked penis. The girl's eyes a little wide as if she had been surprised - perhaps pleasantly surprised!

Jess spent a long time just looking at it.

"I suppose it is one thing the idea: another the reality."

Jim was unsure what she was meaning, "Surely it does not worry you, not after what you've been saying and doing."

"It's, um, I don't know. I mean I did kiss your willy but actually to suck and have you come..."

"Or Luke."

"Or Luke." There was a pause, "He's going to want to do that, isn't he? As much as I suppose you do?"

Jim nodded.

The girl's hand under her skirt was moving. He could see rippling in the denim. He moved the slide show onwards. This time the photograph showed a man wanking himself into a girl's mouth. The man's hand on the penis and the spurt caught as it travelled twixt penis and mouth. The mouth was open and the stuff was landing on her pink tongue. Jim glanced at Jess imagining doing just that with her. Her eyes caught his and she teasingly licked her lip.

"What's it taste like? I suppose I'm going to have to try."

Jim nodded. "It does not need to go down your throat, Jess. That's porn not real life. Those actresses are sort of experienced at that."

"But am I right in thinking coming in my mouth would be better than just in my hand?"

Her eyes were looking at his eyes but he was looking at her mouth. She opened it a little way and Jim almost came there and then. Certainly he stopped stroking. The idea, the idea! His penis sticking out of his fly was rock hard.

"It is really nice Jess. It's not just it feels warm and wet - yes like a vagina - but there is the whole mental thing of... well visual too, of being in a girl's mouth."

"Sort of unnatural."

"I think only 'sort of.' I imagine its being going on for a really long time!"

"I should charge you, shouldn't I? Only I think I need the practice first."

"Shouldn't I charge you for lessons?"

Jess pouted.

"Tell you what, it'll be free IF you swallow."

Jess broke into a broad grin and punched Jim on the shoulder. "Jim! That's not fair. You know how keen I am to make - and not lose money."

He began rather obviously wanking again. He knew what he would be doing - if not that day then in a few days' time. And it was a very pleasing prospect.

Jim moved the slide show onwards. Some nice shots of couples out in the countryside. Fine young upstanding men in the open air and sunshine with pretty naked girls. Jim had liked the shots of the men just being with the girls or with the girls simply holding their erections.

"It'd be funny being outside naked and with you..."

"Or Luke!"

"Yeah! Yeah, outside like that."

Jim moved the show on and the couples were shown copulating (and sucking).

"Be nice, I expect, having the sun all warm on one's skin. Like the beach but more so."

And, of course, Jim had included some nice beach shots of couples at it on the sand and in the surf.

"Jim! He's, he's in her bottom!"

He had not been sure whether to include any anal photographs but he had put in just the one and, undoubtedly, the young man was inserted in the other place. The normal place was completely visible - and empty.

"I don't think I'd really like that."

"It's on your price list."

"Meant as a joke really, Jim. I mean, you wouldn't really want to do that."

"Try me!"

"You don't really fancy doing that do you?"

"Well, if I'm honest..."

The next photographs were rather more tame - only there were two men and only one woman in the shots, and then two women to one man. All rather nicely taken and of beautiful people.

Jess seemed to like the pictures of two men and one woman. Jim was watching her hand. She seemed amused at having one either end, he mentioned the term 'spit-roasting' and got a giggle.

"This is nice, Jim, looking at pictures together and..."

"Wanking?"

And that is what they did for quite a little time. It was on the second time around the set and when they were looking at the ejaculation over the girl's bottom that Jess came. It was so lovely to watch. The wide-open eyes, the increased activity under her skirt, the way her mouth dropped open and then her eyes screwed tight shut as she shuddered and rocked on her chair. So good to watch. To have the privilege of seeing a teenage girl orgasm next to him and to be able to stare - and wank.

Jess' breathing slowed and she opened her eyes and looked at Jim.

"Mmmm." Her eyes flicked to his erection. "I thought you might have - too."

"No, not yet."

"You going to?"

"Of course - if you don't mind."

"Mind! No of course not. Which picture?"

"You choose."

It was rather exciting having Jess do that. Having her choose the picture. She chose the one of the surprised looking girl with the man coming in her mouth. Jim liked that one, though there was not actually any photo in his set he did not like. He liked the thought - unsurprisingly.

"Off you go then."

It was different, different from wanking alone. He was on show rather than simply coming in a tissue or across his skin whilst staring and thinking about a picture. Jess was watching his penis intently, waiting for it to shoot. He felt it was going to be messy. He had been wanking for some little time. Further it seemed somewhat aesthetically not pleasing to cum onto a tissue. He undid his shirt and trousers and made himself more open.

"You can do it if you like."

"No, Jim, you do it."

Stroke, stroke, stroke. Up and down went his foreskin. The picture on the screen was really good. Jim thought of coming in Jess' mouth. He glanced at her. Her lips were a little open, she was staring at his moving hand. Might she really want lessons?

"Oh, Jess, I'm...!" The addition of the word 'coming' was rather superfluous.

His fingers moved the faster and Jim came, not looking at the picture on the screen, but at Jess' mouth, imagining pumping his hot male 'cream' between those lips, filling her mouth before she swallowed. Imagining his semen all around her pink tongue; maybe a little cum on her lips, perhaps left behind as he withdrew from her mouth; thinking of her tongue peeking out to lick. The reality was warm spurts falling all across his exposed stomach watched by the girl. Jim had not touched her and she had not touched him. It had been merely wanking together. Quite delightful! When he had finished ejaculating he found he had done rather well.