Chapter 11: Sweet Caroline!

As I was walking towards Caroline Herschfeldt's place I thought about how mum had nearly persuaded me to stay home last night. 'Oh Justin given this afternoons experience are you sure you wouldn't you like to come to the party tonight. I think I can pretty much guarantee you a warm welcome' is what she'd said.

I remember turning to face my parents who had been frantically fucking in an attempt to speed things up so that they could finish dinner, clean up and be ready for their Saturday night sex-fest. 'I don't think so mum' I had told them 'I think we should keep my... pardon the pun... coming out party for next week. And besides, I am saving myself, remember?'

Mum had nodded and smiled in the middle of the good fucking she'd been getting. 'So what will you do tonight?' She laughed. 'Go search for more teenage sluts?'

'Actually no mum' I'd said in reply 'right at this moment I think four blowjobs has sated even my sexual thirst. No, having bowled this afternoon I think I might pay a visit to 'Shoot 'Em Up' and rack up a few frames of snooker'.

'Yes well you know where to come if you get bored too quickly' my father had said as he lifted Mary off his cock, bent her over the back of the chair and fucked her from the rear, 'you know where to... er... come, so to speak. Now fuck off and look after our dinner while I look after your mother'.

I had simply laughed and moved to the kitchen thoroughly contented with life now that I was beginning to get a little of what most men seemed to take for granted.

I couldn't believe I had come so close to staying home last night. Oh I know it would've been fun and I would have enjoyed myself at the time, but I would have felt like I was somehow cheating either Vikki or Caroline. Strange huh?

Caroline was on the doorstep when I got there. She was dressed simply in a navy blue mini skirt and a plain white blouse, but to me she couldn't have looked lovelier. Then I wondered if she would, but then thought why should she, a painter with the pick of the male models, even want to? Maybe I would be posing for her, after all she did approve of my physique, even if it wasn't perfect. But that would be all wouldn't it? After all if she wanted or needed anything else she'd have her favourites wouldn't she?

I had come to all of these conclusions as I walked into her house because I didn't want to suffer a letdown later. Besides which I didn't really fancy the idea of making a total fool of myself.

"I've got some coffee on or their's some orange juice in the fridge if you'd like," said Caroline as she led me into the kitchen looking me up and down. "Uhhmm, you look hot. Would you like to freshen up first?"

Now what did I do? She was only looking at me and I was already on edge. I had to settle down, and the bathroom with a splash of cold water seemed like a good place to start. Nodding hesitantly I allowed Caroline to lead me to the bathroom. I began to take off my sweatshirt but she would have none of it, even ordered me to hold my arms up so she could take it off herself.

"Uuummm, I should have done this yesterday, you know you really do have a good physique considering the shape you used to be in."

"B-But I'm n-not... I-I'm n-not..."

Caroline had put her hands on my shoulder just in case she upset me, and now that she had she massaged my shoulders gently yet firmly. "Justin I'm not having a cheap shot. It's just my way of telling you what a great job you've done with your body in such a comparatively short time. Do you even know how much strength of character and willpower it takes to accomplish what you have? You've got some great muscle tone now, an upper body that's coming along quite nicely, and your handsome, take that from someone who knows. Does it embarrass you if I tell you that?"

She'd said something similar to me yesterday, did that mean that... ? I didn't know so I simply nodded my head ever so slightly. It was still difficult for me to accept, after all the knock backs at school and the three recent Julie Morris incidents, that people, Kim Carver and Joanna Walsh included, could say things like that and really mean them. But then Caroline was exuding an aura of sexuality that seemed to flow from every pore of her body.

"Everybody needs someone sometime to tell them things like that. It gives people confidence, makes them feel better." Caroline threw my shirt to the floor, moved forward and was about to reach for my shorts when I stopped her. "I'm sorry Justin," said Caroline in a breathless voice that gave just a hint of what could be just around the corner, "maybe I'm rushing things a little, I thought that maybe... well anyway you freshen up, I'll take your sweatshirt and put it in the wash, then I'll check the coffee, it should be ready."

Well now I knew, or at least I thought I did, that things were going to be okay, and that this was going to be the exciting afternoon that her lascivious behaviour indicated. Maybe I would even lose my dreaded virginity that seemed to hang around my neck like a lead weight. Yes even I know that blowjobs and pussy licking doesn't count, that it's actually having your cock in a cunt - that word I just love it - that matters!

I used the slightly perfumed soap to wash myself, then rinsed off as I thought about this remarkable woman. It was obvious what was happening; at least it seemed obvious now. Caroline Herschfeldt clearly had something planned for me. The question was did I want to? No that wasn't really a question, of course I did. The real question was could I change the feelings that were second nature until two days ago, could she maybe. And what about Vikki, where did she fit into all this?

Back in the kitchen I sat where I had the previous day and watched as Caroline turned her chair in my direction, watched as she crossed those marvellous legs of hers just as carelessly as she had yesterday. This time there was no doubt, she was wearing panties, black ones.

She leant forward, rested her left elbow on the table and took a long sip of her coffee. It should have been an innocent act but Caroline Herschfeldt turned it into something sensual. "Do you have any idea who I am or what I do?"

I nodded and over a period of a couple of minutes stammered out an answer. "My parents have one of your paintings in their bedroom. They were always in full agreement of your fight for freedom of expression and against censorship. So they think what's happening now is just wonderful."

Caroline, who had waited patiently for me to finish my stuttering response, smiled.

The smile was one of such unrestrained delight that I couldn't help but smile too.

"Oh really," said Caroline finally. "Well you've no idea how refreshing it is to know of someone in this town who actually possesses one of my paintings." She looked at me with interest. "I don't suppose you'd tell me which painting it is?"

"It's called 'The Best of all Indoor Sports' Mrs. Herschfeldt, it's the one with..."

"Mrs. Herschfeldt is my mother, please call me Caroline."

Unable to speak I simply nodded in agreement and waited for her to continue.

"I remember that picture, it gave me a lot of pleasure painting it." She put down her coffee cup, placed both elbows on the table, clasped both hands together and thought for a long moment as she rested her chin on both outstretched thumbs and looked directly into my eyes. "Can I ask you a question Justin? It's got nothing to do with your parents painting, but there's something I have to know."

I nodded my head a little warily.

"How come your parents are as enlightened as you say, have one of my pictures and yet you're so shy, so scared of any physical contact with women? I mean surely your parents would've, under those circumstances, been fairly liberal with your upbringing?"

What else could I do but shrug my shoulders. I couldn't answer because I didn't know. The only thing I really knew was that I craved physical contact with women outside of my mother, the incident with Kim and Joanna having been put in its proper place in the back of my mind.

More than anything in the world I had this fierce desire to behold the female form, to have an open relationship of any sort with a girl my own age. That was why Vikki Thompson was so important and why this woman scared me so much.

She moved her chair closer until our knees were practically touching. "Would you like to change, or more to the point do you think that you could?"

I looked into Caroline's eyes and decided that if she was going to help then why not give it a try? However not wanting to appear too eager I shrugged my shoulders and allowed her to continue.

"Since these new censorship laws, and since all of these city ordinances as part of that Sexual Freedom Charter that have been enacted by a Liberal Government that has finally lived up to its name, I've been asked to paint some pictures for a showing here at the town hall, and I also have a contract to supply a second collection for an upmarket massage parlour in Sydney. Of course it goes without saying that they are going to be highly erotic, people used to call them pornographic, paintings. Naturally I'll need people with particular appeal for different types of paintings. Now it was your physique and those wonderful muscles you've begun to develop that first attracted me to you. You see I reckon that you are very strong, strong enough to help with an especially large canvas that I have in mind. Do you think you'd be able to pose for me?"

Now it was time to think about what was being asked of me, could there be another model involved? Of course there had to be otherwise why would she talk about my strength being important. Would I have to... could I if it was demanded of me, perform on request?

"I don't know Mrs... er... Caroline. I've never taken my clothes off in front of anybody since school."

Okay a little white lie maybe, but it was the truth until the recent encounters with my parents and that extraordinary encounter with Joanna Walsh and Kim Carver.

"Even in the boys showers I'm a little shy, unable to join in their childish games and show off the way they like to do. I guess they treated me like some kind of freak, which is often why I preferred showering at home if I couldn't get in and out first," I continued hardly even stammering any more. "It's just the way I was, or still am I guess. It's nobody's fault really, my parents were and still are very liberal in my upbringing. Not that it seemed to make any difference to the way girls treated me. I guess a lot of girls are like boys in that they don't seem to like boys who are fat and not what they would call 'spunky looking'. I mean when boys want to go out with girls looks come first and personality usually runs a distant second.

"Anyway, after a while I sort of gave up. I know my parents are happy that I'm with you, and they are more than willing to support whatever you decide to do. In fact they'd like an option on any painting or at least a print if it's not possible to buy the original," I said needing to talk as a way of taking my mind off her breasts, which were pretty much on display as she leaned forward gripping my shoulders. "But I suppose that rather depends on your showing and of course whether you manage to help me overcome my natural shyness?"

Caroline sat back in her chair, folded her arms underneath her chest and looked at me. "You certainly seem to have overcome your problems talking anyway, and that's a start. Now all we need to worry about your is shyness when it comes to your body and any physical contact in public." She stood up, walked behind me and began to massage my shoulders. "The first thing you need to know is that Bill doesn't worry about what I get up to when he's away as long as no modelling takes place while he's here. He knows their has to be a certain amount of sexual contact and he won't stand in my way on that as long as I don't worry about his little affairs on his interstate trips."

Well that certainly gave me something to think about, hell, I thought, maybe she does take some of her models to bed; maybe my parents were right. Then I saw her look at the expression on my face and realised that she'd been reading my mind.

"Do I take my models to bed and does he mind? The answer is yes to the first question and no to the second." She moved her fingers down over my ribs and began to massage my stomach, which was still a little fleshy, as she pressed her breasts into my shoulders. "Now you have to answer my question. Are you ready to take your clothes off?"

Maybe I was, maybe I wasn't, but I wanted to see her reaction to a negative response, so I shook my head.

She wasn't phased in the least she simply continued her questions. "Would you like me to take mine off, would you like to see me in the nude? Be honest Justin please."

Did I want to see her naked? I wanted that more than anything else in the world, but I didn't want to seem too eager so I took a several seconds to respond.

While she waited Caroline did what I had been half afraid of and moved her hands from my stomach and onto my semi-erect penis, which blossomed, into a full erection in a matter of seconds.

Now my stammering, which had all but disappeared, returned with a vengeance. "Yes I would," I finally managed as she took a firm grip of my cock. "I've seen plenty of pictures, videos and stuff as you would have probably guessed, but I've never seen the r-real thing close up one-on-one. I mean I went to the ten-pin bowl yesterday where the girls and women, and even some younger girls, were all but nude and that was an experience but I haven't been with a naked girl or even a naked woman where it's just the two of us." Another little white lie of course, how could I tell her about my mother? "That is with the exception of my mother, and that only through the almost see-through nighties she wears." My stammering and stuttering was so bad that that little speech which should have taken maybe thirty seconds took what was probably a conservative two and a half minutes.

"That's quite a speech for you Justin my sweet, and quite a piece of equipment if my fingers don't deceive me." She grinned as she maintained her grip. "Does my doing this embarrass you at all Justin? No don't answer that, your rather nervous stammering has already supplied the answer. And I truly am sorry you sweet boy, that really was the last thing I wanted to do."

I answered her anyway. "It... it d-does a l-little I-I-I'm afraid. I'm afraid I'm just not used to this sort of familiar contact."

I was keeping up my little white lie of course. I guess I was getting used to it, but somehow having my penis handled by a classy lady like Caroline Herschfeldt made it seem like the first time. And I certainly didn't want to tell her about the episode with Joanna Walsh and Kim Carver, something told me to keep that little piece of information to myself and maintain an air of total innocence.

Caroline rubbed my penis between her thumb and forefinger until it was practically bursting from my pants and she kept on rubbing until I pushed her fingers away.

"Well I'm sure you'll get used to it in time." She smiled and moved around to the front. It looked as though she was ready to take command, which she did. "All right, I will take my clothes off for you but not until you let me take your clothes off first." She stopped smiling, stood to attention with hands on hips and barked out an order. "NOW STAND UP!"

What else could I do? She was so dominant and demanding, I was meek, shy and submissive, almost like putty in her hands. And besides she wanted to see me naked, I wanted to see her naked, it seemed to be the perfect compromise. And who knew, maybe it would lead to... Well, a man can hope.

I did as ordered and watched as she took my runners and socks off and moved her hands to the waistband of my shorts. Now was the time if I was going to stop her, my heart was pounding and my penis was so hard it hurt. Then suddenly the shorts and briefs were gone and my hard-on was spearing the air like a telescopic aerial.

"Simply gorgeous. Oh Justin that is simply a work of art." Caroline Herschfeldt who was kneeling down helping me step out of my clothes looked suitably impressed. "I don't understand why you would want to hide a cock so beautiful." She gripped it in one hand and weighed my balls in the other. "Uuummm delectable! I think that if you agree to model for me young man that you will find the experience very enjoyable and, I should think, extremely enlightening. In fact I can pretty much guarantee you'll be in great demand."

That's not what I was thinking of at that moment. I was concentrating more on looking down the neck of her white blouse, trying to see if she was wearing a bra, concentrating on her wondrous thighs as the navy-blue mini skirt was stretched to its limits.

"Do you like them?"

I looked into her face as she began to stroke my erection with her right hand.

"My breasts, do you like them? What about my legs?" She gripped the hem of the skirt in her left hand and pulled it up and back against her waist as she gave me a full view of her panty clad hips. "Talk about my body Justin, describe how you feel about wanting to see it, tell me what it's like, what you'd like to do to it."

Just standing there naked with Caroline's hand on my cock was bringing me near to a climax and she wasn't even rubbing it. If I didn't do something soon I'd shoot my semen all over her, and while I didn't figure it would greatly upset her it would sure embarrass the hell out of me. So my relief was palpable when she stood up and moved back until she was standing beside her chair.

"Don't worry about that." She pointed to my cock as she sat down. "We'll get back to it later. Now start talking about me Justin. You have to learn, learn to be relaxed about sex, your body, your partners body, in fact the whole box and dice. Especially if your going to spend a lot of time here. Now being naked in front of me is a good start. Remember I paint highly erotic pictures that reek of eroticism, of lust, of good old-fashioned sex. And part of that whole scene is the earthy language, the risqué talk, and the smut that makes it all so much fun. That's why this sudden world-wide relaxation of censorship and the Sexual Freedom Charter and all of its accompanying by-laws is so sensational."

Now this really was awkward, me naked and Caroline dressed. I mean it was all right for her but it wasn't easy for me to talk directly to a lady about her body? And especially a lady like Caroline who was just dripping with culture and class. "I suppose I like your legs and er..." I said finally putting my hands to my chest unable to say the words.

"Breasts Justin, breasts. Or you can call them tits or boobs if you like." She put her hands to the buttons of her blouse and began to undo them, and once undone she slipped the garment off and immediately reached behind her for the catches of her bra.

I was mesmerised, unable to take my eyes off them as she removed the bra and dropped it on top the discarded blouse. They were perfectly round; the pink areola was the size of a fifty-cent piece and an erect nipple crowned each one. "Ooh they... they're b-b-beautiful." I was close enough to touch them, but I didn't - not that I didn't want to - instead I kept my arms at a safe distance.

"Not good enough Justin. I'm not taking anything else off until you tell me what you think of my breasts."

I took a close look at them, knew what I wanted to say but the question was how to put it into words? Then I simply decided to put in the words she expected me to use. After all she was asking me to. Wasn't she? "I like your tits Caroline. They're so firm and round, and I just love those perky nipples that just beg to be... to be..." Why couldn't I say it when I knew it was what she wanted to hear?

"Come on Justin, remember what I said."

I took a deep breath and let it out very slowly. "They make me want to f-f-fondle them." Her smile at those words almost immediately relaxed me. "They make me want to take the nipples in my mouth and suck them, maybe even bite them a little as I squeeze the tender flesh of each tit between my fingers. I feel as if I want to run my tongue over every inch of each one and circle the nipples with the very tip of my tongue. You know I kind of wonder what it would be like give you a... give you a titty-fuck. You know lay you down, grab your..."

"Yes I get the picture," she licked her lips, "and I like it." Caroline smiled as she stood hands on hips. "That means you must really must want to see my little pussy. Come on Justin!" She lifted her skirt up and rubbed herself through her panties. "I can see from your hard-on and all that pre-cum dripping from your cock just how much you want to but I need you to tell me."

"It's all I've ever dreamed of, pictures and videos aren't the same thing as seeing it in the flesh, and ever since I first laid eyes on you I've wanted to see you naked, wanted to see your... er..." God I couldn't say the words, not pussy, and especially not cunt, "... vagina." I finally managed.

I stopped then hoping that would be enough, I should have known better.

"Oh come now, Justin you can do better than that. My mother, my grandmother and my auntie have vaginas. If you can describe my breasts that way you can do the same with my vagina." She allowed her skirt to fall back in place and sat down with her knees primly together and her arms folded over her breasts. "I'm not even going to let you look at my breasts."

I thought about it for a moment. She was right, she knew she was right. More importantly I knew she was right. So I took a deep breath and went ahead. "Do you know why want to know why I want to see your cunt Caroline? If I can't see it, I can't touch it. And if I can't do that and run my finger between the lips of your little slit I can't turn you on, and if I can't turn you on and get you all wet and horny then you won't want me to fuck you. So Caroline would you please, please, please do us both a favour by undressing and spreading those pretty little legs of yours!"

I was red in the face and embarrassed by using that sort of language, but I was satisfied that that was what Caroline wanted to hear and I sat back in my seat waiting for the woman's reaction.

"Better Justin, better. All right I'll take them off, but first you'll have to answer a question. Have you ever or do you masturbate, and if so what sort of things make you want to play with yourself? For instance if I posed naked, would you masturbate over me if I asked you too? Would you feel comfortable spraying a load of cum all over my naked body?"

I was staggered. First my mother saw me wanking, then there was the blowjobs and then she had me spray my semen all over her. Now Caroline was talking about doing the same thing. My first reaction was to shake my head. "N-n-no I've..." But then the idea of denying it seemed too ridiculous for words so I nodded my head very slightly. "All right C-C-Caroline you win, sometimes I can't help it when I'm watching a movie or looking at a dirty magazine. I even do it reading erotic novels and while I'm dreaming. Wet dreams, isn't that a laugh? As to whether I'd do it in front of you, or cover you in cum while you were posing for me, I guess only time will tell."

Caroline got out of the chair and reached for the side of her skirt. "And you feel slightly ashamed because you've been taught that real men don't do that, right!" She allowed the skirt to drop to the floor and reached for both sides of her black panties as I nodded my head a little more convincingly this time. "What if I told you that one survey said that sixty eight percent of men did it at one time or another, or that another group of so called experts said that all men did it at some point in their lives, would that make a difference?" Her hands were still on the waistband of her panties as she watched me shake my head this time. She shook hers in response and I had the frustration of seeing her take her hands away from the waistband of her panties. "What about if I said that I masturbated and so, as far as I know, do the rest of my family, all of them. Parents, brothers and sisters." She walked over, stood directly in front of me and began to move her hips gently from side to side; the slight movement caused her breasts to sway just a little and like a chain reaction made my already huge penis grow even more.

Now I was more than a little bemused, nobody admitted that they played with themselves; it was an unwritten law, something you just never owned up to. But this woman... this woman, like my mother, was turning all my ideals upside down and inside out. I wondered how long this had been going on. First had come the astonishing behaviour of my parents, that extraordinary Joanna Walsh, and now here was Caroline Herschfeldt taking my sexual world and shaking the life out of it (or maybe that should be shaking the life into it!). And tonight I was going out with Vikki Thompson, surely the same thing couldn't... ? No don't be silly, I thought to myself still unable to believe that these things could happen to me that would be too much to ask for.

Caroline sat back down still dressed in her panties. "You know Justin all of my life I've been comfortable with my body and fascinated by other peoples, male or female. I've been curious about the erotic pleasures to be had. Sometimes, given the right setting and mood just looking at another naked male or female or seeing a couple making love can be a sensual experience or a real turn-on. Even knowing that someone is mentally undressing me, like you were Justin can be stimulating especially if I've been teasing him, or even her, a little. I don't preach sexual attitudes, I don't dictate the way people should behave and I don't expect them to dictate to me. My husband and I remain a happy couple because we know each other's desires and were honest enough to tell each other from the beginning. Honest enough to admit that we desired other people sexually. Honest enough to admit that sex was fun, and that love came from the heart not Bill's cock or my pussy."

God where had I heard that before? From my parents that's where, and now from Caroline; would I get the same thoughts from Vikki? I certainly hoped so, I looked down at my erection, at the foreskin that circled the knob halfway down and pulled it the rest of the way off the head.

Caroline looked at my erection, and at her own panties before continuing. "Just because I'm standing here almost naked and turning you on, and your naked and doing the same for me means only that we'll have a good time for as long as these feelings lasts." She grabbed my cock again - a dangerous thing to do under the circumstances - and gave it a couple of friendly little tugs. "I could do that and make you climax, or I could have passionate sex with you and say I love you while your cock is deep in my cunt and one or both of us climaxed, but all it would mean was that I loved you while you were fucking me!" She gave my penis another couple of tugs. "Do you know how many of these and how many pussies I've painted over the years?"

I shook my head.

"Neither do I and it doesn't matter, nor do the erotic pictures or the desire to take a model to bed, because at the end of the day I'll still love Bill and he'll still be my husband. And just in case you're wondering, yes Bill still loves me despite his passionate little flings on those interstate trips."

I was just beginning to get some idea of what I was letting myself in for and starting to relish the prospect. I looked at her legs, at the wisp of panty that hid her cunt - there was that word popping into my mind again - from view. Her legs were so long, so slender, so beautiful and I wanted desperately to feel them, touch them, and enjoy the thrill of having them wrapped around me.

Caroline saw me looking and smiled. "Start from my feet and work your way up, when you reach my panties you may take them off."

I knelt down so that both knees were touching the carpet, and my erection was sticking out in a slightly upward direction as I touched each leg above her ankle and slowly moved upwards. "They feel so silky smooth, and when I touch them with the tips of my fingers I can feel a little electricity." My fingers quickly went to the softer flesh of her thighs. "There's no feeling like it, knowing that I'm getting ever closer to... to..." I looked up at Caroline. "And when my hands stop shaking and I get closer to... closer to your..." Even though I'd said it before Caroline had to help me out, again.

"Come on Justin! You said it before you can say it again. If you can't say pussy, or cunt, or even slit or twat at least say vagina if you can't use the vulgar but far more exciting terms. Just don't use that awful word quim; it makes a woman's sex sound like piece of fish. Really it doesn't matter what you call it as long as the word pleases you and doesn't offend your partner." She thought for a second and smiled. "Or partners!" She grabbed my hands and pushed them up near the crotch of her panties. "If you stick a finger just under the leg band you'll feel a little pubic hair. Does that get you a little excited?"