Sketchbook

Anastacia's hand began to move between her legs, bangles rattling, her voice now a raw rasp. Her language had changed too and her words were now those of a gutter-whore. "Wank for me Josh. Come for me. Look into my eyes when you shoot your fucking load. Burn the image of my face into your mind for eternity as you wank over me. There is nothing but me - no-one else but me. This is not a picture, Josh. This is the real me telling you to fucking come hard. I want to see you spurt and hear you moan. I want you to scream my name when you shoot. Fucking come, Josh. I'm coming - come on, fucking come with me!"

As she began to speak, I had wrapped the panties around my erection and gone at it furiously. Her gutter talk was amazing - spurring me on, making me stroke harder as the wet fabric teased me. "Come on, fuck your hand like you did Trix's. Shoot, you bastard - let me see you... oh fuck!"

She came panting, her fingers dripping juices, her eyes wide. I felt myself about to unload and realised I would be ejaculating onto the bed covers. I tried to step back but she pulled me closer. "Come - fucking do it!" She sounded almost desperate.

I locked my eyes onto hers as I came. I screamed in ecstasy as I spurted a thick white jet onto her bed covers. "Oh Anastacia, oh Angelfire - fuck yeah..." I trailed off into incoherent sounds and flopped back into the chair, sweat pouring from me, elated I had done as she had demanded.

She lay back purring. "Good start. Keep the panties. I think we shall reconvene at eight in the morning. I fancy a bit of fun before work and I'm in Brighton for the weekend, so an early session is in order. I wonder what the sketchbook will have in store for us then?" She rolled over and opened her bedside cabinet, pulling out a few pieces of wicked looking plastic. She glanced over her shoulder at me. "Show's over. Go."

Shocked at my summary dismissal, I rose and tucked myself back into my shorts. Resisting the urge to speak, I merely walked from the room and returned home with my new prize. I had been doing some research on the internet for when my folks were away and knew exactly what I needed to do now. I picked up a large watermelon from the kitchen. There was already a hole in the top and I had scooped out as many seeds as possible. I had also bored a little hole in the side to release the vacuum as instructed on the website. I dug in my bedside drawer and found my packet of 24 condoms. There were still eighteen in there and none had been used in anger. They mocked my inability to have any meaningful relationship with a female member of the race. I used my seventh one and picked a random older woman movie out on my tablet. I set the melon on a pile of towels on the bed, held Anastacia's panties to my mouth and nose and sank into the cool, flesh of the fruit. Half an hour after coming in front of her, I was calling her name again as I slammed into my new inanimate lover. I lasted an hour the second time and again felt a frisson of guilt as I awoke at two in the morning still inside it. Then elation swept over me - only six hours until my second encounter with Anastacia.

Chapter 9: Halfway to Paradise

This time, the sketch was a two-parter. The first was of a boy lying on his back on a bed, naked. He seemed to be secured to the headboard by his wrists. The second showed a fully clothed woman straddling his legs, masses of dark hair falling around her. She had his erection in her hand.

Oh my God, was she going to do it for me? I walked into the room expecting her to be there, but it was empty other than a sheet of paper on the bed. There were five words on it. 'Strip. Lie. Use the handcuffs.'

I looked at the headboard and sure enough, two sets of handcuffs were dangling from the metal rail. A shiver went through me as I removed my clothes and lay down. The first cuff was easy enough, but the second took a little longer. I lay there helpless, heart pounding, wondering what was going to enfold. Minutes seemed to turn into hours and I had a slight panic attack that maybe she was just going to leave me there. After what felt like an eternity but was really only five minutes, the door to her ensuite bathroom opened and she came out smiling. She was in her usual voluminous skirt, but this time head a leather waistcoat over her habitual white embroidered blouse. I made to say something but she merely shook her head and put her finger to her lips.

From the dresser, she picked up a plastic bottle which she dropped on the bed beside me. She leaned over and I thought she was going to go down on me, but she took me in her left hand and opened her mouth wide. I could feel her hot breath on the head of my erection and I began to tremble in anticipation. How many times had I wondered what it would feel like? To see it disappear between willing lips. To feel the tongue and teeth work on it gently. To feel that explosion as she sucked and the cum dribbled from her mouth.

She held me like that for a long minute before pursing her lips and blowing softly down the shaft. She held her tongue a fraction of an inch from my frenulum and I strained to touch her, but she merely smiled and pulled away. "Maybe next week? We'll see..."

I groaned in disappointment and she laughed. "Oh the impatience of youth!" Then she picked up the bottle, slathered her hands in sticky lubricant, took up the position I had seen in the sketchbook and proceeded to tease the shit out of me for fifteen minutes until I was literally begging her for release. I had never been so turned on and the handcuffs were amazing -- I was literally under her control and she did everything to keep taking me to the brink and then bring me back. The feel of the oil was sensational and her deft fingers worked and squeezed and stroked, running her palms over the head, then encircling the shaft with her fingers. She tickled with her fingernails, rubbed me between her palms and tugged gently on my balls as Trix had done in the gallery.

It was when she slipped an oily finger into my anus that I couldn't take any more. I cried out as I spurted three, four inches in the air and watched it splatter back down on my belly and over her hand. I was pulling at the handcuffs, shaking like a leaf as the huge orgasm washed over me. There was a second smaller spurt and smiling, she rubbed my now softening erection around my belly, coating it with my cum.

Looking at her hand, she shook her head. "Oh, naughty, dirty boy!" She wiped the excesses off on my chest and disappeared into the bathroom. I was still panting when she emerged. She made for the bedroom door. "Have a nice weekend Josh, see you Monday!" She stopped, grinning back at me. "Sorry -- two things I forgot."

She walked back over to me, her hand going beneath her skirt. When it emerged, her forefinger was wet at the tip. She held it to my mouth and I sucked on it, licking every drop of her juices from it. "Sneak preview of Monday!"

She unclipped the handcuffs and I winced as circulation returned. I had been so 'in the zone' I hadn't noticed until then. She kissed me on the forehead. "One-word review?"

I thought for a moment. "Wow!"

She shrugged. "Predictable, but it will do. Right young man, clean up, work hard and I will see you on Monday evening for round three. At one o'clock this lunchtime I would like you to come back up here, open my sketchbook to a picture of Trix fucking. When you masturbate, think of me fucking her with a large strap-on in the flat over the gallery. It's our little Friday thing -- just to whet our appetites for the weekend, you understand. Then we head down to Brighton for a little get-together at Izzy's old apartment with Josie and a few good friends. If you want to understand better what that means, peruse sketches sixty-five up to around one-hundred and that should give you an idea."

And with that she was gone leaving me on her bed at eight forty-five in the morning, my chest and belly covered in my own cum.

I worked my arse off all morning and just before one o'clock, I transferred my big, round green lover to Anastacia's bedroom and put down layers of towels. I was just about to slip inside it and think of Anastacia and Trix getting it on when I heard my message chime on my phone.

Trix and I just about to start, but fucking hell boy, get that bloody melon off my bed. There's a Fleshlight in the beside cabinet. Don't forget the lube. Trix says 'hi'. She also says, 'come on Angel, fuck me' so bye-bye.

I should have known she'd be watching. I fished out what I thought was the Fleshlight and examined it. I texted back, Thx looks like fun. Lucky Angel, lucky Trix. Have fun!

I didn't know how realistic the Fleshlight was, but once I had Googled some instructions it was bloody sensational. I smashed up the melon and used it for compost in the garden.

It was a long and frustrating weekend. The weather, which had been great all summer suddenly broke and our cricket games were cancelled as thunder and lightning struck the area and the rain teemed down. Of course, the Devil found work for idle hands and as I seemed to have been given carte blanche to do as I pleased at Anastacia's, I explored her toy collection and even though most were designed for females, I got some very pleasant results. Intrigued as to how amazing her finger had felt inside my anus, I lubed up her smallest butt-plug and tried that. With that and one of her vibrators whirring away just beneath my balls, I came so hard that I thought the Fleshlight was going to shoot off across the room.

Monday was equally a chore with a wet garden to contend with, but I got through it and just before I was about to finish, I heard a tapping on the conservatory window behind me. I turned and she was standing there naked, legs apart, her hair cascading down as usual. She held up all five fingers on one hand and three on the other and pointed upstairs. I swallowed hard and nodded. No way I'd be late.

The sketchbook was unequivocal that night. Anastacia's mouth was wrapped around an erect penis and her lover's face was clamped between her legs. She licked and sucked at me for a long time before I got to taste her, allowing me time to take in and relish my first blowjob. It was utterly exquisite and to see her go down on me was beyond my wildest dreams. Her lips and tongue were so soft and gentle and her teeth nibbled and teased.

I fell in love with the scent of a female at my first touch. She guided me and showed me just where to lick, suck and nibble. She loved having gentle breaths exhaled onto her and she showed me just where to put my fingers, how to press on her g-spot and tease her clitoris. Once again, her language as she came was so at odds with her normal demeanour. I was exhorted to 'fucking suck that cunt,' over and over as she squirmed beneath me and I felt her flood into my mouth. I prayed she would allow me to come in her mouth or on her face but I had to make do with her incredible breasts. I didn't spurt this time but seeing my cum coating her huge tits was such a turn on, especially when she let some drip from her fingers into her open mouth.

She got up and went into the bathroom to clean up and I hoped she wasn't going to make me go home as she had done previously and was delighted when she slid back onto the bed and cuddled me in. "Three down, four to go. Enjoy that?"

I licked at one of her fat nipples and felt her stiffen. Her voice was cold? "Did I say you could do that?"

I pulled away, mortified. "Sorry... I..."

She laughed. "I didn't say stop either, did I?" She pulled me back onto her and I suckled like a baby, nibbling and licking until she moved so I could even up the score on her left breast. As I put an arm around her, I felt thick ridges of scar tissue on her back. I ran my fingers along them as I sucked.

She turned away and held her hair up. I now saw four long, raking diagonal lines, partly hidden by a beautiful tattoo that covered most of her back. I had never seen either before thanks to the mass of hair that usually covered it. They were deep and obviously very old and must have been agony when they were inflicted upon her.

My voice was a whisper. "What happened?"

She turned back to me and shuddered. "Nice, eh? The story I told you the other day - their way of ensuring compliance along with the drugs. Five lashes with a full-on bullwhip. Only four scars, but one is deeper where the fucking thing hit me twice. I thought I was being torn apart. Once you have tasted the lash like that, sodomy, bukkake and triple penetration are child's play and there is no way you are going to give them a reason to use it on you again."

I was almost speechless. "Is that really why you do it? Because of what happened to you back then?"

She nodded. "Yeah. After it all, I was celibate for five years in my late teens, early twenties. Then I got clean, got counselling and started making up for lost time. When I was thirty, I painted myself for the first time. And for the first time in years I didn't hate myself. Around that time I was aware that a younger girl was becoming infatuated with me as I had been years before. I was angry with her and lashed out. I hurt her deeply and pushed her away. After a few months I realised how much damage I had done to her. I sought her out and we became lovers. We are still friends. She was the first of many. I seem to specialise in lost souls."

I looked at her. "Is that how you see me?"

"Honestly Josh? Yes. There seems a void in your life. I can offer you this sex, this breakthrough if you like, but I am beginning to think that something will be missing for you."

I was silent for a long time. "I just want a girlfriend. I've put people like you, Izzy, Josie on a pedestal and fantasised over them for so long, I'm not sure I can have a normal relationship."

She stroked my hair. "This debauched life we lead isn't for everyone. Most people would run a mile if they saw a fraction of what we do. I'm forty-seven years old and I've done things most people couldn't do in a dozen lifetimes."

I did a double take. "Forty-seven? The Courier article -- it said you were..."

She let out a throaty little laugh. "Yeah, yeah, never believe what the papers say, huh? I just knock off my five lost years when I need to and I'm forty-two again!" She looked down at me. "Are you ok being in bed with a forty-seven-year-old?"

Emboldened by our talk, I leaned up and kissed her on the lips. "I don't see age; I just see sheer beauty."

She returned my kiss more passionately. "Thank you, Josh. I hope you do find a girlfriend soon. She will be a lucky girl."

There was something I had to know. "Anastacia -- those pictures -- the ones you said were of the parties at Izzy's. Are they real?"

She nodded. "Yep, all either done from photos or composites from memory. Why?"

I was about to say it was nothing, but I needed to know for sure. "There's a girl in some of them. I'm sure I know her. She's in the fantasy ones with Izzy and some of the party ones."

"Bethany Hamilton?"

It was my turn to nod.

"Yes, she was before my time -- before Trix introduced me to Izzy and Josie and started going to their little shindigs. It seems she was quite a little force of nature. She, Izzy and Josie had a thing going for a while and Trix still eulogises about a single night they had together after one of the Brighton parties. Then Bethany met some guy, fell head over heels and dropped out of the scene. She's still friends with the Napier-Joneses but it seems her wild days are over; more's the pity because when Izzy asked me to do the sketches and I saw her photos, I thought she was a complete stunner. I really must do a set of her and Trix together."

I still couldn't believe that Sam's fiancée had been like that but it had to be true. I wondered if he knew. There were still the fantasy pictures with Izzy and I pressed her about that.

"Oh, Izzy's little fantasy story? She wrote a mad tale of elves and sorcery and called it the Amberdown Rebellion. She based the characters on herself, Josie, Bethany and a few others in their little gang at the time. She has a vivid imagination and turned herself into a hermaphrodite. Bethany was always called a pixie or an elf or something and Izzy became the heroine rescuing Bethany's elfdom. It's actually quite a funny read and very well done. She was hoping to expand it and make it into a full-length erotic novel and I was going to do some illustrations but getting it published was a bit tricky given that it is pretty explicit. Maybe one day."

She let out a long sigh. "Anyway, enough talk young man. Just because I like you, I am now going to be very nice to you." She reached behind her and produced the bottle of lube from the bedside cabinet.

She squeezed it hard and let it dribble down between her amazing boobs, slathering it everywhere. She pinched her nipples hard. "Come on, what you waiting for? Get that fucking cock of yours up between these puppies. Nothing like a good tit-fuck. If you hit me on the chin with your jizz, I'll give you a bonus!"

I didn't manage that, but it was utterly incredible. Afterwards, she let me eat her pussy again and to my great delight she told me I could stay the night. It felt wonderful to wake up to someone lying next to me and seeing her there it was hard to believe her age.

Chapter 10: Paradise Lost

Once again, she left me to go to the gallery with cum all over my tummy and I couldn't wait to see what the fifth instalment of my little adventure would bring later that evening.

I cleaned myself up and went down to start my day's work. The garden was coming along and I would be finished on schedule. As I walked through Metcalfe's Corner, I noticed a blank sheet of art paper and a pencil on the work desk. Next to it on a Post-it note were the words, 'Draw your greatest fantasy. '

I thought about it long and hard as I worked through the morning. I went through a whole gamut of scenarios including Anastacia and Izzy sharing my load, through being teased and denied by Josie to being the guy that Bethany Hamilton was taking in her mouth in her orgy picture.

Eventually I stopped work, sat at the work desk and drew what I now knew was what I wanted more than anything. I recalled the look that Bethany had given Sam Atkins as he scored his hundred - that look of sheer, unadulterated love. My illustration was clumsy but it got the point across. In the distance, a young man in cricket gear was raising his bat to the heavens. The scoreboard read, 'Adams (J), 100.' In the foreground a girl with her back to the artist was jumping for joy, arms aloft. Her hair was flying and there were little lovebirds circling around her head.

She was just a generic girl -- no-one on my fantasy list. There was no menage a trois with the Napier-Joneses, no double blowjob with Anastacia and Tess, no cum swapping. Just a girl who was hopelessly in love with the guy who had just scored his hundred, making him the happiest man on earth.

I didn't know it at the time but that picture cost me the chance of Anastacia Kempston taking my cherry, but it also changed my life immeasurably for the better.

As usual, I went home after my day's work and showered. I was too nervous to eat -- was this going to be the night? I was buzzing as I let myself into the house and made to go upstairs. I couldn't wait to see what the sketchbook had in store for me.

I did a double take as I passed the loungeroom door. The table that had been set up outside the bedroom was now here, the sketchbook open. I looked down to see a professional copy of the rough image I had drawn earlier. Everything was obviously drawn to a much better standard, but this time the girl resembled Trix. I heard a voice from the lounge room.

"In here, Josh."