The Naughty Boy

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Double Penetration

I don’t really know into which category to put this piece. It’s an incest role-play between a mature lady, a celebrity actress (to whom I make no reference to reality, she’s imaginary) and a young man for whose services she pays.

Wherever it ends up, I hope you enjoy it. feedback is good, even critical as long as it’s constructive. Feedback can be in public comments below, PM on Lit, or email. If you want a response from me for some reason then email is probably best.

Forgive any errors, I do this on the fly.

GA – Belize City, Belize. 20th May 2012.

Sitting on the edge of her bed, naked, legs crossed, she carefully applied her make-up. Mrs Monroe swivelled at the waist, turning to look over one shoulder. ‘Are you spying on me?’ she asked, smirking; knowing I was now looking at her tits — big, heavy jugs — in three-quarter profile. She knew I had more than a passing interest in her breasts. I could see the glimmer in her eyes, heard the catch in her voice. She loved this game — I mean she really, really enjoyed it. Keeping in character, Mrs Monroe spoke again, ‘You naughty boy … Spying on Mummy like that when she’s all bare.’ She paused, a look of disapproval on her face which I knew to be false, all part of her game. ‘Come in here,’ she called to the door, which was slightly ajar, me peeping, as instructed through the gap. Mrs Monroe beckoned, the bracelets on her forearm jangling. ‘Come in here, I want to talk to you.’ I paused for a long moment, drawing the anticipation, giving Mrs Monroe her money’s worth.

When I’d met her, her age wasn’t a surprise; I usually get recommendations via word of mouth, there are a lot of horny ladies out there of a certain age with a surprising amount of disposable income. Who she was surprised me; I recognised her of course. Mrs Monroe, because of her celebrity, was one of those women who take pride in their appearance, who work damned hard at the cross-trainer and treadmill. She was cool, poised, and elegant when we met in one of the classier bars in town, but underneath she was probably nervous. In fact her first words to me, as they nearly always are when I meet a client, were: ‘I’ve never done this kind of thing before,’ — by which she meant paid for it. I suspect Mrs Monroe has at least attempted to play out her ‘little kink’, as she called it, in the past, but this time, since I was a professional and she was paying the piper, the piper would play any fucking tune she wanted him to. I imagine that her little scenario would turn some men on, it certainly got me thinking after our first encounter, but some would be appalled; and I think a lady like Mrs Monroe, with a professional reputation to think of, would need to be very circumspect about to whom she revealed her peccadillo.

Think middle-aged British actress, television and film, in the UK and you might guess at who she is; but I’m not telling, so I’ll call her Mrs Monroe — or Mummy when it’s appropriate, which is very inappropriate. So I recognised her immediately but, ever the professional, played it cool.

‘I’ve heard you’re very good at what you do,’ Mrs Monroe revealed as she sipped gin. ‘But,’ she went on in that familiar voice, ‘I have to ask a couple of questions right at the off.’

I nodded when she peered intently at me. ‘Sure,’ I replied. This was pretty usual, and in her case I could understand her need for utmost discretion.

‘Do you recognise me?’ she asked first. Then, straight afterwards, without waiting for my answer, she ran on with another question. ‘How old are you? I was expecting someone … older.’ And then, with the first two questions unanswered she finished with, ‘And can I count on you to be discreet?’ She glared at me then, quite belligerently, letting me know who was boss.

I sipped the tall glass of iced water — I said I was a professional. Never drink on the job, which is a bit of pun.

‘I know who you are, Mrs Monroe,’ I said seriously, adding: ‘I’m twenty-five.’ To which she nodded approvingly. ‘And as for discretion,’ I assured her, ‘well, I’m a professional too and, like you, my reputation is everything. I might be young, relatively speaking, but I’ve been doing this for three years now …’ I held up a palm to cut off her words. Mrs Monroe had opened her mouth but I wanted to be as concise as I could. No interruptions. ‘… and it’s taken me some effort to build up my name. I’m at a stage where I’m …’

I paused, I didn’t want to refer directly to the money; some clients were squeamish about the business end of the deal. I’ve known ladies who preferred to think of us as something more than we were; they found that references to cash were vulgar reminders of what our relationships were really about.

‘… Doing well,’ I finished eventually.

She took a little more convincing, but she had an itch that needed scratching and we finally took a room in a place where discretion could be assured.

Mrs Monroe got a free sample.

When it was over, Mrs Monroe outlined kartal escort bayan her wants. She lay bedraggled and panting, make-up ruined, a fortune in hair-styling resembling a bird’s nest, yet still looking gorgeous, Mrs Monroe surprised me, shocked me even, but I named a price and we agreed.

The first attempt at her role-play was a bit wobbly for the pair of us, but here we were again, only a day later. She was so eager.

I pushed the door open after deciding Mrs Monroe had waited long enough. She gasped and put a hand to her mouth in shock — she really was talented at her craft. ‘Oh my!’ she shrieked through her fingers, eyes wide. ‘You’re all bare too.’ There was a pause while the woman took in my nakedness. Despite being a tradesman I’m still a man and my cock pulsed at the sly expression that twisted Mrs Monroe’s face. ‘Oh you naughty boy,’ she crooned, the words dark and low. She loved it, absolutely adored this game. ‘Look at you all naked and stiff. Are you all excited from looking at your mummy with no clothes on?’

Her words tickled an indefinable spot way down deep inside me. I nodded, whispering, as instructed, eyes downcast with contrition, ‘Yes, Mummy.’

‘Come here,’ the woman commanded. ‘Let Mummy look at you.’ I moved a step or two closer. I saw Mrs Monroe swallow heavily, gulping her arousal. ‘Such a lovely big boy,’ she murmured, her gaze on my cock. ‘I know you’ve been watching me,’ she whispered, looking into my face. ‘I know you’ve been spying on me. And I’ve been teasing you, letting you watch me while I get dressed.’ She rose from the bed and took a pace towards me. ‘Would you like to watch Mummy get dressed up, darling? Would you like to see Mummy put on her stockings and shoes?’

It was my turn to gulp. She was so fucking good at this.

I nodded again. ‘Yes, Mummy,’ I murmured.

I really wanted to pull my cock. I wanted to watch Mrs Monroe in this act, watch her dress up and talk the talk while I just yanked my erect penis. Struggling to hang on to my professional cool I collapsed onto the huge bed.

‘Just watch me,’ the woman continued, excitement cracking her voice. ‘Watch Mummy as she dresses up for you, my darling.’ She clasped a lacy garter belt around her waist, red to match the evil-heeled shoes I saw in the corner. Next she rolled a pair of light denier stockings, black, onto each leg, and secured the hose with the dangling garter straps at her thighs. She walked to the shoes and slid her feet into them. Then, tottering precariously atop those stilettos, she carefully negotiated the few steps to her make-up stand.

She lifted a scarlet corset, holding the garment close to her body and turning her back to me. ‘Help me with this,’ she instructed, looking at me coyly over her shoulder. ‘No touching, you naughty boy,’ she giggled when I knelt on the mattress and took a squeeze at her buttocks. ‘Not yet,’ she chastised further, slapping at my hands as I reached around to her front and made a grab for her breasts.

I was desperate for her, almost frantic. This was the first time in all my professional encounters that desire overwhelmed my business sense, and it was only Mrs Monroe in her role that kept me in check. If she’d let me loose at her then it would all be over in minutes.

With my fingers occupied hooking the corset closed across Mrs Monroe’s slender back, I leaned in and licked her neck. She groaned, a hand reaching behind her to clasp my head as she craned her neck, somewhat awkwardly, and pushed my face to her mouth. We kissed, tongues sliding, breath mingling, and with my erection nudging between her legs along the crease of her vulva.

‘Oh, Mummy,’ I had the presence of mind to say when the kiss broke, playing the game and pleasing her. ‘We shouldn’t be doing this. I … I shouldn’t be kissing you like that.’

‘But I want you to kiss me,’ she gasped. ‘My lovely boy, kissing his Mummy and loving her like he should.’ She turned to face me and placed her hands on my shoulders. From her slightly elevated position, standing whereas I still knelt on the bed, Mrs Monroe stared down at me intently. She eased closer, her shins butting against the frame of the bed. ‘Kiss me again,’ she breathed. ‘Kiss your Mummy’s mouth.’

This time, as our tongues slid and swirled, my hands slid from where they’d automatically clasped around the woman’s waist to her buttocks. She moaned into my mouth as I squeezed at her. The kiss went on, my hands massaging taut flesh until an expeditionary finger slid along the crease of her buttocks. She gasped when my forefinger found her opening, the molten heat of her sex.

‘Touch me there,’ the woman sighed, her breasts, which had spilled from the inadequate cups of the corset, squashed against my chest. ‘Feel me, darling. See how wet I am for you? That’s how excited you make me.’

She was sodden; the stuff was sliding from her, this little kink of hers was something she really enjoyed. I knew that she had two real-life escort maltepe sons, both older than me, and this must have been something on her mind for a long time. Not that she’d ever live it in reality but, by proxy, with me as a stand-in, she was letting herself go. I’d never even contemplated this scene before, but the more she got into it, the better it became for me. If Mrs Monroe wanted to be my mother, then I was happy to play along. In fact, if I had her for a mother in real-life, I’d be tempted to fuck the taut, toned, tanned arse off her.

‘Oh, Mummy,’ I babbled. ‘You’re so beautiful.’ I wasn’t really making any of this up either. She really was gorgeous.

‘So are you, darling,’ Mrs Monroe gaped. She pushed a hand between our bodies. ‘Your tummy,’ she sighed, ‘so tight and muscular. I love your abs … your chest …’

And so she should, it was all part of the deal with me; the hours I spent in the gym probably matched the time she spent in her own gym. This was the pay off for me though, to hear a woman like her compliment me.

She kissed me again, her hand reaching lower. ‘My baby is so big and strong,’ Mrs Monroe whispered against my neck as she licked and nibbled at me. ‘I love your big cock,’ she said, eyes gleaming. ‘I want you to put that thing inside me … soon.’ I saw her grin; saw lascivious intent on her face. My cock throbbed with arousal. Fuck, she was turning me on with this Mummy stuff …

Stepping back a pace, but keeping one hand around the shaft of my cock, Mrs Monroe squeezed her breast. A forefinger teased the nipple into elongated arousal. Her fingers worked at me with an underhand grip while she fingered and pulled the other nipple into a taut point of desire. She gasped when I wedged my hand between her legs and fingered her soft, slippery labia.

‘Touch Mummy there,’ she moaned. It’s so naughty.’ She stared into my eyes, her hands back on my shoulders now as I fingered her. I watched her expression change from bright-eyed eagerness to slack-jawed distraction. ‘Oh, darling,’ the woman gasped. ‘You’re touching Mummy’s clit … You’re making me feel so wicked. This is so bad … you touching me there.’ Her heavy-lidded, half-closed eyes snapped open. She grinned at me again as her fist curled around my jutting length. ‘We’re touching each other, aren’t we darling? We’re both being so naughty. Me and you together, just like it should be, loving each other.’ She pouted at me, her lips a questioning moue. ‘Do you love your Mummy?’

‘Oh yes,’ I replied.

‘Do you like watching me without any clothes on? Do you like it when I dress up in sexy clothes for you?’

I almost whimpered in response. I thought I’d be splashing the hot stuff all over her wrist, her stomach and the bed if she kept up this litany of incest. To my gulping relief she released my cock. She took another pace back and held her breasts in her palms.

‘Oh, Mummy …’ I groaned, my eyes sliding over her body. I looked into her face.

‘It’s time,’ she whispered, ‘time for you to show me how much you love me.’ She paused, perhaps sensing that she was having an effect on me; the first one to actually crack my professional facade. She used her experience as an actress to draw the moment out. The way she looked at me, the way she was dressed, the timing and the language she used were devastating. ‘Mummy wants to ride your cock,’ she said. ‘I want you to fuck me.’ She grinned at me again, adding, ‘Do you want to fuck Mummy’s cunt?’

I was on the bed, on my back, and she was crouched over me. I had a momentary image of those heels rending the sheets, but I didn’t really care about Mrs Monroe’s furnishings, what I wanted was for her to lower herself down an inch or two. She held me upright, reaching between her legs to grip my cock to aim the thing towards her opening.

‘Are you sure?’ she asked, pausing. Oh the agony of anticipation.

‘Please,’ I gasped, hands around her corset clad waist to steady her. I watched entranced as her big tits swung and swayed.

‘We can’t ever go back,’ she continued, but rubbing the head of my cock against her dribbling opening. ‘Once this thing goes inside Mummy we’ve done it. We will have done such a naughty, wicked thing, my darling. Are you sure you want Mummy to sit on it?’

Fuck yes, I wanted to scream, but somehow held on to the character she expected me to be. ‘I want to, Mummy,’ I stammered, swallowing heavily. ‘I want to love you like I should. I want to love you properly.’

‘Oh, my darling boy,’ she sighed. ‘Love me.’

We both groaned when the heat of her engulfed me and I slid from tip to balls inside her. Her insides clenched around me while her lust oiled our conjunction. The stuff dribbled out of her, cooling on my thighs as she rode to the tip of my erection. She paused, hovering over me, staring at my face while her tits hung suspended. I reached for her breasts and she chuckled.

The first few minutes of our fucking were both arousing pendik escort and frustrating. I sucked at each of her breasts, nibbling and licking her long, thick nipples as she slapped her body up and down hard against my cock. The continuous slide of juices from Mrs Monroe soon caused us to lose momentum. There was just too much of the stuff oozing out of her.

‘You’re making Mummy so wet, darling,’ she crooned, lifting a leg over my thighs so my cock plopped out of her. She walked to the en-suite and I watched the sight of her backside swinging and swaying as she moved, using my hand against the slippery shaft of my cock. She reappeared a moment later holding a hand towel. ‘Play with yourself,’ she said, eyes bright as she dabbed the cloth between her legs. ‘Let me watch you play with it.’ She wiped herself a final time and dumped the towel on the floor. Lying alongside me on the bed, she ran her palm over my stomach. I stroked my cock gently, just enough to allow the semen boiling inside me to cool.

We kissed again, gently at first but then harder and more insistent as the woman’s passion flared again.

‘Put it back in,’ she urged, laying on her back and opening her legs. ‘Fuck Mummy, darling. Fuck me hard and make me come.’

I scrabbled into position between her thighs. Mrs Monroe, supple and pliant as a gymnast spread her legs so wide she was doing the splits on her back, legs straight, toes pointed as a ballerina’s, heels slicing dangerously.

She held herself open with her fingers. ‘Shit,’ I groaned at the sight of her hot, scarlet and gaping.

‘Fuck me,’ she repeated. ‘Make me come on your lovely cock.’

‘Oh, Mummy,’ I groaned as I slid into her again.

At first, with me virtually slumped on top of her, we kissed, murmuring endearments, our bodies moving together slowly. Then we began to fuck in earnest, the desire for release driving us on. I wanted desperately to just let it go, to let the stuff gush from my cock in a long rush of pleasure. My professional pride held me in check, as difficult as it was I had to stay in control until Mrs Monroe — Mummy — was satisfied. This was a tough job.

Sweat began to pool on my forehead and run down my chest as I hefted myself onto my palms, straight-armed, my erection the only part of me in contact with the gasping, writhing woman below. I used different speeds, depth of penetration, and altered the angles of my thrusting to keep the woman entertained. For her part she snarled and spat at me; glared at me with near hatred in her eyes, an expression I’ve come to recognise as an extremity of lust.

‘Oh that’s good,’ Mrs Monroe grunted, face twisting and grimacing. ‘By cunt’s burning,’ she gasped. ‘It itches … Darling, make Mummy come. Please, make me come …’

‘I love you, Mummy,’ I grunted. I knew she wanted to hear this. ‘I want to do this to you every night. I don’t want anyone else; I don’t want you to do this with anybody else either. Just me, Mummy; you and me; us doing this together; doing this every night.’

I rose onto my knees, holding her waist to keep my cock inside her. Using a little technique I learned from a very kinky lady with a penchant for leather and group sex, I used my hand to angle my penis into Mrs Monroe so the head of the thing rubbed a place inside her. After three goes at it the woman suddenly stiffened, her whole body going rigid. There was a pause and then her eyes opened wide, a look of surprise crossing her face. She blurted a single loud, ‘Fuck!’ as her mouth formed a huge O. I pushed my cock head against that place again and then withdrew just as the spasms started in Mrs Monroe’s thighs. She shrieked and grunted, fingers clawing at the bed while a squirt of viscous liquid gushed from her opening.

‘Fuck,’ she squealed again. ‘I’m …’ Another harsh gush squirted out of her. A large damp patch spread across the bed cover. ‘Oh, I’m coming,’ the woman called, a laugh bursting from her throat. ‘You beautiful man … I’m coming … I’m wetting the bed … I’m so wet …’

Eventually, when the juddering in her thighs and hips had ceased, while she lay panting on top of the rumpled, stained bed, Mrs Monroe stared up at me. ‘That was lovely,’ she murmured. ‘You made Mummy come.’ I reached for the towel next to the bed. She wiped herself, smirking at me, embarrassed. ‘Look at the mess.’ Then she held her arms out to me. Her legs opened. ‘Fuck me again,’ she said softly. ‘Come and do it again. Fill me with your spunk this time.’

I lay between her legs, her thighs sticky and shining with her outpouring. Easing down onto those pillowy breasts I kissed her. I kept the kiss slow and tender, my tongue languidly exploring her mouth as I slid in and out of her body. She began to respond, her hips moving against my thrusts, her breath panting into my mouth. I looked at her face, flushed with exertion, hair limp against her forehead.

‘I’m going to come, Mummy,’ I gasped. ‘Can I do it?’

‘Yes, darling,’ she sighed. ‘Just let it all go. Let it go into me. I want to feel you coming inside me.’

And then we both climaxed, my jizm squirting into her accommodating body while her arms and legs came around me. When I was spent she held me against her, my cock still inside her body.

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