A short tale of Ricky's initiation into the world of anal sex. Thanks to Solivagant for the checks and spotting.
Leonora moved in next door to us in the summer of 1972. I was 20 at the time and our new neighbour was a ripe, finely mature forty-five years young. I was in lust from the moment I first saw her and that first sighting actually took my breath away. It wasn't until my brain registered the tightness in my chest that I made a conscious effort to breathe; such was the intensity of the moment. Leonora, to me, was stunning and although I didn't know it at the time, she was going to influence my life enormously.
Leonora's seduction of me was so clichéd I'm embarrassed to recall the circumstances. Callow youth, mature woman, sultry Saturday evening, her husband absent, wine... Need I go on? The result of that first encounter was an affair that was to teach me a lot about how to please a woman, and for that I have an undying gratitude for my talented instructor.
Leonora wasn't my first, there'd been other girls, but she was my first woman, my first really experienced woman. When she made her move on me on that first evening I was astounded by her boldness, her directness and although I'd experienced sex before, this was a whole new world to me.
Leonora's figure was superb and her lovely, big breasts were the reason for my subsequent propensity for fuller figured ladies. Leonora held my eyes with her stare as she unhooked her bra and let those big jugs free.
'You like my big tits, don't you Ricky?' Leonora held her breasts in the palms of her hands and tickled her stiff teats with her fingertips.
'Er... Yeah, I do,' was all I could manage by way of a reply. I was speechless at the situation I was in and couldn't believe what was happening to me. Was I really going to fuck my neighbour?
'Take your clothes off, baby,' Leonora said in a low, husky voice, 'and then come and suck them for me... I do love my titties to be sucked.'
Moments later Leonora was stroking my hair and almost purring with contentment as I feasted on her big creamy breasts. We were sat on her sofa and as I circled each nipple in turn with my tongue I felt Leonora's cool fingers grip my cock tightly.
'That's it, lovely boy,' she whispered, 'suck my tits, while I feel your lovely thick cock, God it's so stiff!'
Leonora pushed me away from her body and moved so that her face was near my cock. She tugged at my shaft several times and then surprised me by sticking out her pink tongue and licking the head of my cock.
Leonora licked me tenderly for a few moments and then wrapped her painted, red lips around my harness. She sucked at me in a sudden frenzy and used one hand to wank the root of my cock while she sucked. I looked down at her and saw her cheeks bulge as the big domed cock head distorted her face and I pushed my fingers through Leonora's thick, blonde hair to push more of my cock into her mouth. She didn't flinch and took my entire length into her mouth and partially down her throat.
Leonora spread her smooth thighs and fingered her squelching pussy while she continued to give me the best blow job I think I've ever had. She was moaning around her mouthful of meat when I felt the surge of a toe curling climax. My cum squirted and Leonora swallowed and as my cream jetted from my cock Leonora's own orgasm hit her.
'Yes! Oh yes!' Leonora cried out after my cock had sprung from between her lips. 'I'm coming,' she whimpered unnecessarily as her whole body stiffened. She continued to massage her clit as she climaxed and the sight and sound of her climax kept my cock rock hard. 'Come on Ricky,' Leonora said enthusiastically when she'd calmed a little. 'Take me to bed, it's time to fuck.'
She walked from the room and left me staring at her fantastic rear as I sat on the settee. My cock was oozing cum and was full of the ardour of youth. I followed Leonora upstairs to her bedroom and found her lying gloriously spread on top of the covers.
'Come, come here,' Leonora indicated the bed between her legs and I clambered aboard eagerly. 'Stick that fat cock into me lover,' she said with shocking directness and used her fingers to hold the big flaps of her sex apart for me. I noticed that her opening was flushed a hot, exciting pink and that she was gooey with anticipation where her excitement had flowed from inside her.
I pushed my cock against Leonora's body and felt her heat as an inch or two slid inside. I steadied myself on my outstretched arms and slid deeper into Leonora's accommodating grip.
'Yes, that's it,' she said quietly. 'Feed me your cock. God it feels good to have a young cock inside me; I love fucking young men.'
Leonora began to move her hips jerkily as she tried to fit more and more of me into her body. I moved with her and began to fuck her in earnest. I watched her face contort with the pleasure she was getting from me as we fucked and Leonora squeezed and mauled at her big breasts as her excitement grew with each passing second.
'Come on Ricky, fuck me hard.' Leonora was panting with the exertion as she fucked her hips up to meet my pounding thrusts. 'Use my cunt,' she said, 'use my cunt and fuck me. I'm such a dirty slut.'
As shocked as I was by the filth that poured from Leonora's mouth, the obscenities turned me on and spurred me to fuck her harder and faster. I was rewarded by a huge groan from Leonora, which was followed by a series of animal grunts as she came. Leonora pulled me down on top of her and kissed me fiercely as she climaxed, her tongue working deep in my mouth against my own.
That was our first coupling, we were to continue our torrid affair throughout the summer, but it wasn't until the fourth or fifth meeting that Leonora really showed how dirty she could be.
Leonora had invited me over to the house, as was usual when her husband was away, and since I was near obsessed with my randy neighbour I was only too pleased to accept her invitation. Leonora was naked when I arrived and I gazed at her contoured body hungrily.
'Feeling dirty are you?' she laughed when she read my expression. 'Well, I've got a dirty surprise for you tonight.'
She had me out of my clothes quickly and was soon on her knees sucking my ever-ready penis. I loved the way Leonora sucked cock, she was so ...zealous. Once she was bathed in the full glow of her lust my normally refined neighbour turned into a complete slut. She would slurp with uninhibited abandon over my cock head and would usually end up with her cheeks and chin smeared with her saliva and my precum. She wasn't averse to taking the brunt of my gooey attack over her face either and would cry out happily when the hot stuff splashed onto her skin.
This is what Leonora did on this particular night. I didn't realise at the time that she was feeling particularly wanton and depraved, but I was to find out soon enough.
'Do I look like your little slut, Ricky? Do I?' Leonora was looking at me with her face liberally smeared with my spunk. Long ropey strands hung from her hair and even her breasts were spattered with the stuff. I had to admit, she did look a complete slut, but somehow I found that the more debauched Leonora appeared, the more I desired her. Damn, she was a sexy bitch.
'Now I want you to fuck me,' Leonora whispered and scooped a dangling thread of cum into her mouth. This wasn't news to me. Leonora always wanted to fuck, but I didn't count on just how she wanted it this time and her next words caught me off guard completely. 'I want you to stick your lovely cock in my arse.'
Leonora knelt on the bed on all fours and wiggled her delightful rear at me. She then pulled the cheeks of her buttocks apart and revealed the dark stain of her rectum. I saw her sticky labia peel apart as Leonora held her cheeks wide for me and I felt the lust burst inside me. I knelt behind Leonora and dabbed the tip of my tongue against her clit. Leonora squealed when she felt my tongue on her body and then moaned softly as I continued to lick her.
'Yeah baby,' she sighed, 'tongue my clit, lick my hot cunt, I'm so fucking naughty.'
Leonora's foul mouth never failed to arouse me and my cock was stiff and large, all set to ravage Leonora's tender anus.
I pushed my tongue deep into Leonora's pink centre and managed to have her writhing and groaning loudly in an instant. I pushed two fingers into the wetness of her juicy opening and manipulated the spot inside her that I knew would make her moan some more. Leonora didn't disappoint me and was groaning so loud that I was sure my family next door could hear.
Leonora was clawing at the bed by now and as I fingered her dripping sex I held her buttocks apart with the other hand and dipped the tip of my tongue into the rosebud of her arsehole. Leonora went berserk as I probed at that most intimate place with my tongue. She gasped loudly and let her head fall forward; lost in a wave of intense pleasure that left her breathless.
'You dirty, fucking bastard,' she whispered when she'd recovered sufficiently. 'I love it. I can feel your wet tongue in my arse. God, that's so... so...'
Leonora was lost for words and she gave up trying, surrendering herself to the sensations that were pulsing through her body. I felt her insides clench around my fingers and I knew that Leonora was close to a climax. Sure enough she bucked and writhed in ecstasy as she came and when I pulled my fingers from inside her, they were covered in her syrupy goo.
'Up my arse, Ricky, please... Fuck me in my arse.' Leonora was frantic now and after a couple of tugs on my cock I simply pushed the head of it up against Leonora's brown hole and pushed. There was a slight resistance and then I felt Leonora's sphincter stretch and then tighten around my cock when it popped inside her suddenly.
'Oh God, Ricky,' Leonora murmured. 'Fill my arse with meat, stretch it, make it burn...'
I gulped and eased myself ever so slowly into Leonora's rectum. I was afraid of hurting her in this unknown territory and tried to be as gentle as I could. I needn't have taken such with Leonora's backside however, because once I was fully inside her she begged me to fuck her. Hard.
'You're in aren't you, Ricky?' Leonora said when my balls touched her body. 'You're right in my arse.'
She pushed back against me as though trying to fit even more of my cock inside. I gritted my teeth as Leonora's sphincter tightened around the shaft of my cock and I had a sudden moment of panic when I thought I was going to come right then. I took several deep breaths and forced the fear from my mind. Then I held onto Leonora's wide hips and pulled out a little.
'Fuck me now, baby,' she sighed. 'Use your cock and fuck my tight arse, please.' I slid in and out of Leonora for several tentative strokes, still unsure about the fragility of Leonora's anus. Leonora swivelled slightly and looked round at me. 'I said to fuck me, not tickle me.' She pushed her hips back at me for emphasis. 'Now, fuck my arse, pound me; come on.' Leonora pushed again and this time I reacted. I dug my fingers into the flesh of her hips and pushed forcefully all the way into her. She sighed with the pleasure and so I fucked her a little harder.
'Harder, come on, do me harder.' I strengthened my thrusts some more and was soon pounding into Leonora as hard as I could. My stomach was slapping against Leonora's lovely buttocks and I revelled in the sight of her arse cheeks as they rippled under the onslaught of my thrusting cock. All concern for Leonora's pain was forgotten and I slammed into her roughly.
'Oh yes, baby, that's divine,' she cried as I ravaged her arse. 'It's so bad, so dirty... Oh God, I love being used in my arse.'
Leonora was squealing and tossing her head up and down. She looked back at me over her shoulder and I saw the light of pure abandoned lust in her eyes. She reached out and raked her fingernails along my muscled chest; the look of undiluted rapture on her pretty face made my cock swell and throb. It was a look that will stay with me forever and had me on the verge of shooting my load right then. Leonora's eyes were glazed as though she as lost in her own private reverie. Her eyelids were heavy with lust and her mouth was hanging open as she panted heavily.
'Ricky... Please. I'm... I'm going to come. Ream my arse... Oh God...' Leonora's head dropped forward and she let out a wail of pleasure as she climaxed.
She writhed madly and almost pulled away from my cock. I was having none of it however and continued to pound her mercilessly. I was close to the edge myself, but I wanted to teach the slut a lesson and continued to stuff her rectum with my cock.
Leonora's climax began to fade, but my own orgasm was hurtling along on its own unstoppable course. I grunted massively and gripped Leonora's hips with unconscious cruelty. My semen spurted from the eye of my cock and gushed into Leonora's bowels.
'Oh fuck,' she shouted when I came. 'I can feel your spunk. You're coming in my arse; you're filling my arse with cum! That's so bad, so dirty!'
Leonora spasmed again as the wave of yet another climax broke over her and I spat jet after jet of my seed into her body at the same time. I'd never experienced such excitement in a woman before. Leonora had been wildly passionate when we'd coupled in the past, but the display of wanton abandon she exhibited when she was fucked in the anus was staggering.
'Oh baby, that was so fucking good...' Leonora kissed me while we lay on the bed. She had slumped forward when her orgasm subsided and thick dribbles my cum had squelched obscenely from Leonora's used hole when my cock plopped out of her body. 'Did you like fucking my dirty arse?' Leonora asked as she cuddled up to me in post coital bliss. She didn't wait for a reply and added, 'I loved it. I want you to fuck my arse again real soon, OK?' Leonora turned so that she was facing me and smiled wickedly. 'Next,' her grin broadened, 'I'd like you and my husband to fuck me at the same time.' She laughed when she saw the shock on my face. 'What? You think he doesn't know?' Leonora shook her head and continued despite my shock. 'Oh yes,' she said unconcerned,' he knows all about us... He positively wanks himself silly when I describe what we've been doing together, wait till I tell him how well you reamed my bottom, I'm sure he'll want to join in next time.'