Ali’s First Anal Play Ch. 02

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Last week Ali had shared something with me she had been worried about doing for some time, and she had enjoyed her first anal play and small plug more than she was expecting. Her orgasm caught her by surprise, and as I filled her pussy with my cum, I could feel the plug against my cock, filling her completely. A week later and Ali had challenged me…. to fill her even more fully…. and I think we both understood where that would go… We met at her secluded apartment, and as she let me in I whistled at the vision before me. Ali is stunning, and I cannot work out why I am so lucky. We have been friends for years, confided most things but to get to enjoy her fantastic, sexy body had never been on my radar. Now I could not get enough.

Ali was wearing a black dress that clung to her curves and emphasised her shapely figure. The hemline was short, designed to show off her long, slim legs which today were covered in a fine, barely black nylon and ended in steepling heeled shoes, emphasising her slim toned legs even more. Her auburn hair fell around her smiling face, and I noticed the top two buttons on the front of this slinky dress were already open, showing a perfect cleavage. As we kissed, hungrily and gorging on each other, my hands roamed her body, knowing I would find evidence of suspenders or hold-ups as Ali never wore tights. I was not disappointed, the straps from her corset or basque could easily be felt holding up those shiny black stockings. As we took a breather Ali led me to her bedroom, no pretence at conversation or idle chit chat, this was about pleasure first, talk later.

We kissed hungrily again, and I started to stroke her back and ass cheeks. The dress clung so tightly I could feel every strap, every curve through the skimpy fabric. Lifting the hem my hands found the firm round globes of Ali’s ass cheeks and I began to fondle the firm, smooth flesh under my fingers. Stroking lightly at first as we kissed, our tongues fought for space as we caught up on years of apparent frustration. Her ass cheeks were so firm yet supple, the flesh silky soft but the muscle tone keeping them tight as I stroked and lightly touched my way around. I could feel Ali’s chest rising and falling as she pressed against me, our mouths never parting as we continued our long lasting embrace. I toyed with the suspender straps, stroked her cheeks and slowly inched my hands lightly between them. I found what I was wanting to find. Ali had foregone her usual lacy thong and I pressed lightly on the small flange of a plug nestled between her gorgeous flesh, a small plug already snugly inside her ass where I had asked for it to be. I pressed a little harder, and was rewarded with a growl into my mouth as we kissed.

Finally we broke as Ali stroked her way around my thighs, my ass and ran her nails gently up the front of my now bulging chinos. I undid another button as I looked at her flushed but smiling face, and pulled her in slightly so I could stroke the flesh of her cheeks again. I undid another button, revealing more of her fantastic cleavage and the lacy fabric of the black basque barely containing her breasts.

“Mmm, well done, when did you manage to ease the plug in?”, I asked, toying with it gently and bringing groans from Ali as I did so.

“Just before you arrived, the…oooh… I wasn’t sure if I could stand it for long…. aargh….,” replied Ali, occasionally distracted as I twisted the plug in its oily home.

“Feels good to me… as does the rest of your amazing body. Are you ready to do as I ask, no questions? Just let me take control and take you in whatever way I fancy?”

Ali’s eyes glowed, lighting up as she smiled her reply. Kissing me hard on the lips, then standing back demurely with her hands beside her she nodded, smiling coyly as she said in a quiet voice, “I am all yours,… do what you will…”

I pushed her shoulders and Ali understood immediately. She knelt down and undid my chinos, letting them slide down and getting my to step out. My silk boxers and socks quickly followed, before Ali’s eyes and all her attention became focussed on my cock. Stroking it lightly she started to tease the end, and I groaned as the sensations flooded through me. My cock twitched every time its sensitive end was lightly flicked and Ali grinned as she stuck out her tongue and gently licked the side of my straining member. More groans, and Ali got to work in earnest, licking more and more around the shaft of my cock, on to the top to suck away the precum forming, before licking güvenilir bahis back down the lengthening and hardening flesh. Cupping my balls one by one she sucked them into her warm and willing mouth, gently holding them, bathing them before coming back to lick the flesh of my solid cock again. Finally spreading her lips she sucked just the head of my cock into her mouth and held it there.

The sensation was fantastic, electric, and I almost came at the touch but as if sensing that, Ali pinched the base of my cock and stopped her mouth movements for a moment until I had re-gained control. Then she set to work on my cock, sinking her mouth further and further onto its shaft, sucking more and more of its length into her wet and warm mouth until a slight gagging brought its progress to a halt. Sliding her mouth off and back on she began to fuck my cock with her mouth. Ali worked her mouth up and down my cock, using her tongue to tease the tip and lick of my precum that kept on forming as her fantastic fellatio was getting me closer and closer. I wanted to cum now so my cock would stay harder for what was to follow, and I was not going to stop Ali. Holding her hair to one side I watched in awe and excitement as she bobbed up and down on my now fully erect and highly aroused flesh. Finally, Ali started to lightly toy with my perineum, teasing the flesh lightly and occasionally rubbing a nail gently around my anus as she sucked and bobbed up and down on my cock. That was too much and I could not stop the explosion. I struggled to hold back, tensing hard as finally my cock slowed then shot pulse after pulse of my cum into Ali’s waiting mouth. As the first pulse hit Ali eased off my cock a little so she could accommodate all the cum that was spurting out of my throbbing flesh. Finally I finished, and Ali gently sucked the last few drops from my now sensitive member before easing off and swallowing the last remains. Looking up and smiling, she cocked her head as if to ask if it was OK. I stroked her hair and cheeks, and smiled back.

“Mmm, fantastic, exactly what I needed and I hope you enjoyed it. Now we can get my cock back hard… I want to fuck you for so long you will beg me to stop.”

Ali stood and I completed undoing the buttons and slid the black, sheath like dress off her body. The basque holding her stockings up was of a black silk, boned to bring in her already slim waist and with lacy quarter cups clearly showing off her fine brown nipples. These were standing proud, pushing at the fabric, rubbing against the lace, aroused by the action that we had already played out. I folded down the lace and teased each nipple in turn, bring gasps from Ali each time I lightly pinched the end of her nipple. Rolling each one in turn between my finger and thumb, I gave them a gently pull, stretching out the taut flesh before letting it bounce perfectly back into position. Ali was writhing at this, the sensitivity of her breasts clear as she tried to get away from my insistent teasing.

I pushed her gently back towards the bed, and laid her on her back. Stretching her legs wide with her knees raised so her heeled shoes were flat on the bed I went to work. My softening cock had already started to show interest again, and the lewd sight before me was only going to help it get hard again. Ali’s hairless pubic area was a sexual joy to look at, smooth flesh and already pink engorged pussy lips, even though I had yet to fully explore them. Clearly visible below was the pale blue flange of the small plug filling her rear hole, and contributing to those sensations. Her slim legs were such a turn on, and I started lightly touching the heeled boots. the soft leather was sensual to my touch, I guess it must be good to wear judging from Ali’s interest in such things. Stroking my way I found her calves, her ankle and lightly trailed my fingers up and down the nylon covered flesh. It felt so sensual, so sexy I just had to taste it, and started to lick the her legs through the fine material of her stockings. Tracing my way up her left leg with my fingers, and her right with my tongue until I found the silky smooth thigh where the stocking ended on each leg. Stroking and licking gently towards my goal and I looked closer at her now wide and engorged pussy lips. Ali’s head was back and gentle sighs were coming from her. She tried to rise up and down as little waves of enjoyment went through her, until I rested my lips onto her pussy lips. She started slightly, and gasped as I slipped just the tip between her outer lips and türkçe bahis slid it up and down the crack, drinking in her sweet juices. Ali grabbed my head as I did this, gasping as the light tracing of my tongue found its way further into her cunt. Using my hands to hold her outer lips apart I watched her inner lips and tube contracting as the pleasure mounted, then dove back in with my tongue, lashing at her pussy mercilessly. Ali rewarded my with a yell, and ground her cunt onto my face as she strove for her orgasm. I could feel my cock getting harder, the erotic nature of our encounter already getting me erect again.

Finally I moved my tongue out and up onto her hidden bud, her clitoris. Even as I did so I swiftly replaced my tongue with a couple of fingers, sliding them deep into her pussy as my lips fastened on her slit. Whipping my tongue across her bud, back and forth, time and again I had Ali writing and shouting above me… my fingers hooked into her cunt, seeking her g-spot as she reached her orgasm.

“Aargh, ooooh godddd…yes, yes.. fuck…. nnrgh…,” her screams became unintelligible as I forced a third finger into her already full pussy. I could feel the contraction gripping my fingers, feel the hard rubber plug in her anus making her pussy tighter than ever. As she came, creaming and thrashing it was hard to hold my mouth over her clit, lashing at it time and again until she begged me to stop… even Ali had become a little sensitive it seems. her juices were flooding onto my hand, coating m finger, my tongue, my face and I was wet with the sticky, heavenly cum that she had produced. I was also hard again…. and as I left Ali’s pussy I was ready to start my next onslaught….

Ali looked slightly dishevelled as she came down from her huge orgasm, but I was ready to take her further again. Before I did I needed to make sure I was hard again, and I laid myself in between Ali’s widespread legs and positioned the tip of my hardening cock at the entrance to her sopping wet pussy. Even though it was not yet fully hard it slipped into her well used vagina quite easily, coating the length of hard flesh with her copious sexual fluids, juices I had enjoyed the taste and feel of. Ali groaned and mouthed, “Are you sure… ” but I slid in easily, feeling the firm plug again as I did so. This was not my final goal though, just a way of arousing my cock to its full size, and after only a few slow plunges in and out of her tight cunt I withdrew, and stepped off the bed. Walking to the side of Ali I invited her to continue her oral ministrations, to arouse me further, and Ali went at it with abandon. Kneeling up again she sank swiftly onto my cock, her lips parting and taking its full length straight away. She sucked and licked off all her own juices, making throaty noises of pleasure as she did so. My cock was getting more erect as she worked, filling more and more of her mouth until I felt it was time to take back the control and give Ali her final rewarding experience of tonight. I gently pushed her head back and away from my wet, purple, engorged penis and laid her back on the bed.

I reached for the ties and cuffs I had brought with me to get Ali into the perfect position for what I wanted to do. Pushing gently on her legs I raised them in the air and bent them back, exposing her fantastic firm ass properly, the plug’s flange clearly embedded in her perfect ass. Slipping a soft cuff on each ankle I fastened a tie to each one, and then took the ties to the cast-iron bed head, keeping her splayed legs wide apart and in the air, her pussy and ass perfectly exposed to me. Her firm, shapely legs were spread, the vision starting with her soft leather ankle boots with their spiky high heels and ending in the straps of her basque, the pale firm flesh of her thighs stretched taut. To complete her surrender to my ministrations I cuffed each wrist and laid her arms flat on the bed, tying them off to the end of the bed, leaving her little movement and not chance of now stopping me from having my way with her. My cock was so hard at the thought…

Kneeling between her legs, and stroking the nylon covered flesh as I worked, I licked my way up and down the inner thighs of my partner, and her attempts to get away were always foiled by the ties holding her wide open. I licked around the plug, teasing her filled ass with my tongue, bring gasps from her as I slipped a finger into her pussy at the same time. Taking hold of the plug I played with it, pulling it out and letting it slide back, watching güvenilir bahis siteleri her ass open and stretch before it filled it again. Ali was moaning now as my fingers worked at her plug and her pussy, playing with them time and again, pulling and filling her ass and inserting up to four fingers into her overflowing cunt at the same time. Her groans were reward enough and I knew she was enjoying it. She was watching my face as I played with her smooth silky flesh, stroking her legs, tweaking her nipples and rolling her firm breasts around, anything to keep her excitement building. At one point I could feel the contractions of her vaginal walls start around my fingers and I stopped my thrusting… “Nooo, so close… go on you… go on…, ” was Ali’s cry as I slid out and started again elsewhere.

Finally it was time. Ali’s breathing was heavy, her pussy was pulsing often as she kept getting closer before easing away from her orgasm and I knew she couldn’t take much more. I slowly inched my cock into her slick, wet cunt for the last time, coating its thick hard flesh with her juices but before she could bring herself off on its penetration I reached for the flange of the plug below my cock and tugged it out. I felt it leave her ass, pulling past my embedded cock as it went, easing the pressure on Ali’s full cunt. Quickly I slipped out of her pussy, slicked some of her own juices down to her already well lubricated ass and pushed the head of my cock against the well stretched entrance. It popped in, nestling tightly and snugly into her ass. Ali yelled, and I felt a small wave pulse through her. I waited, adjusting to the slight tightness compared with her pussy. Supporting myself on my arms and looking down into Ali’s sexy eyes, I eased a little further in. Ali was speared by my cock and her widespread legs left her in no doubt what was happening, Her eyes widened as my cock worked its way into her virgin ass…. She was rolling her head around, wide-eyed and almost gasping in short breaths as inch by inch I filled her rear hole. I checked with her, stopping every so often to see if she wanted this to stop, but she was glassy eyed and concentrating, nodding me to go on. Working in, slightly out, in again I teased and pushed, and slowly slid into her ass. Finally I felt I had filled her completely. God it was tight, but what a fantastic sensation for me, such a slick, warm feeling so different from her pussy. Her ass was contracting around my cock, squeezing it hard as I filled her, her orgasm so close on just this sensation. I looked at her, this gorgeous, sexy woman who had overcome one of her own taboos and seemed now to be enjoying this kinky pleasure. I was such a lucky man. Not only was Ali such a sexy attractive woman to look at and admire and be seen with, she was a hot and horny woman away from public view, with a mind to try as many things as she could, and I seemed to be the lucky recipient of this.

“How is it, shall I start to fuck your ass gently…?” I asked my lovely partner.

Ali bit her lip, and nodded.

So I did. I slid out a short way and drove gently back in, filling her a little deeper and feeling her gasp and react as I did so. Again and again I moved my cock in and out, her ass now easily accommodating its length and thickness as I worked it further and further out and in, but all the time taking it slowly so as not to hurt her. She was panting, wild thrashing of her head as the sensations built. I was beginning to get close to my own orgasm, the tense, tight sensations too much even for an already used cock. I found the plug and as I eased my cock out I slipped it into her pussy before thrusting deep into her ass again. Ali exploded, crying out and yelling like I had never heard before. Wild head movements were all she could manage, her lags and arms restricted by the bonds but she was still moving madly around with the heaving, contracting, stomach clenching orgasms now seeping through her. I felt the sensations around my cock, tight assed she was cumming around it, gripping it subconsciously as she peaked again and again. Finally I was able to start my thrusting again and exploded myself, filling her ass with my second load of cum that day, pulse after pulse of hot white cum going deep into her.

Finally it stopped, and her hair was lightly sticking to her sweat covered brow, the exertions too much. I quickly released the cuffs and we sank down, my softening cock still embedded into her no longer virgin ass. I kissed her as she burst into tears at the orgasmic relief of her tensing body, the pressure on her sexual organs beginning to subside.

“Was it OK?” I asked as I stroked her hair and cheeks.

Ali smiled… and whispered, “Mmm, not sure, you might have to do it again in case…”

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