Toying with Aria's ass

Tom had been using a popular fetish website for years, mostly to browse other people's content. Occasionally, he would add his own writings and pictures featuring his fucking machine and anal sex toy collection. One day, he received a message from a beautiful woman in his area. She said she was new to the site but had noticed his collection and expressed interest in trying them out. However, she made it clear that her only requirement was that they engage in anal play exclusively.

They agreed to meet up at a hotel, where Tom planned to show her his fucking machine and extensive collection of dildos. He also prepared a large batch of J-lube in a container for their play session. Prior to their meeting, Tom inquired about the woman's experience with anal play to determine what type of toys she could handle. She shared that she had only experimented with anal play using toys on her own and was eager to have a partner who could help her push her limits with larger toys. She even sent pictures of her biggest toy, a 2-inch diameter butt plug.

When she arrived, they both knew it was going to be an amazing night. She was dressed in a pair of soft, worn jean shorts and a plain white crop top that revealed a belly piercing. After introducing themselves for the first time in person, even though they had been chatting online for a few weeks, Aria expressed excitement about their play session but admitted to feeling a little nervous. Tom reassured her that it was understandable and that they would start off very gently.

Tom brought Aria inside and began showing her his collection of toys, starting with his dildo collection. The first toy he presented was a small, 5-inch long silicone dildo that was about 1.25 inches in diameter, which he believed would be no problem for someone with her level of experience. Aria blushed, which Tom found adorable, but he didn't say anything further. He then proceeded to show her the rest of his collection, including a slightly larger realistic-looking dildo, a fantasy dildo shaped like a horse cock that had an insertable length of about 8 inches, a more flexible dildo with an insertable length of around 10 inches, and a clear glass cylinder plug that was around 6 inches long and 2 inches in diameter.

Aria's eyes widened when she saw the glass cylinder plug and asked if it would fit inside her. With a twinkle in his eye, Tom reassured Aria that they would start off slowly and work their way up to that toy. He promised that by the time they got there, it would slip in easily.

Tom proceeded to show Aria the fucking machine in detail, pointing out the variety of attachments it had and the various angles it was capable of. He then plugged the machine into an extension cord and demonstrated the range of speeds and thrusting depths it could achieve. As he spoke, he noticed Aria's breathing becoming heavier, and he could see the arousal building in her eyes at the idea of having a dildo attached to the machine and penetrating her tight ass.

After discussing their plan, they agreed to start off slowly with fingers, then move on to the smaller dildo, and gradually work their way up to the larger ones as the night progressed.

Tom asks Aria to give him a bit of a strip tease show. She complies, taking off her crop top to reveal a white lace bra. Tom wonders if it matches her panties. He then asks her to spin around, facing away from him, dressed in her jean shorts that perfectly cup her small, firm cheeks. Aria bends forward into doggy position on the bed, looking back at him for a moment before looking away demurely. Tom comes up behind her and struggles to get the tight shorts down for a moment, but Aria assists him by releasing the button and zipper, which causes them both to giggle. Tom pulls the shorts down little by little, exposing the brilliant white of her untanned ass cheeks. He is ecstatic to see that she's wearing full white panties, hugging her ass cheeks and creasing gently into her crack.

He runs his hands over Aria's smooth skin, starting at her upper thigh and running up towards her firm ass cheeks. He squeezes her right cheek firmly, eliciting a moan from her, before sliding his hand around to the left side of her ass and repeating the process. With his other hand, he reaches between her legs and cups her pussy through her panties, rubbing her hard clit with his thumb. As he does, he notices the fragrant wet patch in her panties and leans forward to take a big sniff, startling her and making her blush. He tells her that she smells amazing, which makes her smile shyly.

Moving his face closer to hers, their lips almost touching, Tom kisses her lightly on the lips, lingering for a moment before moving back slightly. Aria opens her mouth slightly and he slides his tongue out, gently flicking her tongue with his own. He feels her body respond to this and she moans a little louder, pressing her body against his. Tom reaches back to unclasp her bra and free her small tits. Aria feels self-conscious and looks for affirmation, but he reassures her that they're beautiful and that he's more interested in her gorgeous tight ass than her lack of tits.

Tom takes Aria's hard nipple in his mouth, sucking gently before flicking it up and down with his tongue. He repeats the process on her other nipple before sliding his hands down her stomach and grabbing her panties by the waistband, pulling them down her legs forcefully. He pushes them all the way down to her feet, revealing a completely shaven pussy. Aria has large inner lips that poke out from between her outer lips, which Tom finds incredibly attractive. He grabs her ankles and spreads her legs wide apart, revealing her tight puckered hole to him. He licks her juices from the inside of her knee, up her inner thigh, and to the apex of her pussy lips. He can taste her sweet arousal, but he wants to taste more.

Using one hand on each ass cheek, he spreads them apart as far as they will go, then releases them back together again, watching how her tiny little sphincter reacts and enjoying the crease her butt cheeks make when they come together. While he holds her cheeks together, he licks up and down the crack with the flat of his tongue, causing her to giggle and squirm. He parts her cheeks as much as he can, bringing his face closer and closer to her puckered hole. She can feel his breath on her tight forbidden hole. He uses his tongue to trace a ring around her tight pucker, coming closer and closer to the center of her anus with each swirl. Eventually, he uses the flat of his tongue to press directly onto her gradually dilating anus. It's as if she's trying to push herself away, but he persists, and soon enough, he's pushing himself inside. She moans loudly, and he immediately feels her muscles relax around his tongue. He starts to lick up and down her anal canal, pausing periodically to flick his tongue across her sensitive opening.

When she starts to squirm again, Tom asks her if she likes it. Aria replies that she doesn't just like it, she absolutely loves it. This is the first time she's ever had a partner paying attention to her backdoor and the first time she's had a partner this enthusiastic about providing oral sex.

Tom continued with his oral ministrations for a while before grabbing his container of lube. Aria looked on in anticipation as he opened the lid and poured some into his hand, spreading it around until his fingers were coated. He then slid two fingers into her pussy, holding them in place while he lubricated her asshole. After he finished, he rubbed her ass with his slickened fingers before pressing them against her puckered hole.

Tom withdrew his fingers from her puckered hole and changed his mind, telling Aria to give him a show with the initial penetration. He handed her the bottle of lube, and she coated her fingers, rubbing them in slow circles over and around her anus. Tom watched as her hole started to pucker and the outer sphincter began to relax slightly. She re-lubricated her fingers and rubbed them over her little pucker a few times before bearing down and starting to ease a finger in gently. It slowly sank in to the first knuckle, then the second knuckle. Tom could see a wave of lube forming around her finger as the tight sphincter pushed the lube along her finger. Eventually, her finger was buried as far as the angle of her hand and wrist would allow, almost all the way into the palm. Tom let out an involuntary breath that he didn't know he'd been holding. "Wow, that was incredible," he told her. She moaned and told him to imagine how she was feeling.

Tom could see Aria flexing her muscles around the finger inside her ass and reached around her to grab a handful of her hair. He pulled her head back so she was facing him before kissing her deeply on the mouth. She kissed him back passionately, her tongue twirling around his own. He broke off the kiss and looked at her with lust burning in his eyes.

"Loosen yourself up for me a bit, baby," Tom whispers in Aria's ear. She complies by flexing her anus and moving her finger in and out. Soon, she's thrusting her finger at a slow pace, then a medium pace. She pauses her thrusting to pull the finger out and apply more lube. As her finger exits, Tom sees a hint of pink/red inner tissue as her outer sphincter pulls closed again. Aria goes back in with her freshly lubed finger and then adds a second one. "Don't you want to take over from here?" she asks with a sultry glance over her shoulder, her hair falling forward over her face slightly.

Tom takes the bottle of lube back from her and lubes up a finger, easing it into her tiny, tight, hot, and moist hole. He feels the way the sphincter muscle is clamping down on his digit before easing up and letting him in. He pulls out and adds more lube, swirling the finger around her hole, using gentle circular pulling motions to help convince both the inner and outer sphincter to relax and open up. When he pulls out again, her beautiful little pucker gapes just a fraction for a tiny moment before closing down again and then winking a few times by reflex. He lubes up again and then eases first one finger and then the second into her tiny hole, causing her to gasp and moan. He eases the fingers in and out, twirling and swirling. He uses his mouth to apply pressure to the sphincter as his fingers swirl in and out, deeper and deeper. Sometimes he pulls completely out, sometimes halfway, sometimes he thrusts with short motions deeper inside. There is so much lube that it's dribbling down the sides of her ass cheeks and mingling with the liquid escaping from her drenched pussy.

Tom instructed Aria to hold her right ass cheek tightly open while he used his left hand to hold her left cheek wide open. While doing this, he kept thrusting his fingers in and out a few times, and he noticed the muscle of her sphincter start to loosen up and show a bit of an air gap between her sphincter and his fingers. Occasionally, he could hear some squishy wet sounds as he thrust his fingers. He pulled out, and the combination of the relaxation of her sphincter and the spreading of her ass cheeks caused her anus to remain gaping open for a second or two before closing back up tightly again. He could see her anus pulsing slightly with anticipation of what was to come.

Tom then got the smallest dildo ready and covered it with an excess of lube. He rubbed some additional lube directly onto her anus, feeling it twitch with excitement and anticipation. He rested the tip of the dildo against her ass, and she bore down slightly, allowing the dildo to slide easily into her relaxed anus. He pushed in gently, inch by inch, until he felt a slight resistance and adjusted the angle slightly to account for the internal bends of her rectum. Eventually, he had the dildo buried balls deep inside her ass and paused to enjoy the sight of her anus tightly gripping around the dildo.

He guides Aria's hand to the base of the dildo and instructs her to hold it deeply inside as he prepares a lube launcher filled with lube. Tom takes control of the dildo again and wiggles it gently before withdrawing it completely, telling her to remain relaxed. He gently eases the lube launcher completely inside before using the plunger to squirt the lube contents deep inside. He then slides the dildo back into her deeply lubricated rectum.

Moving the dildo slowly in and out, Tom rotates it, pulling almost all the way out before pushing it back in. He can feel Aria's anus contracting slightly each time he pulls out, and relaxing each time he pushes in. Eventually, her anus becomes incredibly relaxed, and a stream of lube pushes out from around the dildo as he thrusts. He watches the thick sticky stream easing down the inside of her thighs with delight.

Tom removes the dildo completely and licks into Aria's slightly gaping anus before it closes up, causing her to gasp and shudder. He then brings the dildo to his mouth and sucks it, tasting the lube mixture on the dildo. He offers the dildo to Aria to suck, and at first, she is hesitant, but then realizing that he's already had his tongue directly inside her anus and the very same dildo in his mouth, she relents and licks the tip gingerly. It is not at all unpleasant, as she was expecting it would be, and she raises her eyes to meet his, seeing the unbridled lust he is feeling watching her commit this lewd act.

He pushes the dildo balls deep inside her once more and then withdraws it to refill the lube launcher, squirting another full launcher of lube deep into her rectum. As he continues to thrust the dildo faster and faster, Aria starts making unintelligible moaning and groaning noises with pleasure, and her pussy starts to leak a small stream of clear liquid as she has an anally induced orgasm. Tom can feel her rectal walls clamping and releasing around the dildo with the spasms of her orgasm, so he slows the thrusts and times them between the contractions. Eventually, he stops thrusting with the dildo about halfway inserted, leaving Aria delirious with pleasure and unable to move or think straight.

While Aria recovers, Tom prepares a slightly bigger dildo with realistic ribbing and generously coats it with lube. He spreads additional lube directly onto her relaxed and twitching anus using his fingers. Tom brings the dildo up to her anus and uses gentle pressure and release motion to gauge her readiness until her sphincter relents and allows the dildo to slide slowly all the way to the base, with only a gentle re-alignment around halfway through. Her rectal walls have relaxed to allow easy entry and her anus is quite dilated. Tom prepares another lube launcher and injects it deep inside her after removing the dildo. The length of this dildo means that the tip is pressing up against her recto sigmoid junction when it's inserted balls deep, so he needs to go gently at first to allow the insides to relax. He tells her to bear down gently as he thrusts, which she does. Soon he can feel the junction start to relocate and slip around the tip of the dildo as it opens up and moves slightly downwards. He picks up speed, ultimately thrusting the dildo balls deep, making a slapping noise as the balls contact her flesh. Aria is making grunting noises of pleasure and soon has another anal orgasm, collapsing onto her side in a blissed-out state. Tom leaves the dildo deep inside her while he prepares the next biggest dildo and another lube launcher full of lube. Eventually, her spent anal canal pushes the dildo out, and it flops onto the bed in a puddle of sticky lube juice. Tom licks it clean and then gets the next largest dildo ready for her. This one is just shy of 2" diameter and quite long. He uses lots of lube and spreads it liberally over the head of the dildo and her anus. He introduces the dildo gently, causing her to grunt as the thick tip presses against her rectum and slides slowly inside. Tom gently guides the dildo as deeply as it will go, knowing that because of the length, this one will not be able to go to the base at first.

He pulled the dildo out and squirted another deep launcher of lube, reinserting it right after. Starting with a gentle thrust to the maximum comfortable depth, Tom picked up speed soon after. He asked Aria to bear down while thrusting, feeling the tip of the dildo negotiating the recto-sigmoid junction. He kept going, gently pushing deeper and deeper, unable to reach the base with this dildo yet.

Tom removed the dildo and lubed up a longer, slightly thinner, and more flexible one. He squirted lube deep inside before reinserting it to the previous maximum. Aria was asked to bear down gently while Tom rotated the dildo slightly, pulling it back and then thrusting it deeply, over and over again. Soon, the dildo reached new depths, and after a few minutes, Aria was able to take it all the way, at which point Tom pulled it out and re-applied a deep lube launcher full to her sigmoid.

Starting to thrust the dildo all the way in, Tom sometimes pulled it out until just the tip remained inserted, other times only about halfway. He started thrusting only about 1/4 of the length of the dildo in and out, but all the way inserted. Aria couldn't handle the pleasure she was feeling and her body shook. She was completely lost in semi-orgasmic bliss.

Finally, Aria orgasmed with a flood of liquid from her pussy. The contractions from her anus pushed the dildo directly out of her ass, and Tom lost his grip, causing it to shoot off the bed, landing with a wet splat on the floor!

At this point, Aria's anus is partly giving up, gaping between winks and appearing very dilated and relaxed. Tom grabs some lube and inserts first two, then three lubed fingers as deeply as he can. He can feel the distinct band of muscle at the recto sigmoid junction with the very tips of his fingers. He asks Aria to bear down and feels the sling of muscle travel down slightly over the first digit and a half of his fingers buried deeply inside. He jiggles and slightly rotates and splays his fingers deep inside, feeling the muscles relax and become more pliable. He pulls out, adds lube, and then reinserts first two fingers, then three, and works up to four fingers. He can feel how open and relaxed Aria's anus is now, she's ready for the next step!

Tom brings out the glass cylinder dildo and shows it to Aria, explaining how it will give him a clear view of her stretched anus once it's inserted. He lubes it up and approaches her anus, which, despite being relaxed, resists the dildo's size and blunt shape. Eventually, the gentle pressure causes her anus to open up, and Tom can see the inside of her anal canal through the clear glass of the dildo. He gradually inserts it deeper and deeper, marveling at the way the walls of her rectum remain relaxed and open even as he withdraws the dildo slightly. He takes a picture of the clear glass plug gaping her anus, showing it to her before deleting it and asking her to roll over onto her back.

Aria complies, and Tom is treated to the sight of her open pussy folds and the clear plug still stretching her anus. He positions himself between her legs and savors the scent of her arousal before licking at the girl juices escaping from her pussy. He then moves up to her clit, flicking his tongue back and forth over it before focusing on broad vertical strokes. He gauges her body's reactions to find what drives her wild and focuses on that until she has a mind-blowing orgasm that makes her squirt all over his chin and the bed.

Her anus is desperately trying to clamp down with the contractions from the orgasm but is held wide open by the enormous plug, adding immensely to the pleasure of the orgasm. The orgasm lasts longer than she ever thought possible until she pushes Tom away, and the plug falls out onto the bed. Her anus is a gaping, inflamed red mess, but she is relaxed and happy. At this point, she is not ready to try the fuck machine, as her body is unable to handle any more pleasure for now.