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He had been in conflict with himself and his self-confidence, so she was going to help him realize who he was meant to be...
With one of her arms, she reached over to the side of the bed, beside the pillow where she stashed her toy and its harness. For easy access just in case she brought somebody home, she didn't think she'd bring somebody as perfect as Ashley here, but she supposed she lucked out.
Stealthily, she brought the toy around their bodies, taking care to peak open during their kisses and make sure Ashley wasn't looking. Thankfully he seemed so enraptured with her after she introduced him to the world of anal delights, so he didn't see. But she knew she would need a little more lube in order for him to not have an unpleasant experience. And their session of sloppy kisses seemed like the perfect source for some.
So mid-kiss, Selena pulled back, earning a little noise of disapproval from Ashley, but she shushed him again, and brought her free hand up to his lips. Tracing the kissable pink there with her digits, like she was rubbing some lip balm over them. And like candy to a baby, Ashley took the bait, closing his eyes and poking his tongue out curiously. Selena bit her lip as she watched him almost shyly lick her fingers. Indulging in the desire he felt downstairs, lifting his head just a bit to envelop her fingers in his lips and suck on them.
"Oou..." Selena cooed, watching such pretty lips sucking on her like that. It made her body feel hot, she was ready to get to the action, so quickly she slung the harness between her legs, using expert skill to clip it in the back and set it into place. One of her tools for pleasure already set in the slot and ready for fun.
She pulled her fingers from Ashley's lips and again replaced them with her own mouth, kissing him lustfully as she carried her saliva coated fingers down to the dildo, setup in the strap on harness. Rubbing the boys spit in to help lubricate it for penetration, stroking it like she was masturbating, getting as much of it she could all over the tip.
Then she scooted forward on her knees, situating herself more comfortably between his legs, and bringing her pelvis dangerously close to his vulnerable hole. Next, she ran her hands up Ashley's petite frame again, trailing all over his velvety smooth skin until she got to the underside of his arms, then kept going. Pushing up on his arms until they fell back, landing above his head, and she ran her hands up the skinny limbs until the got to his wrists and held them in place there.
He was probably gonna squirm, might get a little scared, she just needed to hold onto him until the initial fear passed, then he would embrace it.
She continued to kiss him, but in-between smooched, she spoke, "Are you ready baby?"
Again, all Ashley could do was nod, he was in a whole new world right now. How she held him down touched him everywhere, continued kissing and fondling him, everything was on fire. He didn't care about anything but her right now, and just wanted more.
No idea what was about to come.
"Okay...here we go..." She warned, ready to take his virginity, and to change his perspective on sex forever.
Selena lowered her hips, precisely aiming the dildo directly at his entrance. And the moment the bulbous tip of the thick eight incher touched his hole, his eyes shot open.
"Wait...what?"
With a good amount of pressure, and both her and his spit lubing him up a good amount, the tip of the fake dick didn't take long to carefully break through his anal ring. Piercing into his virginal hole, and immediately sinking in a few inches.
"AAAH!" Ashley gasped and screamed at the same time. Feeling something large, long, and thick suddenly breeching into his forbidden place that Selena had kissed a short while ago. It felt like a burning sensation in his butt along with being split in half at the same time as Selena sank the cock into him. "G-gah! Haaah....Se...Seleeena!? What are you...d-doingggg?" He moaned, both in pain and shock...and...
A wave of emotions slamming into him hard, he squirmed in her grip as she expected him too, but her hold on his wrists kept him in place, his legs still bent at her sides kicking gently, straightening and curling again as his body was overwhelmed with these odd sensations unlike anything he had ever felt before.
Selena softly kissed the side of his face and tried her best to comfort him, "Sssssh...relax baby...stay calm...relax...breathe..." Quietly kissing his cheek and neck.
"Aaaaahhhaaaaa..." He moaned again, feeling a tremor quake through his form. And glanced down over Selena's shoulder, down by her hips, he saw these strange leather straps wrapped around her hips and legs. Just above where her leggings were pushed down to, they hugged her tightly and disappeared around the front of her pelvis.
Where she was pressing tightly to his body...
"She's...she's..?!" His brain knew what she was doing, but couldn't manage to get past that thought, whether it be due to shock or disbelief. But either way it was happening.
Selena was fucking him.
It took maybe two or three minutes of steadily pushing and pulling the black, veiny textured dildo in and out of him before she finally managed to push it aaaaalll the way inside. Her pelvis touching Ashley's hip bones signifying that she had bottomed out. His inner muscles having to stretch to accommodate this odd, large intruder.
Ashley's jaw hung wide open, the burning sensation thankfully having passed, but now was replaced with this strange...full feeling. He didn't really know how to explain it but it was very...intense and...and...interesting...
Selena continued kissing him, her lips just making light, comforting smacking noises as she slowly rocked her body. Keeping him held down under her and controlling his little body with her own. She wasn't thrusting yet, just very carefully adjusting herself, making sure his inner muscles got all the time that they needed in order to relax and get use to the sensations.
Her lips made their way back over his cheek to his lips and gave them another kiss as well. Although his lips were still parted in panting gasps and had a little trouble responding appropriately.
"Are you okay?" She softly asked.
Ashley's eyes refocused on hers, "Y...yes...aah...what are you...why did you..." He kept speaking in fragmented sentences.
"Because baby..." She started, cutting him off. "I knew what you needed from the moment I met you." She chewed her lip and gyrated her body again, drawing out more mewling from Ashley. "Such a tiny, tight little body...so perfect in every way...ooh fuck...just thinking about how tight you are...ouu....wrapped around my cock..." Delicately she shimmied her hips, "It makes me so fucking hot..." She made sure to look into Ashley's eyes next, "You needed a girl like me in your life. And I needed a..." She paused, thinking about what she wanted to say next. "...sweet little thing like you in mine..."
Not just yet, she'd probably do well to save the dirtier stuff after he was good and broken in.
"Aaah..." Ashley groaned, "But...my...my butt..."
"It feels good doesn't it?" She interrupted him again, "Nice and full?"
His lip was trembling and he continued to squirm, "I...I don't knoooww ooohhh..." Selena began to draw her hips back, pulling the long dildo carefully out of Ashley's depths.
"Listen to me Ashley...just relax...I want you to feel...my cock inside you..." Moving her body slow, she pulled the strap on out almost all the way, until only the tip remained just barely inside, held in place by his anal ring. Then began to push it back in at a similar speed, "Feel every inch of it..."
"Haaaaahaa..." More submissive, practically pathetic sounds worked their way out of Ashley's throat. His body was having a meltdown, the foreign intruder invading his anus like this had everything flipping upside down. His belly flopped all around in his abdomen and every nerve was ringing the emergency bell. But what confused him the most about this whole odd coupling...was that his cock...Was so...incredibly hard... "Aaaaaaaahh..."
Selena set a slow, steady pace, pulling out almost the entire length of her dick, and carefully pushing it back in. Keeping Ashley's legs up and bent at her sides and his hands pinned above his head. A look of concentration and almost serenity on Selena's face and a look of conflict and confusion on Ashley's.
The pain of her movements had subsided, but now was replaced with something else. A strange feeling in his tummy that stopped his struggling, all the while Selena continued to whisper to him. "I...am really happy...you came home with me tonight...ouu...I knew I wanted you as soon as you walked into my life...I had to have you...nnf..." She began to nuzzle her face into the nape of his neck, tickling him a little. "Ohh yeeaaah...keep making those sounds baby...mmm you've got me so fucking horny..."
She sounded like she was really liking this! Ashley glanced over at her, seeing from her profile, her eyes closed and her teeth still gnawing on her lower lip. Plus she was making little noises of pleasure too!
"Is that...because of me?" He thought watching her body move, keeping that steady rhythm of thrusts. "I'm making her feel this good?"
"If...haah...you're okay...I'm gonna go a little faster now...alright?" She asked him breathily. Leaning up to watch his facial expressions as she asked. And much to her relief, he didn't look scared, or really confused anymore, he almost looked...interested. Like the pain and initial shock were gone, and now all that was left was the seed of anal pleasures planted in him. Selena planned to take full advantage of that. "If it starts to hurt...just tell me to slow down okay?" She threw in really quick as she leaned up on her elbows to watch him as she fucked him. Then began to up her pace.
Before she had been racking in maybe one slow thrust every two to three seconds, but now she upgraded to about one thrust per second. And wasn't being as gentle as she was when they first started.
Ashley's jaw dropped a little lower as this happened and his legs began to sway back and forth in the air with the force of her stronger thrusts. "Aah! Aaaaah! Haaah...aaaah!" His moans now coming out regularly, not spaced out or reduced to tiny squeaks. Now he was beginning to feel...something.
Every time she pushed into him, he felt that large rubber cock touching something deep inside him. He didn't know exactly what, but every time she did, it sent an electric whip cracking throughout his tunnels, which multiplied the sensations of his anal walls being stretched out. He didn't know that he could feel something so intensely, something that made his toes curl and his voice sing out a chorus of girly moans in response.
Only now did he really begin to process what he was feeling, pleasure. He had no idea something going in and out of his butt could feel so incredible. Plus, his view was pretty great too, as Selena leaned up to start thrusting more, she exposed her busty chest to him. Showing off her twins as they swayed with each motion, her tight abs rubbing against his little dick creating a friction that made it practically squirt out precum.
Selena also was breathing heavily over him, both of their bodies were beginning to work up a thin layer of sweat. Exerting these pent-up sexual desires and giving the both of them a workout. The bud of the dildo pressed firmly onto her clit with every push in, sending waves of bliss coursing through her own veins as well.
"It's...haah...good...isn't it?" She asked between ragged breaths. And at first Ashley didn't answer, still a little too embarrassed to outright admit that he was very much enjoying something plundering the depths of his booty. But that didn't stop her from asking again, "Go ahead baby...aah...tell me...you like it...don't you?" She smirked, pouring on a little dirty talk to help Ashley get even more into it.
"Uuuhnnn!" Another girlish moan erupted from within him before he replied, "Aaayee...yyy...yyyeess..." He choked out, "Yyyeeesss..."
"Mmmm there you go baby..." She lowered herself down again and kissed him once more. Staying connected with his lips this time though as she thrust into him.
And up'd her pace some more...
"Mmmmmm!" Ashley moaned into her mouth as her hips moved faster, fucking his ass with determination now. The bed making quiet creaks in tandem with her harder shoves.
Eventually she unlocked their lips and sat up, only this time, she didn't plan on leaving Ashley on his back. "Aaahh...come here Ashley..." She released his hands, but replaced her hold on them with a new hold around his arms.
She scooped up his light body, lifting him off the bed and sat back on her heels. Placing Ashley into her lap and sitting him down fully on her cock. "Uughh!" He squealed again, squinting one eye shut and gritting his teeth as the dildo buried itself further inside. It felt like it was touching his little tummy it was going so deep.
But she didn't stop there, Selena picked Ashley's supple legs up, wrapping her strong arms around them and essentially bear hugging the tiny boy in a tight grasp. His feet ending up over her shoulders and his arms pinned down by his sides. Unable to move or really even wriggle about in her tight grasp. She had him entirely under her control.
"I'm gonna fuck you now baby..." She warned him, looking down at his adorable, ablush face. Baby blues eyeing her nervously, pleading with her... "Are you ready?" Begging her for...
Ashley hesitated for just a second, but when his muscles flexed around the thick tube plugging up his love tunnel. He knew he had to have it, his eyes were begging her for more...
He nodded. "F...Fuck me..."
That was all she needed, and Selena used her upper body strength to effortlessly lift Ashley up and impale him back down on her cock. His eyes immediately both squeezing shut and his face crumpling up, contorting with pleasure and intense joy.
Selena watched him with a wide open-mouthed grin as she bounced him on her. His weight helping to push the dildo down onto her pussy and rub it harder and harder. She tilted her head back and let out a few ecstatic moans of her own as she indulged in the pleasure her boy toy offered her.
The dildo hammering so far into Ashley and squishing his innocent little prostate with every deep curve. His dicklet was crying tears of joy as her cock milked the little pleasure button for everything it had.
Ashley's voice arched, nearly a full octave higher than what he normally spoke at, which was already pretty high-pitched already. But now, he was practically full on screaming like a girl as he was manhandled by his ebony Goddess. Working him up and down on her big fake dick like a sex toy, body comparable in weight to a glass of water in her hold.
This felt like it went on forever, Ashley bouncing, his world whirling, his toes curling, his tummy twisting and body spasming in forbidden delight. All the while Selena stared him down with a look of predatory lust, taking what she wanted from him, robbing him of his innocence in the most delicious of ways. Flailing him about on her dick like a pleasure doll, and he was in love with the idea of it.
His brain couldn't think of anything other than getting more pleasure, as the coil in his belly began to tighten. Everything else was going blank. "AAAH! HAAAH! HAAAAAAHAAA! OH GOD! OH GOD SELENA! AAAH! I CAN'T! I CAN'T TAKE...ANYMOOOREEEE AAAAHHH!" He screamed, looking into her orbs, looking as if he was about to cry himself.
Selena grit her teeth, fuck his face looked so hot. "Ugghyeeah...are you gonna cum baby?"
Ashley's head nodded faster than it had for anything else tonight, "YES! YES! YES! AAAH I'M GONNA CUM! OH GOD I'M GONNA CUM!"
"Aaaahhh...do it baby...ooou cum for me...oohh fuck!" Selena grunted, his minimal weight really had to be shoved down onto the dildo in order for it to rub her hard enough to get her close. But the knowledge that he was almost there definitely helped guide her closer to the edge. "Ugggghhhyyyeeessss...cum Ashley...I want you to cum for me...do it...do it!" She held him tight, bucking her hips up into his as he came down onto her.
Her words mixed with the massive stimulation from the hard pegging was enough. And for the first time in his life, Ashley felt the rising tingles of an orgasm begin to bubble up, without ever once having his cock touched. "AAAH! YESYESYEYSYESYESSSS! AAAAAAHHHHHHH!" Ashley let out a full scream as his climax hit him hard.
She could feel his little prick squirting out a nice warm couple of shots on her chest as it twitched, desperately firing out his first ever prostate orgasm. "Ooohhh that's iit...yeeeess..." Selena growled, continuing to bounce him on her, loving his desperate cries of release and allowing him to ride out his high.
It was unbelievable, Ashley had never quite experienced anything so intense. His cock throbbed and his body spasmed, his anal muscles clenching up around the thick rubber dildo while it wrung out his little p-spot. His eyes rolled back and he convulsed at the peak of his pleasure, feeling it surge throughout him so hard. He literally couldn't take it; his small form quickly became overwhelmed. His toes pointing straight out and his back arching harshly.
Up until his brain turned completely to mush, all he could see was white, and after one final pulsation from his singing prick...
Ashley passed out.
His tiny frame slumping forward in Selena's grip and going completely limp. At first, Selena didn't even realize anything was wrong up until she dug her face into his neck again and kissed him some more.
She hadn't reached her own climax yet, but boy did she get really close. If she kept going she was sure she could get there, but when she realized that there was literally no movement or reaction from Ashley at all, that's when she figured out he was gone from the waking world.
"Oh shit." Selena cursed, carefully maneuvering Ashley's frail body in her grip so that his legs fell from her shoulders and she could look at his passed-out face more directly. "Ashley? Hey? Sweetie?" Out cold, he was breathing of course, but definitely unconscious. "Craaap..." Selena groaned, "I guess I was too much for you huh?" She chuckled at her own joke but then got a little more serious. "Well...if you're out then I guess no orgasm for me cause I'm not gonna keep going without you baby." She talked to him as if he was awake, even though her words fell on deaf ears.
But that was okay, she was willing to forgo a release of her own if it meant not hurting Ashley. She didn't wanna keep going and use him while he was unconscious, that was a little too rapey for her tastes.
So instead, she carefully shifted their bodies around on the bed, spinning his little form in her hold so he was facing away from her but not removing the dildo from his ass. He was so light that it was actually much easier than one may think, especially without him squirming. She then laid the two of them down on the bed, scooting up to him from behind and spooning him closely. Pulling her blankets up over their bodies so that they may go straight to sleep this way.
Well, at least she could go to sleep tonight knowing that she gave him an orgasm so good he literally fainted.
She wanted to giggle at that, but held back the urge to and instead just gave Ashley one more little kiss on the cheek. Sitting up on one elbow while she watched him sleep, she trailed her finger up and down his bare arm.
"Sorry if I was a little forward...but...I knew I had to have you. You're just so perfect..." She spoke softly, "I've been a little...lonely lately and...I get the feeling you might've been too. So...I hope you forgive me for rushing into this and...I hope you stay..." She leaned down and kissed him again, "I really hope you stay."
