Trust Me, Baby

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She didn’t know that she liked anything in her ass yet, but Dale planned to teach her that tonight. After 4 weeks of dating, Lucy and Dale were still red-hot and fucking nearly every day, but she still hadn’t really let him near her butt. The exception was last weekend; they had both woken up in the small hours of the morning, and Dale heard a familiar happy sigh when he had reached around Lucy’s front and began lightly tracing circles around her areolae. When she started to push her ass back against Dale’s crotch, he felt his half-erection quickly balloon to its full length and girth.

Lucy’s ass. Dale could have written poetry about Lucy’s ass. It’s been a source of embarrassment for her, because it’s pretty large for her thin frame. Her big round cheeks are soft and faintly dimpled. They jiggle deliciously when spanked or when Dale fucked her from behind; he loved to watch them.

On that evening, Dale’s cock swelled right in between her butt cheeks. He knew she felt it. Then, to his utter shock and delight, she began grinding up and down his dick. With her asscheeks. Dale wasn’t a huge guy, about 7″ inches hard, but his dick was girth-y and had a bulbous mushroom head. There was no way she wasn’t doing it on purpose, the way she clenched her buttocks together, squeezing his cock tight. Sliding up and down her luscious crack was heaven, and Dale didn’t dare inch too close to her anus, worried she would recoil.

Eventually, Lucy rolled over to face him and they proceeded to have particularly raucous vaginal sex. Dale would never know, but as his thumb rubbed an orgasm from Lucy’s clit while he fucked her doggy-style, she replayed the memory of his pleasure at playing with her ass.

Dale thought that with some wine and persuasion, she could be ready. Two weeks after Lucy had jerked Dale off with her asscheeks, he decided it was time for her to learn the full pleasure-potential of her back passage. It seemed appropriate that Lucy had worn a tight sweater dress that perfected hugged her heart-shaped ass to the party they had attended earlier in the evening. He had smiled inwardly at her innocence of what awaited that ass later.

When they returned to Dale’s apartment, he wasted no time. Sitting on the edge of his bed, he asked Lucy to lay belly-down over his knees. At this point, Lucy still had no reason to suspect this was anything out of the ordinary; Dale loved to diddle her pussy while she was laid across his knees (although, she was unaware it was because he loved to watch her soft butt jiggle as she came).

He reached underneath her hips, and softly traced from the buttom of her pussy lips to the top of her slit. He could already feel her wetness, and stroked her like this for a few moments before he began shallowly dipping his finger into her damp folds and spreading the moisture upward. Lucy’s breathing quickened as Dale stroked loose circles closer and closer to her clit. When he lightly brushed his finger over it, she inhaled sharply at the gentle, delicious jolt.

Dale slid his finger down again, slipping it into her very wet pussy. This time when he withdrew his well-lubricated finger though, he began spreading back towards her asshole. Lucy started at the feeling of having her ring touched.

“Dale? What are you doing?”

“Do you trust me?”

“I do, but I’ve never had anyone touch me there.”

“This might be weird at first, but I promise it will pay off.”

“Okay, I trust you.”

Dale couldnt believe she had agreed that readily. He wanted to push his whole finger up her butt right there to celebrate, but he knew it would be uncomfortable for her. Instead, he picked up the vibrator he kept for their nights together, and gently pressed the tip against her anus. He had no intention of inserting it, as it was too big for an ass virgin, but he knew it would feel good against her sensitive ring. He turned it on.

“Don’t worry. I’m not going to insert this.”

With that, Dale saw the worry on Lucy’s face quickly dissolve into as expression of relaxed pleasure. The vibrations made her asshole pulse and sent tingles through her pussy and thighs. Despite her embarrassment- and she really did feel embarrassed that her boyfriend was looking at her asshole- she had thoughts of him pushing the toy into her and feeling the tingles even deeper. She began to whimper softly. Dale was delighted at her delight.

After a sweet and agonizing couple of minutes, Dale began to apply more pressure to her tightly bunched ring. The pulsating in her anus began to intensify. Lucy felt her rear end- the backs of her thighs, her buttcheeks, her asshole begin to loosen as she gasped and sighed in ecstacy. To her disappointment, Dale switched off the vibrator. She felt his finger replace it and he began to apply gentle but firm pressure. His fingertip slid easily inside her before catching at his knuckle and pulling at her delicate pink star. It drew an adorable grunt of surprise and discomfort from Lucy that appealed to Dale’s more sadistic, perverted tendencies. With a slightly rougher touch, Dale applied even firmer pressure while using a screwing motion; her asshole began to stretch over his knuckle.

“Ah- canlı bahis ahhhhhhh- ahhhh” said Lucy, as the largest part of Dale’s knuckle sank slowly through that little hole at last.

“Trust me, Baby,” said Dale, as he wiggled his tightly constricted finger in her back tunnel. Lucy tried to relax her muscles despite the strange sensations invading her ass. She did trust him with her pleasure, and she had to admit to herself that the stinging in her sphincter had taken on a strangely erotic quality. Lucy’s butt muscles and elastic opening started to slacken, allowing Dale’s finger to roughly drop the rest of way into her. She couldn’t help but gasp. The finger in her back passage made her feel intensely full, even bloated; his digit was thick and at least 3 inches of it were inside her.

Fuck, this woman feels good, Dale thought as he attempted to swirl his finger in a circular motion. Lucy tried not to wince as he digitally probed her tender rectum. It was only necessary for her to tolerate the discomfort for a couple of minutes, as she grew accustomed to the intrusion quickly. She still felt self-conscious, but was unable to stop herself from lifting her hips to push her butt further onto his finger. Dale slowly began to withdraw it from Lucy’s anus. She started to protest, but before she could make her petition, Dale firmly pushed the digit back into her ass. Her anal muscles twitched and she yelped, though Dale noted a breathy, still latent desire in her voice. He wiggled his finger in her bottom again for a moment before repeating the withdrawal and swift re-insertion. Lucy’s rectal walls were beginning to loosen their iron grip on Dale’s finger, seemingly with each torturous pump to her asshole. She was now moaning softly, guiltily enjoying her first anal finger-fucking.

When her tight ass had grown fully supple to the digital massage, Dale produced its next visitor: a string of four closely-set small beads, each about an inch in diameter. Lucy’s eyes grew wide with concern when she saw the toy.

“Dale, that’s weird. I’ve never had a toy back there and those balls look really big.”

“How are you going to take all of ME if these are too big?”

There, he had said it. Dale could no longer pretend that fucking her in the ass wasn’t where this was going.

“I don’t know if I can take it. I’m nervous, Dale.”

“Well,” Dale said, switching the vibrator back on, “I can understand how you feel that way, but…” he pressed the tip of the vibrator against Lucy’s anus again, “you might find you like it. You might be surprised. “

Lucy began to moan loudly as Dale applied even harder pressure on the toy this time, pushing the pulsating tip just inside her outer anal ring. She felt light whimpers begin to escape her lips. Perhaps he was right.

“O-okay,” she whispered, “I’ll try.”

Dale withdrew the vibrator. He picked up the anal beads and drizzled oil on each ball. Lucy shivered at the size and felt a chill up her spine when she felt its cold, broad surface press against her butthole for the first time. He marveled at how tiny her star looked next to the bead before beginning to push firmly against her hole. Lucy gritted her teeth and squeezed her eyelids shut as the top of the ball began to disappear through her outer ring. The widest part pulled ludely at her asshole, make her groan with embarrassment and at the strange, overwhelming pressure. Dale smiled devilishly at the sight if her little ass struggling to consume the full width of the bead. Lucy held her breath as he pushed harder, finally lodging the bead in her rectum and allowing her inner sphincter to close shut around it.

The bead felt heavy and large in her ass. A moment later, she felt the second ball begin to press into her. Lucy’s ass had become more pliant and she felt only minor discomfort this time as her anus stretched over the diameter of the bead. It was driving the first bead further in, gently probing her back passage; there was a stinging sensation mixed with occasional tingling. When the second ball had been fully buried in her, Dale pulled lightly at the cord connecting the beads, tugging the second ball partially back through her hole.

“Ooooooh,” Lucy squealed as the mouth of her little hole stretched backwards over the bead. When it was again stretched over the full diameter, her anus expelled the bead with a popping sound. A wave of embarrassment rolled over her as Dale chuckled. What a cute, unwilling little butt. This time, he was able easily reinsert the bead with light pressure; Lucy drew her breath in sharply as it popped back into her rectum. Two beads in her rear end felt intense.

She almost asked him to stop when Dale began to push the third bead in. Her anus had slackened, allowing it to pass with relative ease, but the thick beads were pushing deeper into her bowels, feeling impossibly heavy and extremely deep.

“Ugh” she said as her asshole swallowed the fourth bead. Her butt felt so stuffed and full; the beads were uncomfortable, but they didn’t hurt. Despite the strange tension and embarrassment, Lucy was beginning to like the feeling of having her ass filled.

Her cheeks were bahis siteleri faintly trembling as she adjusted to being stretched. Dale savored the view of the looped handle of the toy disappearing between her thick, quivering cheeks. He caressed the small of her back before slipping his hand underneath her hips. He traced the slit of her pussy as she shivered with delight, noting that she was wet with arousal.

Dale slowly caressed her slit from her perineum toward her front with a feather-light touch, dipping in just enough to spread her moisture upwards toward her little hood. Lucy moaned as his finger tugged gently against it at the end of each long stroke. Every so often, he hugged her whole mound, softly pressing her lips and making her smile at the delicious warmth of his hand.

Sliding one finger into her slippery pussy, he relished in her silky wetness which had so lovingly hugged his cock so many times. His finger ticked her insides delicately. “Dale…” she whispered tenderly. He drew out her wetness and began to draw circles around her most sensitive place, starting lazily and loosely and gradually targeting her pleasure center. Her clit grew swollen and her breathing quickened in anticipation of the ecstatic jolt she knew was going to be delivered.

When Dale brushed her clit at last, Lucy cried out softly. His finger stroked warm pulses through her pussy. As her pussy and asshole contracted with pleasure, she became acutely aware of the beads holding her back passage open. The fullness was intoxicating and only became more pronounced as Dale’s circles tightened on her exposed clit.

He began flicking his finger up and down over her little button with light pressure but vigorous speed, and Lucy was gasping and moaning in pure bliss, feeling a building tension in her pussy, hips, and ass. His tickling touch sent waves of warmth and butterflies into her belly.

“Oh,” Lucy said “Oh fuck, fuck, I’m gonna come in a minute.”

Dale felt his cock twitch, loving the sight and sound of her orgasm. He continued to strum her swollen clit for a moment more, and then Lucy cried raggedy as the first pulse of her climax caused her muscles to contract. Dale watched her luscious ass dimples deepen as her buttocks tightened and clenched together. Her pelvis was seizing and she began to grind her hips uncontrollably as the spasms overtook her. She could feel her tightening and loosening rectum throttling the beads; they held her ass relentlessly open, intensifying the luxurious pulsating in her rear. Dale grinned evilly to himself, watching her gorgeous asscheeks jiggle.

Just as her orgasm peaked, Lucy felt her anus suddenly pop open as Dale jerked the beads from her ass. She shrieked with surprise and sheer ecstacy as her sensitive ring stretched and winked shut- one, two, three, four times-in quick succession as each ball burst out of her tightly clenching sphincter, making lude puckering noises. It was the most intense orgasm of her life.

Her breathing was still returning to normal when Dale smugly asked “So…have you surprised yourself?”

Lucy ignored the question. “Please,” she breathily said “I’m ready. I want to feel you in my ass.”

The success of Dale’s plan surprised even him. His cock was like a steel spike, he was so hard for this woman. He literally could not believe it was about to be up the most perfect ass he’d ever seen and furthermore, that she actually begged HIM for it.

“Get on all fours.”

She complied. Her shyness was gone and she arched her back wantonly, pointing her flared, rounded ass back at Dale. He knelt behind her, and placing a hand on her upper back, gently pushed her torso down so just her ass was in the air and her face was on the bed. He produced a bottle of lube from the nightstand and pushed the nozzle into Lucy’s anus. He squeezed firmly, wanting a fairly juicy load to ease her first anal fucking. She felt the cool liquid shoot into her, coating her tight back tunnel.

Finally, Dale lined his cockhead up against her loosened anus. It was slightly puffy from friction and no longer puckered. It was still going to be a tight squeeze, though; his mushroom head was large, a broad 2 inches in diameter. He would have to take it slow, giving Lucy’s ass lots of time to adjust. Guiding his cock with his hand, Dale begun to push into her virgin butt.

Feeling her backside open, Lucy had a moment of panic at the size of the intruder. Her elastic ring inched over the first millimeters, slowly submitting to its final invasion. The feeling was indescribable for Lucy; part of her was afraid her asshole was going to rip apart, but this fear was overridden by her hunger to feel Dale deep in her most private place. When his fat knob reached its widest point, Dale paused to admire her formerly tight anus twitching around it, stretched wider than it had ever been.

“Lucy, Baby, you should see your little asshole now. You are so fucking sexy. Are you ready for more?”

Lucy’s pussy and ass clenched with erotic anticipation, sending a shock wave up Dale’s dick. Her anus felt even tighter and more divine than he had imagined.

“It hurts a little. But, fuck yes I’m bahis şirketleri ready. Go slow.”

With that, Dale pushed his hips forward with a moderate, steady pressure, driving the rest of his cockhead through her yielding but still-taunt sphincter with an audible pop. Lucy squealed as her rectal ring gripped her lover for the first time. After a pause, Dale resumed his steady pressure.

Primed by the beads, the generous glob of lubrication injected into her ass, and her arousal, Lucy’s rectum accepted Dale’s cock as he slid into her, torturously slow. The fullness made her drunk, the stinging burn taking on a hot, tingling quality. Slightly less than a third of Dale’s dick was now buried in her back tunnel; her butt was strangling his cock and his urge to ram it in was unbelievable. He paused again for a moment, both to give Lucy time to adjust and to reign in his own pure carnal desire.

Pulling his hips back, Dale slowly withdrew, leaving only his large head inside. Then he pushed slightly forward again. Lucy sighed lustily. Her ass was hungry for his dick and in that moment, she just wanted him to anally ream her. With considerable restraint, Dale instead began to ease the first 2 inches of his hard pole in and out at a slow but constant pace. She was groaning as he fucked her butt with the tip of his cock.

Dale continued to deliver his slow, shallow assfucking, after a few minutes pushing another inch firmly in. Lucy grew even more impatient with desire. He had intended to give it to her one inch at a time, but she was ready.

“Dale. I want all of you.”

“We should go slow. I don’t want to hurt you.”

“Well then, hurt me. Fuck me in the ass. I’m yours.”

At her words, Dale fell in love and nearly came simultaneously. He’d give it to her like she asked him, them.

He placed his hands on her hips and began to drag them back, impaling her further onto his erection. Lucy cried out in agony, realizing she had underestimated what it would feel like to have his bulbous cockhead so far up her virgin ass. The depths of her passage felt like they were on fire. She would have regretted her hubris if not for the bursts of warmth radiating into her belly from her speared backside. Never in her life had Lucy felt so deliriously whorish.

Although he felt guilty about it, Lucy’s helpless, pained squeals made Dale’s cock jump in her tight chute. She felt it twitch, was aware of every pulsing vein in his monstrous penis. The invasion was relentless this time, and he continued to push until his hips were pressed tight against her soft buttocks. Lucy’s ass swallowing his thick pole was the hottest thing Dale had ever laid eyes on. He could see the side of her face and noticed that it was no longer contorted; instead, her jaw was slack and her eyes half-closed in shock and langorous rapture.

Her bowels strained against his thick 7 inches, twitching occasionally as her obedient butt gradually relaxed to accommodate him. Holding her hips in place, Dale began to swirl his pelvis in a circular motion, screwing her anus and insides open even more. When he pulled back, his cock dragged against her rectal walls, making them ache. Pulling halfway out, he pushed himself back into her depths with a short thrust. Lucy grunted. He repeated the motion several more times, prepping her rectum for longer strokes.

When she felt the knot of his cockhead begin to pull further out of her ass, Lucy gasped at the feeling of her back passage trying to suck Dale’s cock back in. He continued to pull out until only the head remained buried in her asshole. Then, in one swift, fluid motion, Dale thrust his entire cock up her still stinging rectum. Lucy let out a strangled cry of pain that quickly became a loud moan. She emitted more little cries and gasps as he began to slowly pull most of the way out again, her ass clinging to the intruder. Again, he firmly buried his length back into her anal cavity. Dale could not believe the erotic sounds coming from Lucy’s mouth; he knew he’d made an anal addict out of her.

Within a few longer strokes to her ass, Lucy’s muscles relaxed enough that Dale felt comfortable putting on speed. No longer pausing between thrusts, he began pumping her butt with a constant, staccato rhythm. The burning in Lucy’s rectum intensified and sent hot jolts into her gut, her pussy, and her clit. The pain mingled deliciously with the intense pleasure.

If Lucy had been hoping for a hard fuck, she was not disappointed. Her ass felt like warm butter to Dale as he fucked her faster and deeper, her hot passage offering less and less resistance. Soon, his hips were loudly slapping against her big, jiggling ass cheeks as she moaned and cried out shamelessly. Lucy’s ring felt completely torn and used, and she was ecstatic. Everytime Dale’s cock drove itself back up her ass, an electric current buzzed through her butt, through her body and down to her fingers and toes. She began to come when Dale folded his body over her back, the weight of him forcing his thick knob further up her ass than it had been before. His thickness held her rectum open as she orgasmed, driving up the pulsating and delicious twitches in her backside and pussy. As Lucy’s orgasm subsided, Dale began to come as well. Lucy screamed when she felt the first burst of semen shoot into her, and felt her pelvis again erupt into spasms as he deposited hot blast after blast.

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