September 27, 2022

Crazy Lenny: Lilian, The Virgin IX (18+)

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Crazy Lenny: Lilian, The Virgin IX (18+)

Lekan was typing upstairs when he saw lights shining out from under his daughter Lilian’s door at the top of the darkened landing. He gently tapped on her door so as not to disturb his wife, Toyin, who had already headed off to sleep.

“Lights off in ten, young lady,” Lekan reminded her through the door, “It’s getting late.”

“Okay, Dad,” he heard her say through the door, “I just want to finish this last chapter for school tomorrow.”

Lekan smiled to himself. So many of his colleagues at work complained about their teenaged daughters, bemoaning their irresponsible and reckless behaviour: staying out at all hours, having promiscuous sex, drinking, doing drugs, failing out of school… But not his Lilian.

He and Toyin had only been able to have one child, but Lilian was a joy: responsible, respectful, innocent, straight-laced, a straight-A student with a full ride to university around September. Lekan sighed contentedly and felt very grateful.

He and his wife were either extremely lucky, or they had to be doing something right. He walked down the darkened hallway to the master bedroom and entered quietly so as not to wake his wife.

As soon as Lilian heard the door to her parents’ room shut, she got out of bed and walked over to the full-length mirror on the wall. She studied her reflection. At five foot two, Lilian had always been petite for her age, and while she had her small frame to thank, in part, for her success as a dancer, she couldn’t help but wish she had a more womanly shape.

She lifted her nightgown over her head and dropped it in a pile on the carpet, and stared at her own naked body. She turned sideways, studying her tiny breasts in the mirror.

After feeding her Mom some story about regulating her periods, she had finally started taking the pill a few weeks ago, and she wondered, was it just her imagination or were her breasts filling out slightly? She didn’t want huge boobs, as that would interfere with her dance, but even at 19 years of age, she barely filled out her A-cup bra. Her tiny nipples stiffened in the cool air-conditioned air.

She lowered her eyes past her flat stomach and down to her pussy. She often covertly studied her teammates’ private areas when they were showering in the locker room, and she was always a little self-conscious about the way her puffy lips made a visible pouch in her leotard.

But ever since she started seeing her Dad’s boss, Chidi, her opinion about her pussy had changed. It must not look as weird as she imagined because he loved the way her pussy looked and told her often, calling it her “perfect peach”.

Lilian thought about the amazing tongue-lashing he had treated her to earlier that evening, feasting on her little peach until she came all over his face. She smiled as she remembered the gift he had given her: even now, she could feel the metal plug lodged tightly in her virgin ass.

She turned around and studied her round ass in the mirror, looking over her shoulder. Her long hair hung all the way down her back to her tiny waist. Standing on her tiptoes, she reached behind her and spread her little taut cheeks apart and gazed fascinated at the sparkly pink jewel peeking out between them.

She had kept the butt plug in during the bus ride home, all throughout dinner, homework and her shower, so long that she almost forgot it was there. She loved the little reminder that only a few hours ago, she had her 45-year-old lover’s tongue buried in her ass.

She thought about what Chidi had said to her, that he was training her ass to take his cock. She shivered just thinking about it. The thought intimidated her slightly, but as an accomplished athlete, she wasn’t afraid of overcoming a physical challenge. She trusted Chidi implicitly with her body and her pleasure, and if he wanted to fuck her in the ass, she was determined to be the best he ever had.

Lilian went over to her desk and perched naked in her desk chair, feeling the plug press deeper in her ass as she opened her laptop. Quietly typing so as not to wake her parents, she entered the parental control password that her parents thought was a secret. Next time my parents want to keep a password secure, they shouldn’t make it “Lilian”, she thought to herself.

She held her breath as she opened the search screen and gingerly typed “anal sex”. She was immediately bombarded with hundreds of images and websites. She typed in “teenager anal sex” and pressed enter. She clicked on the first website. Her eyes widened as it loaded.

The website featured pictures and videos of a girl no bigger than Lilian taking a muscular man’s thick hard cock up her ass in a variety of positions. In one picture, she was bent over a sofa as the man stood behind her, his massive tool stretching her tiny tail hole impossibly wide; in another, he lay on his side spooning her, his tattooed arm lifting her leg high to give his cock better access to her ass.

She saw a link to a video below and covertly turned off the sound on her computer before pressing play. In the video, the same girl was balanced helplessly on the handsome man’s lap while he held her legs back and fucked into her widening butthole from below. The girl was moaning and biting her lip, and she played with her tiny pussy while he bounced her on his cock.

Then the man effortlessly lifted her off of his massive cock like she was no heavier than a rag doll, and she could see her open asshole gaping wide before he lowered her onto his impaling dick again. The girl licked her lips and smiled as she took this thorough ass-reaming.

Lilian felt her pussy start to tingle and get wet as she watched the rest of the video. It seemed perverse and wrong to let a man stick his penis into such a dirty, private hole, but maybe the perverseness of it was what turned her on. A horniness like she had never felt before coursed through her body, and she felt her stretched asshole throbbing around the metal plug.

The girl in the video’s body looked a lot like hers, with small tits that barely bounced even while she was taking a hard pounding, a flat stomach, and a round bubble butt. The only difference was that Lilian kept the tuft of hair growing on her pussy mound and the girl in the video had shaved hers completely bald. Well, if that girl can take such a mammoth cock, I can probably take Chidi’s, she thought. After all, taking his large cock in her pussy was once intimidating, and now it was easy.

Lilian snaked her fingers in between her slick pussy lips and rubbed her little clit while she imagined the man in the video was Chidi, and he was fucking her little asshole. Lilian squeezed her eyes tight and bit her lip as she came in a series of intense spasms.

When she came down from her powerful orgasm, Lilian entered “teen butt plug” in the search engine and studied the images that came up. She found a few pictures that looked like selfies: otherwise, normal-looking teen girls posed lewdly in front of mirrors, exposing the butt plug hidden between their cheeks to an imagined audience. A few of the pictures even featured bejewelled ones like hers.

Lilian closed her laptop, grabbed her phone and stood with her back to the mirror. She bent over and looked between her legs at her open ass in the mirror. She clicked a few photos and then stood up to study them. Looking at that jewel lodged between her cheeks and her puffy pussy lips peeking out below made her hot again. She picked out the clearest photo and texted it to Chidi with a little winking face.

Sitting up in his hotel bed, Chidi reached for his buzzing phone and smiled at what he saw. Slowly, he reached his hand under the sheets and sought out his already stiffening cock…

“…so are you in?”

Lilian snapped out of her reverie and looked up from her bag. Her best friend, Hadiza, was staring down at her with a slightly annoyed, expectant look on her face.

“I’m sorry… what?” Lilian asked. Hadiza rolled her eyes at her. She could barely contain her frustration.

“Jesus Christ, have you even been listening to one word I’ve said??” Hadiza snapped. Lilian shrugged delicately and waited for her friend to repeat her question. Hadiza turned her back to Lilian and started vigorously brushing her hair into a ponytail. Lilian could see in the mirror that her best friend’s face has concerted with indignation.

“Sorry, I’ve just been a little distracted…” Lilian offered by way of apology. She knew she had been acting strange since she started to see Chidi, and she could sense Hadiza was on to something. Hadiza had been her best friend since primary school and Lilian had never kept a secret this big from her in her life. She just couldn’t risk anyone finding out that she was screwing her Dad’s boss every weekend. She immediately felt guilty.

“No kidding, you’ve been distracted,” Hadiza muttered into the mirror. “I was saying that my parents rented a car for Bayo and me, and I wanted to know if you and Sammy had decided whether or not you wanted in on it or not. The grad party is only two weeks away, you know.”

Lilian did know. In fact, she and Hadiza had dreamed about double-dating to the party since they were in junior school. Lilian had her dream dress picked out before her senior year had even started, and she had been the envy of every girl in her class when Sammy, captain of the football team, had asked her out. But ever since she had given her virginity to Chidi, Lilian had to admit to herself: she had lost some interest in the guy. As is, she could only see him on the weekends, and frankly, spending a Friday night anywhere but in Chidi’s bed felt like a bit of a disappointment to her.

“Oh right, sorry,” Lilian said, pulling her leotard out of her bag and heading to the bathroom, “I forgot to ask him. I’ll let you know as soon as I can.”

Hadiza sighed as her friend shut the door of the bathroom stall. She peeled her uniform skirt down her hips and tugged her blue polo shirt over her head with irritation. Why was Lilian acting so strange? Wasn’t she excited about the grad party? Hadiza caught a glance of her hot pink push-up bra and matching panties in the mirror and smiled to herself. Her small breasts looked a lot bigger in the bra. Maybe I’ll wear this under my dress, she thought to herself.

In the stall, Lilian quickly peeled off her panties and stepped into her team leotard. She didn’t dare change in front of her friend today, as she had a little secret: Lilian had been wearing her butt plug to school all day. She decided to pee, so she didn’t arouse any more suspicion. She felt her asshole clench around the plug as she squatted over the toilet and pissed quickly into the bowl.

She couldn’t help brushing her fingers over the jeweled plug as she wiped herself and stood up. She pulled her arms through the tight sleeves of her leotard, making sure the crotch of her leotard held the plug snugly in place. Lilian felt a tingling in her asshole and pussy… she was being so naughty. Chidi would be proud.

She flushed the toilet and exited the stall to wash her hands. She caught Hadiza’s eyes staring at her in the mirror. “Hey,” Hadiza said smiling, “I think I want to buy some new underwear for party… you wanna go to the mall after practice?”

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Written by
Dr. Deolu Oniranu-Bubble

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