Popping His Cherry

Mayıs 1, 2024 Yazar admin 0

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Summary: Taylor, 18, meets a Loren at a bar and she takes his virginity. Themes include humiliation, crossdressing, domination, feminisation, anal.


“Hey good looking. You’re eighteen right? how’d you like to spend the night with-“

“I’m a guy.” Taylor squinted and tried to deepen his voice as much as he could.

“Oh, shit, sorry!”

Taylor growled to himself as the creep left. Taylor was looking to lose his virginity in the summer before college. Unfortunately, he seemed to have a lot more luck having guys ask him out that having any girl exchange words with him. He was a smart guy, just not the big and confidant type. He wore a flannel button down, jeans, and his short golden brown hair was styled neatly. Unfortunately he just froze around girls. After shuddering out a pickup line they usually rolled their eyes and walked away. He knew it wasn’t because he was ugly. If that were the case, guys wouldn’t be asking him out so much!

It was maddening! If he didn’t get his dick wet now, he was going to be a virgin forever.

“Hey good looking.” He took a deep breath and turned angrily,

“I’m a guy-” he suddenly realized that the one talking was actually a girl.

“Really?” She raised an eyebrow. He couldn’t tell if she was making fun of him or not. She was wearing a leather jacket. Her black hair was long and tied back in a ponytail. Her eyes were grey and smokey. She was tall and lean but Taylor could see a flash of black lace above the waistline of her jeans. “Can I buy you a drink, ‘guy'”

“Uh, no, actually, I’m under age.” Taylor gulped. “My name is Taylor.”

“Loren.” She responded. She moved slowly and subtly like a ghost. It was graceful and foreboding all at once. Her eyes wandered up and down his body. “Nice to meet you. You a high school kid?”

“Yea. I mean, graduate. I’m headed to North State in the fall.”

“Ah. I’m a senior there actually.” She was pretty, in a bad girl kind of way. “Well, this doesn’t seem like the place for you kid.”

“I guess so.”

“Let’s say you come to my place.”

This couldn’t be happening. Taylor’s throat was closing up. Was it really going to be this easy? After all this time? Should he be playing hard to get? “What will we do there?” He asked stupidly.

“Have some fun I hope.” She smiled. “That is what you want, right?” Taylor nodded. “In fact, if you don’t mind me guessing,” She inched closer to him. Her eyes were clear and bright, swirling with a hypnotic stare. “You’re a virgin, aren’t you? And you came here to change that.” He nodded, his hands in his lap. “Don’t worry little boy, I’ll take good care of you.”

“Y-You will?”

“Sure thing. Follow me.” She got up. Taylor felt like he was dreaming. She was so much taller than him. So much older. Loren led Taylor outside and mounted a motorbike. “Hop on.”

“My mom said not to ride these things-“

“Are you fucking serious?” She looked amused, her hands on her hips.

“Er, ha, no!” Taylor coughed. He had to act more cool. “Sure, um, let’s go-” He mounted the bike behind her and felt her backside against him. It was great. She raised an eyebrow at him as she gave him a helmet and put one on herself. Taylor hugged her waist as they rode through the streets. This was insane. Taylor had never done anything like this before. The streets sped fast under him and his felt the cold wind bite into his skin.

Taylor was going to get laid. And it was going to be with a hot chick with a motorbike. This was going to be awesome. He was already trying to figure out how to explain this to his friends when they stopped at a small apartment complex. She parked and led him in. “It’s not much, but it’s a place to sleep.” his hands were shaking, from anticipation, the cold, or the exhilaration he didn’t know.

Her place was disheveled, but not too bad. In need of a good weekly cleaning, but Taylor was a bit more of a neat freak than most. “So, uh, what next?” he asked as he put the helmet on the counter next to hers.

“I like you.” She said, taking off her jacket. She still had on a T-shirt, but seeing her istanbul escort back arch and her chest more sharply was enough to send a spark of lust through Taylor’s body. Her spine had a natural curve and the shirt was sheer enough for him to see the outline of the bra underneath. “Let’s start out here.” She sat on her couch. She threw a couple of books and shirts out of the way to give him a seat. She tapped the cushion playfully. He sat down, knees together, several feet from her. “You’re cute.” She said with a smile. She moved in closer. Taylor swallowed hard as she put an arm around his shoulders. “Tell me more about yourself.” Her body was flush with his.

“Well, I play the flute. And-” Taylor realized she was unbuttoning his shirt, still looking into his eyes.

“Keep going.” His chest was bare underneath.

“Are we going to do it out here?” Taylor asked. It seem a bit open. The blinds weren’t even drawn.

“Just keep talking.” She gave a cute pout.

“Okay. Um. My father is a pastor…” Once all the buttons were gone she began to play with his nipples. Her fingernails were sharp but precise. “What are you doing?”

“Boys always get so weird about their tits.” She complained. “But everyone has them. And I think they are really sexy. Especially when they are sensitive.” she circled them and pinched. Taylor shivered. He had never played with them before, but she was doing wonders. “It there something you’d rather I play with?”

“Well, yea.” Taylor said, looking down at the growing bulge in his jeans.

“So greedy.” Loren shook her head and clicked her tounge. “So soon? And we’ve just gotten started.” She molested his chest.

“Maybe you could play with your nipples?” Taylor suggested.

“Good thinking. You want to see my tits don’t you?” She smiled and said, “How about a trade?”

“A trade?” Taylor asked.

“I’ll take off my bra,” She said playfully, “But you have to put it on.”


“It’s what I’m into.” She said bashfully. “Well?” She reached back and unclasped her bra under her shirt. He could see them sag slightly.

“Okay.” He said quickly. It was weird, but he’d go for it.

She playfully put her arms inside her shirt, maneuvered herself, and pulled her bra out from under. Taylor could see her nipples poking against the fabric of her t-shirt. Then she pulled his shirt off and strapped it on. “Look at that. So much better on you.” it was loose, but did wonders to make Taylor look even more like a girl, even with his shirt off.

“Your shirt-“

“Stays on for now.” She said, teasing him with a caress down his side, “Unless you have another trade?” his eyes looked down to his budding erection. “Ah. That. But we still haven’t even kissed yet! Don’t you want this to last?”

“I guess you’re right.” Taylor swallowed as he felt his mouth fill with saliva. It was going to happen. She came in and touched her lips with his. She commanded his mouth with hers. She enveloped and penetrated him, sucking and fucking Taylor’s mouth with expert skill. She nibbled on his lower lip.

“Ahh!” He groaned.

“Sensitive lips too. You are a horny virgin.” He felt his jeans loosen. He felt her roll him to his back. Then he felt, in one fell swoop, his pants and boxers go down to his knees. Then she broke off the kiss to strip them completely off. All he was wearing was her bra. She saw all of him now out in the open. He felt suddenly terrified and froze. He opened his mouth to say something, but she quickly silenced him by kissing his midriff, caressing his thighs, and running her tongue down to his hips. She was headed toward his cock and he wasn’t going to slow her down.

“Oh!” He shivered and he felt his hips slowly grind with desire. He felt her soft shirt brush against his knees. He began lay back more, his head on the armrest, and let it happen. Her mouth kissed just above his pleasure.

“Wait just one second.” He heard as she fished for something in her pocket. He saw her spread lotion on her hands and slather them. Her hands were lubed thick as she massaged his groin. She was warm escort bayan and wet and delicate. Her ass was up higher than her head and he could see the crack under her jeans that were beginning to droop down, and her undergarments riding up. Her rear end swayed as she fondled and rubbed.

“Ahh!” She was so good. Everything was dripping wet. She touched him everywhere. His thighs, under his sack, over and around the base of his erection. She stroked his cock once and he already felt close. She was really good at this. “Not so fast!” His voice whimpered high. “I want it inside first!”

“Of course.” She smiled, she pressed her cheek and nose on his cock, her face shining with lube where it touched her. “We can’t have you leave here a virgin, can we?” She avoided touching his cock again and caressed his balls and legs.

“Ohh!” Taylor wanted to see more of her. Her shirt was riding up too, he could see most of her back as it it curved into her amazing waistline. He could see those hanging, covered breasts. It was more than enough to keep him high. It was just so embarrassing to be played with by this woman who was barely indecent. But if this is what it took to finally be a man, Taylor would endure it. After a minute she smiled and licked his cock. “Oh wow!” He said breathlessly. He had never been so turned on before. She slowly kissed the head, almost putting just the tip in her mouth and another hand fondled his taint. She drooled on his cock as her finger circled around his backside. “Right there!” Taylor croaked. He felt it enter. He slowly felt his cock enter her mouth, and her finger push against his rectum. It felt so good, and so unexpected, all at the same time. He wanted to tell her to stop and speed up all at the same time. “Th-Thats-” he started, but she was so slow and it felt so good he didn’t continue his sentence. He just let it happen. “Ahhh!” it was like letting his muscles relax in a hot tub. His whole body was warm and fuzzy. His cock was in her beautiful face, and her strong, hard finger was inside of him. It was everything he could do to keep from coming.

Her mouth played shallow, making circles around his cock. Stringy precum linked her lips to him. She didn’t toy with his behind however. That was calculated, powerful, and methodical. Once he was relaxed she held up one leg high to spread him wide and fuck him knuckle deep with the strength of her bicep and shoulder. She put her whole weight behind it. Her finger hooked and fucked and massaged on the inside. Her touches on his cock were so delicate, he almost didn’t notice when she stopped sucking and exclusively fucked his behind. Her breasts were bouncing with each thrust into him “Getting close?” She was starting to get tired too. She was finger fucking him hard now, another finger slowly joining the first. Taylor felt like a little girl now, but if felt great. He hid his blushing face. She couldn’t know how turned on he was. If any of his friends knew he was doing this he’d be a laughing stock.

“Loren!” Taylor called out, “I’m-” She pulled out and he sighed, panting for air. This was a wholly new experience, but what he really wanted was to finally fuck, in the biblical sense. To finally become a man. “I’m ready. Please, let’s go all the way. I’ll do anything!” Taylor was afraid he’d come too soon just looking at the way she looked at him. “Please?” What would it take to get his dick inside her?

She smiled, “Anything?” She unzipped her jeans, then pushed his knees so far back that they touched his ears. His cock touched the bra on his chest. It almost hurt. He could see her smiling above him. “Don’t make promises to a girl that you can’t keep.” her clothed boobs pressed on his legs.

“What do you want?” Taylor asked.

“Commitment.” She said, “I don’t want this to be a one time thing. I want you to be mine and no one else’s. Understand?” Taylor felt her lower her jeans. He saw bits scanty lace underneath, but still not the whole thing.

“Yes!” Taylor was desperate. “Please-“

“You know what that means right?”

“You want to be my girlfriend?” Taylor asked. She smiled.

“You Kurtköy escort get it.” She bit her lips and adjusted her knees to kneel taller over him, “But I also want you to be mine.”

“Okay. I’m your boyfriend.”

“No. Girlfriend.”

“What?” She adjusted herself, leaning back and he saw a rubber cock hanging from her hips. It was strapped tight over her panties, and to her thighs. It flopped on his ballsack and she pulled it back as she leaned forward to point directly at his asshole. Taylor was frozen in shock as she held his ankles up and pushed it it. “Ahh!” It was big, but well oiled. She pushed it in without much trouble. It slipped in stayed tight. Taylor was too shell shocked to say anything. This was all happening so fast.

“You are going to be my girlfriend.” She said. “My personal plaything.” She humped his plump girly rump. “How does it feel to finally get fucked?” She thrust the cock deeper. “Everything you dreamed it was? Finally becoming a woman for the first time-“

“Ahh!” Taylor groaned. This is not what he had in mind. His cock was uselessly sliding around the bra on his chest, just inches from his face. “Loren!” He called out. “This,” She was ramming him so hard Taylor’s whole body was moving with each thrust, “This isn’t-“

“I know. The first time is always rough. It’s embarrassing, Sometimes even a little painful.” She interrupted him. She was panting, fucking him hard and fast. “Don’t worry. I understand. But you will get used to it. Don’t worry.” She was on top of him, pushing him into himself. She bent him back like a pretzel. He was being driven into the couch. He tried to reach for something to grab but only managed to brace himself on his own knees. She pushed until her face was close enough to kiss his and she did. He tasted his own cum in her mouth. He moaned and squirmed as she forced him to taste more and more and she kept bucking into his butt like his ass was a trampoline. She broke off the kiss to gasp, “I love pounding your pussy Taylor.”

“I’m,” Taylor was close. She bent him back even more and his cock began to dangle inches over his face. “Wait!” He called out as she held him upside down and fucked him silly. “I’m, i’m,” Taylor felt a overpowering wave of sex swelling from within. It was nothing like masturbating. This wasn’t just getting off. This was getting fucked. He was getting fucked and he was turning into a slut. “Oh god Loren!” She fucked it into him. Just above his cock he saw her dominant, smug face looking down at him. Taylor felt it start like an earthquake. He shook and the electric tingle of sex exploded out from between his legs. He opened his mouth and wailed just as strings of his own sex poured out all over him. It was raining cum and it splashed on his tongue and teeth. He felt like he was in a cavern of steam surrounded by his own sex, cum, and long legs. Semen pooled on his face and chest. His cock shot cum in his screaming, panting mouth as she watched with amusement. Taylor came in time to the rhythm of her hips and she fucked the juice out of him like she was milking a cow. She drilled into him until the flow turned into a drip. In order to breath he needed to swallow mouthfuls of his own cum. He gargled on it as he gasped and bucked. He had never felt so defeated. He had never felt ashamed. He had also never felt so great.

“Good girl.” Loren removed her cock from him and he relaxed his spine, laying down on the couch. She layed on him, pressing herself on his cum soaked body. He felt her plastic cock rub against his shrinking member. “That was a lot of cum. You sure do like getting fucked, don’t you?”

Taylor nodded with a whimper.

“I’m honored to have been the one to share this moment with you.” She said. “You never forget your first.” She played with his nipples under the bra, wet with his own cum. He nodded blankly, unable to think of anything. “Now, tomorrow, I was hoping if you were free we could have our first date.” He nodded. He’d have agreed to anything. “I wanted to go shopping because, well, we don’t have clothes for you do we? We’ll get your some cute hair ties, maybe a few pieces of cute underwear, some skirts, leggings, the whole nine yards.”

“Sounds good.” Taylor heaved. “Wait, skirts?”

“Cute ones. I want to show you off to all my friends. Wont that be fun?” She pecked his nose with her lips. “Girlfriend?”

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