Unexpected Hooup

Foreword: I know a lot of literotica stories often claim to be a true story. While you may doubt the truthfulness of those claims, be certain that this is 100% based on a true story.

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Sean stumbled into the street drunk as hell. He and some friends had decided to celebrate their new fake i.d.'s by getting hammered at the local bars. Being only 19 they had never been to bars or even drank alcohol before but tonight had chugged beer after beer at the bar, ogling the hot older women and trying to work up the courage to talk to them. But now the bar was closed and a bouncer had told Sean it was time to go. As he looked around for his friends however Sean realized he had lost them in the huge crowd of people leaving the bar now that it was closed. Whatever Sean thought. It was already late, all the bars were closing, and he was drunk and tired. All he wanted right now was his bed and pillow, and so he began walking home. His house was a few blocks from the downtown bars and it was a walk of only ten or twenty minutes or so. However after a few minutes walking he saw something which caused him to halt in his tracks. It was a woman, the most beautiful woman he had ever seen in his life.

She was stunning, about 30 years old with caramel brown skin and smoldering black eyes, appearing to be a mix of some asian and Filipino. She was wearing a tank top cut very low, displaying her large breasts to anyone who wanted a glance. She also wore a skimpy pair of booty-shorts cut well above the curve of her round ass, showing off the lower half of her lusciously large cheeks. Sean had never seen a woman so attractive, and knew he had to say something to her. She strutted down the block, quickly glancing up and down the street as if looking for something. Sean, emboldened by the liquid courage, approached her and asked, "Are you waiting for a taxi?"

She whirled in surprise and looked him up and down, as if studying him. Seemingly satisfied she replied, "Nope."

"Oh," Sean said, realizing he had not prepared a second line. She looked at him expectantly, as if waiting for him to say something else. "I thought you were waiting for a cab," he said flatly.

"Do you wanna go?" she asked abruptly, gesturing with her head down the street. Go Sean thought. Go where? But he didn't care. He was so drunk and she was so hot he was willing to go anywhere with her.

"Sure," he replied, drunkenly slurring his s. She looked up and down the street again before asking, "Do you have a car?"

"Car?" Sean asked, confused. "No..."

"Here," she interrupted, seemingly mildly irritated. "I have a spot."

She grabbed his hand and began walking down the street at a brisk pace, pulling a drunken Sean behind her. As they walked, Sean took a moment to consider what was happening. A super hot girl was taking him to a "spot" after asking him if he had a car? Sean didn't know what was going on.

After about five minutes of walking they arrived at her "spot", an alley between some buildings next to a seemingly deserted road. After she pulled him behind some trash cans, she turned to him. "Okay honey," she said. "It's 200."

That was the final piece of the puzzle. Sean finally realized what was going on. The skimpy clothes, the question about the car, the "spot" in the alley. This woman was a street-walker, albeit the hottest one Sean had ever seen. Even drunk out of his mind, Sean second-guessed having his first sexual experience ever with a prostitute. Sean pulled out his wallet and was semi-relieved to find he didn't have 200, only a $100 bill. "I only have one," he responded, expecting her to refuse. Instead he was shocked when she snatched the bill out of his hands and stashed it in her purse. She began pulling at the front of his jeans, trying to undo the button and fly.

"Wait," he asked, trying to stall. Was he really about to do this? Of course he was tempted, but at the same time a part of him was hesitant to lose his virginity to a prostitute. He scrambled for an excuse to stall longer. "We need condoms."

"No we don't baby," she said, still pulling at his pants. Finally she undid the button and unzipped his fly. "I'm clean."

Suddenly she fell to her knees, pulling Sean's pants and boxers down to his ankles as she did. Sean's cock sprang loose, rock hard at the thought of fucking this hot older woman even if she was a prostitute. Before he could stop her she grabbed his cock and wrapped her lips around its head.

"Mmmmm," she moaned, staring up into his eyes as she began sucking on his cockhead. Sean's eyes closed and his head fell back in sheer pleasure. The feel of her warm, sucking mouth on his cock was better than anything he could've imagined. All doubts about his time with this prostitute evaporated as Sean enjoyed the feel of his cock in her warm, wet mouth. Smiling at the effect of her initial sucking, she began bobbing up and down his cock, using saliva and suction to maximize the pleasure. Sean was lost for words, overcome by the sheer pleasure of this older woman's sexual experience. Subconsciously he reached down and slipped his hand into her tank top, where he grabbed and squeezed her right tit.

"You really know what you're doing," Sean murmured, his eyes still closed from the pleasure. The woman took Sean's cock out of her mouth for a moment to reply "Thank you," in a dusky voice before returning her lips to his member. She began using her tongue to rapidly lick up and down Sean's penis, an act which caused him to groan in pleasure. He fondled her tits, enjoying for the first time the feel of a woman's round full breast in his hands.

"What cup size are you" he asked as he fondled her breasts.

"Double D's" she responded, before completely engulfing Sean's cock in a deep-throat. Her lips wrapped around the base of his cock, she looked up at Sean and gazed into his eyes. Sean couldn't believe this hot woman was deepthroating his cock, and the intimacy of the moment nearly caused Sean to explode right into her throat. However before he did she removed her mouth from his cock, causing Sean slight disappointment. But what she did next excited him even more. She stood up and rapidly unbuttoned the front of her shorts before quickly sliding them off. She turned around and bent over slightly, one hand on the wall for support while the other hand reached under her to grab Sean's cock and aim it at her pussy. As Sean saw her firm ass pressed against his crotch, he couldn't believe he was about to fuck this hot woman. He eagerly waited for his cock to make contact with her pussy, placing his hands on her hips in anticipation. After a second of her getting into place he felt a warm, moist feeling at the tip of his cock, just for a second. He thrust forward eagerly, trying to get back to that warm feeling, and they both cried out as his cock stabbed into her moist pussy. The warm, slick feeling of it was even better than her mouth, and Sean luxuriated in the sensation. After a second he thrust forward again, stuffing his entire cock into her, causing her to exhale sharply as she felt Sean fill her vaginal canal.

"Fuck me baby," she said. "Fuck me hard." She placed both hands on the wall as she braced herself for the coming fuck.

Obliging her, Sean began to thrust hard and fast into her pussy, his hips hammering against her ass. The pleasure he was feeling from her pussy was incredible, and he had to concentrate hard to not cum immediately. Reaching under her, he pulled her tits out of her top and grabbed one in his palm as he continued humping her. With his other hand he grabbed a handful of her firm ass, kneading the flesh in his hand as he fucked her.

As they fucked, Sean looked down at her ass bouncing against his groin. He couldn't believe it, he was actually fucking her. When he had first seen her he had no idea that a few minutes later he'd be balls deep in her pussy. But now here they were, fucking in an alley. This thought turned Sean on even more and he began driving even harder into her, causing her to begin breathing rapidly as Sean's cock plowed her pussy. He slapped her ass hard, eliciting a small squeal from the hooker.

"Oh fuck" she panted, "Fuck fuck fuck fuck" Her stream of endearments caused Sean to fuck her even harder, and she lowered her head as Sean ravaged her from behind.

The alley was filled with the echoes of their sex. Sean's grunts of pleasure and her quick breathing, the sound of his hips slapping against her ass, the wet noise of his cock plowing her pussy.

Sean's balls were churning, and he was getting close. He took his hand from her tit and grabbed her hips, slapping her right cheek as he began powering into her even faster, his teenage hormones kicking in.

He heard a laugh on his left and turned his head, seeing two men standing at the end of the alley. One was laughing while the other had his phone out. Sean saw a bright flash as the camera went off and for a moment he felt a tad bit embarrassed.

"Come on baby," the hooker said. She reached under again and lightly gripped Sean's balls. She began to roll them in her hands. "Oh God," Sean groaned. His attention 100% focused on her again, Sean tightened his grip on her hips and began humping her harder than ever.

"God, I'm gonna cum," Sean exclaimed.

"Don't cum in me," the hooker said, turning her head to look at Sean. "Finish on my ass."

Sean didn't hear her or didn't care, and with one final thrust he shot massive burst of cum into her pussy. Feeling his warm sperm fill her vaginal canal the hooker tried to stand up and disengage her pussy from Sean's cock but he held her firmly by the hips, repeatedly thrusting and pumping more and more cum into the prostitute. As his balls began to empty and his cock lost hardness he gave her ass one final slap and squeeze and pulled out of her. A few drops of cum dribbled out of her pussy as he did, landing in a puddle on the floor. Standing up she turned around and glared at him as he breathed heavily from his orgasm.

"What did I say? I can't believe you just did that," she said irritatedly. She reached one hand down to her pussy and held it up to the light. It was covered in thick white slime. "God what a mess," she said. She reached down to her handbag on the ground and pulled some wet wipes from the bag to begin cleaning herself up. Sean stayed there, not knowing what to say and still staring at her tits, which were hanging out of her tank top. After cleaning herself up she quickly pulled up her shorts and began to put her tits back into her tank top. Sean made one final grab and groped her right tit, trying to remember its feel before she removed his hand and put it back into her tank top. She ran her fingers through her hair, combing it, and then looked at Sean.

"Ok babe that was fun. See you again maybe," she said. She gave him a small hug and then turned to walk down the alley, her ass jiggling slightly as she did. Sean, at a loss for words and still in a daze, pulled his pants back up and buttoned them. He looked at his watch and realized it was almost 3 a.m. He realized he had to get home and began walking home again.