Hailey was a naive girl. She was cute but not exactly sexy, thin body and a pretty face but she didn’t carry herself in a way most men would call sexy, nevertheless, she always haf the attention of boys and she always thought she had them under control. So, after a couple of years of being a college girl, sometime after her 20th birthday, she decided she was going to get a sugardaddy. She believed she could find a rich man online willing to just buy her stuff because she was pretty and to keep it like that for a while. She hoped that at most, she’d have to send him a picture of her tits without her face every once in a while.
Today, five months after that great idea, and four days since she was left alone in a crappy motel room. Disappointed. Humiliated. Used. Still laying naked on the bed, cum dripping off her, sweat drying on her skin. Today she remembered him and she hated that she kinda liked him that night. She hated that she enjoyed the sex, that she was so foolish. She hated that she expected more and didn’t get it. She hated that he didn’t care enough to take her back home.
She was very much into the idea of a luxirious life and she thought she deserved it just because she considered herself pretty. She wanted expensive shoes and purses, maybe even an apartment of her own. Would he help her with car payments? A whole car? A vacation? She expected too much for what she was willing to do, and she soon realized it was probably just going to be a fantasy.
Eventually, she let men think there was a chance for a meeting, never intending to follow through, and the attention didn’t last long. At least she got some cash from a couple of them, not much. Still she didn’t want to give up or whore out much. She never thought herself as a sex worker, just a flirty girl who wanted free stuff and was due some pampering, because her fake interest was worth it.
Only one man seemed to actually just enjoy what she offered. He got her some food a couple of times in the first week, and told her that he wanted to gift her something if she promised to send him pictures wearing it. She did. And he actually bought her a pretty dress from the wishlist she showed him. A pair of heels a couple of weeks later, she was trying to hook him with pictures and flirting and she actually felt aroused with the power she thought she was having over him. Next gift was lingerie, a sexy outfit with stockings. She hesitated to take those pictures because he wanted to see her face in those, otherwise he would just find someone else, but she sent them anyway. Even one with her hand in her panties. She was such a tease. Things were going slower than she hoped, but moving forward. He kept getting her some take out inbetween presents.
He sent her a swimsuit next and asked for a video of her masturbating. She said no. He promised jewelry. She still said no, so he stopped messaging her. After a few weeks of not getting genuine attention from anyone else, she tried to contact him again. He told her that he was very clear from the beginning he expected to meet at some point and for her to be playful. He wouldn’t be interested anymore. She apologized and sent him the video to be back in his good graces. He bought her some fancy earrings for that. She still thought she had the upper hand, he made a lot of promises after all. She imagined he had quite a bit of money, so she eventually agreed to meet after some more gifts.
She dressed nicely. Ready to impress. When he arrived for her she was dashing. He was not. He looked like his pictures, with less spark and more hunger. With lust. He touched her thighs too quickly, he went for a kiss in a hurry. His car nor his clothes were as luxurious as she expected. He took her to a fancy restaurant but he didn’t eat a fancy meal. He wanted her and she knew it. Still he was kind and fun and handsome, not a rich man though. A middle class, hard working man who just seemed infatuated with her.
After the meal he didn’t take her home, he expected alone time with her. He parked at the side of the road in a place with a great view. He charmed her. They kissed. He grabbed her by the waist letting his hands fall on her tight butt and she felt him getting harder through his trousers. She agreed to join him in a hotel and laughed all the way until she saw where they were headed. To a cheap, horrible motel known to be used by hookers. She wanted to leave and he told her to trust him. She did, and she regreted it.
As soon as they were inside, he pulled her close. Walking with one hand on her waist and the other entwined with her hair. And for a moment she forgot where she was and what was about to happen. He kissed her lips, her neck and her lips again. He pinned her against the wall and she felt that tingly feeling on her crotch when he rubbed himself against her as he groped her.
Suddenly he was almost growling. He wanted her so badly. She didn’t want to do it there, it was gross. But she didn’t want to disappoint him again. She thought of the gifts and the promise of more. She was panting, drowning her moans. He lifted her dress and took off her bra. He played with her nipples slowly, licking, sucking, touching. She whimpered and opened her legs more. She reached for his cock with her hands and gave him an innocent look biting her lips as she kneeled. He was thick and she slowly played with her tongue on the tip. She could barely take him but she did her best and after a few minutes of her enjoying that cock, he pushed hard as deep as she could handle it. Her watery eyes made her mascara run. Her panties were soaked.
He lifted her and tossed her on the bed. She spread her legs and sneaked her hand in her panties. Touching for him, waiting for him. As soon as he took off his clothes, he hurtled towards her, ripped off her panties and rammed himself inside of her. She felt every inch stretching her tight pussy. She moaned loud as he groaned when he thrusted in and out of her with desire. Harder and faster. They looked at each other and he whispered in her ear how her wet and warm pussy felt, how he was going to explode inside her. How every penny he spent to be inside her was worth it. And she was so close. She was almost at the edge, she told him to fuck her harder to fill her up and shortly after she reached her climax for an orgasm, she felt the creamy thick cum inside her.
She closed her eyes for a moment, she enjoyed her post orgasm bliss thinking about all the gifts and money he’d get her, besides good sex. When she opened them up, he was dressing in a hurry. He left her cash for a cab, said goodbye from the door and never contacted her again.
Source: reddit.com/r/Erotica/comments/bscndh/almost_a_sugarbaby_mf