Caitlyn's anal awakening
Caitlyn wore her new red dress to the party. She knew it made her look hot. It was sooo short, it was off the shoulder and it had a cutout on one side. She teamed it with her silver platforms and a little red thong. It was Jessica McKinley’s 19th birthday party. Caitlyn didn’t know Jessica well at all, but Jessica was a friend of Caitlyn’s bff Shona. Shona was also dating Jessica’s brother Jeff. Jeff was on the basketball team and he was hot! He was the only white guy on the team. Jeff’s dad was the coach.Shona had given Caitlyn a ride to Jessica’s house. Shona rang the bell. Jessica’s dad Coach McKinley opened the door and brought them straight through the house where all the other teens were, out into the back garden. “Mind if I take some pictures, girls?” He asked. “You look so hot!” Caitlyn was a little embarrassed but she and Shona let him take a picture anyway. Shona was wearing her black dress, she called it her slutwear. She had on pink stripper heels and a little silver bracelet. Shona was a little taller than Caitlyn but Caitlyn knew she was hotter. They had both got their cunts waxed that afternoon, just in case.Jeff McKinley came out to the garden and said hi to the girls. Shona and him went to look for beers in the house. Caitlyn was going to follow them but Coach McKinley asked her to wait. He wanted to take another picture of her, on her own. You look really hot tonight, darling, he said. What’s your name? She told him. You’re gonna tease all those boys, you little whore, he joked. She giggled uncomfortably.Caitlyn went back into the house. It was getting dark, and the lights were off in the lounge. Music was playing and some k**s were dancing. She found the drinks table and poured herself a vodka. She couldn’t see Shona and Jeff. Where were they? She didn’t know anyone else at the party. She chatted to Jessica McKinley for a few minutes but she could tell Jessica didn’t like her, the bitch. She got another drink and sat in a chair. More k**s were dancing. Where the fuck was Shona? A guy asked her to dance but she said no. She got another drink, a big one. Boring! It felt like she sat there for hours. She didn’t even have her phone because she hadn’t bought a bag yet to match the red dress. Then, someone was standing in front of her. It was Coach McKinley. He asked her if she’d like to dance. WTF? The guy was at least fifty. He reached out and caught her hand, pulled her up to her feet. Come on, he said, I’m a great dancer. He wasn’t joking. He must have learned to dance during World War II, Caitlyn thought. Foxtrot, quickstep, all that shit. He had his arm around her waist like a gentleman. Maybe this wasn’t so bad after all.Then the music changed to a slow song. He still kept his arm around her and pulled her close. Caitlyn knew his wife had died a few years ago so she guessed he wasn’t doing anything too wrong, but it was a bit creepy cause he was old enough to be her dad. Poor fucker, she thought, probably hasn’t got laid since his wife died. She put her arms around his neck and brushed her cheek against his cheek. He had his hands on her waist. One hand was touching her skin where the dress was cut away.Another song, and they kept dancing. Then she felt his hands slide from the small of her back, a little lower towards her ass. Dirty old bastard, she thought, but in a weird way she was kinda turned on. She held his neck tighter and brought her lips up to his ear. I got a bikini wax, she whispered. She wasn’t sure if he had heard her because the music was loud and he was probably a little deaf, but his hands slipped lower onto her butt so then she knew. He was pulling her ass tight into his crotch. They started to grind together. She could feel a bump. Christ, she thought, he’s getting a boner. He was holding her so tight she couldn’t move, she could scarcely breathe. He moved his head a little so he could whisper to her. Caitlyn, he began, but she couldn’t hear the rest of the sentence. At least he had remembered her name. She thought he had said something about pussy but she wasn't sure.Suddenly, Coach McKinley spun her around so he was standing right behind her. He still had his arms around her waist. He moved her arms back, so that she was reaching behind her, holding his hips. One of his hands moved up, onto her breast. The other hand moved down. He slipped it under her dress where the hole was, and down into her panties. She was glad she had worn the thong, just in case. His middle finger slipped into her cunt, searching for her clit. He pulled her hard back into him. His mouth was against her ear. He was breathing very heavily and tonguing her ear. I love your shaved pussy, she heard him whisper. Cailtlyn hoped he wasn't gonna have a heart attack. He was massaging her tit and fingering her clit. It felt good. She was drunk, she knew, but this was hot. She could feel his boner against her buttocks. Coach McKinley took his hand off her breast for a moment, did something behind her, and then put it back on her tit. What had he done? She wasn’t sure. But his dick felt bigger. Then she realized he had taken it out of his pants. She reached behind and felt for it. Jeez, it was huge. She couldn’t close her hand around it. She let go of his dick, and he pulled her back onto him so that the cock was between her ass cheeks. He was still fingering her cunt. Move over to the wall, he rasped. They moved across the lounge like a strange four-legged a****l, bodies pressed together, she in front. He was holding her steady as she walked in her silver heels. Had anyone noticed his dick was out? Probably not, coz it was dark and he was pressed right up against her.They got to the edge of the room, where there was a bookcase against the wall. Put your hands on the shelf, he commanded. No, the lower shelf. She was bent over, arms reaching out in front of her, both hands holding the shelf for balance. The heels lifted her ass up, level with his crotch. He had one hand reaching around under her, still diddling her clit. The other hand pulled down her thong. She could feel his urgency. The dress was up around her hips. Fuck it, I don’t care who’s watching, thought Caitlyn.Her pussy was wet, ready for him to enter her. But he didn’t enter her pussy. She could feel his thick cock behind her, still rubbing her ass cheeks. Then she felt it push against her butthole. What was he doing? The head of his dick was right against her asshole and he was pushing. He was in completely the wrong place. Had he forgotten where a cunt was? Was he going to dry hump her ass crack? He was pushing hard now, but there was no way that dick was going to reach her cunt from that angle. She turned her head sideways towards him. He was bent right over her so he was really close. What are you doing, she whispered? I’m gonna fuck your ass, he replied. Christ, thought Caitlyn. I’ve never done that before. She had seen it in a porno once but she never thought it would happen to her.Coach McKeever reached over on the bookshelf and picked something up. It was a tube of lubricant. Christ, thought Caitlyn, he had this planned all along. He squeezed some lube onto her ass and moved his right hand back onto her buttock, massaging the gel into it. His left hand was still fingering her cunt. His right hand was rubbing lube up and down her ass crack, squirting it right into her bum. Then he put the tip of his middle finger into her butthole and began to work it in, with a slight beckoning motion. The finger went in easily, assisted by the lube. It felt kinda weird to Caitlyn, like a dull sensation. He slid out the finger for a moment, then pushed it back in with his middle finger too. Both fingers, all the way in. It felt kinda like taking a shit in reverse. Then he pulled his fingers out of her ass and put the straight into her mouth. What the fuck? She could taste lube and the fingers smelled of ass. It was gross, unhygienic! She almost retched. But it was also very very sexy. It was the dirtiest thing Caitlyn had ever done. Coach McKinley was turning her into his buttslut, and she loved it. His fingers went back into her asshole, then back to her mouth, then back to her ass again. She slurped on his fingers like she was licking honey off them, not lube and shit. She knew she was a real dirtbird.Then another squirt of lube, and the cock was back again. The head was pushing against her butthole. Her buttocks were clenched so tight. His cock was so fat. Her little ring was fighting against it. He relented for a moment and slid the two fingers back in. Then a third, that made it really tight. Then the fingers went away and the cock was back. It pushed and pushed. She was up against the bookshelf now, head against the wall, trying to get as far away from the cock as she could. But it kept pushing, pushing, against her sphincter and the lube was making it hard for her anus to resist him. Come on baby, he grunted, give me your ass. You can take it baby. Let me in there. Unnngh.Caitlyn felt something move back there. He had gotten the head in. It felt huge, like her asshole had been stretched 10 centimeters wide. Her sphincter was gripping his dick tightly, but now the dick was inside the ring, stretching it out, not just pushing against it from outside. Christ, it was huge. Now baby, just relax he said. Easy for him to say, thought Caitlyn. At least he’s in now and he’ll come, she thought.But he wasn’t in. Only the tip was in. He put both hands on her hips and bent her over, fully 90 degrees. She was still teetering on the silver heels, holding onto the bookshelves. He didn’t care about her clit anymore even though she hadn’t come. He held her hips firmly and thrust against her. The rest of his penis started to follow the head, penetrating her anus. 1 cm, 2 cm, 3 cm. The pain was intense, it felt like he was splitting her bum open. 4 cm. Unnnngggghhhh. With every centimeter it went in, her ring was stretched wider and wider until the full thickness of the thing was inside her. 5 cm. She wanted to scream but she didn’t want to draw attention. He kept pushing and pushing, deeper and deeper. 6 cm, she couldn’t take it much more. 7 cm, then it suddenly it was past its maximum girth. Her anus was able to close a fraction, and the pain started to subside a little. But Caitlyn began to feel something else. 8 cm, 9 cm, he was still thrusting. 10 cm, 12 cm, 14 cm, it was like there was a giant log in her rectum. He was still pushing and she could put up no resistance. More and more of his cock slid into her butthole. Like a giant turd. Now it was pushing up against her stomach or lungs or something. How big was this thing? It felt like her whole body had been occupied by his cock. Finally, after a few more thrusts she felt the warmth of his ball sack touching against her pussy and she knew that he had gotten the whole thing in, thank god.Good girl, she heard him whisper into her ear. Now I’m gonna pull out, very slowly. Wow, feeling his penis withdraw was a sensation that Caitlyn could describe perfectly. It exactly like taking a giant dump, very slowly. It was a familiar and pleasant feeling. He pulled his cock backwards gently and smoothly. There was a quiet pop, and then suddenly it was completely out. For a moment Caitlyn felt like her ass was cold. She could feel the breeze on it. The she realized that her anus must be gaping like in that porno she watched with Shona. Where was Shona anyway? Fuck her, it didn’t matter now.Coach McKinley entered her ass again. This time it didn’t hurt. His cock slid right in. He moved his hands onto her ass cheeks, pulling them apart to that he could get his cock right in, down to the balls. He pulled out slowly, and she gaped again. In, a little faster. Out, a little faster too. In, out. In, out. He was pumping her ass now, faster and faster. Every time he went in, he went deep deep deep in. Sometimes when he pulled out he pulled right out and she gaped. Other times he thrust back in before he was completely out. His cock was still fat and long, but she could take all of it now. Was he gonna cum inside her ass, she wondered?He pulled out again and moved his hands to Caitlyn’s shoulders. He spun her around and pushed her head down so that she was squatting in front of him. For the first time, she wasn’t facing the wall. She could everyone in the room. They had stopped dancing and were standing around in a circle watching the coach fuck her ass. Coach McKinley pulled her face onto his dick. She sucked for all she was worth. It tasted of lube and shit again, like his fingers had. He pressed her face into him, deepthroating her. Held her there for what felt like 30 seconds. Then let her back for air. She gasped and spluttered. There was spit and drool all over his dick and all over her face. She sucked him again, working his glans with her tongue stud. He began to moan. He grabbed her hair, facefucking her, faster and faster. The suddenly, unngh, he pulled out and grabbed his dick. Caitlyn knelt in front of him. He aimed his load, not into her open mouth but onto her eyes and into her hair. Jeez, she thought, how much degradation can a girl take in one evening? Finally, Coach McKinley was finished. He helped Caitlyn back onto her feet and helped her fix the dress back down around her hips. There was cum running down her cheeks, and lumps of cum in her hair. One of her fake eyelashes was hanging off. Coach McKinley kissed her on the lips. Right boys, she’s all yours now, he said. It was at that moment that Caitlyn realized that the circle of people watching them included all the guys on the basketball team, and they were all standing there with their stiff dicks in their hands.