tagAnalChelsea's Anal Adventures

Chelsea's Anal Adventures


"Did you miss me baby?" George grinned as he saw his mistress sitting elegantly at the bar. She was wearing a red sequined dress with high heels. Her hair was down around her shoulders and her skin was tanned just right. She was sipping a glass of white wine and George knew that it was probably the most expensive wine in the bar.

"Of course. It's been way too long sweetie." Chelsea tilted her head so that he could kiss her neck. She had enjoyed checking into this hotel. It was the most expensive hotel in the city and she enjoyed taking in everything in both her room and now the adjoining bar.

"I know. Work has been so busy and sometimes you distract me." George sat down and motioned to the bartender to get him the same as her. He sipped the crisp wine and continued. "Mr. Nico referred me to a few of his friends so business has been wonderful. That means a huge pay raise, but less time to play with you."

George and Chelsea had been together for almost two years. He had met her on her eighteenth birthday when her immature friends had been stupid enough to buy some drugs from an undercover cop. George was one of her friend's father's lawyers and had taken a liking to the cute girl. She had no ride home because her mom was probably out being drugged up herself. An innocent kiss on the cheek to wish her a happy birthday had ended up turning into a night of intense sex in her childhood bedroom.

"You don't have to apologize George. I know the arrangement. You just call and I'll go wherever you want me to be. I have to say that this is a very nice hotel." Chelsea had finished her wine and was now stroking his arm softly. She had crossed her legs and she knew that her skirt was sliding up her thighs.

"I know baby, but I'm allowed to miss you." George cringed inside as he said that. After their first night together, he had told himself that he would never see her again. Then he had been asked to bring his girlfriend along to a get together with colleagues. He had called her up and she had dropped everything to go skiing in Whistler. She was so excited about the trip that George had innocently said that anytime he went traveling she could come along.

"How badly do you miss me?" Chelsea slid her hand from his arm down to his leg. She giggled as she massaged his inner thigh. His cock was hardening and now was throbbing against his pants.

"I have lots of work to do, but you're first."

Chelsea giggled again and let George lead her by her arm towards the elevators. He used his hotel room card to summon the penthouse elevator and they entered quickly.

"I love the dress. Did I pay for it?"

"Yes you did sweetie. I have matching panties and bra as well."

"I love it."

The doors opened to their floor and the couple walked quickly to the double doors that led to their room. George entered first and grabbed Chelsea roughly. He kissed her hard, kicking the door shut. He ran his hands through her thick locks while walking her backwards towards the king size bed. Chelsea fell onto the bed and arched her back. She spread her legs wide so that George could see the red lace material covering her pussy.

"Take them off." George was undressing himself while keeping his eyes on her. He removed his tie and placed it on the closest chair. He always made sure to fold his clothing nicely. Chelsea never said anything, but figured that if he didn't do that she would rip it off him instead.

"Fuck my ass baby." Chelsea had that innocent schoolgirl look as she said those words. They had an adventurous sex life, but had rarely had anal sex. George knew she loved feeling his cum inside her.

"You serious?" George was naked now. His clothes were folded neatly. His tall muscular body was not as tanned as hers. His cock was throbbing and there was a drop of precum on the tip. Chelsea subconsciously stuck her tongue out, wanting to taste it.

"Yeah. I know you want it. You've been staring at my butt since you walked into the bar."

George grinned. She knew him too well. He watched as she flipped over onto her hands and knees and flipped her skirt up. She was wearing stockings and he could see the garter snug against her tanned legs. He fumbled in his wallet for a condom and rolled it out onto his cock. He very rarely wore condoms anymore, but knew it was necessary.

"Wiggle your ass for me. Spread your cheeks." Chelsea did as she was told and George rubbed his cock against her pussy then slid it gently into her ass.

"Jesus Christ." Chelsea screamed out as her body shook in pleasure. She didn't realize how horny she was and how much she missed him until the tip of his cock spread her asshole. She shook violently and pushed back, making his cock slide further inside. George gripped her small hips and rocked back and forth. He normally lasted a long time, but knew he was not going to last another second if she kept shaking.

"Stop moving or I'm going to blow my load." George gripped her hips tighter and moved her slowly back and forth on his cock. Chelsea felt her wetness against her thighs and knew her pussy was pulsing. She wanted to touch her clit, but had to grip the sheets for balance. Her legs were so wide she was almost touching the bed.

"Fuck my ass. That's it baby. I'm yours. Always." Chelsea really did enjoy being George's mistress. They had a level of respect and had always been in harmony when it came to sex. George grunted and spanked her gently. He spanked her again, this time harder.

"That's it George. I've been a bad girl. Spank me harder. I've played with my pussy while you were away. Punish me." Chelsea knew this was turning him on and when he spanked her so hard the slap echoed in the room, she knew he was close.

"You're a very bad girl. You need to be fucked hard. I'm going to cum so hard in your ass." George had let go of her hips and was spanking her ass cheeks repeatedly. She was wiggling back and forth faster and he massaged her ass cheeks then slapped them again.

"Oh Fuck!" George pulled out suddenly, whipped off the condom, and jerked his cock against her ass. He moaned as his cum oozed all over her red ass cheeks, dripped down the crack, and pooled under her.


"Yeah wow is right. Being away from you for a month is almost worth it. Almost."

Chelsea smiled.

"Do I get you to myself for the weekend at least?" Chelsea waited for a response. Sometimes she would fuck only him until he was too exhausted to walk. She had been shared with some of his colleagues and clients in the past and was interested in knowing what would happen this visit.

"Um. We'll talk about that in the morning."

Chelsea stretched out in bed. Her muscles were sore and she knew exactly why. She and George had fucked pretty much all night and had both passed out around two in the morning. The alarm clock next to the bed said ten and since George was not in bed, he was either out with a client or working in the office.

Chelsea and George had an interesting relationship. Technically, Chelsea was paid to be George's girlfriend at important functions. They also fucked, a lot. She was always at his disposal unless it conflicted with school.

She slid out of bed and tiptoed to the bathroom. After fixing herself up a bit, she wrapped herself in the plush white robe that was hanging on the door and walked towards the office. She entered and saw George talking on the phone.

George was almost twenty years older than she was, but he was in great shape. He was an international lawyer and traveled a lot for business. After meeting almost two years ago, their relationship was exactly what both of them wanted. She had learned quickly how to act around his clients. She knew when he wanted her to be cute and cuddly and when he wanted her to be rough and nasty.

George waved her in and then finished the phone call. She stood in front of him, not wanting to distract him from his work. She was about to say something, but the moment he hung up the phone, he grabbed both her breasts and twisted the nipples.

"What do you say about being a little sex toy tonight?" George let go of her breasts to undo his pants. He needed her again.

"Sure". Chelsea's level of horniness had doubled in the few seconds he had been rough with her. She removed the robe and climbed into his lap, watching as he guided his throbbing member into her pussy.

"Mr. Nico is in town. I was just talking to him. He wanted to know if you were still around." George was bouncing Chelsea on his cock, feeling her juices on his balls. She was always so tight, but so wet.

"I don't mind being shared." Chelsea smiled. She loved knowing that she was good enough in bed to be passed around. Her mind was spinning, wondering what George was going to propose to her now.

"Anthony, one of his bodyguards, saved his life. He was almost assassinated. He asked him what bonus he wanted and he said you."

Chelsea could not help but laugh. George grinned. He knew what she was thinking. Mr. Nico could give them almost any amount of money they wanted. He could give them cars, houses, jewelry. He had such power in Europe that if they wanted a porn star to fuck for a night he could arrange that. After saving his boss's life, Anthony had wanted Chelsea.

"I didn't think I had that much influence." Chelsea rotated her hips in fast circles. She loved doing this because it meant that George's cock rubbed her pussy in all the right spots. George grunted. This little vixen was going to make him cum again.

"Fuck baby. You turn me into some horny teenager. Damn it!" George gritted his teeth and exploded inside her. He used to pride himself on lasting for hours, making his lovers beg him to stop. It was different with Chelsea.

"Sorry". Chelsea looked genuinely concerned. She slid off his cock, closing her legs as his cum dripped down her inner thighs.

"It's fine. You know I used to last for fucking hours before you. Hey! We're not done." George saw Chelsea put the robe back on and start walking towards the door.

"But you came." Chelsea knew she was pouting. She was trying hard not to, but knew that when George was done it was done.

"Go get the silver dildo and come back." George couldn't help but chuckle as Chelsea's face went from pouting to a big smile.

Chelsea rushed to the bedroom and looked in her bag for the dildo. She had many sex toys. Some of them were for when she wasn't with George. Some were toys that he wanted to try out. This dildo was thin and long. She brought it back and was about to open her mouth to say something, but shut it quick. George was on the phone again, but motioned to her to come over. She was confused, but then smiled as he bent her over his desk and began to push the dildo in and out of her pussy. He sat down in his chair, facing her spread legs. He slowly pushed the dildo into her ass.

"Oh." Chelsea bit her hand to muffle her moans. The dildo felt so good inside her. She rested her head on the desk as George skillfully fucked her ass while talking on the phone. Chelsea was not paying attention to the conversation. Her pussy juices were dripping down her thighs and she wondered if George realized that she would soon soak the important papers on his desk.

"George. Baby. I'm going to gush." Chelsea was desperately holding back. He was pushing the dildo exactly where she needed it to gush. George calmly moved her off his desk and laid her across his lap. He continued chatting on the phone while fucking her ass harder with the dildo.

"Mmm." Chelsea bit down hard on her hand to muffle her cries. She was gushing all over his leg and she was wiggling back and forth. Her pussy contracted, and Chelsea's toes began to tingle. George was still chatting on the phone. Chelsea slid off his lap and smiled at the wet spot on his pants. He finished the conversation as Chelsea wrapped herself up in her robe.

"Anthony will be over in a few hours. Go shower and put on the green nightie I bought you." Chelsea giggled and kissed his cheek before rushing off to shower.

Chelsea laid on the king size bed in her green nightie. It was a sheer material and completely see through. The material hugged her breasts tightly and barely covered her belly button. She wore no panties even though they had a matching gstring. George had gone out to dinner with some clients and she was waiting for Anthony to arrive at any moment.

Chelsea was George's mistress. She had been asked to be shared with one of his client's bodyguards. She was excited to comply. This wasn't the first time she had met Anthony. The last time was at his boss's villa in Italy where she had been gangbanged by Anthony, Joe, and Giovanni. Now, she got Anthony all to herself.

The door clicked open and the tall Italian entered. His hair was shoulder length and he looked so damn sexy her pussy got wetter than it already was.

"Hi Chelsea. You look stunning."

"Thanks. So I heard you saved Mr. Nico's life." Chelsea watched as Anthony slowly began to undress.

"Yeah. Bunch of creeps wanted to kidnap him. I beat the shit out of them while Nico got away. It was so fucking amazing."

Chelsea listened intently as she slowly circled her finger around her ass. Her pussy was freshly waxed and she lubricated her finger with her pussy juices before slowly fingering her ass.

"Fuck. I haven't had a good piece of ass in ages. Flip over." Anthony grunted and stepped forward. He was completely naked now and stroking his hard cock.

"Condom?" Chelsea didn't care, but knew that it was better that way.

"Oh yeah. Put it on me baby." Anthony reached over to grab a condom from his wallet. Chelsea sat up and took the package. She opened it then slid the tip onto his cock. She then wrapped her lips around the condom and slid it down onto his cock. She loved that she could do that. Living in a sorority had its advantages.

Once the condom was on, Anthony slid his cock first into her pussy to get it wet and then slapped her finger away from her ass so he could enter her.

"Oh yeah baby. That's it." Anthony grunted again as he pushed his cock into her ass. She stretched a bit, but was still so tight against his member. He continued to push until his balls slapped against her pussy. He gripped her butt and slid her back and forth slowly against his cock.

"Fuck. You're driving me crazy." Chelsea arched her back and buried her head in the pillows. She was feeling an intense fullness and each stroke made her moan louder. Her pussy was quivering, begging to be filled.

"You're so fucking tight Chelsea. Did George fuck you this morning?" Anthony was in awe of George. He was old and not sexy like him. The fact he scored with such a hot little slut was amazing. He began to speed up his thrusts, feeling his balls slap against her clit.

"No. He used a dildo. He was on the phone with a client."

Anthony imagined Chelsea lying on a big office desk while being fucked by a dildo. He wanted to be the one doing that. He loved fucking Chelsea and had spent many nights jerking off to the image of her kneeling between his legs.

Anthony wrapped his arms around her hips and picked her up. He sat down on the bed and lay back. Chelsea bent her legs and placed her feet firmly on either side of him. She slid up and down at the exact same speed as he was fucking her. Anthony watched his thick cock enter her ass and then pull back. Her bare pussy lips were covered in juices and he reached around and thumbed her clit.

"Fuck. I need to cum. Now. Right now." Chelsea had been in a strange mood lately. She went from enjoying sex to desperately needing to cum right this moment. She sat up and fucked his cock aggressively. Anthony could only watch as she used his cock to get off.

"That's it baby. Use my cock. Fuck my cock. Cum all over my cock." Anthony massaged her cute butt as she slammed down hard and cried out. He felt wetness on his thighs and knew that she had gushed a bit. Chelsea lay back, whimpering as his cock pushed up against her.

"You're such a good little slut Chelsea. I want to cum all over you. Lay back." Anthony pushed her off him and watched her lay on her back. He knelt beside her and jerked hard and fast. The tip of his cock was a deep purple and his cock was covered in precum. He wrapped his large hand and stroked his cock, running the tip against her hard nipples.

"I'm going to cum all over you. You're not going to move until George gets back from dinner. I want him to see his mistress covered in my cum. Mr. Nico said I could do anything to you."

Chelsea only nodded. She watched as Anthony grunted again and began to cum. She felt his cum land on her breasts and stomach. She looked at him and gasped as some of his cum landed on her face. He continued to cum, aiming his cock to cover her bare pussy. The last spurt of cum trickled against her nipples.

"Fuck I wish you were mine. You are a hot little fuck." Chelsea grinned. She didn't say anything while Anthony got dressed and then left the room. She closed her eyes and lay there, feeling the cum dry. She must have fallen asleep because the next thing she remembered was George shaking he gently.

"Chelsea. Go shower then come to bed." Chelsea opened her eyes and climbed out of bed. George was grinning from ear to ear. He was pleased with her.

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