House Sitting on Halloween

"So, you'll stay with Chance this weekend?" asked Lily.

"Yeah, I'll stay with him. He always throws up on my rugs when he tries to stay with me. Seriously, your dog hates my apartment," said Anna.

"Cool! My cousin Ben might crash on the couch on Friday night, after he's done with his Halloween bar hopping. So, if you hear someone stumbling in after last call, it's him. Ben has a key to my building and to my apartment so, he won't bother you. Actually, he'll probably be gone before you even wake up. That's what he usually does, anyway," said Lily.

"Ok. Chance and I will be fine. He's always a good boy when he manages to keep his food down," said Anna.

On Friday, Halloween, Anna went over to Lily's apartment as promised. Anna would be dog sitting while Lily's boyfriend whisked her away for a romantic fall trip to Vermont. It always seemed to work out like that. Lily's Halloween would consist of a glamorous masquerade ball at the resort with Mike, her stockbroker boyfriend. Anna, on the other hand, would spend the evening watching Netflix with Chance the Golden Retriever.

That night, Anna ordered a pizza and watched Mean Girls, Legally Blonde, and Clueless. Every once in a while, a kid from the building knocked on the apartment door and shouted "Trick or Treat!" When that happened, Anna, wearing cat ears in her long wavy hair, answered the door and gave the kid a snack sized chocolate bar. The trick or treaters stopped around 8:00. At 9:00, Anna and Chance went on his final walk of the evening. Later, around 10:30, Anna shut down her computer. After that, she took a leisurely bubble bath while Chance laid on the bathmat and watched. They both went to sleep after that.

Around 3:00 in the morning, Chance started to whimper. Anna roused slightly. She was about to go and see what was wrong when she heard someone speak to Chance. He immediately quieted down. Ben must be there. Well, he'd be fine. Anna had made up the couch with a pillow, a blanket, and some sheets before she went to sleep. So, no matter how drunk Ben was, he'd be able to sleep comfortably.

Anna slowly drifted back to sleep. When she was almost asleep, she saw him. Ben entered the bedroom, wearing his Halloween costume, and turned on a desk lamp. He was dressed as an old fighter pilot. If Anna had to guess, she would say World War II. The costume looked good on him. Actually, Ben could make anything look good. He looked like a model -- tall and muscular with broad shoulders, chiseled cheekbones, and a square jawline. To top it off, he even had dimples.

"It's you," he said. "I've waited so long to see you."

"Me?" Anna asked.

"Yes, you, my darling," he replied. Ben turned the lamp off and walked over to the bed.

Anna decided that he must be very drunk. But, he seemed sober. No slurring or stumbling. Maybe it was all just a joke.

Ben sat down on the bed and removed his leather boots. They looked authentic. He must have spent a fortune on his costume.

He then took off his leather jacket and put it on the nightstand. After that, he got into bed with Anna.

"Ummm...what are you doing?" Anna asked.

"It's been so long. I need to hold you," Ben said.

Anna decided to just go with things. She was barely awake and not in a mood to deal with Lily's cousin's long, drawn out joke. Plus, he was super hot. If Ben wanted to cuddle to keep the joke going, Anna wasn't going to stop him.

Ben slid under the blanket with Anna. Anna turned onto her side and closed her eyes to go back to sleep.

Next, Ben moved to the center of the bed. He pulled Anna against his chest and put his arms around her. It had been a long time since Anna had been with anyone. Back in March, she'd caught her fiancé in bed with another woman and she hadn't been with anyone since their breakup. So, feeling Ben's muscular chest pressed against her back was most welcomed. Inwardly, Anna congratulated herself on wearing a pretty, satin nightgown instead of her usual oversized t-shirt and shorts. She hadn't anticipated anyone seeing it but, it turned out to be a good choice.

As Anna relaxed into Ben's embrace, she felt his lips on her neck. He tenderly kissed the back of her neck and where her nightgown's straps exposed her shoulders. Ben's kisses were soft but urgent. Anna even felt his tongue a few times. He was definitely into her.

As Anna pushed herself closer to Ben, she felt it. His dick was hard and ready to take things to the next level. Well, so was she.

Anna turned onto her other side so that she was facing Ben. She put her hands on his face and kissed him deeply. Their tongues slid against each other as they both tasted the other. Finally, Anna pulled back a little to catch her breath. When Ben made a disappointed sound, she leaned back to nibble his full lower lip.

As they continued to kiss, their hands started to explore. Anna put her hands on Ben's chest. He still wore his aviator's scarf. The silk felt smooth as she unwound the scarf from his neck. Anna dropped the scarf on the floor and then started to unbutton Ben's shirt. As she did this, his hands were up her nightgown, roaming over her ass and back. After the buttons were opened, Anna pushed the shirt off of Ben's broad shoulders.

Ben's chest was definitely something to behold. Anna couldn't resist running her tongue up and down his pecs. As she did this, he began to moan and his caresses became more insistent. Ben became especially vocal when Anna's tongue came down over his abs to the waist of his olive, army pants. She slowly pulled the waistband of his still buckled pants away from his skin so she could lick underneath it.

Ben couldn't take anymore. He gently pushed Anna down and positioned himself between her thighs. Then, he slid his hands up her nightgown and pulled off her panties.

Ben smiled at Anna and said "Your turn!"

With that, Ben crouched down to begin licking and teasing Anna's pussy. She was already wet from their kisses but, she became far wetter with his ministrations. Ben swirled his tongue around her clit and slowly eased a finger inside of her. While he licked her clit, he massaged her G-spot with his long index finger. All of this brought Anna almost to the brink of an orgasm but, not quite.

Anna reached down and knotted her fingers into Ben's thick hair. She tugged a little to get his attention. He looked up at her, unsure of what she wanted.

"Please...I need you inside of me," she said.

Ben's face lit up. He quickly unbuckled his belt and removed his pants and stood for a moment in his olive boxer briefs. Anna couldn't help but think that he took Halloween seriously. His costume extended all the way down to his underwear. This thought quickly evaporated when Ben removed his boxer briefs and then stood naked, gloriously naked.

He slowly crawled onto the bed and knelt next to Anna's chest. He reached down and pulled the hem of her nightgown up. Anna sat up a little to help. Ben never took his eyes off of her as he removed her nightgown. Now, they were both naked.

Ben laid back down next to Anna. She turned towards him and they started kissing again. This time there were no barriers between them.

They kissed and resumed exploring each other's bodies. Ben reached up and started massaging Anna's breasts. Her nipples ached for his touch until he bent his head down and started sucking on one. Ben sucked until the nipple became long and hard. Then, he turned to the other one. Once again, he sucked and swirled his tongue around her nipple until it became long and hard.

Anna could feel the wetness seeping out of her pussy. She had never been wetter. Her thighs were slick almost to her knees.

"Please..." she whispered.

Ben smiled. "I thought you'd never ask," he said.

Ben positioned himself over Anna. She spread her legs and he nestled in between her damp thighs.

With a surprising delicateness, Ben eased his very hard dick into Anna's very wet pussy. He waited a moment to allow Anna to adjust to him then, he began to thrust.

The two of them fucked in perfect synchronization. Each thrust was met with its perfect counter thrust. It seemed like they had been built for each other. Each time Ben thrust, the tip of his dick hit Anna's G-spot. Plus, each time he pulled back, his shaft stroked Anna's clit. For her part, Anna's wet pussy enveloped Ben's dick wonderfully. The pressure and friction were exactly what he wanted.

Soon, Anna felt the tension in her muscles build. She began to buck her hips faster and more wildly. Ben reached down and began to massage Anna's clit with his fingers. Eventually, she couldn't hold on anymore. Her orgasm felt like something exploded in her. She went limp and saw stars for a moment.

Realizing Ben hadn't come yet, Anna started moving her hips again. She also tightened her vaginal muscles around Ben's dick. Plus, she started licking his neck. She alternated licking with wet kisses.

Then, it was Ben's turn. He came with a loud groan. Anna felt him squirt a load of hot semen into her pussy.

Satisfied, they stayed intertwined for a while, enjoying the feel of their connected bodies. After a while, Ben softened and his dick slid out of Anna. They fell asleep spooning.

About 6:30am, Chance started to whine. Dam Chance and his early morning walks. Anna knew she had to get up and take him out. Well, at least she'd get a chance to have breakfast with Ben afterwards. Maybe they could talk then.

Anna rolled over to get a look at Ben in the early morning light. To her surprise, Ben was gone. On his pillow she found his silk aviator's scarf and a note. The note said "Until we meet again." So, they wouldn't get to talk. Ben could have stayed for coffee or, at the least, left his phone number.

Chance and Anna took a quick walk around the neighborhood. Chance did his business and Anna fumed. She didn't want to ask Lily for Ben's number but, it looked like she had no choice.

While eating breakfast, Anna's phone rang. It was Lily.

"Hey Lily," Anna said.

"Hey. How was last night?" Lily asked.

"Ummm..so, Ben..." Anna started but, Lily interrupted her.

"Oh, I forgot to tell you. Ben texted me last night. He'd found a last minute flight to New Orleans. Something about a séance at Marie Laveau's tomb. So, he didn't need the couch," Lily said.

"What? Of course Ben slept over last night," Anna exclaimed.

"No, Anna. He didn't. He's in New Orleans," Lily insisted.

"Well, someone slept over. Him and I...we...uh...well, we had sex," Anna said.

"Anna, honey, you didn't. It must have been a really vivid dream," Lily said.

Anna started getting embarrassed. So, she let the issue drop.

"Yeah, I guess you're right. The couch doesn't even look slept in," she said. Anna said this to placate Lily. She knew what had happened. Her slightly sore pussy proved it. Plus, someone had definitely come inside of her. She'd had to clean herself up before taking Chance on his walk. Whether it was Ben or not, was a different story.

Anna quickly wrapped up her call. She had one more night with Chance before Lily came back. She decided to take Chance to the dog park and think about her night.

While walking through the lobby, Anna noticed a framed photograph on the back wall. It was Ben in his Halloween costume! She went closer to get a good look.

As Anna looked at the photograph, she remembered her wonderful night with Ben. Her pussy instantly started to moisten.

A glint caught Anna's eye. Underneath the photo, there was a small, gold plaque. It said:

William Butler

Beloved Son and Brother

1921 -- 1944

An elderly woman came up next to Anna.

"Handsome, isn't he?" the woman asked.

"Yes," said Anna. "Who is he?"

"Oh, he's the landlady's older brother. He died in World War II. It's a shame," the woman said. "The landlady's had this photograph hanging in the lobby of this building since she bought it. Such devotion!"

"Yes, it's very sweet. Well, I must be going now," Anna said. She tugged on Chance's leash and the two of them walked out of the lobby. Anna certainly had a lot to think about. But, one thing was for sure, she was definitely going to be moving into that building as soon as possible.