Personal Assistant Pt. 04

James had just finished eating his dinner when he heard the front gates of the house opening. He glanced outside his guest house which had a good view of the driveway to see a limo pulling into the circle.

The limo pulled around the circle and stopped by the front doors of the main house where Anna lived.

He saw the unmistakable tall curvy figure of Anna as she stepped out. Then 3 beautiful women joined her getting out of the limo. It was hard to tell just how pretty from this distance, but he could see enough to tell that they all had killer bodies.

The tallest girl had long blond hair and looked thin. Her boobs looked huge but compared to Anna everything about her still seemed small. The more average height girl had beautiful red wavy hair and a curvier frame with large boobs. The shortest girl had more natural looking blond hair and looked very fit, like the other girls she also had large boobs.

James always felt a little intimidated in Anna's presence, but with these 3 bombshells, he had no idea how he was going to keep it together.

They grabbed their bags and disappeared into the house. James was a little unsure what to do but didn't want to rush over too soon to meet everyone. He decided to take this opportunity to freshen up and make sure he was ready.

About an hour after he first saw the limo drive in, he got a text from Anna.

"Come over and meet the girls, don't be shy, they won't bite. At least not at first..." it read.

James' heart was fluttering, she was already starting to tease him. What was he getting himself into? He took a couple moments to gather his nerves and headed over to the main house.

He could hear music playing inside and it sounded like the girls were already partying. He opened the door and made his way to the kitchen where he could hear them all talking and laughing.

"Hello." He announced his presence so he didn't scare them.

"There he is." He heard Anna state from the other room.

As he turned the corner he was met with 4 beautiful smiling faces as the girls greeted him.

The alcohol was all out on the kitchen island as the girls were making drinks and gossiping. Anna came around and gave James a big hug pressing his head firmly in her massive breasts. She had her 3 inch heels on so she towered over him by 8 inches.

The girls came around and stood before him waiting for introductions. Anna released James and motioned to her friends. "James, I would like you to meet my best friends." She pointed at the tall blond first.

"This is Candy." Candy stepped forward and walked up to James. She was indeed tall, with her 3 inch heels she was eye level with James. She had innocent brown eyes and a beautiful long face. He couldn't believe how much she looked like Charlotte McKinney.

"Hey James." She said in a cute bubbly voice. Before he realized what was happening she leaned in and gave him a passionate kiss on the lips and then gave him a nice long hug. Her breasts were nothing compared to Anna, but they were still very large and he could feel their full size pushing into his chest.

As she pulled away she gave him another kiss, this time on the cheek. "It's nice to meet you." She let her hand linger on his chest as she looked him deep in the eyes almost trying to tell him something.

"Okay, okay, slow down tramp." The beautiful red head pushed Candy out of the way and proceeded to give him a friendly hug.

"Hi James, I am Jess." She said as she stepped back with a friendly smile.

Jess had intense blue eyes and a beautiful face. Her long red hair was shiny and smooth as it cascaded down her shoulders and along her back. Her boobs didn't look as big as Candy's but were still large by normal standards and complimented her curvy figure.

"And this is Alexa." Anna continued with the introductions.

"Hi James." Alexa stepped forward and gave James a friendly hug like Jess. Unlike Jess when she pulled back he felt a little pinch on his butt and she gave him a mischievous wink.

Alexa was the shortest of all the girls but looked the most fit. Like all the girls she had large boobs that she used to her advantage. She had shoulder length natural blond hair and pretty green eyes.

"Nice to meet you. Wow you are all so beautiful." James blurted out. They all smiled at the compliment.

"You are so sweet." Alexa said. She stepped forward and ran her hand along his arm as she said that and stepped back in line with the other girls.

"What would you like to drink?" Anna offered pointing to the assortment of alcohol arranged on the kitchen island.

"You are already a couple drinks behind." Candy said pointing out the obvious. "You better start drinking."

James made himself a Vodka soda and lime as the girls kept talking and giggling about something they were discussing before he came in. He felt very nervous being in the presence of these stunning women.

After James was finished making his drink and took a couple sips Candy walked over and put her arm around James like an old friend.

"So Anna tells us you are an artist." She asked, as kind of an ice breaker.

It helped ease him a little as he was able to talk about something he was passionate about. The girls were so nice and asked inquisitive questions making the conversation easy.

The whole time he was talking, Candy still had her arm around him. The girls moved in closer as well, clearly not having personal space issues.

"Why don't we go sit down in the living room?" Anna suggested.

Everybody agreed and walked into the grand room to sit by the fireplace. Candy and Alexa sat on the couch while Anna and Jess moved over to the chairs opposite the couch.

"Come sit here James." Alexa said as she patted the space between her and Candy.

"Okay." James said nervously as he sat between them.

Candy put her arm behind James so it was along the back of the couch and leaned in a little. Alexa put her hand on his leg and gave it a reassuring pat before she returned her hand to her lap.

The girl's attention was intoxicating. They smelled so good as their perfumes mixed together given the close proximity.

The conversation continued as the girls updated each other on what was going on in their worlds. They were all so comfortable with each other, James could tell they all got along well and were true friends.

Even though most of the conversation was among the girls they would keep him involved by explaining things and even asking things about his life.

He was really starting to get a feel for the 3 girls personalities which were all so different but all worked together.

Candy was from Texas and had a slight southern accent. She was bubbly and light hearted and seemed the nicest of the 3. She was very touchy feely like she was flirting, but more innocent.

Alexa was also from Texas but didn't have an accent at all. It seemed like her and Candy hung out a lot and maybe even lived together. She was a huge flirt and was constantly touching James and pushing her boobs into him. She was the funniest of the group and very spunky.

Jess was from New York and had a tough exterior. It was all for show but she was definitely a lot more intense than the other girls. She was very sarcastic and kept everyone on their toes.

Eventually James started to relax and get comfortable. There was no judgement from these girls and the bottom line was they were a lot of fun. The time just flew by and before anyone knew it, it was midnight.

"Well ladies and gent, I need to get some sleep. I have something I need to do early in the morning. Don't worry; I will be ready to party late tomorrow night." Anna declared.

With that she got up and all the girls gave each other long hugs goodnight. James also got a nice hug before she said her goodbyes.

Now that Anna was gone James was unsure what he should do. That question was quickly answered.

"You need to stay up with us James, the night is young." Alexa declared.

"Okay sure." James said as they all sat back down in the chairs.

"So what do you think of the house?" Candy asked.

"It's amazing. It's easily the nicest house I have ever been in." James responded.

"What do you think of the bedrooms downstairs?" Jess asked.

"What do you mean, aren't they just guest rooms?" James responded.

"You haven't looked in any of the bedrooms downstairs?" Alexa said with a chuckle.

"No...why?" James asked. Now he was getting curious. Anna kind of mentioned the rooms but never really made it seem like they were a big deal.

"Oh, you have to come take a look. It's going to rock your world." Alexa said jumping off the couch and pulling James up with her.

The other girls got up and headed to the basement stairs. Candy hung back and took James' arm to escort him along.

She pulled him in close to her as they walked to the stairs as if she wanted to tell him something.

"So James, from what I have heard you haven't been doing so great with your test." She said in a low voice.

"What test, am I doing something wrong?" He asked in a panic.

"No, you haven't done anything wrong, but you aren't passing with flying colors either. My best advice is you just need to relax a little." Candy explained.

"What do you mean, what test?" He asked again.

"I am not supposed to be telling you about this, but Anna has been testing you since you started. You just need to trust us. Do you trust us?" She asked, looking him in the eye.

"Yeah, I do." He responded.

"Good, then come on." She said as they made their way down the stairs.

The other 2 girls were already downstairs waiting for them. Alexa was giddy with excitement.

"Down this way first." Alexa skipped down the halfway to the right of the basement stairs. She stopped at the first door.

"Room 6." She said.

James looked at the door and noticed the number six was nailed to it like an apartment number. Alexa opened the door and flipped on the lights.

It was a dungeon. James couldn't believe his eyes. It looked like it was straight from the middle ages with stone walls and floor. It had a table with straps on it made of leather and old wood timbers. On the other side of the room two wood timbers formed an X with what looked like straps for arms and legs at the ends. Hanging on the walls was a large assortment of whips, chains and handcuffs.

James marveled at what he was seeing as he tried to make sense out of some of the other things in the room.

"Pretty cool isn't it?" Alexa asked. She was entertained by the look of confusion on James' face.

"Is Anna into BDSM?" He asked.

"Sure, among other things. This is just the first room we showed you." Candy answered.

"There is more?" James asked.

"Yup, come on let's check out room 5." Alexa said.

We all followed her to the next door which had the number 5 on it. She opened the door in a similar fashion with that look of mischievous excitement.

Room 5 was similar to room 6 except the style. Instead of a dungeon, this room was all red with what looked like velvet wallpaper and wood floors. The accessories looked a little more modern instead of the medieval theme in the first room.

"Wow, this is something." James said as he moved around the room checking everything out.

He had never been into bondage, but with Anna he could see why she would be into this stuff, it seemed like she liked to be in charge. Honestly the thought of doing anything with her got him excited.

"The next room is pretty cool, wait till you see this." Jess said.

"Oh yeah, this one is fun." Alexa added.

They went back out to the hall and made their way to room 4. Alexa opened the door and flipped on the lights. This room was completely different. There were a couple leather chairs and a table along the wall but most of the room looked like a big wrestling mat.

"This is the wrestling room, or more often the oil wrestling room I should say." Alexa explained.

"No way!" James exclaimed.

"Oh yeah, I have had some fun in here." Jess confessed.

"Really." James said, raising his eyebrows.

"You look pretty strong, but I think I can take you." Jess boasted.

James had so many questions. It seemed like the girls were all too familiar with all the rooms downstairs, like they regularly use them.

Like all the other rooms down here he could see this one also had a private bathroom connected.

"The other rooms are more my speed." Candy said. Everybody walked back out into the hall. They had to backtrack down the hall and take a right. The hallway was a T shape and he could see the window to the pool up ahead now.

Room 3 was like a honeymoon suite. It was all red with a big round bed in the middle. Room 2 was like a superhero theme. It had a cityscape along one wall and the other 3 walls were vibrant red, yellow, and blue colors. This room had a big closet which had all kinds of superhero costumes in it.

This brought us to room number 1.

"This is my favorite room." Candy admitted.

When they walked in and flipped on the lights James first noticed how bright it was. It was extremely well lit but not blinding. James looked around in amazement. Every wall including the ceiling was a mirror. What wasn't a mirror was bright white including the huge bed, molding, and soft carpeted floor. The bed seemed to float as light poured out from underneath.

"The bed in here is amazing, try it out." Candy said. She gave him a push so that he lost his balance a little and decided to go with it and jumped on the bed.

She was right; it seemed very plush and comfortable. Before he knew it Candy jumped on the bed next to him and Alexa jumped on the other side sandwiching him. Both girls had their hands all over him caressing him in a slow and sexual way.

All of a sudden the mood of the room shifted. The girls seemed a little more serious and James couldn't help but think he just walked into a trap.

"So what did you think of the tour?" Jess asked standing over them with her hands on her hips.

"It was a lot to take in." He said nervously.

He tried to sit up but the girls pushed him back down. Before he knew it Candy was giving him light kisses on his neck. Alexa continued caressing him and her hand found its way under his shirt and was now caressing his stomach and chest.

"Ah guys, I don't know what is happening, but I don't want to screw anything up with Anna." James said.

As incredible as this was, he didn't want to jeopardize his relationship with Anna. He felt like he was having real feelings for her and didn't want to mess things up.

"Ahh, how sweet guys. I think he really likes Anna." Jess said. She wasn't condescending but sounded like she genuinely was touched at his gesture.

It did nothing to stop the girl's efforts. Again, James tried to sit up.

"Do you trust us?" Candy said looking James in the eyes. She was so sweet he couldn't believe there was anything they would do to hurt him.

He also noticed she used that phrase again. She asked him that same question before the tour when she told him he was being tested. Was this part of the test he wondered. He looked deep into her beautiful brown eyes and decided she was trying to help him.

"Yes, I trust you." James admitted. She smiled and leaned in giving him a passionate kiss that made all his worries melt away. She guided him to lie back on the bed.

He could feel Alexa's hand go south a little as she started to caress under his pants. At this point James looked to the foot of the bed to see Jess starting to undress. In no time she was fully naked standing there looking spectacular.

Her body was even better than James realized. She had big round boobs that sat on her frame perfectly. They had to be at least a DD maybe even bigger. She was very curvy with a small waist and flat tummy. Her legs and butt were very thick but looked smooth and muscular.

She wasted no time and began removing his socks and pants. Alexa assisted by unbuttoning his pants and then started removing her clothes.

James could tell Alexa was fit and his observations were confirmed when she was done removing her clothes. Her boobs were a little smaller than Jess's but almost seemed bigger on her petite frame. She was toned all over and had a nice six pack. James had been to enough bodybuilding shows to know that she would be a good competitor in the bikini competition.

As soon as Alexa was naked, she began removing the rest of James' clothes. This broke Candy away from kissing James to start getting naked herself.

Candy had a tall lean body that was capped with huge boobs. She had the biggest boobs of all 3 girls by at least 2-3 cup sizes. Amazingly all 3 girls also looked like they had natural boobs; nothing on these women looked fake.

By this time Jess had removed James pants and was pulling down his underwear to finally reveal his extremely hard and huge erection. All the girls gasped when they finally saw him naked.

"Holy shit! That is the biggest dick I have ever seen!" Jess blurted out.

Alexa grabbed on and started stroking his cock in front of her face. Her eyes were wide with amazement.

"OMG, it's amazing." Alexa said.

"Oh wow, you better take it easy on me with that massive thing." Candy warned. "I have never had a cock that big either."

This was an extremely interesting turn of events for James. He usually got the opposite reaction from girls when they see his cock for the first time. These girls looked genuinely excited at the prospect. Most women are scared when they see him the first time.

He is always gentle when he is with women and has never had much of a complaint. He has never been able to get more than half of his cock in anyone, so he was hopeful things might be different tonight.

Jess went into the bathroom and returned with some lubricant. She rubbed it all over her hands and started stroking his cock up and down. While she was doing that Alexa was kissing and caressing his abs.

Candy had propped herself up and was letting her massive boobs hang in his face so he could get a good feel for how big and natural they were. James was in heaven as he felt her soft pillowy boobs smother his face.

Before he knew it he could feel Jess straddling him on the bed as she got into position.

"I gotta feel this monster cock in me." She said.

It was the most amazing feeling to have 2 girls on either side of him with their hands all over him and to have a 3rd woman mount him and start to pull his cock inside of her. The sensations were all over and overwhelming.

James did his best to relax and enjoy the moment. He could feel Jess slowly envelope his cock as she eased herself down. She gave a small moan of pleasure as she started to gently grind the tip of his cock taking it real slow.

Jess started to pick up the pace as she got more comfortable with his size. After a couple of minutes she was able to take a little over half his length. It felt great but James always wondered what it would feel like to go all the way into a woman.

Right now Jess took center stage as she leaned over James giving him long passionate kisses. Candy and Alexa were kissing his neck and all over his body.

Jess slowly picked up the pace as she got more into it. Her sexual energy was also going up as she sounded like she was getting close to climaxing. James wasn't even close to climaxing but was getting into it as well.

After a couple minutes of intense screaming Jess finally let loose a passionate orgasm and collapsed on top of James breathing heavily.

"How are you doing big boy?" Candy whispered into his ear between hot kisses.

"Ready for more." James responded.

"My turn." Alexa declared.

Jess, still breathing heavy, rolled off James and Alexa jumped on top. Instead of traditional cowgirl, she turned with her back facing James so she was in the reverse cowgirl position.

She grabbed onto his cock and started to rub her vagina with his tip. The sensations were great as he propped his head up to watch the show.