tagGroup SexAnother Late Night

Another Late Night

byjclancy3©

It was another late night at the office. Rick was at his desk and had just finished up a phone call. He and Emily were the only two there at around 8:00 PM.

Emily, one of Rick's younger assistants, was an energetic young woman with curly brown hair down to her shoulders, a beautiful face with soft Greek features, a smooth, tan complexion, and wide green eyes.

She was wearing a black, silky shirt that was just a bit tight over her larger than average sized breasts. Rick always loved to see her in this specific shirt as it seemed to exaggerate the active movement of her breasts as she walked. They would jiggle uncontrollably like they were just about to escape the loose confines of her bra.

"I've been working on this but I guess I'm a bit stuck, Rick. Could really use your help," Emily said as she walked over to stand next to him at his desk holding a memo she'd been typing away at all day. As she walked, her breasts were jiggling like crazy. It was a bit chilly in the office which caused her nipples to protrude from her blouse. She must have really long, hard nipples Rick thought as he looked probably too long at her chest. He saw that her areolas were puffed up and sticking out as well, showing the complete outline of what must have been an amazing view.

As she stook beside his chair, he leaned back, glancing casually at her ass. Nice and round, very full. He wondered if she was wearing a thong since he couldn't see any panty lines.

"Let me see it . . . the memo," Rick said, shaking himself out of his daydream. He looked it over but just couldn't focus. "How long have you been working on it, Em?" He really wondered why she was here this late working on something so miniscule, but he wasn't complaining.

"A few hours. I have nothing better to do." Rick instantly thought of several better things they could do to fill the time, but he steered his mind back to the memo.

"Why don't we get a drink and talk about it," Emily offered.

Rick looked up and saw a look in her eye that he hadn't seen since she first came to the office for her interview. He couldn't read exactly what it was, but knew that whatever she was working on was important to her, and she was being a bit flirty to get his help.

Rick knew how to play this game as he had played it over many times in his head. "Sure, Em. My boss has some in his office. Let's see what he's got. You lead the way."

Emily walked toward the inner office and Rick followed behind her, his eyes fixated on her ass as she swayed her hips. The bottom of her butt cheeks were jiggling just like her tits, and Rick longed to grab on to them.

In the office, Emily opened the door of the closet where she knew 'the stash' was hidden. Rick sat on the corner of the desk as Emily poured two glasses full of what must have been a higher-end bourbon. She handed Rick a glass and clinked hers to his in a quick toast. "To late nights!'" she giggled.

They both sat down. Rick nursed his bourbon while Emily put back three or four. She started getting very giggly and expressive as she talked. Rick smiled and pretended to listen. What would it take to --

"--so then Maria asked me if I'd ever kissed another girl and I blushed thinking about college!" Whoa. The conversation obviously took a sharp turn toward the more interesting, and Rick decided to jump onto that topic.

"What happened in college, Em?" Rick asked thinking about Maria who was a beautiful Italian girl who had worked for Rick for a few years now. She was a little older than Emily but younger than Rick. Her age was starting to show just a little as she put on some weight, but she still had a beautiful face, petite tits, and a nice round ass on top of solid, muscular legs.

Looking at Emily, Rick noticed that she was obviously not a heavy drinker, and her face was red from embarrassment and drunkenness. Her nipples looked like they were about an inch and a half long above her large areolas, and for the first time Rick noticed that they were just a little off-center, pointing out to either side of her body. He immediately imagined she and Maria together on the couch, acting out their college experiences.

"Well, you know, sometimes you get curious," Emily continued, "and I had been drinking and my roommate and I kissed and did some stuff -- no big deal, right?"

It was a big deal, big enough to start a noticeable bulge in Rick's suit pants. Emily looked at Rick's lap and said, "I can see you liked that little story. Maybe I should tell Maria!"

Rick decided to go in for the kill. He'd always heard of guys taking advantage of their female assistants, but never had the guts to try it himself. But the same instincts that got him to the top of the office were in high gear now. "And I can see that you're either freezing cold or extremely excited yourself, Em!" he said, pointing at her chest that was pointing back at him.

"Oh, you noticed?" She said putting down her glass and pointing to her nipples. "Yeah, I can't keep the girls under control. Hey, you want to see them?"

"If you want to show them," Rick was very quick to reply.

With that, Emily stood up and stood in front of Rick so his face was about a foot away from her stomache. She lifted her shirt and grabbed her bra on the way up. Her breasts jiggled after their release and stuck out against her chest. They didn't sag a bit, and as Rick has noticed before, the off-center nipples pointed way out to either side now that they had been set free. Emily looked down with one hand and grabbed her left nipple, rolling it between her finger and thumb. "Believe it or not they get bigger!"

Rick was amazed. There they were, the nipples he had dreamed about, right in front of his face. They were light brown, and at least an inch and a half long. Her playing with the one had caused it to get so stiff that it looked as if it grew to two inches!

"Wow, Em," he said as he continued to stare. He lifted his hand up and grabbed her right breast. It started to jiggle just like he had imagined it would when he touched it. He grabbed the nipple and did exactly as she was doing with her left one. She giggled and threw her head back looking very content.

He pulled her closer and licked the tip of the nipple she had been tugging. He felt her shiver with delight in his arms, and she let out a small moan. He then put the whole nipple in his mouth and started lightly sucking and tickling it with his tongue. The moaning got louder and more intense as he sucked harder and harder.

His hand dropped from her right breast and reached down beneath her skirt. Her ass was very full and smooth as silk. His rod was bigger than it had been for a long time, and he could feel it throbbing.

"Oh god, Rick, are you going to do me or what?"

Remembering that he was the boss, he looked up and said, "first you have some work to do."

She dropped to her knees as Rick stood up, reversing their previous position. She took off her blouse the rest of the way, unsnapped her bra, and wriggled out of the straps. As it fell to the floor, she undid Rick's belt, unzipped the pants, and reached her hand into his boxers.

"Oh my God! We were right!" she said.

"Right about what?" he asked as she worked the nine solid inches out of his boxers.

"We knew you must have been huge, but we had no idea -- "

"Who's 'we'," Rick interrupted.

"Oh, Maria and I. You know how girls talk," Emily grinned. She stared at Rick's throbbing unit and opened her mouth. She licked right around the top of his helmet where it was already moist. She then slowly took it into her mouth. Every time her head moved back and forth she took it in a little farther. Rick thought he was going to explode, but kept control as he looked down. He could see her tits bounce around with every jerk of her head.

"Too bad Maria isn't here now, we could have a real party," Rick joked. He grabbed Emily's hair, and started jerking her head a bit faster. She looked up and smiled as best as she could with that huge cock in her throat. She took it out and looked up at him with devilish eyes and said, "well turn around big guy!"

Maria was standing in the office door! She was wearing the extra Oxford button-down shirt Rick kept in his office. She didn't have on pants, and looked incredible in his oversized shirt with nothing but her tan legs under the shirt tails. She smiled at Rick.

He tugged Emily's hair motioning her to get up. He motioned for Maria to come in. They were both smiling devilishly at him. "How long have you been here, Maria?"

"Long enough," Maria answered in a low, sexy voice.

"So you were wondering about something," Rick said pointing down to his prick that was in Emily's hand. With that, Maria walked over and pinched Emily's nipple. Seeing his shirt on her body was driving him crazy. It was open just enough at the top that Rick could see her own brown nipples poking into the cotton of the shirt. She was smaller and more 'compact' than Emily, but Rick couldn't wait to see them.

He stopped and looked at the two of them standing in front of him. He couldn't believe his eyes. Emily had worked her skirt off and was standing there in just a black thong. Maria unbuttoned the rest of her shirt, and let if fall to the floor. She stood next to Emily in her white cotton panties in contrast to her dark tan skin. He decided that he'd better get the situation under control.

"OK, look," Rick started. "I'm not sure how this happened, but now that you're all here, you're mine." They looked at each other, smiled, and nodded in agreement.

"Have you seen these before Maria?" Rick asked pinching one of Emily's nipples?

"Oh yeah, many times, Rick," she said. "They're amazing!"

"Well watch this," Rick said as he grabbed Emily and turned her around, her tits bouncing madly as he spun her. At that, his pants dropped, and he grabbed his dick and held it out toward Emily's ass. He bent her over the desk so that her palms were flat on the desk top and her ass was sticking out toward him. He motioned for Maria to get on Emily's right side.

"Emily, Maria's going to help me here."

Emily nodded and kept looking down at the desk.

"Maria, keep those nips stiff," Rick demanded. Maria immediately grabbed Emily's right breast with her right hand and put her left hand on Emily's right ass cheek, giving them both a squeeze. Rick reached over and cupped Maria's left breast, causing her to move in closer to him. Both of her breasts were dark tan, just like the rest of her, and her nipples were small but very stiff.

She had larger hips than he imagined, but her skin was tight and firm without an ounce of cellulite anywhere. She looked at him through the wisps of her brown hair which covered up her face when she looked down. It was a look that sent a pulse through his cock that was resting on the top of Emily's ass.

While massaging Maria's relatively tiny breast, Rick reached to his left and grabbed Emily's hanging free tit. He gave it a good hard squeeze, and moved it around in his hand.

"You have to get her ready for me," Rick told Maria. She moved Emily's thong to the side and stuck two fingers into her wet hole. Emily started to breathe hard and moan with every move of Maria's small hands.

"OK, that looks pretty good, Maria," said Rick, as she grabbed his prick and gently slid it into Emily's hole as she stretched it open. He slowly slid in the head, which caused a stutter in Emily's breathing pattern. This encouraged Rick to slide it in a few more inches, making it impossible for Maria to keep her fingers in.

As he kept poking his cock into Emily, he decided to get a little creative. He started easing back, and once the head of his cock emerged from Emily's cut, he lifted it up an inch and rammed it into Emily's asshole, which caused her to whip her head around and look at Rick in shock.

Maria reached down and started to kiss Emily on the mouth as if to help relieve the shock as Rick pounded his fuselage into her ass. Maria used her free hand to tickle Emily's clit, which helped keep her excited.

"Get down on your knees, I'm about to go," Rick commanded. Rick pulled his cock out of Emily's ass, and started to stroke it. As he did, he aimed it toward Maria's face. The first wad of jizz hit her right between the eyes. The second and third squirts landed on her chest. As he started to turn toward Emily, who by then was on her knees, two pumps left their mark on her forehead and cheek before she grabbed it and stuck it in her mouth to swallow the rest.

Maria let the first deposit drip down her face while rubbing the others into her breasts. Emily finished milking Rick's cock and immediately leaned over to slurp up the mess on Maria's chest and face before she rubbed it all in.

Once her chest was clean, Rick told Maria to lick the cum off of Emily's face. As she did this, Maria took Emily's hand and put it down her panties. She moaned as Emily started to get her off.

Once all of the cum was consumed and Rick's prick had relaxed down to a normal state, he told Maria to take off her panties and lay on her back. He then told Emily to come over and complete the '69' position by straddling Maria's face while burying her own face into Maria's neatly trimmed muff. As they started to grind into each other, Rick sat back and watched them. He couldn't believe that his prick was starting to get hard again.

He was almost hypnotized by the movement of Emily's swaying tits as she writhed on top of Maria's body. Both girls came to orgasm at the same time. As they did, Rick noticed that his prick ws ready to unload again, so he kneeled next to them and deposited his load between them, right onto Maria's overheated body. Emily lowered her stomache onto Maria's, and they both slid around until Rick's cum had soaked into their skin. It was the first time he had ever came twice in such a short period of time.

When they both calmed down, he told them to help each other get dressed. "Wow, Emily, you need a bigger bra," Maria said as she packed her tits into the cups. They both kissed Rick good night, and left the office without saying another word.

The next morning, Rick and Maria were sitting at their desks working in silence. Nikki, the office manager, came back and said, "Emily called in sick today. Said she couldn't get out of bed."

They waited until she left the room and started to laugh.

"We'll have to go over tonight and cheer her up," said Rick.

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