Author's Note: All characters in this story are at least 18 years of age, and, even in role play, are "playing" characters at least 18 years of age.
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The birthday boy was center stage, as all his friends, the guests at his party looked on. He was sitting in a chair made of dark wood. On the matching wooden table behind him, was a mess of unopened presents, cups, soda bottles, and a cake that had yet to be cut into. The open room set-up meant that his friends in the living room could look right at him in his kitchen, as it all blended together into one area with no walls. The only real distinction was the sudden changeover from comfortable carpet to cold tiles. Everyone was looking his way, and he was nervous as hell, but not because of the people looking. No, he was nervous because, just like the people looking on with held breath, he knew what was coming next.
The party consisted of only his straight, male friends; and there was a reason for it. His Dad had proposed for his 18th Birthday, that he hire a very expensive call-girl from the town's famous, and infamous, high end service. With that kind of thing, you needed a bit of discretion involved. So his guests had been carefully chosen, close friends only. Plus, they had all been in on it in advance so that no one freaked out and bolted last second. Some of his buddy's couldn't make it because of work, or family vacations, or some pretty big sporting events that happened to be going down that same weekend. But those guys hadn't been told what they'd be missing, so it was understandable. Besides, the birthday boy was already a bit worried about the male to female ratio since, hiring this woman meant that there was exactly 1 woman, and, at current numbers, 10 guys... plus his Dad.
That had been how the whole thing started. He and his Dad had been watching a movie, when an intimate scene came on. One of those rated R affairs, where the pretty people get into it and nudity is shown, but the actual sex is hidden and brief. Then, out of nowhere his Dad had blurted out that he'd always had a fantasy about a "Father-Son team-up". Apparently he had been the Son when the fantasy started, but, he didn't stop talking about it. He just kept musing about it outloud. He started by talking about how it started, then how it stuck with him, then how he'd thought about the nearby whore-house (called The Resort) over the years. Before he was done an hour had passed and he was excitedly suggesting the very plan that they were now all carrying out. He and his friends were going to share a very beautiful, very expensive, very talented call-girl for his birthday. But, before anyone else got to touch her, the birthday boy and his Dad were going to double team her first.
So, there they were. Him and his friends, all waiting while his Dad met the woman at the door, and got ready to bring her in. When she came in, she came from behind him and to the side. His Dad had, very specifically, wanted to bend her over and take her from behind, while he got a blowjob from her in the chair. Again, tying back to his Dad's fantasy from when he'd been younger. Honestly, he didn't care how much his Dad had made it about himself; he was kind of psyched for the whole thing anyway.
When she came into the room, his buddies all gasped. Some of them blushed, a few of them said "no way" like they couldn't believe it was really happening. A couple of others commented on how it was "So hot!" But, as gorgeous as the woman must have been to garner those reactions, he couldn't bring himself to look. He knew he was blushing and he was insanely nervous.
She WAS gorgeous though. The place they'd hired her from had a reputation, not merely as one of the best around, but as one of the best in the country. She had long strong legs that were capped with the most perfect ass any of them had ever seen. Her breasts were huge, and her clothing only served to highlight how truly breathtaking her cleavage line was when they were pushed together by said clothing, or a pair of hands. Her long hair was truly beautiful, and she had eyes that almost matched that same level of loveliness. One look at her, and you understood why wealthy people paid small fortunes for access to her time. And that wasn't even all of it. In her profession, there was a lot more to the job than simple looks or skill in the bedroom. The best of the best were charming. Smart, funny, easy with a laugh or a flirt; and this woman had charm to spare.
Of course, he knew all of that about her at a glance when his Dad asked, "Ready for this buddy!?", and pushed on the woman's shoulders. As he did, she smiled, gave a wink to the boys waiting in the "audience", and bent forward until she was hovering over the birthday boy's bulge. His Dad told him to "take it out already", not even pausing when his Son gasped and his eyes went wide at the sight of the woman he'd brought in. His Dad had his pants around his ankles, and was working to get her dress hiked up over her ass before he even paused long enough to ask, "What?" in a semi-annoyed tone.
But while his Dad may have started out as annoyed, his Son's answer turned that mood around in an instant as he gasped out, "I know her!" At first, he gave him an approving grin, and continued to get himself into position as he remarked; "No way! Nice going stud. How on Earth did you manage to afford that?!" But as his Dad began bumping the head of his cock into the plump, wet lips of the woman's pussy, causing her to give an approving little moan and glance back at him wickedly, his Son clarified what he'd meant.
He tried to get it out before his Dad could, you know, finish doing what he was doing... But he didn't manage to spit it out in time, and so the sound of him saying, "She's my best friend's Mom! It's Misses (my last name)!" was immediately followed by the sound of her moaning loudly as his Father finally lined everything up properly, and buried the full length of his cock inside of her very snug pussy.
At first, he didn't believe his ears. He didn't know all of his kid's friends, so he sure as hell didn't know all of their parents. But the kid he was talking about had been his Son's best friend for YEARS. He'd heard the name a thousand times, even if he didn't know a ton about him. In the moment, he paused. In part because his brain was trying to process what he was hearing, but just as much so because he was currently balls deep in the tightest, most amazing pussy that he'd ever felt in his life. After a second, he managed to swallow some of the overwhelming pleasure he was feeling down, and ask outloud a question that he was sure that his Son couldn't possibly be right about the answer to.