Mom at the Fraternity House
I was waiting with my friend Kyle at the most discreet entrance of our frat house. It was a little side door with no clear walking path, and a driveway that was accessed separately from the main one. This was because it wasn't our driveway, it was actually for a different building. But you could see our little side door from it, so whenever we were trying to sneak something or someone in, this was the place to do it from.
In the case of Kyle and I, we were sneaking in a prostitute. This wasn't something I normally did or anything. But, in the month since I'd joined the frat, my roommate had gone on and on and on about how into married women he was, and he'd eventually taken to saying that he needed to hire a prostitute to play the part. After weeks of that, I finally caved and pointed out that we literally had a famous brothel about an hour away from us; and he should either do it or stop talking about it.
Mind you, Kyle was the kind of guy who normally wouldn't do either. So I was surprised as hell when he said that he was going to do it. He wanted to set the whole thing up, but then kept asking for my help. He didn't have a credit card so he wanted to give me the money and have me use my card. He got their phone number, but was afraid to call and ask himself. When I directed him to their handy-dandy website, he was quick to point out that they had rates for two, and then go off on how, I was the one who had told them this was an option. As if that gave me some moral obligation to go in on it with him. But, mid-argument Kyle pointed out that if I caved and lost, my "worst case scenario" was getting a blowjob from a beautiful prostitute wearing Wedding Rings.
So, after he offered to pay for half of my share, I genuinely decided it was worth it. Not just because of a BJ from a certified hottie/professional (mostly that), but also because it would make Kyle stop whining about it. Fast forward a few weeks, and a car pulls into our little side drive that I recognize. The moment it happened, my heart dropped out of my chest and I felt myself go cold with growing horror. Like, in the back of my mind I knew it was a possibility, but I just kept telling myself that the odds had to be stacked against this happening. And in fairness, the odds were crazy low. But crazy low and zero are not the same thing.
Kyle, on the other hand, was thrilled when he saw her. She had long beautiful hair, lovely skin, really big tits, and, as she spotted the two of us and began to walk over, you could easily add great ass and sexy walk to the list as well. But as Kyle looked at me, awash in excitement, he saw that I wasn't excited. And, god fucking help me, the best my stupid-ass brain could come up with for what was wrong when he asked was, "Oh uh. She just, um, she looks like my Mom is all. It's kind of weird. That's it." I sounded like Han Solo saying, "Everything is fine here! How are you?" in Star Wars. Only an idiot would believe me.
Thankfully, as my Mom, a woman who definitely looked like my Mom, was walking up to us, Kyle's blood had abandoned his brain in favor of his dick. So, he was, at the very least, a temporary idiot, and accepted my terribly worded excuse without question. In fact, it didn't even occur to him that getting a blowjob from someone who looked just like my Mom might be an issue. In fairness, all he cared about was, "Was she wearing Wedding Rings?" And, as she walked up to us, the familiar sparkle of her real wedding band paired with her real engagement ring was clearly present on her left hand.
As Mom walked up and got a good look at us, there was the briefest drop in her guard. She saw me, and, for just a moment, that professional, beaming smile of hers, faltered. But it was only a moment, and luckily, Kyle wasn't staring at her face when it happened. So Mom's low-cut top had saved the day.
That said, low-cut didn't do it justice. Mom was wearing ripped up denim shorts; I think they called them Daisy-Dukes. They were paired with short, heeled black boots, and a white shirt that probably would have gotten her arrested if she'd taken the bus. The shirt white cotton. It was also cinched up, tied in a knot, and doing everything it could to communicate that my Mom's very large, very lovely tits were braless underneath it.
She had a little black shoulder purse as well, that I knew would be full of lube, oil, and condoms.I knew this because before I'd left for college (the day after I turned 18), I finally asked Mom why she had a separate purse for work. I'd just recently been told what she did for a living, and the fact that she was gorgeous, a prostitute, and my Mom, had been giving me very mixed feelings. I learned something about myself though when, in a semi-sexual tone, Mom had answered my question of "What's in there anyway?" She grinned, and replied, "Lube, body oil, and condoms." In the weeks that followed, I had masturbated to the memory of her saying that, dozens of times. A fact that really cleared up the whole, would I really fantasize about my own Mom, thing.
But now, here she was. Lube and all. And she'd been hired by my roommate to give us both blowjobs while playing up the fact that she was married, so there was that. I honestly half expected her to have some cool excuse, or clever words that would get us out of this situation. But instead she just walked up to us, and with a big smile on her face she said a line about the weather that was her side of the passphrase that the website had prepared us for. Kyle, smooth for the first time in his damn life, replied back with our side of the phrase, and without another word, Mom gestured for us to lead her inside.
We led her to our room, and, once we got there, Kyle tried to introduce himself. But Mom cut him off by pressing a finger to his lips. She was gentle with the touch, and her smile was so charming that I think we both adopted some really goober looking grins in reply. Mom, for her part, just said, "not like that." Then she asked us where the shower was.
It wasn't random of her. On the website Kyle had to put in a bunch of stuff about his fantasies, his likes, and his deal breakers. I made him delete one of his likes, and when he griped about it, I reminded him that he was supposed to be filling it out for both of us. But, long story short, he had a fantasy about sex in the shower, and while we hadn't paid for sex, Kyle's excitement when he started to show her the way, clearly said that a bj in the shower was just as good.
My thoughts were racing with how I might back out of this, or stop it somehow. I honestly (I SWEAR!), couldn't believe she was there. This might sound like a weird thing to say, but my Mom cost way more than Kyle and I could afford. Dad had called her one of the brothel's top performers, and implied that it took a small fortune to get her attention. Now, I would later learn that Mom was filling in a friend who just needed to take a break, so she was attending all of her appointments and for the money that her friend normally accepted. That was how she'd ended up at our door. But at that moment, it was extremely confusing!
As my thoughts raced, things happened so fast that I could barely keep track. We got to the bathroom and I was asked to close the door behind us. Mom told us to strip, and began to get undressed herself. Then she told us to get in the shower, and she got out an oil of some kind that she used to make her absolutely gorgeous body glisten. Mom was careful to mostly keep all that lovely hair of hers away from the oil, but she also didn't use a hair tie to put it up. For the record, that time, all of it, was when I was lost in my thoughts. Kyle and my Mom were in the shower, naked, with Mom's sexy curves all oiled up and ready, and I was still just standing by the door fully dressed.
Kyle went to say something to or about me, but Mom interrupted him with, "Ready for that introduction?" and he was quick to accept the distraction. I could hardly blame him, only a fool would be looking at anything other than the absolute goddess that was standing naked in front of him at that moment. Kyle nodded, and started to introduce himself again, but Mom once again gently touched a finger to his lips.
"Not like that," she said with a suggestive smile. Then she dropped down to her knees. Looking up at him, she used her left hand to articulate as she spoke. Gesturing to herself or to him with it, and of course, drawing attention to her Wedding Rings as she did so. "With a regular Married Woman, you would introduce yourself with a handshake, and as you did, you would exchange names. That is true. But I," she said, touching her hand to her very impressive chest, "am not a regular Married Woman." Then she batted her eyes prettily up at him as she clarified, "I am a Married Woman, and a Whore. And we do things a little differently."
Kyle was rock-hard by this point, and Mom actually had to move her head a little to the side so she could look at him around the dick that was now bobbing in front of her face. "Now," she purred. "What's your name sweetie?" He answered her, and Mom smiled, and then swallowed his cock in one smooth motion. She moaned, and sucked, and bobbed her head. Her lips slid up and down the length of Kyle's dick as he cried out in pleasure and surprise. It was only a few seconds, but to Kyle and I it definitely seemed much longer! When she was done, she popped her lips off of him, looked up into his eyes and said, "Hi Kyle, I'm Missus (Mrs.) S."
After a second, Kyle laughed, and looked at me, which had my shaking my head and thinking "don't you fucking dare!" But it was too late, the thought, like a seed, was already planted. Mom tipped her head to the side a bit, and asked with curious amusement, "What's so funny?" Kyle apologized, but was quick to let her know that it was funny that she was Mrs. S., because, "The first thing Steve said when he saw you was that you looked just like his Mom. And his last name is Smith."
Mom held her hand to her chest and laughed a little, admitting, "That is kind of funny. But, you know what's extra crazy about that?" Kyle took the bait and asked what, so she replied, "That is kind of my thing usually. I roleplay as people's Mom. You know," she said suggestively. Then she held up a hand to the side of her head and added, "While I'm working" and as she said it, she sucked on the imaginary dick she was holding.
Kyle's face flushed red, and even though he'd had zero reaction to my comment about her looking like my Mom, when she said that roleplaying Mommy was something that she did, he was clearly into it. "Wow, that is kind of hot..." he muttered. In reply, Mom smiled up at him. "Yeah?" she asked. "Then we should totally do it!" she added.
