The Whore at the Glory Hole

 The Whore at the Glory Hole

The club I ran catered to a lot of things. At first, my girls and I just did massages with happy 

endings. But over time, we picked a reputation of being the best of the best. So, as the money 

came in, I expanded. You would think that working in a town where half the city was basically a 

red light district, would make it difficult to just run a straight up whore house... but you’d be 

surprised. See, it was one thing to go into a discreet building and have your needs met by a 

beautiful individual who was acting out your fantasy, and quite another to go to a car wash and 

have that same fantasy put on display in public. For the 2nd type, there was much to be gained 

by doing it “for real”. But for the first type, a little discretion would always be valuable. 

Because of this, as my business developed, I ended up adding a lot of areas that could be found 

elsewhere in the town. Yeah, you could go to the hotel in the red-light district and they could do 

anything you could imagine to you, but we still had a little fake hotel hallway, complete with fake 

elevator and a line of fake rooms. The duplication never hurt my business model once, and so I 

duplicated as much as I could. 

One of my favorite bits was the truck stop/convenience store. Built into the inner courtyard of our 

complex, was a fake parking lot, and a little area that acted as a real convenience store, and 

looked a lot like a truck stop or gas station complete with convenience store. This came with its 

own “ask for the key” bathrooms, and, of course, some of them had glory holes. So if you 

wanted to get your sleazy roadside fantasy on, in a very clean, very private, and very safe way; 

well then, my girls had you covered. 

So, suffice to say, we could get in a lot of different fantasies under our one roof. Over time, my 

little parlor had evolved into the most successful business in the city, and was currently more of 

a complex, consisting of multiple buildings and outdoor areas that drew in customers from all 

over the country. Though, naturally, we got our share of locals as well. After all, they were the 

original point of all of this. Now, one of those locals, was my Son… 

I have two, but I’m referring to my oldest at this point. 19, 1st year of college, and very handsome 

if you ask me. I knew, of course, that a horny teenager was going to find his way to the red light 

district when he lived in the city with the single greatest red light district in the country. I’d even 

figured he might end up at his Mom’s place of business, considering how successful that 

business was. But, what I wasn’t prepared for, was when one of my girls confessed to me that 

my baby boy had a Mommy fetish!

I was shocked, and turned on, and shocked… and did I mention turned on? I thought at first that 

maybe it was just that “Mom” role, and not me personally. After all, parents are the single most 

common fantasy. But, when she explained that he’d had her wear a wig that looked an awful lot 

like my hair, and that he’d actually taken out his phone and texted me at one point, while looking 

at photos of me on other occasions, well… there wasn’t much mystery to be had now was 

there? 

After that, I made a point of knowing when he came in, who he asked for, and getting a little 

breakdown of his adventures after the fact. I admit, I was surprised again when I learned that it 

was ALWAYS me. Like, didn’t the boy have other fantasies besides his Mom?!? But then… then 

one day he asked for the glory hole fantasy. No roleplay, no one to see, and no dirty dialogue 

from a full mouth; just a straight up nasty and naughty good time. And, heaven help me, but as 

someone who’d been masturbating to hearing about his fantasies for months, at that point, I saw 

an opportunity. 

My Son had already set everything up, and he was just waiting in the faux truck-stop to get a 

bathroom key, because there was a wait (filthy-sleazy realism at its best, trust me). Eventually, 

he got a key, walked around to the side of the building, and entered a bathroom stall with a glory 

hole, graffiti, and all the pretend dirtiness and grittiness that we could get away with. He actually 

went to the bathroom, left, washed his hands, and came back before going up to the glory hole 

so, points to his Mom, am I right? But a minute later, a large, if soft penis, was offered to whoever 

was on the other side. 

A delicate, and very skillful hand, took over from there. He was cupped, stroked, and played with 

by the best of the best. In no time at all his cock was rock hard. Then, only after his voice asked 

through the wall, “will you suck it”, did warm lips finally envelop the head of his cock. And from 

there on out, he was in paradise. My girls are amazing at what they do, and what they did was 

make men practically hyperventilate from pleasure. After a few minutes of licking, sucking, 

moaning, and utter bliss; I saw to it that he got a text from his Mom. 

Mid-blowjob, his phone rang out with my personal text tone, and I knew that someone with a 

Mommy fetish would not only, not be able to resist, but would find it utterly hot. So, naturally, he 

fished out his phone, to reply to my “Hey there sweetie! How are you today?” He texted back, and 

asked after me. Normally I’d have said it was because he was such a good kid, but since he was 

getting his cock sucked while texting me, and looking at my profile photo, he got fewer brownie 

points this time around. 

We texted back and forth a little bit, and eventually, small talk led to him asking what I was doing. 

So… for the first time ever, I actually teased him about what I do for a living. I mean, he KNEW. 

I’d never hidden it from him. But I knew for a fact that this was the first time that his text history 

with me had anything like what I’d just typed, which was, “Being naughty at work today. Wanna 

see?” 

His hard cock bucked, and he gave a half-moaned “Oh fuck”, through the wall of the bathroom 

stall. Eventually, he texted back with the most well-mannered and politely delivered request for a 

sexy text that I’d ever seen. “I would like that very much Mom.” It honestly made me smile. I sent 

him a reply text that read, “As an admin, it usually takes an awful lot of money to get me out of 

my office and ‘out on the front lines’, but I ran into a special case today.” 

Then I held out my phone, took a little video of “what I was doing”, and hit send. 

“Oh my god! Oh fuck!” His voice called out from the other side of the wall, as I heard him hitting 

play, and listened to him watching a little video of his Mom sucking someone off through a 

gloryhole. I flicked my tongue teasingly along the head of his dick as he pounded his fist against 

the wall, leaning against it for support, and swore a few more times under his breath in agonizing 

pleasure. Then I sent him another text. “I know I’ve never sent you work pics before sweetie, so I 

hope that wasn’t too much… if it was too much I can not send stuff like again”. 

Immediately, he texted back that he was TOTALLY fine with what I’d sent. In fact, he wanted 

more, and I almost felt him realized that there were two possibilities besides what he’d first 

thought. First, there were plenty of stalls, and his Mom might be in a different one. Second, his 

Mom might very well be in the next stall, and not know that it was him on the other side. He 

relaxed, ever so slightly, let out a big breath, and tried to play it cool as he continued texting me 

like nothing strange was going on. 

I texted him, and asked him if he would like another little video or gif of “the aftermath”, once I 

was done with my client, and he replied swiftly and many typo’s. Honestly, I almost laughed. But 

instead, I texted him again, and upped the ante. “Now, be clear for me sweetie, because this is 

our first time talking like this. Would you be okay with it? Or do you really, really, really want it?” 

For a solid two minutes, there was no reply from his end. So, I moaned…

I know that might sound crazy, but I’d been teasing him with his ultimate fantasy, so while I was 

giving him absolutely magnificent head, I was also going very slow. I was stopping on occasion, 

and generally dragging it out. I had very carefully kept my voice out of it as much as possible. 

But, if he wasn’t going to text his Mother back… 

I drew my mouth off of him with a depraved slurping noise, and moaned loudly as I began to jerk 

his cock a little faster. When I wrapped my lips around him again, I did so with gusto, as I began 

to bob on him and stroke him in ways that I knew would be making his whole body tremble with 

overwhelming pleasure. When I knew he was almost too close to back off, I backed off. Taking 

him right up to the edge… but then letting him catch his breath. 

“Running out of time to answer”, I shot off in a quick text to him. Before very gently, and very 

slowly working on guiding him towards a more stable, and not so, on the verge of cumming, 

place. He replied that he wanted it, that he really, really wanted it. And I felt like that kind of 

honesty deserved a reward. 

“I’m so glad to hear that sweetie!” I texted back. “I was worried for a second there that you might 

have a problem with what I do when you got to this age. But you not only don’t have a problem 

with it, you like it… Don’t you?”

He did good, and replied yes without the delays or the games from before. Which also deserved 

a reward, so I kept it up. 

“Yeah? You like that Mommy is a whore?”

“Yes”, he replied. “You like seeing your Mother’s face with a big dick being stuffed into it?” 

He moaned from the other side of the wall, and then replied with “yes” again. “Do you want to 

see me, your own Mother, looking like the whore I am. My face covered in cum?” And once more, 

he replied yes. But I threw him for a loop when I told him, “Then say so!”, and when he texted 

back that he wanted to see it, I told him, “No, not with your phone.” 

Confused, and building towards orgasm from just the texts now, he asked me what I meant. 

However… I answered his question without my phone, so he would be sure to understand. I 

noisily popped my mouth off of his cock, and called out through the wall with the most familiar 

voice in his whole world. Mom’s voice. “It’s simple sweetie”, I said. “You just yell it through the 

wall like this... Just say, Mom, I paid my money so that a dirty whore would hit her knees and 

suck me off in a sleazy bathroom stall, and now I really want to see my cum on her face.”

But, he didn’t say any of that. Instead he just screamed “FUCK! Oh God! Oh Fuck!”, and went 

straight into orgasm mode. I was, a little caught off guard, but not too much. I jerked him off nice 

and hard, and I told him how good he was doing, and how big his cock was, and how I came out 

of my office today just to be his dirty little whore, and stroke his nice big cock off for him. He 

rattled the wall as he practically fucked my hand in one, long, powerful, continuous, orgasm; that 

never seemed to end. 

Sadly, because he came so much sooner than I expected, I didn’t get to aim those first few 

splashes of cum at my face, but I was still able to send him a lovely little video of some of his 

cum hanging off of his Mother’s chin. It was also splattering my jacket in some places, my hair in 

others, and a big old dollop of it had hit the floor at my feet. He moaned out something along the 

lines of “oh my god!” when I heard him get my text, and watch the video on the other side of the 

wall. 

When it was all done, things played out normally. I left out of my private exit, and he out of the 

stall. We both got cleaned up, and, seeing as he didn’t have more money to spend on another 

fantasy, he was guided very politely to the door and offered refreshments before he left. Now, at 

home, things were a little different. 

He’d known what I did for awhile now, and I’d known what he’d been up to as well, but this was 

mutual, and real. It is one thing to know, for a fact, that your Mom has sex, and quite another to 

feel her moaning. Feel that moan vibrating through her lips and into your cock as she bobs on 

you and sucks you until you cum. And, we were in that second place now. 

At first, we just kind of played it off like nothing happened. My husband got in his hello dears, and 

we exchanged our usual flirtations as he teasingly asked me how work was. I told him, “So 

busy”, because I knew it was an answer that would make him shudder with delight. But later on I 

made dinner, and we all sat down for our meal like a family as if nothing had happened. 

The next day was the first time I really had a private moment to talk to my Son, and so, after his 

Dad had left for work, he came to me and asked, rather cutely, if there was anyway that what 

happened the day before could happen again, but on purpose. Which, was just SUCH a relief for 

me. I hadn’t realized what a gamble I’d been taking in the moment, but it was the whole world off 

of my shoulders to know that our relationship was intact. Better than that, we had a whole new 

aspect of it to play with. 

So, I thought about it for a minute, and eventually, I decided that the best answer I could give him 

was that, my place of business did house calls. And maybe, when he was away at college, he 

could shoot us an email, and ask for someone who looked exactly like me. Then maybe she 

could slip up to his dorm room and show him a good time. Since I approved all the house calls… 

Two weeks later I was in my Son’s dorm room, as ordered, and this time there was no bathroom 

stall between us. Honestly, it was amazing the first time I felt him slide into me. His cock 

spreading open my pussy, the feel of him throbbing and getting harder inside of me as I leaned 

into the hottest part of the whole affair and asked him to please call me Mommy while he fucked 

me. 

But, he never seemed to stop being shy about it. I went back 5 more times, and every time I had 

to build his confidence again, and remind him that I was, literally, a whore, again. He eventually 

got there, and he was a natural, but he couldn’t seem to get past my perfect image as his angel 

Mother. I wasn’t sure what I was going to do about it, or if there was anything I even could do, and 

then the perfect opportunity once again fell into my lap. 

I was giving him a goodbye kiss and walking out of his room one time, and I almost walked 

straight into one of his fraternity brothers. I had a little laugh about it, and he apologized, but then 

he asked who I was, and my Son froze. I understood why. On the hand, “Oh, this is my Mom”, 

made perfect sense. On the other hand, he was fucking me pretty regularly now, and if he said 

that, and then someone found out… 

So, I smiled and said, “Allow me to introduce myself”, before handing him my business card. It 

had my first name on it, my place of business, and my phone number. But, my place of business 

was very famous, and so I naturally got a stammering, “You’re a…” from my Son’s little friend. 

But I just smiled, nodded, and then I told him, “Not only that, but I specialize in, ‘family play’. So if 

you ever want to know what a blowjob from your Mom feels like”, and I sensed hesitation, so I 

added, “Or a blowjob from HIS Mom”, and I shot my Son a wink. “...Give me a call.” Then I gave a 

very Motherly “By sweetie!”, and left. 

Well, my poor Son thought that I’d saved the day, and sure enough, he was back to treating me 

like a pure and perfect angel the next time he invited me over, but I had a feeling that the way he 

saw me would change pretty soon. And, sure enough, about a week after that, my Son saw me 

at his Fraternity again, but this time, he wasn’t the one who’d invited me. 

About a dozen of his friends were getting ready to watch some sporting event, and they’d taken 

great pains to tell him that they had a surprise for him, and that he needed to be there, while also 

keeping said surprise a secret. And, oh my, was he surprised…

They were all gathered around the television when I walked into the room wearing a skimpy bit of 

lingerie and carrying a massive tray full of snacks. As requested, I gasped when I saw my Son, 

and said something along the lines of being just, SO surprised to see him; and that I didn’t know 

that this was HIS frat house. When I did, all his friends laughed, and explained. 

When their buddy had shared with them his story about running into me, and showed off my 

card, they’d decided to pool their cash, and invite me back. But since my specialty was Mom 

play (and none of them was about to have the guts to step up and cop to an incest fantasy), they 

asked me if I would play my Son’s Mom. 

They all thought it was hilarious, and hot. But, there I was. Their friends “Mom”, and also their 

bought and paid for whore. And as hard as it was for those boys to scrape up the kind of rates 

that I charge, they were hell bent and determined to get their money's worth. 

After that day, my Son had a much easier time realizing that I was more than his perfect PTA 

Mom, and that I was also a very dirty woman, with a very high sexual appetite. But then, a full day 

of watching your college friends stuffing their big cocks into your Mommy, right in front of you, as 

they brag about how much she obviously loves it… Well, that will do that…