As you may have guessed, I didn't even make it out of childhood with my cherry in tact! I lost my virginity on Christmas Day in 1993 to Andrea, the young black lady who was the deputy-manageress of the whorehouse. She ran the whorehouse with my mom and was really great, like a resourceful and caring Aunt, or indeed, a second mother.
Andrea was a native of New York but her parents had both been immigrants from Nigeria. She was very pretty with a good body, coupled with a very friendly manner and perceptive intelligence. Her skin was an incredibly dark shade of brown and her hair was long and braided, her tits vast underneath the tight, revealing tops she wore. With my mom and her friends watching TV and drinking wine in the living room, I sat in my bedroom on the floor, setting up the new Hi-Fi I'd got from my mom that morning (even though we celebrated Christmas, I was never told to believe in Santa Claus, God or any of that shit. My mom was too practical and intelligent to fill my head with such silliness). There was a light knock at the door and Andrea came in, all smiles and holding a half-full glass of wine.
"Hiya sweety," she said, "What ya doin'?"
"Setting up this stereo," I cheerfully replied, "What about you?"
"Just having a drink with your mom. I'm feeling a little...horny though. How about you?"
"Er...I dunno really," I shrugged. Whilst I was more than aware of all the sex that took place downstairs in the brothel, being just 12 I was usually too busy playing, watching cartoons and generally mucking about to be pre-occupied with it. At least, until recently anyway.
"You started jacking off yet?" Andrea asked, sitting next to me on the floor. She was wearing a low-cut white T-shirt that showed off a lot of her deep cleavage, as well as denim cut-offs that displayed her long legs.
"Yeah," I admitted, casually, my mom not having afflicted me with the shame and guilt a lot of kids have, "Why?"
"Well, I fancy jacking off too. Women do it as well you know. I'm feeling pretty horny at the moment! Anyway, I was wondering if you'd fancy having sex. With me. I suggested it to your mom who advised me to go for it! She said it was about time you lost your virginity. You fancy it Randy?"
This sounded good to me. I'd started whacking off a few months ago and had been wondering if I could have sex with some of the girls who worked at mom's brothel, but I wasn't sure how to suggest it. Luckily, good old Andrea had just negated any need to raise the subject. She put her glass of wine aside and undressed. I stood and watched gleefully as Andrea stripped naked. At the time, the hot lady I often referred to as Aunt was a relatively young, in her mid-twenties, and her body was elegantly slim, her tits large and firm and her ass perfectly sculpted.
"Take off your clothes now honey," Andrea said, and I obediently removed my jeans, T-shirt and underpants. Standing naked with my bald prick jutting upwards against my flat belly, I was short, skinny and very pale compared to Andrea, but she was seemingly pleased with my nude appearance as she invited me to kneel in front of her on the bed. Once I'd done so she began stroking my cock, her touch sending a shiver of pleasure up my spine.
"It's quite big for your age," the Andrea crooned, stroking my prick, "A good five inches! You're going to be hung like a bull when you grow up kid!"
"You look really nice," I told Andrea. I'd spotted her topless a few times when I'd given her a massage or two down the years, but seeing her right in front of me totally nude was fantastic!
"Your mom has told you about the facts of life hasn't she honey?"
"Yeah."
"About normal intercourse and stuff?"
"She's told me about that. There's probably a lot more I don't know though, I was only told the basics at an early age, before I really cared."
"There's a lot more to sex than just the basics," Andrea grinned, taking her hands from my cock and stroking her lovely big breasts, "These, as you know, my breasts. Or tits. Nice and big eh? You should pay a lot of attention to these parts of a lady because they're very sensitive, especially these!" She pulled on her nipples which were very dark and clearly as stiff as bullets. Then, Andrea reached down and stroked between her legs whilst I watched carefully. "This," my mentor continued, "is my vagina. Or pussy, cunt or slit. This is my clit, and here, through the lips, is the entrance to my cunt. The lips are sensitive, as are the insides. That's where you'll be putting your dick in a minute. It's very warm and wet up there and you'll enjoy it."
"I think I will," I agreed, stroking my cock, feeling more aroused by the minute. Andrea then turned round and got on her knees and elbows, her lovely bare butt thrust back at me.
"Never forget the ass," she smiled over her shoulder, reaching round with a hand and clapping it to her buttocks and rubbing the puckered hole between them, "Because you've got one yourself, you'll know this is the anus. It's mainly for shitting but it's also a great source of pleasure. Some prudish women...do you know what prudish means?"
"Boring?" I suggested.
"Sort of. It means women who don't like to fulfull their sexual needs because they're all neurotic and screwed in the head. Basically, 'prudish' women don't like sex and avoid it."
"So I was right then. It means boring."
"I guess," Andrea laughed, "Anyway, a lot of prudish women don't like their butts being played with and get all upset at the suggestion of sodomy...or butt-fucking, buggery, anal...whatever you want to call it. However, there's plenty of nerve endings on the asshole, a whole lotta feelings of ecstasy to be gained from it's use, and myself and other girls love taking cocks up this hole. You're gonna fuck my pussy first, Randy, then I want you to fuck me in the butt so you get the best of both worlds! That way you can see which entrance you enjoy the most. To be honest, I tend to prefer taking it up the ass because it feels a lot tighter. For the same reasons some guys prefer it too."
Andrea finally turned back round and kissed me gently on the lips.
"Let's fuck!" I grinned. Andrea agreed.
"A bit of foreplay first," she explained, then leaned down and sucked my dick, this feeling far better than just jerking myself off. An accomplished cocksucker, Andrea fellated me wonderfully for almost fifteen-minutes before she finally got up and invited me to lay back. She mounted me, my cock sliding up into her pussy with ease as she began to ride me, both of us grinning with pleasure as we fucked away. I was fascinated by those big wobbling tits above me, and I stroked them lovingly whilst Andrea's firm ass smacked against my thighs whilst she bounced on my dick.
"Having fun?" Andrea asked me.
"Yeah!" I answered, "It's great! Are you having fun?"
"Absolutely. Here, do you want to go on top?"
"Okay."
Andrea got off me and lay on her back with her legs spread. I mounted her, pushing my prick into her hot slit once more and proceeding to fuck her.
"OOooh that's good honey," Andrea crooned, reaching round and lightly raking her long nails over my little white ass-cheeks, "Fuck Aunty Andrea sweetheart!"
"Shall we do this a lot!" I asked, Andrea's big tits pushing against my chest me as I lay on top of her, humping away.
"Oh, yes honey! We'll do it a lot. And in a week or so I'll get some of the girls downstairs to fuck you too so you can get a good variety of pussy!"
"Is that what you, mom and the others do downstairs in the whorehouse?" I asked Andrea, my ass still rising and falling between the lady's spread thighs as I cunt-fucked her with hard little thrusts.
"It is," Andrea confirmed, still stroking my buttocks with her fingers, "At least, this is just the simple stuff, just being cunt-fucked like this. There's all kinds of different things we do; watersports, fisting, group, a bit of bondage..."
"What are those?" I asked.
"Well," Andrea began, "Watersports is guys and girls pissing on each other. Fisting is pushing the whole hand into a woman's cunt or ass, group is self-explanatory and bondage is where one partner is tied up."
"There's a lot I don't know about sex!"
"Don't worry about it, you're a fast learner, I can tell. Anyway, us hookers do anything the guy pays for."
"Why don't these men do them with their wives though? Mom said a lot of men coming here are married or have girlfriends, and sneak here without anyone knowing. If they've got a chick at home, why not do it with them."
"Maybe their wives are boring."
"And prudish?" I suggested, energetically fucking Andrea throughout this conversation.
"Yeah, that's right! Society is prudish and boring, always condemning stuff that doesn't concern it. For example, a lot of people out there would be horrified at what me and you are doing right now. Shit, I could probably go to prison if someone ever found out."
"Why? We're not hurting anyone."
"Well, there's no reasons for them to complain except their own stupid, bigoted ones. For starters, it's considered 'wrong' for people to have sex with other people outside of their age groups. I'm a grown-up, a 26-year-old woman, whilst you're a little lad of 12, and though we're unquestionably having good, consensual fun here, I would be arrested and damned for 'abusing' you."
"That's dumb," I said.
"Exactly! Culture worships youth, encourages men to lust for young girls and women to lust for hot young studs, but then condemns anyone who acts upon these desires. Also, some idiots think that sex outside marriage is sinful, and also that people - especially women - should just have sex with one other partner at a time, despite it being clearly more fun to have multiple partners! A lot of people think that sodomy is wrong too just because it says so in the bible, and that, my hot little stud, is what you'll be doing with me next! Finally, a lot of other people - usually religious ones again - would condemn us two for fucking just because I'm black and you're white."
"That's dumb," I repeated with genuine outrage, "Those people can fuck off."
"That's right honey. The world is mostly dumb, run by retards who don't have the intelligence to have fun so just stop other people from doing so. Forget 'em! You're mom is very liberal and open-minded, as are her friends, including myself. That's why you don't go to school - you don't learn anything there except how to cope with doing a shitty job for the rest of your life, to get you used to uncomplaining as you spend 40 hours a week at a desk doing something you hate. Still, as long as those retards out 'there' are kept busy running after dollars and nothing else, they won't pay attention to us and we can get along with having fun eh?"
"You're so cool Andrea," I grinned, fucking her a bit faster as I sensed my climax rising, "My lovely, big-breasted anarchist Aunt!"
Andrea laughed and kissed me.
"Now fuck me hard sweetheart!" she urged me, "Shoot your hot sperm into my cunt! Fuck me as a way of giving the finger to any cunt who'd dissaprove! Uuuh, God I think I might cum too...oh Randy, yeah, baby!"
"Yeah, Andrea!" I panted, going faster, "God, I'm gonna cum soon!"
"That's it! Yeah baby, fuck my cunt, fuck me!"
My orgasm struck me hard and I cried out with pleasure as my young sperm fountained up into Andrea's hot pussy. My body tensed as it rubbed against Andrea's, my cock pulsing and throbbing as it disgorged it's creamy loud.
After I'd dismounted her and lay on my back, Andrea took my cock into her mouth and sucked it. She then got me to raise my legs and pull them up to my chest so she could get down before me and noisily lick and suck my hairless nut-sac and my asshole, her warm, wet tongue rimming my sphincter and sending little ripples of pleasure through me. She even inserted a long forefinger up into my anus, all the while deep-throating my cock which grew harder and harder thanks to this fantastic treatment. Encouraged by my joyful panting, Andrea fellated me harder whilst now sliding two fingers into my tight ass. I was soon fully aroused once more and after slicking up her butthole with KY-Jelly, Andrea got on her hands and knees and invited me to fuck her in the ass, her naked buttocks spread and shining in the bright spotlights over the bed. With no hesitation, I pushed my stiff dick into her bum, instantly realising that anal-sex was going to be my favorite method of fucking. It felt so nice and tight! I fucked her shit-hole fast and hard, Andrea's big boobs wobbling beneath her whilst she gripped my Teenage Mutant Ninja Turtle bed-covers. CLAP CLAP CLAP went my hips as they smacked up against her bum-cheeks, Andrea panting with pleasure whilst I watched in fascination as my hard cock slid to and fro in her asshole. The hot chick before me urged me on with shocking profanities, wailing "Fuck my shitter! Fuck my ass Randy you little stud, fuck me!!"
This time I lasted twenty-minutes until I came hard, my sperm spraying up into Andrea's clasping anal-track. Afterwards, we both sat against the headboard, streched over the covers as we got our breath back, naked and sweaty. Mom casually came in after a moment with a tray, smiling as she clearly figured out what we'd been up to. She wore a bright red jumper and black jeans
"Finally lost your cherry sweety?" mom smiled, handing Andrea a fresh glass of white-wine and me a big glass of milk.
"Yeah mom," I responded.
"Good," my mommy said, "Miseltoe attack!" she suddenly announced, plucking a sprig of misletoe from the tray, holding it over my head and kissing me on the lips.
"Do I get one?" Andrea asked. My mom obliging leaned of me and kissed Andrea on the lips with the misletoe held over them.
"I want an encore!" I said, and mom happily gave me another kiss before, finally, she bade us farewell and sauntered out the room.
Andrea drank her wine whilst I guzzled my milk, after which the naked lady beside me decided to show me how to perform oral on a woman. I was a natural at it, licking and tongueing Andrea's wet slit until she came hard. I was erect once again soon and I fucked her cunt and asshole for an hour before Andrea invited me to cum in her mouth, and she swallowed every drop of my youthful sperm. Then, we washed, dressed, and looking very innocent we joined mom and her other friends in front of the TV. I sat on the sofa between mom and Andrea, drinking a bit of wine before I fell asleep half-way through a movie, my head resting against my mother's shoulder as I snored quietly.

Shortly afterwards I began fucking some of the other girls in the place, and they were happy to offer me 'freebies' in between their paying johns. Even as I approched my teens, the hookers still thought of me as their little brother. I made a nice change from the line of old guys coming in for a shag.
The brothel was a very friendly place. Mom only took 30% of the client's fee- most would have taken 50% - with the remaining 70% going to the hooker, and so there were always a plentiful supply of temporary and long-term girls wanting to work here, as well as clients who liked the relaxed atmosphere and wide variety of girls. The few cops who hung around this neighborhood largely ignored us because we weren't hurting anyone, but we did have to keep the underage hookers behind closed doors though.
Even the prostitutes who didn't work at the brothel and instead walked the streets around the neighborhood were allowed in to use the kitchen and lounge area of the whorehouse as a kind of drop-in center. If I was the adopted brother of all the hookers, mom was the wise, caring mother-figure of us all. She was well-respected by all the vice-workers in the area.
I took up weightlifting in my mid-teens, enjoying giving myself a good, strong body which the women and girls around the place really like. Sex never got boring and I never tired of fucking Andrea or the hookers. Anal-sex was great still my favorite, and Andrea liked it too so I frequently butt-fucked her in my bed, often tugging myself free of her tight shitter and cumming all over her big bouncing tits!
Most of the whores in the brothel were aged between their mid-teens to mid-thirties so I was used to just having sex with women older than me. It wasn't until I was 16 that I finally fucked a girl who was younger than myself, a lovely brunette schoolgirl who was aged 14. She ran away from home for a month in late 1997 and came to work at the whorehouse for a few weeks. She ended up spending a lot of the time in my bedroom where I sodomized her repeatedly. Despite having a good time, the novelty wore off and she returned to her parent's home in New Jersey. She did, however, return a couple of years later to work all summer.
My mother was a very tall lady and I seemed to be taking after her, growing up in height fast with my dick seemingly growing faster than the rest of my body! My prick was soon approaching a foot in length, and some of the younger girls were a little put off by it at first! Luckily, most of them just got more hot when they saw how big I was, and before and after their shifts at the brothel, plenty of the girls came up to the apartment for a fuck. Even though my prick was almost as thick as a child's forearm, my lovely Aunt Andrea was always more than capable of taking my long, heavy rod in her ass with the minimum of fuss.

Late Summer 2000. I've just turned 19 and continue to live at my mom's apartment, still in the same big bedroom I'd slept in as a kid (though the Teenage Mutant Ninja Turtle bed covers had been replaced!) Most days I sat around the apartment or at the nearby park, reading books or smoking pot, or perhaps helping mom around the house and brothel. Whenever I felt horny, I went downstairs and had no difficulty in finding one of the many hookers around who was up for a fuck. Fully grown, I'm now 6-foot-3 with broad shoulders and strong limbs. I have short black hair, big brown eyes and down below I pack a 12" cock who's growth I attributed to all the use it got from an early age!
Today was different, as I'd soon find out shortly after waking at five in the morning. Because the brothel downstairs was open 24-hours, and we didn't have regular lifestyles, neither me or my mom had ever stuck to normal timetables. We slept and awoke whenever we felt like it, regardless of what the world was doing beyond the windows. I was lying in my bed in my large room, which was decorated in a very neo-hippy kind of way; large rugs, lava-lamps and funky, hand-made ornaments from various craft stores around the neighborhood. The whole apartment was decorated in a similar manner. Born in 1955, mom had only just caught the end of the swinging-sixties as a teenager, and so was trying to recreate the whole decade, an eternal Summer of Love.
Under my bright orange satin blanket, I was naked and feeling my large prick throbbing stiffly over my stomach, prompting me to plan a quick trip downstairs to see which of the hookers was free for a quick fuck - rarely did any turn down a quick, friendly romp with me. I yawned and sat up, then turned to the bedside table. It held a large ashtray and some smoking gear, with a bag of cannabis and a couple of ready made joints. I lit one up and inhaled deeply, feeling nice and relaxed and thinking of the big breakfast I'd feel compelled to eat after working up an appetite of both sex and weed.
There was a knock at the door.
"Come in," I called.
It was my mother who entered the room, striding in with a big smile on her pretty face. My mom was now aged 45 and very sexy looking. She was very tall - 5-foot-10 - slim with long legs and flaming red hair that hung that tumbled half-way down her back. Her eyes were big and blue and her skin very light. She was wearing a simple black T-shirt that reached half-way down her long, toned thighs.
"Hi sweety," mom said, as I sat up on the bed, "You busy?"
"Not really," I shrugged, "I might go down and see one of the girls though." That was a euphemism for 'I'm horny so I'm going to fuck one of the hookers'.
"You fancy doing something different today Randy?" mom asked as she sat on the bed. It was a big double bed, underneath the large bay window, the drapes open and revealing the panoramic view of the city, the Empire State Building jutting upwards in the hazy distance.
"Sure," I shrugged, "Want a smoke?"
"Thanks honey," mom said, and took the offered joint. She took a deep drag of it then smiled at me again, "Listen honey, I've seen you, for many years, having sex with all those sweet girls downstairs. And Andrea of course."
"Yeah," I nodded, "You don't mind do you?"
"No, no of course not. Don't worry about that sweetheart! I encourage it! What I wanted to ask was, how about fucking me?"
"You?"
"Yeah. You're dear old mom! Come on, I can just work as the owner of this place and still earn a fortune, but I carry on seeing the clients because I love fucking! I can't help but get a bit jealous that all those lovely sluts down there are getting a go on your big ol' dong and I'm left with a line of middle-aged men. I must admit that sometimes, on my way to bed or wherever, I've heard you screwing in here and I have peeked through the crack in the door. I've seen that foot-long cock of yours driving into the orifices of the teenage whores around here, heard them squealing with orgasm after orgasm whilst you - even in your early teens - fucked them senseless. And since you were 12 Andrea has bragged of how her asshole often hurts with pleasure because you've buggered her that hard and that often! I want a go too."
"You want me to fuck you?" I asked, still a little shocked, despite mom's casual attitude to sex and her openness about her career.
"Of course! Oh honey, mommy loves cock sooo much, and the cock I think I'd love most in the world is yours. I think it'd make me cum a lot! Do you fancy it? Do you want to fuck your mother?"
"Sure, of course I do! Jeez mom, you're the hottest girl in New York! I didn't think I'd be good enough!"
"Oh don't be silly," mom laughed, then after another toke on the joint gave it back to me, "You're a sweet young stud, the hottest guy in New York in my view! I've heard the girls downstairs boast about big your dick is, how you fuck them repeatedly and hardly ever seem to tire! I'm at my utter peak of sexual-hunger, and you're my handsome, well-hung young stud who's clearly got a massive fucking boner underneath these blankets! C'mon, let's fuck!"
"Right on mom!"
I smoked some of the joint as I watched mom stand up and remove her T-shirt. She was totally nude, her legs very long and toned, her breasts heavy and topped with dark nipples, each piereced with a golden ring. Her cunt was furry with hair the same fiery-red shade as the hair on her head, and her finger and toenails were painted red. There was a small, blue tattoo of a flower on her left ankle and a rose on her right shoulder-blade. Like I said, I'd seen her nude before, loads of times, but it's a totally different experience to see a woman unclothed in a casual, as-nature-intended kind of way, and seeing her naked and in heat, ready for a fuck.
I took a last, long toke on the weed and stubbed out the joint, feeling pleasantly light-headed as I got to my feet. The floor in my room was dark oak, but my bed was placed on a huge, plush African rug. It was thick and warm beneath my bare feet. Mom gave me a gentle kiss on the lips then elegantly stepped onto the bed, getting down into a kneeling position.
"Come here son," she said, patting the bed before her, and I was soon kneeling in front of her, briefly recalling the time in here at the beginning of my adolesence when I was kneeling in front of Andrea naked. Now, at the end of my adolescence it was my naked mom in front of me.
"Fuck knows why we haven't done this before," I said, "I've always wanted to fuck you mom, at least in the back of my mind, but I've never got round to actually asking you!"
"Well, we're going to do it now! My my, what a cock! I've never seen one so big!"
Mom stroked the aforementioned member, a whole foot of throbbing, steel-hard prick jutting at her naked, lean body. She tilted her head and her long, blazing red hair hung down one side of her upper body, her breasts wobbling a little as she masturbated me with both hands.
"Think you can take this on mom?" I asked with a boastful grin. Mom looked up at me with bright, azure eyes.
"I think I can son! Oh my, it's going to be a challenge though!"
She leaned down and, with a bit of effort, crammed the purple head of my dick into her mouth, sucking expertly on it whilst still jacking off the shaft with both her hands, her long slender fingers barely reaching round my girth.
"Ooooh mom," I crooned, stroking my hands through her lovely long hair, "You suck dick well! Mmmm!"
After a few moments I asked if I could return the favor. Mom wasted no time in laying on her back with her long legs spread, and I got down and started licking at her cunt. The hookers downstairs had trained me well at this over the last five years, and I lapped and tongued mommy's moist pussy until she was bucking her ass off my bed and crying out with joy. When I lifted my head up, my tongue aching from it's effort, mom opened her arms.
"Climb aboard son!" she panted, lustily, "Come and fuck mommy!"
"Try and stop me!" I announced, mounting mother and plunging my enormous prick into her pussy. She cried out in pleasure, wrapping her arms around me, her long nails lightly raking my upper back and sending a lovely shiver down my spine as I settled into her cunt. I kissed mom hard and began fucking her, mom humping her groin up to meet me. Her big soft tits were squashed against my chest and her body felt lovely and warm beneath me. Fucking Andrea and all the hookers downstairs - I reckoned I'd slept with almost ninety already, without paying once - was fun, but fucking my lovely mother was the best of all. Mom was soon pulling her mouth from mine and moaning loudly in ecstasy. She was a damn good fuck for sure, but then she'd have to be! She'd had lots of practise, having boasted last week that, according to her estimates, she'd fucked about 3,000 different men and 'at least' 300 different women since losing her virginity in 1969, aged 14. Writhing beneath me, mom continued to cry out "Oh fuck me son! Fuck me, fuck mommy! YEAH!" as my orgasm rose.
"I'm cumming mom!" I gasped, "Oh yeah!"
"Cum in me!" my mother urged, "Fucking cum in me, yeah! GOD!"
With a long sigh of pleasure, I began spewing my cum up into mom, flooding her pussy as I continued to fuck her. For a good thirty-seconds my sperm shot up into her until my orgasm finally died away. I collapsed on top of mom as we got our breath back, until I eventually pulled out and rolled off.
Mom slowly sat up and took the second joint from the bedside table and lit it up. We exchanged it frequently as we lay back together, nude, getting pleasantly stoned.
"That was a good fuck!" mom concluded after some silence, "Do you think so sweetheart?"
"Absolutely!" I agreed, "The girls in the brothel have been great fun, and I'm sure I'll still fuck them sometimes, but you're the best mom."
"I've told Andrea the girls downstairs that I intend on seducing you today. None of them care, they don't mind. Andrea said she was surprised I hadn't done it before. We won't be disturbed anyway."
"Let's fuck again mom! Hell, I'm feeling horny already!"
"That'll be the dope," mom smiled, blowing a large plume of smoke from her lips and passing the joint to me.
"That'll be the horny chick next to me," I smiled, taking a toke of the joint. It'd much run out so I stubbed it in the ashtray and knelt up. My foot-long prick was fully erect and nodding heavenward in a very stiff and menacing fashion.
"What a cock!" mom crooned, stroking it with a flutter of her long fingers, "Let's carry on fucking through the sunrise shall we?"
"Lets do that!" I agreed.
"Wanna take me up the ass?" mom asked, grinning wickedly.
"Yeah, I'd like that!"
"I know you'd like that honey! The girls downstairs have told me how much you love fucking them via the back-door all the time! Luckily, I prefer anal too so it seems we're gonna be pretty compatible!"
"Some worry I'll tear them though, cos I'm so big! With a lot of lubrication though it should be okay."
"Well, honey," my randy mom continued, getting on to her hands and knees and thrusting her lovely bare ass at me, her anus pink, hairless and puckered between her firm buttocks, "I would never turn down a cock that's hard and prepared to be shoved up into my shit-hole. I've taken countless cocks in my ass - thousands, literally - and whilst I've never had one as big as yours up there, I have had some fair sized dongs before! Grease me up, sweetheart, and get up me! Show no mercy to mommy's ass!"
I took the jar of Vaseline from the bedside table and lubed up my long rod, then applied some to my mother's twitching anus, pasting the grease around her and fingering the entrance to her sublime butt until it was loosened up. Then, I got into position and began to push my cock up into mom's ass. My mother braced herself as her sphincter began to slowly part, my prick making good headway and mom urging me on whenever I asked her if she was okay.
"Shove it up me," she panted, the head of my cock now buried in her butt, "Fuck it up there!"
"It's going up mom!" I told her, easing up inch-by-inch, "Slowly but surely....fuck yeah! It's almost half-way up...almost...yeah, shit. Six inches up there!"
"Keep going," mom begged me over her shoulder, "Slide it right up mommy's shitter! I've had a lot of cocks up my ass before! I'm capable of handling it...uh, uhhhhhn it's going up..."
"Getting closer mom," I informed her, pushing ever onward in my quest to fully sodomize my mother, "Eight inches up your butt...nine inches now at least....a bit more....yeah..."
"Keep...going....NNnnng! Uhhhhhh!....UH!"
"Ten inches up now mom...not much further! Shit, just a bit...more..."
"Don't...stop....Uuuh!"
"An...inch more to...go....just a quick...HEAVE!"
"Nyaaaahhhuhhhhh!"
"...and it's there!"
"God f-u-u-u-ck! Uuuuh, f-f-f-fuck YEAH! Oh yeah! Oh shit son...my ass...GOD! That is...fantastic!"
I remained stationary for a moment, my mom spluttering obscenities with my 12" dick wedged fully in her rectum. Her sphincter began to get accustomed to it's immense invasion.
"That's sooo good," mom said after a moment, "Fuck me! That was worth it, it's utter fucking heaven!"
"You like my big dick mommy? You like your son's nice big prick up your asshole?"
"Fuck yeah! It's all the more pleasurable for all the effort it takes to fit it up there...phew! Fuck! Right, start fucking my butt! Don't stop until you've flooded my guts with cum!"
I slowly pulled back, pulling half of my long cock from mom's butt before plunging back in, reducing my anally-impaled mother to a grunting mass of ecstasy, and then I began to repeat this quicker and quicker. I held mom's hips in my strong hands as I fucked her, the dope I'd had making me just a little bit high.
For twenty-minutes I ass-fucked mom at a steady pace before I increased my speed. Me and mom both cried out loudly as my sperm shot forth, thick, white pumps of sticky goo ejecting hotly deep, deep up into mom's colon. Her sphincter tightly twitched round the base of my cock as I emptied my balls up her shitter, my hips 'whack whack whacking' against her ass-cheeks and the backs of her thighs.
Finally, all spent, I eased my wilting prick from her sperm-filled ass and we fell back on the bed, breathing hard.
"I tell you one thing," I said after a few moments, "Between fucking you, and that weed, I'm as hungry as a motherfucker!"
Mom laughed, and we eventually summoned the energy to get up together and head to the kitchen, planning a little breakfast in bed.
We made a large cooked breakfast, using all the organic stuff mom had in her fridge (she was a vegetarian, which meant I was too, except for the occasional McDonalds!). We scoffed waffles and toast in bed, drinking coffee and smoking a little more weed. That finished, I was horny again, so I fucked mom in the ass for a second time. It was easier entering her as her butt was still a little loose, and she lay on her belly on my bed, me on top with my torso flat against her back, my breath hot in her ear. I lay sprawled on her hot body as I roughly fucked her ass with my big hard cock, burying it deep inside her rectal passage, mom bucking her butt up to meet my thrusts and urging me ever onwards. My orgasm was a long time in coming, and it was even more powerful than the first two. My cock exploded sperm up into my mother's ass and I almost passed out on top of her with the intensity of my climax. When it finished, I rolled off mom, my soiled prick slipping out of her with a wet 'pop' and we fell asleep - sometime around 7:00AM - within minutes.

It was noon when we awoke. We could hear a couple of the hookers from downstairs in the nearby kitchen, just helping themselves to some food as they were welcome to. Mom sat up next to me and I stirred when she held my cock, which was rock hard.
"Morning wood again?" mom smiled at me.
"That's right mom!"
"Some of the girls are out there getting some lunch, by the sounds of it. Shall we go out?"
"Why not?"
We got up off the bed and, stark naked, me with my prick rock hard, we casually left the room and padded into the large kitchen. In there were two of the more veteran hookers. The elder was Jessica, a tall brunette aged 29 who specialised in anal (my favorite!) and bondage. She'd been here for three years and was brewing up some coffee, standing in just a pair of knee high leather boots, a black thong and matching bra. Her 'working' uniform.
The younger lady, who sat at the big table by the window and smoking a cigarette, was Kate. A quiet girl in her late teens, who'd left her previous job as a secretary for a stock-broker, Kate had established herself as the 'Watersports Queen', gleefully pissing on clients and letting them piss on her in turn. Average height and slim, Kate had pale skin with jet black hair and a tendancy to wear purple eyeliner and black lipstick, giving her a gothic look. She wore just a pair of black panties and nothing else. Her breasts were heavy and round, almost white in the bright mid-day sun that entered the window above the sink, the smoke from her Marlboro floating up gently above the table.
"Hi all!" mom greeted the girls, me not far behind. Kate and Jessica said their hello's, greeting me too.
"Did you seduce him then?" Jessica asked, pouring out coffee for us all.
"I sure did," mom boasted as me and her sat at the table next to Kate, "Just like I promised."
"Looks like you didn't completely drain his balls like you promised!" Kate pointed out, blowing cigarette smoke from her dark lips and reaching under the table to pat my big stiff prick. I'd fucked both her and Jessica a lot in the past so this was hardly unsual behaviour.
"We've just got up," I insisted.
"He fucked me three times at dawn," mom pointed out, "Once in the pussy and twice in the butt. Oh, my, I tell you girls, how big is my son's lovely cock?! It took a while to squeeze it up my ass that first time."
"You'll get used to it," Jessica said, placing a cup of coffee before me, Kate, mom and finally for herself as she sat down with us, "I've been by taken Randy up the butt a lot. "
"I've only managed it a few times," Kate admitted, handing Jessica a cigarette and lighting it for her, "Randy is just a bit too big for my ass!"
"Wimp," Jessica laughed.
"I feel so fucking horny right now," I admitted, sitting back, my prick thrusting up against my belly and reaching almost up to my chest, "Especially with you lovely ladies!"
"Well," began Jessica, "better save all your lovely cum for your mother! She's waited years to finally fuck you! She was really excited last night after you'd gone to bed and she was smoking joints and bragging of how she was going to finally get fucked by you this morning!"
"Mission accomplished!" mom bragged.
"How long are you two working for?" I asked Kate and Jessica.
"I'm here for another few hours," Kate said.
"I'm finished for the day," Jessica admitted whilst flashing me a sexy grin, "I'll stick around though if you two fancy it."
"Sure," I admitted, "What do you say mom?"
"The more the merrier," mom grinned.
We finished our coffee before Kate got up and went off downstairs back to the whorehouse below. Meanwhile, Jessica, my mom and me went off to my mother's room.
It was a large bedroom, very bright with garish, psychadelic shades in the decor; bright orange carpet, floral wallpaper and swirling patterns painted across the ceiling in shades of purple and yellow. The most normal looking part of the room was an impressive TV and Hi-Fi set-up in an oak cabinet, flanked by two full-length mirrors. There were freaky posters of fractals on the wall, the furniture with a primitive look about it, all dark wood and unvarnished. A large walk-in wardrobe held hundreds of my mom's far-out, hippy outfits.
A huge window looked East towards Greenwich Village, and beneath it was the bed. Custom made, the bed was low off the ground and as wide as it was long, and five people could sleep side-by-side quite comfortably on it - or do more than just sleep! The covers were stark white whilst against the headboard were stacked plenty of cushions of contrasting colors and patterns. Flanking the head of the bed were two squat oak tables. On the left one were several large dildos of varying sizes, a big jar of Vaseline and a hardback book titled The Ultimate Guide To Anal Sex For Women. On the other table was a big bong, a bag of marijuana, an unopened bottle of Jack Daniels and yet another dildo. The possessions pretty much summoned up what kind of woman my mother was. And what a woman, eh?
I climbed onto the bed, my unwieldy prick nodding ahead of me as I was joined by my mother. Jessica took off her underwear and got onto the bed with us, wearing just her knee-high black boots. Her tits were fairly big and wobbled delightfully as she moved about, and her clit was pierced with a gold hoop. The two women quickly lay me down and shared the job of sucking me off, licking my vast cock and sucking on the head, moaning pleasurably as they did so whilst I ran my hands through there hair.
Jessica mounted my prick first, sliding her cunt onto me and widing me hard as she grunted in joy. She may have finished an eight-hour shift and been fucked by a dozen or more men, but this was for pure pleasure. My mom knelt nearby, sometimes kissing me and draping her tits over my face so that I could lick her pierced nipples, or sometimes kneeling upright and kissing Jessica hard on the mouth as they rubbed each other's tits. I'd had many threesomes before where the two chicks got it on with each other, and I'd sometimes caught my mom having sex with other girls before, but this was the first time I'd fucked two women who also got it on together with one of them being my mom! It was great! Shortly, Jessica got off me and now my mother rode my prick, and I slammed my hips off the bed and shafted her pussy whilst Jessica sat on my face. I lapped at her cunt, digging my tongue up her wet slit whilst fucking my mother.
Soon, we moved apart.
"You want it up the ass again don't ya mom?" I asked her, stroking my long cock.
"Damn right!" my mother confirmed, "But Jessica is our guest honey. Do you want to go first Jessica?"
"Sure thing!" replied Jessica, and she got on her hands and knees. Me and mom greased up the woman's asshole and my dick, and then I began the operation of penetrating Jessica anally. With patience and skill, I soon planted my long prick right up inside the young woman's shitter, Jessica shivering with joy beneath my slow but deep thrusts. Mom kept nearby, kissing me repeatedly on the lips, neck and chest, sometimes reaching under Jessica to frig her clit or pull on her nipples. Jessica just kept spluttering and groaning with joy as her asshole was soundly fucked by me.
Eventually, I tugged myself free of Jessica and once she'd moved aside, I watched delighted as mom took her place, getting on her hands and knees. I used the KY-Jelly on mom's anus before repeating the sodomistical operation, mom remaining firm and strong under the major penetration. Triumphantly, I let out a sigh of pleasure when I finally slid the entire 12" of my cock up into mom's anus. She was driven wild with lust and pleasure, bucking underneath me as I butt-fucked her hard and fast, Jessica also turned on by this explicit display of incest. She stood and offered her cunt to my mouth and I tongued her pussy whilst fucking mom, later asking her to turn round so that I could lick Jessica's anus.
Jessica fancied another go after a while, so my mom politely moved aside and allowed Jessica to get down on all fours. Eagerly, I shoved my prick up into her butt once again, fucking her hard as I felt my orgasm approach.
"Cum up her ass," mom instruced me, kneeling nearby, "Shoot your load up there!"
"Okay mom!" I panted.
"Oh fuck," Jessica was crying out, joyfully, "Oh yeah, fuck my ass, cum up there! Uh! Uh! Uuuuh!"
"You look fantastic when you cum," mom told me, then kissed me hard. She also reached round and shoved a finger up my butt, this unexpected pleasure triggering my climax. I shoved my tongue down my mom's throat as my cock exploded in Jessica's rectum, thick sperm pumping out and into her guts. My orgasm was long and powerful and I was shattered when we all pulled apart, sprawling over the bed and breathing hard.
"I'd better get going," Jessica eventually announced, sitting up, "It's been fun!"
"When are you back Jessica?" I asked.
"Tomorrow morning."
"We'll see you then!" mom said.
Jessica got up and put on her panties and bra. The rest of her clothes to go home in were downstairs, and she said her farewells before leaving. Me and mom lay across the bed still, tired but not finished yet!
Mom stirred first, reaching over to the small table at the foot of the bed and preparing the bong. She sat up and, using a lighter with the CND symbol engraved on the side, she took a great big toke. Smoke bloomed up above the bed as mom coughed and spluttered, descending into a pleasant, soft grin as the dope hit her brain. She handed the bong to me and I took a big lungful of burning weed too, putting the bong aside as I breathed out the smoke and began to feel pleasantly high. It also made me feel even hornier than I already was, and I turned to mom who'd read my mind and already got onto her hands and knees. Without hesitation I mounted that lovely whore and plunged my cock into her anus. Mom arched her back and let out a long sigh of ecstasy as my thumping great prick burrowed up her clammy wet rectal chute, pushing her shit back a week, every inch of my dick lodged in her bowels. I fucked her hard, the bed-springs squeeking as I buggered mommy passionately.
My orgasm rose after just ten-minutes, but I wasn't going to shoot off just yet. I'd been fucking since the start of puberty and I was blessed with the willpower to hold back. I slowed down until the critical moment passed, before recommencing my thrusting. I did this several times, approaching orgasm but never reaching it to ensure I was still going strong and hard after almost forty-minutes. Mom was certainly not tiring out yet, and I eventually withdrew my soiled prick from her bum with my climax still held in check. We took a break, toking on the bong once more and guzzling a glass of mom's home-made lemonade each.
We soon got back on with the action. I fired my prick back into my mom's ass and humped away, mom urging me on with profanities as her anus gripped my huge cock, her anal-passage holding me in a wet, slimy grip. Her tits flapped beneath her and her long red hair stuck to her sweaty face. The air became so humid with the smell of sweat and weed that I had to withdraw from mom and open up a window to let in some fresh air. With a nice breeze entering the room - and all the sounds of the busy streets a hundred feet below - I got back to bum-fucking the wild slut who'd given birth to me 19-years previously. My orgasm finally hit me a full hour after we'd started, my climax prolonged and hard. I almost passed out as, still high from the bong, I shot a dozen thick squirts of sperm deep into my mother's shitter.
I pulled out and fell back onto the bed, mom crawling over to me and resting her head on my heaving chest, stroking my softening dick.
"Do you like fucking mommy?" she asked.
"You don't need me to answer that do you?" I said, "I love it!"
"Goood! You're my beautiful son, and I've finally realised that, despite all the men I've fucked, despite all the great sex I've had, nothing will ever compare to you!"
"Likewise mom! I don't intend on giving up screwing the other chicks here, just as you won't give up fucking clients downstairs, but I want to give you priority with my dick!"
"Fantastic! God, I just love your cock son. I love you! I want to be fucked by you as frequently as possible!"
"I'll do my best mom! I can't get enough of you!"
"And fuck my ass as often as possible will you honey? I love anal more than anything!"
"Out of all the women's bums that I've fucked, yours is the best, without a doubt mom!" I stated to her, factually, "I'd fuck your ass yet again if I wasn't worn out."
"Let's build up your energy then honey!" mom said as she sat up, "Let's have another hit on the bong then get dressed and go to that little cafe round the corner. We'll have a big slap up feast then come back here and you can butt-fuck me throughout the afternoon!"
"Sounds good mom!" I agreed, also sitting up.
"We can invite a girl from downstairs to join us if you want. How about that Kate?"
"Maybe this evening mom. Right now, I want to spend the rest of the daylight hours with you alone. Just you, me, my dick and your ass!"
"Sure thing honey! Come on, let's get stoned, then we'll eat and then we'll fuck!"
"Superb idea mom! Who's turn is it on the bong?"
We got a bit more stoned then finally showered and dressed. The brothel was well looked after by the senior hookers downstairs so mom was easily able to take the day off, instead just taking me to the cafe down the road. We had a big lunch and went to a bar where we shared a bottle of wine. Finally, back at the apartment, me and mom shut ourselves in the bedroom and fucked. We smoked plenty of joints and scoffed cookies and chips in between, soon growing sweaty and we had sex on the bed high above the city. By the time we collapsed, exhausted, that evening, I'd cum four times up mom's ass and fired a fifth load of sperm over her nice plump tits. Stoned and satisfied, we phoned for a couple of big pizzas for dinner, Andrea from downstairs being kind enough to bring it up for us! She had a big grin on her face and knew that she'd be invited for the night-time session on the bed.

Sex continued frequently between me and mom as the months went by. I still had fun with the prosititues whilst mom saw clients, but more and more mom just spent her time in the apartment with me. We couldn't get enough of each other, and we slept through most of the days and spent our nights screwing, me fucking mom in the ass the majority of the time. She loved anal and so did I! Sometimes I came up her shitter so often in a single, marathon session that my sperm would be running out of her gaping asshole like it was a fucking cum-tap, and I'd stem it up by just thrusting my dick up there yet again. Like a typical teenager, I was insatiable and tireless, and when I wasn't cumming up mom's butt I was jacking off in her face, or her mouth, or all over her tits and stomach. We had plenty of threesomes too with the hookers downstairs. Andrea eventually left her apartment a block away and moved in with me and my mom, and we had plenty of threesomes together - or foursomes and fivesomes sometimes. At least once a week we'd have a big orgy with lots of hookers from downstairs and several of their male friends turning up, mom's apartment filled with naked bodies fucking away.

Whilst most youths like myself might spend a Saturday morning going to play football, lying in bed, sleeping of a hangover or even doing some schoolwork, I spent this particular Saturday morning downstairs in the reception area of the whorehouse. It was a spacious room, complete with a plush red carpet, erotic prints on the oak walls and big plants standing in the corner. There was a lounge and kitchen area next door where the hookers sat around in between clients. At the moment there were 9 prositutes on 'duty', which was average for a Saturday morning. That evening would be the busiest time and there would probably be 20, of whom half would be seeing clients at any one time. When a guy buzzed the door outside, whoever was at the front desk - either my mom, Andrea one of the other more experienced hookers - would let them in, take their cash and then the hookers were come in, in various stages of semi-nakedness. The guy would pick which girl he wanted and be lead to a room, soon to be joined by the girl. It cost a basic rate of $50 for half-an-hour, or £80 for two girls for half-an-hour. The clients could pay a bit more if they wanted some kinky extras, but often this wasn't necessary. My mom didn't like the idea of employees been willing to do no more than the basics, and consequently every prostitute at her brothel was required to do not just full sex but also oral, anal, external-cumshots and girl-on-girl for no extra charge. Because my mom was a fair and good employee, this requirement in no way depleted the large number of women who came here for work. They could earn a lot of cash here and have a good time in the process. Safe, anonymous and relatively cheap, the place was also a big hit with men from all walks of life. Andrea often joked that there were more orgasms occuring in this whorehouse than there were in the whole of the state of Utah!
At the desk this morning was Jessica, the lady I'd fucked along with my mom when mother had seduced me. She wore a nice looking little black dress with a pair of shiny black shoes, her hair tied up in a bun and making her look very smart and formal. As she lounged behind the desk, smoking cigarettes and drinking coffee, I sat in a nearby leather armchair, drinking a bottle Coke and smoking a joint. I'd been up all night night and was feeling horny as I chatted to Jessica in between clients coming in. As always, it was relatively busy, and I took a strange enjoyment out of watching the different types of guys who came in and seeing which hookers they'd pick.
A High School athlete came in around 8:30AM and picked a girl his own age. Then came a fat guy who selected a black lady. A nervous looking man shuffled in next, clearly his first time here, but he would be well-cared for by the big-titted 18-year-old blonde who he eventually selected from the line of hookers he was presented with. Two wealthy looking, middle-aged stockbrokers came in with their briefcases and suits, looking as if they were on their way to the office. They looked very similar, and probably had similar wives in similar suburban homes. Their tastes in whores were different though, and whilst one selected a buxom Latino lady, the other quickly picked out a dainty blonde girl in her teens. Then came a cheeky looking kid no more than 14, and though he was a little short on cash - he only had $45 - Jessica kindly let him in. Probably about to lose his cherry, the boy was soon scampering off to a room with a blonde woman who was more than twice his age and stood several inches taller than he did.
I was wondering whether to go upstairs and see if mom or Andrea were around for a fuck. Fatigue and light-headedness caused by the cannabis was making me horny and also I hadn't cum for hours. However, it soon seemed I was about to be called into service.
An old guy with thinning silver hair shuffled in, wearing a smart suit and holding a walking cane. He spoke quietly but with authority, explaining that he wanted a bit of "whips and chains stuff", adding that his advanced years meant that he needed to "spectate before I can participate." In short, he wanted to watch a young lady be spanked and fucked by someone else - either a man or woman - whilst he watched before joining in. He was introduced to the four girls on duty at the time who did bondage and selected a Japanese girl called Ainoko. After taking the old man to the 'bondage' room, Ainoko returned and came up to me. She was a sexy little lady a couple of years older than myself, only 5'1" in height and rather buxom. Not strictly plump, but just with a few extra pounds around her hips giving her a chubby ass. She wore just a thong and a lacy black bra.
"Randy," she smiled to me, "Fancy doing the honor of joining me?"
"Most certainly," I replied, stubbing out my joint and standing up, towering over the short, sexy chick in front of me. She seemed very pleased that I was to join her. I followed Ainoko down the hallway to the bondage room, watching her round buttocks wiggle in front of me as my dick stiffened. In the few months Ainoko had been here, I'd only got round to getting a blow-job from her (in the kitchen upstairs during one of mom's wild parties) and I was looking forward to fucking her.
The bondage room, at the far end of the corridoor, had big black drapes over the windows and was lit up with lots of bright red spotlights, giving it an eary appearance. The walls were painted black, and a white spotlight pointed from the ceiling towards one of the walls, which held an X shaped cross to which a person could be strapped to with the wrist- and ankle-cuffs at the ends of the beams. A shelf nearby held big dildos, assorted spanking impliments and some candles and matches. In the middle of the room was a 'raping stool', a tall bench with a padded leather surface and cuffs on the legs, over which someone could be bent over.
The old client was naked in a chair nearby, clearly used to satisfying this fetish, already stroking his limp prick as me and Ainoko got on with putting on our show. Bondage was Ainoko's speciality because she simply happened to enjoy it, and though I wasn't used to doing this kind of thing, I was more than capable of making it up as I went along. With my partner and myself naked, I strapped Ainoko to the X shaped cross facing outwards. I started off by applying some nipple clamps to her plump little tits, then used a thin riding crop to lightly whip her thighs. Then I moved onto some wax-torture, lighting up a thick red candle and dripping the crimson wax onto Ainoko's shoudlers and tits, the girl moaning in mock pain, even though she was actually getting off on this! My cock was as hard as a motherfucker by now and I pushed it up into Ainoko's tight, bald pussy and roughly fucked her whilst she remained cuffed and immobile. The old guy in the seat nearby was enjoying this, his prick semi-stiff as he watched with wide eyes. He was, I thought with an amused smile, probably a respectable guy in his normal life. Like most people, he was reduced to satisfying his desires in secret like this. Shame, really. Things were much better for me and mom and all the others who did what the fuck we wanted without shame.
I pulled out of Ainoko dangerously close to my climax, and whipped her thighs some more with the crop. Then I uncuffed her and took her to the raping-stool, over which I bent her roughly, Ainoko playing her victim role and pretending to resist. Snapping the cuffs on the stool's four metal legs over Ainoko's wrists and ankles, she was almost doubled over, securely restrained with her fat little ass thrust out, vulnerable and spread.
I took a short leather strap with which I spanked Ainoko's ass and lower thighs, the leather producing a resounding 'SMACK' that sounded extra loud in the small, musky room. Ainoko wailed in mock agony and I spanked her harder, enjoying this and almost forgetting about the old guy in the corner who still jacked himself off but was not yet erect. My cock as hard as steel, I got in behind Ainoko and entered her pussy from behind, roughly fucking her whilst reaching for the burning candle. I tipped it over Ainoko's back, dribbling red wax over her as I fucked her, the wax going hard and crusty within moments of striking the young woman's pale flesh.
I withdrew intact and resumed whipping my willing captive's asscheeks with the riding crop, before continuing this activity with my bare hands. Ainoko's buttocks could take a lot of punishment and soon they were bright red and evidently stinging. I took some KY-Jelly and quickly lubed up my prick before getting in behind Ainoko once more. I entered her tight ass, squeezing the head of my cock into her puckered anus. I shoved and grunted as I sank the first 6" of my dick into her rectum, then with a long thrust rammed in the remaining 6". Ainoko squirmed with delight underneath me and I fucked her shitter roughly, holding her wax-encrusted shoulders as I buggered her. I could see that the old man watching intently had now finally achieved an erection and it was about time for him to join in, and so I finished off quickly, letting my orgasm rise and explode, my prick pumping hot semen into the Japanese girl's rectum.
Once I'd pulled out and stepped to one side, the old man quickly got up, and clearly fearful that his long sought after erection may desert him, he rushed up behind Ainoko and stuffed his small, stiff dick into the girl's asshole. He panted and cried with joy as he buggered her, and his orgasm didn't take long to arrive, the old dude almost passing out with pleasure as he ejaculated into the bowels of a girl young enough to be his grandaughter.
Like a lot of men, the client was seemingly ashamed of his actions once he'd cum, and after hurridly dressing, he left Ainoko a $50 tip and left the room on his own. I untied Ainoko and helped her up, the girl grinning and clearly having had a good time. It was fantastic, the girls so frequently told me, that they were paid for having fun!
"I've been fucked by him before," she told me as she rubbed the red marks running round her wrists, "A few times. He always likes the same thing, to see me being whipped and fucked before he joins in, though until now it had always been by another girl. He likes me I think!"
"You must be complimented!" I said.
"Yeah, he's a sweet old dude. I talked to him once, when he actually bothered to stick around after he'd cum. He's actually in his 70s! He's a retired judge and is still the CEO of a half-dozen companies that probably own half of downtown!"
"If I was that rich I'd buy a fucking brothel and use it all myself!"
"Me too," Ainoko laughed, "But I'd fill it full of men like you and have them tie me up and fuck me all day long!"
"Why did he fuck off so quick, like he was ashamed?" I wondered.
"I don't know," Ainoko shrugged, "Fuck knows why some men feel guilty about such things. Whatever is enjoyable is justified, even fucking young girls in the ass after watching them get whipped and spanked! There's nothing shameful in anything so long as it gives you a hard on."
"Yeah. For fucks sake, I fuck my own mother, up the ass, and I'm not in the least bit ashamed."
"You're enlightened," Ainoko grinned, and kissed me, "and you're mother is one lucky slut to have a big-dicked motherfucker like you for a son. Anyway, enough of the psychological analysis of rich old men. I'm gonna have a shower to get all this wax off me. I've got another few hours before I go home"
"I'm off upstairs to rummage through the fridge, I'm fucking hungry."
Ainoko left the room, naked and carrying her clothes as she went off to one of the various showers in the whorehouse. Meanwhile, I slung on my clothes and left to go upstairs, feeling horny again already.
In my mom's apartment, my bedroom was first down the entrance hallway, and I popped in there and took off my clothes again. I liked just strolling around the place naked, my cock swinging between my legs like a heavy club which invariably attracted the attention of my mother. I left my bedroom and strolled down the hallway and into the large living room, where I could hear the sounds of the TV.
My mom was slumped on the sofa, sipping a glass of lemonade and wearing just a tight T-shirt and a pair of lacy black panties. She was watching a video of some indie band live, the guitar music moderately loud as it pumped through the speakers. In an armchair nearby, Andrea was sitting and reading a book titled The Story Of 'O' and was completely naked except for a pair of mirrored sun-glasses. That big-breasted whore was now 33 but still as sexy and as beautiful now as she had been 7-years ago when she took my virginity.
"Hi sweety," mom smiled, not at all surprised at my appearance nude, "How are you?"
"Fine mom," I replied, giving her a kiss on the forehead as I stood before her.
"I thought you'd be downstairs all day, fucking the girls," mom continued.
"Yeah, I fucked one, that Japanese girl, Ainoko. I whipped her in the bondage room, spanking her before I fucked her whilst some old dude watched and jacked off. Pretty fun eh?"
"So you're all shagged out are you?" Andrea asked, taking off her sunglasses, "Shame."
"I'm far from shagged out," I smiled, "Certainly not with you two around. Look here mom, I shot my sperm not five-minutes ago and I'm semi-hard. Fancy getting me fully hard?"
"I'm sure I can do that!" mom replied, reaching out to stroke my prick. My cock reacted immediately, and as I stood in front of the sofa, mom rubbed my prick until it was as hard as an iron-bar before jacking it off with both hands and sucking on the end.
Andrea put her book aside and walked up to me, stroking my firm chest and lightly kissing my neck.
"Are you nice and stiff?" she asked me, her lips close to my ear.
"Yeah," I gasped, my mom meanwhile sucking deeply on my long cock, "As stiff as possible!"
"You're mom is a good cocksucker," Andrea continued, "She's got you as hard as a steel-rod. Now, what are you going to do with that big penis eh?"
"I'm gonna stick it up mom's ass," I grinned to Andrea, turning my head and giving her a hot kiss on the mouth, "Then you are going to suck it clean and then I'm going to bend you over and fuck your tight shitter."
"Sounds like a fine idea to me ya motherfucking stud," Andrea laughed, and then kissed me again, her huge breasts pushing against me. She then stepped back and mom, who'd frigged her pussy whilst listening to this conversation with growing excitement, took my prick from her gullet and stood up. She removed her panties quickly, then whipped off her T-shirt so that she was completely nude like Andrea and myself.
Mom got on her hands and knees on the sofa, thrusting her firm ass out, her lovely, puckered anus winking up at me. I sat behind her and systematically set about hungrily licking out her asshole, rimming her thoroughly and pushing my tongue up her but. Meanwhile, Andrea, her deep brown skin contrasting with my mom's pale flesh, knelt in front of my mother and offered her tits to suck. Mom sucked hard on those big juicy breasts, licking the erect nipples whilst Andrea friggered her pussy and panted in pleasure.
Having finished giving mom a good ass-rimming, I knelt up on the sofa and performed the operation me and mom were so familiar with. I forced the saliva-dripping head of my cock into mom's anus, slowly easing forward until my foot-long prick was wedged fully in her rectal chute. Mom continued to deeply suck on Andrea's tits whilst frigging her own clit, whilst I wasted no time in bulding up a solid pace as I fucked my hefty prick backwards and forwards in mom's gripping asshole.
Shortly, mom was panting hard with lust and uttering barely coherent profanities. Andrea had got up off the sofa and stood nearby. She'd lit up a joint and smoked it sexily whilst watching us, getting off on just casually standing and getting lightly stoned whilst watching a handsome young stud bum-fuck his mother.
A few minutes later, Andrea clearly couldn't stand to merely watch any more, and she sauntered over and handed me the joint.
"Pull out," she ordered me, kneeling in front of the sofa, "Tug that fat cock from mommy's asshole and give it to Aunty Andrea to suck!"
I did so, sliding my shaft from my mom's anus and tending it to Andrea who clamped her fat lips over the soiled head and began to slurp and suck. I smoked the remainder of the joint, watching Andrea kneeling and fellating me whilst my mother fell forwards on the sofa, exhausted, her anus gaping and leaking saliva and pre-cum.
By the time I'd finished the joint Andrea had done a great job of licking my dick clean.
"You promised to stick it up my ass," that hot lady told me, "You ready sweety? You ready to fuck my shit-hole?"
"I sure am Andrea!" I told her, then playfully smacked one of my mom's buttocks with my hand, "Move over mom, you 'aint the only whore in this place with an anal-addiction, Andrea wants a go!"
My mother rolled off the sofa and sprawled on the floor, grinning happily and watching as her place was taken by Andrea. I got down and rimmed her asshole until it was nice and slick, before I knelt up and dealt her the same treatment as my mom had just received. My pelvic muscles worked over time as I humped Andrea's ass hard, my dick thrusting repeatedly up into the wet depths of her hot, buttery crap-chute. She friggered her clit, urged me one with wild cries of passion and generally went out of her way to act like the fantastically wanton, shameless slut she was.
"Where are you going to cum son?" my mother asked, sitting up, now recovered from her own hard fucking, "Up Andrea's asshole? Or are you going to fuck me again?"
"I think I might cum over the pretty faces of you two sluts," I told them, still sodomizing Andrea, "Yeah, that's what I'll do! I'll shag you both up the bum again then I'll ejaculate over your faces. Would you like that?"
"Yeah," mom grinned.
"Absolutely!" Andrea agreed, "But make sure you give us both another ass-fucking first! We can't get enough of this."
"I know," I replied, "Neither can I!"
After another few thrusts, I yanked my prick from Andrea's anus.
"That was good!" she panted, staggering off the sofa, "My asshole feels like it's on fire, the way it should be after an ass-fucking! I hate it when I'm fucked in the ass by nervous guys who go slowly and softly-softly in case they hurt me. If a hole is worth fucking, it's worth fucking hard and rough!"
"You should write a sex-guide," I smiled, and Andrea blew me a kiss as she then knelt on the floor.
"Is it mommy's turn now?" my mother asked, standing up.
"It sure is mom!" I told her, "Come on, climb aboard the sofa!"
Mom did so, bending over before me and shaking with pleasure as I re-inserted my long shaft into her hungry anus once again. I fucked her butt solidly for quarter-of-an-hour, before I pulled out. Mom's place was immediately taken by Andrea who, likewise, was subjected to another good butt-fucking.
Finally, I stood up and had both my mother and Andrea sit on the sofa in front of me, sitting next to each other and facing my throbbing prick with mouths wide whilst I jacked off. I pumped my long cock with both hands and soon felt my legs tremble.
"Here it is!" I announced, and sure enough, there was a sticky explosion of white fluid that shot out in thick, creamy wads. Moving my cock from side-to-side, I ensured the fountain of sperm was evenly spread over both lady's faces, my ejaculation long and excessive. Mom and Andrea's faces were slathered with semen afterwards, and even though they'd caught plenty in their mouths, they still had a good amount of my jism hanging from their faces, running down their cheeks and dotted over their shoulders and tits. I fell back in the nearby armchair, helping myself to the glass of mineral water Andrea had been drinking whilst I watched both women kiss each other on the sofa. They licked the cream off each other's faces, kissing hard and frigging each other's pussies and assholes.
"Who's for some lunch?" mom shortly asked, smiling happily.

In November of 2000 a girl called Jennifer came to the apartment, asking for employment downstairs. Aged just 15, Jennifer was tall, slender, big-breasted and had golden blonde hair that reached almost to her waist. She was very pretty and very keen, so she was considered an 'employee' immediately. She had no place to stay though, having left her home in the Bronx with just a suitcase of clothes, but my mom let her stay in the spare bedroom.
Jennifer was a great hooker as, like a lot of the girls who worked for my mom, she enjoyed the sex more than the money she got paid for doing it. Jennifer put in great long shifts, seeing loads of guys and fucking and sucking them dry, earning plenty of tips from gratefully satisfied men.
It wasn't long before I ended up fucking her. Mom was out that day and, mid-afternoon, I'd been just watching TV in the living room when Jennifer had come up. She'd finished a shift and had showered, and joined me on the sofa. We watched stupid sitcoms and smoked a couple of joints before we soon went off to my bed, stripping quickly and fucking hard. I shafted her tight pussy and gave her three orgasms before I climaxed myself, spurting hot seed deep up her hot womb.
Afterwards, we lay next to each other, sipping a glass of wine and smoking a joint each.
"So you live up here with your mom then?" asked Jennifer.
"That's right," I admitted, "I started fucking her just a few months ago. I don't know why I didn't start sooner."
"Do you fuck all the girls who work downstairs?"
"Mostly," I shrugged, "It's not like an obligation for them, it's just that most of them - like yourself - enjoy sex just as much outside of 'work' as they during it. It's good fun for us all!"
"When did you start fucking?"
"When I was 12, with Andrea, the co-owner of this place."
"Hah, beat you," laughed Jennifer.
"How do you mean?" I asked.
"I lost my cherry when I was only 9. It was to my father who seduced and fucked me. That's why I'm not at all shocked by you fucking your mom. Incest is best, as they say!! My dad fucked me almost daily and taught me how to suck his dick and swallow, and my mom got in on it too, teaching me how to lick and finger a woman. Mom was very pretty and young - she'd given birth to me whilst still in her teens - and I loved fisting and fucking her. I did prefer being fucked by my dad though, and daddy deflowered my ass on my 11th birthday. I loved anal-sex so much that after my periods began when I turned 12, I talked my dad into fucking me nowhere except up the bum so that I'd avoid pregnancy!"
"It sounded as if you had a great time Jennifer. How come you left home?"
"Well, last year my dad began to tell me he was worried that he might get caught fucking, so he stopped. However, I think it was just an excuse because he then just turned his attention to my younger sister. He likes 'em young daddy does! Anyway, not having interest in school I left home to come here to seek more sex and maybe a fortune too!"
"If you like anal," I said, putting out my joint and sitting up, my cock rock hard, "You've come to the right guy!"
"I know," Jennifer smiled, finishing her joint and her glass of wine, "You mommy told me you love taking her up the ass, and I've been dying to take that big fucking prick of yours up my shitter too! Let's do it!"

As time moved on, I fucked Jennifer more and more along with my mother and soon I considered the teenager to be my girlfriend, even though we happily fucked other people.
Four-months later on February 7th, 2001, it was my mom's 46th birthday and she decided to have a big party.
"Plenty of sex, drugs and rock 'n roll," mother insisted that morning, "plus more sex!"
Because Jennifer was going to turn 16 exactly a week later, it was decided that mom's party would be a joint birthday celebration for both her and Jennifer. Plenty of weed and wine was available and the whorehouse was closed and all the hookers due to work that evening invited upstairs as we all got stoned and merry into the evening. A few of Jennifer's male friends - teenage boys - came along and it soon descended into an orgy with some of mom's friends and mine turning up. The number of males was boosted when we invited up some men who turned up to the closed whorehouse downstairs for some freebies (they couldn't believe their luck!) and a great time was had by everyone. Mom and Jennifer even had a contest to see who could satisfy the most number of guys at once. On the living room floor, Jennifer took a cock in her cunt, ass and mouth and jacked off two teenage lads with her hands. Mom won the contest when she managed to take two guys in her anus at the same time, along with one in her cunt, mouth and each fist, making six men having sex with her at the same time. All six guys hit their climax in a short space of time, mom having half-a-dozen cocks spurting in and over her, the five guys seeing to Jennifer also shooting forth their sperm. I was in the audience of revellers watching all this, sitting on the sofa and being fellated by Andrea, spurting my seed into her warm mouth whilst watching my mom and girlfriend get gang-banged on the floor.
On a Saturday night a month later, Jennifer suggested a visit from her younger sister, the one who had taken over Jennifer as their father's willing sex-object.
"She's called Diana," Jennifer explained, "She's a month shy of 12 and is the sweetest little thing! Dad's fucked her in all the holes and she's as well versed in sexual practices as any whore here! Problem is, our daddy is away on business for a few days and mom's too busy with chores, so Diana gets bored and miserable if she's not being fucked."
I was naturally eager to meet this pre-teen nympho, and she soon came round to the apartment. Diana was very pretty; like her sister she was slender and blonde, but her hair was cut short. With a bald pussy and very tiny titties not big enough to require a bra, the delicate youngster looked very much a sweet, innocent girl. However, within minutes of inviting her into the apartment it was clear the 11-year-old was not so innocent! As we had a cup of coffee each, the minx swore like a trooper, dropped innuendo's into every conversation and was the first to suggest rolling up a couple of spliffs 'to make us more horny!'.
As delicate as that child may have seemed, she was a little animal in bed! I cunt fucked her until she came hard under my thrusting but held myself in check so that I could ensure Jennifer was not left out too. I climaxed quickly that first time, jacking off my cock and flooding Diana's face with sperm, Jennifer wasting no time in licking her sister's face clean. We resumed almost immediately. As delicate and pert looking as Diana's ass was, that lovely little bum was more than capable of holding the full length of my fat cock in it's tight grip. I came up her rectum twice and her sister's once during our hot fuck-fest that lasted into the early hours of the morning, and those two sister's brought forth six more ejaculations from my cock in the encore session that lasted most of Sunday.

Not all the clients of the whorehouse were males, as I discovered that May when I was introduced to a woman called Joanne, who's respectable appearance disguised a fetish for bisexuality and incest. A married Jewish lady from New Jersey, Joanne was short, plump and big breasted with a very pretty face. She was in her mid-thirties and had a son who was with her on her visit to our den of whoredom and depravity. She handed over her money at the reception area of the brothel and whispered her desires to my mother. Apparantly, Joanne wanted to see her son - a dark haired, handsome little boy aged 9 - being anally fucked whilst she herself was seen to by teenage girls. I was selected for the task of buggering the child, and whilst I didn't normally go for males, kids that age were pretty much asexual, and being an ardant fan of anal anyway, I decided to go along with it.
The fun took place in one of the larger rooms in the whorehouse, a huge double-bed sitting in the middle of the brightly lit room, mirrors on the walls enhancing the view of the action. Joanne insisted on being fucked by the youngest prositutes around, and luckily that afternoon there was a beautiful Pakistani girl who, despite being just 14, had been with us for almost a year and was skilled enough to be entrusted with seeing to the very particular desires of this Jewish lady. She was accompanied by Jennifer, my girlfriend. With everyone nude and prepared, Jennifer and her younger companion fitted big dildos to their groins and buried them in Joanne's cunt and asshole in a position that gave her a perfect view of the bed where myself and the boy were. Urged on by Joanne, I greased up my prick and sodomized the woman's young son. Joanne had regularly fucked the boy with a strap-on herself at home so his little ass was capable of standing up to it's massive invasion, my prick buried in tight little butt to the hilt. Despite some initial reservations about fucking a male child, I found it to be damn good fun, and I eagerly buggered the 9-year-old whilst his mother watched and climaxed as she herself was fucked by the two teenagers she was sandwiched between.
I ejaculated deep inside the child's ass, and once he'd rolled aside, I jacked off my cock until I was stiff once again. Joanne now disengaged herself from her female fuckers and came over to me. She got down on her hands and knees on the bed, her big bare ass thrust obsecenely at me, and I shoved my big cock into her pussy. Joanne was already in heat with the previous activities and it didn't take long for me to make her climax loudly whilst I shafted her cunt. I withdrew and proceeded to insert my monstrous member into her chubby, matronly ass and resumed fucking her, the randy mother inviting her son to come over so that she could suck his soft little dick whilst being butt-fucked hard. She climaxed a second time and I eventually had my second orgasm too, my sperm flooding Joanne's rectum in hot squirts whilst her tight sphincter gripped my thick shaft.
Joanne and her son dressed and the very satisfied mother paid me and the two teenage girls a $100 tip each and promised to return. In fact, every Sunday Joanne came to the whorehouse with her little boy to repeat the previous activity. She swore she could not imagine anything would give her more pleasure. She even recommended us to a couple of her friends, bored housewives who had too much free time and cash. These fine Jewish ladies were content with just being fucked one-on-one by me, and as pleasurable as it was, these simple sexual activities would become monotonous were I to recount them in all detail.
I was called into action a few other times too at the brothel. A bisexual lady came once and wanted to be fucked by a man and woman in a threesome, myself and Jennifer volunteering for duty. One evening, a couple turned up, the guy wanting to just jack-off whilst watching his wife be thoroughly fucked by a young stud. The next week another guy turned up with the exact same request, except he was accompanied by his teenage daughter who he wanted to watch being fucked. In both these occasions I was naturally happy to be of service!

Mid-afternoon on an Summers day and I made it into the apartment building just as it started to rain outside. I rode the elevator upstairs to the top floor, and entered into mom's apartment. I'd been shopping for some clothes and I dumped the bags onto my bed before heading into the living room. There were two hookers there, both in their late-teens, presumably having just finished a shift downstairs as they sat in dressing-gowns fresh from a shower. I said hello to them and indulged in a bit of polite small-talk, before leaving and going into my mother's room.
Sure enough, mom was there. And sure enough, she was having sex.
On her knees and elbows, mom was nude and panting with pleasure as Jennifer knelt behind her. Dressed in just a pair of fish-net stockings and a black garter belt, Jennifer was pushing a greased fist up into my mother's anus, steadily sliding in her forearm and giving mom a great climax.
"Fuck me Jennifer!" wailed mom, frigging her clit, "Stick your whole arm up there! Oh GOD thats fantastic, oooh! YEAH!"
Jennifer eased her arm up further, her fist sinking further into mom's colon. I acknowledged the women with a brief nod of my head and a lewd grin, before I quickly undressed, my prick erect. Jennifer's ass was already greased up so I got in behind that hot young girl and shoved my long dick into her asshole. I fucked her hard, spurring her on to fist my mom's butt deep and forcefully, cries of pleasure soon filling the air.
There was a switch in positions shortly, and with her entire right-forearm slathered in Vaseline and shit, Jennifer got down and took my mother's greased fist into her butt. Mom pushed her arm further and further up Jennfier's rectum whilst I in turn gripped my mother's shoulders and steadily fucked her, first in the pussy, then in her ass. It wasn't long before all of climaxed, Jennifer frigging her clit with shit-stained fingers and crying out with pleasure, her own butt now impaled on mom's forearm. Meanwhile, I ejaculated in my mother's crap-chute whilst making her climax by reaching round and frigging her clit.
Fifteen-minutes later we were showered clean and sitting on the long sofa in the living room, all dressed and sipping a cup of coffee each and sharing a joint. It was pouring down outside now, the sounds of the rain hammering at the big windows in the living room drowned out by the Beethoven's Fifth Symphony playing on the stereo.
"Mom?" Jennifer began.
"Yes honey?" my mother responded, delighted that Jennifer had begun to refer to her as 'mom'.
"Me and Randy were talking last night of marriage."
"Is that right?"
"It is mom," I admitted, toking on the joint and handing it to Jennifer, "We were considering getting married legally. We know it's not all that necessary, that we love each other anyway, but it would be nice to have it down on paper."
"And it'd be a good excuse for a big party," Jennifer giggled.
"Well I agree utterly," mom said, "I'm pleased for you two! Come here, gimme a kiss!"
We both kissed mom on opposite cheeks, then settled back, listening to the music and getting pleasantly high.

The official wedding of me and Jennifer was a quiet little affair in a registry office with my mother, Andrea and Jennifer's sister Diana present. It took place in late August 2001, not long after my 20th birthday. The more informal reception took place in mom's living room, with lots of male and female friends of all ages present. Like the joint birthday party earlier in the year there was plenty of drinking and dope-smoking before and orgy took place. I avoided alcohol throughout the afternoon so that I was capable of fucking long into the evening. I climaxed eight times that day, and had a go at fucking over two-dozen women, from my mother, to Diana, to various hookers and, of course, Jennifer. My new sweet-sixteen wife was the center of the attention of a lot of the males who were present, mostly the boyfriends and friends of my mom and her hookers. Jennifer was fucked to exhaustion and like myself, she fell asleep as soon as we went to bed. We had to wait until the morning until we could fuck together and alone.
Afterwards, we carried on as before, me and Jennifer sleeping with my mother most nights, Andrea, Jessica, Ainoko and pretty much every other hooker around the place still a big part in our prolific and non-stop sex-lives.

Despite all that had happened so far, the fun - for all of us - was still only just beginning...

(C) Ermberto - August 2002