When I met her, I did not know where our relationship would take me, but it was a wild ride.
The Wildwood Society
I met Aileen by chance, shopping for vintage clothes in Kensington Market. She is buxom and beautiful, soft dark waves of hair to her shoulders, smoldering green eyes, full lips, and wide inviting hips. We fell in love instantly. She took me to her mansion in Etobicoke, Baby Point, and we consummated our love. We abandoned our current partners.
Our passions for reading, cooking, ancient history, art, music, all coincide. Most of all is our passion for sex.
We began to research all forms of sexual behaviour and sexual experience. We read clinical literature and classical works of pornography from John Cleland’s Fanny Hill to The Pearl to the stories of PowerOne.
We began to explore video porn downloaded from the Internet and often fucked in front of the wide screen TV full of porn. We found that Japanese uncensored porn is the most arousing and gives the strongest and most frequent orgasms. We masturbated each other and ourselves as we watched bondage porn, and we played with toys. We fucked in every position we saw on the screen. We made photos and videos of our sex play and used them to arouse each other.
But as we grew more and more excited by our sexual explorations, we found we still wanted more. Finally the day came when we had the frank conversation about fucking other partners. Secure in our love for each other, we got married and then went on the swingers’ scene.
At first, it was new and exciting. We visited suburban homes, met new couples, stripped, and fucked them. Then one couple introduced us to the Lakeshore Swingers club. At the first meeting we attended, held in a local hotel, we danced in the ballroom with fifty other couples of all ages and chose one who seemed eager. We went to their suite, stripped, bathed, and fucked. It was exquisitely arousing to watch my penis fucking in a stranger’s vagina with blonde pussy hair while beside me I could see Aileen’s dark cunt hair forked by a stranger’s penis. Several such sessions followed.
Then one Saturday night at a swinger session, the couple we had just fucked invited us to their home. We had been discussing our explorations of sexual behaviour and sexual fantasy, as well as our escalating need for arousal and more intense sexual experience. Harold was fifty or so, dark and powerfully built. He had given Aileen quite a ride in bed. Marissa was thirty or so, honey blonde and full of luscious curves, including the curves of her vulva lips, which really turned me on and got my cock rigid. I had fucked her hard and came in a strong orgasm that lasted many intense moments as I squirted into her vagina. It was the first time a swinger couple had not demanded condoms.
Their home in Port Credit was on an isolated parcel of land along Lake Ontario. The “no exit” sign on the paved lane into their driveway proclaimed their privacy. They got us drinks in their living room and continued to ask us questions about our exploration of sexuality. We both became quite excited, but they focused mostly on Aileen. I found later that they knew the woman was the key. We just expected another swinger fuck, but instead they opened the door to a whole new world.
“Have you heard of the Wildwood Society?” asked Harold casually. They described it as a group of very wealthy people who wanted to explore all forms of human sexuality. Their only requirement was total secrecy. Any violation was met with death. Harold went on to describe two examples of members who had attempted to leak their secrets and had met horrible deaths. “Even my telling you now puts you both under threat of death, as well as me and Marissa. You must never tell a soul even the name of the Society.” “You are both members?” I asked. He nodded.
We assured them of our secrecy. We were scared but very excited and demanded to know more. The Society met in secrecy at remote locations, a new one each time. No expense was spared. Harold believed one older man in his sixties who was fabulously wealthy was behind it all. No sexual act was barred. Couples were expected to assume at various times both dominant and submissive roles. The Society seemed unlimited, well beyond kink. However, their primary focus remained on heterosexual fucking. “We in the Society feel that sexual intercourse between a man and a woman yields the strongest orgasmic experience.” We were fascinated. We were hooked.
“Why are you telling us this?” I asked. “Do you want us to join? Did you and Marissa think we would make good members?” Harold nodded. “Yes, but Marissa and I will have to screen you both first before we propose you for membership. If they like our report, you will have to attend a meeting with the full Society and earn their approval before they will accept you for membership. Are you willing?”
We asked more questions and agreed. They took us upstairs to their bedroom. Their immense bed was bigger than king size. The frame included wood and metal posts with restraints attached. They stripped us and tied us to the bed on hands and knees, faces in pillows, naked buttocks in the air. “You will have to be able to accept restraints whenever a Society session demands it, “ explained Harold.
Then he and Marissa took large paddles with studs from under the bed and began to spank us until our bums were red and sore. “You will have to be able to accept punishments also whenever a session requires it,” explained Harold.
Then he mounted Aileen and fucked her. I could see her tits rippling with each thrust. He pinched her nipples and slapped her breasts. His cock was a blur in her cunt. He came hard in her vagina and left her labia dripping with his semen. To me he said, “I know you can handle watching another man fuck your wife, but you will also have to watch her gangbanged. She will have to accept being fucked in restraints. Ah, she’s smiling now. That’s good.” Aileen had had a strong orgasm while he had fucked her.
I was still tied. Before I could wonder why, Marissa approached me with a dildo strapped to her crotch. She lubricated it with Vaseline and pushed it into my anus. Only a doctor had invaded that orifice before, but I buried my head further in the pillow and let her fuck my ass. Surprisingly, I found my cock getting hard. She reached under me and masturbated me with her hand while she stroked the dildo into my butt. I came almost immediately onto her bed sheets.
She withdrew and nodded at Harold. “Good,” he said. “Many men can’t handle ass fucking, especially under restraint. You will also have to accept having a real cock in your ass eventually.” He removed my restraints. “Do you want to fuck Marissa now? I owe you one.” I grabbed her and pushed her onto her back. I cuffed her wrist over her head and pulled her legs apart, fastening them to side posts on the bed. Then I mounted her and fucked her hard in her pussy.
“Good,” said Harold when I had withdrawn. “You know how to be dominant too. We only need an STD panel from both of you by next week to submit with our report recommending you for Society membership. We’ll let you know the Society’s decision. Oh, and stand still for photos. They go with the report. Our hidden cameras already have video of this session.”
I thought about this and got quite excited at the idea of my sexual acts being captured on video. It showed as Marissa took images of my erect cock and balls close up as well as front and rear naked standing photos. Aileen really got into the session, looking seductive as Harold photographed her nude front and rear, up from the floor between her legs, then spread wide on the bed, her labia pulled apart. The Society would certainly see what they were getting.
We had a nervous and excited two weeks. Then the call came. We could go on to the initiation step. It would be a Society session in a secret location focused specifically on us to test our sexual limits. If we performed acceptably in the initiation, we would be offered membership. We could still refuse membership at any time during the initiation, but we would always be under threat of death if we reveal the existence of the Society or the identities of any of its members.
The session was on the following Saturday night. The location was a rural address deep in the Caledon hills. Harold and Marissa picked us up in Long Branch and drove us. They had become our sponsors. Our performance tonight would reflect on them. I could tell Marissa was a bit nervous. “Any advice?” I asked Harold. “Just let yourself go,” he said tersely. “Let them do whatever they want to you, and when you see an opportunity, take it.”
The paved county road led to a gravel road that led to a grassy lane uphill through heavily wooded grounds. The mansion was a modern ranch style house with Georgian columns. Immediately behind it was a low roofed barn. We were stripped in the living room of the house to our underwear and marched out the back door and into the barn.
The lights were low. The barn was surprisingly warm and cozy. The assembled Society members were all naked, men and women. The walls were equipped with cabinets that held cuffs and whips and all manner of punishment tools. Various pieces of bondage furniture stood around the room. Overhead were mounted track lights, banks of them to illuminate any portion of the room. Overhead tracks also held fixtures for pulleys and chains with electric motors attached.
The murmurs in the room died down as Harold and Marissa led us into a pool of light at the centre of the gathering. A man and wife came forward. Harold said, “My Lord, these are Mr. Hemlock and Miss Osier. They wish to become members of our Society.” He and Marissa bowed to them and stepped back into the crowd.
The man was in his sixties, a grey spare fringe of hair around the sides of his bald head and a significant paunch for a belly. He was of medium height and rather pleasant features. Most impressive was his long, thick penis hanging below his testicles. Aileen and I couldn’t help looking at it. Then he spoke.
“I am Lord Whimsy, the head of the Wildwood Society. You will address me as ‘My Lord’, as you’ve heard Harold do. You have expressed a desire to join us. Harold and Marissa have screened you and recommended you. You have been told the rules. You will be tested tonight in every way. My wife, Lady Whimsy, and I will supervise. When the test is over, we will confer with the members of our ***********ion committee who have been investigating your backgrounds. We will then deliver our decision about your membership. It will be final. Do you understand?”
We nodded and said, “Yes, my Lord.” He took my arm and pulled me aside to stand beside his wife. Lady Whimsy was in her fifties and in good shape, dark brown hair and a neatly trimmed pussy bush. She wore a leather halter that surrounded her large breasts with holes where her nipples stuck out invitingly and a leather harness around her hips and through her crotch that framed her prominent pussy. She carried a riding crop in one hand that she slapped against her thigh. Before I could think too much about the implied threat, Lord Whimsy ordered couches brought and set in a circle around him and Aileen. The members took seats.
He stood with Aileen in the centre of the gathering and removed her bra. He fondled her breasts and pinched the nipples. He slapped her hard on both breasts. Some of the male members stoked their penises to erection. The female members rubbed their own nipples and stole fingers into their vaginas. Lord Whimsy pulled down Aileen’s panties and fingered her pussy. “I always have first rights with a new girl, my dear. Privilege of ownership, you know. You see, I founded the Wildwood Society.” He pulled her face to his for a deep kiss while pushing two fingers violently up into her vagina.
He broke the kiss. Aileen moaned as he sawed his fingers in and out of her cunt. “Well, gentlemen,” he said to his audience, “We seem to have a live one tonight.” He pulled out his fingers and tasted them with a leer. “Spread your legs, dear,” he commanded Aileen. “Show the members your pussy.” He separated her labia with his fingers and flicked her clitoris, watching her reactions. She flinched and her breathing became shallower as she was aroused.
Men came from the audience and clamped her ankles to rings set in the floor, her legs spread wide. A rattle from the ceiling announced the arrival of a chain hung from a pulley as a naked man slapped handcuffs on her and attached the cuffs to the hook dangling at the end of the chain. He pushed a button on a control and the hook rose, pulling Aileen’s hands over her head and stretching her body taut.
There was a pause as Aileen’s body shone with sweat in the spotlight. As she twisted apprehensively left and right to see what would happen next, the men in the audience let her see their upright penises, ready to plunder her sexual orifices. She trembled with fear and lust at the thought of being penetrated by all these strangers.
Lord Whimsy appeared behind her out of the shadow. In his hand was a long, leather whip with three tails, each embedded with metal studs. He walked in front of her and held up the whip handle. “Are you ready for the first test, my dear?” he asked calmly. She bit her lip in fear when she saw the whip and saw its ebony handle shaped like a thick penis. Screwing up her courage, she nodded briefly. “Yes, my Lord,” she said. “I’m ready.”
“Good,” he said and jammed the whip handle up into her pussy. She screamed briefly at the sudden distention of her vagina, and then began to moan and pant as Lord Whimsy vigorously and rapidly plunged the ebony penis in and out of her pussy for several minutes. The audience watch with rapt attention, licking their lips and imagining how their cocks would feel up her cunt now engorged with the ebony penis. He stuck the handle up her pussy hard and held it there, feeling the softness of her cunt lips on his hand, the gentle brush of her pubic hair there.
Lord Whimsy stood up and pulled out the whip handle. He walked behind her, took aim, and laid the first blow across her buttocks with the whip. Aileen screamed again and as she fought for air to scream again, the second blow landed. He was thorough. I counted five, ten, then twelve lashes. Then he moved up to her back for a dozen more, and then down to the backs of her thighs for ten more, and then a final ten across her buttocks once more.
Aileen was sobbing and groaning, twisting in her bonds as her bum was whipped. Her buttocks were red and crisscrossed neatly with purple welts. I found myself intensely aroused and vowed to myself to find an opportunity to whip a buxom woman like Aileen. I was sure it would be very arousing, and indeed as I looked at Lord Whimsy, his cock had grown to twice its flaccid length and stood out straight from his body.
He walked in front of Aileen again. “Well done, my dear,” he panted. “You haven’t fainted or asked for mercy. That’s very good. Now I want to introduce my associate, Mr. Black.” A tall man in his mid-forties with a muscular build and thick wavy black hair approached from the shadows. His penis, like Lord Whimsy’s, was large and erect. Aileen glanced at him apprehensively, wondering what new lustful perversion they intended to inflict on her naked body.
“Mr. Black is one of our *********** committee, a long contributor to our Society. By the way, you’ve noticed that we don’t use real names in the Society. He will help me with our next test.” Lord Whimsy glanced down at her legs. “I see quite a dribble down your thighs, my dear. Can it be that a whipping arouses you? Ho, that is excellent in a female candidate, especially for a first time.” He grasped his penis and moved closer to her. “It will also help you for this next test.”
With that, a mechanical whir signaled that a circular section of floor where Aileen was standing began to rise slowly. When Aileen’s pussy hovered just above Lord Whimsy’s cock, it stopped and the chain above her pulled up her arms to make her body taut again. He rubbed the massive head of his penis up and down her vulva lips and then pushed his cock into her cunt. He grabbed her buttocks and began to thrust inside her pussy. Then he moved his hands up to her back to keep her body close as he fucked her. Mr. Black appeared behind her, a long bamboo cane in his hands.
Aileen was focused on the fucking she was getting from the old man in front of her. His breath and body odours were pleasantly fragrant, and his huge cock was scratching the itch that the whipping had produced deep in her cunt. She was completely surprised as the cane whistled through the air and delivered a searing cut across her buttocks. She screamed in pain and pushed her hips forward to escape the cane, just as Lord Whimsy lunged forward with a vicious thrust of his penis up her vagina.
Caught between her two tormentors, Aileen could only scream and cry as she was battered between them. Lord Whimsy could see the cane whistling toward her buttocks and timed his cock thrusts with the cane strokes to catch Aileen’s futile forward lurches to escape the pain as the cane bit into her bum cheeks. This forced his cock deep into her cunt with every stroke of the cane, and Lord Whimsy was clearly enjoying it beyond enjoyment. He was lost in an ecstatic fog of lustful pleasure; he was totally immersed in the intense pleasure of arousal that his penis was giving him as it rampaged in Aileen’s vagina.
By the time Aileen had received a dozen cuts with cane, she too was in a fog of pain and pleasure. Never had she hurt more, but never had she felt so aroused. Suddenly her whole body stiffened in her bonds. “Aaaaaaggh,” she screamed as an orgasm raced up and down her whole body. Lord Whimsy could feel her vagina clenching his cock, and he stopped thrusting. He nodded at Mr. Black, who dropped the cane and approached Aileen from behind.
As Aileen recovered her senses a little from her orgasm, she felt Mr. Black’s cock probing at her ass. He pushed his cock across her lower cunt lips to wet it and then shoved it against her rear sphincter. I could see she was about to protest. We had never attempted anal intercourse with each other or with another couple, but I knew this was different. The Society had no rules, and anyone in a submissive role had to do whatever was demanded. She bit her lip and felt Mr. Black’s penis entering her rectum, pushing inward until she could feel his thighs tight against her sore buttocks. To her surprise, it felt rather soothing.
Then the two men began to thrust, Lord Whimsy in her pussy and Mr. Black in her ass. Like the caning, they co-ordinated their thrusting. They pulled back together. They thrust into her together. Then each went solo with an individual rhythm. Lord Whimsy was perspiring but loving every second. “I can feel his cock in your ass, my dear,” he told her as he fondled a breast and nodded at the cameras capturing Aileen’s ordeal. “How do you like being skewered like this?” Aileen licked her lips and managed a small smile, and then a short nod. Lord Whimsy pulled her tighter and thrust harder. “Ho ho,” he chortled. “I love this one.”
The double fucking built in speed and ferocity. Both men panted and grunted out their obvious pleasure, and then “Aaaarrrrrgghhh” as they felt the divine stiffness in their penises as they began to come. Their thrusting ended with the ejaculation of their semen in deep in Aileen’s rectum and vagina. The white trickle from both orifices was proof for the camera. Birth control was the member’s responsibility. I discovered later that some women chose not to take the pill because they wanted to become pregnant. It gave them time off from the Society’s sexual demands and produced children who were above average in strength and intelligence.
The chain was lowered and Aileen’s shackles were removed. “You are a marvel, my dear,” Lord Whimsy exulted. “Not a murmur of protest and even an orgasm or two. My, my, I think membership is likely for you. But we do have another final test for you later, and remember that your partner must pass his test too. But I think things are looking good for all of us.”
As he sat down with Aileen, fondling her breast, I was pulled from my seat by Lady Whimsy and led to the centre of the circle in the spotlight. Like Aileen, I was stripped of my underwear, a blessing because my cock had been making an uncomfortable tent in my shorts. She forced me to spread my legs, then cupped my balls in one hand while the fingers of the other played up and down the shaft of my cock, stopping to flick lightly around the corona.
She turned me around slowly to display my erect penis to everyone in the audience. “Ah now girls,” she crooned. “See what a magnificent stiff stander we have here. Let’s hope it stays that way through all the tests. It would be a pity to lose it, wouldn’t it?” A ripple of giggles moved through the audience seated in the shadows. “What a nice arrow shape to the head!” She continued to rub and flick my glans penis with her fingers, making my cock bob and lift as the intensity of my arousal grew. “We’ll enjoy feeling this long thick cock tickling our pussies, won’t we?” More laughter.
She nodded to a man who emerged from the shadows with handcuffs that he proceeded to fasten on my wrists. “This is Mr. Green. He will assist me with your first test.” As Mr. Green lowered the chains, hooked my cuffs to the chain, and began to pull my arms over my head, I examined his lithe features. He was slim with wavy brown hair and a vacant look in his eye as he regarded me, as though I were just a piece of meat. It was chilling. His cock was long and thin, now fully erect.
Mr. Green locked my ankles to the floor rings so my legs were spread wide, as Aileen’s had been, and took up the slack in the chain so my body was stretched up tight. My cock stuck straight out in front of me. The head was a coral red where Lady Whimsy had been frigging it.
Suddenly she approached me from the front, arms extended out the side, and with a swift sweeping motion delivered two hard slaps to my penis, left and right. My cock swayed and I held my breath as the pain surged up through my body, but I could also feel my sex organ getting hotter, more aroused and eager to penetrate something. Lady Whimsy watched this reaction and then continued her slaps to the delight of her audience.
After a dozen or so, my cock red and hot and stinging, she stepped back to observe her handiwork. “Still nice and stiff. Very good, sir,” she commented. “Thank you, my Lady,” I replied.
Stepping behind me, she took from Mr. Green the very whip her husband had used on Aileen. Before I knew it, the greased ebony handle pushed its way up my anus. I could feel Lady Whimsy’s warmth as she closed with me, reaching around with one hand to frig my erect penis while buggering me with the whip handle in the other. The simultaneous stimulation of both my cock and my rectum elevated my arousal unbelievably. If this was typical of Society activities, I wanted more.
I was also aware of being watched. The members of the audience, especially the females, were quietly leaning forward to watch my naked body being abused, noting the shape and size of my cock and balls, lusting after me and imagining all sorts of depraved sex acts with me. It made me even hotter.
Lady Whimsy stepped back and pulled the whip handle from my rectum. Mr. Green handed her a clean cloth to wipe the handle. With a firm grip on the handle, she laid the first lash across my bum. The pain seared into me like a knife, and I thought I would instantly lose my erection. But as the second lash tore into my lower buttocks, narrowly missing my testicles, I felt a surprising warmth flood through my lower abdomen and into my cock. It stayed erect. As the whipping went on, it got even hotter.
I got ten, then twelve lashes, as Aileen did. Then Lady Whimsy handed the whip to Mr. Green and walked in front of me, examining my penis. “Hmmmm. Still quite stiff, I see,” she noted. “Very good, Mr. Hemlock. Very good, indeed. Tell me how you like this.” From behind her leg she produced her riding crop and brought the leather pad at the tip down viciously on my cock head. As the pain raced through the glans penis and into my brain, she brought the crop upwards in a hard sweep against the underside of my cock head. She followed this with a quick series of short slaps of the crop up and down and side to side, making my cock jump and leap with her blows.
Then she lowered the crop between my legs and caressed my balls with its leather tip. “How did you like that, Mr. Hemlock?” she asked. I was breathing heavily with the pain and arousal, so I couldn’t answer. I realized she didn’t really want one. “Look ladies,” she said to the audience. “He’s still stiff. Let’s see if he can stay that way bit longer.”
She took up the whip again behind me and laid on another dozen lashes, some across my back, some across the backs of my thighs, and more on my buttocks. The last couple flicked inward and caught my balls, crossing the sensitive sack with livid streaks and causing me exquisite pain. But my cock stayed stiff.
Nodding with satisfaction, Lady Whimsy nodded to Mr. Green who pushed buttons to lower slightly the circular platform on which I was standing. Positioning herself in front of me, Lady Whimsy clasped my waist and guided my erect penis into the valley of her vagina. The warmth and wetness of her cunt was a balm to the burning pain of the whippings. Stretched as I was, I could only hope she would do the work. And she did, bobbing up and down on my cock, at least until her body shook with a violent orgasm. Then she stepped away, her pubic hair wet with her cunt juices.
She nodded into the shadows and another woman appeared. “This is Mrs. Blue. She will assist us with the next test.” Mrs. Blue was a Nordic Amazon: tall and blonde, solidly built with wide cheekbones, wide mouth, and wide hips. Her large breasts like Lady Whimsy’s were caught in a leather harness with openings for her nipples and very large areolas. Between her legs was a large, thick lipped cunt covered with brown pubic hair. Some of the seated female members appeared to have bald pussies, but many had left their feminine parts adorned with nature’s foliage. I liked that. It holds those wonderful pheromone odours from the pussy so well and leads to such bloody marvelous erections and orgasms.
Like Lady Whimsy, she approached me from the front and lowered her cunt onto my throbbing cock, still not released from its arousal by orgasm. No sooner had she begun the up and down motions of fucking her pussy on my sex organ than I felt the soft but stiff head of a cock at my anus. Mr. Green was about to bugger me.
I have never been interested in anal intercourse. I’m a pussy man and happy to remain so. I haven’t even been bi curious, as they call it. But in this situation of forced sex acts, I found myself observing my own reactions with curiosity. How indeed would it feel?
It felt marvelous. As Mr. Green’s long, thin penis invaded my rectum and began thrusting, I found myself responding with my cock in Mrs. Blue’s cunt. As the meat in the sandwich, I had double sensations, arousal in both my ass and my cock. They got into a rhythm, Mrs. Blue timing her squats that pushed my penis deep into her vagina with Mr. Green’s thrusts into my rectum. Mrs. Blue had an orgasm, throwing her head back and moaning in lustful delight. Lady Whimsy appeared out of the shadows and laid into Mrs. Blue’s bum with her riding crop. This drove Mrs. Blue’s cunt harder and faster on my cock, and I could feel her pussy muscles contracting around my penis with each crack of the crop across her ass.
This violent action brought on the crisis, and I had the most intense orgasm of my life to that point as I squirted great gobs of semen into Mrs. Blue’s vagina. At the same time, I could feel Mr. Green ejaculating into my rectum. The aftershocks of fucking continued for some time as they held me tight in the sandwich and bathed ourselves in the afterglow of sexual pleasure.
There were murmurs and polite applause as I was released from my bonds and helped to a seat beside Lady Whimsy. I watched as Lord Whimsy got up and supervised the next test. He ordered a bed brought into the spotlight, a rather ordinary four poster bed with a white sheet on the mattress. Then he pulled Aileen into the spotlight again.
“You have done well, my dear,” he began. “Public display of your naked charms, public restraint and arousal, public flogging and whipping, and public fucking and buggering are all part of our pleasures in the Society. This is the last you must endure: the public gangbang.”
He paused to gauge her reaction. We all could see the fear and apprehension on Aileen’s lovely face. I knew she had never had more than one man at once. How would she react? Could she take the pussy pounding he was promising?
“I’m sure you will do well,” Lord Whimsy reassured her. “Most women do. We just need to be sure your sweet cunt won’t dry up on us during a long session. Sometimes our most popular victims attract quite a crowd of violators.” He paused. “Speaking of violators, the male members of the *********** committee should come forward now.”
He introduced them one at a time. “Mr. Grey, Mr. Brown, Mr. White, and you know Mr. Black and Mr. Green. All right, gentlemen, restrain her.” The men took Aileen to the bed and pushed her down on her back. She thought they wanted her lengthways in the normal way, but they grabbed her arms and legs and turned her sideways, pulling her arms out to the side where they were shackled by the wrists to the posts at the top and bottom of the bed on that side.
On the other side, they pulled her left leg over to the top post and shackled it there by the ankle. Then they slowly forced her right leg wide to the other side, down to the post at the bottom of the bed and shackled it there. Aileen’s legs now spread painfully wide apart, her ass and cunt open wide for all to see. Her tits heaved as she fought to control her panicked breathing, and her belly glistened with the sweat of anxious fear.
“Behold, the sacrificial victim,” announced Lord Whimsy. “If she survives this test without fear and without using the safe word to make it stop, she will become one of us.” Moving into the valley between her legs, he pointed to her cunt. “This is why, gentlemen, we formed this Society: unfettered access to luscious female bodies. Life is the cock in the cunt. Look at this one. Such a prominent Mound of Venus to pound on. Such a luxurious bush of dark pussy hair. Such juicy thick pussy lips to lick and suck. Such a cute little clitoris to flick and munch on and to grind on while fucking this beauty. Is she not a beauty and a desirable object of our lusts? Isn’t this the best part of her initiation into our lustful tribe?”
They all nodded with dissolute expressions of lust and depravity on their faces. Lord Whimsy advanced to Aileen’s crotch and flicked the head of his penis up and down her pussy slit. “I’m going to go first, my dear. As I told you, office has its privileges. Now at my age, even with an extra dose of Viagra, I will only manage one more orgasm today, and this one will be a long time in coming, if you will excuse the expression. But it will be a great one because I do love fresh cunt.”
With that, he pushed the head of his penis into Aileen’s vagina and then climbed onto the bed, squashing her breasts against his chest. “Here we go, Aileen honey. Pricks up your cunt. Enjoy the ride.” Lord Whimsy’s buttocks began to rise and fall heavily as he drove his penis into her vagina and sucked her nipples. Spread open, arms and legs shackled wide on the bed, she felt helpless and abused as his cock rampaged in her cunt.
He grunted and wheezed as his ample belly flopped on hers with each thrust of his penis. He felt his arousal grow and grow as he ground his cock into her pussy; he reveled in dominating her, feeling the heat and moisture of her cunt that enveloped his unbridled prick; he ravaged the naked female spread and shackled under him, powerless to stop his plundering her most secret treasure with his depraved lust.
Then Lord Whimsy suddenly stopped fucking her. “My dear” he whispered in her ear, feeling his cock lying in her cunt, twitching and eager for release from its torture of arousal, “you do know, don’t you, that we are making a movie right now?”
She opened her eyes wide from her miasma of sexual arousal caused by the pounding of his cock in her cunt. Her eyes held the question. “Oh no, my Lord,” she breathed. “Whatever for?” He grunted a laugh. “For us, of course. We view them later for our pleasure. We sell them on the Internet for the pleasure of others and our profit. Look up.”
In the shadows overhead, she saw a television monitor. Its view shifted every few seconds from a wide angle view of the bed with Lord Whimsy lying on her naked body, his buttocks hunching forward as he drove his penis into her vagina, to a low angle view of his cock and balls rising and falling on her pussy mound, her breasts and face visible as his bum rose, pulling his cock part way out of her pussy, ready for another thrust inside.
Aileen had never been fucked such a long time by one man. Thoughts she had about having a video made of her initiation ordeal were pushed aside by the need to focus on breathing as her breath was pushed out of her lungs by the heavy body forcing itself on top of hers, pounding its pubic bone onto hers as Lord Whimsy’s thick cock rammed in and out of her pussy. She wondered idly how bruised her cunt would be, and whether she could take the fucking to come. His rhythmic penis thrusts went on and on and on as his pleasure grew slowly and surely to a climax.
Then thankfully she felt his rhythm speed up, his cock excited to that delicious point of no return when the automatic response to stimulation triggers an orgasm. Lord Whimsy clamped his mouth on hers in a long kiss as he hammered his cock into her cunt harder and faster and harder and faster.
Then he slammed his penis deep into her vagina and held it there for a moment, raising his head in a wild groan of profound pleasure as the orgasm hit him and he felt the first jet of semen spurt from the head of his cock. Then he continued thrusting into her cunt as his cock kept spraying her cervix with his semen in decreasing amounts and with less violent contractions of his penis muscles.
Even after his cock had quit spurting, he continued to move it up and down the length of her birth channel to prolong his pleasure. It shrank and shrank back to its normal flaccid state in a warm glow of sexual release. He finally came to rest on her shackled body with a sigh of contentment.
Everyone waited until he raised his head and then reluctantly climbed off Aileen’s nude bound body. Lord Whimsy regarded her naked charms for a moment, the trickle of semen from her cunt lips made coral with the vigour of his fucking, her heavy breathing, and her lidded eyes. Then he nodded to the other men waiting to fuck her.
Mr. Grey was nearly as old as Lord Whimsy, and he was eager to ravish the restrained beauty. His short, thick cock was soon sheathed in her cunt. He accompanied his rapid fucks into her pussy with loud grunts of sexual satisfaction. When he came, it was almost silently. Only when he withdrew his cock from her vulva did we see the new flow of white cream from between her inner labia.
Mr. Brown was black, a muscular man of medium build with a big penis, long and heavy in its erection, with a cloud of tight, wiry black pubic hair above it. He forced its broad head between Aileen’s pussy lips and flicked her clit several times with his fingers, forcing a groan from her. Then he pushed his cock up to the hilt into her cunt. His cock thrusts when he started to fuck her were determined and solid. She moaned and closed her eyes as he built her sexual response into a violent orgasm. Lord Whimsy noted the orgasm with satisfaction. Mr. Brown continued to fuck her hard and then slowed his thrusts, eventually pulling back and out. He had come in her pussy. More thick white semen leaked from her abused labia. Her pubic hair glistened in the spotlight with beads of sweat.
Mr. White was, in fact, yellow. He was Asian, probably a wealthy Japanese businessman with many local investments and a taste for both Scotch whisky and white women. His penis was long and thick with the biggest cock head I had ever seen: broad and menacing with a wide urethral opening. As he pushed it against Aileen’s labia, it spread her cunt lips wide and forced a groan from her as it burrowed up into her vaginal passage.
Like Mr. Brown, Mr. White gave free rein to his lust and continued to fuck Aileen with regular, determined strokes of his penis. His pleasure built. He sucked on her nipples, then slapped her breasts hard. He leaned forward and kissed her on the mouth as his fucking picked up speed and he slammed harder into her pussy mound. His cock foamed in her labia with cunt juices and semen. Then he slowed as his orgasm hit him, and he withdrew from her body with a groan of satisfaction, his semen flowed copiously from Aileen’s pussy and stained the bed sheet.
Now in a daze of sexual arousal, Aileen had lost count of her orgasms and was unaware that the end of her initiation was close at hand. Mr. Black mounted her but did not take long to reach his climax. I thought it likely that he preferred her ass to her pussy, given his performance in the Aileen sandwich with Lord Whimsy. Similarly, Mr. Green took little time leaving his contribution in Aileen’s pussy with his long, thin penis, possibly because he preferred men to women anyway. I began to wonder what sexual preferences were represented in the membership of the Wildwood Society.
Lord Whimsy brushed a lock of matted hair from Aileen’s brow and kissed her cheek. “Bravo, my dear. Well done. We are indeed fortunate to have a luscious bit of crumpet such as you wanting to join us and have it off some more. If your partner can pass the final test, I personally will be very happy to welcome you to our Society.” Aileen smiled wanly at him as Mr. Black and Mr. Green released her from her bonds and helped her off her bed of trials.
I felt Lady Whimsy beside me get up. She drew her lips and took my hand, pulling me with her to the bed and nodding to Mrs. Blue to help her. They shackled me to the bed on my back like Aileen. Lady Whimsy took hold of my upright cock and smeared it with an ointment that felt warm at first as her hand frigged up and down my shaft, but then it began to itch and burn. The frigging got harder and faster. The itch stretched my cock to its limit. My glans penis felt swollen and hot. My balls ache. When I came, the jets of semen flew into the air and splashed ten feet away onto the carpet. Murmurs and applause rippled through the audience. “My, my, you do have quite the strong cock, luv,” cooed Lady Whimsy. “I’m sure all our ladies will want to feel it going off in their hot little love tunnels.”
She giggled and then, without breaking eye contact, mounted me, stuffing my cock into her own love tunnel. She rubbed her palms up and down through the hair on my chest as she rocked her pelvis on my cock, driving it up and down her moist cunt passage. She leaned further forward and rubbed the hard nubs of her nipples across my chest as she fucked on my cock. Then she sat up straight and wiggled her bottom to get my penis as far into her vagina as she could. I could feel the head of my penis pushing against a mucous wall that had to be her cervix. Her head fell back and her eyes have closed in ecstasy as she felt my cock probing in her very depths.
Lady Whimsy pushed up a bit and fell back down onto my cock, driving it deep again. “Aaaaah,” she moaned and repeated the action several times, each time groaning with pleasure at the extreme penetration of her pussy. Then she began bouncing with surprising energy for a woman of her age until my cock suddenly stiffened and I felt the first jets of sperm shooting out from my cock head and splattering her inner vagina walls. “Oh, oh, my, that’s good,” she breathed and kept bouncing until my slackening penis could no longer invade her cunt and flopped out.
She planted a kiss on my cheek. “You’ve got a good stiff one there, luv. I think you’re going to be OK if you can come one more time.” I wasn’t sure about that. I’d already come three times, the most I’d ever achieved in a whole evening, and that was when I was younger. I could only hope my magic penis pleasure machine stayed serviceable for one more romp tonight.
Mrs. Blue took her time releasing my shackles as Lady Whimsy explained that this last test involved trying NOT to come until told to do so. That would be quite a trick, considering that my penis had already spurted its load of semen three times. If I could keep it erect long enough to invade a couple of vaginas, it would want a quick release of seminal fluid in an intense and prolonged orgasm so that it could rest for a good long while. How many vaginas for how long was a question I couldn’t answer.
“Let me introduce our ladies on the *********** committee. You know Mrs. Blue. This is Mrs. Pink, Mrs. Mauve, Mrs. Vanilla, and Mrs. Sunshine. Your task will be to give each one an orgasm in a different position without coming yourself.” I stared at her horrified. Five beautiful women and no orgasm: I doubted I could last that long. I was lusting after them already.
First was Mrs. Pink, a petite brunette with a pink, rosy complexion. She looked about thirty as she flopped on the bed on her hands and knees and presented me with her gorgeous backside, two luscious globes of flesh with her secret slit surrounded with pussy hair nestled between. “Mrs. Pink wants it doggy style,” announced Lady Whimsy.
It wasn’t difficult. Mrs. Pink’s love nest was full lipped and wet with anticipation. I kneeled up behind her and found my cock standing at full attention. As I pushed my cock head into her cunt, she wiggled her bum and murmured approvingly. I thrust firmly into her vagina with steady strokes, feeling her ample breasts swaying under her. Her breathing got faster and shallower, and then she suddenly crumpled flat on the bed, her body shaking with a massive orgasm.
Next on the bed was Mrs. Mauve, a tall red haired beauty with big boobs with freckles on them. She pushed me aggressively onto the bed on my back and mounted me, stuffing my cock into her warm wet tunnel. Her pussy hair was real red, not strawberry blonde, and her pussy lips were thick and full. I was really turned on as she bounced on my cock, and I thought “This won’t do. I have to avoid coming.” So I pulled her close on my chest and hammered my cock into her cunt hard and fast. I got the response I wanted. Her orgasm built quickly and hit her as she gasped for breath. I pulled out of her cunt quickly to cool my cock and avoid coming myself as Mrs. Mauve shook beside me in the throes of orgasm.
Mrs. Blue pushed herself to the head of the line and mounted me as I lay on my back. She reversed herself and stuffed my cock into her waiting cunt. Then she leaned back on my chest as a video camera came out of the shadows to capture my cock thrusting in her cunt between widely splayed legs. As I had done with Mrs. Mauve, I fucked hard and fast into Mrs. Blue’s cunt, white foam of cunt juice coating my cock shaft. “Unngh uunnnngh,” she grunted as her orgasm hit her and I pulled out of her pussy, my cock vibrating and hot. I knew I was getting close to orgasm.
Mrs. Vanilla was black, or at least a dark cream colour, quite attractive with delicate features and a dark triangle of curly hair covering her pussy. She lay down beside me on her side and lifted one leg, inviting me to penetrate her pussy from behind. Being a gentleman, I accepted her offer and found her vagina to be remarkably warm and fragrant. As I thrust languidly into her pussy, hugging her delicate body close, I started daydreaming how nice it would be to come in her cunt and fall asleep.
Suddenly, I realized my cock was getting very hard and ready to come. I immediately jammed my cock up her cunt and held it immobile. While I waited for my cock to calm down a bit, I absently caressed one of her nipples and fondled her breast. To my astonishment, she began to moan. As I squeezed her breasts harder and pinched her nipples, she began to shake in a massive orgasm. I knew some women have sensitive breasts. Some can even achieve orgasm with nipple stimulation. It appeared Mrs. Vanilla was one of those. I was saved. I withdrew my over stimulated cock.
Lady Whimsy approached the bed, followed by Mrs. Sunshine. Mrs. Sunshine was Asian, possibly a spouse to Mr. White, and of the same age. She had that delicate beauty of the Japanese geisha, perfect body proportions, fine features, jet black hair on her head and on her pussy, and full breasts. “Mrs. Sunshine,” Lady Whimsy announced to me, “is old fashioned. She wants to be taken in the European matrimonial position, also known as missionary style.” She shook her head slightly, as if to say this was too boring for the Society. “You’ve done well, so this time, we will let you come.”
I sighed with relief. I knew I was home free. I took Mrs. Sunshine ceremoniously by the hand and laid her on her back. I caressed her body and breasts, spread her legs, and licked her pussy into a receptive lather. Oh, she tasted so fragrant, so pungent, so good. I was so aroused. Then I mounted her and had one of the greatest fucks of my life, thrusting and thrusting into her pussy mound and erupting into a prolonged orgasm that shot jet after jet of sperm into the depths of her vagina.
Aileen and I sat together afterwards on a couch in the semi dark, waiting for the *********** Committee to make their decision and whispering to each other. My cock and balls ached from repeated orgasms and her pussy and tits were sore from repeated pummeling, but we were very happy. “That was the most awesome sex I’ve ever had,” she breathed. “Yah, me too,” I whispered. “I hope they accept us. If this was an initiation, I just have to find out what else they do in their other sessions.”
There was a rustling as naked people got up from their seats and mingled, but in an orderly way, whispering to each other. The men ended up on one side of the room, the women on the other. The bed was removed from the centre of the room under the spotlight, and then Lord and Lady Whimsy appeared there.
“Ladies and gentlemen of the Wildwood Society, your *********** Committee has reached a decision,” announced Lord Whimsy. “Mr. Hemlock and Miss Osier, will you come forward, please.” I took Aileen by the hand and we walked into the bright light and stood in front of the Lord and the Lady.
“You have both performed beyond expectations tonight, my dears,” he began. “We of the Society have rarely seen such endurance and such lustful response to the sex acts that we made you perform. Your obvious enjoyment of every depravity is an inspiration to us all, and we hope you will want to contribute to the design of our sex sessions so that we can benefit from your active sexual imaginations.”
We looked at each other and smiled with a hint of smirk as our imaginations began to work. They wanted us to be dirty with them. “And so, my dears, we welcome you now into the Wildwood Society. May your orgasms be many and powerful.” The group broke into spontaneous applause.
“And now, we ask you to indulge us in an old custom of welcome into our Society. The assembled members have enjoyed watching your performance tonight. Now they wish to be acquainted with your naked bodies.” Lady Whimsy produced two sets of handcuffs and fastened them to our wrists behind our backs.
“Miss Osier,” said Lord Whimsy in a formal voice, “please move down the line of men over there.” He motioned to Mr. Black, who took her arm and guided her to the first of the naked men, who fondled her breasts and cupped her pussy mound, sliding an exploring finger into her cunt. One by one, they passed her on, kissing her on the lips and on the tits, pinching her nipples, slipping between her legs to lick her pussy, or grabbing her buttocks and spreading her cheeks to slip and exploring finger into her asshole.
My own introduction to the women was similar. Mrs. Blue led me down the gauntlet of women who kissed and licked and rubbed my cock into erection, teased my balls, or slipped sly fingers into my asshole. Sore from rubbing and slapping, my penis felt grateful when the end of the line arrived and I was returned with Aileen to the spotlight circle beside Lord and Lady Whimsy.
“And now, ladies and gentlemen,” he began again, “I must thank you for welcoming these new acolytes into our mysteries of the human libido in such an enthusiastic fashion.” Lord Whimsy chuckled as he glanced pointedly at my erect penis. “Please feel free to indulge your passions in the usual ways.”
Several men came over to us and took hold of Aileen, talking and laughing and charming her into sitting and then reclining on a couch where they could take advantage of her female charms. Soon cocks were introduced into her cunt and she was being fucked savagely and repeatedly on the couch: cocks in her cunt, in her ass, and in her mouth.
Some of the women surrounded me and pulled me over to another couch. One bleach blonde matron called Miss Patty pushed me onto a reclining damsel whose naked charms I had noted before. Her name, I later discovered, was Nella. She was part English, part Maltese, with a beautiful, oval face and full lips, long dark brown straight hair to her shoulders, and olive skin like silk. Her pubic hair was luxuriously thick and dark brown covering a prominent mound and fat, full pussy lips. As I eased my erect penis through her bush and into her vagina, I found my libido revving up again, my cock getting stiff and hot, and my hands roaming all over her naked body.
The other naked women surrounded us and began to comment on our fucking. “I’ll bet you’re enjoying that big cock of his, aren’t you, Miss Patty?” one mocked. “That greedy maw of yours loves a fat cock, doesn’t it, Miss Patty?” jibed another. Nella ignored them and so did I. I kissed her passionately and kept up a thrusting rhythm that built our passion to a mutual climax and orgasm. As we subsided in each other’s arms, the group dispersed and we were left alone.
“So who are you, and how do I contact you?” I asked. Nella smiled and bit her lip. “You don’t,” she said. “It is forbidden for members to call each other. But think. Do you not know me?” I stared at her, examining her facial features and exquisite body again. They were indeed familiar. “We knew each other years ago at college. I had a boyfriend you knew. He went away on vacation without me. You consoled me.” The light dawned. “Nella!’ I exclaimed. “Ssssh,” she said. “No names. Look me up on the Internet. It was so good seeing you here tonight. I’d like to do it again.”
She kissed me on the lips and was gone. The meeting broke up, Aileen and I retrieved our clothes at the house, and we drove home making plans to see Nella and help me live again a love of my youth.