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.