Separation Trial (Trial Separation)

We had been married about three years, when my wife and I decided that it just wasn't working. We agreed to a "Trial Separation" with the proviso that we could see others if we wished to, but somehow I didn't think that Gayle would do anything about it in a physical sense. I had always been a gentle lover, and she seemed like the quintessential "ice queen." I just couldn't figure her out. I had been raised to be nice to women, and I certainly tried.

After living on my own apartment for about a couple of months, I had went out one night to drown my sorrows, and ran into a mutual friend of ours. Morgan was the antithesis of Gayle. She always seemed to be riding right on the edge, unlike my very conservative wife. She hadn't changed much, bright red hair, black lipstick, and a leather outfit, also in black, that made my eyes pop out. We got to talking, not having seen each other for awhile, and before you could spell "forlorn," I was crying in my beer about Gayle to her. I must have done something other than just cry in my beer, because I woke up next morning in Morgan's bed with an ache in my chest and the head of my dick. These were swiftly overcome by the splitting headache I had. Morgan came into the room, without a stitch on carrying coffee, rolls, and a large glass of orange juice. "Oh look! It's alive!" she said. I don't think I agreed with her, and certainly wasn't feeling as cheery as she was. I took a sip of blazing hot coffee, and the burn on my tongue damned near made me forget about my head. "What the hell happened last night?" Was the first thing out of my mouth after I had shouted "Fuck" at the coffee.

She gleefully filled me in on the details. After about an hour or two in the bar, she had dragged me out into the cool night air. We had been discussing how conservative I was, and I was determined to show her that I wasn't. On a dare she had taken me to a Piercing/Tattoo parlor, and that was the source of my chest and cock pains. I looked down, and sure enough, there was a ring in each of my nipples, and what I later learned was called a "Prince Albert" in the head of my cock. "Jesus!" I cried, "how drunk was I?" Morgan said that I had passed out during the "PA" and the guy in the shop and her had to drag me out to a cab, and the cabby was kind enough to help her get me into her apartment, which was fortunately on the ground floor. I said I wanted them out "now," but she advised against it, saying that I needed to heal a bit first or that I could get a bitch of an infection. I noticed the piercings in her nipples and navel, and figured she might know what she was talking about. I reluctantly agreed, and she clapped her hands, and said, "That's it cupcake, let Auntie Morgan take care of it for you." (Cupcake?)

She certainly did, and over the next few weeks, I spent more and more time at her place. Unnoticed to me, she soon had me on the road to perdition. She discovered that I liked to eat pussy, and that was my penalty for having her take care of the piercings. I think she may have overdone it a bit, but on the other hand, the piercings quit aching in about three weeks, so I couldn't complain. I was taking a fairly passive role in the relationship, and when she said it made her hot to see a man in panties, I didn't argue, and besides, they felt real good against my rapidly healing cock. She also took to having me wear a satin tank top in lieu of a T-shirt, and the fabric glided over my nipples so that they felt good too.

About six weeks since my downfall, I was in thrall of her. And when she pronounced my "PA" all healed, she celebrated by giving me the blowjob of my life, accompanied by a couple of fingers, massaging my prostate. It may not have been love, but it was the best cum I had ever had. I had been storing it up for awhile now, and I think it all came out in one fell swoop. I passed out it was so intense. When I came to, it was confession time on her part. She gushed about how much I had cum, and confessed that me in panties had made all of her repressed lesbian feelings come out. I was now free to have the rings removed, but she really wanted to make me into her lesbian lover. I had grown used to the feel, if not the sight of the rings in my flesh, and I had to admit, they more or less kept me aroused most of the time. I was curious where this would lead, and so far, she had not lied to me, so I acquiesced.

One thing led to another, and soon Morgan had made my ass the center of my sexuality. I certainly was not a "tight ass" anymore, having been prodded by a variety of instruments, stretched by an ever-increasing diameter set of butt plugs, and royally fucked by Morgan's strap-on. Worst of all, I was not running for cover, I was enjoying myself, perhaps for the first time since reaching my maturity. Still, she thought that I needed more intense training, and when my vacation came up, I found that she had me enrolled in a so-called "Sissy Academy." It started on the Friday beginning my vacation with a trip to a salon owned by a friend of hers. Morgan had been dissatisfied with me wearing wigs, and my hair had begun to grow longer, so why not have it styled in a unisex manner? The session started with laser removal of all of my hair below my hairline. Erica, (Morgan's friend) took care of that and more, giving me a makeover that astonished me when I got my first look. I really did look feminine! She had lightened up my color a bit so that it even approached the color of Gayle's hair. (It seemed an eternity since Gayle and I had parted, and worst of all, I was still in love with her.) I was so taken aback, that I almost recognized her in my reflection! After that, while I was still in shock, she bundled me off to "The Academy."

The Academy was a bit more than I expected, first the Maitresse insisted that I am tightly corseted, and I was required to wear high heels. That was an adjustment. I could hardly breathe, and I tottered around on heels that started out at 5 inches, and progressively increased. My figure and my legs looked sensational though, and I thought how pleased Morgan would be. I was also introduced to varying degrees of bondage, to enhance my "femininity," but was probably more to keep me from loosening my stays and unbuckling the ankle straps from my heels. When I was required to be anywhere, I was led via a light chain clipped to my "PA." The first couple of times this happened, I was so embarrassed I could've died, but I learned to enjoy this also. I was instructed in hair care, makeup, putting on stockings, how to walk, sit, and in general how to "pass" as a woman. This seemed a bit more that would be required for the relationship that Morgan and I had, but after all, she had enrolled me.

The first weekend at the Academy, I was loaned out to a dominant woman who sold erotic toys. I was the "demonstration model," and all manner of whips, crops, plugs, nipple clips, gags, and penis restraints were demonstrated on me, while I was bound helplessly with my arms hung from a chain from the 10 foot ceiling. Two women were so taken with me that they offered to buy me, but settled on seeing me serve their slaves, orally and anally. The last one made me cum and they were absolutely delighted by this outcome. I had tasted my first cock, and had been fucked like a woman by a man.

The next week was spent fitting me with higher heels, and tighter lacing, and introducing me to armbinders. Talk about helpless. Try walking when you can't breathe, your feet are crying out from the position they are forced into, and unable to balance properly on the stilts, while your arms are forced together behind your back. This "woman" business was not at all easy. During this week I did get a bit of relief, due to the daily fucking, and milking I was subjected to. I acquired a taste for cum, being required to lick up and swallow all that I spent, sometimes being spoon-fed the stuff. I was on a vegetarian diet, so it actually tasted kinda sweet. One of the instructors thought it was amusing to see me lick and suck my ejaculate out of a "cocktail" glass. This was all to prepare me for my graduation.

Saturday night was the Academy graduation ceremony. All day I was carefully prepared, no hair was allowed below my eyebrows. I was subjected to another session with the laser removal process, my hair was prepared, makeup added, an enema administered (twice), and I was dressed. Dressing took quite a long time, due to the fact that I fainted while being laced into the corset, and time was wasted reviving me. It was lovely though, starting just below my pierced nipples, cut high on the hips so that I could at least sit, eight suspender straps, holding up my perfectly aligned white stockings. It was a vision in white satin, heavily boned, with a locking strap at the top, bottom, and at the waist. There were rings sewn in on either side right above my hips, and my wrists were placed in satin covered matching cuffs, and clipped to these rings. Coming up from the center in the front was another strap, which led to a satin covered collar with four rings, one on each side and one in front and back. The collar was also locked. My nipples were darkened with rouge, and larger gauge rings replaced the ones I was wearing. The Prince Albert ring was also replaced, and all three combined to stretch my appendages and cause them to throb anew. I was fitted with locking ankle boots, and a short (12 inch) chain was clipped to the "D" rings on the inside of my ankles. One further enhancement was added.

The blond instructor brought out a metal fitting that looked like three rings clipped together, only, unlike a standard cock restraint, these were adjustable. She placed the largest ring around my cock and balls, the next size around my balls, and the smallest at the base of my cock. She proceeded to lick and suck me to a full erection, and then adjusted the diameter of the rings so that they were tight against my skin, causing me to throb. I could feel my heartbeat throughout my scrotum. At the juncture of the cock ring and the scrotum ring, a strap was brought up to the bottom of my corset and locked. A similar strap was fitted to the joint of the scrotum ring, and the ball ring, only this one had a large cock-shaped butt probe attached. It took a lot of lube and some effort on her part, and relaxing on my part, before all 7 inches were shoved home, and the strap locked to the back of my corset. I was now screaming for relief. I was instructed to open my mouth, and a large red ball gag was inserted, and its' straps locked behind my head, stretching my crimson lips around the ball tightly. Little bells were clipped to the ring in the front of the ball gag, to my recently pierced earrings, my nipple rings, and to the PA piercing. One of the instructors commented with a wry grin that I was really now a "Tinkerbelle."

They circled around me, making last minute adjustments, then released my wrists, and laced me into a boned satin armbinder, which clipped to the back of my collar. My elbows were crushed together, and such breasts as I had were forced into prominence. I was judged to be ready, and the light chain lead was clipped to my PA, and I was left to stand for an indeterminate period, when the auburn-haired instructor picked it up, and I was led out of the room through a door.

At first I thought that there was a mirror on the opposite wall, because it appeared that I was being led into the room from the opposite side, this was clearly impossible though, because the bound figure was being led in by a man! I was momentarily confused, and then I noticed that my mirror image had no cock, and was being led in by a chain attached to a ring in her clitoral hood. Her breasts were a cup or so larger than mine, and her thighs glistened above her virginal white stockings. It couldn't be! As we drew nearer to a fitting in the center of the room, I finally recognized Gayle! Her eyes were somewhat glazed, and then they went wide when she figured out who I was.

The fitting in the center of the room consisted of two metal frames opposite each other with holes drilled in approximately 2-inch increments. Centered between them was a double dildo rising on a shaft bolted to the floor. Gayle's armbinder was removed, and two large men lifted her and her ass deposited over one of the dildoes. Slowly they slid her down, using her own weight to slowly impale her on the 2x8-inch monster. Her legs were folded back during this process, and she was left kneeling, impaled. A bar was slid in at an appropriate height, and her elbows were looped over it, and a short strap was used to attach her wrist cuffs together in front. Her ankles were then clipped together. Now it was my turn. The same two men approached me while my instructor busied herself removing the butt plug I was wearing. With little effort, they lifted me like Gayle, and positioned me back to back with her, and slowly the dildo slid into my wrinkled hole. My arms were looped over the bar, outside of Gayle's, and attached by a strap in my front just like hers, my ankles were re-clipped with the 12-inch chain, and we were locked in place. About a dozen people, both men and women began to circle and inspect us. Two of the women were the ones who had treated their slaves to my mouth and ass the previous weekend. Wine was served and cocktail chatter went on while we were left kneeling, impaled, back to back.

A fork banging on a wineglass and the announcement interrupted this by Morgan, whom I had not even seen, that the snack bar was open. With predatory grins, my tormentors from the previous weekend shed the covering from their sex, and had a short discussion about whom wanted which suck slave. The brunette selected me, and the bleached blond positioned herself in front of Gayle. Our gags were removed, and immediately our heads were crushed into sopping cunts. They must have had themselves pretty worked up, because it could not have been 5 minutes before one after the other they exploded against our licking tongues. Next up were two men who promptly fucked our mouths, holding our heads immobile while they slaked their lust on our helpless tonsils. The pattern, continued, women and men alternating in pairs until all had cum. Through excitement or discomfort or both, Gayle and I had wound up rubbing our asses together as we served. Someone commented that we were real "bitches in heat."

The suggestion was made that that condition could be "rectified," to accompanying groans at the pun, and I was released, and taken over to a crotch high bench where a strap was wrapped under my armpits to the bench, and another was used to secure my waist. The side rings of my collar were clipped to the bench, and my wrists were again fastened together under the bench. My ass rested on the very end of the bench, and my legs were allowed to dangle towards the floor. Gayle was brought over then, and I saw what had made her thighs glisten. I obviously was a combination of cum and her own juices, and as she was positioned straddling my head, I got my first taste of semen dripping out of her obviously well fucked pussy. She was bent over, and my stockinged legs brought up under her arms. Her wrists were cuffed together under the bench, preventing me from lowering my legs. A thin strap was looped around each on my thighs, and run through the rings of her collar, fastening her in place with my screaming cock safely ensconced in her very wet mouth. Then a "Fuck the Bitches" roulette was started like before, with the women employing strap-ons and the men using their built in equipment. I licked her, and Gayle showed an amazing new talent for sucking a cock. AS our asses were fucked, my cock was shoved further into he mouth with each thrust, and damned if I know how, I came twice during the ordeal, while Gayle just seemed to be in a constant state of orgasm. We were used for at least an hour or so, then released, and half walked, half carried into another room.

We were stripped, and cleaned off with warm towels, and left in a king-sized bed to sleep our ordeal off. I awoke before Gayle, who was still sleeping soundly, and began to muse about my "Ice Queen." Things certainly have changed. We talked for the rest of the day interrupting ourselves with short bouts of sex, and came to the conclusion that the reason our relationship had failed was we hadn't been honest with each other due to embarrassment about what the other would think. Having been exposed to each other as lusty submissive sluts, that didn't really seem important anymore. Ten years later we are still together. We alternate topping each other, and spend our weekends as bondage sluts to Morgan and her friends.