The Greater Anal Delight

She hugged me close, wet tears on my neck, repeating, "Thank you, thank you, thank you, maybe just the once. I don't know. You really do love me don't you."

I didn't know to what I had just committed but obviously she needed it and I would give it to her. No matter what. The woman who depended on me so much, who loved me despite my own flaws, who surrendered her precious ass to me, that woman deserved no less.

Anna bounced in from work two days later and announced, "I found a candidate to do it for us!" I didn't have a clue about what candidate was going to do what for us. I waited to hear more about whatever got her so happy. "So, John, he's on my floor, so it'll be easy to find a time to ask him. About a year ago I overheard him talking once about not caring who did it to him or who he did it to, even if it was a guy. So I know he's open to it. He's good looking, clean cut...You're good looking and clean cut...Thank you, Baby!!" She hugged me hard. "You said you would do something big for me too. And it's actually going to work out." Gradually I started to realize what she meant.

In a flash, all the important turning points of the last week coalesced in my mind. She had been deeply affected by the two boys' randy game, by her feelings toward Pam. It imprinted it's carnal script upon her. She had given a previously reserved part of herself fully to me. And lastly, we had made some twisted deal unknown to me but which she fully expected me to fulfill.

She had every right I suppose, I got my end of the deal. I owed her this much and now it was time to pay up. The most important, and feared, detail of all was that it was going to include me engaging in gay sex.

At first I felt trapped, manipulated. But she loved me completely with all her body and soul. She proved it just days ago. I had just misunderstood something kind of big. And in that instant I knew I would do it. Not only would I do it, but I would give my all to the love of my life. Who knows, maybe it would fix her.

I managed a half smile. As if I weren't fazed at all. Nonchalantly, "Uh, so he's clean cut? Is he gay?"

She put her hand on my shoulder, "No, Silly. I told you. He's willing to do it 'even if it were a guy' which means he's not gay. In fact, he's married, he has two kids, and you're gonna like him."

I cut her off without meaning to, "Do, do you expect me to like him, you know, hugging and kissing?"

"You're still being silly. You're mine, Baby and you always will be. We're just gonna have a little crazy fun. It's all physical, nothing emotional. It'll turn you on, it'll turn me on...and I'll keep pleasing my love with anything you want."

I knew it wasn't going to make me happy in any way, but I was pretty sure by now it was going to push some of her buttons, buttons that had been deep secrets until very recently. It was hard to believe she'd kept that secret. It seemed just as hard to believe she had revealed it. It also explained a lot about the contradictions in her sexuality. How she could be so inhibited one time and so free another. And I did want more of her ass. I wanted other stuff too.

I answered, "Well, that's a relief (not much I thought), if it's just physical." Images formed in my mind. Images of two guys being physical. Images with me as one of the characters. I didn't like the images one bit. I worried it would hurt if his dick was big so I asked, "Is his penis big?"

"Oh, you boys and your obsession with size! I have no idea how big he is and really, size doesn't matter. It'll be just as fun if he has a small weeny. I'll talk to him soon and let you know if we get lucky."

Then changing the subject, she added, "Baby, I'm sorry, I rushed in here with our great news and I didn't even think to ask about your day. You look like it's been a rough one. So tense. Come relax on the sofa and tell me all about it."

Once seated she asked me about my day then seemed to act on an impulse surprising me by immediately dropping to her knees between my legs and blowing me. She said it was to relax me. It was a wonderful departure from the norm, but even a great BJ couldn't get me to relax. I kept having the images. I replayed the conversations of the last days. I saw all the places where I went wrong. I saw all the times she had told me what she meant. Times that I had missed in my single-minded obsession with her derriere. One more thing occurred to me: I realized I had missed that she intended me to be the "girl" in this little therapy of hers.

For the next two days I hoped he would turn her down. That it would all fall through. But I realized she would just look for another 'candidate'. This situation seemed better than other scenarios I could envision. Alas, my hopes were dashed on Thursday.

Anna came home bouncing again. Anything could explain her happiness but I had an inkling that I knew what it was. She sauntered over with a really sexy look on her face, kissed me hard, and with a conspiratorial wink said, "We got 'im." My heart sunk, then revived. It was going to happen and it was going to be awful. But on the other hand it was going to happen and I could be responsible for making her long time fantasy come true.

I mustered up a smile and lied, "That's great, Honey!" I wondered if this really was just a fantasy of hers, or if maybe it too was an obsession.

"But we're not gonna be able to do it soon" She said with a pouty voice. She ran her finger down the buttons on my shirt stopping when they tickled my balls. "And he's got some conditions of his own too. He wants us to wear matching outfits.

I pictured Tarzan and Jane, then a duo in Roman togas. "You mean like couples costumes on Halloween?"

She laughed tossing her long hair slightly, "I don't think that's what he meant. We'll go shopping and text pictures of ideas while we're waiting for them to get back from vacation. That's why he can't do it this weekend. "We can start at that sleazy little shop you always wanted me to go to." Then grinning she flashed her eyebrows at me, "Maybe we can get something for us while we're there." That did sound nice. I dreamed about the two of us in that store, holding and discussing the purchase of a vibrator, with a main part for her pussy and a prong for her tush.

Saturday she let me choose anything I wanted. I ended up getting her a purple jeweled butt plug. She didn't seem keen on the idea but she kissed me sensuously and told me that if I wanted it then I could have it.

It turns out John had a good sense of humor so texting pics and reading his comical responses gave us some good laughs. Also, if I focused on shopping I could deny the rest. After a few attempts to find suitable clothing John settled on a Japanese School Girl theme.

Anna was stunning (literally I felt stunned) in her white crop-top blouse, and a red pleated skirt. Her raven black hair really worked to accentuate the asian feel. They gave me a similar futanari school girl costume except I had a long aqua wig and coordinating blue scarf and skirt. I kinda hate to admit it, but I got into the spirit of the dress up games a bit. I agreed with Anna that we might want to keep getting costumes for our own fun too. To me that meant her as a slutty nurse and me as a rugged fireman.

When her big day arrived she prepped me for hours before. Shower, shave, enema, even make-up. The person in the mirror was not me. It was a little Japanese girl - and she was cute and alluring. Anna described me as scrumptious. Amazing what can be done with make-up!

Once while she was rummaging around in her closet looking for a concealer I peeked to see what my dick would look like dressed this way and popped a boner, but I willed it away before she caught me.

The dreaded doorbell rang with a foreboding sound. I waited for Anna to get it but she called from the bedroom for me to get it. I watched the futanari girl stand frozen in alarm in the mirror. It chimed again, then a third time. She gave me a partial hug from behind on her way to get it, "It's OK. Don't worry. He's going to like you."

If he didn't like me would he drop it? Could She? I looked closer at the porcelain china-doll face, big smoky eyes, and the C-cup boobs under my own cropped blouse and knew he wouldn't drop it. I was going to get the living daylights fucked out of me, or worse he would want my mouth.

From the other room I heard Anna call out, Baby Girl, it's not John." I started breathing again. Popping her head around the corner she giggled, "It's just this big strong school teacher." She led John into the hallway where they stood, eyes fixed on my delectable form, an object to gratify their wanton intentions.

John put his hand around Anna's waist and told me how hot I looked. I glanced at my reflection again. The girl in the mirror really was enticing and provocative.

Anna removed his hand from her waist and told John that he was my date and she was just here to support me on my first day of school. I felt super relieved that nothing was going to happen between them, even if it further made the point that something was going to happen between him and I.

John was tall and handsome and even through his shirt and tie I could tell he worked out. He extended a hand, "Hi, I'm John, but you can call me Headmaster." I went to shake his hand then remembered not to shake with a firm grip but to put mine out in a more feminine manner.

Grabbing my hand he pulled me in, wrapped his arm around my waist, and stuck his face into my cleavage (like some sophomoric jock) smelling the scented powder Anna had sprinkled on me.

His strong hands roamed up and down my body grabbing and squeezing here and there. It felt wonderful for a big strapping man to like me, and grope me that way. My body hummed its gratitude. I grew just a little weak in the knees. A girl could almost melt in the presence of a man like this.

Anna didn't melt. She was unmoved by him. She deserted me to set up drinks in the living room. I desperately needed a drink.

Once seated she goaded me into thanking John for coming over and for "making my first time so special". My mind was in a fog and in my buzzed and dulled mental state I couldn't place my finger on it but there was something in those words that made me uneasy.

I gulped down two more drinks in rapid succession. John and Anna sipped theirs casually.

John broke the ice, "You've been a ba-ad girl and need to be punished." Anna giggled. He took me by the wrists, twisting them so I fell to my knees between his feet, and placed my hands in his crotch. It was already very excited. I could feel it's power and I knew that any second it would be in my mouth. John was desirous to get started right there. His left hand wrapped around the back of my neck entangled in the blue hairs of my wig while with his right he unzipped.

My dear wife was next to speak, "Oh but Mr. Headmaster, bad girls need spankings." Brilliant! A diversion. I really didn't want to taste it or smell it. These activities seemed too intimate. Spanking would be much better.

She stood up quickly, enthusiastically, grabbing us both by our hands and leading us into the bedroom. When we got there I wanted to stay in character so I tried to think what position would be best for a naughty girl to receive a spanking. I glanced around then realized that the rebellious teen wouldn't submit so easily. With arms crossed in front of my padded bra I complained, saying, "It's not fair. I didn't do anything wrong. She was there too and she's not getting a spanking."

John was unbuttoning his shirt. He ignored my words as he continued getting undressed. Anna got into the role too. She added, "We all know that only you did it and only you deserve to get it." John was down to his underwear only. They were, of course, tighty whities, the kind that I suspected would fuel her fires.

I protested more, "Well I'm not going along with this. I'll tell my Daddy, and he pays your..." It was at this moment that he removed his last vestige of clothing and sat down on the edge of our bed. It stuck up from his groin like some surreal human club. I gawked at it, slack jawed. I had seen photographs of erections before but this was very different. It loomed large, protruding there proudly for us all to see.

I checked on Anna curious to know if she also thought it was unrealistically magnificent. She was looking at it but I saw no indication she was surprised or impressed. Her eyes would linger on it for a few seconds, then moving her gaze to me, would appraise my bum. There was no doubt she was connecting the two.

I had seen her turned on plenty of times before. If I had to name that usual feeling I would call it 'romantic passion'. But that night I saw a new kind of lust on her face. This could more accurately be thought of as sexual hunger. Remembering her story about the party I knew she was right: that day long ago had marked her indelibly and it was coming to its lecherous fruition just now.

I looked back at this manly cock. I saw only primordial strength. The skin of this beastly thick cock had an angry reddish hue unlike my more tanned look. It appeared to be a little moist only in the way real skin can be, very unlike my wife's plastic dildo. Her hand on my back pushed me gently closer. I took the first step of three estimating its size at the same time. I would say it was seven inches compared to my six. So not that much bigger really, except that it was a lot thicker. Also, the mushroom head flared out with sharper defined angles.

As I took the last two steps she began to turn my body at the same time that he took my wrist, also twisting my body into the position they wanted. I was helpless in their coordinated maltreatment of me. I ended up lying prone across his lap. My head was on the corner of the bed and my knees were on the other side of his legs.

He rested his hands on the back of my skirt chuckling, "This is going to hurt you more than it hurts me." Anna snickered once at the joke. Next he lifted my skirt reaching underneath. I felt his fingers prying under the top of my tights then slowly he started to tug them down my smooth legs to mid thigh.

Next he tucked one finger under the seam of my aqua panties running it all along the edge, feeling the crease where my buns met my legs. Then again his fingers pried at the top. Even slower he peeled them down, rolling them as they descended until they stopped at the bottom of my globes.

Again his large hands returned to my butt. I waited for the first blow wondering how badly the sting would hurt, but instead he caressed the two hemispheres. I heard a low humming moan emanating from my lascivious wife.

In the next scene of our little play Anna's hands joined in rubbing my exposed behind. I relaxed a little feeling the beautiful sensation of four hands massaging and pleasuring my butt. I felt one of them behind me open my ass cheeks. A rough finger circled my freshly washed spot causing me to jolt briefly.

After a couple minutes of this, something new happened. A tiny mysterious something was inserted into me. Trying to look back, then around the room, I caught sight of our reflection in the vanity.

I had forgotten how we were dressed so I was surprised at how super hot we three looked. The image in the mirror was of two seductive babes in a threesome with a hunky stud. Again Anna's eye-popping gorgeousness caught me off guard. The slut stretched powerless across the legs of the muscular stud had an ass I wanted to fuck.

But what really surprised me was the strange instrument in Anna's hands. She was holding some large syringe with a flexible rubber tube on the end.

She caught me looking then simply told me it was lube. She depressed the plunger squirting the entire contents into my rectum, filling me with slippery goo. It was cold and sloppy. Anna giggled, "Baby, this is so freakin' fun!" The look on her face was pure glee. It was a contagious glee. If anyone had asked me two weeks ago if I would ever feel happy to be laid across a naked man's lap, getting filled with lube as preparation to a royal fucking, I would have laughed out loud. I guess I'm a such a sucker for my wife's desires. Apparently, even her 'broken' desires.

When she was done injecting me John let go of my cheeks allowing them to spring back together which squeezed out a tiny glob of lube. He jiggled them a bit which he must have enjoyed because I felt his cock lurch up poking my tummy from down there between his legs.

Still watching the shemale being made ready in the mirror I saw my darling lift one leg to yank the pretty jeweled plug from her own butt and offer it to John. I felt some ambivalence since I had thought that was only for us, but this use seemed pretty sexy too. Wasting no time he plunged the warm metal into me with one push. Joyously I let them abuse my helpless backside knowing she craved it.

John wanted us to model for him. I had to remove my tights and panties then she and I, School Girl Twins, locked ourselves arm in arm, and pranced about the room. I was constantly aware of the plug the whole time. He had us lift our skirts and bend over a few times, always commenting on how sexy I looked with the sparkly adornment.

For her part, Anna even flashed her boobs for us, subsequently leaving her titty-boner nipples on full display. Shortly, she suggested it was time for the main event. I had been having fun but with the imminence of being violated the fun drained out of me.

I was led to slaughter and laid upon the bed on a pile of pillows. My smooth ass was high in the air, a gift on a feather pedestal. Anna arranged me to her liking with my legs spread and my skirt flipped up. She knelt beside me stroking my worried limp dick and vulnerable balls with lube that had leaked from me.

My penis was yanked back so it pointed south. As I hardened the angle became painful. Surely this would ruin the view for John, spoiling any illusion he might have that I was fully female. I thought he might object. Instead, John told us he loved the look of a tranny girl's stick since you could always tell when they were turned on.

His words forced me to consider that I was indeed turned on. I loved being used by a man for my wife.

"I'm going to put him in you now. She said. By his sudden intake of air I could tell that she had grasped his tool. She pulled the big cock over to my tiny hole narrating all along. "Here it comes, Babygirl. It's gonna be there in another foot. Aren't you soo excited it's finally happening?" She didn't wait for an answer.

She pulled the plug out. I felt her spread my asshole apart then felt the head of his cock was against my defenseless target. Anna was saying, "It's right there touching you." I hardly needed the commentary since I was very aware of his cockhead pushing against my virgin bunghole.

Her fingers played joyfully all around the place where my exploited butthole joined with his dickhead. Her right hand fingertips touched both his penis and my entrance trying obsessively to meld them together. I heard the squishy noises of her left hand fingers playing among the folds of her pussy. I could smell her arousal. I loved bringing pleasure to my broken wife. "I love you." I told her. "Do it."

Again she pulled my cheeks apart as far as she could. His hands now guided the scary pole into my puckered anus. He pressed into me with one go, stretching my opening with the huge head of his cock. My ass clenched uncontrollably, rhythmically for several contractions. My tightening clasping butthole hurt like a motherfucker. I yelled out, "Stop!. Stop it! Stop it. Ooh, wait. Please just give me a minute. He can do it. I just need a minute."

She stroked my back gently, soothingly. As soon as my ass stopped clenching it stopped hurting. "OK", I said "He can go on." I don't think he ever stopped or cared. He just kept pushing on forcing me to accommodate his girth.