A Pegging For Dessert

This one is called “A Pegging For Dessert.”

I was cleaning up the kitchen after my lovely Wife Karin had made a delicious Swedish meatball dinner for three: the two of us and Her best friend and former lover Joanne, who was visiting and would be staying all week. Karin and Joanne had already retired to the bedroom, and were presumably discussing what I would be made to do to pleasure the both of them that night.

I suppose “made to do” isn’t the appropriate phrase. I am always eager to please Karin in any way She desires, and the same goes for any of Her friends that She chooses to introduce me to. Eleven years ago, on my first date with Karin, She had given me a set of rules for our relationship, and Her being in charge was the first of them. Second was that our relationship always would be an open relationship as She enjoyed multiple partners of both sexes, and third was any of Her friends, or any other woman that She wanted to bring into the relationship, was to be obeyed just as I would obey Karin Herself. My 18-year-old, still-virgin self had wanted to be with much-older Karin so badly, I agreed to everything She wanted, without having ever heard of terms like “FLR” or “polyamory,” although I did know what Karin being “bi” had meant.

My love for Karin, and my desire to please Her in every way possible, has only grown stronger in the 11 years since that first date. To my eyes, She is absolutely beautiful, and many men my age and younger also find Her to be a very attractive older woman. Slender but not quite “petite,” She stands five-foot-four when not wearing heels, and weighs almost exactly 100 pounds, with sparkling blue eyes almost always behind a stylish pair of glasses. Wearing Her hair in a neat bob, She very much looks like the older high school teacher of every straight teenage boy’s dream.

Despite being 64, Karin can believably state that She is between 45 and 48 when She has Her hair dyed dirty-blonde like it was previously. When She is sporting Her truly stunning natural multi-shaded grey hair, She will claim to be between in Her early fifties, eliciting questions about who does Her hair, and how they manage to get it to look so natural. The 35-year age gap between Karin and me frequently shocks others, but feels completely natural and normal to the two of us.

At 58, Joanne is six years younger than Karin. She is slightly taller, and much heavier than my Wife, a “pear” type of BBW with voluptuous hips and a soft round belly. She wears her hair long, dyed a very bright shade of red, and she wears a pair of large glasses with thin golden wire frames.

Karin never allowed me to use Her dishwasher for dishes, cookware, or utensils. She insisted that I wash everything by hand every time. The dishwasher was reserved for cleaning and sanitizing toys only. I had finished washing, drying, and putting away the dishes when I heard Karin call me into the bedroom. Karin and Joanne were both standing by the bed, each wearing a harness with a dildo attached. It was clear that I would be getting pegged tonight.

Karin’s dildo would have been frightening to a man who had never been pegged before. It was about seven and a half inches long, and just under two inches thick at its base. For me, it would be a very pleasurable pegging as I had taken this same dildo from Karin dozens of times in the past.

Joanne’s dildo, on the other hand, was frighteningly large to me. It was thicker than the barrel of a baseball bat at its base, probably three to three and a half inches thick, and well over a foot in length. Even the head was a bit over two inches thick, thicker than the base of Karin’s dildo! I’m sure I could take the head and first few inches with sufficient lube, but there was just no way that whole thing could go into me. It swung between Joanne’s ample legs like the pendulum of a long-case clock, the head reaching a couple inches below her knees.

Karin pointed at the floor in front of where She stood, a silent instruction for me to kneel before Her. I knelt before my Wife, which placed Her lavender dildo right in front of my face. Karin didn’t have to say a word; I knew what She wanted me to do. I opened my mouth, taking in Her dildo. It tasted like a woman, but a woman who was not my Wife. Enjoying the taste, I continued to go down on Karin’s dildo.

“You’re tasting Joanne right now,” Karin said. “We were playing around a bit while you were doing the dishes, and Joanne had used that one for a few minutes.”

I continued to bob my head on Karin’s dildo until She had decided I was finished, pulling my hair to hold my head still as She withdrew it from my mouth. To my relief, Joanne didn’t try to put her dildo into my mouth.

“Miss Joanne, you taste wonderful,” I said to the larger of the two ladies. Early on in the relationship with Karin, it had been determined that I would address any of Her friends with “Miss” and their first name, regardless of age. Even a 21-year-old college girl, I would have to address in this way. With Karin Herself, it was “Miss Karin,” “Ma’am,” or sometimes “Aunt Karin.” She said it reminded me that She and/or Her friends were always in charge and that it also ensured I showed proper respect toward the women.

“Thank you, Mickey,” Joanne replied. She had been friends with Karin for nearly 40 years. Like Karin, Joanne had also been a teacher; they had met while working at the same school and had become very close friends. Close enough friends that they had shared previous boyfriends and their first husbands with each other. But Karin and Joanne hadn’t seen each other in person for just about 20 years, however, when there had been a tiff over Joanne sleeping with Karin’s first husband by herself, without Karin being there.

“Clean yourself up for your pegging, and get a shower,” Karin instructed me. I replied with a “Yes, Ma’am” and went into the bathroom, closing the door behind me. I knew Joanne wouldn’t want to see me giving myself an enema. Karin insisted on them before any anal play. Karin had a nurse friend of Hers, Miss B, teach me how to clean myself thoroughly on my second date prior to Karin pegging me for the first time. I had since given myself an enema well over a hundred times, and that it was not a turn-on to watch someone doing it.

After I had completed my enema, I showered and shaved my face, even though I didn’t think I needed to, having already shaved that morning. I wanted to make sure I was as presentable as possible for Miss Joanne, and I thought that if I took long enough getting ready, Karin and Joanne might start playing with each other, and possibly allow me to watch them finish before it was time for me to be pegged.

I emerged from the bathroom, fresh and clean, and smelled cinnamon. She and Joanne had been passing a slender red vape pen back and forth while I was getting ready, now I regretted taking so long to get clean.

Joanne was holding a pair of leather cuffs with a roughly yard-long steel chain between them. She motioned me to get onto the bed and lie on my back, which I did. Putting the long chain around one of the bars of the headboard, Joanne tightly fastened the cuffs to each of my wrists and to each other, binding my wrists together, but allowing me to be positioned nearer to the foot of the bed. She grabbed both ends of the chain just above my fastened wrists and gave a strong two-handed yank to ensure it was secure.

“That headboard was built from solid oak and wrought iron, and it’s bolted into the wall studs. Trust me, Joanne, he’s not going anywhere,” Karin said, “He’s flexible, but there’s no way he’ll be able to touch himself in those cuffs, either. Joanne, start whenever you’re ready.”

I had been watching Karin, but Joanne began to kiss me, her mass of red hair leaving me unable to see what my Wife was doing. I could taste the cinnamon flavor on Joanne’s lips and tongue, it was very pleasant. I felt Joanne’s hand slowly stroking my cock, just enough for it to stand at attention, then she stopped touching it. With her lips still pressed against mine, and her tongue still in my mouth, Joanne allowed my cock to soften, then began to stroke it again, even slower this time, and again ceased touching it once it became erect.

I felt Karin squirt some lube into my ass, before slowly sliding the dildo into me. There was far more pressure on my prostate than I expected, and I felt more stretching of my ass the deeper She went. Once the dildo was in all the way, Joanne stopped kissing me. With her thick red hair out of the way, I was able to see Karin, and a naughty smile on Her beautiful face told me She was up to something. She held a small wired remote control in Her hand and pushed the button, and the vibrator She had tucked into Her harness came to life, bringing a lustful look of pleasure to Her beautiful face.

Karin had not only swapped out the dildo She had been wearing with Her largest one, but She had also put one of Her bullet vibrators inside the harness. I could feel the vibrations through the entire ten inch length of the dildo shaft. It made me fully erect even more rapidly than Joanne’s kissing and gentle stroking of my cock had done.

The strong vibrations of the vibrator brought Karin to orgasm quickly accompanied by Her moans of pleasure, and a look of satisfaction on Her face. She turned the vibrator off, withdrew all but the head of the dildo and re-lubricated it. She then began to actually fuck me with the dildo, full-length slow strokes, with just a slight snap of Her hips at the end of each stroke, making me grunt softly with every snap.

Being restrained and looking up at my beautiful Wife as She pegged me in front of Her friend was a tremendous source of excitement for me. I was leaking pre-cum and my cock was quivering. “You are not permitted to cum yet,” Karin admonished me. I knew it was hopeless, that She was going to make me cum despite my best efforts to hold back, and I would have to endure a punishment that She and Joanne had probably already decided on back when I was washing the dishes.

Karin turned the vibrator back on and pushed Her dildo its full length into my ass and began to grind, putting extra pressure on Her clit until She came again, more forcefully this time than the first, letting out a beautiful half-scream, half-moan of ecstasy in the process. She arched Her back and raised Her head toward the ceiling as She came, as a wave of wonderful satisfaction washed over Her.

Karin turned Her vibrator off. More pre-cum had leaked from my throbbing, quaking erection. “Do not cum until I tell you to,” Karin ordered.

“No, Ma’am, I won’t cum,” I replied, grunting out the words. I knew I was most likely lying to Her, as I felt like I would explode at any second.

Karin added a bit more lube and resumed the long, slow strokes of Her dildo in and out of my ass. I felt the urge to ejaculate and fought it as hard as I could, tightening my pelvic muscles to stop the inevitable spurt. Karin, so in tune with my body, was able to feel this as resistance to Her penetration, and turned the vibrator back on, making it harder for me to not cum.

I saw Karin wink at Joanne, who at some point had squeezed a bit of lube into her hand. Joanne began to stroke my cock slowly. I tightened my pelvic muscles so hard, desperately wanting to not release my load all over myself.

“Husband, you do not have my permission to cum yet!” Karin ordered.

But I was receiving stimulation from Karin’s dildo, Karin’s vibrator, Joanne’s hand, as well as my own feelings of love and lust for these two amazing women, and I could not hold back any longer. The first squirt was so powerful, my load landed on my face, in my hair, and above my head on the pillow and the bed. The second flew and hit my chest, the third pumped out onto my stomach, the fourth simply oozed out onto Joanne’s hand.

Karin plunged the dildo its full length into my ass again, grinding Her way to a third orgasm, moaning beautifully, a deep, erotic sound of absolute pleasure. I’m sure there was an equally beautiful look on Her face but I had been looking at all the cum She and Joanne had worked out of me.

“I’m sorry, Miss Karin. I held out as long as I could,” I was genuinely sorry that I had disappointed Her, regardless of any punishment that would ensue.

Joanne was inserting her sticky fingers into herself, depositing some of the semen from my huge load into her vagina. “Not a drop of your cream will be wasted,” she said, taking a small coffee spoon off the nightstand and scooping a small amount of my jizz from my body onto the spoon.

Karin’s dildo was still fully inside of my ass. She pulled out so only the head remained, then slammed it into me forcefully. I grunted in a mix of pleasure and pain, but more importantly, more semen oozed out of my softening cock. Karin repeated Her forceful full-length thrusts until nothing more was left to trickle out, then added three more hard thrusts for good measure before turning the vibrator off and fully withdrawing the dildo.

Joanne held the spoon to my mouth, making me eat my own cream. She took small amounts at a time and spoon-fed me slowly, deliberately making the process take several minutes. Joanne seemed to relish making me eat my own cum from that spoon.

I didn’t utter a word of protest, and obediently ate my cum as Joanne fed it to me. Karin had trained me to perform cum cleanup since our first date, so it was something I was used to doing. I offered to go down on Joanne and eat the cum that she had placed into herself as well, but she declined my offer and said that she had wanted to keep that for herself. For the last spoonful, Joanne gave the spook to Karin.

“My husband loves eating his own dessert,” Karin said to Joanne, as She fed me the last of my cum, before saying to me “You will serve as Joanne’s husband the rest of the time she is here. She will administer your punishment tomorrow.”

“Yes, Ma’am,” I replied to Karin, before turning to Joanne. “Miss Joanne, I am yours,” I said to Her, acknowledging that I was to serve Her.

Joanne had no additional duties for me to perform that night. I was relived, and yet somewhat disappointed, that I wouldn’t be taking a pegging from Joanne that night. Joanne released me from my cuffs, the ladies removed their harnesses, and the three of us climbed into bed, with me in the middle. Karin and Joanne passed Karin’s vape pen back and forth for a few hits before we all fell asleep for the night.

The next day, I had to clean the entire house under Joanne’s supervision, while wearing a French maid outfit and a large butt plug. It took all day to get the work done, as She was constantly groping my cock, slapping me on the ass, and making me kiss Her. It reminded me of the harassment that secretaries had to endure in the 1960s – at least what I had seen on TV.

Joanne even made me go down on Her on the kitchen floor as Karin watched, which meant I had to clean it a second time.