The Pegging Date

The Pegging Date

Based on a real encounter. The names have been changed.

My amazing Wife Karin, a retired teacher, loves to peg. Not coincidentally, I love being pegged. Karin also enjoys having multiple partners in Her sex life. So I was surprised a date like this hadn’t happened before.

Recently an opportunity came up for a date with another couple that had some specific desires. The couple, Lucy and Brett, had a profile stating what they were looking for and Karin had contacted them. Lucy, who was 32, wanted an older woman with pegging experience to peg her 21-year-old boyfriend for the first time while also teaching her how to peg. Lucy had wanted to peg Brett for some time, but had no pegging experience of her own. Lucy thought that introducing pegging would take her relationship with Brett to another level, and Brett was OK with trying it out.

The day where we were to meet Lucy and Brett at the hotel, Karin had told me to make sure I was clean down below as She might need to use me when teaching Lucy. After I had cleaned and showered, Karin locked my cock in the metal chastity cage and placed the key around Her neck.

Before leaving for the hotel, Karin had me pack a large assortment of Her dildos, harnesses, lube and other items including a few pairs of restraints. Karin wore a black dress with black stockings and moderate heels, and had me dress more casually, loose-fitting black jeans and a plain black T-shirt.

We arrived at the hotel and went to the room we had reserved; the other couple had arrived shortly before us. Lucy invited us inside. Lucy was a petite woman, just over five feet tall and maybe a hundred pounds, give or take. She had brown eyes and short, dark brown hair and appeared generally to be of Latina descent. Her younger blue-eyed boyfriend towered over everyone in the room, standing at least six feet four. His shoulders were wide and his waist lean, a classic athletic build. His light brown beard was neatly trimmed, but his hair grew wild, beyond shoulder length, like a hockey or soccer player might wear it.

Lucy told Brett to strip naked and remain quiet; he complied without a word. She then explained in detail what she wanted Karin to do to her boyfriend. Brett remained silent the entire time as Lucy described her plans for him. It sounded like a wonderful time to me, but Brett clearly looked nervous as Lucy spoke.

Karin had me strip naked first, revealing my cage to Brett, then showed him the key around Her neck before opening Her bag of goodies. “You can relax, Brett. Mick won’t be fucking anyone tonight. He’s not into guys and I he doesn’t have my permission to touch Lucy either,” Karin assured him as She handed Lucy a pair of leather restraints for his hands.

“Lie down on the bed, on your back, baby,” Lucy told Brett. He did as instructed, and allowed Lucy to cuff his hands. The headboard had no bars to attach the restraints, so Lucy attached them to the legs of the bed frame.

While Lucy was restraining Brett, I helped Karin unzip Her dress and put on Her black leather harness, pulling the straps snug behind Her. Seeing Karin wearing a strap-on harness was always guaranteed to get me aroused, and my cock swelled inside its cage, uncomfortable but not painful.

Karin removed a red translucent jelly dildo from Her bag. It was one of the larger toys in there, ten inches in length and two inches in diameter. My cage became even tighter as I imagined Karin working my ass over with that dildo, although She had used bigger toys on me before.

Brett didn’t utter a word, but his eyes said it all.

“Brett, baby, don’t you want me to use my favorite toy on you?” Karin asked him, already knowing what his answer would be. Brett still didn’t say a word, but shook his head instead.

“Baby, you can speak now, I just wanted you quiet while I talked to Karin,” Lucy said. She was fitting a strap behind his head and around both ankles to hold his legs in the air. Not having to support Brett’s legs would make pegging him much easier for Karin.

“Please no, Miss Karin, nothing that big,” Brett replied, politely, shaking his head again. His voice was far softer than I expected.

Karin took three small toys from Her bag next. The first one was hot pink, completely smooth, and about five inches long. The second was blue, with a defined head and ribbed shaft, slightly thicker and about six inches long. The third was purple, and other than the color, looked like a real cock, with a realistic head and veined texture. It was a bit over an inch thick, and about half an inch longer than the blue one. Just like the red monster Karin had showed Brett first, they all had a flared base so they could be used with the harness She was wearing.

Karin showed Brett the smooth pink dildo. “This is what I’m going to use in you first. It’s five inches long and not even a full inch thick. I promise it won’t hurt a bit,” Karin said.

Next, Karin showed him the blue one. “The head on this is wider than the shaft, just like you. It’s six inches long and the head is an inch thick. I won’t use this until you’re used to the first one,” Karin said.

Finally, Karin showed him the purple dildo. “The head on this is an inch and a quarter, the shaft is an inch thick, and it’s six-and-a-half inches long. I’ll only use this on you if you’re comfortable with the blue dildo,” Karin told Brett.

Lucy started recording on her phone. “Hi, I’m Lucy. This is my 21-year-old BOYfriend Brett. This is Miss Karin. This is Miss Karin’s husband,” Lucy said, moving the phone along with her introductions to include her own face, bound and helpless Brett, my Wife from the shoulders down, and my caged cock in the video. Lucy had agreed neither Karin’s face nor mine would appear in the video.

Lucy turned the phone camera back onto her face. “Miss Karin is going to make a man out of my BOYfriend, pegging him for the first time tonight, and you’ll get to see it all!” Lucy said excitedly.

Lucy turned the camera back toward my Wife, aiming low to keep Her face out of the video. “Miss Karin, tell us about your dildo collection.” Lucy held the camera to the bag, which was on a chair, out of Brett’s view.

“This pink one, it’s small and smooth, perfect for a beginner like your boyfriend,” Karin replied, holding the small pink dildo for the camera. She continued, “The blue one has a ribbed shaft, a slightly enlarged head, and is an inch longer overall,” and held the blue dildo for the camera.

Karin returned the first two dildos into Her bag and continued, “This purple dildo is more realistic in detail and shape than the first two. It’s a half-inch longer than the blue one, six-and-a-half overall, and the head is about an inch and a quarter thick.” Karin was holding both the purple dildo and a second hot pink dildo that matched the color of the smallest one, but was just slightly larger than the purple one as She spoke. Karin winked at Lucy and I immediately knew what She had in mind.

“This red one, it’s ten inches long and two inches thick. My husband can take this easily,” Karin said, showing the red dildo to the camera. “This one, I first used on my husband to consummate our marriage. Eleven inches long and two-and-a-half inches thick, this is what I use to remind him that he belongs to me,” Karin said, as She held the colossal clear jelly dildo up for the camera.

Karin returned the dildos to the bag. Instead of taking out the smallest one, She grabbed the larger hot pink dildo, put it through the O-ring on Her harness and snapped the fasteners holding the ring down. She removed an applicator and a bottle of lube from the bag, then filled the applicator and lubricated the dildo heavily after it was secured to Her harness.

“Before you start on Brett, tell us a bit about yourself, Miss Karin,” Lucy said, the camera directed at Karin’s glistening wet, realistic, hot pink dildo.

“I’m a retired teacher, 65 years old. My husband is only 30 and very submissive, we’ve been married five years and have been together since he turned 18,” Karin said.

“You’re 65? With a body like that, I thought you were in your forties!” Lucy exclaimed in disbelief, zooming in on Karin’s slender waist, slowly moving the camera up and down, showing off Karin’s entire body from Her bare shoulders down to the high heeled shoes on Her feet.

“A lot of cardio, good genes and I never leave the house during the day without sunscreen. Even in the winter,” Karin explained.

“Did you hear that, baby? You’re going to get pegged by a 65-year-old woman!” Lucy teased her boyfriend, “She’s more than triple your age!”

“Cool,” Brett said, unfazed.

“Are you ready to get fucked by a woman?” Karin asked Brett.

“Yes, Miss Karin,” he replied.

“You can still chicken out now if you want to, baby,” Lucy said to Brett as Karin inserted the applicator into Brett and squeezed out its contents into his ass.

“No, Ma’am. I want to experience this,” was Brett’s reply to his girlfriend.

Karin approached the bed where Brett was tied up. Brett didn’t know that Karin had switched dildos, the hot pink color was all he had noticed. Lucy had climbed onto the bed, kneeling over Brett, her phone camera directly above his face to capture his expression upon Karin’s initial penetration.

Karin knelt on the bed between Brett’s legs, which were held in the air by the restraints. She placed the head of the pink dildo against his sphincter, cupping Her beautifully manicured hands underneath Brett’s ass cheeks. Karin bent down slightly and gazed into Brett’s eyes. Lucy moved the phone camera slightly to keep Karin’s face out of the shot.

“Look into my eyes, Brett,” Karin said. “Are you ready for me?”

“Yes, Miss Karin,” Brett replied, looking into Karin’s eyes and preparing himself.

With Her hands under his butt cheeks, Karin pulled Herself into Brett. Her dildo slid in a little more than halfway. Brett’s mouth opened with a soft exhale and a moan of pleasure. Karin didn’t attempt to thrust deeper right away, nor did She withdraw at all.

“That was beautiful, Brett,” Lucy said, keeping the camera focused on Brett’s face.

Karin allowed Brett’s ass some time to accommodate the dildo, for about a minute, She didn’t move at all, just waiting for the right moment to continue.

Digging Her fingernails into Brett’s tight butt cheeks, Karin steadily and gently penetrated Brett with the full length of Her hot pink dildo. Brett closed his eyes and let out another soft pleasurable moan.

“Brett, baby, you are enjoying this too much,” Lucy stated, smiling at him, then nodding her head to Karin.

Karin began to slowly work Her dildo in and out of Brett’s tight rear. Lucy kept recording Brett’s face as Karin increased the speed of Her thrusts into his ass. Brett’s moaning grew louder as Karin had Her way with him.

Feeling that his ass had loosened up enough, Karin began using Her wonderfully toned hips to snap-thrust Her dildo into Brett’s butt. His moans of pleasure became grunts in time with Karin’s forceful thrusts.

“Brett, baby, you know the safe word if it’s too much,” Lucy said to him, still keeping the camera aimed at his face.

“Please don’t stop, Miss Karin,” Brett said, “I love this. I can’t wait for Lucy to do this to me.”

Lucy handed her phone to me. I continued to record, alternating between capturing Brett’s facial expressions and Karin expertly working his ass with Her hot pink dildo. Karin continued to fuck Brett for several more minutes. She occasionally changed between a slow and steady pace and a more vigorous series of thrusts several times.

Lucy watched, enjoying as her boyfriend took it from Karin the entire time. Brett’s facial expression and the sounds he made changed in concert with Karin’s pace, and I managed to get everything on video, before Lucy decided it was time to allow Brett to get off.

Lucy took Brett’s semi-erect cock into her lubed hand and began to stroke it to a full erection, nearly nine inches in length and about two inches thick – well larger than the dildo Karin was using on him. Karin continued to expertly work Brett’s ass over as She stared at his cock.

I backed up from the bed just a bit so I could capture all of the action in frame: Karin’s pegging, Lucy’s stroking, and the expressions of lust on Brett’s face. Brett’s moans became more intense as Lucy stroked him in conjunction with Karin’s pegging. Both ladies knew Brett was close to orgasm, so Karin shortened Her stroke length and increased the speed of Her thrusting, while Lucy jerked Brett faster and used her thumbnail to stimulate the underside of his glans.

Brett’s moan turned into a scream as several ropes of semen burst from his cock, landing on his chest. Lucy continued to milk him until her stroking led to no more semen being produced. Karin continued to work Her dildo gently into Brett for a few long, slow thrusts after Lucy had stopped her stroking of Brett’s dick, which was now no longer fully erect.

Karin slowly withdrew the hot pink dildo from Brett’s ass. It came out just as clean as it had gone in.

I continued recording with Lucy’s phone, not knowing if Karin and Lucy had any post-pegging plans for Brett. Lucy was retrieving something from the nightstand so I pointed the phone at her to get whatever was about to happen next on video.

“Brett, baby, how did it feel to be fucked by a woman?” Lucy asked.

“It felt amazing,” Brett said, “Thank you, Miss Karin.”

“So you want this again sometime, baby? With me fucking you this time?” Lucy asked.

“Yes Ma’am, please,” Brett replied.

“Show me how much you want it,” Lucy said. Karin moved to straddle Brett’s face, Her hot pink dildo directly above his mouth.

Brett, still restrained with his legs in the air, opened his mouth and moved his head up slightly, accepting about half the dildo into his mouth. Karin lowered Herself over Brett, allowing him to decide how much of Her dildo to take. Brett eventually took about five of the dildo’s seven inches into his mouth, sucking it until Karin withdrew it from his mouth.

Lucy showed Brett the spoon she had taken from the nightstand. “You’ll like this taste better,” she said, and scooped up a bit of the sticky cream from Brett’s smooth-shaven chest. She held the spoon near his face and he opened his mouth wide, ready to accept his own cum into his mouth. Lucy didn’t put it into his mouth yet, instead opting to gather an entire spoonful to feed him.

Lucy put the spoon into Brett’s mouth and he took the load into his mouth and swallowed. There was still semen left on his chest, so Lucy gathered up a second spoonful and fed it to him again as I recorded the entire sequence with her phone.

“Brett, baby, tell me which tasted better, your ass or your cum?” Lucy asked Brett.

“My cum, Ma’am, definitely,” Brett answered.

“Tell me what you want, baby,” Lucy said.

“I want my girlfriend to peg me and spoon-feed me my cum, Ma’am,” Brett replied.

“Miss Karin used a bigger dildo than you expected, did you enjoy that?” Lucy asked.

“OMG, Yes, Ma’am, it was perfect,” Brett said.

“Brett, baby, you’re no longer my BOYfriend,” Lucy said. Brett briefly had a puzzled look on his face. “You’re no longer a pegging virgin. You’re a man now. You’re MY man, you belong to me,” Lucy said, grabbing his cock tightly.

“Yes, Ma’am. I belong to Lucy,” Brett agreed.

Lucy motioned for me to stop the video and I did. She and Karin unfastened the restraints that were holding Brett to the bed.

It would be Brett’s turn to watch his girlfriend fuck me. Karin showed Lucy how to wear the harness and attach the big red ten-inch dildo. I laid down on my back on the bed and allowed Karin to restrain me in the same way Brett had been restrained. Karin did not remove the cage from my cock, however.

Lucy flaunted her new red cock in front of Brett. “Brett, baby, I’m hung even better than you!” she exclaimed. He watched in amazement I easily took the full length of Karin’s favorite dildo, attached to his girlfriend, inside of me.

“Brett, I peg my husband at least once a week with that dildo, sometimes more often,” Karin said. “Eventually, if Lucy has her way, you’ll be able to take it just as easily.”

“Lucy always gets her way, Miss Karin,” Brett replied.

Lucy continued to peg me while restrained for several minutes. My cock, wanting to grow erect, pressed outward against my cage in all directions. Karin gave Lucy tips and pointers at times as Lucy pegged me, sometimes slowly, sometimes with wild abandon. After about ten or fifteen minutes, Karin had Lucy reposition me, this time on all fours on the bed, hands still restrained, with Lucy behind me.

Another several minutes of pegging, and another position, rinse and repeat, all at Karin’s instruction. Karin had Lucy peg me in all sorts of positions, both restrained and unrestrained, all while Brett watched. But Karin and I both believe the woman should always be in control during pegging sessions, so I was never just allowed to ride on Lucy’s dildo.

Karin then had Lucy return me to the original position in which Brett and I were pegged: on my back, hands restrained, legs held up in the air by the ankle strap. Finally, Karin unlocked and removed my cage. My cock had grooves in it from the cage’s metal bars after straining inside of it for what seemed like an hour. Finally free, my erection immediate grew to its full size as Karin began to masturbate me, almost exactly as Lucy had done earlier with Brett.

Except Karin didn’t stroke me to a full orgasm. She brought me to the edge, then took Her hand away at just the right time, ruining my orgasm. “You don’t get to cum for Lucy, you belong to me,” Karin said, lightly slapping my balls with each of Her last four words for emphasis.

“Yes, Ma’am. I belong to Miss Karin,” I said.

Two more ruined orgasms later, Karin had Lucy straddle my face and insert the big red dildo into my mouth. I sucked as much of the dildo as I could take into my mouth, about half of its ten inches.

Karin scooped up the cum that had dribbled from my cock during my ruined orgasms into another spoon. Unlike the spoon that Lucy had spoon-fed Brett his own seed with, this one was large enough to hold all of my messy fluid at once.

“Thank you, Miss Karin, for the tasty dessert,” I said, before opening my mouth to accept the spoonful of my baby batter. I didn’t swallow immediately, holding the cream in my mouth for Karin and Lucy to observe first. After about ten seconds, Karin told me to swallow it.

Karin let me free from my restraints and re-fitted my cage, then told me close the bathroom door and take a long shower, then to get dressed and remain in the bathroom until Karin knocked on the door to tell me I could come out. Once I had finished my shower and the water had stopped running, I was able to hear the sound of a fun time – some laughing at times and moans of pleasure from all three of them.

Karin finally allowed me to emerge from the bathroom – which had amounted to well over an hour of alone time. I could tell from the smile and glow on Her face that She had gotten laid, and that Brett, or Lucy, or both of them, had been good in bed.

I held Karin tight and kissed Her passionately. I didn’t say anything at all about what She might have been doing in my absence. I was happy that Karin had enjoyed Herself, and was pretty sure She would tell me all about it at some point in the future, probably while pegging me again.

Watching Karin teach Lucy how to peg while She took Brett’s virginity was an amazing experience. So was being Lucy’s first – Brett was definitely a lucky man.

I would love it if Karin started teaching other women about pegging on a more regular basis.