Cuckolds Regret

I looked up into his dark eyes, on my knees, beneath him, getting what I had wanted, no, begged for. But now, my mind was full of nothing but questions and regret. It had all started very innocently three years ago with a simple "R" rated movie. My online streaming account had a section called "things you might like to watch". For the most part, the recommendations were right on. Late one night the app recommended "The Girlfriend Experience". The short description sounded interesting, so I hit play. The story was about a young law student that finds herself slowly falling into sex work. The story was well written and a bit addicting. I found myself binge watching it till all hours of the morning.

Late in the series, the lead actress finds herself acting out a cuckold scene for one of her clients. The scene was erotic and extremely hot. I found myself glued to the scene, hand down my pants, slowly stroking my very rigid cock. I had never seen or even thought about cuckolding prior to that evening, however, the thought of my wife being in her position made my heart race out of my chest. It was just so wrong, so dirty and taboo. That scene had my mind twisted and my cock rock hard, so I jerked off and went to bed.

The next morning, I woke up thinking about that scene. It was like the song that won't leave your head. My wife calls them ear worms. This was a mind worm. My mind wandered the whole day at work. I got nothing done as my mind replayed the scene. When I got home that evening, I popped open my laptop and typed "Cuckold" into the Porn Hub site. Tens of thousands of videos showed up.

Many hours later, I was deep into the morass of online porn on the internet. The first few videos were couples in what looked like threesomes, enjoying themselves. As I clicked through more, they became more intense. Men railing married women while their husbands watched. The first few, the husband looked thrilled. As the night progressed, the husbands began to be verbally abused, sometimes locked in chastity. As I spiraled deeper, things soon became more taboo. White wives fucked by hung Black Bulls after which their husbands were made to clean the lovers cum from her pussy. It was all too much. After hours of jumping from video to video, I jerked off and went to bed.

As I laid next to my gorgeous wife, Pam, my mind raced. How would I feel if she fucked another man? Why did the thought of it make me hard? Would she ever agree to do it? What would happen if she enjoyed it? Although I had just came, my cock was rock hard again. I needed to get these thoughts out of my head. I fell asleep only to have dreams about sex all night. I woke up the next morning totally spent.

Weeks passed and my sick thoughts continued. I finally got the balls to ask my wife if she would ever be interested in fucking another man while I watched. Her reaction was exactly what I expected. It was no, that she loved me and would never cheat on me. She then asked if the thought of it made me horny. I shyly admitted that it did. She laughed and told me I was a sick puppy. She then gave me a sly look and then said, "maybe one day you will get lucky."

I decided to make my own luck. I purchased Pam a dildo. The next time we had sex, I asked her to play with it while I watched. She agreed. My wife laid on the bed and stared into my eyes as she slid the dildo into her tight pussy. My cock had never been harder. The sight of another cock penetrating my wife was overwhelming. I stroked my cock furiously and shot my load all over the bed. My wife played with her clit and fucked herself to orgasm. Afterwards, Pam commented that she had never seen me so excited. I told her that watching another cock inside of her fucked with my mind to the point of making me go crazy. Pam giggled and told me that she liked it when I got jealous. Little did she know it had nothing to do with jealousy.

The next time we made love, she looked at me with a sly grin and grabbed the dildo and asked me if "John" could fuck her first. I shook my head yes. She told me that I could not touch my cock, she wanted me to be hard and ready once she came the first time. My heart nearly beat out of my chest. I agreed. My wife then inserted John into her wet pussy, closed her eyes and slowly fucked herself to orgasm. I stood by the bed trembling. After she came down from her orgasm, she softly whispered that I needed to take my turn. I eagerly jumped on top of her and slipped my cock into her very wet pussy. It didn't take a minute before I exploded deep inside her. After we both had finished, we snuggled and chatted. She said that she liked how excited I had gotten recently during sex. She said it made her feel sexy. I told her that I loved how she teased me with the dildo. Things seemed to be going my way.

Over the next six months we had some of the hottest love making sessions we had ever had. As time passed, she became more vocal while playing with her dildo. Sometimes she would talk to "John" while she fucked herself, which added to my mind fuck. Then one day out of the blue, she told me to wear a condom while we had sex. I asked why, as she was on the pill. She said that only "John" got to fuck her bareback. I nearly shot my load right there. I ran to the bathroom, found a condom, then rolled it onto my rock-hard shaft. She made me watch her fuck herself, then told me it was my turn. I mounted her like a dog in heat and pounded her hard. Being denied the feeling of my cock against the walls of her wet, silky-smooth pussy was too much to handle. It took less than a minute before my cock began to fill my cock's latex prison. As I came, I screamed like a mad man. Pam grabbed my face and pulled my lips to hers. Our tongues attacked each other in a lustful dance. My head was spinning, heart racing as she grabbed my hand and pulled me out of bed and into the bathroom. She told me to remove the condom and throw it into the toilet. I did as I was told. She then sat down and peed, drenching the cum filled condom. As she did, she looked into my eyes and smiled, but said nothing. I nearly passed out. She had a way of fucking with my mind that drove me wild.

It had been a year since I had approached the subject with my wife. Our sex life had exploded into horny, lust filled sessions where she would make me watch her get off on her dildo, then have me fuck her while wearing a condom or even denying me her pussy and making me jerk off while she watched. She also became more vocal during our sessions. She often talked to John, telling him how good of a lover he was. While I fucked her, she would tell me about how John fucked her and how he was a better lover. This would always take me over the edge. She then began giving me a time limit in her pussy. At first it was three minutes. I had to cum in the allotted time. If I did not, I would have to pull out and jerk off. Three minutes became two, then one. One minute to cum, with a condom on was a challenge but the alternative was my hand, so I tried my best to perform.

All this dirty talk and denial had really spiced up our sex life. We both loved it and things seemed perfect. Then one day it happened. We were preparing for making love. She had her dildo in her hand. She walked up to me, hugged me, and whispered in my ear, "I am ready for the real thing." Stupid me, I asked her what real thing she wanted. She pulled back and looked me in the eyes and told me she wanted a real "John" to fuck her. My heart stopped; I could not speak. I responded, "really?" She said that she had been secretly looking at my search history for the last year. She had watched almost every video I had watched. She said at first, she thought it was sick and perverted, but overtime, she found herself getting off while watching the videos. It was time, she was ready to make my dream a reality. However, there were some rules.

My wife said that it was my job to find her a lover. He had to be someone she was attracted to. Sex would be on neutral ground, in a hotel. I agreed and told her that kissing was off limits as I felt kissing just seemed more intimate and something reserved for us. I would be there to watch, and he would have to wear a condom too. She agreed, then told me I had a week to find her a lover. My mind raced, not knowing where to start. The next morning, I was at the gym, on the bike. Across from me was a late 20's something guy. His name was Greg. We became friendly and often spoke while we worked out and in the locker room. He was tall, handsome, and very muscular. This was exactly the thing my wife would love. He was not married and had often complain about the "women today", how shallow they were and how they always wanted the "bad boy". Greg was an attorney at a local firm at the beginning of his career. He worked crazy hours and had little time to date. I decided Greg was my target.

After we worked out, the two of us were in the locker room. I asked him why a handsome guy like him wasn't married. He laughed and just said, "women!" We both chuckled. I told him I had been married fifteen years. He said I was lucky. I admitted that I was. We were both supporters of the local college football team. I asked him if he would be interested in coming over on Saturday to watch the game. He thought for a minute then said he thought that would be great. My mark was now in my sights. I came home and told my wife who I had chosen and that she would meet him on Saturday.

Saturday came quickly and at 1 pm there was a knock at the door. Greg showed up in his team jersey and a case of beer. I invited him in, and we went to my mancave. My wife joined us a short bit later. Greg was talking to me and stopped mid sentence. His eyes glued to something directly behind me. I turned to see what had caught his attention. It was my wife. She had on the tightest short shorts that she owned and a nearly see through white cotton top on, without a bra. The whole ensemble was capped off with a little pair of white ankle socks and her hair pulled back into a long braid. The sight of her nearly made me cum in my pants. I took a breath then calmly introduced Greg to her. She bounced over and gave him a hug and welcomed him to our house, then told him that she would give him anything he desired or needed. You could cut the sexual tension with a knife. Greg sputtered, then gained his composure. We then grabbed a seat and turned on the pregame.

My wife made it a point to come in every few minutes to deliver drinks and food. She would drop things and bend over to show off her amazing ass. Greg tried not to make it obvious, but he was enthralled by her. It was early in the game when my phone buzzed. It was a text from "work". I looked down, text read, "you did a good job, I want to fuck him, right now, go away." I stopped breathing for a moment. I excused myself and went into the kitchen. My wife gave me a look of lust and told me that she wanted to fuck him now and for me to excuse myself, then go hide in our closet. She said her rule of neutral ground could be broken as he was hot as hell, and she was super horny.

I went back into my mancave and told Greg that I had a work emergency and had to leave. He was welcome to stay and watch the game with my wife. As I said that, she came in behind me and insisted that he stay. Greg did not resist. I kissed her goodbye and acted as though I had left. However, I slipped down the hallway and hid so I could eavesdrop. Within seconds, my wife went into full seduction mode. She hopped onto the couch next to him and began flirting with him. She laughed at all his jokes and soon touched his arm when she spoke to him. As halftime approached, I heard her tone get really serious. She asked him if she could share a secret with him. He said yes and turned to look at her. She grabbed both of his hands and told him that I was impotent and that we had not had sex in years. She did not feel like a woman anymore and she missed the feeling of a man inside her. Greg looked dumbfounded and sputtered a bit, not knowing how to respond. I nearly passed out hearing her. She should be nominated for Best Actress.

She then looked into his eyes, like a sad puppy, and asked Greg if he thought she was pretty. Greg responded in a split second that she was gorgeous. She looked back at him and said, "make love to me." She grabbed his hand and guided him off the couch. I quietly darted to our bedroom and climbed into the closet, leaving the door cracked a bit. Within seconds, they arrived. My wife knew my hiding place and made it a point to stand where I could watch her. She stood in front of Greg and slowly removed her top. He stared at her perky B-cups. She took his hands and placed it on her breast. It was his signal to get busy. In a split second, he had her head in his other hand and was pushing her lips to his. Kissing was a no-go zone. My wife's lips parted as did his and soon their tongues were dancing a ballet in each other's mouths. A shock of jealousy mixed with adrenaline cursed through my body. I wanted to burst from the closet and stop this. However, I was rock-hard, and my heart was pumping as if I had run a marathon. It is what I had wanted and begged for, for over a year, so who was I to stop it.

Soon his hand was cupping her pussy, feeling her wet anticipation. He threw his clothes off and they headed to our bed. Pam sat naked on the edge of the bed as he stood in front of her. She reached up and lifted his ample cock to her lips. Her eyes locked to his as she slowly slid his cock into her warm, wet mouth. I nearly screamed as this was one thing, I had always wanted her to do to me, but she told me she did not like sucking cock. In fact, in our entire marriage, I had gotten only three blow jobs, each of which had taken weeks of begging beforehand. Greg moaned softly as she expertly teased his hard cock with her tongue. His hands dropped and cradled her head as he began to gently fuck her mouth. Her left hand gripped the shaft while her right massaged his huge balls. Her expert abilities got him very close to cumming very quickly. She realized this and stopped then pulled him down onto the bed. Greg was on his back as she straddled his groin. Cock in hand, she rubbed the head against her clit then placed it on her labia.

Slowly, she lowered herself onto his waiting shaft. From the darkened closet I watched as his youthful, veiny, hard cock slipped into my gorgeous wife's pussy. I watched as another man took what had been mine and mine only for the last 15 years. Something that would have been exclusively mine for life, had I not had my sick obsession of seeing her with someone else. Every chemical in my body was at maximum level. Adrenaline, endorphins, and testosterone were all filling every pore of my body. I was dizzy and tingling, on the verge of passing out. My heart was beating so hard, I was afraid they would hear it. My cock stood at rock-hard attention and pulsed with every beat. Then lightning struck.

Greg said, "wait, shouldn't I put on a condom?" My wife said she wanted to feel what it was like to have a man's warm seed deep inside her pussy again, so no, he needed to fuck her bare. That caused a reaction that I had never had in my life. Cum began to ooze from the tip of my rigid cock. It wasn't an orgasm; no, it was as if my balls were under extreme pressure and a leak had developed. I looked down and watched as cum slowly bubbled to the tip, then oozed out into a little stream that then leaked down the shaft.

My wife slowly rode his hard shaft while her hands played with his muscular chest. He looked up at her in amazement. You could see it in his eyes, how lucky he was to have such a beautiful woman giving herself to him. She leaned down and kissed him softly, then told him to fuck her. The way she said fuck left nothing to the imagination, her intent was obvious, she wanted to be taken. She wanted to be ridden hard. Greg flipped her onto her back without even coming out of her. He looked down into her eyes with purpose. She responded by telling him, "Fuck me hard."

The next ten minutes was some of the hardest fucking I had ever witnessed. Our marital bed squeaked and groaned. It moved across the floor in fits and starts. Pam moaned and squealed with sexual pleasure. Her legs wrapped around his waist while her ankles locked together ensuring he could not escape. Her long French tipped nails dug into his back and ass like a koala in a windstorm. Suddenly, I watched as her toes curled and her feet turned in. Her body began to shake as her nails dug into his ass so hard as to draw blood. She let out a scream, then another. She reached up and grabbed his hair and pulled his lips to hers and kissed him so deeply, I thought her tongue would come out the back of his head.

That was enough to set him off. Gregs body stiffened, then his back arched a bit. He stopped breathing for a moment then let out a roar like a victorious lion. His hips shot forward, impaling my tiny wife with his large weapon. One, two, three, no eight thrusts, each delivering his hot, virile seed deep into my wife's womb. Filling her womb to the brim with his potent, Alpha manhood. Giving her the fucking, she had so desperately desired. Their bodies remained locked in lust for close to an hour before Greg got out of bed and made his way to the bathroom. As he did, Pam hopped out of bed and walked to the closet and whispered that she needed me inside her as soon as he left. She scooted back to the bed and acted cool.

Greg exited the bathroom and grabbed his clothes from the floor, then sat on the bed and gave Pam a kiss. He told her he should probably leave. She asked him if he would like to come back again. He instantly told her yes. She said that she would call him the next time she was alone, and he could come over for a "play date". Greg got dressed and left.

Pam called me to join her in bed. I eagerly climbed in next to her. As I started to touch her, she reached over to the nightstand and grabbed a condom and told me to put it on. I protested but she told me that her pussy was too full and that from now on, her lovers fucked her bareback, but her husband needed to wear a rubber. I sputtered a bit, but she said after seeing all my porn searches, she knew that was the way I knew it should be. I reluctantly agreed and put on the condom. A minute later I had shot my load uselessly into its rubber jail. Moments later, it was covered in Pam's piss and flushed down the toilet, while her lovers cum, warmed her belly.

For the next seven Saturday's the gameday play date continued. Each time, work would call, I would leave, and they would fuck like rabbits as I watched from the closet. On the eighth Saturday, they were going to be "caught" in the act. It went down like any other gameday. I got called to work, they went and fucked, but this time, I came home early. I walked in right as Pam had orgasmed but just before Greg had shot his load. The look on his face was priceless. He immediately began to apologize and tried to pull out, but Pam had him locked in a death grip. I looked at the two of them as if I didn't care and told Greg that I could not satisfy her, so she could fuck whomever she wanted. I then left the room. There was a long period of silence that was broken by the sound of Greg filling my wife with his hot gift. About ten minutes later he sheepishly came out of our bedroom and walked to the door. I told him he was welcome to come back anytime, and that Pam enjoyed his company. He looked shocked and said, "ok, is next Saturday good?" I told him for sure and that I was looking forward to it.

The following Saturday was a bit more tense. Greg seemed nervous. As soon as the game started, I told him to go fuck Pam. He slowly left for the bedroom where Pam was already waiting. I followed a few minutes later and stood and watched from the darkened hallway. The sight of them together drove me nuts. I knew it was wrong, taboo, against nature. It made my insides turn upside down. She was my wife and mine alone, yet I had given her to another man, a man that she obviously enjoyed fucking. Was I losing her? Was my sick perversion the end of my marriage? We still loved each other. We still were affectionate. Our sex had changed. Over a year ago, I fucked her like he was fucking her. Now, my sex was timed, and my penis always wrapped in a condom. My cum was always uselessly deposited into rubber then thrown in the toilet like shit, only to be pissed on while she looked at me and smiled. It was degrading, demoralizing, but I got a strange, sick, joy from it. As I watched them fucking, my whole body reacted. I never felt so alive, so excited. I could feel every pore of my body. Yet once I had my minute of pussy time and I had wasted my sperm, I felt so dirty. Watching Pam piss on my cum, while his seed filled her fertile womb knocked me to my knees. I was small, insignificant, a beta submissive to my wife's Alpha lover. The flood of emotions was a level of mind fucking that deserved medical research.