Confessions of a Cuckold

by UpstaterNY


He describes beginnings of cuckold lifestyle.





I am a cuckold. Which means that my wife freely engages in sexual activity with other men, while I'm not allowed to have any kind of sexual relationship outside of our marriage.


Oddly enough it was my sexual desires that got the ball rolling so to speak. While we were dating I was always trying to get her to dominate me sexually. It started when I saw a copy of the erotic-story publication -- Penthouse Variations. Immediately I was drawn to the section titled 'Femdom'. The idea of submitting to a beautiful & powerful woman really turned me. I asked my then girlfriend to try a few things had read about. Nothing too extreme, just the usual handcuffs & spanking.


From there it really grew into a fetish that I craved. It seemed like a constant struggle for me to try and get her to do more in the way of dominance. She had much more vanilla sexual tastes although about once a month she would indulge me in my fantasies. I looked so forward to our 'special nights'. I would fill her head with hints about what I'd like her to do to me. One night I may be 'forced' to wear women's panties and be chastised for being a naughty little girl. Then next time I might 'lose' a wrestling match to her and be made to tongue her ass until she was thoroughly satisfied.


This arrangement continued throughout our dating and into our marriage. However I always felt a little guilty after we would finish a session. Each 'special night' would conclude with my orgasm. As soon as I had cum I wanted nothing to with being submissive or be humiliated in any way. I can remember asking her so many times – "Is there something wrong with me?" She would always answer no and of course by the next day I was back to crave the delicious torment. Eventually the guilt wore off but the fact remained that once I had cum I wanted no more of the kinky stuff, I didn't even want to talk about it.


Things in our marriage weren't going very well after about three years of being wed. Our sex life was the same and neither of us seemed too unhappy with it. But the overall relationship was suffering. We barely did anything together, we didn't have much in common, and our communication was lacking. It was about this time that during our 'special nights' I asked her to role-play a scenario. The idea I had was the she was a cheating wife who had just come back from a date and I was to be made to give her oral sex. For the first time she seemed to really enjoy the role-play! At first I was very concerned. Did she actually want to cheat on me? Was she wanting to develop feelings for another man?


I actually got the nerve up one night after I had cum to ask her about it. She flat out told me that she wasn't interested in cheating on me, but just the idea of her having sex with someone else turned her on. We went on to have a true, open, & honest conversation. Our first in a long time! We talked a lot about sex and what each of us wanted. She explained that she got so turned on by having sex with someone else because she was thinking of it in a purely physical sense. No emotional attachment with the other man and not damaging her current relationship (with me). She had partners before me, albeit not a great number, but they were all boyfriends that she had dated. She never had a one night stand. She asked me if I thought about being with other women. I told her that I occasionally fantasized about it but like her had no intention of cheating on her. She expressed to me that it would hurt her so much if I had sex with someone else because she would automatically equate sex with love. That somehow I would love her less and the other woman more. On the flip side I made mention that if there were no emotional attachments between her and the other man that I would be OK with it. In a strange way it was nice to see that we could have different views on the same subject and express them to each other without getting upset at one another.


For the next few months, things gradually got better between us. Our 'special nights' got hotter also. She really got into the role-playing of her being with another man. Strangely enough my post-cum feelings were disappearing. Even after cumming the idea of her sucking another man's cock and having her getting fucked were still a wonderful image in my head.


One night we were at home together and she had a bowl of grapes in front of her. I am notorious for being a picky eater and I had never even tried a grape. She teased me by offering me some.


"Honey, you want a grape?" she said.


" way!" I protested.


"Aww, come on you've never even tried one before. You might like it."


"No way."


"OK, if you try one I'll let you see my tits!"


"I see them all the time, we're married remember. I see you every morning in the shower."


"Oh that's right," she joked "Well how about I give you a blow job?"


"Well," I said "that sounds pretty good but you give me those on a pretty regular basis..."


"And?" she asked.


"Well it's just that if I don't bother to eat the grape I still think that sometime in the near future I'll get another blow job."


We both had a playful laugh.


"So I'd need to offer something special then huh?" she asked.


"Yes." I replied.


"If you eat a grape," she said as she looked directly at me "I'll have sex with another man."


At first I wasn't sure what to say, we had been kidding all along but she seemed to look kind of serious about it. Just the way she said it got me really turned on. My brain gave way to my cock at that point.


With that I popped the grape into my mouth.


I was surprised that I actually did it and she was too. I think she was just trying to bluff me some but suddenly things got 'real'. It wasn't a question of a fantasy or role-play. Now the issue was more life-like, was she really going to sleep with another man?


We got into another conversation about her actually doing it. I again stated that I could handle it, even get very aroused by it as long as there was no emotional attachment between her & her 'lover'. She questioned me about that, saying that I would be singing a different tune if I weren't horny. I made a sarcastic comment like 'You wanna bet?', that I figured she'd not respond to.


To my surprise she stood up and in the middle of the kitchen told me to strip completely naked. I was more than willing, figuring that one of our 'special nights' of role-playing was beginning. Once I was fully nude she commanded me to start jacking off in front of her. She got into the role a little telling me that by eating the grape, I had given her permission to be with other men. I was getting very excited and the pace of masturbating picked up. She held her hand out palm up and told me to cum in her hand. With that I exploded, bursting my creamy jizz all over the palm of her left hand. I felt relieved and satisfied. But still intrigued with the idea of her being with another man.


Looking at me directly in the eye. She stated "If you really want me to fuck another guy I have one more thing for you to eat." She then gestured toward her hand that was still covered in my spunk.


"I'm serious," she said "I know how you are after you cum. You want to forget about all the things we just role-played. Well if you lick up all this cum, I'll know that you truly want it to happen and I'll do it for real."


I was stunned. I stood there for a second, but it felt like hours. My own cock, which had almost immediately got soft after cumming started to get hard again.


"Oh my!" she exclaimed "Look at you. You're getting hard again. Come on baby lick up that cum I know you want to."


Hesitantly I bent forward and started to lap up the mess that I had made. It was like an out of body experience, but it made me so horny again. When I was done she just smirked at me and headed upstairs.


"Where are you going?" I asked.


"I need to go figure out who I'm going to fuck."


With that I realized that I was going to be actually cuckolded by my wife.




Confessions of a Cuckold Ch. 02

by UpstaterNY



Cuckold fantasy becomes reality.



There I was standing stark naked in the middle of my kitchen. My cock rock hard minutes ago was now starting to go flaccid again. What have I gotten myself into? I asked myself. I had taken my wife’s “dare” to eat my own cum. The dare came with the promise that she would fulfill a shared fantasy of ours – for her to have sex with another man.


I gathered my clothes up and decided I really need some time to think about all of this. I went for a long walk. Along the way I tried to understand why the idea of my wife being fucked by another man while I watched was such a turn on. The answer of course is impossible to explain. But those of you who share it know exactly what I’m talking about. Then I started to think about more important matters, like how it would affect our relationship.


After a couple of hours I came home and my wife was sitting on the couch reading.


“Where did you go, honey?” she asked.


“Just out for a walk” I replied.


“Is everything OK?” she asked somewhat nervously.


“Yes. Yes it is. You know that we’ve had this fantasy of you fucking another man, and tonight it just seemed like we taking it to another level.”


“I know, I felt the same way. So do you think we’re ready for this?”


“Well, I came up with a few concerns…”


With that I explained that I had criteria that must me met.


#1 the person she chose was healthy #2 someone she trusts #3 not someone she or I see on a regular basis


and most importantly…


#4 That it would be just sex, and would not trample on our relationship at all


She had a look of absolute relief on her face. She explained that she was thinking almost the exact things. She also said that she had someone in mind already. I was a little surprised that she said Derek, her hairdresser.


I had met Derek a few times, actually since he was a hairdresser I figured he was gay. However my wife told me that he’s actually hit on her before and that she was sure that he’d go for it. As coincidence would have it she had a hair appointment with him the next day.


All day at work I was watching the clock so I could race home to see if she asked Derek. When I got home I was pleasantly surprised that he was more than willing and that he was coming over in two hours!


I thought I was going to pass out I got so turned on instantly. We went upstairs and I helped her prepare for our date. I picked out a sexy black bra, matching string bikini panties, garter belt, black stockings and topped off with a pair of black high heels. She finished off the outfit by putting on a tight white tank top and a black leather mini. She really played up the whore-look with a ton of make up and teased hair. When she was done she looked hotter than ever.


It was only about 15 minutes before Derek was supposed to arrive and my wife told me to sit down. She then went on to explain that I was to do exactly what I was told and to not question her.


I bowed my head and said “Yes, mistress.” Right on cue the doorbell rang.


I was instructed to strip down put one of her bras and a pair of panties and to wait in the bedroom.


She left to answer the door and from the bedroom I could hear the faint sounds of their voices. It seemed like an eternity but then I finally heard two sets of feet climbing the stairs to the bedroom.


The door opened and my wife led Derek into the room by the hand.


“Derek, you have met my wimp hubby before right?” she asked.


He nodded with a smirk.


“Well as you can see,” she explained “he’s clearly not man enough to handle me. So I was hoping you could fuck my brains out and maybe needle-dick over there can watch and learn.”


“No problem” said Derek.


With that they began to kiss, a charge went through my body like never before. Standing there in bra & panties as my wife was being mauled by this other man, it was like nothing I could imagine. I was so turned on my cock strained against the silky fabric of the panties.


Without much effort Derek removed both his & her clothes leaving my wife in just her garter belt, stockings, and heels while he was stark naked. Roughly in pushed his cock in and out of my wife while she moaned with passion. They were both insatiable. I heard my wife have at least two orgasms. Not long after the second one, Derek’s body tensed and I could see his balls tense up as he deposited a load into her cunt.


With a satisfied look on his face Derek withdrew, got dressed, and casually said goodbye to both of us as he left. My wife was on her back on her bed, I could see the jism starting to trickle out her well-fucked pussy. My own cock had started to ejaculate some pre-cum making a mark on the front of my panties. She crooked a finger at me instructing me to come to her. Hesitantly I approached. She guided my head towards her pussy and I could smell their mixed scent. I paused for a moment looking at the glorious cream pie in front of me. I stuck out my tongue and tasted her. Immediately she was turned on as well. I continued to lap the cum out of her gooey pussy. I took my time and made sure I got it all.


She then finally turned to me and asked if I wanted “sloppy seconds”.


Immediately I said yes and shed the bra & panties I was wearing. I slid my cock into her and it felt wetter than ever. With all the excitement of the night I lasted all of about 2 minutes before I shot my own load into her.


With that, we looked at one another, said our “I love you’s”. Then went to sleep.




Confessions of a Cuckold Ch. 03

by UpstaterNY


Another episode for the cuckolded hubby.



It must've been the soundest sleep I've ever had. I woke up and saw that it was already 9:34am, my wife Brooke was fast asleep in the bed next to me. I laid there for a while trying to re-live in my mind the previous nights events. After a long time of role-playing, Brooke actually cuckolded me. She had sex with Derek, who is her hairdresser, in front of me while I was wearing one of her bras and a pair of panties. It was the most intense sexual experience of my life and it couldn't have been better. I could almost still taste the remnants of Derek's load that I lapped up from Brooke's pussy right after he left. The sensation of sliding my 5-inch cock into Brooke for what she called 'sloppy seconds' was deliciously humiliating.


Gently I caressed my sleeping wife's nude back as she started to awaken. We exchanged "good morning's" and just stared at each other for a little while.


"Last night was amazing honey." Brooke said.


"I know, it was better than I could've imagined" I agreed, "this may sound strange but did you have a favorite part?"


"Yes, definitely," she stated "I felt like a total slut. I know that usually is associated with being a bad thing. But I think a lot of women would like to be slutty without the social stigma of being a slut. Like I knew that since you were enjoying it as much as I was that it was OK and that being a 'slut' was a good thing."


"You're a great slut, dear" I said with a smirk.


"Oh, Sean," she said sarcastically "that's the nicest thing you've said to me in a long time!"


We both had a laugh but we really were on the same page. She enjoyed that idea of being slutty and I craved the domination that she doled out along with it. We both knew that it wasn't our entire lives. We were 'normal' people but had this kinky side that we liked to explore in our sexual play. Our friends and neighbors didn't know anything about that side of us and that's just the way we wanted it.


We continued our little role-play situations with great enthusiasm. Brooke would dress real slutty and come into the bedroom, slap me around, verbally abuse me -- calling me a 'faggot' or 'sissy' and force into wearing her underwear. Then she'd go into great detail about all the men she'd fucked while sitting on my face. Needless to say we really enjoyed all of it.


About six months went by since our night with Derek, when Brooke asked if I'd be interested in another night of actual cuckolding. Well it took me about 2 seconds to answer "Yes!"


"OK, then" she explained, "This Friday, I'll set something up. I'll make all the arrangements."


Friday came and I was dreading my workday, it seemed to drag on forever. Once 5pm came I raced home to find Brooke on the couch leafing through a magazine.


Going straight into her dominate slutty persona she greeted me with "Oh, I see my little faggot hubby is home. Are you happy to see me?"


"Yes, mistress."


"Well then show me. Get over here and lick my feet."


Hurriedly I went over to her and began to tongue her sexy peds.


"That's it," she cooed "you know where your place is."


She went on to tell me that she was going out tonight and that I was to stay at home and wait for her. With that she went upstairs, into the master bathroom, and closed the door. Not knowing exactly what to do I waited for her just outside the door. It took over an hour, I heard her in the shower, blow-drying her hair, etc. When she came out she was a vision. She wore a tight pink mini-dress that showed off her long legs and deep cleavage. Her hair was tied back in a ponytail and she just looked unbelievable.


"Do I look hot, slave?" she asked.


"Yes, dear. You look beautiful."


"Do you think I'll have any trouble getting some cock tonight?"


"No. Not at all."


"OK, here are your instructions" she said as she handed me an envelope and left the room.


I tore it open and followed them to the letter. I shaved all my body hair below my neck, showered, and put on the outfit that she had laid out for me. The outfit was a complete French Maid getup, including the dress, lace apron, & high heels. All in my size! The ensemble was topped off with a blonde wig. When I saw myself in the mirror I realized that I made a pretty good cross dresser!


Brooke was pleased upon seeing me and I passed her inspection. With that she told me again that she was going out and that I was to perform my maid duties and clean the house from top to bottom.


On her way out she simply said "See you later, cucky!"


I started my chores and figured Brooke wouldn't be home for quite a while. So I did the best I could to keep busy and keep my mind off of what Brooke might be doing. A few times I had to stop and literally catch my breath, the excitement I felt from the idea that Brooke was out banging & sucking guys was almost too much.


The house was as clean as ever. I scrubbed every floor, all the bathrooms, vacuumed, did laundry, and every other household chore I could imagine. It was about 1am when I finally figured that there were no more duties that this sissy maid could possibly do. Just sitting there was the worst since I had no idea of when she would come home.


I got lucky because it was only about 45 minutes later when I heard the car come up the driveway. I could hear voices as the front door opened. Brooke was the first to enter and she was followed by Derek, the hairdresser she previously banged. To my amazement a third person entered. A tall muscular black man I did not recognize.


"Hello there sissy," my wife said "the house looks so nice. You remember Derek, don't you sweetie?"


"Yes, I do."


Brooke then made me curtsey to greet him.


"And this is Derek's friend Chris."


Again I had to curtsey, then I was told to hang their coats and return with beers for all three of them. I came in with the drinks to the sight of the three of them on the couch all sitting close to one another. They made small talk and laughed while drinking their beers. Once the drinks were gone Derek & Chris each started to feel Brooke up. Their hands roamed freely across her tits & ass. She had a look of lust on her face and after instructing me to put on some music began a strip tease for the two guests.


Slowly she shook her beautiful round ass in their faces and stripped down completely nude. Both men took their cocks out and began to stroke themselves. I had seen Derek before and was impressed with his size, but Chris was even bigger. I even wondered if Brooke would be able to accommodate his size.


Brooke then got on the floor on all fours and the two guys each took a position. Derek went behind her and slammed his cock into her pussy while Chris got on his knees and fed his monster cock into her mouth.


Rhythmically they began their welcomed invasion of Brooke's holes. I was sitting on a foot rest only a few feet away and had the best seat in the house. Derek began pumping faster & faster, then he pull out of her pussy and let loose a stream of cum all over Brooke's ass.


Brooke then took Chris' cock out her mouth and told me that it was 'clean up time'. I got up and started to the kitchen to get a towel.


"Where the fuck do you think you're going?" she angrily asked.


"To get a towel to clean you up."


"No, no, no. I don't want you to dirty a towel. I want you to use your tongue to clean Derek's jizz off of my ass."


Nervously I positioned myself behind her round ass. I was a little hesitant having both men watch as I licked the spunk up. Apparently I wasn't doing a good enough job because Brooke turned around and slapped me in the face. She chastised me for not being a good enough maid and that my duties were to clean up any and all messes. For my transgression she lifted up skirt and used Chris' belt to beat my panty covered ass. When she was done I returned to my duties and eagerly licked the rest of the cum from her ass.


I had it all lapped up when Brooke said "I think there is still a drop or two."


I didn't understand what she meant until she pointed to Derek's cock. On the head was a drop of semen. Having never even touched another man's cock, let alone lick cum off of one, I was a little scared. But the stern look I got from Brooke and the fresh belt marks across my own ass got me motivated. I licked the head of Derek's cock, with that all three of them started giggling at the site of me tonguing his cock head.


Brooke went back to blowing Chris and before long he exploded into her mouth. Turning to me she gave me an open mouthed kissed and used her tongue to push the creamy load from her mouth into mine.


The three of them lied there in a relaxed state and I was ordered to get more beers. Again as soon as they were finished with the beers they started to fool around again. However this time Brooke said that our guests needed some 'encouragement'. I was then made to get in front of a sitting Chris and ordered to give him a blowjob until he was hard enough to fuck my wife. Straining to get my lips around the massive cock, I began to bob my head up and down on his cock. Before long his cock was plenty hard, he got up, got on top of Brooke and started banging away. Derek took his place in front of me and I repeated the task. Right on cue Chris came in Brooke's pussy just as Derek was ready to go. Within minutes he too deposited a load into my bride's cunt.


The guys then got dressed, I got them their coats and the headed off. Left alone with just Brooke and I, I knew that I had a new mess to clean.


"So now you're a cocksucker," she said "Well I always thought you were a faggot, but I guess now I know for sure. Since you seem to like cum so much, bring your cocksucking mouth over her and clean up this pussy!"


I sucked at her wet, well fucked snatch like there was no tomorrow. I heard her moan with pleasure and she orgasmed right there.


We then went to the bedroom and I was allowed to shed my maid outfit. But I was told that I was to wear a baby-doll nightie that Brooke picked out for me. I thought I would be permitted to get my 'sloppy thirds' but Brooke informed me that since I hesitated the first time when asked to lick Derek's cock that I was not allowed to fuck her, instead I had to jack myself off.


It took a total of about 5 pumps of my little tiny cock to unload my own load, which of course Brooke scooped up with her finger and fed to me. With that, I rolled over and had another great night's sleep.


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