It started off innocently enough. I met my wife when I was in the military. She was a party girl. I was serious and reserved. Somehow, we clicked and after a couple of years we got married. Before we got married, quite a few people told me of her reputation. She definitely got around. But, hey, she was single and it was her life. It was me she picked to settle down with, etc, etc.
Once we got engaged, inevitably, out of curiosity I told myself, I wanted to know how many partners she had. When I asked her, she was kind of demure, and asked me to go first. I told her six which was a little exaggerated. The real number was two before her. I could tell she was sizing me up when she said it was six for her, too. I instantly felt charges of jealousy that kind of paralyzed my body. My breathing increased, and I was obviously flustered. Before I even had time to say something stupid, she went down on me and gave me the most amazing oral sex. That’s how I think my ‘cuckold conditioning’ began.
A couple of months before we got engaged, one of her friends from another state visited. She said he was like a brother to her, and he was treating her to a weekend at Disney. We were kind of boyfriend/girlfriend at the time. I don’t think there was any formal declaration or anything, but we were practically living in each others’ dorms. Since I had no reason to doubt her, I never let myself question her intentions at the time. But, once I got her sexual partner history, I couldn’t get her Disney excursion out of my head. I didn’t know how to ask her, but it turns out it didn’t have to. He called her at work, and one of her coworkers told her in my presence that her ex-boyfriend, Tony the fireman, left her a message. That was the name of her ‘brother’ that she went to Disney with. That and, her face went completely splotchy red when she got the message in front of me. Again, it was like an atomic bomb of pure adrenalin that went off in the pit of my stomach.
I tried playing it off, but my speech was off. My actions were off. When we got back to her place, she went straight to the bathroom. I sat down on the couch. My mind was swirling with how to broach the subject. I was pissed off, jealous, and I couldn’t get the image of her on her back for a weekend with some other guy. She got out of the bathroom and sat down at the foot of the couch. Before I could say a word, she took off my shoes, unzipped my pants, and started kissing me through my boxer briefs. Funny thing was I that I was already hard before she even got out of the bathroom. I was embarrassed that she noticed, too.
Then she said, while still kissing me through my briefs, that it was her ex-boyfriend that she stayed with at the Disney hotel. She slipped of my briefs and started licking, nibbling, and sucking my balls. My heart was pounding. After a few seconds, she said that she wanted to come clean and she said that they did fool around. Before I could ask for more information, she licked from the base of my balls all the way to the tip of the head which was oozing precum. She saw all the precum and shot me a quick glance.
She said that she didn’t intend for things to get sexual, but they had a great time and had a few drinks and it was nothing important. Then she started licking the head of my penis and down the sides. I desperately wanted her to take it into her mouth, but she was making it all the more intense by taking it slow. I finally asked in an surprisingly gruff voice, “Did you have sex with him?” She looked up while licking the sides of my penis, and nodded yes, and then proceeded to stuff it all in her mouth. She started stroking and vacuum sucking, and I literally was almost ready to cum when she stopped stroking, and went back down to my balls.
“Did you go down on him?” She looked up at me with her pretty brown eyes, and nodded yes again. My body was numb, but I was beyond turned on. She took off her top, and then slipped off her bra without undoing the straps. She said, “I did this too.” And, she proceeded to place my dick in between her tits and pump it in her cleavage. After few more seconds she went back to sucking and stroking, until I patted her on the shoulder that I was getting close. She pulled out, and rubbed my dick on her tits as I shot load after load on her pretty chest.
She didn’t clean off any cum, and she put her head on my lap and occasionally kissed my penis as she said she was sorry she wasn’t truthful before. She said she was embarrassed that it got sexual, and she didn’t want to hurt me. She said that was the last time she had sex with anybody before me, and once we got engaged, she told Tony that she didn’t want to stay in touch anymore. She said she was Mrs. Faithful from here on out.
I thought about it, and I figured that since we weren’t married or even engaged at the time, that it wasn’t a big deal. I rationalized her lying to me by saying to myself that I would have done the same thing. And, truth be told, for some unknown reason, it turned me on more than anything else that she was desired by others to that point. We got married, still married after 14 years, and she’s been a great wife, housewife, and mom to our kids.
The thing is that her past sexual experiences have always intrigued me for lack of a better word. The thought of her with another man just drives me crazy with jealousy and sexually excites me at the same time. So, I brought up the topic of a threesome – with another man – and how it was a fantasy of mine. I asked her about it after one of our ‘date nights’ where we went out for dinner and a movie. She looked at me with a quizzical look like she didn’t know what kind of answer I wanted or expected. I told her that I still found it exciting thinking of her with her sexual partners in the past. She kind of laughed it off and commented that she couldn’t see herself in a threesome with another man and me at the same time. Maybe another woman, but even then, it wasn’t something she actively wanted to pursue.
I told her that her handful of past partners made her all the sexier. She laughed and said “handful was right” or some comment like that. I then asked her how many partners she had again, and she quickly said eight. I don’t have the greatest memory in the world, but I did remember her way back saying only six. So, I reminded her about that conversation. She paused, and laughed, and said, “Do you really think a woman is going to tell you the ‘real’ number?” She said, “I wanted to marry you, not run you off.” Then she told me that women usually decrease the number of sexual partners and men inflate them, which I kind of already knew anyway. I asked, “So, what’s the real number, then?” She said, “You don’t want to know.” That response actually got me hard and charged up. “I do want to know. Look, we’ve been married forever. It doesn’t mean anything anyway. That was your past. Plus, you know how much it turns me on.” I said it in as cute a way as I could muster up at the time. She said, “It’s more than eight. That’s all you’re getting from me. Now let’s talk about something else more interesting.” As much as I wanted to finish the conversation, I let her off the hook, because I figured she was at the point of locking up anyway. No reason to make things uncomfortable. I wanted her to see it didn’t bother me, and that I was okay with it.
When we got home and finally got in bed, she started rubbing my crotch and kissing my neck. When I got hard, she slipped off her pj’s and climbed on top of me. It slipped right in. All I could imagine was her on top of one of her eight boyfriends, and it was such a turn on. She pressed her tits to my face and said under her breath, “I’ve had eight steady boyfriends since I was 15.” I was a little confused and wondering what the hell that meant. Then she said, “Steady to me was at a month or two.” Okay, I thought, she’s setting the foundation for something.” “Now as far as hooking up, girls don’t usually count that. I don’t count that.” And, that was it. She didn’t say anything else about it, because she pulled me out right before I started to cum and stroked me until I coated her muff and my stomach with a half dozen spurts of cum. That was amazing. We cleaned up, made a little small talk about nothing, and she went right to sleep, and I laid there in fantasy land for about an hour.
In the morning, we woke up about the same time. It was a weekend morning, so we just relaxed lazily in bed. She flicked the TV on for background noise. I then asked, “You know I’m going to ask you for more info.” She laughed it off and kissed me and said, “I know, but that doesn’t mean you’re going to get it. Now does it?” I said, “Come on now. You know how much it turns me on, baby!” She laughed again, “I know. I know. It’s just weird to me.” I said, “Weird?” She said, “You know what I mean. Not weird, weird. Maybe a little perverted weird.” She giggled and crawled under the sheets and pulled my pj’s down and started to suck me. I said, “Ok. How about sucking me the way you sucked someone else?” She stopped and looked up and said, “What? What do you mean?” I said, “I’m sure other guys probably liked it a certain way.” She said, “A blowjob is a blowjob. It’s good if you cum.” She giggled again, and then stuffed her mouth full. After a couple of seconds, she paused. “You know, now that I think about, this one guy made me hold his abdomen when he came from a blowjob. It was like he was in pain or something.” I said, “Really?” She said, “Yeah, if I would forget, he would grab my hand and put it on his abdomen.” Just hearing her say something intimate about her with another man made my dick beyond hard. I was at the point of almost cumming, and she was just holding my dick – not even stroking it. She said, “And he liked me to put pressure underneath the head with my thumb.” She illustrated it on my dick, and it hurt a little, but she could tell I was in la-la land. She finished me off in mere seconds after that. I forgot to warn her about cumming, but she sensed it and pulled out in time. My chest was visibly heaving, and she looked up at me from between my legs and said, “You are so fucking weird.” She giggled and kissed me on the cheek, and then went to the bathroom and started brushing her teeth.
Later that night after the lights were out, I got up enough nerve to ask her about penis size. I had to know. She disappointed me by saying she couldn’t remember. They are all about the same. The most I could get was some were a little bigger or a little smaller. Then I asked if she was every sore the next day. She thought for a sec and kind of lit up and said, “Yeah. There was this one guy. And, yeah, he was big.” The adrenalin hit was like a drug to me. It burned my insides and heightened my sexual being. She looked down at the bulge in my shorts, and reached under my boxers and smiled at me as she rubbed me. She then said they had intercourse only the one time, and after that she only gave him head the two or three times they hooked up. She said she remembers him because after a night of sex with him, she was so raw that it burned when she peed the next day. She said she was drunk which helped, and the only way they could have sex was doggie style. Missionary hurt too much. Even her on top hurt too much, because he would grab her by the hips and plunge her down onto him. She said he was a couple of inches bigger than me which was manageable. It was his girth that was painful. She said she could barely touch her thumb to her index finger when she went down on him. When she sucked him the most she could get into her mouth was his thick head and maybe an inch more of his cock. That did it for me, and I exploded in her hand underneath my shorts. “You are so strange,” she said and we turned in for the night. My progression into cuckoldry was starting to accelerate much faster.
Our sex life was always good, but with this added dimension, it was amazing. We didn’t ‘talk’ about her past often, maybe once or twice a month, but it was always in the background for me. I’d get visuals of her having sex with another man while we were having sex. Then, about a year ago, as we were chit-chatting right before bed, she dropped a little bomb on me. She said a guy at work was flirting with her, and he was cute. That was it. She was feeling me out by volunteering the ‘cute’ part. I asked her what she thought about it. She said, “It’s flattering, but I’m not interested. Definitely not interested.” I said, “If you did go down on him, show me what you would do.” She said, “Not going to happen. Nope.” I said, “Just for fun, show me.” She reached under the sheets and felt my hard-on, giggled, and said, “Okay weirdo.” When I got close, I touched her shoulder. She didn’t stop. She let me cum into her mouth, which she doesn’t do a whole lot because she doesn’t like the taste of cum. Then, she made it a point to let me know she gulped it down. She hardly ever swallows. Maybe like two or three times during our entire marriage. That blowjob was probably one of the top three she’s ever given me during all of our years of marriage. She kissed me quickly on the lips and then went to brush her teeth again.
Every night after, I’d try and direct the conversation toward her work – specifically her ‘cute’ coworker. She said she made it clear to Matt that she was married and nothing would ever happen from their flirting, but at the same time, she didn’t put a definitive stop to the flirting. It was harmless as she would say and confined strictly to the office environment. She said their talk sometimes got sexual – like a coworkers huge boob size, or an ill-fitting cameltoe on their general manager. It was stuff like that until somehow he got on the topic of oral sex. She described their conversation like a funny competition where each one of them was bragging about how much better at oral sex they were than the other. She said after they got up for lunch, she could tell he was trying to shift around because he had an erection. She was laughing as she said it. I asked her how she felt about it. She said, “I was a little turned-on, too. But, don’t even think about it.” I innocently replied, “About what?” Then, I asked, “What exactly about him turned you on.” Her answer about floored me. I thought she would say his eyes or his looks or something like that. She said, “It’s not the thought of him going down on me. What turned me on about him was thinking about me going down on him when I was describing how I give blowjobs.” I shot her a surprised glance. She quickly reminded me, “Never going to happen, dear.” In my mind I was thinking that maybe it might.
As much as she protested that their flirtation was meaningless, I could tell she liked the attention. So, I suggested to her a couple of times that maybe we should invite Matt over for dinner. She replied it would be too weird and wasn’t keen on mixing her office life with her private life. She then came home from work the next day telling me she had a nice surprise for me. She invited Matt over for a BBQ with us on Sunday. I thought I would be excited, but I at once became a little guarded and not so sure it was a good idea. I never really thought my wife would actually go through with the invitation. Still, I knew nothing was probably going to happen, and I was curious about who this guy was and what he looked like.
As the week progressed, she constantly checked with me to see if it bothered me. She said she had no problem canceling, and personally she thought it might be better to leave her office relationships at the office. I told her I trusted her, and I would never feel threatened when it came to her. Inside, I wasn’t so sure, but any misgivings I might have had were washed away with my horniness of imaging my wife with another man.
I made it point to have Matt’s favorite beer on hand. I also broke out the blender and made my wife’s favorites: Pina Coladas and Strawberry Daiquiris, and I wasn’t stingy with the alcohol. Matt turned out to be a really nice guy. He was about our age, divorced, about my height, and liked sports as much as I did. For awhile we were talking football and baseball so much that my wife was standing in the kitchen twirling her hair while she shot me a silly little grin. She mouthed to me, “BFF”, like Matt was my new best friend.
After several drinks, the tension kind of melted away. My wife sat down in front of me on the couch, and we were talking small talk. They would drift off every now and then into office talk, which would ordinarily bore me, but kept my interest this time knowing that this was the guy flirting with my wife. They started talking about this girl, Mary, who got fired along with a division chief for giving him oral sex in a supply closet. They were laughing at how they were caught in the act by security because there was actually a camera set up in the supply closet due to someone stealing staplers or something stupid like that. Then Matt made a veiled comment about my wife’s special office talent. I wasn’t sure what he was talking about, until my wife commented to Matt that she told me about their “oral sex discussion” already. Talk about uncomfortable! I was beyond uncomfortable and Matt was worse than me. It was almost to the point where he needed to leave, and then my wife broke the ice and said it was true, she was a pro in that department. Just ask me. She patted my crotch and smiled at me. I said, “Yes you are, baby.” She was feeling good – tipsy for sure. Matt laughed a little and said to me almost sheepishly, “You’re a lucky guy.”
I excused myself to use the bathroom. As I started to take a leak, I noticed a little string of precum dripping down from my dick. I never thought my wife could be so bold in front of another man. I washed my face and was wondering what direction this was going and then I started second-guessing if this was even a good idea. I looked in the mirror, forced a smile, and then went back into the living room and saw my wife on her knees between his legs and sucking his dick!
I froze. I felt instantly cold and panicked. Even though I had mentally pictured, fantasized, and dreamed about my wife with another man, I don’t think I was truly prepared to see it in real life. He had one of his hands lying atop the couch and the other hand at the back of my wife’s head. He was staring at the ceiling, and she had her eyes closed with one hand cupping his balls and the other hand gripping his shaft as she worked her head up and down. He started to moan and looked down at her at about the same time she opened her eyes and looked into his. Then, he grunted and started to cum in her mouth. She was taken by surprise and started gagging for a sec as she turned her head inward towards his thigh. She coughed a couple of times and then started giggling. “That was a lot of cum,” she said. And it was. There was cum on her chin and some on her shirt.
Then, it was Matt’s turn to freeze when he saw me. He started to stammer, and I saw my wife turn to look at me. It was a little tense until I said, “It’s okay.” That was all I could muster. My wife got up from her knees, and walked toward me with a big smile. “You okay,” she asked. I nodded yes. “Good, that was for you.” She kissed me full on the lips, and walked into the bathroom. I tasted and smelled his cum on her kiss. I noticed Matt fumbling with his jeans, and getting his shoes on. He said a quick goodbye, and off he went. I sat down on the couch in a daze. It was like being alive inside a dream – except it was real and there was no taking it back.
My wife walked in and asked again, “You sure you okay, baby?” I said, “Yeah. That was intense, huh?” She said, “It was nice. Now let’s take care of you. I want you to sit right where Matt just was.” I scooted over and she undid my pants. She kissed me again – this time toothpaste kisses. She kissed her way down until she was on her knees, took off her shirt and bra, and then started to give me oral sex. It lasted all of 30 seconds, maybe less, before I came on her tits. She then took me by the hand and led me to the bedroom. We had intense sex for the next hour or so. It was strange how much of an effect Matt had on our sex lives.
We talked it through and decided to take a break for awhile. She was a little worried about how Matt would act at work, but he was a gentleman to her and things settled down. At first she was a little reluctant to talk about her work relationship with Matt, but she mellowed out and things returned to normal for the most part. It was me who suggested another dinner with Matt. This time she didn’t put up any resistance at all. She grinned and said, “Okay, weirdo.” She called him later that day, and he came over for pizza and beer.
The second time around definitely was much easier. My wife still needed a few drinks to loosen up before things started getting sexual. As she handed him a beer, she leaned into him to kiss him and squeezed his crotch with her hand. Then she stood up and held her hand out for him. She started walking to the bedroom with him and held her hand out for me. “Just a sec,” I said. It was almost too much for me thinking of my wife leading another man to my bed. I sat there stunned with my mind reeling. I was jolted into reality when I heard my wife calling for me. The second time she called, I responded I was coming.
When I walked into the bedroom, I noticed Matt was lying naked on my side of the bed. My wife had her top on but her skirt and panties were off. She was kneeling between his legs with her face bent down low while she was sucking on his balls. Matt looked at me for approval, and I nodded it was okay. When his dick went limp, my wife turned and looked at me. I was just standing at the foot of the bed watching them. She pulled me over toward the bed, and sat on the bed with me standing in front of her. She took of my shirt, then my pants, and then lifted my boxers over my erection before she gave me an intense blowjob. I shot my load into her mouth in under a minute.
She walked over to the sink, spit, and then brushed her teeth before coming back to bed. I was still standing like a retard on the side of the bed, and Matt had pulled a sheet over his private parts. She jumped on the bed, still bottomless, and patted the bed motioning for me to climb onto the bed. Once I got on the bed, she turned her full attention to Matt’s dick. She started back down to the underside of his balls. Outside of porn and a locker room, I’ve never really seen another man’s dick up close. Matt’s balls were huge and hung really low – like a big flabby sack. She sucked one of his balls, and he winced, so she started sucking a lot more lightly. The whole time she was stroking his dick with her left hand.
His dick looked a little gross with a giant blue vein bulging on the top side. I thought his dick was kind of small until my wife’s mouth started having its effect. As he got harder, his dick got much fuller. When he was completely hard, he was clearly bigger than me, but not by a huge amount. When he was sticking straight up, she positioned herself over him, and the squatted herself down onto his dick. As big as it was, it went in easily. She rubbed her tits all over his face as she started to ride him. Her pussy was puffy and you could tell she was turned on. I remember thinking, where’s the damn condom?
After a couple of minutes, she leaned forward and whispered into his ear. She lifted off of his dick, and then got in doggie style position facing me with her face resting on my abdomen. He got behind her, spread her legs a little, and then inserted his penis back into her. He started slowly pumping her, and she was slowly leaning back into his thrusts. At first she was looking right at me, but after a couple of seconds, she closed her eyes and I could see pure pleasure on her face. Matt leaned forward a little and had his gaze fixed squarely on my wife’s ass and his penis going in and out of my beautiful wife.
His thrusts got more and more rougher to where he was even moving me on the bed as he pumped my wife. She didn’t make a whole lot of noise and just whimpered every now and then. Then he gave my wife a light smack on her heart shaped ass. She opened her eyes and gasped at the same time. She looked at me, and flashed a wicked little smile. “Spank me, Matt. I’ve been a bad girl.” He then started swatting her ass with more frequency while his thrusts got more forceful and abrupt. I started to feel sorry for her pussy! Then he yelled that he was cumming. My wife hunched her hip forward forcing his dick out. He started grooving my wife ass cheeks with his dick until he started shooting rope after rope of cum all over her back and ass. He rolled off her and pulled the sheets over his midsection. She lurched her chest forward with her ass still high in the air. She asked me to get her some water.
I pulled my boxers on, and went to get some water. When I got back, Matt was asleep, and my wife was still lying on her chest with her ass sticking in the air. Her ass cheeks were splotchy red where he smacked her bottom. His cum was still shining in the light all over her lower back and ass. Her pussy lips were red and puffy. She had a big workout with Matt. I handed her the water, and she looked up at me adoringly and said, “I love you, honey.” I kissed her after she took a couple of drinks. She then said, “Are you going to make me ask?” I replied, “Huh?” She said, “Climb on, baby.”
I dropped my boxers in a flash, and then proceeded to have sloppy seconds with my own wife. What a turn on! My dick slipped in effortlessly. I thought his big dick must have stretched her out a little. I saw the cum on her ass, but I still couldn’t help reaching for her hips as I started pumping her doggie style. My hands drew back when I felt his sticky cum on her hips, but I got over it. I stared at my wife’s cum-covered, reddened ass as my dick went in and out of her pussy like Matt’s just did. I was running on pure adrenalin with such a charge. I didn’t bother to pull out of my wife. I just shot my load deep into her womb. I almost collapsed onto her back until I remembered Matt’s cum on her ass.
Matt must have awoken during our sex. He reached over and started fondling my wife’s tits, and started making motions like he was going to fuck her again. She politely said, “We’re done for now Matt.” He stopped suddenly and looked a little hurt. She said, “I am going to need a little rest down there after you two big boys.” She smiled at him, and he then smiled back at her. She leaned over and kissed him full on the lips and said she would see him at work on Monday. He got dressed and left.
Things kind of went like that for the next few months. Matt would come over every other weekend, and we would have our little party, and then he’d leave. My wife and I couldn’t stop talking about how good our sex life had become with our new ‘little’ play toy. Little did I know how things would soon change.
I came home from work one day and saw Matt’s truck full of boxes in my driveway. Matt and my wife were sitting at the kitchen table. My wife said, “Hey. Uncle Matt’s moving in for a little while.” I was dumbfounded. I asked my wife to step out into the pool area so we could talk. I asked, “Are you for real?” She said, “It’s just for a little while.” His lease at his apartment is up, and he needs a place to stay until they finish building his new house.” “For how long?”, I asked. She said, “Maybe a couple of months.” Before I could protest, she leaned into me, grabbed hold of my crotch, and then whispered, “It will be so good for you. Trust me.” I marshmallowed my okay.
Sex really did get a lot better. We literally had sex every night. The only thing I had trouble was that my wife and Matt cuddled and shared the same blanket at night. My wife and I evolved over the years to where we each had our own blanket – she’s a blanket hog and we compromised. We used to cuddle a lot when we first got married, but started cuddling less the longer we were married. Now with Matt, she would kiss me, and then roll over into his arms. I’d wake up in the morning with them embraced or spooning.
Plus, Matt and her had way more sex than she and me. My wife would take turns at night with us kind of like we had always done. Then, we’d say our goodnights. But, sometimes, Matt would still be a little horny, and I would have to lay there listening to her sucking his dick or him fucking my wife. He liked to hold my wife’s legs straight up with her feet in his face. As he would fuck her with a pillow under her ass, he would lick, kiss, and suck her feet and toes. Or, they would tangle their legs with him over my wife and her lying on her side. As she bent herself fetal style, she would reach in between their legs and massage his balls and prostrate. He’d would smack her ass, and really plow into her pussy the whole time. After he came, he would roll over to his side, and go right to sleep. She would curl up under his arm and sleep with his cum still inside her pussy or down her throat.
He even got my wife to try anal for the first time. It took her about 15 minutes just to get the head of his cock inside her ass. Once he finally did, he came in like five seconds. They still laugh about it to this day. She says it was painful as hell; he never really got it all the way in; he premature ejaculated her anally; and her butt was sore for the next month! Still, she says Matt took her butt-cherry and deflowered her ass. Me? I came in my pants just watching them.
I still get that special charge when she is with him. And, I get to be a part of their sex life – their sex life is part of my sex life. In addition, she spends all of her time outside of the bedroom with me. We are still a strong couple in every other sense of the word. I know I am making a cuckold of myself, but it doesn’t feel like such a bad thing. I don’t consider myself a true cuckold even though I openly admit that is exactly what I am. I am a cuckold, and I like it.