Going back in history, how I was set up or conditioned to be a cuckold.

How I got started: Part One

All rights reserved, no posting without written permission.

I’m a cuckold, a wittol and even a candaulist. Actually I am a cuckold fetishist, a bit of a submissive cuckold fetishist to be a bit more precise. You can’t really be a cuckold with a girlfriend but I did feel very much a cuckold when Kate, an old girlfriend in a relationship that lasted six years, had sex, had lovers and fucked other men without my permission and without my knowledge. My wife (first marriage for both of us) of almost thirty years drops her panties, spreads her legs and fucks other men and has romantic relationships including sex with other men with my knowledge and it gives me pain and pleasure. Brandi and I first welcomed another man into our bed (yes the first time was in our bed in our bedroom) for over twenty-two years. At various times in our married life Brandi has been pretty easy, she guesses she had about forty or fifty lovers or bed partners as a single woman and so far she has had at least that many as my wife meaning that she has enjoyed or at least known in an intimate way at least a hundred cocks.

We started with a mfm as a step to swinging but as time past we drifted into hotwife games and cuckolding. I find pain and pleasure in my wife having lovers and me being submissive to her sexual needs and desires and her lover’s needs and desires. Cuckolds tend to call those feelings “cuckold angst”. The total pleasure we get has to be greater than the total pain for it work. I’d never have thought that I would actually enjoy, actually love being cuckold. I don’t love my wife having sex with other men, I just like my wife fucking other men.

But I love my wife having lovers and “making love” with her lovers, knowing my wife is fucking other men is hot but knowing my wife is “making love” with lovers is incandescent. For me

I hate and enjoy my wife having wider sexual limits with her lovers and even “friends with benefits”. She knows that she can do pretty much anything that she and a lover want to do without having to do the same with me. One reason my wife enjoys long term relationships with her lovers is her love of bareback sex. My wife wants to feel her lover’s come on her and in her. She doesn’t she has been with a lover unless he comes in her pussy. Brandi does not feel that she has been a naughty wife unless her lover comes in her cunt. She also enjoys the romantic touches with some men, her lovers. The romance is important. While she considers some men lovers there have been about four or five that have been “Lovers” with a big L, men that she really loved, so there is a bit of polyamory in her approach to cuckolding me.

However there certainly is some down and dirty sex, some nasty fucking as well. For example once I was on a trip she celebrated one of her birthdays with four other men, she promised to let me watch her sometime with four or so men but it has been at least five years and I am still waiting. She has spent the night with lovers, had semi-public sex downtown with a lover, let lovers kiss and fondle her in public including revealing her breasts, ass and pussy. It has been at least ten years since I have come in my wife’s mouth, some of her lovers cannot make that claim. She tells me that I might get to come in her mouth again “sometime”. So how do you define “sometime”? I’ve been in my wife’s ass once, right after a lover was there, she tells me that maybe I might get to try that again but she also tells me that if a lover really wants her ass and asks in the right way…my wife will be delighted to let her lover enjoy her ass. My wife pleasing her lovers and herself and putting their sexual needs and desires first causes me pain and pleasure.

So I consider myself a submissive cuckold. That does not mean I am a “sissy cuckold” but I have worn panties and will again if my wife and or one of her lover’s want me to wear panties, and it does not mean I am submissive in other ways to her and to others. Indeed I am guilty at times of “topping from below”. Brandi would not have affairs, be a cuckoldress or a hotwife unless she enjoyed the sex and the relationships including the romantic relationships and wanted to do it for her own reasons but she also would not do it unless she was sure that I enjoyed the pleasure and pain that it causes me and that I want and need her to have lovers.

How did I go from a normal marriage, monogamous and all that to having a wife that so far has enjoyed at least fifty cocks since we have been married and a life time total so far of at least double that? I would guess that she has had about four or five real Lovers rather than lovers or fuck buddies since we have been married.

It started long before I ever met my wife. I was a teenager in the 60’s and an avid reader of Playboy, Penthouse, Adam and a lot of swinger magazines and newspapers. The thought of swinging was a big turn on. I knew I had to try that. I spent part of my growing up years in South East Asia. So my first sexual adventure was in a house with a professional woman not too long before my fourteenth birthday. She cost two dollars plus tip and a few drinks. Hey, this was at a mid-range price and quality house but keep in mind that the dollar was worth a lot more in 1965, think what minimum wage was back then!

I am sure that this had a lot to do with my later attitudes as well as giving me a profound liking if not admiration for working women. The ladies there were great, not always beautiful but great. A lot of the girls were really pretty and were pretty nice to customers. I have never been with a pro in America but from what I have seen the American pros and dancers seem to view a lot of their customers with contempt. So, I have had little temptation to indulge with hookers in as we used to say, “the land of the big PX”.

So, loaded with all this information about sex, swinging and all I started college and had my first real girlfriend not too long after. Kate was young, but no virgin. She had started having sex at an early age too, early in her thirteenth year and had two or three boyfriends before me and enjoyed sex to various degrees with all of them. To be honest we played some before sex. I can remember spending hours in bed with her; starting with us both dressed. A few dates later and I was in my underwear and Kate was in a bra and bikini panties, eventually in just her bikini brief with me naked (and hard) and at last both of us naked. It was fun, the kissing and touching each other. It was great. The suspense was great.

It wasn’t all that long before Kate and I started having sex. She had a lot to learn but so did I. I learned that intelligent girls are far more open to trying things in and out of bed and we both were quick learners. In the beginning we had to use rubbers but in a few months Kate was on the pill. After a good while I started trying to talk her into swinging and we came close in the six years we were together but we never did. We did spend the night at an infamous motel near the Oakland airport called the Edgewater that usually had a lot of swingers, we didn’t play but it was great to see my girlfriend swimming and chatting with a few guys while she was naked. I had to admire how cool and calm she was with it. I also tried to get her to try a threesome and toward the end I even tried to get her to go to bed with another guy as long as she kept me posted and completely informed.

We spent a few summers apart, at least three. Hard on any relationship. The first time she was gone teaching English and learning Spanish in Mexico I noticed that we would talk some about sex but not much and we didn’t have phone sex. No privacy was part of the problem. I also notice that while I would share my sexual thoughts with her and write erotic letters to her, she would not, except to say that she missed me and our lovemaking. She returned home and our sex life was hot again. I did flirt some and came very close to going to bed with a few girls but never went quite all the way. Even then I enjoyed going down on a woman and making her scream with pleasure. Hey it wasn’t real sex if I didn’t actually have my cock in them, right?

We both enjoyed flirting and Kate had a certain kind of sexiness about her. When she was going to college one of her fellow students hit on her and did get her interest. A Mormon of all things and they did date some. He was kind of devout and a bit of wuss. She gave him a few hand jobs and sucked him twice, she let him come in her mouth and swallowed but that was as far as it went. By this time Kate was great at both hand jobs and cock sucking. She did want to go to bed with him but he was reluctant to take that step so they never did fuck.

One summer she went off to Tennessee for a while. Lived with my brother and his wife. Kate and Pat, my brother’s wife, went way back as friends. Dated some there but didn’t go to bed with anyone, or so she said. Looking back she did mention that a manager at the restaurant she worked at made a pass at her and they did go out on a few dates. So I would guess that he might have been Kate’s first black lover. By this time Kate was an outstanding sex partner, she was open to a lot of things. She would strip naked and suck me as we were driving. I don’t know how many miles we drove with Kate naked in the passenger seat with her lips on my cock and or my fingers teasing her pussy. No bikini was too small for her to wear. She seemed enjoy others seeing her naked or almost naked. Anyway sex was an important part of her life at this time so the chance of her spending an entire summer without sex seems kind of remote.

Another summer things got more interesting. She was visiting my brother and his wife in North Carolina. After a while it got harder and harder to actually talk to her when I would call her, she was out or busy all too often. She showed up back home in SLO a few weeks later than planned and to be honest she had changed her hair and other things so much that when she stepped off the bus I wasn’t sure it really was my girlfriend. Funny how that caused some temporary problems. I don’t think I got any that night.

We had a lot of talking to do but it wasn’t really until a year or so later that I got most of the real story. She first admitted that she had enjoyed some dating. Then she mentioned some kissing, touching and then admitted to just a little sex, one or two times. Then it came out that she had actually moved out of my brother’s house and into an apartment with her Marine boyfriend. As time went on I got more of the details. It hurt but it also turned me on. I felt betrayed that she hadn’t shared what had been going on as it was happening.

As it turned out Kate had been busy. Very busy! Her lover, the one that she had moved in with was not the only guy that had enjoyed her hot little pussy that summer. He was messed up enough on drugs that he really wasn’t too good in bed, Kate was getting into drugs at that time so the major thing they had in common was drugs, mostly pot but they did get into other things. This was not too long before the services started drug testing so I wonder what happened to him? She had several other sex partners that summer, not often enough to call them lovers in my opinion. But she had done something different, something that I had wanted her to do with me. Something that was very hot but also hurt a lot.

It took a while but after several conversations I think I got most of the details of this one adventure from Kate. She was over at her boyfriend’s place where she was living and they were getting loaded on some pot. A male friend of his stopped by and joined in on the getting loaded. At that time getting loaded made Katie very horny so she started kissing her boyfriend, let’s call him Mike since I think that was his name. He didn’t seem to enjoy or respond to that so she gradually worked her way down, pulling up his shirt and kissing and nibbling. The picture I have is that Kate was on her knees between her boyfriend’s legs. She started opening his pants and he still did nothing to stop her and did lift up a bit so she could get them down a bit. She fished his semi-hard cock out of his underwear and was soon was giving him a blowjob in front of their friend. Due to the drugs Kate’s lover had some problems getting it up at times and this time was no exception. As Kate had her head in he boyfriend’s lap she felt hands caressing her butt. She said she had kind of forgotten any one else was there. Startled she looked back and of course it was their friend, we will call him Tom since I have no idea what his name was or is. She expected her boyfriend to say something but he didn’t, so Kate went back to sucking on his cock.

Kate kept sucking on her boyfriend and their friend kept caressing her butt. No one said or did anything to acknowledge that Kate was sucking her boyfriend cock in front of their friend and their friend was caressing Kate’s butt. After a bit, Kate guessed that Tom realized that his friend, Mike, Kate’s boyfriend, and Kate were not going to protest. Kate felt his hands begin to explore more of her body. She was in a bit of a drug and lust induced fog and was not sure what was going on, how far things should go, or might go or how she really felt about it. She did say she was getting very turned on. She did wonder what her boyfriend thought as well as what possessed their friend to join in their play. But all she did was keep sucking on her lover’s cock and playing with his balls. Kate really enjoyed giving and getting oral sex and liked playing with cocks. Just like my wife Kate found men and their bodies fascinating and enjoyed touching and playing with them.

Kate kept busy with her boyfriend as their friend explored her body. She felt Tom’s hands running over her butt, down her legs, up her back, around to her breasts. Then she felt his hands exploring between her legs. A little shocked but she didn’t do anything to stop him. On one level she told me she expected her lover to say or do something. Since he didn’t do anything to stop him she didn’t do anything to stop him either and she told me she kind of acted like it wasn’t happening. She did say that she thought about closing her legs. Tom applied a little pressure to the inside of her legs and without thinking about it she opened them a bit. He caressed her a bit more including between her legs. Pushed again at her upper thighs and Kate said she didn’t hesitate to open her legs a bit more.

Then she felt Tom’s hands tugging at her belt and getting it open. Then he got her jeans unbuttoned and unzipped. Then his hands started wandering over her body again. Caressing her butt, up her back and down to cup her breasts again. Unbuttoned her shirt and pushed it up and then he was fondling her breasts through her bra. Kate had only 34B’s, really they were fair sized 34A’s or small very small 34B’s but they were cute! Kate’s cute nipples would show through a bra when she was turned-on or cold. Then she felt Tom’s breath on her neck as he nuzzled and kissed her ears and neck. No sign of any reaction from her boyfriend.

Then Kate felt his hands back on her butt, and then he was working at her jeans, slipping then down her rounded butt. She admitted to moving a bit to help him work her tight jeans down off her ass and down her legs to above her knees. I could have guess that since Kate wore her jeans so tight that unless she was willing to cooperate it was impossible to get them off of her. Again she fell his breath on her neck and ears and his lips brushing her skin. Then his hands were caressing her butt through her panties. She was embarrassed but she had been getting very turned on and when Tom’s hands went between her legs, she was very aware of how wet her pussy was getting. Kate knew that he realized how wet she was by the way he was teasing her pussy through very wet crotch of her panties. I love how wet Kate would get, I have had her so excited that her jeans looked like she spilled cup of water on them. It is not at all unusual for Kate to get actually dripping wet, running down her legs wet when she was excited.

Kate said that she didn’t look up, she kept her head in her boyfriend’s crotch and her lips on his cock and balls, she was trying to show no reaction to Tom’s touching. Somehow trying to pretend that nothing was happening as a guy was slowly undressing her as he was caressing and fondling her body. Still no reaction from her lover, or at least no negative reaction from Mike. Kate felt Tom’s hands explore her mostly bare back. Then he slipped them around to her front and she felt his hands on her bra, caressing her breasts again. He fumbled with the front clasp of her bra and opened it up and pushed her open bra and her shirt further up. She could feel Tom’s his breath on her ears and neck as he kissed her neck and fondled her breasts. She remembered his hands as feeling quite hot and her nipples being quite sensitive. Kate’s breasts are small but she had cute puffy aureoles with medium sized nipples and her nipples are very sensitive.

Then she felt his hands back on her butt pulling her panties down just a little, exposing her ass. He caressed her full butt for a few moments and then kissed and licked her butt. She kind of knew what was coming but she still had a sense of wonder that her boyfriend didn’t react any to what his friend was doing to his girlfriend. Kate felt her panties being tugged further down, about mid-thigh. Tom was able to caress Kate’s pussy and tease her clit, she admitted to opening her legs a bit more to make it easy for Tom to tease her pussy and get a finger between the lips of her pussy. She felt Tom’s hands leave her body and then felt him untying and slipping her shoes off. Then Tom started pulling at her jeans and she lifted her legs one at a time as he worked then on down past her knees and finally all the way off.

His hands went back to my girlfriend’s ass and pussy, fondling and caressing her. Try to picture this, Kate had her panties a bit above her knees, legs open, stretching her panties so that Tom could reach between her legs and play with her pussy. Kate’s bra and shirt were pushed up so she was naked from below her shoulders to right above her knees. Tom had his hands exploring and fondling Kate’s breasts, ass and pussy. My girlfriend and her local live-in boyfriend were pretending nothing unusual was happening, everything was normal! All of this exposed skin gave Tom a lot of my girlfriend’s body, naked body to explore and enjoy. Kate kept her head in her boyfriend’s crotch, licking and sucking on him. Tom’s hands seemed to move faster and Kate thought he was getting very excited. In his growing excitement he then pulled, really yanked Kate’s panties down and off her left leg and left them around her right ankle. I think he was getting a little excited. Kate was now naked below her waist, except for her socks and her panties on her ankle and her bra and shirt that were almost to her neck. Still no reaction from her boyfriend.

She felt him between her legs, she opened her legs a bit to let him get close to her. She was shocked a bit when she felt the heat and hardness of his very firm erection pressing against her, against her ass. His hands were wandering all over her, cupping her tits, teasing her nipples, between her legs, spreading her lips and teasing her wet pussy. She opened her legs a bit more as he moved, she felt the tip of his cock between the opening and wet lips of her pussy. He teased her for a bit with the tip of his tool. She admitted to moving around a bit trying to get him into her, into her pussy.

At last she felt him ease in a bit working the tip of his cock in her entrance, teasing her a bit. Once he was sure that he was lined up he then thrust hard into her, all the way, she felt his balls slap against her. She told me she was so wet and ready he had no problem going all the way in, that surprised me a bit since Kate had a rather tight pussy. She told me she had to moan, his big and very hard cock felt so good to her after having to deal with her boyfriend’s soft erections. Part of her was wrapped up in how good it felt but she also felt like she was watching it, almost not being part of it, wondering what was going on, how it was happening.

She moaned with pleasure, her mouth still full of her boyfriend’s cock which she suddenly realized was now getting harder. No reaction from him beside his cock getting firmer as her lover’s friend started fucking her. Kate told me that she had an orgasm almost immediately, right when he first rammed his cock into her. She doesn’t think that he lasted all that long, but she admits to being rather carried away by the whole thing including the lust, drugs and the lack of verbal reaction from her boyfriend, an erotic fog that she told me tended to blur details. After her first big orgasm she had a couple of small orgasms. Tom’s hands were all over her, teasing her breasts, playing between her legs, adding to her pleasure and helping her to her small orgasms. Then she felt Tom pick up his pace, start to thrust harder and deeper into her pussy. She told me that she felt rather sloppy at this time, her juices running down her legs, very open and wet for Tom’s cock. Then she felt him thrusting harder and deepening his thrusts, grab her hips and pull her onto him as he thrust hard, almost savagely deep into her, and start to moan as he came, she came again, a really big one. She could feel his cock all the way into her, his balls pressed up against her, she felt his cock jerk and she sensed or felt the heat and wetness of his come in her, he would thrust, gripping her hips hard and hold as he spurted, then slide back and thrust and hold and spurt again and again, gripping her hips so tight it almost hurt. She told me that his come felt burning hot in her and she felt very wet, hot open, very sexual she was thrashing around in Tom’s hands as her orgasms swept over her. As she jerked around a bit her boyfriend started to come and she took a spurt in her mouth and the rest of his load spattered on her breasts as she lifted her head up as she was coming. She told me that she was very aware of Tom’s balls hitting her as he was doing his final thrusts deep into her as he was coming. The heat and wetness that she felt in her pussy made it clear to Kate that he had filled her with a very big load of come. She could feel their combined juices oozing down her legs, Tom quit thrusting and almost was collapsed on her back, his breath hard and hot on her neck. She said it felt good and very erotic to feel his still hard cock in her, the warmth of his body and their juices running down her legs.

She remembered rubbing her lover’s come into her breasts as she pulled herself more erect. She could feel her new lover’s breath hot on her back and the warmth of his body as he was still pressed up against her. She put her face back down and everyone took a little breather, her face in her boyfriend’s lap, her nostrils full of the scent of his come and sweat. His friend with his still hard cock in her pussy and his sweaty body bent over her also sweaty body, breath hot on her neck as he gasped for some air. The room reeked of sex, of fucking, she said she was very aware of the scents at that moment.

After a bit Tom pulled out of her pussy, still half hard and she stood up and stretched. She watched him pick up her panties that had slipped all the way off and wipe his cock clean on them. She thought she saw a little smug look on his face. She wondered if Tom was smug about using her panties to wipe his cock off or was he feeling smug about fucking his friend’s girlfriend in front of him? Her boyfriend pulled up his pants up and Tom got dressed. Kate slipped her bra off in that way that women can without pulling her shirt off. She picked up her jeans, socks and panties and tossed them and her bra on their bed. Went into the kitchen and got everyone a beer. Left her shirt open as everyone made small talk. She said that she was very aware that her boyfriend’s sperm was drying on her breasts, her lips were tender from sucking his cock, his taste was in her mouth and some of his come was on her face, her shirt was open and they could see her breasts and her pussy and the lips of her pussy were open and she was leaking, leaking a lot from her well fucked pussy and she felt the sticky mess at the top of her legs. She could feel it seeping out of her pussy and a couple of trails of come running down her legs and she knows both guys looked at it, looked at her almost naked sweaty body. No mention was made of what they had just done.

Kate said that they never had another threesome and nothing was ever said by any of them about what had happened. However she admitted that she fucked her lover’s friend several if not many more times that summer and fucked a few more of his friends. Tom just assumed that they would keep fucking and she didn’t mind since her boyfriend was still having problems getting it up due to the drugs. Not sure why she fucked the other guys except she said she felt she had no real reason not to. She became very casual about wearing just a shirt, partially buttoned with or without panties or a t-shirt and no panties or just a bra and panties around the apartment when male friends were around. She told me that she would also get “caught” coming out of the bathroom naked after a shower or a bath on her way to the bedroom get something to wear. She actually enjoyed being “caught” not dressed and at times would plan how she would expose herself. She was sure that after a short while it was obvious that she was deliberately exposing herself to Mike’s friends.

Mike never said anything about it, but she did sense he seemed to enjoy it. The other men wouldn’t say anything unless Mike was not within earshot. After a bit some of the guys would take a quick discrete feel. The showing off, mostly to men that she had fucked, was very arousing to her. Seeing other girls look at her with disgust mixed with a bit of envy was also a turn-on.

The pain was intense, each detail slowly added over time just increased my pain. I really loved Kate and I was hurt by her actions, how could she fuck all those guys, how could she do things like that? But even in the beginning I was bothered by her not telling me about it, making me a part of but as time by that pain started to change. I also had to admit that the whole thing was very arousing to me. Along with the pain that each additional detail caused me, each added detail added to my arousal and lust. We would re-enact parts of the scene and other things she did that summer and other times. Some of my images come from seeing her showing me what happened, like slipping her bra off, her panties on her ankle, such details things added to my arousal and my pain. Her casual telling me and showing me what happened made it very real to me. The mental image of my girlfriend, my true love between two men, one slowly undressing her, exposing her beautiful pale Irish ass and her small but adorable breasts while the other man was enjoying her considerable oral talents was so exciting. Kate really enjoyed sucking cock and she enjoyed feeling you come in her mouth.

My love having a boyfriend, a lover and then fucking another guy in a threesome and then her being such a slut for the rest of the summer, so hot, why didn’t…why couldn’t she do that with me! So hot and so painful.

Later, after we had broken up I found out more from her about that summer. She told me that she and Mike never talked about that threesome or that she was fucking most of his male friends. When he had shift work at first Tom, or later as she took on more lovers, or one of the other ones would stop by and they would fuck. In the beginning she would not use their bed. But a few weeks after Tom started stopping by while Mike was at work she started using their bed with him. The fucking on the floor and sofa got to be too uncomfortable. Sometimes Mike would get home minutes after Tom or one of the others would leave.

One afternoon after a long and intense session with Tom Kate closed her eyes for a second rather than running for the shower. Sure enough she drifted off into a nap. Mike got home, found Kate naked on the bed, just waking up, bed messed up, her bra, panties, jeans, and shirt in the living room and a big wet spot on the bed. As Kate woke up she saw Mike ripping his clothing off, then he joined her on the bed. First he started kissing and fondling her. She tried to keep his hands away from her wet and open pussy but he forced his way there. After teasing her to the point she was moaning he then went down on her and ate her to an orgasm. He commented on how wet she was and then ate her to another orgasm then he moved up between her legs and slid his cock into her very wet and open pussy. Moments, seconds later he came.

Kate is sure that Mike knew more of what he ever let on, the days she had sex with one of his friends were the days that Mike just had to have her, including eating her out. He never commented on her obvious wet and used pussy or the wet spot in the bed. She got so she didn’t try to hide things. Mike would come home and bottles or glasses for two or more would be in the living room. Her clothing would be scattered around the house, a bra here, a pair of panties over there, jeans on floor by the sofa. She would be naked, at times asleep, in the bed, her pussy wet and open, a wet spot or two in the bed. She was never caught in bed with one of his friends but Mike would come home to find her and one of his friends having a drink and she might be in a t-shirt and panties or just a long t-shirt with some of her underwear scattered around and the bed messed up and with a wet spot or her clothing on the sofa and a wet spot there. A few times she had more than one visitor during the day or night when Mike was on duty. She realized that it had gotten out of hand when during a little get together not long before she left to return home and to school she was in the kitchen at their place talking with some of Mike’s friends. It hit her that she had sex, she had fucked and sucked all six of the men in the room and Mike was not in the room at that time. She felt a bit naughty and a bit hot.

She was so turned on thinking about that she had to drag Tom away to the garage and sucked him hard and then turned around and bent over a car as he jerked her shorts and panties down and her top and bra up and had a quick but intense fuck. She was sure that all of her “friends” knew what she and Tom had just done and she was turned on by them knowing she had just fucked him. She left her bra and panties in the garage and noticed later that she had a wet spot on her shorts from Tom’s come and her own juices.

She said it was such a rush looking at all those guys and knowing she had enjoyed all of them in her mouth and pussy and “knew” them! Kate had no idea how many guys she was with that summer, most of Mike’s male friends and some of their friends, guys that she would meet at squadron parties and other gatherings. Such a naughty girl.

Some other things that I think influenced me from my time with Katie should be told. One time we were visiting my brother and his wife down in Santa Ana. A friend of Kate and Pat’s (my brother’s wife) came up with her husband from the San Diego area. She was the sister of another one of Kate and Pat’s friends and closer in age to Pat. She had married a nice guy but things were rocky for them, lots of living on love and Rice Crispies. The husband was a nice guy and tried to be a photographer. He got the women to pose nude, I never got to see all of the shots but Kate was by far the best looking and he was a terrible photographer, horrible pictures. Kate and Pat were cute to very cute and Kate had certain “girl next door” type of sexy cuteness about her and he had managed to make all three women look bad! I did find Katie being seen naked by two other men to be exciting. Pat was and is cute but the other girl had a somewhat sloppy body and large saggy breasts, I didn’t find her at all arousing. “Meow!” Pour me a bowl of milk!

One day on that same trip we were alone in my brother’s apartment. Kate and I started fooling around and soon we were both naked. I had bought a twelve-inch double-ended dildo made in a soft plastic for us to play with. Kate enjoyed being filled with it. It had a life-like shape and to be honest it was just slightly thicker than my cock and I was almost seven inches and that was just about all Katie could handle of the dildo. I would get that fake cock in her and nibble on her clit and she would just about bloody my nose with her orgasms. It was fun. I also used in on her ass a few times and I think I enjoyed that part of it more than she did. She did say that she enjoyed the feeling of both holes being filled but wished it was a bit smaller. I really enjoyed the few times I got into her super tight ass and to be in her tight pussy while she was responding to her ass being filled was fun. Anyway we were down there, playing frisky risky games and we were naked in my brother’s apartment in the living room.

I had Kate on the sofa with her legs spread wide and about half that thing filling her tight little pussy with me teasing her clit with my tongue. After her first orgasm one of us, might have been her, got the idea of her keeping it in her pussy and fucking me with the other end. She frequently wondered aloud what it was like to have a cock, how did it feel to have a cock and to fuck with it. Kate’s first boyfriend turned bi and one of the steps on to deciding he was bi was giving up on girls for a while. That did make her a bit interested in what made men bi or gay. She told me Vern was a pretty nice guy, well endowed and a fair lover. Not too long before we broke up I did have the chance to see Vern naked and erect and Kate was right: I could see why she thought he had a nice cock but that is another story. Anyway the experience of Vern being very gay and at times very swish for a while did not turn her against gays and seemed to make her more open to her trying bi, which she later did and she certainly was not a homophobe.

So a few minutes later she is behind me, that dildo hanging from her pussy and I am on my knees and bent over with my face and shoulders on the sofa. I felt her fingers spreading my cheeks and lubing up my virgin ass. I tried to keep a little bottle of lube with the sex toys and took them and the Kama Sutra oils with us when we traveled, one has to be ready for any opportunity! I was excited but I also felt more than a bit submissive and a bit weird. I mean I was bent over and my girlfriend was getting ready to slide a fairly large toy in my ass. That toy being a rather large fake penis made me feel more than a bit funny!

She knew I was tight and nervous. She took her time. She got more lube on me and worked it into me with first one finger and then two teased me a bit, saying such things as, “I’m going to fuck you with my big cock! Going to stretch that tight ass of yours!” The sensation of her fingers teasing my ass and going just a little way in and being well greased felt sensual, erotic, pleasurable but when I would think what she was planning on doing I would get nervous and feel my whole body tighten up. But she kept working her fingers in me and adding lube, working the oil into my tight ass.

She lubed up the dildo and then moved between my legs. With some effort she got the tip of it where it needed to go. Holding it, guiding it with one of her hands and the other on my stiff cock to hold me still she tried to force it in. It felt huge! I was ready to call it quits but Kate is really getting into it. She lets me know that she is determined to do it, to fuck my ass with her fake cock. She wants to try to feel what it feels like to fuck and she wants me to feel what it feels like to be fucked! She spreads a little more lube on what she is calling her cock and on my ass. I feel her rubbing that fake cock between the cheeks of my ass. She gets on target and pushes as she holds my cock and pulls on me to stop me from trying to get away. I was trying to pull away.

I feel that huge thing pushing at my tight ass. It really seemed much bigger when she was trying to fuck me with it than it looked. She pushes harder and the tip starts to slide in, spreading that tight ring, it hurts but not as much as I thought it might, burns a bit. She pulls back and lubes it up again and greases up two of her fingers and not very gently pushes them into me and works them around opening me up more. She is getting very determined to do this and I am getting more nervous but still excited.

Words are being muttered by my girlfriend, not sure of the exact words but the meaning is clear, she was going to do this to me, my girlfriend was determined to fuck me! I feel her hand between us, holding her plastic cock. She has her other hand back on my cock, holding me, stopping me from getting away. She guides the head again up to my sphincter and pushes. I start to open, I feel it opening me up. It feels giant. I try to move a bit, to ease the pressure and she holds me tight. The pressure eases a bit and then she pushes it harder, harder into me and now the tip is almost in me. She eases the pressure and then pushes again and eases and pushes then again and the tip is in me. I can feel the tip, the slightly smaller area right below the tip of the head of that toy cock enter my sphincter as I moan. She eases it out. Ah, relief. I feel her hand move from between us and feel her squirting more lube on the dildo. The lube feels chilly as she moves her plastic cock up between the cheeks of my ass again.

Kate moves back and forth just a bit and then presses firmly forward and I feel the thick tip of that fake penis against my little bud, my somewhat opened and lubed bud and it starts to give to the pressure that Kate is applying. Kate mutters, “I’m going to fuck your ass!” She pushes a bit more and again I open to the pressure and I feel the head of the dildo slide, force its way in, the head is in, I feel the slight relief when the head is in me and the toy gets slightly smaller. I feel full! She eases the pressure and then moves forward and gains a bit more, not more than a half inch, back again and then an inch, again, now a couple of inches and in a bit she can’t fit her hand between us, pushing more she has it all the way in, all six inches that are not in her very wet pussy. “How do you like my cock in your ass?”

She slaps my ass cheeks. “Like being fucked in the ass?” I moan, mostly in pain and embarrassment. I feel silly, more than somewhat submissive, a bit humiliated and a bit turned-on. At times she is slapping my ass, spanking me and other times she has both hands on my hips as she tries to fuck me. She keeps asking me how I like it, how does it feel, do I like having her cock in me, fucking me and so on. “Like that cock in you…Like me fucking you…you look great with a cock in you…you want a real cock…want to get fucked by a real cock?” I gasp out a few answers but she doesn’t really hear them, it doesn’t matter, Kate is in some sexual zone, a hot one. My growing humiliation, my submissiveness turns her on more and more and her arousal turns me on.

I am bent over in the classic doggy position, Kate is bent over me, her legs between mine, forcing my legs apart, opening me to her “cock”. I feel her body heat, her small tits against my back, her bare skin against me, so this is how it feels? I feel that toy in me, feels giant. She tries to fuck me but the dildo will not stay in her, she is too slick and wet. It seems that fucking her boyfriend’s ass turns her on. She pulls back letting the toy slip out of her wet pussy. She grabs it and not too gently starts fucking me with it, Kate lets go of my cock. I look back and see that her face is contorted with passion and lust, her hand between her legs playing with her pussy and her other hand is still on the toy fucking me.

I watch her face, I grab my cock with one of my hands and start stroking. I see her shudder, moan and convulse in an awe inspiring orgasm! I’m close, very close. She pushes my hand away and starts stroking me, hard. I hear her moaning, muttering as she works the toy cock in me, “like that cock up your ass…queer…like being fucked…fag…take it…like that big cock…fuck…fuck…”

I put my head down into the sofa and take it, submerge myself into what was happening. I moan that I am about to come and her hand, her grip on my cock gets harder, stroking me hard, not at all gentle, hurts but it is hot, she shoves the dildo hard into me, grabs her pussy again and I feel my sphincter grabbing at the toy as she shoves my t-shirt under my cock and I come…bucking against her hand as she hangs on stroking my cock, I am very aware of the toy in my ass, aware of her coming again as she feels me coming. She keeps jerking me off as I sink down, spurting, a mess and she shudders and falls over me. She keeps stroking my cock as the pleasure goes to pain and the last of my come dribbles out. I have to yank her hand off my cock. The t-shirt is wet with my come and I feel the mess against me. I am very aware of that big fake cock still deep, over six inches deep in my ass. We pant, gasping for air. I slump to the floor and she is slumped against me, both of us are drained, beat, orgasmed out. In a few moments she giggles, tells me it looks silly seeing that toy cock sticking out of me and then she eases the plastic cock out of me, my ass feels empty but a bit sore. She rolls off of me, flat on her back on the floor, naked, legs open her pussy wet and open. She looks so fuckable!

I start to get hard again, I had only gone half soft. In moments I crawl between Kate’s legs and start to nibble on her wet pussy. Only a few moments until she has a violent orgasm, almost bloodying my nose. She pulls me up, begging me for my cock, demanding that I fuck her. In a flash I am in Kate, my cock still wet with my come and her pussy is wet, hot and open. Kate was usually tight but she was hot, soft, open and so wet, delightful. I feel her fingers again teasing my ass, in my somewhat sore ass. It isn’t long until we both come again, not as intense as the ones we just had but still hot. We snuggle, naked, her pussy leaking, my ass feeling a bit abused and with the lube still wet on my cheeks, feels slick back there. I feel good but also wonder. I felt “taken”, “used” or something, a bit submissive, yes a bit sub and very fucked, very hot and a bit shamed. Loved it…but? We did get cleaned up and dressed before my brother and his wife made it home. That would have been something, to be caught naked, bent over with a naked Kate right behind me, fucking me or to my side ramming a large dildo in my ass while she was stroking my cock!

We never did that again even though we did some ass play, I think maybe we felt it wouldn’t be as intense or maybe there were other factors, like no place or time for such a session. Not long before we broke up Kate mentioned a few times trying to get together with Vern, her first lover and having a threesome. Katie had a detailed fantasy (she kept most of the details to herself and told me she often used the fantasy while she was masturbating) of the three of us having some wine and fun at the hot tubs in Avila Beach. Never happened for more than one reason but Kate later told me that she wanted to see two men together, she was sure it would be hot and she was positive that Vern would like my cock. Kate also assured (assured?) me that Vern found me attractive. I had met Vern a few times at one of Kate’s friend’s house and Kate also told me that she and Vern thought I had a cute ass. If she was trying to make me think or wonder or worry, she did.

I used to tell her that as interesting, fascinating and sexy I found women it made sense to me for women to find other women sexy. Kate told me that she wondered why more men didn’t find other men sexy or sensual. She later explored her bi side and enjoyed it, but did not find the romance that she was seeking there…but she did enjoy the sex! Thinking back to her comments and efforts for us to have a threesome with her old bi lover Vern…did she see me?…us?…oh never mind!

After that my brother and his wife were visiting San Luis, we go out after a few drinks at a nice bar and then to the local hot tub place, Sycamore Springs. Wine. Naked. All of sudden I am kissing Pat and caressing her body and Kate is being explored by my brother. No penetration, that I know of, at least that is what Kate tells me later. She also tells me that I am a lot larger, longer and thicker than my brother and she likes the thickness of my cock. Makes me wonder if my brother got to try Kate’s tight little pussy in Tennessee or later in North Carolina? I think a very good chance he got to enjoy it.

Another time we were up in Sacramento, again visiting my brother. This was getting close to the end of our relationship. We were getting ready to go out. Showering together she looked so cute and sexy, I played with her until she came, expecting that I would be able to bend her over and fuck her from behind after her orgasm. After she comes she grabs my hard cock and starts to jerk me off. Again not gentle. I try to escape her grip but I can’t. I move, twist and dodge and she hangs on. I don’t want to come but her grip, her stroking me, she has me at her mercy, she just might hurt me? The shower tub floor is wet and slippery, we are sliding, I am very aware of the risk of falling, we are thrashing around some. One of her hands is on my ass, teasing my little puckered bud, sliding in one finger, then two, the soap lubing me for her fingers and burning a bit at the same time and her other hand stroking me, jerking me off. What an orgasm, intense, wrenching, lots of come spurting. Her hand still jerking on my cock, her fingers still in me. So intense that I slide down the side of the shower, moaning as she keeps her hand stroking my cock, jerking me off. I struggle with her, it hurts now, at last she lets go and it takes a while for me to recover enough to get up. She rubs the come on her hand on me, smearing it around on my skin. I feel beaten, a bit ashamed I couldn’t hold off or get her to fuck me or get away. I really wanted into her pussy and she knew that. She chose to have me spurt my come on her hand and into the shower, not into her! But the orgasm was intense. Some hot submissive feelings again.

Toward the end of our dating I would be out with Kate in a group of our mutual friends, I’m in town for the weekend at her urging, we would be in a restaurant and I would be caressing her one of her legs working my way up to her crotch and find another man’s hand there caressing her. I later found she was indeed fucking a few guys while I was gone and even while I was home, visiting at her urging. She would beg me to come down and then when I was there tell me that she had a date and couldn’t see me! We would have dinner and she would go over to one of our mutual friend’s house and fuck him! Arrgh! North Carolina did make me feel like a cuckold but to a certain extent that cucked feeling was after the fact, now I was really a cuckold, if one can be an unmarried cuck, since I would sit in my car with a friend and we sit outside her lover’s house and know she was in there getting fucked and of course she was enjoying it very much! At first she told me that she wasn’t having sex with her friends, our mutual friends but later she admitted the obvious truth, she was fucking them.

All of our friends must have known my long term girlfriend/lover was sleeping around, fucking around. My brother and his wife knew that Kate had been dating and probably sleeping around in Tennessee and knew that Kate was living with her lover in North Carolina and my brother may have fucked her a few times himself, the public knowledge, the public humiliation hurt but also excited me. It all made me want her more… But I guess it wasn’t meant to be.

I found another love after a few false starts and we started to drift even further apart. But all of a sudden Kate found me more interesting and we had a few great sex sessions as we drifted further apart. Once we went to the hot tubs in Avila and had some wine and necked in the hot water. She swung over me and lowered herself in the water onto my erection, to my surprise it was obviously a very practiced maneuver for her, she had gone from being a bit uncomfortable or unskilled at fucking in the hot tubs to being a pro at it. She was working at McClintock’s (a nice dinner house) as a waitress in Shell Beach at the time and I later found out that they, the workers would party a couple of times a week at Sycamore Springs in the hot tubs and she was fucking several of her fellow workers. That explained why she never let me go out with her on one their after work parties and how she was so good at fucking in a hot tub. She had indeed lots of practice swinging over a guy in the tub and lowering her wet pussy onto his hard cock! I am sure toward the end of our relationship I had sloppy seconds a few times and I had my first taste of cream pie.

It was a bit funny but after we had broken up but were still friends she told me that she had always been careful to have only one lover during a “period” so that she would know who the father was. I brought up her playing with her fellow McClintock’s workers at Sycamore Springs as well as her summer in North Carolina. Then I brought up my visits home that she would somewhat grudgingly have sex with me while also seeing at least two other guys as well as the McClintock’s crowd. She blushed, looked a little shocked and laughed. If Kate had got knocked up, just who would have won the prize?

Not sure why things came apart, her cheating when she could have been playing was an important factor, it hurt at the time, and it still hurts. On the other hand knowing that others had enjoyed her cock sucking skills and her tight pussy was very exciting. I have to say that she was great in bed, open to trying things, very oral, really enjoyed sucking cock and she swallowed. Unlike a lot of women Kate really liked come, she would joke about “all those little spermies swimming around in me” and she would rub come onto her skin, her belly, breasts, around her pussy. Kate would show you her mouth full of the white come she had just nursed out of your cock. Tease you with it and then swallow it all. She liked the mess of sex and liked large loads in her pussy or on her skin or in her mouth. She loved come! She would hold, fondle and caress your cock and balls between fucking sessions, she liked men and their equipment. I loved the fact that she liked being wet and sloppy, full of come after sex. She even enjoyed the wet spot. At times after sex she would get dressed and the crotch of her jeans would get soaked through, she didn’t mind, it was like she was boasting about just having fucked. She didn’t mind hot tubing with other couples or with just some of the guys and didn’t get shy, she still went in naked, we got walked in while we were making love at a few parties and that didn’t bother her at all, I think it turned her on. I would have loved to see her playing with another man or woman and didn’t mind, heck, I loved the idea of sharing her but with one added point. I love the idea of sharing my wife or lover…as long as she made some effort to make me a part of her play.

She loved having her little pussy eaten, that beautiful tight little pussy that she tended to keep mostly shaved and her even tighter well rounded ass was available to being nibbled on and I did get my cock in there a few times. She had lots of enthusiasm for sex. Not as orgasmic as my wife Brandi but she bloodied my nose more than once as she came from my tongue. She could thrash around and come hard, a bit more effort to get her to come that Brandi takes and Brandi is easier to get to that multi-orgasmic state. I could not say she was beautiful (she really was to me) but she was attractive and sexy in a “girl next door” way. About 5’6”, 130 or so, dishwater blond hair, blue eyes, very fair skin, pale Irish looking with some freckles, slightly pug nose, pert scant 34B breasts with great nipples, slender on top with a fantastic curvy ass that was generous in size. Her ass might have been her best feature but her little tits with her fantastic nipples looked great under a tight top with no bra.

I can see how some of the “bricks” were laid on my way to building my “cuckold wall”. I must admit that without meaning to my darling Kate had laid a firm foundation for my later desires. Sitting outside a house while inside I knew she was busy fucking a mutual friend was upsetting and arousing. The anger at her asking me to come down and visit and then spend time fucking others was just plain maddening. The knowledge that she was getting to be a bit of a slut and had shared herself with so many lovers and fuck buddies is still a turn on for me. When I think about Katie and her first threesome, the mental image of her pale white body between two men, sucking one and the other fucking her brains out, or at least filling her tight cunt. I see her gorgeous pale curvy ass gleaming in the daylight and her tiny tits moving, faint tan lines. I see it in my mind and I still get hot and bothered, my cock gets so hard! What a glorious image, one guy deep in her tight little pussy, his hands on her pale ass when he isn’t reaching under her and fondling her small but beautiful tits, those tiny tits with her hard fantastic nipples swaying and her curvy full ass rolling with his thrusts into her wet pussy and his hands full of her small tits and his fingers teasing those great nipples. On other end she is working her oral magic on her boyfriend’s cock and balls! What an image, what a woman. What a hot little fuck!
Yes, she was the first to “cuck” me and it is obvious that she really started me down this path! Thanks Kate…I still lust after you and love you!