Tell us about an encounter of sexual inadequacy

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inactiveduty
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Tell us about an encounter of sexual inadequacy

Unread post by inactiveduty » Sat Jul 22, 2023 5:30 am

I think a lot of cucks got their start by realizing they were unable to perform. I’d love a thread where we share a time we were obviously noticed by our partner as being sexually inadequate. I can go first.

Back in college I was dating this Italian-American girl — pretty eyes, nice smile, a little overweight, big features, olive skin, big boobs, brunette, about 5’4” or so — and I was going down on her. She moved her foot down and having a foot fetish I started humping it while licking her pussy. I was able to cum really quickly and we never ended up having sex. She was a little surprised but I think a little impressed with herself that she was able to cum without doing much. She later told her roommates (friends) and she referred to it as “the foot incident”. She didn’t cuck me directly but we did stay in touch and she would later tell me about fucking better lovers.

Alimpy4K
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Re: Tell us about an encounter of sexual inadequacy

Unread post by Alimpy4K » Sat Jul 22, 2023 1:16 pm

When I was 22 I had a flirtatious situation going on with a coworker. Cute blonde with glasses, nice curves, big tits and just super sweet and cute in general. It was a small town, so I came to find out that I knew her sister. The sister actually called me out of the blue and told me if I was interested I should hurry and ask her out because she was thinking about moving away. So I thanked her for the tip and the next day at work I asked the girl out.

I took her on a date and at the end of the night I ended up fooling around in her bed. She stopped and said she didn't want to have sex with me yet, but said she'd give me a blowjob - she later told me she really gets off on sucking dick. Anyway, so that was cool and all and we continued dating for a short time, during which I got several more bj's.

But, long story short there was an argument caused by her not being able to hold her alcohol. She didn't normally drink, so I figured we could patch things up after a day or 2 and not let that one night ruin things. So I started coming back around her house to hang out. But things had changed. Now all of a sudden she had multiple guys knocking at her door per day, calling her phone, etc. It was clear that while I was letting things calm down for 24 hours or so after her drunken outburst, she had been actively reaching out to 'see other people' if you will. I did get maybe 2 more blowjobs, but I gave up on seeing her because it was just too late.

We ended up not working together much longer either. So a few weeks go by since I had seen her at all and I ended up talking to the sister I mentioned earlier, who I had known for years. The have a love/hate sisters type of relationship, so she started talking bad about the sister I had dated for whatever reason. At some point she mentioned that her sister was very slutty/generous with her giving out of blowjobs to a lot of men. And she said she liked to do it before fucking a guy to see how big his dick is. Well, I had gotten some blowjobs (And only blowjobs, no pussy) so I couldn't helped asking, "Did she say anything about how big mine is?"
I could tell by the look on her face immediately that she had. She hesitated awkwardly, and said, "She said it's just not as big she's used to"

beta boy

Re: Tell us about an encounter of sexual inadequacy

Unread post by beta boy » Sat Jul 22, 2023 3:45 pm

inactiveduty wrote:
Sat Jul 22, 2023 5:30 am
I think a lot of cucks got their start by realizing they were unable to perform. I’d love a thread where we share a time we were obviously noticed by our partner as being sexually inadequate. I can go first.

Back in college I was dating this Italian-American girl — pretty eyes, nice smile, a little overweight, big features, olive skin, big boobs, brunette, about 5’4” or so — and I was going down on her. She moved her foot down and having a foot fetish I started humping it while licking her pussy. I was able to cum really quickly and we never ended up having sex. She was a little surprised but I think a little impressed with herself that she was able to cum without doing much. She later told her roommates (friends) and she referred to it as “the foot incident”. She didn’t cuck me directly but we did stay in touch and she would later tell me about fucking better lovers.
Should have hung out and told her about your foot fetish and wait till you recovered then give her a go again. I would have asked if I could start by kissing her feet and promise her a good fuck.

p_jimi
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Re: Tell us about an encounter of sexual inadequacy

Unread post by p_jimi » Sat Jul 22, 2023 3:48 pm

I started to masturbate at the age of 15. I was not a very macho type of guy, so when I was young I was not around girls. At the age of 18, my eyes opened and I started dating. It often happened that my dick didn't get up or I came too fast. I managed to marry a girl who was full of inhibitions and almost never enjoyed sex. I was also guilty of this because my cock never stayed hard for more than a minute or two. I wanted my wife to really enjoy sex. Anyway, the thought of my wife sleeping with other people excited me, so I started to encourage her to sleep with other people as well. She hesitated for quite some time, but finally decided to sleep with other people. Her first lover was a real stud who fucked much better than me. When it turned out that she had a lover, we discussed that she would regularly fuck other people, which she tells me at home, which really excited me. We still had sex for a few years, but after that she only had sex with other people.

beta boy

Re: Tell us about an encounter of sexual inadequacy

Unread post by beta boy » Sat Jul 22, 2023 4:31 pm

I have many storys. I'm very small. One time my friend and I went to the city to get blow jobs. We found this hooker and bargained a price.He went first while I waited out side the car taking a short walk. When it was my turn he waited out side the car.I noticed her kind of snickering and asked. She said oh nothing, just thinking of a funny thing that happened eariler. When she was done blowing me she was getting out of the car and my friend was getting in. I heard her tell my buddy that I had smallest cock she ever saw. And this was from a NYC hooker. Another time when I was with my first girl I had no experience but knew I needed to use a condom. We got together in the upstairs of our barn for what I thought was going to be a good time. She had already been around a bit and had some experience. So she took my condom and unwraped it and started to get me hard with her hand. Suddenly she says is that all you got? And started giggling. She tried to roll the condom onto my cock but it was only one third of the way unrolled when she reached the base of my tiny penis.She couldn't help laughing and I was so embarassed and humiliated. She told me I don't even take up half the rubber and It's so lose It might fall off. She got up and left still laughing and telling me this wouldn't work out and I needed to find a way to make my dick bigger or maybe to become a girl.

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BBCfan
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Re: Tell us about an encounter of sexual inadequacy

Unread post by BBCfan » Mon Jul 24, 2023 9:20 am

I had never felt inadequate in my life, having received compliments always about my size And abilities.

Even though I know women tend to compliment guys  regardless, I know from stats that I am above average and supposedly in the 10 to 20 Percentile Above average.

The only woman that has ever commented on me being very average  sizewise is my wife.

This also led to me finding out she dated many guys very very large. Shockingly so.

  Even though she never gave me reason to feel insecure about my performance, The fact I knew she could handle and enjoy Endowments far far bigger than me, caused me to have huge insecurity  In a way i'd never experienced before.

Even when we had sex I began to realize more and more that there was a lot more room, especially depth wise inside her that I would never reach and that she has had reached many times before.

My cuckold thoughts and fantasies emerged from that,  and hearing stories about her massive exes and how challenging a few were, but how amazing they felt as well.

Now I no longer have the insecurities but instead feel so blessed to be with a woman that not only can please me, but can also please porn size dicks with great pleasure.

Hopefully I can see her doing so again soon!
Our hotwife journey story so far
viewtopic.php?f=48&t=60133

excitedPotential7

Re: Tell us about an encounter of sexual inadequacy

Unread post by excitedPotential7 » Sun Jul 30, 2023 11:05 pm

The first time I was going to have sex was with this incredibly cute and shy girl from work. She was the nicest and sweetest girl I had ever met. Long story short, I took her to a hotel and once there we started kissing and getting naked. Eventually I put it inside her and started doing the best I could. I came after a few minutes but I noticed that even as I was thrusting as hard as I could, she hadn't made a sound. She Just laid there. After I was done, I looked up and she gave me a weak smile and said she had to go to the bathroom. She took her phone with her. Originally, we were supposed to spend the entire night there but once she left the bathroom, she apologized and remembered that she had to be home. I was shocked but took her home anyway. 15 minutes after I dropped her off, I realised that perhaps I had messed up so I drove back to her house to try and salvage the night. I knew her parents wouldnt be home but she wasn't responding to my texts so I decided to leave. Anyway, the following Monday at work, a co-worker buddy of mine was excited to show me something during our break. He didn't know about my weekend date for the record. Anyway, once we were alone, he pulled out his phone and showed me a video of that same shy coworker from my date, the one I couldn't get a reaction out of no matter how hard I tried, literally bouncing and riding his cock as she moaned with extreme passion and pleasure. To see this shy girl turn into that was breathtaking! Beautiful even. I felt inadequate but that was part of the delicious sensation. Apparently after I dropped her off he picked her up ten minutes later and took her to another hotel where they went at it ALL NIGHT LONG. He had plenty of videos,texts, and pics too prove it! He kept fucking her brains out for more than a year while I did everything to treat her like a queen. What a fun experience

MartasBoy
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Re: Tell us about an encounter of sexual inadequacy

Unread post by MartasBoy » Mon Jul 31, 2023 2:26 am

There was this girl I met, a really hot Jewish girl with big brown eyes and long thick brown hair and a voluptuous body. We flirted for a while through our work connection and decided to hook up. She told me she found me really good looking and was really looking forward to having sex with me.

She had a three-year-old daughter and didn't want to have me over at her place. I had a roommate, and not a very private situation of my house. She wanted to wait until her 3-year-old daughter wasn't around.

Then she called me one night and told me that her daughter's dad had moved to town and had her daughter over at his house and she had her place to herself. I went over and she was all over me. She was excited because her ex was going to take her daughter with him the next day, for two weeks, to go visit his family, and we would have a lot of time together.

I had trouble getting a very strong erection and my penis kept falling out of her. I needed a lot of help from her to get hard again each time we tried to have me inside of her again. Finally she got frustrated and pushed me off of her and brought herself to orgasm with her vibrator.
The next morning she called her ex and asked if she could go with him on his trip. She told me that I had helped her realize how important good sex was for her.

MartasBoy
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Re: Tell us about an encounter of sexual inadequacy

Unread post by MartasBoy » Mon Jul 31, 2023 3:43 am

I remember another woman with whom my poor performance was actually a benefit to the relationship. Our first night together I had my usual trouble staying inside and maintaining an erection. Each time my penis fell out I would need her help to get hard again, and for her to guide me inside of her. On the 3rd or 4th attempt I came a little then lost my erection for good. I apologized for not giving her an orgasm and started to go down on her with my mouth. She pushed my head away and said she never liked having men slobber all over her down there.

Our second time together was the same. She admitted to me that night that she had never liked sex. She had been molested by her uncle when she was a little girl, and raped by a guy in college, who she thought was her friend. She told me that she had always found sex gross and messy.

On our third time together, just as I made it inside of her, she said it was uncomfortable. She brought her legs together and I popped right out. I asked her why she even tried having sex with me. She said that she knew that guys liked it. She also was willing to try three times with me, because she said I didn't act animalistic like most guys when they get turned on. She said she always hated the way that most men acted animalistic when they got sexually aroused.

We dated for about a year and a half. She was a nurse and worked weekends. I didn't have laundry machines where I lived so she let me do laundry on Sundays at her house while she was at work. She would leave a key for me and I would go over and do my laundry. The deal we worked out was that I would do her laundry too.

Each Sunday I would go to her house to both our laundry. I would fold her bras and underwear and put them away, up all of her blouses skirts and slacks for her. She would come home from work, make us dinner, and let me stay the night. To offer me a reward for doing her laundry, and to tend to my sexual satisfaction, she would give me a handjob when we went to bed. She called it "giving me my time".

She said that she felt most safe with me of any guy she had been with, because she knew that I could never force myself on her, because of my small penis, and the fact that, in our three times that we had intercourse, I needed her help to get hard and be guided inside of her.

So each Sunday I would go to her house do her laundry and put it away. She would come home and we would have dinner together then she would say, "Let's go to bed and I will give you your time." She required me to where an unlubricated condom with some KY inside for lubrication for me, but so that she wouldn't get any mess on her hands. Then I was required to take off the condom, wrap it in tissues, and dispose of it in the kitchen trash. Then I went to the bathroom, cleaned myself up and put on underwear and pajama pants so I didn't mess her sheets.

shesaidtome
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Re: Tell us about an encounter of sexual inadequacy

Unread post by shesaidtome » Mon Jul 31, 2023 7:43 am

Stamina has always been the big issue from me, and in my early twenties, just after college, I dated a girl for a few months and was just a DISASTER with her. Of course I took care of her other ways, but when it came to intercourse, especially back then, honestly the most common thing was for me to be losing control as I was sliding in for the first thrust. I could really sense her building frustration, and started telling myself... "Ok, this is IT. You really need to do better or you're going to lose her." SO, after masturbating earlier in the day to hopefully make sure things wouldn't be IMMEDIATE, I decided that I was going to slide in and then just WAIT, calm down, and when I was ready, at LEAST try to give her more than 6 pumps (my record "best" at that point)... Hoping that she'd be like, "Ok, he's at least improving!" And then I'd blow her mind with oral and all would be perfect. Right?

SO, that night, after some making out, I climbed on top, and slooooowly slid in. Made it! Time to take some breaths, calm down, and then do my best. 15... then 30 seconds past of me just totally still on top of her, not moving... Both of us silent... And then... I felt a little tickle. Fuck. At that moment I just KNEW what was going to happen. All the time, NOT moving, absolutely NO friction, and I could feel an orgasm building. I remember looking down at her and her looking up at me with sort of a confused look on her face, like, "What is he doing?" I was absolutely mortified, I could feel my face flush, and all I was thinking was "No no no no no oh god please no". I held it in as long as I could, but after a bout a minute of nothing, I quickly, frantically pulled out, and with a very not sexy grunt, grabbed my cock and started spurting all over her stomach. I remember her saying "Oh my God!" and I also remember my hips sort of humping in the air and me grunting uncontrollably (which all felt really pathetic) and just trying to WILL the orgasm to stop... But it was spurt after spurt and so much... Which made it even MORE embarrassing... Like it was some EARTH SHAKING ORGASM... after absolutely nothing. And she was covered with so much come... After getting absolutely no pleasure at all.

Breakup soon followed.

w770
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Re: Tell us about an encounter of sexual inadequacy

Unread post by w770 » Mon Jul 31, 2023 7:59 am

I suppose the most notable time was when my wife took two younger guys in our bed, both of them having no problems bringing her to orgasm multiple times while I watched. Afterwards, when it was my turn, I got on top of her, made love to her for less than a minute before cumming in her, both of the guys smirking and laughing at the stark contrast.

MartasBoy
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Re: Tell us about an encounter of sexual inadequacy

Unread post by MartasBoy » Mon Jul 31, 2023 9:43 am

I remember another time when I was with a woman who shared with me that she enjoyed having a man restrain her arms, and her then being taken somewhat forcefully and aggressively. I tried it several times. I would get really turned on and have my full erection. She liked to put up some resistance and struggle. I managed to contain both of her arms and hold them above her head but with my little penis and soft erection I couldn't find my way to get it inside of her. Then, in my attempts to get inside of her, I would lose my erection. I had to let go of one of her hands, and ask her help to me get hard again, and to guide my penis inside of her. Then I would grab her arm back and restrain her again and try to return to the role play. But it lost the excitement for her and she just rolled me off of her and said, "Never mind. Forget it. Why don't I just use my hand to make you come and then I'll use my vibrator for myself." That relationship only lasted a few weeks, before she started seeing some guy she met at the gym where she worked out.

MartasBoy
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Re: Tell us about an encounter of sexual inadequacy

Unread post by MartasBoy » Mon Jul 31, 2023 12:14 pm

On the small handful of one night stands, when a woman has invited me home with her, they have had to help me get hard and help guide me inside of them. Usually I come very quickly and lose my erection. Generally these women have suddenly remembered something they had to do early in the morning and asked me to leave.
After I've come, I've rarely been asked to stay the night.
Whenever they have given me their number so I could call them again, it was usually the number to a pizza place or a dry cleaners.

cukgrl69
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Re: Tell us about an encounter of sexual inadequacy

Unread post by cukgrl69 » Mon Jul 31, 2023 12:58 pm

This may be a sort of strange response. I've always been a pretty good lover. My cock is almost 8" and I'm pretty good in bed. Most women I've been with have been impressed and very happy with my performance.

However, I've always had a sort of fetish for being inadequate, or rather, for wanting to be with women whose sexual appetites were so extensive that I would be unable to fully satisfy them. To me, I always felt sort of let down when a woman told me that I was amazing and that she was satisfied. I always wanted women to say that I wasn't enough for them or that my cock wasn't big enough or that they needed more, etc.

My first experience with this was a woman in her 40s that I was with for about 2 years in my mid-20s. We hooked up at a bar and I went home with her and we kept seeing each other. But she told me that she was not going to be exclusive with me because, she didn't care who is was, one man wasn't enough for her. But she did expect me to be faithful to her. In fact she said I couldn't be with anyone else while I was with her. This was really hot. I started liking it when she would see someone else before or or have plans to see someone else after I would leave.

On another occasion, in my late 20s, I hooked up with another older woman. She said, while dancing at a night club, she was only interested in "big dicks". I told her I was big, I said 8". So we ended up getting a hotel room. When she took my cock out to suck is she said, "Not bad." I could tell she was pretty loose as we started going. Then I told her to get on her knees. Her pussy was naturally gaping. When I put my cock in her I literally couldn't feel her, it was like I was in a tunnel and not hitting bottom or the walls. I was trying hard I was pressing all the way into her. I then kept pulling out to get a good look at her gaping hole. She started rocking back saying, "Come on." So I started licking her. I tried fucking her some more and I could tell my cock was doing nothing for her, which made me harder and then I came.

But she rolled over and was like, "Did you cum?" I said "Yeah, sorry." And then she just started masturbating. We laid in bed for about 30 minutes after that talking. I was hoping to get hard again and get another chance, but then she said she had to go. I've though about that many times.

Now as for my wife. For a long time we had I guess you would call it, a "good" sexual relationship. We had sex often. She said I had a big dick. She said I was one of the best guys she's been with. She always came when we had sex*. However, she always came by rubbing her clit, which I didn't really pay that much attention to.

But as years went on she told me about other guys she'd been with, etc. She talked about being with bigger guys and that she'd been with a few guys that were able to give her vaginal orgasms, but I wasn't one of them because my dick wasn't quite big enough and I can't fuck her quite long enough. Around this time we started getting into fisting and I was able to fist her to orgasm and she'd start telling me that she preferred fisting, which I thought was really hot. I loved it when we'd be having sex for like 10 minutes and then she'd ask me to fist her instead.

Then we started talking about having a 3-some with another guy and that then led to us finally meeting another guy, with a BBC BTW, and then going to a sex club. And its all been down hill from there. Now she loves talking about my inadequacy and how I can't possibly satisfy her anymore. Knowing I can pound her with my large cock as hard and long as I possibly can and it won't be enough for her is amazing.

ucaneffher
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Re: Tell us about an encounter of sexual inadequacy

Unread post by ucaneffher » Mon Jul 31, 2023 1:19 pm

inactiveduty wrote:
Sat Jul 22, 2023 5:30 am
I think a lot of cucks got their start by realizing they were unable to perform. I’d love a thread where we share a time we were obviously noticed by our partner as being sexually inadequate. I can go first.

Back in college I was dating this Italian-American girl — pretty eyes, nice smile, a little overweight, big features, olive skin, big boobs, brunette, about 5’4” or so — and I was going down on her. She moved her foot down and having a foot fetish I started humping it while licking her pussy. I was able to cum really quickly and we never ended up having sex. She was a little surprised but I think a little impressed with herself that she was able to cum without doing much. She later told her roommates (friends) and she referred to it as “the foot incident”. She didn’t cuck me directly but we did stay in touch and she would later tell me about fucking better lovers.
I never got turned on or into the lifestyle because any sexual inadequacy or anything remotely close to it. I will admit that I was 15 and was dating once of the hottest girls I'm my high school in my opinion of course. She was a friend before we became a couple and she always exhibited very flirtatious and promiscuous behavior. She always spoke so openly about sex and wanting to get laid all the time. For nearly a whole year before we became bf/gf and exclusive, she would tell me about all her dates and I even set her up with a few of my friends. While she was still a virgin, she would tell me about how they would give her oral, finger her, and strip her down in their vehicles.

Once we were exclusive and her sisters had met me, they were trying to steer her into the same direction that they were currently in which was being "players" and always meeting men and going on dates. Eventually I realized that it was two hot ass sisters and several slutty girl friends of hers versus myself, not to mention that my gf was already a huge flirt and had an army of guy friends while only having 3 friends who were already considered the school sluts anyway. At this point I felt it was the inevitable and it was only a matter of time before she joined her 2 girlfriends and her two sisters in being promiscuous. Her best friend was caught giving head to several guys during a School function and got herself quite the reputation.

By sophomore year I had accepted that it was only a time before the football team was also fucking my girlfriend just like they were fucking her best friend. I came clean and told her that I would prefer that she slept around and hung out with other guys instead of leaving me. I gave her the green light and spent sophomore, junior, and Senior year of high school hoping that my girlfriend would start dating guys and getting herself a similar reputation to her two girlfriends all while still having me as the boyfriend who allowed it and stood by her side supporting her slutty behavior.

She never did anything but she did go on several dates in senior year with no result but by the time we were out of high school and 19 years old, she began sleeping with men, lots of men. Once she started, she never stopped and dating other men became a part of her even while still being my gf. For the remaining almost decade of relationship, I never got to have my girlfriend entirely for myself and supported her for nearly a decade of meeting new men which became friends. Supported my girlfriend through nearly a year of friends with benefits and several boyfriends.

Tryagain
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Re: Tell us about an encounter of sexual inadequacy

Unread post by Tryagain » Wed Aug 02, 2023 6:30 am

I do not remember why I started having 3 somes with my wife, Jean. Perhaps it was because she was so beautiful that I wanted to show her off. I was 24 and she was 23 and drop dead gorgeous. Anyway, our first two 3somes were with my best friend. They were fun – we both fucked her and she was happy with the way things went. But there was something else that I found I had to prove.

This was before the internet but there was still some porn available and sex newspapers like “Screw.” Somehow I thought that big cocks were better than my barely 6 inch thin one. I set out to prove that. We answered an ad in one Screw issue that simply said something like “Swedish American sailor, very well hung, seeks single women or couples for good times.” We sent off a response – a letter - which included our phone number asking for him to call us. He called and I answered. I was new to this so I asked a few questions – basically height, weight and how big his cock was. He said “I am 28 years old and there isn’t an ounce of fat on my body and I am 9 inches.” I asked him to confirm “Are you really 9 inches?” He said yes so I made a date for him to come over to our apartment.

My wife, whom I love dearly, and who has always been very adventurous and open, knew about the ad and agreed to meet him. But she insisted that “If I don’t like him, I am not doing anything, period.” Okay.

He arrived late because he somehow got lost on the way. He stepped in and my immediate reaction was “this guy ain’t too cute at all. This is not going to happen” He was very tall – about 6 ft. 2 in. and very very thin. I thought “at least he did not lie about that.” As we ushered him into the living room, my wife gave me a distinct frown that said “I don’t like him.” He and I sat on the sofa and my wife sat in the chair opposite us. We began small talk. He was a clam digger on the south shore of Long Island. He also said that he had been a male stripper out on the island and that he had been asked but the editor of Screw, a porn newspaper in NY, to participate in a porn movie, which he had not made yet.

Well…this seemed to intrigue my wife very much. I could see her face brighten up with considerable interest. He asked where the bathroom was and he excused himself. She then said to me, motioning with her hands,” Did you see his pants? It looks very fat” and said it with a grin. I asked if she wanted to do this and she enthusiastically said yes. When he came back, she stood up and said she was going to the bathroom, leaving us alone. I told him we were going to do it. We sat for awhile in an awkward silence until he said ”Sometimes in these 3 somes, the women have multiple orgasms” This somehow set off a little alarm in my head – like – really? Jean was not yet having orgasms very much at all. And they were resulting from oral sex only.

Jean came back in and then I excused myself to use the bathroom. She later told me that he said “you are very beautiful. You do not have to do this if you don’t want to”. We went into the bedroom and Jean disrobed quickly and got under the sheets. Ken was starting to undress and then I began to undress but felt too embarrassed to look at him - like he would see me looking at his cock. At a later time, Jean said when she saw his cock, she knew the sex was going to be different. Somehow we all ended under the sheets with Jean in the middle. I pulled the sheet down a bit to reveal her breasts (they were somewhat small/average at the time. Now, after birthing, they are huge.) I started to suck her left nipple and then he started on the right one. It never takes much to start Jean off in a swinging scene! She immediately turned toward him and they started to kiss. I noticed that her left arm seemed to be moving. I really wanted to see if his cock was as big as he said so I slowly pulled down the sheets most of the way and saw her hand wrapped around his cock, which seemed very big but not sure if it was 9 in.

They were kissing and stroking each other and then he went down on her. She responded like she had with me. After a very short time, he knelt up and started to finger her pussy with 2 fingers. I thought “I never do that because I want to enter her when she is tight. Does he know what he is doing – short oral and then fingers?” And intending to fuck her so quickly without much foreplay?” I now know he was quickly proceeding to the real thing – the real reason why he was there. He prepared her for the missionary position. No condoms were used. He knelt up and stroked his cock and now...yes now I could see he was really 9 inches! And perfectly straight, not like my curved one.

He entered her slowly and her eyes became very wide open. She seemed to be feeling overwhelmed by it. He continued to put it in and out slowly and I thought “Why doesn’t he put the whole thing in?

She began to quietly moan (not like these days when she lets herself go) and moan some more and breathe heavily, so heavily like I never saw before. They fucked that way for a long time – longer than we ever fucked... I noted to myself “This ain’t like it was with Phil, my friend.” That time it seemed playful and fun. Now, I felt intimidated by him and realized that Ken and Jean were totally wrapped up in each other. There was no room for a 3some between these two. And by the way, I have no erection at all!

After a long while watching from the foot of the bed, looking at his ass and balls bouncing against her and hearing her moan in passion, I wonder to myself ‘ Why the heck are you doing this? She is having her brains fucked out and I am simply watching with no erection.

Anyway, she then asked to go on top. He obliged. She began going up and down on him furiously...again and again and again. I noticed that she was not going all the way down on his cock so I grabbed her waist and tried to force her down more on it but she slapped my hand away. She later told that, of course, she could not take the whole thing in without hurting (her young pussy). I lost track of time but I stared in disbelief that she was going up and down for so long! With me she always got tired after a few minutes. Finally she said to him ”I have trouble having an orgasm so you can finish up”. He placed her back in the missionary position, fucked her a bit and took it out and orgasmed a big load over her stomach – just like in a porn film.

Spent, they laid back down with me on the left side of her again. Jean and I had a cigarette lying on top of the sheets this time – all of us naked. I could not help to stare at Ken’s cock and compare it to mine. It was ridiculous... He was still all fluffed up – not hard though - from his erection and I had not had an erection at all that night. His cock looked at least 10x bigger than mine. Jean later innocently told me - not trying to make me feel bad or anything, just being her lovely but niave self - they did not even look like the same organ!

So after finishing the cigarettes and speaking for maybe 3 minutes, Jean reached over and grabbed his cock and turned towards him and they kissed. He immediately got up and set her up in the missionary position. We had a queen bed so things were tight, and he opened her legs and her left leg hit me in the head so I got up fast. Talk about feeling useless and in the way! Again another marathon fucking and more moans. I wanted to get involved somehow so I told her to move so she could eat me while he fucked her from behind. She complied and started to eat me but she could not do it. He was fucking her from behind, and she later told me it was so intense, so deep, and actually hurting her, that she had to stop and change positions. She said she wanted to be on top. And this time when she was on top she started making loud moaning sounds I never heard before and I thought “Ok, she is now having an orgasm from fucking him .” And I touched his cock as he was going in and out of her pussy and noted the rock hardness of him and a thick vein/ridge running along the back of it facing me. Man...was he hard! Shortly after that he came inside of her.
They rolled over in bed and, this time I felt like I had to do something sexual with her so, since I could not fuck her because I was not hard, I would go down on her. I put my face in her pussy and got such a shock; I felt pussy juice and cum, lots of it, all over my face from my eyes down to the bottom of my trimmed beard – my entire face. I was aghast! I was not expecting that. I immediately got up, went to the bathroom to clean my face and laid down next to her again.

Another cigarette…a little small talk ...and then I could not believe it. She grabbed his cock again! She wanted more! He once again got fully hard immediately. This time they did not kiss, but moved right into their familiar position - missionary – and he began fucking her slowly. I laid next to her and could see his cock go in and out but never all the way in. I reached out and, with my finger, stroked the top of his cock as it went in and out. He now reached over and grabbed my soft dick briefly but I was never going to get an erection that night. After a very short while, Jean said “I am feeling sore. Can you finish?” Like the gentleman he was, he said “no ...no more” And I will never forget seeing him on his knees slowly taking it out but he looked like he took 3 steps back in order to get it all out. And it sprang up and out from his hardness.

As if all of this wasn’t enough, Jean motioned to him and said “come here”, motioning him to kneel over her chest. I stared in total disbelief as he moved over her with his huge cock pointing straight at her mouth. She wrapped both hands around it and began to suck him with a loving look. – like she was really trying to please him. It did not take long to get him to the point of orgasm. And just like a porn star would, he took it out of her mouth and shot a load right onto her face. And then…she grabs it and smears his cum all over her smiling face. WOW. I could not believe she was so turned on and frankly so grateful and giving to him.

We all laid back down for a few minutes and, since it was getting late on this weekday night, he got up and went to the bathroom and Jean and I got up, and put something on to prepare for him to leave.

She had gone to the kitchen when Ken came out of the bathroom and got dressed. I will never forget the way he shook my hand and said ‘thanks, I hope she had a good time” but with an unmistakable smile/smirk that said “I really rocked her world, huh.”

Though I was dying to talk about things, she said she was tired and wanted to go to sleep but she did ask a rhetorical question with a smirk as well “I guess he was really 9 inches?” All I could do was nod in agreement and we went to bed.

The next day I could not wait for her to come home. When she did, I eagerly corralled her into the bedroom where she changed into casual clothes and we sat back on the bed. She was smiling and knew I was busting to ask questions.

She said she would like to do this again but I said something stupid like “yeah but he probably is just a one-time thing and will not return.” Of course 2 weeks later he called and got her on the phone to ask about getting together again. She told me he called and asked if we could do it again and I said “no. I really don’t want to do this” And like the terrific, loving wife she has always been, she agreed.

I began by simply asking “So how was it last night?” ( like I didn’t know already). My heart was pounding and I could feel the blood pulsating in my ears. I steeled myself for what was coming. She is a very sweet and loving lady ( I am so very lucky) and she asked me “ Do you really want to know?” Exercising great control over my emotions, I calmly and softly said ‘yes.” Because she is both caring and simultaneously wanting to be honest as well asked ” Are you sure because I don’t want you to feel badly?” Guys, I knew what was coming – but not really. With heart pounding harder I said “yes.” She seemed relieved and with great enthusiasm said “ I felt like I was fucked for the first time.” I asked her to go on. She said “fucking him was not the same thing at all like fucking me. Now I know why people say that they fucked for hours.” I tried to get more information but all she could say was that she enjoyed being all filled up and stretched. And she did not take the whole thing because it hurt too much but she did love the feeling somehow of the pain of his cock hitting the back of her vagina.

Well…I had my fucking answer – I was right all along. So now what? So I felt really deflated – that she could enjoy fucking so much – and with a perfect stranger!…yet somehow I also felt sexually excited. It was bizarre and I just could not figure out what was up with me.

Though I did not get hard that night, and thought that yes, I proved myself right that big cocks are so much better, for about 2 weeks after our scene with Ken, whenever I went to jerk off to think about that night, as soon as I started to jerk off, I came immediately , like in 2 seconds! And I had never had a problem with premature ejaculation at all.

About 6 months went before I experienced a strong desire to do this again, perhaps to somehow prove this was a one- time thing, that she did not really like a big cock that much, that it had been because he was somehow special. Boy, was I wrong!

SheLikesWhenIWatch
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Re: Tell us about an encounter of sexual inadequacy

Unread post by SheLikesWhenIWatch » Wed Aug 02, 2023 11:10 pm

Long story short:
My wife decided to jump in with both feet and cuck me in 2007.

My wife, less enthusiastic about cucking me than I was in being cucked, decided that she rather liked having a second cock around. For more than 15 years, he became her lover, and they cucked me often…..weekly. Despite my encouragement to try another man, she SWORE he would be her one extramarital relationship. She certainly fucked him solo a lot, but when I was occasionally (often?) around, she discovered she liked watching me masturbate while he fucked her and came in her.

Sexual inadequacy? Him watching me jerk off next to the bed where he’s fucking her. (It’s one thing for her to watch me. It’s her kink. It’s something different for him to watch me yanking on my dick and cumming in my hand while he fills her up. I guess it’s his kink, too, now….fucking a man’s wife right in front of him.)

Most recently, however, my wife decided to take ANOTHER lover. (She SWORE another one would never happen, but here we are!)

This time, we’re both A LOT more comfortable in our roles, and we thought it best to give them some space before she drops it on him that I like to watch AND that she likes when I watch. So, I haven’t seen her new boyfriend fuck her yet. (He fucks her about once a week.)

Still, she comes home and tells me detailed stories (which always end with me getting super-horny and fucking her).

Apparently, she says, his dick is smaller than mine, but “he’s sooooo much better at using what he has” than I am. “He’s more energetic. He’s more spontaneous. When he cums, it’s a lot and it’s thick. He’s better at going down on me. He’s better at fingering me. His cum tastes better. We’re the perfect height for 69ing with each other.” (And the list goes on.)

Sexual inadequacy? Knowing that a fellow with a smaller dick is pleasing my wife better than I ever have.

(I can’t wait to see this guy in action some day!)

i-wanna-be-a-cuck
Prepubescent
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Re: Tell us about an encounter of sexual inadequacy

Unread post by i-wanna-be-a-cuck » Mon Aug 07, 2023 6:56 pm

"Nothing worse than a dead fish". That's what one of my earliest girlfriends wrote in her diary about the first (and only) time she tried to get me off.

Ellen was gorgeous and way out of my league. By the time I dated her I was 18 and had had a few girlfriends. Getting a handjob and fingering were the extent of my sexual experiences at that point. Ellen was what I always strived for. My friends were jealous. Older guys at restaurants would mentally undress her from across the room. She was a good Catholic girl and we started slow. I worked up from touching her tits to fingering her.

One humid summer night we found a secluded spot by a neighborhood lake. We started heavily kissing. I was feeling her up and fingering her. She reached down to unbutton my shorts. My heart was racing. This was the moment I was waiting for with her. Sweet, religiously repressed Ellen was going to get touch my hard cock and make me cum. i was quite proud of my dick (and still am) being of a good size and always had the confidence she'd be impressed.

Well, that's not what happened. My whole body - except for my cock - went stiff. Nervous energy raced through my body. She pulled my shorts down and stroked my completely limp dick. It will get better as she stimulates me i assured myself. Nope. As I realized what was happening, my brain and heart started racing more. Nothing was happening down there. After about a minute of stroking my floppy, shruken, unimpressive penis she just stopped, pulled her hand away and stared at the lake. Obviously embarrassed I pulled up my shorts and made small talk like nothing happened. I tried to kiss her and she reciprocated but was very unenthusiastic.

She broke up with me a few weeks later. We stayed friends. Several years later in college she invited me to the college she attended to stay with her. We went to a party and then slept in separate rooms since she made it clear i was in the friend zone. The next morning she had to get up early to go to work and told me I could just sleep late and let myself out. I woke up and she was gone. It was just me in her apartment. I knew she kept a diary. This was my chance to know her deepest thoughts.

I found her diary on a shelf and flipped to find the date of the limp dick incident. All it said for that day was "nothing worse than a dead fish". I cringed and almost threw up. Then I read ahead to the next few months where she dated a guy whose parents owned a boat. She wrote about how they would be together alone on the boat and she would "take care" of him each time and how he "got relief". I was so jealous of that guy.

This incident still plays a role in how I think of myself sexually. Similar incidents occurred a few times in my life but each had much greater weight than it should because of what she thought of me that night. I'm only a wannabe cuck, but if I ever make it a reality it can be traced back to this feeling of inadequacy.

armyguyot1
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Re: Tell us about an encounter of sexual inadequacy

Unread post by armyguyot1 » Mon Aug 07, 2023 9:20 pm

Welcome to the forum I-wanna-be-a-cuck.

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