Cuckold in Courtship

By TooSmallDave.

Nowadays, my wife Emma is reluctant to acknowledge that I have a smaller dick than any man she ever went to bed with. (Although this is a fact and one that she felt compelled to remind me in the early years of our relationship constantly)

She firmly refuses to indulge my desire to be teased, scolded, or humiliated about the smallness and uselessness of my penis.

Nor will she be drawn into telling me intoxicating tales of her sexual adventures with the well-hung and dominant lovers who preceded me.

She tells me that my craving for humiliation, scorn, and derision is unhealthy and weird and that regardless of how much it might excite or arouse me, she will not bring herself to be mean to me.

More significantly, she adds that if she were to indulge my submissive and cuckold inclinations, it might well unleash feelings in her; resentment, desire, lust, and frustration: she has deliberately repressed, which could take our marriage down a path that we would both come to regret.

However, the myriad ways in which she has occasionally let slip her frustration at my inability to satisfy her sexual needs and her contempt for my small dick have been so delicately humiliating that they can entrance and arouse me far more than my recollections of cruelty and infidelity at the hands of previous girlfriends.

From the very beginning, our relationship was infused with a subtle yet powerfully intense and intoxicating narcotic perfume of jealousy, humiliation, and submissiveness. Ironically I felt it most keenly at the start when I was still painfully unaware and blinded by devotion.


I met Emma at the house of Lance, a mutual friend, and her ex-boyfriend. He was well known amongst our crowd as a sexual adventurer, a stud, a rough, dangerous man with a very big cock. Their relationship had ended, but she would still come to see him whenever he called. Indeed she was still seeing him regularly when we started going out together. She assured me it wasn’t serious and that she no longer had any feelings for him.

When we started dating, we told one another about our previous relationships and our future hopes. Emma told me that she’d been a wayward girl who had got into lots of trouble – usually involving sex and was always attracted to the wrong sort of man. She said she was keen to put her old life behind her and thought I might be Mr. Right as I was so different from the men she’d been out with before. She had always wanted to get married and have kids, as had I, and we were both at that age in life where we only have one last chance before it’s too late. Consequently, it was very early in the relationship that I was taken home to meet her parents, then her sisters and aunts, and the rest of the extended family. I was invited and obliged to attend many Sunday lunches and family events where I worked hard at getting Emma’s family to like me and approve of me as a partner to Emma, which they did.

Emma was adamant that we mustn’t rush things as regards our sexual relationship. She felt that that was where things had always gone wrong in the past. And she thought it would be more romantic and exciting: a proper, old-fashioned courtship. She made it very clear that if my feelings towards her were true and serious about marriage, I would be prepared to wait, woo her, and treat her with respect. It would demonstrate my suitability as husband material.

I agreed to whatever she said. She was (indeed still is) a gorgeous, powerful woman, and I was in awe, in love, and very proud that she was with me.

And indeed, there was a great deal of truth in her contention that sexual abstinence could be intensely exciting and romantic: I was constantly horny, which somehow intensified my feelings of love devotion. I would do anything she asked in this state of celibate courtship. I put all my frustrated libido into being the perfect, devoted fiancé.

I must confess that this was also a cause of some relief since I was nervous about sex because my cock is very small. At 3 inches in length when fully erect, it is little compared to most men, let alone our mutual friend, Emma’s ex-boyfriend, the famously well endowed Lance.

Although we didn’t have sex during our courtship, we dated, held hands, caressed, kissed, and cuddled. Emma dressed very sexily, and she allowed me to touch her voluptuous body until I became too excited, at which point she would kiss me on the nose and send me home. She never let me stay overnight at her flat.

I was desperate to see Emma every day if possible, but this wasn’t easier as she was very much the busy young woman around town going here and there with little time to spare. So I was more than happy to drive her around whenever she needed driving. She would phone me at any time of day or night to pick her up from here and there: work, the gym, friend’s houses, pubs, and nightclubs and take her to her flat or her parent’s house or friend’s houses in my car. I sometimes felt a bit like her chauffeur, but I was only too grateful that I could be useful and of service to her.

She would often phone me to collect her from Lance’s place, a house he shared with some other mutual friends, some of the guys I worked with.

The first time I went to his house to collect her, I was let in and waited downstairs. I knew his housemates and thought we would chat. But they seemed to avoid me and gave me funny looks, so I made an excuse and said I had to wait for her in the car. I waited for over an hour, watching the door from where I was parked over the road in a state of nervous excitement and a growing knot of sexual jealousy in my stomach. When she finally came out of his house and walked to my car, got in, and kissed me, I was so relieved and happy to see her that I felt mean for imagining that they’d been having sex. She was so lovely to me as I drove her home. She even let me put my fingers in her cunt when we made out in the car outside her flat.

She said that Lance was very disappointed with me for not waiting in the house so he could say hello. I was to phone him and apologize to him for avoiding him. He was hurt because he really likes me, which I was surprised but flattered to hear. When I tried to explain that I hadn’t felt welcome, she said I was being silly and made me promise to wait for her downstairs the next time I had to pick her up from there. Which it transpired would be the following day as she was going to his place straight after work. She would phone when she wanted me to come and drive her home. She didn’t know what time it might be.

So it was that the following night she phoned for me to collect her around midnight and I was invited in to wait downstairs for her. I sat there making small talk with Lance’s housemates, waiting while she was upstairs in Lance’s room. I had to wait for over an hour again, and when she finally came downstairs, she looked as though she’d just got dressed. Her makeup looked as though it had been freshly applied in a hurry. She was patting her hair, adjusting her clothes, carrying her shoes, and hobbling. Lance followed behind her, wearing nothing but a pair of shorts and looking like he’d just got out of bed. He was very friendly with me, inviting me to stop for a beer, but she was keen for us to go as quickly as possible, and I was tired as it was now almost 2 am.

It was much the same whenever I picked her up from Lance’s, which was usually two or three times a week, sometimes more.

As our relationship progressed, she began to invite me into her flat for an evening. I would cook a nice meal, and afterward, we lay together on her sofa, holding hands, drinking wine, and watching films. We became more intimate and passionate. She let me go down on her, and I worked very hard to bring her to orgasm with my tongue and fingers. Previous girlfriends had told me I was good at that. But I found she wasn’t so easy to satisfy.

The first time I went down on her, I was busy licking her as skilfully as I could with my tongue and using my fingers to penetrate her cunt when she suddenly let out a cry of irritation and told me to stop:

“God, Dave, if you want me to cum you’ll have to go a lot deeper and a lot faster than that.”

I apologized and asked her to be patient with me, but she was cross with me and told me to go.

That stuck with me. I can still hear her saying it now, twenty years later. When I remind her, she laughs and says she doesn’t remember.

I was anxious about the size of my penis. I’ve often been told it’s too small. When our relationship developed to the stage, I let her see my dick, and I was pleasantly relieved by her response. She didn’t laugh or sneer, make fun or get cross, as has so often happened. She didn’t make any disparaging comments about it being much smaller than other men’s dicks. Instead, her face lit up with delight, and she made a fuss of it, saying that it was cute and sexy and sweet. She asked me how long it is and I lied a bit and told her that it sometimes got up to four inches.

She laughed and said there was no need to exaggerate and always be candid with her. I said sorry and admitted it was 3 inches when erect. I confessed my worries about my size and told her some of the nasty things girls had said in the past. She said they were mean and told me to stop being so obsessed with size. She assured me that size isn’t the only important thing and that she’d had enough of rough macho men with big dicks. She said mine wasn’t even the smallest one she’d seen and told me about a guy she’d had a one-night stand with once who had what she called a ‘pencil dick’ that was “even smaller than yours, so don’t worry.”

She told me about previous boyfriends who’d been in rock bands or were drug smugglers and mercenaries who’d been in the SAS. She said she had to be honest with me before we started and shocked me with her experiences of group sex with bands in hotel rooms, one-night stands with strangers, and jobs accompanying gangsters where she had to pose as their girlfriend and even let them fuck her. She admitted that she had been obsessed with powerful guys with big cocks and hated herself for allowing men to control her with sex.

Finally, and with her consent, I asked for her hand in marriage. It was a very formal proposal. I had champagne and a ring, and I went down on one knee and begged her to be my wife. She said yes.

That night we lay together in her bed, and she told me to make love to her.


Because my dick is so small, I have to be careful that it doesn’t slip out when I have sex which means the woman not moving her hips or bum too much. And because my strokes are necessarily short and quick, I always cum quickly. Or not at all; if I lose my erection. They can’t always feel my dick inside them anyway. I will never know what it’s like to make a woman shudder with passion as she has an orgasm. I’m usually concentrating more on myself, trying not to slip out or lose rhythm.

To make up for it, I always make sure I go down on the woman and do my level best to give her an orgasm after I’ve cum. I don’t mind the taste of my own semen. Either way, it’s a much more submissive role than it would be for a man with a big cock.

That first time I could tell she couldn’t really feel me inside her, but she made such encouraging noises of pleasure, and when I did cum she looked at me and squealed with mock delight as if I was a child or a puppy dog that had done something clever.

I found that strangely both humiliating and arousing.


Shortly after we had announced our wedding and set a date, she disappeared for a weekend without any warning. I couldn’t get hold of her. I hunted around, called on people we knew, her family, and girlfriends. They couldn’t help but assured me she was fine and told me I mustn’t worry. They would try and change the subject, congratulate me, and tell me how excited they were about the wedding. I suspected that some of her friends weren’t being entirely honest with me. I spent the weekend in a state of sexual jealousy and humiliation, drinking and wanking.

I phoned her workplace on Monday, and they said she’d phoned in sick. She wasn’t at home or her parents.

She finally phoned me on Tuesday night and told me to stop worrying, asked me why I’d had to leave so many answerphone messages, and pester all her friends and family. She didn’t want me to come over but admitted she had no food in the house and eventually said I could see her if I went to the supermarket, and she sent me a long shopping list.

I finally got to hers to find her in bed. She said she just hadn’t been very well and was very sorry. I fussed over her and made her hot drinks, and she got a bit cross at my fussing. She told me I could get into bed with her, and when I went down on her, she told me to be very gentle as she was very sore down there.’ She appeared to have a small orgasm with my tongue and then lazily said, it was okay for me to have my turn now’ but to be gentle as she was sore and tired. She managed to murmur with affected pleasure while falling asleep, and she began to snore while I was inside her. I found this so shameful and arousing that I came, and she sensed it saying “Ooh lovely, good boy, so nice” in her sleep.

The next morning she told me that she hadn’t been ill but that she’d been at Lance’s all weekend. She said she hadn’t intended to stay that long; she’d only meant to go for one last night of sex to get him and his big cock out of my system once and for all’ before committing to marriage and a lifetime of loving sex with me.

When I admitted I was upset and told her of my feelings of humiliation, jealousy, and inadequacy, she became cross with me. She told me that if I didn’t see what she’d done with Lance as a sign of her commitment and love for me, perhaps we should call off the wedding.

I told her I was scared and embarrassed to meet Lance and her friends and family who knew about her affairs. They would all be at the wedding.

At that, she became impatient with me and began to lecture me:

“Okay. Yes, they might all know about Lance and me, and, yes, they might all know about you having a smaller than average penis, but who cares? It would be best if you remembered that they also all know that it’s you I’m marrying, not Lance or any of those other guys, and surely that’s the only thing that matters. That’s what you should be proud of: I’m marrying you, not them. Regardless of how small your dick is.”

And that was her last word on the matter. Ever.

So no matter how I crave to be mocked and humiliated about my small penis. No matter how I fantasize about being her cuckold and imagining Lance fucking her. No matter how much I want her to tell me what it’s like to be fucked by a real cock, not my little penis. No matter how much I go online and masturbate while she lies in bed upstairs. She will never allow herself to discuss the matter of penis size.


The End.


*This story has been edited to fix spelling, punctuation, & basic grammar, but the narrative and plot have remained the same. Just remember, even with the limited editing we do, it doesn’t mean any possible major flaws in this story were fixed.

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