Sometimes, Cuckolding Can Be Painful (But Oh So Good)

Most of the time, you love being a cuckold. Most of the time it’s an absolute thrill ride where your sexual fantasy comes true over and over. Most of the time you and your wife get to experience stunningly pleasurable orgasms as a result of your willing embrace of an alternative sexual lifestyle.

Last night was wonderful. Your wife’s boyfriend came over and she let you watch them fuck in your bed. You witnessed the intense pleasure she feels when they’re together. You witnessed her climaxing with another man’s cock inside her.

“Would you like to kiss my pussy?” she asked when they were finished and her boyfriend had excused himself to the bathroom to dispose of the condom and wash up.

You nodded and your beautiful wife spread her legs to invite you between them.

“Come,” she said.

You crawled into the bed and took your place between her legs. You studied her swollen, slippery pussy lips and smiled at the beautiful reminder that she’d just had sex with another man.

“Kiss my pussy,” she said softly.

You pressed your lips against the folds of your wife’s freshly-fucked flesh and kissed it. You kept your tongue in your mouth and stayed away from her clit. She gets too sensitive after being with her boyfriend and finds it rather unpleasant if you try to make her cum.

Instead, she likes when you kiss her pussy. She likes feeling the warmth of your lips against her flesh. She likes it as a form of reclamation. It shows her that you’re still her cuckold, that you still find it thrilling to watch her have sex with the man she welcomes into your bedroom on a weekly basis.

“Play with your cock,” she said. “Kiss my pussy and play with your cock.”

You kissed her pussy over and over. You coated your lips with her juices. You licked them clean. You tasted her. You tasted the sex she had with her boyfriend. You tasted the sex you watched them have.

“Mmmm, that’s so good,” she said. “I love it when you kiss my pussy like a good cuckold. Stroke your cock faster.”

You did as you were told. You stroked your cock faster.

“Put your tongue inside me. Taste me. Taste us. Taste the sex I just had,” she said.

You pushed your tongue into her perfect, slippery, still-gaping pussy. You tasted her juices. You soaked up everything you could. Your cock was rock hard in your hand as you moved your fingers up and down the precum-soaked shaft.

“Do you want to cum?” your wife asked.

“Yes, please,” you said.

“Put on a condom,” she said.

You moved from between her legs and grabbed a condom from the nightstand. You tore it open and put it on as your wife rolled onto her side.

“Cuddle with me,” she said.

You moved into the bed, playing the small spoon. Your wife pressed her body against yours and kissed your neck as her hand found its way to your cock. She stroked you in the condom, applying the perfect level of pressure to deliver an astonishing burst of pleasure.

“Think about his cock filling me,” she whispered between kisses on your neck and upper back. “Think about him fucking me. Think about his cock sliding in and out of me. Think about how much you loved watching.”

You closed your eyes and gave yourself over to the thrilling sensations coursing through your body. The handjob, the soft kisses, and the whispered dirty talk combined to bring you right to the edge of orgasm.

“Think of me sleeping in his arms tonight,” she whispered. “Think of me spending the night with another man in our bed.”

You came hard, filling the condom with your load thanks to your wife’s skillful work. She released your cock and pressed her hand against your chest to pull you closer.

“I love you,” she whispered.

“I love you too,” you replied.

She granted you a few more minutes of cuddling time before gently rolling away. You left your bed without having to be told. Her boyfriend was spending the night, as he always did, which meant you’d be sleeping in the guest room.

“Sleep well,” she said.

“You too,” you replied before leaving the bedroom and gently shutting the door behind you.

You removed the condom and dumped it in the guest bathroom trash before changing into the clothes you’d laid out on the guest bed.

You grabbed your phone and got under the covers. The good part of the evening had ended and the difficult part was about to begin.

It didn’t really start until you heard the moans again. Your wife and her boyfriend never have sex just once. They always enjoy each other two or three times before going to sleep. You’re only ever invited to watch the first time, though. She likes having time alone with him. She likes to make love to him when you’re not watching. You know that’s what she’s doing, which makes the moans even worse.

There’s pleasure in it. You can’t avoid feeling at least a little turned on by the idea of your wife having beautiful sex with someone else. It’s scary, though. You know she has feelings for him. They’re mild. She’s not going to leave you for him. She has feelings, though. She thinks about him all week. She looks forward to spending Saturday night with him. She looks forward to the sex and the pillow talk. You look forward to it too, but once you’ve had your orgasm it all starts to feel a little bit painful.

The sex seemed particularly passionate last night as her moans were a little louder than usual. You heard his far deeper moans too. You heard them cum together. You imagined them cuddling and talking afterwards. You imagined your wife telling him how much she enjoyed having sex with him. You imagined her bond with him growing a little stronger and it made sleep exceptionally difficult.

Eventually you drifted off, sleeping through the night as dreams of your wife and her boyfriend having sex filled your head.

Now you’re awake. It’s a little after 8 a.m. The smell of freshly-brewed coffee fills the house. Normally, that would be a great reason to get up. Sunday mornings are an exception, though. On Sunday mornings your wife’s boyfriend is in the house. He’s usually the one that makes the coffee.

You know what you’re going to see when you leave the guest bedroom. You know it’s going to be a little bit painful, and yet you can’t help but give in to the little tug of desire that’s ever present as a cuckold.

You get out of bed, make a quick pit stop at the bathroom, and then make your way to the kitchen. Your wife and her boyfriend are embracing as you enter. She’s looking up at him with a kind of joyful wonder in her eyes. You know why. You know it’s because she spent the night before having great sex with him. You know it’s because she’s in that place where she’s completely enamored with the new man in her life.

That’s the painful part. It’s seeing how enamored she is. It’s the fact that she doesn’t look at you the moment you walk into the kitchen. It’s the way she takes a few moments to share a beautiful kiss with him before turning to you.

“Good morning,” she says. “How did you sleep?”

“Good,” you say. “How about you?”

They both smile at you and your wife takes her boyfriend’s hand in hers before she says, “We slept very well.”

They look at each other and smile. You imagine her falling asleep in his arms after the sex they had. You imagine the pleasure of an orgasm coursing through your wife’s body as she cuddles up against his body and drifts off to sleep. In that moment you feel the pain and pleasure of being a cuckold. You feel the agony of knowing that your wife has developed great sexual chemistry and an emotional connection with another man. That same knowledge brings pleasure, though. It fills you with desire. It makes you wish she’d send him away so you could fuck her, or go down on her until she cums.

Your wife kisses her boyfriend again and watches him go as he heads towards the bedroom. She turns to you with a giddy smile on her face.

“Thank you,” she says.

“For what?” you ask.

She steps closer, presses her body against yours, and says, “For being a wonderful husband. For being a wonderful cuckold. For finding pleasure in the fact that I kick you out of the bedroom one night a week in favor of another man.”

“You’re welcome,” you say.

“We’re going to make love again before he leaves,” she says.

You’re a little hard. It’s painful to hear her utter the words ‘make love’ but you’re excited.

“You can watch if you want,” she says. “Would you like that?”

You nod.

Your wife smiles and takes your hand. She leads you to the bedroom, gives you a kiss on the cheek, and joins her boyfriend in the bed.

You lower your pants, free your cock from your underwear, and sit. You watch your wife and her boyfriend share the most beautiful, tender kisses imaginable. You watch as their hands move over each other’s bodies. You watch as they work to arouse each other.

She moans as her level of desire grows. Their kisses get more fervent. Her fingers find his cock and his move between her legs to play with her pussy. You stroke your cock slowly. You know you’re not supposed to cum until they’re done. Your wife likes to be the one that gets you off.

Your wife doesn’t look over at you. She’s too caught up in her lust for the man in your bed. She knows you’re watching, though. She knows you’re sitting there stroking your cock like a good cuckold and it turns her on. She likes having an audience. She likes knowing that her husband is there, offering his support of her need to enjoy the pleasures another man offers.

She moves between her boyfriend’s legs and takes him in her mouth. She strokes his shaft and looks up at him as she sucks on the head. He watches with a smile on his face and lets out the kind of appreciative moans a woman loves to hear when she’s offering oral pleasure to the man she craves.

“Will you get me a condom?” she asks you before taking him in her mouth once more.

You smile and get up to retrieve a condom from the nightstand, but there’s a little bit of pain there too. She wants you to help her prepare her boyfriend to fuck her. She doesn’t want you to fuck her. She doesn’t want to take your cock in her mouth. She just wants you to get a condom so she doesn’t have to move from between his legs.

You pass your wife the condom and return to your seat as she tears open the wrapper and puts it on his long, thick, exceptionally hard cock. She looks up at him, smiles, and straddles the man that satisfies her sexual needs.

She takes him inside her and your eyes dart from your wife’s face to his. You watch them both experience that moment of joy when you first start having sex. It’s a mixture of intense pleasure and the sense of anticipation that comes from knowing that you’ll soon get to experience a wonderful orgasm.

Your wife leans down and they kiss as she rides his cock in a slow, sensual manner. They’re making love. They’re connected. They’re completely lost in their desire for each other. Another man’s cock is inside your wife’s pussy and she’s overwhelmed with pleasure. It’s exactly what you want as her cuckold, and yet it’s hard to watch. Your cock is stiff and you’re filled with desire, but there’s also a sense of anxiety roiling inside you.

You don’t make love to her like that anymore. Not since he entered your bedroom. Now he provides your wife with that connection and that pleasure. You still have sex occasionally, but it’s better with him. You know it is. That’s why she prefers having sex with him.

That’s how it’s supposed to be. Why would she bother fucking someone else if it wasn’t better? It still stings a little, though. The pain is there right alongside the pleasure. There’s something about it that feels right, though. Shouldn’t there be a little bit of pain? Isn’t your wife making love to another man because you can’t quite satisfy her the way she needs?

They switch to missionary and your wife wraps her legs around him. They kiss as he thrusts in and out of her body. They moan together. You’ve watched enough to tell that they’re getting close to their climaxes.

Amazingly, they cum together. Your wife closes her eyes and arches her back as he thrusts inside her and unleashes his load into the condom. You stroke slowly and witness the dual orgasms unfolding in front of you. You savor the intense pleasure both your wife and her boyfriend are feeling and you savor a little bit of the pain that comes from knowing that someone else is better at fucking her than you are.

Afterwards, they share lots of long, slow kisses with his cock still inside her. She caresses his face and smiles. They whisper to about how good it felt, about how much they crave each other, about how they can’t wait until they see each other again next weekend.

Her boyfriend pulls out and heads towards the bathroom as he pulls the condom off. Your wife swings her legs over the edge of the bed, hops off, and saunters towards you with a smile on her face.

She drops to her knees in front of you, pulls down your underwear, and leans forward. She kisses the head of your cock, eliciting a moan of equal parts surprise and pleasure.

“You’re such a good cuckold,” she says between kisses. “You deserve a reward.”

She wraps her lips around your dick and offers a blowjob so intensely pleasurable that your mind immediately goes blank. The room goes quiet except for the sounds of sucking and your wife’s quiet moans. Pleasure like you haven’t felt in months spreads from your loins.

Your wife hasn’t taken you in her mouth since the first time her boyfriend spent the night in your bed. You’d forgotten how good it feels and how talented she is when she’s determined to get you off.

“I’m close,” you say, warning her in case she has no intention of swallowing your cum.

She keeps sucking. She plays with your balls. She strokes your shaft. You groan and climax in her mouth. You grip the edge of the chair as one pulse of pleasure after another rushes through your body.

Your wife pulls her mouth from your cock, sits back, and smiles. Then she comes closer. Her hand moves to the back of your neck and she pulls your lips to hers. She opens her mouth. Her tongue slips past your lips.

You taste your cum. She’s sharing it with you. She moans like she’s about to cum. She’s encouraging you to go along with it. She wants you to accept your load from her. She wants you to be a good cuckold.

You do as your wife desires. You immerse yourself in the filthy pleasure of sharing a load of your cum. You suck on her tongue. You taste your seed. You swap it back and forth.

Eventually, she pulls away and wipes the cum from her lips. She swallows and smiles at you. You do the same. You swallow your cum. You swallow the load you just shared with your wife.

“That was incredible,” you say. “Thank you.”

“Thank you for being a good cuckold,” she says.

Sometimes, being a cuckold means experiencing the most intense pleasure of your life. Sometimes, it means experiencing deeply cutting emotional pain. Most of the time it means a little bit of both and you’re okay with that. You welcome that. You love that.