Cuckolding Myself

I rolled off of my wife and lay beside her on our bed. The cum filled condom hung loosely on my limp cock which was quickly shrinking back to its flaccid state. Neither of us spoke a word for the few minutes that followed. By that time I was quite familiar with the dreaded silence that followed every time we had sex. In fact, we were both familiar with the whole fucked up routine.

It would start with me kissing and fondling my way down her body till I reached her pussy, and then trying desperately to get her off with my fingers and tongue. She would then stop me when she feels I have tried enough, and tell me to fuck her. She already knows how it is gonna end, but she is faithful to me, and she has needs, and thus she remains hopeful. I, however, know, by the time I put on a condom, that my cock is way too tense with anxiety that it is ready to shoot its load as soon as I thrust into her. I climb on her anyway, my cock already throbbing in my hand as my anxiety gets worse with every inch closer to her I get. I position my cock head at her opening and thrust in hard. Karen gasps as I penetrate her, she always does. I keep fucking her hard and fast, already ejaculating on the second thrust and trying to get as many thrusts I can before my cock becomes too soft. Karen's moans quickly turn into frustrated grunts, which I take as my cue to stop.

I pulled off my condom and tied it into a knot before throwing it in the trash bin. I looked over at Karen, she lay with her arms crossed over her head, eyes on the ceiling. I could tell she was frustrated and disappointed, and I was once again overcome with shame.

"I can't keep doing it like this." she sighed.

"You know I've tried everything. I don't know what else to do."

"I know, honey. I'm not saying you don't try. I'm just so tired of all this."

I knew it was only a matter of time until her patience runs out, and she would leave me. I couldn't blame her. I had to find another way to satisfy her. It was the only way to save our marriage. I had been thinking about it for months, but I wasn't sure how she'd react to the only solution I could think of.

"What if...," I hesitated.

"What if what?"

"What if we got someone else to do it with you?" I asked nervously.

Karen stared at me with a shocked expression on her face. "Are you crazy? Why would you even think that! You want another man to fuck your own wife?"

"I just want you to be happy. I love you, but I know I'm not gonna be able to satisfy you in bed. I just can't help it."

Karen was now eyeing me as if trying to figure out if I was playing a trick. "Are you really serious about this? Do you understand what you are asking me to do?"

"Yes, I am serious. I know you love me and you'd never cheat on me, but I know our marriage won't last like this. This is the only way."

"But would you be okay with that? I don't want to hurt you."

"Yeah. I think I can handle it. At least I'll know you aren't going behind my back."

Karen chewed the tip of her thumb while pondering the thought. I knew she was warming up to the idea. She had been dealing with the frustration long enough for her to want to take any chance to be free of it.

"Let's talk more about it in the morning." She said finally. "I don't want to do anything until we're both sure we're okay with it."

"Yeah, okay. That's a good idea." I rolled over and put my arm around her. "I love you, baby." I kissed her cheek.

"I love you too." I wrapped my arms around her and she pressed up against me in the spooning position. As she fell asleep in my arms, I found myself wondering if I was doing the right thing.

*****

When I woke up the next morning, Karen had already gotten up. I took a quick shower and headed to the kitchen where she was sitting at the table sipping coffee from a mug, and had a second mug ready for me. I could see her watching me from the corner of my eye as I went to pour myself a bowl of cereal before I sat down across from her. She was still watching me as I put a spoonful into my mouth, but she didn't say anything. She was waiting for me to bring up the subject.

"So... about last night" I said when I swallowed.

"Yes?"

"Well, what do you think?"

Karen blushed. "Are you sure about this?"

"Yes. And you?"

She nodded. "How do we find a guy?"

"Let's put up an ad on the internet. Don't worry, we won't share any personal information until we find a guy you like. Although, maybe we should put a picture of you in it."

"What? No! I don't want to put my picture in it."

"More people will respond if there's a picture. We'll hide your face. We'll make sure you're not recognizable."

Karen did not seem too happy about it, but we finished our breakfast and went back to our room and I picked out a short sundress for her to wear for the pictures. She was reluctant about it as she had put on some weight since we got married, but I assured her she never looked more beautiful. She finally put it on and I got her to pose seductively and I made sure to capture as much of her thighs and cleavage as I could without being too obvious. I found myself getting excited at the thought of other guys checking out her pictures, and I found myself secretly hoping Karen would strip down for some of the pictures.

Within the next hour we posted an ad on craigslist and even created profiles for Karen on several adult dating sites as a married woman looking for some fun with no strings attached. We even checked out some of the guys on the dating sites that Karen found attractive. She seemed to like the big muscular guys, particularly the black guys. I noticed her biting her lip as we checked out the guys, and decided to tease her a bit.

I opened an ad on craigslist for a bull looking for a cuckold couple. It had a picture of a black guy with rock hard abs and a huge cock which looked as if it was a foot long and thick as his wrist. I heard Karen gasp as she saw at it.

"Look at the size of that cock. It's gotta be at least three times as big as mine. Just think what it would be like to get fucked by that monster. Do you think you could take it?" I teased.

"What- no way, that's way too big for me!"

"I guess you're right. You wouldn't be ready for something like that after only taking my tiny prick all this time."

"That's not what I meant."

"No, it's okay. But, man! Just imagine what he can do with that thing. You'd probably cum just from taking that fat cock head in. That thing's so thick you'd even have a hard time putting it in your mouth. And judging by the size of those balls he would pump several mouthfuls of cum in your mouth."

"You're really enjoying this aren't you?" Karen frowned. "I thought you were just doing this for my pleasure, but you actually seem to be getting off on some guy having sex with me."

"I'm just excited for you, that's all. Aren't you excited?"

"Of course I am. I just never thought you'd turn out to be so much of a cuckold."

I laughed. "I'm just as surprised as you are. Now tell me, what kind of guy do you want to fuck?"

"Well, a nice, decent guy. Not the arrogant type."

"Do you want him to have a big cock?" I stroked my hand up her inner thigh under her dress.

"Not too big. But bigger than yours." She grinned at me slyly.

"Around 8 inches maybe?" I asked, cupping her crotch over her panties, feeling her warmth and wetness.

"Yes! And twice as thick as yours."

"And what will you do with his big cock?" I rubbed her wet pussy over her panties.

"I will lick it up and down from his balls to the tip, and then I will take the head in my mouth and circle it with my tongue. Then I will take him deeper in to my mouth." Karen moaned.

"You haven't done that to me in ages." I pushed her panties aside and rubbed her clit. Then I pushed two fingers inside her. She was dripping wet and squeezed her pussy tight around my fingers.

"That's because your little prick would cum as soon I put it in my mouth." Karen giggled, grinding her pussy against my hand.

"Are you saying I'm not man enough for you? Is that why you want a big strong man to satisfy you?" I leaned over her and kissed her neck while I pushed my fingers deep in her pussy.

"Oh, yes! I need a real man, not a sissy like my husband who can't control his little prick. I want a real man with a big hard cock that I can worship."

"That's right. You no longer have any need for your sissy husband or his little prick. You won't be able to feel the tiny thing after you have had a real cock inside your pussy." I kissed my way down her neck and licked and sucked the tops of her big boobs while my free hand fumbled with the zipper of her dress from behind her back. Karen continued to grind her pussy against my hand while my fingers rubbed against her G-spot.

"Mmmmhh... Yes, the only use I'll have left for him is to lick my pussy clean after my lover cums inside me."

"Oh, are you gonna fuck your lover in front of your wimp of a husband?" I pushed her dress down to her waist and sucked her breast into my mouth forming a seal around her areola and gave rapid flicks of my tongue over her nipple while she moaned and and bucked her hips against my hand.

"Yesss... He needs to see what a real man can do for his woman. He needs to see what a real cock looks like. Then he'll... ohhh!... and then he'll know how pathetic he really is."

I was so turned on by her demeaning words that my cock was straining hard inside my pants. I ignored it and focused on her pleasure.

"You should make him stand there naked so that your lover can see what a tiny prick he's got. You will make fun of the little thing while you are getting rammed by that huge cock. You will tell him how much better your lover is, and how his little prick is not worthy of your hot pussy, and how it doesn't deserve to be called a real cock."

I felt Karen's body tense up and she clutched the back of my head and pressed her lips against mine, and her other hand gripped on to my back. I rammed my fingers in and out of her pussy as she screamed and bucked her hips as she came harder than I ever saw her cum in ages. I pulled my fingers out of her pussy and sucked each one dry. She laughed and pulled me in for a kiss, and we kissed deep with our tongues in each other's mouths.

I broke our kiss and took a step back to look at her. She couldn't stop smiling and blushed when she saw me looking.

"You're such a pervert." she shook her head, still smiling.

"Don't tell me you didn't enjoy that."

"I loved it! You haven't made me cum like that in ages."

"I loved it too! It was so hot. My cock is still hard."

"Oh, is it?" Karen asked rubbing my crotch.

"It's OK. You don't have to."

"Someone has to take care of the little thing." she said mischievously.

She undid my pants and pushed them down to my knees. She then slipped her hands under my shirt and slid them up my stomach to my chest. I pulled my shirt over my head and dropped it on the floor. She rolled my nipples between her fingers and then took one in her mouth. She let her other hand slide down my stomach and inside my briefs where she lightly caressed my hard cock with the tips of her fingers. She took her mouth off my nipple and leaned close to my ear and spoke just slightly above a whisper.

"Are you enjoying yourself sissy? Does your pathetic little prick feel good when I touch it? I bet it is already on the verge of cumming, isn't it?"

I moaned. She was right. I was already struggling to hold back as her teasing fingers brought me closer to orgasm.

"It really is just a useless little prick. You will never satisfy a women with that thing. It's barely longer than my finger. Can't be any more than four inches.."

"It's five inches, ma'am." I realized I just called her ma'am without her even telling me to.

"That's right, from now on you will address me as ma'am. Five inches, huh? You think five inches is enough to satisfy a woman? Maybe if you were able to fuck for more than five seconds. But you are just a sissy little bitch who is a slave to his little prick. Aren't you?"

"Yes, ma'am."

She let go of my cock and yanked down my briefs. It was lucky she had stopped touching me or I would have cum right then.

"Look at that little thing." Karen said cupping my balls. "It's already struggling to hold back when I have barely touched it. This is exactly why you will never satisfy any woman. This is why you need a real man to do your fucking for you, because what you have between your legs is nothing more than a child's plaything."

It was so humiliating, but at the same time I never felt so excited. I felt like she truly was my mistress and I her slave. I would have gladly dropped down on my hands and knees and kissed her feet.

Karen wrapped her hand around my cock and started stroking me slowly. I felt the familiar panic rising in my chest as I felt the orgasm building already. "I will allow your little prick to cum this time, but afterwards I'm gonna cage it and lock it up. You will only have an orgasm when you've earned it. You understand?"

"Yes, ma'am. I'm cumming." I moaned, as I came on her hand.

"I knew you wouldn't last more than a few seconds. You're so pathetic." she said as she milked the last drops from my cock.

She then held her cum coated hand up to my face. I looked at her, confused.

"Clean it up. It's your mess." she demanded.

"Baby, you can't mean-"

"That's ma'am to you. And yes, I want you to lick it all up and swallow it. Every single drop."

After having cum, now that my head was clearer, it wasn't so appealing to me to drink a man's cum, even if it was my own. Karen glared at me impatiently, and I had a feeling it was best not to upset her. If I wanted this to work out, I would have to play my part, which I had foolishly established as the 'sissy husband'.

I reluctantly licked the strings of cum from her hand and forced myself to swallow it. I then looked back at Karen as if waiting for her approval.

"Good boy." she smiled slyly. She put her arms around me, grabbing my ass cheeks roughly. "We should have done this years ago. You were never meant to be a man. You were born to be a cuckold. Isn't that right?"

"Y-Yes, ma'am."

"I'm glad you've finally found your place. I must say I'm loving this new side of you. It's really cute." She smiled at me lovingly.

"You really think so?"

"Yes. And I'm so happy that we're both gonna enjoy our new arrangement. It just wouldn't have felt right fucking someone else if it made you feel bad."

"Are you really going to cage my cock?"

"I think I might," she giggled. "I have a feeling you would like it."

It actually did make me excited when she said it. I felt like I wanted to do anything to please her even if it meant torture for me. Maybe she was right. Maybe I was born to be a cuckold.

"If it pleases you, ma'am."

"My god." Karen laughed. "You're so into it. This is going to be so fun. I love you so much, baby."

"I love you, too."

We shared a long, loving kiss. I felt so tender in her arms as she caressed my back and my ass cheeks, and I let my hands wander gently over her beautiful body. I couldn't wait until she was wrapped in another man's arms.