Cuckold Initiation

[ This is an original fantasy story; please attribute properly ]

A few days ago my wife mentioned that she had invited a special friend over this weekend. She was excited about the visit and about me meeting Richard, but she didn’t provide a lot of details. I detected a coy attitude as she talked about it, and slightly sexy inflections when she mentioned him. But I didn’t ask questions, it seemed normal enough, probably just an old friend. She has been reconnecting with a lot of people thanks to Facebook.

Saturday came, and she reminded me that he was coming over. She said it would be for dinner and some activities afterwards. I assumed she meant something like Scrabble. Boy was I wrong.

About 3 hours before his planned arrival time, my wife showered. I remember noticing, because she had also showered in the morning. She also called me in to shave her legs, a submissive thing she has me do for her sometimes. She teased me with her luscious pussy as I carefully ran the razor across her thighs.

After drying her hair, she started to get busy in the kitchen cooking. I offered to help, but she said she wanted me to go get ready instead. I asked her what she meant, and she said “Oh, didn’t I tell you? Richard is really cool about crossdressers. I told him you like to dress up, and we thought it would be fun for all of us. So I’d like you to go put on your maid’s uniform. I think your white thigh-highs with a garter would be nice, with black heels, and take some time with your hair and makeup.”

I was stunned. But also a bit excited. It would be the first time that we would entertain at our house with me crossdressed. I agreed, and went upstairs to get ready. After about 45 minutes I was ready. I thought I looked pretty good, and went downstairs to present myself to my wife.

She looked me over and decided I looked presentable. She told me to set the table, which I proceeded to do. She was finishing up the meal, putting things into the oven and microwave. Then she said “I’m going upstairs to get ready myself now. If Richard arrives before I come down, let him in, take his coat, and visit in the living room. Meanwhile, I want you to sweep the living room and kitchen floors.” I curtsied and replied “Yes, Ma’am”.

While sweeping, I realized just how distracted I was about this whole evening. I hadn’t even noticed that she had me set the table for two, not three people. There were also several nice candles on the table. It was then I knew she was planning on having me be their personal servant during dinner. The maid’s outfit suddenly made more sense. Well, that was fine, I like that role.

I finished sweeping and was straightening up the living room when the doorbell rang. My heels clacked on our hardwood floors as I went to the front door and opened it. “Hello, you must be Richard!” I said in my feminized voice. He looked me over, and boldly stepped in and past me.

“Yes, of course,” he said, “and you must be the sissy husband.” I was a bit taken aback by his straighforward statement, but it was of course true, so I replied “Yes, Sir”. He took off his coat and handed it to me, and proceeded to walk over to the couch and sit down. I hung his coat in the closet, and hesitated about what to do or say next.

Just then a door opened upstairs, and I looked up to see my wife coming down the stairs. I could not believe what I was seeing. She was dressed stunningly and extremely sexy. She had on a short dress that showed her figure beautifully, pretty heels, bare legs, and as I looked up the stairs at her I could see she was not wearing any panties. I’m pretty sure I stood there in shock with my mouth open.

By the time she reached the bottom of the stairs, Richard was there with open arms, and they embraced. Right in front of me they kissed deeply, and their arms were around each other. Then he was looking her over, telling her how stunning she looked, and that dinner smelled wonderful. I noticed both his hands were tightly cupping her lovely ass and pressing her body against his.

Clearly enjoying his strong embrace, my wife turned to me and said “Go to the kitchen and put the food on the table for the two of us. Light the candles, and run the microwave for 2 minutes.” They went resumed kissing, their moans and the clacking of my heels the only sounds.

I started the microwave, brought some food to the table, and lit the candles for them. Before long they joined me in the kitchen. The two of them sat down, him holding her chair. They talked between themselves as I served. Once all the food was out, I just stood nearby, awaiting further instructions. They chatted and began eating, mostly ignoring me. Richard said he wanted some catsup, so I retrieved it from the refrigerator for him. And my wife needed her water glass refilled.

Eventually my wife addressed me directly. “Sissy, come here.” I stood next to her. “If you haven’t already figured it out, Richard is my new boyfriend. As you can see we are becoming very good friends. We will probably be seeing much more of each other in the future.” What could I say, but “Yes, Ma’am”. I wasn’t quite sure what she meant exactly by “boyfriend”.

My wife continued, “After dinner we have an initiation for you. I won’t tell you exactly what will happen, but I will tell you that I expect you to comply with everything that either I or Richard tell you to do. If you even hesitate, I will instantly add another 6 months to your chastity time. For each offense. Is that understood?” “Yes, Ma’am”. Ok, this was getting pretty serious now.

Richard asked to see my chastity device, and my wife said “Lift up your dress, Sissy. Show Richard the tiny, useless cock you have.” I walked over to Richard, lowered my panties, and raised the front of my dress. He looked down and laughed. “Unbelievable. No wonder your wife is not sexually satisfied. Your dick is a joke. It’s pretty damn obvious why she calls it utterly limp and worthless.”

He asked if my cage had spikes, and I replied “No, Sir.” Richard suggested that my wife consider having them added so that my attempts at erections would cause significant pain. He pointed out to my wife that, over time, this would extinguish that annoying sexual reaction. He said he liked the idea of having the only functional cock in the house. My wife said she’d look into having spikes added to my chastity device.

My wife said to Richard “Her little clitty is always less than two inches. That’s smaller than my pinky! Isn’t that hilarious?” She held up her pinky, bent over like my limp, worthless cock. They both laughed. “A baby’s dick is bigger than that!” Richard said, and they both howled with laughter. My wife leaned over and whispered something to Richard that I couldn’t hear. They both laughed and laughed at that.

Finally they stopped laughing, and my wife said “Put your dress down, dear, stop flashing our guest.” I lowered my dress and my head, feeling very embarassed. My wife noticed, and laughed. “Look, her sissy cheeks are all red. She loves this. ” They both chuckled again.

Richard continued to ridicule me. “Your wife tells me you actually like to dress like this, and that you even put your own makeup on, is that true?” I replied “Yes, Sir.” He laughed again. “I wasn’t sure whether to believe that. But you really are a sissy. That’s a really pathetic excuse for a husband. Your wife deserves a hell of a lot better, doesn’t she?” Again, “Yes, Sir.” He replied “She sure does,” leaned over to her, and they kissed again.

They went back to talking between themselves. Richard asked some detailed questions about my chastity, how often she lets me cum, whether I am permitted masturbation or intercourse, and other very personal questions. My wife gladly told him everything, even how she milked my prostate and fed me my own cum. That made Richard shudder with disgust. He said he had never tasted cum, but that it was appropriate for sissies to learn to love it. He looked at me, and I said “Yes, Sir.”

My wife also offered that, like a true sissy, I enjoyed being a total cock slut and taking it up the ass. “I suppose you could hire her out as a cock whore and earn some money that way.” My wife seemed to consider the idea, then they both burst out laughing again.

They finished their food and my wife got up from the table. She told me to clean the table, put the food away, fill the dishwasher, and then meet them at the couch. Richard followed her out to the living room, but then I heard them both go upstairs and into our bedroom. I was relieved to hear them come back downstairs after only about a minute.

I cleaned up the kitchen and dishes, listening to their talking and laughing wafting in from the living room. I couldn’t hear what they were saying, but they were clearly enjoying each other’s company. They also talked more quietly at times, and I suspect they were planning the next events.

Eventually I finished my chores and joined them in the living room. My wife was sitting on Richard’s lap and had his arms around him. He was kissing her neck and fondling one of her breasts inside her dress. His other hand was very high on her inner thigh. Her eyes were closed, and she was clearly enjoying his attentions. I stood there quietly, watching and waiting. Richard seemed to be taking his time fonding my wife in front of me.
Eventually my wife opened her eyes, and noticed me standing there. “Isn’t it nice to see your wife getting some well-deserved attention from a Real Man?” she asked. I could only respond with “Yes, Ma’am.” They looked at each other briefly and
smiled, and then she said “Sissy, do you remember what I said about obeying tonight?” “Yes, Ma’am, I clearly remember”. I had already endured 2 months of chastity, and only had 6 weeks left before my next release. Six more months was very scary. She said “Good” and moved off his lap to sit next to Richard.

He then addressed me. “I hear that you are a pretty good cocksucker. Let’s see. Get going, and no teeth.” I was shocked again, but realized that I was starting to hesitate, which would be disasterous. So I sat down next to him and reached to unbuckle his pants. He stopped me, pointed to the floor between his feet, and said “No, down there. On your knees where you belong.”

My wife giggled, and I got off the couch. He moved his legs apart, and I knelt on the floor between his knees, facing his crotch. He allowed me to unbuckle his pants this time, and I pulled them along with his boxers down to his thighs. His cock was thick and semi-hard, and he had lots of pubic hair. A very manly smell wafted up. I looked up at my wife and she lightly nodded, indicating “get busy”.

I took Richards cock in my mouth gently, holding it between my lips. The tip of his cock was in my mouth and I worked my tongue around it. He moaned and put his head back. I felt him getting harder as I licked and sucked. I used all my
techniques on him, and after a while he started bucking his hips as if to fuck my mouth.
At that point my wife stood up and said that it was time to go upstairs. I looked at her, and she was grinning and looking at Richard. The instructions she gave me next were yet another surprise for this completely unexpected evening.

“Sissy, you will now go up to our bedroom and take off your dress and your panties. Sit on the chair, and tie yourself securely to it. Put in the ball gag and put on the blindfold. Then use the handcuffs to lock your wrists behind your back. When you are ready, stomp 3 times on the floor. Go. Now.”

My wife turned her attention to Richards cock, wrapping her hand around it and gently stroking it. I went upstairs and did as instructed. I found the chair had been moved from its usual location to be at the bottom corner of our bed. I partially disrobed, and sat in the chair in my bra, garter, stockings and heels. Some white rope was on the floor by the chair, and I used it to firmly ties my ankles and waist to the chair legs.

I enjoy bondage, so just this was enough for me to be aroused. My cock strained against the cage. I put in the ball gag and blindfolded myself. I closed one end of the handcuffs around one wrist. With my hands behind my back I closed the second cuff around my other wrist. My heart was pounding. As directed, I clomped my heel on the floor three times and waited.

After a few minutes I heard the two of them enter the bedroom. They were very quiet. My senses felt like they were on overdrive, as I listening intently. I heard my wife crawl onto the bed. “Ok,” she said, “remove Sissy’s blindfold and then join me here on the bed.” Richard walked over to me and took off the blindfold. It was bright, and as my eyes adjusted I saw that my wife was completely naked on our bed, looking at me and smiling.

Richard, still standing next to me, started taking off his clothes. My wife got up and rubbed her body against Richard, who reached out and gave her lovely ass a squeeze. She walked around behind me, and then rubbed her bare breasts against the side of my face. Her nipples were large and harder than I’d seen in a very long time.

She pointed across the room to something I hadn’t noticed. It looked like a cell phone on a little tripod, pointing at me. “Richard’s recording a video of this on his phone. Isn’t that cool?” With the gag in, I could only mumble. “Now I will tell you about your initiation. You’re going to watch Richard fuck me. Isn’t that wonderful?!”

I tried to talk but couldn’t. She put her finger gently over my lips and whispered “Shhhhh. Just relax, little Sissy. I know you want this as much as I do.” I let out a little whine. She gave me a look that told me I was dangerously close to some very bad consequences. Richard was now naked, and he crawled onto the bed that my wife and I sleep on every night together.

My wife leaned over and lifted my chastity device a bit, apparently for the camera. “Isn’t it true that you have a tiny, useless cock?” I nodded my head. She said “I can’t hear you!”. Through the gag I tried to say “Yes, Mistress” as I more vigorously nodded. “So you admit that your dick is worthless to me. There is no hope of it ever satisfying me, is there?”. My words, “No Mistress” were again garbled, as I shook my head back and forth.

She slowly crawled onto the bed next to Richard. “Since my own husband can’t satisfy me, I had to find a lover with a Real Man’s Cock who can satisfy me. Sissy, you want your wife to be happy, right? You want me to fuck Richard right here and now in front of you, isn’t that right?” My choice was six more months in chastity, or to agree right now.

I nodded my head. “Say it nice and loud!” she said. I said “Please Mistress, fuck Richard,” but it was a mumble. “Louder!” she said. I repeated it, and it was almost understandable. They both snickered. “Sissy, it will be our pleasure to initiate you as a cuckold. Enjoy the show.”

Richard was on his back, and I watched as my wife straddled him. She has very strong legs, and sheh took her time lowering her pussy onto the tip of his very hard cock. Richard’s penis is average in length, but noticably thick. My wife is smaller in stature and definitely not a size queen. She prefers quality to quantity — although apparently I have too little of both for her tastes.

Richard took her breasts in his hands and gently kneeded them. She slowly started bobbing up and down, and I watched his cock go deeper and deeper into her each time. He lay there, letting her warm, wet pussy hug and slide on his manhood. My wife put her head back, clearly enjoying his cock in her. They both were moaning and breathing more heavily.

I became aware that I was straining against my bonds, and I tried to relax. My cock was still trying to get hard, pointlessly of course. All two inches of my tiny dicklette were straining against the chastity cage, getting nowhere. I was grateful to hot have spikes digging into my sensitive cock flesh. I could do nothing but watch as they fucked. It didn’t take her long to reach her first orgasm.

I guess that officially made me her cuckold. The moment quietly passed.

They changed positions, and my wife laid diagonally on the bed with her pussy pointed right at me. Richard moved between her legs and took her ankles in his hands and raised them up. Between his thighs I saw my wife reach down and guide his cock towards her pussy. He gently and slowly slide his cock into her again.

This time he was fucking her. Another man was fucking my wife, right in front of me, on our bed, as I sat watching helplessly. The concept hit some chord in me, and I started to quietly cry. It was blurry, but I watched his manly penis sweetly pleasuring my wife.

I was awestruck by how fascinating it was to warch his cock slide in and out of my wife’s vagina. Of course I had fucked my own wife before (although not for many months now), but I had never really seen it. It was magical! As he pulled back, her labia lips revealed themselves and wrapped snuggly around his glistening shaft. When he pushed back inside her, her tender flesh folded inside and hugged his cock even tighter. It was beautiful. More tears.

Of course I longed for that to be my cock, caressing her from the inside, feeling her warm wetness. Instead of the hard, oppressive steel cage, I craved to be a Real Man enjoying sex with my wife like Richard was. It wasn’t long before the crescendo of her moaning signaled her second orgasm.

He stopped, and I recognized her gently sighs as her being in that wonderful, post-orgasmic space that I love to see her in. My tears kept quietly flowing. I felt joy, pure happiness for the pleasure she was savoring. Those feelings mixed inside me with the sad reality of my inability to provide adequate sex to my own wife. I felt grateful for Richard.

He manuvered himself and her gently, spooning with her. He slipped inside her pussy again from behind and gently rocked his hips as they both began moaning again. It didn’t take long for her to orgasm again. It surprised me to realize just how horny she was tonight. And he really had impressive stamina. I was happy my wife had such a capable lover.

He kissed her and she rolled over to face him, wrapping her arms and her legs around his body. He caressed her hair, gently running his hands along her curves, her ass, her thighs. She whispered to him, he nodded, and she whispered some more. Even after three orgasms, I suspected she was orchestrating at least one more.

She layed diagonally on the bed again, on her back, but this time with her head near me. She reached out and held my chastity device in her hand and looked at me. She saw my tears and smiled. I looked pleadingly at her, but Richard had manuvered between her legs and was entering her. Her eyes slowly closed as she felt him filling her pussy for the fourth time. He held himself there, fully inside her.

She opened her eyes. “There is an important cuckold ritual next that will complete your initiation. Are you ready?” I nodded. “Good. I’m going to let Richard cum inside me now.” My eyes got big and she saw my shock. She calmly continued “Oh yes. Richard is going to fill my pussy with his semen and sperm. It’s going to be wonderful! Then I’m going to empty my pussy into your mouth. I expect you to enjoy and swallow every single drop.” I nodded meekly.

Richard started fucking my wife at that point, slowly at first, then more quickly. Her eyes closed, but her hand was still around my chastity device. Their bodies moved back and forth as they copulated, and her hand moved back and forth between my thighs. I wasn’t able to feel anything on my cock, of course.

He was watching her carefully. I realized he was timing his release so they would have simultaneous orgasms. I marveled again at his impressive lovemaking skills. Their breathing got faster and their moans increased. Oh the pleasure they were having that I had not felt in months! I sat helplessly watching as they both built to their climaxes.

And then it happened. Her orgasm started, and he followed her lead. I could see his tempo change, and it was clear that he was pumping his cum into her. My wife startled a little, and I suspect she felt the force of his spray inside her. Their moans were more like yells as he pumped her full of his manly load. They slowly wound down, and he lowerd himself to all fours above her, with his cock still inside her.

After a short while they both caught their breath, and they kissed. She really kissed him, clearly thanking him for one of the best rounds of sex she had ever had. She whispered in his ear, and he reached over for two pillows. Pulling out of her, he quickly put the pillows under her ass, elevating her hips. Obviously they didn’t want any of his seed slipping out of her.

He then walked over to me and unbuckled the ball gag. My wife said “Sissy, show your appreciation to Richard for doing an incredible job satisfying your wife. Clean his fabulous cock.” Looking at his cock I could see some white splotches of his cum, it was wet and slick with my wifes juices, and I recognized the smell of my wife’s pussy. Richard stood in front of me, put his hand behind my head, and stuffed his semi-hard cock all the way in my mouth. I sucked and cleaned his cock as best I could. I could taste more salty cum as it dribbled out of his penis onto my tongue.

He pulled his cock out of my mouth, and then surprised me by turning my chair around. Before I knew what was happening, he had tipped the chair back on the bed. The top of the chair and my head rested on the bed. I was looking up at the ceiling.

In a moment my wife was kneeling above me, and she was holding her pussy lips together with her fingers. “Now, Sissy, it is time to complete your cuckolding. By eating his seed from me, you accept your role as my fully cuckolded husband from this point forward.” She did not wait for an answer and lowered her pussy onto my mouth, removing her hand at the last moment.

I gently licked her labia, again tasting both of their sexual flavors. I slid my tongue between her lips and got a surprise. What seemed like a whole cup of warm, salty sperm poured from her vagina into my mouth, coating my tongue. I swallowed several times. She directed me to take my time and clean her deeply and thoroughly.

She sat there on my face for quite a while as I worked on the inside and outside of her pussy, cleaning and swallowing as much of their juices as I could get. Richard sat down opposite her and they resumed kissing. My tongue muscles were getting sore from all the cleaning, first of Richard, then of her.

Abruptly she got up. The two of them tipped my chair back up and turned me toward the camera. She sat down on the bed and looked at me. “Tell me what you are now,” she said. Trying not to hesitate, but struggling to come up with the words she wanted to hear, I said “I am now your cuckold husband.”

She smiled, and said “Go on.” I wasn’t sure what to say, but I could not risk hesitating. “I am happy that you have such a capable lover that can satisfy you, since I cannot. Thank you for allowing me to watch. Thank you for feeding me his cum from your pussy. I want you to have as much pleasure as you want, since I am sexually useless to you.” I hoped that was what she was looking for. I was suddenly aware again that all of this was being recorded on Richard’s phone.

My wife continued “That’s very good, just one more thing. Do you want me to keep fucking other men?” The look on her face made it clear that there was just one correct answer. I responded immediately. “Please, dear, I want you to feel free to fuck as many other men as you wish. My worthless cock means nothing, so please find Real Men with Real Cocks that can give you the pleasure you deserve.” She smiled.

“Is this what you really want? What you really, truly want?” she asked. “Yes, Ma’am, it is.” The smile on her face made it clear that she completely agreed.

So it’s official. In addition to being her pantied, sissy, chaste husband, I am now her cuckold as well. I am lucky, and I am glad that she is so very happy.

[ Story continues with “Advanced Cuckolding” ]

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