How I became a Hotwife and turned my sissy into a Cuckold
- 9 months ago
- 27 min read
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I laid there still panting with my pussy quivering and my entire body uncontrollably spasming from my second orgasm and quite possibly the best sex I have ever had from a man that I didn’t even know. I could feel the bed beneath me soaking wet from my juices and I could feel his amazing cock, which had just been so deep inside of me that I could almost taste it. It had started to soften and all I could think about was, please don’t, please fuck my married pussy again. A voice was screaming inside my head, “Oh my god, I’m a slut, I just fucked a guy that I just met last night, and he made me feel like more of a woman than my husband ever has”. I think I knew then that this would not be the last time I became a willing slut for men I did not know. That is when I looked at my husband on the side of the bed and said those three little words...
Before I tell the full story of how I became a Hotwife, you should know a couple things about me. I am a classy, sophisticated, and refined woman in my late 40s who was married for a long time to a great man. I am considered by everybody that knows me to be the perfect suburban housewife who raised amazing kids, always looked her utmost best and spent all of her time being the best Mother and Wife I could be.
I am also a woman with a very strong libido.
I have been very sexual ever since high school and have always considered sex an especially important part of my life, but it was always confined to my marriage bed with my husband. We had a great sex life, and I loved every minute of it, I just didn’t know at the time that it was what most would call vanilla.
When I finally got over the ending of my marriage, I began to date and as fate would have it, I was contacted by an old friend who I hadn’t seen in 30 years and we agreed to meet for coffee to catch up. He was a guy that I knew from college who I’d never dated, but I knew he was a good guy, and I knew through social media that he had divorced a couple of years prior. I didn’t expect anything from the meeting, I wouldn’t call it a date, other than to see an old friend and try to learn how to start dating again.
When he showed up, I was pleasantly surprised by how well he had aged over the years. He was tall with broad shoulders, a tapered waist and muscled upper body. The conversation between us was the most natural thing even though we hadn’t seen each other for so long and I found myself wondering if he was interested in me. After our “meeting” it didn’t take him long to settle that question when he asked me out on a real date. We began to date and quickly fell in love.
As we began to get intimate, I quickly realized that he was at least as sexual as I was if not more so. He was also so much more open to experience all things sexual than I was. The sex right from the beginning was amazing as we explored each other’s bodies and learned how to turn each other on.
He had an average length cock, which was very thick that felt amazing inside me. The combination of his cock and a vibrator on my clit gave me explosive orgasms. He also had an amazing ability to pull out every deep fantasy I’ve ever had from the inner recesses of my brain and he began to paint pictures, scenes and stories in my head while we had sex. His words described things that I wanted but was always afraid to express out loud. Those words turned my wants into deep needs and cravings.
From the very beginning, I found that he purposely held off his orgasm so that I could have one… or as many as I needed, oftentimes without himself coming.
Frankly, this puzzled me.
I was used to sex being a two-way street where both people orgasm and then roll over in bed and fall asleep. This man didn’t want that. He wanted to bring me to climax (again and again) and then to cuddle me all night without himself achieving orgasm. To be honest, I didn’t know how to interpret that… after all, while I love coming myself, I also love giving a man the pleasure of an explosive orgasm.
It took me months to understand what he kept telling me and to believe him. He taught me that making me orgasm gave him more pleasure than having his own could ever do and that by denying him orgasm, it kept him in a constant state of horniness, which made him a better lover, a better cuddler, and what I would learn later… very compliant to my wishes and desires. That was the first of many lessons I learned from him on my journey to being in that bed with a strange man.
As our love for each other deepened, he began to be more open about elements of his personality and sexuality that only a woman that loves him would understand. He told me that he enjoyed wearing panties and occasionally more than just panties. That news turned me on because it gave me something to give back to him… the ability to embrace his feminine side. When he saw how accepting I was of his “panty fetish” he finally admitted that he was an experienced crossdresser and that the reason he dressed up as a woman was to embrace the submissive nature that was hidden deep inside him.
I’ll write more in the future about how that admission affected me and how I’ve made him evolve from a crossdresser into a proud, devoted sissy, but this blog is about making him my cuckold. Just know that over the years, I have made him into the perfect submissive sissy that now gives me orgasms on command, is my willing servant, finds men to fuck me AND most importantly, loves me unconditionally. I now call him Sissy B whenever I’m in a dominant mood.
OK… So, how did I become a Hotwife and turn my sissy into a cuckold? Well, it all started with him. He kept painting these pictures in my mind about me being with other men, while he stands by and plays with himself. Sometimes the fantasy would involve him sitting in a chair as a man, and sometimes he would be dressed as a pathetic sissy, but he would always be submissive to me and my lovers. In all fantasies, I would degrade him in front of whatever man I happened to be with. I would tell my fantasy man that my husband was a pathetic sissy faggot with a tiny cock who didn't deserve to be called a man anymore. This fantasy was my go-to during sex and would always result in explosive, mind blowing climaxes, often with several follow-up orgasms.
As my sissy’s sexual submission deepened and I grew into my dominance over him, I began to understand that my fantasy could be so much more than just a fantasy. The realization hit me that there was nothing to stop me from experiencing for real what I’d been dreaming, fantasizing and talking about for the past two years. It was at that point that I decided that I would live it out… and become a Hotwife.
One week later, after an evening of mind-blowing sex for me (I had since adopted a strong tease and denial program for him and he hadn’t orgasmed in almost 3 weeks) I informed him that it was time for me to make him my cuckold. His reaction to those words just confirmed that I had made the right decision. He was like a puppy getting a treat. If he had a tail, he would have wagged it. He was so excited and such a willing puppy that I decided to let him orgasm as we were talking about our upcoming adventure.
I started stroking him as we talked about how we were going to make it happen. I continued stroking him as we talked about the logistics. He was rock hard by this point. I looked deep into his eyes and kept stroking as I told him what I wanted the man to do to me. As I started to tell him whether I would let my new lover cum inside of me, he started to moan. His balls pulled up and his cock started quivering. I gave him 3 more strokes and just as he was about to erupt, I released his cock and grabbed his hands so he couldn’t finish himself off. I sat there and watched as cum meekly spurted from his sissy dick. His hips were bucking as if the friction from the air would help him to finish his orgasm and he seemed to almost be sobbing from the ruined orgasm. I gave his balls a firm swat that made him yelp and said, “sissys that get turned on from their wife being fucked by other men, have no rights to ever orgasm again.”
My pussy was so wet from the conversation, the anticipation of finally fucking a stranger and from the power of ruining his orgasm so I climbed on top of my throne (his face) and fed him my dripping juices till he gave me my third orgasm of the night.
Afterward, we spoke for the next hour about my rules and how I wanted him to set it up. I required that it was with a younger man and somebody that we didn’t know and of course, he had to have a bigger cock than Sissy B so that I could degrade my sissy with how good it feels to have a man bigger than him. I had never seen my sissy so turned on as I instructed him on when, where, how and the type of guy that he had to find. Just knowing that it was finally going to happen made the love of my life act like a teenage boy who had just groped his first pair of titties. It was intoxicating doing this to my Luv, my sissy, and my cuckold-to-be that I climbed on my throne and orgasmed one more time.
As is my nature, after telling my Luv what I wanted, I stepped back and let him be the obedient, compliant and industrious man that I knew him to be. I knew I did not have to get involved in the setup because he would ensure that every detail was taken care of.
See… I wanted to have a completely anonymous experience for our first time. I needed it to be with a man I’d never met, and that Sissy B didn’t know. This was to enhance the intimacy of our relationship and all we were doing was bringing a sextoy into bed with us. When it was done, we would quickly kick the toy to the curb and relish in the deeper intimacy we shared together.
Our adventure happened in a beach resort in Santa Barbara, California. We had gone there for a long weekend. Our second night was to be the night that I made Sissy B into a sissy cuckold and while I was nervous about having my first truly anonymous sexual encounter, I loved how horny and obedient my Luv was and knew that this night would be amazing for us both.
As instructed, Sissy B brought full sissy attire. When I say sissy, I don’t mean French maid outfits or pinafores, I mean full femme with heels, thigh highs, wig, makeup, fake boobs, etc. I’ve worked hard on turning the man I love into a completely obedient and almost passable girl and I absolutely adore how ultra-submissive she becomes. I wanted to make sure my new lover would see that. (I’ll write more about how I found resources at CircleofQ.com to help turn her into the perfect sissy husband.)
I had instructed Sissy B to ensure that the man who would make him a cuckold knew that he was a pathetic sissy and that he loved being emasculated more than he loved making love to me. He was told to give his sissy name and to make sure the real man wouldn’t be nervous about another “man” --as if he still deserved to be called that, lol--being there. That thought alone always results in my panties becoming completely soaked. :-)
I didn’t allow my Luv to see me getting ready. I wanted it all to be about me getting ready for another man and I wanted to deprive him of helping me with that. Luckily, we had two full bathrooms in our suite, so we got ready separately.
When I was ready, I walked to the terrace where my Luv--no longer a man, but a beautiful, sexy feminine creature--sat with her legs crossed sipping a glass of wine.
The terrace overlooked the ocean, and the sunset was stunning as I just stood in the doorway looking at her sitting there and knowing that she loved me so much that she was allowing me to explore my sexuality to the deepest depths. My own love for her then was so powerful that my heart almost leapt out of my chest.
She looked up at me to see the outfit that I would be wearing as I turned her into a cuckold for the first time and she just melted. Her gaze started at my 4” ankle strap stilettos and up my legs covered in silky thigh highs held up with a sexy garter belt. The peignoir I selected left only a little to the imagination as it showed off my tight ass. It was low cut to show off the cleavage of my perfectly done breast implants. Her gaze stopped at the necklace I was wearing, and a broad smile broke out on her face as she read the one word that I had chosen to describe myself tonight…
I could see the passion, the love, the desire explode inside of her, and I watched all remaining masculinity drain away as she completely accepted her role for the evening.
We sipped wine and chatted in an incredibly nervous way ‘til my sissy got the text that told her that a real man was there to make him a cuck.
The hotel required that you have a key to get into the elevator, so I made her go down to the lobby to bring him up.
Yes… she was fully feminized and 6’4” in 4” heels and I made her go get him. She would certainly stand out in this posh hotel. Knowing that made it more exciting for me to make her walk the gauntlet. I sat in the room and imagined the thrill of her embarrassment and emasculation.
I visualized the blush burning on her cheeks and the terror she would feel as she was ogled by everybody in the lobby. The thought of my sissy walking down the hallway into an elevator and then into the lobby looking for a man to fuck me almost made me want to grab my vibrator and orgasm before they came back up. But I used every ounce of self-control I could find and just enjoyed the sopping wet feeling between my legs.
When my sissy returned to the room with a real man, I was immediately captivated by him and was incredibly pleased with my sissy. She had found a gorgeous man.
He was in his early 40s, very distinguished and handsome. I could tell from his stylish and polished clothes that he was a successful man and his athletic build added to my excitement. He had broad shoulders, a small waist and I could see the muscles in his arms and shoulders through his well fitted shirt.
I gave him a quick hug as I learned that his name was Brad and he commented on my outlift.
I was so nervous I almost couldn’t speak.
It wasn’t ‘til after the hug when he looked at Sissy B and said, “Hey sissy, get me a glass of wine”. Hearing him immediately take control of my husband made my nipples harden.
As Sissy B was getting the wine, he put his arms around me, gave me a quick kiss and looked into my eyes. As we stood there with his arms around me, he kissed me again, this time harder and longer, I could feel his cock getting hard against me as I ground my dripping wet pussy against him. He was still holding me as Sissy B walked back into the room. The gorgeous stranger looked at her for a moment and then said to me, “I can see why you need a real man to fuck you. Your husband looks like a little sissy faggot.”
I grinded into him harder hearing that and said,
“He is Darling, he truly is”.
Brad grabbed my hand and told Sissy B to follow us out to the terrace where we sat on the couch cuddling together. Sissy B tried to give us the wine, but Brad stopped her and said, “you’re not worthy to serve us standing up, get on your knees you pathetic bitch”.
I swear to you that I almost orgasmed right there. OMG, the way this man took charge of the love of my life was absolutely intoxicating to me.
My hand reflexively dropped to Brad’s crotch as I rubbed his growing cock inside his pants. Sissy B dropped to her knees in her pretty dress and handed us the wine. Brad then made it noticeably clear that he was the Man as he turned to me and spoke.
“I’d like to make sure we’re clear on roles tonight. Your husband contacted me and admitted to me that he’s a Sissy… and that you made him that way. Now that I see him, I think he’s a lot less than a sissy… he’s a pathetic little cunt. I don’t see an ounce of manhood in him. He, and I use that term lightly, told me that he is not man enough to fuck you like you truly deserve and because of that you told him to find somebody like me. Is that true?”
That statement made so matter of factly by such a gorgeous man, as my husband kneeled next to us, made me just want to explode with lust.
I reached inside his pants and wrapped my hand around his massive cock. I looked up at Brad, hesitating for a moment and then kissed him with such passion that it surprised both of us.
The kiss was the most sensual of my life and lasted at least a minute as his tongue explored me and I tasted him. When the kiss ended, Brad looked at my Luv, smiled and said, “OK sissy cunt, I told you what you would have to say to make this happen, now is the time if you’re serious about this”.
Without hesitation the love of my life said “I’m a sissy. My wife knows that, and she needs a real man. I cannot satisfy her like you can. Will you please fuck my wife?”
Hearing the love of my life say that to another man made me melt with passion. Brad immediately started kissing me deep and running his hands all over me… and all I knew was that I wanted him… needed him.
I needed this huge cock that I was stroking inside of me.
Making out with him as Sissy B watched was exhilarating, but I wanted so much more. I begged Brad to take me to bed and fuck me like the slut that I wanted to be, making sure that my sissy could hear.
He turned to Sissy B and said “I want to make sure you hear that, you cunt. Your wife is begging me to fuck her. Do you see how hot she is and how turned on she is? Look at her hand inside my pants rubbing my cock. This is what happens when your wife is with a real man. She is so excited right now, I could probably kick you out of the room and she’d spend the entire night with me.”
He looked at me and said “Do you want that baby?”
I was so excited and turned on that I would have agreed to absolutely anything this gorgeous man wanted. All I could do was nod my consent. Brad laughed out loud and said “Did you hear that sissy? Your wife doesn’t want you anymore. She wants me to kick you out in that sissy outfit you’re wearing and let me do anything I want with her the rest of the night. What do you think about that?”
The fear, angst and excitement on Sissy B’s face was like catnip to me. She was so excited, but also was so scared that Brad might actually do it. That’s when Brad reached out so fast that I almost didn’t see his hand as he slapped Sissy B and said “I asked you a question you pussy.”
OMG, seeing the fear and surprise on Sissy B’s face as she accepted a slap from a real man made me reach down with my free hand to rub my soaking wet pussy. I had no idea how seeing my husband completely emasculated by another man would turn me on so much.
Sissy kept her eyes to the ground as she said “Please don’t, please let me stay here. I’ll do anything”.
Brad looked at me and said, “Did you hear that? She’ll do anything. Your sissy is so pathetic.”
He turned back to Sissy B and said “OK. Here’s the deal, I will let you stay, but only after you do the following. I need you to look deep into your wife’s eyes and repeat after me. Are you ready sissy?”
Sissy just nodded and Brad continued “OK, look at your gorgeous, sexy wife as she strokes my cock and repeat after me. I am a sissy. I am not a man.”
Sissy B started to murmur those words, but I watched as Brad’s hand reached out with lightning quickness slapping Sissy B a second time and said “You don’t mumble when you answer me Sissy cunt. Say it loud and proud or you’ll get slapped again.”
Sissy’s cheek was bright red from the slap as she loudly repeated the words. I was so turned on by this that I was ready to just bend over and beg Brad to stick his amazing cock in my pussy and fuck me like he owned me. But Brad wasn’t ready for that yet. He could tell how much this was turning me on so he continued.
He looked again at Sissy B and said, “Good girl… now continue. I am Brad’s bitch and I will do anything he says.”
Sissy B looked deep into my eyes and repeated those words. Hearing my husband tell me that he was another man’s bitch gave me a feeling of such lust. I could feel another gush of wetness inside me and I felt like my hand was sinking into a warm bath.
Brad continued, “I will always be a sissy and I will always beg real men to fuck my wife.”
Sissy looked into my eyes and I could see her acceptance of that statement as she repeated it to me.
Brad then said “OK. I think you’re not just a sissy. I think you’re a faggot too, but we’ll let that go for now, because your wife needs me now and I want to take her in the bed. So crawl your sissy ass into the bedroom, get the bed ready for us and then kneel at the foot of the bed.”
Brad’s cock was rock hard by then even though he was still wearing his pants. I was rubbing my clit and felt an electric shock with every word that he had said to Sissy B pulse through my pussy.
Brad slowly led me to the bed and sat me on it as he stood in front of me. He kissed me as I stripped off his shirt and began kissing his chiseled abs. He rubbed his hands all over me and took off my slinky robe that covered my negligée. While kissing his abs, I ran my hands over this man’s amazingly firm and muscled ass. I couldn’t stop myself.
As I started to unbuckle his pants, Brad grabbed my hands, stood me up, looked into my eyes and said, “Let’s make your sissy do that.”
I kissed him deep and stood to the side as he looked at my Luv and said, “OK faggot, crawl over here and take off my clothes. Do it fast or I’ll make you use only your teeth to get them off.”
Seeing the love of my life take off this man’s clothes was almost more than I could take.
Brad was fondling my breasts and had his tongue deep in my mouth as my pathetic sissy husband took off his pants and underwear. I heard a gasp from Sissy B as he finally got a look at what I had been stroking… Brad’s gorgeous manly cock.
It was long, but also a perfect shape and thickness. I knew that my sissy recognized that it was so much bigger than hers as she looked up at me with fear in her eyes.
That look alone almost made me cum.
I could not help myself, I reached down, grabbed Brad’s amazing shaft and dropped back on the bed so I could get it in my mouth. Finally tasting his rock-hard cock gave me a feeling of complete bliss.
He was so hard, and he felt like heaven in my mouth. I played with the tip as I savored the taste and feel and then licked the shaft from his balls to the head before taking it in my mouth again, and slowly gliding all the way down as far as I could go.
Brad moaned, telling me that I was doing exactly what he wanted. I loved having his muscled ass in my hands as I greedily sucked his cock. My excitement was amplified knowing that my husband, sissy and soon to be cuckold was kneeling no more than a foot away…. and it was the most natural thing in the world.
As I was worshipping Brad’s amazing cock with my mouth, I heard him talking to my sissy and the conversation made me want him so much more. He made my sissy tell him how pathetic it was that she had to have another man come in and pleasure his wife. I heard Brad say, “Tell me that you’re not a man. Tell me that you are a pathetic sissy and don’t deserve to be with a woman as amazing as this.”
I heard my sissy mumble and then heard the sound of a slap as she gasped in surprise. I looked up in time to see the shame on Sissy B’s face and another red bloom on her cheek.
Brad said, “I told you about mumbling.”
I was so proud of my sissy when she took the continued slapping like a good bitch should and loudly proclaimed, “I’m a sissy. I’m not a man. Only a real man like you can give my wife what she needs.”
This time I got to see as Brad slapped my sissy again, but on the other cheek as he said, “Good sissy. You are so pathetic. Now ask me again.”
My true love, my sissy and my protector immediately looked up at Brad and said, “Please, please fuck the love of my life.”
I was so excited, I couldn’t help myself as I took my mouth off of Brad’s cock and said, “Slap her again, please.”
I went back to sucking his cock to the sound of a hard slap quickly followed by another yelp of pain from Sissy B.
The rest is almost a blur.
I know that Brad picked me up, laid me on my back and climbed on top of me. I vaguely remember him telling my sissy to put a condom on him, hearing another slap, and then feeling his hard, thick cock penetrating me.
I was so hot and wet, that it slid right in on the first thrust and that’s all it took.
OMG the orgasm hit me like a tidal wave.
He wasn’t even fully inside me and yet my pussy was convulsing around his amazing cock and my body was surrendering to him.
I typically require a little more play than that to climax, but I was so turned on by the degradation of my husband and by this amazing man on top of me that I orgasmed for what seemed like minutes as I gave myself to him.
His cock felt so good and his body felt so perfect on mine. When he kissed me, it felt like I was being taken possession of and I relished that feeling.
Brad stayed inside of me, allowing me to enjoy the feeling rushing through me. But it didn’t take him long to show me that I was there to pleasure him. He started to slowly move his cock in and out of me. I still wanted more and encouraged him to please take what was his. That is when I remembered that my sissy was in the room… had honestly completely forgotten about her.
She was kneeling by the side of the bed and I looked over at her and mouthed the words, “I need this so bad”, as Brad started pounding me hard. She grabbed my hand as I felt my next orgasm building.
Brad was still on top of me and I felt like his cock was up in my throat, it felt so good. His body was made for mine and we fit together like I’ve never fit with another man.
I wanted to make him come.
I wanted to make this gorgeous hunk of a man shoot his massive load of cum inside of me.
I loved the feeling of being a true slut that fucks strangers.
I loved showing my pathetic sissy husband what her future looks like.
I loved the emasculation that she felt as I writhed under this man.
I loved showing my sissy how much pleasure I get from real men.
I wanted to do things for this man that I would never do for my husband.
I wanted so much from this and my second orgasm was so close.
At that moment, Brad said, “Your sissy husband doesn’t deserve to fuck you anymore. He’s too much of a pathetic bitch boi.”
He could tell what that did to me as my orgasm got closer and closer. He then looked Sissy B in the eye and said, “I’m going to cum in your wife you fucking pathetic sissy faggot.”
OMG… with those words, I found Nirvana.
I erupted with the most powerful orgasm of my life as I felt Brad explode inside of me. I could feel every twitch and throb of his amazing cock as I spasmed and screamed from the absolute pleasure. My body was uncontrollably writhing against him as wave after wave of orgasm hit me again and again. Hearing him moan and grunt on top of me as his cum filled the condom made my orgasm last even longer. It had been so long since I had been truly fucked by a real man and felt one orgasm inside of me…
It was heavenly.
We stayed in that position for what seemed like hours even though I’m sure it was only minutes as we reveled in the passing orgasm. Brad kissed me deeply as we enjoyed the last moments of pure utter sexual passion.
Out of the corner of my eye, I saw my sissy kneeling at the side of the bed. I looked over at her as this man was still on top of me, his cock still inside of my well used pussy, his lips kissing my neck and mouthed those three little words…
I love you….