Fiction: Journey Into Feminization

[Cuckold Tales]

Heather suggested swinging shortly after we were married, but it wasn't long before she wanted me to watch her only and swinging evolved into her becoming a hotwife. A dominant side of Heather's began to emerge over time, and I started becoming more submissive while she was with FBs and FWBs. Within a span of 12-18 months, swinging evolved into cuckolding. Heather and I continued to have sex, and I enjoyed the new sexual dynamic to our relationship.

A new FB, Rex, quickly became a FWB, and then became Heather's regular. She lost interest in looking for FBs, and Rex was the only one that Heather was interested in. Rex observed the cuckold dynamic to the relationship between Heather and I, and didn't say much about it or get involved. He accepted it and appeared to not have any interest in being a part of it.

Having a regular BF added several new aspects to the cuckold dynamic of my relationship with Heather. One aspect was the routine that developed when she and Rex were together at our house. Heather often didn't want me to watch her and Rex, so I would often be in other parts of the house while they were together. Heather began at one point to text me instructions from the bedroom, one of which was to go to the spare bedroom, remove my clothing, and lay on the bed. Heather would then come into the room completely naked and straddle my face.

I remember how surprised that I was the first time that she did this, and the scent of her and Rex's sex. Heather settled down on my mouth and pushed Rex's cum into my mouth, and I felt a salty, slimy liquid on my tongue and sliding down the back of my throat. It was not a pleasant experience for me, and Heather didn't speak as she continued to push Rex's cum into my mouth.

Heather continued this ritual of having me clean Rex's cum from inside of her. She would then get off the bed when I was done and silently leave the room to return to the master bedroom where Rex was. I would lay there with the taste of Rex's cum in my mouth, wondering if Rex knew that his cum was slowly working it's way down to my stomach.

[armyguyot1]

Welcome to the forum Cuckold Tales.

[Cuckold Tales]

One of Heather's rituals was having me give her a foot massage after she returned from work. Heather was an executive at a large company often spent long days in the office. Heather established the routine of where I would kneel or sit on the floor while she sat on a chair or the couch in front of me and I would remove her high heels and massage her feet. Heather said one time while I was massaging her feet that men are lucky that they do not have to wear high heels. I didn't give it much thought until the following Saturday, when Heather instructed me to wear an older pair of her high heel pumps around the house. She laughed as I awkwardly walked around the house trying not to fall down. She let me take them off after 15 minutes, and I realized how good it must feel to her to have her feet massaged after wearing heels all day.

Rex and Heather were together in our bedroom later that evening, and I received the text message from her to go to the spare bedroom. I saw the pair of high heels from earlier in the day on the bed and froze. I heard the notification sound on my phone alerting me to a new text message. I slowly raised my phone to see a text from Heather, "Put the shoes on Mike." I removed my clothing, put the heels on and laid on the bed. Heather entered the room several minutes later and the familiar ritual of cleaning Rex's cum from inside of her began. I was very aware of the fact that Rex was in our house while I laid there wearing a pair of women's high heels. I guess that someone else would think that the fact that I was being fed Rex's cum from Heather's pussy would be more of a concern for me, but it was the high heels that I was worried about at that moment.

On a related note, I was used to the taste of Rex's cum by this point in our relationship I could tell differences in the taste from day to day. Rex's cum tasted more bitter on certain days, and I just wanted to quickly swallow it to get the taste out of my mouth as quickly as possible. His cum tasted "sweeter" on other days, and I would find myself not so quick to swallow it and let the taste and texture linger in my mouth longer. I wouldn't say that I enjoyed the taste, but I could tolerate the taste more on days that it was sweeter. I wanted to ask Rex what kind of food that he ate on days that it was sweeter, but I definitely didn't want to explain to Rex why I was asking him!

Heather climbed off of me after I finished cleaning her, and she stood next to the bed for a moment and looked at the high heels that I was wearing. She said, "I think that I like those on you Mike!" and left to room to return to Rex. I laid there wondering what I should do next. Should I leave them on or take them off? I ultimately decided to take them off, as I wanted to leave the room and didn't want Rex to know that I was wearing high heels.

I went into the bathroom for what had become a familiar routine for me after I cleaned Rex's cum from Heather. I wiped the mix of Heather's and Rex's juices from the area around my mouth and rinsed my mouth with the hope of removing the taste of Rex's cum. I looked at myself in the mirror this time and pondered for a moment. Where was this going? Was Heather going to make me wear high heels more often? Would I have to wear them when she saw Rex? My mind raced as the thoughts continued.

[Cuckold Tales]

As that weekend was winding down, Heather instructed me on Sunday evening to go to the spare bedroom and look on the bed. I saw a shoe box on the bed with a pair of red high heel pumps in it. They looked similar to the heels that she often wore, but somewhat lower and kind of chunky instead of a stiletto like hers. I brought the box to the room where Heather was, and she instructed me to put them on. They were my size, so they felt much more comfortable than the pair of hers that I had to briefly wear. She stopped me when I tried to take them off and said, "You will wear heels for me whenever I ask and can only take them off with my permission." I wore the heels for the remainder of the evening and she gave me permission to take them off when we were getting ready for bed.

She texted me after I got home from work the next day, "Put the heels on." I went to the bedroom and put the heels on, and attempted to continue with what I was doing. It was hard to walk around the house in the heels, and I often grabbed things to hold onto. Heather was pleased when she got home from work and observed me walking around in them, frequently laughing. After dinner, she said that she was going to give me some advice in how to walk in heels. She led me to the hallway and told me to watch her feet as she walked in her heels. She then watched me and quickly stopped me. She gave me several tips, "walk from heel to toe", "take smaller steps", "stand up straight", "pretend that you are trying to walk on an invisible line, place one foot in front of the other." I listened intently as I tried to follow each tip. It began to get easier, and I didn't have to reach out so often to prevent myself from falling.

I returned from work the next day to the same text, "Put the heels on." I did as instructed and groaned as my feet still hurt from wearing the heels the previous night. Heather noted how much better I was getting at walking around in heels than the day before. Heather gave me a break the next night and didn't make me wear the heels, but I had to wear them the next 2 nights. Rex came over on Saturday, I was very glad to see that Heather didn't make me wear them while he was there.

The next week was similar as the week before, and Heather made me wear the heels every night after work. My feet were killing me, and I wondered if that would ever stop. Heather called me to the bedroom on Thursday night that week, and she was on the bed. She told me to take off the heels and get on the bed. She pulled out 2 bottles of nail polish and began to show me how to paint my toenails. She had me watch her paint her toenails and then watch her paint mine. My toenails were bright red when she finished. I was glad that I did not have to put the heels for the rest of the evening on since my toenails were still wet and had to dry.

I was very self-conscious about going to work the next day with red polish on my toenails. While no one knew, I felt very nervous all day, and was glad when I came home. Heather sent me a text just after I returned home, "There is a new pair of shoes on the bed. Put them on." I went to the bedroom to see a shoe box on the bed. Inside of it was a pair of high heels that had straps and you could see more of the foot in them. I loved it when Heather wore these kind of high heels, because they looked so sexy. It took some time to put them on, as the straps made it a bit difficult. I looked down and suddenly realized why Heather painted my toenails the previous night. I could clearly see my red toenails sticking out of the end of the shoes! I quickly realized that these shoes were harder to walk in than the other shoes, and I noticed after a while that they were a bit higher. I sat down after a while and instinctively crossed my leg as I sat. I immediately noticed my red toenails, and my focus shifted to my foot. I decided to cross my legs the way that a woman nearly does, and I looked down at the foot of the leg that was crossed over the other. Just looking at that body part only, I realized that it looked kind of sexy. I then stood up and walked around and looked at my feet sticking out of the bottom of my jeans as I walked. They looked sexy! I looked sexy!

Heather cooed as she came in the door from work, "Oooo, those look so cute on you!" Once again, she didn't make me take them off until we got ready for bed. To be honest, except for the pain from walking in them, I didn't want to take them off.

[Cuckold Tales]

Most days, Heather would text me after I returned to work to put the heels on, and I was becoming more used to wearing high heels. Heather bought me several new pairs of high heels, and they were somewhat higher and had more of a stiletto heel than the first pair. She bought a shoe rack and put it in the spare bedroom closet for me to keep all of the shoes. It also became routine that I would wear heels while cleaning Rex's cum from Heather, and I usually picked which pair that I wanted to wear.

Heather took things to another level one weekend while Rex was there. Heather texted me to go to the spare bedroom as usual when I cleaned Rex's cum from inside of her. I saw a pair of women's panties laying on the bed when I entered the room, and another text from Heather to put them on. I slide the panties on and felt the strange feeling against my skin. I felt my cock harden as the silky material touched the underside of it. I then put a pair of high heels on and laid on the bed. Heather entered the room and stopped for a moment, smiled at me, and then straddled my face. She climbed off of me and silently left the room.

I laid there for a moment as I heard the door to our bedroom shut, and wished that Heather included me more in her sex life with Rex. I missed watching her have sex with other men, and she became different when she started having sex with Rex. Aside from me preparing the bedroom before Rex came over, Heather now only had me clean Rex's cum from inside of her. She was usually silent when I cleaned her, and it appeared that she was thinking about Rex the whole time and then quickly return to our bedroom without saying anything to me. I felt excluded.

Heather told me to put the panties on again the next day after Rex left, and I wore them under my jeans all evening, with the high heels that I wore almost all of the time at home now. I was erect most of the evening, and I could even feel some wetness from the pre-cum that was leaking from my erect cock. Heather stopped me as I began to take them off as we were getting ready for bed. She told me, "I want you to sleep in those panties." I didn't sleep well as my erection was distracting throughout the night.

I could have guessed what happened the next day, as I got a text from Heather after I got home from work, "Put the new panties that I got you on, I left them on the bed." I walked into the bedroom to see a pair of pink lace panties. I put them on and noticed how much less of me was covered by them. I slid my jeans on over them and could feel my bare skin of my butt against the jeans. I noticed that feeling all evening as I walked around the house and sat down. Heather told me the next morning that I was to wear the panties to work that day, and I got dressed for work with a fear that everyone would know that I wearing women's panties under my pants. I used the bathroom stalls, instead of the urinal, when I went to the bathroom in case someone else noticed.

The panties quickly became part of the routine of the high heels that I wore around the house most of the time, but Heather seemed to make me keep that panties on when she let me take the high heels off. She told me one day a few weeks later that she was going to make some changes. Heather began to tell me the what would become the new "normal" for me. She told me that I would wear women's shoes at all times around the house, and that she bought me several pairs of new shoes that would not hurt as much as high heels. She explained that she bought sandals and flip flops for me to wear to give my feet a break. She also told me that I would be wearing women's panties permanently, and that she had replaced all of my underwear from my dresser with panties. I briefly tried to refuse to do this, and I let her know that I was thinking that this was a game or role-playing.

Heather let me know that she initially felt the same as me, that this was a game that we played together. She went on to say that she was making this part of our cuckold relationship. She explained that she was developing deep feelings for Rex, and that was contributing to the declining amount of sex that we were having. I had noticed that we did not have sex very often since Rex and her began seeing each other regularly. She said that Rex had become her primary sex partner, and she felt our relationship was evolving beyond a stereotypical husband and wife to one where I was a full-time cuckold. She continued, saying that it was easier for her to see me as less of an "alpha male" and more of a cuckold when I was visibly showing more feminine traits. I was open to becoming more of a cuckold to Heather, and I was willing to do this for her if it helped her to think of me as a cuckold.

[mwmbound]

love the story, can't wait for more!

[OOAA]

Very exciting story!!!! Congratulations!!!!

What a pity she is not interested even in wanking him....

[Cuckold Tales]

The weeks went on, and I was able to often wear the women's shoes that weren't high heels. The felt more comfortable, but they were all the style of shoes that showed my bright red toes. I was still very self conscious about this, and it took some getting used to. I walked outside on our patio one day, wearing a pair of women's sandals with a pair of shorts, and Heather said "Yuck! Those hairy legs look horrible with those shoes. Come with me." She led me to the bathroom and proceeded to show me how to shave my legs. I watched as she used an electric trimmer to remove most of the hair and then a razor and shaving cream to remove any remaining hair. After we went back outside, I noticed how much sexier my legs looked than before. Heather instructed me later that night to include shaving my legs as part of my showering routine. I realized that it would not be possible for me to wear shorts outside of the home without other people noticing that my legs were shaved.

Heather pushed me further one Saturday by revealing to me yet another dynamic. She called me to the bedroom in the early afternoon to show my that she had bought a bra for me. As I looked at the bra, I asked her why I would wear a bra if since I didn't have breasts. It was at that point that she opened a box on the bed that contained 2 fake breasts. I stared at the box for a moment, and Heather picked one up and handed it to me. I felt the silicone materials and squeezed it. Heather said, "These are your breasts." She proceeded to help me put on the bra and insert each breast into the bra. I stood there, now in a bra, panties, and high heels, and saw how feminine I looked. I was aroused and humiliated at the same time.

Next, Heather returned from the closet holding a dress. She showed me how to put it on and said, "Wait, I almost forgot!" She went into the closet and returned with a wig with curly, blonde hair. She put the wig on me and told me to look at myself in the mirror. I looked at myself in the mirror and was once again surprised how feminine I looked. With the exception of my face, the rest of my body looked like a woman's body. Heather stood next to me and admired her work. She said, "You like very cute in your new dress, Mike."

She paused and then said, "Mike doesn't sound like an appropriate name for you at this moment. Let's call you Melissa instead. Follow me Melissa." Heather led me to the toilet and said, "Let's show you how to go to the bathroom in a dress." She helped me pull the dress up as I sat down on the toilet. I stood up after a minute and we both left the bedroom. I spent the rest of the afternoon in the dress and wig and into the evening.

Heather was drinking several glasses of wine after dinner and then told me to follow her to our bedroom. She went to the closet and emerged with another dress, this one was shorter and looked more "slutty" to me. I took the dress that she gave me earlier on and put the new dress on. Heather told me to go to the spare bedroom and wait for her. She came into the room a few minutes later, wearing a harness around her waist with a dildo attached to it.

Heather instructed me to get on me knees in front of her, and she guided the dildo to my mouth. As I looked at the dildo closer, I noticed how small that it was, and I didn't know that you could buy a dildo that small. Heather slid the dildo in my mouth and held it there a moment. She said, "Go ahead Melissa, suck it." I took more of the dildo in my mouth and realized how difficult that it is to not gag. Heather laughed as I attempted to take the dildo deeper and gag each time, and finally stopped and told me to inhale through my nose as I pushed it deeper in my mouth. I tried again, inhaled through my nose and the dildo slid deeper down my throat. Heather spoke softly to me, "Just relax Melissa and focus on breathing through your nose." I held the dildo deep in my throat and followed her instructions.

I pulled my mouth back after a few moments and gasped. Heather said, "That's a good girl Melissa." I caught my breath for a moment, and Heather instructed me to spit on the head of the dildo this time so that it slid down my throat easier. I spit on the end of it and began to push it down my throat again. I held my mouth against the harness that Heather was wearing, and focused on my breathing. I felt Heather's hands on the back of my head, pushing the dildo deeper down my throat. Heather said, "Suck it Missy, suck it deep." I began to gag, and Heather held my head down while saying, "Take my cock bitch, take it all!" I could feel drool spilling out of my mouth as Heather fucked my throat with the dildo.

Heather finally let go of my head and I immediately pulled my head back and saw a large amount of drool spill out of my mouth on the to floor. I coughed several times and caught my breath. Heather got down on the floor with me and held me softly. "There, there Missy. That was a good girl. You did a great job." She held me for a moment and then stood up. She then instructed me to get on all fours on the bed. I had a feeling that I knew where this was going, and I was right. Heather started working one well-lubricated finger, and then 2 into my ass. After 5-10 minutes, she removed her fingers and positioned herself behind me.

I felt the tip of the dildo against my asshole as Heather got ready to push it inside of me. Heather began to ease it in slowly, stopping several times to allow me to get used to having it inside of me. I could feel that harness that she was wearing against my skin after several minutes, and she began slowly moving in and out. She often paused when moving out to apply more lube to the dildo. It was then that I realized Heather hadn't started fucking me yet.

Heather grabbed my hips and began moving in and out faster, and pulling my hips closer to her and pushing the dildo deeper inside of me. I tried to not focus on the pain, but it was difficult. Heather began making noises and say things like, "That's it Missy, take my cock." and "Tell me who owns your ass." When I didn't respond, she barked "Tell me!" I meekly said, "You do." She kept going, fucking me with a steady rhythm now. She said, "Tell me what you want Missy." I said, "I want you to fuck me." Heather said, "Come on, tell like you mean it!"

It was then that a switch flipped inside of me. I was in a slutty dress and heels, getting fucked from behind, and I mentally began to feel like a woman. I moaned loudly and said, "I want you to fuck me, fuck me like the slut that I am!" Heather said, "That's what I am talking about and began fucking me faster and harder." It hurt so much, but I didn't dare say anything to her about the pain for fear that she would fuck me even harder. Instead, I begged louder. "Fuck me, fuck me hard! Give me all of your cock!" I looked down to see the fake breast in the bra that I was wearing bouncing forward with each thrust from Heather. I felt Heather's hand smack my ass as she fucked me relentlessly. I screamed, "Fuck me! Fuck me like a slut! I'm your slut, I'm your slut!"

Heather finally stopped fucking me and collapsed on top of me. She kissed the back of my neck and said, "I love you Missy."

[DonaldElliott11]

Terrific, and I urge you to continue. Rex needs to meet Missy. After all, "a man can't be a woman for a woman. A man can only really be a woman for another man." I think Abraham Lincoln said that. Or Confucius.