Journey to Cucoldry

For the longest time, I have been turned on by what some might consider abnormal fantasies. I did always think I was a bit odd, but I learned to own my kinks and enjoy them with my wife. I very much enjoy being teased and denied orgasms, as it keeps me on edge and extremely horny for as long as my wife keeps going. Unfortunately for me, she usually gives in within a couple of hours, we have sex, and go back to normal everyday activities. The best denial session we ever had was one evening she wore sexy lingerie and kept me in my CB3000 chastity belt that we got for such teasing. She told me how much she wanted a big cock inside her, but that I had to choose between using her big dildo on her or my cock. I have an average sized cock and I love fucking her after stretching her pussy with the very large 10" dildo I bought for her. I get seriously excited when I get to push the dildo into her wanting pussy and listening to her moan. Just to keep things interesting, I opted for the dildo, thinking I could convince her to let me fuck her as well. I fucked her with the dildo for what seemed like hours and after making her cum several times, she said she was done and she removed my CB3000. I tried and tried to get her to fuck me, but the only thing she would do was put my dick in her and hold it there to feel how loose she was. I went to bed frustrated and horny as hell. She has also fooled around with other people a bit, but she never lets anyone but me cum inside her. With that introduction, I lead into the present situation, where sex has slowed considerably due medical issues of her second pregnancy and pure exhaustion from dealing with our energetic toddler. Before you ask, both of the kids are mine, though we were thinking of adopting a third instead of the normal route.

After moving and getting settled into our new jobs and neighborhood, we take our son and newborn daughter to introduce ourselves to the neighbors. We meet several of the families who are very much like us and after lots of conversation with our next door neighbor while the kids were playing in the other room and the newborn was asleep in her carrier, we were told that they were part of a group of ten or so families that would watch each other's kids so the parents could have special dates for sex. We were a bit taken aback by the conversation, but they were quite open about it and even mentioned that sometimes couples would double-date. We got the gist of it and were interested, especially since we never had anyone to watch the kids before, but we would not take advantage of it for several months when the new baby was older. However, we happily watched our neighbors' kids on their date nights.

After several months, we finally left our kids with a family that was staying in that night and we went on a wonderful date...dinner, movie, cuddling, and when we got home...making out. We felt like teenagers again. We finally got to the part that I was looking forward to all night. She told me she wanted me to pull out her dildo and fuck her with it. I paused, seeing as I thought we would just have sex, but apparently she had not forgotten my kinks or she wanted something bigger than me in her. I fucked her with the dildo until she came hard telling me how she liked big cocks and wished she had a real one to fuck her. I always got hot when she would talk dirty like this to me. After I finished with the dildo, my wife hands me a condom and tells me to put it on just to be safe as she was not ready to be pregnant again. I examined the condom for a moment and realized it was a different type than we usually use. It was very thick and as I slid it on, I felt a bit of a tingle.

"There is a desensitizer in it. I thought with the lack of sex over the last several months, you might be a bit trigger happy. Hopefully this will prolong your enjoyment," she explained as she started playing with my balls. She teased me for several minutes under the pretense of waiting for the desensitizer to take full effect. When she finally lowered herself onto me, I had to admit to her that I could barely feel anything with her being all stretched out and my dick being sheathed in relatively thick rubber with a numbing agent. She just smiles at me.

"Now you know how it feels for me after you stretch out my pussy before fucking me. I can barely feel a thing. You may have just liked the feeling, but stretching out my pussy has made me accustomed to a bigger cock than what you got. So what do you think? Do you want to keep stretching me out with that dildo, or shall we throw out the dildo and use only your dick? If it's the latter, I hope you can keep up with my needs," she said as she bounced up and down on my cock, knowing that I would be so turned on, I would not be able to think straight.

"Of course, I want to keep stretching you. You know I prefer when you give me fewer very strong orgasms while keeping me turned on constantly, which is rather more enjoyable for me than many weaker orgasms. I know you can cum strongly over and over, but I have to build up to it, so now what do you propose?" I replied.

"Well first of all, since you prefer this mental stimulation over physical, I think you will wear these new condoms whenever we fuck so you will only cum once you are so turned on that the slightest physical touch will cause you to explode. Secondly, I am too accustomed to our dildo, so I want you to order a couple of even bigger ones for me when we are done here. That should be enough new rules for now," she said as she hopped off me and walked into the bathroom and turned on the shower. I got up to follow her but she shook her head and closed the door and locked it. I sat there and listened to her masturbate for a few minutes then went to order the dildos. I got a huge 12" super-cock that was so thick that I seriously doubted it would fit inside my wife. The second was an expandable dildo that started at 9.5" long and 2" thick, but could be pumped up to 12" long and as thick as it would stretch.

By the next weekend, we had received our toys and we decided to have another date night. This time, I cooked my wife a nice meal and we ate, talked, and enjoyed each other's company. After dinner, she went to the bedroom and came back with a condom and told me to strip and put it on. I did so as she put a movie in the dvd player. It was a porn video of a woman getting fucked by three extremely well-hung men. One of them was black and had a huge cock. My wife climbed up into my lap and lowered herself onto my dick. She handed me our camera as well.

She whispered in my ear, "Since you want to continue stretching me out and making me feel like a slut, I want to start documenting your progress. I am fucking you now so you feel how nice and tight I am," though when I mentioned that she felt nice and loose to me, she continued, "I used our old dildo on myself at least once a day when you weren't around, so you could feel my pussy in the condition you always preferred it. I promise you that when we finish, you will consider this nice and tight."

She had me take pictures of me fucking her. After a while, I managed to get some very nice angles that showed her pussy lips caressing my cock. Then she hopped off and had me take pictures of her open pussy in its already stretched state. I was seriously turned on and this was not helped that throughout this entire process she kept teasing me saying she would have preferred it be her in the video that was playing. After she was satisfied that we had enough evidence of the current state of her pussy, she had me go get the new dildos. First, she took some comparison pictures of the huge dildo and my condom-covered dick. My dick never looked or felt smaller than it had at that moment. Then she had me fuck her with the expandable dildo. I pumped it up until it was very large inside her, but after a few minutes, she asked for the huge one. I barely got the tip of the head in before I had to stop because it was hurting her.

"You have taken well to my first two rules," she said as she glanced at the condom on my dick and the dildo in my hand, "but now I will add another, albeit temporary, one. Before I tell it to you, I am going to go play with my expandable dildo in the shower while you jack off to the movie and then I want you to put your CB3000 on."

She went back to the shower and I jacked off imagining my wife as the star in the porno. I eventually went and listened at the bathroom door to my wife to finish getting off. Once I did, I put on my CB3000 and eagerly awaited my lovely wife.

She came out to the living room wrapped in a towel and asked, "You like listening to me at the door, don't you?"

"I enjoy the sounds you make and without the images it leaves a lot to my overactive imagination," I responded.

"Then I shall have to make sure you have to listen more often in the future, but that is for later. For now, your new rule is that you will remain in you CB3000 and will not fuck me until I can take the huge dildo inside me," she proclaimed as I sat there sputtering.

After that night, she masturbated only with the expandable dildo and at every chance I got; I also fucked her with it, pumping it up as big as it could go without hurting her. When I asked her about why she wanted this rule one night when I was really horny, she told me that she had decided that if I had wanted to continue playing around with my fantasies that she wanted to push them further because the halfway acted out fantasy with me stretching her pussy then fucking her was decreasing her physical enjoyment of sex with me as she got accustomed to the dildo. She wanted to be mentally involved in the fantasy and possibly enact a few of her own, so it was to be all or nothing. I told her I still wanted it all, but wanted to know where she got the idea of this rule. She then explained that she remembered how excited I was one night when I was wearing the CB3000 and she was playing with my balls and ass. She reminded me that this was the night I had begged her to leave me in the CB3000 for a week and to tease me every day, so she decided to grant my wish. Instead of a set time period she had decided to give me a goal, which she got the idea of the dildo from an erotic story I had written where the wife only allowed her cuckold husband to fuck her after she had fucked another man. My wife assured me that she did not think the erotic stories I wrote were realities I wanted because these stories were pretty extreme, but she did say they did give her a bit of inspiration. I was satisfied that my wife was being so creative and involved.

The next four weeks were excruciating because I was horny all the time and I had to hide the fact that I was wearing a CB3000 while using the restroom. The fourth week, I got a reprieve because my wife suggested I take a week vacation from work and seriously get to work on her. I did so and whenever the kids were at day care, I would fuck my wife silly with her dildo. I had to go to the store a couple of times to buy additional lubricant. When I asked my wife if she was getting sore after all this because she used to get sore having sex with me more than three days in a row. She told me that for some reason she was not sore at all and to shut up and work on that dildo some more. On our date night that Saturday, with my vacation nearing an end, I tried the huge dildo yet again and it went in. It even went nearly all the way in, but I could not get that last inch or so in. Then I took it out and waited expectantly to have my CB3000 removed, she told me that I did not get it all the way in. I was so frustratingly horny, that I nearly cried when she told me this.

The next day, I was surprised when I came home from grocery shopping to an empty house. I found a note saying that she had arranged for neighbors to watch the kids for us and to strip naked and lay on the bed blindfolded. I found the blindfold and did what she asked. After waiting nearly 30 minutes, I heard the door open and then felt a tongue licking at the base of my balls. Soon there was a slim finger playing at the entrance to my ass and I squirmed a bit as my dick strained against the inner walls of its confinement.

"Turn over," ordered my wife's voice, and after doing so, I felt something being pressed against my ass. Only thing I could figure it was my wife's old dildo. Lubricated, it entered my ass and it felt good even with the pain. I have never been attracted to men and never will be, but after solid weeks of nothing...this violation of my ass was very enjoyable.

"I thought so. You seem to like big cock nearly as much as I do," she said and then she leaned close to my ear and whispered, "I know you don't like guys, but one of my fantasies is to see a real, hard cock being thrust into your ass. Maybe you can do that for me some day, perhaps you would if I starved you of other forms of sex for a while beforehand."

I was so drunk from the feelings going through my body, all I could do was groan and nod slightly. She removed the dildo from my ass and took of the blindfold and told me it was her turn. I gladly lubed up the huge dildo and worked it inside her. She came several times, but I could not get it all the way in. That evening we spent with the kids, but I was distracted because all I could think about was getting that huge dildo into my wife. I did not get to try again until next weekend, even though every night I would sit outside the bathroom door and listen to my wife fuck herself with the expandable dildo.

When date night rolled around, I did not even bother with an actual date. I just went to work with the dildo. I licked her clit while pushing the monster dildo into her. She moaned and arched her back pushing back against it. After working at it for nearly an hour, I got the last bit inside her as she came hard on the dildo. After she recovered, she took my CB3000 off and took my pre-cum covered cock in her mouth and sucked it until it was hard. It took nearly 20 minutes to get fully hard and even then it seemed diminished in size. She slid a condom on me and got the camera. I took pictures of her wide open pussy and she took ones of my hard cock next to her huge dildo, which was still covered in her juices. Then she laid back and opened her legs and told me to come and get it. I leaned forward and licked her pussy. I just could not resist. I pushed my tongue inside her and ate her out. As she was building up to another orgasm, she started telling me how wonderful I was at eating her out and how much she loved me, even if my dick was not able to get her off anymore. I gawked a bit at this statement, but did not say anything. After she came from my tongue, I was determined to make her cum again while fucking her. I put my dick inside her (it was literally put as there was no pushing involved). I started to fuck her in earnest and the whole time she told me how she could not feel my little cock anymore and that if I ever misbehaved, she might have to limit my "pointless grinding" in the future. She was really laying on the dirty talk tonight and even though I could barely feel anything myself, I came. I came buckets into the condom, but even then I was not satisfied. I was still horny as hell, but she stopped me and took me to the computer. She showed me some pictures she had taken. Apparently, she took frequent photos of her pussy using the timer during the last 5 weeks. She even took daily photos during the week I had off, including some of my cock in the CB3000 while I was sleeping. She told me that she was saving them for a big surprise, but then would not say anything else.

For the next 7 months we continued very similarly, though she let me out of the CB3000 more often and a few interesting encounters did occur. I could not tell if it was so I could fuck her, or so she could reassure both of us that I could not get her off with my dick anymore. I had loads of fun trying though. When I first had the fantasy of being taunted for my dick not being big enough to satisfy my wife, I had thought that I would feel dejected and ruined if it was actually true, but I did not. I was driven to satisfy her in any way I could. I would eat her out constantly and work the huge dildo in and out of her, even though doing so prevented her pussy from shrinking down back to a normal size. She was nigh insatiable. She even thought of new and creative things to do to increase my angst regardless of whether I was wearing my CB3000 or not. About 2 months in, she took to calling out during her shower sessions, pretending that she was urging some young stud to fuck her long and hard. This was the farthest she had ever taken my cuckolding fantasies, even the only one I had seriously requested of her, which was having an MMF threesome. She had originally told me she was not ready for something like that and may never be, so I had chalked it up to remaining in the fantasy realm. However, five months in, she did something that made me wonder if she was getting closer. One night, she removed my CB3000 and after 20 or so minutes of coaxing my dick hard she just climbed on top of it without a condom. I asked her about it and she told me that it was the safe time of her cycle and she wanted something different tonight. I came within minutes and she got off me and told me she wanted an orgasm. I started to jack myself off to get hard, but she told me that my cock would not be able to give it to her and to eat her out instead. That was the first time I tasted cum. It was not as bad as I had imagined, and it helped that she came really hard while telling me how wonderful I was and how much she loved when I ate her out. I was happy to oblige.

After the seven months had passed, our daughter was over a year and could be without her mother for a longer at a time. One weekend, my wife told me she had a double date weekend trip scheduled for us. We went with a couple who were close friends and in the group to a nice resort hotel. I thought it was odd when we got there... we only had one room with two beds. After dinner, my wife pulls out her dildo and smiles. She then goes on to explain that she had talked with our friends about our fantasies and they understood the ground rules, but she had to explain them to me. First, only her dildo was allowed to fuck her this weekend, though anyone was permitted to use their tongue on her. I was permitted to eat out the other woman, but my dick must remain in the CB3000 all weekend. The other man was permitted to fuck either of us (his wife or me), which he was fine with since his dick, though larger than me, was still not big enough to fit well in my wife's pussy. We fooled around and the couple and I took turns fucking my wife with the dildo and eating her out. I got to watch the other guy fuck his wife several times, and he even took her in the ass. It was so hot, but it did not compare to Sunday.

After getting massages in the morning at the spa, we continued where we left off. After a bit, my wife announced that she wanted the other guy's cum in her ass and straddled her dildo on the bed, while presenting her ass to him. He was ecstatic and lubed his dick up in his wife's pussy before pushing it against my wife's virgin asshole. The whole time he fucked her ass, he was saying how tight and hot it was and how lucky I was to have a wife with such a wonderful ass to fuck. My wife quickly pointed out that I never got to fuck her ass and he switched to saying that he was lucky one with two asses to fuck, seeing as he had already fucked his wife's ass the previous night. My wife was quick to correct him again...three. She then asked if I was ready to fulfill her fantasy. I told her I was and leaned over the bed. He pulled his cock out of my wife's ass and started to push it into mine. It slid in fairly easily and as he started to fuck me, he said that my ass was loose compared to my wife's so he had to wonder who the bigger slut was. His wife chimed in saying that she thought I was the bigger cock-slut and urged him to fuck me harder. It had hurt at first, but started to feel much better. By the time he started to cum in my ass I was so worked up that cum dribbled from my CB3000. I had actually cum without touching my dick. After cleaning up a bit, my wife took a shower with the other man since she had not gotten his cum in her ass yet. She even locked the bathroom door behind her. The other woman made me eat her out, while I was listening to my wife urging the other man to cum in her tight ass. I could hear little thumps each time she was pushed up against the wall by his dick thrusting into her ass. She came twice before he finally came. She told me later that night that she left his cum in her ass and then thanked me for making her fantasy come true. I told her that I loved her so much, even with how tortured I felt by not being released this weekend. She whispered to me that soon she would grant the MMF fantasy I had requested of her.