My husband Ron and I have been going through some rougher than normal patches for the last few months or year. We have been married for 15 years and together for 17 years. We met early in life, actually while still in high school. Yes, we were high school sweet hearts but, neither of us were completely “unexperienced”. While I believe my past was a little wilder than his, he was handsome, sweet and made me want to be a good woman for him. Ron, was always a quite person and didn’t talk much about his past. That was good for me because I didn’t really want to talk about mine either. So, through the years we grow together. Yes, there were some fights but, nothing major.
One night a couple years back, Ron and I are talking like the best friends we are, while we are drifting off to sleep. He tells me that he used to dress in women’s clothing. This didn’t completely shock me, I’m aware a lot of boys crossdress at some point growing up. I console him, telling him that is no surprise and we fall asleep soon after.
A year so ago, Ron sits me down and tells me something has been on his mind. He tells me that he still enjoys crossdressing. I don’t quite understand because I’ve never seen him crossdress and it hasn’t crossed my mind since that night mentioned before. Ron tells me that he’s started buying some clothes of his own, oblivious to me, he was using my clothes before. He wanted to come clean before I found some and assumed the worst. I was still in shock and hurt that he’s kept this secret from me. While I did my best to keep my composure, I wasn’t sure what else he was hiding from me.
A week or two passes and I open a box, yes it was addressed to Ron but, we always open each other’s mail. I found panties, a chastity cage and some female clothes. I went back into shock, yes Ron had warned me but, I couldn’t believe it. I immediately went to his computer and started looking around for clues. Was Ron about to leave me, did he want to transitions to become a woman, has he been cheating on me? All the questions were going through my head and I needed answers now. Ron never hide things from me, always left his phone and computer unlocked. I never really snooped around before but, I needed to see for myself now. After a few minutes, I found an online profile of Ron, or Jenny as he called himself. Pictures of him wearing my things, pictures of him in disgusting positions and hundreds of chat logs. I was sick to my stomach. After looking through everything, I was too angry to talk to him when he got home.
We had our biggest argument ever. He refused to see my side that he was cheating even though it wasn’t in person but, we agreed it needed to stop, now. This is when things took a turn for the worst. We haven’t been the same since. Ron started locking himself in chastity, I didn’t know this but, he slipped the key for his chastity device on my key ring. One day, many weeks after our big blow up, I was feeling frisky and brushed up on him after getting home from work. Much to my surprise did I find a rigid small item where my husband’s penis should be. I shouldn’t have been surprised but, after pulling his pants down for inspection, I found panties and that chastity cage. This brought us to another long discussion as to why is it on. I told him I didn’t like it but, would tolerated it as long as he kept his end of the agreement of chatting and I didn’t have to see it.
Another day or two later, we are in bed and we’re feeling frisky. Ron does great work with his fingers and enjoying give me cunnilingus. That night was no different, except Ron spent an extraordinary amount of time down there. I was well past ready for him. After pulling him up, I found that stupid chastity device on him. I told him I wanted it off now but, he couldn’t find the key. I was completely turned off and frustrated at this point. We ended up going to bed and not finishing. The next night, we talked about what happened. He confessed to him his other secret desires.
Crossdressing was only part of sexual fetish. Apparently, he wanted to become this sissy cuckold thing. I didn’t even know was a cuckold was. I again, felt completely numb when hearing this. This man I married, a man I’ve loved for many years has this dark side. Not only that, he wants me to be accepted of his perversion. I have always been open minded and not shrewd in any way but, this was well outside my comfort zone. I spent the next few night researching. I was trying to understand what Ron got out of this. After reading about this fetish, I found something that might accommodate him.
One evening I started drinking, more than my usual glass or two of wine. I told Ron to make sure he had his special underwear on and then proceeded on with the night. I put on some lingerie and teased Ron for a while. He was very attentive to my needs and wants. When I was ready for more, I pulled out a box, with a blindfold and new dildo. Ron didn’t know anything about this one, it was a little larger than I was expecting, bought it online, but, decently bigger than my other one and Ron for a fact. Ron was shocked and physically taken aback. I laughed and eased his mind, letting him know it wasn’t for him. Well, it was for him to use on me. If he was going to wear that cage to bed, he needed be still fulfill his husbandly duties. Things got pretty crazy then. Ron spent hours eating me and fucking me with my new black dildo. When we woke up the next morning, Ron and I silently agreed to not speak of that night, as we were both ashamed of ourselves.
This type of event went on and off for a month before Ron wanted more. He wanted me to use a dildo on him. He had purchased and been using one secretly for a while. I told him I wasn’t okay with using it. Ron understood that my boundaries were already pushed to the edge. He wanted to give me the key to his cage, officially. He said he’d only take it off when I gave him the key. I didn’t approve but, didn’t see any harm in it. I asked him how often he wanted to be let out and he told me every couple of days. I wasn’t aware until soon after, how powerful it made me.
The first few weeks I let him out every day for a few hours and he would put it back on in the morning. Apparently sleeping in it can be uncomfortable due to involuntary morning/night wood. We got busy in life and a couple days went by before I remember Ron hadn’t been released recently. I apologies and told him he should have reminded me. He said that’s not how it works. I had the control and he wasn’t allowed to ask for release. We had some great sex (normal) sex that night and Ron preceded to put the cage back on the next morning. Over coffee, curiosity got the best of me and asked him how long he goes without masturbating. Without the chastity cage, he would once or twice a day on average. And I prodded, with the chastity cage? Every 3 or 4 days, he responded. I asked how does that work, and he reminded of the dildo. Now, I had heard stories of prostate generated orgasms but, thought they were fake. Ron assured me they were not but, required a bit of work and built up frustration.
By this point, I was a bit comfortable letting Ron keep the cage on during our sexy times. We had a decent sex life, 1 to 2 times a week I guess. Ron could play out his fantasy once every couple of weeks. He had begun wearing more lingerie during this time. While I had never had a desire to be with a woman, this did turn me on. Feeling the soft silk and satin on his body.
I left Ron in chastity for a solid 5 days. That night, I asked him to show me what he does to masturbate. I knew I screwed up when I saw his eye light up in excitement. Up to this point, I had never really seen dressed, other than panties. We always made love in the dark, while I could feel his lingerie, the picture wasn’t burned into my head. Ron was a 5’10’’ average, athlete, slender man; weighing in at about 145 pounds. He was never a burly, tough guy but, nothing I could have considered a sissy. While I laid in bed sipping on yet another glass of wine, Ron finally appears. I never get this picture out of my head now. Ron was wearing a wig, brunette, straight, shoulder length hair. Black lace trimmed bra with matching satin panties, which had a little budge from his cage penis. Black thigh high stocking to include garter straps. If I wasn’t looking at his face, I wouldn’t be able to tell it was him. He quietly comes in the room, holding this dildo, not huge but bigger than I would be comfortable sticking up my rear. I quickly finished my glass of wine before he got on the bed.
Ron climbs into bed and we start kissing. He’s shy and doesn’t seem to want to follow through. Me in all my wisdom said we’d come this far, might as well see what you like. He grabs some lube and pulled his panties to the side. Kneeling next to me, he slowly positions the dildo and then starts sliding down on it. I’m again, shocked at how easy he’s taking it. Ron and I tried anal once but, he was too big for me, and his dildo was about his size. I watch his eyes roll back as he starts to adjust and enjoy the feeling. I’m turned on and ashamed at the same time. He leans forward, kissing me and asking if I want my pussy ate. We get into position but soon realize he’s distracted. After a few minutes I suggest we modify the position to where I sit on his face. This way he can do whatever with his hands and I can grind to climax. I underestimated the visual simulation from looking down and seeing what appears to be a female body under me, with only a slight bulge it the panties. I started rubbing his body, watching that dildo slide in and out. He soon generated a large white cum stain in his panties.
After a whirlwind of orgasms, I dismounted his face, handing him my large black dildo. Told him he needed to fuck me harder than he’s ever done before. It wasn’t long before I was screaming another man’s name in the throws of a great orgasm. I was telling Ron about the dark fantasies I was having now. We soon collapsed in exhaustion. We went to bed that night without saying a word.
Over the last few days, Ron and I have been talking to several men, bulls. We have a date scheduled for tonight. I hope Ron and I’s rough patch is behind us now.
Source: reddit.com/r/sexystories/comments/7fmao8/cd_to_cuck_wife_tells_the_story_of_how_it_started