A slave’s intro to Cuckholdry

One of my little sissy slaves was so cute to type ME a little story of how he entered the Cuckhold scene..we wish him well in his journey….as he (AT MINIMUM) has decent taste in lingerie.

How I became Sophia’s Chasity boy (A TRUE SLAVES TRANSITION TALE)

It all started when Sophia and I started dating about six months ago. We met over a sales presentation. She was shy, demure woman, but exuded confidence and sexuality. By the end of her presentation I was no longer thinking about the product she was selling, I was thinking about getting in her pants, where I am sure I would find a smooth hungry, tight pussy. I decided to ask her out. I asked Sophia if she liked sushi, to which she responded “YES!” We set it up for the following Friday night.
We had a great dinner. We laughed a ton, did shots, sake bombs, and ate amazing sushi. I was feeling very comfortable with her so I steered the conversation toward sex. I asked her whether or not she liked to watch porn; and was surprised when she looked over at me, straight in the eyes, beaming, and said “Yes, the dirtier the better.” Well the conversation quickly got very hot with her telling me she was into anal, bondage and was open to anything I wanted to try. I was so hot I almost came in my pants. Sadly, by the time we got back to her place it was late, the booze had taken its toll on me, and my cock, and I had to get up early. Despite Sophia pleadings, kissing, feeling me up, I told her I had to go…sadly
I called Sophia the next day and asked if she would go out with me again, and told her that I was sorry if I was too forward. She responded by saying she had had a great time and was excited to go out again soon. In what seemed like no time we were having the most amazing time. We watched porn, and played with each other all the time. Quickly, I realized that Sophia did whatever I asked of her, willingly. I did some research and found out that many women like to be told what to do sexually, in the bed room, while leading an alpha life everywhere else! I decided to ask Sophia to be my submissive on our next date!20160622_203750
Dinner was going great and so I decided to bring it up. It could not have gone better. Sophia was totally into it! We agreed to go shopping together at our local sex shop to buy some things, and that I would write up some rules and mutual commitments. We agreed to go shopping the next day! It was during that shopping trip for the toys that the Sophia’s real agenda surfaced. While we were shopping for lingerie and toys she asked me if she could use some of the toys on me, and that she thought we should get a chastity cage. I really didn’t give it much thought at that time so I said “sure!” However, Sophia was not happy with what she saw and said she would do some research. We went on with our night, and from there had several weeks of amazing sex, both vanilla, and where Sophia was my bound submissive. It was amazingly hot! She would dress for me. Plug for me. Follow my instructions to fill her ass with the dildos I bought and make her send me pictures of her filled holes. I would tie her in the most amazing positions and fuck all her holes and make her beg to cum, which she did. Sometimes I would be an ass and not let her cum, which pissed her off but made me feel in control and happy!
I guess it was about a month later Sophia brought it up again about a chastity device. She had done research and wanted to have one made. It has been so great with her that I agreed, and said I would pay for it too. A few days later Sophia came over with some rings and said she was going to take some measurements of my cock for the device, but that it had to be as flaccid as possible. We had a few cocktails and shortly thereafter Sophia said the best way to get flaccid for this task do this was for me to strip and put on some panties. I protested just a bit, but actually was kind of tuned on by the idea! Well that didn’t work, and I got hot and horny. Sophia said this was not fair because she had done everything I had asked of her. I apologized and asked her how I could make it up. She waited a minute then said she had an idea. She went to her bag and brought back a bottle of hair remover. She said she it would sting abit and make me soft. I agreed, and was cool with the idea. Well she quickly slathers that cream on my cock, legs and ass. And Sophia was right, before I knew it, it was very uncomfortable and I was totally flaccid. She measured, and measured for about 10 minutes. Then ordered, yes ordered, me into the shower to clean up. When I came out of the shower Sophia was waiting for me with a different panty. She helped me put it on, which I did willingly. I was amazed how good it felt to be smooth and how nice Sophia’s hands left on me. This is when she flipped the tables on me, so to speak. She said that now it was her turn to be in charge and asked if I would do as she requested for a while. Though I was embarrassed to be in panties, I was also excited. So we agreed Sophia would be in charge for the next few weeks and I would follow her instructions and directions to the best of my ability. We had the most amazing sex that night!
The next day Sophia said we were going shopping, and to be sure to wear the panties she had put on me the day before, which I did. We jumped in the car and she started driving. Quickly she reminded me she was now in charge and I had agreed to follow her directions. To this I said “Sure!” I was really excited and a bit nervous. We dove quite a way just to pull into a strip center with Victoria Secret store. Before we went in Sophia explained that she wanted me to wear panties for the time she was in charge, every day, and that we were here to buy them. Somewhat embarrassed, because my cock was so hard, I said okay. We went in. Sophia knew where everything was and started to choose panties for me while I wandered around. One of the sales girls came up to me and asked if she could help me to which I responded “no, but maybe my girlfriend needs help.” A few minutes later both Sophia and the sales person came up to me smiling and said they had everything I needed, and it was time to check out. Well, she had more than panties. She had garters, hose, and a bunch of other sexy things. That was the first night I ever wore garters and hose, but certainly not the last. It was also the first night Sophia fingered my ass deeply.
For the next few weeks Sophia kept increasing the things she did to me. She made me dress in lingerie under my street cloths. On days that we did not get up together I had to take pics and send them to her both before I left for work and while I was at work. On occasion she would put lipstick on my mouth and make me suck a dildo that she would slid in and out of my mouth while she rubbed her pussy. She started to put things in my ass every day. Some days it was a dildo, some days it was a plug, and finally she used a strap on to fuck me while I was dressed in thigh highs. I had gotten used to the lingerie and anal penetration and it actually turned me on. I liked it! Sophia would make me eat her pussy to no end, but let me fuck her pussy less and let me cum less…
Then Sophia insisted that I try having something in my ass when I went to work, while wearing lingerie. She said it made her so hot for me, and that she would let me fuck her, so I agreed. She presented me with this steel plug with a jewel on the end. I was amazed at how prepared she was. Fridays were a half day for me, so I thought what the hell, I like the way it feels, I’ll do it! The next morning, she picked out my lingerie, white thigh highs with lacey top, and garter and lacy lacey panties to match. After I showered, she lubed up my hole and popped the metal in my ass. Sophia said that it was now a pussy and wanted me to refer to it that way. That turned me on too. I was surprised how good it felt and how comfortable it was.
Then, just before dressing, Sophia then said she had a test for me, to prove she was in charge. To this I said she must be kidding because I was already smooth, in lingerie and had a jeweled plug in my “pussy.” She said told me to get on my knees, and she pulled my head into her ass. She said if I could follow her directions I would be rewarded that night. Sophia said to put my tongue in her asshole deeply, and keep going until she said I to stop. I was so horny I would do anything, so in I went. She had the wand out, and was pushing that on her super wet pussy. She came really fast and said I could stop and sent me off to work, without being allowed to cum or wash my face. One the way out Sophia said she loved me and knew I would do anything for her. She was right. Then Sophia said I was making excellent progress and that this afternoon she would have the best surprise ever!
I came home that afternoon and was pretty horny from not having cum in long while, and from being plugged and wearing lingerie. I came home to find a note on the kitchen table from Sophia. It said that she was picking up a few things for us, and that I should go upstairs and put on what she had laid out on the bed for me and that she would be back fast. Intrigued, I ran up to see Sophia had laid out ankle and wrist cuffs, a collar, and crotch-less panties. I was super excited! I put on everything and sat on the side of the bed. It was not too long before I saw Sophia’s car pull into the garage. She came straight up and saw me as directed. I was in our leather cuffs, hose, collar, plugged and in crotch-less panties. Sophia said she was impressed, and that I was going to love the next surprise! She laid me back on the bed and attached and tied off my arm and legs as tightly as possible. This was exactly how I had tied her when I was in charge.
Tied on the bed spread eagle, Sophia then put lipstick on my mouth and attached clover clamps to my nipples which made me breath hard. Then she put a blind fold over my eyes and said this was going to be the best orgasm I had recently, and that it would be the last one for a long time, so I should enjoy it, to which I said thank you Sophia. She asked me if she was could gag me with the O ring to which I said, “anything as long as I can fuck your pussy” she laughed and proceeded to strap it in tightly, which is how I liked to be tied and gagged! Then to my surprise she put a condom on my very erect cock. I could not really ask what was happening. She then mounted me reverse cowgirl and said I could not cum until she came, and if I did cum before she finished, there were be a sever consequences. She then put the vibrator under my balls and started to move up and down on my cock while pulling on the chain attached to the clover clamps attached to my nipples. I tried to tell her to stop, she was telling me not to cum, but I came, fast. Very fast.
Sophia then laid down next to me, and said she like being in charge and asked if I liked it. I nodded my head yes and kind of mumbled. She kissed me and said “Excellent.” Sophia said I disobeyed and that she was going to punish and if I was willing to accept HER punishment. Again I nodded my head yes. She kissed my mouth and said “good.” She popped up from the bed and I heard some plastic and the such. I then heard what I can now tell you was tape being pulled off a tape roll. Sophia then grabbed my now softening cock, that was wrapped in a condom full of cum, and kind of giggled. She then came up to my head and dumped the condom into my mouth though the cock ring, and put the tape over my mouth. Even though I struggled it was to no avail. Sophia then said that going forward, when I was allowed to cum, which would not be often, I would cum into a condom while bound, and she would make me eat all that I came. Then it happened.
Sophia said I looked great tied, gagged, taped with a mouth full of cum in lingerie and plugged but I need one more thing. I hear the cling of metal and a weight on my chest. Sophia then got a warm towel and clean my now very, very flaccid cock. Then Sophia rubbed some lotion on my cock, which actually felt pretty good. Then I felt smoking cold and hard go over my cock. Sophia said the next part would hurt and it did. It felt like she pulled my balls though a tiny hole, which she had. Then I felt another piece of metal go over my shaft, it was pretty small. Sophia said it was a perfect fit.