My Journey Begins

M

mantoy1

Junior Member
May 16, 2008
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1
First I would like to thank Mistress Watchful for starting this wonderful site. I wish You well and I hope the future holds much happiness for You. I found this site through one of the Yahoo groups and so far I am very impressed with the things I have seen here.

After many stops and starts the date has finally been set for my chastity to begin. Next weekend, which is Memorial Day weekend here in the US, will be the beginning of the end for me. My wife/Mistress has decided that next weekend will be memorable for me in many ways. On Saturday she plans an evening of erotic lovemaking. I will be allowed the use my cock on her in any manner I desire. As she says, it will be a three hole evening. The only rule is that I am not allowed any orgasms on Saturday. On Sunday I will be bound naked to Her bondage horse. She will then stroke my well lubed cock while explaining to me how much I am going to enjoy being her chaste, cocksucking cuckold for the rest of my life. She will explain to me how Saturday was the last time my cock would ever be inside a woman and that from this day on all cocks would be inside me. She has promised that as I start my orgasm she will make sure that I understand that it is the last orgasm of my life because I will be locked permanently in chastity from that moment on.

How I have gotten to this point in my life and what the future holds is why I am starting this journal.

Thank You again Mistress Watchful for this wonderful opportunity.

mantoy (a soon to be sex toy for men)
 
In the beginning...

How did I end up at this juncture in my life? I often ask myself this questions and there don't seem to be many obvious answers. Eight years ago I was single, financially secure and a strong and willful Dom. I had been in the BDSM lifestyle for over 20 years and had been on the Dominant side for about ten of that. One day while looking through a local BDSM web site I noticed an ad for a younger submissive woman. Her ad was appealing but I didn't feel like I was ready to enter into another relationship so I let it go thinking it would be gone in a week or two. Over the next three months I went back to that ad several times as if it were calling me in some strange way. Finally, I took the plunge and responded. She responded back fairly quickly and we started an email exchange were we got to know each other better. We made a date to meet in person and the evening went well with her ending up in cuffs and on her knees servicing me. Within two years we were married and she was my collared submissive.

Early in the relationship she had indicated that two of her hard limits were sex with women and being Dom herself. Over time I convinced her that if she were truly submissive then she would do whatever I commanded without question as long as she wouldn't be injured. So when the time was right, I commanded that she go down on a woman friend of hers to prove her true submissive nature. While she hesitated at first she did follow my command and found the experience quite to her liking. It seems from that time on women are no longer off-limits and in fact she enjoys playing with them as much as men.

Of course, since women weren't that bad, she decided that she should try being Dom with me for a weekend to see if that hard limit was wrong too. After much discussion and teaching on my part about Dominance we decided on a weekend that I would give up control from Friday evening to Sunday evening. The weekend came around and Friday evening was a time for her to explore having me cater to her every whim. I prepared a romantic dinner, she dressed in heels and stockings and I spent a large part of the evening with my head buried between her legs. By the time she finally went to sleep she had had so many orgasms she could hardly speak or think. Saturday morning I prepared her breakfast, bathed her, did her nails and hair. I was surprised that she put on her heels, stockings and black leather skirt and see through blouse so early in the morning but figured she was just getting into the spirit of things. Before long she had me bound to our horse and was bringing me slowly to an orgasm by stroking me with her lubricated hand. I was really hoping I wouldn't be cumming so soon as we still had a day and a half of play ahead and like most men I tend to loose interest after an orgasm. As these thoughts were going through my head, there was a knock at the door. I panicked thinking that there wasn't any way she could get me untied quickly enough to see who was there without revealing me all bound in the living room. Without a thought she reminded me about how a true submissive does as commanded and proceeded to answer the door. In walked this guy I had never seen before. She hugged him and without any small talk he walked over to where I was bound and proceeded to undress in full sight of me. He was young and hung. As he stroked his cock to erection she put her hands on the back of my head and in her most commanding voice demanded I open my mouth. Without even thinking I opened my mouth to object but before I could even get a word out his cock had filled my mouth and she nearly screamed "suck it". His first orgasm was pretty quick but I swallowed every drop. His second orgasm took longer in my ass. I spent the rest of the day trying to coax his third orgasm out of his cock. It seems funny now how the two of them chatted like old friends while I was on my knees sucking his cock. I had a strange feeling inside when later he took me into the bedroom and began pounding my ass again. I was aware that she was standing at the door watching and my real fears began to materialize when I heard her have the first of several orgasms while watching the action.

More later......
 
Continued

I sucked off her new house-boy last weekend. He has a nice big cock that cums real hard. He will come over once a week to clean the house and fuck me. He will be the first to fuck me after I have my last orgasm next Sunday. I am very nervous and a little scared. I won't be horny at all and so it will be all about submission to my Mistress. He has a pretty big cock.


*************************

That first time for her to Dom me was quite an experience. We talked about it a lot over the next couple of weeks. She couldn't get over the feelings of power that had come over her. She wasn't really sure she liked it. For the next two years I lives changed very little. We went through some tough times when I lost my job and was unemployed for over a year. She had to be the strong one and support us. But during that year her confidence grew and I became more and more submissive to her. Not sexually, but I cooked, cleaned and waited on her in every way possible. She become more assertive and become very dominant in our day to day lives. But not sexually. She still didn't feel comfortable Doming me. Two years ago we decided to try chastity. We bought a CB-3000 and after the appropriate fittings she locked it on me for 60 days. By the second week I was all over her every chance I got. I went down on her every night. As the time passed she also became more assertive. She wanted massages and all kinds of play with various toys. She teased me all the time and was always nude around the house. I felt 19 again. I was horny all the time and couldn't find any release except in sexually pleasing her. About the 6th week I began to crave cock. I don't know why I did but I thought about that first time every day. I thought about how good it would feel to have a cock in my ass again. I met a guy online and he came over and fucked me silly. He fucked me 2 more times before my chastity ended and the last time was the most intense experience I had ever had. I thought I would cum but couldn't quite make it happen. He on the other hand came twice in me. After I was released my orgasm with my wife was intense but not nearly as intense as my last fucking. I came out of that period totally submissive to my wife but she still wasn't ready to take the Dom role. That changed when she met her boyfriend.

More later.....
 
Continued again

Saturday I meet two new guys. One is a Massage therapist and the other is a top trainer for bottoms. She wants me to give the Massage therapist blow jobs so she can get massages. The trainer will teach me how to bottom for guys. Last time sex with her Saturday night. Why am I giving up fucking women for the rest of my life? I am getting very scared and excited.


*************

We talked a lot about that first time in chastity. And while we both enjoyed it she still wasn't ready to be a full time Mistress for me. Late last year or about a year and a half later we decided to try again. It was pretty much the same except I started craving cock in two weeks. I ate a lot of pussy and cock over the next 6 weeks. It was even better for her because she had been seeing her boyfriend for over a year and a half by now so things were even more enjoyable. She had the best of all worlds. Her boyfriend is married and would loose everything if he divorced his wife and my wife doesn't ever want to loose me so she gets both of us.

That period of chastity ended in November and everything began to change. Finally in December she declared that she was ready to take charge of all aspects of our relationship and train me to be her slave if I was willing to accept her terms. Her terms were pretty simple. Permanent chastity. Never would I be able to use my cock for pleasure. I would never be allowed another orgasm except if I should happen to cum while being fucked. In any case, my cock would never feel the inside of a womans body for the rest of my life. I don't know why but I agreed. So here I am now starting this journal of my journey for my Mistress.
 
Four Days to go

I am getting somewhat apprehensive now. Four days to go and the fear of the unknown is starting to play on my mind. I masturbated to orgasm Monday night looking at closeup pictures of pussies. It's the last time I will every masturbate that way. I am trying to imagine my life without the use of my cock for pleasure. The Wife/Mistress says that in a year it will be 25% smaller than now and in 5 years about half its current size. She says that in 10 years it will just be a flabby piece of meat between my legs. She says to look at in a positive light, that most men don't know when they will be struck by erectile dysfunction where in my case I know the exact day and can plan my life accordingly. I am not sure if she is right but I am committed.
 
Date Night

Mistress is out on her weekly date. Dinner then they will come back here for play time. She milked me this morning. I really don't like prostrate massage. It's an orgasm without the "O".
 
Life is good

Mistress Watchful, there are still days when my Wife/Mistress struggles with her dominance but over time it has become easier and easier. There are days when she really doesn't feel Dominant at all but fortunately for Her there are very few days when I don't feel submissive. On those days I still try to fulfill her every need and I think that really helps center Her. The things that I see You are doing indicates that Your dominance is also a long term proposition and as such will be that much stronger over time. Nothing worthwhile happens overnight.

o2cum, thanks for the encouragement. I was beginning to think that no one was really reading my stuff even though I am not writing for the general public, this forum allows me to record my thoughts. Hopefully others will offer encouragement and support during this difficult time of adjustment for me.
 
Date Night Cont...

Date night is really a strange time in my life. The man She has been dating for over a year has actually become a good friend. We always chat before he leaves and I actually look forward to the time he spends in our home. In a different time and place we would probably be comfortable in a poly household. He has gotten me involved in my main hobby, saltwater aquariums, and is constantly advising me on my tanks and fish. He is just an all around nice guy.

I am one of the lucky ones that the CB-3000 is perfect. It fits well, is comfortable for the long term and despite my many attempts I can't get out of it. Wife would like one just like it made in stainless steel. If anyone knows where such a device can be found let me know otherwise we will have to have one custom made. She thinks that the fact that I can see my cock is a constant reminder that I have one. In steel I won't be able to see it anymore and it won't be so obvious that I have a cock. She thinks that after 6 or 7 years I won't need it anymore as nature will take its course rendering it useless anyway (more useless that it is now anyway). That is really scary.

I really admire those men who have decided to become sissies. In my younger years I really enjoyed wearing women's clothing. I was especially fond of thongs, stockings and heels and corsets. Unfortunately it no longer appeals to my sense of self so it isn't something we will be pursuing. I am very much the masculine man these days. I ride my Harley every day and can come across as the total macho biker. It's a good thing my biker buddies can't see me when I am on arms and knees taking a hard one up the rear. I don't think they would find that humorous. Of course that is part of the excitement for Mistress. She thinks it is great that a biker like me does those things in the privacy of our home.

Less than 3 days to go now. I meet my new trainer tomorrow morning and am a bit nervous about the training regimen. He really believes that I can learn to orgasm while being fucked. He says I just need to do it a lot and the longer I am in chastity the easier it will become to just let go. At the very least I should be able to get the same effects as a prostrate massage. That's great, more orgasms without the "O". Mistress says I need to accept it and move on. I have also confirmed with the massage therapist for tomorrow afternoon. Twice in one day and I am not even locked up yet. This one really excites Mistress because she will be getting regular massages from a professional and She doesn't have to do anything for it. I guess you could say that I will be getting massages too, only mine will be internal.

More as time permits.
 
One day to go. I just finished with the trainer. I guess I am well and goodly fucked. He sure did a workout on me but now I am ready for the next guy in about an hour. Mistress wanted all the details since she wasn't here to watch. It is sometimes really strange telling her how a man has used me. She likes to hear the details.
 
mantoy1 said:
One day to go. I just finished with the trainer. I guess I am well and goodly fucked. He sure did a workout on me but now I am ready for the next guy in about an hour. Mistress wanted all the details since she wasn't here to watch. It is sometimes really strange telling her how a man has used me. She likes to hear the details.
Click to expand...

Hello Mantoy-

Could you please elaborate on this "trainer?' It seems to pop out of nowhere in the story. Is this something you KH imposed? Who are these guys? What is the purpose of the training? We'd sure like to know the details of the training sessions themselves. Inquiring submissive minds want to know.

:bigsmile:

Thanks in advance.

o2cum
 
Trainer

The trainer I am referring to is a gay man that was referred by one of the Dommes in Mistresse's FemDom group locally. He specializes in training sissies and straight men the art of sucking and fucking. We spent the first hour this morning with him teaching the various techniques of cocksucking. We worked on everything from how to suck the head to deep throating. The second hour was spent learning how to fuck. First we did doggy style then with me sitting on his cock. He taught me how to prepare myself for anal sex, safe sex practices, relaxing techniques, depth control,how to keep your ass in shape for long periods of anal sex and prostrate massage with a cock. I used the deep throat technique on the guy this afternoon and he actually came deep in my throat and I didn't even taste his cum. Even though I won't actually be a sissy, I will only be capable of having sex like a woman since that is the only way I will have sex after tomorrow.

I hope this answers your questions and I am sorry I didn't explain first.
 
The seconde guy

The second guy today was really great. Big guy with a big meaty cock. Mistress really likes him and so do I. He really knows how to take his time and I really enjoyed it. He agreed to give Mistress massages for sex with me. He is married but just loves to do submissive guys when he can (like at least once a week). Mistress is so happy.

Less that 24 hrs to go.
 
Saturday night was my last night to have sex with my Mistress. She tied me spread eagled to the bed and started her torture. First, she took my cock in Her hands and played with it until it was fully erect. Then She looked up at me and said "Last Time" and put my cock in her mouth. She sucked until I was near orgasm and stopped letting me rest for a second. Looking me in the eyes She said "try to remember what this feels like". She then took me in Her mouth again and ever so slowly sucked me again to near orgasm. She followed with Her pussy saying the same things and finally Her ass. When She was done I was so hot and horny I couldn't hardly stand it. Finally, She locked the CB on me and said that tomorrow night at 9 would be my last orgasm.

The next day was hell. The time just seemed to drag yet seemed to fly by. Nothing was said about the upcoming evening but the house-boy kept looking at my CB and smiling. He was spending the day and night over so that he could help Her with my doom. Finally 9 arrived and he strapped me to the bondage horse. Once strapped in, she removed my CB and began to play with my cock. She had put on a surgical glove so I didn't get the total feel of Her hand but it really felt great and I knew I wouldn't be long in cuming. As I was nearing my "O" She had the house-boy present his cock to my mouth saying "This is your new sex life, learn to enjoy it". With that the house-boy pressed his cock against my lips and I opened my mouth to receive him. As he began to pump in and out She said, "enjoy your last orgasm from a Woman and if you are lucky you will learn to cum in other ways". Slowly I spiraled down into sub space and I am still only vaguely aware of Her telling me to have my last orgasm now. I came and came as he continued to pump my mouth. Finally I was spent and I wondered where my life was going. To add to my torment I was aware of her releasing my arms and body straps, having me stand up and look at the CB. It was all in place except the lock hadn't been closed. "Lock it" She told me and without thinking I reached down and snapped the lock shut. She had me back in bondage immediately and the house-boy moved to my ass. She sat on the couch with one of her favorite dildos to watch as the house-boy finished my torment.

It has been 4 days now and my hormones are still at a very low level but I am beginning to feel the old cravings coming back. Soon I won't be able to live without sex and sex means cock, lots of it. Saturday the trainer will be back and Sunday the masseuse will be over. Even at nearly 60 forever seems to be a long time.
 
Two weeks

It has been two weeks now since my Mistress locked me in permanent chastity. Things are progressing as well as can be expected. 4:30 am and I am up with the nocturnal erections, or attempts at one anyway. I got to the bathroom and that usually is enough to let me go back to sleep. Otherwise no problems so far. Mistress told me she is going to take another lover and since I can't I guess She might as well get all the satisfaction She can. My training continues and I am getting pretty good at it. I look forward to my weekly sex with my trainer and my arousal rate is getting higher and higher. I had a slow fuck this morning and am really starting to enjoy the prostrate stimulation. I wonder if I will learn to cum that way. Mistress really wants me to.

Life is good.
 
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