[csp807]'s Journey

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csp807
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[csp807]'s Journey

Post by csp807 » Wed Aug 22, 2012 3:07 pm

I have been interested in chastity for a long time, both as a kink and as a realization that I am a frequent and shameless masturbator. I was married for several years, and towards the end, when our intimacy was sporadic and I found out she was having an affair, I suggested chastity as a option, amongst many, to get things rekindled and focused in the right direction. It didn't work (the suggestion), and aside from lots of other personality issues (she felt intellectually inadequate) we couldn't make things work. After some soul searching and a divorce, things have gotten more interesting.

Last year I dated a Chinese doctor. On our third date we were making out and she rubbed herself against my thigh to orgasm then gave me a handjob. It was the first of many times of her getting off w/o traditional intercourse and her giving me a handjob. She claimed that my dick was too big. I am only 5.9" x 4.9" which is average. She also told me that she had an affair with a married man (another Chinese doctor) when she was a student and he had a very large penis and that she fucked him all the time. First, I was bested by an Asian guy, which is atypical and Second, she did not have a problem with his much larger cock. I think she knew that she was messing with me by intentionally putting out a contradictory story.

She masturbated every morning. We only saw each other on the weekends. She told me that she preferred if I didn't cum during the week (did not play with myself). I casually mentioned to her that I liked the idea of her getting off everyday but I had to wait. She made a note and for about 2 months, she would tell me how she got off in the morning and to remind me that I was not allowed to cum. I would obey her wish and probably went 3-4 days at a time without release while she teased me.

To finish up with Chinese doctor (I'll make another post later with my current situation), she once went out of town for nearly a week and would tease me at night on the phone about waiting for her and how satisfied she was. When we finally got together, she teased me for a few hours until she let me cum.

I never used a chastity device with her, but made plans to at some point but we broke up (personality issues). She was kind of crazy the other 90% of the time. She did do other hot stuff too, like stick fingers in my bum, make me kiss her feet and suck on her toes, put her panties on my head/around my neck when we played around, and rub my cum all over my chest and neck after I came.

One other thing about the Chinese doctor is that aside from her liking to put her panties on my head, rub them in my face, and hang them around my neck, she once held them up against my hips like she was trying them on me. I asked her if what she was doing and she said nothing, to which I replied, do you want me to put them on and she said no.

We never touched on the issue again...things were beginning to fall apart...but she left clothes at my house. She is almost as tall as me and is probably a size 9/10 in girls, so, as I would soon find out, I could wear a lot of her clothes. I had lost a lot of weight in the preceding 6-7 months, getting down to 5'10" 160. So I started cross-dressing. First just wearing her panties, then wearing some Forever 21 dresses I bought for her, then just buying a lot of my own clothes. We broke up soon after (she didn't know about the cross-dressing) and I began dressing at home, a lot. I work from home a lot, so I have the luxury of wearing 24/7 for days in a row. I got pretty good at make-up and dressing. I even went out with other CD friends in public a couple of times, including a 3 day trip to New Orleans, by myself, as a girl the entire time.

So, I decided to spend 3 days in New Orleans. I left the house dressed and brought no boy clothes. I had a fabulous time and think that I "passed" most of the trip. On my last night there, I met another CD, we went out and had a fabulous time. We made love that night in my hotel room. It was very special, but we both knew we lived too far apart to stay romantically involved. I came home and eventually jumped back into vanilla world.

About a month later I decided to stop CDing and start dating. I went out with a couple of very successful and very cute women. I really connected with one and have been together for over 7 months. Now to the interesting stuff...

I kept all of my girl clothes, of which I have a lot. I felt like it was a bit of a distraction and finally, about a month ago, got rid of it. I sent a bunch to my friend in New Orleans, some to a local friend, and donated a bunch. Finally, I kind of left that stuff behind and wanted to focus on my girlfriend.

Now for the not so vanilla...my girlfriend is an American girl of Chinese descent (I like the Asian girls). She is very well educated, very smart, very pretty, and awesome in almost everyway. She is very petite, probably 5'4" and 105lbs. She is also 2 years older than me, which is a first (dating someone older). For some interesting emotional reasons, she did not want to have intercourse for the first six months, although we did, with protection of course, a handful of times. She now wants to wait until September to do it again. We have also agreed to abstain from oral sex, although I have desparately wanted to go down on her. Despite that, we have had a pretty incredible sex life. There has been lots of mutual masturbation, solo masturbation, and rubbing our parts against each other in imaginative ways.

So, back when we first started dating, I think on our second date I spent the night with her. We did nothing naughty, but literally slept with each other. She did make a point of rubbing her cute butt against my hard cock all night. About a week later, we played around, with her only cumming that evening by laying on top/side of me and rubbing her pussy against my thigh until she came, then we both went to sleep. She jerked me off in the morning, before masturbating in front of me and cumming again.

We did a lot of this. Sometimes only she would cum. I told her that I thought it was hot but she always worried about the state of my balls.

One day she say on my phone browser that I had been on literotica.com. She seemed bothered by it and later asked me if I played with myself by myself. I told her I did, not realizing that she didn't. She was upset and I told her that I would stop for her, but she didn't want to talk about it. I kind of slowed down (I usually jerk-off 1-3 times a day) but then got back in an old rut.

About 2 weeks ago I decided that I wanted to make a change in my life and started to eliminate some negative and selfish things from my life. Porn and jerking off were two of them. I stopped and actually put on my CB6000s last Sunday, about 1.5 weeks ago. We saw eachother on Friday, me sans CB6000s and cuddled that evening and then went to bed. I was dying for release, but loved the idea that I had gone 6 days. On Saturday morning, we played, with her jerking me off and me playing with her until she came. I then told her what I had done and she seemed really excited. I told her that I wanted to stop masturbating, but needed her support and she agreed to help. Later that afternoon we started playing and she asked me to jerk-off for her, and then she masturbated for me. We played around again on Sunday morning and after she left, I put my CB6000s on again.

It has been 9 days since I last selfishly jerked off alone, and I feel great. I hope that I can stick to it and can eventually introduce her to keyholding and get a nice chastity device from Mature Metal. As for kinkiness, two interesting things happened over the weekend. First, on Sunday morning, when we played, I started it off by giving her a long massage, to which she returned the favor. However, she was so turned on that she crawled on my back and began rubbing herself against my bum in such a way that it was almost as if she was fucking me from behind. It was hot. Second, I like to keep my feet very pretty and my body hair trimmed. Well, I forgot that I had clear nail polish on my toenails and Sunday afternoon, while laying on the couch, she exclaimed "OMG, you have clear nail polish on your toenails!" I denied it, but she insisted and said how smooth they were. I still denied, and she said, "it's ok, I like it." I never admitted, but was super surprised to hear that from her...

One other cute tidbit about my girlfriend. She told me that she owns a dildo that she bought at a sex toy party. She told me that it was the smallest one they had and that she rarely used it because it is too big. I asked her if it was bigger than me and she said it was, but that all dildos are big. She then said that it was the smallest one they had. So even my average size cock could not compete with her "small" dildo.

One thing that happened this week may hasten things in regards to revelation to her about my desire to wear a chastity device. I rubbed a part on the back side of my scrotum kind of raw and I don't think it will heal to an unnoticeable condition by Friday afternoon when I see her. So aside from having to forgo my CD day 3 into an at least 5 day run :-(, I may have to explain to her what the marks are from. So Friday afternoon/night and Saturday morning, I run a very high risk of her seeing it. I could think up a BS excuse, or spill the beans and see what she thinks. I could also skip release and play this weekend as punishment for being a dummy and pushing release out until the following weekend...choices, choices.

Anyway, I am loving the journey and feel really good, refraining from masturbating and trying to remain chaste.
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csp807
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Re: [csp807]'s Journey

Post by csp807 » Wed Aug 22, 2012 10:41 pm

I would love nothing more than to tell her point blank what I want and her to be totally on board, but as we all know, that is easier said than done. I am really trying to approach this as a means to put more effort towards our relationship and to cut masturbation completely out of the equation, so I think my mindset is probably more healthy in regards to chastity than it has ever been before.

Of course, she has bought the dildo, she is into some light BDSM stuff and has even been to a bondage club in LA and watched as a guy spanked and fucked a girl on stage, so she is not completely innocent in regards to fetish stuff. Also, she responded ambiguously to the toe nail polish thing (I am sure she knew I was full of it), so that she was not completely freaked out by that is positive.

I talked to her today, she is out of town, and told her that I had been good this week and she told me she liked that. She also told me that she couldn't wait to play on Friday, and told me that she got turned on during a meeting earlier in the day when I sent her a text message explaining how hot it was that she rubbed her pussy against my bum.
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csp807
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Re: [csp807]'s Journey

Post by csp807 » Sun Aug 26, 2012 9:40 am

quick update...

It has been 2 weeks since I last masturbated alone. My self-imposed chastity began on August 12, and I went 6 days without release until having 3 orgasms over 2 days then had a five day stretch before having 2 orgasms on consecutive days. I am now safely locked in my CB6000s on Day 2 of a likely 6 day run.

So Friday afternoon I want to my girlfriend's house. We basically spent the evening in, lounging around because of mutually stressful weeks. She was aware of my efforts to remain chaste except with her and has reacted very positively.

I am naturally very affectionate, but was paying her a lot of attention, rubbing her back, legs, feet, but not trying to be overly sexual. She liked all the attention a lot, but kept commenting that I must be really horny. I am not sure if I just didn't see it through my horniness haze, but I didn't feel like I was being overtly sexual. One thing she has told me in the past is that I don't paw at her like most guys have done in the past, so maybe my subtle touching equals my horniness in the standard she has set for me.

We laid down to go to bed on Friday and I wasn't pushing her. She started kissing my back and touching me and I finally rolled over and told her that I wanted to make love. She told me she couldn't (time of the month). I asked her if she wanted me to wait. She said no, and that she wanted to make me cum. She gave me a super hot handjob while telling me a story about how I am wearing my uniform (I am a veteran) and come in to see her at a house of ill-refute where she is working as a lady of the night. Of course I am shy and only visit her, and she always looks and anxiously waits for me. It is very much like the relationship of the two main characters in The American. It was hot, she made me cum, then we went to bed.

Saturday morning we were talking about my clients and she was worried that I would be late to a morning meeting and I told her it was ok because I am important and they can wait for me. She thought that was hot, and I talked to her about a scenario where she is a client and she is late and I punish her by making her masturbate on my couch and then have sex with my secretary, after which I come in and fuck her hard for making me wait. She gets off, then asks me to jerk-off for her. I do, then cum all over her stomach and breasts while she masturbates and cums again.

We talk about things. I tell her how good I feel since I started saving myself for her and I really like waiting. She seems genuinely glad and tells me she likes it too and that it is hot.

I have decided to wait a while to talk to her about key-holding. I am privately wearing my CB-6000s for now. I think that a couple of months of action and self-denial is better then just saying, hey, I am weak, lock me up. If I show her my improvement and that I can go without, I think that will be more persuasive when I talk to her about how I would like it if I could wear something that would give me a little more insurance that I won't slip up.
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TwistedMister
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Re: [csp807]'s Journey

Post by TwistedMister » Mon Aug 27, 2012 2:43 am

We talk about things. I tell her how good I feel since I started saving myself for her and I really like waiting. She seems genuinely glad and tells me she likes it too and that it is hot.
There's your intro...when this conversation occurs again, after she says she likes it and thinks it's 'hot' you can ask the question "Do you think it would be even 'hotter' if *you* could control when I get off?" or "Do you think it would be even 'hotter' if *you* had complete control of when and whether I get off or not?"

Something along that line anyway. After you ask the question, if she doesn't respond immediately, just let it drop and let her think about it.

Variation: "I think it would be even hotter if *you* had complete control of when I 'get off' [and I didn't have any say in it]." <--- This one doesn't imply that you are waiting for (or need) a response from her, you are just making a statement and you drop the subject and let her think about it.

Or, since it appears that you and she are into role-playing, you could introduce a scenario where she is in control and gets to decide how/whether/when you get your rocks off, which could then lead into a question/discussion of how 'hot' you/she thinks it is for her to be in control of your orgasms.
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02/11/18 "The idea of me fucking someone else really turns you on, doesn't it?" --Mrs. Twisted

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csp807
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Re: [csp807]'s Journey

Post by csp807 » Mon Aug 27, 2012 7:35 am

TwistedMister wrote:
We talk about things. I tell her how good I feel since I started saving myself for her and I really like waiting. She seems genuinely glad and tells me she likes it too and that it is hot.
There's your intro...when this conversation occurs again, after she says she likes it and thinks it's 'hot' you can ask the question "Do you think it would be even 'hotter' if *you* could control when I get off?" or "Do you think it would be even 'hotter' if *you* had complete control of when and whether I get off or not?"

Something along that line anyway. After you ask the question, if she doesn't respond immediately, just let it drop and let her think about it.

Variation: "I think it would be even hotter if *you* had complete control of when I 'get off' [and I didn't have any say in it]." <--- This one doesn't imply that you are waiting for (or need) a response from her, you are just making a statement and you drop the subject and let her think about it.

Or, since it appears that you and she are into role-playing, you could introduce a scenario where she is in control and gets to decide how/whether/when you get your rocks off, which could then lead into a question/discussion of how 'hot' you/she thinks it is for her to be in control of your orgasms.
Both of these suggestions are great. As for the first, I think she may feel like she is already there, but I am sure that I can come up with some creative way to get into that line of questioning, it is part of my profession after all.

As for the second, I think I could come up with a scenario where she accidentally finds me masturbating, then ties up my hands and teases me over several weeks before I again am allowed to cum. I'll have to think about it :-)
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csp807
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Re: [csp807]'s Journey

Post by csp807 » Wed Aug 29, 2012 10:43 am

I had a bit of a slip up on Monday night. I have not worn my CB6000s lately because I had a bit of pain and marking on the back side of my scrotum. So, Monday night I talked myself into a "ruined" orgasm, pulling my hand off about 3 seconds before I spurted all over my belly. It was hot, frustrating, and a bit disappointing. It was definitely a different feeling and left me horny.

I have since changed the spacer on my CB (and ordered another metal device), going up 2 sizes. The spacer change has made a world of difference and I have been in for about 20 hours w/o a problem.
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csp807
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Re: [csp807]'s Journey

Post by csp807 » Wed Aug 29, 2012 6:49 pm

Ok, so I have been a little horny... :-/

I started playing with an aneros while wearing my CB6000s and felt like I was close to milking (started getting that need to pee feeling) but couldn't quite get there. I have never been able to do it but felt close.

I then decided to do a ruined orgasm again, playing and pulling my hands off a few seconds before...resulting in cum dribbling out on my stomach. I then started back up and did it again, a second ruined orgasm...it was pretty hot.
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Re: [csp807]'s Journey

Post by csp807 » Thu Aug 30, 2012 6:21 am

I really feel like a cheat this morning, having "masturbated" yesterday.

I edged myself on several occasions and had multiple "ruined" orgasms. Like I posted above, I had two "ruined" in a row, then came back about 30 minutes later for 4 "ruined," then about 30 minutes after than again for another 2 "ruined." I think I started to run out of cum. So something like 8 mini orgasms, or 9, but still horny and hard.

Ok, it was hot. First time that I feel like I am having multiple orgasms. They all felt good, but not complete, with me still feeling very horny afterword.

Nevertheless, it is pleasure w/o my gf, so I will consider it a partial relapse and rededicate myself to abstaining but maybe incorporating my ruined orgasms into our playtime. :twisted:
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