hello everyone, just getting started here

I have been a lurker for a while, so thought that I better join.

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 chasity 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.

Like I said, I will post more about my current blossoming situation (she isn't crazy!!) later today.

 

Ok, just finished my morning jog, so I can now pick this back up. One thing I left out 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.

More on that later...(but for now, here are a couple of pictures of me when dressed).

 

Ok, I am back...

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 :manga_beat: ). 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...

Anyway, it's great to be here...locked and horny.

 

Wow, this section of the forum is slow...thought I would have more replies or suggestions.

Thanks! Yes, I agree, I think she might be open to it, but you know, it may seem super wierd too. I got to figure out how to approach the issue. One thing that happened this week may hasten things. 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.

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.

 

I think I will have to play it by ear. 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.

 

Thanks!

I was thinking of one other thing for tomorrow. Right now, my feet are still pretty with clear nail polish on my toe nails. With the idea that she might be looking tomorrow (will be sitting on couch with bare feet on ottoman in front of us while watching TV), should I leave the polish on, or take it off?