[Shorty] I was a preschool cross dresser.

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Shorty
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Re: [Shorty] I was a preschool cross dresser.

Post by Shorty »

I recently had a dream that seemed unusually real. I think telling the story of my journey has brought back some forgotten memories. In the dream I was trying on coats but none of them fit. My brother appeared and said I needed to grow since the coats were too small. Then he was sticking his penis in my mouth. It was strange because it was like it happened the first time. His uncut penis was fairly large, about 8 inches, and fat. When he pushed it into my mouth it pressed into the back of my throat and nearly made me retch. Then he pushed it into the side of my mouth and pushed my cheek out. Soon my jaw started aching from opening my mouth so wide. After that I awoke.

I remember that my brother, who was only 1" taller than me, had a flaccid penis that was about 5" and my erect penis was only 5 3/4".

Despite all that I miss my brother who passed away several years back.
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Do nothing out of selfish ambition or vain conceit. Rather, in humility value others above yourselves, not looking to your own interests but each of you to the interests of the others.
– Philippians 2:3-4 (NIV)
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Shorty
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Re: [Shorty] I was a preschool cross dresser.

Post by Shorty »

One of the odd things about my brother was, in spite of his kinky behavior, that he didn't want me to masturbate. He said it was wrong and a very bad habit and I shouldn't ever be allowed to jerk off. Since this was my only way to orgasm I wasn't too fond of his edict. He was cuming almost daily and since he saw nothing wrong with that I figured I could too. So, whenever he wasn't around I took every opportunity to wank. Since I didn't want him or my mother to find any evidence and since I was already consuming semen almost daily, the solution was to eat my own cum. For many years after I would eat my cum whenever possible.

When I was 14 my brother decided he was going to screw me in the ass. I told him he would never fit but he said I just needed a little stretching. For several weeks he had me stick stuff like candles and screwdriver handles up my ass to enlarge it and then periodically he would give it a try. Try as he might, he was never able to get his cock to fit in my ass. My butt hole is still virgin :mrgreen:
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Do nothing out of selfish ambition or vain conceit. Rather, in humility value others above yourselves, not looking to your own interests but each of you to the interests of the others.
– Philippians 2:3-4 (NIV)
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Shorty
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Re: [Shorty] I was a preschool cross dresser.

Post by Shorty »

Today after I did my morning exercises I was extremely tempted to rub one out. I even stuck my fingers through the cage for some stimulation. Fortunately, since solving my masterbation problem is one of the primary reasons for wearing a cage, I was unable to do anything but painfully pinch myself.
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Do nothing out of selfish ambition or vain conceit. Rather, in humility value others above yourselves, not looking to your own interests but each of you to the interests of the others.
– Philippians 2:3-4 (NIV)
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Shorty
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Re: [Shorty] I was a preschool cross dresser.

Post by Shorty »

I have been extremely busy both professionally and personally and therefor the "chastity" part of my life has taken a back seat. Right now my greatest desire is to have eight continuous hours of sleep.
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Do nothing out of selfish ambition or vain conceit. Rather, in humility value others above yourselves, not looking to your own interests but each of you to the interests of the others.
– Philippians 2:3-4 (NIV)
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wishful4
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Re: [Shorty] I was a preschool cross dresser.

Post by wishful4 »

Shorty wrote:I have been extremely busy both professionally and personally and therefor the "chastity" part of my life has taken a back seat. Right now my greatest desire is to have eight continuous hours of sleep.
Shorty,

I have really enjoyed following your journey to date. If you are wearing a device 24/7 as I do, it does take some time to get used to sleeping in it. Nocturnal erection attempts are going to happen, nothing you can do about it. Often it takes me longer to actually fall asleep, as well. Hang in there, it will get better. Wanted to let you know someone is reading. :)
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locked4her55
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Re: [Shorty] I was a preschool cross dresser.

Post by locked4her55 »

wishful4 wrote:Hang in there
Sounds like there won't be a whole lot of "hanging" going on. :lol:
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Shorty
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Re: [Shorty] I was a preschool cross dresser.

Post by Shorty »

wishful4 wrote:
Shorty wrote:I have been extremely busy both professionally and personally and therefor the "chastity" part of my life has taken a back seat. Right now my greatest desire is to have eight continuous hours of sleep.
Shorty,

I have really enjoyed following your journey to date. If you are wearing a device 24/7 as I do, it does take some time to get used to sleeping in it. Nocturnal erection attempts are going to happen, nothing you can do about it. Often it takes me longer to actually fall asleep, as well. Hang in there, it will get better. Wanted to let you know someone is reading. :)
Thanks for your nice response. Actually I have not been wearing a device for a while; tonight is the first time for several days. The lack of sleep is more due to being very busy and somewhat stressed. Lots going on both in my personal life and in my job.

Since you have mentioned nocturnal erections let me say that the one of the main reasons I've ordered a MM Jailbird is due to the very intense experience of wearing a Looker type cage with urethral tube at night. It's not a bad experience, just very very intense when my penis tries to expand.

Thanks again for your response and for following my journal. Much of what I'm writing has been buried inside for many years and letting it out helps me to understand much about myself.
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Do nothing out of selfish ambition or vain conceit. Rather, in humility value others above yourselves, not looking to your own interests but each of you to the interests of the others.
– Philippians 2:3-4 (NIV)
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Shorty
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Re: [Shorty] I was a preschool cross dresser.

Post by Shorty »

locked4her55 wrote:
wishful4 wrote:Hang in there
Sounds like there won't be a whole lot of "hanging" going on. :lol:
That one went right over my head the first time. I just now chortled when I got it. :lol:
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Do nothing out of selfish ambition or vain conceit. Rather, in humility value others above yourselves, not looking to your own interests but each of you to the interests of the others.
– Philippians 2:3-4 (NIV)
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Shorty
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Re: [Shorty] I was a preschool cross dresser.

Post by Shorty »

In 2007 due to an inflamed and swollen prostate and the inability to urinate, I received a Foley catheter for five months. The relief from a swollen and painful bladder was wonderful but one of the last things the urologist told me was "no sex, no orgasm" with the catheter inserted. The doctor didn't know me very well and after four months and no end in sight at the time, I took matters into my own hands. :D Since that seemed to work, the next thing was figuring out how to have sex with a plastic tube sticking from my penis.

After some experimenting I finally ended up with the tube looped down and taped to my erection with surgical tape and covered with a condom. Easy-peasy. Orgasmic bliss. It never ceases to amaze me how inventive humans can be when it comes to sex. :mrgreen:
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Do nothing out of selfish ambition or vain conceit. Rather, in humility value others above yourselves, not looking to your own interests but each of you to the interests of the others.
– Philippians 2:3-4 (NIV)
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Shorty
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Re: [Shorty] I was a preschool cross dresser.

Post by Shorty »

If you're going to take Viagra, remember to remove your cage first.

That is all!
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Do nothing out of selfish ambition or vain conceit. Rather, in humility value others above yourselves, not looking to your own interests but each of you to the interests of the others.
– Philippians 2:3-4 (NIV)
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