[Shorty] I was a preschool cross dresser.

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Shorty
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[Shorty] I was a preschool cross dresser.

Post by Shorty »

There I finally admitted it. Yes, from my birth until I was almost 5 years old, my mother dressed me as a girl. She had always wanted a family with two boys and two girls and when I came along she already had two boys and a girl. The solution was simple. My hair was left to grow long and I was dressed as a girl. There are lots of pictures of the family including an 11x14 family portrait that shows two boys and two girls. I was also referred to by the feminine form of my first name. I can still remember that I wanted to dress like my brothers but wasn't allowed. I also recall a neighbor who knew I was a boy using my real name and my older brother correcting him. Finally my father put his foot down and said I couldn't go to school like that and my dear mom let me dress like a real boy. Unfortunately, some of the neighborhood kids remembered my unusual type of dress and for years after I was sometimes called by my cross dressing name. Life can be cruel.

I sometimes wonder how different I might have been if my mom hadn't been a little off kilter.
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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 »

After starting school things were fairly normal for me other than being bullied regularly by one of my older brothers. He was mean, manipulative and domineering most of the time and usually for no obvious reason and frequently out of no where he would pounce. He would occasionally do something really nice but then he was quickly back to his old ways.

When I was eleven he caught me masturbating and threatened to tell the parents. At the time I was wanking almost daily but was still too young to have much ejaculate. Still it always felt great and I didn't want to have to quit. When he discovered me he said I owed him for not telling and he would have to think what it would cost me. I figured I would be doing his chores or paying him what little money I had saved up. Unfortunately it wasn't that easy.

Several days later he came to me and asked me what it was worth to me for him not to tell. I said I'd do his yard work for two weeks but he just laughed at that. He asked again and knowing that he probably already knew what he wanted I replied that I had no clue. That was a mistake because it opened the discussion up to anything he wanted and he said he would tell me before the day was out what his price was.

By bedtime he still hadn't told me and I certainly wasn't asking. The lights finally went out and soon I dozed off. Not for long though because my brother woke me up and said he was ready to collect. To my shock he said he was going to jack off into my mouth. I immediately said "no way" but he quickly answered that it was a minor price to pay considering what my parents might do if they found out I was a little pecker pulling pervert. He also threatened to beat my ass if I didn't pay my due. So that night he did finally shoot a load in my mouth after warning me not to spit and as I gagged I said never again. Little did I know then that this was just the start.

For several weeks after he would wake me at night and say "it's payment time." That of course meant him wanking a warm load cum into my mouth. If I refused he'd punch me in the stomach and threaten disclosure of my pastime. Then after several weeks of this he shocked me when he said it would be easier if I just sucked his dick. This was really a line that I didn't want to cross because I thought it would turn me into a "homo." My manipulative brother however came up with the reasoning that since it was a debt that I was paying it wouldn't affect me and I better get sucking. So for the next several years nearly every night I sucked the copious issue from my older brothers rather large cock.
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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 »

When my brother finally got his drivers license and the opportunity to date girls he suddenly lost interest in our nightly sessions. It was a relief to me. Even though I had overcome my aversion to sucking cock and eating cum, it wasn't really something that I wanted to continue. I too was becoming interested in the fairer sex. At 14 my first "girl friend" was an neighbor named Rebecca. Dark haired, thin with beautiful round tits, a great ass and long legs. And incredibly bossy. We would go down into her basement (me hoping to cop a feel) and she would start giving orders. "Shoes off." "Don't sit in that chair." "Talk quietly." "Change the music." "Rub my feet."

Always the feet. At first when I started going over there she wanted her feet rubbed. Unfortunately that wasn't the part I wanted to rub. She would go on and on "Rub my feet" 'Please rub my feet" "Why won't you rub my feet?" " If you really liked me you'd rub my feet." I figured maybe if I rub them she'll let me rub her thigh. So I would massage he feet and gradually try to move up. She wouldn't have any of that. She did on several occasions try to get me to kiss her toes which I eventually did. Then after several months of foot massages and nothing more for me, she finally got an older boyfriend and moved on.

ETA one thing I forgot to mention was that this girlfriend on several occasions wanted to tie my hands behind my back as I kissed her toes.
Last edited by Shorty on Tue Jun 18, 2013 10:22 pm, edited 1 time in total.
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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 »

Tomorrow is the last day of this lock-up period for me. My wife has been out of town for three and a half weeks and while she has been gone I've not been allowed to wank, something I love to do. I'll be spending several days at my MIL's house before returning with the love of my life. We will then spend a day on slow, drawn out lovemaking. I can barely wait.
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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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Joined: Fri Jun 14, 2013 5:55 pm

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

Post by Shorty »

The cage with 8/10 urethral tube was removed this morning. It's a very odd feeling after almost a month of having it on.
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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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Joined: Fri Jun 14, 2013 5:55 pm

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

Post by Shorty »

Well, I went and picked up my wife from her visit to her mother. We were both a bit stressed for various reasons and the reunion was a bit of a bust due to my boorish behavior. I have apologized and she has forgiven me but I will have to pay a price.

The time together making love didn't end up as I had hoped. She reached her O fairly quickly after lots of back massage and external genital stimulation and PIV but I ended up with a ruined O. :o She did however relent and later let me have an O while inside her. It was glorious if a bit subdued due to the earlier O.

I'm back in the cage.
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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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Joined: Fri Jun 14, 2013 5:55 pm

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

Post by Shorty »

The device I'm wearing is similar to a Looker 2 except that the non-removable hollow urethral tube is 8mm with a 10mm bulb on the tip and it sticks about 15mm past the A ring. http://www.ebay.com/itm/Stainless-steel ... 337e94254f. Although it's not a perfect fit it is close enough that I've been able to wear it for some extended periods. The penis tube does take some getting used to but I have not really had any trouble with it. It slipped in with no trouble the first time and I was able to gradually move to 24 hour wear after only several days. Night erections are quite the experience though. With the penis tightly hugging the inserted tube and the cage squeezing from the outside it can be a really intense experience; a major mixture of pleasure and pain all tied together.

The only issues I have been experiencing is leaking precum fairly often and urine dripping from the tube if I don't dab it dry after using the restroom. A tissue in my shorts seems to be an easy solution for the precum. Also if I sit for long periods it causes some crotch sensitivity.
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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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Joined: Fri Jun 14, 2013 5:55 pm

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

Post by Shorty »

I ordered an MM Jailbird today. I think it will be more comfortable for daily wear without the issues of sensitivity caused by the urethral tube of my present device when sitting for long periods. I usually have been taking my cage off prior to departing for work and putting it back on when I arrive home. For almost 4 weeks while my wife was gone though I had it on 24/7 and it sometimes became difficult to sit through long meetings. I'm hoping the Jailbird will help solve this issue.
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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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KeyheldHubby
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Re: [Shorty] I was a preschool cross dresser.

Post by KeyheldHubby »

Congratulations on your purchase.

I've had my JB for just over 5 months now (156 days as I write this), and have been locked up for 110 of those days. My longest period locked was about 2 weeks. No issues whatsoever during the day, or even at night. The comfort is such that I occasionally forget I'm wearing it. When I'm not, I often find myself missing it. Complete comfort. I have found that a small dab of lotion rubbed into the skin on the bottom of my scrotum where the base ring comes in contact with my skin completely prevents any "hot spots" or pinching during the day. I do this each morning when I get out of the shower and get dried off. Not a fan of the urethral plugs myself, but it's not my place to judge others on their likes and dislikes. No plug with the JB, and I find that my penis expands (to the limits of the cage anyhow) and contracts freely during the day without issue. The open cage design makes hygiene a snap, but the spacing of the bars makes self-gratification impossible (at least for me). I hope you're happy with your purchase... I was!
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Various home builts for almost 2 years. Current: Jailbird since January 2013.
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Shorty
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Re: [Shorty] I was a preschool cross dresser.

Post by Shorty »

Thanks for the kind words KeyheldHubby. I have heard so many good things about MM that I hope I'm not raising my expectations too high.
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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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