Shorty Dressed Like a Girl Before School

I finally owned up to it. From the time I was born until nearly age five, my mother dressed me as a girl. She always wanted two boys and two girls for her family; by the time I arrived, she already had three children—two sons and one daughter. The fix was easy: let my hair grow long and treat me like a girl. There are plenty of photos to prove it, including an 11x14 portrait showing four kids, where I’m clearly among them as the second boy or perhaps the disguised girl. They even called me by a feminine version of my given name. I distinctly remember wanting to dress up just like my brothers but being kept apart from that style. A neighbor who knew I was biologically male used my actual name, and my older brother quickly corrected him. Eventually, Dad drew the line, insisting I couldn’t go to school dressed this way, so Mom let me wear proper boy clothes again. Still, some neighborhood kids remembered how I used to dress, and for years afterward people sometimes called me by that cross-dressing moniker. Life can be harsh. I often wonder if my personality would have been different had Mom not been a bit eccentric.

School started and things were mostly normal for me, except that one of my older brothers bullied me regularly. He was mean, controlling, and bossy most of the time, often without clear reason, suddenly pouncing on me out of nowhere. Occasionally he did something kind, but it didn’t last long before he reverted to his usual self. When I turned eleven, he caught me pleasuring myself and threatened to tell our parents. At that point, I was doing it almost every day, though my body hadn't produced much fluid yet. It still felt wonderful, and I didn't want to stop. When he found out, he said I owed him for keeping quiet and would need to decide what the cost would be. I assumed I’d end up doing his chores or giving him some of my saved pocket money. But it wasn’t that simple. A few days later, he approached me asking how much not telling was worth to me. I offered two weeks of yard work, but he just laughed at the idea. He asked again, and realizing he likely already knew what he wanted, I admitted I had no clue. That mistake gave him free rein over his terms, and he promised to reveal his price before nightfall. By bedtime, he still hadn't said anything, so I stopped asking. Lights out, and soon I fell asleep—not for long, because my brother woke me up ready to collect payment. To my surprise, he declared he would jack off into my mouth. I immediately protested, but he countered that it was a small price compared to what our parents might do if they discovered I was some sort of pervert. He also threatened to beat me stiff if I didn't pay up. That night, after warning me not to spit, he finished in my mouth; as I gagged, I swore never again. Little did I know then that this was only the beginning. For several weeks afterward, he woke me at night saying it was payment time. Naturally, this meant receiving his warm load into my mouth. If I resisted, he punched me in the gut and threatened to expose my habit. After a few weeks of this routine, he shocked me by suggesting it would be easier if I simply sucked him dry. This crossed a line for me because I worried it might label me as gay. However, my manipulative brother argued that since I was paying off a debt, it wouldn't change who I was, so I better get to sucking. For the next several years, nearly every night I took care of his generous seed from my older sibling’s large cock.

When my brother finally got his driver's license and started dating girls, he suddenly lost interest in our nightly routines. It was a relief for me. Although I had gotten past my dislike of sucking cock and swallowing cum, it wasn't really something I wanted to keep doing long-term. I too was becoming interested in women. At fourteen, my first "girlfriend" was a neighbor named Rebecca. She had dark hair, was thin with beautiful round breasts, a great rear end, and long legs. And incredibly bossy. We’d go down into her basement (me hoping to touch) where she would immediately start giving orders: "Take off your shoes." "Don't sit in that chair." "Keep it quiet." "Change the music." "Rub my feet." Always about the feet. At first, when I started visiting, she wanted them rubbed constantly. Unfortunately, foot rubbing wasn’t exactly what I hoped for most from her attention. She would keep going 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 thought maybe if I complied she’d let me touch higher up. So I massaged her feet and gradually tried moving upward. She wouldn’t have any of that. On several occasions, she even asked me to kiss her toes, which I eventually did. After months of foot massages with nothing more for me, she finally got an older boyfriend and moved on. ETA: One thing I forgot to mention is that this girlfriend sometimes wanted my hands tied behind my back while I kissed her toes.

Tomorrow marks the last day of this lock-up period for me. My wife has been away for three and a half weeks, and during her absence I haven’t been allowed to wank—a habit I truly enjoy. I’ll spend several days at my mother-in-law's house before returning with the love of my life. Then we'll have a day dedicated to slow, drawn-out intimacy. I can hardly wait.

The cage with the 8/10 urethral tube came out this morning. It feels very strange after nearly a month of wearing it continuously.

Well, I went and picked up my wife from her visit to her mom. We were both a bit stressed for various reasons, so the reunion was somewhat of a bust due to my boorish behavior. I’ve apologized, and she’s forgiven me, but now I’ll have to pay the price. Our time together making love didn’t go quite as hoped. She reached orgasm fairly quickly after lots of back massage, external stimulation, and PIV, but mine was ruined.:o However, she eventually relented later on and let me climax while inside her. It was glorious if a bit subdued because of the earlier event. I’m back in the cage now.

The device I'm wearing is similar to a Looker 2, except its non-removable hollow urethral tube measures 8mm with a 10mm bulb at the tip and extends about 15mm past the A ring. ... 337e94254f. Although it’s not a perfect fit, it is close enough that I can wear it for extended periods. The penis tube takes some getting used to, but I haven't really had trouble with it. It slipped in smoothly the first time, and after only several days, I was able to move up to 24-hour wear. Night erections are quite an experience though. With the penis tightly hugging the inserted tube and the cage squeezing from outside, it can be a truly intense sensation; a major mix of pleasure and pain all tied together. The main issues I’ve been experiencing are leaking pre-cum 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 handle the pre-cum easily. Also, sitting for long periods causes some crotch sensitivity.

I ordered an MM Jailbird today. I believe it will be more comfortable for daily wear without the sensitivity issues caused by my current device's urethral tube when sitting for long stretches. Usually, I take my cage off before leaving for work and put it back on when I get home. But for almost four weeks while my wife was gone, I wore it 24/7, which sometimes made long meetings difficult to sit through. I’m hoping the Jailbird will help resolve this issue.

Congratulations on your purchase. I've had my JB for just over five months now (156 days as of this writing), and have been locked up for 110 of those days. My longest continuous lock was about two weeks. No issues at all during the day, or even at night. The comfort level is so high that I occasionally forget I'm wearing it. When I do notice it, I often find myself missing the sensation. Complete comfort. I discovered that a small dab of lotion rubbed into the skin on the bottom of my scrotum where the base ring contacts prevents any "hot spots" or pinching during the day. I do this every morning after showering and drying off. Not particularly fond of urethral plugs myself, but it's not for me to judge others' preferences. No plug with the JB means my penis expands (to the limits of the cage) and contracts freely throughout the day without issue. The open cage design makes hygiene easy, but the spacing between bars prevents self-gratification (for me at least). I hope you're happy with your purchase... I was!

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

I recently had a dream that felt unusually real. I think sharing the story of my journey has brought back some forgotten memories. In the dream, I was trying on coats but none fit properly. My brother appeared and said I needed to grow since the coats were too small. Then he stuck his penis in my mouth. It seemed strange because it felt like happening for the first time again. His uncut penis was fairly large—about 8 inches—and thick. When he pushed it into my mouth, it pressed against the back of my throat and nearly made me retch. He then shifted it to the side of my mouth, pushing out my cheek. Soon my jaw started aching from holding my mouth so wide open. I remember that my brother, who was only 1" taller than me, had a flaccid penis around 5", and mine when erect was about 5 3/4". Despite all that, I miss my brother who passed away several years ago.

One odd thing about my brother was that despite his kinky behavior, he didn't want me to masturbate. He said it was wrong and a bad habit, and I shouldn’t ever be allowed to jerk off. Since this was my only way to reach orgasm, I wasn't too fond of his rule. He came daily without issue, so since he saw nothing wrong with that, I figured I could do the same. Whenever he wasn’t around, I took every opportunity wank. Because I didn't want him or Mom finding evidence—and since I was already consuming semen almost daily—the solution became eating my own cum. For many years afterward, I ate my cum whenever possible. When I turned 14, my brother decided he was going to screw me in the ass. I told him he’d never fit, but he insisted I just needed a little stretching. For several weeks, he had me insert things like candles and screwdriver handles up my backside to enlarge it, then periodically tested his progress. Try as he might, he could never get his cock to fully enter my butt hole. It remains virgin:mrgreen:

Today after doing 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 masturbation problem is a primary reason for wearing a cage, I ended up unable to do anything but painfully pinch myself.

I have been extremely busy professionally and personally, therefore the "chastity" aspect of my life has taken a back seat. Right now, my greatest desire is simply to get eight continuous hours of sleep.

> member_07672b2123 wrote:I have been extremely busy professionally and personally, therefore the "chastity" aspect of my life has taken a back seat. Right now, my greatest desire is simply to get eight continuous hours of sleep. Shorty, I’ve really enjoyed following your journey so far. If you are wearing a device 24/7 like I do, it does take some time adjusting to sleeping in it. Nocturnal erection attempts will happen; there's nothing you can do about that. Often, it takes me longer to actually fall asleep as well. Hang in there; things will improve. Wanted to let you know someone is reading along!:)

> member_7f5b971d37 wrote: > Hang in there Sounds like not much "hanging" will be going on.:lol:

> member_7f5b971d37 wrote: > > member_07672b2123 wrote:I have been extremely busy professionally and personally, therefore the "chastity" aspect of my life has taken a back seat. Right now, my greatest desire is simply to get eight continuous hours of sleep. > Shorty, > I’ve really enjoyed following your journey so far. If you are wearing a device 24/7 like I do, it does take some time adjusting to sleeping in it. Nocturnal erection attempts will happen; there's nothing you can do about that. Often, it takes me longer to actually fall asleep as well. Hang in there; things will improve. Wanted to let you know someone is reading!:) Thanks for your nice response. Actually, I haven’t been wearing a device for a while; tonight marks the first time back after several days away. The lack of sleep stems more from being very busy and somewhat stressed. Lots happening both in my personal life and at work. Since you mentioned nocturnal erections, let me add that one main reason I ordered an MM Jailbird is due to the intense experience of wearing a Looker-type cage with a urethral tube at night. It’s not bad per se, just very intense when my penis tries to expand within it. Thanks again for your response and for following my journal. Much of what I’m writing has been buried inside me for years, and letting it out helps me understand myself better.

> member_56a3d51043 wrote: > > member_7f5b971d37 wrote: > > Hang in there > Sounds like not much "hanging" will be going on.:lol: That one went right over my head the first time around! I just chortled when I caught it.:lol:

In 2007, due to an inflamed and swollen prostate that made urination difficult, I received a Foley catheter for five months. The relief from the swollen bladder was wonderful, but one of the last things my urologist told me was "no sex, no orgasm" while the catheter was inserted. The doctor didn’t know me well enough to guess otherwise, and after four months with no end in sight at that time, I took matters into my own hands.:D Since that worked out, the next challenge became figuring out how to have sex with a plastic tube sticking from my penis. After some experimenting, I finally settled on looping the tube down, taping it securely to my erection with surgical tape, and covering everything with a condom. Easy-peasy. Blissful orgasms followed. It never ceases to amaze me how inventive humans can be when it comes to sex.:mrgreen:

If you're going to take Viagra, remember to remove your cage first. That is all!

> member_07672b2123 wrote: > If you're going to take Viagra, remember to remove your cage first. Seems like that could be an exceptionally frustrating situation—taking viagra while locked.:twisted:

> member_1f353e1d87 wrote: > > member_07672b2123 wrote: > If you're going to take Viagra, remember to remove your cage first. > Seems like that could be an exceptionally frustrating situation—taking viagra while locked.:twisted: Since my beautiful wife needed some loving, it was a bit frustrating for both of us until I finally managed to get the cage and base ring off. I don’t get opportunities often enough, but a long slow session of tantric-esque lovemaking is one of life's joys. Most importantly, I know my wife loves it too.

I’ve been trying to wear my cage for longer stretches throughout the day. It hasn’t gone so well at work because of what I do there. Most of my time is spent sitting at a desk, and even with frequent breaks, that position makes it quite uncomfortable. Long meetings can also be tricky, plus sometimes I’m out on the factory floor, which means climbing ladders to overhead catwalks or bending down to check processes. Initially, I worried the tube would cause internal irritation, but usually it’s the base ring that gets in the way, causing pinching and swelling. No problem wearing it over the weekend, but hitting eight hours at work is a struggle. On top of comfort, I occasionally have to present to clients or other managers while wearing one, which feels a bit odd. Fortunately, my office has a private restroom, so I strap on the cage right before leaving for home. I keep it on through the evening and night, taking it off once I’m back at work in the morning. Recently, though, I’ve been delaying removal longer into the day—sometimes until 10:30 or 11 AM depending on my schedule. I have an MM Jailbird coming soon, and I hope its oval base ring will let me wear it around the clock. If the JB works out, I’ll be a happy camper, though I do like my current cage. It’s not custom-made but fits pretty well for me. What I love most is the urethral tube.:shock: When I first saw it in the ad, I felt this strong urge to have both the cage and that tube inserted up my shaft. It was as if I had to impale myself on stainless steel. Once it arrived by mail, I sanitized it right away and slid the 10mm bulb end into my urethra with ease. It just seemed like it belonged there. I might order a custom Looker 2 eventually; I think that would suit me better than the JB. Then again, maybe the JB is exactly what I need.

I’ve been incredibly busy lately, so my posting has slowed down. The JB arrived and fits perfectly. It’s far more comfortable than any of my other setups. Now it looks like going 24/7 is actually possible.

A few things have helped boost comfort and convenience: I followed the common advice to put a little lube under the base ring to stop pinching. The real challenge was carrying it—mine is silicone-based personal lubricant. The original bottle was too big for my pocket and wasn’t leak-proof, while other options were either bulky or prone to spilling. I ended up using an empty eye drop container instead. It’s small, discreet, secure, and makes dispensing tiny amounts easy. After cleaning out an old one, I now keep it in my pocket for随时 use. Another issue was aligning the cage with the ring on the JB until I discovered a trick: lining up both holes is much easier if you press the plastic tip of a ballpoint pen (not the metal point) into the hole from the opposite side of the screw. It’s simple enough.

It’s been a week since the JB arrived, and I’ve worn it nonstop except for about an hour on Saturday with my wife. I just took it off briefly to clean it before putting in my A088 Looker clone instead. The JB has proven much easier to live with, though getting through the workday remains tricky, especially during long meetings. Aside from that, usage is straightforward, and I’ve been sleeping soundly all night too.

Ever since I was born, and especially during my time at school in Phoenix, my mother dressed me like a sweet little girl. I inherited her long hair, which is something of an asset since she’s always cared for it well throughout my childhood.

It feels good to know there were others who had similar experiences at such an early age.

I truly enjoy reading about your journey too; it has inspired me to share my own story and get it out there, which feels wonderful:) thanks

I'm on day 67 with my MM JB. I get out every morning for a shower and whenever my bride needs me to attend to her requirements. Interestingly, I find that I notice the cage more when it's unlocked than when it's locked. Recently, while looking through some old family photos, something from my childhood suddenly came back to me. When I was nine, my eleven-year-old brother and I decided to sneak away to spend our saved-up change at the store. The trip involved a long walk across a busy street, doing so secretly since we weren't supposed to be out. Someone spotted us, called home, and we were caught by my furious father before we could head back. Dad delivered his usual lecture along with stern words and privilege restrictions for bringing me along. He then sent us early to bed, telling us not to see or hear him for the rest of the day. My brother, who had been annoyed at me for joining this misguided adventure in hindsight, placed all the blame on my shoulders. In our upstairs sleeping room was a large cloth bag filled with long, narrow strips that my mother used for weaving rugs. Declaring that I brought it upon myself, my brother pulled out several fabric pieces and tied my hands together. He took off my shorts (we rarely wore underwear in summer) and bound my feet similarly. Having me sit on the floor near the bedpost, he secured both my hands and feet to it. Just when I thought things couldn't get worse, he formed a slipknot with another piece of fabric, looped it around my genitals, and tied that end to the bedpost as well. There I sat, unable to stretch out, naked, hugging the post. At first I wasn't too worried, but as time passed, I realized this wasn't meant to be temporary. Soon I began begging him to let me go, which only seemed to irritate him further. I warned that he would get in trouble if someone found me there, but since my oldest brother was staying at our cousins' and my parents weren't likely to check on us, he remained unconcerned. Surprisingly, being tied up didn't bother me much; in fact, I thought it was quite a cool idea. What bothered me more was the inability to stretch out or lie down properly in bed. I slept intermittently and was released by morning. After that incident, I became more cautious about following my adventurous brother's whimsical ideas, yet he remained my older sibling whom I looked up to for his predictable excitement.

During the summers, our family would spend several weeks at my uncle's cottage by the lake. My parents, brothers, and sister joined my aunt, uncle, and cousin for two fun-filled weeks every August. We enjoyed organized activities like swimming, fishing, archery, hiking, and canoeing, along with plenty of free time to enjoy the warm days. One summer when I was thirteen, my brother convinced me to go on a hike around the lake. Knowing it would be a long trip, we packed canteens and sandwiches into a knapsack and set off early. The south end of the lake wasn't as developed back then as it is now, so we mostly followed footpaths across the water's edge. After about three hours of hiking, we reached a small secluded cove where a creek emptied onto a sandbar. It seemed like a perfect spot for lunch and an afternoon rest, so we dropped our gear, stripped down, went skinny dipping, and cooled off. Then we eagerly ate the sandwiches and drank most of the water. Soon after, both of us were lying back on a large moss-covered log, soaking up the sun and drifting toward sleep. Suddenly I heard my brother call out, "Come here and take care of this." At first I ignored him, but he called again, saying, "Come here, I need you to get me off." I looked over at him and sure enough, his member was standing tall. "Come here and suck me." "No, someone might see us." "There's no one around; do it." "What if a boat comes?" "We'll hear them from far away. Besides, I can't walk back with an erection like this, and we could be here forever. Do it." After several more exchanges, I finally knelt between his legs on my folded shorts while he sat on the log, my head bobbing in his lap. It didn't take long. With a grunt and half a dozen spasms, he was finished. Then, to my surprise, he jumped up, pulled his shorts over his still-hard member, slipped on his shoes, and took off down the trail. "Hurry up," he hollered back, "we're going to miss dinner!" Standing there with clothes in one hand and the knapsack in the other, I suddenly realized this had been the entire point of our hike. Back at the cabin, privacy was scarce due to daily activities and shared sleeping arrangements; we had been at the cottage for twelve days. He had gone about two weeks without release. Before, I sometimes felt put upon or annoyed with my brother, but now I felt overwhelmingly used, lied to, cheated on, and hurt. It is a feeling I would experience again later in life.

In high school and college I dated quite a bit but never settled with one woman. That finally changed after graduation. I had started working for a small engineering firm when I met "M," and we soon began dating, which progressed to her moving in and then marriage. She was intelligent, funny, athletic, beautiful, and very sexy. We both became busy with our careers, but there was always time for intimacy, which increasingly took on some kinky elements even as frequency slowed a bit. We had ups and downs but seemed to get along well. Then things changed. M worked at an NGO managing a small group of grant proposal writers. It involved many long days in meetings or racing deadlines. One afternoon she called to say their big proposal was accepted, everyone was going to celebrate at the restaurant/bar on our office building's ground floor, and she wanted me to join. I had an early flight out the next morning, so I begged off; she said she wouldn't be too late. I went to bed around 9:30 pm even though she wasn't home yet. When I woke at about 1:30 am and heard the shower running, I needed to pee, so I entered the bathroom and was suddenly hit by the smell of beer, nicotine, and sex. The water was on, so she didn't hear me; I slipped back out. Not long after, the shower stopped. Unable to contain myself, I re-entered the bathroom. She stood in front of the mirror combing her hair. I asked how the celebration went. She said they were relieved about the proposal acceptance. At that point, I asked who she had slept with. She denied it at first but eventually admitted infidelity under the weight of evidence. I pressed for names; she wouldn't say directly until I suggested that because of rug burns on her backside, it must have been 6'8" and 350lb Lonnie. Then she broke down and told me it was all seven of them. They had returned to the office after drinks, and when she asked what they wanted as a reward for their hard work—thinking days off or bonuses—one laughed and said he wanted a blow job. She described it as if someone else were speaking in her voice: "Who wants to be first?" From there, things went way out of control. Oddly, she didn't seem too worried about how this would affect our marriage but was very concerned what everyone at work would think and whether she could ever face them again. That marked the beginning of my first experience with chastity. For the next fourteen months, I abstained from sex or even an orgasm. My wayward wife decided she didn't know who she was anymore and needed to find herself. Over the following year, she moved in with a series of different men. One evening she came to my door wanting to talk. She said she still loved me and wanted us back together but admitted she wasn't planning to stop sleeping around. A divorce soon followed. Not too long after that, I met my future wife (beautiful, funny, intelligent, assertive, and very sexy). After an eight-month courtship we married. She's quite vanilla but a bit demanding in the bedroom, and hopefully, I'll always be ready to meet her needs. That has been 38 years now, so I think it will last. I am one happy guy.