I started wearing women’s underwear at a very young age. I think I would have been only around 9 or 10 years old. I have no idea why but I developed an obsession with Mum’s panties. She had lots of full brief nylon panties. They were way too big for me, coming almost up to my armpits but I think that was what made them feel so good. I was cocooned in lovely slippery nylon. I also loved her full slips and girdles. Back in those days it was not unusual at all for me to be left home alone while my parents were at work. We lived in a very quiet area and they just trusted me to not do anything stupid. So I would pretend to be too sick to go to school and Mum would usually just believe me and let me stay home. She was fairly casual about that sort of thing. So this let me have whole days where I could walk around in her underwear to my heart’s content. I would also walk around the back yard in just her panties and lingerie. That’s when I first developed my love of being outside in broad daylight, dressed only in women’s underwear.
Fast forward a few years and my older brothers and sister had all left home. I was around 13 or 14 and my hormones were raging. I masturbated every single day, often several times a day. Almost every night and morning, I would hump my pillow until I came. Mum never said a word, just kept washing the pillow cases. I suppose she knew I was going through this hormonal change and just tolerated it.
My obsession with panties and lingerie was also raging. Mum and Dad often went out at night and would take my younger sister with them. If I didn’t want to go with them, it was no big deal, I could stay home by myself. Of course, this just led to lots and lots of dressups in Mum’s stuff. But I also got braver. I started to sneak into the neighbours yards, looking for women’s underwear hanging on clothes lines. I would be completely naked while I did this, my little cock stiff as a board and hard up against my belly. On the rare occasions I actually found something, I would take it off the line and put it on briefly, then put it back. I had to be so careful not to cum in them as I didn’t want to leave any traces of my visit. I never once actually kept or stole anything.
Several years later when I was nearly 18, I’ve moved out of home and was sharing a flat with a couple of mates. They would often stay out at night, only coming home the following afternoon. So what did I do? Of course I did! I would get naked and prowl the neighbourhood looking for panties. One memorable time, I was so fucking horny that at 2 in the morning, I walked around the entire block stark naked. I snuck into a few places but found nothing. I ended up walking back partly on the main road but not a single car came along. My cock was dripping pre cum so much it was running down either side of my vertical dick and starting to run down my legs. I used to produce huge amounts of that lovely clear oh so slippery liquid. Oh how I miss those days!
Speaking of those days, when I was at my peak in my late teens, early twenties, I could shoot cum easily ten feet. I would generally have around 5 to 7 huge spurts and then taper off for the next few. Because my cock was always hard against my belly, if I was laying down and came, I always ended up with cum all over my face and on the wall behind me.
Fast forward again and I am now in a relationship with D, whom I would eventually marry and 38 years later, we are still very happily together. I never got the courage to tell her about my previous crossdressing. But I would take any chance to drop hints. One time we were in bed together and she had on some panties that had only thin straps on each side. One broke. She said she was going to throw them away and I said “No, I can fix them” So I got out of bed and just tied the loose ends together and put them on in front of her to prove they were fine. She laughed but didn’t tell me to take them off. I got back into bed still wearing them and slept the night like that. I had my first genuine wet dream that night and woke in the early morning to see that I had shot a little cum on D’s bottom. She was still sound asleep so I quickly wiped it off. It was intense.
A few more little episodes like that and D finally twigged that I liked wearing panties. I can’t remember all the details now but it got to the stage that she would buy panties for me. I would ask her to get me some pink nylon granny panties on the excuse that I just found them more comfortable than men’s undies. She must of seen straight through that lame excuse but bought them anyway. I would come home from work and find them under my pillow on our bed.
This was long before our k**s came along and D became quite tolerant of my panty wearing. I was eventually able to walk around the house in front of her wearing only a pair of pink nylon granny panties. We would occasionally have sex while I was wearing them. She liked being on top of me and while I was buried in her, I would pull the front of my panties partially up over her bottom and hold her tight to me. She would also suck me off through the panties sometimes and damn, that was so fucking hot. Sometimes I would take the panties off and while licking her cunt, I would slowly stuff them inside her, getting as much of them in as I could. When I knew she was close to cumming, I would suck her clit into my mouth and then slowly pull the panties out. She used to cum so hard, bucking and writhing, I would worry about her dislocating her hips! Man, she came hard.
I finally got brave enough to go into a lingerie shop and buy myself a teddy. The sales woman would have seen straight through my lies about how I was buying it for my wife’s birthday and how she just happened to be as big as I was. But, I got through it and finally had my prized possession. I used to actually wear it to work under my clothes occasionally.
One very memorable night, D had been out with friends. I had been playing in my panties and lingerie all night and was horny as fuck. When I heard D come up the driveway, I got crazy brave. I lay on the couch in my teddy and pretended to be asleep. She came in and saw me and was initially shocked. She didn’t know I had the teddy yet. She wasn’t exactly over the moon about it but didn’t tell me to take it off. So I left it on and we went to bed. As soon as we were in bed, I went straight down and started licking her cunt. She absolutely loved getting licked and was instantly aroused. We ended up with her on top, grinding her soaking wet pussy hard against my cock inside the teddy. I came gallons and completely soaked the front of the teddy. She came again also but, unfortunately, she made it clear that wasn’t going to happen again. I had overstepped an invisible line apparently. I was still able to wear panties around her but never any other type of lingerie. She was fine with me having lingerie, but definitely did not want to see me in it. Such is life. Damn it…
Another vivid memory; At one time we were renting a house and D’s sister T was living with us. On one particular day, I was getting ready for work and could not find a clean pair of undies anywhere. I sometimes wore D’s panties even though they were a bit small for me but all hers were in the laundry basket as well. We had simply failed to keep up with the washing. Out of the blue, D said “Well, we’ll just borrow some of T’s undies” I could hardly believe my ears!! We walked into T’s room, both of us naked, my cock hard as a rock. D just took a pair of plain white cotton bikini panties and slipped them on but there didn’t seem to be anything that might fit me. I didn’t get to try any of them on, D just pulled out various pairs of small lacy nylon panties and kept saying “Nah, these will be too small” and putting them back. Meanwhile my cock is throbbing watching her handle all of T’s panties but D just ignored it. Finally she found a pair of white cotton full briefs. The Cottontail panties if you know them. D laughed and said “Oh look! T has granny panties! Try these on” I did and they were snug but comfortable. As soon as I put them on a wet spot appeared at the tip of my dick but D had already turned and was walking out of T’s room. I followed, my raging erection almost painful in T’s panties. This was a major, major fantasy almost coming completely true. Trying on someone else’s panties while D watched. It didn’t quite work out that way but it was close! I wanted to fuck D right there in the kitchen but she just shooed me away. I did go and have a nice wank outside when D got in to the shower. I can still remember the feeling of that orgasm. It was very, very intense. I never did return those panties. Which leads to another good memory…
When we were building our second house, we were poor as church mice and couldn’t afford to rent a place while we were building. Our good friends Jill and her husband let us build a shed on their bush block and stay there. Not long after we moved in, her husband got a job on a remote mine site and was away 3 weeks out of every four. Jill had been a very long time friend of ours and her and D were very close. I knew that Jill knew I liked wearing panties. Apart from D telling her, I was sometimes less than discreet and she caught a glimpse of pink nylon up the leg of my shorts or sticking out the top of them. Nothing was ever said, Jill was just one of those accepting and tolerant people.
I came home from work one day to find her next to the water tank. It had sprung a leak and she was trying to fix it, but of course nothing would stick to the outside while the water was running out. D was out so Jill couldn’t call on her for help. She asked me if I would go inside the tank and stop the water while she applied a patch to the outside.
I said “Yeah, no problem. I’ll just strip down to my jocks and hop in” I took my shirt off and then went to drop my shorts. At that moment I remembered! I was wearing T’s white cotton panties!
I said to Jill “Umm…Jill…can you turn around for a tic? It’s just that I’m not wearing my jocks”
“What?! Are you wearing nothing under those shorts?!” she said
“Well, no, I am wearing something…it’s just that…you know” I replied, turning bright red in the face from embarrassment.
“Aahh…I see” she said “Oh, look, don’t worry about it. We have to get this tank fixed. It’s only underwear anyway. Come on, hurry up”
So I dropped my shorts and there I was, standing in front of Jill wearing only T’s panties. My traitorous dick started to rise of course so I got in the tank as quick as I could. As soon as I got into the cool water (it was a very hot day) my cock went to full mast. (I have always loved wearing wet panties. I would wear them in the shower, soaping them up like crazy and then letting the water rinse the soap off. Feels wonderful. You should try it!)
So we get the tank fixed and it’s time for me to get out. Jill is just standing there watching me. I asked her to turn around while I got out but she just said a short, sharp “No” with a little smile on her face. She was enjoying my embarrassment, obviously. So, I climb out, my erection clearly visible through the wet cotton. I did my best to try and hide it but she got an eyeful, there’s no doubt about that. I grabbed my clothes and went to walk back down to the shed we were staying in. Jill waited until I had no choice but to walk in front of her. So she was probably watching my wet pantied bottom the whole way. I was so, so hard in the panties and when Jill finally peeled off to go back to her house, I started to wank myself in the panties as I walked. I only got a short distance before I came in them. I’m still not sure to this day if Jill saw me do that, but I really hope so.
Another time, D was out overnight visiting her sister. It was late in the day and I was in the shed wearing just a short white t-shirt and some pink nylon panties that had lace trim around the legs and waist. D had bought them for me for my birthday and they were my current favourites. Now, at this time, Jill had a dog that was a real handful. It would go over the road into the other people’s yard and start barking at their chooks or anything else that moved. The people were really pissed off about this of course and had told Jill there would be problems if she didn’t stop it happening. This day, I was sure Jill was out so when I heard the stupid dog start up, I just went outside and started to call him back. I called and called but the mongrel thing wouldn’t stop. Next thing I hear is Jill’s voice calling the dog. I spun around to see her walking towards me, but looking over the road towards the dog. Fuck, she was home, not out as I thought! I tried pulling my t-shirt down to hide my panties but it was no use.
I said “Oh shit Jill, I didn’t know you were home! I’m sorry about this!”
It was only then she looked at me and saw what I was wearing. She just gave a little laugh and said “Cute! Lucky the neighbours can’t see you…”
We stood there for quite a while, her calling the dog, which finally came home, and me standing there in frilly pink panties. We just made small talk about the day but I was struggling to concentrate on the conversation. As usual, my cock came up and tented out the panties. I know Jill could see it because this time I didn’t try to hide it. But, she never deliberately looked down at it and she just kept chatting away. She finally turned and walked back to her house. I, obviously, had a very nice wank as soon as I went back inside.
I’ve just remembered another very nice thing that happened with Jill. The house that we were renting with D’s sister had a pool. Jill would often come around late in the day for a swim and we always swam naked. I would always get an erection and it got to the point that I gave up trying to hide it. D and Jill would tease me about it relentlessly but I just couldn’t help it. It never really bothered them, it was just the way I was. We would also often share a joint that Jill would bring around, after swimming. This day, I had also had a few beers and the joint she brought gave me a particularly nice buzz. Jill and I were sitting on the back steps of the house. D was inside, preparing dinner. I had an erection as usual but this one was abnormally hard. My cock was throbbing. The beer and the joint combined to completely remove any inhibitions. Jill was sitting right next to me when I leaned further back to get more comfortable and this of course, fully exposed my rigid penis. Which turned me on even more. My cock was twitching and pre-cum was dripping from the tip. Jill kept making small talk but I was high as a kite and incredibly turned on. She was glancing at my dick from time to time. She could hardly ignore it. Without warning, I felt myself start to ejaculate. I let my head fall back and spread my legs. A good 8 or 10 spurts of cum shot out of my cock and went all over my belly and legs. I didn’t even touch it, it just went off on its own. Jill just said “Oh, for heaven’s sake! You’re hopeless with that thing!” I went inside to clean up and later apologised to her, saying it must have been a very strong joint. She just gave me a quick hug and assured me that she wasn’t bothered at all about what happened.
All of the above happened many years ago. Jill was just the most wonderful friend and still is. There was never a hint of anything sexual happening between us, D is the only woman for me. Jill is just one of those wonderful, tolerant, accepting people who just takes you as you are.