Girdle Confessions

As a 15 year old virgin male who'd been masturbating since entering puberty, I was more than a little interested in seeing a naked female or one partially dressed; to be honest any female in her underwear or less. While on holiday at my grandmothers. After spending a few hours in the local cafe, I was walking home (she lived in the country in a small group of houses) on what was a pitch black moonless night and I knew that a 50+ year old lady lived in a house nearby lived on her own and seldom had any visitors. As I walked along the very dark path, I could see the lights of her house and as I could easily hide under the cover of darkness I decided that maybe I could peek at her through her curtains. I slowly made my way into her garden and moved as quietly as I could towards the light shining out through the bottom of the window. To my great surprise and delight, the curtains were short and there was a one inch gap at the bottom where the hem was above the window sill. She was watching TV. After about 20 minutes with nothing happening, she turned off the TV and it seemed that she was going to bed. She turned off the lights in the room and a few seconds later a light came on in what was a nearby room on my right. My heart was racing and I was praying that this was her bedroom and that her curtains would have the same gap, which in fact turned out to be the case. I lowered my eyes to sill level and there she was in front of me, less than ten feet away and totally unaware of my presence. She was wearing a floral dress that unbuttoned down the front. My cock was instantly hard when she started undoing them and stepped out of the dress. She stood before me wearing a white bra, a tan coloured girdle and tan coloured stocking; she wore no panties and her hairy pussy hairs stuck out under the bottom of the girdle. With cock in hand I stroked for all I was worth as the unclipped her bra and dropped it on top of her dress. She rubbed her free tits and I could see her nipples getting hard. Next came her stockings and girdle and as she stood naked before me I came. It was clear she had no idea she was being peeped at and appreciated though once naked she left the room and I guessed that when she left the bedroom she went to the bathroom. That was over forty years ago and I have never forgotten that experience or that night. I had seen my first mature naked female in all her glory and I was horny and excited enough to want to see more.

#peeping   #stripping   #naked   #girdle   #dress   #bra   #stockings   #unbuttoned  

When I was a teenager way back in the early eighties, I was taunted by some of the other boys at school for being overweight. I was a little, but in my mind at the time I was convinced it was a lot. It got to me so much that a few days before the start of the new school year I went into town with some money I'd been saving and (I can still barely believe it even after all these years) I went into a department store, went into the lingerie department and, with a bright red face, bought myself a panty girdle. Even though I dreaded the thought of wearing it, I thought a girdle would reduce my belly, tighten up my backside and get the bullies off my back. As I was excused gym class on medical grounds, there would be no problem there. And surely I'd get used to it? The assistant was initially astonished and thought I was joking at first, but when she realised I was serious, I guess she figured my money was as good as anyone else's.

So, on that first day, I headed off to school as if everything was normal, went into some derelict buildings along the way, took off my trousers, quickly tugged on my long-leg Playtex "I Can't Believe It's A Girdle!", got dressed again, and headed off to school, wide-eyed and stiff legged. My "weight loss" since the start of the summer break was noticed, but I was still bullied. And now I had to get used to wearing a tight girdle every day to maintain the weight loss illusion - I could hardly get paunchy again overnight!

Have you ever had that terrified sinking feeling in the pit of your stomach when you realise you've really screwed up? That's how I felt when it dawned on me what I'd done and that there was no going back. The whole idea was dumb from the start, had failed totally in its objective, my initial overconfident attitude about getting used to it had died the moment I'd put it on and realised as it compressed my belly, backside and thighs exactly what it was I was going to have to get used to...and now I had no way out! I felt sick as I realised I was going to have to wear a girdle - a Playtex panty girdle! - every day from now on. For no good reason. And it was all my own damn fault.

By the end of that first day of being firmly held in, I could definitely believe it was a girdle! I'd fidget around in my seat trying to get comfortable - sit forward, sit back, legs apart, legs together - but I could get no relief. It was a girdle, and it did what a girdle was supposed to do. I'd catch myself gasping as I stood up or sat down, and walking up or down stairs was...an experience. By lunchtime I felt like I just wanted to scream, but I had a long afternoon in front of me before I could take it off.

After school, I hurried back to the derelict buildings (as quickly as I could manage!) to get out of my tight new panty girdle. I was almost crying with frustration as I fumbled frantically with my belt buckle in the rush to get my trousers off and get the bloody thing off me. The relief I felt as I peeled it off was incredible. But I just had to get used to it being part of my uniform from that day on. I'm not ashamed to say that, as I tugged it on the next morning, I was actually crying. I did eventually come to terms with the situation and get used to it, but it did take a very long time.

I guess that was about the only notable thing I achieved at school, though being the only boy to have his underwear made by Playtex is something I was quite happy to keep secret!

#bullying   #school   #crossdressing   #girdle