I won, but...
(by Carg, October 12th, 2020)

Yesterday I got into an argument with my girlfriend. From somewhere she had gotten this piece of clothing that somehow was not quite a pair of overalls, and not quite a jumpsuit, but something in between. She still called them overalls though. Indeed they were of denim, and had shoulder straps, but the sides were much higher than with regular overalls, and they had a zip up the back, of all places.
The argument was not about what they were called though, but that she claimed they were unisex, being denim overalls. She just wouldn't believe that they would not suit a man, and stated that she would only be convinced if she could see for herself that they didn't look right on a man. And since I was the only man around, and I didn't want to let her get away with such an outrageous opinion, I finally agreed to put them on to show her. (We have a fairly similar hip size, and she wore some of my pants before.)

So she held them up and let me to step into them. So far not so different from normal jeans. But then she pulled up the upper body piece - I'd call it a bib, but with the sides so much higher I don't know if that would be correct - and I got a surprise. The shoulder straps, that seemed to be buttoned to the front, were actually attached there and the buttons were only for show. They actually seemed to button in the back, but since she had already opened them I wasn't quite aware of the details. She seemed to cross them before attaching them to the back, which was almost as high as the front.
Then she started pulling up the zipper, which didn't go up easily, but after she ordered me to pull in my stomach, it finally passed the waist and further upward. Then it started to get tighter again since my rib cage is definitely wider than a woman's, but at breast height there was more room again, and the zipper went all the way up without much struggle.

Finally I was in the thing. It was a strange feeling. Normally I wear loose clothes, and although I have a few tight-fitting pants too, the tight denim around my upper body was totally new to me. And since I'm somewhat taller than my girlfriend, the straps were pressing a bit on my shoulders, which also put some pressure on my nether regions. Still, the hugging feeling wasn't totally uncomfortable.
But how it looked was quite another story: it seemed to me that my point was irrefutably proven: the cut was quite wrong for a man, there were these seams to accommodate for a woman's breasts, no fly, and the tightness made the bulge in my crotch quite apparent. My girlfriend didn't give up the fight quite yet, and looked at me from all sides, before finally admitting that she was wrong and they were not suitable for a man.

And then she told me I could take them off again if I wanted. But that was easier said than done. First I tried to pull the straps over my shoulders, but like I thought I felt before, they were crossed in the back, and there was no way they would fit over my wide shoulders. So I needed to unbutton them. But I could hardly reach the top of the back, and then I didn't feel any buttons or holes at the back either. I finally concluded that they probably buttoned on the inside. So that was why my girlfriend buttoned them up before pulling up the zipper! So then I tried the zipper, but it ended just between my shoulder blades, and even though I just managed to touch the pull with one finger, I couldn't get a grip on it, much less pull it down. I had to conclude I was stuck in this thing!

In the meanwhile my girlfriend watched my struggles from the couch, with a very amused look on her face. Just when I told her to help me, she said "Not now - the news is just starting. I'll let you out later; nobody will see you anyway.". OK, so first the news. So I sat down on the couch next to her, and needed a fair bit of wiggling and pulling to prevent the 'overalls' from squeezing me in the wrong places, while my girlfriend poked me to be quiet. But when the news finished, our favorite sitcom was just starting on another channel, and she didn't want to interrupt that either. Instead she cuddled up to me and started stroking me through the tight denim, and paid special attention to my bulge, which caused mixed feelings: it was quite exciting, but with things expanding there it only became tighter. Still on the whole it was quite pleasant, and an interesting change from our normal quickies.
Then a detective started, and she still didn't bother to get me out. Finally my bladder started protesting, and when I threatened her to pee through the clothes, she finally gave in and helped me out.
By then it was so late that we called it an early night, and my freed member finally got the attention it was craving for. My girlfriend also seemed rather enthusiastic.

So now I am enjoying my loose clothes again, and basking in the glow of a rather seldom win of the argument. But thinking back on it, I wonder if she planned losing the bet deliberately, to goad me into putting them on? Still, it was an interesting experience. Perhaps one day we might get into another argument about them? ;-)