A true story from my youth that has kept me in masturbatory fantasy for a long time!
I think this must have happened when I was about 12 as I remember it being quite soon after I first started 'playing with myself' as I called it then.
For years my mother had been a friend with a woman who lived up our street and I had known her and her two daughters for a long time. My mother's friend kept a small holiday chalet on a development by the coast and we regular used to get invited there for the weekend. It was at this chalet that these events took place.
My parents and their friends had gone to the clubhouse to drink leaving us kids alone in the chalet. The two girls were slightly younger than me: probably 10 and 11 at a guess. When our parents had left we amused ourselves by playing cards. It was not long before one the younger of the two girls suggested we play strip poker. I readily agreed as I really wanted to see a naked girl in the flesh - something that had completely eluded me until then.
I had no idea of the rules and I they were made up as they did resemble poker in any way, rather it was a simple whist like game where the loser of a trick took something off. The first few rounds were pretty even and we all lost some clothes but were all still 'decent'. Even so the thought of the girls undressing even a bit had given me a solid erection in my small pecker. The things changed - I think the girls probably were cheating by I don't know how and I was the only one losing. Soon I was down to just my underpants and my stiff cock was clearly visible like a little tent pole under them. The oldest girl pointed at it and giggled.
'You've got a stiffy!' she called out and her sister laughed as well. I blushed but did not know what to say so stayed silent.
We played a couple more rounds and thankfully I did not lose. It ended up with both girls in their underwear: panties and small training bras I think they were called. They did not really have any breasts but they still wore these little bras. Looking at them I felt myself blushing, but also felt my cock rock solid in my underpants.
The next round I lost.
'Take them off.' said the younger of the girls.
'Okay I agree I lose, let's play something else' I stuttered to try and avoid the inevitable.
'You know the rules, you lose a round, and you take something off.' I blushed and did nothing.
'Come along. Strip. Strip. Strip...' both girls started chanting.
Reluctantly I stood up, turned away from them and slipped my underpants off. Somehow I quickly sat back down and crossed my legs so they could not see my cock.
The girls were both blushing I saw as was I. Strangely nothing was said, the cards just dealt again. As we played the trick I could see both girls looking where my cock was and I crossed my legs harder to cover it up. It was rather uncomfortable as I was very stiff. I lost again.
'Forfeit.' Called out one of the girls. 'You've nothing left to take off so you need to do a forfeit!'
'What shall we make him do?' asked the other.
'He should stand up and show us his willy' was the inevitable reply.
'Come on!' Ordered the younger girl again.
Slowly I stood up, my hard cock jerked free as I uncrossed my legs. I just stood naked in front of them and they looked in silence. It felt as if I was blushing all over.
'Are they all like that?' asked one of the girls.
'I guess.' I said 'Can I get dressed now?'
'No, we still want to play' the older replied.
They dealt the cards again and I sat down.
The girls lost the next few rounds and suddenly we were all naked. I could not help staring at their growing nipples and just developing breasts. Strangely the younger girl was more developed with a noticeable swelling for breasts, the other just had what looked liked swollen nipples. Both girls had just a few whisps of pubic hair around their 'front bottoms'. The sight of my first two naked girls was getting me very turned on and I could feel some watery fluid oozing from my cock. I do not think any of us really what to do next so we just dealt the cards again.
We played another trick and I lost again.
There was a little bit of debate between the girls about what my forfeit should be. Eventually they settled on me putting on one of their dresses. I did as I was told and felt very silly sitting in the dress but at least it covered up my cock so I did not mind two much.
I lost another trick and this time they made me put on some lipstick. One of them applied it to my lips. I lost more rounds and they continued to make me up like a doll. They applied mascara, eye shadow and even face power. Finally they got bored with this and when I lost again the younger girl said:
'Play with your cock for us?'
I pretended not to know what they meant.
'You know: wank yourself.'
'I don't do that' I lied.
'You lost. That's your forfeit! And if you don't we'll not let you have your clothes back and you'll have to wear that dress all weekend!' she continued as she grabbed my pile of clothes and pulled them towards her.
I stood up and made a fist around my foreskin and started to masturbate. I saw the girls watching me and blushed yet again.
It felt very, very strange being dressed in that dress pulling my cock in front of the two girls but I was enjoying it. As I pulled faster and harder I saw the girls rubbing themselves too. I had not known girls did that, but something inside of me knew they were doing the same as me. The embarrassment meant I did not cum very quickly and I think one of the girls beat me to it as I saw her rub herself very hard and fast then breathed very hard and stopped. Seeing that pushed me over the top and I felt myself cum. I squirted think white cum all over the dress I still had on and almost fell over from the intensity of the experience. As I came down I saw the youngest girl feel my cum with her hand and rubbed herself so hard I thought it must hurt with other. She groaned loudly and her body jerked just like mine did when I came.
We all were quiet for a bit and I heard the youngest girl saying to the other.
'See, I told you boys did it as well.'
We all giggled and the girls said I was now an 'Honorary Girl' seeing as how I was made up, in a dress and had played with them.
Sadly these events were never repeated, but they have shaped my life. I have a life long taste for being submissive to women, like to be told to wear their clothes and love to perform for them!