How I Lost My Virginity - Sex Stories 🍒 Unveiling Sensual Narratives

Fetish
2007-01-14

My name is Mike. This is a true story of how I became a man at 18 years old.
I was looking around boys wear at Myers Department Store on the Gold Coast. I guy I would consider myself an average 18 year old boy. I loved swimming and the beach.
I was minding my own business buying some underwear which my mother sent me out to buy. A lady came up to me and said would I help her.

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I said how can I help you. She told me that she was trying to buy some cloths for her sisters son. She told me that he was the same height and build as I was. She said she would give me twenty dollesrs If I would spend an hour or so and help her. I said OK. Well at 18 years old twenty dollers is a lot of money. She pulled out a list from her bag.
We looked at socks and I tried a few pairs on and she picked the colours I liked. She then asked me which I prefer boxers or briefs. My face went red. I replied breifs. Nice she said. She said what size. I told her I wear size 18 She grabbed a few pairs of bikini breifs and some hipsters breifs and took my arm. Lets see what looks better she said as she led me into the change room. The staff must have thought she was my mother. I walk into the change room. I thought she would have stayed outside till I picked what i thought he would like, but she came in and locked the door behind us. I said what are you doing. She replied I'm helping.
My own mother hasn't help me try on jocks even since I was about 7. She told me to kick of my shoes. I did as she said. OK now drop your jeans. I stand there in shock. But before I could say any thing she is undoing my belt and pulling down my zipper. Nice little bulge you have there she says.

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I now stood there in my pale blue bonds bikini breifs. I look down and see my penis slightly bulging at the front. She grabs my polo shirt and pulls it over my head. There she says now we can see how these now undies fit better. I didn't know what to do.
I stood there thinking, I came to the conclotion that undies don't show any thing my swimmers don't. I picked up a pair of the new briefs and proceeded to pull them on over my undies. She grabs my hand and takes the new jocks from me. First you must remove the old ones she barks. I stand there staff as a board. With a quick tug at each side she pulls down my undies.
I now stood ther in just socks and undies around my ankles. My penis is flopped there for her to see. It would have only been around 12 cms long with a light covering of hair. She asks me if my dick is small or large for my age. I reply that i think it's average. She grabs it and tugs it up and down. she tells me that she needs to make sure the briefs fit even with an erection as boys get them all the time. after a tugs my dick is rock hard. it's pointing up and around 18 cm's long. I Pull on a pair of undies but she pulls them back down.................tbc