Skipper had always been shy, but when he started work at 18, he matured and then the fun started
This is the first in a series of stories based on my own, true to life sexual adventures. All of the stories have had names changed, but are true to life as they happened. Obviously they start off a little tame, but as the years pass, and my experience grows, the adventures become more erotic, sometimes kinky and more in depth. Anyway, I hope you enjoy. In All of the stories I am 18 or older.
As a teenager, I probably grew up like most teenage boys, lusting after girls at school: teachers, local women, neighbours etc.
I spent many an hour in my room or the bathroom, wanking furiously thinking about seeing them naked, doing things with them etc.
I was always a bit shy around the girls at school, but once I hit 18, and went out to work, my confidence grew. And I started to get bolder.
My first job was in a local department store, a few miles from home. It had the usual clothes departments, a cafe, shoe department, homeware department etc. All staffed by a variety of women ranging in age from their early 20s through to their late 50s. There were quite a few stunners, and a fair few very good looking women amongst them.
As one of a handful of males in the whole store, I was the youngest by a fair few years. A few of the women would tease me, flirt and do things and say things that now would probably get people sacked!
I grew accustomed to this, and began flirting back, responding to teasing comments with some of my own. As I said earlier, getting bolder.
So one lady, Sam, was in her mid 30s, a curvy brunette who would always try and embarrass me by making rude comments or asking questions about my (non-existent) sex life, whether i liked boobs or bums better. Things like that. I would try and reply with innuendos of my own, and began getting better at it as time went on.
One day I was taking invoices around the store, when I reached Sam's clothing department. The assistant told me Sam was in their stockroom, getting something. To be honest I thought nothing of it and went in to look for her. As I went inside I was greeted by a sight I had imagined a few times as I wanked my young cock.
Sam was on all fours, rooting around in some boxes. To make it easier for herself she had hitched her skirt up slightly, and I could just see a glimpse of stocking tops, but also her amazing looking arse, skirt tight over it.
I felt an all too familiar feeling in my trousers. I coughed politely and Sam looked back at me, first at my face, but then at the pretty obvious bulge at my crotch.
Standing up, Sam said,
"hello, just what do we have here then? Enjoying the view there were you?" smiling and laughing at me.
I don't think she was expecting my response as I replied,
"Well, I think you can see I was enjoying the view!" As I gestured towards my bulging hard-on.
Sam stepped closer to me,
"I can indeed you naughty boy, and I don't think you can go back out there, mmm, like this, can you?" As she rubbed my cock through my trousers!
I couldn't believe it, this sexy older woman had just groped me. My lust was intense.
Sam didnt stop there. She reached down and unzipped my trousers, and fished my cock out of my boxers. Her warm hand felt amazing as it circled my shaft and she began pumping my cock up and down, looking straight into my eyes as she did so.
"Let me take care of this, but you must not tell anyone. I bet you have wanked this thing a few times thinking of me haven't you? Tell me."
I closed my eyes with pleasure and groaned in response,
"Oh fuck! Yes, I've wanked thinking of you lots of times."
Sam's hand tightened around my throbbing cock as she sighed and said
"Mmm that gets me so wet! I hope you always make yourself come thinking of me."
All I could do was nod, as this sexy woman wanked my teenage dick. Her other hand was caressing my balls as she pumped my shaft up and down with long hard strokes.
Sam began softly kissing my neck, and my ear before whispering to me,
"I want you to cum for me now. I want to see that spunk shoot from your cock. Come on, give me a big load!"
Well, that was all too much, and i felt my balls tighten, and Sam started with long, slow tight strokes of my cock as I began to twitch. I shot what must have been six or seven big spurts of cum over Sam's hand and onto the floor of the stock room.
Sam smiled at me looking at the mess I had made.
"Good boy! Thats a lot of spunk. Now remember, this is our little secret, between you and me."
Although I was still in a state of shock about what had just happened, I nodded my agreement. I had just had my first ever orgasm at the hands of someone else, a sexy older woman I worked with. I couldnt believe it.
Sam wiped her hands with a cloth before using it to mop my cum up off the floor, gave me a kiss on the cheek, and left the stock room.
I waited for a few minutes and left the room, getting a quizzical look from the assistant. I went on my way and carried on with my duties.
So although I was still a virgin, that was my first actual sexual experience. It was only the start.