I still think about that night more than I should.
She was my manager at Choices Video, and it was her leaving party in Shifnal. We’d been flirting for weeks and I was stupid enough to think something might actually happen.
I’d spent the last month wanking over her every night, convinced that once she wasn’t my boss anymore I might finally get to fuck her.
After the party, she and her friend took me back to their hotel. I got drunk and emotional and ended up crying about an ex while they watched. I already felt pathetic before anything started.
Later, when we got into bed, she lay underneath me and let me try. I kept slipping out. Every time my dick fell out, she made sure I knew how useless it was.
“Fucking hell, again?” she said. “It’s so small it can’t even stay inside me.”
I tried pushing back in. She let out a short, irritated laugh.
“My ex could actually fuck me. This feels like nothing. I can’t feel you at all!”
Her friend was sitting on the bed watching. When I slipped out again, she just said it louder:
“Look at it! It’s tiny. It keeps falling out on its own.”
I started going soft. She felt it immediately.
“Are you getting soft already?” she asked. “We’ve barely done anything.”
She turned her head toward her friend and spoke like I wasn’t even there.
“He told me he was six inches. It’s nothing. Look how small it is. And now it’s going soft.”
Her friend smirked. My manager shoved at my chest.
“Get off. This is embarrassing.”
I rolled off her and passed out not long after.
The next morning she was cold and distant.
“That was a waste of time,” she said while getting dressed.
“I’ve had better with my fingers. Don’t ever tell anyone about this.”
A few days later she came back into the store to see the others. I wasn’t working that day, but she told two of the lads exactly what had happened, how I’d cried, how many times I’d slipped out, and how small and useless my cock was.
One of them was a mate from college. She even said my dick was smaller than an iPod. I still don’t know exactly who she told or how much detail she went into. Every time I walked into work after that, I wondered who already knew that their ex-manager had tried to fuck me and found out I was tiny.
I still hear her saying it sometimes. Especially the part where she looked at her friend
and said how small I was.
