Very long read and 100% true.

I live and work in Toronto, a notoriously expensive city to rent and live. I originally moved here for a public facing sales job in a niche industry. The wage was paltry, but if you were good (and I was), you could make six figures with uncapped commission and bonuses.

The team was awesome, we all worked hard, helped each other on sales, and partied hard, but there was a distinct gap in talent and earnings. One woman and I became fast friends. She was petite, blonde, amazing body, and very meek/shy - which is odd for sales but she knew her shit, and being tiny blonde and dripping in sex appeal helped. She got by most months, but just barely, she just didn’t have the charisma to be a huge earner.

We quickly became best-friends, and she would confide in me that things were tough paying rent some months. She had a deadbeat boyfriend who couldn’t hold down his part-time pizza job, and he was blowing any disposable cash he had on huge amounts of weed. To boot, the weed was giving him ED and she was feeling insecure. At first she was sad, and as time passed angry about her situation. One time, she was ranting about her terrible boyfriend (which she often did at this point) on one of our lunch dates, and asked if it would be weird if she shared her google-drive of dirty selfies, and masturbation videos for me to critique and confirm she still has it. I couldn’t possibly resist, I had jacked-off thinking about that body, now she wanted me to see her naked and watch her fuck herself? I’m only human. So, I did. She sent it, then and there, hundreds of photos from age 18- (at the time) 29, and a dozen or so videos. I saw a side of her I never expected. This meek little girl was fucking nasty. Amazing small tits, tight little body, and a big ass. I couldn’t believe my luck. I was supportive, and told her how sexy she was, and she shouldn’t worry about her looks at least. But, she was still in a rather precarious financial spot.

A week or so goes by, and I am absolutely burning out this folder, and it keeps growing with new content that she adds, but not much is said besides, ‘like the new stuff?’ And my glowing reviews. So, we’re at lunch, and she’s increasingly getting more stressed about money and her bf left his shitty job so he couldn’t help with rent, and she suspects he’s been stealing money from her because he always has weed. Then out of the blue she asks ‘ have you been jacking off to my folder?’ I was surprised at her bluntness, but not embarrassed because I think it was obviously assumed that I was, and I confirmed. She smiled, and tilted to look under the table. I was dressed nicely in slim dress pants and I have a BWC 8” long 6.5 in girth. My dick was raging. She just smiles, and looks at me straight in the eyes and says, ‘what do you think about this: I need money, and I consider you my best friend. I trust you. What if I suck your dick when I need the money, and you put a big sale under my sales code?’ I nearly blew my load. I said if she needs money, I could just give her money and she could owe me? She said she didn’t think she would ever be able to actually pay me back, she had burned through her savings,and she was working harder than ever and her sales weren’t improving enough and she was worried about losing her apartment. I thought on it, and agreed. We came to a loose agreement. I asked her how/when/where this would go down. She said, ‘ well here’s the thing, I don’t think I’ll make rent next month and I know you put out a huge sale today, can we leave lunch early and I’ll suck your dick in the basement at the store right now?’ The building was this 100 year old building with this crazy labyrinth for a basement. So off we went back to the store. I went upstairs and changed the sale in the system and she went downstairs to wait for me. I head down, and she makes me look for her a little bit. There are staff lockers and I find her in a little nook, near them and on her knees waiting. Immediately, she takes my dick out and gets right to work. She’s sucking it like she needs this money bad. Being an absolute slut (I mean that in the most loving way). This isn’t some ‘fuck-I-can’t-believe-it’s-come-to-this’ blowjob. She’s got spit running down her chin, she’s going deep gagging, and gasping for air, moaning, eye-contact. She lifts her shirt and takes her small tits out, and grabs my hand to grope them. She is actually enjoying herself. I’m loving every second, and it feels amazing, and I can feel myself getting close to cumming and feeling pretty adventurous myself. ‘Can I cum on your face?’ ‘Mmhmmm’ I take my dick out, and unload on her. Trying my best to not get it in her hair or on her shirt. I lay ropes across her face (my favourite) all over her lips, mouth, forehead, eyes, and unfortunately a bit on her shirt. I feel shakey, and stunned, and maybe in love a little? Haha. I immediately ask her if I can help her clean up. Her face is covered in cum and her own drool. She nods her head quickly without saying anything, trying to balance the cum and not let it drip all over her. So I ran over to where the lockers were, and grabbed a box of Kleenex that was lying around, and start ripping them out, suddenly, I’m acutely aware of where the hell I just had my dick sucked. Did anybody hear by chance, or come downstairs and we didn’t notice? Did anybody notice we went down together? As she’s cleaning up, I ask her if she enjoyed it and was it worth it? ‘ Honestly, the moment we met I knew I was going to fuck you, and I needed the commission so.’ ‘We didn’t fuck though’ ‘This isn’t a one time thing’ I was floored. From them on, when she needed the money, and sometimes even when I was just horny, we would smile at each other on the sales floor, or text, and tell everyone we were going to grab a coffee together. Over the next couple months, I don’t know how many loads she took, but she even started letting me bend her over this old shitty table, and raw fuck her. I even fucked her ass once down there. That building is now being turned into a condo (surprise) but when I walk by, I always smile and get a little hard.