28M/38F RAOMD [Success] The Unforgettable Milf

Hello all intrepid redditors!

-drum roll-

Tonight I bring you a tale of triumph. The joining of two complete strangers, brought together by a muff wanted ad, posted a few months ago.

I have phases with Reddit. I'll be active for a while then randomly stop. I was approached once before on RAOBJ and things didn't click so nothing happened. I was aware my posts were still up, but didn't expect anything to really come of it.

I recently started educating myself on polyamory. A week or so after I posted a question I received a message from a woman that I'll call V. She offered to sit down and talk to me about it, as she was knowledgeable on the topic. She was in town for a few days and wanted to meet. We swapped numbers and planned a meetup location.

So it begins, I'm sitting at a table in a busy mall waiting for her to arrive. She's a few minutes late and I'm looking at people trying to assess if that's her. All I knew was she was 5'5, brunette with very green eyes, and the real kind of curvy.

That ti(m)e I was paralyzed by a blow job

This is a story from a time not so long ago.

I was 24, working a cellular gig at a larger Canadian company. A very pretty blonde that we'll call Sarah comes in needing a battery for her phone. I had owned the same phone as her, mine was cracked so I'd updated it and still had the battery at home. Let's be honest. I offered it based purely off how insanely attractive she was.

The date was set and Sarah and I met up for the swap. We ended up talking for a good half hour and realized there was quite the connection between us.

So Sarah and I started hanging out. I lived in a skyscraper on the 11th floor parallel to another building. My suite faced the other building. We both smoked weed at the time and her favorite words upon coming over was

"Do you want to smoke weed then fuck, or fuck then smoke weed?"

God I loved hearing that. She was way out of my league at the time.

That time I had sex on webca(m) for strangers

I was probably less than 6 months into being 18, I'd met this girl who worked at a bar. Her name was Sammy, we had started dating and had been together for a couple of months. One of the girls from the escort agency I worked at, had recommended a cam site (see other post for exciting escort story)

The site was shockrooms I haven't been there in almost a decade don't know if it still operates. How it worked was you were on cam and people would tip you stars that could be exchanged for cash. So Sammy and I get it in our head we were going to try this.

So we set up our 1.3 MP webcam in the corner pointing towards the bed, we are ready to go!

I started out by going down on her, nibbling and lightly flicking my tongue. I was nervous, I'm fairly large at 8.5" and quite thick so I wasn't concerned there. However having a live audience of about 15 people was still foreign to me. I kept going down on Sammy getting her as worked up as I could.

That time I banged (M)y bosses girl(f)riend while at work

Names have been changed to protect other identity.

When I was around 19 years old I got a job under the table answering the phone for an escort agency. I worked for a guy named Frank who owned the agency, all I did was answer the phones and dispatch the escort from where ever they lived. The phones were operated out of his personal home. He was married to a woman who, I'm fairly certain was more lesbian than anything else. But he had money and life was kushy. He also had a girlfriend named Laurie who stayed with them.