This kinda changed my outlook
I'm in my early fifties, divorced, and struck up a friendship with another guy about my age, let's call him Dan. Dan lived alone in a small flat at the end of a row of similar ones, so it was all fairly private. In previous visits to him I had also met his friend Ann, a plump dark-haired woman in her late forties who always seemed to be bulging out of her dress. Sometimes I saw up her short skirt but she didn't seem to mind that I noticed, and neither did Dan. Each time I looked, I saw pink panties. I gathered they sometimes got into bed together, though Dan didn't say much.
Anyway, one afternoon I drove over to see Dan, who knew I was coming. I was a bit late arriving, and when I did, all the parking spaces had been taken so I had to leave my car on the street and walk to the back. When I finally got to his back door I noticed it was open, so I figured he had left it open for me and was probably working in the garden or somewhere. So I walked in without bothering to knock.
As I looked down the hallway, Dan came into view, naked and semi-erect. I hadn't seen him like this before and his penis glistened as if he'd been rubbing some lube on it. Dan didn't seem at all embarrassed, in fact he was giggling like a schoolboy. I could smell booze and aftershave.
Penis leading the way, Bill came up and put his finger to his lips to tell me to keep quiet. He whispered, 'Hey you just gotta see this', and pointed to the bedroom. Starting to feel a bit excited, I followed him. There was Ann, asleep on her back with her legs apart, still in her dress which had been pulled up, wearing no panties so her brown bush and pink lips were showing between her fat thighs. 'Ain't she sweet?' Dan whispered, grinning. I looked down and he was stroking himself while talking. Looking at me, he added 'Jerk off if you want to. Just don't make too much noise.'
I was a bit shocked at his suggestion, but becoming aroused too and seeing Dan looking at her, too, rather than at me made it less threatening. First I unzipped and shyly let Dan see my penis but soon threw caution to the winds and quietly took off my shoes and stepped out of my pants and underpants altogether. Dan handed me some lube and we both masturbated side by side while I stared hard at his girlfriend.
Ann must have heard some strange sounds. She opened her eyes abruptly, yelped at me 'What are you doing here?', brought her legs together and pulled down her skirt. I didn't know whether to run or not.
Dan saved the day by lying down next to her, giving her a big kiss and cuddle and saying it was all his fault. Ann, blushing angrily, said to him, 'What do you think I am, a whore?' But she still seemed interested in my penis, which had gone limp by now. Dan noticed this and said 'You should have seen his hard-on.' I was afraid to resume masturbating. I apologized to Ann, who replied 'It's not your fault, it's this pervert over here,' looking Dan in the eye.
Ann soon realized how absurd this all was. She turned her attention to me, perhaps hoping to make Dan jealous. 'Did I make you hard?' she smiled. She hoped I didn't see her as a fat bitch. Of course not, I told her. Dan went out and returned with drinks for all of us. He asked Ann to show me her breasts and she replied 'Well, you've seen everything else, so why not?', and took the rest of her clothes off.
I must say she did have nice big nipples, and noticing my interest, Ann allowed me to suck them, which really broke the ice. One thing led to another, and before long I actually had my fingers in her vagina while she was holding onto my penis. Dan seemed not in the least bit jealous, and when he unexpectedly shot his load in front of us something came over me and I did the same, shortly followed by Ann with some help from me. There were lots of ooohs and aaahs all round.
I haven't told anyone else about this menage a trois, but the three of us still play together as well as do other things I won't mention here.