The evening started with Deb phoning me asking me to meet Phil in a local bar.When I arrived Phil was already there dressed as a very convincing female and greeted me with a big hug and kiss we got our drinks and moved to a relatively quiet part of the bar where Phil explained Debbie & two of her pals had done his make-up and dressed him including strapping his cock up tightly so it didnt show through his dress and they had inserted a butt plug in him to get his arse ready for my cock because tonight was to be our first go at anal sex.I was a bit shocked at this but excited at the same time as was evident from the bulge my cock was making in my trousers.Debbie then arrived and said it was time to go to their house as her guests had arrived it is only a five minute drive to theirs so we all went in Debbies car.When we pulled up at the house Debbie sent Phil in to the house but led me to the garage where she helped me to undress and after a quick suck on my stiff cock led me into the house there were eight women in the lounge of varying ages from about 30-55 most of whom I had met at some point but didnt know their names.They had already undressed Phil down to stockings & suspenders and one of them was removing his butt plug while another was wanking his huge cock.Debbie then led me by my cock to the middle of the room and said it was time for Phil to lose his anal virginity and as the others led Phil to us Deb started applying some oil to my cock.Phil was made to kneel in front of me with his arse sticking up and Debbie gleefully rubbed my cock against his bum before telling me in no uncertain terms to fuck him.I only gave a little push and found myself entering his tight arse and soon I was all the way in with my balls nestling up against him.I was aware of the gasps of some of the women and Phil let out a groan I asked him if he was ok and he nodded and Debbie said"of course he is ok his cock is still stiff now fuck his arse till you both come" well my stiff cock didnt need telling twice and I pumped it in and out of arse just as I normally do with Debbie.While I was doing this two of the women had undressed and one of them had slid her head under Phil to lick his balls the other had pushed her pussy into Phils face so he could give her a good licking.Just as I started to feel my spunk rising ready to come the woman underneath informed everyone Phil was cumming and Debbie gave my balls a squeeze and said "Now fill his arse with spunk I want to see it dripping out him".I couldnt hold back any longer and for the first time in my life I shot my load into another mans arse.When I pulled my softening cock from his bottom the women all gathered round and made him stand up and hold his bum cheeks apart so they could see my spunk drip from his arsehole and they took it in turns to lick it up.Now that both of our cocks were limp we were instructed to serve drinks for the ladies and that when our cocks were stiff again they would require us to satisfy all nine women before either of us spunked again.Let you know how that went at a later date.
