I have an occasional fwb where we fuck once or twice a month. He felt real adventurous today and asked if he could stuff my holes until they were full. I never had a cock in my vagina and anal before but I have been putting fingers in my ass and thought it would be quite fun.

I had a dildo in my ass and his cock inside my pussy as well as him pounding my ass with my pussy filled as well. I did not expect what was about to happen next but as I was trying to come back to my senses, he went ahead and put the dildo and his cock into my pussy. It hurt so much that I leaped forward and asked him what he was thinking. We talked it out and agreed that he could continue only if he started slow and built up to it. Needless to say, it was the best sex I’ve had in so long. Having my pussy stretched just before the point of feeling like it’s torn is something I’ll do more of