My girlfriend knows that anal sex has been a long time fantasy of mine, and recently she decided to try it. We were in the shower fooling around, then we had vaginal sex. She suggested I put it in her ass, and, of course, I gladly obliged. I gently placed my dick at the entrance of her sexy asshole, and she pulled her ass cheeks apart for me. I slowly tried to push my dick in her ass, but it was like pushing my dick against a wall. I was just not going anywhere. The funny thing is that I was fully lubed up and so was she. She was also very relaxed, so I don’t see why I couldn’t get my dick inside her. My dick is about eight inches long and three inches thick, could this be the reason?
–Stranded in the Shower
It sounds like your girlfriend has never had anal sex before, and a nice warm shower does not qualify as warming her up! I am not surprised it felt impossible to get inside; the sphincter muscles are a tight ring of muscles and they’ll keep you from going anywhere you’re not welcome. In this case, you weren’t welcome because you tried to go from 0 to 60 in five seconds. So let’s start over and introduce her to this wonderful activity properly, shall we?
Begin exploring your girlfriend’s ass with analingus, external stimulation, and one finger. As you lick her pussy or stimulate her clit, slip a well-lubed finger inside her ass gently and slowly. Build from this experience and make sure to let her set the pace. Don’t proceed to add another finger or try out a toy until she’s ready.
Once you’ve had many sessions of anal penetration with fingers and toys, only then are you ready to put your dick in her ass. It sounds like your dick is both longer and a lot thicker than average. Get a dildo that’s just slightly smaller than your erect cock, and begin playing with it. Once she can take that dildo comfortably and it feels really good, then you can give your dick another try. If you return to the shower for the big event, make sure to use a silicone-based lubricant, since water-based lubes will simply wash away.