Sorry if there are typos I am writing this on my phone very quickly!
My girlfriend and I have been dating for a long time now. We are both early 20’s and I would consider us to both be attractive people.
Last night was a normal night. We had dinner together and then turned in for bed around midnight but before we went to sleep we started to get a little frisky. One thing leads to another and we start fucking missionary. Now she usually grabs me around my lower back ass area and pulls me into her but last night it escalated a bit. She slowly starts creeping closer and closer to my asshole until both of her hands are spreading it. I hestitate a little bit but then resume my rythym. Soon enough she starts to massage my hole and I slowly realize that I enjoy it. I had never had another person and not even really myself touch my asshole like that. After a bit of massaging she slowly works in a finger while I’m still thrusting into her. This continued on for a few minutes and after a little longer I couldn’t take it anymore (in a good way). I shamefully stopped and went to the bedside table to grab some lube. She chucked at me and said, “well I guess that means you like it.” I climbed back on the bed and assumed a doggy style position. While kissing my neck she lubed up my hole and her finger and then slid in her finger. I had enjoyed it before but now I was loving it. I began to mean with pleasure. After a bit I was laying with my face in the bed with my ass in the air while she fingered my asshole. Then I got what I never thought I would ever get and she gave me the ole reach around. Having someone jack me off while also pounding into my ass was a weird but amazing experience. I couldn’t even speak it felt so good and I ended up cumming all over the sheets beneath me. I laid in my cum for a while and then rolled up red faced to see her just smiling at me. She asked how I liked it and I could do anything but smile, laugh, and say, “you can do that to me more if you want to.”
I pushed her on her back and ate her out until her hips began to buck and her juices squirted into my mouth. After we finished and I went to bed I couldn’t help but feel a bit empty in my asshole. Never thought I would enjoy assplay but now I can’t wait till we do it again.
Source: reddit.com/r/gonewildstories/comments/6jobsm/gf_did_some_exploring_on_me_last_night_mf_assplay
Great story! That’s how it started for us a few years ago and it really is a pleasurable thing. It’s one of my favorite things in sex now. My wife loves fingering my ass about as much I enjoy it.
Wait and see what happens when you find out if she can take things as well as she dishes it out
You got a winner. Don’t be stupid and mess it up. You know what I’m talking about.
Great story, you def gotta try with a toy next
Time to add some toys to the mix…or maybe another guy and you can both take turns getting filled