I didn't see anywhere to put this so here goes
I met my girlfriend shortly out of high school. She lived at home with her parents and sister. Things moved along from groping to heavy petting to oral(lots and lots of it!) after a while after getting both of us good and sloppy wet she would slide the lips of her shaved pussy up and down my dick(but no penetration). She would also slide me up and down the crack of her ass.
Then one night she grabbed my cock and put it up against her asshole. I moved back for a second and she whispered "where are you going?". My heart raced and I said "I'll go wherever you want." As she pushed herself back I couldn't believe how tight she was and I heard her let out a soft moan as she grabbed the bed. I let her control how fas/far things went. Once she got the head in she began to rock ever so slightly. After a bit I asked if she was ok, she didn't say anything just nodded and pushed in the last bit. As I reached around to her pussy I found her to be absolutely soaking wet, I mean thick wet pussy juice. After hearing her moaning into the pillow and digging her nails into my leg, pulling me into her, I came hard. After cleaning off her ass and back, she asked how as it, I was blown away, I was amazed she did that! I asked how she did, she said it hurt for a second or two then felt great and once I started fingering her it sent her over the top.
We've revisited it quite a few times since
