My largest age gap was a 21-year-old I dated when I was 28. She was a short-haired tatted-out yoga instructor with a thick behind and perky breasts, five feet even. We went on a few dates before we hooked up; she wore a bandanna as a shirt to one of them and it sealed the deal for me.  I walked her back to her place and we made out on her front porch.  We were kissing passionately and when she pulled away from me, we realized her bandanna had slipped down and both of her tits were out.  Her nipples had barbell piercings.  We were both initially in shock and she pulled the bandanna up again, looking around to see if anyone on the street had seen.  We laughed about it and then she invited me inside; I met her roommates and then we retired to her room.

We made out some more on her bed.  She asked me if I wanted to fuck her face, so I stood up and unzipped my pants and pulled my boxers down.  My cock was swelling up and it sprung out. She took it in her hands and said "wow, your cock is...very nice." She tried to take me into her throat but I couldn’t get past the back of her mouth because I was too hard. She was disappointed and said she could usually deepthroat. We tried again later that night when I was softer and we managed to cram my half-hard cock down her throat.

Her pussy would cream when I was fucking her, the base of my cock would always be ringed with a thick white sauce. I'm only 7.5" x 5" but she was really into my penis; when I would wake up with morning wood I would park it between her ample cheeks and just hotdog it like that until she couldn’t take it anymore. She was uncontrollably loud when we had sex, which wasn’t a problem at my place, but I would often have to gag her with my hand over her mouth at her place so her roommates didn’t complain about the constant noise.

The relationship lasted about 8 months ended with a messy breakup so we didn't see each other for a while afterwards.  She picked up some shifts at a restaurant my friend worked at and told her that she wanted to fuck me again but wasn’t looking to rekindle the relationship again, she just wanted the dick. My friend told me this to warn me, but I remember getting hard when I heard that she was thirsting again and wasn’t sure I would be able to say no.  Sure enough, one day she called me up out of the blue and said she needed help changing the inner tube on her bicycle. I told her to come by my place she showed up with a 6 pack. The tire got changed and we had a few beers on the couch and eventually started making out. She got up and started leading me to my bedroom but I stopped her in the doorway and started grinding against her ass. She arched her head back to look up at me and we started making out like that, me behind her choking her and kissing her and rubbing her pussy and breasts. She was pressing her butt into my crotch as hard as she could, leveraging against the door frame. She undid her jeans and I helped her pull them down and got my cock out. I teased her with it for a minute, sandwiching it between her asscheeks and running my shaft along her asshole until she started to moan for it, then I pushed her onto the bed and ate her out for a little bit. I stood up at the edge of the bed and reached down to guide me in herself. It must have been a while for her, or I must have been extra hard that day, because it was a tight fit.  She winced and looked at me "Holy shit, did you get bigger or something?!" 

I went down and ate her out some more and worked on her with my fingers, getting her ready.  After she came I gave her a few minutes of the slow game with my cock, stretching her with gradually deepening strokes.  I flopped onto my back and she got on top and started squatriding me hard, full shaft, yelling "yes yes yes" loud as hell. She started repeating "Your big fucking dick is going to make me come!"

I did not last long after that. We stayed up late trying out new stuff on each other that we'd learned from other partners, and in the morning she blew me a kiss and biked away.  That was the last time we fucked and I like to think it repaired our friendship.