First time writing something like this….
Katie and I had been best friends throughout highschool and for a few years after. She’s drop dead gorgeous. She’s 5’6″, olive complexion, 36C, ballet dancer. After both of us going through numerous failed relationships, when we were 30 we decided to give things a go. She had a kid and was an absolute MILF who did yoga religiously. She was the type that would do anything to please a man.
One night, after a good fuck session and cumming on her face we were spooning. She kept rubbing her ass against my dick, and I knew she was wanting more. So was I. She had told me multiple times how much she enjoyed anal. Something I had never done. After a few minutes of her teasing, I was rock hard. She had moved her body up a little and I licked my finger and began to trace it around her asshole. She let out a moan and my finger easily slid into her ass. Slowly fingering her ass while I gave her nipples some attention with my free hand. After a few minutes she pulled away and turned over. We started to kiss and she climbed on top of me saying she wanted my dick in her ass. Of course, I wasn’t going to say no. She slid her very wet pussy onto my dick and rode me for a short time. She tells me that fucking her ass will be easier this way and pulled herself up and then guided my cock into her ass. She moaned again saying holy fuck that feels good, taking almost all of my dick easily. I’m 6″ and very thick. I could immediately feel the difference being in her ass and I loved it.
I began to slowly thrust into her while playing with her pussy. She told me to stop and took control, bouncing her add on my dick. I couldn’t believe how fucking hot she with my dick in her ass. She wasn’t lying when she said she loved anal. She fucked differently with a dick in her ass, she was more passionate. She wanted me on top of her and rolled over. Spreading her legs, I licked her from asshole to pussy and buried my face into her wet cunt. I love eating pussy and she started bucking her hips into my face. I knew she was going to cum soon. I placed my hands on her hips and held her down. She told me she was cumming and I kept licking that sweet tasting pussy. She told me to put my dick back in her ass and fuck her hard.
I kissed up her body to her mouth, letting her taste her juices. I pulled back and rubbed the head of my dick along her pussy a few times and then put just the tip in her asshole. Teasing her with just the head of my cock, she started to beg me to fuck her. I thrust into her hard and she let out a yelp. I kept up a good pace while rubbing her clit with one hand and squeezing a nipple with the other. I saw some milk on her nipple and she tells me she lactates when she’s close to cumming. I don’t know why, and can’t explain it, but I found that hotter than fucking her ass. I slowed down and payed closer attention to her nipples with my mouth, tasting her milk. I guess she knew I was close because she told me to cum in her ass. After a few more hard thrusts, I came hard in her ass. Laying down next to her exhausted, she started rubbing her ass against my side. She turned and kissed me. With a huge glowing smile on her face she said “you came in my butt” and wiggled her ass at me. We had a good laugh and she goes onto to tell me how she loves the feeling of cum in her ass.
That was the fist time of many. Things didn’t work out between us but she was a damn good fuck.
Source: reddit.com/r/gonewildstories/comments/hkez4f/first_anal_with_exgirlfriend_mf