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My (M26) first time being fingered in the ass by my gf (F28)
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This happened shortly after my previous post, where essentially my gf started becoming a lot more dominant in our sexual relationship. I never admitted to liking her dom side, but she knew.

During our trip to Mexico, we had planned on having sex at least 3 times a day. We had some of these encounters planned out, one of which she wanted to keep a secret. So on the second to last night of our trip, we were already making out and undressing each other when she whispered in my ear, "I have a surprise for us." She gave my ear a lick and told me to stay on the bed. She goes to the closet and gets her purse. Going through it, she pulls out a bottle of lube.

I was excited because I thought she was finally allowing for anal. I started to get up but she told me not so fast. She then explained that she was not letting me fuck her ass because she wasn't ready for that. The lube, she told me, was for my ass because she was going to finger me. I had a weird feeling of disappointment and excitement. So she put me onto my back and told me to hold my legs in the air. I complied with her orders and she started rubbing the cold lube all over my asshole. I have to admit it felt amazing just to have my asshole rimmed with her finger. My dick was standing straight up. She teased me for it, "well someone's excited".

Then she put a finger in. That was a lot more uncomfortable. I let out a grunt that was a combination of pain and pleasure. She worked the lube in with her picky, slowly fucking my ass with her finger. After about 5 minutes she moved up to her middle finger and without long was picking up the pace. By this point I was moaning and she had a smirk on her face.

She leaned forward and started playing with my nipples with her lubed fingers and just then I almost lost it. I didn't want to cum because the idea of cumming from just my ass being fingered and nipples massaged made me feel embarrassed, so I decided I would hold out as best I could until she got bored. For 5 minutes I rode that edge, coming so close to releasing all over myself.

Eventually she decided she had her fun and stood over my cock and lowered herself onto me. In less than a minute I was filling her pussy with my creampie. She was so proud of herself that she got me to cum so quickly, once she started riding me, but in reality it's because I almost came from her fingering my ass.

Edit: paragraphs and grammar.

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1 year ago