It was the middle of summer when the two of us decided to jump in her pool for a late night swim, around midnight. My girlfriend and I were cute and cuddly, not intending to do anything special. After floating around for a while I gave her a quick kiss and felt her come back a little stronger than expected. Without any second thought I kissed back again and felt her tongue slide into my mouth, and we slipped over to the edge of the pool where I pinned her against the wall and we began to make out even more intensely.
After this went on for a while my hands began to slide my way down her body and grip her thighs. When she didn't react I started to drag my fingers toward the inside of her legs and instinctively she pulled herself away from me. Concerned, I asked if I had gone too far, but she said no and hinted to me that it was just her time of the month. I was okay with this, but admittedly a bit excited at this point, and I could tell she realized it too. In what was a very awkward conversation, she started to tell me she felt bad because she, too, was really in the mood and she had been considering trying something new. She didn't want to say what it was, and it took me a while to pick up on the hint when I asked her if she thought she'd like it. Her response blew my mind: she grabbed my wrists, wrapped my arms around her by her lower back and told me she really wanted to find out. I slipped my fingers into the back of her swimsuit, thinking I would tease her a bit first and see how she reacted. As my hands went lower she just continued to look me in the eye and so I began to kiss her again as I slid a finger down and played with her ass hole a bit. I just played with my finger around the outside and slowly slid a finger in just a bit, waiting, and going a little deeper. She enjoyed it, as her breathing got stronger as I did.
Not long after she stopped kissing me and said we should go inside. We got out of the pool, dried off, and we decided to go down into her basement. She wanted to change out of her swimsuit, so I put on some basketball shorts while I waited for her to come back downstairs. In the beginning it was very awkward, as neither of us knew how to approach this situation, but eventually it was incredible. I asked her how she wanted it, and she got in front of the couch, facing the back, and kneeled on it. She reached back and pulled her pants down to expose her ass to me. I grabbed the lube, poured plenty onto her ass and began to play with my fingers again. I spent less time teasing and sliding in a finger to loosen her up a little bit, applying more and more lube whenever I felt I needed it, or if she implied it hurt. I watched her grip the couch cushions for a while when she told me to fuck her.
With her kneeling in front of me and her perfect ass right there I applied more lube onto her and myself, while slowly sliding my cock into her tight ass. She gasped in pleasure and I thought it was the most amazing feeling in the world. It wasn't just the tightness and the lube, but I think the anticipation and nervousness of trying something so taboo increased the excitement, too.
Once my rock hard cock was all the way inside of her and she felt more comfortable, I began to slide myself in and out of her. She groaned and breathed deeply no different than in vaginal sex, so I wrapped my arms around her and grabbed her breasts or pulled her hair as I continued to fuck her from behind. The excitement continued to rise quickly both with this incredibly sexy position of my girlfriend kneeling and arching her back right in front of me, and with the taboo of anal sex and experiencing something new for the first time.
As a result, I began to reach orgasm quicker than I ever had, and I thought she'd want me to pull out so I told her I was going to soon. Instead she grabbed my arm and said she wanted me to come inside her. So I didn't stop, I continued to thrust into her ass hole until I felt cum spurt out deep inside her in what was the most intense orgasm I had ever had at that point. As I came I grabbed a handful of her hair and listening to her gasp was what really took me over the edge.
We haven't done it since, just because the conversation hasn't come up, but I still fantasize about the opportunity to do it all over again.
Source: reddit.com/r/gonewildstories/comments/3ufdoz/trying_anal_mf