[M]y [f]irst post here, hope you enjoy it. | 2016

It took 41 years but last night I finally had anal sex. I have been with my awesome 21 year old fiancee for about 15 months and aside from all the other great things she has brought to my life, our sex life has been in-fucking-credible. Here's a little background:

We are very open with each other and have indulged in a number of our sexual fantasies. We have talked about letting me try anal on her and she was interested. My cock is definitely not huge by any means but kinda thick, so we decided to get her some butt-plugs first to experiment with. We used the plugs last weekend and she did quite well as a first timer and managed to get the medium sized one (we bought a 3 pack w/ a sm, med, and lg.) all the way in her tight little asshole. Then we had completely awe-inspiring PIV sex with butt-plug in her ass. The feeling of her being so "full" was amazing for us both.

Fast forward now to last night We were having a little fun with foreplay last night and before I was to take her sweet little pussy with my tongue, she breaks out the anal-ease and lube. I look at her inquisitively as she applies the anal-ease to her butthole. She is aware that she has captured my interest and says for me to lick her clit and maybe she will have a surprise for me. I proceed as directed and within minutes I am swallowing a mouth full of her girl nut.

Now as the perverted fucker that I am, I had in the back of my head that she was preparing to put the plug into her little butt. She pulls me up from her soaking wet pussy and without hesitation says she wants me in her. I proceed to squeeze my cock into her pussy as she tells me that I don't get the surprise until she cums on my dick. "Challenge accepted" and within a matter of minutes I can feel her vagina squeeze and contract on my cock. She asks me to get on my back, I oblige her. She straddles me, reaching behind her back to grab my cock and cover it in lube. She then smears some lube on her asshole and holds the head of my dick to the opening of her tight ass. Slowly, at her own pace she sat on my cock pushing it deep into her ass.

HOLY SHIT, the feeling was so....amazing. So warm, so very tight, and the mere thought and sight of this great deed were absolutely mind-blowing. She rode me like this for a couple minutes until I turned us so that she was on her back again. I lifted her legs up so her knees pressed against her beautiful tits and slowly pumped at her ass. At first they were just little pushes, not really pulling out so much as pushing into her virgin ass. I began to stroke in and out of her ass at her direction, going from short, slow strokes gradually getting longer and faster. Within a span of 5-10 minutes I was on the verge of cumming. I looked down into her eyes and told her I was gonna cum in her sweet virgin ass and she nodded her head in approval. That is all Daddy needed. A couple more strokes and her tight ass pushed me over the edge; I came very hard inside of her ass. I came in her ass and it felt fucking fabulous.

I have to be honest, as a 41 year old male that had never had anal sex before, I wanted more than anything to just pound away at her ass, but I respectfully fought that urge. I know this is not the hottest story to most of the readers here probably, but for me, it was definitely worth writing about. Thanks for letting me share. Oh, and for those interested, feel free to look through our profile, she LOVES to hear ALL the comments from men and women.