Cuthroats Grand Adventure
I was nineteen, she was the thirty six year old mother of one of my friends, Austin. I had been drinking with them and some friends. We ran short on booze and they decided to make an alcohol run but I was getting pretty tuned up and didn't mind hanging with Austins mom who was a gorgeous MILF. She had been looking at me more than what would be considered normal prior to this so my mind was already going places where it didn't belong.
Neither of us said anything for the first few minutes that my friends were gone then she got off the couch saying that she was going to go and get a glass of water; asking if I wanted one as well but I said no. She saw me look at her as she was getting off of the couch - usually I can check a chick out without it being totally obvious but as I stated I was feeling the alcohol and this women was smoking. She was probably around 5'5" slender, gorgeous dark hair that ran along the full length of her back right to her perfectly rounded ass. The grey dress she was wearing didn't extend much past that and was tight enough I could see the outline of her panties.
She smiled and stuck her tongue out and licked the corner of her mouth, raising her eyebrows as she walked away. I could feel my face flush and I didn't know at this point whether or not she was teasing me or actually flirting with me. Turns out she made that pretty clear shortly after.
She was gone for maybe a few minutes before she came back into the living room hiking her dress up as she sat on my legs, facing me "so...do you have a girlfriend?". My heart was beating like mad but I managed a no. I tried to keep my eyes on her face but they kept darting down. Before I knew it she had slid off me and was now kneeling on the ground right in front of me. "well I'm going to teach you how to really treat a girl right" she said undoing my belt and unzipping my jeans.
She slid her hand in and grabbed a hold of me, not with to much force but not lightly either pulling my already throbbing dick out of my pants. As she did she raised her eyebrows again and let out a forever etched in my memory "ooeh honey, god liked you"...Next thing I knew her lips were around my dick and her head began to bob up and down - every now and then she would stare back up with me and that eye contact made it so much more intense.
After a few seconds she slipped her hands under her dress and began running her hand up and down her pussy. Her mouth would break contact with my dick every few seconds as she let out a soft moan. Finally I had enough and said lets go to your bedroom - She smiled and I picked her up, locking the front door as I walked past it.
I threw her down on the bed, tearing her dress off but when it came to unhooking her bra my trembling hands were taking a little to long and she soon aided me unveiling her beautiful perky C's...how she was this old and still had boobs this great was unbelievable. I ran my tongue around her areolas for a few seconds before playfully tugging at her nipples squeezing her breasts. But then I went to what I love more than anything...I spent probably fourty five minutes eating her out during which the doorbell rang a few times, little did Austin know I was ringing his moms bell. Lol.
After about fourty five minutes, she let out an, "Oh my god I want your big cock in my pussy"...She didn't have to ask twice. She was wet and ready to go and I slid in without any trouble; her moaning music to my ears as I took her doggy style. After about ten minutes I already had her on the verge again when she said "put it in my ass!" I was a little confused and hesitated for a few seconds as I had never met a girl that would actually do this before. She began rubbing her clit screaming in ectsasy and again said "fuck my ass!" so i pulled out and she was wet enough with sweat and her own secretions at this point that I was able to slowly push my way in...it was so tight it was painful initially but once I was in I adjusted and began pounding away while she continued rubbing her clit. I reached under her squeezing her tit's, rolling her nipple between my fingers as she continued to let out "ooooh yah's" until my little soldier reached his bursting point.
Needless to say there were a few more times after this before I went back to college for the fall. Austin hates me because during a minor disagreement I told him I fucked his mom which didn't go over well. I still think about her sometimes but there has been a few other women since in the five years since that glorious night.
Best anal story ever. I was hoping to see another post or two like this one. Great job man.