I'm working on a story for every category. Here is my submission for the Anal category. Let me know what you think.
The first girl that I ever had sex with was also my first girlfriend. We were together for our last 2 years of highschool and I was pretty sure that I loved her. We were both virgins when we first started having sex and we had no idea what we were doing. We eventually got pretty good at it, learning how to get each other off and I loved making her cum 2 or 3 times a night. She was smoking hot, with a tight little body that she kept fit by dancing on the school dance club. She had dirty blond hair and light freckles on her nose. Her boobs were a nice C size and her ass and thighs were very tight and toned. She kept her pussy in various states of grooming, ranging everywhere from full on bush when we started out, to full brazilian wax.
Almost all of our sex took place at her house. I have 4 younger siblings and our house wasn't very big, so it was hard to find any privacy. Plus my parents were pretty strict and I wasn't allowed to have girls in my room. Kate's house was the complete opposite. She had 3 older sisters that were all out of the house. Her dad was hardly ever at home, and I never quite understood what he did. That left her and her mom home alone for the most part. Her mom had raised 3 very beautiful girls who were very "popular" in highschool so she didn't seem to mind too much what we did. There were many times that I ended up staying the night, and Kate's mom would make breakfast for us in the morning.
I was over at Kate's house one Friday night towards the end of our senior year and we started to go at it. Kate's mom was out and her dad was in Germany of something so we were home alone. Normally we take it to her bedroom, but as we were watching TV things started to get pretty heavy. I put my hand up her t-shirt and started to fondle her boobs over her bra. Her hand went down my shorts and she started stroking my 8" cock.
As we were getting into it the front door opened and in walked Kate's mom, with my hand up Kate's shirt and her hand down my pants.
"Oh, I'm so sorry you two. Don't mind me, I'm just going up to bed," she said.
Kate kept her hand down my pants and just said "OK, goodnight mom."
As her mom went upstairs I asked, "Should we take this to your room?"
"No, I think we're OK," Kate replied, and started unzipping my pants. I wasn't about to protest and got back into it with her. Pretty soon I had my hand down her pajama bottoms and was rubbing her smooth little mound.
It didn't take too long until I had her pants off and was on my knees between her legs. I love oral sex and was giving her a thorough tongue lashing while she pulled and squeezed at her nipples. As I was focusing on her clit I reached down and lifted her feet up onto the couch, opening her completely up to me. As I sucked on her clit she came for the first time, soaking my lips and chin with her sweet juices.
As she came off her orgasm I started to lick up and down between her tight pussy lips, splitting them apart and lapping up all the cum that remained. As I moved my tongue up and down I let it go lower and lower every time. I finally got to her smooth piece of skin between her pussy and her asshole, but I wanted more. I kept going down and eventually had my tongue rimming around her tight little asshole.
I loved her smooth little anus, but that was the final frontier so to speak in our sexual maturation. I had tried anal with her many times, but she kept telling me that she just didn't think it would work. She liked me to rim her, and even put a finger in, but if my cock got anywhere near she would quickly move it out of the way.
I stayed down there for a minute, ringing my tongue around her wrinkled skin. Then I started to run it back and forth over her opening, until stopping with the tip of my tongue just inside her tight hole. As I tongued her ass I used my thumb to rub her clit and in no time she was cumming again. I could feel it trickling out of her pussy and tickling my nose.
At that point I needed some action and stood up. I figured I had just gotten her off with my tongue about an inch up her ass, so I may as well give it a try. I took my cock and put it right up against her ring. To my surprise she didn't push me out of the way. I gave her a second and started to push.
"I don't know Jim, I don't think it will go in," she protested.
"Come on babe, just relax a little," I responded, ready to give up as usual.
"OK, go," she said after a second.
I pushed again and she started to wince. All of a sudden I felt a pop and realized that her ring gave and my head had popped in. "Holy shit," I thought, "I can't believe this." I looked down and sure enough the head of my cock was in her tight little hole. In fact it was so tight that the pressure was almost too much. I realized that I wasn't going to last and started to push in.
"OWWW," Kate said loudly. "It won't go in anymore."
With that her sphincter clenched down very hard on my cock head. I normal circumstances it probably would have hurt, but since it was her ass that did it for me and I lost it, cumming just inside her asshole. As I finished cumming she squeezed so hard that it actually pushed my head right out, with an audible "pop." I then sat back and watched as she pushed all my cum out of her asshole, all over her pajama bottoms. It was probably the hottest thing I've ever seen and when it was done I got up and kissed Kate passionately on the lips.
She fell asleep very quickly, still naked from the waist down. I quietly got up and went to the upstairs bathroom where the shower was to cleanup. Everything was dark and I was still naked, with my cock sticking out 8" in front of me. I walked quietly down the hallway so I didn't disturb Kate's mom and opened the bathroom door. As I turned on the light I was shocked with what I saw. There sitting on the toilet with her underwear around her ankles was Kate's mom, with her hand between her legs.
"I'm so sorry Mrs. White, I had no idea anyone was in here," I said as my face blushed.
"It's my fault,, Jim, I didn't lock the door," she replied, staring intently at my raging boner.
"Oh, sorry" I said and reached down to cover myself.
I turned to leave and she said, "You can come in and do what you need to."
I couldn't believe what I just heard. Her mom had always been cool and all, but this was completely different. I had just caught her clearly masturbating and she was acting like it was nothing at all. I had never thought much about it, but Kate's mom wasn't bad. She had 4 kids and had to be in her late 40's, so she had some extra weight, but she was by no means fat. Her ass had a very mesmerizing jiggle as she walked and I had noticed it on many occasions. Her tits were much larger then Kate's and she wore bra's that accentuated her ample cleavage.
I turned back around and said, "Erm, OK." I walked back in and moved my hand away from my cock.
"My heavens Jim, that impressive. I see why Kate likes you so much," she said as I walked to the shower.
I was shocked and turned around to face her. She had moved her hand and her legs were spread wide open, revealing her pussy to me. As opposed to Kate she had a thick bush of light brown hair around her pussy, and her lips hung down below the hair.
She stood up and took a step towards me saying, "But, I can understand why she can't get this into her little ass." With that she reached out and lightly petted my cock, which sprang at her touch. "And no wonder you want that tight little ass so much, I wish mine were that hard," she said, turning around and sticking out her ass a little.
"No, yours is fine Mrs. White," I stuttered.
"You don't have to lie Jim, I'm sure it's nothing compared to the tight little teenage ass your used to. But, there are some advantages to an old, experienced ass," she said, looking back at me over her shoulder. She reached behind her and grabbed my cock, pulling my toward her ass until it was rubbing on her fleshy cheeks.
"I'm sure there are," I reply and start to guide my cock to her crack. I get there and watch as my head disappears in between her cheeks. My cock is buried about half way in between and it stops. I figure I must be at her asshole and start pushing.
"Just a minute there stud. No wonder you hurt poor little Kate. You need to get an asshole ready before just shoving that monster up there. From Kate's moans it sounds like you know how to get it ready."
With that she got down on her knees and lifted her ass up in the air. As much as I love Kate's hard tight ass, Mrs. White's 2 thick cheeks spread apart was the hottest thing I've ever seen. Her hairy pussy was clearly visible just below her asshole. The light brown hairs followed a path in between her legs and up around her large dark skin surrounding her hole.
I dropped to my knees and dove right in. I licked all around, wetting the hair with my spit. The aroma from her pussy and ass was intoxicating and I couldn't get enough. I didn't even touch her pussy and just kept my tongue rimming her ring. Then I placed my lips right on her hole and started to kiss and suck. I put my tongue right on the opening and started to push in. It got in a little and I started wiggling around. As I did that Mrs.. White started to moan. I took that as a good sign and kept pushing. My tongue just kept going up her ass, much further then I could get it in Kate's. Finally my tongue was all the way in and my lips were planted firmly around her opening. I then started to tongue fuck her ass.
For the first time in my life I was drunk with lust and could have stayed there all night. Instead Mrs. White said, "Jim, give me your cock now."
That's all I needed and stood up. I took hold of my cock and aimed it right at her asshole. I expected to have to push hard, like I did with Kate, but just after I started it popped right in. I stopped, not wanted to hurt her and she said, "Don't worry hun, you won't hurt me, now fuck my ass."
With that I shoved my cock all the way into her ass and she replied with a "goddammit." I had lost all control and started to fuck her ass hard and fast. I had a great view of my cock jackhammering in and out of her sweet asshole. My balls we slapping so hard against her pussy that Kate had to be hearing it if she was awake downstairs, but I didn't care.
"Fuck Mrs. White, I'm going to cum," I moaned as I buried my cock all the way up her ass.
"Give me your cum Jim, shoot is up my ass just like you did with Kate," she said.
With my cock in there I started to unload, for the 2nd time in about 30 minutes. I thought I came a lot up Kate's ass, but I just kept shooting up Mrs. White's. Finally I was done and just sat there with my cock in her ass.
"Well Jim, how was it," she finally said.
"Fucking amazing, your ass is so hot," was all I could say, not believing what I was saying to my girlfriends mom. My cock was still hard, but I started pulling it out. Instead of popping out of her ass it slid right out and her asshole was left gaping open, enough that I could see into it about 2 inches.
It stayed that way for about 10 seconds then closed, but to my surprise opened back up. As I was watching she blinked her asshole 4 times, until on the 5th a small spurt of cum came out and ran down her ass. She did it again and this time a much larger wad came out and leaked down onto her pussy, then dropped on the floor. One last time her ass opened up and the rest of my cum came up and pooled there in the opening.
I couldn't resist and leaned over to give her sweet asshole one last kiss, despite the fact that a pool of my own cum was there. She giggled and said, "You better get back down to Kate."
As much as I wanted to stay there worshiping her ass and licking her clean, I realized that she was right. I got up and without cleaning my cock at all gave her a tap on her right cheek, watching it jiggle as I walked out.
I went back downstairs and cuddled up with Kate, who apparently stayed asleep all through it. I was still completely naked and my cock was wet with a mix of my cum and Mrs. White's ass, so I was careful to not let it touch Kate. Soon I had drifted off to sleep.
I dreamed about Mrs. White all night and woke up in the morning with Kate's hand around my ragging boner. Before I was completely awake I realized that she was on her knees and taking my cock into her mouth.
"Dirty boy, didn't you wash yourself off last night," she said to me after a minute, obviously tasting the dried cum.
"No, I was too tired," I replied with a smile.
I put hand gently on her head and lowered it back to my cock where she proceeded to clean up the combination of dried cum, and her own moms ass. As I shot my load all over sweet Kate's pretty face I glanced up at the stairs just in time to see a foot disappearing behind the wall.
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<a href="http://www.lushstories.com/stories/anal/loving-my-girlfriends-moms-ass-1.aspx">Loving my Girlfriend's Mom's Ass</a>