Well, I am known to love anal sex.
Any time a guy wants to stick it in my ass I am up for it! But, a lot wonder how I came to love anal sex so much. So, I will tell you a little story today about my first time having anal sex. Now, here is my “tail.”
When I was 16 I had already had sex with a few partners since I was 15 but one day I met someone who would change my life forever. I went with my cousin to her work and sat at the bar while she poured drinks for people. Girls my age shouldn’t sit there but I didn’t look like a girl at all. I was approached by an older gentleman wearing a button down dress shirt and tight slacks that could barely contain the hard bulge in his pants.
He sat next to me, I smiled because he was very sexy and I was so horny. I started feeling my young little pussy getting slick from being so excited. He turned to me and said “Well, hello there. My name is William. May I just say that you are very beautiful, my darling. What is your name?” I smiled and looked down at the floor giggling and looked up at him with my eyes wide and smile wide and said, “My name is Bailey, thank you!” He smiled at me and asked if I wanted a drink, I ordered an apple martini since I had seen my cousin order them before. Since my cousin was the bartender she looked rather puzzled but smiled and made my drink. He had a whiskey on the rocks. We talked about life for a couple hours and I just mostly listened to his exciting life. He was a very successful lawyer who had been divorced a couple times and had 3 kids and was just looking for something carefree.
He asked me later on if I would like to have dinner the next night.
I thought in my head “Shit, I have cheer practice! What do I do? Hm.. well, you can always practice another day. Go for it!” I agreed and he was going to pick me up at 6 pm. We parted ways and I waited for my cousin to get done with her shift. On the way to my house she asked “So, I see you were talking to that guy. What’s going on there?” I replied, “Haha I got asked to dinner,” she questioned, “Does he know that you’re only 16?!” And I said “Nope. I honestly don’t care. And neither should you.” She just smiled and dropped me home. When I was getting out of the car she yelled out her window “Don’t get locked in a cellar for 15 years!” I just rolled my eyes, laughed and walked inside my house. When I got to my room I just jumped on my bed smiling and thought about what to wear. “Maybe the dress you got for formal? No, too sparkly. How about your sun dress you got while visiting grandma last summer?! No, you look like a little piece of cake. Hmm.. what is there?” I shot up from my bed and remembered mom still had clothes from when she was younger in the basement. I ran downstairs and to the basement, mom didn’t know what I was doing.. she was too busy arguing with her boyfriend about how he needs to spend more time with her. In the basement, there was one light overhead and I clicked it on. In the left corner was boxes marked “MOMS STUFF.” Found a box of shoes, some old diaries, pictures and then finally clothes. I looked through the box and at the very bottom was this PERFECT tight black dress. Halter top, tight, ruched on the sides and just above my knees. I went upstairs to find the perfect shoes for them. Black patent 6-inch heels. Now everything is ready. I couldn’t wait.
School was a normal day… lots of homework but I couldn’t care less.
I had a date and was ready to get home and get dressed. I got home at about 4:30 and got in the shower and scrubbed myself clean. Mom was at work until 9 pm that day so I would have had to feed myself anyway. I got out of the shower, blow dried my hair and set curlers in it. I took my towel off and sat at my vanity looking at my perky tits. They were already big and I was only 16. I jiggled them at myself and pinched my nipples and got wet just thinking about being fucked by William. I shook myself and started applying my makeup and took the curlers out to start styling. Of course, when I got up from my chair I noticed it was soaking wet from my pussy and I cleaned it up with a paper towel.
I put on a push-up bra to help my cleavage look good and make me look a little older, then I found my sexiest thong and put it on. Black and lacy.
I waited outside for him, smoking about 3 cigarettes from being so excited and trying not to play with my pussy on my front steps. Finally, a shiny black Mustang pulled up and I felt my pussy throb. I jumped to my feet and walked to the car. There he was.. he opened my door and said “Wow. You look absolutely amazing.” I smiled and sat down. He couldn’t stop looking over at me but we had a quiet car ride to the restaurant, other than the Prokofiev CD he had in the car. When we got to the restaurant the valet opened my door at helped me out.. and he was looking up my dress which turned me on a bit and I felt my young little pussy throb again. Well, we walked into the place and were seated at a table next to a window.
The date went well, we talked and laughed and had a nice time and when it was time to leave…
I didn’t want to. In the car, I looked to him while he was driving towards my house and I said “I don’t want to go home yet,” and grabbed his inner thigh and continued, “Can you take me to your place?” He smiled devilishly and we drove on. We got to this amazing condo with a pond in the front yard and he helped me out of the car and up to his door. Inside the house, it looked like a fancy bachelors pad. Leather couch, hardwood floors, a Playboy on the coffee table. He turned the lights down and I couldn’t help myself… I was so fucking horny and needed to get off somehow so I grabbed him by his tie and kissed him. He didn’t resist at all and I could feel something getting hard up against my tummy. I tossed my hair to the side and he unclasped my dress and let it drop to the floor. He picked me up, wrapping my legs around him and grabbing my tight young ass taking me to the couch. I stopped myself and pushed him and said “Wait! Wait, wait. I have a secret to tell you but you can’t be mad.” He looked at me with worried eyes and said “Alright.” I then looked away from him and told him the truth since he didn’t know, “I’m… I’m only.. 16. And I hope you don’t care about that! I just can’t help myself. You make my pussy throb!” He smirked and reached behind me and unhooked my bra and said “I know. And I don’t give a fuck. I want to fuck you so hard that you will remember this forever.”
He sucked on my hard nipples and bit them a little. I writhed in pleasure just thinking of him just touching my little cunt. He moved down my body and ripped the thong right off me revealing my smooth, pink, young pussy and licked his lips getting closer to it. I laid back spreading my legs wider and his tongue touched my clit and it twitched as he flicked it. He sucked on my pussy until I came so hard that I screamed.
He then flipped me over and grabbed my hair and whispered “I’m going to show you one of my favorite things. Anal sex.”
He unzipped his pants and showed me his big cock. It was 10 inches long and 6 or 7 inches around! He then spat on his cock and licked my ass making it nice and wet, I was so scared of not knowing what he was doing. He then stuck his head up to my asshole and told me to take a deep breath. I did and then I felt an intense pain as he slid his cock into my ass! I started to cry and try to get away but he held me down and told me to “Shut the fuck up. You’re going to LOVE THIS!” He went slowly at first as I cried.. and then the pain subsided and he went faster. There I was, getting fucked in the ass for the first time by a 53-year-old! I felt amazing!
I gripped the arm of the couch and bit my lip just feeling his cock slide in and out of my tight asshole.
He was spanking my ass and gripping my hips, then, I felt it.. my pussy was twitching again! This time I reached for it and fingered myself and I screamed in pleasure as I came. I thought it was just a regular orgasm.. nope! I had squirted all over his couch and he was happy about it.
Then he gripped my hips tightly and started breathing faster and moaning and grunting.. then I felt his nails dig into my hips as he moaned and I felt his cock twitching deep in my ass as he filled me up with his hot cum. I smiled and he pulled out of me and his cum was dripping out of my ass. He licked my ass, sucking every drop of cum out of it and slurping it all up. He kissed me and said “See? You’ll remember this night for the rest of your life.”
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