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    I am a petite, 5”2”, 110 pound women with a very small ass. It turned out that anal sex with Al was impossible. The first time we agreed to try it when Al put the head of his nine inch cock near my anal opening, and tried to push it inside me, the pain was excruciating. The head of his cock was just too large to pass my sphincter. My small tight ass just refused to allow him in no matter how we tried. I asked my doctor about it, and he explained “your anus is unusually small, you could damage yourself if you put something that large in your ass”. I knew there was just no way Al could ass fuck me. So we just decided to rule out anal sex.Then we met our neighbors Tony and his older wife Carol, soon we were having group sex together but no wife swapping. One day Carol and I were talking about anal sex and I mentioned our dilemma. I told her I just couldn’t accommodate Al’s massive cock. Carol had seen Al’s monster cock during our joint lovemaking sessions. She laughed and said “I couldn’t either, that thing would split me right open”. Carol then suggested “why not let Tony fuck you in the ass, I don’t mind, as long as I can watch, we all can see his smaller cock would fit in you pretty good”. Al and Tony nodded in agreement and we all that next Saturday night my ass would be deflowered by Tony.To tell you the truth I couldn’t wait for Saturday. That week I watched some online anal sex porn to learn the right techniques and positions. I must have watched six hours of anal sex vids. Saturday night came and Tony and Carol arrived. Carol immediately asked “where’s our virgin”? I came down the stairs dressed in the skimpiest shorts that were two sizes too small for me. They were so small I found them in the teen section of JC Penny. My firm ass cheeks were half exposed and you could see my hard nipples under the red halter top, my white gym shoes topped off my innocent gym uniform look. We all had a few drinks and began some kissing and fondling as a prelude to sex. Carol could see that I was horny as hell and said well, “what are we waiting for, let’s go upstairs and deflower this young ladies virgin ass”.I couldn’t wait and rushed excitedly up the stairs to our guest bedroom. I had bought some new heavy sheets Astro-Glide lube but wouldn’t need any condoms. We had all agreed to let Tony bareback me so I could really see how a real cock would feel inside me. I was so horny my ass was actually tingling with excitement. I immediately stripped naked and got on all fours on the edge of the bed. This was the position I chose after watching all that porn. My ass was slightly hanging over the edge of the bed so Tony could stand up and assfuck me.Tony discarded his clothes and his six inch cock was fully erect. I knew I could take that inside me with no problem. I handed Tony the Astro-Glide and said “be careful at first until my ass gets used to it, I’ll let you know when”. I knew Tony was no jerk, he applied a generous amount of lube to his fingers and inserted first one finger in my anus and gently pushed it in. I flinched a little from this first insertion. Tony gently ran his finger in and out of me to so I could get used to the in and out motion. Then he put two and then three fingers inside me, soon I was very relaxed. My ass was ready to accept something bigger. Tony then stood by the edge of the bed and lined up his cock with my asshole.I looked back at Tony and whispered softly “I’m ready, go ahead”. With that Tony’s cock went between my ass cheeks. It didn’t hurt at all until it met my sphincter and the head of his cock met the entrance to my ass. As Tony pushed against my outer anal opening it hurt like hell. The head of Tony’s rock hard cock was bigger than I expected, but Tony knew what he was doing and quickly inserted the head past my anal entrance. As the head entered me I screamed, “God that hurt’s, but don’t stop, I’ll get used to it”. After the head and half of his shaft were inside me, Tony just held it there until I got used to a cock inside me. He was an experienced assfucker and knew when I had relaxed enough to take the rest. I said, “it still hurts but go ahead give me the rest”. With that Tony slowly pushed his cock deep inside me. I flinched and again said “that still hurts your stretching me, go slow when you fuck me”. Tony began to slowly withdraw his cock a little and then thrust it forward again. The pain was replaced by the feeling of his cock pushing in and out inside my anal orifice. I grunted each time Tony moved his cock in and out but slowly my ass was getting used to having an organ move inside it. Tony never withdrew it totally so the head would not pop out. I would not have to endure the pain of him having to push it in my anal opening again. All of a sudden the feelings of discomfort gradually changed over to feelings of extraordinary pleasure. Tony was a great lover and kept up his slow even strokes as he fucked my virgin ass. Soon I was enjoying the feeling of a man’s cock moving in my ass. After several minutes, I had accepted the wonderful feeling of sensual excitement that Tony was stirring inside me. Then just like in the porn movies I had watched I began moving my body back and forth to meet Tony’s cock. I was riding him like the sex craved anal whore. Tony’s pole went in and out of my ass as we both started to rapidly fuck each. Every time Tony’s cock entered me all the way the head of his cock hit my “G” spot. Soon Tony had found my spot so many times I began panting heavily and knew I was about to have my first anal orgasm. I moaned like a lusty bitch as my husband watched Tony bring me to my first anal orgasm. I didn’t moan or scream the feeling were so intense my whole body was frozen in ecstasy, all I could feel was every fiber of my body was centered on the feeling of that cock going in and out of my ass. Tony’s cock had total control over my mind and body. Tony kept fucking my ass and a second orgasm followed with a third on the way. I screamed “fuck me, fuck my ass, and don’t stop until you cum in my ass”. Tony was so turned on by this I could tell he could not last much longer. He grabbed my hips to hold me still and began fucking me faster and faster. I didn’t care, my ass was on fire as Tony let out a loud moan and thrust his cock all the way in me as his cockhead exploded inside my ass. At the bottom of my womb I felt a warm sticky liquid being deposited inside me. Tony’s throbbing organ continued to pump his semen deep inside me where semen had never been before. It was a great feeling he continued to thrust inside me until he went limp and withdrew.We both fell back on the bed exhausted. Suddenly, Carol said, “Come on Cindy, spread your legs let’s see that creampie in your ass”. From the movies I had watched I knew just what she meant. I lay on my back on the bed and raised my legs up so they could all see my anus. I knew that from this position they would be able to see the gobs of sticky white semen running out of my ass. Tony’s sperm ran down to my pussy onto my thighs. Tony must have dropped quite a load in me; it took a while for all of it to seep from my ass. I was now broken in and I had loved it. I didn’t want to, but I knew I would have to find a boyfriend with an average cock who could service my ass.

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