This is the story of the first time I did anal. I wrote it on vacation at my parent's house, got a little carried away reliving the experience in my mind, and got very excited ... so sorry it is so long. I got so excited that I actually soaked through my panties and
my sweat pants. I have posted a pic of me after writing this story, wetness and all, and a pic of the guy from the story (well, at least his cock, which took alot to talk him into letting me take it).
My First Anal:
I was never interested in anal until I started dating this guy John about 8 months ago. John had an anal fetish and would always try to sneak a finger in while we were doing it doggie style, and I would always push his hand away. One night while he was going down on me his tongue strayed a bit south of my juicy tid bits and flickered on my little asshole a few times. I was completely shocked and before I could say anything, he has his tongue running all up and down my crack and lightly circling my puckered hole. I really liked it so I decided I would try taking his finger that night. It felt weird at first, but once I got comfortable I really did like it. We kept dating for about another month and we worked up to being able to fit two fingers in my hole. After we stopped dating I started using my fingers and a small vibrator in my ass while I was masturbating. It made me feel so dirty and felt so good, I loved it. I would often take a finger or two in my butt while having sex, and even worked my way up to a small dildo.
The first time I actually had anal sex was Thanksgiving night of this year. I stayed in town because I had to work until 5 on Thanksgiving. After work I went out to a bar with one of my fairly boring coworkers because my roommates and my friends were out of town for the holiday. By about 11 my friend decided she wanted to go home. The combination of a bit tipsy and knowing I had the apartment all to myself made me pretty horny, so I decided to stay and see if I could meet a guy. My friend left and it wasn't 10 minutes until this very very cute guy walked up and started talking to me. His name was Matt and he was really tall and had a very trim, athletic build. He started buying me drinks and flirting. He bought me drink after drink and I was pretty d***k. I started talking a bit dirty to make sure he was coming home with me, and we got one last drink for last call and headed back to my place.
When we got to my house we started making out on the sofa and as I ran my hands over the front of his jeans I felt a huge bulge. After rubbing the bulge a bit more and determining it really was a huge bulge, my horniness swept over me and I had enough of kissing and making out - I wanted to see what was under those jeans! I took off his shirt and started kissing his chest while undoing his pants. I started to make my way down and pulled out his dick. My mouth dropped; I had never seen anything like it. It was HUGE. I am not talking big, but huge. I put one hand around the base and another hand on top of that hand and there was still enough of his dick sticking out that I could barely fit it in my mouth. I was so wet.
After I sucked him for a few minutes he lifted me up and put me on my back on the sofa and started to kiss my stomach before slowly sliding off my skirt. I looked down and was actually embarassed by how wet I had gotten; my panties were so soaked that they had turned a darker color, it was actually running down my legs. He started to go down on me and I did something I normally don't do, I pulled his head up and told him that "this is what I want" as I grabbed his dick. As he put on the condom I was both anxious and nervous that I was about to get fucked by such a huge dick. Did I mention it was huge, because it was! He started to fuck me on the sofa missionary style. He was difficult to take at first, and it hurt, but once I loosed up it was amazing ... I had never felt that full before. The more I got into it the harder he pounded until he flipped me over and entered me doggie style. It was so deep and so amazing. Somewhere in my moans, I told him to stick his finger in my butt, which he kindly did. As he was pounding away I felt another finger go in. With every thrust into me he thrust his fingers deep in my ass. I came so hard from being so full. Unfortunately, he came too.
He apologized for coming too quickly, even though we had been fucking for about 20 minutes, and said that he will last much longer during "round 2". I got up and led him to my bedroom where he threw me on the bed, said "I have been wanting to do this all night", and started going down on me. His tongue was amazing, especially since I was so soar for the pounding I had just received. He seemed to know just when I was about to cum because he moved from licking my clit to kissing the inside of my legs. He went back to work and started to bring me close to orgasm again and then started licking my asshole. It was utterly amazing, I wanted to cum so bad I tried to touch myself but he pulled my hands away. As I lay there feeling his tongue circle around my hole and then flicker on top of it, I kept trying to touch myself to bring myself to orgasm, only to have my hand pulled away time and time again. He flipped me over so I was on all fours with my ass high in the air, stuck two fingers in my literally dripping pussy while rubbing my clit with his thumb, and buried his mouth and tongue in my butt. He kept licking my hole and rubbing my G-spot with his fingers until I was ready to explode and would then pull his hand away depriving me of another orgasm. He then used 2 fingers to rub my G-spot and put two fingers into my ass, which was incredible.
Then came the question: he asked "do you like anal sex". I told him I hadn't before and was super eager to try, but that there is no way he is going to be able to fit that monster in my ass! He laughed and I could see that he was once again ready for action. This time he fucked me in every position imaginable for about half an hour. Once again, every time I was about to cum he would pull out and stop and my orgasm would start to fizzle ... it was so frustrating as I was so horny and wanted to cum so bad after being fucked hard for such a long time by such a big dick. All of the sudden he stopped, lightly smacked my ass, and told me to get some lube. I looked at him in horror and he assured me he wouldn't do anything I didn't want to do. I handed him some lube and he pushed me down on all fours and slowly entered my pussy with his cock. He was doing slow, deep, long strokes and I felt a cold blob of lube land on my asshole followed by two fingers slowly twisting their way in. His lubed fingers were like magic in my ass, and his long and slow stokes of his dick in my pussy made me so horny yet just kept me at the edge of orgasm. I felt his hand leave my hip and felt pressure on my asshole as he put yet another finger in my ass. He was swirling around the two fingers from the one hand as he pumped the other finger slowly in and out of my ass. Then another finger. He kept fingering my ass, 4 fingers on 2 hands, but would pull his hands apart slightly while pulling out his fingers, stretching my hole wider. It was so amazing and I got so turned on and kept thinking to myself "Wow I am a four-finger whore, I am such a dirty little girl". It was the first time in my life that I felt like I was a dirty little porn star, which is my fantasy. I was so turned on and wanted to cum so bad that I turned my head and told him I wanted to try anal, but I wanted him to go slow and promise me if it hurt he would stop.
He smiled, pulled out his fingers, and slid his dick out of my pussy. I buried my head against the bed, gripped the sheets tightly with my hands, and closed my eyes in anticipation. I recoiled slightly when I felt my cheeks spread and felt something press against my asshole, but I calmed down when I realized it was just the lube bottle after I felt a stream of cold lube squirt into my little hole. As I lay there in a mixture of nervous and excited anticipation, I kept thinking "I can take it like a dirty porn star, I can be nastier than them, I doubt any of them were willing to take such a huge dick in their ass for the first time, I can do it". I then felt the head of his dick press against my ass and a buildup of pressure as he gently tried to push it inside, making my asshole pucker up tight. As I started to relax my hole I felt it start to open as his tip started to enter. It wasn't long before it started to really hurt, almost like my hole was on fire. I moaned "it really hurts" and he quickly pulled out, rubbed the small of my back and told me that it would be OK, that the pain would pass in a minute and we could try again. I looked back at him and asked how much of it went in, he showed me ... it was barely anything .... I got really scared looking at all of those inches and thinking if I can't even take an inch, how can I take that entire thing! He started to finger my pussy and I was instantly building up towards orgasm. I noticed that my hole no longer felt like it was on fire, although I wasn't sure if I was going to be able to take that huge dick in such a tight little hole. I think he could see the hesitation in my face when he asked if I was ready to try again and assured me that it won't hurt after he gets it in. I was so turned-on I agreed to try it again, but told him I needed to do something first and would be right back.
I returned with my laptop, set it on the table next to me bed, and put on an anal compilation porn to watch for inspiration (I think it was: http://xhamster.com/movies/66515/anal_assfuck_compilation.html
). As he lubed up his dick and relubed my hole, I kept watching different girls getting fucked hard in the ass and really wanted it to be me ... I kept telling these girls in my head "I can be a dirtier slut than you can, just watch and see how dirty I can be". I felt the pressure of his dick on my hole and tried to relax as it started to go in. As it was slowly going in it started to hurt again and I just gripped my sheets with my hands and dreamed of being fucked in the ass hard like the girl in the video as he slid in in a bit farther. The pain became so intense that I told him to stop because it hurt. He stopped but only backed his dick out slightly and told me to tell him when the pain passed. I told him to push it a bit deeper, he went very slow, and it hurt for a minute and then he told me the head was in. My ass felt like it was on fire! He pulled it completely out to let the pain subside but this girl in the video was getting fucked really hard and it made me so jealous -- I wanted to be her. I told him to stick it back in. This time it went in easier, it still hurt a little, but I could feel his dick slide deep into my ass. It was amazing. He was going really slowly in and out, but it seemed like only half of his dick would fit; every time he would push it in it would hit a point that would hurt and I would start to pull away, almost like it hit bottom and couldn't go in any further. After a minute or two my ass no longer felt like it was on fire, and the feeling of being so full was amazing, but it still hurt when he would try to stick it in deep. He suggested that we try it with me on top so I could control the speed and depth of penetration.
He pulled out, layed on his back, and grabbed my ass and pulled me so I was straddeling his face. He stick two fingers in my pussy, slowly rubbing my G-sopt, and then started teasing my asshole with his tongue. It felt so amazing and then I felt his tongue snake slowly into my asshole. I couldn't believe it, he had his tongue up my ass, like literally up my ass! His soft, wet tongue felt amazing squirming around in my hole and it made me feel like such a dirty little girl. He pulled his face from my butt, pushed me down and squirted more lube in my hole, then lubed up his dick as I moved around to get on top of him. I knelt down on top of him, my legs next to his waste, grabbed his dick and put it against my butthole, and slowly eased my way down. This time there was no pain, just a feeling of being extremely full until it got really deep and I couldn't get it in any further. I put my hands on his chest and started slowly riding him, slowing down when it would start to get too deep. As I kept riding him slowly, it began to feel utterly amazing; when it would go as deep as I could take it the pain of it "hitting bottom" turned into an odd combination of pleasure and pain. It hurt a little as it felt like his cock was hitting a wall deep in my asshole, but it felt so good at the same time -- I had never felt anything like it. As I continued to ride his cock slowly, I was watching the porn and getting so turned on watching the girl on the screen getting fucked in the ass really really hard. I started to slide my hands to my clit and started rubbing it, only to have him pull my hands away right before I was about to cum. He said "you are not allowed to cum yet, trust me, when I finally let you cum you will cum so hard baby".
As I pointed at the porn playing on my laptop I told him I wish I could fit his entire dick in my ass so I could get fucked like that girl, and mumbled that I wanted to be a dirty little girl just like her. He chuckled and said it was only about 1/2 way in, but that if I wanted to try to take it deeper he was "an expert" and that I just had to trust him. He grabbed my hands, removed them from his chest and wrapped them around his neck, pulling my head against his chest. He kissed me on the head and said "you can do it you dirty girl, just relax" as he started to rub his hands up and down my back. While one hand continued to rub my back, he pushed my ass up slightly and placed the other on the small of my back, pulling my stomach close to his and arching my back slightly. He said "relax" and then gently started pushing his cock deeper into my ass. I let out a moan as it started to slide in deeper and I couldn't believe the mix of pleasure and pain I was experiencing. He stopped pushing deeper and started moving his hips slowly in a circular motion, transforming the small amount of pain into pure pleasure. He asked if I was ready for more, I took a deep breath, and he pushed the rest of his huge dick in my ass. I moaned as it filled me up, it really hurt, like really fucking hurt .... it felt like his cock was going to poke out of my chest! I whimpered a little from the pain, and he lay still and started rubbing by back. As the pain started to subside, I turned my head to see a girl getting nailed in the ass on my laptop. It got me so horny. I started to move my hips around, and slowly started to lift myself up, once again placing my hands on his chest. As I was gyrating my hips, I started to move up and down, beginning to move his dick in an out from deep in my ass. The pain started to give way towards pleasure. It started to feel better and better as I bounced lightly on his cock. I pulled my legs up and planted my feel right beside his hips, now squatting on his hard dick. I started to move up and down, and it felt amazing. Any pain was gone, and the pleasure when I would sink my ass the entire way to his balls way amazing. I turned to look at the porn on my laptop, looked at him and said "I want you on top. I want youo to fuck my ass".
I slowly pulled my ass from his dick, and got down and ready to take it doggie style. He got on top and slid his cock deep in my ass, my hands clenching the sheets while I bit my lip. He started going slow with long strokes, in and out ... it was amazing. He started to go a bit faster and a bit harder and the mix of pleasure and pain was amazing. The faster and harder her went, the more difficult it was to bear, it was hurting! Then with one hard, very deep thrust something happened. He hit a spot that gave me the most pleasure I had ever felt in my life! He pulled out and thrust in again, and again he hit that spot! It felt so good, yet hurt, yet felt sooooooo good. I looked back at him and said "I want you to fuck me hard, I don't care how much I scream, don't stop until you cum! I'm your dirty girl". He built up the power and speed of his thrusts over time until I was getting fucked in my ass really hard! I felt like such a dirty girl. I don't know what I said, or what I did ... it was all a blur ... I just remember gripping my sheets, biting them, and basically holding on for dear life ... mouth open in pure astonishment as my ass got completely and totally fucked. I was in that state, squirming from the pain and pleasure for about 20 minutes, until he came. It was amazing and I can't wait to experience it again!