Mirrorthrone
01-03-2016, 12:25 PM
Hi all.
This is my first story ever, and it's a true one! It's the story of my first anal sex experience that happened when I was 19, about 5-6 years ago. It happened with the first girl I'd actually consider a "girlfriend", though we were only together about 6 months. First, a little about me. I'm a taller guy, around 6'1. Fairly skinny build, though I work out I'm definitely not ripped, just what I like to consider in shape. I have dark hair and hazel eyes. The part people are probably wondering about, my cock, is what I believe to be a good size, measuring just under 9 inches long. You can see a picture in my profile. I am very sex crazed, like most guys, and am constantly thinking about it and girls (hence my long membership to this website!). I lost my virginity to a girl who was a friend of mine when I was 17. She was very pretty, had great tits, a shaved tight pussy that blew my mind when I slid in for the first time, and I consider myself very lucky for having her. I have a deep obsession with the female bottom. I'm a straight up ass man, and I love everything about them. The different shapes every girl has, the way they sway when a girl walks, everything! Anal porn is my favourite to watch, and it dominates most of my sexual thoughts since I was probably 18 years old.
Now on to the story. At the time, like most 19 year olds, I was hitting night clubs really hard with my best friend pretty much every weekend. Being where I am in Canada, you can drink/smoke/gamble/anything you want when you turn 18 years old. One night at a country club downtown in October we were tearing it up like we usually did. My best friend had more money then most 19 year olds, due to him working for his filthy rich parents. So we would often get some attention from girls at the clubs by buying excessive amounts of shots and drinks and handing them out to any girls around (basically something now that I'm a little older would consider a huge douche bag thing to do). We were with a few other friends that night as well. Usually we would go out just the two of us, but being in the club scene as much as we were we knew people at basically every club every night of the week, whether they were people we went to school with or I worked with. At this time I don't remember the occasion of this night, but we were going really hard, dancing and drinking like crazy. Eventually we split up as we sometimes did on our quest to meet girls and hopefully hook up. I found myself on the dance floor exchanging eyes with this borderline petite blonde girl. Very cute face, shoulder length bright blonde hair, brown eyes, decked out in a dress. Upon closer inspection, she had smaller, probably a-cup breasts, very skinny build down to her hips which expanded quite a bit. I knew right away what was behind her... a booty that you would not normally find on a girl of this size. We moved in a little bit closer to start dancing. As the songs got more intense, so did our moves, with grinding and feeling eachother up. The dance floors packed, so it's not like you ever get noticed what you're doing. We chatted briefly with some small talk as it's obviously very loud, and I moved in with the classic move "lets go get a drink!". We moved to a bar, I bought us some fruity shot that we were into at the time, as well as a hi-ball of our choosing. We talked a bit more, exchanged names, what are you doing here, etc. Her name was Kim, and she said she was here with her older sister and a few friends whom she was separated from when we began our little dance on the floor. I said I'd help her find them, and she said her sister would be hard to miss as she was wearing a bright yellow dress.
After a few minutes of us two walking around the bar, holding hands of course, a friend of mine walked up to me and said "Hey man, Derek (my buddy) is on the dance floor with some chick in a yellow dress!". Kim and I immediately went over and saw the two of them grinding and dancing in a similar way we were. "Mission accomplished!" and we had a quick laugh and decided to get another drink. We were in the corner chatting and sipping away at our drinks, and after a while the booze really started to settle in. I had my hands on her hips and she was definitely giving me the look, and I decided to move in. We started to kiss gently, which quickly escalated into a hardcore make out session. I moved my hands up and down her, feeling her small boobs, then down to her plump round ass. This lasted a while, till eventually out of the corner of my eye I saw her sister approaching with no Derek in sight. I was quickly introduced to her stunning sister, who was taller then Kim, larger C-cup sized tits, and in very good shape. I would later find out she's a personal trainer. She said they were leaving soon, and insisted Kim go with her. I later found out that nothing happened with the sister, Ashley, and Derek. We quickly exchanged phone numbers, and she was gone. I quickly linked up again with Derek, and we were on our way back to his duplex where he lived alone, and was our central hub to party at basically.
Waking up the next morning to our usual hang over (which was nothing when you're 19... those were the days!). I had my car parked at his place as I often did, so we said our good byes and I was on my way back to my place. When I parked at home, I checked my old iPhone 3g, and had a message from Kim. "Hello" is all it said. I responded with a smug "Hello". We quickly got to chatting about last night, rapidly responding to eachothers text messages. I'd exchanged a lot of numbers with girls at bars, but would rarely pursue the next day. Kim was fun to chat with however, as we seemed to get along really well. We agreed to meet for a date, and met for coffee by her place. I picked her up, and we chatted about life. I was in my last semester of college, and she was taking a year off between graduating high school and going to college. I also wanted to note that she had been a dancer her whole life. I graduated young, which was why I was in my final semester of my two year program before I was 20. When I dropped her off back at her house, we had a quick little make out session, and called it a night. I watched her walk back to her place to make sure she got inside, the whole time staring at her beautiful bottom she no doubt earned from the years of dancing.
The following week I moved into my brothers house for 2 weeks so I could house sit for him and his wife. He had a great new place that I knew was going to be a blast to live at. After texting a bit with Kim, I convinced her to come over late one night and hang out. It was a school night, but I was getting the vibe that tonight could be the night I hook up with her! She finally agreed to come over after her dance practice, and I sent her the address. I let Derek know it was finally going down. I had an empty house, and I knew I could get this done! He asked if I had a condom... and fuck! I didn't! It wasn't super important to me to get one (being young and stupid) but he had a good point that a lot of girls may use that as an excuse to not have sex. We quickly hatched a scheme where he was going to pop by, and if Kim had beaten him to my place, then we would claim that all liquor stores around here were closed so Derek was picking up a 40 of vodka I had as he was on his way to a party. Then, during the exchange of vodka, he would slip me a condom.
Kim arrived, we caught up on our days events. I mentioned that Derek was coming by quick and the reason why, who she knew so she wasn't really concerned or anything like that. We were just watching TV when he showed up. We quickly made the exchange and Kim and had no idea as she wasn't really watching. Derek was on his way, and I received the ol "Good luck buddy" text. We were watching TV spooning on the couch. It quickly escalated into another make out session. We finally had the place/time/privacy to get to the next level. I pulled up her top and began fondling her tits, while she unzipped my jeans and pulled my stiff cock out. She began gently stroking it, then I said "let's go to the bedroom". She said she wasn't sure, as our relationship was still very new. I tried hard to dodge her objections, and eventually she started to come around. Then it came... "well... do you have a condom?" "Absolutely!" I snapped back almost instantly. We were then on our way to the bedroom. A quick glance at the clock and I saw it was 2:00 am. I had class at 7:15... "Fuck!" I said in my head. But I knew it would be worth it. We quickly undressed each other. She had completely shaved smooth pussy, which I loved. I gently fingered her for a few minutes while making out. I then moved down to suck on her small tits, and got them nice and hard. Then I knew she was ready. She put the condom on, and I began to move into position. I pushed in slowly, as being a bit bigger in that department I didn't want to hurt her (though its not like she didn't have the hips to accommodate). She was very tight, as expected, and it was great. We got into a good rhythm of fucking. We moved into a spooning position, and I got a great top view of her ass. It was as perfect naked as I had ever imagined. I gently spread her cheeks open while my cock pumped in and out of her warm pussy, so I could see it in all its glory. We graduated to full on doggy style much to my excitement, as she looked amazing from behind. I was pounding away, and glanced over at the clock. 3:00 AM... fuck fuck fuck. I knew I had to wrap this up soon. "Baby, I'm getting close. Can we take the condom off and have you finish me?" "Fuck yes!" she quickly turned around, pulled it off and devoured my cock in her mouth for the first time. Bobbing up and down for a few minutes, I knew it was coming, and she pulled it out of her mouth and began pumping furiously. Then it happened, and I erupted a huge load all over her tits and stomach. Mid way through she proclaimed "Wow!" as my load was definitely huge. But hey, fucking for an hour and 19 years old? Of course it was huge!
We cleaned up and she left. I went right to bed. It felt like I hit the pillow and my alarm went off at 5:30 AM. "God dammit..." I thought, and set off for school. We sent a few casual texts back and forth throughout the day, nothing awkward, just "Last night was fun" "Can't wait to do that again" etc etc. I had some drinks with Derek the day after and we exchanged high fives. He mentioned the weekend prior to these events, he hooked up with this girl that we went to high school with (who I actually had sex with about a year prior to this story). We had a laugh about it, and then he mentioned something that I couldn't get out of my head. He fucked her in the ass. I was dumb-founded, and extremely jealous he got to experience that! After that, I knew I had to fuck Kim in the ass, no matter what it took. I had never had obviously never had anal before, but had watched it many times in porn. I never thought, however, that normal girls would be willing to do that sort of thing, and that it only really happened in porn!
Kim and I continued to see eachother over the next few months. It was a standard routine, we would either go to a movie or for coffee, back to her place, fuck, then I would be on my way. Our sex was improving with each session. She didn't care about condoms anymore as she was on the pill, though I never did end up cumming inside of her as she felt it was still to risky. Fine with me! She did however let me cum usually where I wanted, either on her ass, her tits, and eventually she let me cum in her mouth. I'll never forget that, as it was valentines day, and I had told her about how good it feels to have your cum sucked out of your cock (I had only experienced that one time before this). She quickly complied, and swallowed a huge load after a night of sex. Then she swatted me on the arm "OMG! that was like a liter! what the hell!" she said. "Sorry babe! it just felt so good!" I replied. We had a good laugh then off to sleep.
I eventually worked up the courage to mention anal sex to her. She wasn't as repulsed as I thought she may be. Turns out, she had tried it before with some guy, but they could never get it in. She said she was more worried because my dick was thicker and longer then the last guy she tried it with. I pleaded with her that we would take it slow, use lots of lube, and if she wanted me to stop we would. She said she would think about it. In my head all I could think was "so she's saying there's chance!".
The next couple times we had sex I would work my way down to her sexy little butthole. I would gently probe it with my finger, rim it around and see how much of it I could get into her before she would stop me. I would use some of the residual wetness from her pussy as lube, and gently work her asshole as if to mentally and physically prepare her. I eventually got my whole thumb in her ass during a doggy style session, which was great, as she was bucking hard and cumming her brains out on my dick. I quickly pulled out and exploded over her ass, with her small hole slightly agape from my thumb. I knew the time was coming soon she would agree.
Then one day in class I got a text. "I got lube". We had never used lube before, as it quickly became our ritual for her to suck my cock before sex, and I would finger her to get her juices flowing. I knew why she got the lube. The end of class couldn't come fast enough. I bolted home, showered up and got ready, then headed to Kims place right after dinner. I picked her up, and she insisted we see a movie. I don't even remember what movie it was, as all I could think about was penetrating her deepest, darkest hole with my steel hard cock. We started making out in the theatre, and I moved my hand down into her jeans. I slipped my hand inside and gently started to rub her clit. Her pussy was already soaked, so it's obvious the anticipation of tonights events was on her mind as much as it was mine. We left the movie the second the credits began to roll, and we were off back to her place. Her parents were home, and Kim said she'd prefer it if they weren't there for this. I said "Well obviously I don't want your parents in the next room while we have anal sex... but what do we do?". She thought for a second then had an idea. "hey mom, we're thinking about going to the casino, want to come with?" "Sure! when?" her mom responded. "Right now! Why don't you guys go ahead and we'll meet you there!" "Sounds great!" and they were gone. I couldn't believe it! They fell for that?!! Unreal! I told her this probably wasn't going to be over quickly, and she said her parents loved the casino and won't even care if we didn't show up. "Alright then... different kind of people" I thought to myself.
She showed me the lube. It was some "yours and mine" stuff that I had never seen before. Whatever, I didn't really care. We started undressing and kissing, and started with our usual rhythm. I began to gently finger her asshole while fucking her from behind again, and she reached over and grabbed the lube. We moved into the spooning position. She slipped my cock out of her pussy, and lubed me up. I took the other bottle, and put some on my finger. I gently rimmed it around her asshole and began massaging it inside. I was so bloody excited that I felt almost drunk with lust. Her ass was perfect. Her ASSHOLE was perfect! I had to have it. I took my lubed up cock and position it at the entrance. "SLOW!" she snapped. "Of course of course... relax or this won't work at all!". And so I began to push in. The hole was very tight at first, almost as if I hadn't been fingering it at all. I pulled back my foreskin to make it a bit easier. I had about half the head in, and Kim was taking it great. She wasn't doing anything except laying there, with her one hand pulling open her butt cheek to allow me to enter. Eventually, a little "pop" happened, and her hole sucked in the whole head of my cock. "Incredible!" I thought, as her asshole was now co-operating to take my cock inside. I slowly pushed inside until I had about 2/3s of my cock in. I started to feel a little resistance, so I didn't want to push my luck and stopped there. I gently withdrew up to the head, then thrust back in that same depth. It was amazing. I had never felt something so warm, smooth and tight around my cock. Not to mention the thought of being inside this perfect ass. I glanced over and noticed she was playing with her pussy while I fucked her rear entrance. She was moaning slightly, and I moved in and started kissing her neck, and clutched her boobs with my free hand. "Baby your ass is the most amazing thing I've ever felt in my life". She had no response just moaning a little louder. "Where's my cock, baby?" I whispered. She was totally infatuated with what was going on, and I could feel her butt gripping me even tighter. "My ass". I figured she was close to cumming as I could see her aggressively rubbing her clit. Then it happened. She moaned deeply, and I could feel her ass squeeze and suck me a little deeper inside. Her ass was cumming on my cock. I couldn't believe it. It was all I could do to keep from exploding myself! We lay still for a minute after, and she kept rubbing her pussy. She then whispered "I think someones getting a little jealous". I had no idea what she meant. She reached behind and slipped my cock out of her bum, and moved it to her pussy. I just let it happen, maybe her bum was sore and she didn't want to admit it. I fucked her pussy for about 5 minutes, then pulled out and came on her lower stomach and pussy. We passed out for about a half hour then I woke up, we said good night and I went home.
I slept like a baby. She texted me the next day expressing a little remorse we had vaginal AFTER anal. I agreed, but she never got an infection or anything, so it worked out. I had lunch with Derek the next day and a few other buddies. I texted Derek while we were at the table so it was just between us two. I wrote "I fucked Kim in the ass last night". And he spat his drink out while reading it and laughed. We high fived in private after lunch.
Kim and I stopped seeing eachother a few weeks later. I wouldn't really consider it a break up since we were never really official. She started to get really weird and clingy. It became evident that there wasn't a future there. We had a clean break and never saw eachother again. I was quickly deleted off facebook and that was that. I had since graduated college and began working full time in a new position at my same place of work, which had ample amounts of women working there in their younger 20s who loved to party. I knew this was the beginning of my next chapter, and would eventually lead to what will hopefully become Part 2 of this story.
Still I never forgot Kim as the first girl I ever had anal with.
This is my first story ever, and it's a true one! It's the story of my first anal sex experience that happened when I was 19, about 5-6 years ago. It happened with the first girl I'd actually consider a "girlfriend", though we were only together about 6 months. First, a little about me. I'm a taller guy, around 6'1. Fairly skinny build, though I work out I'm definitely not ripped, just what I like to consider in shape. I have dark hair and hazel eyes. The part people are probably wondering about, my cock, is what I believe to be a good size, measuring just under 9 inches long. You can see a picture in my profile. I am very sex crazed, like most guys, and am constantly thinking about it and girls (hence my long membership to this website!). I lost my virginity to a girl who was a friend of mine when I was 17. She was very pretty, had great tits, a shaved tight pussy that blew my mind when I slid in for the first time, and I consider myself very lucky for having her. I have a deep obsession with the female bottom. I'm a straight up ass man, and I love everything about them. The different shapes every girl has, the way they sway when a girl walks, everything! Anal porn is my favourite to watch, and it dominates most of my sexual thoughts since I was probably 18 years old.
Now on to the story. At the time, like most 19 year olds, I was hitting night clubs really hard with my best friend pretty much every weekend. Being where I am in Canada, you can drink/smoke/gamble/anything you want when you turn 18 years old. One night at a country club downtown in October we were tearing it up like we usually did. My best friend had more money then most 19 year olds, due to him working for his filthy rich parents. So we would often get some attention from girls at the clubs by buying excessive amounts of shots and drinks and handing them out to any girls around (basically something now that I'm a little older would consider a huge douche bag thing to do). We were with a few other friends that night as well. Usually we would go out just the two of us, but being in the club scene as much as we were we knew people at basically every club every night of the week, whether they were people we went to school with or I worked with. At this time I don't remember the occasion of this night, but we were going really hard, dancing and drinking like crazy. Eventually we split up as we sometimes did on our quest to meet girls and hopefully hook up. I found myself on the dance floor exchanging eyes with this borderline petite blonde girl. Very cute face, shoulder length bright blonde hair, brown eyes, decked out in a dress. Upon closer inspection, she had smaller, probably a-cup breasts, very skinny build down to her hips which expanded quite a bit. I knew right away what was behind her... a booty that you would not normally find on a girl of this size. We moved in a little bit closer to start dancing. As the songs got more intense, so did our moves, with grinding and feeling eachother up. The dance floors packed, so it's not like you ever get noticed what you're doing. We chatted briefly with some small talk as it's obviously very loud, and I moved in with the classic move "lets go get a drink!". We moved to a bar, I bought us some fruity shot that we were into at the time, as well as a hi-ball of our choosing. We talked a bit more, exchanged names, what are you doing here, etc. Her name was Kim, and she said she was here with her older sister and a few friends whom she was separated from when we began our little dance on the floor. I said I'd help her find them, and she said her sister would be hard to miss as she was wearing a bright yellow dress.
After a few minutes of us two walking around the bar, holding hands of course, a friend of mine walked up to me and said "Hey man, Derek (my buddy) is on the dance floor with some chick in a yellow dress!". Kim and I immediately went over and saw the two of them grinding and dancing in a similar way we were. "Mission accomplished!" and we had a quick laugh and decided to get another drink. We were in the corner chatting and sipping away at our drinks, and after a while the booze really started to settle in. I had my hands on her hips and she was definitely giving me the look, and I decided to move in. We started to kiss gently, which quickly escalated into a hardcore make out session. I moved my hands up and down her, feeling her small boobs, then down to her plump round ass. This lasted a while, till eventually out of the corner of my eye I saw her sister approaching with no Derek in sight. I was quickly introduced to her stunning sister, who was taller then Kim, larger C-cup sized tits, and in very good shape. I would later find out she's a personal trainer. She said they were leaving soon, and insisted Kim go with her. I later found out that nothing happened with the sister, Ashley, and Derek. We quickly exchanged phone numbers, and she was gone. I quickly linked up again with Derek, and we were on our way back to his duplex where he lived alone, and was our central hub to party at basically.
Waking up the next morning to our usual hang over (which was nothing when you're 19... those were the days!). I had my car parked at his place as I often did, so we said our good byes and I was on my way back to my place. When I parked at home, I checked my old iPhone 3g, and had a message from Kim. "Hello" is all it said. I responded with a smug "Hello". We quickly got to chatting about last night, rapidly responding to eachothers text messages. I'd exchanged a lot of numbers with girls at bars, but would rarely pursue the next day. Kim was fun to chat with however, as we seemed to get along really well. We agreed to meet for a date, and met for coffee by her place. I picked her up, and we chatted about life. I was in my last semester of college, and she was taking a year off between graduating high school and going to college. I also wanted to note that she had been a dancer her whole life. I graduated young, which was why I was in my final semester of my two year program before I was 20. When I dropped her off back at her house, we had a quick little make out session, and called it a night. I watched her walk back to her place to make sure she got inside, the whole time staring at her beautiful bottom she no doubt earned from the years of dancing.
The following week I moved into my brothers house for 2 weeks so I could house sit for him and his wife. He had a great new place that I knew was going to be a blast to live at. After texting a bit with Kim, I convinced her to come over late one night and hang out. It was a school night, but I was getting the vibe that tonight could be the night I hook up with her! She finally agreed to come over after her dance practice, and I sent her the address. I let Derek know it was finally going down. I had an empty house, and I knew I could get this done! He asked if I had a condom... and fuck! I didn't! It wasn't super important to me to get one (being young and stupid) but he had a good point that a lot of girls may use that as an excuse to not have sex. We quickly hatched a scheme where he was going to pop by, and if Kim had beaten him to my place, then we would claim that all liquor stores around here were closed so Derek was picking up a 40 of vodka I had as he was on his way to a party. Then, during the exchange of vodka, he would slip me a condom.
Kim arrived, we caught up on our days events. I mentioned that Derek was coming by quick and the reason why, who she knew so she wasn't really concerned or anything like that. We were just watching TV when he showed up. We quickly made the exchange and Kim and had no idea as she wasn't really watching. Derek was on his way, and I received the ol "Good luck buddy" text. We were watching TV spooning on the couch. It quickly escalated into another make out session. We finally had the place/time/privacy to get to the next level. I pulled up her top and began fondling her tits, while she unzipped my jeans and pulled my stiff cock out. She began gently stroking it, then I said "let's go to the bedroom". She said she wasn't sure, as our relationship was still very new. I tried hard to dodge her objections, and eventually she started to come around. Then it came... "well... do you have a condom?" "Absolutely!" I snapped back almost instantly. We were then on our way to the bedroom. A quick glance at the clock and I saw it was 2:00 am. I had class at 7:15... "Fuck!" I said in my head. But I knew it would be worth it. We quickly undressed each other. She had completely shaved smooth pussy, which I loved. I gently fingered her for a few minutes while making out. I then moved down to suck on her small tits, and got them nice and hard. Then I knew she was ready. She put the condom on, and I began to move into position. I pushed in slowly, as being a bit bigger in that department I didn't want to hurt her (though its not like she didn't have the hips to accommodate). She was very tight, as expected, and it was great. We got into a good rhythm of fucking. We moved into a spooning position, and I got a great top view of her ass. It was as perfect naked as I had ever imagined. I gently spread her cheeks open while my cock pumped in and out of her warm pussy, so I could see it in all its glory. We graduated to full on doggy style much to my excitement, as she looked amazing from behind. I was pounding away, and glanced over at the clock. 3:00 AM... fuck fuck fuck. I knew I had to wrap this up soon. "Baby, I'm getting close. Can we take the condom off and have you finish me?" "Fuck yes!" she quickly turned around, pulled it off and devoured my cock in her mouth for the first time. Bobbing up and down for a few minutes, I knew it was coming, and she pulled it out of her mouth and began pumping furiously. Then it happened, and I erupted a huge load all over her tits and stomach. Mid way through she proclaimed "Wow!" as my load was definitely huge. But hey, fucking for an hour and 19 years old? Of course it was huge!
We cleaned up and she left. I went right to bed. It felt like I hit the pillow and my alarm went off at 5:30 AM. "God dammit..." I thought, and set off for school. We sent a few casual texts back and forth throughout the day, nothing awkward, just "Last night was fun" "Can't wait to do that again" etc etc. I had some drinks with Derek the day after and we exchanged high fives. He mentioned the weekend prior to these events, he hooked up with this girl that we went to high school with (who I actually had sex with about a year prior to this story). We had a laugh about it, and then he mentioned something that I couldn't get out of my head. He fucked her in the ass. I was dumb-founded, and extremely jealous he got to experience that! After that, I knew I had to fuck Kim in the ass, no matter what it took. I had never had obviously never had anal before, but had watched it many times in porn. I never thought, however, that normal girls would be willing to do that sort of thing, and that it only really happened in porn!
Kim and I continued to see eachother over the next few months. It was a standard routine, we would either go to a movie or for coffee, back to her place, fuck, then I would be on my way. Our sex was improving with each session. She didn't care about condoms anymore as she was on the pill, though I never did end up cumming inside of her as she felt it was still to risky. Fine with me! She did however let me cum usually where I wanted, either on her ass, her tits, and eventually she let me cum in her mouth. I'll never forget that, as it was valentines day, and I had told her about how good it feels to have your cum sucked out of your cock (I had only experienced that one time before this). She quickly complied, and swallowed a huge load after a night of sex. Then she swatted me on the arm "OMG! that was like a liter! what the hell!" she said. "Sorry babe! it just felt so good!" I replied. We had a good laugh then off to sleep.
I eventually worked up the courage to mention anal sex to her. She wasn't as repulsed as I thought she may be. Turns out, she had tried it before with some guy, but they could never get it in. She said she was more worried because my dick was thicker and longer then the last guy she tried it with. I pleaded with her that we would take it slow, use lots of lube, and if she wanted me to stop we would. She said she would think about it. In my head all I could think was "so she's saying there's chance!".
The next couple times we had sex I would work my way down to her sexy little butthole. I would gently probe it with my finger, rim it around and see how much of it I could get into her before she would stop me. I would use some of the residual wetness from her pussy as lube, and gently work her asshole as if to mentally and physically prepare her. I eventually got my whole thumb in her ass during a doggy style session, which was great, as she was bucking hard and cumming her brains out on my dick. I quickly pulled out and exploded over her ass, with her small hole slightly agape from my thumb. I knew the time was coming soon she would agree.
Then one day in class I got a text. "I got lube". We had never used lube before, as it quickly became our ritual for her to suck my cock before sex, and I would finger her to get her juices flowing. I knew why she got the lube. The end of class couldn't come fast enough. I bolted home, showered up and got ready, then headed to Kims place right after dinner. I picked her up, and she insisted we see a movie. I don't even remember what movie it was, as all I could think about was penetrating her deepest, darkest hole with my steel hard cock. We started making out in the theatre, and I moved my hand down into her jeans. I slipped my hand inside and gently started to rub her clit. Her pussy was already soaked, so it's obvious the anticipation of tonights events was on her mind as much as it was mine. We left the movie the second the credits began to roll, and we were off back to her place. Her parents were home, and Kim said she'd prefer it if they weren't there for this. I said "Well obviously I don't want your parents in the next room while we have anal sex... but what do we do?". She thought for a second then had an idea. "hey mom, we're thinking about going to the casino, want to come with?" "Sure! when?" her mom responded. "Right now! Why don't you guys go ahead and we'll meet you there!" "Sounds great!" and they were gone. I couldn't believe it! They fell for that?!! Unreal! I told her this probably wasn't going to be over quickly, and she said her parents loved the casino and won't even care if we didn't show up. "Alright then... different kind of people" I thought to myself.
She showed me the lube. It was some "yours and mine" stuff that I had never seen before. Whatever, I didn't really care. We started undressing and kissing, and started with our usual rhythm. I began to gently finger her asshole while fucking her from behind again, and she reached over and grabbed the lube. We moved into the spooning position. She slipped my cock out of her pussy, and lubed me up. I took the other bottle, and put some on my finger. I gently rimmed it around her asshole and began massaging it inside. I was so bloody excited that I felt almost drunk with lust. Her ass was perfect. Her ASSHOLE was perfect! I had to have it. I took my lubed up cock and position it at the entrance. "SLOW!" she snapped. "Of course of course... relax or this won't work at all!". And so I began to push in. The hole was very tight at first, almost as if I hadn't been fingering it at all. I pulled back my foreskin to make it a bit easier. I had about half the head in, and Kim was taking it great. She wasn't doing anything except laying there, with her one hand pulling open her butt cheek to allow me to enter. Eventually, a little "pop" happened, and her hole sucked in the whole head of my cock. "Incredible!" I thought, as her asshole was now co-operating to take my cock inside. I slowly pushed inside until I had about 2/3s of my cock in. I started to feel a little resistance, so I didn't want to push my luck and stopped there. I gently withdrew up to the head, then thrust back in that same depth. It was amazing. I had never felt something so warm, smooth and tight around my cock. Not to mention the thought of being inside this perfect ass. I glanced over and noticed she was playing with her pussy while I fucked her rear entrance. She was moaning slightly, and I moved in and started kissing her neck, and clutched her boobs with my free hand. "Baby your ass is the most amazing thing I've ever felt in my life". She had no response just moaning a little louder. "Where's my cock, baby?" I whispered. She was totally infatuated with what was going on, and I could feel her butt gripping me even tighter. "My ass". I figured she was close to cumming as I could see her aggressively rubbing her clit. Then it happened. She moaned deeply, and I could feel her ass squeeze and suck me a little deeper inside. Her ass was cumming on my cock. I couldn't believe it. It was all I could do to keep from exploding myself! We lay still for a minute after, and she kept rubbing her pussy. She then whispered "I think someones getting a little jealous". I had no idea what she meant. She reached behind and slipped my cock out of her bum, and moved it to her pussy. I just let it happen, maybe her bum was sore and she didn't want to admit it. I fucked her pussy for about 5 minutes, then pulled out and came on her lower stomach and pussy. We passed out for about a half hour then I woke up, we said good night and I went home.
I slept like a baby. She texted me the next day expressing a little remorse we had vaginal AFTER anal. I agreed, but she never got an infection or anything, so it worked out. I had lunch with Derek the next day and a few other buddies. I texted Derek while we were at the table so it was just between us two. I wrote "I fucked Kim in the ass last night". And he spat his drink out while reading it and laughed. We high fived in private after lunch.
Kim and I stopped seeing eachother a few weeks later. I wouldn't really consider it a break up since we were never really official. She started to get really weird and clingy. It became evident that there wasn't a future there. We had a clean break and never saw eachother again. I was quickly deleted off facebook and that was that. I had since graduated college and began working full time in a new position at my same place of work, which had ample amounts of women working there in their younger 20s who loved to party. I knew this was the beginning of my next chapter, and would eventually lead to what will hopefully become Part 2 of this story.
Still I never forgot Kim as the first girl I ever had anal with.