Training of an Indian Finance Analyst
- 4 years ago
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Training Her For Double Anal free porn video
We were training her ass for double anal sex, or at least that was the plan. We had already had success taking her virginity; opening up her pussy to a dildo, then to my dick, then to double vaginal, and even some anal. We had talked about fisting, along with other things that were pure fantasy. Like, what monster would you fuck? (her answer: a werewolf)... But after our success with letting two men in her pussy, she became intrigued at the idea of doing the same with her ass. She agreed to let me try and "expand her butt" one afternoon when she was over, Tom couldn't make it. I figured we could use her dildo in his absence.
The last few times we had met, we had just begun to try anal. Surprisingly, Lauren took to it almost immediately. Her pussy took several sessions to really relax and learn to open up… but it seemed like her anus was open and ready from the first time we tried. I had made it a point to go softly and slowly with her asshole at first, so as to build her enjoyment and love for anal. As with all of Lauren’s training, the goal was to make her enjoy all the ways I would use her little body.
Much to my pleasure, she was an anal queen in the making after our first "ass session". The first time Tom was able to join us after that, we had started into our usual double-occupation of her pussy, and she looked back at me as I worked our stacked dicks into her from behind, and asked "aren't you guys going to fuck my ass and pussy at the same time? I want to show Tom how I can use my ass now. Or, how HE can use my ass". She smiled and let out a little giggle. That day, we would fuck both her holes simultaneously for over an hour. She loved the feeling, and when I asked her if she preferred that to having both in the same hole, she answered "I don't know. They're both different, but amazing, so it's hard to say. I should probably do both more before I really pick a favorite. I like when you and Tom are both inside me, in my pussy, because it feels closer… like you could both make me pregnant at once (giggles). But I liked it today with one of you in my ass, too… it felt more nasty like that. And I also liked the feeling on the skin that separates my ass from my pussy… I could feel both of you rubbing on either side. It's like your dicks were trying to touch inside me, and the little piece of skin was cock-blocking them (giggles).
It was her comments on that day, which got me thinking about trying double anal. It seemed like a natural progression, anyway… since Tom and I loved sharing her pussy and mouth, and Lauren apparently loved accommodating our dicks in new and interesting ways.
Today was just me and her. We were lying the bed facing each other, on our sides. My hands were reaching underneath her, each hand palming one of her ass cheecks. She was so petite, that one of my hands almost completely covered her ass cheeck. As such, I could grab her ass with both hands, and spread it completely apart, gaping her hairy pussy and exposing every inch of her ass and cunt region. Her ass was small enough that, with both hands spreading her ass like so, and without moving my palms, I could get both index fingers into her asshole, and spread that apart as well. This made it easy for me when I was the bottom man during a DP, as I could easily grip her ass open and give the top man a good view and easy access to her holes.
Anyway, there I was, with my hands holding her ass wide apart. I had already worked her anus open with my fingers and her dildo. I also had her coat my dick in lube. I wanted to have some fun, so I began lining up the head of my penis against her semi-open butthole. I was not using my hands. After a minute or so, I felt the round indent of her sphincter and let my dick rest at its entrance. My body pumped more blood to my dick, making it move and jerk. I began to push my cock into her ass, while stretching her ass apart further with my hands. I could hear Lauren moan, then wimper. Her little butthole barely resisted, and soon I was halfway, then fully inside of Lauren's asshole. As I sunk into her completely, I could feel her wet pussy against my pelvis and pubic hair. As I started to pump her little body, I felt her insides grip my dick and almost turn themselves inside out on every back-stroke. Eventually, the lube worked into her ass, and her little hole began to feel slick and loose.
This is where we make the magic happen, I thought to myself. I said to Lauren "remember what we talked about, earlier? About practicing for me and Tom inside your ass together?". She whispered "yes" in my ear. I reached over and grabbed her dildo at the edge of the bed. Still in the same position, but my dick had fallen out of her ass by this point. I reached under Lauren, and put the dildo in her ass. No problem so far. I worked it in a bit more than halfway… then I felt around the rim of her anus. I was working blind from this position, so I had to find the seal between her butthole and the dildo by hand. Once I found that, I aimed my dick towards that soft edge, and began to push. As I did, I could hear Lauren softly whine in pain. More importantly, my dick wasn't gaining entry. As I would push, her entire ass area would deflect my lubed up dick. Between the slickness, and the tightness of her ass, my dick just wasn't penetrating the edge of her already filled asshole. I pulled back and tried again. This time, I attempted to use the dildo as a guide, and slide my dick up alongside it, and into her. Still no entry. I tried again, but this time was able to get the tip of my finger inside her ass, and used it to stretch open a small space for me next to the dildo. As I was able to get the tip of my dick in, I still found no purchase, as my erection was softening and my dick was spit out of her tightly filled asshole.
I should mention, that this was actually a vibrator with a silicone "jelly" skin, which makes it a little harder and less flexible than a proper dildo. In fact, in a double penetration situation, ANY dildo is going to be less pliable, squeezable, and forgiving than a real dick. A real dick is actually very flexible, even when totally erect. This is very necessary when putting two of them in the same hole, as real dicks tend to "mash together" in a way that's comfortable for the vagina they're in. Not so much with hard dicks made from plastic and rubber… This is a bit of knowledge that would serve me for years to come.
So there I was, with a deflating dick, shoving a dildo up the ass of a beautiful little Asian girl wrapped around my waist. Her arms were still around my neck, and she was breathing heavy in my ear. I had to think fast if I was going to accomplish this double anal.
I pulled the dildo out of her ass, then hooked one finger in her ass to pull her sphincter open. While doing that, I used the other hand to squeeze the base of my cock, maximizing what erection I had left. I guided my now hard dick into her open shithole. I began pumping to feel the blood rush back into my erection, then buried my self in her ass balls deep. Without skipping a beat, I picked up the dildo off of the bed, and began working its hard tip into the space between my dick and her ass sphincter. As I pressed in steadily with the dildo, her tight little shit hole gave way. My dick still buried to the hilt, her ass began to expand further, and further until it was finally accepting the dildo as well; her asshole had no choice. At this point, I felt Lauren physically protest. One of her hands flew down from around my neck, and back under her butt. She was trying to stop my hand that was holding the dildo. As her as opened, she desperately flicked and slapped and my hand, trying to stop it from pushing the hard blue silicone dick further into her asshole. It was no use- I didn't stop. We had previously discussed a safe word, and she didn't use it, so I had to assume that she wanted me to continue despite the pain.
The dildo was mostly in her ass now, right along side my dick. While by dick was still buried all the way, the dildo had yet to pass it's thickest point. Lauren had stopped trying to slap my hand away, but her ass itself was still resisting quite a bit. Her breath had become short and excited by this point. She was panting into my ear, with her entire body still pressed against mine. I began to slowly pump my dick out, then in, making half strokes while still holding the dildo in her ass. Right as I pulled out an inch, I pressed the dildo in, past it's thickest point. At this point, I could feel her asshole "break". It was extremely tight up until that point, but once the thick part of the dildo and my dick passed that threshold, her anal ring seemed to instantly relax. And it relaxed considerably… there was now room to fuck properly. Lauren gasped. Her breathing increased in speed, and her hand swung down below her again in a vain attempt to stop my pumping. "hey there, breathe deep. Relax your butt. You'll be okay" I whispered to her. She seemed to acknowledge my advice, and her breathing relaxed. At that point, I believe her soul broke just as her sphincter did a second earlier. First, her entire body went limp. Then, she raised her head, with both arms back around my neck, and looked up at me. While looking directly in my eyes, she said "fuck my ass… don't hold back. Show me how you and Tom are going to fuck it together.". Upon hearing that, I just let go. I started fucking a lot harer,moving both my dick and the dildo in and out, and an alternate fucking motion. I started to lose rhythm, and soon was shoving my dick and the dildo in and out simultaneously, as if they were one giant cock. “You like that? You like your ass being torn up by two dicks?” I grunted at her. Lauren didn’t respond. Her body had gone limp, and her breathing had settled to a medium pace. “Just use my torn up ass. Use it for your pleasure. Cum whenever you feel like it” she said quietly.
I fucked her hard for about ten minutes, and worked the dldo against my dick the whole time. Her ass stayed tight (or reasonably so) most of the time, and only began to really get loose around eight minutes or so into it. At that point, only the extra friction from the dildo made it possible to cum. I pulled out after I had finished and told Lauren to turn around and lay flat on her stomach. She did, and I was able to spread her ass checks and watch her gaping, distended asshole leak my cum. It slowly closed, and I could see a little blood trickle out along with my semen.
Later that evening, after Lauren’s mother came and retrieved her from my house, I talked to her on the phone. “You know, my ass was bleeding when I got home.” she said. I told her that was normal for her first time taking two dicks in her ass, and that it would be easier next time, and it would be even easier with me and Tom instead of a dildo. She seemed happy to hear that. “Are you proud of me?” she asked. “I am. I definitely am”. I replied.
The last few times we had met, we had just begun to try anal. Surprisingly, Lauren took to it almost immediately. Her pussy took several sessions to really relax and learn to open up… but it seemed like her anus was open and ready from the first time we tried. I had made it a point to go softly and slowly with her asshole at first, so as to build her enjoyment and love for anal. As with all of Lauren’s training, the goal was to make her enjoy all the ways I would use her little body.
Much to my pleasure, she was an anal queen in the making after our first "ass session". The first time Tom was able to join us after that, we had started into our usual double-occupation of her pussy, and she looked back at me as I worked our stacked dicks into her from behind, and asked "aren't you guys going to fuck my ass and pussy at the same time? I want to show Tom how I can use my ass now. Or, how HE can use my ass". She smiled and let out a little giggle. That day, we would fuck both her holes simultaneously for over an hour. She loved the feeling, and when I asked her if she preferred that to having both in the same hole, she answered "I don't know. They're both different, but amazing, so it's hard to say. I should probably do both more before I really pick a favorite. I like when you and Tom are both inside me, in my pussy, because it feels closer… like you could both make me pregnant at once (giggles). But I liked it today with one of you in my ass, too… it felt more nasty like that. And I also liked the feeling on the skin that separates my ass from my pussy… I could feel both of you rubbing on either side. It's like your dicks were trying to touch inside me, and the little piece of skin was cock-blocking them (giggles).
It was her comments on that day, which got me thinking about trying double anal. It seemed like a natural progression, anyway… since Tom and I loved sharing her pussy and mouth, and Lauren apparently loved accommodating our dicks in new and interesting ways.
Today was just me and her. We were lying the bed facing each other, on our sides. My hands were reaching underneath her, each hand palming one of her ass cheecks. She was so petite, that one of my hands almost completely covered her ass cheeck. As such, I could grab her ass with both hands, and spread it completely apart, gaping her hairy pussy and exposing every inch of her ass and cunt region. Her ass was small enough that, with both hands spreading her ass like so, and without moving my palms, I could get both index fingers into her asshole, and spread that apart as well. This made it easy for me when I was the bottom man during a DP, as I could easily grip her ass open and give the top man a good view and easy access to her holes.
Anyway, there I was, with my hands holding her ass wide apart. I had already worked her anus open with my fingers and her dildo. I also had her coat my dick in lube. I wanted to have some fun, so I began lining up the head of my penis against her semi-open butthole. I was not using my hands. After a minute or so, I felt the round indent of her sphincter and let my dick rest at its entrance. My body pumped more blood to my dick, making it move and jerk. I began to push my cock into her ass, while stretching her ass apart further with my hands. I could hear Lauren moan, then wimper. Her little butthole barely resisted, and soon I was halfway, then fully inside of Lauren's asshole. As I sunk into her completely, I could feel her wet pussy against my pelvis and pubic hair. As I started to pump her little body, I felt her insides grip my dick and almost turn themselves inside out on every back-stroke. Eventually, the lube worked into her ass, and her little hole began to feel slick and loose.
This is where we make the magic happen, I thought to myself. I said to Lauren "remember what we talked about, earlier? About practicing for me and Tom inside your ass together?". She whispered "yes" in my ear. I reached over and grabbed her dildo at the edge of the bed. Still in the same position, but my dick had fallen out of her ass by this point. I reached under Lauren, and put the dildo in her ass. No problem so far. I worked it in a bit more than halfway… then I felt around the rim of her anus. I was working blind from this position, so I had to find the seal between her butthole and the dildo by hand. Once I found that, I aimed my dick towards that soft edge, and began to push. As I did, I could hear Lauren softly whine in pain. More importantly, my dick wasn't gaining entry. As I would push, her entire ass area would deflect my lubed up dick. Between the slickness, and the tightness of her ass, my dick just wasn't penetrating the edge of her already filled asshole. I pulled back and tried again. This time, I attempted to use the dildo as a guide, and slide my dick up alongside it, and into her. Still no entry. I tried again, but this time was able to get the tip of my finger inside her ass, and used it to stretch open a small space for me next to the dildo. As I was able to get the tip of my dick in, I still found no purchase, as my erection was softening and my dick was spit out of her tightly filled asshole.
I should mention, that this was actually a vibrator with a silicone "jelly" skin, which makes it a little harder and less flexible than a proper dildo. In fact, in a double penetration situation, ANY dildo is going to be less pliable, squeezable, and forgiving than a real dick. A real dick is actually very flexible, even when totally erect. This is very necessary when putting two of them in the same hole, as real dicks tend to "mash together" in a way that's comfortable for the vagina they're in. Not so much with hard dicks made from plastic and rubber… This is a bit of knowledge that would serve me for years to come.
So there I was, with a deflating dick, shoving a dildo up the ass of a beautiful little Asian girl wrapped around my waist. Her arms were still around my neck, and she was breathing heavy in my ear. I had to think fast if I was going to accomplish this double anal.
I pulled the dildo out of her ass, then hooked one finger in her ass to pull her sphincter open. While doing that, I used the other hand to squeeze the base of my cock, maximizing what erection I had left. I guided my now hard dick into her open shithole. I began pumping to feel the blood rush back into my erection, then buried my self in her ass balls deep. Without skipping a beat, I picked up the dildo off of the bed, and began working its hard tip into the space between my dick and her ass sphincter. As I pressed in steadily with the dildo, her tight little shit hole gave way. My dick still buried to the hilt, her ass began to expand further, and further until it was finally accepting the dildo as well; her asshole had no choice. At this point, I felt Lauren physically protest. One of her hands flew down from around my neck, and back under her butt. She was trying to stop my hand that was holding the dildo. As her as opened, she desperately flicked and slapped and my hand, trying to stop it from pushing the hard blue silicone dick further into her asshole. It was no use- I didn't stop. We had previously discussed a safe word, and she didn't use it, so I had to assume that she wanted me to continue despite the pain.
The dildo was mostly in her ass now, right along side my dick. While by dick was still buried all the way, the dildo had yet to pass it's thickest point. Lauren had stopped trying to slap my hand away, but her ass itself was still resisting quite a bit. Her breath had become short and excited by this point. She was panting into my ear, with her entire body still pressed against mine. I began to slowly pump my dick out, then in, making half strokes while still holding the dildo in her ass. Right as I pulled out an inch, I pressed the dildo in, past it's thickest point. At this point, I could feel her asshole "break". It was extremely tight up until that point, but once the thick part of the dildo and my dick passed that threshold, her anal ring seemed to instantly relax. And it relaxed considerably… there was now room to fuck properly. Lauren gasped. Her breathing increased in speed, and her hand swung down below her again in a vain attempt to stop my pumping. "hey there, breathe deep. Relax your butt. You'll be okay" I whispered to her. She seemed to acknowledge my advice, and her breathing relaxed. At that point, I believe her soul broke just as her sphincter did a second earlier. First, her entire body went limp. Then, she raised her head, with both arms back around my neck, and looked up at me. While looking directly in my eyes, she said "fuck my ass… don't hold back. Show me how you and Tom are going to fuck it together.". Upon hearing that, I just let go. I started fucking a lot harer,moving both my dick and the dildo in and out, and an alternate fucking motion. I started to lose rhythm, and soon was shoving my dick and the dildo in and out simultaneously, as if they were one giant cock. “You like that? You like your ass being torn up by two dicks?” I grunted at her. Lauren didn’t respond. Her body had gone limp, and her breathing had settled to a medium pace. “Just use my torn up ass. Use it for your pleasure. Cum whenever you feel like it” she said quietly.
I fucked her hard for about ten minutes, and worked the dldo against my dick the whole time. Her ass stayed tight (or reasonably so) most of the time, and only began to really get loose around eight minutes or so into it. At that point, only the extra friction from the dildo made it possible to cum. I pulled out after I had finished and told Lauren to turn around and lay flat on her stomach. She did, and I was able to spread her ass checks and watch her gaping, distended asshole leak my cum. It slowly closed, and I could see a little blood trickle out along with my semen.
Later that evening, after Lauren’s mother came and retrieved her from my house, I talked to her on the phone. “You know, my ass was bleeding when I got home.” she said. I told her that was normal for her first time taking two dicks in her ass, and that it would be easier next time, and it would be even easier with me and Tom instead of a dildo. She seemed happy to hear that. “Are you proud of me?” she asked. “I am. I definitely am”. I replied.
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