Anal Virgin But Not For Lo
- 2 years ago
- 17
- 0
First Time Anal (True Story) (Long) free porn video
This is a true story with some aspects and details changed to keep the person/s anonymity. This story happened a couple of weeks after my first glory hole visit. You can find my first glory hole visit story in my posts on my profile. Skip to 'The action' If you want to get to the sex, enjoy.
The Beginning
Since my visits to the glory hole, I've started to crave cock more and more. Jerking off to regular porn wasn't doing it anymore, I needed something more exciting. I started to watch more and more sissy and shemale porn and had bought some toys to mess around with, a couple of different sized butt plugs and a 5 inch slim dildo.
Every night when I had time, I would strip naked and lay down watching sissy porn, while I trained my tight little virgin boi pussy. Each night I tried to take a bigger butt plug, until I was comfortable fucking myself with the 5 inch dildo. It took my ass about 5 days of hard stretching til I was able to fuck myself comfortably. And OMG it feels amazing. I did not know getting fucked would feel so good.
During all of this experimenting, I had posted an ad asking if there were any local daddies that would like to teach a younger man the ropes. After a solid week of vetting, I found an older guy who lived very close to me, he said he could host and would love to teach me how to take cock the right way. Let's call him Chris. Chris and I chatted and exchanged pics. He was in his late 40's, tall, medium build with a nice 6.5 inch cut cock and it was thick. We then agreed on a date.
Days leading up to the meet, we would chat back and forth, both exchanging pics keeping us both excited for the meet. Chris said that he couldn't wait to deflower my tight boi pussy. This got me excited, my hungry little hole was ready.
Chris messaged me his location the morning of, and I planned out my day around this schedule. This is it, I really am going to get fucked by a real cock. I got super horny, but knew I had to save my load for later that afternoon.
I rock up to his house, double checking the address, making sure I had the right house number. Chris sent me specific instructions on where to meet him. 'When you arrive, go to the left hand side of the house and enter from the back door, first level. I'll leave it open for you.' I did as he outlined. I walked down the left side of the house, following the small narrow walk way that lead to the back. The old brick house had 2 storeys with a very high wooden fence with a pool at the back. I approached the wooden door nervously, second guessing myself, 'maybe I should just ghost him' I thought. But my mind drifted back imagining his cock in my hands as I guide into my ass. 'Fuck it' and I opened the door and entered.
The action
I wandered down the tight corridor and I voice called out, "In here", I followed the voice which lead me to a room. There he was sitting on the bed facing me. Chris was wearing a dress shirt and dress pants, "You've been a bad girl." he said, "You need to be punished." I was confused for a moment then it hit me, 'Daddy role play' I remembered, It was something I suggested and we agreed that he would be daddy and I would be his little princess.
I immediately dropped to my knees in front of him, "I've been a dirty girl daddy" I teased. "What's my punishment daddy?" I asked licking my lips.
"Maybe you can start on this." Chris stood up and released his semi hard cock from his trousers, which danced in front of me as he moved his hips left to right. I licked the head of his cock, teasing him as I pulled his shorts down and out of the way. My lips slowly suck the head of his cock as I run my hands up his legs from his ankles and my hands eventually reach his heavy and low hanging balls. I stopped sucking the head and focused my attention licking and sucking those beautiful balls as I stroked his thick cock, which now is getting hard.
Chris puts his hand on my chin and moves me towards his face and we kiss gently. My hand is still stroking his shaft as we make out, tonguing each other and tasting each other. I usually do not enjoy kissing other men, but this one was different and not too bad. Mid way through our embrace, he placed his hands on my ass and gave me a good spank. I let out a moan and his kiss moves down to my neck whilst his hands slowly move up and pulls my shirt up and over my head. My hands stops stroking his shaft and I pull down my pants, revealing my 6 inch cock which already semi erect.
Chris unbuttons his dress shirt and sits down on the bed eyeing my body. "Holy shit, you are amazing!" he exclaimed. I bent down on my hands and knees and showed him my little boi pussy, moving it side to side like he did with his cock.
"Come up here," Chris ordered as he laid down on the bed, I followed his command and parked my butt on his face, which also gave me access to his cock. Without a word I engulfed his cock, which grew more and more in my mouth. While I was preoccupied with his cock in my mouth, he enjoyed his meal, sucking my cock and fingering my little eager hole. It was a few minutes into 69ing, when I felt a warm sensation in my boi pussy. "Oh daddy, that feels so good." I moaned, "Fuck"
He stops for a moment, "Is my baby girl enjoying that?" Chris asked as he continued to tongue my ass.
"Yes daddy, don't stop." I moaned, this time in a more slutty voice, and then going back to burying my face on daddy's cock, taking it as far as it will go down my throat. Before coming up for air. "Fuck" he moaned, "You like daddy's dick don't you sweetheart?"
"I do daddy." I replied while stroking his now fully erect cock that's glazed with my saliva. "Fuck me daddy, I need you inside me right now." I continued. He reached over on the drawer next to him and pulled out a condom and some lube. He passed the condom over to me, I took one more taste of daddy's cock and put a rubber on him.
"Stand up and bend over the bed" he ordered, I did as I was told. Chris stood up and lubed up my cute little pussy. He leaned over onto my right side and whispered, "Daddy loves you" as he slowly pushes his thick 6.5 inch cock into my ass. He pulls back and grips his strong hands on my hips and slowly thrusts me. With each thrust the pain slowly replaced itself with pleasure and soon after all the pain was completely gone. He thrust deeper and I could feel a wave of pleasure each time he is all the way in. This pleasure is a pleasure I have never felt before, no wonder why girls love being fucked. As I got comfortable, he leans over and hugs me with his strong arms as he quickens his pace. He kisses my back starting from the bottom all the way to my neck. With one hand he turns my head and we kiss, I stand up as he fucks me and feel him hitting my prostate. Still kissing and moaning with pleasure, his hands explore my body and eventually finds my fully erect cock. "Mmmm.. you're all wet and hard darling." he says. I couldn't reply, I was in heaven. He collects my leaking pre cum hanging off my cock and brings it up for me to sample. "Mmmm.. You are a dirty little slut arn't you?" he added.
"Only for you daddy" I quickly replied. His hands drift back to my cock and begins jerking my cock, which is now glistening with pre cum. "Fuck I'm going to cum daddy" I moaned with pleasure. He didn't reply verbally but physically by quickening his pace. The head of his cock is now hitting my prostate hard and fast. I couldn't hold it any longer. "Yes daddy don't stop" I continued to moan, "I'm gonna cum." My cock erupted with 2 days worth of cum all over the wooden floor. Chris, however, did not stop and continued to destroy my ass for the next what feels like hours, but was probably 5 minutes. "Get on the floor slut," Chris barked. I knelt on the floor where I had just came minutes before, the cum had now got cold and started to stick to my knees. I felt like a fucking dirty little whore. He took the condom off and threw it on the floor next to me. "So you like cum, slut?" he asked, lubing up his cock with his spit.
"Yes daddy, I want your cum." I replied nodding my head and sticking my tongue out. He stroked quickly and aimed the cum cannon at my tongue. And soon after I was rewarded with ropes and ropes of cum, some of which my tongue caught and others had covered my face. I quickly wiped up the cum with a finger, guiding it towards my mouth and swallowing it all down. Chris laid on the bed, with his cock softening quickly. I stood up and got dressed.
"Leaving all ready?" he asked.
"I can't stay, I have to get home and change for work." I replied. Chris looked upset but nodded to as if to say he understands. "Next time." I continued and walked over to give him a long kiss on the bed one last time.
I left satisfied and happy. We met again 2 more times. But I'll save those for another story.
The Beginning
Since my visits to the glory hole, I've started to crave cock more and more. Jerking off to regular porn wasn't doing it anymore, I needed something more exciting. I started to watch more and more sissy and shemale porn and had bought some toys to mess around with, a couple of different sized butt plugs and a 5 inch slim dildo.
Every night when I had time, I would strip naked and lay down watching sissy porn, while I trained my tight little virgin boi pussy. Each night I tried to take a bigger butt plug, until I was comfortable fucking myself with the 5 inch dildo. It took my ass about 5 days of hard stretching til I was able to fuck myself comfortably. And OMG it feels amazing. I did not know getting fucked would feel so good.
During all of this experimenting, I had posted an ad asking if there were any local daddies that would like to teach a younger man the ropes. After a solid week of vetting, I found an older guy who lived very close to me, he said he could host and would love to teach me how to take cock the right way. Let's call him Chris. Chris and I chatted and exchanged pics. He was in his late 40's, tall, medium build with a nice 6.5 inch cut cock and it was thick. We then agreed on a date.
Days leading up to the meet, we would chat back and forth, both exchanging pics keeping us both excited for the meet. Chris said that he couldn't wait to deflower my tight boi pussy. This got me excited, my hungry little hole was ready.
Chris messaged me his location the morning of, and I planned out my day around this schedule. This is it, I really am going to get fucked by a real cock. I got super horny, but knew I had to save my load for later that afternoon.
I rock up to his house, double checking the address, making sure I had the right house number. Chris sent me specific instructions on where to meet him. 'When you arrive, go to the left hand side of the house and enter from the back door, first level. I'll leave it open for you.' I did as he outlined. I walked down the left side of the house, following the small narrow walk way that lead to the back. The old brick house had 2 storeys with a very high wooden fence with a pool at the back. I approached the wooden door nervously, second guessing myself, 'maybe I should just ghost him' I thought. But my mind drifted back imagining his cock in my hands as I guide into my ass. 'Fuck it' and I opened the door and entered.
The action
I wandered down the tight corridor and I voice called out, "In here", I followed the voice which lead me to a room. There he was sitting on the bed facing me. Chris was wearing a dress shirt and dress pants, "You've been a bad girl." he said, "You need to be punished." I was confused for a moment then it hit me, 'Daddy role play' I remembered, It was something I suggested and we agreed that he would be daddy and I would be his little princess.
I immediately dropped to my knees in front of him, "I've been a dirty girl daddy" I teased. "What's my punishment daddy?" I asked licking my lips.
"Maybe you can start on this." Chris stood up and released his semi hard cock from his trousers, which danced in front of me as he moved his hips left to right. I licked the head of his cock, teasing him as I pulled his shorts down and out of the way. My lips slowly suck the head of his cock as I run my hands up his legs from his ankles and my hands eventually reach his heavy and low hanging balls. I stopped sucking the head and focused my attention licking and sucking those beautiful balls as I stroked his thick cock, which now is getting hard.
Chris puts his hand on my chin and moves me towards his face and we kiss gently. My hand is still stroking his shaft as we make out, tonguing each other and tasting each other. I usually do not enjoy kissing other men, but this one was different and not too bad. Mid way through our embrace, he placed his hands on my ass and gave me a good spank. I let out a moan and his kiss moves down to my neck whilst his hands slowly move up and pulls my shirt up and over my head. My hands stops stroking his shaft and I pull down my pants, revealing my 6 inch cock which already semi erect.
Chris unbuttons his dress shirt and sits down on the bed eyeing my body. "Holy shit, you are amazing!" he exclaimed. I bent down on my hands and knees and showed him my little boi pussy, moving it side to side like he did with his cock.
"Come up here," Chris ordered as he laid down on the bed, I followed his command and parked my butt on his face, which also gave me access to his cock. Without a word I engulfed his cock, which grew more and more in my mouth. While I was preoccupied with his cock in my mouth, he enjoyed his meal, sucking my cock and fingering my little eager hole. It was a few minutes into 69ing, when I felt a warm sensation in my boi pussy. "Oh daddy, that feels so good." I moaned, "Fuck"
He stops for a moment, "Is my baby girl enjoying that?" Chris asked as he continued to tongue my ass.
"Yes daddy, don't stop." I moaned, this time in a more slutty voice, and then going back to burying my face on daddy's cock, taking it as far as it will go down my throat. Before coming up for air. "Fuck" he moaned, "You like daddy's dick don't you sweetheart?"
"I do daddy." I replied while stroking his now fully erect cock that's glazed with my saliva. "Fuck me daddy, I need you inside me right now." I continued. He reached over on the drawer next to him and pulled out a condom and some lube. He passed the condom over to me, I took one more taste of daddy's cock and put a rubber on him.
"Stand up and bend over the bed" he ordered, I did as I was told. Chris stood up and lubed up my cute little pussy. He leaned over onto my right side and whispered, "Daddy loves you" as he slowly pushes his thick 6.5 inch cock into my ass. He pulls back and grips his strong hands on my hips and slowly thrusts me. With each thrust the pain slowly replaced itself with pleasure and soon after all the pain was completely gone. He thrust deeper and I could feel a wave of pleasure each time he is all the way in. This pleasure is a pleasure I have never felt before, no wonder why girls love being fucked. As I got comfortable, he leans over and hugs me with his strong arms as he quickens his pace. He kisses my back starting from the bottom all the way to my neck. With one hand he turns my head and we kiss, I stand up as he fucks me and feel him hitting my prostate. Still kissing and moaning with pleasure, his hands explore my body and eventually finds my fully erect cock. "Mmmm.. you're all wet and hard darling." he says. I couldn't reply, I was in heaven. He collects my leaking pre cum hanging off my cock and brings it up for me to sample. "Mmmm.. You are a dirty little slut arn't you?" he added.
"Only for you daddy" I quickly replied. His hands drift back to my cock and begins jerking my cock, which is now glistening with pre cum. "Fuck I'm going to cum daddy" I moaned with pleasure. He didn't reply verbally but physically by quickening his pace. The head of his cock is now hitting my prostate hard and fast. I couldn't hold it any longer. "Yes daddy don't stop" I continued to moan, "I'm gonna cum." My cock erupted with 2 days worth of cum all over the wooden floor. Chris, however, did not stop and continued to destroy my ass for the next what feels like hours, but was probably 5 minutes. "Get on the floor slut," Chris barked. I knelt on the floor where I had just came minutes before, the cum had now got cold and started to stick to my knees. I felt like a fucking dirty little whore. He took the condom off and threw it on the floor next to me. "So you like cum, slut?" he asked, lubing up his cock with his spit.
"Yes daddy, I want your cum." I replied nodding my head and sticking my tongue out. He stroked quickly and aimed the cum cannon at my tongue. And soon after I was rewarded with ropes and ropes of cum, some of which my tongue caught and others had covered my face. I quickly wiped up the cum with a finger, guiding it towards my mouth and swallowing it all down. Chris laid on the bed, with his cock softening quickly. I stood up and got dressed.
"Leaving all ready?" he asked.
"I can't stay, I have to get home and change for work." I replied. Chris looked upset but nodded to as if to say he understands. "Next time." I continued and walked over to give him a long kiss on the bed one last time.
I left satisfied and happy. We met again 2 more times. But I'll save those for another story.
Grace
- 04.11.2020
- 12
- 0
