tutoring a sister brother love story
- 2 years ago
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Tutoring My Friend's Sister In Sex Ed (Part 1 free porn video
My friend's little sister Samantha was nervous about pleasing her first boyfriend and asked me to help give her some hands on experience during the course of their relationship.
All of my stories are true accounts of my experiences. If you haven't read the story about my first time with Nancy, check it out. Otherwise some quick background: I'm a 32 year old Asian-American engineer. I went to college only about 10 minutes from where I went to high school which led to a number of story worthy encounters. I'm athletic, 5'7", and my penis is not small but not huge (6" length, just a hair under 6" girth) and that's enough about me.
One of the interesting things about staying near my high school for college was that as my friend's were flying across the country for school, their little sisters were left without their big brothers for the first time. I was always somewhat of a womanizing man whore so I'm not sure why a number of my friends asked me to look after their sisters for them, but they did. One of them was my friend Frank who had a little sister named Samantha. Sam and I had gotten to know each other pretty well over the years because she was like Frank's shadow. She was sweet, innocent, and very sheltered.
They were Thai. Sam has a very petite build. She was 5'5 98 lbs with long legs. Her A cup breasts added to her cute and innocent appeal but like many Thai women, she had these beautiful full lips that were made for sucking dick and I could tell she was one of those girls that would be seen as sweet and innocent in public, and a wild slut in bed. Turns out that she just needed my help to bring it out of her.
At the start of my freshman year in college, she was a sophomore in high school. Sam messaged me telling me she met a guy she liked. He was a senior but I found out later he was actually older than I was. They were going out that weekend and in my substitute older brother role, I reminded her to be good and to let me know if I needed to beat him up for getting out of line. She seemed happy and things were staying relatively innocent between them.
About a month later, she was working on a school project and asked me if I could take her to my school's library to do some research. Even though she was a sophomore she already had her license and a brand new BMW so she said she'd meet me after she got out of school the following day.
I actually forgot that she was coming and had brought this Korean girl named Gina from one of my classes back to my room to hook up. I had Gina topless in my bed and she had pulled my boxers down around my ankles and was stroking my cock. Gina had just put her lips around the tip of my cock when there was a knock on my dorm room door. Gina told me to ignore it but then I heard a voice say "it's Sam, are you there?" I told Gina sorry and tossed her her shirt and pulled my boxers and a pair of basketball shorts up and scrambled to the door.
I opened it and was greeted by the sight of Sam in knee high white stockings, a plaid skirt, and a white blouse which she had clearly unbuttoned at the top and bottom after school. I felt a lump in my throat as I forgot that she went to Catholic school. Bubbly and cute as ever, she asked if I was ready to go. I introduced her as my friend's little sister to Gina and told Gina I would call her after we were done at the library. I caught Sam staring at my six pack abs and the obvious bulge in my basketball shorts as I pulled a t-shirt on so we could head out.
As we started our walk to the library, I asked her how things were going with her boyfriend Oliver. She told me good but she wanted to ask me about something later. Sam smirked as she said "so who's this Gina girl? I hope I wasn't interrupting anything" and this time she gave a deliberate look down to the bulge that was finally starting to come down. I laughed and told her I'd go finish with Gina later.
We walked in the library and found the stacks where the books she needed were. One of the books she needed was at the top of the shelf and as she stepped up onto the step ladder to reach the book, I got a view of her cute little ass in a pair of black lacy panties. I felt my cock start to swell again so I suggested we go find a table to sit at so she could start researching.
While she was flipping through the books, I asked her what she wanted to talk to me about from before. She looked around and there were a few other students around so she asked if there was anywhere more private we could talk because she was embarrassed. I took her over to the group study rooms so she could talk freely. She told me that on her last date with Oliver, she let him reach up her shirt and feel her up through her bra. The older brother figure in me wanted to be angry, but my cock was rock hard while listening to her tell me what happened. Oliver had placed her hand on his cock through his pants but she pulled her hand away and he didn't push the issue. She told me that Oliver's ex was a girl at her school named Stacy.
"Stacy Tran? Vietnamese junior at your school now?"
"Yah that's her, she's kind of a slut"
"Oh yah, I know"
"Wait what? How do you know?"
I just raised my eyebrows at her and gave her the "you know" glance.
"OMG ewww! Gross! When? What did you do with her?"
"We met at a party last year and she gave me a blowjob. We hooked up a few more times before I graduated too."
"Wait. Oliver was dating her all of last year. Gross what a slut. I can't believe you hooked up with her. Yuck."
She continued on about how Oliver asked if she would give him a handjob. She said she wanted to but
was afraid it wasn't going to feel good for him compared to what Stacy did. She asked me if Stacy was any good. When I told her that she honestly was, that didn't make her feel better. I tried to reassure her that it wouldn't matter to Oliver. I wished I had just told her Stacy was terrible but I doubt she would have believed me anyways. She started crying and asked "what if I'm no good at it and he breaks up with me for someone better?" I told her if that happened then he's an asshole that didn't deserve her and I'd kick his ass. She stopped crying and forced a smile and said "thanks, it's nice to know that you care"
I put my arm around her and she leaned her head on my shoulder while I tried to comfort her. Then she looked up at me with her innocent eyes and said "do you think you can help me?"
"What do you mean help you?" (obviously I knew what she meant)
"Maybe you can give me some tips on how to make it feel better?"
"What like watch you stroke a banana or something?"
"Shut up. Stop acting like you don't know what I mean!"
"I really don't though"
"UGH! Will you let me practice jerking you off? I want to stroke your dick until you cum! Are you happy? I said it"
"No Sam! Absolutely not! Your brother would kill me! You're like my little sister!" My mind was saying all the right things but my cock was betraying me as the tent in my shorts was quite obvious by now.
"Oh really? I don't think my brother would have been looking up my skirt before or get one of these around me" as she reached over and squeezed my throbbing cock.
"I can't..." I tried to force the words out of my mouth but all that escaped was a moan as she continued to gently squeeze my cock.
"Please. It would really make me feel a lot better. Besides, I feel like I owe you since I made you walk out on Gina earlier before you were done"
She realized my silence was my will power admitting defeat. She got up and locked the door and pulled the blinds down on the window to the study room. She grabbed my hand and led me to the couch. She pulled my t-shirt up over my head and sat down on the couch in front of me. She placed her hands on my chest and slowly lowered them down over my abs before grabbing my waistband and pulling my shorts and boxers down. My cock sprang out as it was released and I saw Sam lick her lips while she was staring at my thick cock.
"You know this is the first dick I've ever seen" as she slowly wrapped her fingers around my shaft "the first I've ever touched"
She slowly started to stroke my cock with her soft hands. I went to lie down on my back on the couch and she knelt down between my legs and continued to run her hands up and down a rock hard dick for the first time. She asked me if it felt good and I told her it felt amazing but it's even better when it's wet. She parted her lips and allowed some of her spit to fall onto my cock. She repeated this making sure my dick was well lubricated and glistening from her spit shine.
I grabbed her hand and helped guide it up and down my cock showing her how to use a twisting motion. She asked if it felt good. The look on my face was all the answer she needed. I guided her other hand to my balls and she started to gently massage them while continuing to stroke my cock. I started moaning louder and she paused for a second before asking if my cum was going to shoot everywhere. I told her it felt so good that it might be unpredictable. She said she couldn't get stains on her blouse or skirt. She stood up and unbuttoned her blouse and laid it on the chair revealing a light pink bra covering her small but perky A cups. She unzipped the side of her skirt allowing it to fall to the floor as I got a full view of those lacy black panties. I asked her to turn around slowly to give me a full view of her tight young body.
As I watched the half naked body of my friend's little sister move back between my legs, I noticed she was no longer acting like the sweet, innocent girl I had known since she was in the 4th grade. She spit on my cock picking up where she left off stroking my dick with her right hand with a lustful cock hungry look in her eyes. Her left hand slid down between her legs and soft moans became louder and louder as she rubbed her pussy. She pulled her panties to the side giving me the first look any guy had had at her sweet tight virgin pussy. As she plunged her fingers into her own dripping cunt, she said "I can't believe we're doing this. I've had a crush on you since the first time you spent the night at our house".
She continued to spit on and pump my cock while finger fucking her sweet little love hole and the things coming out of her mouth got progressively dirtier and sluttier as she moved us both closer to cumming.
"God your dick is so fucking thick and hard. I love having my hand wrapped around it. My pussy was dripping just looking at your cock."
I told her she was being a naughty girl.
"I'm like your little sister? Your naughty little sister stroking her big brother's huge cock. I want you to cum for me baby. Do you like watching your little sister finger fucking herself? God I want your dick inside of me right now. I want your cock to stretch my virgin pussy out until you cum deep inside of me"
Watching Sam unleash her slut side for the first time was so hot I knew I wasn't going to last much longer. I told her I was going to cum soon. She pulled her panties down around her knees and gave me a full view of her fingers thrusting in and out of her little teen love hole. She had left nothing but a little landing strip of hair above her slit. She pulled herself closer to me so my dick was only inches away from her finger filled cunt.
I felt the eruption building in my balls. The first rope of cum shot at like a cannon landing on her belly button. She screaming "oh my god I'm cumming too baby...let it all out for me". I watched as her pussy pulsed around her fingers with her orgasm and she pulled every last drop of cum out of my cock until her fingers and pussy lips were covered with my hot sticky load. We both caught our breath and I told her that she had grown into one extremely sexy young woman and she had nothing to worry about when it came to pleasing Oliver.
We realized there was nothing around to clean up my cum she was covered in. She pulled her panties all the way off and wiped away my cum and hers with them. She handed them to me and told me to keep them as a thank you for helping her out. I still have those panties to this day and they remind me of that hot day in the library every time I see them.
She said how hot what just happened was and I agreed. She told me she wanted to do it again soon but I told her that wasn't a good idea. Even though we both wanted more, we agreed to pretend like nothing had ever happened. But something did happen and our relationship was changed forever. We were good about sticking to that plan for the next month until one day she called me and told me she had something to ask me about. Oliver wanted a blowjob and Sam was going to need to learn how to suck a dick.
That's the end of Part 1 of Sam and I's story. I would end up being her first everything over the course of the next year so I'm sure you can imagine what Parts 2, 3, and 4 will cover. If you want to hear more about how Sam and I's story develops, please like / leave a comment.
Thanks for reading. Hope you enjoyed.
All of my stories are true accounts of my experiences. If you haven't read the story about my first time with Nancy, check it out. Otherwise some quick background: I'm a 32 year old Asian-American engineer. I went to college only about 10 minutes from where I went to high school which led to a number of story worthy encounters. I'm athletic, 5'7", and my penis is not small but not huge (6" length, just a hair under 6" girth) and that's enough about me.
One of the interesting things about staying near my high school for college was that as my friend's were flying across the country for school, their little sisters were left without their big brothers for the first time. I was always somewhat of a womanizing man whore so I'm not sure why a number of my friends asked me to look after their sisters for them, but they did. One of them was my friend Frank who had a little sister named Samantha. Sam and I had gotten to know each other pretty well over the years because she was like Frank's shadow. She was sweet, innocent, and very sheltered.
They were Thai. Sam has a very petite build. She was 5'5 98 lbs with long legs. Her A cup breasts added to her cute and innocent appeal but like many Thai women, she had these beautiful full lips that were made for sucking dick and I could tell she was one of those girls that would be seen as sweet and innocent in public, and a wild slut in bed. Turns out that she just needed my help to bring it out of her.
At the start of my freshman year in college, she was a sophomore in high school. Sam messaged me telling me she met a guy she liked. He was a senior but I found out later he was actually older than I was. They were going out that weekend and in my substitute older brother role, I reminded her to be good and to let me know if I needed to beat him up for getting out of line. She seemed happy and things were staying relatively innocent between them.
About a month later, she was working on a school project and asked me if I could take her to my school's library to do some research. Even though she was a sophomore she already had her license and a brand new BMW so she said she'd meet me after she got out of school the following day.
I actually forgot that she was coming and had brought this Korean girl named Gina from one of my classes back to my room to hook up. I had Gina topless in my bed and she had pulled my boxers down around my ankles and was stroking my cock. Gina had just put her lips around the tip of my cock when there was a knock on my dorm room door. Gina told me to ignore it but then I heard a voice say "it's Sam, are you there?" I told Gina sorry and tossed her her shirt and pulled my boxers and a pair of basketball shorts up and scrambled to the door.
I opened it and was greeted by the sight of Sam in knee high white stockings, a plaid skirt, and a white blouse which she had clearly unbuttoned at the top and bottom after school. I felt a lump in my throat as I forgot that she went to Catholic school. Bubbly and cute as ever, she asked if I was ready to go. I introduced her as my friend's little sister to Gina and told Gina I would call her after we were done at the library. I caught Sam staring at my six pack abs and the obvious bulge in my basketball shorts as I pulled a t-shirt on so we could head out.
As we started our walk to the library, I asked her how things were going with her boyfriend Oliver. She told me good but she wanted to ask me about something later. Sam smirked as she said "so who's this Gina girl? I hope I wasn't interrupting anything" and this time she gave a deliberate look down to the bulge that was finally starting to come down. I laughed and told her I'd go finish with Gina later.
We walked in the library and found the stacks where the books she needed were. One of the books she needed was at the top of the shelf and as she stepped up onto the step ladder to reach the book, I got a view of her cute little ass in a pair of black lacy panties. I felt my cock start to swell again so I suggested we go find a table to sit at so she could start researching.
While she was flipping through the books, I asked her what she wanted to talk to me about from before. She looked around and there were a few other students around so she asked if there was anywhere more private we could talk because she was embarrassed. I took her over to the group study rooms so she could talk freely. She told me that on her last date with Oliver, she let him reach up her shirt and feel her up through her bra. The older brother figure in me wanted to be angry, but my cock was rock hard while listening to her tell me what happened. Oliver had placed her hand on his cock through his pants but she pulled her hand away and he didn't push the issue. She told me that Oliver's ex was a girl at her school named Stacy.
"Stacy Tran? Vietnamese junior at your school now?"
"Yah that's her, she's kind of a slut"
"Oh yah, I know"
"Wait what? How do you know?"
I just raised my eyebrows at her and gave her the "you know" glance.
"OMG ewww! Gross! When? What did you do with her?"
"We met at a party last year and she gave me a blowjob. We hooked up a few more times before I graduated too."
"Wait. Oliver was dating her all of last year. Gross what a slut. I can't believe you hooked up with her. Yuck."
She continued on about how Oliver asked if she would give him a handjob. She said she wanted to but
was afraid it wasn't going to feel good for him compared to what Stacy did. She asked me if Stacy was any good. When I told her that she honestly was, that didn't make her feel better. I tried to reassure her that it wouldn't matter to Oliver. I wished I had just told her Stacy was terrible but I doubt she would have believed me anyways. She started crying and asked "what if I'm no good at it and he breaks up with me for someone better?" I told her if that happened then he's an asshole that didn't deserve her and I'd kick his ass. She stopped crying and forced a smile and said "thanks, it's nice to know that you care"
I put my arm around her and she leaned her head on my shoulder while I tried to comfort her. Then she looked up at me with her innocent eyes and said "do you think you can help me?"
"What do you mean help you?" (obviously I knew what she meant)
"Maybe you can give me some tips on how to make it feel better?"
"What like watch you stroke a banana or something?"
"Shut up. Stop acting like you don't know what I mean!"
"I really don't though"
"UGH! Will you let me practice jerking you off? I want to stroke your dick until you cum! Are you happy? I said it"
"No Sam! Absolutely not! Your brother would kill me! You're like my little sister!" My mind was saying all the right things but my cock was betraying me as the tent in my shorts was quite obvious by now.
"Oh really? I don't think my brother would have been looking up my skirt before or get one of these around me" as she reached over and squeezed my throbbing cock.
"I can't..." I tried to force the words out of my mouth but all that escaped was a moan as she continued to gently squeeze my cock.
"Please. It would really make me feel a lot better. Besides, I feel like I owe you since I made you walk out on Gina earlier before you were done"
She realized my silence was my will power admitting defeat. She got up and locked the door and pulled the blinds down on the window to the study room. She grabbed my hand and led me to the couch. She pulled my t-shirt up over my head and sat down on the couch in front of me. She placed her hands on my chest and slowly lowered them down over my abs before grabbing my waistband and pulling my shorts and boxers down. My cock sprang out as it was released and I saw Sam lick her lips while she was staring at my thick cock.
"You know this is the first dick I've ever seen" as she slowly wrapped her fingers around my shaft "the first I've ever touched"
She slowly started to stroke my cock with her soft hands. I went to lie down on my back on the couch and she knelt down between my legs and continued to run her hands up and down a rock hard dick for the first time. She asked me if it felt good and I told her it felt amazing but it's even better when it's wet. She parted her lips and allowed some of her spit to fall onto my cock. She repeated this making sure my dick was well lubricated and glistening from her spit shine.
I grabbed her hand and helped guide it up and down my cock showing her how to use a twisting motion. She asked if it felt good. The look on my face was all the answer she needed. I guided her other hand to my balls and she started to gently massage them while continuing to stroke my cock. I started moaning louder and she paused for a second before asking if my cum was going to shoot everywhere. I told her it felt so good that it might be unpredictable. She said she couldn't get stains on her blouse or skirt. She stood up and unbuttoned her blouse and laid it on the chair revealing a light pink bra covering her small but perky A cups. She unzipped the side of her skirt allowing it to fall to the floor as I got a full view of those lacy black panties. I asked her to turn around slowly to give me a full view of her tight young body.
As I watched the half naked body of my friend's little sister move back between my legs, I noticed she was no longer acting like the sweet, innocent girl I had known since she was in the 4th grade. She spit on my cock picking up where she left off stroking my dick with her right hand with a lustful cock hungry look in her eyes. Her left hand slid down between her legs and soft moans became louder and louder as she rubbed her pussy. She pulled her panties to the side giving me the first look any guy had had at her sweet tight virgin pussy. As she plunged her fingers into her own dripping cunt, she said "I can't believe we're doing this. I've had a crush on you since the first time you spent the night at our house".
She continued to spit on and pump my cock while finger fucking her sweet little love hole and the things coming out of her mouth got progressively dirtier and sluttier as she moved us both closer to cumming.
"God your dick is so fucking thick and hard. I love having my hand wrapped around it. My pussy was dripping just looking at your cock."
I told her she was being a naughty girl.
"I'm like your little sister? Your naughty little sister stroking her big brother's huge cock. I want you to cum for me baby. Do you like watching your little sister finger fucking herself? God I want your dick inside of me right now. I want your cock to stretch my virgin pussy out until you cum deep inside of me"
Watching Sam unleash her slut side for the first time was so hot I knew I wasn't going to last much longer. I told her I was going to cum soon. She pulled her panties down around her knees and gave me a full view of her fingers thrusting in and out of her little teen love hole. She had left nothing but a little landing strip of hair above her slit. She pulled herself closer to me so my dick was only inches away from her finger filled cunt.
I felt the eruption building in my balls. The first rope of cum shot at like a cannon landing on her belly button. She screaming "oh my god I'm cumming too baby...let it all out for me". I watched as her pussy pulsed around her fingers with her orgasm and she pulled every last drop of cum out of my cock until her fingers and pussy lips were covered with my hot sticky load. We both caught our breath and I told her that she had grown into one extremely sexy young woman and she had nothing to worry about when it came to pleasing Oliver.
We realized there was nothing around to clean up my cum she was covered in. She pulled her panties all the way off and wiped away my cum and hers with them. She handed them to me and told me to keep them as a thank you for helping her out. I still have those panties to this day and they remind me of that hot day in the library every time I see them.
She said how hot what just happened was and I agreed. She told me she wanted to do it again soon but I told her that wasn't a good idea. Even though we both wanted more, we agreed to pretend like nothing had ever happened. But something did happen and our relationship was changed forever. We were good about sticking to that plan for the next month until one day she called me and told me she had something to ask me about. Oliver wanted a blowjob and Sam was going to need to learn how to suck a dick.
That's the end of Part 1 of Sam and I's story. I would end up being her first everything over the course of the next year so I'm sure you can imagine what Parts 2, 3, and 4 will cover. If you want to hear more about how Sam and I's story develops, please like / leave a comment.
Thanks for reading. Hope you enjoyed.
Safiya
- 19.06.2022
- 30
- 0
