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My Sister, My Tormentor
by Anonymous Author (1999)

***

A boy is caught masturbating by his older sister and is 
blackmailed into doing it for her and her friend, which 
leads to an humiliating experience. (m-teen-solo, ff, 
mm-reluc-1st-bi-expr, teens, huml, mast, inc, voy, 
blkmail)

***

It all started when I was 13 years old and just 
discovering my sexuality, being so young and at that 
time inexperienced I used my imagination and of course 
dirty books to excite myself and that is how my problem 
started.

I was at home alone, mom and dad at work, and Julie (my 
sister and 16 years old) at her friends as usual, I had 
just got home from school and with nothing better to do 
so I decided to amuse myself by well playing with 
myself. I had been doing this for about a year now and 
enjoyed it very much. 

There was nothing better than lying in bed and stroking 
yourself to that magic moment when you thought nothing 
could be better and life was good. I had taken off all 
my clothes and propped up my pillows got my dad's best 
dirty magazines and started to slowly enjoy myself. 
Looking at these women got me excited and I was soon 
stroking my 6' cut cock (wish I could brag like many 
people do in these stories and say my 9 or 10 inches but 
I'm just average).

I had been stroking for about 30 minutes and had a lot 
of pre-cum on my belly, I was at that point where I was 
trying to decide, did I want to finish up or continue on 
for awhile longer? I decided to do something that I had 
up to that time not tried yet and that was to taste my 
pre-cum. 

I can't say that I liked it but can't say that I didn't 
either, but what I can say is that at that time in my 
life I had never been more excited and shot my load all 
over the place. Now what I lack in size I more than make 
up in quantity of cum that I can shot. It had pooled up 
on my chest and belly so I decided to taste it also, I 
guess having just came it wasn't exciting anymore and 
decided that I did not like the taste.

It was at this moment that I heard the slight laugh from 
the bathroom that separated my room with my sisters. I 
just froze, my sister must have sensed that I had 
noticed her and she came walking into my room. I was 
naked with cum all over me and scared shitless.

I was on top of my covers so they were no help and my 
clothes were on the floor at the foot of the bed, I was 
helpless and just laid there in what had to be the most 
humiliating state I had ever been in (at least to that 
point in my life). I started to get up but she quickly 
garbed my shoulder and pulled me back on the bed. She 
told me that I had been a bad boy and that Mom was going 
to be very disappointed. She also stated that Dad would 
probably kill me.

I started crying, begging her not to tell out parents, 
she just laughed and said that it was up to me on 
whether they would find out or not. I thought that maybe 
I would get out of this mess but I was very wrong. She 
told me to lie still and left the room. She then 
returned and had 3 Polaroid's with her.

She had taken them through the window and showed me 
playing with myself and also tasting my pre-cum. She 
left the room and came back with the camera and said she 
wanted more and better pictures, I started crying again 
and begged her not to. She just laughed and said that I 
better get hard again and right now.

I just lay there for a second and she became very angry. 
As she started out of the room saying that Mom would be 
in to see me when she got home, I yelled for her to stop 
and she smiled and came back and said to start stroking. 
I was very scared and with the threats there was no way 
that I could get hard again. She took pictures of me 
naked lying on the bed and then said that if I couldn't 
get hard that I could clean myself up and get dressed. 

I thought that it was over but when I started to get up 
she stopped me and said that I had to clean myself up 
first. Being confused I asked her how I was supposed to 
do that if I couldn't get up. She said that I looked 
like I was enjoying myself when I was eating my cum so 
she wanted me to lick myself clean, again I started 
balling but she just yelled for me to start. 

I started to scoop my cum up with my fingers and eat it. 
She took pictures the whole time and even had me hold it 
above my lips and let it drip down while she snapped 
more pictures.

After she had used all the film in the camera, she 
turned around and left, looking at her works of art and 
matter-of-factly, saying that she was done FOR NOW.

***

The next day all I could think about was my sister 
giving the pictures to my mom or dad, I was pleasantly 
surprised to find out that she would be spending the 
weekend out of town with friends. Saturday morning 
arrived with mom and dad working and me feeling a little 
better about my situation. I decided to go bowling with 
a couple of friends and then we decided to walk down 
town and just hang around. I told them that I meet them 
there and went home to get some more money that I had in 
my room.

I walked into my room and was shocked to see my sister 
Julie laying on my bed waiting for me. I asked her what 
she was doing and she said that she had been waiting for 
me. I asked her why she wasn't out of town with her 
friends and she said that she had better things to do at 
home. 

At that point she told me to take my clothes off and 
that I was going to be her entertainment. I just stood 
there in shock. The tears started to well up in my I 
eyes but she got mad and said that I should quit being a 
sissy or she was going to start treating me like a 
sissy.

I told her that I would not do it and she just smiled 
and got up from the bed and left. I got my money and 
left quickly. All the rest of the day and that night I 
was scared wondering what my sister might do. The next 
day my mom came up to me while I was eating breakfast 
and said that Julie had given her some pictures of me 
that she thought were very interesting. 

I started to babble not knowing what to say when she 
showed me 3 pictures of me when I was about 5 and 
dressed like a clown for Halloween. I was so relieved 
but understood what my sister was trying to tell me and 
that was that she had pictures and was going to give 
them to mom.

***

The next day when I came home from school I found a 
chair at the foot of my bed, I was about to put it back 
in the living room when Julie walked in, she said that 
it was time to get down to business. She through some 
pictures on the bed and said I could do as she says or 
the pictures would be given to mom. She said that if I 
started crying that the pictures would go to mom. I 
could tell by the look in her eyes that she would do it.

I asked her what she wanted and she said to strip and 
get on the bed. I slowly took my clothes off and she 
asked me to turn around before lying down. As I turned 
around she told me to stop and then made a comment about 
my ass, I then was instructed to lie down on the bed and 
to start playing with myself. 

She left the room and came back with the camera. She sat 
in the chair and I started to stroke myself. Being 
scared shitless I again could not get hard. I had been 
trying for about 5 minutes when she got up and put her 
hand just on the inside of my thigh just below my balls.

A shot of electricity shot through my body and my cock 
sprang to life. She then sat down and watch the show. I 
started stroking myself faster and was getting more 
excited than I had ever been, she told me to slow down 
and started taking pictures. After about 15 minutes she 
told me to go faster, the look on her face told me that 
she was getting excited but she didn't touch herself. As 
I quickened the pace my balls got tight and I knew that 
I was going blow, She sensed this also and moved up for 
a closer look.

I lost it at that point and arched my back and shot 
probably the largest amount of cum that I have ever done 
to that point. Most of it landed on my chest and belly 
with some hitting my face and the bed. She sat back and 
told me to complete the job. I knew that she meant to 
clean myself up and proceeded to scoop up the cum and 
eat it.

She then got up and went to her room and shut the door. 
I know that she went in there to play with herself I 
could see it in her face. I got up and went to her door 
and turned the knob but it was locked. This went on for 
the next couple months about 2 to 3 times a week. To 
tell you the truth I started to look forward to it. I 
would get really excited just thinking about 
masturbating in front of her.

***

I asked her one day if I could see her naked, she just 
laughed and said that if I was bold enough to asked her 
that then I was becoming too strong and she would have 
to put me back in my place. I asked her what she meant 
by that and she said that she liked me as a sissy and 
that she had a surprise for me tomorrow. At first I got 
really excited then I started to get worried, what did 
she have in mind for me. I found out the next day after 
school.

I got home from school and went right to my room, Julie 
came in with a smile on her face, she told me to take my 
clothes off, I did and laid on the bed. She left the 
room and came back with her friend Karen, Karen was 17 
and the object of many of my fantasies, She looked at me 
and laughed, this got my sister laughing also, I started 
crying. 

Julie told me to start playing with myself, Karen was 
making comments about my hairless balls and that she 
hoped that I got bigger or else women would be laughing 
at me the rest of my life.

Karen was a lot bolder than Julie she would tell me to 
grab my balls with my one hand while stroking myself 
with the other, she then told me to get up and turn 
around. She told Julie that she was right, that I had a 
cute smooth ass that looked like a females. 

She asked me to spread my cheeks, I did and she then 
told me to stick my finger up it. I shot up and they 
both laughed. They said do it or else they would give 
some pictures to my friends at school. That was more 
serious than giving them to my parents. I proceeded to 
stick my finger up my ass.

Karen then left the room and came back with a carrot 
from our icebox, she told me to take my finger out and 
she then handed me the carrot, I tried to get it in but 
with no lubrication I could get it in. Karen went into 
the bathroom and brought back some Vaseline and lubbed 
up the carrot. She then proceeded to shove it in me. 

Now this was humiliating but exciting also, I can't say 
that it felt good but know that I had a fine looking 
lady fucking me in the ass with a carrot was more than I 
could take and I shot my load all over the bed.

Karen left the carrot in place and looked at the cum all 
over the bed. Julie said see I told you he could shoot 
more cum than anyone that I have ever seen.

Karen seemed quite impressed also. "He'll really lick 
all that up?"

"Yep!" Julie replied.

And I then proceeded to clean up my mess. As I was doing 
this I could see some strange looks on both their faces, 
but they seemed very excited. After I'd done, they both 
said thanks for the show and went into Julie's room and 
shut the door.

I went and listened at the door and could hear them 
moaning and I got hard again. I also heard them talking 
about other things they could do to me. It took me about 
two minutes and I came all over the wall. I cleaned it 
up with a paper towel and left the house.

***

Over the next couple of months they did about everything 
to me that you could think of, not once did they let me 
see them naked, all they ever did was watch and then 
head for Julie's room. They stuffed things in me, had me 
roll over and try to suck myself off. I was limber 
enough but they would hold me in that position and make 
me cum in my mouth. I came so much that it would spill 
out of my mouth and they would laugh at me.

They must have been getting bored with me because all of 
the sudden they left me alone, it had been about 3 weeks 
and I was starting to feel like it was over, I didn't 
know if I was sad or relieved that it was finished. That 
all change though that Saturday. My parents went to work 
and Julie left the house, I was just laying around 
watching a football game when Julie, Karen and some guy 
I didn't know came in.

The guy looked at me and said that he had heard that I 
liked to eat cum, I was shocked and speechless. Julie 
looked at me and said that they and some knew surprises 
for me. I started to get up to leave but Karen jumped on 
me and said the pictures could still be given out and 
that Ken would kick my ass just for the hell of it. They 
took me into the bedroom and Ken took off his pants and 
underwear. He was hard and a little bigger than me, a 
lot hairier though. He was stroking himself and said for 
me to get on my knees and start sucking.

I looked over to Julie with pleading eyes but she had 
that excited look on her face and I got on my knees and 
went over to Ken. I put the head in my mouth and didn't 
like the taste at all, I started to gag but that just 
made them all laugh. Ken grabbed me by the head and 
stuffed his cock down my throat. This seemed to excited 
him a lot as he was pounding my mouth pretty quickly. In 
no time at all he was cumming in my mouth. He grab my 
head real hard and wouldn't let go. He seemed to cum 
forever , it started to dribble down my chin, he let go 
of my head and wiped my face with his dick.

I just sat there hoping that it was over, no such luck, 
Karen told me to take my clothes off, I looked over at 
Ken and saw that he was still hard and stroking himself. 
I got up and made a dash for the door but all three 
jumped on me, they had my clothes off quickly and had me 
on my belly. Karen got the Vaseline and the next thing I 
knew Ken had his cock up my ass.

I was in pain and looked over at Julie she was really 
excited and kissed Karen right in front of me. Ken 
lifted me so I was on my knees and Karen reached around 
and grabbed my cock. Ken kept say how tight I was and 
that he wished Karen was that tight. Karen seemed to get 
mad and squeezed my cock really hard.

Ken must have been really enjoying himself because I 
could tell he was about to cum and he would stop and 
wait a few seconds then start up again.

He must have fucked me for at least 20 minutes. I came 
from Karen stroking me and she scooped in her hand and 
showed it to Ken and said that she wished that he could 
cum as much as me, she then had me lick it off her hand. 
This made Ken really hot and he came in my ass.

I was left laying there while the 3 of them went into 
Julie's room. I went into the bathroom to shower and 
could hear them having sex. I heard Julie say that she 
was amazed that he could be hard again and then I heard 
the sex start.

I took a shower and left still hearing them fucking. I 
have to admit that I was kind of pissed, They had been 
using me for about 6 months now and I had never even 
caught a glimpse of either Julie or Karen naked. When 
they kissed earlier that day was the first time that I 
saw even that.

***

Well I never saw Ken again and I only had to masturbate 
for my sister and her friend a few more times. Julie got 
pregnant a couple months after my encounter with Ken and 
moved out of the house. She got married on her 17th 
birthday and on my 14th birthday I received a present in 
the mail from her. 

It was a box full of pictures with a note saying that 
she thought I should have them. I was relieved and 
finally saw an end to this part of my life. 

I have to admit now that I think back on it, that I 
probably enjoyed it more than I would ever want to say. 
I did not enjoy being fucked by Ken and I'm glad I have 
never ran into him again. 

I have to say though, that it did excite me to think of 
seeing another man's cock and I did have a sexual 
adventure that I must say is a byproduct of my encounter 
with Ken but that's another story entirely.

END

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This story was written as an adult fantasy. The author
does not condone the described behavior in real life.

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Kristen's collection - Directory 70