i used as little punctuation as possible since i noticed that it did chanced in a few letters and symbols.
let me know what you think about the story!
Enjoy and who knows, this might be a true story…
Is watching Illegal?
It all started when I was living with my grandmother. I had some problems getting to school because it was too far away from home so my granny suggested that I would move to her home. When my grandpa died, he left her a lot of money and a big house so she could miss a room. She told us she would love the company so my parents and me agreed with her. Her house was just five minutes away from my school. A lot les then an hour what is was now
I have always had a good relationship with my granny. When I moved in with her, she was about 62 years old but she still looked amazingly beautiful: really dark hair, light blue eyes, a nice firm ass. Her best features were her breasts. She did not have the biggest but they where big enough to see that she that they were as firm as when she was 18.
Being a nearly 18-year-old boy, my grandmother was a recurring theme in my fantasies. The thought of living so closely with her sparked my imagination even further. I was hoping that I could catch a glimpse of her body but I did not expect anything to happen like it did.
The only downside to moving away from home was that I would be moving further away from my girlfriend, who was also my neighbour. We recently discovered the pleasures of anal stimulation. It turned out that we both loved getting fucked from behind in that little forbidden hole. So it was a perfect example of bad timing.
A few weeks before the beginning of this story we were lying in bed. We just had sex but I could go for another one. Anne, my girl, asked me if I would like to stick it in her ass. Knowing her I knew that she would not just let me fuck her ass but I said yes because it was something that I wanted to do since we were together. She said that she would let me fuck her but there was one condition. I would let her do it to me with her dildo. Being so turned on by the prospect of her little star rapped around my cock I agreed to her terms.
She took out her dildo and lubed it. She told me to get on my hands and knees with my ass in the air. I did as she told and she put some lube on my asshole. She took her time, massaging my bum and slowly putting a finger in me from time to time. She noticed that I was really enjoying it and she thought it was time to begin the real deal. She took her 2inch dildo (she like them small so she could get them in and out het pussy really fast without stretching it) and started probing my hole. Suddenly she pushed it in me. It was the best feeling I have ever felt. I felt full, and just so incredibly horny. I think the thought of getting ass-fucked by my girlfriends dildo really did it for me. She picked up a nice slow pace so my muscles could get used to the feeling of getting fucked. After about 5 minutes she started going faster and I started to feel my sperm getting ready to spurt out of me. I did not understand it because I at the time, I had no idea about the concept of a prostate massage. I was still sitting in the doggy position and Anne came sitting next to me so she could jerk me off while she was banging that piece of rubber in and out of me. After 2 minutes of the most intense feelings I have ever had I shot my load. I could not believe how big my load actually was. It just kept coming out of me, spurt after spurt. When I had finally stopped shooting sperm I rolled to my side with the dildo still inside me. I saw Anne taking a little sperm from the sheet between her fingers. She brought it to my mouth and said: a little gift for my good little boy. I just licked it of her fingers and saw her smiling. She laid herself next to me, on the puddle of semen, and we fell asleep. From then on we experimented a lot with anal play, cumsharing, and her dominating me.
Getting back to the story.
After saying my goodbyes to my girl and family I left for my grannys house. She welcomed me in a cute little pink dress that let me see everything I hoped to see. She showed me to my room and let me unpack. I took my time and after about half and hour I went downstairs and the first thing I saw was my grandmother putting on stockings and really sexy high heels. I stopped and stared at her, she smiled at me and proceeded like she did not mind me watching her. I instantly knew I mad the wright choice moving here.
The next few days nothing special happened. I went to school like usual and played some video games, skyped with Anne and got bored after school. Until Joyce, that is grannys name, told me she had to go out for a few hours. I called Anne and told me that I had the place to myself and invited her over. She told me she could not make it for some reason she would not tell me but she had an idea.
She told me to meet her a skype. I let skype start up and waited until Anne showed up. We started the cam session and I saw Anne wearing nothing more then her most sexy underwear. She told me to get naked and stand before the webcam so she could see my dick. Off course I listened to my mistress. I had to start jerking off. Like a good little boy I listened again. I was wanking away and she was looking and playing with herself. She asked if I had put something in my ass the last few days. I did not so she told me it was about damn time I did. I would gladly listen to her but had nothing with me that I could put inside me. Anne then had the idea that would turn my whole world upside down. She told me to go to my grandmothers room and look for a vibrator or something like it.
I went to joyces room and started looking. I had Anne on the phone and put her on speaker so I could look without having to hold my phone. I started looking in the usual places. In her night cupboard, her drawers and al the other places I could think off. I did not find one toy. Then I looked under her bed and I saw a box. I opened it and saw a collection of toys, a few videotapes, a cd or two, a couple of pictures and a big bottle of lube. I told Anne I had hit the jackpot. She told me to take one toy, the bottle of lube and a used panty from the laundry basket.
As I returned to my room, I let Anne see the loot. She was pleased and told me start jerking again while laying on the bed. After a few minutes she said it was time to let my ass join the party. I lubed the dildo and my hole. It slid right in without any pain. It just gave a lot of pleasure. I took place on the bed like a dog so Anne could see my ass spread wide for my grandmothers dildo.
I had to smell her panty while I was jerking so I laid it under my face. I could really smell the juices. The smell together with my prostate being milked I started to moan and I was just about to cum when and told me to stop. Now I had to lie on my back with my ass against the walls and my legs up. I knew where she was going. I had to position myself so that I would shoot my load right in my mouth and over my face. When I had assumed the position I had to put the dildo back inside my ass. I did and I started to jerk again. It only took a minute until I came. With al the excitement of the search and the fact that I was using someone else her toy I came almost as hard as the first time that Anne jerked me off with her dildo in my ass. my face was covered with cum and my dick was still dripping when Joyce suddenly walked into my room. I could imagine that the sight was not great to see. Her grandson in a position that would let him cum over himself,one of her toys in his ass, her bottle of lube next to one of her pantys and his girlfriend watching trough the computer.
Joyce said noting and just left the room. Anne told me to clean up and go apologise to my grandmother. I wanted to grab a shirt to clean my cum of my face but Anne quickly said I had to lick I al up myself as punishment for getting caught. After I had cleaned myself I went downstairs and prepared for the worst. I thought for sure she would kick me out and tell my parents.
When I entered the living room I found Joyce watching tv and I asked her if I could speak to her. She interrupted me and told me that there was nothing to talk about. She should not have come into my room without knocking. She also asked me if I could wash her dildo and put everything back. I told her I would and went back upstairs. After I did as my grandmother had asked me, I went back to her and told her I was sorry and that it would not happen again. She got up from the couch and gave me a hug. She also gave me kiss on the cheek. Since I did not had the time to wash myself I think she would have tasted the sperm that I shot over my face. I went from being relieved back to embarrassed but she acted normal so I thought I dodged a bullet. She told me that I had nothing to be ashamed about and that I could enjoy any kind of sex in her house that I wanted.
She broke loose from the hug and took her place back in the couch. I went back upstairs and called Anne. I told her what Joyce told me and she was happy that should still let me stay there. The next few days everything went back to normal. I kept my masturbation session “normal” and Joyce only came in my room after she had knocked a few times.
Five days after the big adventure I came home from school. Joyce was not in the house so I checked the backyard but it appeared she was out. I went up to my room to check my mails and play some video games. When I entered I saw something lying on my bed. It was the same dildo I had used before, a condom and the bottle of lube. There was also a note that said: could u clean it and put it back after you are done, Enjoyce. To be honest, I was shocked. The thought that my grandma knew what kind of a freak I was was hard enough but knowing that she wanted me to do it was a little bit much. Still, I was getting really horny seeing that dildo just waiting there to get in my ass. I said to myself: just enjoyce!
I did the same as I did fie days ago. I jerk off with my ass in the air and shooting my load over my face. I really started to like the feeling of cum flying in the air and landing on me. After I got all of my semen of my face and in my mouth I took the condom of the toy, washed it and put it back in the box. I went downstairs and watched TV until Joyce came home. She gave ma a kiss on the cheek and nothing more. She did not asked e about the toy or anything like that. It was just business as usual. For me, that was no problem. I started to like the fact that I kind off had to women in my life telling me what to do with my penis.
The next few days I did not find anything on my bed. I was just about to give up hoping when I came home and found a video on my bed. The video had no label and looked quite new. I was thinking to myself: “since it is just a video, let me do something a little bit more dangerous”. I went downstairs and started watching it in the living room. I took my clothes of and stared playing with myself a little but not to shoot my load, I wanted to watch the movie. It was a shock when I noticed that the woman in the video was my grandmother. The idea crossed my mind that she would be starring but I had no idea that she would do the dings that could be seen on the tape.
The first scene was normal sex. Missionary, doggy, 69, blowjob swallow. The face of the man was not visible the first few minutes so I did not know if it was grandfather or someone else. It would not surprise me if it was the latter and that granddad filmed it. From the second scene it started getting interesting. There where 4 guys wanking over one female. The woman was Joyce and she looked like she was really enjoying the view. After about 5 minutes, all the guys had shot their load over Joyce and she cleaned herself up by licking it from her fingers. When she had the most it, one of the guys started to pee over her. You could see by the expression on her face that she was surprised but she quickly started to like it. Because the others saw that she was enjoying it they followed and let loose. Streams of piss were aimed over my grandmother.
I still was not really jerking hard when the next scene began. The first thing you could see was a dog. I think it was a Labrador, or something like it. A man told it to go trough the door. In the next was my grandmother. She was just standing there, naked. The dog instantly went for her crotch and started licking her. This is when I heard he front door open. I began jerking furiously and saw Joyce entering the room. She had the same surprised look as in the movie and then she started smiling. She came to sit next to me in the couch. She did not do anything. She was watching. I focused back on to the screen and the dog was pounding her hard. Seeing her getting fuck by a dog was to much for me. I came and made quite a mess. There were spurts of sperm on the couch, the carpet, me and one on her leg. She took that little drop between her fingers and brought it to my mouth. Off course I licked it up. Then she stood up, gave a kiss and said hello. She started walking away when I asked her: ”grandma, why won’t you join me”? she said to me: “watching is not illegal”.

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