Part 1 : My name is Billy I am in my 40’s at present but this story goes back to when I was a young man. I grew up normal but with very little experience with girls and woman. Being this was the case most if not all of my sexual orientation and experimenting was alone through masturbation, which I discovered at the age of 12 or 13. Starting off that young I was a steady once or twice a day kind of boy. I would find the urge overtook me at different times whether it be in the car hiding somewhere or in my room, always the shower and I even remember doing it in restaurant bathrooms. This brings me to the story I would like to share with you all. I have never shared this with anyone but even to this day the events that unfolded that summer weigh on me heavily and is still my go to source of self-pleasure. It was early July with hot humid long days when it got dark very late. I always would cut through the yards to get home easier when I happened upon a window with the curtains opens on the first floor, movement inside caught my attention. What I saw inside changed my life forever, it was an older woman in her early 40’s id say walking around in her bedroom in her underwear. This was truly the first time I had seen a woman with this little amount of cloths on. My heart was racing and my pants were stirring it felt so wrong but I just had to touch myself, which I did through my shorts just watching her walk around folding her laundry and putting it away. I must have stood there hiding in the shadows for 20 mins just watching this older woman until she climbed in bed and turned off the lights. I was devasted hoping to have seen more and disappointed as I had not brought myself to cum. I walked home hard as a rock the whole time building up saliva in my mouth ran the last few blocks, got to my room spit right into my hand and jerked myself off thinking about what I had just seen. The next day dragged as all I could think about was going back there in hopes of seeing more. Once it was even close to getting dark I went back and took up the same position, I must have waited for three hours but the light never came on. The next day was even longer and again I went back. This time it took about 30 mins of waiting when she walked into the room fully dressed and just cleaning up. I watched intently and waited. Finally, she started to undress again only to the point of getting down to her underwear. I was dizzy with lust rubbing myself through my shorts was longer good enough, my shorts were partly pulled down and was fully stroking myself hard as rock hidden only by a bush and the darkness. It proved to be too much for me and I orgasmed so hard I shot my cum all over the side of her house but again the lights went off and I was left to walk home satisfied but not.
Part 2 : Since that night it had been several days before I was able to sneak off to my post outside her window. This time running the whole way hoping I had not missed anything I got there just in time for her to walk in and start her undressing routine that I enjoyed so much. Cock in hand hard and dripping pre-cum I was ready. This time started out very much the same she undressed down to her underwear, she was not thin but not heavy either pretty face brown hair full beautiful breasts and I could close my eyes and see every inch of her if I choose too. There would no closing of my eyes why I was there I was transfixed on her watching every movement praying for her to take off more even whispering it out loud to myself. Finally, that moment came I watched her reach back an unhook her bra and take it off her back was to me so I just waited for her to turn around and then I was rewarded with seeing the most wonderful set of breasts I still have ever seen. They swayed perfectly as she moved her nipples were large and semi erect and she rubbed them as she seemed happy to have them free. As quick as that had happened she had left the room .. I was heart broken but still stroking myself feverishly. It was a few minutes until she walked back and when she did she was completely naked and I was stunned seeing the outline of her pussy lips and her perfect triangle bush sent my mind spinning and again I shoot my load all over the side of her house. My cum was everywhere including my hands which made my hand slip off my cock and the hit the house I moved sideways and put my back against the house praying she didn’t hear it. That’s when things took a drastic turn, next thing I knew she was grabbing my arm and I was struggling to pull my shorts up and put my swollen cock away with cum all over myself and hands. She starting dragging me towards the front door I fought to break free but her grip was very tight. She was yelling at me calling me a stupid little boy a pervert a sick little pervert and she was going to call the police and my parents. My head was spinning at the trouble I was in and the embarrassment. She pulled me into the house and grabbed her phone to call the police .. I was trembling I was so scared and was apologizing and pleading with her not to call the police. After what seemed like an hour of this she finally showed signs of calming down the whole time was still begging her not to call and that I was so sorry for what I had done.
Part 3: After pleading and almost crying for about 30 minutes for her to let me go and not call the police she finally released my arm and just stood there looking at me on the floor practically on my knees tears in my eyes begging for forgiveness with dried cum on my pants and arm and then she broke the silence and asked if I was truly sorry. I said yes of course .. she said truly truly sorry ? Again I said yes truly truly sorry. She then asked what was a sorry for and asked me to say exactly what I was sorry for. So I looked at her and she said to either say what I was sorry for or she makes the phone call. So sheepishly said I was sorry for peeking into her window. And she said what else .. I looked at her confused and I said I just told you .. she yelled this time and said boy you better tell me everything right now. So again I said I was sorry for peeking in her window and she leered at me and I almost whispered and for touching myself and she said what?? And I yelled back and for jerking off ! that earned me a slap across my face. Then she told me that I was going to have to be as mortified, embarrassed and humiliated as she was in order for her to feel justice was served. Then she told me to strip .. I shot up a look at her and knew she was serous so I stripped down leaving my underwear on. This again angered her and she yelled all of it .No girl or woman had ever seen me naked I was so terrified I was frozen and could not bring myself to do it. So she walked over to me and basically ripped them off of me. She just stood there looking walking around me yelling at me not to cover myself up and then asked how it felt which I replied to was awful. She smiled for the first time and said good you deserve it. Then she told me to touch myself and masturbate in front of her. First off, I had just came not too long ago and was the most embarrassed I had ever been there was no way I could do that and I told her I was sorry again but I could not bring my self to do it. She laughed again and said that I had no issue doing it outside peeking in at her through her window. I just looking down and my small on hard penis and knew that I could not do it.
Part 4: She was enraged I could not do as she asked so again she grabbed me by the arm and pulled me into the kitchen where she pulled out a chair and pushed me down into it and told me not to move. Next came her tying my ankles to the chair legs which put them in a spread position and me hand behind my back to the chair , then came a blind fold . Next thing I felt was her touching me touching my balls and my cock stroking it with something cold and slippery it had like a greasy feel then she stopped and felt her putting it on my balls thighs and even on my asshole. Then there was nothing except her snickering and commenting how my dick was still not hard. I heard her walk away and a few minutes passed I was so terrified of what would happen next. Next thing I felt was the feeling of being licked from my ass hole up my balls and my cock .. it was rough long licks fast though I was confused as I had never been licked or had a blowjob. Then I felt something furry touch my leg and I freaked out and started to cry. She told me not to be a baby and that she would take the blind fold off. What I saw next freaked me out even more. It was a massive German Sheppard licking me, licking off what I now saw to be mayonnaise. She told me to be still and not saw a word or she would command him to bite me. So I just watched in horror while this beast licked off every bite of the Mayo. When he was done with his assault, I was licked clean but still not hard. She was very not happy about this. She leaned down right in my face and told me I had to learn to like what just happened and that I would not be allowed to leave until I came. She applied more the mayo and stood right next to watching the dogs tongue go at me again. I was so mortified I closed my eyes trying not to think about it which was pretty much I’m possible at that point and she making me open my eyes and watch. My cock was starting to feel raw at this point by I tried to just focus on the feeling. Again, I was cleaned off but starting showing a little bit of hard on at this point. She again she went to apply more and I begged her not to that I would do anything but this she laughed again at me and said no and continued to apply more of the mayo .. hers hands felt more gentle this time and I noticed it made me a little more hard. The dog went back at it except this time I was getting harder and harder. the dog was now licking up and down my shaft hitting all the right spots. I started to feel that familiar pressure up in my balls she saw the change and kept reapplying as needed so he didn’t stop. It was then I saw her taking pics and video of what was happening and she said It was so I would keep my mouth shut .. A few minutes of this dog’s tongue and I started to cum. It was the most intense orgasms I had ever had up until this point. Mt cum was spurting everywhere and she pulled the dog back and watched it drip all over me down my cock and balls. Looking down I was mess and again aware of what was going on and the embarrassment set it. she let the dog go and laughed as I squirmed as the dog cleaned me and hit ever ultra-sensitive spot making my almost scream. It did not stop until I was completely clean. She untied me threw my clothes at me and told me to leave and never come back . It was almost midnight the whole ordeal had taken almost 4 hours . I was broken humiliated my cock was raw and so sore . I walked home and passed out .
To be continued