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The Oldest Man I’ve Been With

The oldest man I’ve ever been with was Tom, an 84 year old. We’ve gone to the same church for years and even though he was a quiet old man everyone knew him because he had gone there so long. His wife had passed away a while ago and everytime we talked he would always say I reminded him of her as a young girl.
One day he was talking with me and my mom when he mentioned to her he has trouble keeping up with cleaning because he was getting older so my mom volunteered me to come over and help. I was ok with it because he always seemed sweet and I liked to help so one day after church my mom dropped me off at his place.
His place wasn’t very messy at all but things were getting a bit dusty so I dusted and vacuumed and wiped down a bunch of his stuff while he helped himself to a glass of scotch and watched TV. His house isn’t too big so I finished after about an hour and told him I was all done.
He thanked me a lot and asked if I’d watch some TV with him before I go because he doesn’t have a lot of people visit. I told him of course and sat next to him. He put his arm around my shoulder and I didn’t think anything of it so I laid my head on his shoulder. We watched TV for a little bit and I started getting sl**py so I moved my head down to his lap.
After a few minutes he started petting my head a bit and he started breathing heavier so I could smell the scotch on his breath. Then I felt him starting to get hard. I remember thinking it was strange but I was very comfortable with him and feeling him start to get hard turned me on. I froze for a minute but then I moved my hand and started to slowly rub him through his pants. I looked up at him to see how he would react and he smiled, looked at me, and then kissed me on the forehead saying I was such a sweet girl. I smiled and started to unzip his pants and slide them down around his ankles. I was starting to get excited so I quickly took off my Sunday dress and my bra so I had nothing on but my white panties.
I started to jerk him off for a bit and he kept saying how sweet and pretty I was and how I was such a good little girl. Then I started to slowly suck on his cock and he started breathing really heavy. He kept one hand on my head and the other he had rubbing my body. I sucked his cock nice and slow going a little deeper every time. He kept calling me a good girl and his breathing was getting louder and louder. It took him a very long time to cum like around an hour but he kept talking to me the whole time and I would take breaks and jerk him off if I needed a breather. Eventually I could feel him shaking a bit and moaning quietly so I went as hard and fast as I could. He grabbed my head with both hands and gently pulled my head in as he came deep into my mouth. He came for a long time but once he finished I swallowed every drop and licked it clean. I laid my head on his lap and rested for a minute once I was done. My mom came shortly after and I went home.
Once a month I would volunteer to help clean his house and spend an hour blowing him until after about 7-8 months my mother thought it was strange I enjoyed going there so much so I decided to break it off. The last time I went over there I decided to surprise him. Every time I went he would say I reminded him of his wife so when I got there I asked if I could see try on his wife’s clothes. I thought he might get mad but he smiled and said of course. He took me to his bedroom and was very happy showing me all of his wife’s belongings. He let me try on some of her jewelry and her perfume. Then he told me he wanted me to see her favorite dress.
He pulled out a box and inside was a beautiful white dress. He told me it was her wedding dress and he would love if I tried it on. I said I wasn’t sure but he said please so I told him I would. I undressed down to my panties for him and then he helped slide it on. It wasn’t too fancy or fluffy, just a simple white dress. It wasn’t a perfect fit but it was close enough. He immediately started getting excited once I had it on. He seemed more energetic than ever. He started kissing me long and deep and squeezing my breasts through the dress.
He led me to the bed and had me sit on the edge of the bed. He unzipped his pants and slid them off with his boxers. He walked up to me and slid his cock in my mouth quickly. I couldn’t believe how excited he was. He grabbed my head firmly and thrusted in out. I started to gag after a minute so he slid it out and kissed me on the forehead. Then he laid me back and started to spread my legs. I should have told him to stop, I wasn’t on the pill but I loved how much he wanted me.
I spread my legs and he slid my panties off. Then he turned me around and got me on all fours, climbed on the bed, lifted up the back of the dress and stuck himself deep inside me. It hurt at first but I was very wet so he had no trouble getting it in. He squeezed my ass tightly as he thrusted in and out as hard as he could. I couldn’t stop moaning and he was breathing very heavy. He started calling me his wife’s name Diane. He would say oh Diane that feels so good. And say you’re such a sweet girl Diane. I started saying his name too. Don’t stop Tom. You feel so good inside me Tom.
He went for about 5 minutes before he started to cum. He said I love you Diane and I said love you too as he gripped me tight and thrusted as hard as he could. I could feel him push himself all the way in and feel his warm cum filling me up and I moaned loudly.
Once he was ready he got up and grabbed me a pair of his wife’s pajamas. He smiled at me and said we should probably change out of that dress now so I did. Once I was in her pajamas, he folded up the dress and we got into bed and laid together. We laid there for a while and kissed while he held me tight. I just kept thinking about how amazing he felt slowly dripping out of me. He was pantless still so after laying together for a while I started playing with his cock. It took a couple minutes but he started getting hard again. We kissed while I jerked him off for a minute and then I slid off my pajamas and got on top of him. I wanted him inside me again so I rubbed his cock against my pussy and slowly slid it in.
This time he lasted a lot longer. I started slow and then started thrusting harder and harder. After a while I was soaked in sweat from bouncing on him so much. I started getting exhausted but I didn’t want to stop. He kept saying I love you and calling me sweetie or Diane or baby girl. I kept saying I love him too and moaning at the top of my lungs. I’d bounce on him harder and faster til I couldn’t take anymore and then I’d lay on him for a minute and we’d kiss while I caught my breath.
Eventually I could tell he was breathing really heavy and his legs started to shake. I leaned forward to kiss him and he wrapped his hands around me. Then he rolled us over so he was on top and started thrusting into me as hard as he could. I screamed because his hands were squeezing me so tight it hurt but I loved feeling him thrusting so deep and hard. He went for another couple minutes and then he pushed himself as deep as he could as he came inside me. It felt like he was cumming for a long time, I could feel his hard cock twitching inside me and after he finished he basically collapsed and laid all his weight on me top of me. We were both so exhausted we laid like that for a while and almost fell asl**p. Eventually my mom called so we were f***ed to say our goodbyes and I went home. I still remember feeling him dripping out of me all the way home.

Updated: October 21, 2016 — 1:25 pm

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