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Older Neighbor Part 2 Bottomless Happy Hour

My neighbor Megan and I would often get together for happy hour, and following an evening where we ended up masturbating together, we started to make both happy hour and masturbating together part of a regular routine.Megan was forty-two years old, slender and tall standing about six-three in height. She had long, curly, reddish-brown hair, perfect handful breasts, a beautiful face, and a very tantalizing ass. Most of the time she had a full bush of pubic hair that was bright reddish orange,...

Masturbation

Older Friend

John moved in to the house 10 doors down about 6 years ago, he is a 74-year-old man that would pass for someone in their mis 50s. He moved in with his wife, she sadly passed 4 years ago.I chat to John on a regular basis and help him with his garden and share the od beer over a warm summer night.I had arranged to meet john on Sunday to help out, it was 10am and I arrived at the back door. I knocked, no answer, I called out. The door was open so in I went.This led to the laundry room, there was...

Older Male sex 2

After fucking him a few times he ended up wanting to expand our hot gay sex activities. The town he lived in had a nice big lake that he frequented and so he told me that he wanted me to fuck him there. At first I said no, but he kept asking me and so I figured i'd give it a try, being that I was horny thinking about fucking him again. We met up at his place, again, as we packed our things, and drove together to the lake. A short 15 minute drive. We got there and we took our things as we walked...

Older man teaches me to masturbate 3

I kept going round to Alan's house most weekends all that Summer. Sometimes we would sit together and Alan would watch me as I took my clothes off and wanked over pictures of sexy women in his magazines. He really enjoyed seeing me ejaculate and several times said that I should do it into my hand so that I could swallow my own cum to see how it tasted. The first time I did it, it felt a bit odd although as I'd already swallowed Alan's spunk it wasn't so strange to do. I didn't mind the taste...

Older man teaches me to masturbate 2

I was so grateful to Alan for showing me how to wank and I now had the confidence to carry on like there was no stopping me. I understood that it was probably wrong to do it together like we did so I didn't say anything to anybody about it, it was our secret. That first night and early morning I had masturbated three times and my balls ached which, I guess was normal for the first time. I kept thinking about being in Alan's back room with my pants off and him stroking my penis and when I did I...

Older man teaches me to masturbate

I was just past my fo**teenth birthday and used to go and help a local man out who was retired and didn't get out as much as he used to. It was part of a scheme run by my local Sunday school although I wasn't really a church goer. Alan was about 64 and a widower, he was a really friendly guy, balding and with a bit of a tummy but a really nice guy to spend time with and always showed a lot of interest in me and what I was doing.It was summer time and I went round to his house with some shopping...

Older friend 2

This became a regular thing with Gary as I wasnt seriously dating and my mate big Ray was seeing someone so we didnt get together much. It was always in Gary's house and I made sure no one would see me. I didnt want anyone to think I was homosexual (stupid I know but they were the times then). I justified doing things with Gary was just simple curiosity and sexual release. To be fair it was very exciting and he was very discreet and he loved our sessions as I did too.He used to get me naked and...

Older Man 6 Boys rsquo Second Orgy

This story is complete without needing to read past installments (I think). It is, however, Chapter 4 of the sexual adventures started in Daddy's First Bukkake, Will Strikes Again and Mr Greig and the Boys: Part Three. I would heartily recommend reading those before continuing here.Mr Greig and the BoysChapter 4LATE TO THE BOYS’ ORGY"And I don't even know what's going on in the stockroom," my coworker Sara was droning on.I couldn't have been more annoyed. Will and his eighteen-year-old friends...

Older Guy wanted my pussy

What really happened this morning?I recently made a gym in my garage, I go out there twice a day to work out while my elderly neighbour is doing some projects in his.This morning I came out in my usual sports bra, baggy tee and yoga pants. I caught him looking me up and down, his eyes lingering on my erect nipples, so I smiled and sauntered away, I was working up quite a sweat when he knocked on the garage door.It’s only neighborly to invite him in, but I was in the middle of my run on my...

Older Man Samples Lynn Chapter 3

Charles and my wife lead the way to his bedroom. The bedroom also has a good view. Charles has a king size four poster bed. Against one wall he has positioned a mirror. The covers and sheets are pulled back. There are two pillows stacked in the center. He is obviously prepared. Charles and Lynn passionately kiss standing next to the bed. I cup one of her ass cheeks while Charles cups the other. "Well, my little married slut. Are you ready?" "Yeah, I'm ready." "Ready for what?" She leans on the...

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Older man samples Lynn Chapter 2

This is a continuation of a husband sharing his wife. For context, Chapter 1 should be read first. There are references to incidents and characters from “The New Client Series.” Like the other stories I have written, it contains, wife infidelity, cuckolding, multiple partners, and voyeurism. I appreciate your comments, suggestions and encouragement. The four of us walk down the driveway to the sidewalk. Lynn and Charles are walking next to one another. To the casual observer it would appear my...

Cuckold

Older for Younger

I had only just turned 18 when I happened to stumble across my old head master in a shopping centre. Now I had always had a crush on him when I used to attend his lessons at school. You see I have a thing about a father figure. We said hello to one another in passing like you do on seeing someone from your past. He asked me if I would like to go for a coffee in the precinct. I agreed to his suggestion as I was at a loose end, and I thought to myself, “Why not”. We got talking about the old...

Older man rsquo s first time

I meet him online, his name was Eric. He knew I had never been with another guy before, and after a few more times messaging back and forth, agreed to meet. I nervously asked what we might do when we got together, what was he looking for sexually. Eric said it was always better, and more fun, to let things happen naturally. “Just see where the night takes us” he said.We met at the bar of his hotel and before too long, we headed up to his room. I was incredibly nervous, but he was calm and...

Older lady next door at last

This is a true story about some thing I had wanted to happen for ages.After my wife passed away I moved house only just up the road about 250 yards it was a four bed on a private estate. My neighbors were great one side but the other I used to say hi but that was all then the funny ones put a for sale sign up. They sold to a widow she was a very active 70 year old at the time I was 50 for the story I will change her name, I will call her Ann. Ann was great always talking and chatting when ever...

Older now ready for more

I had finally done it! I stopped fantasizing and started doing. I had placed an ad on a gay dating website and took the leap. I had been with two guys now, one my age, "Joe" and one younger, "Kimmy." I meet them both on the website. Kimmy reached out to me the next day after I had picked him up and we parked. We ended up kissing and sucking each other to orgasm in my car. Joe was a regular guys guy but Kimmy was my feminine, so when Kimmy wrote that he would like to see me again and dress up...

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