Helping Each Other [MF]

I have been a widow for about a year and a half. I’m 67. I had never been with another woman other than my wife. We always kept a very positive view of sex and had a very active sex life. We talked a few times about what we would do when either of us lost the other, and always said that we would want the other to find a new partner. Naturally, things had been difficult so dating is not something that had been on my mind.

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My wife and I went to the same gym for years. The staff at this place has always been friendly to us. A young woman who goes by Maddie has been working at this gym for the last two years. My wife and I got to know her quite well. First with small talk on our way in or out of the gym, but later our conversations became more wholesome. We knew she didn’t make it to college right after high school and had been struggling to make it on her own. She is 22. One day when her car had broken down we gave her a ride home after hours. We developed a sort of parental friendship, you could say. We baked cookies for her and she took care of our dogs when we traveled. My wife and I didn’t have children.

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You know where this is going. I’ve read so many stories here and I’m just excited to tell someone what happened next. I should now brag a little bit and describe Maddie. She is about 5’6″, with light brown, shoulder-length hair and brown eyes. She is incredibly fit, with an hourglass figure, small waist and wide hips. She has round and ample butt cheeks that move up and down perfectly when she walks. She has generous, C-cup breasts and fair skin. Maddie has been sweet to me this last year, and ever since I became a widow our conversations have taken a caring, genuine tone. She has brought me food to take home more than once. Last week after my workout she asked me if I needed anything and I said jokingly “some company would be nice”. I don’t even know why I said it, but once the words came out I realized just how absurd it was.

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“I’m out in 10 minutes if you want to wait for me,” she said. I did not know what to do or say next. “I’m taking the dogs to the park, I’m sure they’d love to see you,” I said. “That’ll be great! I kind of need someone to talk to,” she said. About 10 minutes later, I was outside my home and she was just arriving. She was our dog-sitter, so she already knew where I’d be. We walked together to the park nearby and had a pleasant talk. “It’s nice to have someone to talk to,” I told her. “Yeah, me too,” she said. She told me about her lack of support from her family, and that working 2 jobs was hard, and that her last boyfriend cheated on her. She had been single for a few months now. Also, she couldn’t save enough for tuition and she was feeling a bit desperate. My wife and I had offered to help her more than once and she would decline our help. We could afford some of her costs, no problem. “I was thinking about how you and [my wife’s name] had always offered to help me. I was thinking that I could use the help,” she admitted. I told her that I would be glad to help her out.

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“But I wouldn’t like to, like, do nothing in return. You have always been very sweet to me, and well, I’m kind of tired of men my age. I was wondering if you would be interested in something more… fun to do than walk in the park,” said Maddie. “I would like to *help* you too,” she added. And when she said the word “help”, she reached out for my arm and gave it a little squeeze. I got the hint, but I wasn’t sure I was ready to believe what I was hearing. “Do you mean something more fun, as in, adult fun?”, I finally asked after a few seconds of indecision. “Only if you’d like to, of course! I’m sorry, I don’t mean to be offensive or anything,” she said. “No, not at all,” I told her. “It’s just like, well, I wasn’t expecting you to say these things to me,” I admitted. “You’re kind, you’re a good person, you’re probably missing intimacy as much as I do, so I think it could work out very well for you and me,” she said.

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Within minutes we were back at my place.

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We didn’t really address any of the details for how this special arrangement of ours was going to work out that day. “We’ll sort it out as we go, now let’s just have fun,” Maddie said. I told her that I had not had sex with anybody other than my wife. “That’s so sweet,” she said. “I’ve only done it with 3 guys, and never without a condom, so I’m clean too. I sort of wish I knew how it feels without one,” she admitted. “Oh, it’s the best,” I said. “I had a vasectomy many years ago,” I added. “Really?! Cool! I’d love to know how it feels all-natural like that!”, she said with excitement. I was very shy at first. I’m much older than her, I know I’m not really an attractive man at this age, I have wrinkles and thinning hair. I’m 5’10”, so I was taller than Maddie but didn’t really have much to offer her in the looks department. She could tell I was self-aware. “I want you to enjoy yourself and have fun. I don’t care about looks, but about hearts, and you have a kind heart and I *want* you to make love to me. I wouldn’t do anything like this with any other person other than you and only because we’ve known each other for so long. I trust you,” she said. Her words helped me relax and I got harder under the sheets. I still didn’t let her see much of me.

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Maddie then began to get undressed in front of me. She turned around so I could see her amazing butt. She slowly removed her top, then her bra. Her skin was smooth and had pearly white tone. She had no tattoos or piercings other than her ears. She undid her pants and dropped them. She wore pink laced panties. Her big butt cheeks underneath her panties were like mountains waiting to be taken. “Wow,” I said out loud. Maddie giggled. “Are you a butt guy or a boobs guy?”, she asked me. I told her I was definitely a butt guy. “Good, ’cause I have ass for days! They’re are a real handful,” she said. Then she slid her panties down and turned around. Her breasts were perfect, with small light pink areolas. Her nipples were hardening, I could tell. “This is so exciting!”, she said to me. “Men look at me all day at the gym and stare, they probably all wish they could have me. Have you?” she asked. I admitted that I had.

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With a quick motion Maddie undid the bed and I was finally uncovered. I was nervous. “It’s okay, enjoy yourself,” she said as she reached out to my thigh and began to caress me. This got me harder. Maddie then reached out to my balls and shaft and played with them tenderly. She smiled as she reached down to kiss the tip of my cock. She then licked it just a little to tease me. She could tell I wanted her to keep going. Maddie bit her lip and looked me straight in the eye. She was teasing me. I had never had a blowjob with so much enthusiasm. Her head bobbed up and down with a perfect tempo, each time reaching all the way to the base of my shaft, and then going all the way back up. Up and down she went and it didn’t take me long to moan in absolute bliss. “I want to feel you inside of me,” she said. “Want to fuck me doggy?”, she asked me. I don’t think I’ve screamed the words “YES” as loudly as I did then.

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She got in all fours and waited for me to get around her. I slowly slid my cock inside her pussy. Now Maddie moaned in pleasure. “Wow! This feels so much better! Your dick feels amazing!”, she told me. “Fuck me,” she ordered me. “And when you’re done, fuck me again and again,” she said. Her dirty talk turned me on. Maddie was very vocal. She kept repeating phrases like “I’m yours” and “You own me” over and over. I was in heaven. I didn’t realize dirty talk could be so wonderful until then. My favorite phrase, I’ll have to admit, is when she kept telling me she was 22. “Fuck my 22-year old pussy,” she would say to my absolute delight. I squeezed her breasts from behind her, but kept her in doggy style position. I then pushed her onto her belly so I could ride her from behind. “I’ll be your fuck doll, make me yours!”, she said over and over. Her butt cheeks felt so incredible against my body. Soft, full and round. As they bounced against me, you could see the mounds of each butt cheek jiggle up and down. It was the most beautiful sight I’ve seen in a long time. I let myself go and fucked like I had never fucked before. I moaned in pleasure as I came inside Maddie, filling her pussy with my warm cum. “Yes! Give it to me, it feels SO GOOD,” she said.

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We cuddled and had a very intimate talk about what we like in bed and what turns us on. She said that me being older was a huge turn on for her and that talking dirty in bed was something she enjoyed (and I could tell this was true). I told her that, yes, her age was a turn on for me too and that everything we did that time was just perfect for me. We had sex just the way I like it. “If that’s what you like, then we’ll do it all again when you’re ready,” she said. We had one more round that evening before she went home. The next day we agreed to have this arrangement exclusively with each other while she is in college: We’ll meet 3-4 times a week and I’ll cover part of her tuition so she can drop one of her jobs. This will give her time to actually go to classes. I’ll write more as we have more meetings at my place, but for now I guess I’m a sugar daddy and I’m stoked.

Source: reddit.com/r/gonewildstories/comments/ai6pmc/helping_each_other_mf