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The widowed neighbor
My wife and I recently sold our house and moved to a bigger house in a nicer neighborhood after years of planning. Business is good and it felt like the right time. This was also the neighborhood that I grew up in so I was familiar some of our neighbors, including our new next door neighbor, Cindy. Cindy was my first crush growing up as her daughter and I were friends. Her husband died about 15 years in a tragic car crash.
The week we moved in was also the same week that my wife and son were scheduled to go on a weekend trip with his friend and friend's mom so it was a chaotic week. Friday night, not looking to do anything, I went across the street to the golf club we joined with the sole intention of getting drunk and eating too much food.
Cindy walked in, took her seat, which happened to be right next to me. We made small talk, caught up, and wound up eating dinner and having some drinks together. I noticed her body language was very open to me and my head started to wander a bit. Could it happen? Would it happen?
Not too long after these invasive thoughts, she said, "normally one of the busboys drives me home but since you're my neighbor, would you?" I said, "no problem, should we get our checks and get going?" she nodded yes and we left about 15 minutes later. On the way home, she said, "if you'd like, you can come in for another drink. I have some beer in the fridge for my son-in-law. You can take one of those...that is if your wife won't mind." I said, "sure, shes out of town anyway."
As we were walking in, she said, "can you poor me a glass of wine from the fridge? I need to go upstairs to use the restroom. I'll be right down." I told her yes and waited for her. Finally, 10 minutes later, she came down wearing a black lace push up bra, matching panties, and the bright red heels she had on during dinner. Without saying a word, she walked up to me, put her arms around me, kissed me and whispered "I want you to fuck me."
For reference, Cindy is 65 years old and still smoking hot. She's about 5'5 tall, maybe 110 pounds, solid 32B breasts, and great legs.
I wrapped my arms around her and lifted her off the ground and walked to the couch in the adjoining room. I set her down and she sat on the couch and immediately undid my belt and pants. She pushed them down, took my cock in her hand and said, "So much better than that busboy that normally drives me home." Before I could reply, my cock was in her mouth and she was sucking me off wonderfully. It was an incredible feeling and visual watching the first woman I ever jerked off to blowing me in her living room as I had fantasized about so long ago.
When I came in her mouth, she swallowed, stood up, and said follow me upstairs. We were barely in the bedroom before I had her bent over and leaning against the wall as I inserted myself in her. She let out this moan and just kept saying "Fuck me, fuck me, fuck me." We both orgasmed at the same time and then laid down on the bed. There were a few moments of silence and I said, "so you fuck the busboy every friday?" She said, "Most fridays. not every friday. depends on my mood. He's 18 and made the first move the first time he drove me home so I kept it going." I said, "That's awesome actually. That kid is a legend." She laughed and rolled over on top of me and said, "are we going to do this again?" I said "tonight or in the future? Tonight, absolutely. a few more times. in the future, i hope so." She said smiled at me and said, "Admit it. You had a crush on me when you were younger." I said, "A huge crush. At the risk of personal embarrassment, I'll admit that you were the first person I ever jerked off thinking about." Her eyes got big for a second and she said, "Oh my goodness. really?" I said, "yeah" She bit her lip, kissed my cheek and said, "Anything you want for the rest of the night is yours." I smiled at her and said, "I think another blowjob for now and then I want you to ride me." She said, "I'm going to make you cum more tonight than you've ever cum before in your life. I am so fucking turned on right now." She kissed me and then kissed the trail down to my cock.
By the time we finally fell asleep, I had cum 6 times after fucking her in multiple positions. We woke up around 8am and fucked twice more before I went home.
I see her nearly everyday but we have not yet had a chance for round 2. I can't wait for that chance.
OP here: I had round 2 not too long ago. She came by the house the week before christmas with a plate of cookies. My wife invited her in and they had wine together while I sat silently in the kitchen. When she was finished, I walked her out and said, "See you soon, thanks!" She said, "Your wife mentioned that she's taking your son to her aunt's for a sleepover tomorrow. If you're lonely, stop by." I said, "that's very nice of you. I may take you up on that." She said, "See you at 7." I walked over at 7 and she answered the door in underwear and stockings. We fucked like college kids all night. I walked home the next morning and showered before my wife and son got home. So much fun.
Tracy was the milf on the block, growing up I hung out with her son and daughter. She was on her second marriage, and he had a son also. One day her husband, step son, and her son was involved in an accident where a drunk driver collided with their vehicle, killing everyone in it. After the funeral, I knew this was my way in. Tracy works for an outreach center as a HR rep, she got me a job there as well, so I started to build a bond with her.
After the funeral we got close, I drove her to Doctor appts, helped out around the house, eventually I even rented the basement apartment to help with the bills. We made dinner for each other, started carpooling to work. Her daughter was away at college. It took me 2 years before I was able to be inside Tracy. We flirted all the time.
One night after work, sitting on the couch, she says I wanna sex, stupid me I said okay go find someone, and she replied are you sure you want me to do that? Or do you wanna fuck me? Ever since then, Tracy has been mine. Tracy is not a 10, her face is more like a 7, but her body is definitely a 10, huge tits.
Past 8 years she’s been mine, she has a tattoo with my name, wedding band that she wears now with the date we first had sex, had a secret wedding, vacations together, lots of nudes photos and videos, people still think I sleep in the basement, but I share a bed with her, and it’s the same bed she share with her late husband. Tracy is now 50, and I will be 31, and currently in a relationship. We agreed that even when I get married this will continue
After my lesbian neighbors split up, I was curious and went over to hang out. btw: F/19 & she's 36.
She was drinking wine and confessing how much she missed her ex but she was cheating. She started telling me how crazy she was in the bedroom. Things got heated and we ended up in her bedroom going down on each other and having sex. At the time, she was the oldest and most experienced woman I'd been with. No regrets