[M]y sneakers let me get [F]risky with a MILF

I will admit it, I love sneakers, I have over 60 pairs of them. Basketball, Running etc, and they are always clean, some people call me OCD. A few years ago while running some errands I was approached by a women in her early 40’s during one of my stops and commented on how she like my sneakers. We made small talk about them and we both went on our way. When I leave the store she is walking out at the same time toward the same spot where I parked my car. We cross paths again and I went for it. I formally introduced myself and asked if she was involved with anyone as I didn’t see a ring on her finger. She said she was recently separated and wasn’t seeing anyone. I asked if she would like to grab a drink sometime and she agreed and we exchanged numbers. During the next few weeks we texted and talked but it was hard to find time due to her kids and ex not wanting to take the kids. Finally she had a free night and we met for drinks at an outdoor spot not to far from her house. I got there a few mins early and made sure to get a spot in the corner. In she walks wearing a sundress showing off her cleavage. Some of the guys at the bar were staring at her when she walked by which really turned me on. We talk for some time and the drinks are flowing before she excuses herself to the ladies room. When she returns there is a large smile on her face. She slides close to me and takes something out of her purse and puts it in my hand. I look down and it is her panties, and they are soaked. She smiles at me and suggests we leave and head back to her place. As soon as we arrive we are all over each other. I found out later that she had not been with a man in a long time and it showed. Her hands were all over me rubbing my chest and clawing at my back as we kissed on her sofa before she pulled her dress up to expose a small but firm set of tits. As I begin to suck them she works her way down my chest and unbuckles my belt and reaches her hand down my pants. While I am not lengthy I am extremely thick which she notices. She pushes me back on the sofa and slides off my shorts and starts to work my cock with such passion. Slobbering all over it and taking time to lick my balls and even faintly rubbing my asshole. This went on for a while until I was getting close to cumming. We agreed to move to the bedroom where she jumped on the bed and took off her sundress exposing a shaved pussy that was ready to be sucked and fucked. I didn’t waste anytime and slid my tongue on the outside of her lips teasing her while she moaned. She running her fingers through my hair as I moved to her clit and began sucking on it. This drove her crazy as she let out moans that scared me a bit. I continued with this and inserted two and then three fingers in her tight hole. This pushed her over the edge and she came so hard all over my face. Now covered in her juices I kiss her and she licks it all off and tells me to please fuck me raw. I insert my cock slowly as I want her to be able to take the whole thing. Once in I begin to slowly fuck her as she screams and moans loudly. We stay in missionary for some time and I tell her i am close. She tells me she isn’t on the please not to cum inside of her. I pull out and fire a few loads that land on her flat stomach. We both lay there and laugh as she cleans up with a towel. I spent the night and we fucked once in the pretty early as she had to get her kids. We hung out when she could for the next few months. and had a few more encounters but eventually we lost touch.

[M] [F] Workout turns into long weekend

Like most people during the first few months quarantine I think we all went through this in some capacity. Adjust to working from home, then became home projects then it was super frustrating because the weather was nice and we couldn’t do anything. Around the middle of June I started to ride my bike for longer and longer lengths of time. My goal by the end of the summer was 90 miles in one day. I would ride on weekends and when I was in a bad mood to blow off steam but I really wanted to push myself to see how far I could go. One of the benefits of living in a suburban area is there are tons of parks and trails where if you go at the right time you can have the place to yourself. I would typically go early in the morning before work and then mid morning on weekends. One weekend I was wrapping up a ride when I saw a guy who I played golf with talking to a female. I walk over and to chat and he introduced me to “Andrea”. Andrea was a short Indian girl who was wearing a white sports bra and black yoga pants. She clearly was into working out as her body was fantastic. We talked for a good 10 mins before we went out separate ways. The next morning I get a text from my buddy who asked if it was ok if Andrea gave me a call. Being single and pretty horny I give him the ok. She texts that night and we text back and forth for a few hours before we both turn in for the night. I wake up the next morning to a text from her that says it was nice texting with you last night would like to talk on the phone tonight if you are free. I of course reply i would love to and we chatted that night and the next few nights about everything from work, sports, food etc. The topic of sex never came up and I was ok as she seemed like a very reserved person The week of July 4th we decided to finally get together at my place as the COVID lockdown had been lifted. She shows up on time and looking fantastic in a pair of jeans, black tank top, hair pulled back and smelling amazing. Let me be the first to say as a white guy I am not normally attracted to Indian women but something about her made my cock hard.

[M], [F] Milf Season Round 2

Thanks for the kind words on my last post. This story is from the second time that Anne and I hooked up.

After the last time she came in and we acted like nothing happened it was a few weeks until I saw her in the store again. I did not have her number to reach out to her either. Those weeks were brutal. I would jerk off thinking about licking her ass and while she played with her clit and shooting loads right into her mature pussy. In between Thanksgiving and Christmas she came in looking amazing. We live in a colder climate so she had on those fuck me thigh high boots with a sweater that made her tits look amazing. She pulled me aside and asked if we could talk. My first thought was oh shit she is pregnant. Luckily that wasn’t the case. She apologized for not coming into the past few weeks, she told me she was traveling a bunch for work and her baby sitter was doing the food shopping. Anytime she would come home from her trips she would be with the kids and crash. I told her no need to explain anything to me as it was just a hookup and it’s o.k. She told me she wanted to make it up to me, and of course I said yes. She asked if I was working Sunday night and I wasn’t. She told me she would pick me up in front of the store around 4. Told me to dress up a bit. Not a suit but no jeans.

[MF] MILF Season

[MF] Milf on the Prowl

Like a lot of college kids, I lived at home and worked part time at a grocery store a few towns over from mine. The pay was decent and since I worked there since sophomore year of high school they liked me and worked with my school schedule. Of course you would always see your regulars so you would make small talk with them about sports, weather or whatever was on the news that week. One woman (let’s call her Anne) mid 40ish would come in multiple times a week always dressed very professionally like she was coming from an office and always had a nice smell to her. While not the most attractive face she had a killer body with legs for days. I think the fact that she carried herself so well was a big turn on for me. About me, played baseball and soccer in high school so still in good shape (at the time) and very lucky to be blessed with a thick cock.