SnowboardReddit, Author at NSFW story — Page 2 of 3

Dressing Shopping with [M]y [F]WB

This is a story that just happened over the last weekend. As the majority of us know, with Covid restrictions lifting more and more, it is allowing more and more things to open and get scheduled for the future, and that allowed this to happen. Last Friday my FWB Erin texted me and asked me if I would go shopping with her and help her pick out a dress for a wedding that she was asked to attend in mid-June, having nothing better to do due to rainy, cool weather I agreed.

Erin picked me up on Saturday morning and we headed to the local mall where she had a choice of many stores for a semi-formal dress. When we got there, she explained to me that she had not received a “plus one,” or else I would have been her date like normal, but she always appreciated my feedback on her outfits, usually once they were on the floor, but still good feedback. Over the next few hours, we went in and out of all the stores where she tried on multiple dresses and came out modeling them for me. For those who haven’t read my other stories, Erin is a 46 divorced mom of two who I was introduced to by my former FWB Kat. She is about 5’8 and about 150lbs, but it is all curves; a great “mom” ass and a set of 36D tits. Read more »

Former Coworker Meet at Conference [MF] (Long)

Longer than usual, sexy time starts at ***

I just got home from where this happened and considering my sex life with my FWB has been rather “vanilla,” I thought that something that occurred last night/today would be of interest. If you’ve read my stories before you know that I am a teacher. I try not to brag but I tend to think I’m pretty good at what I do, and apparently the staff at my district has noticed. Anyway, with Covid restrictions easing I was asked to speak to a small regional conference about what my school/district is doing with dual-credit classes where our students earn both high school and college credit if they pass the class, I agreed and got to the site of the conference on Tuesday evening; with the schedule to speak in the morning and the afternoon Wednesday, and then come home this morning.

A little bit of backstory that is important; before I took my current job, I worked three years in the rural part of my state because there weren’t positions in my hometown when I got out of college. I really did enjoy working there, but better pay and closer to family ultimately and a moved home 7 years ago. Read more »

[M] [F]irst Threesome with my then girlfriend and her friend

I normally would be telling you a story of my latest time with my MILF FWB Erin, but while we have hooked up, nothing has been exciting enough to write for you all. Instead after sex one night, Erin asked me “Other than with Kat (former FWB) and I, what is the hottest sex you have ever had?” After thinking about it, I remembered this event with an ex-girlfriend and her best friend in what was my first threesome.

So, a little bit of backstory, this occurred in 2013 and I was dating a girl by the name of Emily, she was a grad student at the college about 30 minutes from my hometown. We were set up by a mutual friend and really hit it off. Emily was 2 years younger than me, about 5’8, but what really set her apart was her tits. Emily weighed about 120 but had a set of tits that spilled out of her 42DD bras; put them in a push-up bra and a low-cut shirt and guys stared whenever she walked by. Anyway, Emily was from the west coast (I live on the east coast) and went home for the holidays, I had never met her father so we decided that I would come out and spend Christmas and New Years with her family so I could meet him and for New Years, we would spend in her undergrad college town with some of her old friends. Read more »

Sex with a [M]IL[F] at a Charity Gala: Part 2

Since a few people have asked for what happened in the morning, here is part 2 of “Sex with a MILF at a charity gala.” A quick recap though: I have a MILF FWB Erin who is 44; she is a lawyer, and I went to a charity event with her where we had a quickie in an empty room of her country club before going back to her house where we had sex again. I stayed the night and woke up the next morning to a note on the door that read: “Come on downstairs, I’m out back in the hot tub if you want to join.” That’s where this picks up. Read more »

All Good Things Must End [MF]

Like always, all good things must come to an end. Since we started back to school/work, I hadn’t heard much from my MILF FWB Kat who is also a teacher with me. I figured we were both just so busy adapting to virtual and in person learning that neither of us had time to consider Kat’s idea of me fucking her over and on top of her desk after school one day. That all changed the other day; when I got a text around lunch time that read, “Come to my room after school, we need to talk.” Never a good sign; I was afraid that maybe one of her kids had found out about us or something was up, so I responded with “Okay, hope everything is all right. See you at the end of the day.” Read more »

Almost getting caught on the boat. [MF]

One of the many perks of graduating college without any debt and inheriting a house from a family friend who had no kids, is that I have been able to spend my pay foolishly as my mother puts it. Last summer I bought a used speedboat and have spent a lot of time over the last 2 summers just relaxing on the river with friends and family; that provides the opportunity for this story/event to take place.

Earlier this week I ( 32, “Dad Bod” Teacher) had been talking to my Coworker MILF FWB Kat (45, 38b) and she was complaining about how her and her sons hadn’t been able to get over to their beach condo due to rentals and how she was bored. I had mentioned my boat before and I said to her, “Why don’t you and the boys and I go out on my boat tomorrow for the afternoon? It’ll be good to catch up with Brad (oldest son) and see Grayson (youngest son) before the school year starts.” Kat responded back, “Well Grayson has to work, but Brad would probably be game, I’ll get back to you.” A few hours later, my phone dinged and showed a message from Kat that said, “ We are good for tomorrow, but Brad want’s to know if Ashley (his girlfriend) can come too?) Since I had both Brad and Ashley in class as high school seniors and now they were juniors in college, I told her, “That’s fine with me. We can just leave from my house around 10:30, just come on over around then.” Read more »

First Time Anal [MF]

Last Thursday, Kat texted me and told me “My divorce finalized yesterday! Why don’t you to come over around 8 tonight. You’re staying the night.” I texted back, “Congratulations and that sounds good ;-). Do I need to bring anything?” She responded with, “Nope everything is good to go.” Around 8, I got to Kat’s house, when I knocked on the door, she answered wearing a light pink silk robe and holding a glass of wine. I could tell that she wasn’t wearing much, if anything under the robe because I could see her nipples pushing through the fabric. I hugged her and congratulated her again on the divorce finalizing. She smiled and said “Yes! That is a huge load off my shoulders. We talked for a few moments about how her kids were handling it as she finished her glass of wine. As we relaxed, Kat began to slowly stoke my thigh, not wanting to rush her or anything I didn’t say anything, but my cock had other ideas. As it began to harden, Kat noticed and said, “Why don’t we head to the bedroom?” Read more »

Installing Ceiling Fans [MF]

Hey everyone, I haven’t posted in a month or so; I’ve hooked up with Kat a few times, but nothing to “write home about.” Last week though, that changed with getting a text from her friend who we’ve had two threesomes with. Erin texted me the week before the 4th of July saying that she had two new outdoor ceiling fans that needed installed on her deck before she had her family over for the 4th and was wondering if I would install them. I agreed and we set up a time to get them taken care of.

I drove out to Erin’s house and when I pulled into the driveway, she came out of the garage wearing a pair of leggings and a tank top. For those who don’t remember or know, Erin is a divorced mom who is 44, 5’8 and totally stacked in the tits (36D) and ass department. She is definitely what porn would call a MILF. We greeted each other with a hug, and she said ,“Thank you so much for doing this on such short notice! I had one of the electrical companies lined up to do this, but they are swapped and had a couple guys quit so they had to cancel.” I responded with “Not a problem, they shouldn’t take too long!” I followed her into the garage where the fans were sitting, seeing they were just standard Lowes brand fans that are a cake to install. I carried both of the fans down to her deck, then grabbed the ladder and my tools out of my truck. Read more »