I [24M]coached a youth team and I slept with one of the single moms [31F] [MF]
Sorry this got a little long - it's a true story from a few years ago with names changed.
I grew up playing sports, and two years after college I got a career job offer I couldn't pass up a few states away. I took the offer, and when I arrived I joined a local men's league to meet new folks.
A bunch of the guys in the league convinced me to put my experience to use and become a certified coach to help their youth program the next season. No need to get into details, but between when I agreed to help out and the start of the season there was a minor financial scandal in the youth program and they lost a bunch of coaches and asked me to coach a travel team of 9 and 10 year olds.
The guys from my league made sure I was put in a good situation, and the kids were talented so we got off to a good start winning most of our games.
A few months into the season the tournaments started, and so did drinking with the parents in hotels (this was pre-COVID). It was at our second tournament and bunch us were in the bar on Friday night celebrating a win while the rest of the parents were at the pool watching the kids celebrate. As the night passed, there were only 4 of use left in the bar. Myself, a couple (I'll call them the Johnsons) and a single mom (I'll call her Emily). I was chatting with Mr Johnson, talking sports and work when the last two kids came in. The Johnson's son and Jake, Emily's son, ready to head up for bed.
Mrs Johnson noticed that Emily still had a full drink, and offered to make sure Jake got to their room ok because we were all on the same floor. Emily smiled, thanked her and and asked if I was going to stay for a bit. I'd had a few drinks, was feeling good, and thinking that Emily was pretty cute, so why not?
Emily was about average height, but fit, she looked like she was blessed the a great metabolism, went to spin class/yoga 5 days a week or both. She had great legs and an ass that I had noticed when she wore yoga pants or jeans. She often wore less revealing tops, so I wasn't sure about her breasts. I knew she wasn't flat chested, but I didn't think she was busty either.
I hadn't chatted much with Emily other than a few quick conversations about the team, but nothing personal. Emily was very personable, and open about her life. She was working her way through school when she got pregnant with Jake and his father bailed as soon as she said she was keeping her child. I was really impressed when she talked about finishing school, getting another degree and a great job all while taking care of her son as a single mom.
Again, having had a few drinks, I couldn't help but say what came to mind, that she looked like she'd also done a great job of taking care of herself, and gave her a wink. She blushed, and said thanks. She confessed that it started out try to lose the baby weight and make her ex jealous, but she realized she felt better when she ate well and worked out. Working out had now become her "me time" and it was nice to hear someone noticed. I commented that I'm sure lots of guys have to notice her. She sighed, and admitted while she did catch guys glimpsing at her, her life was either spent at work or with her son, so no one ever approached her. I could sense a hint of frustration as she talked.
She then turned the conversation to me, and asked if I'd met anyone since moving to town. I admitted that I'd been on a few dates, had some fun, but hadn't found the right woman. Her eyebrow raised when I said I'd had some fun, and with a devilish grin she asked if I cared to share the details of "had some fun". I panicked a little, not wanting to say something wrong I said I wasn't one to kiss and tell. Emily took the last sip of her drink, and said she'd just have to let her imagination run wild then, but it was time for her to head up. I finished my drink and said I'd head out too.
We continued chatting to the elevator, and up to our floor (the whole team had a room block). We got off the elevator and walked to our rooms. I got to my room first, but it turned out she was next door! I thought about inviting her in, but the chat had cooled off in the elevator, and I didn't have a drink to offer, so I felt it was too bold.
Once in my room saw the door that connected our rooms, and once again I thought about inviting her over. Maybe just knock and see what happens? I decided not too, and got ready for bed. Minutes after brushing my teeth and hopping into bed, I started to think about Emily, and slipped my hand into my shorts.
No sooner did my hand reach my cock than there was a soft knock on the door connecting my room to Emily's. I got out of bed and opened the door. Standing before me, Emily looked great. I don't have a milf fetish, but there was something incredibly sexy seeing her standing there in an old tshirt, and bikini panties. She smiled and said, "I heard you don't kiss and tell, is that true?" I laughed and let her in.
Emily walked by me and hopped in my bed, I followed and no sooner did I hit the sheets than we were making out. She claimed she'd been in a dry spell, but her kissing was fantastic. My hands roamed her body, exploring every inch, teasing her more sensitive areas. Her ass felt as great as I thought it would, and my cock stiffened. I eventually removed her t-shirt and, wow. Her tits were a nice handful, with rock hard nipples and her tummy was firm. She should have been showing off more! I kissed along her neck and collarbone, working my way slowly to her nipples. When I finally got there she rewarded me with the hottest moan. I swirled my tongue around her nipples, and even gave them a little nibble.
I eventually worked my way down her stomach, kissing and teasing along the way. I then pulled off her panties. Kissing and licking her legs. Teasing her by getting oh so close to her pussy before finally zeroing in and eating her out. Her well manicured pussy was soaking wet and delicious. I was deliberate with my tongue, paying attention to her moans, and her body's reactions. Her legs got more and more tense encouraging me to keep going, starting to focus on her clit. Her morning increased and she put her hand on my head and pushed my face into her pussy. Soon she said, "I'm cumming" and squeezed my head with her thighs. I kept licking and eventually she pushed me off.
