u/watchingtv33

Spicy stuff starts after ***

I (M28, but 25 at the time) work as a competitive soccer coach. The teams I work with travel 3-4 times a year so that means I get a lot of time in hotels with some of the team moms. I think I’m a pretty decent looking guy, 5’10, tattoos and I’m in pretty good shape, so it isn’t uncommon for the moms to playfully flirt with me. I flirt back a little but never with a married mom I don’t want to push that boundary, but if it’s a single mom and she’s openly flirting with me then it’s 100% fair game.

So a few years ago we’re in Phoenix for a tournament and this mom, Lisa (F39), spends the weekend talking more to me than she usually does. I never met her kids dad, so I correctly assumed she was single. Lisa was a cute, shorter brunette woman who was kind of pale with smaller tits but with an ass that made all the dads turn and look whenever she walked by. I definitely enjoyed the warm Phoenix weather seeing her in shorts that seemed to be getting shorter every time I saw her, but I’m sure that was just my imagination.

After each game Lisa would come and give me a high five and tell me “Great game Coach” regardless of the result. After each game the high five would linger so we’d be holding hands for a few seconds.

Saturday night we decide to order some pizzas for a team dinner at the hotel. I sit next to Lisa and some of the other parents around a small table, and I purposefully leave my leg in Lisa’s space so our legs touch and she doesn’t pull away.
The night wraps up and I hang behind with Lisa to help her clean up the mess the team made, and the rest of the parents go make sure the kids all get to bed.

We pick up the last of the garbage and Lisa turns to me, “God I really wish this hotel had a bar. I could go for a beer.”
I smile at her and say “Well, if you want… I have a 6 pack in the refrigerator in my room. Night cap?”
“Lead the way,” she responds with a cheeky smile.

We get to my room and I grab 2 beers out of my mini fridge and we sit on the edge of my bed as we both take a sip.
“Do you get parents to come up to your room often?” Lisa asked.
“Nope, this is a rare occasion,” I respond
“Why am I so lucky?”
“Because you look so good in those shorts…” I say as I lean in.

***
She meets me and leans in and we start to kiss. Softly at first, but soon Lisa throws a leg over my lap and straddles me. We make out as she starts to grind against my hardening bulge. She’s essentially dry fucking me and her breaths get quicker while she rubs herself desperately against my bulge.

We’re both still holding our drinks so I have to stop her and make her get off of me and tell her to put the beers on the desk in front of the bed. I get up behind her as she sets them down and push her hair aside and kiss her neck. She braces her hands on the desk and bends over for me to rub my bulge on her from behind. Her big ass feels amazing even with the shorts on, but soon she turns around and gives me another kiss before Lisa drops to her knees and pulls my shorts off. Without hesitation she takes my dick her hand and licks from the base to the tip cleaning the precum that was dripping from it. She then takes it all the way in her mouth and looks up at me as she does her best to please me with her mouth. I almost cum just from the realization that I have this beautiful milf sucking me off after I’ve been eyefucking her all weekend.

After giving me head for a little while she stops and stands up. She leans in and gives me a kiss making me taste myself on her. She then drops her shorts and panties standing in front of me in just a tank top. She bends over the bed and I have to tell her, “I don’t have a condom.” And she responds, “I don’t care. Just don’t cum in me. But please fuck me.”

I rub her pussy gently with the tip of my cock before I slowly push it inside of her. As I go deeper she lets out “Ohhhhhh… yesssss….” I grip her hips and fuck her harder and her moans get louder. I’m still in disbelief that I have her in the room with me, and I have this big ass in front of me taking my back shots.

I keep fucking her doggystyle trying my hardest not to cum, but she reaches a hand down between her legs and reaches back and starts to massage my balls and she starts to say “Fuck you’re so big Coach. You’re amazing Coach please let me make you cum.” and nothing gets me going like dirty talk like that, so all I can get is a few more strokes in before I have to announce “Lisa I’m about to cum baby” and she starts throwing her ass back at me and demands “Cum on me Coach please!” So I quickly pull out and shoot rope after rope on her ass and on her back.

She lays there while I grab a towel and help clean her off. She gets dressed and I walk her to the door and she said “Thank you for that Coach. I really enjoyed it. I can’t wait for the next trip.” Lisa gives me a kiss good night and heads back to her room.

Spicy stuff starts after ***

I (M28, but 25 at the time) work as a competitive soccer coach. The teams I work with travel 3-4 times a year so that means I get a lot of time in hotels with some of the team moms. I think I’m a pretty decent looking guy, 5’10, tattoos and I’m in pretty good shape, so it isn’t uncommon for the moms to playfully flirt with me. I flirt back a little but never with a married mom I don’t want to push that boundary, but if it’s a single mom and she’s openly flirting with me then it’s 100% fair game.

So a few years ago we’re in Phoenix for a tournament and this mom, Lisa (F39), spends the weekend talking more to me than she usually does. I never met her kids dad, so I correctly assumed she was single. Lisa was a cute, shorter brunette woman who was kind of pale with smaller tits but with an ass that made all the dads turn and look whenever she walked by. I definitely enjoyed the warm Phoenix weather seeing her in shorts that seemed to be getting shorter every time I saw her, but I’m sure that was just my imagination.

After each game Lisa would come and give me a high five and tell me “Great game Coach” regardless of the result. After each game the high five would linger so we’d be holding hands for a few seconds.

Saturday night we decide to order some pizzas for a team dinner at the hotel. I sit next to Lisa and some of the other parents around a small table, and I purposefully leave my leg in Lisa’s space so our legs touch and she doesn’t pull away.
The night wraps up and I hang behind with Lisa to help her clean up the mess the team made, and the rest of the parents go make sure the kids all get to bed.

We pick up the last of the garbage and Lisa turns to me, “God I really wish this hotel had a bar. I could go for a beer.”
I smile at her and say “Well, if you want… I have a 6 pack in the refrigerator in my room. Night cap?”
“Lead the way,” she responds with a cheeky smile.

We get to my room and I grab 2 beers out of my mini fridge and we sit on the edge of my bed as we both take a sip.
“Do you get parents to come up to your room often?” Lisa asked.
“Nope, this is a rare occasion,” I respond
“Why am I so lucky?”
“Because you look so good in those shorts…” I say as I lean in.

***
She meets me and leans in and we start to kiss. Softly at first, but soon Lisa throws a leg over my lap and straddles me. We make out as she starts to grind against my hardening bulge. She’s essentially dry fucking me and her breaths get quicker while she rubs herself desperately against my bulge.

We’re both still holding our drinks so I have to stop her and make her get off of me and tell her to put the beers on the desk in front of the bed. I get up behind her as she sets them down and push her hair aside and kiss her neck. She braces her hands on the desk and bends over for me to rub my bulge on her from behind. Her big ass feels amazing even with the shorts on, but soon she turns around and gives me another kiss before Lisa drops to her knees and pulls my shorts off. Without hesitation she takes my dick her hand and licks from the base to the tip cleaning the precum that was dripping from it. She then takes it all the way in her mouth and looks up at me as she does her best to please me with her mouth. I almost cum just from the realization that I have this beautiful milf sucking me off after I’ve been eyefucking her all weekend.

After giving me head for a little while she stops and stands up. She leans in and gives me a kiss making me taste myself on her. She then drops her shorts and panties standing in front of me in just a tank top. She bends over the bed and I have to tell her, “I don’t have a condom.” And she responds, “I don’t care. Just don’t cum in me. But please fuck me.”

I rub her pussy gently with the tip of my cock before I slowly push it inside of her. As I go deeper she lets out “Ohhhhhh… yesssss….” I grip her hips and fuck her harder and her moans get louder. I’m still in disbelief that I have her in the room with me, and I have this big ass in front of me taking my back shots.

I keep fucking her doggystyle trying my hardest not to cum, but she reaches a hand down between her legs and reaches back and starts to massage my balls and she starts to say “Fuck you’re so big Coach. You’re amazing Coach please let me make you cum.” and nothing gets me going like dirty talk like that, so all I can get is a few more strokes in before I have to announce “Lisa I’m about to cum baby” and she starts throwing her ass back at me and demands “Cum on me Coach please!” So I quickly pull out and shoot rope after rope on her ass and on her back.

She lays there while I grab a towel and help clean her off. She gets dressed and I walk her to the door and she said “Thank you for that Coach. I really enjoyed it. I can’t wait for the next trip.” Lisa gives me a kiss good night and heads back to her room.

This is my first time posting on Reddit, so let me know if you wanna hear more of my stories!

Spicy stuff starts after \*\*\*

I (28M) recently moved to a new city, and I decided to check out a bar a short drive away. It was a pretty slow night and I was sitting at the bar alone having a beer when I saw this older woman come in. She was about 5’3, blonde, wearing tight black jeans and a white button up shirt with the top 2 buttons unbuttoned and a push up bra underneath. She sat by herself on the opposite side of the bar, so I waited a few minutes to see if anyone was joining her.

After a couple of minutes she was still sitting alone so I decided why not shoot my shot? So I went up and approached her and just told her I thought she was beautiful and if I could sit with her. We chitchat and she tells me she’s recently divorced after her husband cheated on her. 2 beers later she’s holding my hand telling me she has the house to herself tonight if I wanted to follow her home.

I made sure to cover her tab and followed her out. We get to her house and she leads me inside.

\*\*\*

The moment the door closes behind me I grab her arm and gently push her against the front door. We start to make out and her hands rub up and down my back while my hands reach down and grip her ass. I pick her up and she wraps her legs around my waist as she points me in the direction of her room.

I throw her on the bed and unbutton her jeans as she unbuttons her shirt. I peel her skinny jeans off of her until she’s laying there just in a sexy little black thong and a black push up bra. I drop my head between her legs and pull her thong to the side and eat her out. Her moans echo throughout her bed room as she wraps her legs around my head and grips my hair pulling me closer to her wet pussy.

As she’s getting closer she gasps out “please fuck me” so I do as I told. I get my condom on and she gets face down ass up. I used one hand to guide myself in her and one hand to grip her little waist. I’m not massive or anything, but she made a noise like it was the biggest dick she’d ever taken.

Once I was fully inside of her she started begging “fuck me hard please it’s been so long.” I started giving her deep strokes giving her exactly what she needed. Her hair was in a ponytail so I grabbed her ponytail and pulled her head back as I fucked her from behind. She started repeating “I’m gonna cum I’m gonna cum” and I made sure I kept doing exactly what I was doing to help her finish.

Once she finished I was still hard, so she caught her breath and told me to lay on my back. She pulled the condom off of me and gave me head. It wasn’t the best blowjob I’ve ever gotten but she was so enthusiastic and she was being so vocal that it wasn’t long before I busted in her mouth. Unfortunately she didn’t swallow it she ran off to her bathroom and spit it in the sink.

The night ended and I got her number, but when I texted her she told me I was the same age as her daughter and felt weird about seeing me again. Who knows though maybe I’ll run into her at that bar again and she’ll change her mind!