My MILF on the Golf Course [Str8][mF][MILF]

The country club isn’t always a great place to find girls, especially girls my age. Not many 18 or 19 year old chicks hang out at a golf course or the tennis courts unless their parents drag them for some lame brunch. For that reason, my summer job as a caddy was the worst. While my friends were off ogling girls in bikinis while they worked as a lifeguard, I was following middle-aged men around, carrying their golf bags as they knocked back Coors Light after Coors Light. The days were long, the sun was hot, and though I made some decent money, I was bored to tears and tired as hell. June dragged on and July was even worse. There was no way in hell I was going to come back to this crappy job next summer.

All of that changed the second week of August. Mr. Schmidt, one of the club’s top golfers, called me on Monday night and told me there was to be a change for his tee time the following morning. Instead of Mr. Schmidt, his two co-workers, and his chief client, Mrs. Schmidt and three other women from the country club would be taking the spot. When he said this, I was hopeful that he would tell me not to come in, but instead, he asked me to caddy for the four women. I naturally agreed, as my work wouldn’t change that drastically at all. I’d still be carrying clubs either way.

The next morning, I got up my normal time, hopped in my car, and headed toward the country club. When I arrived, Mrs. West was there and getting her clubs out of her Mercedes, but Mrs. Schmidt and the other two women had not yet arrived. I tied my shoes, put on my cap and headed up toward Mrs. West. She was always nicer to me than most people at the country club, so I didn’t mind approaching and saying good morning. As we exchanged pleasantries, three more cars pulled up. Mrs. Schmidt got out of her car and walked over to us. I had never formally met her, but we both recognized each other and introduced ourselves.

“Good Morning Michael. I’m Judy Schmidt, Kevin’s wife. Thank you for your flexibility this morning,” she said, extending her hand to shake mine.

“Nice to finally meet Mrs. Schmidt,” I responded.

“Please Michael, call me Judy,” she quipped back with a smile. That was pretty unusual for a country club member, but I appreciated the casual tone, especially from someone so attractive. Judy is quite a bit older than me, at least 45 or so, but she’s by far the sexiest woman who frequents the country club. The girls my own age are pretty cute, but Judy is in a different league. She’s about 5’6” with shoulder-length, reddish-blonde hair. She is perfectly curvy in all the right places, and I would always argue with the other caddies about whether or not her larger-than-average breasts are real. That morning on the first tee, a warm August morning, she was wearing a white golf skirt, cut above the knee and a pink polo shirt that really accentuated her beautiful tits. As the four women gathered their things and made their way to the tee box, I watched Judy’s round butt swing back and forth in the skirt, for the first time really enjoying my time on that golf course.

The first few holes went by in pretty much the same way they did every morning. The women all took their swings, most of them pretty good shots, hopped on the carts, and followed their balls toward the green. Every now and then I would make a suggestion on a club or an approach to hitting the ball, but for the most part, I just carried clubs. Around the fourth hole, the mimosas started flowing and by the seventh hole, all four women were a bit tipsy. Mrs. West and her best friend Ms. Anderson made a few comments to me about my butt in my shorts which made me chuckle a bit. They are old enough to be my mother, and even though I find them attractive, I felt a bit awkward receiving such a compliment. However, it was Judy that caught me the most off-guard.

At the eight hole, she was the last to take her shot. The other three women started off up the fairway to take their next shot when Judy came over to me for her club.

“I think I’ll take the wood for this hole,” she said, winking at me and gently grazing her hand across my crotch before taking her driver from my hand.

“Umm, what was that, Judy?” I asked, shocked but also slightly turned on.

“I think you heard me Michael,” she said, taking her driver from my hand and heading to line up her shot. As she walked toward the tee box, she moved her hips back and forth and faced away from me. When she bent over to place her ball, she very subtly but very deliberately hiked her skirt up just enough to reveal the very bottom of her ass in a bright-green thong. Completely dumbstruck, my jaw dropped and I just stared at her as she stood up straight and took her shot.

“That was a nice shot Judy,” I stammered, not quite sure what else to say.

“Thank you Michael, but I’ll be honest with you, I’m growing a bit bored,” she said with a mischievous smile. “I think we should take a break for a drink at the clubhouse once we reach the ninth hole.”

“Um, what about Mrs. West, Ms. Anderson, and Mrs. Wilson?” I mumble out, almost forgetting they were on the course.

“I’ve already spoken to them, Michael. They will be fine for the back nine. We can go for a drink and a chat,” she said, grabbing my hand and leading me to the golf cart. We drove up the fairway, Judy finished off her shot, and then instead of going to the next tee box, we went back up to the clubhouse. We walked through to the bar where Judy ordered two mimosas. Even though caddies aren’t technically supposed to drink while working, the club always told us not to refuse a drink from a member, especially if they were as high-profile as the Schmidts. We sat for a few moments at the bar before Judy put her drink down and turned toward me.

“So remember when I asked about that wood, Michael,” Judy said, not very subtly and quite loud as she moved her hand back to my crotch. I quickly grabbed her hand and moved it away from my increasingly hard dick.

“Judy,” I whispered. “We are sitting at the bar. What if somebody sees us. You’re married and I’m 18.”

“What does age have to do with this? Am I too old for you?”

“Ummm, no of course not, but we are still in the middle of the country club and you’re married,” I responded, my mind racing.

“First of all, stop brining up my husband. He’s not here, so don’t worry about him. You are right about us being in public though. Follow me,” she said with a wicked smile. She pulled me up by the hand and walked me down the hallway. I thought we were moving toward the front door but as we passed the door, I grew even more confused. We walked past the pro shop, past the men’s locker room, and stopped at the door for the women’s locker room. She looked over either shoulder and opened the door, pulling me behind her.

When we walked in the locker room, I heard a few showers running. We moved right toward that sound of running water and encountered two women that I recognized from the country club. They were the two always playing tennis, a bit younger than Judy. They jumped and immediately covered themselves when we walked in.

“Relax ladies, he’s with me. You know the drill,” Judy barked. The two women shut the showers off, giggled, and moved toward the towel racks. I wasn’t sure what drill she was talking about, but I did intend to find out. Once they turned the corner, Judy turned to me.

“Take your cock out,” she said to me. I just kind of mumbled something nonsensical.

“Don’t make me repeat myself Michael. Take your cock out,” she said, moving her hands to her hips. I was completely hard in my pants by this point, and started to undo my belt, still not quite believing it. As I unzipped my pants and pulled them down from my waist, my cock sprang to life, poking its head through the hole in the front of my boxers. Judy gave me a silent smile without saying anything.

“What now,” I stupidly asked, but still unsure of what was happening.

“Well, I can see that you’re pretty fucking hard,” she responded to me. “Why don’t you start jerking off and see how hard you can get? I’m going to make myself comfortable.” I complied and wrapped my fingers around my member. I slowly started to slide my hand up and down my shaft while Judy stared right at it. She unbuttoned the top button of her shirt and slid it up over her head, revealing a bra that matched the bright green color I saw on her thong back out on the course. Leaving her bra on, she hiked her skirt up a little bit and backed up toward the bench behind her.

“You don’t mind if I get in on the fun, do you?” She asked me. I looked at her with kind of a bewildered look, my hand still stroking my cock.

“Of course you don’t,” she answered before I could mutter a response. She leaned back on the bench and started to caress herself through the thin silk thong. The whole time, she was looking right at me, alternating her gaze between my cock and my face. As for me, I was looking right at her pussy the whole time, hoping she would take more of her clothes off. Luckily, my boredom and lack of success with girls over the summer led to lots, and I mean lots, of jerking off, so my stamina wasn’t a problem. I think Judy was both impressed and took this as a personal challenge, because she stopped touching herself and stood up. She turned away from me and dropped her skirt, revealing her firm, round ass. I don’t think I’ve ever seen a better ass (not that I’ve seen that many, but still). Hers was better than any girl my age, and reminded me of some of my favorite MILF porn stars. Before turning back around, she unclasped her bra and crossed her arms over her tits. In just the thong and arm-bra, she walked over to me. By this point, I was stroking harder and harder with each pass.

“You are so sexy,” I managed to stumble, still furiously jerking off. Judy giggled a little bit.

“Thank you, baby. You aren’t too bad yourself,” she responded. She dropped her hands to the side and revealed her amazing tits. I couldn’t stop staring, and even stopped jerking off. I was so astounded by her boobs. Finally I had the answer that had plagued me and the other caddies. I was right! They were certainly fake tits, but that didn’t make them any less appealing. They were fucking amazing. Moving her hands up to the buttons on my shirt, she slid the polo over my head. She then caressed my now-bare chest and kissed my cheek. By this point, my hand was back on my cock, stroking even faster than before.

“Wow, you look even better without a shirt Michael. And I think you’d look better with your pants fully off.” Taking her cue, I slid my boxers all the way down and step out of them and my pants. Now fully naked, I was fucking throbbing.

“Can I touch you Judy,” I awkwardly asked.

“You fucking better. What would be the point if you didn’t?” She responded. I put my hands around her hips and moved a bit closer.

“What the fuck is that?” She asked quite aggressively as she grabbed my hands and pulled me in closer. She moved my to her ass and made me squeeze. I almost came right then and there. My cock stood straight out and was poking right toward Judy’s thong-covered pussy. She let go of my hands, wrapped her own around my neck and moved in to kiss me. She slid her tongue between my lips and pressed her tits against my chest as we started to make out. I pulled her in closer to me and slid my hand under the top of her thong, bringing it down her ass with my hand. She pulled back from the kiss and smirked at me, grabbing my dick and slowly stroking.

“My, you are really fucking hard Michael. And you’re making me nice and wet. Why don’t you see how wet you’re making me?”

I quickly obliged by pulling her thong all the way down. Both of us completely naked, I gently ran my fingers over her pussy lips before parting them and easing a finger inside. She was so incredibly wet, I couldn’t believe it. I started to slide my finger in and out of her wet pussy as she increased her stroking speed. She leaned in to kiss me again and held me close as she jerked me off. With my left hand still firmly grabbing her ass, I slid another finger deep insider her pussy. I could feel her tense up with pleasure as she tightened her grip on my cock.

“I want you to lick my pussy babe,” she whispered in my ear. I nodded my head and she backed up again toward the bench. This time I followed her, and as she sat down, I dropped to my knees in front of her and moved my face toward her pussy. She had a thin patch of pubic hair just above her pussy, which I found so incredibly sexy.

“Ok baby, dive right in. Lick my cunt,” she urged me seductively. She ran her fingers through my hair as I dove mouth first into her pussy. She tasted so great as I licked, slowly at first and then quicker. I started to suck on her clit while I slid a finger inside her. She moaned and dug her fingers deeper into my hair. I could feel her starting to tense up as I ate her out. This was the first time I had ever eaten pussy, but I guess porn isn’t completely useless for teaching you how to do things. Her legs started to move up in the air, and I rested my hands on her inner thighs as I tongued her pussy. Before long, she grabbed a tight hold of me, started to grind on my mouth, and convulsed seemingly uncontrollably as she came. I hadn’t touched my cock in several minutes, and neither had she, but I was harder than I had been all morning.

“I think it’s time that you fuck me Michael,” she panted, her hand touching her clit as I looked up at her. I should have figured that that was going to happen, but for some reason, I was still shocked. I merely nodded in agreement. She stood up from the bench, turned away from me, and reached her hand through her legs. I stepped toward her and let her use her hand to guide my cock up to her pussy in order to fuck her from behind. I placed my hands on her hips as she slid me up to her hole.

“Fuck me Michael,” she whispered as my dick slid in between her pussy lips. I slid right in and her tight, mature cunt swallowed my cock. I exhaled quite deeply, and Judy did the exact same thing. I thrust deep inside and leaned forward.

“Oh my God, Judy, this is fucking amazing,” I panted as I impaled her pussy with my hard young cock.

“Shut up and fuck me,” she retorted, slamming herself back on me as I slid deeper inside her. I held onto her hips and kept fucking away as she moaned. I thought about my past conversations with the other caddies and how we discussed Judy’s body in graphic detail. Well those other guys would be amazingly jealous to hear about me balls deep inside Judy’s cunt. I put one leg up on the bench as I plunged deeper and deeper insider her. Judy arched her back and moved her hand toward her crotch, massaging her clit as I fucked her.

“Fill me up Michael. Fuck my cunt,” she groaned, loud enough for anyone in the locker room to hear. At her beckoning, I grabbed her hips harder and fucked her faster. I leaned forward and filled her as fully and as quickly as I could before pulling my cock out of her and stepping back. She turned toward me, sat me down on the bench and hope up on top of me.

“Fuck, Judy. This is amazing. How often do you fuck the caddies?” I panted as she sat up on top of me.

“Only when I see a cock that I want to sit on,” she panted. I wasn’t quite sure how frequently that was, but I didn’t fucking care. I grabbed ahold of her tits as she bounced up and down on my hard, young cock. She reached around my neck and clapped her ass cheeks on me. I was holding as hard as I could to keep myself from cumming before she reached back and started tickling my balls.

“Oh fuck, Judy. You’re going to make me cum!” I moaned, making sure she knew how close I was.

“Cum on my face baby. I want to taste you!” She said as she jumped up off my cock. She kneeled down on the ground and beckoned me to stand up in front of her. I obliged and started stroking my cock, wet from my own precum and her pussy juice. After just a few pumps, I was ready and moved in toward her face. The cum built up in my balls and before I knew it, I shot rope after rope of warm cum all over Judy’s face. I covered her mouth, neck, and chest, and she smiled for each and every shot.

“Mmmmm, cum on my fucking face, Michael! Give me all of your cum,” she moaned. I stroked and stroked and emptied my balls all over her. After finishing, I just about fell backwards and ended up on my ass in the middle of the women’s shower.

“Holy shit. That was…great,” I stammered.

“You bet it was baby. I think we can make a habit of this,” she answered. She used her thong to wipe the cum off of her face and placed it in my hand.

“Keep these baby. Let’s go outside and see if we can keep a straight face while we find the rest of the foursome. Not that we need it,” she laughed.

“Um, ok Judy,” I stuttered out, in a post-cum daze.

“Good baby. Now, if you keep your mouth shut, I can make next time even better!”

Source: reddit.com/r/sexystories/comments/e1sce2/my_milf_on_the_golf_course_str8mfmilf