My First MILF [MF]

My name is Andy. I grew up in a very religious household, so I was a late bloomer. It took me until college to have my first kiss, and I didn’t lose my virginity until I was twenty-one. Since then, I’ve been doing my best to catch up. This is the story of the first time I slept with an older woman:

As I’ve mentioned in previous posts, I’m in the Army. That experience led to a lot of opportunities to travel, see new things, and meet new people. It is not, however, particularly conducive to dating. Fortunately for me, I had plenty of friends who were happy to set me up with people they knew.

One of these friends was an older woman named Janet. I was over at Janet’s house, having a beer with her husband, when she mentioned that she knew a woman who was looking to date. Janet asked if I was comfortable with a woman having kids, and being a little older. At the time I was 24, and the woman with whom Janet was setting me up was 37, and had a 17-year-old son. I told Janet that I was game as long as she was a cool person.

Janet quickly called her friend, gave her my number, and said “he’s very excited to meet you. I told him you’re cool, so don’t blow it!”

About five minutes later, my phone buzzed. It was from Janet’s friend, Laura. Laura and I began texting, chatting about life and trying to get a feel for one another. Periodically, Janet would demand to see my phone so she could see what we were saying. She was proud of her match-making skills.

Laura and I arranged a date for the next night, which went well. She was an exceptionally intelligent woman, in upper-management in her field, and ambitious as hell. Her knack for conversation was captivating, and I felt like we could have talked for days on end.

Laura was also quite attractive. She was taller, which was perfect for me as I’m 6’4″. She had long legs, a shapely ass, and nice perky breasts. She was Hispanic with long brunette hair, large green eyes, and a dazzling smile. On our date she wore a tight black dress with a low neckline that perfectly accented her amazing body. I was captivated.

After a couple hours of talking, conversation turned to sex. I asked how a woman as impressive as herself was single, and she said that her career and her son were higher priorities than her libido.

“I don’t need a man. I have a son for the chores, friends for companionship, and a vibrator for everything else.” Laura said with a laugh.

“So why are you out with a 24-year-old?” I asked, matching her jovial tone.

“The vibrator’s out of batteries.” Laura winked.

I stared at her for a second, gauging her seriousness. While I was looking at her intently, I felt her foot rubbing my leg under the table.

“Come on, young man,” Laura said. “Don’t tell me you can’t take a hint. I can’t be spelling things out for you all night.”

I got the check as soon as I could.

I walked her arm-in-arm to my car. When we got to the passenger door, I spun her around, pushed her firmly against the car, and kissed her. I felt her moan into my mouth as she wrapped her arms around me. I cupped her face in both hands, then pressed my body tight on hers.

We made out in the parking lot for a few minutes, until a passing car honked. We broke our kiss, grinning like idiots.

“Y’know, it’s been a while since I got fucked in a car.” Laura said. I loved how direct she was.

I opened the back door, and gestured her inside.

“After you, ma’am.” I said, giving her a firm spank as she climbed inside.

In my car, we began making out again, but with a greater sense of urgency. Our hands pawed at each other’s bodies, rubbing, squeezing, and fondling all over. I reached my hand under her dress to squeeze her ass, only to find that she wasn’t wearing any underwear.

“Naughty girl,” I growled. She winked, then chomped down playfully on my lower lip.

I kneaded her ass with both hands as she nibbled my earlobe. I slowly crept my hands closer together, getting close to her asshole.

“Ooh, you’re a bold one,” Laura cooed into my ear. “Go ahead stud, you can take my ass.”

I quickly pulled my pants down just below the waist, freeing my rock hard cock. I rubbed my head up and down the length of her pussy a few times, making sure to coat my entire length with her wetness. Then I leveled myself directly at her ass.

I pressed my cock firmly against her hole, then moaned as I entered her. Laura gasped, digging her fingernails into my shoulder and letting out a groan of pleasure into my ear.

I slowly drove myself deeper inside her, pulling her body up and down with my hands.

“You’re so fucking sexy,” I breathed. “You feel amazing.”

Laura responded by bouncing her ass against me, bringing me even deeper inside. We developed a slow, passionate rhythm as I fucked her ass. Gradually, we picked up speed, and the noise of her ass bouncing against my muscular thighs echoed through the car.

“Fuck!” She moaned as I rubbed her clit with a free hand. “I’m cumming! Fuck my ass and make me cum!” I was happy to oblige.

As Laura’s entire body erupted in orgasm, her ass clenched tight around my cock. The increased squeezing was enough to send me over the edge. I let out a deep, guttural groan as I pumped my first stream of cum deep inside her ass.

We both lay there, our bodies spent and shaking. Laura collapsed onto my chest, gently kissing my collarbone as I ran my fingers through her hair. We lay there, talking and joking for a few minutes as we caught our breath.

“So, am I better than a vibrator?” I asked playfully.

“Eh, we’ll have to wait and see. But practice makes perfect,” Laura said as she leaned in to kiss me.

We spent the night together, and saw each other a few more times over the next month. Laura’s sexual appetite was insatiable. We spent days at a time lounging around my house, fucking in every room, and talking. She was amazing.

Unfortunately, after a month of wild sex, my unit went to the Joint Readiness Training Center in Louisiana for a month. I was without my phone for a solid two weeks, over which time I guess Laura chose to pursue her career aspirations. We did not get together after I returned.

Still, I’ll never forget the first MILF I ever had. Thanks for reading!

Source: reddit.com/r/gonewildstories/comments/6zujlk/my_first_milf_mf