First MILF -School Times

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I’m not sure how it started, but I’ve all the time had a preference for MILFs and cougars. The sex had all the time been amazing, and most of you can match my stamina and sexual appetite. My first sexual experience with an older woman happened in school. I was 21 at the time, she was 46.

We met while I was out at a bar with some friends. We had just finished an exam and I felt like blowing off some steam. Most of the crew were in relationships, but some of us were on the prowl. I noticed this stunning woman at the bar, and with some liquid courage in my already made my way over to shoot my shot.

Gloria was about 5’5, and one stunning body. Little on the curvy side, but amazing E cup breasts that were hardly being contained by her dress. I could see she had been trying to get the bartenders attention and since he was a friend of mine I waved him down, ordered my drink and then told him whatever she was having. She turned, thanked me, and said how hard it had been to get his attention (he wasn’t the best bartender but he was a friend so couldn’t complain). Now when I laid the flirting hard, I came with all the compliments. I said some lines about not seeing her in class before, and she blushed. Gloria responded with a “haven’t been in class since I’m out of college for 25 years now.” She knew what I was up to, and she was enjoying it. My friends started to head out, but I continued to chat up Gloria, hoping to see where the night would take us.

We had been talking and flirting so much we didn’t realize when the bar issued last call. We paid our tabs and headed out. I wasn’t sure what was about to happen until Gloria asked if I wanted to have a nightcap at her place. She was within walking distance so we walked arm in arm to her house. Now I’ll tell you, there was no nightcap. As soon as that lock on her dock clicked, she pounced on me like a cougar on meat. She was sucking my face off with her drunken kisses, and I was ready to give her the night of her life. I carried her over to her bedroom, and tossed her on to the bed.

The best part of gonna college in south was the warm weather, which means dress season is almost year round. Gloria had been wearing a floral dress, so made for easy access. I reached in to discover she had gone commando and dove in to begin eating her out. It was an intense feeling being under her dress eating her out as she moaned and begged for more. At one point, she wrapped her legs around my head and keep me there until I felt the warm rush of liquid gush out of her. She was a squirter, so it was gonna be a fun, wet time.

She decided it was time to return the oral favor but first wanted to remove her dress. She slipped out to show off her amazing body, and her tits and ass were perfect. She undid my pants, yanked them down to free the head doing all the thinking now. Her cock sucking skills are still some of the best to this day. She knew how to please a man orally. She was also a loud oral giver, her slurps i feel echoed throughout her house.

“You ready for me” she asked and jumped on the bed and spread her legs open. I pulled a rubber out of my pants and had her slip it on my guy. She was tight as I entered her, and we proceeded slowly. I thrusted carefully, helping loosen her up. With each movement, she gasped or moaned a little. We had not started the full on fucking when I felt her body convulse a little and out squirted a little stream. She had me grab a towel to lay underneath her, but that was pointless as we found out later.

We started again, and this time she had loosened up a bit. I Started to thrust harder and harder, deeper and deeper, and Gloria soon entered sex brain. She was overcome with pleasure she didn’t speak words. Just moans and loud “yes” that could probably be heard down the street.

We switched positions and had her on top for a while, at which point she said she wanted to feel me and ripped the condom and tossed it apart. Before I could say anything, she descended her pussy on to my cock and that was it. She felt even better raw, and that was gonna be it for the rest of the night. She bounced and rode me like I was the last fuck she would ever have, stopping at times to squirt again and again.

She commented how I had not cum yet and she was getting a little tired. I had her got off me, and I bent over the bed. I took her from behind in doggy, and that I went full fuck mode. I joked her ass would be red after I was done, and she loved every second of it. I soon felt the rush of cumming buildup and asked her where I should finish. She asked not inside her and I obliged. I pulled out and shot my ropes on her back, with some hitting her hair. It was the most intense orgasm I had had to date.

After we settled down, we saw the end of our first romp. Her bed was soaked, off it’s center (almost off the box spring), and we had knocked over a lamp and bed side table. We laughed and decided to sleep
In her guest room that night.

I woke up early and when I remembered where I was, I was hoping for a round two that morning but Gloria unfortunately had to work but promised to drop me off back at my dorm. As she drove me, she complimented my sexual abilities and had enjoyed our night together. She asked if I was eager to make it a regular FWB thing, especially on weeks when her ex-husband had their kids. I agreed and we started seeing each other soon after. We dated up until I graduated the next year. We had a lot of fun together, with us both leaning into experiences we maybe would not have done with other partners. I’ll tell more of the stories with Gloria but wanted to publish the time of our first meet.

NSFW: yes


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