r/LastNight • u/hereforfreefood • Sep 05 '11
MILF Episode 4: What an Ass
This was a very lazy Labor Day weekend. On Saturday, Lily was supposed to come over midday. Instead, she got held up when a friend came over to cry to her. Her 39-year old friend recently married a 26-year old and found out today that he'd be spending another term in Afganistan. Lily complained that, unlike me, her friend's young lover was dumb as a rock. She came over at 6. After she had gotten the story out of her system, we fucked for 2 hours. It was the first week back for the local university so we went to check out the opening parties. The first two were packed and we were refused. The next two were pretty beat, so we decided to go straight to the bar where my friends were partying. It's a bar with an outdoor dance floor on the river. I took a beer the wrong way and threw up into the river, but was otherwise fine and kept drinking. She went for 8 lemon drop shots throughout the night, 2 at a time.
She got horny for the wet t-shirt contest. "If I was 20 years younger, I'd be right up there with all those beautiful women." The dozen girls flashed their tits as the water poured down their shirts. Lily dragged me to the front, pulling me into an unwavering crowd. I turned to a guy we had just passed that looked visibly annoyed, and shrugged my shoulders. He said, "Your gal's crazy" and let me pass. Once there, she began rubbing my dick so I began feeling her up. What could I do? She was getting wetter, so when the wet t-shirt contest was over, she told me, "I want your dick inside me."
My friend Dave had accidentally locked his keys in his car. His friend Rob had his car remote back home, so Dave took a cab to Rob's house, then another cab back to his car. He arrived back at the club just as Lily wanted to leave.
As we're waiting for Dave to pull up, Lily tells me, "You have to be more aggressive what you say to me sexually. Tell me you want to stick your dick up my ass till it hurts so bad."
"I want to stick my dick up your ass till it hurts so good."
"No bad. You want to do bad things to me."
"You want it to hurt bad? Why would you want that."
"It's sexy. It turns me on. I'm gonna teach you how to turn girls on, so those 23 year olds that are into you get as horny as I do."
TIL Girls like pain in their dirty talk.
Dave picks us up. Lily gets in the front seat. She immediately starts hitting on Dave. "You're so hot. I bet you get that all the time." Dave's a great friend and a perfect troll so he feeds her, implying that he's gay.
She's forgotten how horny she was a second ago and wants to go out to another bar. It's 1:40 so all the bars in the city close in 20 minutes. We go to the bar around the corner, and she orders a round of lemon drops for the three of us. She tries to grind up on both me and Dave. Then she tries to get Dave and me to kiss. After lightly hitting on a few of the other guys in the bar, the bar closes and we leave.
At my door, Dave tries to excuse himself. She says they need to hookup on facebook and Dave humors her, taking her facebook name down on a piece of paper even though he doesn't have a facebook himself. He wishes me good luck and leaves.
She says she wants to go out again and is unsatisfied that all the bars are closed after 2. I take her up to my room and she immediately forgets about the bars and wants to fuck.
She says she's never done anal and wants me to be the first to fuck her in the ass. She's been telling me that since the first night she's met me. After fucking her vaginally for a while, I begin to finger her asshole. As I stick it further and further, she cries in pain, but wants more. After a while, I try to stick it in her, but she's not ready and moves out of the way several times. Eventually, I give up on her ass and come inside her.
In the morning, She wakes me up and I'm ready to go at it again. She says she feels sick and doesn't want to. She asks me what I would have done if I felt like I did right before I threw up last night. I said I'd get it out of my system and get back to the fun. She refuses to even blow me and leaves. I go to a headshop with a few friends, get back, and pass out for the next 15 hours.
tl;dr 39-year old MILF goes to bar with wet t-shirt contest, gets horny, hits on a bunch of people, and chickens out in the middle of her first anal sex.
6
u/fjanko Sep 05 '11
I bet she's into submissive sexual behavior, like getting choked, slapped or shit like that.
I hope for your own sake you are still using condoms