[MF] Online dating and a wild night with an older woman circa 2007…

Back in the 2000s before I was married I was in my mid 20s I used to do online dating, match and eharmony and I had tons of dates. Some great some crazy and some fun. There was one time when I went on a first date with an older woman, maybe 38-40 years old which is crazy to me now since I’m 42. I can’t imagine going on dates with 25 year olds. So we met for the first time at an Italian restaurant in Chicago. Her name was Mary Anne. She wasn’t smoking hot or anything but she had a sexy look to her. Tight jeans and a nice big ass. She was divorced mind you and had no kids but was looking to date. I told her early on that I had never dated anyone older or divorced before but I was definitely open to the idea. She laughed and basically just said “let’s just enjoy ourselves and see where it goes.”

It was a normal date for a while, drinks and appetizers, but after a while we both started getting buzzed and that’s where things started to turn. She talked about her ex husband and how he was an ass and they ended up divorced. The only thing she missed of course was the sex. She said they had an amazing sex life. I took the bait and asked her what was so great about the sex and she said “well, he had a great dick. Solidly 10 inches and thick, sometimes too big but usually felt incredible.” I laughed and said “well I can’t match that but I think I have a good sized dick.” She laughed as well and says “Hmm okay that will be fun to see one day I hope.” I laughed and said “well hopefully 8 inches is enough.”

I still wasn’t expecting much but I figured maybe we could fuck one day. We keep having drinks and we’re both pretty drunk at that point but she’s really flirting and getting closer and closer. She finally has my leg between her legs and my knee is pretty much touching her pussy over her jeans. At this point I’m getting pretty horny and she’s giving me great vibes. We get to the check and I pay of course when she asks me what I’m doing after and I said I was likely driving back to the burbs from Chicago. As we’re walking out of Francesca’s, the restaurant, she asks if I would drive her home, she lived about 10 minutes away near Wrigley Field. I say I’m pretty buzzed but sure.

As we get in the car we’re talking about random stuff, and next thing you know I’m driving down Clark st. and she reaches over and unzips my pants and starts sucking my dick. She was so hungry for some dick. Holy shit she went to town! It’s a Saturday night in Wrigleyville, so there’s people walking right down Clark and she’s giving me road head. I’ll never forget looking around at the bars with people in line and woman I just met has my cock down her throat. To this day one of the most memorable and hottest sexual experiences ive ever had.

We get to her place and I’m circling the area around her apartment trying to find parking and she’s still blowing me. I finally find parking so she stops and we start kissing. We fuck around in the car for a while and she basically drags me out of the car to go into her house. We make out in the stair well, walk to the stairs and finally get to her place. She had a roommate so we had to stay under control for a second but as soon as we got into her room we started our Wild night. She was so fucking horny and so into it. We got naked immediately and fucked for hours. I fucked her in every position imaginable. From behind, her legs over my shoulders, she was so flexible and at one point she held her legs spread wide and I got so damn deep. She was so loud too, she later told me her roommate heard everything. I think my favorite part of the night other than getting roadhead with people everywhere was when she pulled out her vibrator and dildos. She wanted me to use a dildo on her while she had a vibrator on her clit. Im guessing she missed her ex husbands 10in dick. lol. I had no problem doing this. The dildo she had was a realistic, fat, veiny thing that I wasn’t sure could fit… She had me start slowly but after a bit I had that giant thing deep in her sopping wet pussy.

I’ll never forget ramming this huge dildo in her pussy while she came and started thrusting her hips up and down. Fuck I’m getting horny thinking about that night. We ended up fucking until about 4am when we passed out. I left her place around 7am and drove home.

We ended up fucking around for a few months after that and then lost touch. I have 3 more stories about her that I’ll follow up with if you all enjoy this one.

Feel free to message me with questions or if you want more details.