[MF] my GILF experience | 2016

Online dating can be a gift and a curse. Lots of wasted energy and money. Lots of wild memories. I was never really looking for a type of woman, more just a willing woman. But every once in a while you find a woman who you can’t believe exists. That was Annie.

I can’t remember how it started, but it started on POF. She was pretty so I messaged her back or first. I noticed where she lived, and I figured this would go no where. I wasn’t about to drive an hour for a date. It would just be fun to talk.

The talking was real fun. She was quick witted, and interesting. She seemed to actually like my flirty responses full of innuendo. I knew she was going to want to meet. I flipped a coin and her side won. I agreed to take the hour drive and have a few drinks with her.

Now what I never told anyone at first was that after I split with my ex I moved back home with my parents. It was great except for dating. So, if Annie if I was going to be charming Annie’s pants off, they would be coming off at her house.

On a Sunday night I made plans with Annie. She picked a bar that sounded like I might feel relaxed at. Not divey, but not upscale either. It was fine. I walked in and saw her at the bar. For the first time in many dates she looked exactly like her pics. It was great. A very pretty woman in her early forties. She was dressed very cute. Jeans and a flannel with the top buttons undone to show off her great cleavage. Her huge tits were a big surprise. I was not expecting that.

We talked and sipped our drinks. I usually drank more on first dates but I was driving. So was she so it was more of a real date than a drunken setup for a hookup. I was actually enjoying myself. I could tell she was as well. Our conversation bounced around and eventually landed on kids. I have 3, she has two. I gave my three children’s names and ages, then she did the same. This is where my interest perked up.

She said that her oldest son was 25. It was almost unbelievable. In a dark bar she could pass as 25. I was a little in shock, but things happen in high school. Not the first teen mom I knew of. To try to jokingly move on from this I mentioned that I started a family at 25. I said she better hope her son doesn’t do the same. And then she said it. Her son just had a baby a few months ago.

I couldn’t believe this. I was in awe. This was the coolest date ever. I was making the moves on someone’s grandma. It made things so much more appealing. Milfs are a dime a dozen these dating sites. This woman was a needle in a haystack. I will not say this made me want her, because I already wanted her. But it was a nice little bonus.

After another drink we left the bar to go for a walk. It was really nice. We kissed for a while and held hands. I walked her back to her car. I barely tried to get her to take me home. It was a nice night. She seemed like a really nice lady. We kissed goodbye and I drove home.

We continued to text later that night and the next day. It was even better than before. We were flirting really hard now. She was sending sexy selfies. I needed to fuck this woman. She mentioned that her younger son would be gone for the night later that week. We made plans to hang out at her place. Things were looking good.

A few nights later I took the hour drive again. I stopped to grab some beer and found her house. I walked to the door and she buzzed me up. One knock and there she was. Again another great surprise. The flannel that showed off her cleavage was gone. It was replaced with yoga pants and little white t-shirt. She had a small hoodie on, but I could make out all her curves. Those big tits were a perfect match for her fat ass and thick thighs. This woman was flat out hot.

We settled in to the couch to watch some tv. We talked a little and went out for a cigarette. Eventually she made a point that we were watching the season premier of Fargo. I had seen the movie, but the show was so good. Pretty much too good.

After forgetting that I was not there to watch Fargo season two, Annie made a move. Now my attention was completely on her. We were making out intensely on the couch. Her hoodie came off and she was straddling me. Her tight shirt and pants made feeling everything easy. My hands rubbed her thighs and ass while she grinded away on me. I was wearing jeans but I’m sure she could feel how hard I was through her thin pants. I began biting her neck and earlobes. This was great foreplay.

She took me by the hand and lead me to her bedroom. We fell together onto the bed. I was continuing to kiss her as my arms wrapped around her. I was squeezing her while I tried to unclasp her bra. Finally her breasts were free. I dragged her to the edge of the bed and I got off. I knelt down by the side of the bed and lifted her shirt. I finally got to see her tits, and they did not disappoint. No bra tricks here. They were just so perfect. I was started to kiss each nipple. Sucking slow and soft. I was determined to get everything I could out of these. I wasn’t being touched by her and I was fine with it.

I continued to suck and nibble while my right hand made its way to her crotch. I started to rub over her yoga pants. I could feel how warm she was. I made circles over her pussy, gently spreading her open with each pass. Eventually pushing through the cloth and getting one knuckle on my middle finger inside her. This made her jump a little.

I finally put my hand inside her pants. The silk of her panties and her wetness made my circles go much faster. I started to concentrate more on her clit and push more of her panties inside her. I could tell this was driving her crazy. I slid my hand inside her panties and finally put a finger all the way in her. She was almost too wet. My middle finger would do about 10 circles on her clit before moving back inside her. I kept up all the while going from one nipple to the other. She was ready to go.

I pulled my hand out of her pants and stood up. I quickly ripped off my shirt and unbuckled my pants. As I unbuttoned and unzipped she rolled to her side. She grabbed into my boxers and my pulled out my cock. She started to stroke me slowly. I looked into to eyes with anticipation of what her mouth might do to me at this point. Instead she shot me a look, and then glanced down at her crotch. I knew she could not wait any more. I ripped my pants and shoes off and jumped back on to the bed.

I tore her her clothes off her with pure aggression. He pants and panties flew off her legs and landed at the foot of the bed. I pulled her by the hands to sit up and yanked her bra and t-shit over her head and flying across the room. She fell back as I got between her legs. I dragged the head of my cock along her lips until I knew I was at the spot. A quick kiss, a fierce stare into her eyes, and one small push and I was in.

Her pussy was ready for me minutes ago. I slid out and back in without any friction. I did feel I was continuing to stretch her out with each pump, but without effort. She panted as our pelvises continued to meet at a quick pace. She had an older mattress and it was doing some of the work for us at that point. We bounced off each other at a faster and faster pace. I had to keep more still to ensure I didn’t pop out of her. The bed was doing it’s magic. Springs were squeaking and she was moaning.

Finally the speed had caught up to us. I started to feel a little friction. I could tell this was it. I tried to grab hold of her and push as deep as I could inside her. I stopped the mattress from trembling and gave her a few hard thrusts before I exploded inside her.

She immediately complimented me. Saying that she hadn’t been fucked like that in a long time. Then she commented on how I didn’t wear a condom. I knew she had her tubes tied, but the heat of the moment, not some no condom credo, created this situation. We were both almost positive we were clean, so we just left it alone. We laughed as we found her clothes all over the room and got dressed.

We went and tried to relax in her living room. Except I couldn’t. I polished off the rest of the beers and then started in on a bottle of gin Annie had. In a last ditch effort to get back to bed I took some low dose benzo she had. I was having a great time then...blank

Woke up in her bed with my phone going off. I was going to be late for work. I grabbed my stuff and headed to the shower. I walked by the kitchen to see Annie cooking a full breakfast. This was strange. I jumped in shower. All I could think as the hot water poured down my face was “what did I do?”

I came out to see the whole spread on the table. Home fries, eggs, bacon, sausage, toast, oj, and coffee. She told me to sit. I tried to explain I was late for work. She wouldn’t take no for an answer. I sat and tried to eat as fast as I could. Annie just sat and smiled while drinking coffee. Finally I ate what I thought was a reasonable amount and got up to leave. I went to say good bye and she said “you know, you said some pretty interesting things last night” and just smiled. I just smiled back and gave her a kiss on the cheek. As I walked through the door she said “talk to you tonight honey”

“Fuck, fuck, fuck, fuck!!!!!” What did I say. This was the worst. I got to work and dreaded talking to her. I decided I didn’t want to know. Annie texted that night. I didn’t respond. Same the next day. Four days later she sent me a very painful text to read. I still couldn’t face it. I just blocked her number. I blocked her on POF. She would never see me again. I ghosted the GILF