First time [M]eeting up with a MILF with whom I had some long term [F]un with!

This is from a few years ago pre-covid and all that. I’ll put the usual —–’s where the sexy time begins if you want to avoid the backstory and setup. This is my first post here and I like writing as you’ll be able to tell from the length of this post. Sorry in advance if its a long read.

As I mentioned above, this story is from a few years ago way before Covid where meeting up with a MILF you’ve never met before in a hotel was only risky in terms of being tied up to a bed and being robbed or killed, not contracting Covid as well.

I was in my mid twenties and had hardly any experience with women. Growing up was the same story as well as you can choose the cliche you’d like to go with as I pretty much was the complete package when it came to reasons while I was still practically a virgin. I was pretty shy and not very outgoing with girls. I played all varsity sports in high school and was the type that didn’t allow any distractions from them. I have religious parents who didn’t allow girls over or anything like that, and the bar scene was out since I didn’t really like to get shit-face drunk like all my friends did, etc. etc….take your pick.

My boys were avid Tinder users at the time so I initially tried there, but after hearing some of their horror stories with random girls giving them STD’s and other bullshit, I decided that wasn’t for me. The online thing was still the easiest option since I had limited experience with women, and I could get all the small talk stuff done over text instead of in person. Looking back now, I realize I was a complete bitch being so scared about it, but it is what it is.

So with Tinder and quick stuff like that being out, and me having a complete MILF/Cougar thing, it dawned on me to try Ashley Madison. Most people know what AM is, but if you don’t it’s basically a site/app that’s aimed at married people trying to cheat on their spouse. I’m aware of the morality complications that AM brings about so if this is where I lose you, sorry. Anyways, I joined the site and got to browsing. As a guy on the site they charge you for EVERYTHING while women get it for free and are pretty much bombarded with all sorts of different winks, kisses, or whatever they call each notification. Probably 90% of the women’s profiles are either inactive, fake, or hookers that sent you some chatroom link asking for your credit card, so you have to develop an eye for who you message so you don’t waste any more time and money than is necessary. After having a few other fun experiences with the site, (I can write about those later) I was contacted by a woman who I replied to with my Kik username so as not to keep being charged for every message sent, and we got to chatting.

Long story as short as possible, she worked at a spa across town from me and we got to talking about the usual BS. Family, friends, interests, and why she was on the website. It was the usual issue with her older husband not being able to keep it up for her, and them growing apart. Being the super smooth and experienced guy I was at the time, I responded with the classic ‘’I can’t believe he can’t get it up with you, you’re absolutely stunning!!” that was met with winky kissing emoji.

We kept texting off and on for about a week with some flirting, then exchanging some pussy and dick pics. We both liked what we saw and wanted to keep moving things along. Then things cooled off a little bit, so I didn’t know if I fucked something up or she just lost interest and wasn’t really trying to meet with someone, and was just ‘’testing the waters for the thrill” so to speak.

A few days later, my phone vibrates and I see she sent me a text saying she had a tough day at work and ‘’Wished she could see me for some stress relief’’ I was in. We chatted some more and I told her I would be happy to make a ‘’Special delivery’’ (Corny I know but it worked) anytime she wanted and she said “How about this weekend?”. Going back to my cliche self, I was living with my parents at the time so my place was obviously out just as much as hers was. We both knew a hotel room was the only option, but I was the one to suggest it first as this magical third option that we somehow didn’t think about…and we set the date.

There was the usual daily conversation and sexting leading up until the day of the meetup with the wildcard of her suddenly mentioning she wanted to handcuff and blindfold me to the bed. All I could think about after hearing that was the episode of Seinfeld where George meets a hooker on the train and she cuffs him to the hotel bed naked and robs him blind. I figured if this was some sort of elaborate scheme where this woman was going on AM to trick and rob random guys that I better avoid the handcuff thing at all costs in case I gotta fight my way outta there. I mentioned to her that I wasn’t really down with the cuffs and thankfully she was cool, but I realized that her being interested in that meant she definitely had a kinky side I would find out about later.

So the day came and about 7 or 8pm I hopped in the car and drove halfway across town to the hotel we picked to meet up at. It wasn’t the Ritz Carlton but it wasn’t some roach infested motel either, just a regular Hilton hotel with a king size bed for the usual $90ish a night. I pulled up about 10 minutes earlier than our decided time to check in and it turns out she beat me there for what I assume was to make sure I wasn’t really 3 dudes that were gonna rob and possibly do some wild shit to her. I didn’t see her beforehand, I just knew it was her afterwards because walking her to her car, I remembered the car being there before me. I did the usual check in routine and went up to the room to make sure the air and everything worked, etc.

I texted her the room number and a few minutes later I get a knock on the door. Obviously I was nervous by this whole situation, but luckily I had a moment of clarity while I was silently telling myself to man the fuck up. I opened the door and was greeted by an ear to ear smile from one of the hottest older women I have ever fucked in my life.

She was about 5 foot 9, 140lbs, mid 40’s with jet black hair, and dark blue eyes. She did a little jump of excitement as we hugged and she walked past me into the room as I closed the door behind her. I was washing my hands in the sink prior to answering the door as to not seem like I wasn’t just sitting there like a total goofball waiting for her, so I grabbed a towel and dried my hands off as she went through her stuff and plugged her phone in since I guess it was about to die. We engaged in the usual small talk that carried right over from all our texting and became even more comfortable with one another now that we were sitting eye to eye. After chatting for five or six more minutes while casually watching some basketball on TV, she grabbed her bag, headed towards the bathroom and said ‘’She’d be right out’’.

I muted the volume on the TV, and laid back on the bed acting like I was still interested in the game when in reality I was counting the seconds with half a hard on waiting for that bathroom door to open up.

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A couple minutes later I got my wish as she emerged wearing an all black teddy with garder and stockings, and a black lace thong. We locked eyes and both grinned at the same time as she climbed on the foot of the bad. In the blink of an eye I ripped my shirt off, pants off, and turned off the TV. As I looked up, she was climbing on top of me, straddling me as we passionately began to make out.

We exchanged hot breaths into each other’s mouths as our tongues intertwined with one another. She grinded her pelvis on my rapidly growing cock that was still under my boxers, and I could feel she was already soaking wet through her panties as I noticed the fabric of my boxers was wet as I took those off a few moments later.

We continued making out for a few minutes until it reached a mutual ending with us both gasping for breath. As I mentioned before, I had vetoed the handcuff thing but I was still down for the blindfold if it was what made her happy. As we were still catching our breath, she reached into her purse and grabbed out a black lace blindfold and handed it to me. “Put that on and NO PEEKING!’’ she said. I smiled at her and pulled the blindfold over my eyes.

She began by locking lips, picking up right where we left off while gently brushing her panties against my now rock hard cock while sitting on top of me. Before we could lock back into the same make out intensity we just had, she gently bit my lip, broke away and slid down my body, dragging her hands down my chest and stomach and grabbing my cock.

I could feel her warm breath near the base of my shaft as she ran her tongue from the bottom of my cock all the way to the tip and swirled her tongue around it before taking the top half in her mouth. She slid her tongue back down my cock and began licking and sucking on my balls. Sucking and pulling on them gently as she swirled her tongue on them. She alternated between stroking and sucking my dick for a few minutes until I popped a pillow behind my head and tilted my blind fold up to get a better look. She somehow caught me and scolded me for peeking. I told her I couldn’t help but get a better look. She giggled, and I told her it was her turn.

I popped the blind fold off and threw it near her purse, and switched spots on the bed with her laying near the pillows now. I climbed over her and began making out once again this time moving my tongue down between her breasts then back up to her lips. I broke away and moved down to her panties that we’re even more soaked than they were earlier.

Slowly I slid her panties off as I ran my hands down her legs and to her feet. She spread her legs doing that usual stretch some women do after I finally removed them, then closed her legs back up. I wasted no time opening them right back up as I lunged forward onto the bed using my elbows to catch myself.

I dove straight into her pussy like a kid diving into a swimming pool. Starting at the bottom and moving up to her clit. I ran my tongue down the middle, feeling her lips spread apart as I stuck my tongue in as deep as it would go. I alternated between this and sucking on her clit as I worked her pussy until she orgasmed. She didn’t squirt, but the excess of juices and her moans signaled a job well done.

She then told me she wanted to “Suck on that beautiful cock” again so I told her to turn around and she straddled me, plopping her beautiful, plump ass right in my face as we began to 69. She went right in as she took my entire cock in her mouth and worked her tongue around my shaft while playing with my balls with her hands. On the other side of town, I picked up right where I left off and began licking more of the amazing juices I had helped create. I then grabbed another pillow and put it under my head so I could get higher up and began running my tongue over one of the tightest little assholes I had ever seen to date. (Or tasted for that matter)

I didn’t know if she would go for it at first since I hadn’t played with her asshole while eating her out earlier, but as my tongue brushed over and slightly poked at the entrance of that tight little hole I was met with a deep ‘’Mmmmmmm’’ as her mouth vibrated a little around my cock. I kept going and a few minutes later she let out another deep moan as she said I had made her orgasm again.

I let her come down from her high until she came up for air off my pelvic region, looked back and told me she wanted me to fuck her. I didn’t need to hear anything else as I slid out from under her and told her to spin around. She got on her knees and elbows with her beautiful ass staring me in the face. I gave it a light little smack that triggered a cute little yelp from her. Starting at her pussy I put one hand on each cheek and spread her ass apart and then let go as they jiggled back into place. I slid forward a bit and put my legs on the outside of hers, bringing her legs closer together so I could get her now dripping pussy at the perfect height to get my entire length in her.

I teased the entrance of her slit and she was so wet that I literally slid in by accident as I was still teasing her. I kept sliding more and more of my rock hard cock into her tight pussy feeling it squeeze my cock until my pelvis hit those firm ass cheeks and I stopped. She let out a deep moan that I had not heard until now and and said ‘’Oh Godddd that’s Good!” I started off slow and rhythmic so she could get used to things and picked up my pace as she began asking for me to fuck her harder and faster.

I grabbed a handful of ass in each hand like I had earlier and spread her cheeks as I was fucking her. She loved getting fucked harder and harder and as I spread her ass I gave her a few longer thrusts that buried my cock balls-deep inside her. She let out another deep moan. ‘’Ohhhh yesss!!’’ she said as I kept giving her the deepest thrusts I was capable of. As I slowed down a little bit I would pull nearly all the way out, and then quickly thrust back in as far as I could and held my cock deep inside her. I repositioned my hands from her ass cheeks to her hips. I grabbed her hips firmly and pulled myself even deeper, pressing against her ass cheeks. While still balls-deep, I wiggled my pelvis, working my cock left, right, up, and down in a circle. This sent her over the edge as I could feel her wetness increase as I kept giving her more and more quick, deep thrusts. We fucked like this for a while longer, alternating paces until she said ‘’Time for me to ride you’’.

I pulled out, lied on my back and was relieved to be getting a break as we had been going at it for a while. As I lied there she slowly climbed over me and straddled me as her pussy rested at the base of my cock, dripping onto my balls. She bent over and we locked lips again, our tongues swirling in each other’s mouths. As we were making out I felt her lean forward, reach back with her free hand and guide the tip of my cock against her pussy. She moved the tip of my cock left and right across her lips, teasing them and separating them from one another as they were wet and holding onto one another. As she broke away from our kiss, she slipped the tip of my cock inside her as she let out another moan, leaned back, and began riding slowly. We didn’t go fast like we had earlier, she slowly grinded on me as we alternated between passionately kissing, and her riding cowgirl. This was amazing as the connection we made while she slowly rode was a deep and passionate one. As she laid back taking my entire cock inside her, I could feel her soaking wet lips sliding on my pelvis. As she rode back and forth, they coated my skin with wetness as they were sealed around the base of my cock. While her tight little pussy forming an airtight seal around the entire length of my cock, I rubbed her clit with my thumb as she rode, and she let out another deep guttural moan as she told me she had just come again as I kept gently massaging her clit with my thumb as she came down from her high.

Seeing her in that position, and knowing that my entire length was inside her while she rode me definitely turned me on and had me close to orgasming myself. After a few more minutes I told her I was close and she said ‘’Now it’s your turn to cum baby” as she rolled off of me and instantly took my entire cock in her mouth.

She worked up and down from my balls to the top for what felt like an eternity of pure bliss, licking it clean of her own juices. I told her she was going to make me cum. All I heard was a ‘’MmmmHmmm’’ as her lips were still wrapped around my cock as she replied.

‘’I’m coming!’’ I said, as I shot rope after rope after rope of cum into her mouth as she kept stroking me with one hand and kept her lips sealed around the tip of my cock. After I finished shooting, she gave it a few extra strokes to ensure she had gotten everything she had worked so hard for, and swallowed showing me the clean mouth as a result.

We both rolled over and lay there catching our breaths for round two.

Little did I know round two would involve my first anal experience with a smoking hot MILF that I would never forget. This has already gotten longer than I planned though, I’ll have to post it in another story if anyone is interested.

Source: reddit.com/r/gonewildstories/comments/lzvcd6/first_time_meeting_up_with_a_milf_with_whom_i_had