[M]eeting a sexy cougar leads to a [F]irst date: anal and office sex

I had been in a bit of a dry spell for a month or so and couldn’t seem to break through the slump. All of my go-to apps and sites just weren’t happening. Scrolling through one site I saw a new profile; nothing that stood out, just a close up picture of her eye and a mention of her age – late 40s. Her bio stated she was bored and married – her libido was through the roof and her husband didn’t have the kink or drive to satisfy her. I figured I’d shoot my shot and hope for the best. I took a few minutes to write out a thoughtful response and sent it off. A helpful hint to any men reading: putting even half a bit of effort into replying to posts or messages on dating sites results in an exponential increase in positive responses. You don’t have to be Mr. Sauve, but introducing yourself, responding directly to specific things in their bios, and writing out 3-4 sentences goes a long way towards starting things off on the right foot.

A few days later I got a response from Maggie, she enjoyed reading my response and thought I was cute. She sent me her Kik and we started some casual conversation. She explained that, because of her job, privacy and discretion were very important to her. I understood and agreed to her terms. We were both obviously interested in a strictly physical arrangement so things took a turn for the dirty pretty quickly. We seemed to have a lot of similar kinks and fetishes which fueled already intense sexual tension. Trying to lock down logistics proved to be a bit difficult because Maggie was married and had an active work and social life. We eventually found a good time to have a drink a few days later to make sure neither of us was a 55-year-old obese catfish or organ harvesting lunatic. The meeting, though fast, was great. We instantly hit it off and agreed we would get together soon. After a week or so of back and forth, Maggie told me she would be in my area the next evening and wanted to meet up. Half-jokingly I told her my office building would be empty and I had a new desk I’d been dying to “break-in.” She responded, telling me how she desperately wanted to be fucked in an office on a desk in her heels and skirt. “Fuckin jackpot!” I thought to myself.

The stars had aligned perfectly for Maggie and me. There was a mid-afternoon meeting and once it was over since there wasn’t much time left in the day, everyone headed home early. My building and office were essentially empty. I was a bit nervous the afternoon of the meet because I felt Maggie was a bit out of my league. Maggie was the ideal Cougar. 6’0”, blonde, beautiful perky fake tits, and an extremely fit and lean figure. She looked like the type of corporate woman who would rip your balls off in the office, outrun you on a workout and slam straight shots of whiskey at the bar. I threw back a couple of beers while I waited on Maggie to finish up work and head my way.

When she finally called my nerves had calmed so I gave her directions and impatiently waited in the parking lot for her. She pulled into the empty lot and stepped out in her skirt, blouse and heels. Fuck she was sexy. We walked the painstakingly long walk to my building and into my office. The second the door closed she grabbed me and pulled me into her, greeting me with an aggressive open mouth tongue filled kiss. I absolutely love this. I hate when women kiss like their mouth is a mail slot, barely opening it enough poke the tip of their tongue out. A full, passionate, open-mouthed kiss with your tongues meeting in the middle is where it’s at for me.

I made quick work of her clothes while we kissed, pulling each other in tight as we groped and licked every piece of exposed skin we could. I pulled back from her and took in her sexy figure, admiring her tits and lean body. I pushed her back against my desk and took her nipples into my mouth, one after the other. Pinching, twisting and biting each tit thinking how perfect this was. After a few minutes, Maggie pushed me away, sat up and said: “I want that cock in my mouth.” Now, Maggie got down in a way that drives me absolutely nuts. She didn’t get on her knees but squatted down so she was on the balls of her feet in her heels with her legs spread wide open. She took my cock in her mouth and aggressively started sucking my cock. She had the perfect balance of slow and aggressive cock sucking. Not fast and intense enough to make me cum, but just enough to make me rock hard and let me know at this moment my dick belonged to her. I looked down and Maggie had her other hand between her legs rubbing her pussy. This woman was driving me nuts. I told her, “enough I want to taste that perfect little cunt” and helped her move to lie back on the desk.

I got down and licked her from pussy to ass, not taking any time to tease or play. I spread her cheeks and tonged her perfect asshole as I ran my fingers up and down her pussy lips. After a few moments, she sat up on my desk spread her legs open grabbed my head and demanded that I get back down there and lick her pussy. I continued, alternating between sucking her perfectly sized clit, tonguing her ass and finger fucking her G-spot. As she got more excited I focused more on her clit and working her G-spot as I felt it getting harder deep inside her. Maggie started grabbing my head, pushing me into her cunt yelling out “yes! Fuck that’s my spot don’t fucking stop I’m gonna cum!” She came hard. Her pussy contracted around my fingers and a small puddle of her cum gathered on the tile floor below me. As her orgasm subsided she grabbed my head and pulled me up to kiss her then she turned around, bent over, pulled her ass apart and told me to fuck her.

I shoved my cock into her pussy in one full stroke. No easing it in, no teasing just a hard push; burying my cock to the base and feeling my head push against her cervix. She gasped, closed her eyes and grunted, and moaned “fuck” as I pulled out. I started to slowly fuck her just barely pushing my cock passed her pussy lips, teasing her with wanting the feeling of being full again. She started begging and pushing her hips back towards me, “please fuck me give me your cock. I want it inside me.” I obliged by quickly pushing into her as hard I could. This time I continued fucking her, shoving my cock into her pussy as deep as I could. I picked up the pace and started fucking her in a good rhythm. She kept up the filthy talk as I pounded her from behind. “You like my pussy? How does it feel fucking such a wet cunt? Your cock feels so fucking good please don’t stop!” I committed every detail I could to memory looking over this stunning beauty as I watched her pussy grip my cock with every thrust.

Maggie sat up and turned over, laying back on the desk and spreading her legs begging for me to fuck her again. I quickly got back to work fucking her missionary while I stood up and rubbed her clit as I fucked her. Maggie was rubbing her tits and staring at me with the best look on her face, she told me to fuck her harder because she was about to cum. As Maggie orgasmed she wrapped her legs around me and pulled me into her with her legs. I pulled out and got down and licked her pussy, cleaning up every drop of her wet cum.

When I got back up to continue fucking her she grabbed my cock and looked me dead in my eyes, “do you want to fuck my tight little ass?”
“Fuck yes I do!” I responded. She grabbed my cock and pushed my head against her asshole. Now, I’m no stranger to anal so this was the first time I was having anal with no real lube or build up. The wetness from her dripping pussy was more than enough for her to take my dick. With some firm pressure and a few strokes, I was balls deep in her ass. I asked if she was ok as I tried some short strokes. She looked at me and said “yes! Now fuck my ass!”
Well, she didn’t have to tell me twice. I went to town fucking her with fast full-length hard strokes. I didn’t last too long after that. She could tell I was getting close, “I want you to cum in my ass!” she shouted. I started fucking her harder with every intention of filling her ass with cum. I finally let loose and came as deep as I could in her ass, draining every drop into her.

I pulled out of her ass dripping cum, she immediately grabbed my undershirt and began to clean off my cock. After she wiped it clean she got on her knees and started sucking on me again. I couldn’t believe what a freak she was turning out to be. She looked up at me and asked if I was ready to fuck her pussy again. At this point, I was half-hard from a combination of cumming less than a minute before and her sucking on me for a bit.

She leaned back, opened her legs and started toying with her pussy while telling me to fuck her again. I stepped up and slowly stroked my cock back into her as I grew rock hard again. I worked up to a fast pace and started fucking her aggressively. I held onto her thighs, wrapping my hands around them so I could fuck her as hard as possible. Again she knew as I got close to orgasm and before I could say anything she looked into my eyes and said, “fill my pussy with cum, please! I want all of it inside me, cum in my pussy”. From our previous talks, I knew she had her tubes tied and safe so, without a second thought, I unloaded my second load of cum inside her. I slowly pulled out and my cum dripped out of her lips.

Maggie didn’t move as I stepped back and admired how amazing she looked all sweaty and oozing cum from both holes. Maggie looked up at me and asked me to lick her pussy again because she needed to cum one more time. Personally I have a fetish for eating pussy after I’ve covered it in cum so I didn’t hesitate for a second, dropping down and getting to work. I again started in on her clit and got my fingers to work on her G-spot. She was quickly wrapping her legs around my head and pulling me in tight. Her pussy started contracting and her floodgates opened, as she dripped and lightly squirted through her final orgasm. She came loudly squeezing my head with her legs. I backed off and sat down in my chair as we both panted and recovered.

We dressed and laughed at what happened and she admitted to me that was the first time she had ever let someone take her ass so quickly, but she was so turned on and wet it was like autopilot. Even Maggie was surprised at how easily she was able to take me with how big I am. She was a bit embarrassed at the puddles of wetness she left on the floor, but I assured her I thought it was sexy as hell and I told her how much I loved seeing her make a mess as she came.

Source: reddit.com/r/gonewildstories/comments/dntf53/meeting_a_sexy_cougar_leads_to_a_first_date_anal