So in advance sorry for any taboos I break (first time posting something this large on Reddit, aaaaand I posted it in the wrong subreddit alteady…twice fml). Anyways third times the charm! I can already tell this is gonna be long, so again sorry!
The set up! Back when I was a slightly younger man I used Tinder (gasp) and had an average amount of luck at the time finding dates. Average is the right word to describe my experience on there, I had had a few good dates and a few bad but overall it was enough to keep me interested in swiping right.
One Thursday night, after I had gotten off work, I was browsing profiles and just was not feeling the girls my age (at the time everyone seemed to have the not all who wander are lost quote on their profile) and I thought heck lets mix things up. No avid reader I didnt swap over to guys, but I did bump the age range to the cougar setting. At the time that didn’t really change anything as the population of older women was relatively small in comparison to all the 20 year olds. But I came across one woman in her late thirties that we shall call Jen. She looked happy and beautiful and definitely caught my eye though her bio was pretty much empty. Of course I swiped right and that was it.
Fast forward to 2 hours later I’m about to call it a night when the lil Tinder notification thing goes off for a match! Of course I’m instantly wide awake and I see it is Jen. I’m stunned but I figure she must be a bot. Before I can decide what to do she messages me one word, “Smartass”. For what ever reason this threw me for a loop, I thought how dare she call me that this is a sacred dating site and she’s being catty as all get out. What do I do how do I respond? After 5 min of contemplation I figured I should say something. So I told her, “You’ve somehow managed to see through to my core, what gave me away?” (Dunno if that’s the actual wording but it was something like that).
She told me she could tell I was a smartass as I had swiped on a woman over a decade older than me. I told her that this was a two way street seeing as we had matched. She told me this was true and liked what she had read on my profile, I seemed interesting to her. We talked for an hour or so and just got to know each other (music talk mostly) and the conversation flowed naturally. I learned she was looking to re enter the dating scene again but wasn’t enjoying the men her age (something we had in common). She mentioned she was on a staycation from her OC home and was staying 4 miles away by down town disney so she could attend a club with her girl friends over the weekend.
Not wanting to miss a chance I asked if she was telling me this as an offer of a date. She said she wasn’t sure yet but was tempted, the younger guy thing seemed crazy to her yet she wasn’t against a lil crazy. We talked a bit more about innocent stuff before we offered to swap numbers and go from there. Well that was basically pandora’s box flooding open. We offered to talk on the phone and she loved the sound of my voice (only time I have ever been given that compliment) and wanted to see more. We exchanged innocent pictures for a bit before we swapped to the juicy sex talk. She asked what i was into and told me her interests. (She told me a bit of sexy info that I will share with you later o reader of mine). She also asked what I was packing and to send pics!
So of course I did. I was really excited at the time and was trembling quite a bit but she liked the pics I had sent (guys we can’t just send dick pics randomly, gotta get the ladies interested first then they will want them)! She sent me some risque pics but I told her I wasn’t interested in seeing her naked unless it was over wine tomorrow. She was sold. Told me her room number and we had a wine tasting date at noon the next day! I’m pretty sure I didn’t sleep that night, this was absurd and crazy and probably a scam. Still the next morning I texted her asking if we were still on and if so what wine should I grab. She replied yes and chardonnay. So I grabbed a bottle from Rite Aide along with a bunch of condoms and headed to her hotel.
I was so nervous walking to her hotel room with a brown paper bag of wine and condoms. The elevator ride took for ever and my heart was pounding. It was such a strange sensation, I’m no prude and she wasn’t my first but I had never been in this situation of sex within 12 hours of texting someone who was 10+ years older than me. Somehow I got to the door and knocked and she opened it. Never will I forget seeing her the first time. She was almost as tall as my lanky ass with piercing blue eyes and almost white blonde hair. She let me in and we hugged and awkwardly shuffled around her hotel room. She had her club outfit mostly laid out on one of her two beds. We talked for a bit and she opened the wine (got lucky she liked the Rite Aide chard!) and we chatted about how absurd this was. She mentioned I was sitting too far from her and I beckoned me closer. As nervous as I was i realized she was too. I knew I wanted her. She was gorgeous and we just had this chemistry that was electric; even with our basic conversation I could feel it between our eye contact. I knew if this was going to happen I needed to make physical contact with her. We had been talking about chiropractors and how both our backs needed some TLC, so I offered an ice breaker massage.
Jen gave me a piercing blue eyed look (she told me later she was finalizing that she too felt the same as me and wanted this to happen but was still coming to grips with EVERYTHING) before she agreed. I know she felt me trembling as I worked shoulders but I was on a mission to impress her. I had her finish her wine before having her lay on her stomach so I could work her back. I straddled her voluptuous ass and gently grinded her as I worked her knots out. She cooed and sighed and I took that as an invitation to mix in some kisses to my rubbings as I ran my fingers over her back. She turned her head to me and we made out like that for a while, me grinding her ass and squeezing her shoulders as we both explored the others lips. It wasn’t long until she broke off saying she was sorry, but she needed to see my cock right now.
Jen was sitting up on the bed fully clothed watching me with those amazing blue eyes and I locked eyes with her; wanting to watch her watch me. After getting down to just my boxer i walked over to her, asking if she wanted to open her present. She did, and slid them down proclaiming, “god damn that’s amazing! Get on the bed now!” I pretty much tackled her in an embrace and we kissed like wild horny teenagers as we ripped her clothes off. I got a condom on and prayed I could last longer than I thought i would. We fucked in missionary kissing the whole time until I exploded inside her. My excitement was too much though, and even though I had cum I was by no means anything but throbbingly hard. So we swapped condoms and I fucked her until she was grabbing my hair moaning so sexily and looking at me with those blue eyes of lust.
Eventually Jen wanted to cum too and that usually happened via oral. I was more than happy to oblige her and got my real first look at her soaking pussy. I devoured it, no longer tentative and slow. I wanted to pleasure this woman more than anything. She must have felt the same way as her dirty talk increased and she held my head between her legs. She was almost screaming so many wonderfully sexy things; for example: yes oh yes fucking eat the milf pussy, you like that you’re fucking this milf?! (She knew how to turn me on so hard). After lapping at her clit for a while I learned the rhythm she wanted and found she liked a few fingers inside her as I licked up and down her sweet pink pussy.
I must have been doing a great job cuz she told she was coming and to leave her clit alone and just finger her. I had them wiggling inside her in the come hither motion as she screwed up her face in pain and pleasure as she came (remember that sexy bit of info she had texted me literally 12 hours before hand?). As it happens she was just excited as I was and it manifested in the biggest fucking squirt I have still ever seen. Surprise, Jen is a squirter and she fucking soaked me and the bed in one of the most intense orgasms that hotel has ever seen! I was shocked, she had told me during our flirty sexting the night before that she has squirt in the past but its rare. The excitement had been too much for her though and it was not a rare occurrence at all, almost every other next time I fingered Jen she squirt so fucking much. We spent the afternoon fucking like mad teenagers before I had to leave for work…only to come back 8 hours later to continue fucking and trying out new positions.
As this is already way longer than I intended I’m going to stop here. Thanks for reading and hope I told a good story. Beyond the names it is 100% true. Cheers everyone!
Source: reddit.com/r/gonewildstories/comments/9jlfap/mf_success_story_in_so_cal
Very nice!
Well done!
Cheers mate! Hope you got more to share!