I’m a lover not a writer… so sorry for the grammatical errors. Here’s some back story I was absolutely in love with we’ll call her Ariel, we dated off and on for over 3 years she was 17, I was 19 with a 2.5 years age difference when we first started dating. Now her 42 me 45, I was her first boyfriend, first kiss, first anything and a little over a year into our relationship she gave me her virginity. We always had a lot of intensity and passion but towards the end our passion was exhibited by either fighting or fucking sometimes both, make up sex was our favorite it seemed. Long story short I wanted to spend forever with her, she had never even dated anyone else, we ultimately broke up she dated a couple of guys ended up meeting her soon to be ex (STBX) husband a couple years later. I met my wife a year after that. I always thought of Ariel as the love that got away. About 10 years ago I was going through a self reflection phase and wanted to make a mends to those I had hurt. I sent a Facebook friend request to Ariel so I could apologize for the way I hurt her especially the way I treated her after we broke up. We chatted periodically, we even flirted a bit occasionally. We drifted apart both being married and all so it became the cordial birthday or special occasion message only. About 6 months ago I wished her a happy birthday she thanked me and made a comment about planning to take her kids on vacation to the same place my wife, kids and I just went. I asked just the 3 of you what about your husband. She informed me she left him about 5 months prior. Oh my the sparks were going off in my mind. We started flirting and talking a lot over the next few days about the feelings we’ve both held for each other for almost 25 years. We decided we had to know so we met at a public place half way between us we live about 2 hrs apart so we chose a mall. I got an erection the moment I saw her. Ariel is about 5’9 with shoulder length reddish brown hair with amazing blue eyes and large breast 40D her jeans fit perfectly and did not look at all like mom jeans. We spent a couple hours shopping together she needed to get her daughter a dress for a school dance. The clerk made a joke about dad allowing his daughter to go to a dance referring to me, so we both just went along with it. Ultimately we decided to get a hotel and had amazing sex like we always did. Afterward we parted ways and each went home. We talk, text or video chat daily. We’ve met up about a dozen times or so at various hotels but the specific time I want to tell you about was when I was helping her move stuff out of her marital home that the STBX is still living in so they can sell the house.
*****
The day started innocent enough I made the 2 hr drive to help her. We spent the morning and early afternoon moving boxes and totes around. I found a box of things she had kept that I gave her 25 years ago. I couldn’t help it I needed to kiss her. We were trying to be respectful of the fact that her STBX still lived there for the time being. I think it was a combination of me finding those mementos and her gratitude for my help plus we were already hot and sweaty but the moment our lips touched all limitations were off. I grabbed the front of her shirt getting a handful of her bra where the cups meet and pulled her toward me. My lips less than an inch from hers I looked in her eyes and knew she wanted me as much as I wanted her. I pulled her closer so her lips pressed firmly to mine. We kissed for what simultaneously felt like only a few seconds and an hour. We made our way to the couch as we ripped clothes off each other. Our lips never parting, our tongues explored each other’s mouths. I could feel and taste every breath she took we were breathing as one our hearts were beating together. I sat her on the edge of the couch that her STBX spent hours playing video games on. I knelt on the floor in front of her all she had on was a pair of simple grey panties but at that moment those simple grey panties were sexier than any thong or lingerie. I pulled my mouth away from her lips as I began kissing her neck, my mouth explored down her chest. Ariel’s nipples are always pointy but they were like rockets poking out at me. I took her left nipple between my lips and teeth as I cupped the underside of her massive right breast in my left hand. I replaced my mouth with my right thumb and index finger softly turning and twisting around her nipple. My lips slowly kissed down her stomach. Ariel has this scar on her stomach that drives me wild. I began to kiss and trace the scar with my tongue, she lets out a moan as I do. I continued to kiss lower and lower until I have her pubic bone pressed against my mouth. I yank her legs apart with no resistance and slide her panties to the right as I lick her clit. I take 1 long slow lick the length of her from her clit to her ass then back up, I flick my tongue on her clit as I slide my right index finger down along her labia. I can feel the wetness on her lips. I gently slide my finger into her pussy never wavering from the rhythmic licking. I see the pleasure in her eyes and loved the little whimper she let out as my middle finger pushed it’s way in as well. With both fingers massaging her G Spot, I let her wetness run down her as I press my pinky against her butt hole. She lets out a little moan of pleasure. I use her dripping wetness to get my pinky wet and slide it in she takes it in easily. Ariel has only had anal sex 1 time when we were younger and wasn’t a fan, she refused to do it with her husband which pissed him off that she had let me but never allowed him in the back door. I looked in her eyes to see if she was ok with this intrusion, I only saw joy and pleasure. I inserted my ring finger as well she had to reposition herself a little to accept it. My tongue still working her clit, 2 fingers massaging her G Spot and 2 fingers sliding deeper into her ass. I could feel her body start to tense so I moved my middle finger to the back as well. Her moans were sending shivers down my spine. At this time I could feel the precum drenching the inside of my underwear. I moved my hands to position my left index finger in the flood that was her pussy. I moved my right index finger down to her ass as well. She began to cum so hard, that I thought for a moment she was having a seizure. I slowly pulled my fingers out 1 at a time so she could count how many were in her ass 1-2-3-4. She stood me up and kissed me and could see the wet spot on the front of my underwear. She ripped them down causing my erection to spring up, a drop of precum splashed up at her. I used my left middle finger to remove the droplet from her cheekbone. She moved her head quickly to take my finger into her mouth. She pushed me onto the couch and dropped to her knees and began licking my tip. She took most of my length into her mouth with 1 smooth motion, what she couldn’t fit in right away she used her tongue to slide up and down. She alternated between teasing my tip with slow circles of her tongue and engulfing my shaft. Each lunge went deeper in her throat and brought me closer and closer to erupting in her mouth. She knew I was getting close so she cupped my balls in her hand gently squeezing them as I felt the cum coursing up my shaft and out the tip. She made a final lunge taking me deeper in her mouth than I’ve ever been. While she massaged my balls like she was milking a cow. She swallowed it all and licked every drop up.
As I stood to get dressed she said “You’re not done yet are you?”
I was pretty spent but I said “ Oh of course not.” And kissed her. My face still dripping of her sweet juices and as we kissed I could smell a hint of my cum on her breath.
Then she leaned in to my ear, grabbed my partially deflated cock and whispered. “I want you in my ass right now”. I was no longer deflating. She said “follow me” so of course I followed her right into her STBX husband’s bedroom where she got on all 4s and said “He always wanted to do this but it has only ever been yours. Please fuck my ass in the bed that, that ass hole sleeps in.”
How could I refuse she did say please and she has the nicest ass. I stood behind her and slid into her pussy to find some lubrication. Oh she was still very wet so I thrust into her several times to make sure I was completely soaked. She let out a gasp as I pulled out of her pussy and pressed my tip against her sphincter as I reached around to play with her nipple. I moved her hand to her clit and she knew right away I wanted her to masturbate for a nice distraction. I parted her cheeks and could see a perfect little button sized star. I slid my foreskin back as I gently pressed into her just a bit. She tensed up immediately so I waited, once she relaxed a little I slid more of me in until I was about half way in. I gently started sliding back and forth in and out each time pushing just a little deeper. I felt her finger brush against my balls while she was stimulating her clit. That touch was too much for me to resist I pushed all the way in so my balls could feel the warmth of her pussy as I filled her ass with my cock.
She let out a little scream and I backed off a little, she asked “where do you think you’re going” as she tightened her ass around me then once she was relaxed enough I began sliding in and out again I could feel her squeezing me with each thrust. I don’t know if she could feel how close I was or just suspected it but when she said “fill my ass with your cum” I couldn’t help but explode deep inside her. Her ass started squeezing my cock with every pulse. As my load entered her she began shaking, moaning and screaming “oh fuck, fuck yes oh my god” she kept pushing her ass back further onto my dick as rope after rope of my cum shot into her ass.
After what felt like 5 solid minutes of my dick just being squeezed by the vice that was her ass. Her orgasm subsided and she collapsed onto the bed pulling away from my exhausted penis. I laid on top of her and kissed the back of her neck and face, and rubbed her butt cheeks. After several minutes of silently basking in the moment neither of us could stop smiling as we got dressed. After kissing some more we left to go get some lunch and then I was headed home. My only regret of that day was I didn’t cum in her pussy too.
I never told her this part, as she stood up I saw a couple drops of my cum fall out of her ass onto his bed. Giving me such a chuckle. Hope you enjoyed, I know we did.
Edited for typos.
Source: reddit.com/r/gonewildstories/comments/bs5fxq/my_affair_with_the_one_who_got_away_25_years_ago
Let me know if you liked this story, Ariel and I have more to share if so.
Enjoyed this, more please. Btw, what is STBX?