Caitlin was the first love of my life. We met in high school, but it wasn’t until she came back from college that we rekindled our spark. She had messaged me out of the blue, asking if we could hang out. I remember hesitating, leaving her on read for an hour. The truth is, she had broken my fucking heart.
I still remember her as she was then – slim, soft, and innocent. Her natural red hair framed her freckled face, inset with bright blue eyes that seemed to glow in the dark. Her skin was so porcelain pale that sometimes it tinged purple. Her perky breasts were topped with perfect pink nipples that always sprang immediately to life under my touch. Her pussy was a rare and beautiful thing, rosy and flushed and dusted with ginger hair and *always* wet, no matter how suddenly I initiated sex.
Back then, I would pull her boy shorts down as she was chopping vegetables and slip my cock into her, and in seconds her cream would be lathered on the base of me.
We had taken each other’s virginities at 18 and spent the victory lap after senior year discovering each other, but she had left no room for doubt that she didn’t see a future for us. I got possessive, jealous, pushed for too much too fast. I had been unwilling to face the fact that she came from a good family, had a college scholarship to her first choice of schools, and I was from the wrong side of the tracks and dropping out of high school. Handsome and charming? Maybe. Husband material? Not at all. I was pushing her away by trying to hold her close, and while I was doing that, she found someone else. She cheated on me. She graduated. She left our city, and my life. I was devastated.
“Hey, I’m in town for the holidays. Do you want to see a movie and catch up?” I knew as soon as I read her message, I would say yes. I was in a two year dry-spell. I hadn’t had anyone else since our last night together, when I had fucked her hard and furiously, knowing that the end was coming. I had looked into her eyes as I shot my cum into her and whispered desperately, “I love you,” and she had turned her head away and pulled me into her neck instead.
I looked her up on Facebook and saw she was dating the guy she had cheated on me with. They were living together. Happily. I had never seen her so happy in photos with me. My heart dropped. But… she *had* texted me. What did she want?
I turned over all the memories of our sexual explorations in my mind. How shy she had been when she gave me her first blowjob. The first time my cock has disappeared into her throat, how happy and proud she’d been. Even with spit and drool dripping down her chin. I had masturbated many times to the memory of my cum in her mouth, the way she pinched her eyes shut as she swallowed my load and she showed me her empty tongue through a strained smile.
We made plans, and met up at the theatre and she looked beautiful. Her bright copper hair was longer than I’d ever seen it, her eyes pale and blue, her small mouth curving into a tight, anxious smile. When she took off her jacket I saw she was thinner, sexier, but all her curves were still there – I could see her firm c-cups under her tight wool sweater, and the shape of her plump ass under her jeans.
The movie was my choice – a romantic, independent film that would show off my taste while also hinting at my intentions. She talked about her new boyfriend the whole time, killing my hopes, but then my knee brushed against hers in the dark of the cinema, and the electricity sparked like lightning. She pulled away but I was hopeful again. And hard.
When the movie was done, I suggested we have drinks at my place. She looked doubtful; we both knew her boyfriend wouldn’t approve. But I was on her way home, so we went to my place anyway.
It was no love nest, just a bachelor apartment with a futon, a desk, a closet, and a TV But we didn’t need much. We just talked.We danced around the topic of her boyfriend, never touching it in case the fragile tension between us broke. We exhausted the night with how much we had to say to each other until suddenly, hours and hours later, as her tank top strap was slipping down her shoulder and we were down to the last glass of cheap wine, there wasn’t anything left to do but kiss her.
She hesitated only a moment before her mouth relaxed, and her soft supple tongue snaked into mine just like how I remembered. My hands wandered to the small of her back but she pushed me away and started crying.
My heart was pounding. I sat down on the edge of my futon. “I’m sorry.”
She looked so beautiful in the naked light of my single light bulb, even as she was crying. Her fingers covered her face, and her red hair fell over her fingers like a copper curtain. Her pale shoulders lay bare, begging to be bitten. On her left index finger was the Claddaugh ring, an Irish ring that when turned inward, told others your heart belonged to someone. But to whom?
I wanted so badly to hold her, to comfort her. I wanted to be the guy that could make things better, not the guy that ruined things. “Can I hold you?” I asked. She wiped away her tears and nodded yes. I stood up again and took her into my arms. Her body was warm, almost hot. Her smell was intoxicating. Without thinking about it, I kissed her neck, and I felt her shiver. I threaded my hands into her hair and pressed my lips in her neck again.
She pulled back to look at me, and I froze, letting her lead. Tears were still falling from her eyes, but her mouth was open, she was breathing heavily. Then she kissed me and… I stopped holding back.
My hands slipped into her tank top and I ran my thumbs across her nipples. Her breathing got heavier as we kissed heavily. She ground her thigh into my cock as I pulled her shirt and bra off with one movement and moved her onto the bed, never releasing my embrace. I kissed a trail from her throat, to each breast, to her stomach as I undid her jeans and rolled them off of her.
The sweet smell of her pussy filled the air, and my mouth watered. There she laid before me, as perfect as I remembered, a delicate porcelain doll, biting the tip of her finger as looked at me through heavy-lidded eyes. She was breathing heavily, even tears gathered in her eyes. When I brushed my thumb across her clit, she cried out, in pleasure or anguish or both, and my thumb came away sticky. She was as wet and pink as I remembered, her pussy lips glistening as I kissed the insides of her thighs gently, before I began licking her cunt with soft, delicate laps.
Her whimpers were music to my ears. It had two years. I had, in some ways, been waiting for her to come back to me. As I licked and sucked and kissed her slit, my cock became so hard that it hurt. It felt like two years of pent-up desire and brokenheartedness was fighting to escape through my dick. But I had no desire to rush through what may be my only shot at getting her back.
Caitlin’s pussy tasted just as sweet and clean as I remembered. As I worked I looked up at her, savoring the moment in case we never got the chance to have another one. The way her ginger pubic hair caught the light of my bedroom, the way her breasts lay flat with gravity, how stiff and pink her nipples were. Her hands covered her face as she came, her voice was full of lust and shame. I stopped, licking her taste off my lips. I was uncertain if I had gone too far. She was still sniffling, even with all her clothes off. Was this enough for me to have closure? To know that, even if we couldn’t be together, she still wanted me? Maybe even still loved me? I began formulating an apology in my head, ready to comfort her and send her home.
“Do you have a condom?” she asked. Her voice was quiet, almost shaking
I wiped my face on the back of my hand and pulled a condom from the bedside. I pulled off all my clothes and then watched her stare at my cock as I pulled the foreskin back and rolled the condom along the length of me. I positioned myself at her glistening pink entrance. In my head, I whispered “I love you.” In my head, she whispered it back.
I pushed into her and she was tight and warmer than I remembered. Her little quiet cries spurred me on, I lifted her legs over my shoulders and resolved to fuck my way back in her heart. I watched a few tears slip out her eyes as she dealt with whatever demons raced through her head. But as I moved in and out of her, she mewed and gasped. She made me feel like a sex god after a two year dry-spell. I thrust my whole length inside her and made her gasp, and I pulled almost the whole way out and she whimpered and begged for more.
I tried to last as long as I could, tried to memorise every detail of her naked body. The way her watery eyes looked at me with desire and regret, the way her milky tits bounced with every thrust, the way her pussy juice began to drip onto my balls, the smell of her in the air and on my face, the sound of her voice as I fucked her.
Finally, I came. It hurt. I felt like my cock was turning inside out inside of her cunt. I could feel my cum splashing off the tip of the condom. Intense relief rushed over me, into me. I felt lightheaded. I wanted to collapse onto her, gather her body into my arms, snuggle into her neck and ask her if she would leave him and stay with me. But in the post-nut clarity, I felt shame. All the pain she had put me through by being unfaithful, I was now putting some innocent dumb dude in another city through the same thing, and all he had done wrong was love this beautiful, indecisive, angelic woman.
“Do you want to stay the night?” I asked. “It’s late.”
She shook her head no. “I don’t think that’s a good idea. I have to leave the city tomorrow.”
“Oh,” I said. I hadn’t known that.
We both got dressed, awkwardly. I wanted to say something, but nothing came to mind. Saying “I love you” seemed like the stupidest thing in the world. And I wasn’t sorry, so I couldn’t apologise. I couldn’t beg her to stay, knowing she’d have to give up her school and her life, and I was too proud besides. We were never meant to be. I was lucky I got this one more night.
She pulled on her jacket and brushed her ginger hair out of her face and gave me a shaky smile. “Thanks,” she said.
For what? I thought. “It was nice to see you,” I replied. Then she walk out the door, to leave our city, and my life.
Or so I thought. Because she didn’t leave the city the next day. She came back to my apartment, and we began our affair. But that’s another story, full of more pain, heartbreak, and mind blowingly good sex. Please comment or message if you’d like to hear more.
Source: reddit.com/r/gonewildstories/comments/10cz8hu/mf_i_m21_made_my_exgirlfriend_f21_cheat_on_the
Need more
!updateme
Sad and unhealthy but sexy story.
I’d love to hear more about this story and if it has a happy ending? Or a sad one….
!updateme
!updateme
Heard the boyfriend joined you recently and an eiffle tower was completed. Did you double stuff?
!updateme
FF
Wants to hear the whole story in details
Nice story. Reminds of one of mine when I was 20
That was intensely good! I definitely wanna hear more
I pulled the same on my ex, but I waited till she was married
!Updateme
!updateme
Great story would love to hear more