So, some background. I dated this girl on and off for most of senior year of university, but she moved away after graduation for work and we didn’t want to deal with distance. I ended up moving to the same city for work about a year or so later, but we didn’t keep in contact. I moved into a nice place on the same block as a live music bar venue and regularly hung out there on Fridays. By pure happenstance, her and some of her friends showed up after bar hopping one night, and we started talking.
We talked about moving to the city, rent, all the usual small talk. Given our history and intoxicated state, our past started to creep into the conversation. The bassist on stage started playing, drowning out our conversation. She looked so pretty in the stage light. We danced, grinded, and started to make out on the floor. Her friends told her they were leaving, but she said she was staying behind with me. She pulled her face close to my ear and asked how far away I lived so that we could have a proper conversation.
We waited another couple of songs, I closed the tab, and we left. As soon as we got in the elevator she was all over me: untucking my shirt, popping the top three buttons open, tongue down my throat. I was overwhelmed at how aggressive she was, as we were both shy engineering students when we met. The dim lights of my apartment turned on when they sensed motion, and all of a sudden all of these clothes felt like too much. She unbuttoned the rest of my shirt while I lifted the verdant dress off her shoulders, exposing her skin to the cold of my AC. She shivered as I ran my hand down her arms before pulling her back in so I could reach around her bra. I fumbled with the strap and opened it; she shrugged it onto the floor, pressing her chest to mine for the first time in over a year. “I’ve missed this” she whispered, before kissing my neck and running her hands up my chest to massage my nipples.
I moaned, and she smirked: “you haven’t changed a bit, now have you?”
She pushed me onto the foot of the bed, letting me lean back before fixing her hair. She leaned forward, kissed down my neck, sucked on each nipple, then left a trail down to my belt. She unbuckled it and let my length free, sliding my pants to my ankles. I kicked them off one foot to spread my legs while she gripped my shaft, admiring it before she made it messy.
She started to lick up and down the sides, spreading her spit around to make me nice and wet. After she was satisfied, she started to swirl her tongue around the tip and take me deeper. I tried to push her head down, because she wasn’t deep enough for me to really get into it, but she choked as my head hit the back of the roof of her mouth. I didn’t want to make her uncomfortable, and I let her relax so she could suck me while fingering herself. She jerked me as well, slowly at first, and squeezed to make sure it felt better since she couldn’t take me deep enough.
As she sped up she kept asking me if I liked it, as if she was unsure she was doing a good enough job. Of course, I told her it felt amazing. She kept going, then sultrily climbed back up on top of me. She whispered that she wanted more, that she had waited long enough to have me again, all while grinding her pussy across my length. She purred, “I hope you have a condom lying around…”
Fuck. I didn’t want to kill the mood and run down to the Bodega, but I couldn’t remember where I kept mine, it had been so long since I needed one. The last time I bought any must have been before senior year, so whatever I had was long sense expired. I dug through my dresser first, then my nightstand, then the luggage under my bed. Jackpot: some old lifestyles, expiration date 1 month before today. I tore open the package and rolled the condom down my shaft and remembered why I stopped using this brand: they were much too tight on me, almost crushing the head of my cock. She smirked at me, wholly ignorant of how risky this might be, and leaned back, legs open.
I lubed up the outside of the condom and dragged it along her slit, teasing her, and remembered how the circulation cut off and made me feel nearly nothing. “Oh well” I thought to myself. “If anything I’ll just last longer, and I can take it off and cum down her throat later. Let her enjoy it.”
I slid inside finally and we both gasped, though her more than me. She jeered that I needed to go deeper, but I didn’t want to go too deep because the condom couldn’t completely cover my length, the ring was about an inch and a half from the base of my cock. I figured the rubber would stretch, so I slowly started to get into the motion. Since I was still standing at the edge of the bed, my legs were tensed and I accidentally pulled too far out a couple times. Both times she grabbed my cock and slid it back into her, inadvertently pulling the condom back, meaning my head was completely flush against the tip, no reservoir in the way. I figured it wouldn’t matter because I couldn’t cum anyway, so I pushed her back further onto the bed and climbed on top of her.
She wrapped her legs around my midsection and pulled me in for a deep kiss, effusing about how big I felt and how long it had been since she had been with someone. I lied that I thought about her a lot, and she kissed me back deeper, rocking her hips to signal that I needed to start moving again. I broke the kiss and moved down her jaw to her neck, feeling her squirm as I pumped faster and faster. I started to get used to the feeling of the too-tight condom, even as my cock strained against it.
She pleaded, “choke me,” and I was taken aback as this was not something the girl I knew from college would have requested. Happily, I obliged, tightening both hands around her neck as she clenched herself around my length. I told her how badly I wanted her and how good she made me feel. I could see her eyes roll back through her eyelids as I slightly loosened my grip when I felt her swallow. She opened her eyes and saw my scowl in the dimly lit bedroom, letting out a little gasp as she wrapped her arms around my neck. I relinquished my hold on her neck and balanced on my elbows to lean in and kiss her. She whined at me “why’d you stooop?” And I realized I had just sunk into her in the moment, wanting nothing more than to be close to her. I started back up again, crashing our hips together, trying to pound her into the mattress.
As things got more intense, I could feel a tingling sensation in my head as the condom started to not feel so tight all of a sudden. I groaned and fucked her deeper as I felt the condom split open, exposing the tip of my raw head inside her pussy. The sensation felt a hundred times better than the countless times I fucked her in college, even when we didn’t use a condom. I don’t think sex had ever felt this intense for me. I promised myself I’d let it go a little while longer, then pull out and get another. Every thrust brought a higher level of bliss, making this commitment harder and harder to keep.
As she tended her muscles, the rubber skid further and further down my shaft, making my skin slick with her cum. At last, all that was left was a thin ring of rubber at the base of my cock; my bare shaft pounding deep inside of her, feeling every little ridge and bump. I groaned again as I got closer, her nails scratching at my back, her breath in my ear exhaling “don’t stop…”
“Should I tell her?” I thought to myself. She was on the pill when we dated but that was over a year ago… I tried to slow down to last a little bit longer, to savor the pleasure, but she pulled me back in with her legs. To break the rhythm, I leaned in to kiss her deeply, slowing down until I came to a stop deep inside her. It took all of my self-control to not cum then, my legs were like steel they were so tensed. In between kisses she breathed that she wanted to be on top. Before I had the chance to object, we flipped over and she reached down to guide my length into herself. I could feel her brush the remaining ring of rubber around my base; my heart stopped, fearing she noticed.
She didn’t.
She sank down on my length, oblivious that my entire cock was seconds from exploding inside her—nothing between us. I wrapped my arms around her neck and pulled her close while she sped up, trying my hardest to not finish.
I failed.
I tried to finish as silently as possible, but she clearly felt my cum inside of her. She slowed down, kissing my neck, then caught her breath. As she slid off me, my cum leaked out around my cock. She looked at me and said “what happened to the condom?”
“I… uh… it must have… broken… I didn’t notice…” I couldn’t think of anything to say, my mind was still cloudy from the pleasure. She let her finger trace down the length of my cock, feeling from the tip down to the useless rubber ring. Fearing the worst, I told her we could go to a pharmacy, but she just smirked at me: “I hope you enjoyed that.” I did, of course. I removed the broken condom, threw it away, and showered with her. She spent the night.
Her and I didn’t talk for a while after that, but we one day got to texting over Instagram, which turned into a date, which turned into 3, which turned into moving in together. We both reminisce fondly on that night and often recreate it when we role play. We use oil-based lube and poke holes, the combination of which is often enough to make a condom break without much effort. I genuinely do not understand how I got this lucky, because this fetish is impossible to pull off outside of a relationship. For that, I am forever grateful.
Source: reddit.com/r/gonewildstories/comments/cum66r/mf_how_i_m_24_hooked_up_with_my_ex_f_23_after_a
This was very well written!