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Before settling down, I had a debaucherous past as a single guy in the city. Just good-looking enough for women to say yes, just smart enough to stimulate their imagination, and just safe enough to coax them out of their comfort zones. These are some of my most memorable adventures.
I have a thing for petite redheads. Redheads in general. Their milky skin, seemingly innocent exterior, and higher-than-average tolerance for pain make them simply irresistible. Andie is one of those petite redheads Iâve had the pleasure of having casual sex with twice. This is the story of our second and last encounter, after she ghosted me years ago.
We matched and didnât immediately recognize each other. We shared a few pleasantries before she asked me, âHave we met before?â At first, I wasnât entirely sure because it had been a few years. But when she reminded me that we had whiskey and grilled cheese, I knew exactly who she was. She told me she ghosted me because she had never had casual sex before and felt weird afterward but had since become more sexually experienced.
Andie looked a little different. Now in her mid-twenties, she was more confident and sure of herself. She had grown her hair out from a pixie cut to a bob just below her chin, framing her slim, round face. The last time we met, it was a spontaneous date. It was in the middle of the dayâwinter, if I remember correctlyâand she agreed to meet me within an hour of us chatting. We met at one of my favorite bars, where we had whiskey and grilled cheese before heading back to my place. But thatâs a different story.
After our memories were refreshed and we realized we had already fucked each other, the conversation just flowed with ease, like two old friends catching up. We werenât trying to impress each other in the hopes of getting laid. We just opened up and spoke freely. Naturally, we started talking about sex and shared our own adventures since we last met. Turns out, fucking me spontaneously was just the beginning. Andie had come to terms with her sexuality, and her confidence in what she liked and didnât like was incredibly hot.
We quickly bonded over our shared love for thrills and dangerâhow weâd enjoyed public sex, sex with strangers, and anything with an element of risk. She told me how she picked up a woman during a work trip, and I told her about the sex parties Iâd been to and other casual encounters.
We chatted late into the night, and naturally, we started sharing our fantasies. Even though we had already had sex, we were still practically strangers. I told her how much I love having carnal knowledge of a woman within moments of meeting her, and she shared the same kink. Thatâs when I told her I wanted to fuck her again. But this time, weâd skip the date, and I wanted to be inside her as soon as we met.
She pushed the idea even further and suggested that I just show up at her apartment to find her door unlocked and her naked in bed, where Iâd come in and have my way with her. Without hesitation, she texted me her address and told me to come anytime after 1 p.m. the next day and her door would be unlocked. With my flexible work schedule, I told her Iâd be there without telling her the exact time to add to the anticipation. Iâm sure we both went to bed that night with great excitement.
I arrived a little after 1:30 the next day. She lived in a big building with an old elevator. I tried a bunch of buzzers (but not hers) before being let in. Waiting for the old elevator to take me up to her floor felt like an eternity. When I stepped out, I saw rows of identical-looking doors. My heart was beating as I read each door number⌠11B, 11C, 11D, 11E, 11F.
I turned the doorknob, and the door opened.
The apartment was dark, with blackout shades pulled down. It was a small studio, and immediately to my left, I saw Andie. Naked. She was asleep (she did tell me sheâd had a late night at work). Without exchanging a single word, I lifted her up so her face was now level with my crotch. I undid my pants, and instinctively, she took me into her mouth. It had been no more than a minute since Iâd walked through the door, and my cock was inside her mouth.
I grabbed a fistful of her fine red hair and pushed myself further in. Andie was now on her knees, fully taking me inâa man sheâd only met once before. The blowjob went from sleepy to sloppy quickly, going in and out of her mouth while she alternated between licking and sucking. I continued to undress as she worked on my cock.
Her ass was up as she knelt on all fours, licking my shaft and my balls. I reached over and felt the wetness between her legs. My fingers slid right in, and I fucked her with my hand while enjoying her mouth.
I still had my shoes on and couldnât take my pants off. So, with great hesitation, I pulled my cock out of her eager mouth to finish getting naked. I joined her in bed and pulled her in by her waist.
Andie is petite, with perky, pale breasts. Her ass isnât what youâd call big, but itâs nice and round. I started sucking on her breasts, licking and teasing her nipples while my free hand fondled the other. She moaned softly as I sucked, and squirmed when I bit gently on her tiny, eraser-sized nip. We still hadnât exchanged a single word at this point, and this was all a part of the fantasy.
I laid on my back and let Andie put my cock back into her mouth. She kept her pussy within reach so I could finger her and rub her clit while she sucked me. To the side of the bed was a full-length mirror that Andie must have put there for us. It was clearly taken from a closet and was leaning against the wall, giving me a good view of the rest of her body from a different angle. As my eyes moved between looking down at her and the mirror, I caught her looking. We made eye contact through the mirror before meeting each otherâs glance directly with her mouth full.
Thatâs when I knew I needed to fuck her. I reached for a condom in the pile of clothes on the floor while she climbed on top of me. I rolled the condom on and watched as she lowered herself onto me. I love having a beautiful woman on top of me, especially the view of her beautiful curves. She started off slow and picked up pace, rocking back and forth, up and down. We were both in ecstasy. I reached up and grabbed one of her breasts, squeezing her nipple between my thumb and index finger as I pinched.
I could feel her tense up with the nipple play. What followed was a quiet orgasm that you wouldâve missed if you werenât paying attention. We switched positions, and I got her on all fours with her ass up and her face pressed against the bed. I entered her from behind with ease and continued to fuck her. As I was fucking her, I started to have an out-of-body experience. I looked around at this dark studio apartment, one that Iâd never been in before and would never enter again. I saw myself fucking this beautiful stranger. Her pale body was like a bright spot in this dark room. My hands were on her waist as I fucked her harder and harder. My cock disappeared deep inside her, only to come right back out and in again, filling her up.
I pushed her down with her belly flat while still inside her. My entire weight was now on top of her, while my cock was still buried inside. My face was pressed against her neck while I grabbed both her wrists above her head. I fucked her faster and faster as I held on to her tightly, taking in her scent. And just like that, I exploded inside her, filling the condom.
I laid on top of her briefly before pulling out, making sure my cum didnât spill everywhere. Thatâs when we finally broke our silence, and I asked for some water.
We spent the next little while laughing and talking about how hot that was. She said the waiting was too much and that I shouldâve come over earlier. We said we should do this again and have a different adventure next time. She stayed naked while I got dressed to get back to work.
She ghosted me again, and Iâve never heard from her since.
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