[Preface: Long. First time writing one of these stories. If folks like it, maybe I’ll write up some others. To skip to the saucy bits, scroll to *****]
I knew it would be the last time. I (F25) was moving across the country tomorrow. There was excitement for the future but also sadness about what I was leaving behind. Friends, co-workers, and the comfort of the undefined relationship between me and Tristan (M35). We were friends and...lovers I guess you’d say. We had a connection but were both ultimately looking for different things. That didn’t stop us from exploring our relationship from time to time though. Over the course of two years we on and off explored things. He was someone to lean on in intimate moments. He was a good teacher sexually as well. I was a virgin when we met and eventually he was my first (but that’s a story for another day).
For now, it was my last night in town and our last night together. We were technically roommates at this point. I didn’t move in with him as a couple, I moved into the open room in his apartment when my housing situation suddenly fell through two months before I moved across the country. I needed a place to live and he had an open room. He emphasized that he didn’t hookup with roommates though and that if we lived together we couldn’t continue with anything romantic. I was fine with that, telling him “I care more about not being homeless right now”. So I moved in with him and his 2 other roommates. Our “no hooking up” rule lasted two weeks.
Once we opened that door though it was too fun to close it again. It was a nice month or so: some days I’d sleep in my own room and some nights with him. It was like having my independence while also having a live in “boyfriend”. I had never lived with a guy I was seeing, so this felt like a fun “pretend” for a few weeks.
So when it came to an end after this honeymoon period, it was hard. We both had been caught up in the fantasy, knowing this wasn’t forever, but having a hard time accepting it when it came.
We got settled in for the evening. I finished packing and made sure I had everything ready for my flight early in the morning, the reality setting in. He would drive me to the airport, so I knew we had time for goodbyes, but somehow I knew tonight was our actual goodbye.
I wish I could say I remember every detail about the sex. But what I remember was it was tender and familiar. We knew each other’s turn ons and preferences extremely well by then. We kissed desperately and deeply. He had a way of calmly asserting his dominance. Not in an overbearing way, but in a comforting way. That if this was the tango, he would take the lead. I began to feel that side of him stir as we kissed. A shift I was familiar with. I could lean into him taking control and let go (something I didn’t often get the opportunity to do outside the bedroom).
Over the last month we had explored some light bondage and part of me wanted him to tie me up again and let him take control over me, but reader, I’ll leave those stories for another day too. This was all about goodbye sex. Desperate, tragic, longing, intimate, and hot goodbye sex.
Our bodies squirmed against each other as we kissed, me feeling the tantalizing pressure of him grow underneath me. I slowly rubbed his growing bulge over his boxers, feeling his excitement build. Soon I pulled the waistband down, revealing his glorious cock at attention. I gently played with it as we kissed, getting him ready for what was to come.
He turned me so my back was to him, both of us in a spooning position, laying on our sides. I lifted my top leg up and hooked it back around his legs, opening myself to him. This was our go to position, an odd one I know, but something I found so incredibly hot. I loved the intimacy of this position. I love the feeling of a big strong man behind me (I love doggy style too), but this had the added benefit of having his whole body pressing against mine, his chest against my back, with his arm pressed tightly around me and his hand playing with my clit. I never needed to work at my own orgasm with Tristan, he was devoted first and foremost to my pleasure. I didn’t need to put on a show for him, I could just turn around and hungrily wait for what he would give me.
As he gently played with my clit, he teased me with his cock, a game he liked to do. Rubbing it along me without yet entering me, our breathing getting heavier until we connected with just breath, no words. Gentle thrusting from each of us built as I silently begged for his cock to be in me. I was communicating with my ass, gyrating it against him, my pussy dripping wet at this point. Our rhythmic pumping was having a conversation, asking and teasing each other for more. Our shallow breaths escalating with each other, so much so that you’d think he was inside me this whole time. We had spent a lot of time over the course of two years hooking up without having penetrative sex, and so sometimes the foreplay was just as hot as the rest.
I brought my free arm up and behind me to grasp the side of his face. He was as close to me as he could be, his cheek pressed against mine in intimate urgency, but I needed him closer. I needed his breath closer to my ear, I needed his chest pressing as heavy as he could against me and I needed, above all else, his cock inside me.
After much teasing, FINALLY, he started pressing into me. Just the tip at first but soon the rest of him. His cock was perfect. As a newly former virgin he was the perfect girth to fill me but not hurt. And his length was the perfect fit as well, on the longer side, but stopping just before the point of being too much. (This is something I took for granted at the time since I’ve had some adventures after the fact with larger cocks that have been too much...another story dear reader) ;)
He slowly pushed into me with his distinctive grunt. His mouth open as if in surprise but his eyes with a knowing and hungry determination. “Oooh yes” I moaned, getting up the energy to vocalize what we’d silently been communicating this whole time. I let him take the lead, grabbing my waist and slowly yet firmly pumping into me. My pussy was dripping for him. I wanted this to last all night. He could last an incredibly long time and part of me wanted this sex to go on forever. To delay the inevitable reality of flying away the next morning. I wanted to pause time in some sort of sex time freeze. But at the same time, we needed each other too much in this moment to prolong it.
His hand came back to my clit, his strong fingers expertly working in tandem with his thrusts to tip me towards my own pleasure. As my moans built, they confirmed what a good job he was doing. But he had his own way of letting me know I was pleasing him. He exhaled into my ear “good little girl”. If I had a dial to show how turned on I was hearing that it would’ve shot straight up to the highest setting. I loved being his little girl. We were both adults, me in my mid 20’s, him in his mid 30’s, so while entirely appropriate, our age difference was enough to add some spice as we explored our balance of my submissiveness vs his dominance. It also helps that he’s tall and I’m super petite. I wanted to do good for him. I wanted to receive the pleasure that he was trying so hard to give me. And the pleasure he received back was in the form of my successful pleasure (I guess I’m a little bit greedy, oh well). :)
My moans became more of staccato whines as he picked up his pace, him knowing he was turning me on with his words. I hadn’t always been confident enough to reciprocate dirty talk, my shyness in bed slowly fading over the previous few months. So when I did engage, he knew that not only was I spurring him on for more, but also that I was a good student. I had learned his lessons to verbalize what I was liking. In a high pitched whine I gasped out “oh yeah? yeah?....am I your good little girl?”. I could feel his shock and happiness behind me through his skin. By pushing this verbal roleplay I was unlocking another key to our kinks and something I knew made him incredibly horny. “Ooh yes” he hissed in my ear, picking up his speed pumping into me and rubbing my clit.
I was getting close and I could sense he was too. We were losing our composure more and more by the minute, both of us giving over to the extreme pleasure of the moment. His body thrusting behind me, his hand bringing me closer and closer to climax, my hand around his face pulling him desperately to me. I turned my face slightly and desperately and sloppily kissed him. Our breathing became one and our pace grew in tandem.
I needed to tip over the edge. I was in ecstasy and I wanted to cum for him. I wanted to be a good girl and cum all over his cock.
I challenged him “you wanna make me cum? Make me cum baby”. I turned my head away, making the angle of our bodies easier for entry. “Fuck” I heard behind me. His surprise at how much I was verbalizing my needs. His grunts grew more primal. I knew when I had him this vocal he was in the home stretch. “Mmmm yeah baby make me cum for you, I wanna cum all over your cock. I love your cock in me. Make me cum baby, make me cum! Aaaaaaahhhh!!!” I tipped over the edge and roughly came deeply and severely over his cock. I heard his groans “Oooooh yes, oh god, oh fuck yes” behind me. We came together, just as in sync as before. The pleasure rushed over me and we struggled to catch our breath. Still connected by every inch of our skin, my legs open for him and my cunt pulsing on his spent dick.
Just as quickly as the pleasure arrived, my mind immediately reminded me to savor it, the reality of this being our last orgasm together setting in immediately. It’s such a strange thing to experience such a high of sexual endorphins while simultaneously feeling a crash of sadness. I was on top of the world, but I was also incredibly crushed.
I turned to kiss him, with him still inside me, putting the bookend on our sexual adventures.
The rest of the night was relatively uneventful. We cuddled all night until the annoying blare of my alarm woke us at the crack of dawn to get to the airport. It was too early. My time was up but I wanted to hold onto it longer. Him, and all the memories of this place that I would miss. We drove to the airport mostly in silence, him holding my hand, the reality of this goodbye finally hitting us. When we walked in, the chaos of the airport necessitated an unexpectedly quick final goodbye. I quickly turned around and he kissed me one last time. A hurried kiss. The type of kiss you only have in moments when you’re out of time. There was no time for sad goodbyes or final deep kisses. I was swept up in the traffic heading to security. Our grasp on each other’s hands broke apart. I was onto a new adventure now. I turned away for the last time and walked forward. My future was up to me now.
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from Gonewild Stories https://www.reddit.com/r/gonewildstories/comments/n1hlti/a_final_goodbye_before_moving_fm_long/
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