I (M31) had a FWB relationship with a friend from high school (F30) about four years ago. (I’ll call her M.) Though we’re not together anymore, the memory of our time together still thrills me to my core.
M and I were in the same grade in high school and shared a few classes together. I liked her just fine then, but was preoccupied with other girls and only thought of her as a friend. After high school, M and I fell out of touch for a couple of years before spontaneously reconnecting over Facebook. She remained in our hometown while I went to college out of state, but we soon kept in touch on a daily basis – sharing our goals, thoughts, preferences, and daily chitchat with each other. We both pursued relationships with the opposite sex, but both remained single. We continued that way for five years.
A year after I finished college, I experienced the worst heartbreak I’d ever felt when a near-perfect woman I’d been pursuing for two years turned me down for another man, then abruptly ended our friendship over a fumble I never had the chance to explain. We’d been honestly close until then – working on artistic projects together and sharing personal stories – and I’d waited patiently for a long time while she decided what she wanted. When she was suddenly forever gone from my life, I spent a long time struggling to recover from it. I went through every stage of grief. From my point of view, I’d lost the love of my life. Though I trusted that I could still find someone eventually, I despaired at finding another woman as fine as her ever again, and live a life of half-fulfilled dreams and bitter regret.
I’d been keeping M updated throughout the whole debacle, and she really felt my pain – partly because she’d heard about it since its inception, but also because she’d recently experienced something similar herself. She’d also found a man she thought of as her soulmate, and spent several years obsessing over him. They went on a few dates and shared some passionate times, but he’d decided that she wasn’t what he was looking for – something she found hard to really accept. (He was a co-worker, which made the “moving on” process difficult for her.) Over and over again, she’d tell me that she was well and truly over him just to announce some new effort to win his heart a few days later, or ask me to analyze the meaning behind some comment he’d made in an email. By the time my big heartbreak rolled around, she was on the downswing again – depressed and despondent.
I’d sometimes wondered if M’s continuing interest in me after high school had some romantic element to it. Friendships after high school rarely last, and long-lasting platonic friendships between men and women (while not impossible) are suspect for many. With all the other people we’d both been seeking and opening encouraging each other for, I thought that idea was silly… yet sometimes found it titillating, too. Sometimes I imagined us together. Sometimes I imagined her naked. The idea made me happy, but I never did much with it. As in high school, other women were always preeminent in my mind.
So it was in this post-heartbreak frame of mind – emotionally devastated, and desperate for relief from that devastation – that I heard a particular remark she made one day which – interpreted a particular way – seemed to prod me for romantic interest. I do not now remember what the remark was, but I remember that that interpretation of it was far from a sure thing. It could’ve meant a number of other things, and in light of everything else, I should’ve known that it probably did. And yet I couldn’t get it out of my mind. What had formerly been a fleeting fantasy grew stronger and stronger in an emotional environment desperate for relief.
One night in February of 2019, I worked up some nerve and shared my suspicions with M. She denied that that was what she had meant in that remark, but with the topic of romance between us finally broached – we had never discussed it so directly before – our subsequent conversation circled around it, unable to get away for long. She started speaking in theoreticals – “If I had said yes, what would you have done?” and “Do you think about me that way often?” Eventually, the sexual tension inside of me broke, and I confessed that I really wanted to kiss her. For real.
Within fifteen minutes, she rolled up to my house.
With neither of our home situations conducive to this kind of thing, we found a dark place in the neighborhood to park. She knew that, at the ripe old age of 28, my nerdy, awkward self had never kissed a woman before, and she wanted to make it a good experience. After a few minutes of sitting together, working out some nerves, and confirming that this was really what we both wanted, she leaned over the dash and kissed me. Just a short one at first, then longer. I could scarcely believe that what was happening was really happening.
After kissing again and again for close to twenty minutes, we moved to the back of her car, where we could really make out and feel each other up a little more – shoulders, arms, hands, thighs, sides, and thighs. It was even better than before, and with slow, respectful, passionate moves, the nerves melted away. After what must’ve been another twenty minutes – but felt like so much more – she pulled back so we could take a breather. She asked me if I’d noticed anything about her when I’d been close to her, and I told her that I had: she wasn’t wearing a bra. She confirmed that that was correct, and that she’d specifically removed it before coming here to offer me something we hadn’t discussed in our planning but which she wanted to offer me anyway – the opportunity to feel her breasts directly underneath her shirt.
I hesitated for a moment – I worried about slipping further down this road than I’d taken the time to really think out – and declined her offer. We’d just keep making out like we’d done, I said – that was enough. She respectfully accepted my decision, and we got back to making out. But in spite of my refusal, M was no less passionate, her lips no less powerful on mine. She accepted what I wanted, and that turned me on. I thought about it. I’d spent so long fantasizing about things like this, and now it was here, in front of me. I was nearly three decades old and was not only a virgin, but had been – up until less than an hour ago – a lip-virgin as well. I found myself so tired of dreaming. So after a few minutes, in the midst of our kissing and without saying anything to break the mood, I threw caution away and slowly snaked my hand over to her belt buckle, under the hem of her shirt, up her smooth stomach, and onto her right breast – touching the nipple first, then more firmly cupping around the breast entire. She was perfectly soft and round and firm – far better than I’d ever imagined it. We both panted more powerfully now, and kissed faster and more forcefully.
We continued for another ten minutes, with me stroking her nipple, giving light squeezes, gently scratching the skin of her breast and back, and occasionally switching from one breast to the other. But then someone (I don’t remember who) said that we’d better get back home before anyone missed us. She took me home, then drove to hers alone. When she got back to her place and our Facebook conversation resumed, our conversation was a flurry of thank-yous and I’m-so-glad-we-did-thats and you-were-amazings. She asked me if I’d want to do it again sometime – maybe in a hotel room, where we’d have more time and greater freedom. I said that I would. With the severest heartbreak of my life just behind me, I found that my heart had never been lighter.
“Sometime” came much sooner than I expected. The following day, I came home from work to a message from her, saying that she was about to rent the room and wanted to know what time was best for me. I was surprised – I thought that by “sometime” she’d meant some far-flung day in an unplanned future, not tomorrow! But my mind had been whirling with nothing but her all day, and while I had to make an excuse for another prolonged absence – not my expected behavior at all – I was thrilled at the prospect of more intimate time with M. I Venmoed her my half of the hotel fee and drove on over – finding her already waiting for me in our room, eager and ready in a T-shirt and sweatpants.
We were bolder now. Our time in the backseat had been hampered by nervousness of someone spotting us, but we were free of that fear here. And while we still hadn’t consented to taking things all the way, we’d pushed certain boundaries, and were eager to see if we could push them again.
We kissed and fondled each other without restraint – using our tongues now. We stripped off our shirts (no bra again) and pressed breasts to chest. I kissed and sucked and licked them freely now, squeezing more firmly and rubbing with greater delight. She kissed and rubbed my chest, giving me an erection so hard I had to ask for a break. As the time drew on, I made a suggestion – that we snake our hands into each other’s pants and feel each other’s genitals. She agreed, and we took it one at a time. She told me later that she’d been worried that my penis would be disappointingly small, but was surprised to find it normal. (She’d thought my whole body would be much skinnier than it turned out to be.) When my turn came, I needed a little bit of guidance to find her vagina. (I’d only seen them in porn before, and seeing and doing are two very different things.) It was delightfully wet and tight and warm inside, and with her guidance, I rubbed her nearly to orgasm while she did the same to me.
Two days later, we were in a hotel room again – a larger one this time that I had picked out, and with more time allotted. Our Facebook conversation on the day between the first hotel stay and this one had been hot and heavy. We openly confessed every sexual fantasy we could think of, and made plans to make them true for each other. In that hotel room, we stripped completely naked for each other and kissed standing up, pressing ourselves together. In preparation for oral sex, we showered together – rubbing every inch of each other’s bodies with soap, kissing and fondling each other’s faces and breasts and cock and pussy as the water trailed over us. We tumbled into bed together, bodies still dripping and pleasantly chilly, and with me on my back, she took my penis into her hands. She licked it at first, then sucked and nibbled, and I moaned through all of it. This wonderful woman who I’d spent years talking to, with whom a week ago I’d never spoken of sex, was now gobbling my cock in the most wonderful way. She declined to let me do the same to her – citing a bad past experience I respectfully didn’t ask for details about – but we found other ways to thrill ourselves. I rubbed her to orgasm again and again. I fulfilled a longtime fantasy of mine when I smeared warm honey on her breasts and stomach and licked it all off. We snuggled naked for long, comfortable hours, feeling each other and kissing over and over in absolutely bliss. I pinned her to the wall and ran my penis up and down between the cheeks of her ass while squeezing her breasts as hard as she would allow while she moaned for all to hear. All in all, those golden hours were the most magnificent experience of my life up to that time.
With that third encounter, we were free from nearly every inhibition, and we started meeting in private all the time. In another hotel room, she started one encounter by walking in on me unannounced in the shower while I cleaned myself for her (which remains to this day one of the sexiest things I’ve ever experienced). On another day, I stripped her naked on the floor of the bedroom she grew up in, her family tantalizingly close to discovering us (but without real risk, she assured me), and I ran my penis along her pussy as she laughed beneath me. Later, she got her own apartment, and we spent long hours on her couch, on her floor, and in her bed, kissing and groping and rubbing each other to orgasm. I came on her bedsheets so often we started laying towels down so she wouldn’t have to change the sheets so much. When we got tired, we laid in bed together and watched favorite childhood cartoons naked until we were ready for more. We sexted when I went on vacation with my family. We discussed renting a cabin in the mountains for a long weekend together and falling asleep in each others arms. We discussed sharing her bed with another woman (she’d long been curious about if she’d enjoy lesbian sex, and I’d wondered if I was polyamorous). With M, I went from no sexual experience at all to nearly every non-penetrative act I’d ever dreamed of.
My heart races as I type this. My time with M has become one of the most wonderful times of my life. But as wonderful as our experiences together were, we both knew it wasn’t to last. For the first thing, that was what we’d repeatedly agreed to. Secondly, outside the bedroom, we argued constantly. The boost of confidence we both got from our time together put M back on the upswing with her dreams about her soulmate. Because we’d agreed that our fling would be temporary, we felt no shame about talking about others we were attracted to – and for M, that included her lost beloved. As I had done before, I encouraged her to put away her painful desperation and focus on future opportunities instead – an idea she found infuriatingly unsupportive. We differed in other respects, too – religious views, political views, and in personality. Though she was an amazing bedpartner, M would’ve made a poor wife for me, and I a poor husband for her. We knew this from the start.
And as badly as we both wanted to, the threat of pregnancy kept us from ever full-on fucking (I’m sure you were wondering). She was all for it, but I was, at last, too afraid. Though I knew that pregnancy was comparatively low even without protection – and far less with it – I was terrified of even the slim possibility. Since we didn’t want to spend our lives together, pregnancy would damage if not ruin both of our lives and that of any child we produced. Most importantly, M’s moral opinions were different than mine when it came to abortion… which was something I simply couldn’t involve myself in, no matter what. So we contented ourselves with enjoying everything short of actual fucking. When thinking about this now, this is my one great regret – that I didn’t fuck her at least once.
M and I shared more than twenty near-sexual encounters over the course of three months, and I was still visiting M’s bedroom when I met the woman who would eventually become my wife (who I’ll call J). J and I hit it off pretty much immediately, and within a few weeks of meeting her, I knew that things between us would likely only snowball from there. I consider myself an honorable man, and while I could’ve continued visiting M until things became official with J (and even after, if I’d wanted to), I decided that the best thing to do for everyone would be to break off my near-sexual relationship with M. She took the news with the same respectful grace she’d always had, and we had our final encounter afterwards – very nearly fucking, but stopping just short. I got dressed, gave her a final kiss, and left her bedroom for the final time. We remained close friends after that, but never touched each other’s bodies again.
M and I are both married now, but not to each other. I gave my virginity to J (a story worth its own telling) and lead a mostly fulfilling sex life. J is sexy and passionate and shares many of my fetishes. Both our spouses are aware of the wild times M and I shared and accept them. But even so, M and I rarely speak anymore, and never of the thrills we shared. (Honestly, that’s another thing that makes me suspect her continued interaction with me all those years in college was romantic in nature. I don’t feel used, though – I just wonder if we might’ve shared our bodies for years instead of months.) Looking back, I can honestly say that I made the right decision overall. While every woman has her pros and cons, and every relationship has its bumps and rattles, J is a much calmer, steadier life partner for me than M would’ve been. We have a son now, who brings us great happiness.
But sometimes, when it’s late at night, when my wife is still at her computer in the other room, and the baby’s asleep, and when I’m laying naked all alone with nothing but my thoughts… M is all I can think about. How badly I’d like to share a bed with her again. To feel her skin against mine, her nipples between my teeth, her gently wettening vagina against my leg. How badly I want to kiss her lips and and, at long last, fuck her breathless, coming inside of her warm body again and again in that cabin we might’ve stayed in before falling asleep in each other’s arms as the snow falls silently outside. That, dear reader, is my fondest fantasy.
Source: reddit.com/r/gonewildstories/comments/zq4b3y/surprise_fling_with_a_friend_after_mutual
We all have a mental rolodex of previous partners.
Well written.