Straight dom to bi bottom – all in the space of an impromptu Grindr meet [MM]

Over the years, I’ve occasionally fantasised about testing the boundaries of my sexuality, but had never acted on it until the encounter I’m about to go over. I’ve always thought of myself as straight, but with a keen interest in exploring my limits and kinks openly. Just as importantly for this, I’ve always thought of myself as fairly dominant in the bedroom (although in retrospect, it’s probably – at least partially – forced on me from the women I’ve dated). I’d like to think I’m reasonably attractive – I’m in my late 20s, white, 6’4″ and have a fairly average (leaning towards slim) build. I’m also very well endowed at around 8″.

Our evening, a Friday around 4 months ago, started like many others – in the midst of a global pandemic, I hadn’t gotten laid in a long time, and I was starting to feel desperate. Like I’m sure a lot of people would in my situation, I very quickly found myself browsing porn and letting my browsing take me to various classified subs on reddit – the ratio of men to women across the various R4R and classifieds subreddits on reddit has always put me off seriously looking for an MF encounter, and as before, I let myself consider meeting another guy to suck me off. As time went on, I flicked across RAOB, LondonR4R (hello fellow Londoners!) before opening Grindr, where I had a profile setup from a previous, very similar session weeks before.

I had received a few messages – many of them crude, definitely not what I was interested in (I had made it clear in my profile that I was bicurious, a vers top, and was likely just looking for someone to get me off). One message stood out – he was in his early 30s, articulate and polite, and he had messaged only a couple of hours prior. I’d not been online in weeks, so it seemed like serendipity. In my rush, I replied asking him what he was looking for, not expecting an answer. Less than 10 seconds later, my phone vibrated in my hand and I felt my heart skip a beat.

To this day, we’ve never exchanged names – but in my head, I call him Jamie. “I love edging straight bulls for hours until they can’t possibly hold it in anymore. How do you like the idea of being blindfolded, massaged and edged until you burst?” was the message. I was sitting at my desk, shaft in one hand and phone in another, and could feel my cock gently pulse at the thought. “That sounds nice.” I replied a short while after. “No reciprocation needed. I just like taking control of someone else’s pleasure. ;)” This is probably the point where my brain switched from “just another night jerking off” mode to seriously considering my first MM encounter. My heart was pounding and I was starting to shiver at the thought. Jamie followed up with “Do you like being rimmed?” before I even had a chance to reply. I was still nervous about expectations of reciprocation, and so responded that I did, but didn’t particularly enjoy rimming myself. “That’s fine, I don’t like receiving it, but I love eating ass.” We talked back and forth for a while, the anticipation as he was typing each message convinced me that, yes, this was something worth exploring. We exchanged pictures – none showing our faces as we both stressed discretion was paramount. He was was well-muscled, and well-groomed. Very masculine – not what I had originally thought to be my type (I had been leaning more towards slim/feminine), but I was still intrigued. He didn’t send any cock photos (though I sent several), and I was wondering if it was because he was packing, or because it was tiny. I decided I didn’t really care – I told myself I wasn’t planning on anything more than a polite handjob if it came to that. “It’s getting late,” I wrote, “but you’ve given me something to think about,” and I started moving to finish myself off. A moment went by before my phone buzzed again. “Do you want to meet?” – and at that moment, I exploded in ecstacy, my cock shooting ropes of cum all over my stomach. I stared at my phone sheepishly, the initial waves of disgust slowly starting to set in. I realised that, actually, the thought still made me tingle. “Yes, can you host tomorrow?” I replied. “I can. Message me in the afternoon. Good night.” – and with that, I retired for the night wondering whether I’d go through with it the next day.

The following day I got out of bed as normal, had my morning coffee and shower trying to reconcile the night before with how I thought of my sexuality. I tried to convince myself that when the goal was sexual pleasure, it didn’t matter whether it was helped by a woman or a man, and over the course of the afternoon, I was slowly getting more and more comfortable with the idea. At around 3pm, I messaged Jamie, my heart feeling like it was trying to escape my chest cavity.

“We’re still on for tonight?”

“Yes. Glad to hear it sounds like you are too. Can you come by at 9? I’ll have everything ready.”

My cock tingled at the thought.

“What are you getting ready?”

“Blindfold, oils, music… and if you’re open to it, I have a set of handcuffs?”

The tingling kicked up another notch.

“OK – but be nice, it’s my first time remember ;)”

“No problem… I’ll buzz you into my building, take the lift up to my flat and I’ll leave the door open. Walk into the bedroom, get undressed and lay down face-down with the blindfold on… I’ll be along shortly after. Don’t talk.” He included his address and flat number.

“Are you planning to be naked or dressed?”

“Don’t know yet, I guess we’ll see… but remember that it’s all about you.”

We exchanged a few more details – although I’ll attest to being unable to remember anything specific. The day went by very, very slowly.

At 7:30, I decided to shower and, not knowing what to expect, cleaned myself *thoroughly*, trimmed between my legs, dried off and got dressed. The butterflies in my stomach felt like they were throwing a rave, but I resigned myself to what was coming, thinking that even if I didn’t enjoy it, no harm would have been done – I was simply exploring my sexuality and the fluidity of my orientation and I could say “stop” any time. I set a timed message for a good friend that would fire off at 2am in case I didn’t cancel it (better safe than sorry!) and made my way to Jamie’s.

——–

I parked up nearby (anyone who lives in the London area will know how difficult finding street parking is) and looked at my watch. It was 8:55. I quickly messaged Jamie to let him know I was around the corner and would be with him imminently. He replied that it was fine, gave me some more detailed directions to get to his building, and reminded me of our previous agreement on how I should “present myself”. I felt the palpitations of my heart in my throat as I buzzed his flat – the lock unlatched and I walked in. It took me another 5 minutes to find his door, ajar as he had said, and I made my way inside.

It was clean and pleasant – a good sign, considering I wasn’t sure what I was about to experience, really – and I followed Jamie’s directions to the bedroom up a flight of stairs. I could smell the fresh sheets, and gentle lo-fi beats floated from a speaker in the corner. A padded blindfold and a pair of restraints were placed in the middle of the bed. No sign of Jamie, just as we had discussed. I swallowed, thought “fuck it, it’s now or never,” and stripped down, taking the time to fold my clothes in a neat pile in the corner of the room. I hesitated for a moment, put the blindfold on and lay face-down in the middle of the bed, waiting.

About two minutes later, I heard the sound of bare feet slowly making their way down the corridor towards the bedroom. I was trying to control my breathing – focusing on something in my control – and before I knew it, I could tell there was movement in the room. I lay still, feeling exposed, but comforted by the blindfold obscuring me. I could hear the rustling of clothing coming off. Another minute or so went by, a snap-top bottle opened, and I felt a weight settling at the foot of the bed, and moments later, a pair of warm hands on my back. I took a deep breath.

Jamie slowly started coating my back in oil, moving down my legs, around my ass cheeks and around the inside of my thighs. He started massaging me in earnest, and I occasionally felt his legs and arms brush against me as he worked. I was sporting a slight chub – the nervousness seemingly keeping me from going full mast – but it was still tucked against my stomach. It felt fantastic. After a few minutes, he took my arms, placed them behind my back and I could feel the restraints closing around my wrists. I was now entirely in his control, and I felt completely at ease.

He got slightly bolder, starting to shift my body around as he worked, his attention slowly shifting to my ass and crotch. He spread my legs and lifted my hips slightly, pulling my cock down to expose it. He gently ran his hand along it, and I felt it swell in his hand as he did.

He grabbed my hips again, this time pulling me almost to a kneeling position and let a finger gently run across my asshole. It felt amazing and I shuddered. Moments later, I felt his tongue encircling my asshole, his trimmed beard gently touching my ass cheek. I shuddered and felt my head sink further into the bed and my cock growing even bigger, precum dripping from the tip. He kept at it for what felt like hours, the tip of his tongue slipping into my ass, occasionally running along my balls and then back to swirl around. He eventually stopped letting out a sigh. He kept me in position, his hand reaching around me to rub and jerk my cock and I felt my orgasm building – deftly, he stopped before I could burst and returned his attention to my ass. I felt him slipping a finger in, gently working it back and forth. I’d never had my ass penetrated, and it felt like heaven. He added more lubrication and inserted a second finger, responding to my gentle moans and sighs. I felt exposed and vulnerable, and found myself enjoying the psychological sensation more than I thought I would… so much for wanting to be in control..

After another minute, he slowly slid off the bed and I heard the sound of rustling near me. Again, the snap of a bottle cap opening and I felt something cool rub against my ass – I relaxed, and slowly, he inserted what I guessed was a toy in my asshole. He gently moved it in and out – I could feel the smooth texture of silicone and the small bulbs around the length of it sliding in and out, and the thought of being fucked with a toy made my head spin. I was thoroughly in his power for him to do as he pleased. Moments later, a new toy – this one bigger – took the first one’s place and stretched my asshole wider than I thought possible, then he let go and let it settle. I could feel the flare of the handle against my ass, convincing me it was well and truly in deep.

He gently set me down on my stomach, then nudged my arm indicating I should roll over. I did eagerly, wondering what he had in store for me next. The next 15 minutes or so are a blurry, blended mess – I felt him jerking me off, massaging my balls, teasing the tip of my cock with his fingers until I was ready to burst – then eased off when he could tell I was close. I felt him move around me on the bed and realised suddenly he was laying alongside me, his leg brushing against my cheek, while he kept up the touch on my cock and balls. I was horny, feeling submissive and I wanted him to enjoy it, too – I moved my head slightly – still unable to see – and felt his hard cock brush against my face… I opened my mouth and gently licked the head, prompting an “ohhh” from Jamie. I was a little startled – this was the first sound he’d made since we had begun ~40 minutes prior – and knowing the effect it had felt good. In retrospect, I’m sure his cock was average, but without the visual and a previous frame of reference, it felt huge.

I got bolder, taking the head of his cock in my mouth and swirled it with my tongue, then took it as deep in my throat as I could – not an easy feat without my hands to guide it. Another moan escaped Jamie. I increased the pace, and I suddenly felt Jamie’s hips start to move. Within seconds, Jamie was slowly fucking my mouth and throat and I loved knowing I couldn’t do anything to stop it. Almost as quickly as it had begun, it ended. “I want you to cum soon” he said and all I could muster was a weak “okay”. At this point, I had been brought to the edge of an orgasm at least a dozen times, only to have to reset and start again. My body was aching and my thoughts were fuzzy, and I knew it should end, though I didn’t want it to. I had somehow gotten turned around, my head towards the foot end of the bed, and Jamie shifted to sit against the heard board, pulling me in between his legs and lifted my ass up, pulling me in so my cock was against his. He put his legs under me to put me at an angle – balls and the plug in my ass facing him – and he held both of our cocks cocks in one hand, jerking us both off. He went slowly at first then sped up. I could feel my orgasm building, my breathing quickened and I let out a moan as I shot ropes of cum in the air all over my own chest. Seconds after, Jamie let out a loud moan and let his cum shoot over my cock, up to my chest and against my neck. I felt the tiniest bit flick across my chin. I was exhausted and overstimulated, but felt sated like I hadn’t in months. I had mine and another guy’s cum all over me, and I was *loved it*.

I felt Jamie lean back and slowly begin to extract himself, but not leaving the bed as I lay breathing heavily.

“Was that OK?” he asked gently. “Yes,” I replied, a small smile spreading across my face. The usual waves of regret and disgust I expected (guys – you’ll know what I’m referring to) from my experiences jerking to gay porn were creeping on the very periphery of my consciousness, but more than that, I simply felt satisfied. “Yes, I’m fine.”

“Are you OK with everything that happened tonight?”

“I am. Don’t worry.”

“OK. You are free to take a shower, then get dressed and leave. I’ll be on the balcony until you’re gone. I hope I’ll get to see you again.”

Unceremoniously, I felt him get up, walk across the floor and leave the room. I waited another 10 seconds, then removed the blindfold. I made my way to the bathroom, conscious of the plug still firmly inserted in my ass, and rinsed off. I removed the plug from my ass, and was shocked – and slightly proud – to see [the size of the plug](https://i.imgur.com/MZfqMQP.jpg) I’d had nestled in my ass. I washed thoroughly, and made my way back out to the bedroom, got dressed and made my way down the stairs and out the door.

I drove home to find a notification on my phone. It was a message from Jamie.

“I really enjoyed that, and your ass is delicious. When would you like to come back another time?”

…and that may be for a future story.

Source: reddit.com/r/gonewildstories/comments/if2xgf/straight_dom_to_bi_bottom_all_in_the_space_of_an