A month ago, while on a work trip, I gave a stranger the most delicious head and throat I had ever given. He turned out to be my client, and I've been dreaming of his BBC ever since.
Despite my intentions to keep talking, Reggie (the owner of the perfect cock in question) pretty much ghosted me after we realized he was my client, which I completely understand given the situation. This does not mean that I stopped dreaming about his cock and his cum though, and hoping a new work trip would be scheduled soon, and that Reggie would be part of the team.
To my greatest pleasure, three weeks ago, I got the confirmation that a new trip was being scheduled for early May. I was extatic at the prospect of meeting him again, stretching my throat for him, and tasting his cum, but, this time, I wanted to make sure he also took my ass. I wanted to feel what it's like to take all nine inches of him and feel him release deep inside my hole, and know that I was able to please him in every way he could wish.
As wonderful as that thought sounded, it was a very ambitious one. See, I'm not exactly a power bottom. In fact, I have not bottomed in over four years, with my last regular being of the smaller variety – a massage therapist I paid by letting him fuck me after the massage. The few times I tried letting a bigger guy take me, I never really managed with their size, and usually reverted to my oral skills to finish them. Things would become painful quickly, so I always believed that my ass wasn't built for bigger dicks.
But this time, I wanted to give it a real chance, and I wanted to be sure that, if all conditions were met (if Reggie was there, if he was into some oral fun, and if I could convince him to take my ass), that I would be 100% ready.
But all this was still in a world of fantasies, because nothing guaranteed he'd be there in the first place. A few days passed after I heard the news about the new trip, and no confirmation about Reggie's presence. Chances are he won't be there, I assumed. He would text me otherwise, I figured. Days turned into a week, and still nothing. With the trip getting closer and closer, I was getting used to the fact that this would be a standard work trip, and nothing more.
Until one day, in the middle of a meeting, I got a text. I immediately blushed when I saw the sender – Reginald Client. "Hey man, are you going to be onsite?", he said. My heart started racing. "Hey man, how have you been? Yes I will. How about you?", I replied. A few minutes passed, and no answer. By the end of the afternoon, still nothing, left on read.
I was starting to get pretty pissed at his habit of not answering messages quickly enough… and then I heard a 'ping' from my phone!
"Sorry for the delay man, I was in meetings non-stop and wasn't able to answer properly. Yeah I'll be there, for the first week, landing on Sunday. HBU?", he asked.
"No worries, totally understand! I'll be there from Saturday evening. Ready for an exhausting two weeks?", I immediately replied.
"Oh man I wish I could've gotten a Saturday flight too, it's going to be rough with the jet lag and all. Hopefully I'll find a way to relax and figure out my sleep schedule.", he added.
Coming from him, I knew exactly what he meant by "relax". The first (and only) time we hooked up, that is the exact wording he used to imply he needed some release…
"I'd love to help with that…", I texted
"I'm open to any recommendation you might have for me this time… What's your hotel situation?", he replied.
"I have a few ideas to be honest, not sure how much I can share via text though… but let's say that last time was a great start and I'd love to see if I can find a *new* way to help out… As far as hotel, same hotel, same room actually", I replied, hoping that he would understand that my other hole was at his disposal.
"That sounds good man, I'm looking forward to seeing your new ideas. Sorry I can't talk much these days, so I guess I'll see you on Sunday? I'll text you when I'm all settled at the hotel.", he texted.
"All good man, I'll see you on Sunday.", I replied, trying to keep it as civil as possible, understanding that he has a wife and probably doesn't want things to get too heated while at home.
And we left it at that. Ten days to Sunday, ten days to get ready for his thick 9-inch BBC to fill me up entirely. This is the story of my journey preparing for Reggie's thick 9-incher over 10 days.
Getting The Right Supplies
So I went to Amazon to get all the necessary tools and get my tight ass ready. When I say "tight", I mean tight. Like, one finger with lube is ok, but two fingers is a stretch. I bought some good lube, an applicator, a 4-piece kit of plugs, ranging from 0.85in to 1.6in diameter, and a super realistic 9-inch dildo with a suction cup base and a 1.9in diameter. That dildo looked exactly the right size to get me ready for Reggie. My idea was that I would split the 10 days into five 2-day parts, every time giving my ass ample time to get used to the 0.25in increment, until finally trying my luck at the BBC dildo, using the suction cup to fuck myself and simulate getting fucked. From the way Reggie fucked my throat, I could tell that he is able to control himself, but he does enjoy a deeper, rougher fuck when he's close to cumming. So I wanted to be ready for that. 2 days later, my shipment arrived, and I immediately got to work.
Days 1-2: Getting Used To A Small Plug
I unboxed everything, and … wow! That dildo was big, and heavy. And so fucking realistic. I could not have chosen a better fit for Reggie's cock… The length, the girth, the balls and the thickness of the head, everything was as if it had been molded from his cock. I started feeling woozy at the thought that I would be taking this in my hole in the coming days… But first thing first. I went to clean myself with the douche that came with the plug kit, and applied a ridiculous amount of lube inside and outside my ass, as well as on the plug. The first plug looked so ridiculously small next to the dildo that I felt a bit silly being so cautious and well prepared, but I was serious about sticking to the plan.
I grabbed the plug, and slowly pushed it in. It had been so long I hadn't had anything up my butt that this was legit an orgasmic sensation. Every inch I pushed in, I could feel my cock get harder and harder. Even if it was less than one inch at its thickest, I could definitely feel it stretch my ass, deliciously. In a few minutes, it was done, and the plug was sitting comfortably inside me. My cock was hard as a rock, begging me to relieve it, but I decided I wouldn't, as I wanted to keep my horniness building up until the night. So, horny as fuck, I went around my business for the evening, doing some basic house chores. Occasionally, the plug would slip out of my ass while walking, and I would relube it and pop it back in. After about an hour, my ass offered no resistance anymore, which felt like a great early achievement. I could have stepped it up and grabbed a larger plug, but I decided to stick to the plan. I finished Day 1 bent over on my side, rubbing my prostate with the plug and my frenulum with my index, until I leaked a huge thick load.
The next day, I woke up wanting more. Washed my plug, washed my hole, and proceeded to wear my plug for the whole day (I work from home). By the end of the day, I was completely used to the 1-inch plug, and I rewarded myself with another great orgasm, using the both plug and my fingers this time until my cock leaked another huge load. There's something about a plug rubbing against your prostate the whole day that makes cum production that much abundant. And I'm an absolute cum slut, including for my own loads.
Days 3-6: Getting To 1.3in
With that great start, I was ready to start tackling plugs 2, 3, and 4, with the fourth looking quite intimidating at 1.6in diameter. Days 3 and 4, I took the 1-incher, which gave me no issues at all. It felt as comfortable as the 0.85in, and felt very comfortable walking around during the day. Orgasms were about the same, i.e., insane. Days 5 and 6, I graduated to the 1.3 incher. This one gave me a bit of a harder time fitting it in, but with enough lube I was able to wear it just like the others. At night though, the orgasm was much stronger as the pressure against my prostate felt 10x stronger and I almost felt a burning sensation going down my dick from the pressure of the ropes of cum that were coming out of me. While 1.3 inches felt like a great achievement and could probably prepare me for many smaller guys, I knew that Reggie's dick was much, much bigger, and my biggest challenges were still ahead of me.
Days 7-8: Almost There – 1.6 Inches
I knew for a fact that I had never taken 1.6 inches diameter before – like I said before, I've always had a hard time fitting anything remotely big inside me without pain. I did feel very confident that the work I had done in the days before would pay off, so I took on this plug early in the morning of the 7th day. Cleaned myself, lubed myself, lubed the toy – the normal routine. I started pushing the toy in, little by little, but I was making no progress, as if I was just pushing on my anus, instead of inside it, which made a lot of sense considering the toy's tip was much less flared than the previous ones… I insisted a bit, but started feeling pain, and I didn't want to lose my progress by injuring my ass after so much hard work. So, defeated, I went back to the previous size, which my hole immediately swallowed. Despite the great physical sensation, I was sad that I was stagnating. I went through my usual routine of walking around the house and working with the plug in, occasionally relubing it, but the fun wasn't there anymore. I wanted the bigger one. So I went back to bed, laid on my side, lubed myself up even more, and tried the 1.6-incher again. This time, though, I remembered that the bigger plug came with a vibrating function, which I activated. Immediately, my ass took the first inch in, and I felt much more relaxed than previously, managing to push it in a little more, and a little more every minute. Even as I kept going, I felt no pain whatsoever, just a nice stretch, and the feeling of being filled up, until suddenly, the toy disappeared entirely, deep inside me. With all 4.5×1.6 inches inside me, I could feel the buzzing device press against my prostate, and started leaking precum immediately. I couldn't resist the urge to touch myself and as soon as I put a finger on my frenulum, I had my strongest orgasm of the week, 4-5 thick ropes of cum came out flowing onto the sheets and loud moans came out of my mouth. I turned off the toy, but left it in and fell asleep from the orgasmic exhaustion.
I woke up about an hour later, as if on drugs, the plug by my side (my ass had pushed it out during my sleep), extremely happy with my achievement. The next day, day 8, I managed to slip my big plug on the first try, and the feeling was just as amazing as before, but this time, I decided to not make myself cum as I wanted to keep some extra milk for the real deal – the BBC dildo.
Day 9: D-Day
I woke up on the 9th day with a simple goal in mind: take at least half of my dildo, comfortably. Right after breakfast, I went through my routine – douche and lube up. Just to make sure I was dilated enough to start playing, I went and inserted the 1.3-incher and left it in for a few minutes, and then moved on to the vibrating 1.6-incher. Felt great, as always, and my cock was already leaking precum. With the plug in me, I went to the bathroom, and turned up the heat (I heard that hotter temperatures help you relax), and stuck the BBC dildo on the bathroom floor, a few inches from the wall. I can squat down to a depth of about 5 inches, meaning that about 4 inches of the toy would be inside me when squatting, reaching my goal for day 9.
I lathered the dildo in lube, and started squatting above the toy. My plug was pushed out of my ass as soon as I started squatting, upon which I immediately applied extra lube inside me, and I soon felt the tip of the BBC make contact with my hole. As soon as my hole hit the cock, it felt perfect. I was already slightly dilated, so I managed to take the whole head on my first try, and I could tell my anus was surrounding the head's ridge. My ass was being stretched and relaxed at the same time, as I was basically resting in a squat position above the cock. The sensation was absolutely exquisite, and it felt so much more erotic than with the plugs. It really felt like a cock. I also knew, from extensive prior observation of the cock, that this was the thinnest part of the dildo until past its midpoint. In other words, the cock only got bigger and bigger until the 4th or 5th inch, and then it flared out slightly.
I stayed in the same position, not going any deeper, leaning against the wall comfortably. I started contracting and relaxing my sphincter in intervals of increasing lengths. 5s hold, 5s release, then 10s, then 15s and so on, to tire my hole and dilate it faster. Very quickly, I felt completely comfortable with the tip inside me, so I rode up, and relubed both the toys and my hole. I squatted once more, this time putting my feet a bit farther from the wall to allow to go a bit deeper. My ass immediately swallowed the tip completely, and reached the ridge. I then let myself go down, little by little, without really caring about how deep I was, just focusing on the feeling and the comfort. I could definitely feel the stretch increasing with every millimeter of depth I was gaining, and whenever it would feel too much, I would ride back up, squeeze and release my sphincter for a few seconds, than squat back down until it happened again. Within about 10-15 minutes of squatting, I started feeling the cock filling me up significantly, rubbing hard against my prostate, which made me leak precum like crazy. I kept rubbing and rubbing, and tasting my precum as it kept oozing out of me. I made a point of not jerking off. I kept squatting lower, and lower, until at one point I felt the cock hit something different – like a bit of a wall deep inside me. I had not felt this in any of my previous experiences, neither with toys nor with real cocks. I got back up an inch or two, changed my angle and squatted back down slowly. All of a sudden, I felt the dildo sliding in easier, the deeper I got. OMG. "Did I just pass the midway point of that BBC?" I thought. I leaned forward, ramming the cock against my prostate and leaking another rope of precum in the process, and I could only see the balls and the first inch of the dildo – the rest was already buried inside me! I was in shock, I never expected I would be able to take the whole thing on my first try!! I got back up, just to admire my work, and compared the size of this huge BBC to the first plug I took 9 days earlier, and felt so proud of myself.
As a reward, I stuck the dildo against the wall, lubed it back up, and proceeded to fuck myself doggystyle while pressing the vibrating plug against my cock.. I won't lie, taking the whole length doggy wasn't exactly easy, and I had to ease myself into it. The first few minutes I was feeling some cramps, and so I would back off a bit, and try again once the pain was gone. But after about 5 minutes of fucking myself against the wall, I could start from the tip and swallow the cock – slowly – until my cheeks hit the wall. The full 9-inch. Fuck. That was hot. I had achieved one of my longest standing fantasies, to take a thick, huge BBC deep inside me and cumming from it. I felt so proud, and so excited that I would be able to give Reggie what he deserved. I wiped up my cum on the floor, cleaned up my toys, packed my bags, and headed to the airport.
Coming soon, part 3: My second time meeting Reggie