Should I Stay or Should I Go?
“Welcome to Delta flight 714 ladies and gentlemen, please prepare for takeoff. Our time in flight is 90 minutes so we should have you at the gate in Dallas/Fort Worth by 3:30 this afternoon. Relax and enjoy the flight”.
There was no fucking way I was going to relax for the next 90 minutes. I was on my way to meet the dom I’d met online and pledged complete submission to for the next 48 hours. What the fuck had I been thinking? I was simultaneously terrified and hard as a rock.
It started several months ago when a reader emailed me to comment on an erotic story I had published on a gay erotica website. Master Sam, as I came to know him, reached out to tell me how much he had enjoyed my story in which a late 40s, extremely fit middle-aged guy (me) and a late 20s equally fit athlete became fierce CrossFit competitors and then lovers. Master Sam was an accomplished athlete himself—a wrestler—and admired the discipline it took to achieve that level of performance. We eventually exchanged pics, first chaste, then nude, and finally explicit and were equally turned on with each other. He was slightly older than I, in his early 50s, but tall, lean with a wrestlers build, cut and very muscular, and looked to be about 13 % body fat. His interest in me lied in that he was really into muscled guys and was hugely complimentary of my physique. He made it clear, “I put studs like you in their place.”
The story I’d written had a strong dom/sub and BDSM subtext and my character was clearly the dom. Master Sam was quick to tell me he was 100% dom as well and complimented me on the authenticity of the scenes, my writing style and the intensity of the relationship between two committed athletes.
Our emails became intense and trusting so I finally confessed an important secret I’d never shared with anyone: although I had portrayed myself as the dom in the story, I actually fantasized about a experiencing a truly submissive role. Although I’m a successful executive, leader, and athlete, I secretly long to submit. My porn habits have inched toward hard core submissive role playing and BSDM. I’d often fantasize about ‘what if’? I’d longed to try it but was afraid to completely surrender, afraid that I couldn’t endure the pain that so turned me on in porn. I also feared I’d emerge with physical evidence like rope burns that I wouldn’t be able to explain.
My confession quickly escalated the intensity of our emails. He made it clear that he was a strict, experienced dom and was no-nonsense about what it meant to submit. I finally got the courage to ask him if he would help me realize my fantasies. I offered to come to him and surrender myself. Initially he declined, but I persisted, and we finally agreed on a weekend in September when I’d to fly to Dallas where he lived and he would take me as his sub.
In flight, my mind raced with the erotic possibilities and the potential disasters. Would it be as sexually exhilarating as I’d fantasized? Or would he be a psychopath who would rob, or permanently harm me once he had me restrained? Or something I hadn’t even imagined?
As I sat on the plane, I wrestled with the implications of what I was doing. I have everything to live for, yet I’d be handing over my well-being to a stranger. While I tried to deny it, I found the danger to be as exhilarating as the promise of kinky sex itself.
I was so wound up once we took off, the only way I knew to spend the 90-minute flight was to review the dozens of emails Master Sam and I had exchanged over the previous months. I rationalized that that would mentally prepare me for the next two days and allow me to search, one last time, for any clues I was making a mistake. But truth be told, I simply wanted to relive all the raunchy things he said he’d do to me.
In reviewing the emails, there were several exchanges before the subject of my submission even came up. Once it did, I continued to dance around it until I finally got the balls to ask the following…
Sir, this may be presumptuous of me, but given your expertise in BDSM and experience as a dom, I was wondering if you’d be interested in exposing me to your world; perhaps even tutoring me. As mentioned earlier, I have fantasized about submitting to someone with your strength and experience. I would travel to you in Dallas and, of course, cover all your expenses, including a hotel of your choice if you choose to meet outside your home.
We went back and forth a few times before I convinced him I was serious and he replied with the following…
Thomas, you know what you’re asking for, don’t you? Do you really think you can endure what I have in mind? Sexually? Physically? Emotionally? The humiliation alone breaks most men. Think hard about this before you commit.
His directness scared and captivated me equally. I was drawn in by the unknown; how much could I really endure? Would it be as erotic as I’d fantasized? Part of me said ‘There’s only one way to find out’, and the other said, ‘This is fucking crazy. You’re insane to put yourself in this position.’
But no harm in continuing the emails, right?
Sir, thank you for your candor. I don’t know how much I can endure, but I’m asking you to help me find that out. I would be at your mercy; not only physically and sexually, but because I owe you for your investment in me. If you do this for me, you will be demonstrating your faith in me and I promise not to disappoint you.
That seemed to get his attention…
Don’t worry Thomas, I’ll make it worth my time, you won’t have a choice. But I’m going to be clear with you about what to expect so you don’t waste my time. Are you ready to hear what I will expect?
Hell yeah, I wanted to hear. I wanted every sordid detail. That’s what this was all about. But slipping easily into sub mode, I was uncomfortable burdening him by having to put it into writing.
Yes sir, I’d like to know in as much detail what I should expect when I’m there. The more I know, the more I can prepare myself.
He responded uncharacteristically quickly, and even more tersely than previous emails…
You should expect complete subjugation for 48 hours. You will be bound in a hotel room, likely for the entirely of your visit. You’ll have little to eat other than my cum and that of my bondage assistant who you will get to know intimately. You will arrive with a clean hole and douche repeatedly throughout the experience. You will be restrained, gagged and blindfolded much of the time. Your cock and balls will be stretched unimaginably, your nipples will be clamped, and when you’re not being fucked your hole will be stuffed with toys. You’ll be skull-fucked in every position possible and gang banged in a sling.
In addition to myself, you will submit to my assistant, Lieutenant Rob, who is extremely knowledgeable and experienced in BDSM. He and I often double team our subs.
Finally, you will be shared with my friends, or put less delicately, you will be whored out. Your shame will be on public display. I will judge you by the degree to which you please me and my friends. You will be punished if you don’t perform.
If he was trying to scare me away, he was doing a shitty job. I re-read this passage dozens of times and every time I got more aroused than the time before. Although I still wasn’t sure if my fantasies exceeded my endurance, I had no choice to respond. I worried that if I sounded hesitant, he’d back away…
Thank you, Sir, for your detailed explanation. You’ve been clear about your expectations. After reading this, I’m more energized than ever to be in service to you and your lieutenant.
Not long after we sealed the deal…
Ok boy, you’ve convinced me you’re worthy. Lieutenant Rob and I are free September 14-16 and will expect you then. Arrive mid-afternoon and you’ll be freed mid-afternoon on the 16th. That’s 48 hours of complete submission and public humiliation. I will send you instructions on securing a hotel suite. No backing out.
In subsequent emails he forwarded instructions regarding a specific (and expensive) hotel in the trendy, gay-friendly part of Dallas, insisted on a specific suite and instructed me to talk only to Raymond at the hotel when I made the reservations and let him know I was a friend of his. When hearing Sam’s name, Raymond didn’t seem surprised to be asked for that suite and I was able to secure it for the dates we agreed on. Although expensive, it was a small price to pay to fulfill my fantasy.
As I reviewed these emails on the plane, my heart pounded and my stomach flipped. I was about to surrender to two strangers, fully aware that I’ll be restrained, tortured, possibly even gang raped. But I was cautiously confident that I’d be safe. Throughout the email exchange I was the one encouraging the encounter, not him. Master Sam didn’t lure me in like an online predator. I convinced him to do it, not the other way around.
“Ladies and gentlemen, we’re making our final approach to DFW airport. Please make sure….blah blah blah..” My heart was in my throat. What was I doing? I seriously contemplated turning around and grabbing the next flight back when I got off the plane, but I had made it this far.
Once landed, it seemed to take forever to make my way to one of the exits. Each step was a giant leap to either a fulfillment of a dream or a catastrophe. The unknown made my heart pound with such intensity I could barely breathe.
Taking my time and intentionally deep breathing to calm my nerves, I found my way to an exit, Door E6, and pulled out my phone to let them know I’d arrived, as I’d been instructed. I stared at the phone; it was now or never.
This was my last chance to bolt and put this potential nightmare behind me once and for all.
Although my hand was trembling, I didn’t hesitate. I feared if I did, I’d lose my nerve. I found the number, hit send and waited for an answer.
“Thomas, you made it. Welcome to Dallas”, said the sexiest voice I’d ever heard. “Are you ready?”
“Yes, Sir”, I replied bravely.
The car pulled up remarkably quickly. They popped the trunk, I stashed my bag and walked to the back door and saw the two of them, one in the driver’s seat, one in the passenger’s seat. I recognized Master Sam from his pics as he stepped out of the passenger seat and stood face-to-face with me, clearly assessing me. “You’re as sexy in real life as you are in your pics, boy.”
If I was sexy as hell, he was straight up gorgeous. His pics didn’t do him justice. At least 6’3”, early 50s, broad shoulders, trim waist, exceedingly well groomed and George Clooney good looking. I wanted to return the compliment but was too intimidated by his towering presence. “Thank you, Sir,” was all I was able to respond.
“This is Lt. Rob, and, of course, I’m Master Sam. You will address us as Lt. and Sir for the duration of your visit, that is, when you’re not gagged or have a cock in your mouth.”
“Of course, Sir”, I stammered.
“Good”, he replied. “Now get in the back seat with me”.
We both climbed in the back seat and I started to buckle my seat belt on the opposite side of the seat from him. “No need for that”, he casually mentioned. “I want you naked, with your mouth on my cock for the entire ride to the hotel. You won’t be able to do that if you’re belted in way over there. Get those clothes off. And if I don’t cum before we get there, you’ll be punished.”
“NOW!” he bellowed.
What had I done? I was a mere three minutes into the my 48 hour ordeal and I was having serious second thoughts. I was paralyzed with fear.
But there was no turning back now.
