Bumping into a high school classmate all these years later (m/m) - Part 3 posted 6/13

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JackMurray
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Bumping into a high school classmate all these years later (m/m) - Part 3 posted 6/13

Post by JackMurray »

With Covid receding, it was past time for me to take a business trip out to San Francisco. In between meeting with colleagues in real life, I was looking forward to some down time at night with a hotel room all to myself. Of course, I was also hoping to indulge a long standing fantasy while I was out there. See, I'm a conventionally straight somewhat alpha-ish guy (at least professionally) who clearly looks like the ex-football player that I am. All that said, I'm also hugely turned on by the idea of being helplessly bound and gagged by another man. And after all, what better time to try to experience that while in San Francisco with a free hotel room?

The first night I'm there, I just grabbed dinner in the hotel lobby restaurant.I tried to work a little bit, but perused a bondage personals website where I'd opened a new profile before the trip. I hadn't worked up the nerve to try to message anybody yet, when I suddenly heard somebody quizzically call my name nearby. I maybe a little too quickly put my phone face down, and looked up to see an old high school classmate named Steve.

After I got over my surprise, I invited him to have a beer with me. It turned out he was here for business as well, and caught me up on his life since we'd graduated. I knew him as very nerdy when we'd been in several honors track classes in school. I congratulated him on his success. He also told me that he'd come out of the closet to his family and friends as gay after high school, and he'd been much happier since. I told him that I was happy for him, and apologized if I'd ever teased him about his obvious effiminate bearing in school. He told me that it was all water under the bridge. That was certainly a relief to me, but the next thing he said made my heart race.

"You know Jack, before I was sure it was really you, I happened to notice the website you seemed very interested in. It didn't take very long to find your profile. It just so happens that I have an interest in bondage too, except my particular taste is in dominating straight men and making them give in to their naughty, secret urges. I think I'd enjoy having the cocky football guy from my calculus class tied up in my hotel room for my personal pleasure. Here's what we're going to do, at 9 this evening, you're going to come to my suite upstairs and submit to me. I already know what you're interested in, and I'll respect the limits you wrote into your profile, but I'm in charge the minute the door closes behind you and we're going to explore those limits."

Without another word, he wrote his room number on my open notebook and walked off. The next couple hours crawled by until it was almost 9. I considered bailing out, but we both knew I was going to present myself. I took a long shower, toweled off, dressed, and took the elevator to his floor. I knocked on his door, and he met me with a big smile. "Come on in" he said rather innocuously. I heard the door shut behind me, and his demeanor changed immediately. I was told firmly to strip, and right next to his bed, facing the bed. The world suddenly went dark as he put some kind of blindfold on me. I gave a start as he slapped one buttock, and he told me "ah, I've dreamed of doing that to you for years, but you need to be quieter. Open your mouth." I complied, and he wadded some kind of cloth in my mouth and tied off a cleave gag. "And you don't need the use of your hands any time soon." Soon my arms were very well tied behind my back, and it was very obvious he know what he was doing. "Kneel down" he said, and he guided me down on to my knees (he'd very nicely put a pillow down for my knees), and using a firm hand on the back of my neck positioned me so that my chest was flat on the bed. Next came what I later learned with ropes around my ankles as he put me into a kind of crouching hogtie.

I was told to struggle and try to free myself, but I wasn't making any progress before he told me "just to let you know I'm in control here, but you know what, I think you need a little more restraint to keep you still for what's next." Nothing happened for several minutes, before I felt both of his hands grabbing my ass. The hands slowly started working around my waist. An eternity later, he suddenly took a death grip on my balls with one hand, and very slowly worked over my now very erect cock with the other hand. He did that just long enough to elicit a groan, and some pre-cum before stopping. The hands went away, but then I felt something wrapping around my scrotum until they were pulled down and clearly tied to something under the bed. I now found myself naked and very helpless to even move very much with my naked ass sticking up in the air -- and all at the hands of a nerdy guy from my high school calculus class!

I was left alone to revel in my helplessness for what felt like 20 minutes. I was hard for much of this, but not nearly as hard as I was with what came next...
Last edited by JackMurray 1 year ago, edited 2 times in total.
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TightropesEU
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Post by TightropesEU »

Look forward to what happened next.

I have had the same fantasy, but in mine it is my old school buddy, who tied me up a few times after school in the locker room. We meet again and he remembers how I like being tied up, and he suggest we do it again.
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Post by JackMurray »

Nice, I like that one too. I've got my first business trip in a long time lined up, and it was a timely fantasy slash plan for me:-) The follow up part will come next week.
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Post by JackMurray »

I did get to play out a little bit of this on a recent business trip to the Bay Area. I think both of us enjoyed outselves:)

While I was helpless to do much more than wiggle a little bit in my bondage, Steve amused himself by loudly coming and going from his hotel room. He playfully told me that my naked ass was oh so visible from the doorway (which wasn't actually true as I found out later, but the thought of being almost discovered in bondage like that is a huge turn on for me).

I tried to crane my neck around to see where he was and what he was doing. When he caught sight of me doing that, he rectified the issue by blindfolding me with a tie. Now blindfolded as well, I had no warning for what came next.

"You know, I resented how cocky you were back in high school. And I've longed fantasized about what I could do to this ass if I ever had you under my control" he said, as he ran his hands over my ass. He drizzled some kind of cold liquid on me, and I felt his hands circling my anus with whatever lube he'd used. I admit that I surprisingly loved the feeling, but right after I let an appreciative moan escape, he spanked me. I was shocked, and now felt more vulnerable than ever. Without any warning, that stopped. This time though, I felt him reach around me and start masturbating my cock while his other hand was still playing with my ass. He only stroked up on my cock though, so while it felt great, it was clear I wouldn't be able to cum anytime soon. I had to keep very still, because the rope around my scrotum was clearly still attached with very little slack. He kept this up for awhile, then suddenly worked his hand on the head of my cock for an all too short time before stepping away altogether. I was panting, and eager for more, but nope, he did nothing at all for an eternity (maybe 5 minutes:)).

I finally felt some slack around my balls, and he untied my ankles. I was told to stand up and take a step backward. At this point my hands are still tied behind my back, I'm gagged, and blindfolded. I can tell there's still a rope around my scrotum, which he used as a leash to pull me around the room for a few minutes. Suddenly he stopped me in place, but the leash around my poor scrotum suddenly got tighter as he connected the rope from my balls to the ropes around my wrists. He used the new crotch rope as a handle to keep me in place as he spanked me again. At this point, while I didn't particularly enjoy him smacking me around, the feeling of the rope pulling on my genitals and the humiliation of being so completely under control made me even harder.

I was pushed into a chair, and he quickly tied both ankles to the legs of the chair. This time he used both hands slowly, then quickly to repeatedly bring me oh so close to an orgasm before stopping. Almost without letting up on my almost painful erection, he removed the blindfold and I got a direct look at his erection a few inches from my face. "You know what happens next Jack. Do you want to finish? Be released? Then make this good!" and he removed my gag. I'll spare you the details, but he stepped away happy with his happy ending.

The blindfold and gag went right back in as soon as he'd cleaned himself up, and he whispered in my ear "I didn't say *when* I'd let you cum, so just sit and simmer for awhile." I whimpered through the gag and tried to protest, but he quickly went to work again on my cock -- but this time he steadily built me up until I was moaning, then sped up to throw me completely into a big orgasm. He kept going after I had spent my load, and I had to beg him to stop. Which he eventually did.

After a time, he untied me, and let me clean myself off. As I was leaving, he just said "I'll be thinking about what I'm going to do to you tomorrow night, look for instructions tomorrow afternoon..."
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Post by KidnappedCowboy »

Ah! What a great story!

So many of my own fantasies have centered around getting tied up, gagged, blindfolded, and edged in hotel rooms by a host of characters...old college buds, business associates, the hotel staff, and, especially, burglars. :twisted:

Thanks, [mention]JackMurray[/mention]...

Hope to read more from you!
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Post by JackMurray »

I'd definitely had an experience to remember the night before with Steve, an old high school acquaintance who had apparently turned into a skilled bondage Dom in the years since we'd gone to school together. He'd made it clear that I was to be his Sub the next night, and basically blackmailed me into compliance.

I came back to my hotel after the day's festivities, and there was a nondescript package for me at the concierge desk. I had a feeling I knew who it was from, so I tried to keep my shit together long enough to get back upstairs to my room before opening it. Inside was an envelope with the words "Read me first" on the outside. Under the envelope was some packing peanuts that were clearly meant to obfuscate whatever else was inside.

I opened the envelope, and this is what it said:

"
Jack,

I expect you to follow all these instructions in your room and make yourself ready for whenever I deign to join you. Make sure you're are securely bound and waiting for me by 8PM.

1. Prop your door open so anybody and come in at any time
2. You will only be wearing the jock strap in this box
3. Put in the gag (which turned out to be a ring gag, and yes, I was drooling long before he got there)
4. Sit in a chair facing the door
5. Use the cuffs with the long chain to secure your legs
6. Using the two other sets of handcuffs, fasten yourself securely to the back of the chair with your wrists behind your back and chained to the back of the chair. You're supposed to be an engineer now, so figure out how to make it work

Hugs and kisses, this is going to be fun. For me anyway.

Steve
"

Needless to say, it was hard to concentrate on much else while I was letting time go by. At about 7:30, I cleaned up the hotel room and followed his instructions. And waited. And waited for an eternity -- which he later told me was only about 30 minutes.

I constantly heard voices outside of my hotel room, and he'd clearly read in my MetLife profile that one of my fantasies was almost getting caught in a very compromising position. Finally I heard Steve's voice, and he was clearly speaking with what sounded like 2-3 other guys out in the hallway! I heard him say -- unnecessarily loud -- "hey, Jack said he'd leave his door open so I could borrow a jacket from him. It'll just take me a second to get it, and then I'll be ready."

With that, the door started to slowly open and...
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