A Trip to Boulder

Throughout my fifty-plus years on the planet I've always harbored submissive thoughts and tendencies, but never really had the nerve or the opportunity to act on them. The time, place or partner never quite worked out properly for me to do so.

In many ways I suppose I fit the quintessential profile - in charge during the day, but secretly desiring to just surrender to someone else. Does that make me selfish? Lazy? Unimaginative? Perhaps a combination of all three. I only know what I like (and what I'm scared of, which is perhaps why I've never acted on the tendency). That's why what happened was so surprising, on so many levels.

I can't say what it was that prompted me to do what I did. Knowing that I had a trip to Colorado coming up (safety perhaps in being away from home?), I did a small amount of internet research around my destination and came across something that very much caught my eye. I thought I was too responsible to actually reach out and contact the woman in the ad; it was exciting enough to merely troll the site and imagine. I do have quite the active imagination.

My fear of contacting a self-described mistress was that I would never find what I was actually looking for (if I even knew what that was), and merely wind up being both disappointed and poorer. Is there such a thing as truth in advertising anymore? My stereotypical mental model was that I would only find a plus-sized man-hater who was only in it for the money. Something about this particular ad intrigued me, however. The pictures were not very clear or descriptive, but the language used began to draw me in almost immediately. In spite of my better judgment, I wrote from an anonymous email address.

I received a reply rather quickly, but it was readily apparent that this was a bit of a (well-written) form response designed to weed out time-wasters. Apparently step one was that I would need to prove myself worthy of a continued dialogue. I did not have any of the requested references that I could provide, so I needed to review the questions, and my answers, quite completely. This was indeed a bit of a test, and not one that I was sure I could pass. That being said, being the competitive person that I am, I dove in headfirst. I needed to describe myself, my desires, why I had contacted her, when I was looking to meet, etc. And there it was - I also needed to provide my phone number. So much for total anonymity.

Nothing ventured, nothing gained. Somehow I felt free, unburdened, unencumbered. I described what I liked, and what I didn't, to see if there was hopefully some common ground of interest. If the woman doesn't find the session enjoyable then neither do I. I was not interested in play-acting or insincere role play. A bad porno movie parody was definitely not what I was after.

My concern was that I might be too vanilla for her, but I went with as much honesty as I could muster. I told her that it was the mental aspect of an encounter that intrigued me the most. That I normally eschewed pain. I am strictly heterosexual, not into any form of feminization, and was disgusted by the thought of showers of any color. I was concerned about appearing to attempt to "top from the bottom" (a phrase I learned in my searches), but thought that if this was going to work I needed to be honest but not demanding. To further describe my interests and thinking, I told her that when I fantasized it often included more than one woman at a time. I mentioned that the theme of CFNM was also very appealing, but that I am a big fan of the female form, so appreciate nudity as much as, if not more than, the next guy. I had recently taken an online quiz, and shared that my score described me as a submissive rope bunny who was both an exhibitionist as well as a voyeur. I also stressed the part about my caring about my partner's needs, not only because it was true but also in the hope that it might win me some points. If she wanted to help me stretch any self-perceived boundaries I told her that if the chemistry and trust were right, I'd be open to it. Thinking that was enough (and afraid it may have been too much), I let my responses fly.

Much to my delight, but a bit to my fear, she responded affirmatively. She asked a few qualifying questions, and, apparently satisfied that I wasn't a serial killer but sincere in my ambitions, indicated that we would be getting together. I gave her my hotel name and address and the dates for my seminar, and waited. She told me to be patient, and that she would be in touch via text (she had provided a number for me to use for authorized correspondence). I was instructed to send my room number to her cell phone after check-in (which I of course did, as expeditiously as practical after arrival).

Truthfully, I didn't really know what to expect, and tried to keep my hopes low but my guard up. I wanted to be careful, yet at the same time a part of me didn't. I could not properly account for or describe the sense of excitement that I felt. The anticipation was a strong part of the experience. Let the chips fall where they may.

I visited the ATM machine in town, and, not quite sure why, bought a "Thank You" card from a Stationery Store and put money inside along with a small handwritten note, writing "Tribute" on the envelope. At this point in time I didn't know if she would even show up, or how the encounter would run. I proceeded to attend day one of my four-day seminar, knowing only that I had been instructed to be patient. Paying attention to the seminar, I knew, was going to be incredibly difficult.

The hotel itself was described as "upscale downtown," built in the Victorian style, and near the Pearl Street Mall. Although constructed in the early 1900's, it had definitely been well maintained. My room was more than adequate, and very comfortable. I was back in it shortly after dinner, mildly disappointed that my cell phone had not alerted me to any texts since my arrival. It remained quiet until it was time for me to go to bed, which I set out to do at around 10:30 PM. Having arrived from the East Coast, I was indeed tired already, and it was well past my normal bed time.

Shortly after I had brushed my teeth and performed my other nightly rituals, I stripped to my skivvies and climbed into bed. Although tired, I left the light on for a few minutes to read and unwind from the day's travel and events. And then I heard the knock on the door.

My heart felt like it skipped a beat, and then pounded harder to make up for the one that was lost. Vision after vision raced through my head, and the logical part of my mind told me to slow down. It could be housekeeping (although it was late for that); it could be someone who had the wrong room. Of course, it could also be her, and my mind raced in wonder as to what she actually looked like (oh please, oh please, oh please don't disappoint.)

I put on the complimentary robe found in the room, and opened the door. Standing in front of it was a beautiful girl who I would best describe as a cross between what I remembered a 25-year-old Pia Zadora to have looked like (I told you, I'm in my 50's), and Hayden Panettiere for those of you who need a more current reference. In other words, she was a five-foot tall blond with shoulder length hair, a cherubic face, an impish grin, and a gorgeous body to boot. Jackpot.

She didn't wait to be invited in. She strolled past me, which is when I noticed what she was wearing: form fitting white pants, low cut boots, and what I believe is known as a halter top, black in color (it was warm in Boulder that night). If she brought a coat with her she had left it somewhere else. She placed her surprisingly large handbag on the desk.

In her hand she was carrying five envelopes, four white ones and one red one. She also had a small box which she proceeded to walk over to and leave on the nightstand, next to the Tribute envelope which she casually ignored. I noticed from where I was standing that there was some writing on the box, but I couldn't tell what it said from where I was standing. She returned to me and held out the envelopes like a magician performing a card trick. She had not yet said a word. She merely looked at me, nodded to the numbered cards in her hand, and through her mannerisms indicated that I was to select one. OK, first thought: red or white? Do the numbers mean anything? Are the contents of the envelopes all the same? How deviant might they be? What kind of trick is this? I tried not to overthink it. Scared to select the red one, I opted, for no reason whatsoever, for envelope number two.

Again, I was non-verbally instructed to open it and take out the index card inside. My heart was beating rapidly and strongly when I read the following:

"Boy (for that is how you will henceforth be addressed) -

Read this card and then return it to my friend.

Strip and lie naked on the bed. Masturbate yourself with your non-dominant hand.

Do this now.

Mistress Rose"

I was both confused, disappointed and happy at the same time. The vision before me was not (?) the woman I had expected. Regardless, I proceeded to do as instructed. I went into the bathroom to grab a towel, which was politely but forcefully removed from my hand with a tsk-tsk-tsk hand gesture pointed my way, as she waved the petite index finger of her right hand in a left to right arc in front of me.

I have never before been so self-conscious of my body. I removed the robe and placed it on one of the two sitting chairs in the room, and proceeded to do the same with my undershirt. I made the deliberate decision to keep my eyeglasses on, as I wanted to visually record every moment of this encounter, to the best of my ability. I slipped my thumbs inside the band of my shorts, and lowered them as gracefully as I could. Thankfully, my body was already paying full respect to the woman in front of me, and arousal was not going to be an issue this night. It did not take me very long, though, to realize how arduous it is, even in such a highly erotic situation, to accomplish what had been requested with my left hand. I was definitely excited, but knew that I might have difficulty accomplishing what should have been a simple task. She looked me in the eyes with a mock expression of disappointment after a few minutes. She then sat on the side of the bed and proceeded to blow gently into my groin. With her right hand she grabbed my balls, and began staring deeply into my eyes. She then gently, but somewhat firmly, squeezed her hand, causing a sensation that was a combination of both pleasure and pain. With her left hand she proceeded to reach up to my nipple, at first caressing it and then firmly pinching it. That did the trick. I closed my eyes, my head pushed back, I withheld my breath for a moment, and I exploded. All over myself.

She smiled. She then moved her left palm to my chest, gently pushing me down (as if that were necessary). She took the pinkie of her right hand and bent it as if she were holding a teacup, and used it to scoop up some of the ejaculate that was now on my stomach and chest. Silently (still), and confidently she proceeded to put that finger in my mouth. Now that was a first! Never before had I even thought of that. First boundary stretched. She smiled, patted me on the head, stood up, turned around and walked out the door.

I walked into the bathroom to clean myself up, and it was then that I saw what was written on the box: "Do not open until instructed to do so."

Five minutes later I was clean and dressed for bed when I heard the incoming text. It stated, simply: "Good job, Boy. Rest up for tomorrow. Mistress Rose"

I don't remember my dreams from that night, but do remember they were fantastic. It was one of the soundest sleeps that I had had in quite some time, and I don't think jet lag was the reason. I had not awakened hard in years, but did so the following morning. I knew there was no way I was going to be able to concentrate on the contents of Day 2 for the seminar.

It's funny how your senses can become heightened. All during the day, whether in the hotel itself or at the Mall during the break, I found myself looking for five-foot tall blondes. Although there were a few, given that this is a college town, I did not see my visitor from last evening.

I know I was not the most entertaining dinner guest that evening, as my mind was definitely elsewhere, looking both back as well as forward. I did my best to feign interest in the conversations of my male colleagues, but begged off any post dinner outings, stating that I was still tired from travel, and retreated to my room. The TV was turned on in an attempt to distract me from my own thoughts.

The sound of the incoming text at 9:30 PM nearly caused me to jump from my chair. The instructions were simple: "Open the box."

I removed the brown paper wrapping from the small rectangular object, and found an index card on top of an item wrapped in tissue paper. The card's instructions were also quite simple: "Make sure the door is unlocked. Strip naked. Put this on. Kneel at the foot of the bed." The "this", after removing the tissue paper, was what I would best describe as a rather serious blindfold.

OK, another element of trust to be added. Who was going to come in? How would I even know? Was it safe? I so wanted to run, pretend none of this had ever started, and just say "Sorry for ever bothering you." Yet I continued, both excited as well as afraid.

I took the "Do Not Disturb" sign and made sure that it prevented the latch from fully closing, so that a push from the outside would open the door. I placed a pillow on the ground to protect my knees, and completed the instructions, putting the blindfold on and taking everything else (including my glasses) off. I knelt, and waited. And waited.

What felt like an hour later, but was likely no more than fifteen minutes, I heard the door open and the Do Not Disturb hit the floor (I still had my sense of hearing). My left hand was gently moved behind my back, placed in what I'm guessing were furry handcuffs, and soon joined to my right. Did I remember to enquire about a safe word? No, of course not.

My guest proceeded to make a call. In what I would best describe as a soft and sweet voice, she dialed room service.

"Hello, this is Room 309. Yes, Mr. Fisher's [somehow she knew my real name!?!?] May I please order a bottle of Chardonnay? If you don't mind, would you please send a woman to deliver it. I'd feel more comfortable that way. Thank you."

She sat next to me on the bed, rubbing my hair. She smelled wonderful, a bit like baby powder, but I was terribly confused about where this evening was going to lead, and what I had gotten myself into.

A few minutes later there was a knock on the door, and I heard tidbits of the following conversation:

She: "Hi, thank you for coming up so quickly. I don't want to offend or startle you, but I have a submissive man in my room in somewhat of a compromising position. Are you OK entering, or would you prefer me to just take this from you at the door?"

I couldn't hear the reply, but she must have said OK. I heard the bottle, ice and glasses being placed on the table.

"You mind me asking about this?" I heard the hotel employee ask.

"Not at all" was the casual reply. "Mr. Fisher here is a submissive, and I'm here to have my way with him this evening. You may wish to spread the word to any of the other female members of the staff about him, if anyone else wants to have a turn. Even if you just tell them to smile at him for no reason other than hospitality it will truly mess with his head, because he won't know who's in on his little secret, and who's just being nice."

"Do you know what you're going to do with, or should I say to, him?"

"Actually, I do. It's been a long week, and I'm a bit stressed and a little frustrated. I'm going to use his tongue to pleasure me, to help me relax and unwind."

"Well, I certainly hope you enjoy yourself. Somehow I think you will. I just need this to be signed for, and I'll be on my way. But I do have a few friends in the hotel that I know will just love to hear about this."

"I assume a 40% tip is OK with you? I'm sure Mr. Fisher doesn't mind at all; do you boy?"

There it was again: "Boy". I nodded in meek assent, eliciting a small chuckle from the woman who had brought the wine.

"Hey, before I go - I've had a few jerks that I've had to deal with today, and it would improve my mental state if I could take out a small amount of aggression on your submissive. May I swat his ass a few times? Mind having him stand up for a moment before you put him back in position?"

"By all means - help yourself. And remember there's more where that came from."

As you can well imagine, I was then instructed to stand, was spanked a few times with an open hand, and then knelt back down, thankfully back on the pillow. How would I know who it was that did this? Could I meet anyone who worked here in the eye from this point forward?

Room service thanked my visitor, and left.

After securing the door and pouring herself a drink, my visitor proceeded to place one leg on either side of my body. I felt long fingers begin to stroke the back of my head. She then pushed my head down into what was a ready mound. I sensed, somehow, that she had come in wearing a skirt, which had now been lifted up, but wore no underwear (or had just removed it). I bent a bit too far forward at first, and my nose went straight into her vagina. A small laugh, but then a redirection to get to work.

Never before had I encountered something like this, or even imagined it. I had no idea of the name of the woman in front of me. I had no idea what she looked like. I was trusting that she was disease free (as I suppose she was doing the same). Yet I approached this with gusto. What had gotten into me?

It was evident that she liked the game she was playing. Whatever I had learned over my lifetime in this regard, I put into this. My highest purpose at this point in time was satisfying my guest. I used the tip of my tongue, the entirety of it, small, tender bites on the inside of her thighs, which appeared to be quite slim, to caress her. Anything I thought she might like, I tried, and was happy that her body reacted positively. My face was soon covered in moisture, and she seemed to show no signs of tiring of this activity.

After a few more minutes, she began to shudder, to push my face further and more tightly into her, and the moment she came was unquestioned. I was as happy and as proud as I had been in quite some time, and couldn't adequately say why.

The next thing I knew the handcuffs were being removed, and I felt a gentle kiss on my forehead. I was told not to remove the blindfold until I heard the door close. End of night two.

Unbelievable. Had I really just done that, and emerged both safely and happily?

I went into the bathroom, washed my face, and put on some clothing. I thought about pleasuring myself, but then thought better of it. An even longer refractory period was not such a bad idea. I didn't know if I should expect anything else, but I still had one more night left. Could anything top what I had experienced thus far?

Again, the unmistakable sound of the incoming text startled me. From the number that I now recognized above all others, there was merely a link. For a moment I thought of the dangers of clicking on links and the damage that can be done, and then thought that was a ludicrous thought to be having at this particular juncture. I had obviously extended a significant amount of trust to her. Why stop now?

I was shocked when I followed the link. It was a video. Of me. From tonight. In action.

The camera had obviously been placed on the dresser, just prior to room service delivery. The field of vision included me on my knees, but no faces in the pictures. I could only tell, from her hands, that the wine was delivered by a white woman in slacks and a jacket, but no other details were readily discernable. Although I was not privy to my guest's countenance, I was more than happy with what I did see. My best guess is that she was a very slim African American, taller than 5'-8" and possibly up to 6'-0". For those who watch ESPN my best reference would be Sage Steele, at least in terms of body type. Curious that my high school biology popped back in my mind at this particular instance, as the word "ectomorph" suddenly appeared in my head (and what an ectomorph she was). And yes, she had come in wearing a long skirt that was conveniently moved prior to my performance.