Mistress Chronicles Ch. 06

I could tell that he had really just thrown a shirt and pants over his whole outfit and had barely taken the time to wipe the lipstick off his mouth. He was still wearing his pearl earrings. Since I knew to look for it, I could see where his bra and camisole puffed up against his shirt.

It was rather comical watching him wander through the lounge with his head down looking under tables to try to spot a woman with boots. At one point a waitress asked if he needed a table and he nervously mumbled something at her and kept up his somewhat flustered pursuit.

After circling most of the room, which had a fair mix of men in women in it as there were a number of events going on in the hotel that evening, he finally spotted me. He must have sensed that I was possibly the right one because he only made cursory glances at other women's footwear as he made his way towards me.

When he finally arrived and saw that I sported the correct footwear he asked, "Miss M?"

"Yes, Nancy I am your Mistress"

"I can't believe it. You're so beautiful. You're the best looking woman in the place. Thank you Ma'am. Thank you for seeing me, for everything. I can't believe it...."

"Relax, have a seat. Let me get you a drink. A glass of wine maybe?"

"Yes, that would be fine, thank you. Thank you Ma'am."

I arranged for his drink and we chatted quietly.

I teased him a little about not changing his earrings and that I could see his bra through his shirt. While my comments caused him to get a little red faced, the fact was he remained in awed silence of the fact that he was at long last sitting in the presence of his Mistress. It was like a little kid meeting Santa for the first time -- fear, excitement, wonder, hope all rolled into one.

As I described in the introduction, Nancy isn't all that comfortable around people. It would be generous to say that we had a conversation. More accurately I asked him some questions and he tried to assemble short coherent sentences in response. We continued like this until our glasses were nearly empty and by now the bar area was getting a little crowded.

"So Nancy, you've done a good job and it seems only fair for you to get a reward. Would you like to go back to your room now?"

"Yes Ma'am. Thank you."

Leaning in close to him so only he could hear, "So here is what you will do. I'm going to drop my napkin on the floor. You will get off your bar stool and pick-up my napkin. While you are down there you will kiss the heel and toe of my right boot. You will stand, bow to me and head up to your room where I will find you in the exact position I left you. I mean exact, every detail the same. Nod if you understand me?"

He nodded his understanding and then did as I ordered. I stayed for another drink and was getting moist imagining him kneeling there, blindfolded in his room awaiting my return. I knew he'd wait all night if I wanted to do that. His level of submission was the farthest I had ever taken anyone and it frankly excited me, although I did have some doubts about how much farther I was interested in going.

Heading back to my room I took off my dress and changed my bra for a black bustier. I pulled my hair back and refreshed my makeup to give myself the classic dominatrix look. I was still wearing my black panties, garter belt, black seamed nylons, and 4 inch stiletto heeled boots.

When I was ready, I quietly opened the pass door and found him just as I had left him. He had put his pink wig and pink lipstick back on and was kneeling right where he had been before. His chastised cock was bulging out his white satin panties which matched his camisole and bra. He had put his Mary Janes back on along with lacy ankle sox and the white stockings and garters he had been wearing all day.

Even though he was blindfolded, I knew he could sense my presence. His back was straight and head bowed in perfect submissive position.

Wordlessly I moved close to him and ran the toe of my boot over his trapped member. He was as hard as he could be inside his device and I knew it was probably a bit painful for him.

"Very good little one, you follow instructions well. I'm sure all of the lovely ladies at the bar are giggling among themselves at the guy who was roaming around the lounge checking out women's shoes and wearing a bra. Did you like that Nancy? Could you feel all the pretty women looking at you?"

"Yes Ma'am. It was worth it. It was worth it to see you."

"That's very nice of you to say. Did you like kissing my boots at the bar? I'm pretty sure that red-head in the strapless dress noticed. She smiled at me when you stood up."

"Yes Ma'am. I liked that too. I'd kiss them again now if you'd let me."

"That's fine Nancy you may kiss them. Worship them with your mouth and tongue. Just lean forward and put your face near the floor and I'll make sure my boots are right there for you to adore."

With that Nancy began planting kisses all over my shiny black leather boots, leaving traces of her cheap pink lipstick in the process. Pointing this out, he quickly switched to kissing and then licking my boots, cleaning up most of his mess in the process.

I let him continue for several minutes as his unbridled submissiveness continued to stir my juices. Soon he was kissing and licking my heels. As he started working his way up my boot I stopped him and asked him to get back into his kneeling position.

"That was very nice. You did a pretty good job being blindfolded and all. While I'm sure you would have continued all night, I expect you'd like to achieve release. Am I right?"

"Yes Ma'am, if it pleases you I would enjoy a release. My cock is aching inside its tube. Every time I think of you it just throbs."

"So here's another choice. You may take your blindfold off and I'll allow you to masturbate yourself and cum in your panties or you can leave your blindfold on and I'll give you a hand job myself. Which would you prefer for your release."

"Ohhh definitely blindfold off Mistress. I want to be able to see my beautiful mistress. I know I will cum so fast."

I step forward and remove his blindfold my panty covered crotch is just inches away from his face which remained downturned. "You may begin stroking yourself on my command. You will meet my eyes and not look at my panties or crotch while you do so. Beg me when you get close to cumming. You may not cum without my command."

"Yes Ma'am."

I told him to stand and quickly removed his CB-3000 setting it aside. His cock immediately sprung to its full length and looked quite angry and purple from its confinement. I made little eye contact as I did this but could tell by the way his body relaxed that he must have been enduring more than a mild bit of discomfort.

There was no doubt in my mind he'd cum quickly, but I'd see what I could do to draw it out at least a little. I returned him to his kneeling position and resumed my position inches away from him so he'd need to crane his neck back to meet my eye.

"Begin."

He did a fairly good job of holding my gaze which must have been difficult as I teased my tongue across my lips and did my best to look as wanton and sexual as possible. The fact was, our scene was arousing and though I had a nice orgasm earlier I could feel another one building.

I could see him trying to hold back although his hand moved at a reasonable pace up and down the smooth satin front of his panties. I could see the lust in his eyes, but also some fear. He wanted to cum badly but feared cumming too quickly wanting to prolong his moment as long as he could.

"Please mistress. Please may I cum."

"No. Stop right now"

The surprised and then frustrated look he gave me was priceless. Only his good training enabled him remove his hand and not squirt into his panties anyway -- he was that close. As it was there were some streaks of precum that I chose to ignore.

"That was close wasn't it Nancy. You almost came without permission didn't you?"

"Yyy-eess Ma'am. I was very close. Ummm sorry Ma'am."

"No, don't be sorry. You may stare at the floor until your sorry little unit goes soft. I thought it would be nice to prolong the moment a bit. Just to make it special you know. You've worked quite hard to get here and who knows when we might get together again."

"Thank you Ma'am. I do want it to be special."

It took several minutes for him to finally get at least a little limp and I took a seat out of his line of sight for a few minutes to help him. Getting back up I gingerly removed my panties allowing him, once again, the sight of my bare and moist slot.

"Look up and stare at my pussy Nancy. This is what controls you. This is what you submit to. I bet you'd like to kiss it wouldn't you?"

"Ohh yes Ma'am. I'd love to. I've dreamed about it."

He was already back at full hardness by the time I was close to him. I pulled the waistband of my tiny panties down over his head and positioned the moist gusset over his nose.

"Well you won't be able to kiss the actual thing, but you may kiss the crotch of my panties. Panties which have been rubbing against me all evening, absorbing my scent and juices all night.

Go ahead and kiss the crotch of my panties and jack yourself again. Don't forget to ask permission before you cum. Begin."

"Yes Ma'am. Thank you, thank you"

He immediately began wanking his cock, inhaling my scent and kissing my panties.

In less than a minute he was begging, "Ohhh nooo, please Mistress, Please ohh god, I'm, please may I....."

I knew he was beyond control so I said "Yes. Cum my little sissy. Fill your pretty panties with your sissy seed. Cum as hard as you can while sniffing my panties."

He jerked and twitched several times as he pumped out load after load into his panties. His panting breath and assorted guttural noises made it clear that this was a release of epic proportions and he was holding his breath and doing every thing he could to ride his orgasm as long as possible.

I rubbed my breasts as I watched his display and felt some sparks of my own at his submission. I resisted the urge to touch myself right then as I wanted to finish the scene.

He was limp as a rag doll in front of me as his breathing came back under control. Taking advantage of his weakness I continued, "You know what you need to do. Remove those panties and clean up your release. Sissies love eating their cum and I'm sure you want to show your mistress how much you like yours."

"Yes Ma'am. Thank you Ma'am. I've never cum so hard or so much. Thank you."

It took him a second or two to figure out how to get his panties off while kneeling, but he managed it. Turning the panties inside out so he could get at the cum, he stuck the dripping front panel into his mouth through the leg hole of my panties which were still on his head with the gusset at his nose. He began sucking the cum out of his panties while alternately taking in deep lungfuls of my panty's moist aroma.

Watching this act of submission was all I needed. Leaning against the doorframe I stuck three fingers into my steaming slot and quickly began fingering my clit.

Nancy couldn't figure out where to focus on me, on the panties in his mouth or the panties at his nose. Despite having just released, he was hard again.

In no time at all I had found my spot and was nearing an orgasm of my own. I started moaning and then swearing, "Oh fuck, ohhh fuck yes, mmm so fucking good. Ohh, ohhh, ohhhh"

Once again the waves crashed over me and I went down to my knees to maintain my balance and ride out each jolt. I knew he was watching the whole thing and the intimacy of our shared releases was remarkably satisfying.

We had both given each other what we wanted and were very satisfied by our respective roles. It was a new high point for my career as a dominant mistress.

Regaining my composure I stood back up and moved myself back to my spot directly in front of him.

"Well I hope you enjoyed that. You've quite pleased me this evening. You may stop sucking on your panties for the time being. You may clean them up the rest of the way after I leave."

"Yes Ma'am. Thank you. I'm glad this evening gave you pleasure. I'm so happy to have pleased you."

"You did Nancy. Thank you. Now go ahead and get your device back on. I have some ice in this bucket if you need it."

"Yes Ma'am. I wish you could stay."

"I'm sure you would like that Nancy, but it's probably best for us to stop right here. It's been a beautiful evening, don't ruin it by making me punish you."

"Sorry Mistress. I'll put my device on now."

He struggled a bit to get it on, but didn't ask for any ice. When he was finished, I continued.

"You may remove your device before you pass through security for your flight home, but you will put it in your carry-on bag. I will trust you to not touch my property during that time. After you pass through security, find a men's room and put it back on using the new lock I provided you. I shall mail you the key when I think you need it. You can keep my panties as a souvenir. I expect you'll keep them in a place of honor and treat them royally."

"Yes Mistress, thank you Mistress."

"I'll contact you as normal for assignments. Good bye Nancy, it was nice to have finally seen you in person."

"Thank you Mistress. This was so special for me, I'll never forget it. May I please kiss your boots one last time to say good bye."

"You may"

He leaned forward and reverently kissed each boot and as he sat back up I could see his eyes clouding up as though he was about to cry. I gave him a smile and then closed the pass door, quickly gathered my things and quietly left the room and the building. His desperate look and willing submission lingered with me however and was the source of several good orgasms that night and for weeks beyond.

Post script:

As it happened that was the one and only time I ever saw Nancy. We continued our on-line interactions for a couple of more months before he asked if we could stop. He said that the sessions had lost some of their edge for him once he had finally met me and he couldn't imagine that memory would ever be exceeded. I had to admit that there was some indefinable edge that had come out of our interactions and I was a little uncertain myself as to how to get it back.

We parted with a final live webcam session where I let him see me one final time and he was allowed to release into the panties I had given him. I've not heard from him since. If he reads this and recognizes himself (as he no doubt would) hopefully he will get back in touch with me and tell me how he is doing.