Background
This story involves my on-line subject Nancy, who I introduced in Mistress Chronicles #4. This subject passed all of the tests I described in "A few good subs", but before we were able to arrange an in-person session, he was offered a job in a town a great distance away, precluding in-person meets.
Nancy is a computer nerd. Brilliant at working with machines of all kinds, but hopeless with humans. He's not terribly self-confident unless he's writing software code, where he feels he's 'among the best.' He's early-thirties, slender, but not really physically fit. Scrawny is the word one might use. He admits to having little experience with women and that he has only had actual intercourse one time.
Apart from female domination, his fetish is lingerie and forced feminization. Through our interactions he has gradually built up a sizeable collection of lingerie which he routinely wears to work under his outer clothes.
It's interesting to note that in all of our sessions Nancy has never actually seen me. I have sent him pictures that I have told him look similar to me, but never an actual photo. He has a photo of a vagina that I have told him he may assume is mine which he is sometimes asked to stare at and say devotionals to, but it's not mine, just a photo I ripped from the net.
Scenario
By chance, Nancy is scheduled to attend a seminar related to his job which is to be held in the town where I live. Taking advantage of the opportunity, I offered to meet him for his first in person session. I advised him that some of his limits would be tested both before and during the session. He chose to accept the challenge.
He booked us adjoining rooms at the hotel he would be staying at for his conference and provided me the details. Our session would begin at the end of his first day in town. I would contact him at approximately 5pm on that day. Beforehand, he was assigned a number of tasks, which I have asked him to write about.
Nancy's journal
Thank you Mistress for giving me the opportunity to have a session with you, I will never forget it. My story begins about three weeks in advance when I told Mistress of my travel plans and she made me her gracious offer, which I received on Christmas Eve. Her first order was for me to maintain strict chastity for the following 23 days. I would not be allowed to cum for the entire time.
This by itself was a challenge as Mistress continued to demand that I edge myself each night while conducting my chastity device cleaning ritual. Needless to say I began counting the days right from the start. Not only would I have a chance to see my Mistress for the first time, it would be my first chance to earn release.
The second order for me was my personal grooming. I was required to maintain myself completely clean shaven from the neck down at all times under warning that she could demand 'spot check' photos from me at any time. This was a lot of additional effort as the only area I had previously shaved was my legs. I kept this up every day and I welcomed the chance to make myself nice for Mistress.
The third challenge was during the week before my departure, three times I was ordered to wear women's pants to work. I had done so a couple of times before, but never so many times so close together. I was also wearing panties full time and sometimes was ordered to wear quite frilly ones. I was very worried about co-workers seeing my panty lines.
I did as ordered, being sure to arrive early each day and stay in my cube as much as possible. The third time I wore them, I also wore black women's trouser socks as well. It was so exciting to be completely feminine from the waist down (except shoes) especially with my shaved legs. I could hardly sleep that night. I wanted to cum so badly.
My last challenge related to my flight. Mistress required that I wear panties and black tights under my pants and that my toes were painted hot pink. The clear plastic bag that I sent through the x-ray machine included two lipsticks and the hot pink nail polish in addition to my regular stuff.
Fortunately mistress had allowed me to remove my chastity tube and send it inside my checked luggage (along with a number of other specified items). Instead she sent me a leather pouch which she made me lace on tightly using rawhide cords with orders not to remove anything until I had checked into my hotel room and received instructions.
I had hoped that she might supervise the removal in person, but didn't think that was too likely as I arrived at nearly 11pm. Instead, when I arrived I had an envelope waiting for me. Inside it was three numbered envelopes, a blindfold and a small padlock.
The first envelope included my instructions for that night. I was to remove my pouch and re-secure my tube using my normal lock. I was to keep the other padlock open and with me at all times. I was ordered to wear the baby doll nighty I was told to pack when I went to sleep and to open the second envelope the following morning before dressing for my seminar. Naturally I didn't dare touch her property improperly. I had been saving myself for Mistress and didn't want to make any mistakes.
The second envelope specified that I was to wear the white lacy camisole, panties, garterbelt and sheer white hose that I was instructed to buy and bring. This set was part of a 'bridal' collection and was very expensive and frilly. It looked adorable and I couldn't wait to wear it from the moment I bought it.
I was a little disappointed that my first time wearing it I would have to cover it up. Mistress allowed me to wear socks over my hose. Underneath my regular pants, shirt and sport coat I didn't think it was too noticeable, but I was very afraid of being discovered, you could see the garter tabs through the pants if you were looking for them. I didn't really know anyone, but there were a lot of people at the conference and anything could happen.
The final envelope I was to open at 4pm. It specified that when I returned to my room I was to strip off only my male clothes. I was to set up my laptop and log into a private chat promptly at 5pm and she provided me the information. She had told me to pack several pairs of earrings and that I should put on the "sissiest" ones that I felt willing to wear in public. I chose my white pearl (not really) earrings.
I'm supposed to stop there, but must add my thanks to my Mistress for making this the greatest experience ever. I'll never, ever forget it.
On-line session
(Nancy has entered the chat)
MistressM (abbreviated as M, following): Hello Nancy. I hope you had a nice day today. I saw you walking around the hotel. I could tell you were enjoying your sexy secret lingerie. Don't worry, I don't think anyone would have noticed the garter tabs and panty lines unless they were really looking.
Nancy (abbreviated as S for Sissy, following): Good evening Mistress. I'm so happy to be here. I can't believe it's finally here. Thank you for doing this. It's hard to believe you are just in the next room.
M: Yes, it is kind of exciting to finally meet. It's been more than a year since we started corresponding.
S: Yes Mistress, the best year ever.
M: You'll probably be pretty disappointed if it turns out that I'm really a 55-year old fat bald guy who gets off on sissy boys.
S: I'm sure that's not true Mistress. I trust the pictures you sent me and I've heard your voice.
M: I guess you'll find out soon enough. First I think we need to make sure you are good and ready. How long since your last release?
S: It has been 23 days Ma'am. Christmas Eve. I haven't had a release yet this year.
M: Maybe you'll be able to earn one tonight. We shall see.
S: Thank you Mistress.
M: We are going to play a game. You may remove your device. Let me know when this is complete.
Pause. S: I've removed my device. Thank you Mistress.
M: So this is the game. Please take your small plug and put it in your mouth. You are not to speak. You will respond only via chat. I'm going to call your room in a minute. Pick up the phone and put it on speaker where you can hear me.
Phone rings, Nancy silently picks up phone and puts it on speaker.
"Good, now you can hear me but not see me. On my command, you will begin stroking yourself to an edge. When you are at the edge, you may type edge, into the chat. When you hear my permission you may stop. If you cum, the session will end. Understand?
S: Yes Mistress.
"Begin, Let's see if you can make four minutes"
(every 30 or 40 seconds I made a comment)
"You look very pretty down there on your knees"
"Isn't the silk of that camisole just wonderful. Caressing your little sissy nipples"
"The stockings are so silky too on your hairless girly legs"
S: Edge
"You may stop. That was about two minutes and thirty seconds. You'll need to do better. Go put on your white training bra. It doesn't really go with your outfit, but a sissy should be wearing a bra and I gave you a break not wearing one all day. Let me know when its on"
Pause, sounds of looking in suitcase. S: I have my bra on and I'm back in position Mistress. I'm sorry for last time. I'll do better.
"Begin."
"Such a little sissy. Sucking cock"
"You'd do anything for your mistress wouldn't you?"
"You'd suck a real cock if I told you to."
