Panties Gone Wild

Disclaimer: This is a purely fictional story, any similarities to real people or places are coincidental. The story was created as a Task for my Mistress, sharing it as well. I am not a native English speaker but have done my best for this my first story.

****

I don't know why I enjoyed wearing women's panties at work. It had started years ago when I was in my early 20's and in a short but interesting relationship with a hot brunette named Eva. Me and Eva never really clicked but for some reason we still ended up in bed together, she had a temper and was a lover of drama and I think i knew from the start the relationship wouldn't last. But even so we had some good times together, and with her slim fit runner body she was as sexy as they come.

She was the one who first made me wear a pair of panties. I honestly don't remember exactly why the argument started or what it was really about I just remember her being upset with me for not giving her a straight answer. I guess that's a fault of mine, when put on the spot and expected to give a straight answer there and then I tend to flounder, it was not what she wanted from her boyfriend...

"Just make up your mind already! I cant believe this!"

I was red faced and my heart was pounding, this was exactly the type of confrontation I hated. "I'm sorry alright, it just that I need some time to think. Could you please calm down and give me a few minutes? Or you decide, I don't mind..."

It was the completely wrong thing to say, and I could see it in her face as she set her jaw and looked me straight in the eye. "So you are going to make me the man in the relationship again huh? Fuck Carl, you really need to grow a pair."

I was taken aback, we had been seeing each other for a bout a month now and I knew I deferred to her in almost everything but even so that was a harsh thing to say to my face and worst of all I had no response. As I stood there in the bedroom trying to think of something to say and not even able to muster any anger or indignation over the insults. I wanted to strike back with something, make her realize how out of line she was attacking my manhood just because I needed a few minutes to think things over but I was unable to get think of any actual words to say.

She kept looking me straight in the eyes for a few seconds as I stood there and tried to form a comeback, and then her set tightly pressed lips turned into a smile that I can only describe as having an edge to it. "So I will decide again Carl. Well. Then we do this my way, YOU do this my way."

She spun around, all energy and focus, and went over to her underwear drawer. After some digging she found what she was looking for and threw me something small. "We are going to dinner tonight, and then a walk over at the lake. I will be wearing my purple dress and you will be wearing those."

I looked at what was in my hand and it dawned on me that it was a pair of panties. I did not know much about panties back then but they looked like any other pair, black with a tiny bit of lace but nothing special. Even so. Panties. "Are you serious? There is no way I can wear your panties! First off al-"

She cut me off in the middle of my panicked protest "Yes you will. I wont discuss this with you, I'm telling you. I ordered those online a few months back and ordered the wrong size so they should fit you. And considering how you have been acting lately they will fit you. Now, in going to change into my dress and you change into your clothes and then we're leaving."

I honestly did not know what to do. I knew I did not have it in me to fight her over this, but I could refuse and leave. Flight was an option. But as I stood there looking down on the panties in my hand I felt a tingle of... Excitement. This was some seriously kinky stuff and they did look cute. As I pulled them on and looked down on myself I felt and saw my cock harden in response to the sight, feel and foremost thought of what I was wearing. My cock is on the average in size but the panties made it look both small and big at the same time. I quickly donned the rest of the clothes before Eva found out about my embarrassing erection.

Throughout the dinner and subsequent walk I was reminded of my embarrassing underwear constantly. I would get lost in conversation or the food and forget for a while and then something would remind me and make me feel both humiliated and that in turn would excite me. It could be something as simple as shifting in my chair and feeling the snug fit of my underwear, or Eva suddenly smiling at me for no reason, amused by my secret. As the night went on we had a good time and eventually ended up home. I found myself kissing her passionately before we both ended up in bed naked. She seemed as turned on by the whole thing as I was and we proceeded to have some of the best sex in my life that night.

In the remaining two months of our relationship she had me wear panties a few more times and honestly it turned me on like nothing else, this was a new side of my sexuality I had never really discovered before. Even so, the sexy panties and the following hot sex could not mask the fact that we still did not get along very well outside of the bedroom and we drifted apart and soon broke up. Not really a bad breakup but neither of us had any interesting in being friends so we said our goodbyes and moved on.

****

That was 20 years ago, and here I am still single. Or at least single again, there have been a few relationships over the years but few is the right word. Nothing serious, and not with anyone who I was able to share my fetish with. Because by now that is the only thing I can call it, a fetish. Over the years I have come to terms with it, though nothing compares to the feeling of being forced to wear panties by my girlfriend I still enjoy the secret humiliation of it. Like any other normal single guy I watch my fair share of porn and that's where I found out about Femdom and BDSM. It had become a staple in my masturbation routine but not important or hot enough for me to go looking for a BDSM community or a Dominatrix and explore it further.

If you haven't picked up on it by now my name is Carl and I turned 40 a a while back and stopped counting after that. I'm single and living in a nice apartment in upstate New York. I used to be in good shape, running and mountain biking in the parks and hills around where I live, but now I'm just in decent shape. I have body that I don't really want to show off, but not a body I'm hesitant to show off either. I work in a Construction/Architect office as construction engineer, the office has been growing recently as we passed 50 people and I mostly do drawings for either tricky construction plans or construction drawings for the builders. I used to love my job and for a while thought I was going to make manager but some bad luck and bad decisions on my part led to me peaking as a senior engineer and honestly I'm fine with it but some of the passion is gone. At least as a senior engineer I'm on the same level as the architects I work with all day and don't have to take any crap from anyone.

Today I'm wearing my panties to work again, I also wear a striped dress shirt with a pair of dark gray chinos and polished leather shoes. And underneath that I'm wearing pink panties. Why panties? And why pink? Over the years I have slowly amassed a collection of panties I like and I usually wear a pair at least two days a week. This was one of those days. I have a briefing today with one of the newer architect, Jennie is a cute redhead a few years younger than me. She seems sharp and I am not expecting any trouble. I'm at the restroom, in of the the private stalls for obvious reasons, just finishing up when I hear my boss enter the restroom.

"Carl? You in here?"

I'm instantly annoyed, cant I even have some privacy on the toilet? But on the other hand this is out of character for my boss as he is usually a chill guy so I decide to answer. "Yeah Dave, kinda busy here you know..."

"Shit Carl I'm sorry to interrupt you." Even so I can hear obvious relief in his voice "We have an emergency with the state permit office, we fucked up the time on the drawings you and Jennie was going to review today and we need to get the changes in before 4 today or we are fucked."

I look at my watch and its already a few minutes after 3, to go over changes to the drawings, make the changes, email the updated drawings in less than an hour... Shit we are fucked. I rush out of the stall and head straight to the conference room where Jennie is waiting with drawings already on the table, she has also moved my computer in there and hooked it up so its all ready for me to roll.

"I'm so sorry Jennie, I just heard about the new deadline."

She gives me a quick smile "Don't worry, I hope you don't mind me moving your comp in here. I have already highlighted the changes I want made on the drawings and I think we should be able to get this done in time."

The next 45 minutes are a blur as me and her frantically work over the changes but we make it. The time is 15:58 as I send the email and get the confirmation that they have received it. I lean back and relax finally, I can feel sweat running down my back as I smile towards Jennie.

"We made it, damn that was tight but we made it. Good job!"

She is sitting at the same side of the table as me but a few chairs away, smiling as we are facing each other. "You too Carl, I'm impressed."

She stands up and gathers her stuff, I'm still sitting there smiling stupidly when she looks at me again and smiles. "You really stressed getting here did you? You even forgot something." Her eyes obviously shifts to my crotch between my spread legs "I like your panties."

I'm in shock, not even processing what she is saying, the smile on my face have turned to stone but she continues as though she does not even notice "We should have lunch tomorrow the two of us and celebrate. Tawara, a lovely little Japanese place, meet me there at 12." The last words are said over her back as she is heading out the door.

I slowly look down and face reality, my zipper is wide open exposing my very obvious pink panties. For a second I panic thinking the whole office saw them as I rushed to the conference room. But as I think back I don't think even my boss could have seen, I met no one on the way here. Here. With Jennie. Who saw everything. I try to pull up my zipper but it takes me several attempts since my hands are shaking so bad. I lean forward and bury my head in my hands in shame. It takes me a solid five minutes before I can actually gather my thought and think straight.

So she saw my secret. She did not scream pervert and run out the door, in fact she wants to meet me tomorrow. So she has something planned. Blackmail? I do make decent wages and have a little set aside but she did not seem like the type to blackmail someone. She seems kinda nice, very professional but nice. Thoughts racing but feeling calmer I gather up the last drawings and my computer and head back to my cubicle. As I am gathering up my stuff to head home I spot my boss Dave heading my way with a huge smile on his face. My heart skip a beat, what if she told him?

"Great job Carl!" He pats me on the back to emphasize how happy he is as he continues. "My and the other managers thought a stupid clerical error would cost us this customer but you and Jennie really saved our asses."

I stand up a little straighter and even manage a smile "Thanks man, I don't really know how we made it to be honest."

"Yeah you and the rest of the office. Jennie stopped by the daily managers meeting before she headed home, she said it was all you and she only assisted. You must have really impressed her for her to praise you like that in front of everyone, thanks again Carl."

He moves on and I put on my coat and head out the door. On the drive home his words play over and over again. Jennie gave me all the credit? Why would she do that? To be fair I did the lions share but she was on point and had either of us screwed up or fallen behind we would have never made it. And she seems like a career woman who would jump at the chance for a little fame and some goodwill with the managers. Where as I have given up on any chance of advancing. Hell, I would not even have blamed her if she had went in there and taken all the credit as long as she wouldn't have talked me down. What is she actually playing at?

****

I sleep restlessly, unable to relax. Somehow I'm still not tired come morning, I guess my body is in fight or flight mode and overruling petty things like sleep or hunger. At work it gets a little better as I can focus on the job in front of me and at least for a while forget about whats coming. And now the time is 11:55 and I'm trying to gather enough courage to face Jennie. I'm sitting in my car outside Tawara, a lovely little Japanese restaurant that is quite private, it even has private rooms you can book. As the cars clock hits 11:59 I get out, the only thing I fear more than facing Jennie right now is facing her while being late. As I enter the restaurant she is right there smiling at me and greeting me cheerfully.

"Just on time, perfect. I have booked one of the private rooms in the back"

I mumble some greeting back and follow her into the back room. Once seated at a small table the opposite each other we make some random small talk while we order and wait for our food. I'm nervous and confused, not just waiting for her to drop a bomb on me. After the food comes in and we start eating she finally gets to the point.

"Well then Carl, now that we have some time for yourself I must admit I was pretty shocked seeing your underwear yesterday. Have you been wearing panties for long?"

I feel myself blushing furiously, but don't see any point in lying. "On and off for about 20 years."

She raises her eyebrows in what might be surprise or being impressed, I cant really tell. "That long huh? Wearing panties now?"

I shake my head furiously, no way I was going to wear panties here after what happened yesterday.

"Oh that's to bad, I was hoping you would. You see I was rather intrigued by what i saw. I want to see more. You will show me more. Don't get me wrong, I am happily married so I'm not talking about an affair. But I have been really wet all day thinking about what I can make you do, and what I can do to you."

I'm flustered, what does she mean? "Have me do?"

She smiles again. "Yes. I know your secret, you will do as I say unless you want me to tell everyone and ruin your life. We work in a construction office, there is no way those macho guys would ever let you stay if they knew your secret." She leans back and watches me quietly.

The first thought that goes through my head is how different this is to when another woman dominated me all those years ago. Eva had been all fury, yelling and gesturing wildly. The contrast to the calm woman sitting at the table across from me was stark. And yet the familiar tingle in my body came back, something inside me was liking this. I decided to think this over, she did not seem to expect me to answer right away. Also a stark contrast to Eva, and something I instantly liked about Jennie.

To begin with she was wrong, blatantly wrong the way only someone new at the company would be. True, there was a certain macho culture at the office but it was mostly show. Add to that I had been at the company forever and was good friends with my manager Dave. I also happened to know that his manager, the VP of the company, had a son go through a full on sex change a few years back and had been nothing but supportive of both him, or well her, and the LBGT community at large ever since. Even though I'm not gay I was certain there was no chance at all of me losing my job even if this would become public. I might be branded as perv among my peers at the office and my social status would plummet but honestly, if it came to that it would probably not bother me that much. So, while it would be a pain in the ass that I would rather avoid she really could not force me to do anything to outrageous.

But she did not know that. So if I wanted to I could tell her to fuck off, and if she went public it might hurt me but honestly none of the managers would look kindly at her for spreading that kind of personal dirt around. She might be the one getting fired now that I really thought about it. So what did I want to do, tell her to fuck off or play along and see where this goes? I realized my dick was rock hard and that something inside me wanted her to do this.

"I understand the situation, and I will play along for now. But I'm warning you that I wont kill anyone for you or anything like that." No point in letting her know how weak her blackmail goods really was.

Her small smile turn into a full on grin. "Nothing like that I promise! We will start with something simple, from now on you will wear nothing but female underwear."

"I could do that, no problem."

"Oh honey, that not all. From now on you will also be wearing this." She grabs a plain brown bag from her purse and hands it to me.

I hesitantly accept the bag and open it enough to peer inside. It takes me a second to realize what I'm looking at. "A butt plug? Are you serious! I have never had anything in my ass and this does not even look small."

Her smile gets that edge again as she calmly answers. "Never question me. You agreed to do as I say and this is what I say. I can, and will, pull you aside anytime at work and inspect your underwear and your ass and when I do it better be plugged. In fact, you should probably take tonight to get used to it because tomorrow you are wearing that to work."

I made sure that the bag was firmly closed, hiding the plug and the bottle of lube I had spotted next to it and nodded. Tomorrow was Friday and traditionally a short day at least, if that was any consolation. She changed topic and we continued with some small talk before heading back to work. The rest of day I felt like I had a bag of radioactive waste hidden in my desk.

As I get home I guess there is no stopping this so I might get straight to it. The fact that the whole thing is turning me on like nothing before is really adding to my motivation. I go into the bathroom and unpack the plug and lube and sets it on the sink. Its black and its shiny rubber surface makes it look like liquid oil. I cant believe I'm going to put that monster inside me.

I start off with a long shower, both to relax a bit and get thoroughly cleaned. I wonder if I should be putting it in while in bed or in the shower? I have no real idea of what I'm doing but how hard can this be I think to myself? I turn the shower off and grab the lube and squat down, I start lubing up a finger and gently inserting it in my ass. It actually does not feel bad. I pull out and liberally lube up the plug before placing it beneath me and pointing it to my tight hole. I slowly start applying pressure and realize there is a big difference in size. I could barely get it a third in despite fighting the pain. I hold it there as the seconds go by applying gently pressure but not getting it any deeper. I decide a new approach is need and pull out.

After applying another dose of lube I start to fuck myself with the plug, each pump I try to go a little deeper until it just hurts to much. The pain is real but its also mixed with a new kind of pleasure I have never felt before. I keep doing this for several minutes until I feel like all I need is one big push to finally take it all. So I push. As the widest part passes my inner ring the pain makes my knees buckle as it lodges itself firmly inside me.

I just stay there breathing as the pain gradually subsides and turns into a dull throbbing pain that I can live with. I stand up and as I start walking around I find out its impossible to walk without noticing the plug. I spend some time at home just trying to get used to it before I decide to remove it before sleeping. Removing it turns out to be another painful experience but not as bad. Before I go to bed I boot up the computer and head online. I'm horny as fuck and quickly hits up my favorite porn sites. I usually start out at some random NSFW subs on reddit but tonight I go straight for r/femdom. I spend a solid hour jumping around related subreddits and the sites they link to until I finally cant take it anymore and cum massively. After I clean up I head straight for bed and a good nights sleep.