My Master & My WifebyFunWithDahlia©
"38 year old crossdresser, in good shape, looking for a Master to coerce me into oral and anal. Never been with a man before. Happily married, so discretion is important."
It wasn't the most eloquent three sentences I'd ever written in my life but what it lacked in quality it made up for in passion. I clicked the submit button and the listing went live on the message board.
My name is Greg and I'm happily married to Liz. She's a senior partner in a major oil and gas law firm. She travels to Washington DC one week a month to do lobbying work and to advise Members of Congress on "industry friendly" wording for new laws and regulations. We live in Houston and when Liz is in town, she puts in 60 hour work weeks. I have a part-time freelance job as a graphic artist... and I really just have the job so I don't have to call myself a stay-at-home husband. My work only occupies about five hours of my time every month and the rest of my days are occupied with housework, exercise, looking at porn, and crossdressing.
I loved Liz deeply when I submitted that listing but I never shared with her that I was into crossdressing. When we'd talk about sex and ways to spice things up I always steered the conversation towards what she wanted. I never felt safe sharing my fetish with her. I also knew that, even with my deep and abiding love for my wife, a woman could never give me what I wanted. As a result, I decided to not torture her with it.
About six months before I listed the posting online, I ran across a picture of a woman in sexy lingerie that was bent over a chair. A man was behind her, holding the woman's hands behind her back, and fucking her. Beneath the picture was the caption, "Be honest: who would you rather be?"
That one picture shook me to my core because I realized in that moment that I wanted to be sensually dressed, bent over by a strong man, and forced to fuck him while he admired my body. That one picture forced me to admit to myself that I wasn't just a crossdresser but that I was also bisexual. I bookmarked the page with that picture so I could revisit it. I ended up opening it every day. It called to me and filled my fantasies. Six months after discovering it, I took the active step of finding a man to treat me like the slut I wanted to be for him.
After submitting my listing I went to work washing all of Liz and I's clothing as well as tidying up the house. Houston is a large city so I expected to get a few men sending me pictures of their cocks, tons of spam messages, and hopefully one or maybe two serious replies. I really wasn't sure how many replies to expect so I didn't hover over the computer.
After lunch and my Pilates routine, I checked my email and was surprised that the first reply I received to my listing looked to be serious. It was from someone calling themselves BayouCityMaster and here's what it said:
To the crossdresser that posted the listing,
I am BayouCityMaster. Over the years I have taken both men and women through their fears and inhibitions to their desires and beyond. I am currently wrapping up a season with a couple and am intrigued by you.
To be honest, I think you're sexually unimaginative. Any man will fuck a slut up the ass and let her suck his dick. All she has to do is ask. I want to change you forever, not just give you a one-night stand. Here are some commands I might give you while you serve me:
- Changing the underwear you wear for the rest of your life
- Getting feminine tanlines
- Letting me watch you and your wife have sex via webcam
- Being seen in a semi-public place in drag
- Wearing panties in front of your wife
- Letting me video our sexual session(s) together
If you are serious, here is what you need to do:
- Take the listing down immediately
- At 4:00pm today email me a picture of your driver's license, your women's and men's clothing sizes, your cell phone number, and what you and your wife's calendars look like for the two months.
- Open a video/chat window at 5pm with the link at the bottom of the email. You'll be wearing nothing other than a pair of slutty panties.
If I haven't received the email from you by 4pm, I rescind my offer.
I couldn't believe what I had just read. It was more than I had ever imagined I would receive. I looked at the clock and realized I had 30 minutes to make up my mind. My hands were shaking, my breath was shallow, and I felt the color drain from my face. I pulled up the picture that had taken over my thoughts and looked at the woman bent over the chair. I wanted her life.
I immediately took down the listing, scanned my driver's license, and emailed all of the information to BayouCityMaster. I then ran to the shower and quickly shaved my body. I covered myself in lotion, grabbed a pair of Liz's panties from her lingerie drawer (we're about the same size since I exercise and diet) and slid them on. I looked at the clock and realized I had about five minutes to boot up the computer and get to the chat site.
I ran across the house, my ass jiggling in the red lace thong with each step. I turned on the computer, clicked the link, and sat down. One minute later BayouCityMaster logged on. In the video window containing him, all I saw was a dark grey sportscoat, a white shirt, and a blue tie. The window cut off below his head and above his waist. In my window was my naked upper body and my head. I started typing and my first conversation with Master began.
BayouCityMaster: Hello, Greg [name removed] who lives at [address removed]. Stand up and let me see what you're wearing.
I pushed back my chair and stood up. I saw myself in the chat window and got light-headed with a mix of excitement and fear as I realized that someone was seeing me in panties for the first time in my life. Master asked me to spin around a few times for him. I slowly turned, letting him take in my bare ass and lace-covered erection.
BayouCityMaster: That's a good little bitch. So you know, I am recording everything right now.
Me: I expected that, Master.
BayouCityMaster: Good. Now I'm going to cover my legal ass. You're going to read the following statement that I paste onto the screen with both your face and your panties showing in the video.
Me: Yes, Master.
BayouCityMaster: I, Greg [namewithheld], am participating in a sexual relationship with the person who goes by the online moniker BayouCityMaster. I will fulfill the role of a sexual submissive and he will fill the role of sexual master. BayouCityMaster has my permission to threaten me with blackmail involving pictures, videos, phone calls, and any other method he sees fit. BayouCityMaster has permission to have sex with me in any manner he sees fit. BayouCityMaster has permission to use my property and possessions while I am under his service. I hereby release BayouCityMaster from any legal liability or possibility of lawsuit in perpetuity.
I read it all aloud, realizing what I was doing as I read each sentence. This strange man now owned me. I visibly shivered on the screen as I read the last sentence.
BayouCityMaster: Good, bitch. I'll email you later. Your only assignment for tonight is to put all of your underwear in a trash bag and leave it behind a bush in your front yard.
[BayouCityMaster has left the conversation.]
After Liz went to work the next morning I hopped in the shower. After drying off I opened my underwear drawer and remembered that I no longer owned any underwear. There was a trash bag full of boxers in my front yard. I put on some shorts and a tshirt and checked my email. Master had emailed me in the middle of the night. Here's the message he sent me:
You need a woman's name. I'm giving you the name Gina. I might call you by it if you are a good girl, otherwise I'll call you bitch, slut, sissy, fag, or any other demeaning name I want.
I've retrieved all of your manly underwear. I went shopping last night and got you replacements. They're behind the bush where you left your old underwear. You should be glad that I am wealthy; otherwise I would have made you go and buy everything. You owe me your unconditional obedience in response to my generous gift!
I see that Liz is leaving town in five days. You're going to send her an email with me Bcc'd on it. You're going send her this exact message:
I want to spice up the next five days for us sexually. I've got a surprise waiting for you when you get home.
As soon as you send that email, you're going to strip down naked and only wear your new underwear for the remainder of Liz's time in Houston. Let me be clear: no shirts, shorts, shoes, jackets, robes, or any other piece of clothing other than your new underwear. I've wrapped and numbered each pair. You'll wear #1 today, #2 tomorrow, etc.
I'll be texting you at random times asking for you to take a picture of yourself as proof of your obedience. If you disobey, maybe Liz will have to learn about your fetish...
I practically ran to the front door, grabbed the box, and ran back to my bedroom. I ripped open the box and dumped five small manila envelopes onto bed. I got to see my Master's handwriting for the first time. It was sloppy but bold. I traced the numbers with my fingers as I thought about him.
I placed the packages numbers two through five in my underwear drawer and ripped open number one. It was a men's red gstring with a pouch in the front. I knew it was men's underwear because of the seam/pouch in the front where a cock and balls sit. I started to get anxious as I began to worry about what the other packages held. I took a deep breath and remembered one simple thing: I was not in charge here. I was going to do this whether I wanted to or not. Accepting the fact that I wasn't in control gave me an unexpected peace.
I said aloud as I put on the gstring and looked at myself in the mirror, "I'll wear whatever you want me to, Master."
Four times that day, Master asked me for a picture of myself. It was a welcome distraction but also mildly disconcerting that a stranger's phone had pictures of me almost naked on it.
Throughout the day I devised my best plan for not freaking out Liz and making sure she would be open to seeing me in my new underwear. At 6:30 Liz opened the back door and coyly called out that she was home. She found a note telling her that a bubble bath was waiting for her and that supper was beside the tub. After she had settled into the tub and eaten, she called out for me to come meet her. I timidly walked in with a champagne bottle in one hand, two glasses in the other, and my red gstring holding back my erection.
Liz gasped, giggled, and asked me to spin around so she could get a better look at me. I slowly turned for her, remembering Master's request for me to do the same thing the day before.
"I like it, Greg!" Liz exclaimed.
I told her that I bought a few new pairs of underwear and that I'd be wearing only my underwear for the next four and a half days and that my goal was to serve and please her sexually until she had to go to DC.
Liz looked my body up and down, licked her lips, and said "Mmmmm. If that's the case, why don't you come over here and get started."
Every morning it was surreal for me to stand there in only sexy underwear and kiss my wife goodbye while she wore a pantsuit. I would shower after Liz left, open my package for the day, and be surprised by what Master had for me. The second package had a men's white sheer string bikini. The third had a black thong and I couldn't tell if it was for men or women because Master had cut the tags off of every pair. The fourth package had a satin, leopard printed string bikini brief that also looked unisex.
It was desensitizing to constantly have on only sexy underwear. The first day, when I opened the package, I walked around with a hardon most of the day. By the fourth morning, when I kissed Liz goodbye wearing a leopard print bikini and she patted me on the ass, my cock barely stirred.
On that last afternoon, after I showered and fully shaved my body, I opened the package and pulled out a pink, lace thong. There was no doubt about what gender it was intended for! I took a picture and texted it to Master. I got a reply telling me to check my email. Here's what Master had written me:
You've been a great slave so far. Today is your first day as my little tranny bitch. Let me state clearly what you probably already fear and expect- your wife will see you in panties today. Actually, she has already seen you in panties the last two days!
At lunch, send Liz a text letting her know that you've got something special planned for her tonight. Do not answer her questions if she has any of them.
When she sees you and asks about the panties, tell her you got them out of the "Men's Alternative Section" of the store where you bought the other underwear. After that, what happens is up to you and her.
Have fun tonight!
I sent the text to Liz and she replied with a smiley face emoticon. I got supper ready and expected Liz to walk in the door at 6:30. At 7:00 I called Liz but got no answer. At 7:30 I texted Liz and she told me that the other Senior Partners all went to dinner together and insisted she join them. At 9:00 Liz told me not to wait up for her.
At 10:00pm I texted Master a picture of myself in bed wearing my panties and told him that Liz was staying out late with her coworkers. He replied that she could see me in the panties tomorrow morning as she left for the airport.
I woke up at 6am to cook Liz's breakfast for her. (Actually, I woke up at 4:30 with nervous anticipation and I just stayed in bed slowly stroking my panty-clad cock and daydreaming about what might happen until 6am.) At 6:30 she stumbled into the kitchen, poured a cup of coffee for herself, and turned around to look at me. Her jaw dropped when she saw me standing there, cooking eggs in an apron with a pink, lace thong crawling out of the top of my ass crack.
"Greg, that's a new look for you." was all she got out as she stared at me.
I didn't look at her as I finished cooking her omelet but recited Master's line about getting it in the Men's Alternative Section of the store I bought the rest of my new underwear.
Liz shrugged a little as she walked past me. She sat down at the table and drank her coffee, looking at my panties the entire time I got her meal ready. I took off the apron, walked over to Liz, and put her plate down in front of her.
As I started to turn away Liz put her hand on my ass and pulled me closer to her. My cock was inches from her face as she reached her other hand up and started running her fingernails along it, coaxing it to its full length.
"I never told you this before", Liz said as she stared at my panty-covered cock, "but I had a girlfriend for a few months in college. It was just a phase I was going through at the time."
Liz pulled my cock out of the side of the panties, started running her fingernails up and down my shaft, and cupped my ass cheek with her other hand.
"Seeing you in these panties reminds me of those days. She used to walk around in nothing other than her panties, like you are right now. Do you like wearing them, Greg?" Liz stopped talking and looked up at me for my answer.
I nodded yes and she kept talking, "Have you worn panties before?"
I nodded yes and she kept talking, "Do you do this a lot when I'm at work?"
I nodded yes and she kept talking, "Do you want to do this with me more often?"
Liz was rubbing her thumb across my shaft over and over again. I wasn't close to an orgasm yet but I could feel it building in me, my arousal driving me to keep me answering truthfully.
I nodded yes and she kept talking as she started jerking me off, "While I'm gone, why don't you buy yourself some more sexy lingerie, a wig or two, and we'll have some fun when I get back, OK?"
With that said Liz took my cock into her mouth and put her other hand on my anus, slightly pushing against it. I exploded instantly in her mouth. Liz drank all my cum in, casually turned back to her plate, and finished her breakfast. Slightly dumbfounded, I stood there in silence and watched her eat for a while before I went back to clean the kitchen.
An hour later I kissed her goodbye at the door, wearing my pink thong while I wished her a safe trip.
I couldn't wait to tell Master: my wife was into my crossdressing! I emailed him with all of the details.
That afternoon I received a reply from Master. Here's the message he sent me:
Don't you see now that everything I have you do is for a reason? Throw away all of the underwear that I just bought you other than the pink thong. You're going to walk around naked today.
Tonight, at 3am, you're going to drive to the address at the bottom of the email. You'll only wear a pair of shorts and a tshirt. They shouldn't be nice since you'll never see them again. Bring only your phone and driver's license. Follow the instructions I'll send you by text message.
At 2:30 I got into my car and drove across Houston to the address Master had given me. It was a strip mall off of Westheimer Boulevard, one of Houston's major roads. Because of the hour, there weren't many cars on the road.
As soon as I turned into the parking lot, Master texted me with instructions:
Park under the light with the pink ribbon wrapped around it.
Since there were ten light poles in the parking lot it took me a moment to find which one had a ribbon. I parked underneath it, killed the engine, and waited. My phone chimed after a few seconds:
Leave the keys in the ignition and the car unlocked. Walk around the right side of the strip mall to the dumpster. There's a note on it with your next instructions.
I got out of my car, walked around the side of the strip mall, and saw a piece of paper taped to the dumpster. Here's what it said:
This is your last chance to get out. My first command for you tonight is to throw your clothes into the dumpster. If you do, from that point forward I will do everything in my power to mold you into what I want to make you.
If you walk back to your car, I'll delete all of the pictures and videos of you that I have. It will be like none of this ever happened, other than that your wife knows you like to dress up like a woman.
If you throw your clothes in the dumpster, you'll put on the clothing in the bag at your feet and follow the instructions I text to you... and I'll take you to places you never knew you wanted to go!
Honestly, I didn't even hesitate. I stripped off my shorts and shirt, dropped them into the dumpster, and ripped open the bag at my feet. There was a pair of black booty shorts with pink lace trim that had the word Naughty written across the rear. A pair of black, four inch high heels, nipple clips, and dark red lipstick.
I hurriedly threw on the panties, stepped into the heels, applied the lipstick, and gasped in pain as I attached the clips to my nipples. Instantly I felt the connection between my nipples and my cock. The pain first mingled with my cock and then twisted fully into dark pleasure.
My phone chimed in my hand. I immediately switched it to vibrate and read the message from Master:
You chose well. We're going to have fun together, sissy. I just took your car, by the way. You've got to earn it back. The only way to do that is to complete your journey! Walk to the other side of the strip mall and find another bag with more instructions.
I teetered in the heels, running as fast as I could around the building to look at where I had left my car... it was gone! My heart started racing in my chest as my situation went from sexually exciting to nightmarish. I was in panties and heels, 30 minutes from my house, with no way to get home. Master had already taken me further than I wanted to go and there was no way out other than his way!