Set Up Ch. 01

This is my first attempt into writing an erotica story. This tale will contain themes of female domination, crossdressing, and eventually MM sex. If any of this is not you thing, please scroll on. Otherwise, please let me know how I did.

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Since I was a teenager, I had been bicurious. Not really interested in men, but what is between their legs. My obsession with penis probably started as just watching too much porn. Straight porn turned to she male porn, then to bisexual porn, the gay porn, then sissy porn. I often found myself wanting to be the woman in the videos, so I decided that I would wear women's clothing while watching. First it was my mother's, and after marriage, it was my wife's. Then I started wearing it around home while I was alone. Despite all of this, I had never convinced myself to finally taste a real cock.

One night, I thought I'd post an ad on Craigslist. Too nervous to meet just a man, I tried to find a bisexual couple. For the first couple of days, I never got a response. After giving up hope, I noticed an email one day that read "Single dominant woman. Looking for a sub male to be my bitch." At first I did not know what to think. I did lean toward a submissive attitude, but had never thought much into a dom/sub scenario. Intrigued however, I replied.

"Hi! I'm bicurious, but married so have never gotten to explore my sexuality. I guess I can be submissive, I do like to imagine being in the woman's role of sex. I'm interested in your proposal. Hope to hear from you soon." Five minutes later, I got her response.

"Hello my pet. I'm glad you responded to my post. My name is not important, you may, or should I say MUST call me Mistress. I'm glad to hear you want to take a woman's role, as I'll want my new bitch to take a slut's role. Is it safe to assume my new toy likes to wear women's clothing? Pretty dresses maybe? Sexy lingerie? High heels? What is your sissy name?" I'd had a name in mind for a couple of years. I'd never said it out loud, or even written in down.

"My sissy name is Ashlee."

"Ashlee? That's a very pretty name, although irrelevant, You'll learn to answer to 'bitch', 'slut', 'faggot', etc. When will you be available for my pleasure?" I was afraid to answer, never had my fantasies, and secret life, been so close to coming out in the open. I thought about it for a moment, and knew that I had the perfect opportunity coming next week. I hesitated, then sent my reply.

"I'll be alone for 4 days next week. My wife will be out of town on business."

"Good. I'll be in touch."

That was the last I heard from her. I thought maybe the opportunity had passed me. Then I got paranoid, Maybe it was someone I knew fucking with me. I was so scared someone had found me out. I checked my email nonstop. Finally, the day before my wife's flight, I finally got the message I had been waiting on.

"Hello my sissy bitch. I'm sending you my address, I expect you to be here no later than 8:00 PM tomorrow. If you're late, you WILL be punished. Show up fully dressed en femme, no exceptions. Don't keep me waiting slut."

My fear suddenly turned to excitement. I'd never been talked to like that, and it thrilled me. My wife's flight was at 5. I immediately hopped in the shower and shaved all of my body hair. My makeup was flawless, I'd practiced for years. I picked out some red and black lace lingerie, and a short black dress. I got my silicone beasts out of their hiding space and slid them into place. I looked myself over in the mirror, perfect

My new Mistress' home was a 15 minute drive, and in a very high end part of town. When I reached the address, every light in the house was off. I checked my email, this was the correct address. Looking to make sure no one could see me, I hopped out of the car, my heels clicking on the sidewalk, I scurried to the front door. I knocked, no answer. I knocked again. Then a young, attractive red head was coming down the street walking her dog. I panicked, not wanting to be seen like this. I didn't know what to do. I ducked my head in shame. She paused for a second before whistling my direction and laughing hysterically as she walked off. Humiliated, the door finally opened. I could see into the house, but could make out the outline of a slender, tall woman. She handed me something and said, "Put this over your head."

I was now blindfolded, being led through a strange home. Finally, we stopped walking. "Sit down." I started trying to feel for a seat when she pushed me hard into a cold, wooden chair. "I said sit you stupid cunt." Again the names, I loved it. My own dick was growing hard from excitement. Then I felt restraints being put around my wrists, effectively bounding me to my chair. I asked what she was doing, no answer. She only continued strapping my in. I felt her hands begin to lift the front of my dress, then pull my panties down beneath my balls. I was in Heaven, helpless, blindfolded, and a strange woman about to play with my... WHACK!!

I literally saw stars from the impact her hand had with my dick, now completely deflated. I felt my penis being fed into something small and cold. A chastity cage I assumed, and the clicking of the lock confirmed it. The excitement I felt earlier was now completely replaced by fear. I was in a strange neighborhood, blindfolded, tied to a chair, at the mercy of a woman I'd never seen. Then I felt a hand on the back of my head, pulling my closer. My lips came in contact with something cold and rubbery. I immediately realized she was wearing a strap on. I didn't have time to think, she just forced my lips open. Although it wasn't a real cock, it was shaped perfectly. The head, the veins, the shaft. And she was pushing inch after inch into my mouth. When she reached my throat, my gag reflex kicked in, hard. I choked and gagged on the massive dido in my mouth. Apparently this made her mad. She slapped my face, hard.

"You pathetic fucking slut, take my cock down your throat." She then starting fucking my throat with no remorse, slapping me again everything I gagged. It didn't take long for my throat to open to accept this intruder. Once she noticed I had accepted her "cock", she stopped. I sat there for minutes hearing nothing but my own breathing.

Without warning, my blindfold was ripped from my head. For several seconds, all I saw was bright light. When my eyes adjusted, I realized the light was coming from a spotlight aimed directly at my face. All around me was a scene straight out of a BDSM adult film. Whips, rope, cuffs, swings. So many devices used for sexual submission. The last thing I noticed sent chills of fear down my spine. Pointed at the chair I was sitting in, a small video camera, flashing red light indicating it was active. My fear brought an outburst of cries. I started to scream "What the fuck?!?", but before I could finish, I was again slapped across tge face and a gag was placed in my mouth. I looked up and saw my capture for the first time. She was a little shorter than myself, medium length brunette hair, light makeup, I'd guess around a C-cup. She had perfect curves. I couldn't help, however, feeling like I knew her from somewhere. Then I noticed the black rubber cock between her legs. It was massive, 9 inches, much bigger than my 6. For a moment, I became proud that I deep throated i, but my arousal was subdued by the harsh reminded of the steel cage around my own dick.

"My God, maybe that will keep you quiet you whimpering bitch. Damn. By now you see the extent of what being my slut will entail over the next four days. You will be whipped, restrained, abused, and fucked like the sissy faggot you are. I intend to show you no mercy." I heard most of what she said, but my gaze was transfixed on the red light of the camera. "Oh that? Don't worry, it's an audience of one, for the moment. But it's not my decision who else sees it." I stared at her confused, I wanted to ask what she meant, but the pink ball in my mouth prevented it.

"Hello... 'Ashlee'." My heart sank. I felt all the blood run out of my face. "Did you really think I didn't know about this fantasy of yours? You would think you would be smart enough to delete all of your browsing history. I truly hope all those 'sissy training' videos prepared you for this week." It was Lauren, my wife. "Yes, I know you've been wearing my clothes, stretching out my lingerie, cumming in my panties as you fantasize of being a whore for men."

"You remember Helen, don't you? You've met her once, at the gym with me. Well, I was distraught when I learned that my husband was such a, well, Sissy. She consoled me, told me some men just have fantasies. So, I've been planning this with her. When you posted your ad, it was the perfect opportunity. I have a live feed to everything that happens in that basement. I will see you in four days, and it is then we'll discuss our new living arrangements. Oh, and just so you know, had you come clean about this, we could have had a lot of fun, together. Helen, be a dear and make him regret he didnt."

"Of course Lauren. See you soon."

She grabbed the back of my head, and without hesitation rammed the 9 inches of rubber cock back into my throat...