All the usual caveats If you are under 18 turn back now. If you a bothered by M/M or M/F sex then this is not for you.
While I don't describe the sex in this fantasy as safe. In real life always be safe.
That said the following is a fantasy of me losing my gender identity and control of my actions
If you like it and want to chat more you can email me at johnrain24601@yahoo.com
P.S. I love encouragement and orders
Jessi stood in front of the hotel door knowing if she went through the door her life was going to change. She stood there nervously she had a few minutes to decided before she would be late, and she knew if she was late, she would be punished. Despite her nervousness she checked her hair, straightened her blouse, and smoothed out her short leather skirt. She reached for the door nob and noticed the door was already open, just a little kept that way by the lock that was set preventing the door from shutting. With a gulp she pushed on the door and entered as quiet as 5 inch stiletto heels would allow. She noticed immediately that it was very bright. When she walked past the kitchenette and into the bedroom, she saw that the blinds were open to the balcony letting in sunlight, but also every light in the room and some big lights that were added were flooding the room with light. This shouldn't have surprised her, nor should she have been surprised by the large man laying naked on the bed, with a half hard cock that was a good 6 inches already and the thickness of a red bull can. When he caught sight of her, he commented "Good your early, I like that in my sluts. Step over to the dresser and spin around so I can get a good look at you.
She did as he asked and stopped at the dresser right in front of the metal collar sitting out. She spun around so he could get a good view of her. "Yes, yes, that is nice, worth every penny I spent to get you here." He said, adding "Now pick up the collar, my pretty slut" as he said this he picked up a cell phone.
"Now open the collar and say what we agreed on as you put it on" he smiled as his cell phone beeped indicating that he was now recording.
"I Jessi Wildmist agree that I am doing this of my own free will and that by putting this collar on I agree to obey all orders from Master Dave for the next 48 hours, as long as they do not violate our written agreement, and further I understand that a first punishment will be administered right after I close this collar as a demonstration of what I can expect." As she said this, she looked the collar over, opened it, placed it around her neck, and clasped it shut. When it was clasped, it let out a soft chirp and a beep came from Master Dave's cellphone.
Master Dave pressed something on his cell phone and the collar beeped again and made a loud click. "Good you are now locked for 48 hours and will be punished continually if you go more then 100 feet from this phone. Now for the first punishment as a demonstration." He pressed a button and ZAP Jessi felt a shock hit her neck from the collar. "That was the lowest level, there are 10 levels, and after ever third punishment I will increase the level, you understand that if we hit level ten is might leave a burn mark?"
"Yes Master" She replied.
"Good, now clip on the leash, hold it in your mouth and crawl over her and onto the bed." He ordered in a soft voice that did not convey the seriousness of his command. She promptly obeyed and fell to her knees with the leather leash handle between her teeth. Crawling first to the bed then pulling herself up onto the bed. While doing this she noticed the several video cameras around the room recording her from all angles, She was sure one of the cameras must be getting a good view of her ass as her skirt was obscenely short and she had taken off her panties nearly 3000 miles ago.
She stayed on all fours on the foot of the bed awaiting further orders. He smiled and put his phone to the side. "Good slut" he said as he took the handle from her mouth. "Now, crawl up further between my legs and start by licking my balls"
She crawled up and complied, she started to slowly lick at he hairless balls, watching his cock grow to its full seven plus inches as she did. "Now lick the shaft, but to not suck" as she followed his command as lick up his shaft then all the way around it she heard a clunk, as realized the door had just opened and the been let to bounce on the lock as it closed. They were no longer alone.
"Good run your tongue around my cockhead slut" he ordered Jessie, then he spoke to whomever was behind her "You're here, great, do you have what we agreed on?" He asked, "If you do hand it over then you can lift her skirt and spank this slut, you can even run your cock against her asshole while she sucks me, but do not penetrate her, I get to take her cherry."
The man handed over an envelope and Master Dave took out money, from the envelope, looked down at Jessie and said with a smile "How do you think I planned on making back what I paid to get you here slut, now suck me really well so I can break in your ass." She felt her skirt being lifted exposing her bare ass.
Smack, a blow landed on her ass as she took Master Dave's cock in her mouth. Smack another blow to her ass, as she bobs down on his cock determined to deep throat him, SMACK again but harder.
"A warning slut if I feel teeth you will get punished" she felt her legs be pushed apart and a cock glided down her crack till it hit her asshole and then it slowly circled and slightly poked. Causing her to moan like a good slut. SMACK her ass was smacked again this time with a paddle. The cock lost it's position and slid down, the man thrust forward as he SMACKED her again and his cock bumped up against the base of her balls.
She wondered how she got herself into this. 2 weeks ago, John replied to a message from a young stud in California on Fetlife, little did he know that in just two weeks he would be Jessi a slut that flew cross country to be whored out to multiple men. It started when Master Dave commented on a few of John's pictures and being polite John reached out to thank Master Dave. "I really like the picture of you with a tiara on and a cock in your mouth, I bet you would make a real good slut for me" was the reply he got to his message of "I'm glad you liked the pictures"
The message continued, I sent you some items from your wish list, and I want you to KIK me once you have them on.
The package arrived the next day, and in it were a few toys from his list, but also a personal note and a skirt, blouse, a red wig and 5 inch stiletto heels. He opened the note, and it read, "I know these were not on your list but put them on and KIK me- Master Dave". John hesitated, but then figured what the hell and put on the leather skirt, slight sheer cream color blouse the wig, and the 5 inch heels, with straps and pad locks?!?
When he was dressed, he opened his phone and started a live KIK. Master Dave quickly joined and spoke first. "I'm glad you obeyed slut, you look good" John blushed at the compliment as he thought he looked silly. " I have a proposition for you John, or should I call you Jessie?"
"Either is fine Sir" John meekly replied.
"Don't interrupt me again slut!" Master Dave barked "Now, where was I. Yes, a proposition, you see I think you a just primed to be turned into a passable little slut Jessie, and furthermore I think once we start you will want it, no need it by the end" he paused, and said "Lift up your skirt and if your clit is soft, I will stop right now"
John obeyed, taken aback by his cock being called a clit. But when he lifted the skirt, it was there a hard 5 inches.
"See, your excited. Now, I am going to send you more stuff, a bra, panties, false breasts, makeup, and perfume they will all be there tomorrow. Once they arrive, I want you to shave everything, but you head and eyebrows. Then put everything on, I will send videos for the makeup" here is the wager Jessie. I want you to put them on every day for the next week and then if you want to take this to the next step message me in 1 week all dolled up. If you do, I will issue you your next challenge" with the Master Dave hung up and John was left there to wonder.
The next day everything came via Amazon and John had already shaved everything in anticipation. John had already watched the links Master Dave sent and found himself eager to try it all! And he did every day, he would come home as John and with in minutes start to become Jessie. When the day came, he had fully become Jessie and she opened her phone and KIK'd Master Dave. He spoke immediately and said, "Nice and Pretty little Jessie, is your clit hard?" without hesitation Jessie lifted her skirt and showed her hard 5-inch clit. "Good my horny little girl. Now here is my proposition. You go when I hang up this call to the ABS just down the road from you. Spend 10 minutes shopping and 10 minutes in the first booth and you do this every day this week. If you go and resist the urge to suck a cock, then I will send you $10,000. But if you fail, I will send you a car and driver to take you to the airport and you will fly out to me and be my slut for 48 hours, agreed?
"Yes, Master Dave," John said in as feminine a voice as he could muster.
With that Master Dave said, "KIK me when you fail slut, I want to see that cock in your mouth, now go and have fun Jessie"
John/Jessie only hesitated for a minute before she got in her car and went to the ABS.
The first day she went in browser the man at the counter smiled and she smiled back, her 20 minutes were uneventful. The second day the same, the third day she saw the light turn on in the booth next to her and was surprised when a cock came though a hole in the wall. It was there for a minute and then it pulled back and Jessie saw an eye peek though the hole, look her up and down and then the cock returned as her 10 minutes ended, she ran out. The fourth day as soon as she entered her booth, a cock jut through, and she thought well what is the harm is just stroking him, and so she did and he moaned, and moaned and whispered "please suck me" but all she did was kneel in front of it and keep stroking, just as her timer went off for 10 minutes the cock blasted cum, hitting her nose, cheeks, lips, neck and blouse. She ran out knowing the cashier could see she was covered in cum. The fifth day she decided she would not even look at a cock if one came through the hole. As soon as she opened the door there it was, and she'd seen it enough to know it was the same cock. She couldn't help herself she kneeled in front of it and slowly started to stroke it. She saw the drop of precum on the tip and decided she needed to taste it, a lick isn't a suck right? And so she did, she licked the salty precum and when she did she knew from the moan she heard, come from her own mouth she was lost. She took out her phone and KIK Master Dave and was sucking the strange cock as Master Dave answered.
"Good Slut," he said, "Finish them off and KIK me when you are done, I will arrange you travel"
Them? She wondered? As she put her Phone down on the floor the cock in her mouth erupted and she couldn't help but swallow. As she did, he pulled out leaving a last spurt painting her face. She heard is door open and then quickly shut again. A new bigger cock quickly entered the hole and as she struggled to suck all of it she knew she was going to be here for a while. After her fourth or fifth cock her door opened -- she dad forgotten to lock it. The clerk was at her door, and he said, "when you are done with him come around to the back of the counter." As she swallowed her fifth or was it sixth load she straightened up and went to the door for the counter and entered.
So, Master Dave has asked me to check something, and the old man reached for and lifted her skirt front. And he saw Jessie's hard clit and the stain from where it had leaked cum on the inside of the skirt. "KIK him now the clerk said with a smile. "
She obeyed and Master Dave appeared. "Just like you though Dave, she came in her skirt and is still hard"
"Slut" Master Dave barked, "I will let you choose from two punishments. Either you let Mike take you in the back and fuck you, or you go out with him the center of the store and let him spank you and you suck anyone who offers you a cock, then Mike puts a plug in you. When you decide ask him nicely to do your choice and when you are done go home and KIK me"
"Mike, can I go out front and suck cock and be spanked?" Jessie said dropping to her knees to beg.
"Sure, said Mike, our cameras love a good show" let's go, and he opened the door. When the reached the center of the store there were two guys waiting there already, "get on all fours slut" Mike barked and when Jessie was presented on all fours he lifted her skirt up her back and gave her a good smack on each cheek, a cock soon was presented to her mouth and before Mike even started yelling "Suck bitch" her mouth was already on the cock. She sucked and sucked, and he kept spanking her, but with each swat her legs spread a little wider and Mikes hand move a little more inward. She was starting to get warn and she felt herself twitch but not just her clit, her hole twitched.
As the first cock came in her mouth Mike slaps moved from her cheeks, to landing one between her cheeks and right on her asshole. She cried out "Oh god!" as the cock pulled out.
Mike asked "Did you like that Slut" he smacked again harder but lingered on her asshole.
She tried to answer "Yes" but what came out was "Ysssssss" as cock entered her open mouth.
Mike kept slapping and each time he slapped two things would happen, she would moan on the cock and Mike would run a finger on her hole. This continued till she was fed another load of cum. As the man was cumming, Mike said "If you me to fuck you just say "Please" when he is done.
As he pulled out, she knew what she wanted. So, she said, "Pleaseeee, Mike, fuck my pussy, I need it"
In response she heard Master Dave say "Good Slut, I knew you would, now fuck her Mike" whit that her mouth was filled with another cock, and she felt a cold finger press into her, he hole grabbed onto the finger and didn't want to let it go. Her clit was leaking again, and the finger started to go in and out. Eventually it pulled out with an audible pop and was replaced by Mike's cock.
Mike had been told her and he did. Slowly at first, short thrusts then longer thrusts, but he didn't start to pick up pace until Jessie rocked back on his cock when he started to pull out. That got him to speed up, and she would rock back to meet each thrust, faster and harder he kept fucking her, to the point where she almost forgot about the cock in her mouth. She freed her mouth and yelled "OH GOD YES FUCK I'M CUMMING!!!!" as she did then her ass involuntarily tightened, and Mike erupted into her ass.
"Do you want more slut or are you done?" Mike asked
Her answer was more of a plea full of wanton lust from her still hard and still leaking clit. "YESSSSS MOORREEEEEEEE"
Mike pulled out and a new cock entered in balls deep in one thrust, she moaned and was offered a new cock to suck. And this continued for over an hour her being spit roasted taking cock after cock until everyone was spent.
When everyone was done, Mike told her to stay still and he put in a butt plug, but it took three tries to find one that would stay in her well used hole. "Go Home, don't clean up, and wait for Master Dave's call"
When Jessie got home she found an envelope on her front porch with her plane ticket and instructions.
That is how John became Jessie and property of Master Dave for 48 hours.
Part 2 to come if enough people ask.