by John Dylena
Reed was at a crossroads. On the one hand, he was a straight man, and straight men don’t have sex with each other. On the other hand, he was dressed as a woman and acting like a woman. “I…… don’t know.”
“Raye, you’re a woman, be a woman for Christ’s sake! Tomorrow you can go back to being a plain old secretary. Now, let me take you on an adventure.”
When will I have this opportunity again? I did take this job with the notion to discover what it happen if I suddenly became a woman.
“Ok.” He said, taking a deep breath. “I’ll do it.””
She grabbed the dildo and put it away. She helped him out of the chair and he followed her down the hallway into the heart of her dungeon. She opened one of the doors and inside was a man. He was handcuffed, blindfolded, and naked.
When they walked in, Reed couldn’t takes his eyes off the man’s dick. It was just hanging there, free in the wind. He was entranced by it, almost as if it were a tractor beam, pulling him in.
“Now, Mr. Smith, I have a friend here who needs some enlightenment. You’re going to keep your blindfold on as she pleasures you, then you get to fuck her.”
“Yes Mistress,” he said.
“Go on Raye.” She said, pointing to his dick. Reed walked forward, his knees shaking immensely. He could see the man shaking with anticipation.
He stopped right in front of him. The man was older, probably in his late 40s. He was out of shape and chubby, his body covered in gray hair.
“Good, now kneel down.”
He knelt down, the man’s dick now inches from his face. He was sweating and his mouth was dry. He took a couple breaths then went in, starting by fondling his testicles. Apparently, it was enough to cause the man’s dick to swell. It got bigger and bigger, hardening before his very eyes. It grew inches within his face. The smell was intoxicating and Reed was losing control of his body and mind.
“Go on!” Arina cooed.
Raye leaned forward and kissed the tip. She could taste the man’s precum and she leaned forward and licked the bottom of his dick. The man let out a little groan of approval. She opened her mouth and took in the head.
“Further. Be sure to massage it with your tongue.”
She slid her mouth further down his shaft, her tongue lathering up and massaging the man’s dick. Her hand continued to fondle his balls as she began sliding the shaft in and out of her mouth.
“Faster.”
She slid the dick further into her mouth, the pulled out. Raye increased her tempo as she went further and further, taking more into her mouth. In no time, she was taking the whole thing as the man let out moans of pleasure. The taste of man meat was nothing she could ever imagine. The man climaxed and shot a load off into her mouth.
“Savor the taste, then swallow.”
Reed had never tasted cum before, but he didn’t think twice about it. He was enjoying himself too much and he continued to suck the man off. Mr. Smith shot another load, and when he was about to shoot a third, Arina pulled Raye’s head away and he shot it into her face. The warm and sticky cum clung to Raye’s face as Arina jacked the man off, shooting another load onto her face.
“Good, now turn around.”
Raye went onto her hands and knees and turned around. Arina uncuffed the man, and he knelt down right behind her. He found her asshole and slid his dick in, the saliva from the blowjob acting as lube. Because her ass was already loose from the dildo earlier, he managed to slide it in with ease.
Raye moaned loudly, as wave after wave of pleasure traveled though her body. She remembered the porno she watched earlier and realized she was in the position she fantasized about.
“Ahhh yes, give it to me,” she said. “More!” The man fucked her harder, and her whole body was shaking, she could feel the man’s warm juices shooting up her ass.
“Ohhhh yea,” she moaned. “I’m such a slut! I loved getting fucked and sucking cock!”
Arina knelt down next to Raye and whispered into her ear. “Do you like cock?”
“Yes Mistress.”
“Are you a man?”
“No Mistress, I am a woman.”
“Do you like having a vagina? Big bouncy breasts? A nice round ass?”
“Yes Mistress.”
“Do you like other women?”
“No Mistress.”
“Do you like men?”
“Yes Mistress.”
“Do you have a cock?”
“Only in me Mistress.”
“What is your name?”
“Raye, Mistress.”
“What are you?”
“A woman.”
“Good, Mr. Smith, you’re free to go.” The man blew one last load into Raye and pulled out. He stood up and Arina led him out of the room, leaving Raye laying on the floor exhausted with sperm leaking out of her ass. Her mind was racing, she was confused.
Arina returned to find her curled up.
“Raye?”
“Yes, Mistress?”
“Are you alright?”
He looked up at her, the light in his eyes gone. “What's wrong with me? I… I… ” He said nothing more and collapsed from exhaustion.
Reed and Raye were fighting inside. Arina knew this; she didn’t want him to lose himself. He came here with a question, and she decided to help him. But she was afraid that in the process of finding the answer, Reed, the man that walked through the front doors would never walk out.
For some strange reason, she was attracted to him. It puzzled her, for she hadn’t been attracted to a man in a long time. She had once again pushed him too hard and too far. She couldn’t go any further with this, for Reed might vanish, leaving only Raye. Even though Raye yelled it in her sex induced trance, it is not what she really wanted… it is not what he really wanted.
Arina had got carried away again, this time light-years beyond what happened a couple nights ago. When he kissed her in his drunken daze, she didn’t know how to react so she lashed out.
Now she had to protect him. Reed’s ego was in a fragile state and if she wasn’t careful, he’d break. But she couldn’’t just end the bet, that would be unfair to both parties. She decided that for the remainder of the week while he worked in her shop, she would do her best to keep Reed alive in that body.
No more overly slutty outfits.
“I understand… ” she said, smiling warmly.
She helped him up and he was mumbling something, but she couldn’t make out what he said. She carried him up to her office where she undressed him, cleaned the cum off of his face and anus, and she dressed him in his normal secretary outfit.
She wrote an apology letter, apologizing for pushing him too hard down a road she knew he didn’t want to go. After printing it, she placed it next to his sleeping body and returned to the lobby, where her next client was at the door.
I’m sorry Reed.
THE EXPERIMENT
CHAPTER XII: LOSS
Reed groaned as he opened his eyes. He sat up and found himself on the couch in Arina’s office. “What's this? I'm back in my secretary outfit.” He looked to the table and saw the note she had left him.
You have no reason to blame yourself for this. I agreed to your offer on my own accord.
He forgave her and decided that he would finish this week out. He needed to, his male ego seemed revived, like a phoenix coming back out of the ashes. The session with “Mr. Smith”, while it left a bad taste in his mouth, another sore ass, and some probably permanent mental images, made him determined to finish the week strong. He wanted to beat her so he could get what he desired from Arina, something she wouldn’t see coming. He stood up, straightened out his skirt and adjusted his stockings, the material caressing his hairless legs was now a trivial feeling, nothing to get worked up about.
He headed downstairs, and sat back in his chair. The porno video had long since ended so he exited out of the browser and ran a thorough virus scan. With the all clear from the security software, he got back to work. T
he massive pile of papers was gone, all the information was digitized and the papers shredded to tiny little bits. With that task completed, he moved onto the next item on the agenda: a complete overhaul of Arina’’s website. In the vast amount of free time he had after selling his business, he used the opportunity to learn to code, something he’s always wanted to learn how to do.
He didn’t pause to each lunch and continued typing; his fingernails clicking as they beat down relentlessly on the keyboard.
“Oh, I see you’re back to work.” Arina said, escorting her latest client to the lobby.
“Yes Mistress. I’m working on your website.” He said, scanning the chunk of code.
“Are you feeling ok?”
“Perfect. Don’t worry about me Mistress, I can and will get over it.”
“Good to hear,” she said.
She walked back up to her office and sat down in her big comfy chair. There was something about Reed’s words and overall appearance that bothered her. She felt as though she saw Reed sitting there, not Raye. He looked happy, revived… almost perky, as if what happened to him only two or so hours ago didn’t happen. He was back to the way he was a week ago, when he first started working for her. Her day somehow got brighter, and while she felt both puzzled and troubled by it, all she could do was smile.
Arina’s Journal, Day 10.
It’s been four days. On Monday, I feared that I might have destroyed Reed, leaving only Raye. I dressed him up in this slutty get up, and had him work in that. I caught him masturbating with a dildo that I mentioned was in the desk somewhere and I took it too far. I brought him in front of one of my male clients and encouraged him to suck my client off, then he took it in the ass. I got too carried away, I treated him like one of my clients, and in doing so, I felt as though I pushed him to a point where Reed couldn't come back. When he passed out from the exhaustion, I cleaned him up and changed his clothes, then I wrote out an apology.
I went to the lobby later and he was there sitting in the desk working. He seemed energetic and perky, and that lifted my spirits and renewed my belief that Reed was still there and in control.
However, on Tuesday, and more so on Wednesday, and even today, I began to doubt.
On Tuesday, he was acting more feminine than usual. Last week, he wasn’t acting very feminine, just professional. If anything, he had a slight wiggle in his butt when he walked, but it was barely noticeable. On Tuesday there was a definite wiggle in his stride. All day I would watch him on the security cameras in my office in between clients. Every day following Monday, he showed more developed mannerisms. I would see him examining his nails, making sure they're clean. He crossed his legs more when he sat and he adjusted his skirt more often. One day he came in with some girly magazines and read them throughout the day. At times I thought I saw him looking at men on the internet. He was more flirty with the VIP clients; he adjusted his makeup more often.
He told me that after work on Monday, he went shopping for something to wear at night time, and that he left with an extra outfit or two. Today he came in wearing a black mini dress and knee high 5” heel boots and during our lunch break, he was gossiping with me about all the latest celebrity news, cute stuff he saw while shopping, etc.
I also caught him occasionally checking out the men that would walk by. I tried getting his attention by calling out ‘Reed’, but he didn’t answer. I would follow with Raye and he would turn. I don’t know if he couldn’t hear me, or it was as if he didn’t know his name was Reed, just Raye.
Arina’s Journal, Day 12:
By now I feel as though I am 90% confident that Reed is gone. Today was Saturday, and I could’ve sworn that I saw him stick a tampon into his false vagina. His mannerisms have further evolved as he was getting really chatty, even hitting on some of my clients. He told me that the other night he went out to the movie store and rented some movies, I asked which ones and he told me they were chick flicks or something a normal guy would not be caught dead seeing.
Yesterday and today he came in wearing different outfits he had purchased. One was a plaid miniskirt, white button-down blouse, and black heels, with white stockings. Today he wore a strapless, green body-hugging dress, with matching green heels.
When I was spying on him on yesterday, at one point he stood up from behind his desk and knocked over the stapler. When he bent down to pick it up, and I saw that he was wearing a buttplug underneath the miniskirt. His walk is perfect, his mannerisms were genuine; body language, the way he walked, talked, spoke, hell even answered the phone was way more feminine than the way he was last week.
Tomorrow, I wouldn’t be surprised if he came into work saying he went out on a date one night and he ended up having sex with the man.
What have I done? In two days the bet will be over.
I just hope he hasn’t forgotten about it.
THE EXPERIMENT
CHAPTER XIII: REVELATIONS
Arina sat in the desk looking at the client profiles Reed created. Everything was organized and configured in a way that the user could switch between scheduling and bill paying effortlessly and efficiently. As she admired Reed’s handiwork, she heard the door alarm and the sound of footsteps. Arina looked at the clock on the computer screen.
Monday. Judgment day.
“Good morning Mistress,” she heard Reed say as he walked into the lobby.
“Morning Raye.” She looked away from the computer screen at him, expecting to see some new outfit. Instead he was back in the original secretary outfit, giving her a small sliver of hope.
“You had a lot of clients this weekend.”
“Yes, that is how my weekends are normally.” She replied.
“Some of them were pretty cute, like that blonde on Sunday.”
She stood up from the desk and left the lobby. “Yeah sure. Go on, get to work Raye.”
“Yes Mistress.”
Any hope Arina just had vanished with the comment about the cute guys that came in. What bothered her was that she didn’t remember a blonde guy on Sunday, but then again, she sees so many people and the hectic weekend made them all blur into one.
In her office, she sat at her desk and watched Reed work some more through the security feed. Raye announced through the intercom that her first client had arrived, ending her viewing session. She left her office, letting out a depressed sigh.
Hours went by and Arina saw no change in Reed. The end of the day came with her last client walking out the door. She walked back to her office and sat down on the couch. She broke down and started crying, not noticing Raye standing in the doorway.
“Why the long face, Mistress?”
“Oh Raye, I feel as though I betrayed you and in my actions killed off your male persona.”
“What do you mean Mistress?” She replied, walking up to her desk.
“Last week, I subjected you to your first sex session with a real man, and since that day, I saw no trace of your male self. With each passing day, your femininity increased dramatically. I saw no sign your old self. I only saw Raye.” During her bout, Raye’’s words from earlier replayed in her head.
… that blonde on Sunday…
Then she remembered: the blonde that came in on Sunday wasn’t a man, but a drop dead gorgeous woman. She looked up to Raye who was smiling.
“Sorry Mistress, but I lied to you. During that session on Monday, I discovered the womanly joys of sucking real cock; the taste of cum, getting fucked for real… but that night, I did some soul searching, and I am not a heterosexual woman, but a lesbian.”
“What?!” Arina’s jaw dropped. She stared at him, speechless.
“I am a lesbian. Sucking a dick was fun and all, but it wasn’t for me, I prefer women.” Arina couldn’t respond, she was flabbergasted. While she was searching for words, Raye stripped in front of her. She took off the collar, the voice patch, cleaned off the makeup, and removed the mask.
“Women are too damn sexy to pass on.” He said, his male voice ech
oing in the office.
Tears rolled down Arina’s cheeks. “Reed… ”
“So, did I win the bet Mistress?”
She laughed and all the sadness and depression vanished. “Yes… yes you did.”
He folded and set the clothes aside and removed the body suit. “Ahh, that feels good… gotta let the little guy breathe.” He went to the closet and put on the pair of jeans and the t-shirt he wore the day he started the week long challenge.
The bastard got me. He was so convincing.
“So, what will you have me do?” she asked.
“Well, there are two things.”
“What are they?”
“First: one day this week, I want to come in and not be your secretary, I want to be your assistant dominatrix. I want to wear a similar outfit as you and see what you do.”
She stood up, laughing. “My assistant eh? You want to help me physically, emotionally, and sexually dominate men and women?”
“Yes.”
“That sounds like fun, but in order to do so, you have to wear the body suit and be 100% woman again for the day.”
“Not a problem.”
“And the other thing?”
He hesitated, building up the courage to say it. The whole reason he took on the bet to begin with. The idea to act as her assistant was something he came up with in the days following the session with Mr. Smith. This was the real reason behind it all. “I would like to take you out on a date. Maybe dinner and a movie?”
She was shocked to say the least. Reed was right, she never saw it coming. “A date?!”
“Yes. You’re an amazing woman Arina, and working for you has been an incredible experience.”
Well, he did kiss me when he was hammered. I’m surprised I didn’t see it before.
“Of course,” she smiled. “I’d like that. It would be nice to get to know the man behind the woman.” They both laughed. “Ok, just a second.” She walked up to her desk and looked at the calendar on her computer. “Perfect, come in tomorrow clean and shaved. And how about Friday night for that date?”
