Blackmailed into being a woman: “Are you man enough to be a woman for me?”

“You can keep your job if you are man enough to be my woman and woman enough to satisfy my needs.” Blackmailed into being a woman; Quid Pro Blow.

Word to the wise: When downloading porn files and you only want to “Save” them to YOUR laptop do NOT accidently click on “Save and Share.”

The Setup

Jack is an unmarried college graduate with a degree in corporate finance and a minor in Social Media; he’s was in his first year with a successful privately owned internet Advertising & Marketing firm. For a closeted cross-dresser Jack/Jackie’s future looked bright.

Jackie is Jack’s femme alter ego. In the privacy of his condo, and under his boy clothes at work, Jackie routinely dressed, looked and felt like a pretty young woman. Any one would think Jackie was Jack’s beautiful twin sister.

At home Jack frequently web-surfed CD/TG/LGBQT web sites and had became enthralled with male-to-female photo morphing sites. Jack liked that he could try a variety of make-up, hair styles and looks without the trouble of makeup application and removal; just upload a good selfie head shot and experiment. If you found a look that you liked just ‘click’ and ‘save’. Jack had a special computer file folder labeled ‘Jackie’ where he saved and stored his better femme looks.

Simple: just ‘click’ and ‘save’

On a Friday evening Jack/Jackie got himself into a very dire situation when he accidentally sent a homemade mini porn video and several salacious still photos of Jackie to his coworkers by mistake. While using an online X rated CGI gender morphing site Jackie had clicked on ‘Save and Share’ instead of ‘Save’.

Several co-workers complained to company President Mike Spence about receiving inappropriate images from Jack; they had forwarded Jack’s porn video and images to Mr. Spence.

Mike Spence was founder and sole owner of a very successful social media company. Mike had total control over all aspects of his company. There was a secret (but rumored) side to Mike; that he was a closeted cross-dresser with same-sex fantasies and desires. One fantasy was hiring a ‘tutor’ to assist “Lana” (his femme alter ego) in looking and dressing like a woman. Another desire was to have sex with a cross-dresser while both were dressed in femme. Lana was actively looking for this perfect bisexual encounter when Jack’s video literally dropped into his lap. Spence found Jack’s porn video to be the perfect blackmail weapon to convince Jack to be that tutor and sex partner; comply or be fired.

Rumors

There was long standing office gossip about nail polish residue being visible around the cuticles of Spence’s manicured nails. Obviously shaped eyebrows, mascara flecks at the base of his lashes and faintly stained lips were also routine office gossip topics. Everyone needs a hobby and that includes the boss. It just happens that the boss’s hobby was cross-dressing and lusting after girly-boys.

Reinforcing the rumors is that Mr. Spence had been seen intently perusing “Chicks with Dicks”, “Trans” and related She-Male magazines at the ‘Garden of Eden’ adult book store a few blocks from the office. Office gossip contends that Spence harbors ‘chicks with dicks’ fantasies; receiving Jackie’s porn video was a true gift for Spence. Could it also be good for Jackie?

How it happened

One fateful day while enjoying his favorite gender morphing site Jack clicked on a link that took him to ‘TransFormYou’ (TFU); a high definition CGI quality male-to-female morphing service where every computer generated chick had a dick. All a person needed to do was upload a high quality portrait or head shot and let the website and their imagination take over. The person would still be recognizable to friends but their features would be unmistakably feminine; like an identical female twin.

Virtual ‘Plastic Surgery’

In addition to hair and makeup head shots TFU gave you the option of selecting body shapes, breast size, cleavage, etc. TFU.com was perfect in many ways; it had features not found on other websites.

With a single mouse click you could be dressed to look like a cheerleader, bride, school girl, drag queen, sissy, etc. There were ‘Slut-Me-Up’ and ‘Make Me a Porn Star’ options; video or still images. The finished XX TFU CGI “movies” were amazingly realistic and very erotically stimulating. The resolution was amazing; just click, save and masturbate if the mood was right.

‘Slut Me Up’: Masturbate, Click and Save

Jack had visited the TransFormU site several times trying to become familiar with how to use the many features. It was on his fourth visit when he found the site had added new, adult, features. It was a beta program that was being tested. Once you had selected your basic ‘look’ you could now click on the ‘Slut-Me-Up’ or ‘Make Me a Porn Star’ options. TFU technology was truly amazing.

For a small fee, the site would put you, in your chosen ‘look’, into a three minute computer-generated imagery (CGI) porn movie! $200 got you three videos.

Still images - ‘Be the slut you yearn to be without the fear of STDs’

Jack added black four inch pump heels, 40D size tits, sexy gold chandelier earrings, showgirl makeup, long brunette hair and two inches of cock. For a background he had Jackie standing, with her hands on her hips, at the foot of a magnificent bed in a beautiful boudoir setting with an impressive dangling dick; it was a very artful image! Jack clicked and saved this fantasy wet dream photo.

The final scenario Jack created was a still image of the perfect Jackie Sissy; black patent leather Mary Jane shoes, white leggings, a pretty Sissy dress with a large bow in the back. And of course her face and pouty lips were perfectly made-up and her hair was awesomely Sissy! Jack smiled, clicked and saved “Sissy1” file.

As an afterthought, because the process so easy, Jack used the same file and had his Sissy character smiling and holding up the front of her Sissy dress to display a lovely erect penis in a chrome cock-cage.

Its stiffness was magnificently erotic and perhaps mouth watering to some; let your randy imagination complete the mental image of what this photo looked like. Jack clicked and saved fantasy photo “Sissy2” for later viewing.

Slut Me Up: Click and Save

Viewing and processing each image took a pleasant toll on Jack; as his arousal increased the more he explored what he could do with “Jackie” and TransFormU. Jack had all his virtual creations ‘saved’ and ready for download to his laptop. Jack didn’t want to download only one file, Jack wanted to download and save ALL his files at one time. Click and Save.

Video images - ‘Be the slut you yearn to be’

There was one additional feature of TransFormU that Jack wanted to use; the ‘Slut-Me-Up Video’ option. Before attempting this Jack wanted to change into full Jackie mode; it would fit with what he was about to do. Jack went to his kitchen and mixed himself a Tito’s vodka and Sprite before going to his bedroom.

Life at home with a ‘Slut-Me-Up’ video option

With drink in hand Jackie went to her vanity, sat down and applied facial make-up, eyeliner, a bit of eye shadow and mascara. Her hair was long enough that she could easily backcomb it a bit and shape a believable feminine hairstyle.

Finding her favorite shade of lipstick Jackie enhanced her lips before giving herself a spritz of perfume. After positioning a panty-liner into her high cut panties Jackie was ready to try the ‘Slut-Me-Up’ option on TransFormU. Jackie wanted to look naughty while she was making virtual Jackie naughty; after all she would never forget that Jack had fantasies about having a real life sexual relationship with a man while in full Jackie mode.

Sitting back in her chair Jackie took another swig of her drink, retrieved her credit card from her black Michael Kors cross-body purse, logged into TransFormU and prepared to get virtually slutty. She was weighing which version of virtual Jackie to make “slutty”; ‘Lingerie Jackie’ or ‘Bride Jackie’ or ‘Sissy Jackie’? All were exciting and worthwhile options.

Jackie carefully entered her credit card number, and when prompted, selected ‘Lingerie Jackie’. She had a couple more criteria to click on. For ‘select a place’ (for her movie to take place in) she chose the ‘bedroom’ option; for the ‘with whom’ option she clicked on ‘with a man’. She made a mental note to try the ‘man + woman’ scenario someday.

Her final choice was ‘voluntary or rape’? Jackie wanted to be a willing participant in whatever would be depicted and she checked ‘voluntary’. Jackie smiled as she thought about how the final product would play out.

Before clicking on the final ‘Slut-Me-Up’ icon Jackie modified her ‘CGI self’ by switching to long platinum blond hair, added bangs and ultra sexy, vixen looking, eyebrows; it completed the look she was trying for.

After another sip of Vodka Jackie took a deep breath, exhaled, and clicked on the ‘Slut-Me-Up’ icon. A notice appeared on the screen indicating that the process could take 10 to 15 minutes to complete. She leaned back in her chair, closed her eyes and smiled as she felt her erection begin to tent her panties. Jackie was anxious to view her sexy virtual self but was more anxious to have sex with the penile endowed feminine beauty she had created.

Before Jackie could take matters into her own hand her laptop beeped her back to the present; “Done” was the one word message overlaid onto the TransFormU opening screen.

Jackie clicked the ‘preview’ icon, leaned back and lowered her panties for ease of access to self gratification.

The Preview

The three minute, mini-porn movie was just that; very erotic and very XXX rated. It was well worth what Jackie had paid. Watching the preview, prior to downloading, was like living the experience without actually having to get down on your knees and sucking your boyfriend’s penis. That would hopefully be a real life experience for another day.

Her video showed Jackie, on her knees, unzipping a man’s pants. Feminine fingers with long red shaped fingernails lovingly pulled a man’s turgid penis from his boxer shorts. Jackie leaned forward and sensuously kissed the head of the man’s circumcised cock; she prolonged pressing her lips against the cock head in order to leave tell-tale red lip prints. Her lipstick color was Revlon “Cherries in the Snow” red.

The video made Jackie smile and her panty covered erection grow; she shifted in her chair and pulled a box of tissues closer before beginning her masturbation.

The video continued. CGI Jackie extended her tongue and swirled it around the frenulum, into the meatus and eventually down his shaft before taking the first three inches into her eager mouth; Jackie had the timing of an experienced cocksucker. The CGI rendering was amazingly detailed; veins, ridges, lip print and penis wetness was perfect.

The movie showed Jackie expertly performing a teasingly perfect blowjob; plump red lips gripping and sliding up and down its veined firmness. The erotic slurping sounds of passionate cock sucking were a nice touch; the moment of deep throating was particularly stimulating to see and hear; her muffled gagging was perfect. Manicured and painted fingers stroked the shaft of the penis filling her mouth; her head bobbing speed increased.

The moment of her video boyfriend’s ejaculation was graphically captured; sounds of gulping and swallowing made it seem as if you were right there. Glistening dribbles of viscous cum were seen running down Jackie’s chin and neck as she tried to coax all the love gravy from her lovers testicles; her free hand tickled his ball sacks and sensitive perineum.

Virtual Jackie was rewarded with a last spurt of virtual sperm the moment she inserted her virtual finger partially into her boyfriend’s virtual boy-pussy. The close-ups were amazing in every graphic and audio erotic detail.

Just as she had choreographed Jackie’s virtual penis was clearly shown protruding above her satin panties which would confirm to a viewer that CGI Jackie was a male dressed as a woman having sex with a male. This detail fulfilled Jack’s fantasy of making oral love to a man while dressed as a woman.

As she watched her ‘movie’ Jackie became extremely aroused and by the end of the scene described above she was softly panting like a dog in heat. Her urgent hardness required her to seek blissful self gratification; it was an extremely forceful and memorable release! And then her mini-movie preview was over.

Giving a deep sigh of satisfaction and feeling fully satiated Jackie eagerly looked for and found a few puddles and splatters of her seed on her chest and in her navel. She used her fingers to scoop her ‘treats’ into her mouth and then meticulously licked her fingers clean; it was not the first time that Jackie had savored herself after a jerk-off session. Jackie picked up her soggy tissues and tossed them into the trash.

This first XXX movie was everything that Jackie had hoped for. It definitely was for personal at home viewing only. It was NOT ‘work place safe’ and neither would her next movie.

The Download

Since the video preview was fine Jackie nonchalantly clicked on one of several “download” icons on her screen. It was a Friday evening and she had no place to go until work on Monday and decided to get more comfortable while the video and still images were downloading.

Donning fresh panties and a chemise Jackie pulled on a pretty tropical print sundress, reapplied her lipstick and brushed her hair. Playfully looking into her vanity mirror she said: “Jackie, you’re such a very naughty girl… a digital virtual slut! And I have the video to prove it!” Jackie blew a kiss to herself and laughed. Stepping into her 3 inch pumps Jackie swished into the kitchen to make another drink; Jackie liked her Tito’s.

Jackie squeezed a lime into her vodka, turned on soft background music and sat back into her kitchen chair and thought about her next TFU CGI video creation

“Need” for a second movie?

Now that her oral love making of a man was digitized there was one additional form of man-on-man love that Jack wanted to create; it was something she hoped to experience firsthand someday. Jackie was mentally considering if in her new movie if she should be taken doggie style on her hands and knees; or be on her back on a bed with her legs hanging over her lover’s shoulders; or being bent over the armrest of an overstuffed living room chair with her ass high in the air? The possibilities were many… and all were naughty!

Intermission?

Jackie decided to make sure that her creations were being stored properly in her ‘Jackie’ file. Everything looked routine so Jackie decided to take a potty break. Unknown to her the files were also accidently being ‘shared’!

Friday Night: Her mistake becomes evident

Returning from the bathroom Jackie checked her email.

The first email she read was unsettling. It was from Bob in the mail room at work. It read:

“Dearest Jackie, Thank you for sharing your very sexy photos and video with me. Your steamy video gave me an erection! Your secret is safe with me. I too have a feminine side but am too insecure to let it out. What you did to that man’s penis was very amazingly hot! If you would like to practice on a real person give me a call and I’m yours! I’ve attached, in confidence, a picture of me in my favorite dress. Best wishes and hugs! “Diane” XOXO.”

Jackie’s jaw dropped. Her brain struggled to comprehend how “Diane” knew about Jackie and her porn movie! She refocused her eyes and read the next email:

“Miss Jackie, You are so incredibly hot! Seeing you at work I never suspected that you could femme up so sexy. I’d like to take you on a dinner date to the Sycamore Inn sometime. I’ll leave a tube of L’Oreal lipstick, with my phone number, on your desk Monday. We have the same skin tone and the shade looks great on me and will look stunning on you. Call me. Yours truly, Jonny”

Jackie’s heart was pounding and her hand was shaking. How could this be happening? The numbers of unread emails were stacking up. Jackie logged back into TransFormU and immediately went to the settings area. Quickly checking the download setting Jackie gasped and slumped back into her chair; limp with despair and disgust. The problem was glaringly obvious; a bone-head, amateur, mistake.

OMG! An unsettling Click, Save and Share mistake

Jackie took a slow gulp of her drink and sat staring at the screen of her laptop. In a careless moment Jackie had not only ‘saved’ her files but had also mistakenly ‘shared’ them with the contacts in her email address book. She had clicked on ‘save & send’ instead of ‘save’! “Oh, my God… what have I done?”

Life was about to get very complicated

It could have been worse; her ‘contacts’ email address book only had twenty entries.

It had been a long day

It was 10 PM Friday night and Jackie’s porn files had already set off a flood of email responses. Some replies were not very nice. Jackie had two days to fabricate a believable explanation of what had happened before reporting for work on Monday. That also meant that there were two days for more emails to roll in. “Oh, my God” she thought.

There was nothing should could do tonight so Jackie opted to go to bed. Perhaps the morning would offer solutions. Jackie washed her face free of makeup, changed into her favorite baby doll pajamas, shut off her phone and laptop and went to bed.

Rude Awaking

Awakening Saturday morning Jackie lay in her bed, clad in her favorite satin baby dolls; Jackie always looked good in pink. It had been a deep, relaxing sleep and Jackie was enjoying the solitude and comfort of a lazy morning. She slowly stretched as she began to wake up; a pleasant morning erection made itself known; Jackie smiled. She was reaching for her stiff morning ‘friend’ when the terrifying memory of yesterday’s mistake came to mind.

Jackie bolted upright in her bed and her mind began racing. “What the hell am I going to do!” she blurted out. “I accidentally sent an xxx porn movie of me being a cock-sucking slut to a lot of people!” Jackie swung her feet over the bed, slipped into her fur trimmed mules, glanced into a mirror, fluffed her hair and went to the kitchen for coffee. Glancing at her laptop Jackie decided to deal with it later.

Turning on her cell phone Jackie saw that she had four new messages. Setting the phone down Jackie snuck a cup of fresh coffee while the coffee was still brewing. Adding a splash of milk and two teaspoons of sugar she pulled out a kitchen chair and sat down to think. ‘What the hell am I going to do?!’ she thought. She continued drinking coffee as she pondered options.

Jackie decided to shower before doing anything. Her cell phone rang and she let it go to message as she adjusted the water temperature in her shower. Whoever it was would just have to wait. Hopefully it was not her employer telling her to not bother coming to work Monday. There were several coworkers in her email contacts that she had not heard from… yet. Had they shared her porn with others?

The shower was nice

The warm shower felt great and help clear her head. Grabbing her razor and shaving foam Jackie made quick work of making her legs nice and smooth. She shampooed and conditioned her hair, turned off the water and stepped out of the stall. She toweled her hair and patted her legs almost dry. She applied coconut oil moisturizer to her legs.

Because it was a Saturday she pulled on a pair of French cut tricot panties and a pair of low cut white shorts with a four inch inseam. The tattered cuffs made her shorts cuter as did the embroidered humming bird on a rear pocket. Jackie selected a teal colored push up demi-bra Jackie and a green blouse with a floral pattern. Opting for minimum makeup she chose a coral lipstick, blush on her cheek bones, and her usual black mascara. Inserting 2 inch gold hoop earrings Jackie was ready to face the day.

Slipping into a pair of leopard print flat sandals Jackie went to the living room. Looking down at her feet Jackie smiled and was glad she had recently painted her toenails a Robin Egg blue. The silver toe ring completed her.

Jackie made herself a toasted English muffin, with peanut butter and honey, and went to her laptop with another cup of coffee in hand. She flipped open the laptop and turned it on; the expected new emails were waiting.

A sample of the content

“You disgusting pervert! How dare you send me those disgusting faggot photos? I will call the police on you if do it again. Get some professional help.”

“I found your unsolicited images were very interesting but totally inappropriate for email. If you’d like to share your other similar videos let me know; perhaps we can view them at my house. (You make a stunning blonde.)”

“Damn, you are one hot mama! Why did you send the photos to ME? I’m in a relationship at present but if that changes I’ll let you know. See you at work, Sweetie!”

“Whew” Jackie thought, “the response isn’t as brutal as I thought it would be. Maybe there’s a way to fabricate a plausible explanation, keep my friends and keep my job.”

Taking a final bite of her muffin Jackie drank the last of her coffee. She reached up and felt her hair. ‘Almost dry’ she thought.
Jackie walked to her vanity. Using a brush she quickly had her hair the way she liked in less than a minute; a bit of hair spray and she was done. As long as she was at the mirror she reapplied a fresh coat of lipstick.

Returning to email responses about her cock-sucking video Jackie began clicking through them.

A few replies were very negative, a few were accepting of Jackie’s ‘hobby’ and a few wanted Jackie to ‘make’ them dress as women and paint their nails. Some wanted to have sex with her. “So far, so good” Jackie thought. And then she opened the next email.

Her boss emails Jackie

Unknown to Jackie was that her boss was a closeted, bi-curious, cross-dresser. CEO Mike Spence was fascinated with Jackie and wondered what she could do for and to him. Spence wanted someone that would help with his feminine appearance and also fulfill his man-on-man sex fantasies. Jackie’s video presented opportunities for him to achieve both of his goals and desires. Mike literally throbbed when he viewed Jackie’s video.

The email

“Jack – Copies of your obscene video and photos were forwarded to me by several employees. Those images and you reflect negatively on the corporation. Before I forward your video to HR I want to speak to you. Perhaps we can arrive at a mutually agreeable solution. I will call you at 12 noon tomorrow Sunday. If you do not answer do not bother coming to work on Monday. I hope you answer my call.” – Mike Spence, CEO

Jackie’s gasped and her heart pounded; ‘Oh, my God… what have I done? What the hell am I going to do? What does ‘a mutually agreeable solution’ involve?’ Jackie thought. She had a couple hours to think through options and excuses.

Ace in the hole?

If Jackie played her cards, and her boss, just right perhaps she might be able to keep her job.

Sunday call

Precisely at 12 noon on Sunday Jackie’s cell phone rang. On the second ring Jackie answered her phone and stood up.

“Hello, this is Jack.”

A stern but unmistakable voice announced, “This is Mike Spence. Put Jackie on the phone.”

Taken aback Jackie replied “This IS Jackie.”

Mr. Spence began: “Did you read my email from yesterday?”

“Yes, Mr. Spence, I read your email.”

“Have I made it clear how you and your video are an embarrassment to the corporation? Are you aware that your employment and your future are hanging by a thread… a very thin thread, Missy? And, less you forget, I alone hold that thread.”

Jackie’s heart was pounding and her palms were damp. “Yes, I understand” she replied.

Questions and answers

“Good” Mr. Spence said in a terse tone. “We both understand your situation. Before we speak further, answer my questions. It’s obvious that you enjoy your female side. Why?”

“When I’m Jackie I feel very special. I love the feel of nylons and panties. I find lingerie so much nicer than boring men’s clothes… you know, the usual.” In an effort to blunt Spence’s accusatorial tone Jackie added, “Perhaps you can relate to that feeling Mike.” Jackie’s vague reference to office rumors paused but did not halt Spence’s questions. It did result in a less abrasive tone from Mike. Perhaps if Jackie played her boss just right perhaps she might be able to keep her job.

Quid Pro Quo; Oh!

“Do you like your job Jackie? Do you want to keep your job? If so there will be favors that will have to be done.”

“Yes Mike, I like the company, I like my job and I love my panties. I hope to advance to a more creative and responsible position within the company someday.”

Mr. Spence paused a moment before continuing: “How far have you taken your cross-dressing? Do you shave your legs? Do you have sex with men? Your video shows that you are very proficient with men and their penises.”

Mike was seeking personal non job related information. There was more than a hint of being sexually propositioned by Mike?

“Mike, I shave my legs even when it’s not needed… I find it very pleasurable. I also wear silky panties, camisole and stockings under my boy clothes at work. Did someone get a peak of my bra or garter straps and report me? I’ll be more discreet in the future Mike… if you want; girls like us need to be selective in who gets to see our pretties, right Mike?”

Jackie continued, “In terms of my oral proficiency with firm and erect men my video was done with computer software after a lot of research. Trust me; I have a very good grasp on how to please a man in several ways. Yes, I’ve fantasized about sex with men but I have never acted on those urges; that’s why I made the video. By mistake my photos and video were accidentally sent to several people. I apologize. How many times did you watch my video, Mike? I hope it wasn’t too hard to watch the first few times. Was it hard, Mike?”

In a softer tone Mr. Spence replied with “Hmmm. Maybe there’s hope for you Jackie and we can reach a mutually beneficial arrangement. Which of your photos do you like the most?”

Surprised at the change of tone in the conversation Jackie did not hesitate and replied, “I like my ‘lingerie mode’ first and then it’s a tie with ‘Sissy mode’ with my dress held up; which photos do you prefer Mike?”

Equally quick in his response Mr. Spence said, “I like your ‘lingerie mode’ but I find both of your Sissy photos are… shall we say, pleasant options. Your blowjob video is artistically stimulating.” This admission confirmed office rumors and Mike’s interest in ‘chicks with dicks’ porn.

The phone went silent. Jackie dared not say anything. She thought she heard lustful breathing! Was Mike pleasuring himself as they spoke? The lack of an immediate reply confirmed that Mike was a bit occupied with something.

“Mikey? Are you watching my video as we speak Sweetie? Are you fantasizing it’s your manly firm shaft being gripped by my red cock-pillow lips, Mike?” purred Jackie. Jackie waited for a reply. She clearly heard the sound of tissues being torn from a Kleenex box. Moments passed.

A meeting tomorrow, Monday

Mr. Spence cleared his throat and broke his loud silence with, “I have a proposal that would be beneficial to us both. As a result of your video I’ve arranged for sensitivity training at the office. If we meet tomorrow, Monday you will be off work, with pay, until Monday of next week. This will allow me to make certain corporate arrangements. IF, after we meet, I decide to allow you to return to work I can assure you that you will not have any harassment problems at work.”

“That’s very sweet of you Mikey. A harassment free work environment is already mandated by law. Do you have any other ideas that would be beneficial to me or mutual beneficial to us?”

“The rest of my offer, and your career, depend upon your proficiency in several personal and confidential areas. I will only discuss details in person, not over the phone. When we meet I’ll have a non-disclosure agreement prepared and you will sign it if you want to keep your job.”

There was a pause and Jackie took a sip from her drink. Mr. Spence heard the ice cubes tinkle in her glass. Mike envisioned Jackie leaving a lipstick print on the glass.

“That sounds so exciting! What are you suggesting, Mike?”

“Jack, in order to keep your job are you man enough to be a woman for me?”

Disclosure? Confession?

“Your photos and porn video fueled desires and needs that I must deal with. I also like wearing lingerie and makeup; it makes me feel very alive. Knowing that one of my office personnel shares my love for lingerie and... cocks, makes me very needy. Having you and your sexual interests so close yet, due to societal norms, so unattainable is difficult. To put it bluntly, I find you attractive, desirable and convenient. Like I said, are you man enough to be my woman? Do you have the willingness to provide me sexual relief? Do you have the skills and willingness to help me look like a woman?”

“Can you be more precise, Mikey? A girl needs to know what she’s getting into.”

“I need a person proficient with makeup that will help me look feminine and be submissive enough to give me sexual relief and also be willing to receive sex from me. I’m looking for a commitment from an understanding girl like you; a one year agreement to begin with, subject to extension. You would be required to present as an attractive woman, help me find my inner woman and help me explore my latent bi-sexuality. In return you will be well compensated.”

“What’s in it for me?”

Mike took his time before answering.

“You’d think keeping your job would be incentive enough to become my office tart. I would make sure that your video and photos would never be shared with your family or others; they would remain our secret.”

“And what else?”

“I’d guess that a person with your, shall we say, special ‘talents’ and oral skills would need a better job title and a corner office… there would be special projects that might take us out of town (as a couple), or to bed for several days.”

Jackie was sitting in her chair absorbing all that she was hearing; it seemed so surreal. The office rumors about Mr. Smith were true! And yes, she was being blackmailed for sexual favors.

Jackie sensed a shift from being on the defense to being the dominant negotiator. She had the skills, knowledge, lips and a penis that Mike wanted very badly. Mike had tipped his hand and had metaphorically let his panties down and his inclinations be known. Lust can do that to a person. Jackie’s mouth formed a sly smile.

Jackie was sure that if she played her boss just right perhaps her future would be bright.

Mike continued. “Are you there Jackie? Do you understand what I’m suggesting? It’s a win-win situation. What are your thoughts on my proposal?” There seemed to be a plaintive tone to Mike’s voice that hinted at desperation and a deep sexual need.

Hesitating a moment for effect Jackie softly replied, “It does seem like a mutually beneficial arrangement, doesn’t it?” As the proposal sank in Jackie could feel the start of an arousal. Having sex with a man AND being paid. Would that make her a whore? It didn’t really matter if her bi-curiosity would be satisfied. It seemed like a wet dream coming true.

“So what do you think, Jackie? You’re running out of time and options. Your emails stirred up a lot of problems that the company doesn’t need. Say ‘yes’ and I’ll come to your condo tomorrow Monday at 12 noon to discuss and finalize an arrangement. If we do not meet tomorrow don’t bother returning to work; your final paycheck will be mailed to you.”

Pausing for a moment Jackie asked, “Did you say I would be off work for a week with pay?”

“Yes, but only if we can come to an agreement when I come over tomorrow. I have corporate things that need my attention in the morning but I will be at your place at noon. I want you wearing the pretty things and makeup I see in your photos and video. OK?”

Jackie smiled as she realized that she was suddenly in a position of power; she had something that Mike desired. Holding the phone in her left hand Jackie pulled the zipper of her shorts down and began running a finger up and down her panty encased cock. “Well Mikey, are you wearing panties right now? I am.” A very soft and resigned, “Yes” was the response from Mike.

“What color are your panties Mikey?”

“Red with small white bows at the waist” he confessed.

“What style of panty do you prefer, Mikey?”

“Boy shorts”.

“And if I allow you to come over tomorrow afternoon you must be wearing high cut nylon panties, Sweetie. OK?”

“Yes.”

“And sheer black stockings?”

“Yes.”

“And what name does my pretty cupcake use when she’s all girly-fied?”

“My femme name is Lana.”

“Lana dear, would you like to get dressed up very pretty tomorrow and spend some quality time with me?”

“Yes.”

In Jackie’s mind the trap just snapped shut. She would be the ‘domme’ teacher and Mike/Lana would be her very wealthy student.

“You know I’m a brunette but in my video I’m a platinum blond, right?”

“Yes, I noticed.”

“So how can we solve that problem Mikey if you want me to be blonde for you?”

“I’ll bring you a long, blonde wig.”

Jackie decided to test the strength of her negotiating position. How urgently did Mike/Lana want her? “Platinum blonde, Lana. And not some cheap Gabor synthetic TV wig, OK? After all you own a very successful business, Sweetie.”

Mike replied, “OK, a high quality platinum blonde wig.”

Jackie inwardly smiled. She pressed her position.

Dropping her voice and trying to sound sultry, Jackie said, “You know Lana, if you want me to be your girlfriend be sure it’s a human hair wig. In fact I’d like to be very naughty for you sometimes so also bring a shoulder length auburn wig; it would arouse me. You do want me to be aroused don’t you Lana? We’d both benefit.”

Lana responded with “Ok, I’ll bring two high quality human hair wigs. Is there anything else?”

“Yes Lana, there are just few things more. Bring a bottle of Tito’s for me and a bottle of what you prefer. Be sure your legs and armpits are freshly shaved; bring a wig for yourself and wear high cut nylon panties, stockings and garter belt to prove your commitment to wanting to be my girlfriend. I don’t fool with trash. Is that clear Sweetie?”

“Yes, it’s very clear.”

“And, if the day goes well and if you’d like to feel my throbbing cock when I’m deep inside you be sure to bring a box of sheepskin condoms. You do want me buried deep inside of you don’t you Mikey?” Jackie was sure she heard a gasp from Lana who was breathing heavy like a man in lust.

Jackie continued, “If you don’t already have a bra I’m positive that I have a lovely bra that will fit you. I bet a Sissy boy like you love satin and lace, Lana. I do. I’m looking forward to my new position at the office. So we have a date for tomorrow.”

Lana’s response was, “I’m looking forward to it. I’ll see you tomorrow. By the way, I’m a 38 B.” Lana hung up.

Jackie put down her phone and giggled at the turn of events. Her future was looking brighter if she played her boss just right.

As a bonus Jackie’s “date” might fulfill her own latent desire to experience sex with a man. Unknown to Mike, despite what her CGI porn movie revealed, it would be Jackie’s first foray down that forbidden trail.

Still Sunday

It was a little after 1 PM. Jackie was feeling the need to be at her very feminine best for her boss tomorrow afternoon. Her future and career depended on it. What could she do between now and 11 AM tomorrow to look as femme as possible for Mike? A quick self assessment narrowed her options to hair, eyebrows, nails and whatever the salon could suggest. There were lots to be done and a short time to get it done.

Nagging concern: How can I explain this?

And there was the nagging ‘problem’ with her sex tape and photos. She needed a way to explain them away to her friends and co-workers. The photos of her in various sexy roles were the least of her worries. She could pass the photos off as a lost bet, a dare, a prank… but how to explain the 15 minute porn video?

Getting ready

Using the search engine on her laptop Jackie called House of Beauty Salon a block away. She explained “I need to look as femme as possible and as soon as possible. Hair, brows and nails should do it.” They had an immediate opening and said it would take about two hours. An emergency rush job would cost $150 to $250 depending on what they did; it was an investment in her future. The salon said for her to be there within 45 minutes.

One thing was certain; by the end of tomorrow she’d either be fired or would have a week of paid time off. In either case that would give her a week to enjoy the feminine niceties she was about to have done to her. Perhaps Lana would have a solution.

Jackie mused, “Am I about to gain a boyfriend or a girlfriend?” She chuckled at the thought.

Changing into a pair of mid rise denim pants and a simple print blouse Jackie applied lipstick, grabbed her purse and left for the salon. The beautician asked if Jackie if she’d like to experience a Brazilian wax.

“What is involved with waxing?” Jackie queried.

The beautician explained that with a Brazilian wax, pubic hair is removed from the front of the pubic bone, around the genitals, between the upper thighs, and around the anus. “What look are you trying for?”

Jackie replied, ‘I’m trying to impress an important man so I can keep my job so I think sexy, verging on slutty is a must.”

After being waxed the beautician expertly coiffed Jackie’s hair into a perky shag, complete with a few well placed highlight streaks adding to her female beauty.

Jackie’s acrylic fingernails were perfectly shaped and were a dark scarlet as were her toenails. Her eyebrows were given the super feminine thin arch seen in her ‘Slut-Me-Up’ video. As a special service to Jackie and before waxing her pubes the beautician tinted Jackie’s eyelashes and eyebrows; they wouldn’t fade and her pubic area would be hairless for several weeks. There could be no going back. ‘I hope all this gives Lana the hard-on that she’s looking for’ Jackie thought.

Three hours later Jackie was home and definitely looking and feeling very glamorous. Here bald crotch was very exciting and had caused a mental shift deeper into femininity… with a touch of ‘slut’ thrown in.

Shopping

Before returning home Jackie bought matching pairs of Silky Sheer Cocoa and Jet Black colored pantyhose; one for Lana and one for her, two tubes of KY Jelly lubricant, a box of Ultra Thin Panty Pads, A small box of Tampax Pearl Lite Days tampons and two liters of Sprite for her Tito’s. As an afterthought Jackie picked up two deli sandwiches, chips and a small potato salad. ‘Heck, we need nourishment and I may need practice caring for a man.’

Entering her condo Jackie put her shopping bag down and quickly walked to her vanity mirror and stripped naked so she could admire her new look. Her hairless crotch looked and felt erotic; her erection began to grow at the sight. She hefted her penis and stroked it to complete firmness.

Before pulling her panties up Jackie harvested a glistening drop of pre-cum from the tip of her dick and licked her finger clean. Exercising self-control Jackie reluctantly pulled her panties back on and sat down.

Her mirror became her best friend of the moment. Dark red fingernails, tinted and shaped eyebrows and dark lashes, pouty red lips, pretty hair gave her the look she was striving for. ‘Damn, I’m hot!’ Picking up her eyelash curler she gave them a nice crimping.

Grabbing her cell phone she clicked off five or six selfies, making a mental note to update her TransFormU images in the near future. Picking the sexiest photo she forwarded it to Lana without comment as a tease.

Going back to the kitchen, Jackie put the deli sandwiches and Sprite in the refrigerator and brought Mike’s new pantyhose and a pair of scissors to her usual chair. Sitting down she opened the packages and carefully cut access holes for Mike’s cock and his sphincter. She did the same with her hose. ‘Best to be prepared’ she figured. Jackie wasn’t sure how tomorrow would play out or if the pantyhose would be used.

The evening was fading and Jackie wanted to be bright eyed and eager for Mike. Her fate, literally, was in Lana’s hands. With any luck her dick would also be in Lana’s hands and mouth. It was going to be an interesting day. Jackie straightened the house, removed her lipstick and climbed into bed. She turned off her night light and tried for sleep.

The Fateful Day: Monday

Jackie’s alarm clock woke her at 7 AM. After coffee and breakfast Jackie spent time making sure the condo and her bedroom looked nice and neat. MikLana was due at 12 noon. At 9 AM Jackie began to get ready.

She showered and was grateful about yesterdays pubic waxing as it would save time and aggravation for a long time. ‘Lana better appreciate all the shaving and waxing. At least she won’t be pulling stray pubic hairs from her mouth’ she mused. ‘I wonder if Lana will be smooth for me. I’d like that.’

TFU ‘lingerie mode’

Stepping from the shower Jackie dried and moisturized her waxed legs and crotch. Jackie tucked her penis as usual and dressed in a matching red garter belt and panty set, black stockings, a black and red pushup bustier (with lace trim) that emphasized her cleavage. Breast inserts helped her look very well endowed. Jackie was trying for the showgirl/slut makeup that Lana apparently liked. Jackie was not leaving anything up to chance. Jackie looked very desirable. She carried her black three inch pumps to her living room.

Sitting in her thinking chair Jackie contemplated on how to keep the negotiating power she had asserted with Lana during their conversation yesterday. There were several things that were in her favor. Jackie had things that Mike/Lana desperately wanted; cock-sucking lips and a boy-pussy… Lana had made it clear that she wanted these two things very much. Jackie made a mental note to not seem weak or indecisive. She had to stay in control.

Strategy

With that in mind Jackie removed her hoop earrings, placed them on her vanity, and inserted simple pearl ear studs. Next she wiped her ‘Trollop Red’ lipstick off. There would be time for that color later. She wanted Lana to see her looking fairly plain when she first arrived and would then transform to a sultrier look when the time felt right. This included greeting Lana in boring boy clothes.

Jackie pulled Jack’s khaki slacks on over her garter belt and nylon covered legs and slipped into a pair of Jack’s loafers. Black nylons could be seen where socks should be. Selecting one of Jack’s long sleeved white shirts Jackie put it on, tucked it loosely into the khakis, making sure to leave the shirt cuffs and the top two shirt buttons unbuttoned. ‘Look androgynous at first and then evolve into a sexy woman. How exciting is that!

In stark contrast Jackie’s scarlet acrylic fingernails showed provocatively at the end of the white sleeves of a man’s shirt. Hints of her lace bustier were, on purpose, visible where the shirt buttons had been left open; a hint of cleavage was visible. Jackie made an erotically androgynous image standing there; a woman dressed in men’s clothes, with obvious breasts, exotic fingernails and a shag hair style. Her femininely shaped eyebrows, mascara eyelashes, smoky eye shadow and pearl earrings completed her image. It was part of a plan that would, hopefully, keep her in control of the situation as well as her future.

Miniature surveillance cameras too!

Jackie unboxed four tiny “nanny cams” and strategically placed them throughout her condo; her living room, kitchen, bedroom and vanity areas were completely covered. The sensitive microphones would be put to good use. All recordings would be stored in the cloud as well as her laptop.

Taking care of last minute details Jackie brought an extra chair into her bedroom and placed it next to her vanity. On top of the vanity she staged several tubes of lipstick, bottles of nail polish and mascara. She placed KY lubricant on a night stand, in the bathroom and one on the vanity. She also strategically placed tissue boxes, baby wipes and hand towels throughout her condo and bedroom. Lana’s and her modified pantyhose were conveniently waiting on the foot of her bed.

Retreating back to her thinking chair Jackie closed her eyes and tried to psyche herself up. There would probably be many firsts for her today and cock-sucking might be one of many ‘firsts’. Jackie wanted to be as prepared as possible.

With her eyes closed Jackie did yoga breathing to help calm her and mentally went down a check list. How far would she let Lana go with her? How far would she go on Lana? Would Lana fire her if the events of today didn’t meet her expectation?

At 11:30 AM Jackie checked herself again in her vanity mirror; she thought that wearing Jack’s clothes made her look like a not so subtle lesbian. That mental image made Jackie giggle. She resisted the urge to apply lipstick but did make a few brush strokes of blush to her cheekbones. She placed a solitary dot of perfume behind one ear and on a wrist.

Picking up a lipstick and a small pocket mirror from the vanity she went to the kitchen and placed them conveniently on the kitchen table and started a pot of coffee. Jackie laid out two coffee cups and two drinking glasses, a bucket of ice and a small plate of lime wedges.

She then lit scented candles in the bedroom and living room. After partially closing the living room curtains she sat on the sofa to wait. If today’s events went well she might be able to keep her job.

The boss arrives

Precisely at 2 PM there was a firm knocking on her door. Jackie waited for the second knock before standing and going to the door. At about the time there would have been a third knock Jackie opened the door. Standing outside was a handsome looking man that held a large shopping bag in one arm and a medium duffle bag in the other. “Hello, I’m Mike Spence” he announced.

Jackie opened the door wider and looked her visitor slowly up and down. His look was clean and professional, nails were manicured, hair was combed and shoes were polished; no trash here. Mike held a large handled Victoria’s Secret shopping bag and was towing a wheeled medium sized suitcase. Wigs and wig stands were undoubtedly inside.

Jackie smiled and said, “Please come in, Mike. Welcome to my home and porn studio” she quipped. Mike shuffled his feet, looked left and right (which was a ‘tell’ of his nervousness) before stepping in. Jackie closed the door smiling at what she had just seen. ‘This is starting well’ she thought.

Mike placed his duffle bag on the floor next to the kitchen table and placed his shopping bag on the kitchen counter. He did a careful check of the condo before making eye contact. “Your place looks very comfortable Jack” Mike offered. Jackie stepped closer and, in a manly fashion, firmly shook Mike’s hand and said, “Thank you for coming, Mike. Please call me Jackie.”

While still shaking Mike’s hand Jackie made a quick assessment. Jackie stood about 5’ 7 inches and it appeared that Mike was maybe three inches taller. According to company literature Mike was 30 years old, unmarried and liked snow skiing. Jackie thought Mike had a boyish face and check bones that begged for makeup and blush; he had no facial hair. There were remnants, in both ears, of Mike having pierced ears. He looked to be about 150 pounds and appeared to be fit. Jackie though he was handsome.

Motioning for Mike to take a seat at the kitchen table Jackie asked, “Would you care for a cup of fresh coffee?” Mike took a seat and continued checking Jackie very closely. “Yes, please; black, no sugar.” Jackie poured a cup for Mike and one for herself. She stirred in two teaspoons of sugar and a teaspoon of cream into her cup. She walked the cups over to the kitchen table, sat down and crossed her legs in a feminine manner. Her nylons and leg crossing did not go un-noticed by Mike.

Jackie held her cup with both hands as if she was using the cup to warm them. In fact she was flashing her red acrylic nails in an attempt to gauge Mike’s response. Mike stared in obvious appreciation and said, “Nice nails.” Jackie smiled and nodded in agreement. “If things go well your nails may also look as pretty in the very near future.” With a smile in her voice Jackie asked, “Does Lana paint her nails? Rumors at work say that she does.” Mike fidgeted a bit and then said, “Yes, but mainly on weekends.” Sitting in silence for an awkward moment Mike took a sip of his coffee.

“I came to see Jackie”

Jackie kept stirring her cup, not taking her eyes off Mike. Mike took another sip and then said, “I told you to be dressed… differently than this. I came to see Jackie.”

“Yes Mike you did come for Jackie but let’s not forget that you really came for Lana’s sake. But first I’m sure that you have business to resolve with Jack first, right?” With a free hand Jackie widened the neck of her unbuttoned shirt exposing more of her red bustier and cleavage. “Jack will leave once we’re done with the paperwork.” Mike’s pupils became larger at the glimpse of Jackie’s lingerie. ‘Ah, another tell.’ Jackie inwardly smiled.

“Let’s get the paperwork out of the way first. Don’t you agree, Sweetie?”

The contract

Mike retrieved a file folder from the bag he had brought in and returned to the table with a pen. There were two sets of documents; one set for each partner in this contract. “All of the items we discussed yesterday are in this document. The term of the contract is one year with extensions and performance bonus eligibility after six months.”

“I’ve decided that you will be my “Executive Secretary” with duties and projects determined by me. I’ve set your annual salary at $70k with a chance for performance bonuses. In return you will… (Mike gulped and had to take another sip of coffee to loosen his voice)… you will help and assist me as we discussed yesterday.” Trying to sound managerial and authoritative Mike added, “Is that clear?

Jackie looked demurely over her cup of coffee and softly replied, “Yes, Mikey. It’s clear that you want to suck and fuck me and it’s clear you want me to suck and fuck you. I think, because of the intimate and confidential services I’ll be performing that my job title should be “Special Assistant to the President” with a guaranteed salary in the $75k to $80k range, bonus eligibility, a clothing allowance and a corporate credit card.”

Momentarily taken aback Mike hesitated and nodded yes.

Getting it on record

Jackie smiled and added, “Let’s both agree what we discussed yesterday, Sweetie. We discussed your feminization didn’t we?” Jackie wanted to be sure that her ‘nanny cams’ captured Mike’s words.

Mike nodded yes.

“I’m sorry Mike I didn’t hear you SAY what we discussed. Please respond with more than a nod of your head, is that clear?”

Mike’s jaw tightened at being told what to do but he softly confirmed, “We agreed that you would help in my feminization; my feminization is part of any agreement. I want to look, walk and act like a woman.”

Mike was saying everything that Jackie wanted on record.

“See Lana, that wasn’t so bad… admitting your inner desires. But there’s more to our agreement, isn’t there? Will the company conduct LGBTQ sensitivity training?”

“Yes, it’s all set to go.” Jackie gave Mike a perplexed look and began tapping her pretty red acrylics on the table top. “Mike, don’t you think that it would be best if the company had annual sensitivity re-training?” Jackie asked.

Startled by Jackie’s boldness Mike paused to give her suggestion some thought. “Yes, I think that would be the right thing to do” he said.

“And will I be permitted to dress, within reason, as womanly as I want at work?”

“Yes, dress as womanly as you want. But I reserve the right to make daytime and nighttime wardrobe suggestions; you will be required to attend meetings, dinners, parties and other events always presenting as an attractive woman.”

“I will cover the cost of our clothing, makeup, salon visits, etc. Potential physical body enhancements, if needed, are open for consideration. Your base salary will be $80k.”

“Most importantly we agree to engage in consensual sex… as both a ‘giver’ and a ‘receiver’, which includes cock-sucking and other sex acts, didn’t we?” Jackie mentioned this to get it on record that she was being propositioned to be a whore.

Shaking his head in the affirmative Mike managed to say, “Yes, fellatio of each other, and perhaps other intimate activities, as well as my frequent feminization are part of this agreement. There is also a Non Disclosure Agreement that, if either of us violates it, our agreement is null and void. Most importantly there is a Sexual Exclusivity Agreement. Neither of us can have sex with anyone else. It protects us both from STDs. Frequent testing will be scheduled.” Mike exhaled and slumped back into his chair as if he was exhausted.

Signed and sealed

Jackie signed the ‘Special Services and Employment’ and ‘NDA’ agreements, gave Mike’s hand a gentle squeeze before putting the pen in Mike’s hand. All documents were quickly signed. Jackie folded her copy and put it in her purse.

Jackie placed a warm hand on Mike’s forearm; “Now that that’s done why don’t we get more comfortable? Would you care for a drink?” she asked. Mike nodded and they both went to the kitchen counter where glasses waited.

As Jackie began filling their glasses with ice Mike reached into his bag and produced the promised bottle of Tito’s vodka. Mike poured the vodka and Sprite while Jackie added the limes. Mike made an effort to get a whiff of Jackie’s perfume.

Staring at each other they both raised their glasses. “To a new, sexy and very girly future” Mike pronounced. Jackie smiled and added “And here’s to womanhood and new experiences.” They clinked their glasses, took a drink and they both nervously giggled. It was as if a heavy weight had been taken off them. The hard part, no pun intended, was behind them.

Showtime 1: an audience of one

“I think we are done with Jack for now. Let’s have a seat on my couch for a bit, shall we?” With drinks in hand they walked towards her couch; Mike got there first, put his drink on the coffee table, sat down and studied his pretty Jackie; his legs were spread wide apart in a manly way.
Jackie paused by her kitchen chair and made sure that Mike watched her kick out of Jack’s loafers. Playing to an audience of one Jackie put her drink down and began unbuttoning the man’s shirt she was wearing; her red nails contrasted nicely against the white of the shirt. The upper part of her sexy bustier was now on full display; the illusion of Jackie’s breasts was impressive. Jackie tried to look pouty and sexy as she stripped off the shirt and hung it on her chair; Mike squirmed and was obviously interested.

The removal of Jack’s khaki pants quickly followed. Jackie simply unzipped the pants, unbuckled the belt and let the pants drop to her ankles. Jackie held still and let Mike savor the moment before continuing.

Jackie was now standing in her red bustier garter belt combination; four beautiful black garter straps held her black nylon opera stockings securely in place. Small red satin bows accented the suspender clips. Based on the lump in his pants Mike was enjoying Jackie’s arousing striptease.

Making sure her butt was facing Mike Jackie made a show of bending over to pick up the discarded pants; she patted her butt and wiggled nicely for Mike’s benefit. Picking up the pants in a delicate two fingered limp wrist sissy like manner Jackie dropped them on the back of her chair with the white shirt before turning to face Mike. Noting Mike’s bulge Jackie inwardly smiled at his discomfort. She knew his urges were building and her hidden cameras were capturing it all.

Mike commented, “That outfit is fantastic! You look good enough to eat. I see no maleness. It gives me a goal to strive for… with your help. It also makes me… envious.” Jackie thought he was going to say that she was making him ‘horny’; she was pleased to hear Mike say she was good enough to eat. ‘That audio clip is a definite keeper’ she thought.

The show goes on

Still facing Mike Jackie plucked a tissue from the Kleenex box on the kitchen table and with one swipe removed the bland lipstick from her mouth and tossed the soiled tissue over her shoulder. Picking up the mirrored compact and lipstick from the table Jackie made a show of extending and carefully applying the ‘Trollop Red’ red lipstick she had worn earlier.

She pressed her lips together and made a kissing sound to Mike. Jackie’s red pouty lips solidified her erotic femininity; in a manner of speaking Jackie had just ‘slutted’ herself up! Mike squirmed in penile discomfort.

Jackie continued her seductive metamorphosis into porn mistress by removing her pearl studs and expertly inserting more feminine diamond chandelier earrings without the need of a mirror. The ease in which Jackie tilted her head in such a feminine move and effortlessly inserted her new earrings amazed Lana. Jackie’s feminine image and demeanor had just increased.

Jackie slipped her stocking covered feet into her 3 inch black pump heels, picked up her drink, faced Mike, and struck a not so subtle slutty-girl pose. Mike’s bulge was bigger and would soon need attention.

Jackie picked up her compact mirror and lipstick and sashayed teasingly over to Mike. Jackie dropped the items softly into Mike’s lap and taunted, “Mike are you man enough to be a woman for me?” Jackie sat a half cushion apart from Mike to watch his response.

Mike’s initial reaction was like a cauldron of burning coals had been dumped on his crotch. Mike squirmed in his seat and stared at the cosmetic items. Exhaling in resignation Mike picked them up, held them in his hand as if weighing them and put them in his shirt pocket. Mike took a long pull from his drink and looked at Jackie; she was smirking. Mike knew where this was going; the inevitable was at hand.

Lip up or shut up!

Jackie placed her lipstick marked glass on the coffee table and slid her pantied butt closer to Mike. On purpose Jackie sexily crossed her legs at her ankles; the sound of her nylon covered legs rubbing against each other did not go unnoticed by Mike. In a sultry voice Jackie announced, “It’s time to put on your lipstick, Sweetie.”

Before Mike could respond Jackie added, “So, what do you think Mike? Does Lana like that shade of red?” Jackie could sense that Mike’s mind was whirling.

With no hesitation Mike nonchalantly retrieved the compact mirror and lipstick from his shirt pocket and in less than 30 seconds had expertly colored his lips and recapped the lipstick. Mike stared at Jackie as he snapped the compact closed in a display of confidence; feminine confidence. Lana blew Jackie a Hollywood fake kiss and relaxed into the couch.

“My, aren’t you quite the deft pretty boy” Jackie quipped. “I bet you wore Mommies panties as a little boy, sit down to pee, and can hook your bra from behind without any help.” Pleased with herself Lana stared at Jackie. Lana replied with a soft “Thank you”.

“See anything you like, Precious? See anything you’d like to wear… or kiss? Doesn’t Lana want to kiss a girly-boy; to kiss a ‘Chick with a dick’?”

You’ll do

Lana put her hand on Jackie’s nylon covered knee and said, “You’ll do just fine.” Lana began caressing Jackie’s knee. “You look stunning Jackie; much prettier than in your video.” Jackie spread her legs in an encouraging manner. Lana stared at Jackie’s crotch and continued, “I love the thought of kissing your cock” Lana admitted.

“Thank you Lana, a girl likes to hear that but my cock is disappointed that only kissing it is on your mind when there are other naughty delights to be had.” Jackie reached over and moved Lana’s hand to her crotch. Lana reflexively gave an exploratory and prolonged feel to the outline of Jackie’s turgid penis. Jackie smiled and spread her legs wider.

As she smiled at Lana Jackie thought. ‘I shouldn’t be too slutty… just bold enough to get the juicy parts on tape and keep things in my favor’. The recordings were an insurance policy protecting her future.

Moving Lana’s hand from her hard-on Jackie said, “Make yourself comfortable, kick off your shoes and relax.” Lana removed her shoes and Jackie immediately saw that she was wearing black nylons with a reinforced toe.

Rather than ignore the elephant in the room Jackie pointed at Lana’s nylon covered toes and said, “It seems we both like black stockings. What style of panties are your favorite, Lana; high cuts or boy-shorts?”

Hard to tell

Jackie put her hand on Lana’s knee and gave it an exploratory rub. “I can feel the texture of your stockings under your pants, Mikey; it feels just like me when I’m at work. What I don’t feel are garter tabs. Maybe you’d like to stop by my desk at work sometime to feel my garter straps or perhaps call me to your office for a closer inspection. Do you have a couch in your office Mikey?”

Lana didn’t answer; she diverted his eyes away from Jackie. She licked her red lips. ‘Another tell’ thought Jackie. They both took a sip of their drinks and leaned back into the couch. Perhaps it was alcohol related but a level of tenseness in the room had vanished. ‘So far so good’ Jackie thought.

Jackie pushed further. “With a little effort you will look pretty too. Your face and cheek bones have so much femme potential.” Lana blushed and took another sip of her drink and said, “I would really like that” she confessed.

For the benefit of her recording devices Jackie asked, “What is it that you’d like my Precious?”

“I want you to help me look pretty like you.”

“What did you bring in your bag Lana? Did you bring your favorite heels, a cheerleader’s outfit or maybe a skimpy tennis skirt? A tennis skirt would be very nice with your long legs, Sweetie.”

Lana took a deep breath and said, “I brought three wigs, my bra and panties, lube and a few other things.”

“Three wigs, Lana? I only wanted two.” Lana blushed and replied, “I bought one for me; a shoulder length strawberry blonde.” All of Lana’s ‘confessions’ were perfect for Jackie’s recordings.

Show time 2

Standing up Jackie bent over again and made a display of smoothing her nylons from her ankles to her garter tabs; she adjusted the tightness of one strap solely for Lana’s viewing pleasure. Jackie flashed Lana a pretty smile. Facing her Jackie stepped between Lana’s spread legs; Jackie’s crotch was level with Lana’s face.

“Give my garter a tug Lana, feel the tightness; you’ll need to learn the proper snugness for your garter belts.” Lana hooked a finger under one garter and slightly pulled on it to get a sense of what Jackie had said. She held Jackie’s garter strap for a couple seconds and then ran her finger up and down the strap as she tugged.

“Do you find the red satin bows cute, Lana? Would you like to wear a garter belt Sweetie; maybe under your boy clothes at work? That keeps me so aroused that I need to wear a panty liner!”

With her free hand Lana stroked the inner thigh of Jackie’s stocking covered leg. She licked her lips and softly moaned before releasing the strap. There was a soft snap sound as the elastic garter popped back into place.

“It’s like having someone playfully snap your bra strap. Has anyone ever snapped your bra strap, Lana?” Referring to Mike in the feminine form would re-enforce his mindset; the mindset that brought him to Jackie’s home; the same mindset that drew Lana to adult bookstores and special porn sites.

Break time

Waiting a moment for the reply that never came, Jackie announced, “I’ll take your bag and our wigs to my bedroom while you make us a drink; leave your pants on the couch and then join me at my vanity. I have something that you simply must try on. I do hope you like red, Lana.”

Jackie grabbed the items and for Lana’s benefit did a sexy runway model walk into her bedroom; her heels caused her tight butt to gyrate deliciously. Checking the time Jackie made a mental note to rewind and view the security video of Lana and her bulge applying lipstick perhaps clad only in panties and stockings. That thought created a gentle stirring in her panties.

Once inside her bedroom Jackie unpacked Lana’s bag and wigs and strategically placed Lana’s items next to the female articles of clothing she had previously placed on the bed. Only half of the bed was now available to lie down on.

Jackie immediately unpacked and donned her new platinum wig leaving the other two wigs on a night stand. Facing the vanity Jackie happily brushed her new wig into sultry perfection. Jackie was thrilled with the wig quality and reveled in the girly feelings that washed over her when she looked into the vanity mirror. Her penis was equally thrilled. Thank goodness for panty shields.

The bedroom

Jackie had strategically positioned her hidden nanny cams in her bedroom. After verifying their view was not blocked Jackie took a seat on her towel protected vanity bench and began slowly brushing her sexy platinum hair.

Jackie followed Lana’s movements in the other room with her ears; the sound of Lana’s zipper going down, pants being removed and laid on the couch. Her shirt removal was silent. Then Jackie heard ice going into their glasses, the splash of the vodka, fizz of the soda and the stirring of the mix. Lana would soon be entering her bedroom. Jackie smiled and waited.

Into the love nest

Lana arrived with both beverages in hand. She stopped just inside Jackie’s bedroom door and looked around; nice, neat and feminine. A black and red garter belt, a pair of long black sheer stockings and other female clothing and items occupied half of Jackie’s bed; the stockings had been arranged to show their entire length and sheerness.

The contents of Lana’s bags were neatly piled on Jackie’s bed adjacent to the garter belt and stocking set; spare panties, a blouse, a bra, tube of lube, a small draw-string purse of jewelry, stockings and a short white tennis skirt. Lana was puzzled about several items; open packages of pantyhose, a box of panty liners, a box of Tampax Pearl Lite Days tampons and a pink silicon butt plug with a green jewel on one end. Lana knew she hadn’t brought the plug or the pantyhose.

Protective towels had been placed on the bed, chair and vanity bench. Boxes of tissues, baby wipes and more towels were in abundant supply.

An erotic image

Jackie saw Lana’s androgynous image in the reflection of her vanity mirror; her short ‘boy hair’ looked out of place. Clad in black thigh high stockings Lana was wearing white slip-shorts and a bland but cute lace camisole that she had most certainly been wearing under her boy clothes when she arrived. Most importantly Lana was wearing the red lipstick.

Lana finally focused on Jackie at the vanity and froze in place. Seeing Jackie in her Platinum video wig made Lana gasp in delight; that vision made Lana’s penis twitch and engorge. “My gosh, you are so erotically beautiful!” exclaimed Lana. Lana’s boy-bulge was very evident and would need to be dealt with.

Jackie smiled sweetly and said, “Good girl, such pretty red lips!” She motioned for Lana to take the towel covered seat next to her. “We have a lot to do and you my sweet Sissy, have a lot to learn. You also need to let your hair grow out.” Lana placed both drinks on coasters and sat down.

School is in session

Without turning to face Lana, Jackie said, “Just watch for now.” She picked up one tube of lipstick, extended it, gave it a smell and rolled it back into the tube, pretending it was not quite right. “Fragrance and texture is key to lipstick; some smell and taste like wax. Choose carefully.” Jackie held the tube in front of Lana’s nose for her to smell. “This smells like nothing and tastes like nothing so why bother?” Lana agreed.

Grabbing a second tube of color Jackie removed the cap, gave it a sniff, nodded and began to carefully apply the scarlet red to her lips. Lana sat enthralled, watching every move; her panty bulge was beginning to show a wet spot. “Let me smell that please” Lana requested. “That’s a much nicer aroma.”

Jackie took a tissue and gently wiped at Lana’s red lips. She handed Lana the new lipstick and instructed, “Go ahead Lana; apply this burgundy color over what you’re wearing now. This is just practice; we’ll do things right another time.” Lana leaned forward, completed her task and pressed her lips together for even coverage. Lana smiled prettily, exhaled, leaned back and relaxed; the nervous tension in her neck and back melted away.

“Most girls blot their lipstick on a piece of tissue paper but naughty girls like to blot their lips on their date’s penis. Which kind of girl is Lana?” Jackie rhetorically asked.

Watch and learn

Taping Lana’s growing wet spot twice with her acrylic nail Jackie said, “We’ll take care of this pesky thing a bit later… I think I’ll have you deal with it while I watch. Do you masturbate frequently, Sweetie? I’d love to see you make ‘cummies’.”

Jackie began applying eye shadow, using small sponge brushes to blend colors; smoky black, a lighter gray and some gold highlight. Jackie was getting slutty and Lana was taking it all in. Jet black eye liner and mascara came next. For Lana’s benefit, Jackie finished with an eyelash curler. Glancing over at Lana she announced, “Almost done.”

Turning her newly made-up face toward Lana Jackie flipped her Platinum hair provocatively, batted her eyes and asked, “Is this who you expected to see today when I opened the door for you Precious?” Lana’s eyes got wider. “Wow, you look amazing!” Lana managed to say.

Lana’s turn

“Because today is very special and because you are a new girl I’m going to make you up like me; I’m going to slut you up a bit. Close your eyes and face me” Jackie instructed. As she worked Jackie said, “You watched me do my face and if we have another session you’ll have to apply your own makeup. Your home work will be to practice at home before we meet again.”

It wasn’t long until Jackie was done and Lana was falling in lust with her reflection in the vanity mirror; Lana was enthralled with the results. Her erection was testimony to her happiness.

Jackie picked up an almost identical pair of chandelier earrings as hers and inserted one in Lana’s right ear. “Turn your head like a good girl” Jackie instructed. Moments later Lana was sporting a pair of sparkling danglers. Lana slightly shook her head and enjoyed the subtle sound and feel of “big girl” earrings. Lana smiled broadly.

Jackie leaned over, grabbed Lana by the chin, pulled her closer and proceeded to kiss her on the lips. Jackie made an effort to mingle as much of her lipstick as possible onto Lana’s lips. Jackie broke the kiss with a soft smack sound and told her, “Lick your lips and taste the girly flavor; nice, eh?” Lana was obviously in a state of bliss. The lump in Lana’s panties was more obvious and her wet spot was larger.

Looking into the vanity mirror Lana could see Jackie beside her. Lana placed her hand on Jackie’s inner thigh, leaned over and returned the kiss that she had just been given. Lana boldly used her tongue tip and delicately traced Jackie’s pretty lips before ending the kiss. Jackie’s smile made Lana feel good.

Beauty tip

“Here’s a tip that may come in handy someday when you discover you don’t have your blush with you. Watch and learn.” Lana was surprised when Jackie quickly kissed her on each her cheek bones; two lip prints remained behind. Using the pads of her fingers Jackie quickly blended one lip print into a workable and attractive blush; it was a noticeable improvement. “And now you get to finish the job” Jackie said.

Smiling broadly Lana faced the mirror, leaned forward a bit, and easily completed her ‘make over’; it was a lesson she’d never forget.

“Of course you can’t kiss yourself but you can take any shade of lipstick and make it work. Usually girls like to match our lipstick tones. Just put a small dot of any color on your cheek bones and blend it in.”

Lana was so impressed that she spontaneously kissed Jackie on her cheek. “Thanks Jackie! I’m so glad I came over today. And I’m doubly glad that I bought you your wigs; you’re stunningly delicious!”

Without being asked Lana picked up mascara from the vanity and stroked her eyelashes to a black and feminine length. Following Jackie’s lead she used the eyelash curler to give them a good curl.

“Precious, your eyelashes and blush makes your face pop. Lipstick looks good on you; it’s a good start,” Jackie said. Lana was happily grinning. A few moments passed as they sat looking at each other. Both girls were smiling.

Reference photos

“With you looking so prettily feminine we need to capture this moment for you. The photos will let us match your skin tone with your cosmetics and clothes; colors are very important as we continue to enhance Lara’s looks.”

Using her cell phone and not wanting to appear too obvious about her plans Jackie only took three photos. For one of the photos Jackie had Lana pose as she was happily applying lipstick while sitting at a vanity and staring into a mirror. Lana would get copies and of course Jackie now had proof that her boss was willingly dressings as a woman in her bedroom.

Time to move to the next phase of her plan

Jackie cleared her throat, stood up, walked to the foot of her bed, turned to face Lana and assumed her now classic ‘video slut’ stance. Her hands were on her hips. Lana stood and turned to face Jackie.

In a low sultry voice Jackie announced, “Lana, it’s time to remove your clothes; everything but your thigh high stockings. That is part of our deal, remember?”

It was time to make things happen.

Erotic insurance

As a form of insurance Jackie needed to capture every bit of debauchery that Lana might engage in or talk about; hopefully there would not be another screw-up and all recordings would be perfect.

Lana removed her camisole and hung it on the back of the vanity chair. She was nude up top. Next she dropped her ½ slip and panties and tossed them on the floor. Lana was only wearing a pair of elastic top, black, thigh high nylons. Her circumcised penis appeared to be an above average eight inches with normal girth; nothing too scary. It wasn’t flaccid, it wasn’t erect but there was a drop of clear preseminal fluid dangling from the tip. It was important that her hidden cameras capture all of Lana’s naughtiness and nudity.

Jackie stared at the naked beauty of Lana’s cock and wondered to what degree she would have to be involved with Lana’s penis today; Jackie had no ‘hands on’ or ‘lips on’ experience with another man’s penis. Jackie briefly wondered what it would feel like to take Lana’s cock into her mouth.

Jackie went to her dresser and poked around. While she was looking for just the right thing she said, “Yesterday you said that you like wearing lingerie and feeling slutty; that it makes you very horny, right?” Lana quietly said, “Yes, it’s true; wearing panties, lingerie and ladies clothing make me feel pleasantly naughty. I get feelings and desires that I can’t explain.”

Taking a matching Navy Blue camisole and panty set from her drawer Jackie walked over and handed them to Lana. “Put these on, Sweetie.” Lana pulled the panties on and awkwardly tried to hide her partially engorged shaft.

Jackie stood directly in front of Lana as she put the blue cami on. Lana’s prick began poking above her panties; a preseminal drop attested to her ongoing arousal. Jackie reached forward and gripped Lana’s exposed penis tip and used her thumb to spread Lana’s pre-cum around and around the head of her anxious dick.

Lana stood frozen as Jackie thumbed her glans. “Does this make you horny, Precious? You feel so hard and long!” Lana was slightly trembling as she nodded ‘yes’.

Jackie’s delight

The thrill of holding a man’s penis excited Jackie to levels of arousal she had never experienced before; her naughty man-on-man fantasies were coming true. The warmth and texture of Lana’s cock were amazing! ‘My god, I think I can feel her pulse!’ Jackie’s penis throbbed with delight.

Jackie reached lower into Lana’s panties, wrapped her hand snuggly around Lana’s entire shaft and excitedly explored its throbbing length before beginning to slowly milk her. It was a marvelous bi-curious moment for Jackie; Lana didn’t complain.

As Jackie began stroking Lana she said, “You need to get used to doing this to yourself Sweetie; masturbation is a cheap way to pass the time.” Lana nodded ‘yes’ and spread her legs wider.

Debauchery captured: “Tell me again what you told me earlier.”

Using Lana’s penis as a handle Jackie tugged Lana closer and whispered, “Tell me Sweetie, what else you said yesterday; I need to hear it again. Exactly what did you tell me you wanted?” Lana closed her eyes and softly said, “I want to take your cock in my mouth and make you cum!”

“What would a cute Sissy like you do with a mouthful of cum? Spit it out?”

“I wouldn’t waste a drop; I’d swallow and ask for more!” Lana was very eager.

Jackie smiled and ever so slightly increased her tempo on Lana’s penis. “And my Precious; what else do you want Miss Jackie to do to you? Tell me again, my sweet Sissy.” Lana was becoming desperate for release. “I want you to fill my boy-pussy; to fuck me until we both cum; I want to suck you and have bare back sex with you!”

Jackie kissed Lana passionately on her lips and said, “See Baby Doll that wasn’t so hard to say, was it?”

Not getting the passionate kissing response that she wanted Jackie slipped her hand deeper and further back into Lana’s blue panty and tickled the edge of Lana’s love hole with her middle finger. Lana gasped; her boy-pussy puckered in delight; her passion improved immediately.

“Lana, I want you to masturbate yourself to an orgasm while I watch, OK?” Lana gasped and immediately said, “Yes!” At this point Lana would have agreed to almost anything; her needs were urgent.

“If I like what I see I may let you suck me to an orgasm too.”

More video proof

Jackie took Lana’s right hand, stuck it in her panties and made sure Lana took hold of her erection. “Do you like what you’re holding, darling? Would you like more?” Jackie made a conscious flex of her penis so Lana could feel it swell and contract. Lana moaned with lust at the sensation. “Yes!” Lana emphatically replied. “I want your penis.”

“First things first Missy; I get to watch you play with yourself, remember?”

Jackie walked Lana over to the king size bed, spread a larger protective towel and had Lana lay comfortably on her back; a small neck pillow and a nearby box of tissues helped her relax. Lana’s erection was ready and waiting for stimulation; her naked torso, and maybe her chin, would be a perfect landing zone for her ejaculation.

“I’m going to watch you masturbate to a nice juicy sissy orgasm. If I like what I see then we’ll expand our love making options. Maybe I’ll help you along if it comes to that. Any questions Precious?”

Lana said, “In return you must promise to keep your erection on display for me while I jack-off; to dangle it near my mouth.”

“Oh, does my new girlfriend want to become a cocksucker so soon?” Jackie rhetorically asked. As long as the moment was caught on video Jackie didn’t mind. In fact the thought of having her cock sucked by Lana pleased her greatly.

Looking down at Lana and seeing her black stockings, mascara coated lashes, girly red lips and rampant erection was extremely arousing for Jackie and her bi-curiosity. Lana’s sparkling chandelier earrings and short male hair completed the perfect androgynous image in Jackie’s queer sex dreams.

I get bi with a little help from my friends

“You’re a big girl, show Jackie how you please yourself; just be slow with it. My cock will be close by if you want it.” Lana began slowly stroking her erection. Jackie smiled at the control she had on Lana.

After a few moments Jackie said, “OK, Sweetie you can stop; let Miss Jackie help you out.” As Lana watched Jackie removed her panties and wrapped their silky warmth around Lana’s rigid penis. “Let Miss Jackie give you a helping hand.” Jackie leaned down, gave Lana a kiss on her lips and began the cock milking moves that she was so good at. Lana was enjoying every panty-aided touch by Jackie.

When Jackie thought Lana was getting close to ejaculation she stopped her efforts but left her panties on Lana’s penis. “It’s your turn.”

A frustrated Lana glanced over and saw Jackie’s panty free erection swaying teasingly near her mouth. Grabbing her prick in the traditional way Lana began jerking off with her eyes fixated on Jackie’s rigid appendage. Lana softly mewed and licked her lips as she stroked herself.

After watching Lana’s efforts Jackie leaned over Lana and picked up one of the sheer stocking that had been placed on the bed; Jackie’s penis poked Lana on the cheek. Lana made an unsuccessful attempt to capture Jackie’s swaying cock as it went by.

Dangling the diaphanous black stocking above Lana’s crotch Jackie began lightly dragging it up, down, over and around Lana’s crotch and erection. Lana moaned and her eyes became big. “Oh, god… keep doing that!” she pleaded.

“If you liked that penile tickle tell me what you think of this, Precious.” Slapping Lana’s masturbation hand away Jackie looped the long sheer stocking 360 degrees around Lana’s shaft and began moving her hands back and forth so the stocking slid deliciously slow around Lana’s cock; it was like having a long, soft feather tickle her cock.

From personal experience Jackie knew this to be salaciously satisfying. Lana grunted loudly in approval and exclaimed, “My God, that feels so fucking nice!”

“I call this ‘buffing’ the pole” Jackie said.

Knowing that Lana’s orgasm was building Jackie instructed Lana, “Don’t be so lazy Sweetie. Take over doing this and I’ll give you a special treat.” Lana was soon ‘buffing’ her pole.

An appetizer blowjob, not the full course

“I want you to know that what I’m about to do is just a teaser and you will still owe me a real blowjob.” Jackie leaned closer and lowered her erection to allow Lana’s to experience a cock in her mouth for the first time. Lana turned her head and began nursing on Jackie’s penis and never missed a caress of the stocking. Jackie asked in a low, sultry voice, “Are you feeling slutty yet, sissy?”

In reply Lana sucked more of Jackie’s cock into her mouth. Sucking a penis was becoming addictive to her; Lana smiled which is hard to do with a cock in your mouth. Lana increased the tempo of her new and enhanced method of silky masturbation; moments later she had the most intense and amazing orgasm of her life! Jackie’s unsatiated erection dropped from Lana’s lips.

As expected Lana’s chin, neck and upper torso received her load of warm sperm. Jackie’s ribs were spared Lana’s wetness. Jackie was in dire need of sexual release.

“Lana you really need to finish what you started if you want to experience a man’s ejaculation; you’ve left me and my aching penis in a very bad way; I have a mouthful of tasty fresh sperm waiting for your talented mouth.” Jackie wagged her prick in Lana’s face.
“Thank you Jackie! Just give me a minute.” Lana got out of bed, reapplied her lipstick. Jackie sat on the edge of the bed and waited.

Lana put the cap back on the lipstick, crawled back onto the bed and knelt between Jackie’s wide spread legs. Lana gripped Jackie’s wanton shaft.

The full course blowjob: becoming a real cocksucker

Looking into Jackie’s eyes Lana extended her tongue and licked Jackie’s cockhead and glans several times. “What do I do now?” Lana panted.

“Do what girls like us fantasize about; do what would make you happy if I was sucking your. Kiss it Lana; leave a lip print on it like a good cocksucker.”

Lana kissed Jackie’s cock head and then pressed her lips firmly against it for a moment. Pulling back Lana looked at her red lip print on Jackie’s cock. She circled her hand around the base of Jackie’s shaft and ran her grip up and down Jackie’s shaft a few times just to see what it felt like to stroke a man’s penis.

Lana pulled Jackie’s cock to her lips and kissed it below Jackie’s glans, leaving another red lip print. Lana was finding these acts very erotic; it made her pulse rate and penis increase. Lana was about to suck her first cock.

Taking a deep breath, Lana eagerly took Jackie’s penis fully into her mouth. Lana explored Jackie’s pliable hardness with her lips and the texture of her shaft with her tongue.

Jackie offers advice

“Think of your mouth as the hand you jerk off with. Grip with your lips; hold my cock on your tongue; use one hand to stroke my shaft and the other hand to tickle and tease my balls and boy-pussy. If you really want to thrill your date, towards the end of your ‘date’ insert a finger into their pussy. Trust me, it feels fabulous!”

Placing her hand on the back of Lana’s head Jackie gently guided Lana back to the task at hand. “Increase your tongue action and swirl it around my glans and shaft; suck faster and harder when your date is about to cum.”

Lana immediately got the hang of things. Jackie had her eyes closed and was moaning and smiling at the same time. Lana had made it to the base of Jackie’s cock with her mouth more than once; red rings on Jackie’s shaft were proof. Jackie began making subtle, involuntary, thrusting ‘fuck moves’ into Lana’s mouth as her orgasm built. Lana began probing Jackie’s rose bud.

“Darling, I’m getting really close… get ready!”

A new cocksucker in town!

Heeding Jackie’s warning Lana took as much penis as she could into her virgin mouth. Jackie’s cockhead was well back in Lana’s throat; she sucked, licked and swirled her tongue and in a moment of divine inspiration shoved her middle finger deep into Jackie’s pussy and wiggled it very energetically.

Lana dove down Jackie’s shaft and waited; she was rewarded for her patience with waves of ‘back-of-the-throat’ warm cum spurting forcefully from Jackie’ cock.

Lana made a couple gulping movements (which felt fantastic to Jackie!), swallowed three times (which felt fantastic to Jackie!) And then she did a final cock-milking while keeping her lips snuggly sealed around Jackie’s throbbing appendage (which felt fantastic to Jackie!) Jackie’s wet but clean dick popped free of Lana’s plump red lips. Lana slowly withdrew her finger from Jackie’s warmness.

Lana remained on the bed as she recovered from performing her first blowjob. Before she could wipe her sperm coated lips with the back of her hand Jackie kissed Lana on her wet lips, probing for a taste of her own seed. Jackie was naughtily pleased to have found some. Jackie kissed Lana again.

Sitting down next to Lana’s head Jackie ran her fingers along Lana’s cheeks and softly told her, “You’re a cocksucker for life now, Sweetie; it can never be undone.”

Lana smiled and said, “I liked the way you felt in my mouth. I felt super slutty and horny; it didn’t taste bad at all. You should try it sometime…soon.”

Jackie passed Lana a baby wipe for her middle finger and said, “You were superb. “Thanks for a great time Lana.” Lana managed a smile and restated, “You owe me one.”

Time to go

After several minutes of post orgasm reverie Lana decided that it was time to put an end to today’s activities. She needed to attend to many pressing things other than sex and looking feminine; she had a company to run. There was Jackie’s employment status, sensitivity training; IT scans of all company computers to purge any offending images and there were purchases of a lot of lady’s clothing and cosmetics.

“Jackie, I need to get back to my corporate duties, finalize our special agreement and return to boy mode. While you make a fresh pot of coffee I’ll clean up, get dressed and join you in the kitchen.”

Lana’s words brought a great sense of relief to Jackie. In truth they both had things to do. Making a fresh pot of coffee would give her time to check her spy cameras and emails.

Sunday Coffee Break

Jackie found her high cut panties, replaced the panty liner and pulled them on. She brushed her tousled hair, grabbed a lipstick from the vanity and left the room, topless, for the kitchen.

Before dealing with the coffee Jackie did a quick check of her laptop to insure that her multiple secret videos were being correctly recorded and stored. They were!

Just as she was closing her laptop a “bing!” alerted her to a new and important email; it was from TransFormU and marked ‘URGENT’! Jackie clicked it open.

And then… a miracle!

“Dear valued TransFormU beta user. Your recently downloaded TFU project continues to be in beta development. Our records show that you downloaded still images and our ground breaking ‘Slut Me Up’ video. Unfortunately TFU omitted an essential program security key which you MUST enter BEFORE 6 PM PST today on EVERY device, server and ‘cloud’ service where you have stored your project(s) or they will auto-delete and you will lose ALL of your files.”

“We apologize for any inconvenience this oversight may have caused you. We appreciate your patronage and will grant you three new TFU future projects at no charge to make amends for our oversight. Enter this key ASAP: A147JX-G98PZ2-62KK33.”

Jackie let out a muffled ‘whoop!’ of excitement. A good day and a bright future just got better and brighter! She leaned back in her chair and softly laughed.

She re-read the email and giggled over her good fortune. ‘My “Slut Me Up” porn video and photos will automatically delete from everybody’s computer but mine! Mike doesn’t know! Nobody knows but me! No one will have proof of my porn mistake!’ It was an amazing case of a last minute reprieve. Jackie said a silent prayer of thanks.

Things are looking better

Jackie was an extremely lucky lady. Not only was she not going to lose her job Jackie was being promoted at work and would be involved with “special” projects for her boss. The scary downside was that if she wanted to keep her job AND get the promotion she was going to have to present as a woman, go on dates, and fuck and suck her boss!

Jackie had less than three hours to save her creations. She very carefully clicked on “OK” and carefully typed in the security code to preserve her TFU projects on her computer and then leaned back in her chair and smiled like the Cheshire cat. It was time to rethink options.

Now what?

Jackie pondered new options: ‘Should I kick Lana out now and cancel my date with Mike? No, I need him to conduct the sensitivity training at work or else I can never show my face there again. I need Mike’s offer, money and protection. I need Mike in order to further my career and I need a pay raise. I need Mike so I can safely dress as a woman at work. And I need Mike because… I need a man.’ It was obvious that Jackie needs to make Lana happy. To keep Lana happy there had to be sex; a mic drop moment revelation.

Salvation comes from satisfying Mike/Lana

Things to consider: Mike wants and needs me. All I have to do is satisfy his desires. How? What are his desires? He desires to be femmed up (I can do that) and he desires to have sex with me (I can and will do that!)’. All was not lost.

Jackie did some thinking while making coffee. By now her hidden nanny cams had captured an abundance of damning videos of Lana dressed in drag, applying makeup, sucking cock, masturbating, etc. Hopefully it was enough to ensure Jackie total protection from termination or blackmail. A major side benefit of today’s activities was that her financial security was now secured.

Jackie had nagging concerns if she should return to work. The entire company knew that Jackie was a biological male and they correctly assumed Spence was a bit “light in the loafers” in terms of heterosexual norms. These thoughts were troublesome and weighed on her mind.

Jackie was grateful that she now was the only person in possession of her porn images; there was nothing that could be held over her head as blackmail.

Coffee is ready

Jackie placed two cups of coffee, crème, sugar, teaspoons, a plate of cookies and napkins on a tray for transport to the bedroom; for a feminine touch she added a small vase with flowers in an effort to make her new girl friend happy. The next few weeks would certainly be exciting. There was so much more to accomplish with Lana.

Coffee with the Queens

At that moment a very effeminate looking Mike entered the kitchen and took a seat. Or was it a dyke dressed in Mike’s clothes?

There had been no attempt at makeup removal; blush, eye liner, eye shadow, mascara, and nail polish were on full display; a fresh coat of lipstick had obviously been added. Gold ball stud earrings had replaced the chandeliers. It all made for a feminine image.

Jackie smiled and poured a cup of coffee. “My, don’t you look pretty; here you go love. Have a sip.”

Mik-Lana picked up the cup and took a sip; her red nails and red lip print contrasted with the white cup.

Pointing at Mik-Lana’s fingernails Jackie said, “What about your girly nails and face?”

Lana smiled. “I’m pressed for time and I’ll get squared away when I get home. In fact I pulled on my pants and shirt over my stockings and camisole. As long as I don’t get in a wreck or stopped by the police for a traffic violation I’m fine driving home like this. There is a lot I need to do.”

“Oh?” asked Jackie.

No return

“I’ve decided that you returning to the office would be too awkward and distracting. I’ll keep you on the payroll at the agreed amount and with a better job title. There will be $4,000 deposit in your checking account tomorrow morning; use it to buy us a wardrobe, cosmetics and girly accessories. I’ll replenish the money as needed but only if you ask.”

“I’ll schedule our medical exams for Wednesday and if all goes well we can formalize everything on Friday. I need to start attending to details today so I need to leave.”

“Oh?” asked Jackie. “We need to talk. What if I have important information that you need to know?”

“There’ll be time for that later but not now. I’ll call you.”

Jackie just smiled smugly. ‘Boy, she’s in for a big surprise’ she thought.

Jackie’s farewell was, “And don’t ever come over without calling first! Agreed?”

Her tone took Lana by surprise. She turned to look, paused, nodded her head and said “I won’t forget; and I also won’t forget that you owe me a blowjob.” After putting on a pair of oversize sunglasses Lana patted Jackie gently on her butt and left.

Jackie suppressed an odd urge to call after Lana and admonish, “Call me when you get home!”

END

Dear readers,

I invite you to read my other 25+ stories on this site; stories that range from G to XX ratings. I’d like you to meet two of my favorite characters; Stacy and Sara. Both are amazing heroines as are their individual adventures. Stacy is so special that she appears in a few of my stories.

My Avon Lady trilogy is especially fun if you are old enough to remember the door-to-door sales ladies and the free cosmetic samples they always left. I always intercepted my mom’s lipsticks. Did you?

•Adventures of Sara: Evolving deeper into femininity
•"Girls" for the Summer Club - A Sister's Revenge
•Pretty Stacy: Beginnings
• A Womanless Beauty Pageant: It was the zipper's fault

Please leave a brief “hello” in the comment section of ANY story you read so I know you’ve been there.
Thank you!

Donna T