Previously

“Yes, there are just few things more. Don’t wear underwear, bring your favorite panties, and bring your nylons and a box of sheepskin condoms. I think you’ll like they way I feel when I’m deep inside you.”

Jackie was sure she heard a gasp from Mike who was breathing heavy like a man in lust. Continuing, Jackie said, “I’m sure I have a bra that will fit you. I hope you like lace, Mike. I do.”

“I’ll see you tomorrow. By the way, I’m a 38 B.” Mike hung up.

Jackie put down her phone and giggled at the turn of events. Her future was looking brighter.

Things are looking better

Having gotten herself into a very dire situation when extremely compromising photos and a mini porn video were accidentally sent to the contacts in her email address book Jackie had gotten extremely luck. Not only was she not going to lose her job (and possibly many friends) Jackie was being promoted and would be involved with special projects.

The scary downside was, that for this to happen, she was going to have to fuck her boss, Mike Spence! Having viewed Jackie’s porn movie, even though it was CGI rendered, Mike was infatuated with Jackie. What added to Mike’s obsession was that he was a closeted cross-dresser that literally ached to express his feminine yearnings and for man-on-man sex.

It was a little after 1 PM on a Saturday. 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 12 noon tomorrow to look as femme as possible for Mike? A quick self assessment narrowed her options to hair, eyebrows or fingernails.

As a bonus Jackie’s “date” would be fulfilling her own latent desire to experience sex with a man. Unknown to Mike it would also be Jackie’s first foray down that forbidden trail. There were lots to be done and a short time to get it done.

And there was the nagging ‘problem’ with her sex tape and photos. She needed a way to explain them away. 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 porn?

Taking time to collect herself, and her thoughts, Jackie made herself a drink and went to her chair. She didn’t want to do anything brash. ‘Hair, brows or nails’? she thought. ‘I need to look more femme soon.’ Her laptop alerted her to a new email. Leaning forward she clicked it open. It was from TansFormU!

“Dear valued TransFormU beta user. You recently downloaded an end product of a TFU feature that continues to be refined. Our records show that yesterday you downloaded several still images and our ground breaking ‘Slut Me Up’ video. We omitted an important program security key which you MUST enter on the computer that was used for the download if you want to keep your items from expiring and auto deleting. Enter this security key BEFORE 6 PM PST today or you will lose ALL your creations: A147JX-G98PZ2-62KK33. We apologize for any inconvenience this oversight may have caused you. We appreciate your patronage.”

Jackie let out a loud ‘whoop!’ of excitement. A good day and a bright future just got better and brighter! She took a long sip of her drink and leaned back in her chair, laughing loudly. 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! They have no proof!’ Glancing at a clock she had about four hours to save her creations. She hurriedly typed in the security code to preserve her items, leaned back in her chair, and smiled like the Cheshire cat after eating a canary.

It was an amazing case of dodging a bullet, getting a second chance or whatever metaphor you wanted to use. Jackie said a silent prayer of thanks.

Jackie sipped and thought. ‘Should I cancel my date with Mike? No, I need him to conduct the sensitivity training at work or else I better never show my face there again. I need Mike in order to further my career and get a pay raise. And I need Mike because… I want a man.’
Taking another sip her pondering continued. ‘I need Mike. I need to keep Mike. I need to make Mike want me. I need to make him want to keep me. But how? I need to satisfy his desires. But how? What are his desires? He desires me to look like my porn video. But how? He desires to be femmed up (I can do that) and he desires to have sex with me (I CAN do that!)’ All was not lost.

Getting ready

‘I need to look more femme as soon as possible. Hair, brows and nails should do it’ she thought. Using the search engine on her laptop Jackie called House of Beauty Salon a block away. She explained that she wanted acrylic nails and eyebrow shaping. They had an opening and said it would take a little more than an hour and would cost $50 to $75 depending on what they did. They would be open until 6 PM. Jackie made the appointment for 3 PM. Figuring that she was off work until Wednesday that would give her Sunday, Monday and Tuesday to enjoy these feminine niceties in case she had to ‘butch it up’ with a more manly look on Wednesday. And perhaps Mike would have a solution.

Changing into a pair of mid rise denim pants and a simple print blouse Jackie applied some lipstick, grabbed her purse and left. Two hours Jackie was home and definitely looking… pretty. The beautician, upon learning that it was Jackie’s first salon visit, spent more time and effort with her. Asking if Jackie was trying for a certain vibe or look Jackie had replied, ‘Sexy, verging on slutty’.

Her acrylic fingernails were perfectly shaped and almost ¾ inches longer; definitely more girly looking than before. They were a dark scarlet as were her toenails. Her eyebrows had the super feminine thin arch seen in her ‘Slut-Me-Up’ video. As a special service to Jackie the beautician tinted Jackie’s eyelashes and eyebrows that wouldn’t fade for six weeks. There could be no going back. ‘I hope this gives Mike the hard-on that he’s looking for’ she thought.

Before returning home Jackie bought matching pairs of Silky Sheer Cocoa colored pantyhose; one for Mike and one for her, a tube of KY Jelly personal lubricant, a box of Kotex Ultra Thin Pads with wings, two deli sandwiches, and two liters of Sprite for her Tito’s.

Entering her condo she put her shopping bag down and quickly walked to her vanity mirror. She placed the Kotex Ultra Thin Pads on her vanity. Jackie sat down so she could admire her new look. She held her new dark red fingernails next to her face to confirm how they, combined with her newly tinted and shaped eyebrows and long, dark lashes, gave her the look she was striving for. ‘Damn, I’m hot!’ She used a tissue to remove her daytime lipstick and replaced it with a dark red color that closely matched her nails. Picking up her eyelash curler she gave them a nice crimping.

She had to get away from the mirror as she was infatuated with her look. Her jeans were beginning to bulge. Grabbing her cell phone she clicked off five or six selfies, making a mental note to update her TransFormU images in the near future.

Going back to the kitchen, she 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. ‘Best to be prepared’ she figured. She wasn’t sure how tomorrow would play out.

The evening was fading and she wanted to be bright eyed and eager for Mike. Her fate, literally, was in his hands. It was going to be an interesting day. She straightened the house a bit and retired to bed. She didn’t wear her favorite chemise thinking that she would save it for tomorrow. She removed her lipstick and climbed into bed. ‘I’ll remake the bed with my satin sheets after breakfast.’ She turned off her night light and tried for sleep.

Jackie’s alarm clock woke her at 8 AM. After coffee and breakfast Jackie spent some time to make sure that the condo and her bedroom looked nice and neat. Mike was due at noon and at 9 AM she began to get ready.

She showered and shaved all the areas that needed it and some areas that didn’t need it. She was not leaving anything up to chance. It had been months since she had shaved her crotch so she had to spend a little extra time to get it just right. ‘Mike better appreciate all this shaving’ she complained. ‘I wonder if he will be smooth. I’d like that.’

Stepping from the shower she dried and moisturized her freshly shaved legs. Once dry she tucked her penis and slipped into black French cut panties before going to work on her shag pixie cut hair style. Hairspray was the final touch. She looked pretty.

Recalling her TFU ‘lingerie mode’ look Jackie dressed in her matching red garter belt and panty set, black stockings, a black and red pushup bustier (with lace trim) that emphasized her cleavage. Her breast inserts helped her look very well endowed. She stepped into black three inch pump heels unlike the four inch heels in her CGI movie. Managing to find some dangling gold chandelier earrings she tried for the show girl/slut makeup that Mike apparently liked. On purpose she didn’t apply any eye shadow.

Sitting in her thinking chair Jackie plotted on how to keep the negotiating power she had asserted during her conversation yesterday with Mike. There were several things that were in her favor. 1- Mike didn’t know that all Jackie’s TCU images had deleted themselves by now. 2 – She had something that Mike wanted… and he had made it clear that he wanted it very much; almost desperately. Jackie made a mental note to not seem weak or desperate. She had to be in control.

With that in mind Jackie removed her earrings, placed them on her vanity, and inserted her pearl studs. Next she wiped her ‘Trollop Red’ lipstick off. There would be time for that later. She wanted Mike to see her looking fairly plain when he first arrived and would then transform to a more sultry look after he arrived. It was all about the image.

Kicking off her heels she pulled on Jack’s khaki business slacks 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 she put it on, tucked it loosely into the khakis, making sure to leave the shirt cuffs unbuttoned, and the top two buttons open.

Her new scarlet fingernails showed at the end of the sleeves in contrast to the man’s white shirt. Hints of her lace bustier were, on purpose, visible at her neck. In fact her cleavage was visible. She made an erotically androgynous image standing there; a woman dressed in men’s clothes, with obvious breasts and a pixie shag hair style. Her beautifully shaped eyebrows and well defined eyelashes completed the image. The pearl studs were perfect. It was part of a plan that would, hopefully, keep her in control of the situation as well as her future.

Jackie had sensed a definite shift as who was on the offense during yesterdays call with Mike. There was a defining moment that tipped the conversation in her favor. She felt it when Mike said he wanted her… there had been a plaintive tone to Mike’s voice that bordered on desperation. Jackie wanted to maintain that leverage.

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 the KY lubricant on a night stand and strategically placed some extra tissue boxes throughout her condo. Mike’s modified pantyhose were conveniently waiting on the foot of her bed.

Retreating back to her thinking chair she closed her eyes and tried to psyche herself up. There would probably be many firsts for her today and she wanted to be as prepared as possible. With her eyes closed she mentally went down a check list. How far would she let him go with her? How far would she go on him? Would he fire her? Jackie did some yoga breathing to help steady herself.

At 11:30 AM she got up and lit scented candles in the kitchen and bedroom. Checking in the mirror she thought, being in Jack’s clothes, that she looked like a not so subtle lesbian. That mental image made her giggle. She resisted the urge to apply some lipstick but did make a few brush strokes of blush to her cheekbones. She placed a solitary dot of perfume behind one ear.

Returning to the kitchen she started a pot of coffee, laid out two coffee cups and two drinking glasses, a bucket of ice and a small plate of lime wedges. She went to the living room, pulled the curtains closed and sat on the sofa to wait.

The boss arrives

Precisely at 12 noon 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. “Hello, I’m Mike Spence” he announced.

Jackie opened the door wider and said “Please come in, Mike. Welcome to my home.” Mike 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 walked over to the counter and put his bag down. He did a careful check of the condo before making eye contact. “Your place looks nice” Mike offered. Jackie stepped closer and, in a manly fashion, firmly shook Mike’s hand and said “Thank you for coming, Mike.” While still shaking Mike’s hand Jackie made a quick assessment. Jackie stood about 5’ 7 inches and it appeared Mike was maybe three inches taller. He looked to be about 150 pounds, appeared fit and could best be described as boyishly handsome. According to company literature Mike was 30 years old, unmarried and liked snow skiing. Even by Jackie’s standards Mike was handsome. He had a boyish face, check bones that begged for blush and he had no facial hair. There were remnants, in both ears, of having pierced ears at sometime. ‘He could have been worse’ she thought.

“Would you care for a cup of fresh coffee?” Mike was 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 and asked Mike to have a seat. He did.

Sitting in silence for an awkward moment Mike took a sip of his coffee. 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. But first I’m sure you have business to resolve with Jack, right?” With a free hand Jackie widened the gap of her shirt exposing more of her bustier and cleavage. “Jack will leave once we’re done with the paperwork.” Mike’s pupils became larger. ‘Ah, another tell’. Jackie inwardly smiled and took a sip of her coffee.

“Let’s get the paperwork out of the way first. Don’t you agree?” Mike retrieved a file folder from the bag he had brought in and returned to the table with a pen. “All of the items we discussed yesterday are in this document. The term of the contract is one year with extensions available after six months. I’ve decided that you will be my Special Assistant with duties and projects determined by me. I’ve set your annual salary at $75k with a chance for performance bonuses. In return you will… (he 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 he added “Is that clear? There is also a Non Disclosure Agreement that, if you violate it, will make your life a living hell. And there is a Sexual Exclusivity Agreement. Neither of us can have sex with anyone else. It protects us both from STDs.”

Jackie looked demurely over her cup of coffee and softly replied, “Yes, Mike. It’s clear. And will the company conduct the two day LGBTQ sensitivity training?” “Yes, it’s all set to go starting Monday.” 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. Mike looked momentarily startled by Jackie’s boldness. He paused to give her suggestion some thought. “Yes, I think that would be the right thing to do.” Jackie reached over and placed both of her warm hands on Mike’s hand, letting them linger just a bit; she gave them a gentle squeeze and took the pen from Mike’s hand. All documents were quickly signed and Jackie pushed them back to Mike.

“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 counter where the glasses were. Jackie began filling their glasses with ice and Mike reached into his bag producing the promised bottle of Tito’s vodka. Mike poured the vodka and Sprite while Jackie added the limes. She thought she saw him try to get a whiff of her perfume.
Staring at each other they both raised their glasses. “To a new future” Mike pronounced. Jackie smiled and added “And here’s to 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.

Jack leaves

“I think we are done with Jack. Let’s have seat on my couch for a bit, shall we?” Jackie instructed. With drinks in hand they walked toward the couch. Jackie paused by her thinking chair and kicked out of Jack’s loafers. She put her drink down by her laptop and removed Jack’s pants, hanging them on the back of her chair. The white shirt quickly followed. She was now standing in her ‘lingerie mode’ items. Her nylon covered feet contrasted nicely with the white carpet. Mike was watching and enjoying her transformation. Mike commented, “That outfit is fantastic! I see no maleness. It gives me a goal to strive for… with your help. It also makes me… envious.” Jackie was sure that he was going to say ‘horny’.

Jackie picked up her drink, faced Mike, struck a not so subtle slutty-girl pose and then joined Mike on the couch. They sat a half cushion away from each other. She took a sip and placed her drink on the coffee table. Jackie crossed her legs and moved next to Mike; the sound of her nylon covered legs crossing did not go unnoticed by Mike. He took a gulp of his drink and stared some more. Jackie could sense that his mind was whirling. “So, what do you think Mike? See anything you like?”

Mike gulped and tentatively put his hand on Jackie’s nylon covered knee and slowly rubbed it. “You look, and feel, stunning; much prettier than your video.” “Thank you Mike, a girl likes to hear that. I think that, with a little effort that you could look pretty too. You have a face and cheek bones that would lend themselves to being pretty.” Mike blushed and took another sip of his drink. “I would like that” he confessed.
Jackie reached over and laid her hand on Mike’s knee and suggested, “Make yourself comfortable. Kick off your shoes.” Mike quickly did. With his shoes off Jackie saw that Mike was wearing black nylons with a reinforced toe. ‘He’s got a head start it seems. I bet they are thigh high style’ she thought. Rather than ignore the elephant in the room Jackie pointed at Mike’s nylon covered toes and said “It seems we both like black stockings, Mike. I wonder what other items we share a love for. Do you like panties and lipstick, Mike?” Mike didn’t answer and his eyes diverted away from Jackie. He licked his lips. ‘Another tell’ thought Jackie. They both took a sip of their drinks and leaned back into the couch. A strong level of tenseness had vanished. ‘So far so good’ Jackie thought.

Jackie thought about moving Mike’s hand to the inside of her thigh but quickly shrugged that off. ‘Can’t be to bold… just enough to keep things in my favor. “What did you bring in the bag Mike? Did you bring your favorite panties, heels, or maybe a cute and skimpy skirt?”
Mike took a deep breath and said “I brought three wigs and some stuff.” “Three wigs, Mike? I only wanted two.” Mike blushed and replied “I brought one for me. Shoulder length strawberry blond.”

Standing up Jackie made a display of smoothing her nylons from her ankles to her thighs, adjusting the tightness of one garter. Noticing that Mike was involuntarily licking his lips Jackie flashed Mike a pretty smile and suggested “Give my garter a little pull, feel the tightness. You may need to know the proper snugness someday”. Mike hooked a finger under one garter and pulled it slightly getting a sense of what Jackie had said. He held Jackie’s garter strap for a couple seconds, stroked her nylon covered leg with his other hand, and let it go. There was a soft snap sound as the elastic snuggled back into place. “It’s like having someone playfully snap your bra strap. Has anyone pulled your bra strap, Mike?”

Waiting a moment for the reply that never came, Jackie announced, “I’ll take your bag to my bedroom, you make us another drink and then join me at my vanity. I have a chair waiting. I also have something for those dry lips. Do you like red, Mike?” Jackie grabbed the bag and went to her bedroom.

The bedroom

Mike arrived in quick order with both beverages. He stopped just inside Jackie’s bedroom door and looked around; nice, neat and feminine. He saw the contents of his bag neatly piled on Jackie’s bed, several pairs of his panties, a tube of lube, and his boring white bra lay next to the wigs. He was puzzled about the folded nylons and the box of panty liners on the vanity. He knew he didn’t bring them.

Jackie was seated at her vanity. She saw Mike in the reflection in her mirror and motioned for him to take the seat next to her. He did. Both drinks were placed on coasters on the vanity. Without turning to face Mike, Jackie said, “Just watch for now.” She picked up one tube of lipstick, extended the lipstick, gave it a smell and rolled it back into the tube, pretending it was not quite right. “Fragrance is key to a lipstick. Some smell like wax. Choose carefully.” She held it in front of Mike’s nose for him to smell. “This smells like nothing, tastes like nothing so why bother?” Mike agreed.

Grabbing a second tube of color Jackie removed the cap, gave it a whiff, nodded and began to carefully apply the scarlet red she had pre-selected. Mike sat enthralled, watching every move. “Let me smell that please,” Mike requested. “That’s a much nicer aroma.”
Jackie then began applying her eye shadow, using small sponge brushes to blend colors; smoky black, a lighter gray and some gold highlight. She was getting slutty. Mike was taking it all in. Next came her jet black eye liner and, for Mike’s benefit, Jackie used her mascara and finished with an eyelash curler. Glancing over at Mike she announced, “Almost done.” Jackie picked up her diamond chandelier earrings and easily had them in place.

Turning to face Mike she asked, “Is this who you expected to open the door for you today?” “Wow, you look amazing!” Mike managed to say. Jackie leaned over, grabbed Mike by the chin, pulled him closer and proceeded to kiss Mike on the lips. She made an effort to transfer as much of her lipstick as possible on to Mike’s lips. She broke the kiss with a loud smack sound and told him “I just fixed your chapped lips. Lick your lips and taste the scent. Nice, eh?” Mike was obviously in a state of bliss. The lump in his pants was also obvious.

Grabbing Mike’s chin Jackie closely inspected his lips. “Nope, this won’t do. You need more lipstick if you want full coverage. You do want better looking lips, right?” She handed Mike the open tube of lipstick. “Here doll face, do it the right way.”

With barely a hesitation Mike took the tube, leaned in towards the mirror, and carefully applied the scarlet red. Without looking around Mike lamented “This color doesn’t match by skin tone, it’s to stark.” Without being asked Mike picked up the mascara and stroked his eyelashes. Following Jackie’s lead he used the eyelash curler to give them a good crimping. Looking into the mirror he could see Jackie behind him. Jackie had assumed her now classic ‘lingerie mode’ stance. Her hands were on her hips and she was standing at the foot of her bed.

Mike stood and turned around to face Jackie. “I think you look good in lipstick, Mike, and your eyelashes make your face pop. Very nice; it’s a good start,” she said. Mike was happily grinning. A few moments passed as they stood there looking at each other. In a low sultry voice Jackie announced “Mike, it’s time to remove your clothes, right? That is part of our deal, right? You already have your shoes off; that’s when I saw your nylons, remember?”

Mike removed his shirt and hung it on the back of the vanity chair. He was nude up top. Next he dropped his pants and tossed them on the bed. He was only wearing a pair of elastic top, black, thigh high nylons. No panties. His penis wasn’t flaccid and it wasn’t erect. It appeared to be an above average eight inch with normal girth; nothing too scary. Jackie was staring and wondering to what degree she would have to be involved with it. Hands, lips or both? She had no experience, other than porn, as what to do.

“Mike, select one of your panties and put them on, ok?” Mike shuffled the panties around and selected a navy blue pair of briefs and pulled them on. Jackie continued, “Your choice in stockings is good but in the long run they become too much work. The elastic top weakens, they begin to droop and you spend your day trying to pull them up with your pants on. Eventually you’ll need a garter belt to keep them up or just switch to a garter belt and stockings now. Your other option is pantyhose. There are many styles, with and without patterns and they are convenient. The silky ones feel very nice. Have you worn pantyhose before, Mike?” Mike nodded yes.

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?” Mike quietly said, “Yes, I said that because it’s true. I get feelings and desires that I can’t explain.” Taking a matching navy blue camisole from her drawer Jackie walked over and handed it to Mike. “Here, put this on. It matches your panties and will make you look more femme. It will have to do for today.” Jackie was standing directly in front of Mike as he pulled the cami on.

Tell me what you told me

“You know what else you told me yesterday, Mike? You told me that you find me attractive. There’s one more important think that you told me. Do you remember, Mike? Tell me what else you told me yesterday. I need to hear it again.” Jackie reached forward and felt Mike’s panty encased dick. Keeping eye contact Jackie rubbed Mike’s dick, as sensuously as she could. “Does this make you feel alive, Mike? Does this make you horny, Mike? I think so, based on how big you’ve gotten. Your breathing has gotten a little rough, hasn’t it?” Mike nodded but didn’t move. His cock was protruding above his panty. Still keeping eye contact Jackie used her thumb to spread his pre-cum around and around his dick head. Mike was lightly shaking.

Using her other hand Jackie started to lightly stimulate Mike’s nipple through his camisole. Jackie leaned closer and whispered “Tell me what else you told me, Mike. We both know what you said. Tell me again, I’m waiting.” Mike closed his eyes and said “I want to have sex with you! I really want to have sex with you. I’ve never done this before but I want to have sex with you!” Jackie smiled and moved her hand so she could rub up and down Mike’s dick. “There, that wasn’t so hard to say, was it?”

Standing on her toes Jackie kissed Mike on the lips. Not getting the response she wanted Jackie kissed him with more passion than before. At the same time she slipped her hand into Mike’s panties, circled Mike’s cock at the base, her skin on his skin. She gently drew her circled her fingers tighter and stroked lightly up and down his shaft. She felt a throb. Mike’s kissing improved. “Mike, what did you say you wanted?” Mike made a slight forward thrust and gasped “I want to have sex with you!”

Jackie took Mike’s right hand and held it against her dick and made a conscious throb of her penis so Mike could feel it. Jackie moved Mike’s open palm up and down her stiffening shaft. Mike moaned. “Take my panties off, Mike. I need my panties off.” Breaking from their kissing Mike knelt down and helped Jackie step free. Her cock sprang eye level with Mike and was pointing toward the ceiling. Mike stared at it. “How do you want to do this, Mike?” asked Jackie.

Mike gently grabbed Jackie’s shaft and inspected it for a moment. Taking a deep breath, Mike slowly pulled Jackie’s penis closer to his mouth. He looked up into Jackie’s eyes, extended his tongue, and licked her cock head a couple times. “What do I do now?” Mike panted. Jackie looked down and said, “Try kissing it, Mike. Leave your lip print on it.” Mike kissed Jackie’s cock head and held his lips against it for a moment. Pulling back Mike looked at his lip print on Jackie’s cock. He circled his hand around the base of Jackie’s shaft and ran his grip up and down Jackie’s dick a few times just to see what it felt like to stroke a man’s penis. Jackie made sure to properly throb for Mike’s education. Looking up at Jackie, Mike pulled her cock back to his lips and kissed it again, this time below her glans, leaving another red lip print. Mike was finding these acts very erotic. So did Jackie. They both watched Jackie’s dick grow taller. Mike could feel the difference in Jackie’s firmness with his lips. It made his heart beat increase and his penis too.

“Are you feeling slutty yet, baby doll?” Jackie asked in a low, sultry voice. “You make me feel so good… and hard… and horny. Are you horny, Mike?” Mike softly squeezed and stroked Jackie’s shaft in reply. Fondling Jackie’s penis was becoming addictive. Jackie gave him the twitch he was looking for. Mike smiled.

Going down

Knowing the answer, but actually looking for approval, Mike asked, “Now what.” There was urgency in his voice. While waiting for a response Mike continued to gently stroke his hand up and down Jackie’s shaft. He was exploring what another man’s dick felt like. Jackie sent out another sex throb. Mike smiled at this twitch.

“Do what would make you feel good, Mike. Most girls put the dick in their mouth, seal their lips around the shaft, and suck and swirl their tongue while going up and down the shaft. Think of your mouth as the hand you jerk off with. Just go with it. Lubricate it with your tongue. Make it slippery. Bob your head if it feels right. Go faster when I’m about to cum.” Placing her hand on the back of Mike’s head Jackie gently guided him back to the task at hand.

Still on his knees Mike immediately got the hang of things and was giving an above average blowjob. Jackie had her eyes closed and was moaning and smiling at the same time. With a free hand Mike was slowly giving himself a hand job in slow rhythm with his sucking. Mike had made it to the base of Jackie’s cock more than once; Jackie began making subtle thrusting moves. “Darling, I’m getting really close… get ready!”

Mike made a final dive down Jackie’s penis. He sucked and licked and swirled his tongue, Jackie’s cock head was well back in his throat. … Jackie let loose. Several waves of cum erupted from Jackie’s cock. Mike didn’t spill a drop. He made a couple gulping movements and then a final upward cleaning suck keeping his lips sealed. Jackie’s dick popped free. Mike swallowed but remained on his knees as he recovered from giving his first blowjob. He wiped his mouth with the back of his hand. Jackie grabbed one of his arms and helped him stand.

Jackie hugged Mike and kissed him passionately on the lips. She made sure to use her tongue with the kissing. “Oh, darling, I can taste myself on your lips and it makes me feel slutty. You were superb.” Jackie made a point of rubbing Mike’s cock through his panties. His bulge felt nice. “Thank you for a great time. Come sit at the vanity for a bit. Have sip off your drink.” Mike did as he was told. After a short while Mike looked into the vanity mirror and reapplied the scarlet red lipstick, pressing his lips together for even coverage. “Where did all my lipstick go?” he asked. Pointing to her almost flaccid penis Jackie said “Look”. Mike turned and saw several red rings on Jackie’s dick. “Very impressive, Mike, you left me some trophy rings! By the way, wearing lipstick when performing a blowjob not only acts as a lubricant it also protects your lips from chaffing.” Mike nodded.

Sitting next to Mike Jackie ran her fingers through his hair and tried to sooth and calm him. “So how was it, baby doll?” Mike smiled and said “It didn’t taste bad at all and I liked the way I could feel you throb in my mouth… I felt super slutty and horny.” Taking a sip off her drink Jackie went to her lingerie drawer and brought back a navy blue 38B underwire pushup bra and a pair of breast enhancers. “Lift your arms, baby” Jackie instructed. Jackie removed Mike’s cami and placed it on the bed. Jackie put the bra on Mike, hooked it in the back, adjusted the straps, inserted the tit augmenters and pulled the cami back on Mike. “Your new tits look good on you! You earned them.” Noticing her gold hoop earrings on the top of her vanity Jackie picked them up and slipped one into Mike’s left ear. Handing Mike the other one Jackie said “You insert the other one. Stay here and I’ll be right back. Give me your drink glass.”

Jackie did some thinking while she mixed them fresh drinks. Returning to the bedroom she saw Mike was sporting both hoop earrings and was adding more mascara. His new tits were a definite improvement. Jackie sat down next to Mike and told him to close his eyes. “I’m going to add some eye shadow to show you what a little accent can do for your eyes. Next I’ll use eyeliner for an even better effect. Hold still.” A few minutes later Jackie was done. “Open your eyes, baby doll.” Mike slowly opened his eyes and checked his reflection in the mirror. He broke into a wide smile and said “Wow! My entire face looks better. I love what you did with my eyes.” His hand involuntarily fingered his earrings. He leaned over and gave Jackie a gentle kiss. “Thank you” he said. Jackie returned his kiss with more ardor and said “I’m glad you came over today Mike; it makes me feel pleasantly slutty too.” Jackie tweaked Mike’s panties and kissed him again.

Jackie handed Mike his drink. “To us!” Jackie said. Mike smiled, echoed the toast and they both took a swallow. Jackie put her hand on Mike’s knee and said, “I can’t call you Mike anymore. You’re much too pretty to be called Mike and after what you just did to my penis you deserve a new name. You earned it.

(To be continued)