The Power of a Smile/The First Step Rianna Olsen Transgender/Control riannao75@msn.com
Chapter I
Night after night, it was the same pattern. Jack didn't know what the strange attraction was. It was almost like a force of nature pulling him in. A force, once he gave into it, he realized had been pulling him all of his life.
But tonight he wasn't close to the level of vulnerability, or so he thought. No, tonight was like the past 5 or six evenings since he discovered New Friends, a chat site for singles. Jack settled into the chair, fired up his PC and went right to the Favorites toolbar. If he would have had the power to question his thoughts and actions, he would have surely asked himself, "When did I make New Friends a favorite?" But he did not control the slow and subtle direction that his life was taking. Unknowingly, he was in the tender care and guidance of, well; let's call her by her chat name... Toni.
Jack entered the room, and sure enough there was his new acquaintance Toni. He'd met other "chat" girls before, but the farthest distance along the path of love that they would ever take him was a shortcut through a bar, a bed and goodbye. Jack so wanted to tell himself that Toni was different...
"Christ, how many times have I typed that? I'm sorry Toni, that was as cliche as they get." typed Jack.
"No, you're right this time Jack," Toni replied. "This time is different." "I don't know how to prove that to you without meeting you in person."
"Well, gee, we have been chatting for more than the required four hours, so I suppose a meeting is in order." said Jack.
"Try four days," said Toni. "I know that's still not very long, but I already feel like I've known you forever."
Jack had no idea just how sincere Toni was when she shared that thought. Toni enjoyed hanging out at Ferrante's, a bar and grille on the upper-east side of town. It was a respectable enough place, but not too straight-laced that a woman with the build and beauty and fashion-sense of Toni would feel out of place. One must understand, that when Toni went out on the town, she always made sure to accentuate the positives... both of them. Her blouses were always cut low and her skirts high. Her heels helped both ends stand out in a crowd. Her makeup was exquisite and her long, manicured nails could land jetliners if she wasn't careful where she pointed them.
She was sure Jack would recognize her if, or make that when they met. They had made eye contact before at Ferrante's. Toni fascinated Jack. He wasn't like most of the other male patrons that sauntered in there. Sure, every week there would be a different girl with him, but he never seemed to be happy with any of them. Before long, Jack's forced gaze at his one-night stand would become something between a curiosity and a passionate fascination as it slowly turned and faced Toni. Who was this beautiful woman and why was she always alone? Somehow, he would escape into this whole other universe while his companion for the evening would babble on. Just before he would get up enough nerve to leave so-and-so and approach this woman of mystery, his attention would turn back to his date and Toni would disappear. Countless nights found Jack left wondering who, why and when? Those nagging questions were about to be answered.
"I feel the same way Toni. I can't explain it, but it feels like you know my heart and yet you've never laid eyes on me. Wow, did I just say that?" typed Jack. "I sound like a girl!"
Toni chuckled, "LOL. And what's wrong with that??" "Not a thing," wrote Jack, "unless you're a guy!"
"Well, if you're a real man, you'll let go of your fears and meet me for a drink tomorrow night." said Toni.
"Sigh. OK. You win. Where should we meet?" With a naughty smile and a glimmer in her eye Toni typed in "Do you know where Ferrante's is?" Jack quickly replied, "Sure, but that place is bad luck for me."
"Superstitious, are we?" wrote Toni. "Well, I think your luck is about to change. 8 PM at Ferrante's. I'll be wearing a red silk blouse with a black mini-skirt."
"Why not make it 7?" said Jack. On her end, Toni just formed her glossy red lips into a sweet smile and before he could even give it another thought, Jack said, "No, you're right, 8 o'clock is better for me too. Ferrante's at 8 it is. I'll be in a suit and tie just like every other guy in there."
"Don't worry," said Toni, "I'll know you the minute I lay eyes on you. See you tomorrow, love." and with that, Toni left the room.
Once again, Jack was left wondering, but not for long.
The workday flew by for Jack, and before he knew it, he looked at the clock on his laptop and it said 5:30 PM. Great! Already running half an hour late and he hadn't even left his desk yet. Good thing he and Toni had agreed on 8. 'I guess she really does know me well', thought Jack.
Jack hurried home and freshened up with a quick shave and shower. 'Five o'clock shadow never looks good', Jack thought to himself. 'In fact,' his mind told him, 'I think I remember Toni saying that she liked men who were smooth and sexy.' So Jack stepped back in the shower and began to shave his whole body. Jack's mind began to churn, 'I've never done this before in my life! Why am I shaving from head to toe?' Were it not for the fact that his mind was zooming from one thought to the next, Jack would have realized that his full-body shave was taking forever and he was running even further behind. Jack stepped out of the shower, felt his silky smooth skin, and wiped off the moisture on the mirror.
"Man, that looks good!" Jack said out loud. "Why didn't I do this years ago?!" Jack was getting so excited that his cock began to cry out for attention. Luckily, Jack looked at the clock nearby and saw that it was 20 till' 8. "Oh, shit! I'm going to be late as it is." His pleasure would have to wait. Jack splashed on some aftershave, threw on his clothes, grabbed his keys and his wallet, and ran out the door.
Chapter II
After driving around the block twice looking for a parking place, one finally appeared near the front entrance to Ferrante's. Friday nights were always packed. At 8:15, Jack stepped inside and began to scout the room. He was hoping that after shaving his whole person, he wouldn't be stood up tonight. As he glanced over the crowd, he spotted the same sexy women across the bar. Their eyes met once again, and he gave her a polite if not shy smile. Taking one more look around the room, he became aware of the fact that she was still staring at him. Jack looked back at her and suddenly felt a warmth overtake him as he came to the realization that this gorgeous woman had on a red silk blouse and a black mini skirt. This couldn't possibly be...
The woman lifted up her wine glass with one hand, and with the other motioned Jack over with her ruby red enameled finger matching the shade of her full, moist lips. If there were people in his path, he didn't seem to notice them. All of a sudden, Jack found himself on the stool next to this work of art.
"Jack, I presume?" cooed Toni. "Uh, y-yes." Jack breathlessly answered back. Slightly regaining his composure, Jack turned the question back around. "You can't possibly be Toni, can you? If you say yes, then someone pinch me."
"Oh, I plan on doing more to you than that Sugar" laughed Toni. "And yes, I am her."
Toni extended her right hand. Jack leaned down and kissed it. "Pleased to finally meet you Toni." said Jack. "The pleasure is all mine for now," replied Toni.
"Let me freshen your wine," said Jack as he hailed the bartender. "No, no." said Toni. "I know it's a little unusual, but I want to buy the first round. It took a lot of guts to overcome your superstitions and come up here to meet me. You deserve a reward." The bartender came over and Toni said, "John, we'll have two Flirtinis please." John winked and said, "Coming right up." Toni turned and smiled at Jack saying, "I hope that's not too 'girly' for you Jack. It's my very favorite drink." "I must say, I've never had one before, but with a smile like that, you could make me drink or do just about anything Toni." chuckled Jack.
Before long Jack and Toni were on their second round of Flirtinis and were laughing and chatting like best friends. "So you can't tell me that you don't have someone significant in your life," said Jack stirring his drink. "No, I really don't." replied Toni. "I've dated plenty of guys, but I either scare them off or they're just not worth the effort. Do you find me threatening Jack? I know some guys who would be already out the door if I bought the first round of pink martinis!"
"Threatened? Not at all!" Jack exclaimed. "Intrigued? Mystified? Perhaps. But threatened, no way."
"I am so glad to hear that", sighed Toni. There was that smile again. "Another round?"
"Sure, but this time it's on me and I choose the drink", insisted Jack. "If you say so," said Toni. "John, two more Flirtinis please" yelled John. He turned and grinned at Toni, "What can I say, you've got me hooked." "Tell me something I don't already know, Sugar." Toni replied. As Toni leaned forward to pick up her last drink of the night, Jack leaned forward, gently grasped her hand and kissed it once again. Staring down at her hand, Jack said "Those nails either look like works of art or weapons of mass destruction." He grinned and looked up at Toni. Toni ran her nails up and down Jack's chest and said; "One can find beauty in even the most dangerous of places. Let's finish off these drinks and go for a walk along the coastline. Who knows what danger we might get ourselves into?" Jack quickly downed Flirtini number three, took Toni by the hand, and led her into the moonlit night.
Toni and Jack walked hand in hand along the coast as waves crashed against the rocky shoreline. Toni just listened as Jack poured out his heart. As the moon focused its beam down on them, they drew closer and closer. Finally, Toni stopped Jack mid-sentence and kissed him deeply, practically drawing every breath from his lungs.
"I know, I know. The guy's supposed to kiss the girl first." Toni laughed. "I think we've gotten past any conventional rules, haven't we?" blushed Jack. Toni smiled and kissed him again saying, "You know the old saying, 'rules were made to be broken'. Just as before, the realities of time and space had escaped Jack. Suddenly they were back in front of Ferrante's.
"I just realized that you probably haven't had dinner yet Jack We could order something here, or better yet, I could throw something together for you back at my place."
"Well, if we're at your place, then you can't kiss me goodbye in the morning never to lay eyes on me again." Jack said with a devious smile.
"Why listen to you! I didn't even put dessert out and your already talking breakfast," said Toni.
"I don't even know where you live Toni. Drive slow so I can follow you" replied Jack as he headed for his car.
"Oh, don't be silly. Let me drive. Your car will be fine here until the morning. "I don't know," said Jack, "this part of town is always on the news for something." Toni flashed her smile at him and Jack said "You know what? They can have that lemon. Good luck to the jerk who ends up with it."
They walked up to Toni's fire red convertible and she opened the passenger door for Jack "Rules were made to be broken Sugar." Jack smiled and took his place in the passenger seat. Toni got in and kissed Jack one more time before starting the car. She took off his tie and un-buttoned his Oxford shirt. Running her nails over his chest while stopping to play with his nipples, she said "Ooh, smooth and sexy! You just get better with every minute. Take off that shirt and enjoy the wind against that lovely body."
Toni started the ignition and sped off into the night while Jack closed his eyes and felt the breeze swirl around his soft skin. 'Why didn't I do this before?' he thought to himself as the city lights accented his form.
Before long, they had arrived at Hanover Towers, the most expensive living quarters in the entire city. Toni pulled into the garage and Jack loosely put his shirt back on.
Toni parked the car, stepped out and before he could button the third button, opened the door once again for Jack. Jack started to step out, but Toni took her long nails and placed them on Jacks already tender nipples. "It's amazing how much power these things have over a person," she said pinching and pulling as Jack gasped. "Not to mention this thing," Toni said as she placed her 5-inch heel just below Jack's expanding cock.
She then let go of his tits and extended him a hand. She helped him out of the car and kissed him on the lips. She smiled at him and said, "I hope you enjoyed the ride, Sugar" "Immensely", said Jack. They stepped into an elevator with a clear glass panel that looked out across the skyline. Toni punched in a code and tapped a button. Quickly, the car took them up to the top floor. The elevator doors opened up on a penthouse apartment that was surrounded by endless views of the city and was obviously decorated with an endless budget.
Jack stood in amazement and said "Toni, this place is beautiful!" "Thank you Jack", Toni replied. "Please make yourself comfortable. Let me pour you a drink. I can't make a martini like John can, but I can come close." "Thanks Toni, I am a little thirsty after that ride." Jack walked over to the center of the room and took a seat on the sofa. Soon, Toni joined him with martinis in hand. She handed Jack his drink and said, "I propose a toast. Here's to forgotten fears, daring discoveries and Pink Flirtinis!" "Here, here!" laughed Jack as they clinked glasses and downed their drinks.
Since Jack was now on his fourth martini of the evening, the phrase 'daring discoveries' simply slipped through his swirling mind. He leaned in towards Toni; anxious to continue where they left off in the garage. Toni put her hand on his chest and said, "You look uncomfortable in those business clothes Sugar, why don't we slip into something more appropriate for the evening?" "Well, I'm afraid all of those clothes are across town in my apartment," said Jack. "Don't be silly. I had anticipated your needs sweetheart. There's a very comfortable outfit waiting for you in the bathroom. Why don't you enjoy a nice relaxing soak, and meet me back here in a few."
Jack thought to himself how nice a hot soaking bath would feel right now and quickly agreed. He opened the door to the bathroom only to discover a room twice the size of his bedroom at home. There was a large jet massage bath with a waterfall shower at the end. A track lit mirror ran the length of the counter. Jack undressed, drew the bath and gingerly stepped in. Soon after Jack was settled in, Toni entered the room. "I'm sorry, I just thought you might want another drink to help you relax honey." Toni sat down another pink creation on the tiles next to Jack's left hand. "Oh, and here's some lotion to make sure you're as smooth and silky as you can get." Toni said with that signature smile. Jack felt that warm glow all over him again as he said, "Thanks Toni. I love this feeling of smoothness all over my body. I'll definitely use it." Toni left the room and Jack read the directions on the lotion bottle as he sipped at his martini. He sat on the side of the bath and rubbed the lotion all over his body. That inner voice told him to leave a little patch over his clit...cock, but everything else should go. Jack stepped over to the shower and washed off what little remaining hair he had left on his body. He then noticed some oils and perfumes on the tiles opposite his martini. His mind told him that these would help relax him, so he used lovely lavender and roses combination and soaked for a few minutes longer. Stepping out of the bath he grabbed a towel from the wall and looked into the mirror. His shiny body sent waves of excitement through him. Jack had briefly entertained "going smooth" in the past, but thought that was too effeminate. Now here he was smooth as a baby's bottom and smelling of flowers! 'Why am I always worried about appearing to feminine?' Jack thought to himself. Starting to feel a little chilled, Jack decided to find those clothes that Toni had laid out for him. Jack looked around and saw nothing at first. "Clever girl." Jack mumbled under his breath. Then he saw a closet door left slightly ajar. Jack picked up what remained of his martini (a few sips) and walked over to the closet. The only thing hanging in it was a pink silk teddy, a pair of matching panties, and a pair of pink stilettos. As if on cue, Toni called out "Sugar, did you drown in there?" Jack replied, "No, I'm fine. I was just admiring my evening wear." Toni laughed and said, "Well, what else would you wear to a slumber party after 5 Flirtinis? Besides, I don't make it a practice of keeping men's clothes stashed away in my closets." 'She was right', thought Jack. Earlier in the day he would have scoffed at the thought of stepping into a teddy and panties, but 5 hours, and more importantly, 5 downed pink martinis later, he didn't give it another second's thought. He slipped the silk panties up his smooth legs and over his sack. Then he put the teddy on over his head and onto his hairless chest. He felt the silk rub against his still tender nipples. This brought him back to Toni's talented nails. 'Damn,' he thought, 'Toni really does have a beautiful set of nails. Maybe I could defend myself if mine were as long as hers.' He giggled out loud at this thought as he reached for the stilettos. He stood up and walked out of the bathroom like he'd been in heels since junior prom. Again, he didn't question this for one second.
"Come over here girl!" Toni cried out from across the room. She was sitting in front of the fireplace in a similar outfit but all in black. Jack sat down beside her and Toni leaned in and kissed him on the neck. "Ooh, you smell nice. And you look incredibly hot!" "Thank you Toni." Jack said as Toni's nails caressed his thighs. "I feel incredible! I don't what it is, but I feel horny as hell. And might I add, you look pretty hot yourself!" With that, Toni pulled Jack up closer and secured her lips to his. When she came up for air, she grabbed Jack's hard cock through the silk panties and said, "Something tells me that I have a girlfriend for life." Jack rubbed Toni's breasts and replied "Girlfriends for life!" and then kissed her again.
Toni grabbed Jack's hands and led him up from the sofa. She slapped him on the ass, pointed to the bedroom and said, "I want to see your ass wiggle in those heels Sugar. You go first." Jack giggled and began to head that way. He moved like he was on a catwalk in Paris. Toni smiled and said "I knew you had style the minute I laid eyes on you." Jack turned his head back towards Toni and winked.
They both took off their heels and climbed into bed. Toni pulled off her teddy and then did the same with Jack's. Jack began fondling Toni's large breasts as she began to massage his sack with her nails. Jack was getting harder and harder and Toni came to the rescue as she rolled Jack over and leaned down and began to go down on his cock with her luscious red lips. She took his cock deep and sucked hard, all the time fingering his man pussy with her long nails. First one, then two... Jack moaned louder and louder.... then three and four fingers! "Yes, Toni! Oh shit, yes!" With that, Jack filled Toni's mouth with his cum and let out a loud gasp. Before he could grab another breath, Toni put her mouth to his and shared the spoils of his orgasm. Jack smiled and swallowed it like a pro. He then began kissing Toni's tender nipples and running his hands through her golden blonde hair. As Toni's pleasure increased, she began to push Jack's head down towards her black silk panties. Feeling aroused yet again, Jack started to pull the panties off of Toni. But something was holding them on. Jack was so overwhelmed with passion that he didn't notice a snap on the back. Jack saw Toni's red nails unsnap the latch and pull down the only thing holding Jack back from Toni's... huge cock!
"Roll over Sugar." Toni whispered into Jack's ear. In a state of pure ecstasy with some confusion added for good measure, Jack did just that. Toni climbed on top of Jack's smooth ass and without warning began to stick her cock up Jack's man pussy. She reached around and grabbed Jack's nipples with her lethal weapons and pinched as she pushed further and further in. Jack was overcome with intense pleasure and pain and screamed as Toni's cock pushed all the way in and touched is pleasure point. In and out she went all the time pinching and grabbing Jack's tender tits. Within moments, Toni shook as she filled Jack with her juices. Jack answered back with a second shot of his own. They rolled over on their side with Jack's new sex hole still filled with Toni's cock. The two immediately fell asleep. Jack would need his beauty sleep. The girls had a busy Saturday ahead of them.