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"Yes my boy. I didn't know that you were going to be here," said Richard.
"Well, its for a good cause. Plus you get a really good meal to go with it," he said.
Richard smiled and then his eye went towards Chloe.
"Well, well. Who is this lovely young lady?" inquired Richard.
"Richard, I want you to meet Chloe Windsor. Shes a friend and my date tonight," he said.
"Hello," greeted Chloe.
"Well, its lovely to meet you Ms. Windsor. I am delighted to see you with some good company here Mathew. Especially since your breakup with Shannon Masters," he said. "I am good friends with her father and came to know that you two had been dating for a while."
"Yes we were dating for a while Richard. But it wasn't mean to be," said Matt as Chloe looked on.
"Oh well you are young and have all the time in the world to find the one. Anyway, I hope that you two have a good evening. I will call your office tomorrow Matt and we can finalize the details on the contract," said Richard and bid them farewell.
"So, how long have u been single," asked Chloe.
"Well. I broke up with my ex-girlfriend Shannon just a couple of weeks ago," he said. "We were supposed to come to this thing together, but here we are," he said.
He gazed at her as she gave him a sympathetic stare but with a smile.
"Well, we are here tonight. So lets not talk about the past. What is past is gone. Yesterday is history. Tomorrow is a mystery. Today is a gift," she said.
He looked back at her and smiled. She was quite charming. And not only had she removed the mere thought of Shannon from his mind, but he had butterflies in his stomach now. They sat down and talked and talked. Matt could see that she was excellent company to be with. She was witty, smart and had a way to keep all of his attention. She seemed more different than their meeting earlier in the day. They had their meal and continued to enjoy the evening.
"Hey. Lets dance," said Chloe.
"Oh, I am not much of a dancer," said Matt.
"Come on. I am not either. Plus its a nice slow song," she said and held out her hand.
He took it. He didn't know why. But he did. Shannon had never been able to convince him to dance at any of these shindigs, but he was simply unable to refuse Chloe.
They moved around the dance floor on a nice romantic song played by the band in the back ground. They looked into each others eyes as they moved. He looked rather meaningfully into her eyes and she smiled a small smile and gazed back into his.
"You... are simple beautiful," he said.
"You're pretty handsome yourself," she smiled as she replied to him.
"I have to admit something. I was not looking forward to this night at first. To be honest I was a bit uncomfortable. But now. I mean. Ah," he said
She kept looking into his eyes. Man, those eyes. They were hypnotic.
"I am having such a good time with you tonight," he said.
"Me too," he replied.
"Would it be too presumptuous of me if I kissed you?" he said.
"Do you have to ask?" she replied.
He moved towards her slowly and planted a kiss on her. It was soft, but it was intense. They broke their kiss as Matt looked at her. She leaned into him and rested her head against his shoulder as they continued to dance.
Matt walked Chloe to the front door of her house. There was a silence.
"I had a really good time tonight. Thank you," said Chloe.
"I should really be thanking you," he said.
There was silence again. They stared at each other. And then out of nowhere, Matt leaned in and kissed her again. The kiss was slow. Soft.
"Would you like to come in?" asked Chloe.
Matt thought hard about this. Here he was standing outside a gorgeous woman's house. He so wanted to go inside. But she was a transsexual. He knew he didn't like men. But Chloe was no man. She was beautiful. She was amazing. She was drop dead gorgeous.
"It's ok. I understand if you don't want to," she said.
He kept thinking. Then he thought to himself, that he liked her company. And who would find out in any case. And if she wanted to do anything he wasn't ok with he was sure that they could stop.
"Yes. I would like that very much," he said.
Chloe opened the door and they walked inside. The house as much as it had looked charming from the outside looked even more homely and inviting inside. She had excellent taste. They moved into the living room which was decorated rather nicely.
"Would you like some wine?" she asked.
"Yes. Wine would be good," he replied a little nervously.
She went went into the kitchen and bought out a nice bottle of red wine and 2 glassed. She looked at him and smiled as she poured the wine. He looked nervous. But for some reason, Chloe was getting a little nervous as well. He was incredibly dashing and handsome. He was intelligent and sophisticated. Exactly the kind of man she kept dreaming about. Plus the way he looked nervous was obvious to her that he had never been with a TS woman before.
She finished pouring the wine and they sat down on the sofa and sipped. The sexual tension in the room was very much evident to both of them. Matt then moved close to her and moved a flock of her hair behind her ear. He softly brushed his hand against her cheek and she closed her eyes. She opened them and Matt moved in to kiss her. He kissed her with a little more urgency this time and started to run his hand on her legs. Chloe slowly moved her hands his shoulders and slowly moving them through his hair.
If there was any doubt in Matt's mind about what he was doing or going to do, they had gone completely out the window. They kiss started to get more passionate and intense with every movement.
Just then Chloe broke the kiss.
"Why don't you wait right here and I'll just go freshen up," she said.
She got up and went towards the bathroom. He just sat there and waited and while he waited he noticed the giant tent pole in his pants. He was very much aroused, just as much as she was. Again nervousness was setting in as he kept thinking about what was about to happen.
Then he heard the door open and shut. And she walked into the room. Every ounce of second thoughts were for sure no longer in his mind now. Standing in front of him was a goddess in a black bra, panties, suspender belts and high heels. It seems she was a little more nervous about what was going to transpire next.
He got up as she moved towards him. She stood against him and he kept gazing at her. She then threw her tongue out and licked his lips. This was all the encouragement that Matt needed. He grabbed her and started to kiss her full and hard on her lips. His hands started to move around her body as once again she interlocked her hands behind his neck. He started to kiss her neck and she let out a soft whimper. He started to move his hands on her breasts as he continued to kiss her neck. Slowly but surely, Chloe then moved her hands towards his erection. She kept rubbing her hands over his cock and kept moaning as he continued to kiss her. Matt stopped as he looked on and saw that wanting look in her eyes as she continued to stroke his dick over his pants.
She then knelt down and unzipped him. She put her hands inside his trousers and released his cock from its prison. Hanging out of the zipper was a 8.5inch cut cock full at attention. She stroked it and looked up at him. Watching Chloe do this as she looked at him was making him even more rock hard if it was possible. Then there it was. She licked the head of his cock. Matt could only moan. Seeing that her actions were having the desired affect, she put his cock into her mouth.
"Ohhh Fuckkkk!" cried Matt.
Chloe continued to suck on his meat and letting out a moan every now and then. This was driving Matt nuts. She then released her cock and started to lick the base of the shaft all the way to the top. At this point Matt was starting to loose control. She continued to keep licking his cock and making it wet with her saliva. Now Matt knew that he was getting really close. Before she could continue and make him loose his load, he removed his cock from her mouth, picked her up and sat her down on the arm of the chair.
He noticed a tiny little bulge in her panties. He moved it aside and saw her tiny little penis. It could not have been more than 4inches long.
"You don't have to do this," she said.
Hearing those words coming out of her mouth made his heart warm. But he wanted to make her feel good just like she had done to him. He started to lick it and she let out a whimper. He licked it a few more times and she had to throw her head back. He then took her tiny cock into her mouth and started to suck. For some reason Matt was not feeling anything. He didn't feel any different than he would if he was going down on a real woman.
She put her hand on his head as an encouraging sign and he started to really suck her tiny little cock now. The way she kept moving around, Matt knew that he was doing a god job. He kept at it for a few more minutes, making Chloe moan and whimper. Chloe was in complete ecstasy. Looking down she saw a man who was straight but going down on her feminine boy clit, something that she had nod experienced in a very long time.
"Oh Matt...oh that feels so good...please Matt keep going... aaaaannnnnnhhhhhhh... annnnnhhhhhhhhh," she cried.
Matt was loving every minute of it. It was a new experience for him but giving pleasure to this divine creature was driving him insane.
"Oh...Matt...please stop...stop...I don't want to cum yet...," she cried.
Slowly, Matt stopped sucking on her cock and gave it a final lick. Chloe shuddered as she felt his tongue on her cock for the last time. She got up and gave him a big wet kiss. Then she started to undress him. One by one she started to fling his clothes all over the living room, until Matt stood naked in front of her in all his glory.
He grabbed her once again and put her down on the sofa. He lay on top of her, his erect cock rubbing against her tiny one. They went mad at each other, kissing each other like they had never kissed anyone before. The heat between then could have melted the room around them and they would not have noticed. The was the intensity they went at with each other.
"I want you inside me Matt," whimpered Chloe.
She removed a condom from her bra and handed it out to him. He removed the condom and put it on his cock. Chloe looked at him with lust as he stroked his sheathed cock. He bed over her torso and pushed her legs to her side. Her cock lay limp on her belly as his own manhood touched the crease between her cock and her asshole. He started to tease her gentle rosebud as Chloe continued to moan.
"Please Matt...don't tease me...please...," she cried.
Matt then held his cock and aimed it for her hole. He pushed inwards but had some difficulty. He tried a little harder and soon the head of his cock popped into her hole. Chloe let out a big moan as she felt his big cock enter her tight little hole.
"Are, you ok? Am I hurting you?" he asked gently.
"No," she said as she raised her head began to kiss him once again.
Matt pushed in a little more harder as his cock slowly started to enter into her bowels. He kept pushing in until he was all inside till the hilt. His balls touched her soft ass as her hole had swallowed everything he could give her.
He took her leg gently and placed it on his shoulders. She looked deep into his eyes as he looked into hers. There was an unspoken connection. He didn't move as he wanted to let her feel more accustomed to his cock inside of her. He bent down once again as they kissed. Once Matt broke the kiss he slowly started to move himself going in and out of her tight ass.
He kept rocking his body slowly so that it would not make the experience unpleasant for either of them.
Chloe began to thrash her head around as he slowly fucked her. She was seeing stars as this greek god of a man was fucking her. Panting loud and hard, Matt started to increase his pace. He had never felt this incredible. It was amazing. Never had a woman had such a strong effect on him. We went at it for a few more minutes. And then he slowed down.
He laid back on the sofa and said "Come on top of me"
She got up slowly and got on top of him. She slowly started to gyrate her hips teasing his cock. Then Matt grabbed her ass and gave it smack. She winced a little as he grabbed is cock and positioned it at her entrance. She took the sign and slowly started to impale herself on his hard rod. She could feel her cock rubbing against his stomach as she went all the way down.
She put her hands on his chest and started to move up and down. He grabbed her hips and started at her beautiful face as he continued her movements. She started to move fast. All Matt could do was give himself up completely to her. She started to moan as she felt a stir in her balls. She had started to cum from all the fucking and squirted a few times all over he chest. This drove Matt even more wild as he started to push her down on his cock harder and harder. He was getting really close and she noticed it.
"Yes...Chloe...oh fuck yea...I am getting really close...please keep going...oohhhhhhhhh fuckkkkkkk," grunted Matt loudly.
He had just released himself inside the condom deep inside her ass. She squealed in joy as she saw him squirm and release all his load. She slowed down her movements once he was done. She looked at him deeply as she bent down and gave him a kiss. Matt returned the kiss with as much passion as Chloe was putting into the kiss. She got off him and lay on his chest.
"That was...amazing!" he said.
"I know...I was there," she replied with a smile.
They kissed once again as Matt picked her up and started to move towards her bedroom.
It was 7am when Chloe woke up. As soon as she woke up she turned to the other side. There he was. Lying still, deep in sleep. What a man, she thought. She had never met a man like Matt. Someone who seemed like the perfect man. Yet she could feel that he walked around with the weight of the world on his shoulders. She stared at him as he slept peacefully.
She slowly started to get out of bed, and put on her robe and proceeded to the kitchen. She started to prepare coffee and then she heard a noise behind her. It was Matt.
"Hey," he said.
"Hey... Good morning," she said as she smiled back at him.
She noticed that he had this big grin on his face. But noticed that she was flashing him the same goofy grin back. He moved towards her and gave her a kiss on her lips.
"You are amazing," he said. "I had a really good time last night."
"Why didn't you wake me?" he asked.
"You looked like you were soundly asleep. I didn't really want to wake you," she said. "Would you like some coffee?" she asked.
"I would love to, but I have to get to the office. I'll have to run home and change for a meeting I have at 9:30," he said.
"Oh, that's OK," she said.
She wanted him to stay but he couldn't. She felt something inside but dismissed it almost immediately.
"I guess, I should get dressed then.," he said goofily.
Matt turned around and moved back into the bedroom where all his clothes from last night lay in a heap. Dammit! Why was he so stupid. Why didn't he just say that he wanted to stay. He didn't know why? This was so out of character for him. Firstly, he had hired an escort. A transsexual one at that. Then he she seemed to capture his senses. He slept with her and it was the best sex he had ever had! He was getting all confused. He started to get dressed.
In the kitchen, Chloe started to move around half heartedly. She sipped her coffee as she looked around for something to make for breakfast. What's wrong with me? Why do I want him to stay? He's a client! He's a client! She dismissed the thought from her head once again.
Matt moved out into the hall. Chloe entered and saw him checking if he had everything on him. He saw her standing there in her robe and he got butterflies in his stomach once again. He moved towards her and kissed her.
"Thanks. I really did have a good time," he said. Then he couldn't believe what he said next.
"I want to see you again," Dammit!
"Yea. I would like that. We can set something up," she replied.
Uncomfortably he moved a bit and then instead of kissing her on the lips he kissed her on the head and proceeded towards the door. What was happening to him. He got into his car and drove off.
Chloe stood there as she saw him leave. She quickly had her coffee and heard her phone ring.
"Hey babe...where the hell have you been? I tried calling all of last night and I didn't get an answer," said a female voice on the other line.
It was Karen. Chloe's childhood friend. She had known Chloe since he was known as Charlie. She had always been supportive of what Chloe wanted and had always stood by her thick and thin. The biggest thing was that she knew what Chloe did for a living and still was supportive. It was a true friend like Karen that kept Chloe's sane in this wild world.
"Nothing. I was out last night," she said.
"Oooohh...sounds like you had a hot "date"...hahahaha," she teased.
"Stop it. And yes I was out," replied Chloe.
"Well I sort of guessed since you didn't pick up any calls at home, so I didn't want to disturb anything by calling you cell. Anyways, I am just 2 blocks away from you place. I'm in the mood for something good for breakfast. I was thinking we could go to Bradleys Cafe."
"Yea, ok. I'll get ready in a few minutes and meet you outside."
15 minutes later, Chloe was all dressed and headed out the front door. The red mini cooper was standing right there with Karen inside waving her. She beamed at Karen and opened the door and got in and they drove off.
They reached Bradleys Cafe and got a table next to the window and sat down.
"So, I got news! I broke up with Dominic," said Karen.
"What?? Why?" asked Chloe.
"It was getting too messy. We were always arguing. We were having some trouble for a while. So I just broke it off," said Karen.
"But I thought it was going great," said Chloe.
"Yea, it was. But then these guys create situations and then sort of push us to break up with them. Pffft. Guys! Who needs them," she said.
"You know. You behave just like one. In-fact, I think you were just getting bored with him. So you decided to dump him!" said Chloe.
"You know me so well!" laughed Karen.
"I knew it!" said Chloe.
"Anyways. Leave that alone. How was this date last night?" she asked.
"It was fine," she said and then looked down at her coffee.
"Oh come on. You have to give me more than that!" she said as she looked at her.
"It was a new client. It started off rather weirdly. But it started to get pretty relaxed. We had a good time. He took me to this charity event. We had a lot of fun. He was great," replied Chloe.
"Uh-oh," she said she gave her a look with devilish smile on her face.
"What?" asked Chloe.
"You like him!" teased Karen.
"Oh stop it! He was just a new client," said Chloe.
"Then why do you have that big smile on your face?" questioned Karen almost as if she was interrogating Chloe.
She looked back at Karen sheepishly. "Well he was nice. We had a good time. He was a gentleman in the true sense of the word," replied Chloe.
"ehhhh ewww eh ewwwww ehhhh ewww," retorted Karen mocking Chloe.
"Stop it," cried Chloe.
"I don't know. You look all lovey dovey from all the sex you had last night!" teased Karen again.
"What? How do you know I had sex with him?" retorted Chloe.
"Well that stupid smile plastered all over your face tells me everything! You really like him don't you?" said Karen.
Chloe looked at her. "I don't know. There was something about him. He was unsure in the beginning. But as the evening started coming to an end we were talking and laughing and dancing. And then he kissed me. There was something. I don't know. And the sex. I have never had a client like that. Most punters would come do some small talk, fuck you and leave. But he was different. The second time was even better," she said dazing away.
