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What Left Todd In Shock Tonight

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Competition Entry: New Experiences
Todd was on a business trip to a small town in the Midwest. He had been there several days and was scheduled to leave the next afternoon. Since his business dealings were completed, he decided to go out and sample the nightlife in this little town. Asking at the front desk of his hotel where would be a good place to see some nightlife on a Thursday, the clerk directed him to a small music club a few blocks away. Todd being the cautious kind of guy when traveling opted to take a cab to the club instead of driving his rental car.

The cab let Todd out in front of rather plain-looking club front. He was having doubts about the recommendation he had gotten from the clerk. He walked up to the entry door and it was opened from the inside by a very pretty young lady. Todd guessed she was in her early twenties if that.

“Hello sir, welcome to Club Gather. There is a $10 cover charge or a $25 drink pass, good for six Club Drinks,” the young lady said.

“What is a Club Drink?” Todd asked.

“A Club Drink is a specialty drink we offer here. You can also get on-tap beers,” she told Todd.

“Okay, I’ll do the cover. I don’t know if I could drink six of anything,” Todd told the young lady at the door.

After paying the cover charge, he walked on down a hallway that led into the club. He was rather shocked at the sight of the club. It had a very upscale appearance, bright colors and a pleasant music going in the background. Todd just stood in the entry area taking it all in to get his bearings as to where the bar and other areas were.

Todd finally ventured over to the bar and ordered a beer. Sitting down on the barstool, he was surveying the club some more when he noticed a woman sitting at a small table off to the side of the room. He was appraising her beauty as she suddenly looked his way and caught him staring. Todd quickly looked away, feeling a little self-conscious that he was caught staring.

Todd sat at the bar, chatting with the bartender for a bit about the club and enjoying the music. They didn’t seem to be playing any pop or any hard rock, but a nice mix nonetheless. Todd sat there for a while longer and was considering leaving when the lady from the table walked over to him.

“Hi there stranger! Since you took such a keen interest in me earlier, I thought I would come and introduce myself. I’m Reggie,” she told Todd.

“Nice to meet you, Reggie. I’m Todd,” he replied.

“So Todd, are you new in town or just passing through?” Reggie asked.

“I’m here on business, or should I say I was. I got everything done and I’m catching a flight out tomorrow,” Todd replied.

“Well Todd, one last night out on the town before heading home?” Reggie asked.

“Well, actually it’s the only night out since I’ve been here. I spent most of my time here locked away in a little room with a couple of fat guys. It got rather intense in there a few times!” Todd replied.

“So you need somebody to show you a good time before you’re off to home,” Reggie said.

Todd snapped his head around to stare at her with that statement, and then just smiled at her.

“I see you like that idea, Todd, but hey, don’t read too much into that, Bub!” Reggie stated with a laugh.

Todd turned a shade of soft pink for a second because his mind had gone down the rabbit hole of dirty thoughts. He slowly shook his head for a second, wondering why he had done that.

“Since you caught me with my mind running to the gutter, can I buy you a drink?” Todd asked.

“Sure, a Rum and Coke please,” Reggie replied.

Todd caught the bartender’s attention and ordered two Rum and Cokes for them. They sat there and chatted, drinking their drinks, getting new ones a couple of times.

While chatting, Reggie had placed her hand on Todd’s leg and slowly let it creep up his leg until she had it just below his crotch. She was gently squeezing his thigh as they were talking. With her efforts and actions, Todd was starting to get an erection that was becoming very noticeable.

Reggie leaned into Todd and gently pressed a kiss to his lips. He was taken slightly off guard by her action but didn’t object. Her lips were so soft and delicate pressed against his. He reached out and placed his hand on her bare thigh as they kissed. Very subtly, she redirected it to her breast. They sat there and made out for a bit longer.

“Would you like to go back to my place?” Reggie asked.

“Are you sure about this?” Todd replied.

“Yes, I’m very sure, but if you’re not sure we can stay here for a while longer and say our good-byes,” Reggie replied.

Todd sat there for a moment, thinking about it and decided to go with her. “Let’s go if you’re sure, Reggie,” Todd said.

They left the club and as they stepped outside, a gorgeous red Corvette pulled up. A guy jumped out and tossed a set of keys to Reggie. She caught them in midair and told Todd to get in. Todd just stood there a little dumbfounded, staring, until he heard Reggie rev the motor. Todd slid into the passenger seat to a big smile on Reggie’s face.

“What’s the matter Todd, didn’t expect me to have a car like this?” asked Reggie.

Well, Todd didn’t know whether to answer or just get out of the car before she threw him out, but he didn’t get a chance for either as Reggie rocketed away from the club. Todd stayed quiet on the ride, not knowing if she might just dump him off somewhere as punishment. After crossing through town, they pulled up in front of one of the more modern buildings in the town.

Reggie got out of the car, handing the keys to a young man by the door. Todd jumped out and followed behind her. Todd was thinking to himself, “That is an ass I could follow around all year!

Then Reggie turned towards Todd, saying, “I was wondering if you were coming or not, after the silent routine in the car.”

“Sorry, I was caught off guard about the car and then I seemed to offend you. I wasn’t sure if you were just going to dump me out somewhere in the city,” Todd replied.

“Oh, you’re being silly, Todd. The car catches a lot of men off guard,” Reggie replied with a little laugh.

Todd followed Reggie to a bank of elevators. When the door opened they got on and Reggie pushed the button for the top floor of the building. They rode up in a comfortable silence, but Todd was feeling a little anxious about what might follow.

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Then the door opened and Todd had a wonderful view of a very beautiful condo, all done with a woman’s touch for sure.

Reggie led Todd into the living room and offered him a drink. She went over to a small bar and fixed them both a drink and came back to sit next to Todd. They chatted for a bit until they both started getting a little bolder, moving closer and exchanging light kisses that were rapidly turning into longer deeper kisses.

Reggie had her hand on Todd’s large bulge in his crotch, and he was feeling her perfect breasts as they continued to make out. Finally, Reggie slid to the floor in front of Todd, pushing him back against the couch. She started kissing the bulge in Todd’s pants as she worked his belt, button and fly open. She soon had him down to his boxers, and they were gone just as quickly.

Reggie was holding Todd’s cock at the base, slowly stroking him as she lowered her head onto his cock for the first time. Todd jumped a bit at the sensation of her taking him in but relaxed as she steadily went down on him over and over. Reggie finally was taking Todd’s whole cock in her mouth each time she went down along his length. As she pulled back she would tighten her lips and start dragging her tongue along his shaft. This brought moans of pleasure from Todd at a much greater volume each time she did it. Reggie would stop with just his cock head in her mouth and twirl her tongue all around it enjoying the sensation she was causing Todd.

Before long, Todd was bucking his hips at her as she took him deep. Reggie, sensing that Todd didn’t have much time left before he came, wrapped her free hand around his balls and gently rolled them in her fingers.

“Oh my god, Reggie, I’m going to cum!” Todd shouted out at her.

Reggie, already feeling his impending orgasm, took him as deep as she could and held him there, sucking greedily on his cock to get all of his seed from him. Todd started cumming, with long, deep moans accompany each spurt of his semen into Reggie’s mouth. She swallowed each mouthful as best as she could until a little ran past her lips.

Finally spent, Todd relaxed back onto the couch, catching his breath. Reggie released his spent cock from her mouth and leaned back on her calves and looked at Todd. He could see the white line of cum that ran down her face from her lips to her chin. He thought she looked so hot kneeling there like that. Then Reggie took her finger and traced the white line back up to her mouth and licked her finger off. This little bit of action caused an involuntary moan to escape Todd.

Reggie got up off the floor and disappeared for a moment. She came back with a wash cloth to clean Todd off with. She saw he hadn’t really moved yet, still sitting there with his pants and underwear on the floor at his feet. His cock was still semi-erect, but softening right in front of her eyes.

Kneeling in front of him again, Reggie slowly ran the wash cloth over Todd’s cock and balls, cleaning all the saliva and cum off of him. Once he was clean, she leaned down and kissed his cock right on the swollen mushroom head. This caused Todd to jump a bit; he wasn’t ready for that at all.

Reaching down, Todd caught Reggie’s hands and pulled her up onto his now-soft cock. Reggie was still in her dress and panties, but this position had Todd’s cock resting along her panty-covered crotch. She thought he felt wonderful there. Todd kissed Reggie as he was undoing the buttons on her dress, little by little revealing her breasts to him. Once he had the dress unbuttoned far enough, he slid it off her shoulders, completely uncovering her beautiful breasts for his attention. Todd leaned down and started tonguing the left nipple as his left hand was fondling her right breast. He would encircle her nipple with his tongue and suck on it greedily before releasing it to gently lick at it again. He had captured her right nipple in his fingers and was just rolling it back and forth as he sucked at the left one.

Todd wasn’t giving Reggie much of a break on the stimulation, and she could feel herself becoming excited as Todd continued. She could also feel Todd becoming hard again under her as his cock pressed up against her panty-covered crotch. She knew she only had a few minutes to decide to stop Todd or confide in him the truth about her.

Finally coming to her decision, she pushed back against Todd to move him away from her.

Todd pulled away and stared at her for a moment before asking, “Did I do something wrong, Reggie?”

Reggie slid off his lap and stood in front of him, letting her dress drop the rest of the way off of her body. Standing there in only a pair of thin satin panties, her secret was a little more.

“Todd, I like you and have had fun with you tonight so far, but I need to tell you something I don’t share with a lot of people. I’m a woman by birth, but I didn’t have all my female parts. I was born with a small penis and balls instead of a woman’s vagina.” Saying this, Reggie pulled down her panties.

Todd looked at her like he had been hit by thousand volts of electricity. He just stared at her nakedness as she stood in front of him revealing her most hard-kept secret. After a few moments of no response from Todd, Reggie turned and walked out of the room. She returned a few moments later with a robe on.

Todd looked at her again and stammered out, “Reggie, I’m sorry I froze there, but you caught me totally by surprise.”

“That’s okay Todd, I knew it would be a shock and you didn’t freak out right away on me, so that was a good thing,” Reggie replied.

“I’ve never been with a woman like you and have only seen women like you in porn pictures,” Todd stammered a bit as he was reaching for his underwear. He was feeling a little exposed sitting there with Reggie.

“That’s okay Todd. I was enjoying your attention and was becoming excited. I had two choices - either tell you about me or stop you and push you out the door. I really like you, so I chose to share my secret with you. I hope I made the right choice here, but if you want to leave I understand,” she told him.

Todd sat there for a bit not saying much. Reggie curled herself up, leaning against the back of the couch just waiting for Todd to decide for himself what he wanted to do.

“Reggie, can I ask you some questions? I don’t mean to pry, but I was enjoying my time with you as well,” Todd said to her.

So this was the beginning of a long night of asking, answering, explaining and understanding for them both.

Morning found them in Reggie’s bed together, curled up like the lovers they would soon become.

Published 
Written by Road_Runner
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