Chapter 85
At ten the following evening Valerie and Jason stood outside the Pink Elephant. There were a few people in line outside so they joined the line and waited. Valerie was dressed in jeans and a tight-fitting blouse. Jason had bought a black flared cocktail dress with straps over his shoulders. He was wearing the four-inch heels and the black thong. They had to wait ten minutes before they were let in and when they did Jason headed for the bar where he ordered a double vodka tonic. He was very nervous and drank half the drink before putting it down. Valerie ordered white wine which she sipped on while surveying the crowd.
Since it was a Monday there were a lot of after-work people, who had come for the Happy hour and then stayed. She guessed that there were about three men for every woman which wasn’t surprising. A few women that walked past them gave them a smile or a wink, which both Valerie and Jason ignored. It took almost half an hour before the first guy approached them. He had been sitting with some friend and had kept eye contact with Valerie.
“Hi, what’s your name? I’m Dennis,” he said.
“Valerie, this is my friend Nina.”
He kissed both of them on the cheek and then sat down on a barstool next to Valerie. He had brought his beer with him and when he had finished it he ordered another. While he waited, he said, “I haven’t seen you here before.”
“It’s our first time.”
“So, you are a couple?”
Valerie giggled, “kind of, I guess.”
“Oh, I see.”
“My friend is a crossdresser.”
“Interesting, and what are you looking for?”Content (C) Nôv/elDra/ma.Org.
“Nothing special, just a few drinks and we’ll see what happens.”
Dennis nodded slowly and drank from his new beer. When he finished, he said, “what about you and me continue this party somewhere else?”
“Oh, I thought you were gay.”
“No, I’m bisexual.”
“Cool, can my friend come?”
Dennis laughed, “not tonight, I want a real woman.”
Valerie leaned closer and whispered in his ear, “sorry, we want to have fun together. You wouldn’t know anyone who would be up for a three-sum, with my friend?”
He thought for a while and finished his beer while he did. Then he said, “I just might. Wait here, I’ll go and talk to him.”
“What did he say?” asked Jason when Dennis had left.
“He wanted me only, but he might know someone who is into crossdressers.”
Jason drank from his third vodka tonic. “God, I am nervous.”
“Relax, you will be fine. I’ll be there to help you out.”
A few minutes later a man in his mid-forties came up to them and took Valerie’s hand in his. “Hi, Dennis said you were looking to party? I’m Jerry”
He wore glasses, had a three-day stubble, and wore a dark grey suit. His brown hair was tousled and he had a mischievous smile.
“We might. What are you into?”
“Most things. I heard your friend has a cock.”
“Yes, he does. Are you OK with that?”
Jerry stepped around Valerie and stood in front of Jason, who looked up at him, with a weak smile. The guy was almost a head taller than Jason and much bigger.
“What’s your name?”
“Nina.”
“Cool, I’m Jerry. You are very pretty, did you know that?”
Jason blushed. “Thanks.”
“Have you ever been with a man before?”
“No.”
“Mm, I see. Would you like to try?”
Jason nodded, and said, “yes, I would, but only if Valerie can join us.”
Jerry laughed. “The more the better. Your place or mine?”
Jason asked where he lived and they decided to go to Jason’s since it was closer.
When they arrived Jason opened a bottle of wine while Jerry and Valerie sat down on the sofa.
“Nice place you got,” said Jerry.
“Thanks, it’s close to work so I love it,” said Jason from the kitchen.
“How long have you been a crossdresser?”
“Just over a week, it all came out suddenly,” said Valerie, who was studying the bulge in Jerry’s pants.
“Really? And how did that happen?”
“He kind of confessed to me, and I then helped him to become Linda.”
“Wow, you have done an amazing job.”
Jason placed a glass each in front of them and sat down in the chair opposite them. He crossed his legs and the dress slid up his thigh and Jerry gave an approving nod. After drinking from the wine he said, “out of curiosity. Have the two of you ever got it on?”
Jason blushed and looked at his glass. Valerie giggled and said, “yes, we have. Nina bought me a strap on and we used it the other day.”
“Cool. Did you like it, Nina?”
“Yeah, I did. It was amazing.”
“How big?”
Valerie held up her hands. “About so, it’s seven inches.”
“Then you are in for a surprise, the both of you. I’m eight and a half.”
Jason choked on his wine and coughed. Valerie’s eyes went wide and she swallowed hard. “Wow, I have never tried one that big.”
Jerry laughed. “Are you OK, Nina?”
“Yeah, thanks for asking. I would like to say, please be careful. I have to work tomorrow, and I would like to be able to walk to work.”
“Relax, I am sure Jerry will be gentle.”
“I promise.”
Valerie couldn’t hold back any longer and put her hands on Jerry’s pants. “May I?”
Jerry smiled and nodded his approval. She slowly opened the button and then pulled down the zipper. Jerry raised himself so she could pull down the pants and when they were off, she folded them and put them on the coffee table. Jerry was wearing dark blue boxers and his cock made them look like a tipi. Valerie slowly put a finger inside and then began to pull them down. When his cock popped out she gasped.
“My god, that thing is beautiful. Just look at it, Nina.”