Dave and His Transvestite Blind Date

by james on July 28, 2009

Dave hadn’t spent many days in the city yet. He was from a small town and was here for his job, and he was still getting used to the big city life. Also, he was feeling quite lonely.

Seeing his loneliness, a friend at work arranged a date for him one evening. Dave hesitated a bit first, but the friend insisted. He said, “This will be great for you. Go enjoy with her.”

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So Dave waited in the bar waiting for her to arrive. Dot on time, a very sexy chick walked in the door. Dave’s heart missed a beat. This was a great blind date, he thought. But was it really this one? Yes, it was. She scanned the bar, saw Dave, smiled and began walking toward him.

She introduced herself with a handshake and with that Dave felt a sharp impulse running through his entire body. She had one of the smoothest skins he had ever seen on a woman and she had eyes that told she was game for anything. She sexily rummaged her locks as she talked. Dave found himself not concentrating on the small talk she made. Instead he was ogling at the area between her lips and her breasts. She caught him staring, but she just smiled it away.

They finished their little drink quickly and then started to move. Dave was living in a hotel room and that’s where he asked whether she would like to come. She quickly responded with a “yes”. Almost breathless, Dave guided her out of the bar and into his hotel room.

Dave fumbled with the keys and somehow opened the door. The woman was giggling at Dave’s clumsiness but she was highly excited too. They entered, shutting the door behind them. Dave quickly popped into the bathroom and came out, without a stitch of clothing on his body. The woman looked at him and smiled mischievously. Dave signaled her to do the same. She said, “Why don’t you do it for me?”

Dave found that exciting too. He walked up to her and started removing the buttons that held her blouse. He took it off her. Yes, her breasts were lovely. Not big, but small and pert. Small nipples. Dave loved them that way. He toyed with them. She had a neat belly underneath. Dave nibbled at her belly button.

He went lower. He came to her waist. Softly, he undid her skirt button. There, he felt like he felt something, which was weird. He removed her skirt and let it fall. It was then that his eyes became round as saucers. Inside, she had a long dong! This woman had a penis as big as his own!

Dave recoiled. But the ‘woman’ proved to be stronger. She pushed her penis into Dave’s mouth and made him suck on it. Dave resisted, but gave up. Slowly, he warmed up to it. He even began liking it. He had a go. He was so horny; he masturbated himself too.

Both took turns having anal with each other. Dave felt it difficult at first, even painful, but soon realized why some people enjoy getting anally penetrated. The evening turned out to be a great one, after all.

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