Dave and His Transvestite Blind Date

28 Jul 09

Dave and His Transvestite Blind Date

The city was quite new to Dave. He had come from a town for a good job in the city. Though he had the job, he was feeling lonely here. He was still getting used to the city.

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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In the evening, Dave found himself at a bar, waiting for his blind date to arrive. Right on time, a very pretty woman walked in through the door. She looked great. Dave was pleased. There was a moment of nervousness when he felt this might not be his date, but that was quieted when she looked at him, gave a little smile and walked in his direction.

Dave felt current rising through his body when she shook hands with him. Her skin was smooth, eyes aglow with mischief and she had a wonderful way of playing with her blonde hair while she talked. Dave could not concentrate on anything else but how he would lay this lady. He kept staring at her breasts and lips all the while they talked and, once or twice, he saw that she caught him staring.

They ordered a drink and Dave finished it hyper quickly. Then Dave wasted no time in asking whether she would like to accompany him to his hotel room. She made a silent nod. Dave almost lost his control there. He escorted her out of the bar and led her to his hotel.

Outside the room, Dave found himself fumbling with the room keys. She smiled once again, at his hasty awkwardness. However, she was very excited too. Dave could tell. The door was opened, they entered and they shut it. Without further ado, Dave walked into the bathroom and came out, completely naked. She was a little startled, but then found herself looking at him appraisingly. She let out another one of her smiles. Dave then told her to go in and do the same. But she said, “You do that for me!”

Dave was totally breathless by now. He went close to her and unhooked her top. Her breasts were lovely. They weren’t huge or even big, but they were pert and had small nipples. Dave had a go at them. Her belly was smooth and flat; Dave played with her button for a while.

Then he went lower. He unbuttoned her skirt. He felt something inside that he found odd. He unzipped the skirt and let it fall. That was when he gave the gasp of surprise. This lady wasn’t a lady! She had a penis larger than his!

Dave stepped back. But the ‘woman’ was stronger. She took Dave’s mouth and placed it on her cock. Dave found himself sucking a penis! He resisted, but the ‘woman’ was stronger. Slowly, he got used to it. He was so horny! He also began touching himself. Later, each one of them had anal sex with the other. Dave was scared at first, but as he was learning so many new things, he thought he would learn this too. He actually found it enjoyable once the initial pain was over. It was not such a bad turnout, Dave felt.

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.