Taylor had always been desperate for a girlfriend. It was literally the only thing on his mind 24/7, and he was starting to feel as though it was never going to happen for him. This was until he finally met Jessica...
#crossdress #crossdressing #sis...
Taylor simply could not believe the way everything had just happened. As Jessica had been walking away, he had stared right at her ass and could feel himself getting excited. He saved Jessica's phone number and headed for class, but did not once stop thinking about what would happen after school. Was he finally going to lose his virginity? Or was she going to beat the fuck out of him? He debated in his head. He didn't need any time at all to decide if was worth the risk or not, he was always going to go as Jessica was way too hot to miss out on that was for sure. He didn't see Jessica again for the rest of the school day and, as the bell rang, he decided he would text her and sent a simple "Hi it's Taylor". Almost immediately, he heard his phone ding and she had responded, but it wasn't the message he expected. " Hello Taylor, before you come to my house, shave your face" it read, and Taylor stood for a moment confused. "Ok see you soon!" He responded, thinking nothing of it and went home to shave the 3 barely visible hairs that were on his chin.
As the clocks struck 5, Taylor was about to ring the doorbell when his phone dinged; Jessica had sent him a photo:
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"Fuckkkkk" he muttered under his breathe as he felt his blood rush to his penis. Just as the outline of his shaft had become clearly visible, Jessica opened the door and it was pointing right at her. Without a word, she grabbed it hard and dragged him inside. Taylor followed her with no urge to resist, and she continued to drag him upstairs and into her bedroom " Sit there and wait" she ordered and Taylor did as he was told as Jessica left the room. 60 seconds or so had passed and Taylor had got the picture of her up on his phone again, she looks amazing. Just as he was starting to miss her, she returned and took a picture of him.
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Taylor looked up and noticed she had brought with her a razor and shaving cream. " Take this and you are going to shave your entire body smooth for me, go the bathroom now" she demanded. "Huh? Why?" He replied confused "Just fucking do as I say!" She shouted and he quickly hurried to the bathroom. Taylor didn't really want to shave his legs but after a few seconds of deliberation he decided that it was definitely worth it if he was going to get to finally lose his virginity. Reluctantly, he squirted out plenty of shaving cream and covered his body, before carefully gliding the razor all across his skin, stride after stride until he was completely smooth from the eyebrows down. He didn't want to anger Jessica and potentially miss out on the opportunity at hand, so he made sure to do as best a job as he possibly could without missing a spot. After briefly checking out his new look in the mirror, he returned to Jessica wearing only his boxers in hope that she would be happy with what she sees.
