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#Cuckold #Teen #Trans #Virgin
By August Moon
Jerry finds his true identity in the arms of a man from the far side of the woods.
Jerry was bored with playing games on the computer. Being home alone he decided to surf the Internet. He went on a site called teen crossdressers. He watched as a teen boy was turned into a beautiful teen gurl. He was introduced to an older man who would be her escort for the night. As he watched he found himself getting hard. He watched as the man took her to a hotel where they had sex. Jerry was breathing heavily and felt wet after the video. He had shot his wad in his shorts. He took note of where he found the site. Not taking time to change, he decided to go for a bike ride.
He decided to ride in the woods behind the neighborhood that he lived in. He wanted to investigate them by riding further into the woods than he had been before. On his way, he passed by a house set back away from the path. It looked eerie. He shrugged his shoulders and rode on. He decided that he had ventured far enough and turned back. He came a fork on the path but couldn’t recount which one was the right one. He took the one he thought was right but then he heard a pop and his tire went flat. He started pushing his bike and as he rounded a turn he saw that he was close to the house on the path. As he was passing by he heard a voice.
“Are you having trouble with your bicycle?” Stan Broadmoor asked the boy.
“Yes, my tire went flat a ways back.” Replied Jerry.
“Well bring it out to my workshop in the barn and we’ll fix it.”
Jerry took his bike to the barn. Stan introduced himself and asked Jerry who he was and how old he was. He told Stan that he was thirteen. They made small talk as Stan fixed the leak and put the tire together and on the bike. He asked Jerry if he would like a cold soda and some cookies. They made their way into the house and Stan had Jerry go into the Den while he got the cookies and the drinks. Jerry looked around while waiting and saw a magazine laying open on a table by the sofa. He picked it up and saw it was about boys being gurls. He felt his cock stir. But just as he was about to pick it up, he heard Stan coming. He sat back up.
“It’s so nice to have someone stop by, even if it was for a flat tire. People look at my house and avoid it because of how it looks. Didn’t you have trouble with it,”
“Well, I really didn’t think about it because you looked so pretty and nice. So I just felt okay with you.” Jerry told him.
“Thank you for the compliment but pretty is for young girls and good looking boys like you. And it makes me happy that you feel comfortable with me. I hope you stop by again and you’re welcome to stop by anytime. You are a very pretty Boy and with your long hair and a dress, you would pass as a girl. You really would.”
Jerry’s cock twitched when Stan referred to him as a girl especially after seeing the magazine. He wondered if Stan liked boys dressed as girls. He wanted to come back again to find out. It was getting late and he told Stan that he needed to go. Stan walked him to the door and Jerry reached up and kissed Stan on the cheek close to his mouth. It was a lingering one. Jerry whispered to Stan,
“Thank you and I will be here tomorrow for sure!”
“Bye Jerry, I will be waiting for you pretty boy.”
That night Jerry thought about everything that had transpired today. Especially how he felt when he watched the cross dressing video. And then when Stan called him pretty not once but twice. His cock was rock hard as he thought of all this. He was excited about going back and couldn’t wait to go. The next morning after taking a shower. On a whim Jerry went into his older sister’s room and looking in some drawers found where she kept her panties. He picked out a pretty red laced pair and took them to his room. He put them on and looked at himself and liked what he saw. He liked the feel of them. His cock stretching them. He put his pants and shirt on, ate some breakfast and made his way to Stan’s house. The feel of the silk on his tight ass and cock made him feel good. He knocked on Stan’s door and Stan let him in. As he walked past him, Jerry reached up and kissed him again near his lips. Jerry blushed as he looked at Stan.
“Mmmm, I love those sexy kisses of yours. They are so sweet coming from a pretty boy. I hope we can get to know each other in a closer way.” He said to Jerry.
“Mmmm, I just want you to know how much I am thankful for your helping me. I, I really, well that is, I really wanted to kiss your lips.” Jerry told him and dropped his head.
Stan took him by the hand and led him to the loveseat and sat down with him. He lifted Jerry’s head and kissed him on the lips. Jerry smiled and buried his head in Stan’s chest.
“Sweetie, you can do and say anything that will make you happy. How long have you been wearing panties? Do you wear any other feminine clothing? I can see your red panties.”
Jerry turned red as he looked at Stan and said, “Oooh I don’t wear girls’ things. I just wanted to see how the panties felt on me. I don’t know why I did it, I just did. And I liked how they felt.”
“Well it’s okay with me if you want to dress in girl’s clothes while you’re here at my house. In fact I’d love to see you as a little girl so I could cuddle and give you bunches of kisses.” Stan said looking into his eyes.
“You really would give me bunches of kisses if I dressed as a little girl? That sounds so hot! How would I do that? I don’t know where to get any clothes. Mmmm I just want to kiss you now!”
“Sugar, just kiss me anytime like I told you, you don’t have to ask. Just turn my head and give it to me. My niece left a lot of stuff with me before going to work in Europe. Let’s go see what we can find.”
They went up to the third floor and to a far bedroom that had three big trunks and some suitcases. They opened one trunk that had petticoats and some slips. The other two had dresses and skirts and blouses. In the suitcases were panties and bras.
“Oooh Stan, what would you like me to wear? I think most of this will fit me. Are you sure your niece won’t be coming back for any of this? Mmmm tell me, what do you want to see me in?”
“Put on the petticoats, a slip and a dress, and oh don’t forget your red panties. I’ll be waiting for you in the Den.” He told him and kissed him.
Jerry took his clothes off except for the red panties. He found a pink with white lace silk slip and put it on. His cock was beginning to wake up. He found a yellow lace petticoat and a pink and white one. Then he saw the pretty black lace petticoat. He looked and found a full skirt A-frame dress. He came down and walked into the Den and Stan gave a wolf whistle. Jerry twirled for him the petticoats lifting the dress up. Giggling Jerry ran and straddled Stan and dove in to kiss him. Their lips locked and their mouths opened to allow their tongues to dance with each other. After a bit they broke for air and Stan said to Jerry
“Keep this up and I may just have to take you to the bedroom and make love to you.”
“You can do what you want with me! I never felt so good. I think this must have been in the back of my mind for some time. I want you to love me. You found me now, make me yours in whatever way you want.” He said and started kissing him again.
Stan reached under her dress and began to caress the round little ass. He said, “What if I want to fuck this pussy of yours, can I fuck it?”
“Yes, you found it! But be gentle with me. I want to do things right.”
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By August Moon
#Cuckold #Teen #Trans #Virgin
