The Dresser Files Ch. 3

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Texas trip brings crossdresser son and mom closer together.
2.8k words
4.62
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Part 4 of the 5 part series

Updated 10/29/2022
Created 06/11/2002
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rapidran
rapidran
133 Followers

I awoke to the sound of talking. I opened my eyes and just glancing around, I realized I was in the hotel bed. Then I remember the activities hours before. The voices I heard over my shoulder were from Jan and her son, Curt. Though they were talking softly, I could tune into all their conversation.

"So when did you start wearing my panties?" she asked him. "About the same time I saw you and Kelly laying in bed naked." He replied. "What? You saw us?" she said with a gasp. "Yes mom, you were lying in your bed and I just peaked through the open door." He said. "You watched us?" she questioned him. "Oh yes. From the time you stopped kissing her until the time you buried your face between her legs to eat her pussy." He said with a slight laugh. "I watched you both go down on each other."

"After Kelly left and you went into the shower, I went into your bedroom and found the panties that Kelly was wearing." He continued. "I pressed them to my face and smelled her wet juices. Then I saw yours lying next to the bed. I took both pair and put them in my pocket and left." "And?" Jan asked. "I went to my room, put on Kelly's panties and lay in my bed and pressed your panties to my face to smell your sweet pussy." Jan sighed loudly at that comment. "Since then, I not only wore your panties, I took other lingerie from you. I love the feel of dressing as a woman and as dressed as a woman, I started getting feelings for guys. Don't get me wrong though, I still love tits and pussy too."

"I saw you with Glenn at our house the first day." She said to Curt. "You did?" he said surprised. "Yes, and it made me so hot. I knew you must have been taking my panties. I found a pair in your closet one day while doing laundry. It made me hot to think of you wearing my panties. And, I am sorry to say, it made me hot for you." She said. "And, during an email conversation with Glenn, I told him about my thoughts and you. He is a dresser too you know?" she said. "Yes, he told me. Those were his clothes I was wearing at the house. And he was my first guy, mom." "Oh sweetheart." She replied.

Then the conversation ended and the room got quiet. I slowly turned over on my other side and propped my head up on my hand and elbow. Curt was leaning over his mother and was kissing her. It was very passionate. Jan was moaning as he kissed her and I assumed from her sighs, he was playing with her tits or pussy. His back blocked my view. Jan's hands were holding him close and one hand slid down to cup his panty clad ass. I was getting a boner.

Lying there I watched them grind their bodies together. Jan started sighing and moaning more. It was evident she was getting hot by watching her grip his ass hard and pull him into her. They broke they're kiss. "Fuck me, Curt." Jan said a moan. "Please fuck me now." As Curt sat up and pulled Jan up, she caught me watching. She just smiled with a glazed look of lust on her face. Curt undid her blouse and pulled it off. He unhooked her bra and threw it across the room. Then with one hand, he yanked her thong off. He pushed her back on the bed and her nipples were hard and reaching for the sky. He leaned down and sucked one into his mouth. "Oh yes, suck my nipple. Oh yes." Jan said rolling her head side to side. "Bite it, Hon, bite it." Curt must have done the right thing because Jan moaned a loud, YES!

As Curt was devouring her tits, she reached into his panties and was grasping his hard cock. Her hand frantically caressed his shaft and balls. He had enough. He leaned back on his hunches, pulled his chemise off over his head and pushed his panties down off his hard cock. He grabbed her legs and pushed them back. Her thighs opened wide and her wet pussy was his target. Her cunt shined with her wet juices. She reached down between them, grabbed his hard cock and pulled it to her cunt. She rubbed the large head up and down her wet slit, coating it with sheen of slick wet pussy juice. Then she pulled it to her cunt and bucked her hips up. She gasped as the big purple cock head penetrated her pussy. "Oh yes." She gasped. Curt needed no prompting. He just shoved forward and his hard cock split her open and buried itself deep inside her wet hole. "OOOHHHH GOD." She cried out. She grabbed his ass with both hands and began slamming her cunt on and off his wet cock. "Yes fuck me, fuck me, FUCK ME!!!!" she said loudly as her hips rose to match his slamming ass.

I reached down and grabbed my hard cock. I stroked it watching a mother and son fuck each other to death. It was so hot. I could smell the scent of sex filling the air. Pussy musk permeated the room. The bed shook with they're motions. "Yes, yes, yes." Jan said over and over as Curt jammed his bloated cock in and out of her wet soppy cunt. It was all I could take. I needed some of that action. I sat up and put my hand on Curt' shoulder. He looked at me. "Pull out." I said. Reluctantly, he did. Jan opened her eyes pleading for the cock to return. I pulled her into the middle of the bed and onto her side facing me. "Fuck her from behind." I said to Curt. He lay behind his mom and I lifted her leg. He slid up behind her and I grabbed his cock and pushed into her cunt again. She groaned as he filled her hot need again. He snuggled up to her and began to slowly fuck her again. He kissed her neck and ears as his cock moved in and out of her. I slid down into a 69 position and pressed my tongue up against her open cunt. Her clit was bright red and erect. I whipped my tongue back and forth across it. Her cunt smelled wonderful. I could feel Curt' cock brush across my forehead as I sucked on her clit. I pushed my cock to her face and she immediately drew my bone into her mouth with a moan. Her lips surrounded my cock and her tongue danced around my shaft. I began to match my own in and out motions with Curt' cock.

It wasn't long until she pulled her mouth off my cock and frantically said to Curt, "Harder, faster." "Yes, fuck me, fuck me." Curt increased pushing and pulling his hard cock in and out of her hot pussy. She jerked and twisted as he fucked her. "YYYYYEEEEESSSS! she screamed as she came. He continued to fuck her as her body shook in spasmodic tremors. She jerked one more time and her body slumped back against his chest. She was drained, sated and soundly fucked. I looked at Curt and then down to his still hard cock. "Come over here." I said to him. His cock slid out her used pussy as he climbed out of bed and walked around to my side of the bed. "Take off your panties." I said to him. He stepped out of them and lay down beside me. He still had on his garter and stockings. He pressed his hard cock against mine and I leaned in and kissed him. His mouth opened to accept my tongue. I ran my tongue around his and pressed my cock to his cock. I reached down between us and grabbed his wet sticky cock. I slowly caressed his shaft and then cupped his heavy balls. "I want to fuck you." I whispered in his ear. He pulled back from me and looked directly into my eyes. I mouthed the words again, "I want to fuck you." He closed his eyes and just nodded a, yes.

I pushed him on his back and slid down his hot sweaty body. I lay between his legs, feeling the silk stockings on both sides of my face. His cock and thighs smelled of pussy juice. I licked up his thigh and took one of his balls in my mouth. I rolled it around in my mouth until it was wet with my salvia. His moaning told me he was enjoying all my love. I slid my mouth off his balls and pushed his legs up back. He helped by reaching down and pulling them back. Then I spied my target, his sweet little virgin rosebud. I drew my tongue down one ass cheek and up the other. Then inched my way to the bottom of his ass crack. Slowly I moved up, licking my way and smelling his musky ass. My tongue then touched his hole. He jerked as I rotated my tongue around and around his hole. I pulled his ass to my face and pressed my pointed tongue against his asshole. He pulled his legs back further to give me more access. I pressed the tip of my tongue into his hole. He smelled of sex and I got harder as I tongued his tiny hole.

I pulled my mouth away, put one of fingers into my mouth and coated it with my salvia. Then I pressed it to his hole and pushed it slowly in. He moaned softly as my finger invaded his ass. I pressed my finger in until my entire knuckle disappeared. I pulled it out slowly, smelling his ass scent. I pushed it back in again. I slowly finger fucked him. Once he accepted my one finger, I pushed a second finger in. Again, a groan came from his lips. As I finger fucked him, I felt a mouth on my cock. Jan had been watching and turned around to suck my cock. Her mouth felt hot and wonderful. Here I was finger fucking her son and she was sucking my hard cock. I turned my head and looked down at her sucking my cock. She looked up at me with a lusty glare. "I'm going to fuck him." I said to her. Her eyes closed with a sigh. "Get me good and wet." I continued. She devoured my cock and was coating it with her sticky salvia. She sucked and pumped my cock. I was getting close and had a better place to put my cock.

I patted her on her head and she pulled away. I slid away from her and in between Curt' legs. As I was lifting his legs up, Jan pushed her head between us and went directly to his ass. She pulled his cheeks apart and slid her tongue to his hole. She kissed, licked and covered his ass with her love and her spit. Then she slid out and I moved again between his stocking clad legs. I put his legs on my shoulder. As I got ready to press against him, I felt Jan put her hand around my cock and guide it to his ass. She used her other hand to spread his ass cheeks and pushed my cock to his hole. I pushed slightly and Curt groaned. Jan watched intently as the head of my cock slowly stretched his wet hole. I hoped my fingers had helped to loosen his ass muscles. One push and the head popped in. "OOOhhhhhh, wait." Curt said in a panic tone. "Wait, it hurts." Jan moved quickly up to his face and said, "I know my darl'n, but it will be wonderful soon." She leaned down and locked her lips to his and shoved her tongue into his mouth.

As she kept him occupied, I pushed again, sliding a little more cock meat into his hot ass. He groaned and his ass muscles tightened. "Relax, relax." I said to reassure him. He calmed down and I pushed a little more of my cock in. I waited until his muscles became accustomed to my size and then pushed more in. He kept sighing and moaning into his mother's mouth. Then with one more push, my cock was all the way in his hot ass. I slowly withdrew a little and then pushed forward again. Then withdrew and then forward. Little by little I withdrew more of my cock until I was fucking him with long slow strokes. Jan moved away from his mouth and sat back on the bed. She watched as a man was fucking her son. One of her hands was pinching one of her hard nipples and the other hand was between her legs and she was rubbing her clit with her finger.

Curt lay there with his eyes closed and breathing fast. His soft sighs and moans told me he loved being fucked. I looked down and watched my cock sliding in and out of his stretched hole. His asshole was like a vacuum sucking me in. The room smelled of sex. I began pumping my cock in and out of his hole a little faster. I knew I was going to cum soon. "Yes, fuck me." Curt said opening his eyes. He looked down between his legs to watch my hips push in and out of his thighs. He could not see my cock going in him, but I know damn well he could feel it. "Fuck me good." He said. He turned his head sideways towards his mother. He watched his mother slide her own fingers in and out of her cunt as she watched her son getting fucked. Her son who had just fucked her the hour before.

I was very close. I grabbed his thighs with both hands and slammed my cock deep into his bowels. "Oh god." He moaned loudly. I began slamming my hips forward to drive my hard cock deep into his hot hole. Over and over I fucked him. Fucked him. Fucked him. Curt groaned and his cock shot cum on his chest and stomach. He really came a lot. His sperm covered his body. Jan slid down and began to lick up his hot sticky juice. Her cum covered face bounced each time I slammed into Curt' ass. Watching her just sent me off. I pushed my cock deep into his ass and came. I shuttered as my sperm filled his ass. Over and over my cum spurted out my cock. His asshole gripped my cock and milked me. It was liked someone gripping my cock with they're hand. As I pushed and pulled my cock in and out of his hole, the last of my cum was milked out. I was totally spent. My cock slipped out of his ass, leaving a gapping hole leaking cum. I moved away and lay on the left side of Curt. I watched as Jan continued to lick up his sperm. Her nose, cheeks, chin and lips were covered in a white film. She continued to lick and swallow. She moved down to his limp cock and sucked it into her mouth. As she sucked him dry, I moved up and kissed him. I kissed him softly.

"I loved it." He said as I kissed his cheeks. "Me too." I replied. We both looked down at his mom cleaning house. She let his cock slip from her lips and she moved to his ass. She licked up the cum running down his ass. I knew she needed help. I moved down, pushed Curt' legs up and together, we licked up my sex juice. Then I leaned over and kissed her. Her lips were so soft and coated with cum. I still wanted to fuck her. It was a very hot kiss. So wet, soft and meaningful. She was very hot. I actually felt my cock stir with just her kiss. Or maybe it was just the thoughts of what just happened over the past few hours.

But I still had three more days in Texas and a lot of thoughts ran through my devilish mind. Let's see. There was still Jan to love. Maybe Jan and her girlfriend Kelly. Oh, and I wanted some more time with Curt. This time I would be dressed in my femme attire. I wonder what Curt' girlfriend would think. Or hey, I wonder what she looks like and what fetish might be in her mind closet?

Well, "Happy trails to you. Until we meet again."

rapidran
rapidran
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