My Son Is A Cross-Dresser Pt 5

“I didn’t think I would ever be so turned on by a cock before. I didn’t think seeing a sissy get fucked by my dad would be something that I enjoyed.”

Part 1 | Part 2 | Part 3 | Part 4


The next morning, Eric was up early to get ready for work. While he was dressing as Heather full time now, he still made sure everything was perfect before leaving the bedroom. He still hadn’t told his brother Matt, who he was. He wasn’t sure how he’d feel about it, and how much he would freak out about what he is doing with their dad. Matt was already up and sitting at the table eating cereal.

“Morning,” he said noticing Heather. She was wearing tiny shorts, and a t-shirt under her robe.

Heather sat down to eat something small before getting ready for work. She wasn’t sure how to play everything. Should she tell him everything? Would he be okay with it? Matt would be leaving in a few days, and it would be okay after, but it was getting there. They had some small talk before Matt asked, “So do you stay here a lot, or do you ever go back to your house?”

“Ryan…your dad…said it was okay for me to stay here for a while. I hope that’s okay,” Heather answered.

“Fine with me, I’m sure my brother won’t mind either,” he commented. “Have you met him yet?”

“Yes, he was very nice,” Heather answered nervously. He tried to stay away from that conversation.

“I heard you and my dad last night. Seems like you two are very happy together,” Matt smiled as he continued to eat.

“Oh sorry, we didn’t realize…he makes me very happy,” was all she could say.

“Don’t be sorry. Wish I found a girl like you who could make me happy like that,” he stared at Heather seductively.

“Well, I should really get ready for work. I don’t want to be late,” Heather said getting nervous. She went to their dad’s room and tried to calm down. After fixing her hair and makeup, she tried to find something to wear. She picked out a matching red bra and lace thong. As she did so, she thought she heard a creak at the door. She peered over but didn’t see anything. As she strapped her bra on, she heard it again. This time, she kept going and looked at the door pretending not to notice. She saw Matt there this time, trying to hide in the shadows.

She paused for a moment pretending to fix her bra. In doing so, Matt never left. While Matt didn’t know who Heather was, Heather knew Matt was aware was he was a crossdresser. He didn’t seem to mind as Heather could still hear the creaking of the floor as he watched Heather.

She was turned on as she knew she was being watched. She played with her cock a little bit before she tucked it away. The she got her red blouse and white skirt on. Her tits looked great as she tried to show off more. Her skirt ended right before her knees. It really made her ass pop as she admired it in the mirror. She got her bag and left the room.

“Hey Matt, I’m heading out.” She waited a minute to see where he was. He came out of his room a few seconds later, a little out of breath.

“Sure, No problem. I’ll see you later.” She smiled as she left feeling much better about herself.

All day at work Heather texted her dad and was anxious to see him. She also told him about Matt.

-Maybe you should see if he wants you also


-Only if you’re ok with it

-That would be kinda hot. What if he freaks out

-If he does it’s his problem. I love you no matter what baby

– 🙂

Heather was excited to return home to see how things would play out with her father’s approval. When she got home, Matt was not there. She wasn’t sure when he would return but she decided to change in the meantime. It was a sundress that barely covered her ass. She put on some strapped heels as well to make it go a little better. Her tits weren’t used to being so out and about, but she didn’t think either would care.

About 30 minutes later, Matt had returned home while Heather was in the kitchen still cooking. He walked into a wonderful smell and was surprised she was there already. He was even more surprised when he saw Heather’s dress.

“Wow, that’s interesting cooking attire,” he smiled. He placed everything down and began to get more comfortable.

“Well, it gets hot in the kitchen. Didn’t want to be sweating all over the food,” she answered. He moved a little closer to her. Heather noticed the growing bulge in his pants. She bent down in front of him on purpose, her ass exposed and her cock barely staying in her panties. Matt felt like she was doing this on purpose, although he wasn’t sure why. Maybe she didn’t like his dad and just was some slut. Either way, he didn’t care.

As he got closer, she could feel his cock pressing against her ass. Heather couldn’t believe she was doing this to her own brother. It was hot that he didn’t know, and it was even better that their dad was okay with it, but she wasn’t about to tell Matt that. He got behind her and started to rub her back.

“When I saw you, I was wondering how my dad could get such a hottie like you. Then I peeked into your room and saw you two fucking. Quite an incredible body you have. Didn’t expect to see this flopping around,” Matt said as he reached down and held Heather’s cock in his hand. He could feel it getting hard. He smiled as he moved her hair with his nose from behind her. Her eyes were closed as she felt his cock push against her.

“Did you like what you saw,” she asked, showing she was into it.

“I didn’t think I would ever be so turned on by a cock before. I didn’t think seeing a sissy get fucked by my dad would be something that I enjoyed. Yet here we are, my cock throbbing so hard thinking about it,” he explored her body with his hands.

Heather was done playing games. “Maybe if you want it so bad, you need to take it,” as she spun around. She leaned against the counter, staring at him in the eyes. He didn’t wait a second longer either as he rushed towards her and began kissing her. His hands grabbed her face as his tongue slipped into her mouth. She reached down and could feel his cock even better. She didn’t realize her brother had such a huge member.

“I think it’s time for this thing to come out,” she said with a giggle. He was shocked by how commanding she was as she pushed Matt against the wall. His pants flew off and his cock smacked Heather in the face. She just laughed again. “I love giant cocks like this.” She took a moment to explore it. It was about 8 inches and very thick. He kept it nice and groomed as he had very little hair. His balls looked like he hadn’t cum in weeks.

“Think you can handle all of that baby?” He looked down and gave a little smile.

“You tell me,” She said finally opening her mouth. She started with the tip of his cock, just getting it nice and wet. With each bob of her head, she went down further on the thick cock of her brother.

“Mmmmm yes baby,” he started to moan. Heather was on her knees in her short dress, sucking a cock right in the kitchen. Matt looked down at her ass peeking out. “So fucking hot you are.” She kept going, using two hands now to work his meat. He looked down at her, her mouth full of cock but he could see how happy she was to being doing it.

Matt had been with many girls before, nights of fun that he still talked about, yet as he looked down, he couldn’t believe how this sissy was more beautiful than the rest of them. Knowing there was a cock under the dress made him even more excited and never expected to feel this way. Heather’s mouth worked his cock, and it was so wet, it was dripping onto the floor.

“What an amazing cock you have,” she moaned, coming up for air. He reached down with one hand and grabbed her by the throat. She followed biting her lip, spit and cum, all over her face. He pulled her closer and kissed her with such passion, he could now feel her cock starting to get hard. As they kissed, they moved out of the kitchen, down the hall, and into Matt’s room. Heather had been in this room plenty of times before, but never like this.

She pushed him down onto his own bed. He looked up at her smiling. Heather looked down at Matt, her unsuspecting brother and wanted to feel his cock in her badly. “I’m going to need to get this cock nice and wet before it’s able to fit anywhere.” She bent down in front of him and started sucking the slab of meat on her brother.

“Fuck baby, you really know how to suck dick,” he moaned looking down at her. Her tongue worked his small dick hole. Her hands carefully massaged his balls, even slipping a finger near his ass. He flinched a little but never resisted. Heather then felt the big cock start to twitch. He was about to cum. She prepared her mouth and throat for the coating it was about to get.

“Oh God, fuuuuuck.” Matt shot ropes in Heathers mouth. She took a moment to gather all of the cum in her mouth. She stood up to show Matt how much she caught. “You are incredible. I’ve never cum that fast before. I’m a bit embarrassed to be honest. I wanted to go much longer with you.” Heather did say anything. Instead, she grabbed Matt by the back of the head and lifted his head up. She opened his mouth as she leaned in and let all of his cum from her mouth drip into his.

“This is how good you taste,” she smiled as she gave him a kiss on the lips. Matt was taken back at how in charge she was. The taste of his own cum was sweet and salty. Before he could say anything else, Heather was giving more orders.

“Since we didn’t get to do everything, we wanted, I think I’ll have to be a bit more aggressive this time.” She pulled her cock out from under her dress. It was fully erect and much bigger than Matt thought. “Turn around for me baby.” Matt did as he was told. His cock semi-erect dangled between his legs as he waited for Heather to enter him.

“This is for not giving me a cock in my ass,” Heather said as she began pushing the tip of her cock into his hole. Matt considered himself a very manly guy. Never thought about being with a man or even thinking about cock. Yet as his dad’s cross-dress lover stuck her cock in his ass, he wondered how he ever went so long without it.

“Holy Shit. I’ve never had a dick in my ass before.”

“You enjoying it so far?”

“I…I think I am.” Matt didn’t want to admit he was enjoying being fucked. “Heather began to slowly pump away at her brother’s ass. Slowly but surely, he went harder and faster. “Fuck baby. This is amazing.” The slapping of Heathers balls hitting Matts ass turned them both on so much. Heather grabbed her brother by the hips and started to go harder, pulling his hairy ass deeper on her cock.

“Yes, fuck Heather. Fill me up baby.” Words Heather would never though her brother would say those words, especially because of her. Heather felt the cum starting to get ready and shoot out. A few pumps later, Heather held herself there and emptied her balls into her brother’s ass. Matt could feel the warm seed enter his hole and he felt himself getting hard again. Heather pulled out and some cum dripped out as well. Before either of them could say anything more, they both noticed their dad at the doorway.

“Holy shit. Dad what are you doing… This isn’t….” Their dad just laughed and raised his hand. “Don’t worry son. Heather and I have a very open and understanding relationship.” They smiled at each other still keeping their secret. “I never knew you were into crossdressers and cock before Matt.”

“I didn’t either. There is something about her that made me want to try it out though.”

“Maybe we can finish off this night with helping me finish, if you are both okay with that.” Ryan wasn’t sure if this was crossing a line for Matt but if he was okay with it, he knew he could push him more in the future.

“What did you have in mind?” Ryan smiled and began undressing. Heather removed her dress until they were all completely naked. He gave her a deep kiss before saying, “I think my girl needs to be double stuffed.” They all agreed and quickly moved into position. Heather was on all fours on Matts bed with her dad in front of her and her brother taking behind. Matt was finally able to enter Heather as she sucked her father’s big cock. Heather moaned and slobbered away on the cock in front of her.

Matt’s cock was fully hard again as he gave Heather a similar pounding. Now she knew what her brother did with all those girls when he went out and why he was so popular. He was hitting her deep and felt like she would cum again herself. She looked up at her dad while she was still enjoying his cock and gave him a small wink. He gave one back and loved how this night was going.

Heather pulled away from both of them and asked, “Can we try something new?” They both nodded. She had her dad lay on the bed and she got on top of him, looking down as he entered her. She then instructed Matt to enter her ass as well.

“Unless you don’t feel like having your cock rub against your dads while you both fuck me,’ she teased. He didn’t even need to think as he began pushing her own cock into Heather’s ass. Her asshole had never been so stretched out before. Her moans quickly turned into screams as both men fucked her like crazy.

“Yes, fuck. Give me both of your cum in my ass!” She grabbed her dad’s face as she kissed him, her ass turning beat red. Her cock began to squirt out its own cum from the pounding she was getting. Her seed went everywhere. Her cock was wet as both men were abusing her ass and she loved every minute of it.

“Fuck baby, I’m about to cum.” Her dad moaned. “Me too. Let’s fill her up.”

Both men released their load into Heather’s ass. Each could feel the other’s cum hitting their cock in her ass. As each slid out of her, she made sure to lick the cum that was still on their cocks. Matt bent down and began to suck and lick the mixed cum out of Heather’s ass and swallow it. He couldn’t believe how much he enjoyed the taste and what he had just done. As Heather and his dad made their way back to their room, Matt laid there still naked. He loved every part of being with a crossdresser and planned to look for more in the future even if he didn’t know this one was his own brother.

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