Crossdressing Son and Dad

Eric was a well-built man just finishing up his college life and getting ready to move on into the real world. He had a job already lined up and planned on moving out of state in the coming weeks but was moving home in the time to prepare himself. It worked out as his younger brother just finished up high school and was going to be traveling for the next month. It would be just him and his dad.

Their mom left them a few years back. Dad never said why but he seemed more ashamed than angry but Eric and his brother, Dan, never brought it up and they didn't want to upset their dad. He was a fun guy, in his 50's but certainly didn't look or act like it. They talked a lot while he was away at school but for the last few school breaks, Eric didn't return home to prepare for his job after. While Eric was a great business man during the day, he found a side of him that he loved even more.

Eric had become a very secret crossdresser at night. He loved dressing and going out. Teasing guys when they had no idea of who he really was. He even hit on his own friends one night and they never even realized.

"This is great," Eric thought. "I really am convincing!" Through an app, he meet up with other crossdressers and they hung out, dancing and drinking. But recently Eric started to want more. He wanted to actually be with a man. He was nervous about what would happen if the guy he fooled would be angry about it.

"Eventually," he thought. Once he moved back home, he hid all his dresses, wigs and makeup so no one would find it. He still planned to go out some nights. He found the perfect night when his dad said he would be going out with some friends. "Nice," Eric said. "So am I."

"Just a couple of guys going out on the prowl then," he laughed. I guess that was his hint of, don't wait up for me if I'm not home.

"Oh yea," Eric said. "Definitely would like to have some fun tonight." And he wanted to. Eric planned on finding the right guy to fool around with. He knew there was a gay club nearby and even if he dressed, it might be easier to find someone to actually be with.

Eric's dad left first giving Eric enough time to dress and do makeup. He did his makeup perfectly, his dark eyeliner and red lips standing out from his blonde curly wig. While he was about 5'9 normally, his black heels gave him a few more inches. He tucked his completely shaved cock into some lacy panties and squeezed into a tight-fitting black dress. He made sure it there was just enough cleavage showing.

Even he at time couldn't recognize himself. He smiled to the mirror and headed out. Tonight he went alone without any friends. If he found a man, he didn't want anyone else to get in his way. Inside, Eric got a drink and quickly made laps around the room.

"So many sexy guys here," he said to himself. Before he could talk to anyone, he needed another drink already. At the bar, he already had some interest.

"Looking very sexy baby," the voice said. He looked to be a few years older than Eric but dressed a little outdated. Still, Eric loved the compliment.

"Well thank you very much," Eric smiled back. "You look very good yourself."

"I try. Gym is very important," he bragged. So is style Eric thought but he didn't want to be rude. "I'm Tim by the way." He put out his hand. He shook it.

"Heather," Eric responded.

"Listen, I don't know if you are free but I'm with a few guys who would love to meet you," Tim said. Eric was taken back. He didn't expect so much attention. Did they know he was a crossdresser? Did they care? Should he tell them? He started to get nervous at the thought of it.

"That's very nice but I think you should know I'm-"

"Not a real girl?" Tim laughed while he interrupted. "You're in a gay bar. I just assumed and hoped. At first we thought you were a real girl and almost didn't come over." Wow, Eric thought. This was much better than he thought. They didn't care. They even hoped he was a guy. Maybe this was going to be a good night.

He followed Tim back to their private area. As they walked in, there were a few other "girls" there. They all said hi and introduced themselves. The last person took Eric by surprise.

"Hi beautiful. I'm Ryan." It was his dad. Eric just stood there for a minute before he reach out and shook his dad's hand.

"Nice to meet you," he said. Eric just nodded. Was this right? Why would his dad be here? How long has this been going on for. Eric's head was spinning but didn't want to make a scene so he stayed. He sat at the table talking to all of the guys and for a few minutes he forgot about his dad. He was having a good time before Ryan came over again.

"So, I haven't seen you here before. New?" he questioned.

"Sort of. I travel a lot. Don't get a lot of time to...be myself."

"I understand. My friends here are great but most of my family doesn't know about me. I don't know how they would ever feel so I try to hide it from them," his dad explained. Eric was more interested in talking now. As they did, he found out his mother left because she found their dad with another guy, and she was embarrassed. She left and couldn't stand to be near him anymore.

"She should have never left you or your kids. That was very selfish of her," Eric comforted his dad.

"I know it was my fault, but I will always feel guilty for my family," he looked sad now. Eric didn't want him to feel this way on such a good night, so he asked him to dance. He happily agreed and they started enjoying themselves more. As the night went on, Eric had a lot of fun with his dad. Eric didn't even seem to mind his strong hands gripping his body and caressing it while they dance.

What he did notice was his bulging cock against his ass while they were dancing. This is so wrong, Eric thought. Yet here he was enjoying the night and getting a man hard, even though it was his father. It was getting late and Ryan said he should he going and Eric agreed. They walked out together.

"I had a wonderful night with you Heather. I wish this night didn't have to end," he said slowly walking towards his car.

"Me either," he responded. He wasn't sure why he said what he did next but something inside him wanted to see what would happen. "Maybe it doesn't have to." Ryan smiled. I was hoping you would say that.

He leaned into kiss Eric. His tongue quickly twirling around his sons mouth and he had no idea. Eric didn't care, it felt so good. His dad grabbed his face and got more into it, reaching behind Eric and grabbing his perfectly bubbly ass.

"Maybe we can go back to my place," Ryan offered. This is it, Eric thought. Go back to my house with my dad or make some excuse to end this right now.

"I'd love to," Eric smiled. He hoped in the car and was nervous the whole way back to his house. Good thing I took a cab, he thought. Before they were even in the house, his dad was all over him. Kissing his neck, grabbing his ass wanting more. Eric could feel his dad cock getting harder and harder. Finally inside, his dad admitted he was so happy he came back with him.

"I'm so glad I did also baby," Eric said not even realizing what he said. He sat right on the couch in the living room unbuttoning his shirt. When it was removed, Eric was shocked at how in shape he really was. He must have been hitting the gym even more while he was gone. Eric stood there in his dress but feeling his cock get hard now looking at his dad. His dad motioned for him to get closer.

Eric straddled him and his dress rose a bit and sat in his lap kissing him intensely. Almost by instinct, Eric reached down toward his pants and rubbed his cock from the outside of his jeans.

"Take these off for me baby," Eric told his dad.

"Mmm you got it," he agreed, slipping out of them. He was now completely naked on his couch, Eric now on his knees, staring at his dad giant eight-inch cock. It was neatly trimmed and very thick. So, this is the first cock you are going to suck, he thought. Your dad's meaty cock.

Maybe it was because it was his first time, maybe it was because it was his dad's but Eric jumped on it eager to taste it. A low moan came from his dad. Eric started sucking and licking more. Going gown his shaft, making sure everything was nice and wet. He stroked his cock while he took his dad's balls in his mouth.

"Fuck Heather, you are amazing." I guess it just came natural to me, Eric thought.

He went deeper, his head hitting the back of his throat. He gagged a little and heard his dad chuckle. "You really want that cock don't you baby?"

Eric didn't answer. He just wanted to keep sucking. He could taste a little bit of precum coming out and made sure he licked it all. His dad's cock was dripping wet and he stroked it faster, licking every inch of that huge cock.

"Cum for me baby. I want your cum in my mouth," Eric begged his dad. He didn't say anything but a grunt and he knew he was about to shoot his load. Eric put his mouth back and took every shoot that came out of his father cock. It tasted delicious. His dad thrusted a few more times making sure every bit was out. Eric swallowed with pride.

"You were incredible baby," he said leaning down to kiss him on the lips. He could taste his own cum from this crossdresser mouth. "Your turn," he smiled as he picked him up and threw him on the couch. Eric was now the one sitting as his dad reached up his dress to expose his cock in the lacey panties. He pulled it out from the side, the smooth cock of almost five inches. "This looks lovely," he said quickly taking it in his mouth.

"Ohhhh my god," Eric squealed. He was easily throating his cock getting it wet like he never had before. Hid dad might have thought he was great, but his dad was clearly a pro at sucking cock.

"Fuuuuck," Eric continued. No girl had ever given him a blowjob like this before. This was easily the best. And from his dad no less. He felt a couple of fingers slide into his ass but he didn't care. It made it all the better.

"Fuuuuck. Fuuuuck me," Eric could just get out.

He felt his cock slide out of his father mouth. He smiled and said, "That's the plan baby." Without realizing it, he was being turned over. He was bent over, knees on the couch with his dad standing behind him. His huge cock still was hard.

"Time to really make you cum," he said as he slid his cock into Eric's ass. He had used toys before, but this was ten times better. He started slowly getting his tight ass used to his cock and then began to pick up speed. "God you are so tight Heather. I love it."

"Shit, yes. Fuck me." Eric was loving every second of it. He started to move his bubble ass back and forth as well, going in sync with his dad. He noticed as he let out a moan of his own.

"God you really know how to use this thing sexy," as he grabbed him by the hips and started fucking harder. He kept pumping away getting closer and closer to cumming. "You are going to make me cum all over again in this ass of yours."

"Yes, please cum in me. I want you." That pushed his over the edge and he started cumming into his son's ass, filling it with cum. As he did, Eric began to cum as well.

He turned onto his back and came all over his stomach. His smaller cock twitching from the incredible sex he just had. His dad bent down and Eric watched as his dad began to lick his cum off his stomach. It was amazing to see. When it was all clean, he made his way to his son's ass.

"Now, if I had your cum, you have to eat mine again," he said pressing his lips to his son's ass. He began to suck the cum right out. He used his tongue a bit to make sure he got all that he could. With his own cum in his mouth he motioned for Eric to get closer. He did and opened his mouth. His dad spit the cum that was just in his ass and deposited in his mouth. It still tasted just as good. Eric swallowed and smiled.

The next few minutes they sat there in each other's arms. Finally, his dad said, "We should probably move just in case my son gets home."

Eric just smiled and laughed. "We probably should."