Meeting My Crossdressing Parents - Cover

Meeting My Crossdressing Parents

Copyright© 2024 by GATA_Wolf_84

Chapter 1

Incest Sex Story: Chapter 1 - A chain of events when a young man watches his cross-dressing parents walk into a restaurant.

Caution: This Incest Sex Story contains strong sexual content, including Ma/Fa   Ma/Ma   BiSexual   CrossDressing   Incest   Mother   Son   Father   Anal Sex   Oral Sex   Pegging  

I was sitting in a restaurant booth near my sister’s college. It was about two hours from our hometown and over an hour from the college that I attend, where I recently finished my freshman year. Instead of sitting at home relaxing, I was doing another favor for my sister, many of which she still owes me. I was on a blind date. It was not the first time she had convinced me to do this but this one must be the worst yet.

My date’s IQ was slightly higher than a snail, with the table manners of a two-year-old, and she had spent the last hour whinnying about all her ex-boyfriends. There was no way in hell this date would continue with dancing or a movie. I was thinking of calling it a night. I was just debating whether to ditch her and go home or get a room and bang out the last of her brain cells.

From the main doorway, two older women walked in, as they proceeded to a table in the back on the other side of the room they caught my complete attention. There was nothing spectacular about either of them just slightly above average looking. Most guys would rate them a 7 or 8 on a scale of 1-10. I rated them both 9’s.

One was a 5’7” green-eyed dark hair beauty with a captivating smile, the girl next door body with C-cup breasts, a slight midsection, and wide hips. She was wearing snug jeans, cowboy boots, and a button-down blouse tied low at her waist, showcasing those wide hips and a perfect hart-shaped ass. The image of many late-night masturbation sessions, my mother.

The other woman stood at 5’10” but with 4” open-toe fuck-me heels she was towering over my mother. Big blue eyes over pure cocksucking lips. Medium C-cup size tits above a slim waist over small hips and a runner’s ass that sat on top of long luscious legs. Everything was encased in a knee-length sundress. This beauty could pass for my dad’s twin sister but the problem was my dad is an only child. OMG, this cannot be happening. No not now.

I needed to think about this. I paid the cashier and took my date home. She was upset and wanted more but with many things running through my head and her constant whining, I was rather rude. “Sorry, but the only thing you have got is a killer body after spending the last hour with the rest of you. It has killed all the desire I have left. Goodbye.”

My family history, we were a normal upper-middle-class family. Two working parents, two marginally normal kids, a dog, and a nice house. Thanksgiving and Christmas spent with Grandparents. Really normal, ‘boring’ actually.

We spent a lot of time together as a family with dinner, movies, school activities, sports events, vacations, and more. My parents were always affectionate and loving towards each other and us kids. Hugs, kisses, and hand-holding were not unusual for this family.

My dad was a real male role model when I was growing up. He taught me how to play baseball, shoot hoops, and catch a football, and we even went fishing a few times each summer going so far as enrolling both of us in karate classes for my 12th birthday. So, I was completely at a loss seeing him dressed so enticing as a female.

I remember when I was 10 my dad was put in the hospital. He was there for a couple of weeks, and when he came out the meals at home changed. No more fish sticks, burgers, and pizza. Now it was fresh fruits, vegetables, and plenty of fresh fish. No more breaded and fried foods, only food that was grilled or baked were now served. At the same time, my parents converted the basement into a home gym, and the entire family started working out. My mother contributed this change at home to my current size and physical development.

Now a little about my sex life. The summer before my freshman year of high school my older sister decided she did not want her dorky little brother embarrassing her around girls in high school. Even though I was already prime boyfriend material for junior high girls. I already had several make-out sessions and copped a few feels above the clothes. And two sets of bare breasts. She still thought I needed help.

So that summer she and a few of her friends taught me a lot about high school girls. Most of her friends just wanted the first shot at me. They started with what they thought was the basic ‘Do not be a dork’. I had to learn how to listen to girls and not try to overrun the conversation. Next was using subtle seduction techniques when talking with girls. It progressed to a full make-out session with hands under clothes by the end of summer.

Jenny Newman and Dianna Smith even gave me several private oral lessons. I learned the most about what girls liked from them. If their screams of joy were any indicator, I think I truly mastered eating pussy. Jenny, Dianna, and I managed to get together (separately and together) several times over my high school years to reaffirm my education. The most memorable lesson was just to treat every girl with respect and dignity.

I played many sports in junior high and high school but my favorite was and still is baseball. I was a good enough centerfielder to get a partial scholarship to a minor college two hours from my hometown. When I left high school I stood almost 6’3” and weighed 215 pounds.

I had just finished my freshman year of college and the baseball team did not make it very far into the playoffs when my sister roped me into another blind date.

Back to the present, I needed somebody to talk to. With the subject matter and the town I was in the only person I could think of was my favorite bartender at a lesbian bar. Not surprisingly she actually is a lesbian. How did that come about? That is another story.

I had been in college classes for nearly a month when my white knight protective brother attitude almost got me in trouble. I was attending a party and it was well after midnight when I went to piss out my latest beer before I went home. I was leaving the bathroom when I noticed three upper-class douchebags about my size and bigger trying to drag a staggering drunk girl down the hall.

I asked, “Hey what’s going on here?”

“We are going to sample some fresh meat.”

As I said, protective brother syndrome. “Not going to happen Dudes.”

“Punk get out of the way. We are talking this slut in one of those rooms and making her airtight.”

“That will be hard to do after I bust your head.” The guy in front took a wild swing at me. A quick duck and a jab to his gut followed by an elbow to the jaw and he went down. The next guy charged at me, with a quick step and push he went head-first into the wall and was out cold.

The last guy dropped the girl and raised his hands to fight. Just because I felt like it, I gave him a kick to the nuts before a hard kick to his chest. He flew back into the other wall, sliding down and not getting back up. They did not care about the girl anymore.

Picking up the girl I carried her out to my car. I found her driver’s license in a little clutch purse that she had strapped to her wrist. Her name was Susan and she was 18 years old. The only real problem was the address was in a town over an hour away. It was either taking her to my dorm room or taking her home. I took her home.

The address was located in a nice working-class neighborhood. The house itself was a small two or maybe three-bedroom house. At 3 o’clock in the morning, I was surprised to see several lights on inside.

With a drunk girl in my arms, I knocked on the door. It was opened by a thirty-ish, redheaded woman. As soon as her eyes lit upon the package in my arms, her finger was waving in my face as she went off on me screaming and cursing up a storm. First, she started questioning my parentage, then threatened my manhood and many other bodily violence and anything that she could get out of her mouth.

“Hey, bitch shut the fuck up. Does this puke-covered bag of bones belong here?” She stepped back at my raised voice. “If not, I am going to strap her to the hood of my car and drive back to my dorm so she can sleep off this drunk and finally tell me where the fuck she needs to go.”

That seems to calm the lady down a little. Another lady showed up behind her placing her hand on the irate redhead. “Bring her in. Will you tell us what happened?” While taking the girl to a bedroom I explained what happened to the two women.

When I started to leave the redhead would not let me go until I accepted her apology for her earlier outburst. Then I was forced to sleep on the couch instead of driving home this late. That was the first time that I met Jenelle. The next morning, we quickly became friends and we exchanged phone numbers. That day when I left, I had an open invitation to stop by the bar where she worked at any time, she would buy the first round.

Surprisingly I have not crossed paths with Susan nor the three thugs since that night.

About a month later I was visiting my sister and on my way home. I called Jenelle and she told me to stop by before I left town. The name of the bar was Crystals nothing seemed unusual until I walked through the doors and I knew I was in a lesbian drinking saloon. At the bar, Jenelle was laughing her ass off at the look on my face. Her girlfriend also had a big smile on her face.

As cool and calm as possible I walked up to the bar and in a loud sexy voice said “I want a tall Virgin Mary followed by Sex on the Beach please.”

“What do you really want DumbAss?”

“Just a coke. I’m driving straight home.”

While we were talking a very good-looking Dyke walked over and spoke. “What the hell is a breeder doing in here?” She stood Almost 6 feet tall and very muscular. Her blonde hair was cut short in a Butch-styled haircut. She had on a tight T-shirt under a flannel overshirt, both tucked into her blue jeans. She was also wearing heavy work boots.

Jenelle’s smile turned into a scowl getting ready to lite into the Dyke. But I beat her with a witty comeback. Using the girlish voice as I could muster “Hey I am a lesbian trapped in this old fat man’s body. I like to eat pussy as much as the next girl.” Everyone around that heard busted up laughing including the Dyke.

“Okay, you can stay. My name’s Susan, everybody calls me Sue.” Sticking out her hand to shake. I ignore her hand and pull her into a huge bear hug lifting her off the ground. Using my normal voice, “Hello Suzy, my name is Charles, but most people call me Breeder,” putting her back down.

“Or dumbass.” Added Jenelle. “Now you two quit harassing my customers.”

I visited Suzy, Janelle, her girlfriend, and a few others for about an hour before I headed home. I continued stopping by if I was in the area and had time. I got to know the regulars and even went out as a plus one a few times when one of the ladies needed a beard.

Back to my problem, I pulled into the parking lot at Crystals. I was climbing out of my car, I stopped instantly when I noticed my mother’s car in the parking lot. I called Jenelle’s cell phone. “Hey babe you working?”

“Yes, I am.”

“Do you have an older couple in there tonight? One dark hair wearing jeans and a flannel shirt. And a tall blonde with CFM heels.”

“You know I can’t discuss clients what’s this all about?”

“I need to talk with you but we cannot let them see me.”

“What’s going on? What’s wrong with them?”

“Nothing is wrong with them. The problem is the brunette is my mother and the blonde is my father.”

“Are you shitting me?” Her raised voice got looks from several customers and her girlfriend.

“No, I saw them together earlier at a restaurant. So, I took my disaster of a blind date home and came over here to talk to you for some advice, but I saw their car in the parking lot.”

“Come to the back door I’ll let you into the office and we can discuss this.”

In the office I told her about the night so far then I added. “I had no idea my father was a cross-dresser. I don’t care but I just want to find out what is going on. I think the best way is to confront them while he is dressed. But I do not want to cause a scene in the bar. Still, I feel like it is the best place for a meeting.”

I finally convinced Jenelle I had no ill intentions, so she led me out to their table. I stepped around her and extended my hand towards my father. “Hello, my name is Charles. Would you care to dance?”

The surprised look on my parents’ faces would have been funny if the situation was not so serious. “You don’t have to worry about this big boy. He is one of the good ones. He must have been raised right,” said Janelle. The offhanded compliment put a smile on my parents’ faces, but you could still see their uneasiness.

Still looking at my hand, I asked my father again “And what is your name? Would you please dance with me?”

My father stood slowly, taking my hand, and in a voice, I had never heard said. “My name is Stephanie.”

The song that was playing was good for a slow dance. I led Stephanie onto the dance floor. We started dancing keeping a respectable distance apart. It had been a few years since I was able to look directly across into my father’s eyes. But with her high heels, we were now eye to eye. I did not like the fear that I saw.

“Let me talk for a while. I want you to know that I am not upset or disappointed by what I see in front of me. I am just curious to find out what is going on.” Stephanie finally smiled. “But not here not now maybe at home so we can discuss it openly. I mainly got you out here to explain why I am here.” he smiled again.

“I was on a blind date set up by Deborah when I noticed these two beautiful women coming into the restaurant. Their appearance completely boggled my mind and no, I did not follow the two of you over here. I was not planning on seeing the two of you again tonight. I took my date home. But I needed someone to talk to so I came over to talk to the bartender, Jenelle. That is when I got another surprise. I see Mom’s car in the parking lot of a lesbian bar.” That got a laugh out of Stephanie.

“Hope we didn’t ruin your date or upset her.”

It was my turn to laugh “No it was a disaster long before that. My sister will probably be upset and not talk to me for a few days unless she needs me again.” That had us laughing as we walked back to the table

“We will chat and dance again later. Now I want to dance with another beautiful lady.” On the dance floor with my mom, we danced a lot closer. “No big discussion just a few questions. Is he gay or bisexual?”

“Neither” she replied. “We do enjoy a good pegging.” The grimace on her face showed that she had revealed more than she intended to. That raised my eyebrows.

“Your father has a medical condition. And it causes him some ahh ... bedroom issues. We tried prostate massage it didn’t help but we both enjoyed it so it evolved into me using the strap-on.”

“Are you happy with Stephenie?”

“I am but I sometimes miss what I can’t have.” At my look, she continued. “A real hard cock.” my jaw practically hit the floor and my mother laughed. “Oh, come on! I just met my son at a lesbian bar while I was on a date with my cross-dressing husband. I can be as vulgar if I want.”

We had just sat down when Susie came up behind me placing her hands on my shoulders and asked. “This Breeder he’s not aggravating y’all is he?” I could see my parents getting upset at what she said.

I headed off the potential confrontation. “Hey Suzy do you know Rachel and Stephanie? Ladies I’d like to introduce you to Susan,” in a stage whisper. “Just so you know I am the only one who can call her Suzy” chuckling. I leaned my head back into Suzy.

“Why are you the only one?” Asked Stephanie.

“The same reason she calls me Breeder.”

“But why?” Asked Mom.

“Because she secretly wants me to father her love child,” I said with a grin.

With that Suzy put me in a headlock, smashing my face into her tits and rapping the top of the head with her knuckles while laughing. Suzy flirted with them for a while before making her way to another table. We spent another hour just dancing and having fun. Both ladies were hit on several times when other customers came over to talk to me.

“Well, it is time for me to leave.” After getting up to leave, I sit back down and look at my mother. “Mom, you know that since I reached puberty, you have been my number one fantasy girl,” working my hand in an up and down in a jack-off motion. My mother blushed and Stephanie laughed. “But damn you got some competition tonight.” Looking at my father wiggling my eyebrows. it was Stephanie’s turn to blush and my mother’s turn to laugh. I stood back up and kissed them both on the cheek and headed out the door.

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