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Sam was 22, gay, closted cross dresser. He stood at 5' 5" 140lbs. He has long blonde hair, and green eyes. He has a feminate body. Also he is in college, and lives with his mom and brother. He was looking at his email this morning. Nothing but junk so far. He got to the last email from a gay dating site he belongs too. He opened the email and followed the link to his mail. He always smiled when the picture was taken at his friend's house. Even though his face was blacked out. He was surprised, the letter said. "I think you have an incredible body." "I would be interested in meeting you tonight at Chez Lewayne." Drop me an email if interested."
Sam clicked on the guys link to see what he looked like and read his bio. The picture had a candle. Everything else was blank. He replied,
"I would love to go."
A few minutes later another email:
"Tonight at 7."I'll be in a black jacket, white tie, red shirt." Flower in jacket."
Sam was intrigued by this guy. He figured if nothing else he could walk two blocks and hit the bar. Sam spent the morning showering and shaving.
He shaved his balls, face, legs. He took his long hair and teased it.
As he continued to get ready he got another email.
He opened the letter and clicked the link. He then read the letter.
"Looking forward to tonight." "Wear something incredible."
Sam knew the perfect outfit for tonight. Just then he heard his brother come home. Sam admired his brother Jeff who is 29, a 6ft Marine, crew cut, very muscular, he also dated a lot of women. Their mom hoped one day Jeff would settle down with a nice woman and give her grandchildren. She knew she wouldn't get them from Sam. Though Sam said he would adopt. His mother as much as she loved him knew that would never be the case. "Sam you here?" "Upstairs." Sam put his regular clothes on. As Jeff walked up. Sam closed his email and opened a link to his college for classwork. He knocked on his brother's door. "Hey little fag."
Sam hated being called that. "Jeff can't you ever say..." "Hi Sam?"
"Or hey little brother?"
"Yeah." There was pause. "But I like calling you fag." Sam glared.
"Okay how about Queer Man?" "You sound like a superhero." "Queer Man, Here to protect our fair city from the penis aliens." Sam shook his head as Jeff laughed. "Okay." "Seriously, I'll stop." "Listen." Sam was listening. "I'm going over to Robs." "Tell mom I have a date tonight with a cute girl." "Mom expects you to get married someday." "Maybe this will be my future wife." "We'll see." "Besides, I like playing the field." "And I like pussy." "Unlike you."
Jeff got up and left. Sam started on his assignments. After a few hours. Jeff knocked again on Sam's door. "I'm heading out." "I thought you left already." "No." "I worked out and then made a sandwich." Jeff then left. 5 minutes later Sam and Jeff's mom Sandra came home. "Hey Sam." She was chipper as always. "Hey mom." "Listen Jeff was here earlier." His mother was listening. as he talked. "He has a date tonight." Their mom's eyes lit up. "He says he likes playing the field." He left a few things out. "Well dear he's sowing his oats."
"I have to go back to work." "Will you be okay by yourself?" "Yeah. I'll be fine." His mom gave him a kiss on the forehead. "I have time to make myself a sandwich then go back to the office." After that Sam went upstairs.
He called his friend Tina. "Tina I need my royal blue skin tight dress , nylons and royal blue knee high boots." "With the clunk heel." Ten minutes later Tina was over and she got Sam ready for his date. She did his make-up, teased his hair, made sure he looked hot. Sam looked at the time it was 6. "Want me to come as back-up, just in case?" Sam smiled. "I should be okay." "Wait, I forgot a purse." Tina ran down to her car and brought a purse up. "Don't lose it." "I promise I won't."
After that Sam headed out.
Sam headed to the bar when he got to the restaurant. He was 5 minutes early. After a drink he saw his brother dressed exactly as it was in the email. Jacket with a flower, red shirt, white tie. Sam thought this might be a strange coincidence. He walked over and in a feminine voice. "Hello." Jeff was speechless. "Are you meeting someone here tonight?"
Jeff responded. "My friend set me up on a date with you tonight."
"May I ask your name?" "Sam." He laughed. "My brother has the same name." "Does your friend know the dating site I'm on is a gay dating site?"
Jeff was silent for a minute. "Do you mind if we sit down?" Jeff asked.
"Bar or Table?" "Table." Was his reply. Jeff walked over to the Maitre D and a minute later they were being escorted to a private table.
They got their menus and looked everything over. The waitress came over and took their orders. "Listen, I hope you can keep this between you and me." Sam was silent. "I'm a Marine." "I'm also gay." Sam was still silent. "My brother is also gay." "I give him a hard time cause I need to pretend to be a man." "He's probably more manly than I'll be." "If my mom knew I think she would disown both of us." Sam then spoke up. "Doesn't the military still do the don't ask don't tell policy?" "Yeah but I still need to be careful." "I'm sorry to lay all this stuff on you." Just then the waitress returned with their food and drinks.
After dinner. They left the restaurant. "Think I can see you again?" Sam decided to come clean with his brother. "Jeff, you're a good man."
Jeff blushed. "But you should know..." Jeff was waiting to hear "I'm not interested. Instead he heard. "I'm your brother." Jeff was taken aback. Sam then used his regular voice. "Yes for real."
Jeff and Sam walked home talking about tonight. When they got inside. Their mom was still not home. "Hey Sam?" Sam turned around. "Thanks for tonight." Back in his feminine voice. "Hey Second Lieutenant ."
Jeff turned around. "How would you like me to suck your big massive 10in cock?" Jeff laughed thinking Sam was playing a joke. "Sure." Sam walked over to his brother and dropped his pants. He then slid the undies down and out sprang a hard 10 in cock. Sam went and started to lick the shaft. Slowly working his way up to the tip. Just then he swallowed a good portion of the cock. Jeff grabbed Sam by his head
forcing more of his cock into his brother's mouth. Sam made some noises as he sucked. He then pulled back and spat on it. Looking up at his brother. "I want you to fuck me hard and good Second Lieutenant."
Jeff loved it that his brother was calling him that.
Sam kept sucking and jacking his brother's cock off. After a few more swallows and jerks. Jeff shot a thick white load down Sam's throat.
Sam took some cum and spit it out. Jeff then shot a thick load on Sam's face. Sam got up and took off his dress as Jeff stripped. Jeff noticed his brother's little penis. "I guess it's safe to say." "I am a man." He grabbed his brother from behind. "Sure you want this twink?" "I'm your..." before Sam finished. Jeff inserted his cock into his brother's ass. "Oh Fuck." "Now what were you saying?" "You're my what?"
Sam was loving, getting fucked by his brother. "I'm your... whatever you want." "Sam your my fucking bf/gf." "My fucking bitch." "And my brother." Just then Jeff shot a thick load in his brother's ass. "I want you to take your boots off." Sam complied. His brother walked out with his boots. He came back in a few minutes later. Each filled with yellow liquid. "You can either drink what's in here or I can dump it on you." "I'll drink from one boot." "Then dump the other on me."
Jeff agreed. Poured one boot down his brother's throat. the other on top of his head. The liquids were warm. Jeff sat on a chair in his room. "Sam, I want you to straddle me." Sam did as complied. he took a hand and found his brother's cock and inserted it. He began to slowly go up and down moaning.
"My Sammy." "Such a good twink." "Are you sorry you got me fucking you?" "No." "I love it." "I dreamed of this moment." "Fuck me, Brother." Jeff was more than happy to comply. "I have to admit. "I love fucking you." After a few hours the brothers were spent. They laid in Jeff's bed. Kissing with passion and tongues darting in and out. Jeff rolled on top of Sam. "I have to say I didn't think I would enjoy myself as much as I did." Sam Agreed. Sam then jokes. "Think we can fuck tomorrow night?" "I have a dress I want you to shoot your thick load on." Jeff smiled. "I believe we can." With that they went to sleep.