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There was a knock on the door to my room, “Come downstairs. You are drinking and playing poker with me.” Shawn commanded.
Shawn is my mom’s boyfriend. He is a white 48-year-old 6’2″ tall and athletic former-jock that grew up as a spoiled rich kid. He has never worked for a living and
lives off of his grandpa’s trust fund.
My mother, Gina, and I moved in with him in his fancy 4,500-square foot house about two years ago.
My mother is a tiny lady, about 5’2″, full of energy and spunk. She is beautiful with a thin waist, medium-sized boobs and long back hair. She looks amazing for someone 40 years old.
I can’t complain about us moving into Shawn’s house. It is a beautiful home with fancy foyer and big rooms, including a media room, billiard room and a beautiful swimming pool outside with jacuzzi and rock waterfalls. This place beats any place we’ve lived before by far.
But, Shawn can be an arrogant asshole and verbal bully. He likes to call me a nerd and a girl. He make fun of me for being so short and skinny. He says I look more like a daughter than a son standing next to my mom. My mom and I are nearly the same height and complexion and I have a small frame like her. I love my mom, but, I hate being called her daughter! I’ve always had a low self-esteem and a compex about my height and his insults certainly don’t help.
Besides his money. The only other thing Shawn appears to be good for is his cock. By the sounds coming from their bedroom, I would guess that he is very hung and knows how to use his tool. I have to put headphones with loud music blasting to avoid hearing them fuck. They get ridiculously loud. The bed sounds like it is being slammed against the wall and they both moan and grunt like wild animals in heat.
We ran into some unexpected financial trouble about three months ago. Shawn and the other beneficiaries of the trust got into a nasty fight about the terms of the trust agreement and that fight ended up in court. Then, the assets of the trust were frozen until the court could issue a ruling on the disputed issues. Shawn had no other source of income and the bills piled up very quickly. We received notices that the utilities would get cut off, and, even this did not send Shawn looking for a job. He was not qualified to do anything, even though he had gone to an ivy league school for a liberal education. Consequently, my mother had to get a job to pay the bills while they waited for trust issue to get resolved.
Before shacking up with Shawn, my mother was a paralegal in a big law firm. Her former boss was John Stephens, a handsome and well known asbestos litigation attorney. He is a senior partner in the prestigious law firm of Major & Strong, LLC.
Shawn hated for my mom to work with John and made her quit her job with John several years ago, because, of Shawn’s insecurities and possessiveness. But, the financial situation was getting dire, so, he let her go back to work temporarily.
To make matters worst, my mother often had to work late in the evening and she traveled with John when he had to go out-of-state for depositions, hearings or trials.
She had left with John Sunday night for an entire week, because, she was helping him in a week-long trial in Florida.
Although Shawn is trying to keep his cool, I sense that he is livid under the surface and can blow up at any minute.
I don’t want to be the victim that he takes out all his anger on, so, I was doing my best to avoid him.
He was knocking on my door now. I opened the door to my room and said hi to him.
“Where did your poker friends go?” I asked him. About an hour earlier, eight of his friends were sitting down with him in the kitchen table playing poker.
“They pissed me off and I kicked those bastards out of my house.” He explained.
“What happened?” I asked.
“Josh made a joke about how attorneys screw their clients, and then, Ben made a fucking obnoxious joke about how they also screw their paralegals. I came close to throwing blows with him. He said he wasn’t referring to Gina, but, I know that’s what he meant, the fucking asshole thinks he is a comedian! I kicked his ass out of my house.” Shawn explained.
“What about the others?” I asked him.
“Those bastards all laughed at Ben’s stupid-ass joke! So, I kicked them all out right behind him! Motherfuckers!” said Shawn.
I really did not want to play cards with Shawn. I knew he would end up getting pissed off at me, because, I do not know how to play cards.
“Shawn, I’m playing an online computer game with my friends. I can’t play right now.” I told him.
He looked me in the eye and said, “You ungratefull little bastard! You and your stupid computer geek friends need to stop sucking each other’s dicks and find something better to do than play video games all day. This is why you are 18 and still a virgin!”
I spend a lot of time on my computer and Shawn loves to belittle me about it.
He added, “Sam, quit being such a fucking computer loser! Come down to play poker with me.” He ordered.
“Fine, Pendik Grup Escort Shawn. I’ll play, but, I don’t know how to play poker.” I said.
“Okay, we’ll play blackjack, then.” He said.
I sighed.I really didn’t know how how to play blackjack either, but, at least its easier than poker. I think the object of the game is to get the highest number, but, not go past 21.
I walked down to the kitchen with him and he served me beer. “Drink up!” He said. I had just turned 18. But, for Shawn, that was the legal age to drink. Nevermind what the law says.
We played blackjack for quarters. I was bad at it, so, I lost the $20 I had in my wallet.
Shawn had to lend me money to keep me playing.
“Your fucking mom, she’s out of town for a whole week! How does that make me look to everyone? And, what am I supposed to do for a week? Jerk off, like some loser teenager?” he asked rhetorically.
He looked me straigh in the eye and asked, “Do you think she’s fucking that guy, John?”
“No, of course not. She wouldn’t do that. My mom is loyal.” I said.
He did not seem totally convinced.
After about an hour of playing poker with Shawn, he paused and made some calculations. Then, he said, “You owe me $500!”
I replied to him, “I don’t have $500! I thought this was just a game for fun.”
He said, “Game for fun? What do you think, I’m one of your nerdy computer friends? I don’t play unless there is real money involved.”
I said to him, “Well, I’ll have to pay you back over time, because, I don’t have that kind of money.”
He seemed to get upset, but, then, his expression changed to sinister and he said, “I have an idea.”
He said, “I am going to let you win your losses back. We’ll play another hand and I am going to give you a big advantage.”
“You can start with an ace.” He said handing me the ace.
I asked, “So, if I win, I don’t owe you anything?”
“Exactly.” He said.
Then I asked the more important question, “And, what happens if I lose?”
He answered, “How can you lose? I am giving you such a huge advantage. I am practically just giving you back all your money.”
I asked him, “Yes, I know, Shawn. I get it. But, what if I lose again?”
He said, “Well, then, I will say a dare and whatever I dare you to do, you must do.”
“What kind of dare?” I asked.
“Shit, I don’t know. I haven’t even thought about it yet! Something embarrasing and humiliating, that’s all.” He said.
I looked at him and I must have looked scared, because, her tried to calm my fears, “It won’t be anything that hurts you or leave scars, except that it will hurt your ego. It may scar your ego a little, but, look at it this way. It is not like you can have much of an ego, anyway! I mean, look at you!”
He is such an asshole! He loves to put me down!
I did not want to argue with him, so, I accepted with just one condition, “You will not make me leave the house and be humiliated in public, okay? Whatever humiliating thing I have to do will be in this house and only you see it.”
He thought about it and said, “I’d prefer to humiliate you in public, but, okay, fine.”
I had a lot of misgivings about this, but, I just wanted peace and to get his mind away from thinking that my mom was fucking her boss.
I was used to Shawn humiliating and degrading me, so, I thought that, whatever he does, I can handle it. I’m used to it.
I actually came close to beating him at blackjack, but, he beat me in the end. He won 6 games out of 10. I think he cheated.
I lowered my head and asked him, “I knew this would end up like this. Okay, so, how will I be humiliated today? Let’s get it over with.”
Shawn laughed. He had drank many beers and was acting a little inebriated.
He spent the next five minutes keeping me in suspense while he pondered my dare.
Then, he lit and said, “Ha! I got it! You look so much like your mom. I dare you to dress in your mom’s clothes!”
I said to him, “No, I’m not doing that!”
He responded, “Fuck yeah you are! You lost and I won! You have to do it!” He was getting hostile.
“Shawn, I don’t even know how to dress like a woman. And, its not right to play with my mother’s clothes.” I said to him.
“No worries.” He said, sounding a little calmer. “I will pick something for you to wear; something she does not wear anymore.” He said and left the room.
He came back with an outfit I had never seen before. It was a very revealing little yellow spandex mini dress with cutout sides
“That looks like a hooker dress. That can’t be my mother’s. She would never wear something like that!” I protested.
He chuckled, “This is her dress alright. This is what she was wearing at the club the night I met her. One look at her in this dress and my jaw dropped to the floor. I got a massive hard-on for her. After running a solid game on her, I took her to the bathroom, tore off her panties and fucked the shit out of her up against the bathroom wall! We broke that fucking stall! Pendik Manken Escort It was love at first hard fuck!”
“Shawn, don’t talk about my mom like that! And, there is no fucking way I am wearing that dress! It is gross to even think about wearing that dress!” I said emphatically.
He looked me in the eye and said, “Why? It’s clean. My cum has been washed out and I can’t even remember the last time she wore it for me, even though it’s always been my favorite dress.”
He looked at me getting hostile, again. “Just fucking wear the dress, okay!” He said.
“No!” I said.
“I’ll kick your ass out of my house like I did all my friends! We had a deal! You have to settle your accounts and pay up!” He said.
Then, he said in a friendlier voice, “Look, tell you what. I’ll forgive your gambling debt to me, okay. I feel like shit right now and I need to humiliate you some to get a good laugh and feel better.”
“Fine.” I said about to break into tears. I knew he would make me do something horribly humiliating, but, this exceeded all my worst expectations!
I hate him! He is such a fucking douche!
I just wanted to get this over with as soon as possible.
“Fine. I’ll wear it, whatever.” I said resentfully.
He smiled. The crisis was averted.
Shawn gave me the dress with white panties and bra, white garter belt, white fishnet stockings and white thigh high boots. “You seriously want me to wear all this?” I asked him.
“Absolutely! And shave your legs, too!” He ordered.
I bit my tongue so as not to yell at him, “Fuck you!”
I hoped that my mother was cheating on him. He deserved it!
I walked up the stairs and went to the bathroom in my bedroom. I shaved my legs. It was weird and it took a long time.
I was very upset and almost cried from the humiliation of being forced to dress like a woman. What sick bastard humiliates another man forcing him to dress like a woman?
Making me wear a slutty dress that he fucked my mom in was really twisted and fucked up!
I put on the white panties and bra, the garter belt and the fishnet stockings. I have to admit that wearing silky underwear felt kind of nice when your skin is shaven. I understand why women love to wear this stuff. It was a surreal experience.
“Hurry the fuck up!” Yelled Shawn from downstairs.
I put on the dress and climbed into the thigh high boots. I was not sure I could walk in them. It was like being up on stilts.
I looked in the mirror, and then, something weird happened. I was attracted to the girl I saw in the mirror!
The dress fit me like a glove! I have a thin waist.
The thigh high boots must be like 7 inches tall. They made me feel tall and my butt stuck out. I never realized it before, but, I had a nice butt!
My legs looked longer than they were and the fishnets made my legs look sexy.
Oh my God! I’m getting turned on by my own reflection! I look sexy! My dick was getting hard!
Yet, something was bothering me. If I was a real girl, I would have makeup and longer hair. Why didn’t Shawn ask me to put on makeup and a wig?
My mom has a lot of makeup in their bedroom and she has wigs that she uses for halloween costumes. Shawn should have asked me put on makeup and a wig. Why hadn’t he thought of it?
I became very curious about how would I look in this outfit with makeup and a wig.
Finally, my curiosity got the best of me. I decided, fuck it! I’m going to do it, even if Shawn didn’t ask me to!
I walked into Shawn and my mom’s room. It was difficult to walk in the sky-high boots, but, I was making quick progress in learning to walk in sky-high boots.
“What the fuck is taking you so long?” I heard Shawn yell downstairs.
“Almost done! Just a couple of more minutes!” I yelled to Shawn.
I looked through my mom’s makeup. I picked up a dark red lipstick and put some on. I did not know how to put on any of the other makeup, but, I tried to powder my face a little and I tried to put on eyeliner.
I couldn’t believe I was doing this! I had the urge to experiment with the makeup, but, I was already taking too long and I did not want to piss off Shawn.
I went to my mom’s closet and looked at her wigs. I finally decided on a long blond wig. I put it on and looked in the mirror.
Oh my God! My jaw dropped! Is that really me?
I want to fuck that girl in the mirror! I am hot! I felt a sudden rush!
What is this rush I am feeling? I guess I’ve never looked in the mirror and felt attractive before. This is what it is like to be pretty! It feels great!
I am attractive dressed as the opposite gender, but, at least I am attractive! I became so excited posing in the mirror that I forgot that Shawn was still waiting for me downstairs.
“Just like your mom to keep me waiting! What the fuck is taking you so long!” Said Shawn, walking into the bedroom. He had come up to find me.
I was suddenly extremely self-conscious and looked for a place to hide. I didn’t want him Pendik Masöz Escort to see me. I knew he would ruin this for me! I was not ready to be ridiculed and humiliated! My ego was actually soaring high for once, and, I was sure he would throw a bomb at it and kill it.
I tried to run to the bathroom, but, Shawn grabbed me and stopped me.
I felt embarrassed and ashamed and I braced myself for Shawn’s cruelty.
Shawn looked me up and down and I expected him to laugh hysterically any second and tell me how ridiculous or repulsive I looked. But, he didn’t. He just stared at me.
The suspense was killing me. I thought – Just shoot me already! Say what you are going to say! Slit my throat already!
Then suddenly, he finally, he said, “I knew it!” “Knew what?” I asked.
“You should have been a daughter instead of a son.” He said.
Was that meant to be a slight or a compliment? I wasn’t sure, but, I blushed.
He said, “You look so much better as a girl! Don’t you think?”
I did not want to admit it, but, yeah. I looked a lot better as a girl.
Shawn stood next to me. Even with my sky-high boots, he towered over me.
He put his hands on my shoulders and turned me towards the mirror to look at myself. I almost jumped from the physical contact. He had never put his hands on my body. No one had, except only my mom. Shawn did not remove his hands from my shoulders. It was very awkward.
He said, “See, tell me you don’t agree with me.”
He started massaging my shoulders. Shawn has big hands and he knows how to use them well! His shoulder massage felt wonderful! I nearly closed my eyes. Sure, it felt nice to have my shoulders massaged, but, something was creepy and awkward about it. It must be the alcohol that is making him get so touchy.
I figured I shouldn’t make a big deal about the massage and give it a couple of minutes. Then, I’ll tell him I am really tired and need to go to bed.
Then, Shawn’s big hands moved from my shoulders to my neck. Oh my God! That felt even better than my shoulders! – I thought to myself, I have to stop this! But, it felt so good to have my neck rubbed.
I’ll tell him I am tired and wan’t to go to sleep in two minutes, I told myself.
I watched the two of us in the mirror. It was like watching a sex movie about a hot girl in a slutty outfit and a very attractive older man trying to seduce her. If I was not the girl, I would want to see them fuck! I realized my dick was getting hard. I have to get out of this situation!
“Um, Shawn, I am very tired. I think I’m going to sleep now.” I said to him.
“Don’t you like how that feels?” Shawn asked me continuing to rub my neck. “Yes, of course. Who doesn’t like a massage?” I said.
“Is it getting you turned on? Do you want to, you know, make love?” He asked.
I gasped and moved away from him. I was shocked and put my hand over my mouth. “Oh my God, Shawn! You must be so drunk! I’m a guy and you’re my mom’s boyfriend!” I exclaimed.
He grabbed me and pushed me up against the wall. He grabbed my wrists and pinned them to the wall above my head. I was in shock and did not know what to say!
“We can keep a secret, you and me!” He said.
His body was up against mine. I was trapped by him with no way to escape.
“No! Let me go!” I exclaimed.
“You know you want it! No straight guy gets dolled up like this! You are a girly boy! Let me fuck you, okay. I’m horny!” He said.
“I’m only dressed this way because you made me wear this! I’m not girly!” I protested.
“Don’t pretend that you are not enjoying being dolled up like a girl. Who asked you to put on makeup and a wig, huh?” He asked.
I did not know how to answer him.
I was suddenly getting very confused about everything. Was there any truth to what he was saying? I do like how I look right now.
Shawn was holding me tight and I could feel his massive erection. I was right to suspect that he had a big cock! It felt massive!
Could he feel mine? I was getting hard, too.
Shawn spoke again, “You can’t fool me. I know you are hard. ” He said.
Then, he put his hands on my crotch and I let out a little moan when he touched me.
“Your little clit is hard!” He said chuckling and he rubbed my dick through my panties.
It felt incredible to have my dick touched by another person! I felt like moaning, but, bit my lip to stop myself from making a sound.
“You’re so wet!” He said laughing.
“Please Shawn, stop! You’re my mother’s boyfriend! This is so wrong!” I exclaimed.
“Your mom is a cheating bitch and I’m going to fuck her daughter!” He said!
“I’m not a daughter, I’m a man!” I exclaimed.
He chuckled and said, “Look in the mirror again and tell me what you see. Tell you what I see. I see Gina, only younger and hotter.”
I said, “No! I’m only dressed like this because you made me.”
He answered, “Well, that means you will do whatever I tell you. I’m telling you to be a girl for just one night. It won’t hurt to try for just one night!”
I said to him, “If this is your idea of humiliating me, please stop, it is enough! Please stop now!”
Then, his face turned serious and he said, “This is not bullshit! You want to die a virgin? Or, you want to experience sex that will make your head explode?”
Ben Esra telefonda seni bosaltmami ister misin?
Telefon Numaram: 00237 8000 92 32