Maybe this was the perfect opportunity to catch Tyler cross-dressing, so he could mock him without admitting that he saw Tyler at the milf’s house. Mark knew the code to the back door—he could simply pretend like he randomly swung by to say hello, which was something he did all of the time.
Mark grinned as he carefully climbed down the trellis.
CHAPTER X
Tyler looked good. He wanted to think that he looked like a dude in drag, but he couldn’t help but look good. He even squeezed into the tightest dress he could find in his sister’s closet, hoping it would make his shoulders look broad and outrageous, but the dress just proved that Tyler had narrow, feminine shoulders. It also proved that he had wide feminine hips, a thin feminine waist, and a perky feminine tush.
He tried on a different outfit, hoping the tight dress was just creating an illusion. Maybe it was just the way the dress was cut… but no. Tyler looked good in everything. He even caught himself smiling at one point, because he looked so cute.
So he wasn’t just hallucinating at the trans milf’s house. It wasn’t just a stress-induced imagining—he really did look like a chick. And maybe that’s why they picked him for the deed. No, that’s definitely why they picked him for the deed.
Now, Tyler found himself buttoning up a plaid skirt that made him look a bit like a sexy waitress in an Irish pub. He’d always loved staring at the waitresses when he walked by the Irish pub that was between his house and the school. When they bent over to clean the tables, they showed off their asses and the small bulges in their panties. Now, with his cock tucked back, it kind of looked like Tyler had the same camel toe bulge when he belt over.
The skirt went great with a pair of thigh-high white stockings. No heels were needed. The stockings alone made his feet look incredibly cute. With the skirt he wore a tight black tank top, and then he found himself in front of the mirror, touching up his makeup. At first, he’d only put on makeup in an attempt to prove to himself that he didn’t really look like a chick. But now, he was trying to see how far he could push it—just how feminine he could look. And he impressed himself with the results. The pink lip-gloss made the biggest difference. He loved the way the lip-gloss felt on his lips.
He stood up and did a spin in front of the mirror. And then he stared at himself, half in a state of admiration and half in a state of confusion, trying to figure out what the hell he was doing. Why was he wearing his sister’s clothes? Why did he care if he could look like a girl or not? What difference did it make in the end if he wasn’t actually a girl? Tina wasn’t actually a girl and it made a difference for her…
Tyler noticed a small eyeliner smudge on the corner of his eye. He looked around for a cotton swab to correct the small error, but there were none in his room. But he knew there was a box in the bathroom, so he slipped out from his room and went to the bathroom. The lighting in the bathroom was much softer and brighter. He looked even prettier in the bathroom mirror, so naturally he caught himself once again in front of the mirror, admiring himself as the minutes passed by. Then he saw that smudge again and remembered the point of his bathroom excursion. He fixed the small eyeliner smudge and then he went back to his room.
And it took him a moment before he noticed Mark sitting on his bed, wearing a big, toothy grin. “Looking good,” he said, trying not to laugh.
Tyler suddenly felt sick. His legs felt weak and his eyes were suddenly blurry. He tried to take a breath in, but his lungs were suddenly too shallow. “It’s—It’s not what it looks like.”
“So you aren’t wearing your sister’s skirt and stockings? And I’m assuming then that you aren’t wearing her panties, too?” Mark asked, still with that big grin. He jumped up from the bed and started walking around Tyler. Tyler just wanted to run, but he didn’t know where to run, and he knew that running would be pointless. The damage was already done. Now he needed to figure out how to explain himself. Maybe he could say he was rehearsing for a play… But what play? Maybe he could say that his clothes were all dirty, and he was just using the makeup to cover up some pimples… Yeah, Mark would surely go for that…
“I’m not going to lie, Tyler. You look like a lady. Is this something you do a lot?” Mark asked. He stepped behind Tyler and looked at Tyler’s ass. Tyler was too afraid to look back, to look his friend in the eyes, so he wasn’t expecting the hard slap he got to the ass. “Ouch!” he yelped, jumping forward.
“I was just messing around,” Tyler said, his voice shaking.
“I’m disappointed in your voice, Ty. You pull this look off and then you sound like that? At least put a little bit of effort into the voice. Say it again—tell me you were just messing around again.”
Tyler stood silent, still trembling, still wanting to throw up.
“Say it, Tyler. Hm, I don’t like the name Tyler. It doesn’t suit you. How’s about Tiagra? Maybe just Tia—Tia has a nice ring to it. What do you think, Tia? Tell me again that you were just messing around, but use your best girly voice.”
Tyler took a deep breath. He didn’t know what was happening, but he had a feeling there was a tinge of blackmail behind Mark’s devilish grin. Mark had a lot of friends—and he would only have to tell one of them for the news to spread around the whole school. So Tyler knew that had to play along with Mark’s games. “I was just messing around,” he said with a feminine twang.
Mark’s face lit up. “Great. I love it. You sound so cute, you know that, Tia?” Mark walked back in front of Tyler and stood in front of him. He put his hands on Tyler’s hips and looked into Tyler’s eyes. “Look at those eyes. Where did you learn to do your makeup like that?” Mark asked.
Tyler felt cold and small and short of breath. He took another deep breath and then he shied away. “I told you I was just messing around.”
“When I mess around, I don’t put on my sister’s clothes,” Mark said. Tyler’s heart stuttered because he knew Mark was right. He knew his excuse was terrible and it was too late to go with another one—not that it would have made any difference. Mark knew Tyler better than anyone. Mark wasn’t the smartest guy, but he wasn’t dumb enough to fall for any excuses. The reality was right in front of him: Tyler was getting himself dolled up in his sister’s clothes and makeup.
“Please don’t tell anyone,” Tyler said.
“Ask me again in your girly voice,” Mark insisted.
“Please don’t tell anyone,” Tyler said, this time in his best girly voice.
“Now get on your knees and ask me. I want to hear you beg,” Mark said.
Tyler’s legs trembled and his gut turned. He couldn’t let the world find out about his cross-dressing curiosity. So he sunk to his knees and pressed his hands together. “Please, please, please don’t tell anyone about this.”
Mark’s lips curled into a big grin. “Now ask me with my cock in your mouth.”
Tyler froze. His lips parted and his jaw trembled slightly. He tried to respond, but he couldn’t muster up any words. His spine was cold.
“Girls can’t resist me. So if you want to be a proper girl, you won’t resist me either. So go ahead and take my cock out and suck it. If you can get me off, then I won’t tell anyone. Scout’s honour.” He still had that grin on his face. Was he serious? Or was he just setting Tyler up? Why would he want to be sucked off by his male friend? Was Mark secretly gay? Or was he fooling around? Or did Tyler really look that good with a skirt and some makeup?
Tyler tried to think of something to say but his mind was blank. He felt like he was on the verge of throwing up. “What?” he finally managed to say.
“You heard me. Go on now. Or I’m calling up Sheldon. He’ll think this is so hilarious. And don’t bother telling anyone that I asked you to suck my dick. They’ll obviously never believe you.” And Mark was right—no one would believe that Mark asked Tyler to suck his dick. Everyone would assume that was just Tyler trying to deflect the humiliation.
Tyler looked down at the slight bulge in Mark’s jeans. Could he do i
t? Was it worth his secret remaining safe? He watched as his trembling hands reached forward and began to do away with Mark’s belt. He was actually doing it! But it didn’t seem like he was in control of his own body, as if some alien force had possessed him. He found himself watching as he gently pulled down Mark’s fly, and then he found himself watching as his fingers slipped through the slit. He may have been stuck watching like a prisoner trapped in his own mind, but he could still feel everything. He could feel the warm, throbbing girth of Mark’s cock. And he could feel Mark’s soft pubic hair.
He watched as Mark’s long cock flopped out from his jeans. Tyler looked up at Mark, who was still grinning. Mark’s cheeks were red. “Go ahead. Suck it,” Mark said. He really wasn’t kidding. He really wanted a blowjob from his best friend. So Tyler looked back down at the cock, which was throbbing and growing. He closed his eyes and leaned forward, parting his lips wide. He felt the warm tip press against his bottom lip and he knew there was no turning back.
CHAPTER XI
Mark’s heart was pounding but he kept his composure. His plan wasn’t to get Tia to suck his cock, but he couldn’t help himself once he was in the room with her. She was pretty. She didn’t look at all like a guy in a skirt. Besides, he knew Tia wasn’t going to tell anyone, so what was the harm?
She sucked like a professional cocksucker. Mark couldn’t help but wonder if his was the first cock she’d ever sucked. Judging by her dark red cheeks and trembling hands, it was—but every time she managed to sink his whole cock down her throat without gagging, he wondered. But it made no difference. It felt good and Tia looked hot, even from above.
Mark sat down slowly on the floor, making Tia sink lower. She went from her knees to her hands and knees. She curved her back low like a cat doing her morning stretch. And she managed to continue sucking that cock. Mark squirmed slightly. His anxieties began to shift: from, ‘Should I really be blackmailing my friend into sucking my cock?’ to, ‘What if I come too quickly in my friend’s mouth?’ Tia’s tongue felt good, the way it wrapped around his girth and tickled his tip. She managed to press her lips firmly around his meat, stimulating his tip amazingly.
Tia moaned slightly. Her skirt had slid up her back, revealing her whole butt. She was wearing a thong, but the thin piece of fabric was too thin to even cover her whole asshole, so Mark was able to watch it pucker and beg to be penetrated. And Mark found himself legitimately considering the possibility. “How badly do you want it?” Mark asked.
And for the first time since plunging his cock through her lips, Tia let his cock fall out from her mouth. “Badly,” she said with glowing eyes.
“Good. Don’t move,” Mark said. He hopped up to his feet and walked around his sexy kitten. She watched him with those shy, glowing eyes, her butt still perked up into the air. Mark sunk down his knees behind her, slapping his wet cock between her butt cheeks. Tia wiggled her bum gently, grinding her puckering hole against Mark’s throbbing shaft. “Fuck…” Mark muttered. His cock was so hard that it was actually a bit sore—he wasn’t sure if he’d ever been so hard in his life. A trickle of clear fluid ran down from the tip of his cock—it was either Tia’s saliva or his cock was drooling pre-cum.
“Please just fuck me already,” Tia begged. So Mark aimed the tip of his cock against her tight hole and he began to press in. He pushed hard but he couldn’t seem to penetrate her. He tried spreading her cheeks and spitting into her hole, but she was still too tight.
“It’s tight,” he said.
“Keep pushing,” Tia said, her voice strained.
He grunted slightly as he dug his fingertips into her hips. And then finally, he penetrated her. She let out a sharp whimper and his cock plunged two inches into her hole. He stopped for a moment while he waited for her to relax, and then he started sinking deeper. He wasn’t even inside of her completely before the euphoria started to set in and he realized he wasn’t going to last very long. He felt his cheeks turning red. She looked back at him with those glowing eyes, opened wider than ever as if she could feel that he was about to burst. He tried to hold back, but it was hopeless. She was too tight and too warm and too sexy. He tried to get a few quick pumps in, but that was all he could do before he was filling her tush with his hot load. She gasped and her body became tense. He held her firmly in place while she tried to squirm.
He stared down at her little butthole after he pulled out, and he watched as his cum shot dribbled out. “That was fast,” Tia said with a grin on her face.
Mark felt the colour drain from his cheeks. The only thing more embarrassing than fucking your best friend in drag is coming within seconds of penetration. Mark cleared his throat. “It’s—It’s been a while,” he said. “We can go again in a few minutes. Just give me a few minutes, okay?”
Tia giggled. She had a cute giggle, but it only made Mark more embarrassed. “It would be a shame if Sheldon found out about that, wouldn’t it?” she said.
“What are you talking about? He would never believe you,” Mark said, shaking his head.
“You don’t think so?” Tia held up her phone and then Mark heard the camera snap. He looked down to see his cock was still out, with a dribble of cum hanging halfway to the floor. Tia giggled.
“Give that to me,” he said, trying to snatch it from her. But she held it back.
“No,” she said.
“Delete that picture. Or I’ll tell everyone that you dressed up in your sister’s clothes,” Mark said.
“You wouldn’t dare,” she said. “Because I’ll tell everyone you came in less than ten seconds in my ass.”
Mark’s face was suddenly a shade of purple. “What do you want?” he asked. “What do I need to do for you to delete that picture?”
“Well,” Tia said with a big grin. “Maybe I need to get off. Why don’t you go over to the bed and bend over?”
“You’re kidding, right?” Mark said, his jaw trembling. He tried to force a grin in an attempt to keep his composure.
“I promise you’ll like it,” Tia said. “And I promise I’ll last longer than ten seconds.”
“Anything else,” Mark said, crossing his arms.
“Nope. That’s all I want. Haven’t you ever fantasized about being pegged by a beautiful woman, Mark?” Tia asked. She reached down and wiped the strand of cum off of Mark’s cock with the tip of her pointed finger. She brought it to her lips and licked it off, still with that arrogant grin.
“No,” Mark said.
“Liar,” Tia said. And he was lying. Sometimes at night, those thoughts would creep into his mind: fantasies where he was laying on his stomach while a girl was giving it to him from the top. Sometimes he would even slip a Sharpie into the bathroom with him when he went to masturbate, and he would stick the whole marker into his butt, to make his orgasm more intense.
Now, he found himself on Tia’s bed, laying on his stomach. His heart was pounding. Was this really happening? Was he really about to let his best friend stuff his ass from behind? Would it hurt? Tia slipped her cock out from her thong. It sprung upwards, already erect. And it was a lot bigger than a measly Sharpie marker.
CHAPTER XII
Tyler watched as Mark’s fingers tightly gripped the bed sheets. Mark was cute when he was nervous. Tyler couldn’t help but giggle.
He felt strangely free, but he wasn’t sure why. Once he realized that Mark really did find him attractive in that skirt, he felt his heart swelling in his chest, as if he’d received one of the greatest compliments of his life, even though he knew it shouldn’t have been taken as a compliment. No man should feel proud of how good they look in women’s clothing—at least that’s what Tyler had been raised to believe.
But what was so bad about it? Tyler tried to think of some con to being sexy in women’s clothing, but he could think of nothing. So far there had only been pros: he’d been given five thousand dollars, and now two different people had thrown themselves at him, lusting over him as if he was a fine commodity. He felt good, like he
was finally being noticed and appreciated. There was finally a point to his petite, scrawny body. He finally felt happy—so why should he feel bad about himself? So what if some people think it’s weird to dress up like a girl? So what if society says a man shouldn’t put on women’s clothing? Tina put on women’s clothing and she had breast implants and she was probably taking hormones—and she was one of the happiest people Tyler had ever met.
So maybe he would try Tia out for a while. Maybe he would see if life would be better as Tia. Maybe being caught by Mark was the best thing that had ever happened to him—to her.
She slid the tip of her cock down the length of Mark’s butt crack. He squirmed slightly, his body still tense. But she knew he would relax as soon as he felt her long, throbbing member inside of his body. She needed something as lubricant. She thought about spitting, and then she felt the still-warm cum dribbling down her leg. She reached down and wiped it up and then she wiped it on her cock. She had no idea if it would work, but she was willing to try—to stick Mark’s own cum up his ass.
Shockingly, the cum made excellent lubricant. With the white warm goo slicked all over her cock, she slid in without much effort, even when he started to clench and groan. “Oh, just relax and admit that you like it, babe,” Tia said, as she gently squeezed Mark’s ass cheeks.
She started pumping him, sinking a little bit deeper with each penetration. His whole body was trembling. He was still stiff, refusing to relax. She put a hand on his back and whispered, “Shh, just relax. Surrender.” He remained tense for another moment, and then suddenly, she could hear him taking a deep breath. His body sunk down low and his asshole unclenched, though it was still very, very tight.
There was a mirror across the room. Instead of staring at her muscular date, Tia found herself staring into the mirror, watching herself as she pumped her friend from behind. She really did look good, even when she was mounting another man. The socks she had stuffed into her bra didn’t look terrible, though a nice pair of implants would have looked better. Tia found herself thinking about Tina—maybe she could ask Tina where she got her breasts done.
GIRLIFIED: 15 BOOKS MEGA BUNDLE Page 20