“Good. Then fuck me good and make me come,” Tina said, looking forward again. So Tyler got up on his knees and he snuggled in close. His cock was already rock-hard—and it had been rock hard since the moment she had first reached down to massage it. It had even been hard while he was sucking her cock. Maybe he secretly liked it. Maybe he was discovering something about himself that he never knew before.
He pressed the tip of his cock against her tight hole.
CHAPTER VII
Mark hadn’t moved. He wasn’t even sure if he’d breathed. Well he must have breathed because he’d been standing up on that ladder for nearly twenty minutes. His fingers were numb from the night’s chilly air, and his toes were starting to become numb too. But he hardly noticed. It was hard to notice anything other than his friend, dressed in lingerie, sucking a tranny’s cock.
Mark felt a wave of relief when that cock sprang free—he’d dodged a bullet. He couldn’t wait to endlessly mock Tyler. He couldn’t wait to tell Sheldon what he saw. But then he found himself mesmerized by Tyler and the sexy tranny. He couldn’t stop watching. And now he was watching as Tyler pressed his cock into her big butt and he thought: at least he’s getting laid, and at least she’s a hot tranny.
And she really was a hot tranny—even Mark couldn’t deny that. He’d spent the latter half of the week swooning over pictures of her, and he’d spent that whole evening staring at her and wishing he were in Tyler’s position—until that cock came out.
Mark still couldn’t figure out the cross-dressing. Maybe the perverted old man in the corner—the man who obviously made the classified posting—wanted to see his trap wife get fucked by another trap, and he just couldn’t find a trap to do the job, so he threw five grand at someone who could pretend for an hour. And now it made sense why they picked Tyler and not Mark; Tyler had a small, scrawny, feminine body. Mark was all man: tall, toned, muscular, and rigid.
Tyler was thrusting now, sliding his whole cock in and out of the older milf tranny’s tush. She had her head down against a pillow. Mark could just make out the sound of her moaning through the double-paned window.
Mark even had to admit that Tyler looked pretty good in lingerie. His makeup was on-point and the black-haired wig looked surprisingly realistic. And hell, his legs looked fantastic in fishnets. Mark couldn’t decide if Tyler’s surprising trap potential was something to mock or something to lie about. He figured it might seem suspicious if he were to tell Tyler that he looked like a babe—so he decided he would lie and say that Tyler looked ridiculous.
Now, Mark could only see Tyler’s backside—which wasn’t the worst angle, seeing as Tyler had a nice ass. Mark found himself hoping that in a few minutes the traps would switch positions, so Mark could watch Tyler get stuffed. But he pushed those thoughts away, reminding himself that Tyler was a man, and he was his friend. Why would anyone want to watch their male friend getting stuffed?
Mark didn’t get to see the reversal. Just a couple of minutes after penetrating the tranny milf, Tyler came. He pulled out and coated her back with his sticky white load. The milf squirmed as his huge load slicked her back. Then a neighbourhood dog started barking and Mark realized it was probably his cue to leave, before he was caught and hauled off to prison for voyeurism and breaking and entering.
He climbed down the ladder and then he collapsed the ladder and stuffed it back into the shed. As he emerged from the shed, she saw the lingerie-clad duo walk back down the stairs, headed back towards that dressing room at the end of the hall, probably to get changed back to normal. The milf still had strands of white cum streaming down her back. Mark took one last photo with his phone and then he took off, grabbing his bike off the neighbour’s lawn and then heading straight home.
Mark didn’t go to sleep until the early morning hours. He found himself staring at his phone in disbelief, staring at those photos and videos he’d taken of Tyler and the tranny milf. He couldn’t figure out how to wrap his head around what he’d witnessed. He felt like he wanted to tell someone, but he wasn’t sure who to tell. He couldn’t figure out how to tell anyone without admitting that he stuck around to watch. He didn’t want to tell Sheldon what he’d discovered because he didn’t want to admit that he’d been swooning over a tranny for two straight days. Tyler knew that Mark had been swooning over a tranny, but of course Tyler wasn’t going to tell anyone.
So when Mark finally did get around to going to sleep that night, it was right after he’d decided that he would keep what he saw a secret. He uploaded the photos and videos onto his computer and then he stashed them into a hidden folder before deleting them completely off of his phone. And that night, he dreamed that he was still standing on that ladder in front of that window, watching as Tyler and the mature lady made love.
In his dream, the milf got up and left the room, leaving Tyler alone on the bed with his erect cock throbbing against his abdomen. Tyler looks over at the window. Suddenly, he smiles and waves, as if Mark isn’t being hidden by the lamp-lit reflection inside. Mark becomes stiff, too afraid to smile and wave back, and too afraid to slide down the ladder and run away.
Tyler stands up and walks over to the window. He stops about ten feet back and then he reaches down and begins to stroke his cock. He grins and stares into Mark’s eyes, pulling back his foreskin and then pushing it over his tip, over and over. Mark can’t look away. He’s mesmerized, his gaze glued to that throbbing member. He watches as it begins to twitch and bloat, and then he watches as it sprays streams of cum into the air, nearly reaching the window. Then Mark looks down and sees that he’s got his hand down his pants. He’s stroking his own cock, and he’s rock hard. He squirms and twitches and then he unloads, giving into his newfound taboo fantasy.
When Mark woke up in the morning, he realized he’d had another wet dream.
CHAPTER VIII
Tyler didn’t hear from Mark or Sheldon that weekend. He shot Mark a text message that next morning, but Mark never replied. Tyler was desperate for some sort of activity to get his mind off of what he’d done. He couldn’t stop thinking about it—and now, even with that large wad of cash that was sitting on his desk, he couldn’t figure out why he’d done it. Even if Tina had been a biological woman with a warm, wet pussy, he shouldn’t have done it. Even if they’d given him fifty thousand dollars, he shouldn’t have done it.
Because now he couldn’t stop mulling over it, and he had a feeling it would be in the back of his mind for the rest of his life. When he closed his eyes he could still smell her expensive perfume, and he could still feel her tight anal walls hugging his cock. So he tried not to close his eyes.
He took the old family dog out for a long walk, walking him ten blocks to the off-leash dog park. The dog had only been to that park three times in his ten-year life because it was so far away, but now that distance seemed like a blessing. Though even out for a walk, Tyler still struggled to get that image out of his head: the moment when Tina fished her cock out from her lacy lingerie one-piece. Tyler could still remember his heart stopping momentarily. Even thinking back on it, his heart would throb and clench.
He threw a ball for his dog, but his dog wasn’t terribly interested. After fifteen minutes at the park, the dog wanted to go home, but Tyler wanted to stay out, stay active, keep his mind from wandering. But the park ended up being the worst place as a group of girls showed up. One of them had long dark hair, and she was wearing fishnets under her ripped jeans. Tyler couldn’t help but feel like he looked a bit like her when he was all dolled up. The girl looked up and made eye contact with Tyler, and Tyler looked away quickly. She actually looked a lot like Tyler’s feminine alter ego—they could have been sisters.
Tyler remembered seeing himself in the mirror for the first time, once Tina was finished dolling him up. He remembered being shocked by how feminine he looked. In fact, at first, he thought he was looking at a video screen displaying an actual girl. And if he could look startlingly feminine, did that mean lots of guys could look startli
ngly feminine? Tina certainly looked feminine—the guys all thought she was a sexy milf staring at her photos, and Tyler had no idea otherwise until that cock was out.
Were there more ladyboys walking around? Was Tina just one of many? Was the girl with the ripped jeans over her fishnet stockings actually a guy in disguise? Were her friends guys too? And all of the girls Tyler had ever fawned over—were any of them secretly men wearing panties? Tyler tried not to think about it, worried it could be true. So he started heading home to his old dog’s delight.
His sister was home when he got in. She was in the kitchen fixing herself a snack. She looked over at Tyler and said, “What’s on your face?”
“Where?” Tyler asked, wiping the side of his mouth, assuming she was referring to some missed toothpaste.
“Around your eyes. It looks like eyeliner,” she said, and then she laughed.
Mark wiped his eye and then looked at his hand. There was a small black smudge—he must have missed a bit of eyeliner when he was cleaning his face the night before. He was tired and that changing room was dimly lit. “It’s just mud,” he said, his heart aflutter. “Mark tripped me at the park and I went face-first into a puddle.”
“Oh, that sucks,” Tyler’s sister said, and then she continued making her snack. “I’m going out again tonight. We got invited to this music festival out of town last night, so we’re going to go.”
“Who’s we?” Tyler asked as he casually walked over to the front hall mirror to make sure there was no more makeup on his face.
“A couple of my friends and me. It’s a couple hours away and we’re probably going to spend the night. Do me a favour and tell mom and dad that I’m just at Sandy’s for another sleepover.” She took her snack off to her room to get ready for her music festival.
Tyler went up to his room and tried calling Sheldon, but Sheldon didn’t pick up. Later, he would learn that Sheldon got hammered the night before and spent the entire weekend sick in bed.
So Tyler tried calling Mark again, but Mark didn’t pick up either, which was unlike Mark. Mark was always ready to go out, always ready to hang out, even if it was three in the morning and he had a bad flu. Tyler thought about walking over to Mark’s house, but he was afraid that Mark would be able to tell that Tyler had gotten up to something—and he was still afraid that there was makeup on his face, so he decided to take a shower.
But in the shower, those memories started coming back to him. He could picture Tina crawling on her hands and knees on that large king-sized bed. He could see her gently wiggling her bum, inviting him over, spreading her cheeks to show off her tight hole. Tyler looked down in the shower and saw that he was erect, but he refused to jerk himself off with Tina on his mind—or any tranny for that matter. Tyler had to stay strong, and he had to keep his mind pure. He tried to think of his sister’s friend Sandy—a little blonde with big perky tits. He often masturbated to the thought of Sandy stripping in front of him, and the thought of her bouncing on his cock.
Once he had Sandy firmly in his mind, he let himself reach down and he began to massage the length of his throbbing shaft. It felt nice. He started pumping faster and faster, still thinking of the petite blonde bouncing up and down, her tits flying in every direction. And then he started to imagine something else bouncing around in every direction: a cock. He even imagined a bit of blonde pubic hair. And then he imagined himself reaching forward and grabbing the cock, massaging it until it was hard. He imagined the well-hung Sandy standing up, off of his cock. She took his head and brought it close to her cock, and then she jerked herself off until she was painting his face with her white load.
And then Tyler came in the shower. He opened his eyes and watched as his ejaculate swirled down the drain. And he realized he’d given in to his taboo anxieties. He was worried he would never be able to look at a woman the same way again. He would never be able to fawn over a girl without wondering if she had a secret hiding between her thighs.
But was it so wrong? Was being attracted to chicks with dicks really a bad thing? Of course it was—because Tyler knew that they weren’t really chicks with dicks, but men with tits. They were men with tons of plastic surgery and makeup and wigs. Though Tina didn’t have a wig, and she didn’t look like she had plastic surgery, save for her breast implants, which were amazingly realistic. And when Tyler was all dolled up, he looked like a woman even though he didn’t have any surgeries. What was stopping him from growing his hair out and dying it dark, just like his wig? What was stopping him from taking hormones to change the pitch of his voice?
He pushed the meandering thoughts out from his head. They weren’t welcomed. Tyler was a man and he liked women—real women. And he couldn’t allow one confusing night to complicate that biological standard.
CHAPTER IX
Mark struggled not to pick up the phone every time Tyler called. He was bored with nothing to do, but he still wasn’t ready to face Tyler. He needed some more time to mentally prepare for their next meeting, so it wouldn’t show on his face that he’d been there that night, watching through the window—even though he knew Tyler couldn’t possibly assume that Mark had been there watching through the window.
So Mark spent his whole weekend by the pool, too afraid to even go out to the mall, in case he were to run into Tyler. And it seemed likely that Tyler would go to the mall, seeing as he had five thousand dollars to burn through. Mark went for a dip and then he did some tanning in the sun and then he went for a dip again. And there were a few times when Mark had to excuse himself for the bathroom so he could rub one out to the thought of Tyler taking that pretty milf from behind—and occasionally he got off to the fantasy of Tyler taking it from behind, gripping the bed sheets tightly as his little asshole stretched wide.
As soon as Mark would get off, he would become filled with embarrassment and guilt. He didn’t like that he was fantasizing about his best friend in lingerie, but he couldn’t help it. No other thoughts were cutting it for him. He couldn’t think of anything sexier than Tyler with dark long hair and tight fishnet stockings around his smooth legs. It was Saturday night when Mark started to really think about it. He wondered if Tyler had enjoyed it—if Tyler was planning on doing it again. Did the milf invite him back? If not, was he going to seek out some sexy trap action on his own? Or was Mark just a pervert for thinking about it?
The sun was gone and the pool was cold, so Mark went back up to his room. He found himself repeating the previous night: pacing back and forth, trying to think of something to do. He wanted to know what Tyler had done with the money, but he was too afraid to ask and admit that he knew what happened. But he suddenly had the idea of going over to Tyler’s to see for himself—to spy like he’d done the previous night.
He took his bike over to Tyler’s house, and left it a few houses down, tied to a lamppost. He went down the alley and saw the upstairs lights on in Tyler’s house. Tyler’s room was dark, but the room next to it was bright. He tried to remember which room it was, and then he remembered it was Tyler’s sister’s room.
Mark crept up to the house, looking into the garage on the way. It was empty—Tyler’s parents’ car was gone. Maybe they were out. Mark knew he had to be cautious regardless.
Tyler’s house was easier to scale than the milf’s house. The back wall was decorated with a tall trellis, which was easy enough to climb (when they were younger, they would sneak out together during sleepovers to go to friends’ parties). Mark carefully climbed the trellis now.
And it wasn’t the first time he’d climbed it without Tyler’s knowledge. When Mark was sixteen, he had a huge crush on Tyler’s sister. One night, when Tyler’s sister was having a sleepover with her girlfriends, Mark came over and climbed that trellis to hopefully see some tits. He didn’t end up seeing any tits, but he did end up falling down and nearly breaking his back. He was sore for three weeks after the incident.
Now, he looked into Tyler’s sister’s lit up bedroom. There was no one inside, but the closet w
as open and there were a few outfits laid out on the bed. Mark looked around, trying to see if Tyler’s sister was sitting in a corner, just out of sight, but there was no one to be seen—until a shadow started approaching in the hallway. Mark sunk low, keeping his eyes above the windowsill so he could continue to watch.
Tyler walked into the room, naked save for a pair of pink panties. He had eyeliner and mascara on, and it looked like he had some eye shadow on as well. Mark grinned as his theory was confirmed: Tyler did enjoy his night with the milf, and he was continuing with his cross-dressing. Was this something he’d always done, or was this a new hobby? Mark had showed up at Tyler’s house unannounced dozens of times—maybe hundreds of times over the years—but he’d never caught Tyler cross-dressing until now.
Tyler went to the bed and picked up a dress. It was a slutty black dress, intentionally ripped in many spots to look ‘grungy’ and more revealing. The back was completely ripped open, exposing the entire back, and the skirt was ripped short, showing off the bottom cusp of Tyler’s bum. Tyler admired himself in the mirror for a moment before digging through the closet and pulling out a pair of black sheer stockings. He tugged them up his legs and pointed his toes straight in the air, now admiring his model-like legs.
He stood up and did a few more poses, looking surprisingly feminine without even a wig on his head. His makeup job wasn’t great, but Mark figured it was a first or second try. He watched as Tyler ruffled up his hair while pouting into the mirror like a slutty teen girl would do.
Then Tyler tried to fit into his sister’s shoes. It looked like a tight fit, but he managed to squish his feet into the tiny heels. He stood up awkwardly, throwing his hands out for balance. It took a moment before he started walking—slowly gaining his confidence. Mark was tempted to knock on the window, to scare the living hell out of his friend, but he resisted the urge, afraid to be caught. And then Mark had an idea—
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