Popping His Cherry Ch. 02

Summary: Taylor, 18, continues his relationship with Loren. Themes include humiliation, crossdressing, domination, feminization, oral. All other characters are 18 or older.

~~~~~

"Wow, on the first date? I didn't know you had it in you!" Lana teased and chuckled.

Had it in in him was right. Taylor laughed nervously. "Well, one thing led to another. We just clicked you know?" He crossed his arms defensively. Taylor didn't know if she was trying to put him down or complement him.

"Well, I think it's really romantic." She said in a manner that mixed flirtatious with condescending. Lana was Taylor neighbor, and best friend. He didn't have too many male friends. Her blond hair coursed halfway down her back. She had a tomboyish smirk and wore jeans and a t-shirt. She was pretty in a small and cute way. shorter than him even. They'd grown up close, like siblings. Even if they hadn't, he'd always felt she was way out of his league. "You said she's tall? Did she sweep you off your feet?" she joked.

He didn't know how to answer that. He did remember his feet held up in the air though.

"More importantly." Lana asked with a raised eyebrow, "How 'all the way' are we talking here. I know how you like to exaggerate."

"It's like I said. We went to her place and," Taylor gulped, "One thing led to another, things escalated-"

"It's okay. You don't have to kiss and tell." Lana rescued him. "You're a gentleman."

"We definitely went pretty far enough." Taylor said with certainty.

"Well maybe she will be more talkative than you." Lana teased. "If she shows up. Will she come on her bike?"

"I hope you mean regular bike." Taylor turned to see his mother join them on the back patio. She was strict, but loving. Her hair was cut short and she was dressed for gardening. "You know how I feel about-"

"Yes mom, a regular bike!" Taylor lied.

"Good. Anyone want cheese and crackers?"

"Yes please!" Lana cheered.

"When is this mystery girl showing up?" His mother asked, putting the plate down on the table between them.

"She should be here any minute-" Taylor started before he heard a creak at the wooden gate at the side of the house. Sure enough there she was. Loren in her leather jacket, piercing forward into Taylor's backyard. He adjusted his seating as he saw her. "Loren!" He smiled.

"She really is pretty." Lana said with surprise. "And tall."

"I'm Georgia, Taylor's mother. It is so nice to meet you!" Taylor felt a strange sense of happiness and anxiety seeing these two important women in his life meet and shake hands. "Will you be staying long?" She asked as Lana finished her own introduction.

"No, sorry, we have a date to get to, right, boyfriend?" Loren looked to Taylor.

"Right."

"Well, don't let us stop you then." Georgia waived. "Don't come home too late! Oh, and Taylor," She eyed her son, "Don't be afraid to invite her over for dinner. And we do have a guest bedroom too-"

"Mom!" Taylor could tell he was blushing.

"Sorry! Have fun!" She quickly chuckled to herself. His mother was always trying to inject herself into things, especially now that she was retired. "I love you!"

"I love you too." Taylor said as he got up and followed Loren out the way she came.

"A friend?" Loren asked with a raised eyebrow.

"Neighbor, but yes."

"She seems nice." Loren smiled. "I like your mom too."

"I'm glad." Taylor didn't feel comfortable until they were finally out of earshot. "Thank you too, by the way, for calling me your boyfriend." the tension was being replaced by a bubbling mess of confused emotions. "I know you really didn't want to."

"Did you keep up your end of the bargain?" She asked.

"Yep." he adjusted his waistband, remembering his naughty deeds.

"Show me."

"N-Not here!" She stopped as they turned a corner. She faced him, her fists on her hips. She looked down on him like his mom did when she knew he was trying to get out of something.

"Taylor?" She asked. "Show me!" She asserted.

Taylor whimpered as he made sure the area looked clear. He quickly pulled down on his waistband enough to show the thong he was wearing. It had been riding up all day. The lace was light on his flesh and the elastic was pressing firmly on his skin.

"Lower." She demanded. He pulled his jeans down enough to show the entirety of his rear. "Good!" She seemed happy. "I can't believe your moms stuff fits you so well!"

He quickly pulled his pants back up. "If she finds out about this she'll kill me!" He re-iterated. "I can't believe I'm-"

"And the top?" She asked.

"She's a D-cup, there was no way to hide it-" He crossed his arms again. "Happy?"

"Let's get you something that fits better." Loren teased. "D-cup, really?"

--

"Um, Loren?"

"Yes?"

"Where are my clothes?"

"Don't worry, I'll give them back after we've tried on everything."

Taylor was stuck in nothing but his mothers best lingerie as he waited in the dressing room. "Do I get a say in this?"

"Sure," He hid himself as she entered with two sets of women's underwear. "Red with black lace, or purple and gold?"

"Um, that isn't what I meant." He felt very exposed, despite being hidden on all sides. His junk was barely covered.

"I think this one will bring out your eyes better." She showed the purple one. "Try it!"

"I don't know about this."

"You're right, I think this might fit you better." She handed him the red one. "This is so exiting!" She smiled. He could tell she was enjoying herself.

"Ha ha, right." She left him and he nervously changed. Everything fit like a glove. once Taylor was in a full, matching set, he looked at himself. In the mirror he stared for a bit too long. It was like his body was built for this kind of thing. Even the bra was enough to fool him. Loren entered again and he covered himself bashfully.

"Wow. That's great! Now, how about-"

"I think this is enough." He tried to hint.

"Just one pair for now I guess. But now for something over it!" She showed a short skirt and tight top. "Try it on!" He reluctantly stepped into the clothes. "Oh, and this!" black stockings, a red bow tied into his hair. "Hmm, and maybe this-" A choker on his throat. "Stunning!"

"Loren, can we talk?" He spat out. He looked at the mirror again. He looked more like her sister than her boyfriend. The band around his neck was tight, but in a comforting way.

She blinked and put her hands on her hips. "Sure."

He didn't know what to say. "I feel like I'm not getting a lot of choice in this." He didn't want to jeopardize the relationship, but he also thought this was going a bit far. Loren was so hot. But this was so weird.

"Right." She nodded. "I see. I think I know what to do next." He felt her touch him and he froze. She embraced him from behind and he felt her hands on his hips and chest. "How about a few more minutes of trying on clothes, but then-" He shuddered as she ran a finger down his side and tickled his inner thigh, "You get to chose what I wear." He thought about that. He felt his heart in his throat as her hands moved dangerously close to his manhood.

"Uh huh!" He nodded frantically.

"Great!" She slapped his ass and he yelped as she left to find something else for him to try on. "You stay there! It will be your turn in just a moment!"

He felt a bit better after that. Even after they had left the store with three sets of lingerie and several sets of cute girl clothes, he felt like he was finally getting to assert some power in the relationship. "Where are we going now?" He asked as they walked through the mall. She had convinced him to keep on one set of underwear under his normal clothes, and the choker. The bra felt the most alien. He kept crossing his arms to cover up the lumps, "Is there another shop you like to buy your clothes at?"

"Yep. Well, one piece anyways. Here-" He hesitated before following. "What?"

"This is, um-"

"A sex shop." She answered.

"Uh, yea-"

"Stop acting like you're twelve and get in here."

"Right!" He followed as if she had spanked him again. There was all sorts of lewd things inside. Taylor feared to guess the purpose of much of it. They traveled to the back and Loren pointed to a rack before asking, "Alright, a deal is a deal, how about you choose three of these?"

He looked at his options and felt his body go cold. It was a wall of strap on's and dildos.

"And don't say you don't have a choice. You have dozens of options!" She tried to placate him.

She was making him pick his own poison. "Loren." He felt himself shaking.

"How about this one?" She strapped one on over her jeans. "Clear silicone. Simple. Eh, boreing. How about, ohh!" She brandished another one, "If you've never tried a ribbed one, then you are missing out. Or maybe something real interesting," She showed what looked like a long, strait stem.

"That doesn't look like a dildo."

"It goes inside your cock."

"Not that one please!" He instinctively grabbed his groin. "I'm not feeling that adventurous right now!"

"Then something simple." She shrugged. "Whatever you want really. Well, this," She showed a pink, soft cylinder, "Pocket pussy. I hear it feels alright." She put it in his hands. "This one vibrates!" She smiled and put a rubber cock in his other hand. "Hmm, how about-"

"Taylor?" He heard a familiar voice. He and Loren turned and saw Lana. She was about a meter from him with a shopping back at her hip. Her eyes were wide. They stared at each other in silence. "I didn't expect to see you here." Taylor was mortified. He looked down at the toys in his hands and then back up at her. She saw everything. Her wide eyes went to the toys, to him, and then the rest of his chest.

"L-Lana!" Taylor tried to hide the toys behind his back, far too late. "Haha, w-what a surprise!"

"Your, um," She swallowed, "You're bra strap is showing." Taylor looked at his shoulder and noticed where she was pointing. He must have been red as a cherry. He felt like he was going to explode from embarrassment.

"Ah." He adjusted his sleeve. There was a silence for too long of a time. They both had known each other since they were kids, but they had never talked about sex very openly. Now here they were, silently realizing that they both had a kinky side.

"You're buying the Clockwork Boy?" She blurted out.

"What?"

"The vibrator. I was looking at it last week." Lana explained. She seemed half bashful, half relaxed. As if she were both scared and happy to talk about it with someone.

"It's not what you think!" Taylor tried to defend himself.

"If you are new to all this, I think the Little John is a good choice." She pointed up to the second row. "It's small, but has a good angle, and it's easy to use and clean. But I'm quite partial to the ThunderStroke too." She made eyes towards a larger model on the bottom row. "But it takes some getting used to. I've actually been coming here a while. If you can't tell."

"Well, how do you use it?" Taylor opened his mouth, but Loren was the one to speak. She stepped in front of him. "You know like, uh, front or back door?"

"Oh!" She was surprised at Loren's forwardness. "Well, I'm a simple girl. I don't really know what it would feel like back there. Or for a boy. I just have times where I'm lonely. Actually it happens a lot. Anyways, if you want a suggestion for that," She searched the wall and pulled off a pink, plastic member. "I'd recommend something like this. It's called the BottomBumper, it's made for Strap on's, but you can put it on a suction cup too, or as is. It isn't as intimidating as the others. If I were to try something back there, it's what I would use. Hypothetically I mean." She looked at another box on the shelf, opened her mouth, closed it, then opened it again. Her voice was very quiet when she motioned to it, "I read online, that one is supposed to be great for guys." She was quite red while saying it. "Apparently, if you clench right, it stays in tight and it puts pressure of the prostate without needing your hands or anything." She looked away and twiddled her thumbs.

Loren smiled, "I didn't take you for such a kinky girl!"

"People usually don't." Lana giggled, "In fact, I haven't been able to talk to anyone about it really."

"We should have lunch sometime." Loren nodded. "You have a boyfriend?"

"Oh no!" Lana shook her head. "My family is really conservative! We don't really talk about sex much at all. If my parents knew I had toys like this, well, I don't know what they would think."

"Well, um," Taylor injected himself into the conversation. "I'd really like it if none of this got out-"

"How about we pretend we didn't see each other here?" She suggested. She seemed just as relieved as Taylor.

"That sounds good." Taylor nodded.

"Well, I'll see you around then." Lana nervously stepped away, but before leaving completely she hesitated, walked back, and took one of the BottomBumpers with a blush. Then she turned away and quickly paced to the register.

"Awkward." Loren said as Lana was out of earshot. "Anyways, what are you going to pick?"

~

Taylor was afraid that Loren would bring him back to her place and convince him to do even more girly and embarrassing things. Unfortunately, it was even worse than that. Loren had thought it would be more fun to do it at Taylor's place. She had been invited after all.

"The sausage is delicious Georgia!" Loren said.

Taylor's mother waived a modest hand, "It's a family recipe. I'm glad you like it!" She looked to her son, "Your girlfriend is so polite! I approve."

"Ha, ha, Thanks!" Taylor had been a bit worried that there would be conflict between the two, but they seemed to be getting along fine. His bra itched slightly. He hunched over to try and hide it.

"If you don't mind me asking," Loren started, "I've only seen you around the house. I hear Taylor's father is a pastor."

"We are separated." She said quickly, "Taylor was very young when it happened. He stays with his father on weekends."

"I'm sorry to hear that. I didn't mean to-"

Georgia was solemn, but accepting. "It was a long time ago. Anyway, let me get your dishes for you." She cleaned the table, "I'm sorry to be a a bad host, but have some errands to run out of the house." She gave her son a look, "Can I trust you wont do anything irresponsible while I'm gone?"

"Mom!" Taylor fidgeted.

"We wont burn the place down." Loren confirmed. Georgia gave her a suspicious look before nodding.

"I wont be long. Just an hour or two." She finished up in the kitchen and walked to the door. "Have fun!" Before she closed the door she eyed her son again, "But not too much fun."

"Mom!" Taylor groaned again. She smiled, feeling like she had been understood, and closed and locked the door. He sighed in relief. That dinner had brought up far too many bad and awkward feelings. He was so ready to move out.

"Now that we are alone." He heard Loren start. He gulped and looked at her. She sat spread out and relaxed. "What do you want do to first?"

"What do you mean?" Taylor played with his hair and looked away. She was far too confidant in her approach. "I guess we have some movies. I have some board games-"

"How about you show me your room?" She asked.

"Oh, okay." Taylor rose to his feet and led her deeper into the house. This was going fast. "Here," He motioned. His room hadn't changed much over the years. He hoped it didn't look too childish. It was far too colorful for his liking. He would be happy to leave it once his first semester started. As they walked in Loren closed the door and dropped her bag of goodies on the floor. "Um, Loren," Taylor felt his heart in his throat, "I was thinking-"

"Things aren't even in our relationship?" She asked. "I agree. It is a bit weird isn't it? The unfairness of it?"

Taylor sighed in relief. "Yes. That's what I was thinking."

"I understand." She nodded. "I mean, I went down on you, but you haven't returned the favor yet."

Taylor was confused. "Eh?" He began to realize what she was saying. "You want me to go down on you?" He asked. "Like, right now?" He gulped. That wasn't what he was thinking, but maybe it was a step in the right direction. "I don't really know how though."

"Don't worry, I'll teach you." She smiled and caressed his cheek. This was it. One step closer to really being with a woman they way he had dreamed. "Ready?" He nodded. "Get changed first." She said with a smirk.

"Do I have to?" He asked and looked at the bag she brought in. "I was hoping-" He stopped when he saw her put her hands to her shirt and pull up. He saw her pale skin underneath. Her navel, her abs, her ribs, and then the rim of her bra. It was black as sin against her white skin. She lifted up and over and her shirt fell to the ground. His eyes feasted on her shoulders, her arms, the edges of her breasts.

"Well?" She asked, "Are you going to keep staring, or are you going to get started?"

"Yes mamn!" He nodded and quickly took out one of the outfits they had chosen together. She had the strange modesty to turn as he was changing. Maybe because she wanted to see it all on first? Regardless, he stripped to his bra and panties and put on a mini skirt and crop top. She said she liked the look of his hips and waistline. He put on the bow in his hair and stockings over his legs, even the garter belt was tight on his well formed legs. "Is this good?" He turned and covered his crotch. He saw her caged bosom and begged her to release those orbs with his eyes. Her eyes looked victorious and hungry.

"Just a moment," She took something out from her purse and walked to him. She marked dark lines around his eyes, starring deeply into them as she applied the ink. She blushed his face and put a stick of red to his lips. When she was done she showed him a mirror. She was quite good at it. The Taylor in the mirror was hotter than expected. "There." She smiled. "Even you want to fuck that face, don't you?" She asked. Before Taylor could think about the question he nodded, imagining a cock between those lips. He shook his head frantically when he remembered who that girl was. "So cute!" She ran a hand through his hair. It felt wonderful. She grabbed his ass under the skirt. He thrust against her, his bulge on her thigh. Her fingers gripped deep. Her middle finger was tight between his cheeks. Taylor ground his hips against her in longing. "Beg me." She said. "Beg me to fuck your face."

"Please. Please Loren." His words were breathless whispers. God, he even sounded like a cute girl. He was turning himself on. "I want to make you feel good." he licked his teeth and gasped as she put her thumb inside his mouth, grabbing his jaw. "Gah!" It held his mouth open, and pinning his tongue down.

"Suck it." She commanded.

"Hmph!" Taylor hummed and obeyed. She fucked his face with her finger until Taylor was moving his body all on his own. He was humping her leg as he sucked on her digit. His tongue would joust with the thumb until Loren decided to playfully pin it down again. She was still feeling up his ass, his side, his spine, and causing shivers to run up and down his whole body. She popped herself from him with a smile. He was panting. His chest was heaving.

"You want to feel good too?" He felt her hand toy around with his navel. Then her fingers trailed down a leg and tickled between his legs before they settled under his manhood. Was she going to jack him off? He nodded. The hand moved around his hips to the back. He felt his panties pulled aside and a small wet object being inserted. Where had she even gotten it from?

"Ahah!" Taylor gasped. It wasn't that large, but it curved and prodded the very roots of his pleasure from the inside. Once it was in she fixed his underwear again and gave his butt a firm slap. He felt it in his core. He felt sex try to seep out his cock without his control. "Oahah!" His legs shook. He clenched and felt it fuck him. "Hmph!" He tried to hold in how good it felt. He grit his teeth. Every time he clenched and humped her leg he felt it up inside of him.