trans boy toy

It was their third date, and it had gone just as well as the first two. They’d started at the ice cream parlor Eli had worked at the previous summer, and Lisha had gone a little crazy over the mango flavor. Lisha picked their next destination, taking him to an antique mall she loved. They ended up helping an employee chase an irate starling onto the street. After wandering the downtown area for a while, they reluctantly started to head home. Lisha asked to cut through the park and Eli saw an opportunity to share something else with her. 

“I had my first kiss here,” he told her as took her hand to lead her through the walking path. “There’s a big cherry tree with these HUGE hydrangea bushes. When I was in high school, everybody came here in Springtime.” Lisha was smiling at him, warm and sunny, like he was precious and desirable. Eli hadn’t felt “desired” in so long; he felt a bit drunk on it. 

Lisha loved the tiny garden as much as Eli hoped. She gushed over the blooming cherry tree, and she wanted to sit on one of the nearby benches to admire it for a while. “Admiring the tree” turned into making out. Lisha’s hands in his hair and his arms around her waist while their tongue tangled and their breath mixed. When they finally pulled back, Lisha looked a little starry-eyed, and she said: “I really don’t think I’m ready to go home…” 

For just a second, Eli felt bold. Bolder than he had in years. He caught Lisha’s eye and grinned playfully. When she quirked a brow at him, he reached out and grabbed her hand. “Come on, before someone comes by.” He rolled to his feet, pulling Lisha up after him. 

“What are you up to?” She asked, amusement in her voice as Eli pulled her across the pathway. Heart pounding, Eli pushed past the massive hydrangea bushes circling the cherry tree. “Oh, it’s pretty back here!” 

“And private,” Eli whispered, before backing up against the tree. Still riding this spontaneous confidence, he grabbed her shirt with his free hand and tugged her down. “We can be alone for a while.” 

Grinning, Lisha let herself be led down. “Little minx,” she teased, and kissed him. Not the friendly sort of peck they’d had before. Deeper, and her hands came up to cup his face. Eli sighed into it and got one of his hands into her hair. The other rubbed her neck and collarbone, seeking out bare skin under her dress. “Mmm. Touchy. That’s cute.” 

They continued kissing, Eli standing on his toes to reach her mouth. Eventually, Lisha let go of his jaw to grab his wrist instead. Still sucking on his lower lip, she pulled his hand down her chest to cup one breast. Eli gasped and broke the kiss. “I--um. Okay, you want this?” He squeezed it, a little shyly. 

“Yeah, I do. Go on, play with them a bit.” She grabbed his other wrist, tugging until he released her hair, and repeated the motion. Smiling coyly at his pinkening face, she guided his hands to cup both breasts. “Oh, you’ve got nice hands baby,” she cooed, and Eli squirmed in pleasure. Encouraged by her soft voice, he rubbed and squeezed, earning a look of bliss from his pretty date. “You’re good at this. Keep going…” Breath coming quicker, Lisha let go of his wrists. She brushed his hair off his face and kissed him again, before dropping her hands to his waist. “Gonna touch you too,” she said softly, and Eli froze. 

“Wai-wait. No, I don’t think--” Lisha, instead of answering, arched into his touch. Eli cut himself off with a gasp when her hard nipples brushed over his palms. On pure reflex, he rubbed back, trying to make her feel good even as his anxiety began to spike. Taking advantage of his distraction, Lisha gently undid the button of his jeans. “Lisha, we’re outside!” Eli squeaked, and she laughed against his mouth. 

“Look how big these bushes are,” she said, pulling down his zipper. “No one can see us, honey. If we’re nice and quiet, I’m sure we’ll be fine.”  

Eli squirmed and blushed but didn’t stop groping her. Lisha was so beautiful, so confident and cool; he didn’t want her to think he was a prude, or worse, not into her. So, he continued squeezing and petting her cute breasts while she opened his pants. 

Lisha’s glittery nails slipped inside his open fly and dragged over the front of his boyshorts. “Oh, these are so cute!” Lisha whispered, and kissed the tip of Eli’s nose. “Bright orange. God, I love the way you dress…” The words made him melt, sending a gorgeous heat seeping through his veins. He accepted the next kiss Lisha pressed to his mouth, and dropped his hands to her waist. When Lisha hooked her fingers into the band of his underwear, he gingerly reached under her shirt. “Yeah, go on, that’s it,” Lisha urged. “Nothing to be scared of. I just wanna make you feel good.” 

Lisha’s bra was made of something silky, and had a tight little bow in the middle. Eli rubbed his thumbs between the soft mounds, wishing he could feel her nipples through the fabric. Lisha, for her part, had pulled his waistband down. She lightly scratched her nails down his stomach, towards his crotch. “Fuck! Lisha, please, slow down…” Goosebumps followed her fingers, making his clit throb. His hole was starting to leak, despite his ongoing reservations. He liked Lisha so much, and it had been so long since someone else had played with his body.  

“Come on. I thought you were into me,” Lisha purred, as her fingertips teased his short, coarse hairs. “You’ve been handsy all day. And those looks you’ve been giving me. Bedroom eyes.” Her voice was a tease and she punctuated it with a soft kiss to his ear. “It’ll feel so good. Trust me, I know what sweet, needy boys like you want.” 

Eli’s breath came harder and faster as Lisha got one hand between his thighs. Normally, it was hard for him to get wet these days. Between the hysterectomy and the topical HRT, lube had been a much bigger part of his (mostly solo) sex life. But today, his hole was feeling perky. At the first stroke of Lisha’s fingers over his clit, it started to drip. “Not--not too rough,” Eli whimpered. His clit hadn’t gotten much bigger with T, but it had gotten more sensitive. 

Lisha listened this time, keeping her touches light and tender. His clit twitched and throbbed at the attention, and his moan made Lisha smile. “Here…” One of her hands wrapped around his wrist, and dragged it down. “I need some attention too, honey.” 

Eli gasped as his hand was guided down Lisha’s chest and stomach, then lower, past her thighs, to the hem of her dress. Trembling with a mix of fear and arousal and creeping shame, Eli tried to resist. It was a feeble attempt, and Lisha forced his hand under her skirt. More silky fabric, this time stretched across the bulge of her cock. The heat and the shape made Eli throw his head back, made his hole ache and leak even more. “Lisha...please...we can do this at my place. I can get on top and ride you. Or suck you off for as long as you want.” He still wanted all of that, still wanted her; but not outside, where someone could catch them.  

“Shush. Don’t be so nervous. I know, you’re shy. But I’m going crazy with how bad I want you. You’re just so fucking cute, how do expect me to wait, huh?” She moved his wrist, making his fingers dance over the head of her cock. Something wet bloomed under the tight fabric of her panties, and Eli’s eyes went wide. She was turned on by him. Really turned on. “Jerk me off,” Lisha told him, and Eli felt powerless to disobey. His hand went under the band of her panties and wrapped around her long, smooth erection. “Good boy!” 

Now that her cock was being attended to, Lisha could get back to playing with Eli’s hole. Touches still tender, she rubbed his clit in slow, insistent circles. Eli tried to jerk her off, but his hand kept pausing and stuttering. Every stir of the wind through the flower bushes sounded like approaching footsteps; he was convinced they were being watched. Lisha didn’t seem to mind too much. She bucked her hips in slow, lazy thrusts, rutting against his shaky hand. When they were both panting and flushed, she pushed her fingers further back. Over his sensitive lips, catching on his dripping hole. 

“Take them off,” she ordered. “I want to get you ready.” 

“Lisha--” Eli tried weakly, but she ignored him. 

The hand over his wrist let go and left her skirt, instead grabbing the loose waistband of his jeans. She pulled them down, hard, until they hung around Eli’s knees. He tried to keep his legs closed, but Lisha didn’t let him. Inch by inch, he spread his thighs. Trapped between the tree and Lisha’s body, he couldn’t twitch away, and his breath hitched in panic when her fingers started to tease inside. “Oh, Eli, you’re so tight. Are you still scared?” 

Eli didn’t answer, too busy staring up into the tree branches and trying to breathe. Lisha was still fucking his fist, erection twitching against his palm. Lisha was urging him to relax as she pressed her fingers deeper, but it was hard. His body was clenching hard, trying to keep her out. But every centimeter of her fingers, every thrust of her hips, every brush of her mouth on his jaw made him wetter. “Too much,” he whimpered, and Lisha kissed him to swallow his distress. “Lisha please, I’m not ready--” 

“I’m getting you ready! If you relax, it’ll go much faster. And feel nicer. Please, I want to make you feel good.” Even if Eli wanted to stop, his body was on board. His hole had started to open up around her fingers, letting her in deeper. Getting more excited, Lisha spread them experimentally, and Eli let out a needy sob. His other hand was still limply covering her breast, but now his fingers were curling reflexively. “Yeah, keep touching me baby. That’s so good. I’ll make you feel so nice you won’t come down for days.”

A third finger joined the first two, and Eli went limp against the tree. Lisha fucked his dripping hole with hard, deep thrusts, each time spreading her fingers wider. Her eyes had gone hazy and needy under her painted lashes, and she had gone from fucking his hand to grinding against it. Every movement was a tad feral, almost mindless; even in his shame, Eli was somewhat flattered. She wanted him. So bad she couldn’t stop. 

After a couple more minutes of increasingly greedy fingering, Lisha pulled her hand away. “Okay, gorgeous,” she said, giving Eli a reassuring smile. “Time to take these pants off.” Shaking his limp hand loose from her body, Lisha sank to her knees. Holding Eli’s dazed eyes, she pulled his open jeans the rest of the way down his legs. The whole thing made him squirm with shame, but he lifted each foot for Lisha. “Yeah, good boy. So brave for me.” She kissed each thigh, and Eli stuffed a fist into his mouth, muffling a needy sound. “If you keep being so good and well-behaved, I’ll eat you out later.” 

Lisha was rising to her feet and stepping between his spread legs. “Lisha, please, I can’t stay quiet!” Eli pleaded, but Lisha had an answer for that. 

“I wanna see your cute chest…” She grabbed the hem of his sweatshirt and lifted it to his mouth. “Oh. Oh look at these pretty pecs!” Eli turned redder than ever as Lisha stuffed his shirt into his mouth, encouraging him to bite down hard on the wad of fabric. Now that he was gagged, she stooped slightly, running her hands greedily over his ribs and his top surgery scars. “Those naughty pics you sent me last week didn’t do you justice.” Kisses rained over his chest, his scars, his new nipples. When Lisha had had enough of his skin, she stood back up and grabbed his thighs. “Grab my shoulders.” 

Trembling, Eli did as she said. His hands curled tightly over her broad shoulders, feeling drool soak into his shirt. With embarrassingly little effort, Lisha lifted him off his feet and pinned him harder against the tree. His legs were pulled around her waist, and the head of her cock nudged at his loosened hole. “Do I need a condom?” Lisha asked, dragging the leaking head back and forth. 

Eli took a moment to answer, his brain too full of conflicting emotions and maddening sensory input. “N-no,” he said mumbled, shaking his head as best he could. “I had a hyst...” That was all he could managed past the drool-soaked cotton of his sweatshirt, but Lisha seemed to understand. 

Lisha started to work her way inside, and Eli’s words died into a low sob. Her cock felt even bigger than he thought: long and thick and hot as it opened up his hole. “I won’t cum inside,” she whispered, before she resumed kissing and nipping his neck. “Promise I won’t make a mess, gorgeous, just wanna play with your pretty body for a while.” She kept going deeper, kept filling him up until she was buried to the hilt. Eli was more stretched than he’d been in months, and hung limply in her arms as he tried to catch his breath. Lisha was breathing heavily too, and each gasp against his neck sent shivers down his spine. “Oh, oh Eli, I love the way you feel,” she moaned, and then started to pull back. 

Hot, bright pleasure sparked through Eli’s hips, making him whimper, and then Lisha thrust back in. The whimper turned to a yelp, still mostly stifled by the makeshift gag, and Lisha did it again. In and out, in and out. Every thrust into his unwilling body made his blood light up, made more slick leak from his violated hole. She had to start slow, the prep not enough to pound him just yet. But she clearly loved it. Her face was getting pinker and pinker, and she hadn’t stopped gasping. When she was sank in deep, buried herself to the hilt, her pelvis rubbed against Eli’s needy clit. He’d clench hard around her length, like he was begging for more. It made her moan louder, made her fuck into him faster. 

Every thrust opened him open more, and she could go harder and harder every second. The sparks in his blood turned to flames, and the whimpers in his mouth turned to muffled screams. Any pain he’d had at the start was long forgotten, and no matter how much Eli tried not to enjoy it, his greedy hole had other ideas. Lisha’s cock was exactly what his body had been craving, and she was going to give it to him no matter what his mouth said. 

Lisha lifted her head from the crook of his neck and rested their foreheads together. Eli blinked at her through misty tears, and she smirked. “Keep that gag in your mouth,” she whispered. “I’m not even close to done, handsome, and I’m only going to make you louder.”