Astrid smirked when she heard the pet name. “Princess huh?”
“She called me that on our first date.” Casey looked to the side, avoiding eye contact while tapping his index fingers together. “I didn’t like it at first but uh…well it grew on me. Just her tone of voice, I don’t know…”
Astrid just laughed. “Oh, she has a way with people let me tell ya!”
“So I’ve heard.” By that point, the conversation had distracted him enough that his dick had gone down a bit. He finally started to change and the toy stopped vibrating again when he pulled the garment over his head.
He gave his girlfriend a knowing look, feeling a bit of triumph. Just as he grabbed the skirt he was wearing before, the buzzer activated again. He could tell she was having a little too much fun, and making it go off at particularly inconvenient moments. Feeling himself start to blush, he covered his mouth as he desperately tried to maintain his composure.
“There you go again. Are you sure you’re okay?” Astrid asked, tilting her head.
“Yeah, I’m fine.” He cleared his throat. “I’m just…feeling a little off today but it’s no big deal.”
She shrugged. “If you say so. But maybe you should like, get some tea when you get home or something. Maybe some ginger ale.”
“Uh, yeah I’ll do that.” He hastily put his clothes back on, slipping back into his skirt and trying on the new sweater. “So?” He asked. “What do you think?”
“Not quite my taste, but it works for you!” Ash said, giving him a thumbs up.
Now the most difficult part was over; there would be no more changing clothes, and now he could better deal with the predicament he’d placed himself in. After Ash bought him the dress and sweater, the three moved on to some other stores to look for patches and stickers for their respective jackets and helmets. The bulk of their time, however, was spent browsing. Ultimately Astrid was able to find a few patches she liked, and their little mall trip was topped off with some lunch.
After leaving, Casey decided it would be best to head straight for his apartment since he’d gotten new clothes. Remembering his address, she rode him there on her motorcycle.
The two stepped into Casey’s small, cozy home, its warmth providing relief from the cold winter’s day outside. Before taking off her jacket, Ash pulled out the remote and waggled it in front of him. “You did a really good job of maintaining your composure, I was impressed!”
“Thanks.” Taking his boots off, he released a heavy sigh. “I will say though, this was a little experimental for me and I don’t think I want to do that again. I know I’m the one that suggested it, but actually doing it was different than I expected. Being in public was weird.” Setting his boots next to the front door, he leaned against the wall and started rubbing his temple. “God, and I came across as weird to Astrid too.”
“Well, at least now you know that you don’t like it. And don’t worry about Astrid; like I said earlier, she’s really laid back. I doubt she’ll bring it up again.”
“I know, I just worry a lot is all.” Walking into the living room, he stretched. “Well, enough about that. That whole experience left me feeling pretty horny so what do you say we, uh…”
“I was just about to say: I think you deserve a reward for holding it together.” She walked up behind him, her tall figure looming over him like a shadow. “How about I pleasure you some more, then fuck your brains out?”
“Oh!” He spun around, his interest piqued “So we had a similar idea!”
“Great minds think alike.” She took him by the hand. “C’mon, show me where your bedroom is, and I’ll show you a good time.”
After briefly heading to the bathroom to remove his butt plug, Casey quickly came back into his bedroom where she was waiting. Casey’s bedroom was immaculately maintained, at least when compared to Ash’s. It was also decorated with various anime and video game posters, along with a bi pride flag that hung over his bed.
They idly chatted for a few moments, but before long it was clear that they both wanted to go at it. Still wanting a bit of foreplay, they started kissing. The blushing boy only got a peck on the cheek, however, before she decided to spice things up. Reaching around him, she picked him up. Lifting his body off the ground, she supported his weight by holding his ass.
“I knew you were easily carriable!” She laughed.
“Am I easily carried, or does it just seem that way to you?” He draped his arms over her broad shoulders. “You big strong woman you.”
“You flatter me too much.” She rested her forehead against his, smiling. “But you’re not wrong, I’d consider myself pretty strong. Doesn’t make you any less holdable though. It’s not a bad thing, only means I can treat you right.” Chuckling, she leaned for a kiss. He kissed back, and soon they were passionately making out.
They had made out on their previous dates, but this felt different. She’d previously demonstrated her ability to easily overpower him by pinning him down, but this was different. The fact that she was carrying him, hands firmly on his ass, while her tongue stuck itself into his mouth, made him feel owned. He was all hers. On Ash’s end, the teasing session had gotten her riled up. She could hardly wait to make a mess of him, but she couldn’t dive into things just yet.
After several minutes of kissing, he pulled out. “So…what was that about a reward?”
“Ready for it already?” She gave him a cocky smile, tilting her head to the said. “Just couldn’t wait to see what mommy has in store?”
“I was curious is all. But to be honest, the whole thing at the mall left me feeling unsatisfied and now the way you’re holding me is…” he sighed “Please? I’ve been good, I’ve earned it.”
“Well, I can’t refuse if you sound so whiny.” She set him down on his desk chair.
After he told her where his box of sex toys was, she got it out and pulled out some handcuffs. After binding him to the chair, she knelt before him.
“Now for your reward.” She reached up into his skirt and pulled his underwear down, making his bulge all the more prominent.
“Thank you, mommy.”
“You don’t have to be so polite, kitten. The only thing I want to hear out of you is your slutty little moans.” Holding it by the end, she lifted his skirt so she could look up it. “You know, there’s a lot of awesome things about having a femboy boyfriend, but I just now remembered another bonus.” She looked up at the handcuffed man. “Skirts give easy access.” Giving him a wink, she pushed her head underneath the folds of his skirt. Her head was reduced to moving lumps beneath his clothes, and just a second later he could feel her mouth on his dick.
“Oh my…” he covered his mouth, and his whole face turned red. Something about the way she was sucking his dick without even taking his clothes off was turning him on.
“Well now I know you’re feeling good, I’ve got you talking like a little Victorian lady.” She ran a tongue along his length, while her hands rubbed on his inner thighs. Flicking her tongue at the tip, she started stroking him. She squeezed his thick thighs with her free hand, feeling her fingers sink into them.
Eventually, she started using both hands to work his long, thick shaft while licking at his bulging tip. Lowering her head, she pushed more of his cock into her mouth. She groped his balls as she deepthroated him. Although she couldn’t swallow the whole thing, it still felt incredible. He could feel it going down her throat, while her tongue kept licking him.
She pulled out, taking a deep breath before stroking him again. After a moment of pleasuring him, he heard her groan. “That’s it.” She said, grabbing the ends of his skirt. “As much as I like being underneath your skirt, seeing all the faces your making is like, half the fun of this.” With that, she pulled his skirt up until both her head and his dick were in full view. “There.” Going back to pumping, she licked her lips. “Just hearing the noises isn’t enough, I need to see your other reactions too. Your face, the way your body reacts…” she groped at his balls while her fingers rubbed on his tip. Precum started coming out a little, forming a little drop on the pink head.
Now that she could see his reactions, she was enjoying herself even more. His whole face had turned a cherry red, and it looked like he was desperately trying to keep his voice down. In lieu of full-on moaning, he just let out little whimpers and gasps.
“I’m getting close!” He cried, still feeling sensitive after the little vibrator experiment.
“Let it all out.” She commanded, before sticking it in her mouth again. While the tip hit the back of her throat, she started fondling his nuts as if coercing the semen to come out. He finally climaxed, spurting the thick, white liquid down her throat. She chugged down his load, swallowing every last bit of it. Licking his tip clean, she finally pulled out and took a deep breath.
“Did kitten enjoy that?”
He nodded, trying to catch his breath. “Yeah, it was incredible.”
She rose to her full height and looked down at him with a lustful gaze in her eyes. “God, after spending all that time teasing you, I almost can’t hold back. I want to rail on you all night and leave your pelvis shattered.”
“Then break me.” He didn’t realize it, but he was making a desperate expression.
“That’s a good little slut.” She licked her lips, then started taking off her clothes. She took off her pants and underwear, then unbuttoned her flannel. Leaving the top open to reveal her cleavage beneath, she put a condom over his dick. Positioning herself over him, she held his desperately swollen shaft as the tip pressed against her pussy. Looking him in the eyes, she maintained her smug expression as she slowly lowered herself onto him.
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