In Their Shoes Ch. 03

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Vanessa has her first sexual experience as a guy.
3.2k words
4.39
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Part 3 of the 3 part series

Updated 12/15/2023
Created 12/04/2023
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Vanessa snuck a glance over at Brooke who was still engrossed in her phone. Did she and her son really just sit together and look at those 'meme' picture things all day? What was the point of hanging out then? The phone in Vanessa's hand buzzed, and she brought herself to look at her son's phone again. Her phone, rather, until this mess got sorted out.

It was a text from Brooke, a picture of a puppy cuddled up with a heart pillow. Another text from her, simply saying "us" with an excessive amount of hearts and smiley faces. Vanessa felt so out of touch, so unused to this style of hanging out.

"What's on your mind?" Brooke's voice called out, breaking Vanessa out of her trance.

"Oh, sorry. Just a lot of stuff going on lately." Not a lie, but it wasn't like she could tell Brooke what was actually happening.

"Like your parents?" Vanessa just gaped at the girl, stunned and unable to answer. Fortunately, she didn't have to. "You've been evasive talking about them lately and been begging me to get you out of that house, and I don't think it's because they're grounding you." Her attempt at a joke fell flat in the air. "You can talk to me, whatever it is. You just seem especially out of it tonight."

For a moment, Vanessa felt compelled to answer, as though unburdening herself to Brooke would solve her problems. But then she realized the deeper meaning behind what she said; Corey hadn't told her about the divorce yet. She didn't know. Vanessa bit her lip, shaking her head. Whatever reasons Corey had for keeping it to himself, she'd have to respect that and not tell Brooke either.

Brooke nodded, the concerned look on her face not quite disappearing. "I understand. When you're ready, I'll be here, ok?" She took Vanessa's hand in her own, squeezing it gently. After a moment of just holding hands, Brooke took another step, leaning over and giving a soft kiss on Vanessa's stubbly cheek.

It felt nice, having that casual affection that had been starved from Vanessa's life as of late. Vanessa paused, before turning backing to Brooke. Gently she cupped the side of her son's girlfriend's cheek, and drew her in for a kiss on the lips. Awkwardly, Brooke did her best but there was still uncertainty throughout every movement she made. It was clear she didn't have a lifetime's experience making out like Vanessa did. Even kissing a girl wasn't new to Vanessa, given her history dabbling with the fairer sex before she settled down with Tyler.

Her tongue working deeper into Brooke's mouth, she hungrily kissed her; slowly, Brooke gave in to her feelings and reciprocated eagerly. Their bodies pressed together, padded only by the faintest hint of softness over top of Brooke's own muscles. After a long minute passed Brooke pulled away, both of them out of breath.

"Wh-what's wrong?" Vanessa gasped out between deep breaths. She shifted her legs, trying to hide her erection; it had only been meant as a nice kiss and already she had lost control.

Brooke blushed, shaking her head. "Nothing's wrong, I just..." She hesitated, holding back for a moment. "We talked about this, remember Corey? We're going to wait to have sex with each other until we're ready, since we're both... ya know..."

Vanessa fidgetted, unsure how to take the news. Her son was holding off on sex? Were things really that special with this girl for him, that he would wait for her? And that last part: was her son still a virgin? Was Brooke still a virgin? The room spun for a moment, and Vanessa realized how close she had come to ruining things for her son.

"Oh yeah..." She mumbled, nodding. Guilt sprawled through her mind, and she quickly stood up. "Look, I, uh... I have to go." Vanessa got up and turned away, heading toward the door of Brooke's dorm.

"Wait! Don't--" Brooke's voice cut off as the door opened before Vanessa had even gotten there. Both of them froze, looking at the girl with long black hair as she walked into the room. Her perfume followed her like a cloud, overwhelming Vanessa's senses as the scent of a fresh, rich dessert filled the air.

"Fucking history class," she griped, not noticing Vanessa at first. "Stupid teacher is making me do extra homework." The girl whipped her head up, noticing Vanessa standing there awkwardly with Brooke a few paces behind her. Immediately, her eyes narrowed, while a devilish smirk formed on her lips. "Brooke," she said, not taking her gaze off Vanessa. "Who's the guy?"

Brooke sighed, taking a few steps forward to place herself between Vanessa and the newcomer. "Felicity, this is Corey... my boyfriend. Corey, this is my roommate."

Vanessa nodded, but Felicity cut her off before she could speak. "Yeah, yeah. I thought we weren't having significant others over?"

"Look," Brooke said. "I'm not breaking any rules, and you weren't home. You didn't have a problem with me having friends over before--"

"Yeah, well, you weren't fucking those friends."

Rubbing her temple, Brooke sighed. "We aren't fucking, either. So chill out, ok? You can't be grouchy about everything just because--"

"Hey! Shut it about... that. Ok?" The conversation seemed to die, and Vanessa looked around awkwardly.

"Well... it was nice to meet you! Bye Brooke!" Rushing out the door, Vanessa slipped into the dorm hallway, walking toward the exit of the building. She could hear hushed voices behind her talking - presumably about her hasty departure, or her unwelcome presence in the first place - until the heavy door slammed shut. Vanessa sighed, looking at the ground as she walked. Hopefully she hadn't ruined things too badly with Brooke, she thought to herself. It would be a mess for Corey to come back to yet another broken relationship.

Still, what Brooke had said had bothered Vanessa. Was Corey really a virgin? She hadn't really talked with her son about how active his sex life was, but given the few girlfriends she had met she had just assumed that he was doing stuff with them.

Vanessa shook her head. Maybe that was why she was so horny all the time: her body was backed up, in need of release. It made sense, in a dumb sort of way. It wasn't the kind of release that just jacking off would fix; she'd been at that all day and was still horny. No, it needed someone else, someone that would pull an orgasm out of her and leave her shuddering.

A dirty thought occurred to her as she walked, a temptation that threatened to pull off the path of purity she had promised Corey before leaving the house. There was an adult store, halfway between home and the dorm. It wasn't even going to take her any longer to get home, and then she'd have a toy to mess around with and hopefully take the edge off of things.

Before she knew it, she was walking in that direction. The sleepy neighborhood she was heading through was quiet at night, save for the occasional bar or gas station. The wind rustled through the trees, giving some company to the sound of Vanessa's footsteps along the sidewalk. Finally she made it to the store, noticing the few cars outside. She swallowed, her anxiety high. She'd been here years ago, and was pleased to find the store was still running after all this time.

The bell above the door chimed pleasantly as she let herself in, and she took in the layout of the store. A heavyset man chuckled at her from behind the counter, giving a small wave. "Hey there," he grumbled, his tone sounding pleasant to offset his gruff voice. "You're a new face, what can I help you with?"

A blush spread across Vanessa's face. "Uh, well, I was looking for--"

"For you, or the missus?" Despite interjecting, he sounded genuinely like he was trying to be helpful. Vanessa wondered if he gave everyone the same amount of attention that he was getting right now. Maybe just because it was late, he was focusing on her?

Vanessa looked away, nodding. "Uhm... me..."

The man behind the counter grinned, gesturing at a display of toys on the wall. "There you go, though we're having a special tonight." He leaned in conspiratorially, his voice dropping to a scratchy whisper. "You buy something, you get a trip in the back."

A long pause filled the air. "What's in the back?" Vanessa asked, taking a glance down the hallway. She turned back to see the guy giving her a look, and then it dawned on her. Oh, she realized, this was one of those adult stores with 'private rooms'. Within a moment of her understanding her pants grew tight, and she turned away to investigate the wall of toys.

It was overwhelming, to put it frankly. Women's toys were largely just grouped into categories like "goes inside you" and "buzzes a lot", but men seemed to have more toys. Not only were there those two groups, but also toys for you to go inside of, 'extensions' and other items to make you larger or feel different inside someone else, and things to make you last longer. Vanessa briefly wondered if she needed something like that, uncertain if her current performance was average for a guy or not.

Sheepishly, she grabbed a couple items off the wall - she had her son's wallet for the sake of having his ID, leaving her with his bank card to use. She'd pay him back, she reasoned. Once all this was over.

The man just chuckled, looking over Vanessa's purchase. "Alright young man, there you go." He gave back her items in a generic black plastic bag. "Go ahead and check out the back if you want, she's waiting."

This was it, the moment of truth. She knew full well there would be some kind of sex room or booth or something of that sort back there, and going back committed her to having sex. Not just sex, but sex with a total stranger. A total stranger... The words ran through Vanessa's mind. What harm would there be, having sex with someone that both she and Corey didn't know? Surely that would get this dumb, stupid urge out of her system faster than some rubber toy she'd bought, and then she could just move on.

Even as Vanessa walked toward the back of the shop, down a barely lit hallway that was sketchier than she liked, she knew there was no turning back. Her mind was too made up, it was decided that she was going to go through with whatever was on the other side of the door that loomed ominously at the end of the hall. Hesitantly, she opened it, only to find what looked like a changing room that could have been in any mall department store. A hook on the wall and a mirror, along with a bench adorned the room.

The only thing out of place was the wide, velvet lined hole in the wall at waist height. Vanessa gulped. A glory hole, that's what this was. She'd heard of them before, and of course back in college she'd been to parties where there was rumored to be some, but she'd never been to one herself and certainly never put any part of herself through them.

A finger slipped through the hole, and a soft voice called out from the other side of the wall. "Are you there?" she said, wiggling the protruding digit. Vanessa was unsure what to do, simply linking her own index finger with the one coming through the hole. Soft chuckles filled the air. It was amused laughter, not ridicule or cruelty. "That's ok if you're new, hun." Her finger pulled back after untangling with Vanessa's. "You don't need to speak or do much of anything. Just... go ahead and put it through, ya hear?"

Vanessa nodded to no one in particular, quickly unzipping her jeans. Her hands brushed against the soft cotton underwear she was wearing, the bulge underneath throbbing for attention. After only a second or two of hesitation, she pulled those down and let her cock bounce out of its prison. Her fingers instinctively ran over the shaft, feeling the thick veins that swelled along its length. A soft moan escaped her lips, before she came back out of her trance and realized what she should be doing.

Lining up with the hole, Vanessa slowly slid the hard cock at her hips through. For a moment, she felt wrong about using her son's body - her son's cock - for her own pleasure; especially since he was seemingly a virgin still. But the moment she felt a pair of cool and soft hands run against her shaft the concern was gone. She felt close to coming already, just from this woman caressing her cock. A whimper escaped her lips.

"Hey now, take it easy," the woman purred, her voice velvety smooth. "Just relax, and I'll make sure you feel good." As if to punctuate her point, her lips suddenly pressed against the swollen tip. Vanessa could feel the precum surging from within her, the beads of liquid cooling against her sensitive cockhead and starting to drip.

On the other side of the wall, she was starting to run her tongue up the underside of Vanessa's dick, flicking at her frenulum before kissing the tip again. To top it off, every kiss ended with a little suck, as she drew out the precum that was still dribbling out. It was intense and almost too much to handle, but the stranger was clearly skilled at what she did; Vanessa wouldn't be cumming until it was decided she would cum.

Soft lips wrapped around her tip like plush pillows on either side of her most sensitive flesh. Vanessa gasped out, putting a hand on the wall in front of her. Her eyes were wide as she felt the entire end of her cock being sucked on while her hole was played with by the woman's tongue. With a ragged breath, she tried to focus on avoiding blowing her load right then and there, but it was pointless. The woman started to bob her head up and down Vanessa's length, dragging those glossy lips along her cock.

"Ungh," Vanessa choked out a grunt before finding her words. "I'm... close..." The woman on the other side faintly nodded, enough movement for Vanessa to feel through her cock. The feeling of someone's mouth on her shaft was heavenly, it was divine, it was like an awakening of something deep inside of her. This... this was what she needed. Fuck anything else, she needed to cum in this woman right now. As if on cue, Vanessa could feel her balls tightening. It was happening, she realized distantly. Her thoughts seemed to slow down, her brain focusing on every physical sensation as her world contracted down to just her cock and the mouth on it. It seemed like time itself stood still, waiting for the moment to come when Vanessa would explode.

And then, she did. Her vision blurred as she came into the woman's mouth, her son's virginity long since gone. The thought of ruining him like this drifted through Vanessa's ravaged mind, only enhancing her orgasm. Despite how much she'd come throughout the day, she could feel copious amounts of cum firing off into the stranger's mouth, her throat working around Vanessa's tip as she presumably fought to swallow the thick seed.

The intense orgasm died down, and the woman - after a few moments draining the final drops from Vanessa's cock - finally pulled back and released her. Vanessa staggered back, looking down at her cock. It was sloppy, soaking wet with a stranger's saliva, and covered in dark black stains where her lipstick had rubbed off. Her cock looked used, and Vanessa loved it. She was still hard even as she pulled up her underwear and fixed her pants.

"Hey, I don't say this often, but you've got a sweet cock and even sweeter cum." Vanessa blushed at the woman's unabashed bluntness. "Listen, my name is Noire. Tell the guy at the counter to give you my number, and maybe we can do something else some time?"

"Oh... oh!" Vanessa snapped to attention as she realized what the woman meant. "Th-thank you, Noire." Awkwardly, Vanessa searched for something else to say, but found nothing. She slipped out of the room, heading back into the sex shop. The man seemed to be waiting for her, grinning wide.

"Ah, so how'd it go?"

Vanessa rubbed the back of her neck, nodding. "Uhm, Noire said to ask you for her number?"

The man's eyes went wide before he broke out laughing. "Of course she'd pick you," he said between guffaws, shaking his head. "The girl's got taste, I'll give her that." He grabbed some receipt paper, jotting down a string of digits on it. "Here's her number," he passed along the sheet, shaking his head again. "Well, since I'm sure we'll be seeing more of each other, my name is Corbin."

Vanessa mumbled her thanks, taking the note and stepping out the door. The sky wasn't quite as dark as it was when she entered, and she anxiously checked her phone. "Shit," she groaned, seeing the obscene morning hour. Had she really been with Brooke that long? Or had her 'little' detour to the sex store really taken her until four in the morning?

She quickly started jogging, her bag of purchases banging against her side as she ran. This body... It felt like it was made for running. It made sense why Corey went for morning runs and stayed in such great shape. Vanessa laughed, a giddy wave of excitement washing over her as she ran home. It felt like only minutes, and she was barely winded. This was almost as good as sex, she mused, resolved to keep going for runs and working out - even after swapping back.

"Where have you been?" Vanessa froze after getting in the front door, the angry voice calling out. From down the hall she saw Corey in her own body, marching towards her.

Immediately she cowarded, hiding her face. "I was with Brooke..."

Corey gave her a disapproving look. "She never stays up past midnight. I've been worried about you, what happened? And what's that bag you're holding?"

Vanessa glanced around, not seeing or hearing Tyler anywhere. "What does it matter, Corey? I'm an adult, and I was responsible, and beyond that is none of your business!"

For a moment, Corey looked confused, before shaking his head. "Just... go to bed. We'll talk more tomorrow."

Vanessa stormed off without looking back at him, heading upstairs. She stripped down as soon as she was in her room with the door shut, breathing heavily as she looked at her flaccid cock. It was still marbled with Noire's lipstick. It hardened as she thought about the phone number in her pocket.

It occurred to her that her trip to the sex store hadn't gone as planned, at all. Sure she got some toys to use, but now she'd been with another person. She'd experienced how rich and deep and delightful and earth-shattering sex was as a guy, and... She was addicted, she realized. One taste, a singular hit, and she was hooked.

She bit her lip, already stroking her cock. Was that really such a bad thing, though?

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calebjonescalebjones2 months ago

more soon I hope!

albertaboyalbertaboy4 months ago

This series is fun, 5 stars

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