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Chapter 5 by Nicegent42
What's next?
A done deed
Music continued to play through the headset Bailey wore, while it helped him distract himself from what was coming it wasn’t enough to keep the anxiety at bay. Still his lips moved with the music, the song that just started an oldie that he knew by heart by the time he was an actual teenager.
Any way you want it, that’s the way you need it, any way you want it…It continued to play when he noticed the light that came in from underneath his bedroom door turned off and signaled him that it was time to get things started. Turning off the headset he removed it from his ears and tossed it onto his bed as he got to his heeled feet. ‘You can do this.’ He thought to himself knowing he could because had had before, even if every single time it had been horrible. ‘Just like, do a good job and it will be over quickly.’
Putting one foot in front of another the feminized man didn’t even think about how he rolled his hips with each step anymore. Opening the bedroom door he looked out into the dark apartment, the figure sitting on the couch easy to make out. ‘Here goes…’ Bailey thought to himself as he walked the short distance into the living room.
Pressing one hand to his chest he took a heavy breath, his breasts rising and falling as he took in one deep breath after another. In the dark, blind folded or not, Bailey didn’t want to look at Ryan’s face as he got closer, getting down to his knees. With each passing second his stomach churned with unease till it was practically twisted into a knot. ‘How did she talk me into this?’
Derrick sat on the couch, unable to see anything at all once Amanda turned off the lamp on the end table. When she told him to stay put when she opened the apartment door, he felt a small amount of panic rise in his chest, he was sitting here naked after all and couldn’t fathom what she was doing considering she wasn’t exactly dressed for the outside world. That was when he heard the sound of high heels walking on the hardwood floor that sounded like it was coming from the hallway. Turning his head to the side to track the sound he smiled at who he believed was his girlfriend. ‘Opening the door to put me on edge before running back to the room for her shoes… a little ASMR.’ Unable to see what was going on he tried to justify the sounds he was hearing.
The loss of his sight made this encounter interesting as he felt her hand rest on his right thigh, her nails sliding up a few inches before she did the same on his left. “Mmm” He let out the sound as his manhood twitched, Amanda’s warm hands a contrast to the cool room. The entire situation was incredibly erotic, her hands running along his hardening girth, each of them turning as they grasped him. The one at the base of his member twisting right, the other that held the tip of his cock turning left. Taking in a deep breath he let it out slowly as she pointed his dick up into the air, her tongue touching its base before sliding up. ‘For someone that doesn’t like doing this… God Mandy that feels good.’ Tonight was supposed to be about her giving him special treatment and right now he didn’t dare speak, afraid he would be unable to risk his urge to pull his sexy woman up into his arms. ‘Calm, calm, let her do her thing.’
Hearing the groan from Ryan as Bailey twisted his hands spurred him forward, opening his mouth he leaned in to touch the tip of his tongue to just above the young man’s ball sack. This close Bailey could smell the musk coming from his crotch, feel the heat radiating from the hard member and then he could taste it. Bailey wasn’t sure where Candi was hiding, but part of the plan was she was supposed to be close, wanting to hear her boyfriend call her name, but so far he hadn’t said a word. Some girls he had been with were screamers, a few liked to dirty talk and then there was those that mostly kept silent. Not saying anything didn’t mean they were bad in the sack, but they were his least favorite in bed and it seemed Ryan might be part of that group.
Making a disgusted face, not just at the taste of the cock he had licked but for even categorizing Ry as someone to take to bed. ‘Focus girl, just need to get him off.’ Bailey mentally winced at the thought and really needed this whole thing to be over with, it felt like it was corrupting who he was a man… a man wearing lingerie, high heels and was about to put a cock in their mouth…
Pressing his lips together Bailey blew warm air on the fleshy object in his hands, right over where had just ran his tongue before lowering the cock to point at his mouth instead of up into the air. Swallowing hard before kissing its tip, once, twice, three times before opening his mouth, sticking his tongue out to rolling it around the base of the tip. With a few flicks of his wrists, he bounced the cock in hand off his stick outstretched tongue, feeling it pulse.
“Oh…” Derrick whispered; the sound easy to hear with the only other sound in the room being the light smacking of his dick on his girlfriend's tongue. Then she took the tip of his dick in her mouth, suckling on it while continuing to use her tongue. He had to repress the urge to slide his hands into her hair but wasn’t able to keep himself from slightly thrusting his hips. Then he did it again as he felt her take more of him into her mouth as she bobbed up and down on his prick. “God, Mandy!” Derrick said while groaning, his voice low and strained.
Feeling Ryan buck his hips as he took him more into his mouth, the warm cock pulsing wasn’t lost on Bailey, but his reactions were secondary as he tried to focus on just doing the best he could to end things. When he finally spoke, his hoarse voice hard to understand, the feminized man would have smiled if his mouth wasn’t full. ‘There you go Candi, he said your name, that is what you wanted right?’ He thought at least two people in the room were getting what they wanted, he sure as heck wasn’t.
A cock in his mouth, almost to the back of his throat Bailey tasted a hint of cum, precum was a natural reaction for lubrication but it meant things were going in the right direction. ‘That's right Ry, cum for me, cum for me and Candi.’
Slurp
The sound filled Bailey’s ears as he pulled his mouth free from the cock, saliva trailing between it and his mouth and trailing down the corners of his mouth. Pumping one hand up and down on the member while his other cupped his balls, the action meant to buy him time to take a few breaths and not wanting to lose the momentum. The smell of sex was now in the air as he worked the member, it slick from spit and a small amount of cum. ‘Come on…’ He thought, not sure what would be worse, putting his lips back around it and his mouth being filled with the man’s spunk or it splashing across his face.

Candi had promised her man a blow job, an activity he had been on the wrong side of one too many times, one being the number that crossed the line and yet here he was opening his mouth and trying to loosen his throat to take more of the dick in. The sounds of slurping filled the room along with groans. Ryan’s voice sounded a bit off, but still familiar, not that Bailey paid too much mind. What Ry was saying was for the girl who talked him into this, he had a job to do and that girl truly owed him big for this.
Moaning himself, Bailey made the sounds of pleasure knowing what kind of effect it had on him when hearing a girl enjoy giving a blow job as much as he was getting one he made sure to over act, betting Ry despite being an attractive guy had seen more porn videos than been in situations like this. He tried not to think about how he was both physically acting and sounding like some wonton slut, he reached down, sliding one hand into his thong panties and touched the prosthetics clitoris. Immediately the vibrator wrapped around his own hidden member came to life. Pleasure shot through him, and he yanked his hand away from himself.
It was normal for a girl to touch herself while pleasing her man but experiencing any joy from sucking on a cock was a line too far for the feminized man. Already he knew the title cocksucker fit him and didn’t want the extra taint of enjoying it attached.
Hearing Amanda’s vocal queues, something he knew was a show for him, but still drove him wild, Derrick let out a shuddering breath as he felt that all too familiar feeling of things tightening, his body ready to explode. Amanda’s lips were wrapped around the base of his cock, her head staying put as she groaned, turning her head left, then right, pulling up only an inch before coming back down again he just couldn’t contain himself any longer. “Ah, ah, Oh, Mandy! Mandy I’m going to cum!”
‘YES! YES! I DID IT!’ A feeling of achievement hit Bailey along with a mouth full of creamy, salty cum that partially slid down his throat, the muscles in his neck twitching to swallow. Moving his head up and down a few more times the man’s seed slid down from one corner of his mouth, some of it already covering his chin. ‘Did he say Mandy?’ Bailey asked himself, taking a few gasping breaths as the thick cock came free from his mouth. He didn't need Ryan to say he was about to cum, the fact that the dick in his mouth grew slightly more and started to pulse told him exactly what was about to happen.
Shaking his head, his platinum blonde hair stayed put in its updo as Bailey dismissed what he thought he had heard. ‘Candi, not Mandy.’ Believing he was hearing things, it not making any sense why the young man would call out that name. The slimy feeling in his mouth, coating his tongue and chin disgusted him but before he could run off to the bathroom he needed to slip away and let Candi play nice with her boyfriend after the deed. He cursed himself for not having wet wipes, mouthwash and whiskey back in his room.
Using Ryan’s legs to steady himself Bailey got back to his heeled feet and was ready to slink away when large hands wrapped around him and pulled him into the man’s lap. “HEY!” Bailey said out loud not prepared to be yanked off his feet.
Derrick had just orgasimed under the attentions of the woman he loved, but it hadn’t full deflated by the time he felt her tight little ass press against it as he pulled her to his lap. Immediately things felt off. He could dismiss her voice sounding softer, more musical, but she also felt smaller. His woman had an amazing rear end, but he wouldn’t call it small like the one pressing into him right now. “Mandy?” He asked, confusion filling his mind as she wiggled in his lap, making his lower region think they were about to go for a second round.
This time Bailey was sure he heard what Ryan… no not Ryan, had just said and it made his blood run cold and his body freeze in place. When the lamp turned on next to the couch the glare from it felt like an attack with his eyes wide and used to the dark. He was not being held by a naked Ryan, but by a naked Derrick Connors who had one arm wrapped around him and the other pulling off a makeshift blind fold now that he had turned on the light.
“BAILEY!” Derrick’s voice boomed.
What's next?
Girlfriend's Daughter, What if?
Candi talks Bailey into trouble
This is an out of canon story for Girlfriend's Daughter, a fun sexual tale where Candi convinces Bailey to give someone a blow job and how it gets out of control.
Updated on Aug 28, 2024
by Nicegent42
Created on Aug 10, 2024
by Nicegent42
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