Scene 18

This chapter got away from me, I think I need to cut it down when I publish. Let me know your thoughts. Thanks for reading

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Stepping into the apartment Linc kept one hand on at the base of Jacqueline’s back, just above her rear, pushing the door closed with the other he gave her a partial smile. She hadn’t said much at all on the car ride home, making him apprehensive about what they were going to do together, or at least he was till he recalled Jackson once oversharing his thoughts about a girl he had gone on a date with and the wild night they had. Lincoln was sure Jacqueline’s mind was full of thoughts of what they would be getting up to tonight. Jackson may have been living a lie before, but he was often bold. A trait that he found intoxicating in Jacqueline with how she once took him by the wrist and dragged him off to a supply closet saying how she was going to end his dry spell. She knew what she wanted and the fact she wanted him gave him confidence that he had never had before. Lincoln found it difficult to pull his attention away from her soft brown eyes. He had never been smooth with the ladies, but the way she stared at him intently made it clear she wanted him as much as he wanted her. Without stepping away from the threshold of the apartment and with great effort Lincoln turned his head and called out. “Madison, are you home?”

Taking as deep of a breath as he could with his cinched waist Jackson let the air out slowly, repeating the action three times. The familiar smell of his apartment felt comforting, the trip home in traffic had gone by in a blur. His eyes tracked cars zooming about the roads without a thought in his mind as he tried to decompress after that day. With the feeling of comfort of home around him, Jackson smiled, slowly blinking as he realized Linc was not just holding him with one arm and looking at him intently. ‘Why is he looking at me like that? Is there something on my face? Did I get lipstick on my teeth? He is smiling… he should do that more, he is always so uptight.’ Jackson thought without stepping away. When he heard Linc call out for Maddy he turned his head to look in the direction of his bedroom… her bedroom for now. He blinked slowly, looking at the half open door through the curtain of eyelashes. Jackson’s eyes felt heavy, making him wonder if that was from his prescription or just the day. “I think it is just us.” Jackson said, turning to look back at his friend, his mind picturing Callie. Her standing there in her little black dress with the straps criss-crossing over her shoulders, her standing with her hip cocked to the side in her pink heels and the flirty smile on her pink lipstick covered lips. When Maddy, Callie and him had gone out the previous night she had openly flirted with not just his sister, but also with him.

“Mmmm” Jackson let his body lean into the one pressed into him as their lips met, enjoying the slow sensual kiss. As the body pressed into him, Jackson took a step and a half backwards till his back was pressed against the door. It had taken a few seconds before his mind picked up on the fact that he was feeling stubble on his partner's face. Reality didn’t so much as crash back into place, it was more of a curtain slowly parting, only to stop part way to give a peak at what was behind it. There was no sexy blonde bartender kissing him, it was Linc and even as his mind told him what was really happening it took another few seconds for it to also provide the information that this was not a situation he wanted to be in. A contrast to the pleasurable feeling coming from his neck as his brown haired friend moved his kissing **** from his lips to his collarbone. “Linc…” Jackson said the name in a breathy voice, wishing he wasn’t feeling turned on thanks to his imagination and his **** fueled brain.

Moving his face up slightly, Lincoln gave one last kiss to Jacqueline’s neck, her perfume filling his nostrils as he breathed in and straightened his spine so he could look into her beautiful soft brown eyes. He had looked at Jackson’s face dozens if not hundreds of times and he never gave him a second thought and now seeing those same eyes rimmed and coated with makeup made him never want to look away. His attraction for his friend wasn’t without confusion, he knew who was under the makeup. Now though some of the same traits that felt abrasive felt captivating. The games Jackson played felt more playful knowing it was coming from someone attracted to him, someone that looked like this. She was still the same person as before, but the perspective had changed. No longer was it Jackson the lazy roommate, but a girlfriend that wanted to relax and temper his need to constantly do something. As a couple they could balance one another and right now they were in sync. She wanted what he wanted, but first he had made a promise. “I know, I know. I promised you a massage.”

Lincoln rubbed his jaw, nodding to himself once before stepping away from the bottle blonde. “Why don’t you slip into something more comfortable and I will be right along.”

Opening his mouth Jackson was about to ask if they had to do this, if he had to do this, but no words came out. Instead he closed his mouth, biting his bottom lip as he looked at his friend. Bobbing his head a few times before moving off to their shared bedroom.

Watching her go, Lincoln’s eyes watching Jacqueline’s rear end he wondered what she was about to say. ‘Did she want to skip the massage?’ He looked down at himself, seeing his semi erect member pressing forward in his pants and chuckled to himself having no idea that Jackson was oblivious to what had been pressing against him, his mind unable to process much and what it did all came slowly. Untucking his shirt he started to remove it as he took the few steps needed to move into the apartment’s kitchen. He slung the garment over his shoulder as he gave himself a small pour of honey whiskey. Taking the glass he rolled the container in his hand, watching the liquid, contemplating how lucky he was before tossing it back and following Jacqueline to their bedroom.

In the bedroom Jackson untied the cloth knot at his side, allowing the red wrap dress to open. Sliding his arms front he long sleeves he let it drop to the floor much like he did most of his clothes when he was done wearing them. Instead of proceeding to take off the bra, the corset or even his heels so he could take off the pantyhose, Jackson just stood there. ‘I did it before with Linc… but that was supposed to be just one time.’ His hands came up to cup the D cup prosthetic breasts. In the large rectangle mirror over the dresser he could see the blonde girl’s long red nailed fingers cupping the large breasts in her bra. It looked real, surreal, but knowing where to look allowed him to see some of the seams where the fake breasts met real flesh, the concealing makeup there either having worn off or missed. ‘Didn’t I promise him he could play with these if my team lost? Oh, oh that was all before today.’ Jackson’s eyes shifted down at his knees, seeing a small run in the pantyhose on his left knee. ‘I was with Dunn… now I’m about to do it again. Why am I?’

Jackson’s thoughts broke like brittle glass when Lincoln entered the room and spoke. “You didn’t get very far, did you want my help?” Jackson missed the flirty tone to the man’s voice, his hands moving down from the full bra and to his cinched in waist.

“A little.” Jackson said as he turned slightly to make it easier for his friend to undo the corset. He hadn’t thought about the thing since earlier in the day, a small smile coming to his face when two thoughts collided. That the corset, the vice that was squeezing him had stretched so it was looser and how nice it was for Linc to help get the thing off. He was getting more used to the long nails, but they made everything he did with his fingers different.

Soon Lincoln was helping unlace the corset, his hands grasping and gently squeezing her shoulders, feeling the tightness in her muscles he knew this was the right thing to do. While she wanted him, she was obviously nervous, something he hoped he was masking in himself. ‘Girls like confidence, fake it till you make it!’ When she didn’t turn back around he unclasped her bra, turning her to face him and pull it free. He had heard of or at least seen in movies how girls would do a strip tease to turn their man on, but she was making him do the work and it was making him feel like a kid again. He was removing her clothes like he would take off the wrapping paper for a present. When the bra fell he couldn’t help himself, reaching up to cup one of her breasts in his hand, running his thumb over her eraser like nipples. He knew they weren’t real, but the primal part of his mind didn’t seem to care about that fact at all.

Without the corset on, Jackson was finally able to take a true deep breath, he rubbed his sides, running his fingers of one hand from his side to his stomach, the cool air of the apartment finally able to blow across his skin. A small shiver ran through him as he was turned to face Linc, seeing the smirk on his face Jackson was about to ask him what he thought was so amusing, but then then extra weight from his chest on his back and the bra straps no longer pulling down into his shoulders as the support garment fell to the floor told him what was going on. “Cheeky” Jackson said amused, he wasn’t even sure Linc could take off a girl’s bra, let alone do it smoothly enough for him not to notice. He let himself be led the two steps to the bed, smirking at his friend as he got down on his knees to remove his heels.

When the tiny buckle was undone and the red strappy heel pulled from his foot, Jackson rolled his ankle and bobbed his foot. “I know know…” Jackson said out loud the rest of the sentence playing out in his mind unaware he had stopped talking. ‘...girls wear these all day.’

“I do.” Linc said, looking up at Jacqueline as he took her pantyhose covered foot in both hands and started to knead at the base of her toes.

Falling backwards from his seated position Jackson fell on the bed, his eyes rolling back in his head as he felt magic come to life. It felt like Lincoln’s answer to his question was that girls wore the sexy shoes so they could come home and feel what Linc was now doing to his feet. It didn’t sound right, but he was unwilling to argue the point and risk it stopping.

“As much as I love touching a beautiful girl’s stocking covered legs, these need to come off too.” Jackson opened his eyes, blinking a few times as he felt Lincoln shimmy his body when he tried to pull on the top of the control top pantyhose. He wasn’t sure when Lincoln’s hands had left his foot, but now that their warmth was gone it felt a little cold. A thought bubbled to the surface of his mind at the thought of being cold. “I’m almost naked.”

The pantyhose were only now just down to his thighs when they stopped moving and Linc’s face appeared above him, the bed shifting from the weight as Linc put one hand on either side of him. “That is the idea.” Lincoln said, his face darting in for a quick peck to the topless girls lips before going back to what he was doing.

“Finish what you started.” Jackson called out before pressing his lips together. He didn’t want to be kissed, not by him. Linc’s job was to give him a massage and he had stopped. When Jackson felt the warm hands once again resume their mission from God, Jackson dropped one hand over his eyes to block out the light from above. The pursed lips made a kissing motion as his mind drifted off back to Callie and then to Tabitha. He could feel the press of hands on his feet, easing out the tension in his instep, sliding up to take his calf in both hands and slide their thumbs up and down the muscle. As magical as they felt it reminded Jackson of the last time he had sat on a bed, his legs dangling down at the knee. A pretty girl had been kneeling between his legs, she had been picked up at a bar. Jackson laid there with his eyes closed, unable to remember the girls name, only her head bobbing up and down on him, her sucking on his dick… she had blonde hair. Just like Tabitha… or Callie. “Mmmm… that feels so good.” What was happening in the present and in his imagination mixed together in his **** clouded mind. “Ohhh… yeah, a great cocksucker.” He whispered.

Sliding his hands up to Jacqueline’s thighs Lincoln’s smile grew wider. “Yeah you are, but that is later. For now move onto your stomach.”

“Hmm?” Jackson moved the back of his hand from his eyes, looking at his friend that he had forgotten was there, despite what he was doing.

“I said.” Lincoln smirked seeing her panties doing little to hide the erect dick. Looking at the male member it confirmed in his mind that he was not attracted to male genitalia like Jacqueline was, but it was still flattering that he had caused such a reaction with just touching her feet and legs. “Turn over, I need to work on your back and shoulders.” He wanted to confirm that she was a great cocksucker just like she had said, but he had little experience with dirty talk in the bedroom and had lost his nerve.

“Oh, okay…” The light felt harsh on his eyes, making wanting to turn over an easy enough request, but laying on his stomach with the massive breasts felt so odd to him. A few seconds after he had turned over he felt the weight on the bed and then himself as Linc straddle him. Looking over his shoulder he finally noticed his friend no longer had a shirt on, but was unable to see that he had also removed the rest of his clothes from his angle. Jackson had a brief thought about how Linc would need to keep hitting the gym if he wanted real muscles, but that thought gave way when he felt his friend’s hands grip and apply pressure to the muscles in his own shoulders. “Okay… okay… yeah. Do that forever.” The pull of the bra straps, the weight of his chest, the fact that he sat and stood up straight, shoulder’s back and chest out all day had worn on him in a way he didn’t know till Lincoln’s hands eased his muscles of their burden.

“You want my hands on you forever?” Lincoln asked as he ran his thumb down her spine with slight pressure.

“Mmmm” was his only reply.

Hearing her practically moan at his touch caused Lincoln to grow more aroused, but even without it the fact that the only thing that kept them both from being naked was a thin lacy pair of panties she wore would have been enough. He continued to work his hands across her body, down her shoulders to her biceps, back up again and down to her lower back. Not one minute passing without her squirming, shivering or letting out one of her small playful moans of delight from his touch. ‘I’m giving her a massage and I feel like the lucky one!’

The feeling of his friends' hands roaming his body never came across to Jackson as off or creepy, his mind only had room for the pleasure with a sprinkling of questions about why he hadn’t hadn’t had this done before now, other than the obvious answer of being broke. Thoughts of what was to come hadn’t entered his mind till the weight on him vanished and he sat up and saw Linc standing next to the bed fully naked, with his cock fully erect. “Mmm that was good…” Jackson’s mouth hung open, his mind didn’t jump to the memory of when he had seen this very dick up close before or even the one from earlier that day. Instead the taste of cum haunted his mind and tongue.

“God…” Lincoln said looking at what appeared to be an awestruck mostly naked woman sitting on his bed. She had seen him before, had given him a blowjob before, but the way she acted in awe of what he was working with… she knew exactly how to flatter a guy. Reaching down he tran his hand through her hair, clutching the back of her head as he leaned down, his open mouth touching her own, his tongue moving inside her mouth. He felt her hands press on his body, her shiver in his grip. If Jacqueline hadn’t already made him hard he would have become instantly erect he suspected as she quivered in anticipation.

When Lincoln pulled his face away from her own he kept ahold of her head with one hand, using the other to move his dick closer to her face. In his haste instead of putting it in her open and willing mouth pressed it into her cheek. Feeling her flesh against his member, her warmth, her warm breath drove him wild. To Jackson the moment stretched on forever, things seemed to move in slow motion while he was paused in place. He hardly noticed being kissed, the tongue pressing and dancing with his own. His heart started to pick up speed as he felt trapped, held in place. His mind wasn’t able to panic, the **** emotion was far out of his grasp, but he knew he didn’t want this, but he wasn’t sure if no was a real option. His hands moved up to press on Linc, to push him back, but the **** to push him away didn’t come as one hand came up and made contact with his friend’s erect member. When he touched it he reflexively grabbed on, Jackson gripped the cock in front of him, unable to see as a man’s mouth pressed into his own. When he was free to breathe again he let go.

That was when Jackson felt Linc’s cock slap his face while he was still held still. The slap wasn’t something painful, not even close, but the idea of being slapped with a dick was so insane that it made him stop, stop moving, stop thinking. The halt in his slow thoughts only lasted a short time, but by the time he had mentally rebooted his lips were already wrapped around another man’s dick. ‘I love cock, I love Lincoln’s cock!’ The drunken chant he had said at the strip club with the girls came to mind. ‘I have to do this… I have to do this…’ Jackson’s mind reeled, unable to complete the sentence more as to why he had to. Only able to grasp at it having something to do with Dunn and jobs.

Only the tip was in his mouth, a slight whimper asked his lips around the obstruction. Jackson could feel Linc’s hips thrust slightly, the thick member sunk deeper into his open mouth just slightly, rubbing on his tongue before pulling back, but not enough for it to be free. ‘You have to do this…’ He thought once more imagining a clock ticking, the hands of the clock spinning around, still like this hours from now. As unrealistic as it was Jackson didn’t want this to go on for another thirty seconds, let alone longer and the only way for that to happen was for him to do a good job. Like he had done before. ‘Did I do a good job? Linc liked it.’ He blinked, reaching up to take the base of the tick dick in front of him and sucked in his cheeks, while flicking his tongue from side to side. ‘Do I want to do a good job? If I don’t…’ He continued to think as he pressed his father down further on the cock, allowing it more and more into his mouth.

“Yeah, yeah…” Lincoln said, as he let go of Jacqueline, allowing her the freedom to do as she pleased. “God yes… suck my cock… oh… oh… Jacqueline, you are such a good cock sucker.” He decided to finally play into the dirty talk she started earlier.

“Gul, gul… gulg.” The sounds came out of Jackson’s mouth as he felt the tip of the dick at the back of his throat. Pulling his face back so the thick member rested on his tongue he looked up to meet Linc’s eyes. Being called a cucksucker didn’t feel good, it felt just as wrong as the act he was performing and an act that made the words far too real. ‘Just a little more… just a little more. He is so hard he can’t last long.’ With each passing second Jackson felt the cock in his mouth pulsing instead of growing stiffer before blowing felt like an eternity, making his last thoughts sound hollow. ‘Moan I should moan, I like it when a girl does that!’

“Mmm, mmMMM!” Pulling the dick free from his mouth Jackson took a couple breaths before kissing the dicks tip the way he loved a girl to do it for him the one time a girl had done it for him. It was like she was worshiping his cock and that stroke to his ego had made him that much more turned on. “Come on, cum for me baby, come for me.” He didn’t want Linc to cum for him, in him, on him, but that was how this ended and his male ego that once was stroked by a girl felt brittle at the second. Each bob of his head caused his earrings to move in his ears and the fake breasts to sway. ‘That’s it… your Jacqueline, Jacqueline not Jackson! It is like a role, like when actors do a love scene. Everyone is calling you Jacqueline or Jackie already.’ Memories of voices calling out “Hey Jacqueline.” “Oh I love that dress Jackie! Where did you get it?” “Jacqueline, go make copies of this.” All fluttered through his mind. ‘Jacqueline this is fine for her… this is her boyfriend, this is who she is going to marry… she is just a bimbo secretary, she isn’t real, she isn’t real.’

When Jacqueline started to attack his member with vigor after telling him to cum for her, Lincoln thought he would do just that, but he greedily wanted more. It was clear to him she was enjoying herself, but he wanted her to get off just like he was ready to. So he took her head in both his hands, waited for her to look up at him and slid his dick from her mouth. “Are you ready for more?”

The words didn’t make much sense to Jackson, he needed… no. She needed to get him off. A small part of his brain thought things were over and while the now familiar salty gooey flavor was again in his mouth the sight of the saliva covered cock still there said things weren’t over yet. ‘Jacqueline, be Jacqueline.’ Jackson repeated to himself, taking the saliva covered member back in hand to redouble efforts, not understanding why Linc stopped.

“No sweetheart, get up on the bed.” Lincoln said motioning to the bed she was sitting on with one hand, very much amused at how much she wanted to suck his dick. Getting her on the bed and on to her knees facing away from him took a few directions. To him it felt like she was so lost in lust that she wasn’t sure what was going on. Putting his hands on her hips he pulled her panties down over her smooth ass so that they fell to her knees, when she looked back at him he gave her a comforting smile. “Don’t worry, we will take it slow.” He had never actually done anal before and figured this might be a first for both of them.

Jackson looked over his shoulders, part of his view blocked by his blonde hair that was a mess after Lincoln had his hands in it. What was about to happen should have been obvious to him, yet nothing was coming to mind. That changed when he felt his ass cheeks being pulled apart and something pressing against his anus. “LINC!?” Jackson cried out just before he felt the man’s dick press inside of him.

“Oh God! Jacqueline, you are so tight.” Jackson heard the man whisper behind him. Jackson gripped the sheets on the bed with both hands, his eyes going wide, his mouth hanging open as he let out a silent cry.

“LINC! LINCOLN!” Jackson cried out, not in a yell, but something more akin to someone talking as loudly as they dared in a library. His arms grew weak and fell forward onto his elbows, the rest of his body would have followed if the man fucking him from behind didn’t have a firm grip.

Hearing her whisper his name with intent he pushed himself into her a little more before pulling back slightly and inching in once again. He wasn’t sure exactly how to do this or do it for the most pleasure for her, but the way she fell forward on the bed, having her rear up for him to take her told him he was on the right course. Lincoln wasn’t a virgin, but he didn’t have a lot of experience to draw upon, but the way she called out his name over and over was driving him wild. He wasn’t attracted to men or there… things, but Jacqueline was all girl. It didn’t matter what she had between her legs, he wanted her to feel pleasure like he did. So as he slowly fucked her, going deeper and deeper with each thrust he reached around her waist to take her member into his own hand. He wasn’t so talented to time his thrusts with the jumping of his hand around her growing member, but as it fully came to life he closed his eyes trying to ride the wave of pleasure he was feeling and pass it on to her.

Jackson knew from the last time the two were intimate that Linc was larger than him, but feeling it now, feeling it inside of him it felt like it could have grown double in every dimension. He wasn’t sure how it fit inside of him, but he was sure it wasn’t supposed to be there with how much it hurt. It felt like he was being split in two, any second he would hear something snap and blood come rushing down. ‘Breathe, breath, breathe… Jacqueline, I’m Jackie, I’m Jackie, this is fine, this is fine.’ Laying as he was, Jackson arched his back trying to relax, focusing on the undertones of pleasure that were mixed with the pain. ‘What would Jacqueline do? What would Jacqueline do? Enjoy it… she would enjoy it, God help me she would…’ Biting the edge of the bed Jackson started to move his hips in rhythm with Lincoln. The pain didn’t go away, but it did lessen along with increasing the pleasure.

The fragile grip Jackson had on his sanity as his best friend fucked him was held in place by the thin fabrication of this all being an act. With every other thrust, feeling the mixture of pleasure and pain he repeated to himself how it was okay, because she liked this. This was okay, this was normal, she wanted this, she enjoyed this. Even with the medication it felt flimsy or at least it did till a new sense of pleasure came. Letting go of the bed with her jaw, Jacqueline opened and closed it several times, feeling a hand between her legs, embracing her… pleasuring her all while everything before continued. The repeated thoughts vanished along with any others, the added layer of pleasure made thoughts about anything too much for her clouded mind. “Ha… ha… eh, eh, eh, oh… oh LINC! GOD!” She yelled as her hands gripped the sheets tight enough for her knuckles to go white.

Lincoln felt his friend's dick change in a way, growing tighter just before it shot streams of ropey semen, each squirt had less than the one before, the member growing softer with each pump of his hand. His own breath was coming in ragged breaths, he had been ready to blow back when she was sucking on his member, he could have done it then, on her rear as she waited for him to enter her… and again when he felt her ass twitch and pump against him. A few minutes seemed to stretch on as the only sound in the room was their flesh pressing and slapping against one another and their breathing and now he couldn’t hang on for another second if his life depended on it. When Lincoln came inside of her he kept thrusting his hips, feeling her practically hold him in as her ass squeezed his member, trying to get every last drop of his cum.

His now softening dick still inside of her, Lincoln held onto her hips as he fell to the side. Moving only his arms so he could hold her to him. “Jacqueline…” He paused to take another breath. “You are beyond amazing.” Lincoln almost added that he was falling in love, but he held that back. Unsure if this was the right time to say something like that or if it was real. He still thought of other women, but even Maddy no longer held a place inside of him like she had before. Jacqueline… She was different, not just because she was transgendered, but also because she was really the first woman that wanted to be with him, or at least consistently wanted to be with him.

Laying there, being held as the little spoon, with another man still inside of him, Jackson’s eyes were wide open. They scanned across the room, as he felt the arms around himself, his ass throbbing in pain as something was still inside of him. While it was smaller it was joined by a feeling of something liquidy that was slowly oozing out of him. Laying where he was, Jackson could see the wet spot on the bed sheets where he had shot his own load. He had climaxed… it had felt good. ‘God help me it felt great. It hurt.. It hurts, but it felt… why did it feel good?! Am I gay? I don’t want to be gay… why did Linc fuck me? Why did I let him?’

Jackson let out a whimper, his thoughts that kept rolling and rolling over the same things. As he did he felt the hands around him tighten so that his back pressed more into Linc’s chest. He didn’t resist their pull, despite Linc being the one who did this Jackson knew Linc had to, they had to all because of Dunn. ‘Lincoln Hatch is my friend, God why did it have to feel… it felt good.’ Were Jackson’s last thoughts before he finally relaxed enough to let the sleeplessness of the overuse of the medication bring peace to his mind as he fell asleep in his friends arms.