Scene 15

“Jacqueline… Jacqueline?” Lincoln asked, noticing his friend and lover had fallen asleep. He couldn’t blame her, they had drunk a lot that night, he was feeling the pull of sleep too laying there in the bed feeling their warm bodies pressed together as a cool breeze flowed over them from the fan overhead. The problem was he was still incredibly horny, her passing out before he could finish. Pulling back he examined his friend's body in the dim light of the room. Her smooth legs still encased in her stockings, the bright nail polish on her toes, her body still wrapped up in her corset, with the top of it pulled down, leaving her large breasts exposed. It looked like she hadn’t gotten off either with the bulge in her place thong panties. His eyes lingered there, searching for any internal regret to do thing with someone else that had a dick. He knew he wasn’t attracted to men, Jacqueline was just Jackson dressed up as a girl. Lincoln thought he should have a problem with this, but… his eyes drifted up to the exposed chest with large breasts hanging free, moving with every breath his friend took and then looked up to their face. Jacqueline’s thick pouty lips parted as she breathed through her mouth. The lipstick she wore was long gone, but she hadn’t taken the time to remove the rest or even take her hair out of the updo. He was sure she would regret that in the morning, but mostly he was just sure that he really didn’t care that Jackson was born a man, the person laying there next to him was a woman, and one he was very attracted to.

Reaching over he cupped Jacqueline’s breast, running his thumb over the nipple. He knew she couldn’t feel his touch, but the fake breasts felt real to his fingers, it even was warm like her skin. Touching her chest with one hand he started to rub his still hardened member, his eyes moving between her now double D chest and then up to her lips. The lips looked much different now then when she used them to give him a blow job. Lincoln continued to jerk off thinking about how she demanded he give her his cock, imagining what it would feel like now with her new pillowy lips. It didn’t take long before cum exploded from the tip of cock, shooting onto the object of his desire. “Ahhhh! Ahhh…”

Feeling the release, the ecstasy, Lincoln took a few deep breaths as she fought off the urge to close his eyes. His smile faltered looking down at Jacqueline, realizing his cum had landed on one of her thighs, across her panties and to her lower stomach. The feeling of ecstasy passed, replaced with guilt. “I shouldn’t have done that…” He could just imagine her calling him a creep for what he had done and he couldn’t blame her. Who jerks off to a sleeping girl? With guilt driving his brain Lincoln grabbed some tissues from the night stand, cleaning off what he could from her skin, but the cum had mostly sunk into the blank panties. He had prepared for her to wake up as he tried to clean her off, but his friend didn’t so much as twitch to his touch.

Lincoln rubbed his forehead looking down at her again, covering her body with a sheet and blanket. He could blame it partly on their fun and how she had left him so horny, but putting any blame on her was the wrong move, he could blame the **** and it was partly to blame, but in the end it was on him. “Guess I will apologize in the morning.” Getting comfortable in bed next to Jacqueline, his last thoughts before he quickly fell asleep was how pissed she was going to be in the morning.

Feeling like his bladder was going to burst, Jackson sat up in bed, regretting it right away. His head was throbbing, he had to put his foot on the floor to feel stable as everything spun. “Gahhhh!” Jackson put his face into his hands, wishing he could just lay back down without risking pissing himself. The urge to empty his bladder growing in severity caused him to finally stand up. Jackson felt wobbly, forgetting about the new weight on his chest, making him almost fall on his way into the bathroom. Getting in there he quickly pulled down the panties, his fingers felt something crusty on the front as he did, but he ignored it for the second as he sat down letting his bladder release everything.

Sitting on the toilet with eyes half open he looked over to the bathroom counter, seeing a glass of water and three pills sitting next to it. Leaning forward he flicked on the bathroom light, regretting it instantly as the light assaulted his eyes instead of just doing its job to light up the small room. Closing one eye and squinting with the other he recognized the pills, two were aspirin and one was xanax. Even with the pounding headache Jackson smiled that his sister had left that for him before he went to bed. Taking the offered tribute he sat there on the toilet as some things started to come back to his now waking mind.

He remembered drinking a lot the previous night, Tau throwing an interception that led to a touchdown for the SeaHawks. He couldn’t recall the final score, only that the Dolphins had lost. He didn’t remember going to bed, but he vaguely recalled a vivid sexual dream… Jackson’s eyes moved down to the panties recalling the feeling he had dismissed when he sat down. Pulling them up he saw they were covered in dried cum. He also remembered dashing into the bathroom in the middle of night, falling down and retching over and over again. Jackson closed his eyes trying to recall more from the vague memory. Someone had helped him up and assisted him to the toilet, holding his hair as the contents of his stomach came up with a vengeance. He was sure it had to be Linc, but the memory itself wasn’t clear. Maddy was there too, he recalled hearing her voice and a cold washcloth being put on his neck and then someone helping him back to bed when he had put his face down on the side of the toilet. He couldn’t remember seeing anyone else or what they had said, but he remembered how nice the cold porcelain surface felt on his warm face. Jackson really hoped the wet dream he had happened after the run to the toilet. He was hungover and beyond embarrassed. “I’m never going to drink again.” He promised himself, knowing it was a lie before he had even finished saying it.

Pulling off the panties Jackson tossed them into the hamper that he guessed he now shared with Linc. He made a mental note to make sure he did the laundry so his friend didn’t see the proof of his disgusting deed, knowing it happened while they laid next to one another. He then took his time to loosen his corset enough to get out of the contraption. Jackson wasn’t sure what time it was, but he was awake now and wanted to wash off the shrink that he was sure came off of him after drinking to the point of blacking out and then retching it all up. The hot water and steam worked miracles when combined with the pills he took. He washed himself, but mostly just stood under the hot water, letting it roll off his body.

Standing there he moved one of his hands up to the large chest that was glued to his body. Running his hand along its surface, bouncing both when the other hand joined the first. Seeing the sight his member started to stiffen, but he didn’t move to touch himself. He didn’t really feel like doing anything other than going back to bed really, but he knew soon enough his older sister would come looking for him to help him get ready for another day at the office pretending to be a girl. Letting go of his new assets, Jackson turned around in the shower so the hot water hit his back as he placed his head on the cold tile wall. He wanted to think of a way out of this, any of it really, even a small victory, but his hungover mind gave him no answers. Jackson stayed there till the hot water started to cool before getting out to pat himself dry and starting his moisturizing routine. He was only part way through it, still fully in the nude when the bathroom door opened a fraction of the way and his sister came in.

“Ewww, cover yourself.” Madison said, grabbing a tower off a hook and tossing it to her very naked brother.

“Maddy! You can’t just barge into the bathroom like that and please don’t talk so loud.” Madison gave her brother a flat look. She could have gone her whole life without seeing her brother's equipment and been happy, so she really should have knocked, but she also wasn’t going to admit he was right about anything.

“Don’t worry Lincoln is already up, he is using the communal bathroom. So we don’t need to keep it down on his account. I will go pull some things out for you, finish up here.” Jackson shook his head, just slightly as quick pivots of his head felt like his brain was being smashed around inside. The shower and medication had helped a great deal, but he was still suffering some of the aftereffects of his actions.

“Maddy that isn’t…” He stopped talking when she left the bathroom. Jackson wasn’t looking forward to what outfit he would be wearing for his first Friday at the office as Jacqueline, whatever it was he was sure he would hate it on himself and wish he was just ogling another girl at the office wearing it. Jackson still took his time to finish, positive his sister would also give him a hard time if he skipped anything. It still felt like a bit much, using a face roller seemed crazy, but he did like that his elbows no longer felt ashy. Stepping out of the bathroom with a towel wrapped around his chest to try and contain the massive things he wish weren’t there, Jackson was surprised to find Linc in the room instead of his sister.

On the bed were some clothes, but his eyes were mostly on his friend who stood there smiling at him wearing socks, slacks and an unbuttoned gray button up shirt. “Ahhh, hi.” Jackson said, waving to his friend, holding up his hand and waving his fingers at him. Feel stupid for waving on top of the embarrassment of the wet dream.

Lincoln rubbed the back up his neck, giving Jacqueline an awkward smile. He had a rapid five minute shower, a freezing cold one. He figured she had used all the hot water, but after what he did last night a cold shower was the least he deserved. “I umm wanted to talk to you about last night.” Jackson’s eyes opened wide for just a second in fright, really hoping his friend was talking about all the drinking and betting while they watched the game.

“Yeah, crazy night.” Lincoln nodded, it really was a crazy night, but still he needed to push forward and apologize so things wouldn’t be so awkward between them.

“It was, and I needed to apollo…”

“Oh, no, no. You don’t need to say you are sorry. Look I’m an adult and should know better than to drink so much and your bet…” Jackson moved one hand to hold the top of the towel that contained his new chest. “I can’t blame you for wanting to touch these.”

“So you are not mad?” Lincoln asked wanting to make sure everything was good between them.

“Mad? No, I had fun, you had fun. We should do it again.” Jackson motioned to himself. “I look like this now and getting to just sit there and be myself with you is great.” Lincoln cocked his head slightly to the side, a bit surprised Jackson was admitting to enjoying things between them when so far he had been very repressive with how he talked, a bit contrary to how he asked as Jacqueline.

“So you are okay that I…” Jackson padded over to his friend, poking him in the chest with his long nailed index finger. “Just stop right there. I needed last night, I’m regretting some decisions this morning, but please don’t apologize and please let’s do it all the same in the future… just with less ****, I really needed last night. You have no idea.” Jackson was so happy Linc hadn’t noticed the cum stained panties and he knew football wasn’t his thing, but just having that one masculine thing was something he was going to refuse to let go of. Drinking while watching a game was something he didn’t want to lose. It wasn’t something he could easily do going out to a sports bar now, so he needed his friend to be there for him.

“I didn’t realize…” Lincoln stopped rubbing his neck, still surprised at the candid conversation and doubly surprised Jackson, no Jacqueline liked the fact he cummed on him… err her that she said she didn’t just want it, she needed it. He had watched his fair share of porn where a girl got a facial, but he didn’t think any girl really wanted it to happen. Yet here was Jacqueline saying just that. He thought about for a second, guessing it was a power thing or the fact a man was spilling his seed on him was a feminine act. He wasn’t really sure about it, but that fact she wasn’t mad like he expected, but wanted it to happen again left him in a much better mood. “Well, yeah sure we can do it as often as you like.”

Jackson gave Linc a big smile, patting his chest twice. Thank you, you are a good friend and I’m going to take you up on it. You know Sunday is also game day, so I hope you're up for it.”

“Yeah, absolutely.” Lincoln smirked at her, reaching down to button the bottom button on his shirt before leaning in to give her a peck on the lips. “I will let your sister know you are ready to get dressed. See you in the living room when you're ready to head out.” Jackson touched his fingers to his lips as his friend walked out of the room, shocked by the sudden kiss. He pressed the lips together, feeling just the tiniest bit of lingering pain from the minor surgery as he watched him go. They kissed just like that, a quick peck when they saw one another in the office, saying hi or goodbye to keep up appearances and with that kiss this morning it seemed Linc had made it a habit. One he couldn't exactly discourage to keep up appearances at work, yet he needed to do something to keep it spilling into his personal life. “I’m not a girl dammit.” Jackson said, catching a glance of himself in the mirror over the dresser. He was sure he was frowning, but all it looked like was the girl in the mirror was pouting.

“Sure you are, in fact my little sister is the girliest of girls.” Madison said, hearing her brother talking to himself. Amused that even alone in the room he still talked in that sultry husky voice she picked for how he should talk as Jacqueline. It had not taken really that long to get him to stick to it, but those first few days she had slapped his butt with one of her thin leather belts more than once to drive home the point and now it looked like all that **** had paid off. “You are just going to love your outfit for the day. I just love your closet, it is like having my own life size Barbie doll.”

It had felt like he was exactly that, and when he had asked her why she insisted on making me dress like this at the beginning she only said this is how Jacqueline dresses and then reminded him of the time he poured super glue into just one of her pumps before going to church one morning. She of course got her foot out later, it didn’t just hurt to get it off, but also ruined the shoe.

Today the first thing as always was a pair of panties, today’s panties were a lacy pink thong and then the thing he hated the most. He hated wearing heels, but wearing a corset was the worst of it. With his new assets he was sure the extra back support would help, but it wouldn’t change how he was being squeezed like in a vice and have to just function that way. “Today you have just this white corset to go around your waist, it is a little smaller than the one you wore yesterday, so you are really going to have to suck it in girl. Then I have a push up bra to match your cute panties that show off your tush.”

“Smaller? A push up bra?! Why am I going to wear that when I have these!” Jackson cupped his breasts in his sister's direction.

“Because when we bought you new bras yesterday you picked out a pushup bra, it isn’t my fault you want to show off your goods.”

“Maddy, I didn’t really pick out anything. I pointed at a few things you picked out.” His sister smirked, bobbing her head from side to side in satisfaction. Her brother now had to deal with having a chest bigger than her own and it would suit him right with how many times she had heard him make comments about women.

“I only picked things I knew you would like. I thought to myself what would my little brother like to see a girl in and that always leads me in the right direction for how I know my little sister loves to dress.” Jackson groaned, turning around so she could wrap the white corset around his middle. His head was getting better as time went on, but he still really didn’t want to argue with her. Jackson knew she was paying him back for years of torment, heck anytime when they were growing up that she tried to get back at him he would just tell on her and it would not just end, but she would get in trouble. Now he was paying for it as her doll, but at least he knew she really did care about him. Otherwise she wouldn’t help him at all, or would have helped him in the middle of the night in his drunken stupor.

The rest of the outfit was a sleeveless off the shoulder white blouse, that he was thankful wasn’t low cut to show off his chest, but it was much tighter considering it was purchased when he was using smaller forms. Dark sixty denier stay up stockings, a tight black pencil skirt and a pair of heels he thought they had purchased just to scare him. They were glossy black six inch heels with an inch and a half platform. “Maddy, these are not something any girl would wear to the office, heck these are things a girl would wear to the club and then take off the second they wanted to go dancing.”

“And yet you are going to wear them, think of it as me saying thank you for not listening to me when I said to stop drinking last night and then waking me up from a good dream when you fell to the floor. Also, I bet if you hold your leg out to the side and ask your boss, what was his name?”

“Dunn”

“I bet if you hold your leg to the side and ask Dunn how they look on you he won't say they aren’t appropriate for work, he will just give you a compliment.” Jackson pouted at her correct assessment. “You slip those on and let me go get you some accessories. Thinking I have some thick fake gold bangles for you to wear on your right wrist, ohhh some triple tiered pearl earrings will look wonderful with your blouse. You will want to show them off so let’s do your hair so it is pulled back and bit and have it all come over your right shoulder. This is going to look great!”

Stepping out of the master bedroom Madison yelled “TA-DA!” as her sibling came out after her. “What do you think of your girlfriend’s look for work today?”

Lincoln had been sitting on the recliner watching the morning news, turning to look when Madison came out. His jaw fell open seeing the ravishing beauty that was Jacqueline Hart. Getting to his feet he quickly came closer, his eyes moving up and down her body. Sure nothing much really changed from when she came home last night with the new additions, but he was sure he would have a similar reaction anytime she made an effort to look good. “Wow, wow, wow, wow, wow.”

“Are you complimenting her or trying to bark?” Lincoln’s eyes looked over to Madison who was wearing a red silk nightie, something he loved seeing the beautiful woman in, but the presence of Jacqueline dressed like that next to her overshadowed the older Hart.

“Trying to get my brain in gear to give a compliment. You are gorgeous!” Linc took a half step closer, putting one hand on Jacqueline’s hip as he leaned in to whisper in her exposed ear. “You look so sexy, want to recreate what we did in the supply room right now?” Jackson stepped back slapping his friend's shoulder, wishing the dick wouldn’t mess with him like that.

“Behave.” The platforms on the shoes technically made it so he was walking with only a four and a half inch heel, or at least he guessed that is how it worked. All he knew was they pinched his feet and were not easy to walk in when every step he took he felt his chest jiggle.

“With you on my arm as we go to the office? No promises.”