Don the Degenerate Doorman: Apt. 6B

Apartment 6B The Tipsy Fashionista

(An original story Copyright 2013)

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Intro: Don the degenerate doorman 'helps out' drunk fashionista Emily.

It wasn't the first time Wednesday night that I stood and stretched my tired body to help prevent my muscles from cramping up on me. It was a quarter to eleven and my double shift was mercifully drawing to a close. Ivan, the regular doorman during the three to eleven shift had needed to take a few days off and as was often the case in the building some of us had filled the breach with me taking this particular shift.

Stan, the doorman who'd be relieving me to work the graveyard shift, had already arrived and was in the locker room changing into his uniform. Stifling a yawn I headed outside to get a sniff of the pleasant spring air. It was a relatively quiet night in the heart of Manhattan and in spite of the seasonable May temperature the street was mostly deserted with only a few stragglers out and about.

I was just about to return to the lobby and in fact my hand was on the door handle when I heard a car pull up in front of the building. Turning I saw a yellow taxi had stopped there and it seemed as if the driver was engaged in an animated conversation with the passenger in back. Waiting out front in case it was necessary to hold the door I watched as the driver appeared to be pleading with the passenger until he threw his hands up in the air in apparent frustration. When he observed me watching he climbed out of the cab and headed in my direction.

"Hello sir," he said with a heavy accent, "but maybe it is possible that you help me. You work in this building, no?"

"Yes I do. What seems to be the problem?" I inquired.

"My passenger says she lives here in building but I can't get her out of car. She give me the address and I drive her here but she is just sitting in back crying. I think she is drunk, I don't want to call police but what else can I do?"

"You did the right thing in coming to me, my friend," I told him as I walked to the cab and looked inside. "How much does she owe you?"

"Eighteen dollars sir."

"Here you go. Can you print me a receipt while I help her out? For tax purposes," I explained as I handed him thirty dollars.

"Thank you sir. I get for you right away."

I then turned my attention to the passenger huddled in the back seat who did indeed live in the building and I'd even held the door for her when she left earlier in the evening. She was subletting an apartment on the 6th floor from a long time tenant who was abroad for a year on business. Opening the door to the back seat I stuck my head inside after first removing my doorman hat.

"Good evening miss," I said in my most soothing tone, "do you require any assistance getting out?"

"Huh, what?" she replied as she turned to look at me and her face was a mess.

Don't misunderstand, she was a very striking and attractive young woman but at that moment her eyes were swollen and puffy and her mascara had left black streaks down the length of her face. Her designer blouse had what appeared to be a big wine stain on it while her short skirt had ridden up so high I caught a tantalizing glimpse of her black panties. Normally she was very put together with not a hair out of place but it was plain that something had upset her badly for when she'd left a few hours before she had seemed in high spirits. She stared blankly at me for a moment when sudden recognition lit up her pretty, tear stained face.

"I know you, don't I? You opened the door for me tonight, right?"

"That's correct miss and now I'm here to hold it for you again. You've arrived home."

"Oh, did I? Okay," she replied after which she wiped the tears from her eyes then struggled to get out of the car.

I took a step back to give her some room and at that moment the cabby handed me the receipt which I took with a nod and slipped into my pocket. Fortunately for her I turned my attention back in her direction at that instant for no sooner had she clambered from the cab than she stumbled over the curb. Springing into action I caught her in my arms before she could execute a perfect face dive.

She had let out a shriek which was cut short when her body collided with mine and my strong arms encircled and drew her into my chest. It felt so nice having her soft, pliant body pressed against mine that for a moment I just cradled her. We remained like that until I realized we were standing on the street where anyone could see. My hands moved to her shoulders where they steadied her body before releasing her.

"Are you all right Miss?" I asked her, my voice dripping with concern.

She took a minute to answer as she took stock of herself to make sure everything was okay before then blinking a couple of times as her big, blue eyes met mine and she considered what I'd said.

"Yes I'm okay, but only because of you. Thanks for catching me, if you hadn't..."

"Well no worries since I did. You ladies have to be careful when you wear such high heels," I told her in a matter of fact tone as my eyes fell upon the very high Jimmy Choo heels that adorned her seemingly perfect feet.

"Oh those, yeah they're high, I think almost five inches. But it's probably because I had too much wine to drink tonight."

"Really. Well let's get you into the building then so there won't be any more problems tonight. May I offer you my arm, Miss?" I asked solicitously.

"Okay, but I can trust you right...sorry I don't even know your name. I suppose I should though, I've lived here for three months now."

"No need to be sorry Miss. My name is Don and yes you may trust me for I'm here to help," I told her as I guided her to the front door.

It took a bit of doing to hold the door open while still steadying her but I managed to accomplish this and get her inside the lobby before Stan managed to get off his lazy ass to hold the door. He saw the condition she was in and raised his eyebrows and all I could do was shrug helplessly in reply as I assisted her toward the elevators.

"Almost there now miss, we'll have you in your apartment in no time," I told her like I would a child and it didn't go over well with the drunk young woman for no sooner did I say it then she pulled free of me.

"First of all my name isn't Miss. I have a name - its Emily. And please stop patronizing me; I'm not two years old. I'm just a little tipsy is all."

"I'm sorry Emily that I offended you, it wasn't my intention. I was just hoping to get you home with no further complications. As soon as you're safely there I won't trouble you any further."

"Sure just like every other man I've met. Can't wait to get away from me as fast as you can," she replied as she leaned against the wall for support.

There was no way I or anyone else for that matter would win with Emily in the condition she was in though her last words gave me a pretty clear insight into the reason why she was upset. During the time I hit the elevator call button I turned away from Emily for a second and when I looked back she was in the process of sliding down the wall until she wound up sitting on the rug.

"Whoops I don't understand it, now I'm on the floor," she said with a giggle before bursting into tears.

Ignoring the elevator whose doors had opened I approached Emily and bent down to speak with her. When I did my eyes took a fast peek at her lower half. Her skirt was now almost up to her waist, not only revealing her long smooth legs but her black silk panties as well. The sight of this caused me to forget how tired I was and to think about other, more sordid possibilities.

"Whenever you're ready Emily I can help you to your feet if you like," I told her after tearing my eyes away from her naked limbs.

"Okay Don, I'm ready," she said brushing away her tears and then extending her dainty hand in my direction.

My hand gripped hers at which time she pulled herself up with some assistance from me. No sooner had Emily regained her feet however than she staggered into me when she tried to take a step forward, after which she wrapped her arms around me to steady herself. Like had happened before on the street when her body met mine, all I could think about was how nice she felt pressed against me and I was reluctant to release her.

But with Stan not far away, as well as the lobby under constant video surveillance, I knew better than to prolong this so I gently removed her arms from me and pulled her into the elevator. Not wanting her to fall again I kept my hand on her shoulder as we rode up to the sixth floor. It wasn't until we reached her floor and the doors opened that tipsy young Emily realized that her skirt had ridden up almost to her waist.

"Wait one minute, don't want to give any neighbors a free show," she told me as she tugged it down and as she did my narrowed eyes watched her like a rapacious bird of prey.

After she finished she looked my way and her eyes widened when she saw my burning gaze fixed on her shapely posterior. For a second I thought she was going to say something but instead she smiled slightly and walked off the elevator in the direction of her apartment with me trailing behind. And unless I was mistaken Emily exaggerated the sway of her round hips as she weaved her way down the hall.

When we arrived at her door she began rummaging through her purse though from her muttered curses she was having a hard time locating her keys. Finally with a cry of triumph she pulled her hand out clutching a key ring at which time she managed to drop her open purse and scatter all the contents across the carpeted hallway in all directions.

"Don't worry about that Emily," I told her, "you open the door and I'll get your stuff for you."

She had looked like she wanted to cry again after she dropped her purse but my words seemed to placate her.

"Okay Don, thanks," she answered as I crouched down and began to gather together the spilled items.

There was her smart phone and wallet of course, along with other things that were standard fare for a young woman living in the big city. She must smoke for there was a pack of light cigarettes with a lighter as well as a tin of mints and a tube of lipstick. The most interesting item to my mind was the pack of condoms which were thin for 'greater sensitivity' they claimed. Personally I had no need of such artificial means for I'd been snipped many years before but they showed that Emily was ripe for the picking. Stuffing all the items back in her purse I stood up by which time she had managed to open the door and disappear inside the apartment.

"Emily, I have your purse," I called out as I stepped inside the empty foyer. When there was no answer I called out again, this time a little louder "Emily?"

"Could you please come here for a minute, Don," came her faint reply.

Closing the door I first put down her purse and my hat and then followed the sound of her voice which emanated from beyond the apartment's living room. Down a hall and through the first door to the left I found her kneeling on the bathroom floor before the porcelain throne.

"I don't feel so good Don," she said in a sad sounding voice.

"Do you want me to stay for a little while Emily?"

She nodded yes like a little girl would, her pale blue eyes pleading with me, but I was more focused on the swell of her buttocks as they strained against the tight skirt she was wearing. Many a time I'd fucked some drunken woman in a bar or club bathroom so I found her current position very arousing. On top of that I remembered when her skirt was by her waist and how sweet her ass had looked in her bikini panties. Needless to say my cock was half hard in my pants when I knelt down and gently stroked her auburn hair while pulling it back away from her face.

"Do you think you're going to be sick?" I asked her in my kindest sounding voice.

"I'm not sure, I feel a little queasy. I didn't eat much today and I drank too much."

"Oh, you poor thing," I told her sympathetically, "you have to remember to pace yourself if you're drinking and not do it on an empty stomach."

"I'm sorry but I was so upset."

"No reason to tell me you're sorry Emily. I was just saying it for future reference is all."

"You're right I know but I wasn't thinking clearly. Do you know what it's like to be told during appetizers that you're getting dumped for someone else? And I thought we were out celebrating our one month anniversary tonight."

"Well, all I can say is he must be an idiot Emily to dump a lovely young lady like you."

After I'd said that I saw more than one emotion cross her face although the sad look won out in the end.

"No, I wish that was the case but it's not. This isn't the first time something like this has happened to me. No he was right."

"Emily you have to remember that a young man doesn't know what he's looking for and probably isn't smart enough to realize what he has in front of him."

"That's not it Don. Malcolm isn't young, he's almost fifty and he knows what he wants and I'm not it is all."

"Well there you go. Maybe the difference in ages was too much..." I began but before I could finish she started to shake her head no.

"It isn't that. The girl he left me for is only two years older than I am. It was the same thing that happened back in college with Professor Plumb, only that time she was the same age as I was. No it's me Don, no man wants a girl who can't satisfy them in bed."

It wasn't often that I was speechless but Emily's words caught me by surprise and I had no idea how best to reply to them. Staring at her sexy body as she knelt on the floor it was pretty obvious there was no issue there. Most men would give an awful lot for a chance to tap her so it must have been some other reason that was causing her problems. We remained like that for a few minutes and while we did I wracked my brain trying to formulate a plan to take advantage of the situation. Of course my eyes were feasting on her figure as I did, so when she spoke it broke the spell and made me look at her face.

"Don, you're a man, can I ask you for some advice?"

"Certainly Emily, I'll do my best," I replied.

"Thank you and please be honest, no matter what. Lying to make me feel better won't help. I need the truth if I'm going to improve things."

"Okay."

"What kind of girl does a man want? I don't mean how she looks. I know some men like girls with blond hair or big boobs or whatever superficial preference. I mean what does he expect from her?"

That was a tricky spot she put me in but I saw an opportunity to turn it in my favor though I had to consider my words carefully or risk blowing it. The first thing was to delay her a bit to allow me to fine tune what I was going to say.

"I'll be glad to answer you Emily but let me ask you something first. Are you feeling a little better? Because it would be more comfortable not to be having this conversation on the bathroom floor. Are you feeling up to getting off the floor and sitting down?"

She paused before answering but she nodded her head yes after thinking about it. Once I stood I reached down and helped Emily to her feet after which we went into the living room where she sat on the couch.

"Would you like some water to hydrate?"

"Yes please Don. You are so sweet," she told me and boy she had no clue.

If she knew what I was really thinking those wouldn't have been the words out of her lips. Lips I was imagining wrapped around my hard cock as she sucked. In her refrigerator I found a pitcher of water with lemons in it so I poured her a glass. There were also two bottles of beer, they were light but beggars can't be choosers so I removed one.

"Emily, I notice you have some beer as well. It's been a long day and night for me, do you mind if I have one?" I asked her.

"Of course not, take one. Yeah I usually have some there. I guess you can take the girl out of Wisconsin but you can't take Wisconsin out of the girl."

"From the Midwest, huh? No wonder you're so sweet and innocent," I replied making her blush while I handed her the glass.

So a minute later I was sitting next to her on the couch and after drinking half the beer I turned her way.

"I could tell you what I like in a woman but that isn't really what you want. First I need you to say why you think it's your fault about things never working out."

"Maybe because that's what they tell me Don. Tonight Malcolm said he is too old to try and train someone to please him. 'If you don't know what to do by the time you're twenty three then what's the point?' he said. And Professor Plumb called me a prude and said it was too bad I wasn't Catholic because I'd have made a great nun."

"Okay," I said holding up a hand to stop her from saying more and probably becoming more upset. "Let me ask you something and answer truthfully. Do you like having sex Emily? Because you're very attractive so most guys would have interest in you."

She bit her lip before she answered and when she spoke her eyes darted about, not willing to meet mine.

"I do, I like sex Don. But I am kind of inhibited, I guess. I mean when I'm having it I have a good time and enjoy it but I'm pretty passive," she said in a voice barely above a whisper.

"But?" I added, for I could tell she wanted to say more.

"Well, the thing is, I was raised a certain way. My mom died when I was young so it was just me and my father. He loves me, I think, but he was never one to talk about things like emotions let alone about sex. When I first had my period he gave me a box of 'feminine products' as he called them and a textbook on human sexuality with a bookmark at the relevant section. He was a science teacher so to him that made sense, I guess."

"So you had no woman to talk with about sex stuff growing up."

"Well I talked with my friends some but it wasn't like they were experts either, plus of course the internet. So I kind of muddled my way through puberty. The only other guidance I got from him was when I was fourteen and a neighbor girl got pregnant. He told me in a solemn tone that he couldn't imagine what her poor parents were going through, everyone in town knowing their daughter was a harlot as he put it. Needless to say I was very repressed and was too scared to date until much later than all my friends. Even when I started I didn't let my father know because I knew he wouldn't approve of any of the boys."

"So if you don't mind me asking, how did you ever get beyond that to start having sex?"

"I don't think I've gotten beyond my upbringing. That might be why I still have problems with men. I lost my virginity after the senior prom in high school when I was 18 but my 'boyfriend' if you can call him that was a total jerk who only cared about pleasing himself. So when I went away to college and Professor Plumb showed interest in me, I thought finally here is my chance. He wasn't some young guy only caring about himself and getting off. He was a mature man of the world who would treat me right. What a joke! He was a total sex maniac and I was just one in a long line of students he bedded. I didn't care though and I would have continued going out with him but he dumped me for a less inhibited girl. Then I hoped when I moved to New York things would improve but it's still happening to me."

"Let me ask you about that. Why move here in the first place, this city has a reputation for being decadent? And to be honest guys here can expect too much. Some want a woman to check every box in their profile so to speak and if not the city is full of other women."

"That's what my father said, Sodom and Gomorrah on the Hudson he calls this place. But the fashion industry is my life's passion, that's what I went to school for. I know right now I'm not good enough to be an actual designer but I took some business and writing courses to go along with those on design. Right now I'm working for a major designer while trying to write articles on fashion as a freelancer as well."