Don the Degenerate Doorman: Apt. 6B

"You also seem to favor older men, much older it seems. Any thoughts why?"

"Well my high school boyfriend was my age and he was immature and selfish so I figured I'd be better off with someone older. I don't know; older men seem more attractive and distinguished looking to me."

Now I'm no psychiatrist (though I have held open the door for many) but you didn't have to be Sigmund Freud to read between the lines in regard to what Emily really meant. So we sat there a while after this and I did my best to look like I was contemplating what she'd said when I was really plotting what was to follow. After finishing my beer I met her eyes then took a deep breath before speaking.

"Okay Emily, I believe I can help if you let me. I just need for you to answer another question. Do you ever masturbate?"

"Y-y-yes, s- s-sometimes."

"How often? A lot?"

"N-n-no, not a lot. Every now and then when I get real worked up and need relief and there's nobody to help me."

"Do you use anything to masturbate, like a vibrator maybe?"

"No, I've never owned a vibrator in my life. Sometimes in the shower I let the water hit me there or I rub myself with a shampoo bottle or something."

"Any other objects?" I asked while imagining Emily naked in the shower with the water hitting her clit which made my hard cock twitch in my pants.

"When I was younger sometimes I used my hairbrush."

"Lucky hairbrush," I replied with a leer causing Emily to blush uncontrollably. "Now go get a brush."

"You want me to get one now, but why?"

"To help you conquer your inhibitions Emily. Listen you don't have to do anything you don't want to but remember that I'm just trying to help. It's up to you. But right now you're open to change and the alcohol you had will help with that. If you do what I say we can get you over the hump, I think. Your choice though."

"O-o-okay, I'll do it," she said as she stood.

"Good girl, Daddy Don is proud of you," I said to raise the stakes higher.

She blanched when hearing what I called myself but it seemed as if she was serious about trying to change and without another word she walked from the room with my eyes locked on her ass as she did. Emily returned a couple of minutes later with a hairbrush in her hand and apprehension on her pretty face.

"Are you normally dressed when you masturbate Emily?"

"No."

"Well then maybe you should take off your clothes."

I sat there impassively as she undressed but internally was another matter. My heart beat faster as each article of clothing came off and my cock swelled until it felt like it might burst. She had removed her blouse first and her full breasts looked spectacular even partially covered by her Agent Provocateur brassiere and when she removed that I felt my mouth go dry. She next unzipped her skirt and shimmied out of it leaving her only in her heels and black panties.

"Leave the heels on," I ordered her, my voice sounding hoarse to me.

She nodded then looked at the floor as she slipped her fingers under the waistband and slid her panties down. I let out a low whistle seeing her hairless mound and when I caught a glimpse of her pink as she removed the silky lingerie I had to stop myself from standing. Instead I clenched my hands into balls while my eyes devoured every inch of her nude form.

"Breathtaking is all I can say Emily. You are truly a beautiful young woman."

"Thanks," she replied shyly.

"Now I want you to go to the window and open the curtains."

"O-o-open the curtains?"

"Yes - open them now!" I demanded.

She swallowed hard but then her face took on a determined expression and as I watched she reached out and pulled the curtains wide exposing her body to any who could see into the sixth floor window.

"Now Emily, sit your sexy ass on the windowsill so you're sideways."

Once she was settled with one leg resting on the sill and the other hanging down I stood and moved closer to her though I didn't want to come close enough to make her feel uncomfortable.

"Play with your breasts to start with Emily, nice and slow if you don't mind."

After putting the brush on the sill her hands reached up and cupped her full breasts and then squeezed them, gently at first.

"Pinch those nipples now. Make them nice and hard," I instructed her and she wasted no time in following my words to the letter.

She let out a little gasp when they hardened from her touch and she threw her head back a little while biting her lip from the feeling it gave her.

"That's it Emily. Just imagine all the men in the building across the street watching while you do this. They're getting very turned on from what you're up to. Right now some of them are getting hard and starting to play with their cocks imagining being with you. Does that thought turn you on?"

Emily looked at me after I said this and her mouth opened in surprise when she saw I was in the process of removing my swollen erection from my trousers. I smiled at her as my hand started to stroke my thick cock and already there was some pre-cum oozing out the slit.

"Move one of your hands to your pussy Emily."

Her hand trembled slightly as it moved off her aroused nipple and down her body winding up at the sweet nexus between her thighs. While I watched Emily pet her little, hairless pussy I continued stroking my rock hard cock and more than once I had to stop myself from going too fast. Better to let her overcome her inhibitions slowly rather than rushing her and having a setback with my plan.

"How does it feel playing with yourself, are you getting turned on yet Em?"

"Yes I am, it feels so good," she managed to reply as her breathing quickened from her body's arousal.

"Is your pretty, pink pussy getting all wet and juicy?"

"It is. I'm so wet right now."

"Then show me Emily. Spread your lips wide so I can see your juices, show Daddy Don."

She gulped in reaction to my words but her slender fingers did what I asked and pushed her lips apart. I could see the sheen of fluids in her tiny twat as she opened it for my viewing pleasure when inspiration gifted me another idea.

"Bring your other hand down and put your finger in your pussy for me Em."

When her fingertip slid inside it made a squishy sound as it entered after which Emily began to make mewing sounds but I didn't let her keep it there too long.

"Okay, that's enough for now, let me see your finger."

She removed her finger and presented it to me for approval and I took her hand in mine as my tongue slowly licked the tasty juices off it.

"Hmmm, you taste so good Em. Your puss is delish, I can't wait to eat you," I told her. "Does that turn you on?"

"Oh God yes, I'm so turned on."

"I'm so turned on Daddy Don," I corrected her. "Now play with your clit and you can put your finger back inside your hot little pussy as well if you like," I said as I released her hand.

"I'm so turned on...Daddy Don," she told me as her digit re-entered her channel.

"Slide it in and out," I told her and again Emily wasted no time in following my directive.

Her slender finger disappeared inside her only to re-emerge covered with her nectar before starting the process anew. Wanting to get a better view I moved closer to her and crouched so my face was on the same level as her sweet, fragrant pussy. There I watched her finger being gripped by her inner lips as it worked in deeper then it pulled back when I noticed the forgotten hairbrush sitting nearby. It was made of hard pink plastic and had a narrow handle before widening at the section where the bristles were attached.

"Emily I want you to take your finger out of your pussy and replace it with your hairbrush."

"You want me to put it inside me? I've never done that before. I used to just rub it on the outside of me."

"You mean you used to rub it on the outside of your pussy. I want you to use that word when that's what you're talking about, or you can say cunt if you prefer. You have to remember what we're doing here is trying to cure your prudishness."

"Okay, I'll try but it's not easy after all these years," she told me after taking a deep breath. "I used to rub it on the outside of my pussy Daddy Don."

"Good girl Em. To start with just do that and we'll go from there."

She picked up the brush and true to her word started to slide it back and forth in the furrow of her pussy. The rigid plastic handle split her wet lips as she moved it up and down while her other hand continued to play with her erect clit, alternating rubbing and pinching the erect nubbin.

"That is so fucking hot Emily; you're turning me on so much. Damn you are one sexy girl, just the way your Daddy Don likes them. Now I want you to fuck yourself with the hairbrush, put in in your tight little pussy. Can you do that for me?"

Emily nodded her head and as I watched she adjusted the brush in her hand so the end was aimed at her wet opening. She let out a moan as it started to penetrate her and once a couple of inches had worked their way inside then her young body stiffened and tensed as her hand continued to feverishly rub her clit.

"That's it baby girl, cum for me," I told her though by this time my words of encouragement were no longer needed.

Emily let out a wail after which she bit her lower lip hard as her pale face reddened and glorious orgasm overtook her. That was the final straw that broke my control and I could no longer take just remaining a spectator as the young woman climaxed in front of me. I rose from the crouch I'd been in and leaned my head forward until my mouth clamped on her erect nipple. Emily moaned and when my hand covered hers and guided the handle deeper inside her the moan became louder.

My lips released her nipple then kissed their way up until finding her sweet mouth and she tasted like wine to me. Emily eagerly responded to my kiss, in fact as soon as my mouth opened her nimble tongue slipped inside to wrestle with mine. During this our hands continued to work the hard pink handle in and out of her tight pussy as deep as it could go. Meanwhile my hard cock rubbed against the smooth, silky skin of her dangling leg leaving a trail of clear, sticky pre-cum wherever it touched and inflaming my passion to the boiling point.

With some reluctance I broke the kiss but only so I could sample Emily's womanly essence. My mouth now worked down her aroused body from her slender neck to her hairless mound, leaving a trail of burning hot kisses wherever it went. Finally it zeroed in on her erect little berry and my lips closed around it and sucked hard while all the while I continued to fuck her with the brush handle.

This pushed Emily's body into another orgasm, this one more intense than the last judging by her reaction. She thrashed about wildly and the fingers from her hand not on the brush dug into the flesh of my shoulder as she let out a series of low moans as she came. When her trembling subsided I released her clit from between my lips and straightened my body so I could look her in the eye.

Emily wore the expression of a satisfied woman though we had just begun and had much more to do before concluding. My hand guided hers in removing the brush from her pussy at which time I brought it up near her face. The handle was slick with her juices and I touched her lips with it.

"Suck on it Emily until none of your pussy juice is left there."

Without batting an eye Em opened her mouth and slipped it inside and began sucking. By this time my cock was so hard and ached so badly that I didn't know how I was still thinking straight but I had one more task to complete before thinking of my own satisfaction. I removed the brush from her mouth then stared at her until she blushed and cast her baby blues down unwilling to meet my gaze.

"How did you like the taste of your pussy Emily? Enquiring minds want to know."

Her face got even redder from my bold question and she gave me no answer and continued to avoid making eye contact until my hand took her by her chin and tilted her pretty face up.

"It would've been polite if you gave me an answer but that's okay Em. I know how good you taste and now so do you even if you're not ready to say it. I think we've made good progress so far though we still have a ways to go. I have to say for someone so repressed you have managed to exceed my initial expectations. Masturbating by an open window so anyone can see is a step in the right direction, one might even say it's naughty. And naughty girls need to be disciplined," I told her while making my voice harsher for the last sentence and causing Emily's blue eyes to open wide from my tone. I took one step back after which I spoke again.

"Get off the windowsill now and face outside Emily."

She scrambled into position and once she had I pushed her upper half down so she was bent at the waist.

"Now put the palms of your hands flat on the sill and look straight out the window," I instructed her and as soon as she complied I used my foot to move one of her feet further from the other.

"Were you ever spanked when you were a girl?"

"N-n-no, my father didn't believe in corporal punishment. He believed it was more productive to reason with me instead."

"Well I can tell you that Daddy Don is a firm believer in spanking. In my opinion when you spare the rod you spoil the girl and that's the root of your problem I believe. I'm not going to make the same mistake," I growled right before I brought the brush handle across her taut buttocks.

Emily let out a yelp when it connected with her supple ass and her body flinched a bit so I placed my free hand on the small of her back to hold her in place. For the next couple of minutes I rained down blows on her defenseless flesh as she squirmed and cried though I give her credit for not asking me to stop. I did my best to space the blows out and not hit the same spot too often while making sure every inch of her sweet ass received the attention it so richly deserved.

The reason I stopped wasn't because I felt sorry for Emily or thought she couldn't take more but it was my lust finally got the better of me. Since seeing her panties in the cab I'd desired her and my cock had been erect since she'd been kneeling on the bathroom floor and I couldn't wait any longer. Dropping the brush to the floor I grabbed my shaft as I positioned myself directly behind her. When my swollen head first brushed against her wet sex she gasped and as I rubbed it on the outside of her lips it turned to a moan.

"Emily I want you to take hold of my hard cock and guide it to your pussy, but that's only if you want me to fuck you."

No sooner were the words out of my mouth then her right hand moved from the sill and reached back between her thighs. It was my turn to gasp when her warm hand wrapped around me and she wasted no time in bringing me to her gates of paradise. Once she positioned me at her hole I pushed forward, my head forcing its way inside her tight, pink pussy. It was slow going as she adjusted to me for I was much wider than the brush handle but through perseverance and Em's natural lubricant progress was made until only a couple of inches of cock remained outside her.

"All right Emily, we're almost there," I told her as I marshaled my energy for the final push. "When I say now I want you to push your ass back towards me, okay?"

She nodded her head in reply at which time I said now. Emily pushed back while I thrust forward burying my cock to its limit as my pelvis collided with her ass and my swinging balls slapped her clit. My hands grabbed her hips which allowed me to pull her into my forward thrusts as we built up a fast rhythm. The room was soon filled with the scent of her arousal and the sounds of our coupling bodies meeting.

While watching my cock slide in and out of her clinging flesh I have to admit that my attention was drawn by the puckered rosebud just above her pussy. It seemed to be calling to me as I drove my cock to its limit a few inches beneath and I felt it would be a good test to see if Emily was winning the battle versus ingrained prudishness. However it would have to wait for I had no intention of stopping until I filled her pussy with my cum.

My body bent at the waist until my chest and stomach were brushing the soft skin of Em's back and it felt hot to the touch and excited me beyond what I already was. My lips kissed the back of her sweaty neck as my hands slid from her hips and traveled to her swaying breasts which they seized roughly. I felt her pussy muscles contract on me when I grabbed her and she pushed her ass to meet me.

"That's it Emily, fuck me like you mean it," I grunted as my hips increased their speed. "I can't take much more of this, I'm gonna blow my load!"

My hands squeezed her pillowy breasts while I continued pumping as hard as I could until I felt it begin. I managed a couple of more thrusts when the sublime feeling of my balls releasing their semen overcame me as I drove deep in Em one final time. After that my body remained motionless as my cock swelled then spewed its thick, creamy ejaculate deep inside Emily's puss.

"Fuck yes! I'm cumming!" I called out as I fired spurt after spurt into her.

"Don, wait, don't cum in me," she said in a sudden panic as she felt my discharge filling her vaginal tunnel.

"Much too late for that Em, but no need to worry. I was fixed years ago so I can't get you pregnant if that's what you're worried about," I whispered in her ear as the last drop of my cum seeped into her vagina.

With a groan I let go of her breasts then straightened my body before reaching down and encircling the base of my cock with my hand.

"Get ready Em, I'm going to pull out of you and when I do I want you to suck my cock clean of both our juices. Do you think you can do that like a real naughty girl would?"

"You just watch me Daddy Don," she replied in a determined voice after which I stepped back allowing my softening member to slide from her welcoming depths.

Emily was true to her word and as soon as I slipped free she turned around while staying bent over. Her hand grasped my shaft and a second later her mouth took my head inside and she kept going, swallowing more of me until my tip hit the entrance to her throat.

"That's it Emily, don't forget to use your tongue while you're at it. Lick up all that cum from both of us."

She did as I asked and once the part in her mouth was licked clean she pulled her mouth off me and then began to run her tongue on the section that hadn't fit in her mouth. Not only was she doing a great job of removing fluids but her efforts were also helping me retain my erection for the most part. My hands took her by the shoulders and pulled her up to a standing position and once up I kissed her dirty mouth hard.

Emily eagerly returned my kiss and letting my cock loose she wrapped her arms around my waist drawing our bodies close. My three quarter erection pushed into her belly due to our height differential as our tongues wrestled and we swapped spit until I broke the kiss.

"Your call Em, but what do you say about heading into your bedroom and continuing this there?"

"I say yes!" she told me while taking my hand and leading me from the window.

A minute later found us again kissing as we stood in front of her bed. Seeing no need to delay things I pulled my mouth from hers with the intent of pushing her onto the mattress when I noticed it was covered by many scattered items of clothing. No doubt Emily, like most women I'd known, had tried on multiple outfits before deciding on a final one to wear that evening. Knowing she took fashion seriously and had some expensive designer clothes I bent and scooped the clothing up and tossed it onto a chair clearing a space where I then pushed her onto her back. She looked up at me with a little smile as I quickly began to remove my clothing.