A Shell of A Man

byuppishcarrot©

Six years ago, I was doing well enough to finally afford my dream apartment. It was a studio apartment on the upper side of town. So, I had the job, the apartment, the money... but I was lonely. Very lonely and very horny. Not only would I get all hot and bothered from looking at all of the pretty women at work, but there were also plenty of hot women who lived in my building.

Have you ever seen that show 'The Real Wives of New York?' well, that's the type of breed I had in my new building. All the women were at least 10 to 15 years older than me, all were married or recently divorced... and all were loaded.

Of course, I was always far too afraid to approach any of these women. Sure I'd get glances every now and then, sometimes I'd even smile back but I always knew nothing would come of it. I'm a wimp. I always have been and I always will be. Even though I aspire to be your typical A sexual alpha male, the truth is I'm far from that, in fact I'm quite the opposite. I'm afraid of women, attractive women in particular.

Then one fateful Thursday night, I saw her. It was love at first sight; well it was for me at least.

I was just checking my mail when she emerged from her apartment: Barbara Sheelings.

She was the most beautiful creature I had ever seen. She was an enticing and captivating woman in her mid forties. I was in awe. I stood there like a little boy, staring at her, admiring her beauty. She was tall, very tall, with tanned olive skin, thick jet black hair, high cheek bones, brown almond shaped eyes and a figure to die for. She knew she was 'hot stuff' giving out this aurora. She had rich red lipstick on with a short tight black evening dress showing off her impressive muscular and toned swimmers thighs.

I didn't know what to do. I didn't know where to look. Whether or not I should smile at her, or whether I should even acknowledge her at all.

Just as I was about to give a friendly neighbourly wave: a tall ruggedly good looking male in his mid thirties emerged from her apartment. She clinged to his arm, looking up at him in admiration.

I looked on with a lump in my throat as they exchanged a passionate kiss. They were lovers, it was all too clear. I could not compete with this guy. He was well dressed, dominant and confident.... They were a good match.

I stood there like a little kid, jealous as they walked on by, passing me.

As she came closer, we made eye contact, just for a split second. I waited far too long to wave my 'hello'. Her eyes averted my gaze just as I waved at her.

To my relief, she didn't see that. I'm sure I looked every little bit pathetic that day, standing there with my jaw wide open, staring at her like some pathetic prepubescent boy.

As the weeks went by, my infatuation grew. This festered to the point where it started to affect my work. I was thinking about her all the time. In particular I was thinking about what it would be like to make love to her. 'What would it be like to make love to a woman like that? To have a woman like that admire your body? To have a woman like that scream your name in ecstasy? To have a woman like that moan your name in pleasure? To feel her warmth beneath you?' Needless to say, my mind wondered all the time as I kept projecting myself into some fantasy world where I was her King and she was my Goddess. Of course, it was just a fantasy.

It would always be just a fantasy. I was far too afraid to even acknowledge her. Fortunately for me, this was all about to change.

The day the postman mixed her mail up with mine was the day I learned her name: Barbara.

'Barbara, it seems the postman has mixed up your mail with mine..... oh what a lovely apartment. May I come in?..... Why yes, of course I'd like some coffee.... See your bedroom?.... Ms Sheelings!....' I tightened my grip around my member as I increased the rhythm, 'Oh! Barbara! Oh yeah!!! Mpf!!!! Argh!!!'

Even though I had her mail, I did not have the nerve to go to her apartment and give it to her personally.

Then one Friday night, the unthinkable happened.

I was sitting in front of my television watching reruns of Friends, eating my 'dinner for one' when my doorbell rang.

I was gobsmacked to see a very agitated Barbara Sheelings at my door. I was lost for words, I began to perspire... I certainly wasn't dressed for any visitors. I was wearing an embarrassingly old torn dressing gown. I looked like a hobo, nothing like her 'man'.

"Hi. I'm Babs. I live across the hall. You have my mail" she impatiently held out her hand.

"Oh right, I'm sorry... I, I, I was just on my way to give it to you" I frantically started shuffling through all of my mail to get to hers.

"Why didn't you just slide it under my door?" she said

"I'm so sorry Ms Sheelings, really." Nervously, I handed her the mail.

"You know my name?..... Have you been reading my mail?" she asked

"No! No! Nothing like that! No! I just read your.... to see who's mail it was. Oh god! I'm sorry. I didn't know, I don't know what to call you." I was babbling, rambling on.

Clearly, she thought it was charming. "Just call me Babs kid."

I wondered why she called me kid. I certainly was no kid. I was in my early 30's for Christ sake. No one had called me 'kid' since I was 19.

"Sure, I will" I said.

Babs smiled at me and walked off

"Bye-bye" I called out.

God! I was so goofy, so pathetic. I had no idea she found it so amusing.

Of course, I thought about her and fantasized about her the rest of the week. Excess masturbation is unhealthy, especially when you base your whole day around it. I was letting my work slide just because I was eager to get home and 'rub one out to her'.

The following week, I was checking my mail, oblivious to my surroundings. That's when I heard, "hey kid!"

Anxiously, I turned around to look at her. To my surprise, she was clinging to yet another man: this man was clearly younger, yet he was arrogant and cocky. They were a perfect match.

"err, hi Babs... how are...." My voice trailed off as they walked on by, passing me. It was almost as if she didn't even care. I could've sworn her date chuckled at me as I fumbled with my words.

So, back to the bedroom: my pants around my ankles, my right hand strangling my member, my left hand holding out a folded piece of toilet paper, getting ready to catch the stream of desire. 'mpf! Oh Babs! Oh Babs!' I moaned as I jerked off.

I couldn't distinguish whether or not she actually liked me or whether or not she was merely taunting me. After all, why would she say hello like that? As I ejaculated into the toilet paper I was reminded of the block headed pillar of testosterone that was her date and the fact that he had chuckled at me. It occurred to me that perhaps she was just teasing me, getting my hopes up. Yep, they were probably both having a good laugh about it amongst themselves.

Needless to say, as the weeks went on as did the casual greetings. Sometimes she'd be with one of her lovers, other times she'd be with her girlfriends and other times she'd be all alone.

It was always the same. She'd say "Hey kid" or "Hi sweetie" or "Hey honeybunch" I'd stutter, mumble and fumble over my words. Before I could ever actually say anything it would be too late.

It was a power she had over me. I couldn't figure out why it was that whenever I was around her, I turned into a stuttering, blushing little sissy.

Furthermore, it didn't help matters when she called me names such as 'honeybunch' and 'sweetie'. I couldn't figure out why she was calling me these names. Did she think I was gay? Was she teasing me? I mean, I knew she knew I didn't get out that much. After all, she lived just across the hall from me.

I was always a lonely guy. I always went to the movies alone, always had dinner for one and sex was more than often a solo activity. Of course I wanted to get out there and have a meaningful experience with an attractive woman, and of course I thought about asking her out. But I was a wimp. She was too attractive for me, too outgoing, too experienced, too intimidating. She would never go out with someone like me. It would be humiliating to be shot down and rejected by her.

Yet on a cold night in January, my phone rang.

"Sweetie?" It was Babs

"y,y,yes. Babs! Oh! Hello, my how are you? I'm fine, how are y,y,you?" gosh I was pathetic.

I could hear her chuckling on the other end, "I'm fine honeybunch, just fine. Thank you for asking.... Look, I have a free night tomorrow, I just wanted to invite you over for dinner."

I couldn't believe it. Was this really happening? Was the woman of my dreams asking me out? To her place??? I could not believe it. It sounded too good to be true. "Dinner? Tomorrow night? With me?" I asked.

"You like Italian?" she asked.

"Yes, yes I do."

"Great, come around eight. Okay sweetie?"

"erh, yeah sure I'll be there mamasita" oh boy! Did I just say mamasita? She laughed on the other end before hanging up.

To say that I was walking on air after that phone call would be an understatement. This gorgeous creature was asking me out. How wonderful. My fantasy mind went into overdrive.

The next day I called in sick to work. I know it sounds a little crazy, but I spent the whole day preparing for my date with Babs. I bathed for hours, I shaved, I wore my best shirt, I bought her a bunch of wild orchids... this was going to be 'my' night. Finally I was going to be 'the other guy'. The guy I always envied. The guy I was always jealous of.

At eight o'clock I stood at her door, rehearsing what I was going to say, 'Hello my dear, you look enchanting tonight. I'm in awe of you'. I wanted to be charming, I wanted to be classy. I wanted to impress her.

But when she opened the door, I turned into that blubbering, sputtering idiot. She was looking better than ever. She was wearing an alluring ensemble with a plunging neckline, short black skirt, seamed stockings with stiletto heels. "Hi, erh Babs. You look, erh.... I'm a lovely lady." I didn't know what I was saying, it just came out. It didn't even compute at first.

She arched an eyebrow, "Yes you are" she teased.

"Awww, are those for me?" She took the orchids from me, "they're beautiful. You are such a little sweetie!.... well, come in!" With that, she ushered me in.

Despite a shaky start, the evening was well underway...

Her apartment was quite impressive. It was at least three times larger than mine. It was tastefully decorated with modern art and eclectic furniture, complete with classic and contemporary pieces. It was clear that a great deal of care and attention had gone into designing and decorating this lavish apartment.

She excused herself for a few minutes as she tended to the flowers, putting them in water.

After what seemed like an eternity, she emerged from the kitchen.

That's when the worst thing that could ever happen on a first date happened. I had nothing to say. I was drawing a blank. I desperately searched my mind trying to come up with something to say, about anything.

We just stood there in awkward silence, looking at each other.

"So, you didn't go to work today?" she asked.

"How did you know that?"

"Silly billy! I live across the hall from you." She teased.

"Oh.... I called in sick."

"You don't look sick"

I was desperate to change the direction of this conversation; I sure as hell didn't want her thinking that I skipped a whole day of work just to prepare for our date.

"I love your apartment. It's just divine."

"awww! Thank you sweetie. Let me give you a little tour."

With that, she extended her hand to me. I swear I felt a spark. It was electric, this was pure bliss. For the next fifteen minutes she gave me the tour of her large apartment. It seemed like every sculpture and every piece of art had a story behind it.

The sheer size of this apartment astounded me. It was in fact a three level apartment. Complete with formal lounge, formal dining, a home cinema, a large kitchen and meals area, four bedrooms, five bathrooms, a gift wrapping room and a library. I felt bad for her maid, who ever she was.

Eventually, she led me up to her bedroom: the most lavish room of all. The magnificent view of the city all too clear below. This room was absolutely breathtaking.

"And lastly, this is my bedroom"

My eyes were drawn to the large king size bed, adjourned with pink silk sheets. I began to wonder what type of shenanigans had gone on in this room and if I would ever be lucky enough to revisit this room in different circumstances.

"Just amazing Babs. It's quite large, your cleaning bill must be astronomical" I joked.

"Well, when I was married my husband would do all the cleaning, it was so convenient."

"Wow! He cleaned all this? Why did you two break up?" I asked.

"Let's just say he couldn't handle it. He lives with his mother now, the fucking looser" she burst out into laughter, "I'm joking Frankie, lighten up!"

I laughed along with her, not quite understanding the joke.

She made a lovely three course meal. The appetiser was a light pumpkin soup, the main course was a fillet minion with baked potato and for dessert, a home made triple chocolate mouse complete with whipped cream. It was a meal fit for a king.

So there I was, having dinner with the girl of my dreams as we talked about our families, our careers and our ambitions.

After a good hour or two, we were seated in the formal lounge in front of a roaring fire sharing a bottle of Merlot.

Eventually the conversation died down and once again, we were plagued by awkward silence. To say I was nervous was an extreme understatement. I simply didn't have anything else to say. I desperately wanted to tell her a funny joke or an amazing story.... alas, I had none.

Suddenly she broke the silence, "So, why isn't a good looking guy like you married?" she queried

"ahh, oh boy! That's a good question. I guess I just haven't found the right girl yet you know..."

"Can I ask you a personal question?" she asked

"Sure. Go ahead." I said taking another sip of wine.

"Are you gay?" she asked.

I almost chocked on my wine. I couldn't believe that after all of our conversations and my blubbering that she thought I was gay. Needless to say, it shattered my confidence and I immediately went on the defensive.

"No, no, I'm not. I'm not gay. Why? Why would you think that?"

"It's okay to be gay. Don't get upset" she said.

"But I'm not gay. Absolutely not gay, seriously"

"It's just that, I never see you with anyone." She responded.

I could see how easy it was for her to make that assumption about me. Unfortunately, it was an image I was determined to shake.

"Yeah, I know. I just moved here four months ago. I'd like to meet more women," which wasn't entirely true, as long as I had her, I didn't want to so much look at any other woman.

"awww! I know what it is, you're shy. That's so cute!" she chuckled.

"Yeah. I kind of wish I wasn't. I sometimes wish I was like those guys I see you with." I admitted.

"Oh? Really?....are you sure you're not gay?" she teased

"No, no, I'm not. I just.... see you with them and I'm jealous of them. They are so confident and out there. They can talk to you and not get nervous."

With that, she reached out, grabbing the back of my head, pulling me into her face, kissing me hard on the lips. This happened so suddenly and so unexpectedly, I didn't know what to think. Then, just as suddenly as it happened, she broke contact, forcefully pushing me back.

"Babs, that was ama—"

SLAP! She smacked me across the face hard. I fell back clutching my face, looking up at her like a frightened turtle. 'what kind of sick game was she playing?'

To my surprise, she started to laugh. A playful, innocent laugh.

"I like little sweeties like you. So docile and easily manipulated.... Honeybunch, I'm going to devour you tonight. I hope you're ready"

Before I could respond, she reached out once again and aggressively, pulled me on top of her. She caressed my hair with both hands as our tongues played tag; her right knee was digging into my crotch, rubbing the growing bulge in my pants. "What's this??...... awww, you like me don't you sweetie?" she teased.

She proceeded to unbutton my shirt, slowly running her left hand inside, rubbing my hairy chest.

"A nice hairy chest. I love hairy men. So manly. All real men have hair." She exclaimed.

I was so completely lost for words, that I said the first thing that popped in to my head "You, you're amazing. I dream about you. I dream about touching your tits and sucking on them, they are just so---"

Out of nowhere, Babs broke out into uncontrollable laughter. This went on for several minutes as I sat there, feeling every little bit silly and pathetic. After what seemed like an eternity, she stopped laughing, composing herself.

"oh my! Do you want to see my breasts honeybunch?" she teased

"Oh god yes! really?? Yes, yes I do!" I must've sounded like a teenaged boy.

"Well, that's a right you have to earn." She said with a serious tone.

With that, separated herself from me, sitting on the other side of the couch.

"I hope I didn't say anything wrong" I said

She took a large swig of wine before shooting a look at me.

"Get undressed."

I looked over at her in terror, 'did she just say what I think she did?' She was so straightforward, so in charge, so dominant. This was her show, she was the boss. She stared at me and assertively, she continued...

"Didn't you hear me kid?"

Nervously, I arose from the sofa standing before her.

"Go on" she cooed me on, taking another sip of wine.

I proceeded to remove my shirt, placing it on the sofa beside her. Then I unbuckled my belt and unzipped my pants, letting them fall to the ground. I stepped out of them, one leg at a time, folding them, placing them on the sofa beside her.

I stood before her in nothing but briefs, and socks.

She was assertive without even saying anything. The look in her eyes said it all. I must admit, I was afraid of her, petrified.

Slowly, I reached into the waistband of my briefs and in one swift motion, I slid them off.

There I was, completely naked before the woman of my dreams.

Her eyes were transfixed on my stiffy, Babs took one final swig of wine, clearing the glass.

Slowly her eyes peered back up to me.

She arched an eyebrow as a sly smirk appeared.

Suddenly, her hand shot out, roughly grabbing a firm hold of my penis.

"Well no wonder you're not married. You have the dick of an eight year old," she said in such a tone that sent shivers down my spine. I gulped in utter humiliation. This was not at all how I wanted this to happen. I knew I was small, but I didn't think she'd call attention to it, at least not like this.

"Such a shame. You looked just like a man. But you are not a man, you're a little sissy. Just a dickless sissy," although she was playfully teasing me, I detected a sense of disappointment and disapproval from her end. No one had ever called me a sissy before. I always imagined a sissy to be a feminine male and that just wasn't me. No way, no sir. It wasn't me at all.

"Babs, please don't call me a sissy. I'm not a sissy. I'm a man" I protested.

"No you're not. Men have penises. Low, thick hanging flesh muscles that can please a woman, that can take a woman where they are trying to go every time. You simply don't have that. You have a little itty bitty worm. It looks like a coat hook....... But, you're so hard!" she looked up at me in disgust, "you like this? You like me telling you how small and silly your little clitty is?"

A smile slowly formed in the corners of her mouth, "You like me telling you how pathetically small you are?"

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