Tranny Tales Ch. 07: The Penthouse

I enjoy people. I enjoy company. My wife isn't very social. In the seven years we've been together we've only had one person invited into our home and that was for only a few hours. It was her Uncle Ted, who was up from Texas for a Shriner convention. He came to dinner wearing one of those stupid little red hats with a tassel, which he never took off, even when he went to the bathroom, which was very frequent as he had some prostate complication that most guys over the age of 65 or 70 run into. Claimed his prostate affliction was a result of rarely having sex with his wife. As for my wife, sex is about the last thing we do together, although everything else in our relationship is fine. I don't mean to say we never have sex, but certainly it's not often enough for me. Naturally this leaves me with the conundrum of where and how to have a sex life and as Uncle Ted suggested, how to keep my prostate healthy. Don't worry, I've worked it out just fine.

Although we rarely have visitors at home we do go out every few months to see my wife's friends, sometimes at their homes or more often eating out together in the one of the small and varied ethnic restaurants that fill Hell's Kitchen, that sliver of Manhattan that abuts Times Square and flows right up to the Hudson where they dock an old Destroyer and a huge Submarine. Sometimes I walk over to the dock and watch the young sailors scrubbing up the vessels that are swarmed by tourists on the weekends. Seeing all of them reminds me of the old gang I grew up with. I still miss the comradery; the baseball games, the touch football we played in the park and the bike trips we pulled off that drove our parents wild. I regret that I left them all behind in St. Louis when I came to work here in New York but this is the center of the publishing world and my agent is here. Now it seems that the only people I have occasion to speak to are the strangers I meet when I drag myself down to the laundry room in the basement of the building.

The laundry room is tiled white and the walls are painted white and the paneled ceiling has enough bright neon lights to burn out your corneas. The washing machines and driers are nearly new and line the walls, although the machines sometime balk at accepting a credit card. You have to insert it a few times and hope for the best. Finally if it flashes "approved" the washer starts to fill. The driers are on the other side of the room. When the washer clicks off you have to put your damp clothes in a small stainless steel basket cart and wheel it over to the driers. That's probably when things get lost.

While waiting for the machines do do their work, I sit there on the side, as if on a fishing trip waiting for the right fish, or gal to walk in carrying a basket of dirty cloths and while her clothes are doing a dance in the big round washer windows, I start up a conversation to check if perhaps she needs a break from the hussle of a housewife's life and perhaps has a vagina that needs a fresh insertion or maybe she'd like to spend a half hour playing with my cock while her hubby is sweating it out down on Wall Street. Of course a number of the women, the younger ones, are single and are "hot to trot" if you know what I mean. Of course you are safer with the married ones as they are not looking to fall in love and discretion is the better part of valor as the bard tells us. The married ones strangely prefer you don't use condoms, why? I haven't figured that out yet. But have you ever noticed how differently some of their kids look from one another?

New Yorkers are a friendly lot, contrary to what most outsiders think. I've met a few interesting people down there. If there is no one around I snoop a bit and there is always some unclaimed article of lingerie left behind in the washer or dryer that I can examine. I always wonder which tenant those big bras or panties belonged to. I even found a sexy pair of men's underwear which had the crotch cut out. It must have been from one of the gay guys. We have quite a few gay tenants. Some are old theatrical actors with beards and bald heads, but a few are young and quite attractive in a feminine way. I confess, I grabbed those red men's undies before I even realized they were my size and if I ever have a sexual epiphany, who knows if they won't come in handy in that gay bath house over on 29th street? I stuck the crochless cutouts in the bottom of my underwear draw a few months back and unless some bed bug stole them they are still there. Oh yeah, we had a bedbug problem two years back and the co-op spent untold hundreds of thousands cleaning it up. We still have a dog patrol who run through each of the apartments every month, sniffing them out, but so far there has been no reinfestation. Thankfully, just a few loose dog hairs lying about are the only inconvenience of their visit. Of course, when the dog patrol arrives you'd better not be fucking someone's wife as they knock once and then they have a key to open the door.

My wife is a tall pale white elementary school teacher at PS 103 a short subway ride away. So pale that the Indians would have surely called her "pale face." She is fun to be around but she has absolutely no sense of humor. Even her principle, at the yearly teacher's dinner said, "She's as serious as a heart attack." She has to be at school early so she leaves every morning about 6:10 am and catches her breakfast at the Teacher's Cafeteria. I don't know what she eats, although I imagine it's coffee, a yogurt and toast, same as she does here on weekends. She doesn't go for variety. She is as thin as a rail with long legs, short brown hair and an exception pair of big boobs, that I reach out for when I go to sleep and when I wake up, through hooded eyes, I like to watch her dress, hooking her big bra in the front and twisting it around and scooping her breasts inside, pulling up her panties before she puts on her slacks. Then she waves goodbye and leaves.

Sometimes I try to hold onto her breasts when we go to sleep at night although she pushes me away as I start to squeeze them when I fall asleep. I begin to miss them about an hour after she leaves in the morning. Just thinking about them I develop morning wood. A cold shower gives me some relief or a quick hand job but although I can if I have to, masturbation is not my preferred way of clearing my mind before getting to work.

I do freelance cartoons for several large magazines , you probably have seen my cartoons, probably that one where a one legged war veteran's dog is bringing him a right shoe, unfortunately it's the wrong shoe, it's the right foot that he lost, but you probably figured that out already. Maybe the theme is a little too dark for you, but that cartoon was a runner up for the Pulitzer several years back. I may still snag that award and if I do it will make my career forever.

I can sleep as late as I like unless I am on deadline, but I've got a box of unused cartoons in my bottom desk draw that I've never submitted. I can always pull one of them out or rework it to pull me through. Sometime all this drawing and writing gets me horny. That's when I need a break and head down to the laundry in the basement, not because I need to do a wash, but to see if any one of the equally horny housewives needs a fleshy stopper slipped into their neglected pussy. I don't stop once I get started, they seem to like that. What I've learned from experience is that if a woman lets you fuck her once, she will rarely say no to a second, third or more times. Her cunt becomes an open door forever. Of course you better make sure she climaxes before you stop pumping if you want that door to remain opened...

More times than not the laundry room is empty in the early morning, sometime that gay boy Franz is down there, looking for a cock to suck. If I'm really desperate I'll let him blow me in the corner of the room where the camera can't see, otherwise they'd get me on video and all the building staff would start making crude jokes whenever they saw me; not something I need and sex down there is a bit risky as you may not hear someone walk in with all the machine clatter. If none of the washers are whirling and you've got a horny housewife, you might take the risk in that little alcove, there behind the sink but you'll have to what you do standing up to make sure you are not visible. But as my Uncle Eddie would say, and he was old Navy man, "any Port in a bottle and any port in a storm," especially when your blood is running hot and your cock is perpetually erect.

In all honesty, on that warm summer morning, when the New York humidity curls your hair, I wasn't looking for Franz, I was looking for pussy. Although in a dark room he could pass for a girl, except for the goatee that felt just like puss hair when you were fucking his mouth. I mean, if you are gay, why would you want to give a pussy impression to the guy you are sucking off? Oh well, to each his own and I will give him this, even while he is sucking my cock, his tongue darts out from underneath the shaft and licks my big hairy balls. What can I say, it feels real good. But that day I wasn't looking for Franz.

I was looking for a new tenant who had just moved into one of the tiny penthouse apartments up on the 10th floor. These are two small apartments, hardly 600 square feet but they rent those suckers for three times what I'm paying for the glory of being able to say, "I live in a Penthouse." It must be nice, but I'm content living on a lower floor, paying a modest rent and a swooping in on any new puss that moves into our old building.

I'd met Olga briefly at a building greeting party a week or so back when some insurance guy had picked up the tab offering mixed drinks and snacks, pigs in a blanket and those Chinese fried dumpling which were not bad at all. He of course did all of this with the hope of selling a life insurance policy or apartment dweller's insurance or whatever else you needed. I got stuck with the apartment liability insurance which the co-op requires, and it will come in handy if the bathtub overflows and I get sued by the guy in the apartment below. The policy doesn't cover tears in the walls that were pre-existing or rips in condoms that can lead to child support and a host of worse problems; likewise, if you came home one night to an empty lot and were informed that the building was demolished by accident, they sure as hell are not going to cover that and in New York that has been known to happen.

As I said, I was looking for Olga. We had made a bit of chit chat that evening. She must be around 35 years old, said she was single although many of the unmarried woman of her age are closet lesbians. You never know for sure unless you open their night table and see a black rubber strap-on, or one of those rabbit squirrel thing-ees that do double duty. But when you go fishing for pussy you've got to take your chances, you throw out your hook and you never know if it's a flounder or a tuna, or for that matter a hooker. Best not to be fussy. I took the elevator down, walked along the basement hall looking up at the ceiling filled with overhanging pipes, most of which looked like new replacements and then into the laundry room, but no Olga could be seen. In walked Franz with a cart full of cum laden sheets. I gave him a quick nod and made my exit, but not before he grabbed my soft cock as I passed him and snarked in his high pitched voice, "Come back when you have a hard-on Mr. Softee."

What the fuck, I wasn't going to find pussy in the laundry if Franz was down there showing the fag hags how to fold a long sleeve shirt. I got in the elevator and pushed my floor's button, but I thought better of it when it was too late and hit the top button marked PH for Penthouse. What the fuck is a "Pent" and Penthouse is one word, not two. Maybe the PH stood for Hot Pussy or Pussy Hot, maybe neither, my mind was running in circles. The old elevator door squeaked opened at my floor but I didn't get off, the door slide open, I waited and then it closed and the old elevator began its crawl up past the 6th, the 8th and arrived at the 10th floor where PH was neatly printed on the inside of the elevator door.

I was't ever up there before and I was surprised to find not one but two small penthouses backed into each other. One was under reconstruction, paint cans, yellow tape and warning signs made it obvious it was not Olga's. That left the other Penthouse which looked neat and orderly from the outside and had a screened in patio area. I figured that must have been the right one so I rang the doorbell and heard what sounded like Olga's voice shouting through the old metal door, "Wait, I'm coming." Me too I hoped.

Olga opened the door a crack and looked through the chain, she wasn't taking any chances.

"It's me, Henry, just dropped by to see how you've settled in."

"Oh yes, just hold on a sec," I thought I heard some whispers but perhaps it was just the breeze. Even on a calm day the air this high up was fresh and vigorous. "Oh come right in," she whispered, unchaining the door. "So nice to see you."

She led me into a small living room. I realized she was taller than I'd remembered, about my height. She was wearing fuzzy slippers and a white bathrobe. She had wide shoulders, long blond hair and graceful legs, almost like a ballet dancer. Her waist was narrow, making her breasts and buttocks seem rounder. Her face was tan with a tiny discoloration along the jawline. Maybe the result of teenage acne being treated with dermabrasion. She still had the graceful movements of a young women although I guessed she was at least thirty five, maybe a few years more. New York women are good at hiding their age. She put her arm around me and escorted me into the living room. Seated me on a couch next to a large window that provided a view all the way to the West Side. I could see a little blue of the Hudson River and the rest of the old New York skyline up to where the High Rise Buildings blocked the river. A few modern buildings and some still in construction adding a busy energetic air.

"You've got a nice view, from my apartment all I can see is a dark courtyard and a bunch of garbage cans." She laughed, a deep throaty laugh that gave me hope. Olga's bathrobe lacked a belt, she held it together with her right hand, I could see she was nude underneath.

"Can I offer you a drink, I've got an 18 year old Scotch and a bunch of different vodkas."

"Scotch on ice is fine, thanks."

"Do you mind if I join you, I could use a drink myself."

"Of course not."

She disappeared for a few minutes, I could hear the tinkle of ice against glass as she came back into the room carrying a sparkling cut glass whisky tumbler in each hand. Her bathrobe opened as she carried the glasses revealing her body from her cleavage to her pussy, the view was splendid.

Realizing I was taking in more than the skyline she put down the drinks and pulled her robe closed.

"My, my, you are getting comfortable," she commented, staring at my erection which looked like I'd stuck a zucchini in my pants.

"Those are sure tight fitting jeans."

"I'm so sorry, please excuse me, I'm a man and I find you very attractive. I'm terribly embarrassed."

"Oh, don't give it a thought, I'll take it as a complement."

We sipped a bit of the Scotch, it tasted of smoke and peppery spices and although it was smooth to the throat, oddly it did sting the tongue. I looked around the room and my eyes focused on a fairly large abstract phallic sculpture that sat prominently in the center of the coffee table on a thick granite base.

"Oh that's a house warming gift from Jacob Darth, he's a well known sculptor, I like it but it's a little gay, don't you think?"

"Not really, I kind of like it, I mean it looks like a cock that seems to be going in three directions, what could be wrong with that?"

"Well, that's one way of looking at it," her expression became thoughtful, then her jade green eyes stared into mine.

"So Henry, tell me how you have been, no, instead tell me about you. You live with that tall girl don't you, the one who looks like a librarian."

I smiled, she had already checked me out. "Nothing much to say, I am a successful cartoonist, still clawing my way to the top. You've probably seen some of my cartoon art, the "New Yorker" has bought quite a few and some of the Men's magazines which you probably don't read. I've written a few unpublished, as of yet, novels, but I only have the rejection slips to show for them, they fill the little brass mailboxes down stairs. On the other hand, a collection of my cartoons will be published this spring."

"I probably have seen them, I read the New Yorker from cover to cover. But I'm curious, what do you write about?"

"Oh just the usual, Manhattan night life, boy meets girl, girl meets girl, guy fucks guy, just the stuff of our everyday swim in the gutter."

She picked up on that right away, "are you bisexual?'

"No, not really, I once tried that road but I don't think I'm suited to it, too much of a tight ass."

She smiled, "That's too bad, I like adventurous men"

"Well, life isn't over, what about you?"

"I prefer women to men but," and her green eyes lit up and a wrinkle appeared on her brow as she spoke in earnest, "but let me tell you, a real cock is a treat, I really enjoy one every now and then, like a fine wine or a deep drag on a hashish pipe."

"Wow, you have no problem telling it like it is, do you?"

"No, I don't."

"Would I be too gosh, Henry, if I asked you why you really came up here today, were you hoping for more than a handshake?"

My face grew red at that.

Olga rose from her settee, the white shaggy bathrobe fell from her shoulders and she came across the grey shiny silk Persian rug and seated herself right next to me. I could feel her warm breast rub up against me.

"Let's see why you came up here today to see the Olga."

She handed me my glass from where I'd left it on the glass table, "Drink up little man, you're going to need it."

She placed her hands behind my neck and pulled me toward her. When our lips met she nibbled my lower lip as her hands unbuttoned my shirt and unbuckled my pants belt, then the zipper.

"Oh, no underwear, Henry you are a bad boy."

She pulled me on top of her so my face crushed her breasts which smelled from what must have been Channel #5, the ideal perfume for a sophisticated mature woman. Her nipples were red and thick, her breasts large and firm, I tried to maneuver her into a missionary position but she rolled over onto all fours and with her left hand reached out and grabbed my cock, pulling me closer to her hips and inserting my erection neatly into her warm wet vagina.

"Slow Henry, go slow, I want to enjoy every minute." I clasped her waist tightly, then her breasts and began to pump in and out, then grabbing my cock's root I began rotating it to touch every part of her vagina. At this point she fell forward. My legs were still between hers as I kept pumping slowly, but every now and then I strained forward, pushing as deep as possible into her. Little by little my cock telegraphed my balls that it was time, and then I straddled her ass so my balls were rubbing against her thighs and like a shooting star, my cock would no longer obey me and shot my load, filling her with a good ten days of my sperm. When I sensed she was ready I slowly withdrew as some cum leaked onto her thighs. As we separated she leaned over me, kissed my forehead and said, "Rest darling, rest, we are not done yet."

I must have dozed off for five or ten minutes and when I awoke, I realized I was reclining on the floor and my head propped up, resting on Olga's soft breasts and my nose was filled with the odor of her perfume. Realizing where I was took a moment and then I heard light footsteps on the carpet, I opened my eyes and looked in their direction and there behind the table was a tall black girl, her skin was a reddish ebony color, her dark hair cut short emphasized her exotic cheekbones. She was nude except for a pair of knit tight shorts and red leather high heels covered with little metal spikes. She must have been in her early twenties with small but exquisitely formed erect breasts, a long graceful neck, and her shorts did not mask a generously curved swollen posterior that would have made a Sulton proud to have her in his harem. She moved silently and I could not make out her legs as the table was blocking my view and Olga, who was obviously awake, noticing my head move, whispered in her husky voice, "That's Naomi, she's staying with me for the weekend, in fact we were in bed together when you rang the bell."