Wolf in the Fold

                                             Wolf in the Fold




         In retrospect the whole thing was an amusing blunder, even though I did not see it as anything other than failure at the time.  Still, there was a lesson learned.  Of course, hindsight is twenty-twenty.  And considering this, if I had a chance to do it again, knowing what I know now, I most certainly would.
         I love women.  I have ever since I can remember.  In fact, one of my earliest childhood memories is playing doctor with the neighbor girl, Katie.  I’ll always remember how our tight-lipped kisses would produce a prepubescent stiffy in my pants. And to this day I love most everything about women:  hair, smell, hips, breasts, lips, and Pussy...especially the Pussy.  I don’t just love It as a wet, musky pleasure center, or a gateway to life, or death, in the sense of the way men surrender themselves under its power.  No, there is something more, something mystical and illusive in the gently mounded labia and vaginal folds.  Though I have been with many women, my understanding of the power they have over me remains illusive.  It is for this reason that I could never marry.  I could not be with one woman without straying from time to time.  I want to be with all women!  And I admit this not because I have noble aspirations of staving off a doomed marriage, or because I am concerned with the consequential anger, sorrow, and revenge of my partner.  No, this is sheer selfishness.  You see, I imagine I will always love women, even though I will never understand them.  That’s not to say I haven’t tried. 
         Several years ago, I began dressing in drag.  I rationalized that in order to understand this mysterious power, I must first understand women.  How better to gain understanding than to walk in their shoes, no?  Upon gaining this understanding, it reasoned, I would discover the answer to their mysterious power over me, the power of the Pussy.  Though I found I felt quite comfortable in women’s clothing, cross dressing did not ease my obsession of discovering women’s deepest secret.  After the initial frustration of the lack of enlightenment, I decided to give my experiment more time.  After all, since I was not born a woman, it would take some time to discover their secrets.  Over time, I got fake breasts, assorted wigs, and became proficient at applying make-up.  In fact, I became so proficient at it; I did not look like a man in drag, but more like a handsome woman.  I looked good too.  No one would be able to recognize I was a man.           Now, do not get the wrong idea.  I am a man and I want to remain one.  I have a cock and I enjoy using it.  I’m not rainbow either.  The fact is I never left my apartment in drag.  When I dressed as a woman, I did so only in an attempt to gain further understanding of women, as I said before.  I have never told anyone about my cross dressing until now.  And though I’m as comfortable with that part of my past as I am telling you this today, I still feel a bit of, how shall I say… self consciousness.  Anyway, two or three nights each week I would stay home dressed in lingerie, or an evening gown, or a skirt and blouse.  These nights would be spent drinking chardonnay, watching chick flicks, trying to touch my feminine side, hoping for a moment of clarity and understanding.           
         
One day at the office, a couple of co-workers asked me if I wanted to go out carousing with them after work.  They were in their early twenties, a couple of years younger than I.  Neither of them appreciated the gift women had like I did. 
“Hey man,” said Steve.  He was a tall, blonde, frat boy, jock wannabe.  A nice enough guy, though a bit of a meathead.  “Scott and I are gonna check out this new club downtown.  It’s supposed to be wall-to-wall babes.”
         “Yeah buddy,” Scott added rubbing his palms together.  He was short with perfectly cropped dark hair.  His beady squinting eyes sparkled like a mischievous rat.  He was one of those sales guys; you know the type, just way too eager to be your pal. 
         “I can’t.”  I took a sip of coffee.  “I’ve got plans for tonight.”
         “That’s cool,” Steve said, “maybe next time.”
         “Yeah, let me know next time.”
         “You got it buddy,” Scott blurted.  “We’ll go do a little recon tonight.  We’ll let you know how it went.”
         “Great... great.”

         That evening I had just put on a long blonde wig, one of my favorites – so soft and luxurious, and was about to slip into a white teddy when the phone rang.  It was Jill, a friend.  “What are you up to?”  She asked.
         “Not much.”
         “I’ve got a good show for us to see.”
         “You want me to come by and get you?”
         “That would be great.”          
         “Okay, I’ll see you in a half hour.”
         I met Jill my senior year of college.  I was watching this punk band tear it up.  They were really good, old school stuff, raw, tough, and angry.  Not at all like the run-of-the-mill-pop-offshoot crap you see and hear today.  Anyway, the band finished their set.  I managed to find a seat at the bar.  I ordered another beer, rolled a cigarette of Drum tobacco.  Lit it.  This girl walked up to me.  She had a tall green Mohawk.  Christ, it had to be a foot tall.  Combat boots and black fishnet stockings, a black bodice and a vinyl mini skirt was all that covered her firm, young body. 
         She got her beer and turned to me.  Her green eyes were brilliant.  Glittering, sparkling, whatever you want to call that energy, that life.  Her delicate tongue peeked out and daintily licked the beer foam from her burgundy lips.  She reached over, took the cigarette from my mouth and began to smoke it.  I danced in those green eyes for a moment.  She leaned forward to my ear, saying matter-of-factly, “You want me to give you a blowjob, don’t you?” 
         “Yeah,” I replied with a splitting voice, “right after I’m done licking your pussy.”
A mischievous grin spilled across her face.  We shared the rest of the cigarette.  “It’s a bit unnerving, isn’t it?”  She asked.
         “What?”
         “Meeting like this.  I mean, we could go somewhere and rut like alley cats, but still....  It’s like offering your throat to the wolf.”
         “The ancient Romans said, ‘The Fates lead him who will.  Him who won’t, They drag.’”
         “I don’t know if it’s will or fate.”  She took a sip of her beer.  “I don’t know that it matters.”
         I sat silently for a moment before finally asking, “What’s your name?”
         A sly smile crossed her face.  “Does it matter?”
         I bought her another beer.  I figured she was hustling me for drinks, but I didn’t care.  I was tall and lanky.  Still am.  She was beautiful, funny, and talking to me. 
         “You like to get high?”  She asked.
         “Yeah, sure.”
         “I’ve got some good schmee back at my place.  It’s not far from here.”  We finished our beers and left.
         We walked into an old brick building with metal fire escapes zigzagging down the face of the building.  I don’t know why, but I always wanted to live in one of those buildings.  I’m not certain what romantic idea I have about them, but there is a subtle comfort about them for me.  Perhaps it’s the easy escape out the window, from any situation.
         I followed her tight round ass up three flights of stairs, sneaking peeks up her skirt at her black satin panties the entire way.  She opened the door to her large studio apartment and turned on a lamp.  The walls were exposed brick.  There were paintings and other objects scattered about the room, some finished, others still awaiting final inspiration. 
         “Make yourself comfortable,” she said. 
I took a seat on the futon.  She dropped a tape into the cassette deck, and pushed play.  The room filled with the sound of some obscure punk band I had never heard of, they sounded like gypsies on acid.  She then opened a tool box on her work bench and pulled out her stash.  After packing a bowl she lit some incense, and then walked over in front of me.  Christ, she had an incredible body.  Still does.  She took a deep hit off the bowl, and climbed on the futon, straddling me.  She bent forward placing her mouth on mine and blew smoke down to my lungs. 
When the bowl was finished we were kissing passionately and articles of clothes slowly began to come off, one at a time.  I eased her back on the futon, kissed down her neck to her breasts, licked her pierced nipples, and then traced a lazy line with my tongue over the lizard tattoo on her belly to her wet panties.  After a couple of teasing licks through her panties, I peeled them off and dropped them to the floor.  I leaned in toward her raven mound of pubic hair.  Her sweet musky scent filled my nostrils as my tongue explored her buttery Pussy causing her to writhe in pleasure.  I took my time and made certain I did not neglect any part of her labia or clitoris.  Before long she was gasping rhythmically as she thrust herself harder and harder on my tongue.  She was deliciously wet with tangy juices.  She wrapped her hands around my head and bucked harder and harder against my face letting out escalating moans and squeals.  After she came, she had me lay back and wrapped her beautiful burgundy lips around my juicy comestible.  She licked and sucked until she finished me off.  We cuddled together, tired, drunk, and high, and eventually fell asleep.
         We dated for a few months after that.  But we never moved in together or anything.  She needed ‘space’ for her work.  I was fine with that.  I said I understood anyway.  I was not certain I was comfortable with the idea of being together all of the time.  I loved her, and wanted to keep loving her, but I was afraid if we pushed a good thing it would break.  It reminded me of an old science teacher from high school who reminded us almost daily, “Kids, you can’t force glass.”  In following that advice, we continued to see one another regularly.  We have become loving friends, and the sex is as good as ever.

         I arrived at Jill’s building.  She still lived in the same place.  I climbed the stairs to her door.  She greeted me with a smile and dancing green eyes.  Her hair had grown to shoulder length and was colored red, matching those luscious burgundy lips.  She wore a short skirted summer dress and combat boots.  Her place still had half-finished projects scattered through it.  But her work had gotten much better over the years and she had recently gotten to the point where she was making enough money from her art work she was able to quit her job. 
         When she was ready we walked hand-in-hand a couple of blocks to the club.  Along the way, she told me about her next art show.  “It’s going to be great.”  She smiled.  “They are showing just my work for a month.”
         “That’s fantastic.  When does it open?”
         “First of next month.”
         “Will there be free wine and beer?”
         “I don’t know.”
         “I’m not certain I can make it.”
         “Shut up you ass.  Put it on your calendar.  You’re coming.”
         I opened the door to the club.  Let her in.  There was a big biker dude sitting on a folding chair collecting the cover.  I paid.  He stamped the backs of our hands and then we serpentined our way through a sea of colored hair, piercings and black and plaid, to the bar.  We found a couple of stools and ordered a pitcher.  I rolled a cigarette while we waited.  I lit it, took a drag and turned to Jill.  She reached over, gently took it from my lips and put it to hers.  I poured a glass of beer and handed it to her.  “Congratulations on landing the show, baby.”
         “Thanks.  It’s exciting to see years of work starting to finally pay off.”          
         I nodded and gulped some beer.  “I know.  I’m really happy for you.  It’s good to see this happening for you.” 
She smiled a giddy school girl smile.
         A tall woman with straight black hair, bangs to her eyebrows, approached the bar next to me and ordered a rum and coke.  I glanced up; catching her brown eyes for a moment, then saw her full, pouting lips stretch to a sly smile.  I turned to Jill.  She had noticed the woman too. 
“Roll another cigarette.”  Jill patted me on the knee.  I pulled out the pouch of fine moist tobacco and the papers, and started to work on the bar.  The tall woman left.  “She was hot, wasn’t she?”  Jill’s question took me off guard.
         “Who?”
         “Oh, Christ!  The brunette that was standing next to you.  I can’t believe you are going to try to tell me you didn’t notice her.”
         “I didn’t pay much attention.”  I put the cigarette in Jill’s mouth and struck a match for her.
         “Yeah, well I did.”  She blew smoke through her nose and gave me the cigarette.  “She’s hot.  I’d go home with her.”
         “Yeah, right.” 
         “What?  I’ve been with a woman before.”
         “Really?”
         “Yes.  Twice.  And I’d do it a third time if the right woman came along.  Maybe one like her.  Maybe her.”
         “Okay, wait.  I’m getting a boner.”  I quaffed some beer.
         “I suppose you think you might like to get in on that action too?”
         I didn’t answer.  I drank beer.  Me and Jill and the brunette?  Two beautiful Pussies to taste.  What if I couldn’t  handle it?  What if I went mad?  I decided to throw caution to the wind as there is only one way to find out.  “I’d give it a try, but it’s your call.” 
Jill smiled sheepishly and drank her beer. 
         The first band came out.  They were fast and loud, pretty good.  When they finished the set Jill went to the bathroom.  I got us another pitcher and rolled another cigarette. 
Jill returned to her stool.  “Guess who I ran into?”
         “Who?”
         “The brunette.  She’s not interested.”  Jill took the cigarette.
         “What did you say?”  I was really curious.  How does a woman pick up another woman anyway?  Certainly, they have to be more gifted at it than us men with our clumsy pick up lines and such.
         “I said, ‘My friend and I are having sex after the show and we were wondering if you would like to join us.’”
         “God, I love the direct approach.  What did she say?”
         “She said, ‘Sorry, I don’t do men.’”
         “No way!  Shit!  What a drag!”
         “Don’t worry.  I still got her number, just in case.”  Jill’s lips stretched across her face curling up towards her cheeks, letting her teeth show.  She gave me the cigarette and turned to her beer.  She was amazing, simply amazing.
         By the time the second band finished their set it was midnight and we had a good buzz on.  We went hand-in-hand, skipping at times, back to Jill’s place.  She lit candles and incense.  We got naked.  I went oral on her until she came a couple of times.  Then I plunged into her, like a ship pitching through waves, as she held me tight with her vice-like legs.

         I got to work late the next morning, feeling a bit sluggish and sick.  I went to the cafeteria for coffee and ran into Scott and Steve. 
“Hey buddy,” Scott said.  He was loud and gregarious.  “You gotta hear about last night.  It was hilarious.  Okay, so we’re hitting the clubs, checking out the hotties.  We got to this one place, the Cactus Club, on thirty-second and Washington, and there is nothing but babes in there.  I’m sure we were the only two guys.  You know what I’m sayin’, right dude?  So, we’re getting a good buzz on, then Steve walks up to this little hottie and says, ‘So, do you like to smoke hogs?’”
         I looked at Steve.  Beneath his right eye the skin was light purple and swollen.  He shook his head.  “It was a bad idea man.”
         “What happened?”  I grinned.
         “She threw her drink in my face and beat the shit out of me.  I mean, I couldn’t punch her with her being a woman and all.  Besides, how would it look if I hit a woman because she wouldn’t, ‘smoke my hog.’  So I just had to take it until her friends pulled her off and Scotty got me the fuck out of there.”
         “You should think about getting some eye shadow.”  I replied.  “Purple is a really good color on you.”
         “Fuck you,” Steve retorted in disgust.
         “Smoke my hog,” I teased with a grin.
         I returned to my desk, but had difficulty concentrating on my work.  Scott and Steve, of all people, tripped the trigger of inspiration in me.  What if I went to the Cactus Club, dressed in drag, to pick up a woman?  This idea excited me.  I daydreamed of eating pussy that had never been plundered by cock.  My work suffered as I began writing notes for my scheme, all the little details necessary to bring this plan to life.
         Upon returning home from work, I drew a bath filled with fragrant salts and oils.  Lit some candles and poured a glass of chardonnay.  I shaved my face, arms, armpits and legs.  Relaxed in the warm water, I sipped wine, mentally running through my plan.  When satisfied the plan was flawless, I got out of the bath, dried off and sat on the edge of the tub to paint my toenails in candle light.  As my toenails dried, I pressed false fingernails on and painted them.  I blew out the candles and went to the bedroom. 
I hooked up my bra - 34c with falsies in.  I pulled up my panties, wedging my package down as best I could, then put on a pair of jeans and a teal crew neck too.  I stepped into sandals.  In my excitement I nearly forgot the toe ring.  Then I turned to the mirror and began to apply the make-up, first a base, then a little blush.  I had this eye shadow, I don’t remember where I found it, but I loved it.  It was a soft, subtle greenish blue that really drew out the blue in my eyes.  I brushed out long, thick lashes with the mascara, and then added a soft, dark pink lipstick.  Finally, I donned my blonde wig.  Tossed the shoulder-length hair about until I was convinced it looked natural.  I took cash out of my wallet; there was no sense in taking ID or anything.  I put the cash in my purse with my keys.  I got to the door and stopped.  I wiped my palms on my pants.  I took a couple of deep breaths, trying to slow my heart as it pounded in my throat.  My mouth was dry.  I grabbed the doorknob, took another deep breath.  Then, for the first time, I walked out of the privacy and sanctity of my apartment in to public, dressed as a woman.  Silently praying not to see anyone I knew, I began my walk to the Cactus Club.   
         I was nervous, so incredibly nervous I thought I might vomit.  Imagine if a neighbor or a co-worker saw me, and recognized me.  The embarrassment and the humiliation would be unbearable.  Still, the thirst, the hunger for the hunt overruled these anxieties and I pursued my interests, and I continuously reminded myself of how good I looked as a woman.  As I walked I found my fears of being in public dressed as a woman soon eased.  No one paid any attention to me as I walked along.  It was strangely liberating.  I became more relaxed as I was able to roam the streets of the city known to no one.  A false sense of adventure perhaps, but I was lost in new found excitement.  The streetlights were coming on along Washington Avenue as I continued another block to its intersection with thirty-second street.  I took a deep breath outside the Cactus Club, and then opened the door letting myself in to be the lone cock disguised as another steaming pussy. 
         The Cactus Club was rather small for what I expected of a club.  It had a dance floor which took up half of the floor space.  There were tables here and there.  The place was half full with nothing but women.  Perfect.  I took a seat at the bar.  The bartender approached.  She was butch and gruff and should have been wearing a flannel shirt to completely fit the stereotype.  I ordered a chardonnay and casually observed the ladies in the club through the mirror behind the bar as I twisted a finger through my hair.  They were all different types: young, old, fat, skinny, needy, secure, butch, feminine, long haired, short haired.  It was fantastic.  I was excited to pick one to move in on, but reminded myself to be patient.  I knew the right one would reveal herself as long as I did not try to force something that was not meant to be.
         I had just about finished my glass, twisting my hair with a finger, when a tall, thin woman in a white blouse and khaki pants sat down on the stool left of me.  She ordered a chardonnay.  The bartender asked me if I would like another as well.  I finished my glass and nodded.  I glanced to my left at her.  She was late thirties to early forties.  Broken in, but not broken.  She had brown eyes and light brown hair hinting gray at the tips.  We made eye contact and smiled coyly. 
“Hi.”  She said.
         “Hi.”  I replied discretely.  The bartender brought our wine.  We sat silently for a moment.  I was beginning to feel awkward. 
         “I hope you don’t mind my asking, but...”  I turned to her.  She continued in a thick Long Island accent.  “I’ve never seen you here before.”
         “I’m new here.  I moved to town about a month ago.”
         “Really?  Where from?”
         “Detroit.”
         “So, how do you like it here so far?”
         “It’s been great, but I don’t know anyone.  So it gets a little lonely at times.”
         “Oh, so you moved here alone?”
         “Yes. I thought it was for the best after my partner and I split.”
         “I’m sorry to hear that.”
         “Thank you.”  I gave a weak smile and took a sip of wine.
         “I would be happy to show you around.  It’s always nice to have a new friend.  I’m Eileen.”  She extended her hand. 
         I was momentarily taken aback with the offer of a handshake.  But, I smoothly gripped her hand lightly, careful not to shake like a man.  “I’m Samantha.  Nice to meet you.”
         We chatted over a couple glasses of wine about places to go in town.  As I was new to town, she told me where all the good dyke bars were.  Once she was done telling me about them, a tense silence fell over us.  We glanced at one another and traded coy smiles.  It didn’t take long before I could not stand it any more and I asked her, “What do you do?”
         “I run a small art gallery celebrating women artists and their work.”
         “Oh, how interesting, I always wanted to do something like that.  I’ve just never had the guts to try.”
         “You can do it.  You should just consider going for it.  It is a lot of hard work, but the rewards are both tangible and intangible.”
         “Intangible?  Like what?”
         “Like the enrichment you get from learning from others art.  And there is nothing like being your own boss.”
         “That’s what I’ve always wanted, to be my own boss.  What are you showing now?”
         “Right now I’m showing pottery and sculpture by an artist here in the city.  Most all of the work I find is here in the city.  There is a lot of talent around.  I don’t have to look very far.  Anyway, the pottery is unique in design.  And the sculptures’ theme is about moving foreword with women’s rights.  It is very good, very powerful work.”
         “It sounds great.  I would like to see it sometime.”
         “Well,” she took a sip of wine.  “I don’t normally do this, but if you like we could go over to the gallery and I’ll show you around.”
         “I would love that.”  I smiled.  “Are you sure you don’t mind?”
         “Not at all.”  She smiled.  We finished our wine and left for the gallery. 
         A thought occurred to me as we walked along.  I wondered, if I were able to seduce a lesbian while dressed as a woman and was able to perform oral on her, would that deception qualify as rape?  She was interested now, but certainly she would not have a sexual encounter with me if she knew I was a man.  It was not like I slipped her a mickey and forced myself on her.  But still, it seems such a fine line when using such a deception.  I continued mental debate as we walked along.  I felt no guilt for what I was attempting to do.  Nothing would be forced.  And you can’t rape the willing.  Besides, she would never know the truth that I am actually a man.  And who knows, if she did find out, she might decide she likes men.
         We entered the gallery through the back entrance.  It was small and tidy.  Eileen was not kidding about the work on display.  It was impressive.  The sculpture illustrated women’s’ struggle in a patriarchal society, offering me more insight to women than my cross dressing ever could.  The angst, the power, the passion, it was nearly overwhelming.  “This is great.”
         “Thanks.  You should come next month.  There is a wonderful local painter, Jill Davies, whose work will be on display next month.”
         Shit, Jill, I thought.  What are the odds?  I turned to a piece of pottery while trying to maintain my composure.  I could feel my eyes bugging out of my head.  A moment later I was able to turn back to her with a smile.  “Oh, I’ll be here for it.” 
         She led me to a back room.  There she turned to me and without saying a word, kissed me.  We kissed for a bit.  My hands slid around to the front and began working her belt.  With that undone, I popped the button on her pants, and then slowly, yet smoothly, lowered the zipper.  Her pants dropped to the floor.  She stepped out of them.  I helped ease her to the floor.  She took off her panties, revealing her warm, moist snatch.  She gasped ever so slightly as I kissed her inner thighs.  The gasps turned to moans when my tongue found its target.  This was fantastic, a dream come true.  I could feel my cock grow hard against the floor as my tongue worked her to a fevered pitch.  She writhed on my tongue for quite awhile.  She held the back of my head as she bucked into my face.  Finally, she tensed and screamed. Then she relaxed, taking deep, slow breaths.  I rose to a kneeling position.
         “That was....”  She opened her eyes.  I did not realize my wig had slid to the side a bit.  “What the hell?”  Her face wrinkled.  She saw my hog bulging through my left pocket.  “Fucker!” she yelled and kicked my groin. 
A jolt ripped through me.  I fell back on my ass trying to catch my breath.  Eileen got up and moved to me.  Towering over me, she pulled the wig off my head and threw it at me.  “What the fuck kind of freak are you?”  She drove her fist into my right temple.  White sparks showered through me.  “Get the fuck out of here or I’ll call the police.”  She opened a door to a small office, picked up a can of mace and began shaking it. 
Still stunned, I managed to push myself to my feet and ran out the back door to the alley.  No one was around.  I ducked behind a dumpster and took a moment to collect myself.  I felt the side of my head.  It was swelling, but not bloody.  Realizing I had left my wig behind, I knew I could not walk home like a woman.  After a short debate, I took off my fake rack and reluctantly through it all in the dumpster.  After wiping off my make up as best I could, I cautiously entered the pedestrian thin sidewalk to begin my way home.  I was very self-conscious, and tried to stay in the cover of shadows as I went.
         When I finally got home, I opened a beer and sat on the couch.  My balls throbbed.  My head throbbed.  I leaned back and placed the beer to my temple.  I could not believe the night finished so disastrously.  I did eat Eileen though.  Eileen.  Christ, what was I to do now?  I still had make-up on when Eileen saw my face.  But it was just make-up, not a mask.  I thought, rolled a cigarette, and drank some beer.  Then I realized I had two weeks to try to grow a beard and change style and color of my hair before Jill’s opening.
         A great sense of futility descended upon me as I realized dressing in drag brought me no enlightenment.  I opened another beer and decided to get rid of all my women’s clothes, the panties, the dresses, the teddies, all of it.  They were no help with understanding women.  What I understood then was the simple fact that I am a man, and because of that, I will never understand women.  I’m not supposed to.  Some mysteries are best left unsolved.  I just love Pussy.  And knowing that will have to be enough.