| DEVIL WITH A BLUE DRESS ON
A "Transgendered Adventure" by Web Dazell
"ADVENTURE (noun): an unusual and exciting, often hazardous, experience
Welcome to the second in my new "Adventure" series. My two
previous series "The Arrangement" and "Breaking the Arrangement"(which will
continue) were autobiographical. Everything in them is based on what
actually happened to me as I was growing up. While reliving these
experiences was enjoyable, as a writer it was also frustrating because of
the need to be faithful to what really occurred and not embellish events.
The "Adventure" series has no such restrictions. While some of the
series may have a kernel of truth at their heart, in the main they are pure
fiction, a chance to my wings as an author and go where my lust and
imagination (as well as reader requests) take me.
However, HOW MANY ADVENTURES ARE POSTED ON THE WEB AND HOW OFTEN THEY
ARE POSTED WILL BE IN DIRECT RELATION TO THE NUMBER OF EMAILS I GET AT:
firstname.lastname@example.org. The more (and more detailed) the emails, the more and
quicker will appear. So now that everyone understands the rules,
let's sit back and let the "Adventure" begin.
OK, before we start with this we need to get one thing straight.
Despite what you're about to read, I'm not gay. OK, maybe that's two
things straight, me and my sexual preference. In fact, I'm so not that
one woman, even one as beautiful as my wife, just doesn't do it for me.
That's how I got in this in the first place.
No, I'm not saying it's my wife's fault. She really has nothing to do
with this except for the fact that sometimes she's just too good
looking. I know that sounds like a strange complaint "Hey, my wife's too
attractive," and a problem a lot of would like to have but none the
less it's true.
Screwing a beautiful woman day after day is a lot like eating a rich
dessert meal after meal. Sometimes all that lusciousness gets cloying and
you just want to chomp down on a handful of potato chips to cleanse your
palate. That's what those other women are to me, a handful of junk food
that restores my appetite for what I have at home.
So, when I need a change of diet and that happens more often than you'd
think, I go looking for whores. Not high-priced, hang around in expensive
hotel bars boutique courtesans. Or mid-range escort service companions.
Or even lower-priced massage parlor sex workers. I'm looking for the
ladies of negotiable virtue with the bargain basement prices. The
streetwalkers giving $10 handjobs, $20 blowjobs, and charging $30 to take
it up the ass.
I'm not after elegance or loveliness, I get enough of that at home. The
whole idea on these adventures is to get my rocks off with someone who
contrasts in almost every way from my wife. Mind you, butt ugly doesn't
cut it. I'm not going to stop and pick up a scanky-looking hooker. But
anywhere between plain and homely works just fine for me.
Age is another issue. I don't want a with a hard-edged body
and that would poke your eyes out. When I'm in one of these moods
older women with marks and sagging really turn my crank (in
more ways than one). And since my is white, I usually can't go wrong
with basic black.
I was driving along one of the downtown area streets known as a hotbed
of streetwalkers when I saw her on the stroll. On the opposite side of the
avenue, she was tall, dark, and, at least from the far side of the six lane
boulevard, appropriately coarse and blowzy looking.
In order to get a better look at the merchandise I turned around and
cruised back by her. Liking what I saw, I pulled the car over to the curb,
locked it (after all, this was far from the best of neighborhoods) and
began to walk toward her.
As I got closer my dick started to harden. She was wearing a silky
sapphire blue dress that was tighter than Scrooge McDuck, a strolling
commercial for the benefits of static cling. Its decolletage showed plenty
of cleavage, exposing the upper slopes of unnaturally rounded that
screamed "boob job." But that's all right. Like I said, I was after the
old Monty Python treatment, "And now for something completely different."
Her legs, bare from mid-thigh down to the "fuck me" pumps she was
wearing, were smooth and curvy. Above the knees she was a big-boned girl,
not fat but with some meat to her. Her shiny black hair was relaxed and
smooth, not kinky. Done up in a modified in a pageboy, it parted in the
middle, hanging loosely down over the large gold hoop earrings dangling
from her distended lobes.
Eyebrows plucked almost bare with blue upward arches at the outer edges
hovered above her brown eyes like a pair of demented Nike swoops. An
application of rouge only called attention to the bumpiness of the skin of
her face, bumps that the layer of powder she had applied didn't totally
cover up. Her broad, lips were slathered with carmine lipstick, a
color I thought would look great in a ring around the base of my cock.
In a low-pitched voice, one with that Janis Joplin too many cigarettes
and too much whiskey timbre to it, she asked me if I was looking for some
company, the tip of her tongue lightly brushing against her upper lip, a
small teaser of what was to be. Smiling, I nodded yes and then putting my
hand on her ass, guided her toward my car. I could feel the firm muscles
of her butt roll back and forth under my palm as we walked, making me sorry
I had neither the time nor the money to rent a room. I love buttfucking
cheap whores but it's not something you can do properly in a small car.
We went through the usual preliminaries: "Are you a cop?" "No, are
you?," negotiated over the fee for services rendered and then, following
her instructions, I drove my car down an alley. There, parked behind a hot
sheets motel and backed in between two trash bins, I dumped my load into
her wet mouth.
Now I've always been amused when I read these about how "It was
the greatest I've ever had in my life." For one thing, I'd be hard
pressed to pick out a single blow job as "the best ever." For another,
hummers in cars are a lot like eating McDonald's while driving. Quick,
sometimes messy and never nearly as satisfying as being inside taking your
Then there's the high anxiety quotient associated with automotive sex in
the city. Your attention is always divided between watching the head
bobbing up and down in your groin and watching out for anyone approaching
the car. You worry about whether or not someone will see you; whether
you'll get busted and the car confiscated; and, if you're going with a
hooker you don't know, whether she'll pull a rubber or a razor out of her
So these quickies in the car usually don't provide the ultimate in
sexual pleasure. But this one was pretty damn good.
As she cleaned up the last smears of sperm the removal of the condom had
left on my cock, I did something I rarely do with business girls, I gave
her a tip. Yeah, it was only a lousy five dollars but that represented a
20 percent tip above the money she got for blowing me and she seemed to
appreciate it, giving my crotch a little extra squeeze as she got out of
the car. And, with that, our transaction was through.
Two weeks later I found myself back in the city on business. While I
really wasn't in one of my "moods," I thought it couldn't to check out
the merchandise along the avenue. And there she was again, wearing the
same sapphire dress, wiggling her ass back and forth as she trolled for
johns. And so I pulled over.
This time we exchanged names. Her street name was "Andi." I told her
mine was "Dave." She said she had a new place we could go, one where we'd
both be a little more comfortable. Her new "special place" turned out to
be a loading dock at the back of a vacant factory. Designed to allow semis
to deliver their cargo directly into the storage basement, the roadbed
sloped down enough that the top of the car was well below the level of the
rest of the parking lot. You'd have to be looking directly down into the
dock to see any part of the car.
I let Andi take the lead. She began by wiggling out of the top of her
dress, her squashed leaping out from their silken confinement like a
pair of frisky puppies bounding out of a cage eager to be petted. Each one
looked like a half of a medium-sized brown coconut, the wrinkled nipples
resembling chocolate covered prunes. Thinking their shape was too regular
to be the unassisted work of nature, I asked if they were silicone or
I know the saying goes "Treat a lady like a whore and a whore like a
lady," but as far as I'm concerned that's just bullshit. You don't treat a
whore like a lady, you treat her just like what she is, a business woman
who's renting you her body in exchange for financial considerations.
Hooking isn't about romance and love, it's about commerce and business and
in business no question is off limits, no request is verboten.
Without taking offense Andi replied that they were silicone. As she
lowered my pants and underwear, she told me the pain and inconvenience of
the surgery was worth it every time she saw herself in a mirror; that Dow
Corning's gift to flat-chested broads helped make her feel more like a
woman should. As her hand stroked my erection, she asked me the natural
follow-up question, did I like them? When I replied in the affirmative she
used her other hand to guide my head to her tit. As I captured her nipple
with my lips, my nose was tantalized by a sweet green fragrance I had never
Andi was right, this new location did make me feel a little more
comfortable. I took advantage of the relaxed surroundings to pay more
attention to the woman in the car with me. I watched her hair fan across
my lap while I enjoyed the feel of her lips enveloping my manhood, the hard
vacuuming sucks on the up strokes, the scrape of her teeth on the
In turn I caressed her body, the rasping of my nails down her spine
drawing little moans from her busy mouth, my kneading of her buttocks
bringing them up off the car seat. It was only as I reached for her that she stopped me, explaining that I was the one paying good money to get
off. "Just enjoy letting me do my job Dave, you won't be sorry." Again she
was right as she coaxed another toe-curling orgasm from me.
Afterwards, as we were rearranging our clothes, I found out from Andi
the perfume she was wearing was called "Jai Ose." Unusually talkative for a
streetwalker, she explained how when she awoke from her surgery she had
found a quarter-ounce of this very expensive, very hard to obtain scent on
the dressing stand next to her bed along with a tag reading "New demand the very best."
Andi was never quite sure who had given her the perfume; it could have
been one of her "dates," might even have been her surgeon. Whoever it was
had hit a home run as Andi wore two drops between her every day. The
only problem is it was almost gone and she didn't know where she could buy
more; costly French perfume wasn't the type of thing you usually found in
the inner city "everything for a buck" stores she frequented. Maybe I
could help find some.
OK, I thought to myself as Andi told me the story, here we go again.
Giving her that tip the last time clearly was a mistake, now she's playing
me for a chump. It never pays to get personal with a nymph du pave, they
always want to use it to their advantage. Better to keep things on a
Andi looked a little disappointed as I dropped her off at her usual spot
sans any tip, but fuck her, that's what she gets for treating me like a
Two weeks later she beamed like the summer sun as she unwrapped a new
bottle of Jai Ose. Now a hooker's smile is like a greeting card, they have
one for every occasion and each of them is as artificial as the last touch
of makeup they put on before beginning their daily stroll. But Andi's
smile was the real thing, reflection of pleasure not cunning.
Yeah, I know I was going to keep this purely business but I stopped at
the HiLife convenience store after I dropped her off and used the five
dollars I was going to tip her to buy a Wild Wild Winnings scratch 'n win
ticket. Damned if I didn't scrape off a $100 winner. I'm a firm believer
in a lot of things, including the idea that the fates nudge us in the
direction they want us to go, if only we will listen. Well, I was
listening so I used the money to buy the perfume, which wasn't easy to
find. After all it really was Andi's tip money in the first place. I was
just sort of investing it for her.
On the same date I gave her the perfume she began to "talk game" with
me, telling me about her time as an streetwalker; nothing really personal,
just some of the "tricks" of the trade, what her other customers liked,
what the other were like. And then I asked the question.
"Andi, what's it like to suck a cock?"
"Oh, honey I'm not sure words can do it justice. It's something you
have to do to really understand what it's like."
"Try," I asked as her hand moved slowly up and down my erect shaft.
"Well, to begin with it 's fun. Doing a hummer on a cock is a turn-on for
the guy getting his boner and the one doing the sucking. Eating
some guy 's rod is a big kick for most cocksuckers and I 'm no different.
"Some will tell you it 's just like eating a popsicle. Sheeit,
ain't no way Dave. For one thing a popsicle is cold and a 's tool is
warm. They may both be hard but a cock has that elastic feeling; it 's got
some give to it like the padded handle of a hammer. And a dick is alive,
you can feel that while it 's in your mouth.
"Gotta tell you, I love the feel of a cock between my lips; the way its
weight presses against my tongue and the way it jumps up against the top of
my mouth as I lick it. Even if it 's a little soft there 's nothing as
good as the feel of a guy 's dick as it slides in and out of my mouth
unless it 's the same cock pounding in and out of my ass. And when you get
one in each end, Dave, it 's Heaven.
"It 's not just the physical stuff either. Blowing a guy and listening
to the sounds he makes is really neat. After I've been with a client
several times I can tell just by the noises he makes how close he is to
coming. I mean with you Dave, when you 're getting ready to shoot you
start breathing in these little short deep breaths, 'huh -- huh -- huh,'
and just before you squirt you take a real big breath and hold it until the
condom 's full of Dave 's baby-making juice."
Listening to Andi, who had continued to jack me off while she was
talking, had already brought to the edge of orgasm. Knowing that a few
more strokes of her hands would have me tumbling off the edge of that
cliff, I reached down and held her hand motionless on my throbbing dick.
"But doesn't the taste bother you," I asked, trying to concentrate on
anything but the tingling sensation where her hand rested. "I'm mean
that's why you've never given me a bareback right. We use these
damn condoms because you don't like the flavor."
"Nah, Dave. We use these condoms 'cause I'm AIDS-free and I'm going to
stay that way. Fact is I like the taste of cum. Got a lot of protein in
it, not to mention vitamins and minerals. I eat five or six a week
sometimes. Just depends on my customers."
Now I was insulted. I'd been a steady customer, even bought her the
perfume and she was treating me like a regular john, someone she'd picked
up off the street for the first time. My mood must have shown in posture
because Andi took her hand off my cock and instead placed it against my
cheek, her eyes locking with mine as though she was trying to read my mind
"I like you Dave, a lot. You're one of my special friends. And I'm
willing to give you special treatment. I'd love to your sperm and
I will. I'll even let you come to my apartment where you can cornhole me
and whether or not you wear a condom while you pound my ass is up to you.
But you've got to do some things for me." I waited for her to go on.
"Dave, as much as I like you and I do like you a lot, I'm not a charity
girl. I earn my living doing this. It pays for my food and my apartment
and my clothes. In a good week I can even send a bit of money to my little
girl." This was the first I knew Andi had a daughter, not that it made any
difference right now. "So, if we do go bareback, it costs a little more.
Not a lot but still more than I've been getting."
"I'm comfortable with that, provided you're not asking for too big of an
"Bareback's a $10 surcharge, Dave and believe me it's worth it." Ten
dollars wasn't a lot of money. I pissed five times that much away in
lottery tickets every week. And this ten bucks would buy me a sure winner
every time. I let Andi know the extra cash was fine.
"But that's not all Dave. There's more. I'm not looking to die on the
streets. I'm sure as hell not going to get AIDS just to make few more
dollars. I get an AIDS test down at county health the first Tuesday of
every month. It's free and I get the results back on Thursday. You've got
to do the same. And I've got to see the results, Dave. You show me yours
and I'll show you mine. That way neither of us takes any unnecessary
chances and we'll both be happy, healthy and wise."
"Andi, I've got to think about that for a little bit."
"That's fine Dave. I understand. It's not easy to show up every month
at public health for the test. Sorta gives away your private life, even if
you use a phony name on the paperwork. While you're think about that,
there's one more thing I want you to think about. If we're gonna exchange
bodily fluids on a regular basis you have to agree not to have sex, any
sort of sex including a handjob, from anyone other than me or your wife."
"Now just a minute Andi. I'm willing to pay more. I'm probably even
willing to get tested every month. But how come I can't have sex with
anyone other than you or my while you're still working the streets?"
"Dave, we've been out six or seven times now. You've seen how careful
I've been. I'm just as careful with my other customers. I don't gamble
anymore with my life than I have to. I'll trust you on this Dave. It's
not like the AIDS test. There's no paper you can show me proving you
didn't let some hard leg slobber the virus all over your rod between tests.
Your word will be good enough for me, I know you'll keep it. But you've
got to give me your word Dave. I don't want my little growing up
without one of her parents."
My cock had softened while we were talking, the once proud tower of
power now slumping over like a candle left in a south-facing window on a
sunny August day. Andi reached down and began to play steelworker,
bringing my limp dick back up to a full erection.
"This one's a freebie baby," she said as her hands rubbed me from top to
bottom. "And if you can't live with the conditions I've set we can still
see each other. It's just we'll always be using a condom.
"But Dave, think of the fun we can have if you do agree. Think of how
wet and warm my mouth will be without all that latex in the way. Can't you
just feel my tongue licking the underside of your dick; the roughness of my
tastebuds rasping along that blue vein of yours; the tip of my tongue
poking right into your pisshole trying to hold back that flood of come like
a finger in a dike and failing, your sperm gushing around it, flowing over
it, sliding down my throat to puddle in my stomach.
"And my ass. Honey, my ass is waiting for you. It wants your dick,
wants it bad. Think about the head of your dick popping past my sphincter.
I bet you can hear the whimpering sound I'll make when it pushes through.
I'm tight back there honey, real tight. And I can use my asshole to draw
your cock all the way in without your even having to push." At the thought
of finally buttfucking Andi, I shot so hard the reservoir tip on the condom
seemed to leap out from the rest of the condom like a hot air balloon
I gave Andi's conditions a lot of thought over the next two weeks. I
didn't want to catch AIDS any more than she did. Since I lived in another
county, I could give a fake name and address to the health department. No
one who mattered would ever know I was getting a monthly test for the
virus. But giving up sex with everyone but Andi and my wife. That was the
As good as she was, and she's plenty good, my by herself wasn't
enough to satisfy me. That's why I dated streetwalkers in the first place;
I got jaded doing just one woman, especially one who hated anal sex.
True, since our second date I hadn't picked up any hooker other than
Andi; hadn't really wanted to come to think about it. But how long could
this state of affairs last before the same wave of sexual lassitude washed
over me; before even reaming Andi's taut ass with an uncovered dick became
the same old, same and I was out looking for new thrills again?
Still, if the wanderlust, emphasis on the lust part, returned I could
always end my relationship with Andi. She was right about one thing
though; if I did agree to her terms I'd honor them. As long as we were
doing it bareback she wouldn't have to worry about me going out with
You expect important government papers to be printed on expensive
parchment, with glittering gold foil seals and elaborate red, white and
blue ribbons. A letter from the Publisher's Clearing House had more
pizzazz than my report from the county health department. Based on its
looks, the thin yellow copy of a triplicate carbonless form, a pale and
scratchy blue note at the bottom indicated I was AIDS-free along with the
time and date of my next appointment, could have been the receipt for the
repairs on my lawn mower.
For the first time, I had trouble finding Andi. She wasn't in her usual
spot when I went by and I checked at several different times over several
different days. Unless you have a phone number or an address, finding the
same hooker can be a hit or miss proposition; that's why a lot of us who
date go with a wide variety of girls, better odds that one will be
available when the urge strikes. But, whether it was a regular schedule or
just good luck, Andi had always been on the stroll when I looked for her.
Her absence from the scene gave me mixed emotions. I was worried
something had happened to her; I was pissed I had gone to all the trouble
of meeting her conditions only to have her disappear. And, underneath the
other two, my Greek lineage had me wondering if Klotho, Atropos, and
Lachesis weren't sending me another message, this time nudging me away from
this choice. Being sensitive to these little vibes, I made up my mind to
take one more run at locating Andi; I'd come downtown the next afternoon
and, if she wasn't to be found, I'd move on and give my business to someone
I'd driven about a half mile up the avenue when a flash of familiar
sapphire blue across the road caught my eye. Andi was descending from a
city bus. With the nearest turnaround four blocks away, it took some time
to cross the boulevard, time Andi used to disappear. After making several
unsuccessful passes up and down the street, I decided the way Andi had
vanished couldn't make the message any clearer, this one was over. On the
way back to the freeway, I pulled into the parking lot of a local bar,
intent on having a beer before I went back home to fuck the wife. Andi was
sitting on the third stool, nursing a Jack and water, her mood as sour as
the mash for her whiskey.
We sat together at a booth, getting slightly hammered while she told me
her story. Hearing her Lateesha had taken sick, Andi had gone to
see her kid only to have her estranged mate turn her away at the door. If
Mary, Andi's grandmother, hadn't been left alone with the child Andi never
would have gotten through the door. Except for Mary, Andi's had all
renounced her and, since in their opinion Andi wasn't a proper role for her child, they had cut off all contact. The money Andi sent to
Lateesha was funneled through Great-gramma Mary.
I agreed with Andi that it just wasn't fucking fair; that she loved her
daughter as much as anyone else, that she should be able to see her
daughter whenever she wanted, and through the front door, not sneaking
around through the alley gate.
I told Andi that she was right that she shouldn't be ashamed of what she
was and that she should be able to openly help support her with
the money she earned, no matter how she earned it. Money was money and it
spent just as well if you got it in exchange for cleaning a house or for
cleaning a man's pipes.
Before things got too maudlin, I told Andi of my decision, giving her
the yellow form and asking if she was interested in making some more cash
for Lateesha's school fund. With two quick swallows she finished her
drink, slid out from her seat and walked toward the door. I left the rest
of my beer behind as I scrambled to catch up.
Once in the car, Andi wasted no time continuing her lament about the way
her was treating her, pausing only long enough to take a hit from a
joint she had pulled from her purse. When she passed it to me I thought
what the hell and took a big drag. The shit was smooth, hookers do have
the best drugs. By the time we pulled down the ramp to the back of the
factory I had a very pleasant buzz on and Andi's mood had brightened
She apologized for not being able to go to the apartment right away.
She knew I was anxious to have her take it up the ass but her roommate was
home and she didn't like to bring her customers there without telling her
first. The feel of her fingers encircling my hard-on made me forget any
disappointment I had at having to stay in the car.
To provide lubrication for her efforts she bent her head down, hovering
about three inches above my cock, her open mouth allowing her saliva to
slowly drool out, descending in a silvery string to spread along the head
of my cock. As her hand picked up speed I took another hit from the joint
and then blew the smoke back into her mouth, our tongues dueling as they
met for the first time.
Laughing she pulled away from me and lowered the top of her dress. I
dove for her, inhaling the intoxicating scent of her Jai Ose as my tongue
played "Indians and the Wagon Train" riding around in ever smaller circles
until I captured her wrinkled cocoa nipple. I at it as though it
were a water spigot and I had just crawled in from the dessert.
Pushing me away, Andi's fingers returned to my cock, gently brushing
against the sides, fleshy feathers drifting down to the base. Just as
softly she moved her hand upwards, making little calming noises as I
reached for her, the tips of her fingers lightly squeezing the head. Her
hand retraced its way back down, her palm cupping my scrotum, rolling my
balls around like a gambler caressing a pair of dice for luck before a
Her nails wandered back and forth along the top of my groin, a jagged
edge catching on a stray hair before returning to my tumescence. Nails
scraping upwards left pale white lines in their wake, thin tracks which
turned within seconds. At the top she pinched the head, not hard
enough to really but hard enough to feel.
Then it was back to the base to restart the process, this time adding
pressure to her touch. My universe centered on my groin and Andi's
manipulations. Lazily she massaged my cock while I felt my balls fill with
sperm, pre-come starting to ooze from the tip. Andi tightened her grip,
slowly milking my dick, forcing more clear liquid from me. Now my pre-come
was trickling freely down the shaft.
With the index finger of her free hand, Andi harvested the glistening
fluid from the sides. When her finger reached the crown, she gave my dick
one more milking, distributing the pre-come onto her finger like a line of
toothpaste on a tooth brush. Smiling as she released her grip on my cock,
Andi moved her finger to hover at the outer edge of my lips. "Come on
honey, open up."
I looked at Andi in disbelief. She couldn't really want me to lick that
finger clean. Jesus, what'd she think I was, some kind of a faggot?
"Don't be a baby Dave. I know you're curious about how it tastes.
You've asked me often enough. Here's your chance to find out. It's just a
little pre-come, it won't kill you." Appalled I shook my head no.
"Come on sweetie, do this for me. Here I'll even make it easier for
you," she said as she wiped her finger against her nipple. "I know you
like to suck on these tits. Just pretend they've got a little salad
dressing on them."
Confused, I considered her offering. I did wonder what semen tasted
like, just as I wondered what it would be like to suck a cock. A nipple
coated with pre-come wasn't the real thing but it was a close as I wanted
to get. It's not like I was actually a cock for god's sake. And
that wasn't really on her nipple. Why not experiment a little?
Taking another hit off the roach to bolster my courage, I leaned forward
and, gingerly extending the tip of my tongue, made contact with her tit.
Expecting to be repulsed, I found my pre-come had very little actual
flavor. It was thick, just a shade below the consistency of glycerin, but
what taste there was wasn't unpleasant. It certainly didn't taste like
salad dressing, more like undercooked egg white than anything else. I
enveloped the entire nipple with my mouth, my tongue lapping her clean.
When I raised my head from her tit, Andi's finger found its way into
my mouth, this time without protest.
"There ya go Dave. I knew you could do it. How'd you like it? Did it
taste good? Want some more?" Busy licking the last remnants from the web
between her finger and thumb, I could only grunt my approval. "Yeh, I
thought you might like it. Be a good and later on you might get a
taste of the real thing."
After inspecting my janitorial efforts and finding them acceptable, Andi
returns her attention to my groin, dropping to her knees in the space
between the two front seats. Dissatisfied with the space available, she
had us move to the back; perching me on the seat so my balls dangle free in
the air while she positions herself between my legs. The joint moved with
Her broad tongue began to lave my scrotum like a bathing a
kitten. The touch of her without any intervening barrier felt wonderful. I
took another hit of the weed. Strong arms tugged me forward, pulling my
ass entirely off the seat; hunching over, I balanced on the small of my
back. It was an uncomfortable position. brown fingers pried my
buttocks apart. Andi's moist warm breath started to play against the crack
of my ass as her face descended, her tongue extruded outward. I took an
involuntary breath, more of a gasp really, as her tongue began to swab my
asshole. Impatient with the progress she was making, her lips attached
themselves to my rosebud like a leech, sharp stabs of her tongue forcing an
entry into my tight anal passage.
I shuddered with delight at the unexpected sensations this aroused in
me, each thrust allowing her to delve deeper into my ass, each thrust
giving a greater degree of pleasure. Uncritically, I allowed her to
replace her tongue with first one finger then two. I gave myself
completely over to Andi's ministrations. Eager student to her
knowledgeable teacher, obedient tourist to her experienced guide; willing
to learn what she wants me to learn, go where she wants me to go.
As her fingers began to fuck my ass, Andi's smooth mouth engulfed my
dick. The humid heat of her oral cavity was glorious; each lollipop lick
of my rod sending blue flames of tingling pleasure throughout my body; the
wet slick sounds of her fingers and mouth mingling with my moans of
excitement to fill the car.
Soon a third finger entered my ass to join its counterparts in their
massage of my prostate. As the sensations threatened to overwhelm me I
wondered what it would be like to have a real cock up there, to be
buttfucked by a in the same way I had sodomized so many women.
Reaching the crisis stage, my respiration came in short little pants,
"huh -- huh -- huh." The feel of flesh against flesh instead of flesh
against latex really was breathtaking. Recognizing the sound and what it
meant, Andi pulled back on my cock until just the head was in her mouth.
Then, instead of sliding up and down, she was rotating her entire head in a
circle using my dick as the axis. I could feel my balls beginning to boil
over and then I was shooting, wad after wad spurting from my dick into
Andi's eager mouth. As the sperm continued to pour out I felt as a rapidly
deflating blow-up doll must, shrinking with each spasm until finally I was
as empty as an airless balloon.
But Andi still wasn't finished with me as she crawled her way up my
body; her rubbing themselves against my khaki shirt; her cheeks
distended like a chipmunk carrying its winter forage. Her head level with
mine, she tilted to one side readying for a kiss. Obligingly I followed
suit. Our lips met and began to dock, mine open, hers opening. Expecting
her tongue, I was rewarded instead with my own sperm. I didn't pull away,
remaining in place until Andi finished emptying her mouth into mine, the
mixture of sperm and saliva covering the bottom of my mouth up to the top
of my tongue.
Whether it was the dope, or the sensual spell Andi had placed on me, I
wasn't not disgusted to find myself with a mouthful of my own seed.
Thoughtfully I swirled it around while Andi watched, scrutinizing me like a
horse player studying a tout sheet.
The taste shifted depending on which part of my tongue was asked. At
times it was salty, at other times coppery. Like my pre-come, there was a
hint of underdone egg white but the sperm seemed to have added an overtone
of raw oysters. It wasn't an awful taste, at times it wasn't bad at all.
You might even call it somewhat tasty, if you liked the taste of men's
As my throat worked up and down, Andi smiled as though she had just
opened a package contained what she had wanted for Christmas. "So, how'd
you like it Dave."
Trying to maintain my cool and regain some control of the situation, I
gave an insouciant reply, "I'm not sure I'd want a steady diet of the stuff
but an occasional mouthful in the course of some of our sexual gymnastics
would be perfectly acceptable." It was the first time I'd heard Andi
giggle, usually she had a booming laugh in the lower range of tones. This
sound was high-pitched as though some tension was being released.
"Sexual gymnastics is right. Dave, if we're gonna keep this up either
you've got to get a bigger car or we have to start going to my apartment."
Three days later, when once again I found myself looking for Andi, I
felt like a serial killer. No, I wasn't out to murder a string of victims
but I couldn't help thinking about all those movies; you know the ones I
mean: Manhunter, Silence of the Lambs, Se7en and Tightrope. The killer is
always on some sort of a strange cycle where the time between each killing
gets shorter and shorter, a sure sign of their ongoing mental degradation.
It was getting to be that way with me about Andi.
My episodes used to take place six weeks or a month apart. Between
those times I was perfectly content just having sex with my wife. Then I
met Andi. Six weeks turned into two weeks. Two weeks shrank into weekly.
Weekly transformed itself into every third day. My desire for Andi was
turning into a constant craving. I lusted after her delicious brown body
the way a chocolate addict yearns for their daily Hershey bar.
Mind you, my wasn't suffering. Between bouts with my dusky houri I
was banging my like a big bass drum. She even asked if I was taking
some sort of herbal supplement. I couldn't tell her it was Andi I was
taking, taking every chance I got.
This time Andi was walking her usual route. I had no trouble spotting
her from several blocks away, her sapphire blue dress had burned itself in
my mind. Sometimes a mere flicker of blue perceived in the corner of my
eye could act like an azure lightening bolt, paralyzing my thought process,
leaving me standing a zombie awaiting a command, conversation trailing off
to disjointed mumbles. It was embarrassing, responding like one of
Pavlov's to a learned stimulus, but yet it happened, happened
repeatedly even in situations where I knew Andi couldn't possibly be
In the trashy romance novels my reads the characters are always
"burning with the flame of their desire," or "drawn to each other like a
Morning Glory to the sun," or some other such nonsense. But there was no
denying my lust for Andi had become a major component of my psyche. My
infatuation was starting to become an obsession. I craved Andi the same
way a repentant sinner craves absolution and for much the same reason.
I'm not a religious person, at least not in the sense of organized
religion. The hellfire and damnation services I attended in my youth
seemed to me to be more the work of a devil who wanted to pit people
against each other for his own purposes than the wishes of a loving deity
responsible for the creation of each and every one of us. But I understood
the basic principles of religion, including the notion of absolution. And
that's what Andi provides me. Not absolution, most organized religions
would hold our actions to be mortal sins, but the sense of acceptance and
inner peace that's said to follow absolution.
I had a short moment of panic when another car rolled slowly by my but the driver must of had poor taste because he drove away without issuing
an invitation. Stupid bastard, I thought to myself smugly, he doesn't know
a good thing when he sees one.
When she got in the car Andi gave me the good news, her roommate was
gone for the day. Finally, after all the waiting, her ass was mine.
Andi's apartment was about three blocks east of the avenue. She and her
roommate shared apartment 12 on the third floor at the front of the
building. The elevator was out of order, forcing us to walk up the stairs.
I made Andi go ahead of me, not only to lead the way but to allow me to
watch her ass move in the tight confines of her blue dress. Each step she
took upward was marked by a corresponding increase in my level of sexual
excitement. I didn't think I could get any harder, hell the last time I
was this hard I was 16 years getting my first handful of bare tit.
Once inside the apartment I took Andi into my arms, my hands mauling her
ass. She broke our embrace, dropping to her knees and rubbing her face
against my erection, I started to pull off her frock, only to be stopped by
her request "to slip into something more comfortable before you ruin my
While she changed, I stripped determined not to wait any longer than I
had to to sink my cock deep into her nether channel. There would be no
foreplay, I wanted raw, primitive sex. I wanted to chastise Andi for
making me wait by driving my dick into her ass and hearing her make those
sounds whose descriptions had tempted and taunted me for weeks.
Andi returned to the room, dressed in a satin slip the same solid shade
of blue as her dress. The slip was cut low in the back, with high slits on
each side. She looked carrying with her a small woven basket of condoms
and lubricants which she set on a small table next to the couch in the
middle of the room.
Andi sensed my desire and acted on it, walking around to the rear of the
aptly-named "love seat" then leaning over, moving her legs back and her
feet apart, presenting her ass for my pleasure. I untied the cross-straps
of her slip, allowing both the material and her to dangle over the
couch's back toward the front cushions. An flip of blue cloth and the
object of my longing finally revealed itself to my gaze.
By now I was so hard I but, as much as I wanted to, I couldn't just
ram it in. For one thing, my level of excitement was so high I'd probably
spurt all over her the minute my cock came in contact with the cheeks of
her ass. For another, Andi deserved better than a "ram and jam, the hell
with you mam" fuck. So I did the unexpected.
Even as my right hand moved toward a container of Astroglide, my left
found its way to the nape of Andi's neck. Brushing her hair aside, I
kissed the hollow where her spine disappears into her skull. She gave a
little quiver, and began to slowly grind against the sofa.
My finger bumped its way slowly down the xylophone of her spinal column,
pathfinder for my shadowing tongue which left a liquid pathway of saliva in
its wake. Halfway down my hands strayed from the trail to caress her
sides, abandoning the tongue to complete its journey unescorted.
Ignoring her ass, I stroked her thighs, her hips, her back, gently
blowing against the warm flesh after my hands had passed. I listened to
her breathing quicken, heard the escape of a half-buried moan. And then I
stepped back, ending all contact, to admire what was soon to be mine.
I loved the way Andi looked arched over the furniture, inviting,
vulnerable, her legs beginning to tremble from the effect of holding her
pose. And her ass, Andi's ass was like an overripe peach ready to at
any moment. I dropped to my knees and gave each buttock five broad long
licks, inhaling the scent of dark spices her body gave off. There was
nothing buried about her moans now.
I pried her tight cheeks apart and for the first time, saw her pink
anus, Clenching her butt, Andi had her wink in invitation to me, not
that any was necessary. I coated my throbbing rod with Astroglide and,
moving closer, squeezed a large glob of lube onto her tailbone. Again Andi
shivered, whether from the temperature of the gel or desire or fear to this
day I don't know.
Digital Picassos painted her rosebud with lube, teasing the crinkled
edge of her puckered before sliding their way inside, one at a time
until an advance team of three fingers were camped out in her colon,
stretching and relaxing her for my entrance. The swirls of the Astroglide
looked especially wicked against the dark chocolate skin.
As I started to move my cock toward its target, the hand guiding my rod
brushed against something, something out of place, something that shouldn't
have been there; a hanging bag of flesh. Moving back I grabbed Andi by the
arm, forcing her to turn around and stand up at the same time.
The expected female genitalia were missing. There was no nested
between the front of Andi's thighs, its lips wet with anticipation.
Instead there was a semi-hard black cock, its dripping crown emerging from
its foreskin like a gopher peaking out of its hole. It wasn't the
monstrous black cock the size of a baby's forearm you read about in all the
porn stories. If fact, it was a little less in size than mine but it was a
cock and it was jutting out from where a should have been.
For a moment Andi and I both looked at each other, her eyes betraying
her worries. As she started to speak, I lifted my hand to her face. She
flinched away, expecting to be struck. Instead I placidly brushed my palm
against her face before resting a single finger across her lips.
Again I took her arm, turning her back to the sofa, pushing on her back
until she was once again hunched over its top, ready to provide me with
She turned her head to look at me. I turned it back down to look at the
"Just be quiet Andi, There's nothing you need to say."
As the tip of my dick made contact with her rosebud Andi pushed back,
enveloping an inch with her first thrust. Now it was my turn to moan as
she contracted the muscles of her sphincter around my rod, dragging another
half-inch into her hungry hole. A moist warmth spread its way down the
length of my dick until Andi's ass was nuzzled up against my pubic bone,
our low hanging sacks bouncing against each other as I began to set an
uptempo rhythm to our motions.
Andi fucked like a starving tiger, growling as she rode my rod back and
forth, its reddened length pistoning in and out of her tight, distended
hole, I buried myself to the hilt, luxuriating in my mastery, however
temporary, over the body underneath me.
Stretching out I laid myself over her back, our commingled sweat
providing the lubrication where our torsos rub against each other.
Although this position took half my dick out of Andi's ass and slowed down
the momentum of our movement it had its own rewards in the feeling of my
nipples being raked against her shoulder blades, the green apple scent of
her shampoo wafting from her perspiration-damp hair, the heft of her
breasts against my palms.
I turned Andi's face to meet me, her lips hot on mine, my tongue darting
into her mouth like a minnow, exploring along the inside of her lips,
across the front of her teeth, now back out to tease the corners of her
mouth, now in again, our mouths sharing the same air, our lungs breathing
the same breath, Her dark brown eyes were closed as I moved my tongue to
shower them with butterfly kisses.
Then it was back to savage fucking again, pure mental lust translated
into physical motion, the room filled with our grunting and panting,
ecstasy given voice. Grabbing the free sides of Andi's slip with my hands,
I used it as an aid in our coupling, pulling her on and off my cock even as
she pressed herself tighter against the sofa, using its bulk to add
strength to her answering motions. I pushed forward, Andi pushed back. I
pushed forward, Andi pushed back. As our excitement rose so did the force
of our lunges.
My orgasm ripped though me like a tsunami, carrying me high and far on
its crest before spending itself against the shore. I lay slumped against
Andi's back panting for air. As my breathing became more even Andi wiggled
out from under me and guided me the front of the love seat. She
disappeared only to return with a warm wash cloth she used to bath my
groin, giving the head of my dick a lingering kiss as she finished her
clean-up. I patted the cushion next to me but Andi shook her head, rushing
instead to the bathroom. The sound of running water obliterated any other
noises she was making.
I was surprised, but not stunned, to find out Andi was a she-male.
Almost all of the indications of her true nature had registered with my
subconscious: the heavier than normal make-up and the follicular bumps, the
low voice, the fingers, the fake tits; the clues were all there.
As a psychologist I know each of us has a primeval shadowself inside; one which eats at our table and shares our bed without anyone
knowing it; one which whispers to us at night; tempts us with rough
forbidden desires, black-veiled pleasures interwoven with liquid crimson
ribbons. The one we keep under a thin veneer of civilization, the
one we want no one else to see, the one we keep shrouded from others and
often even from ourselves. Despite my professional knowledge I'm no less
subject to this duality of person than anyone else.
A central motif of religions both ancient and new is the personification
of the tempter, the one who promises to fulfill our deepest longings if
only we will stray from the path of righteousness. Heaven sends us good
meat while the Devil sends us cooks. But, as Shakespeare might seek to
measure it, "Is this her fault or mine? The tempter or the tempted, who
My relationship with Andi quenches thirsts I never knew I had. I'm not
gay. I still make love with my wife. I can honestly say I've never had
sex with another man. Because when I bury my cock deep in Andi's ass, let
her lips caress me, even when I suck on Andi's appendage and savor the
reward of her coating my tongue, I'm not with another man; I'm
with a very special woman, one who does for me things no other woman can
I've taken Andi off the streets, found her an apartment and a good
paying job as an administrative assistant with a friend from college.
After all his mistress was my secretary for several years so turnabout is
fair play. Our trysts are regular and rewarding. Sin or not, I'm content
to love my own personal "Devil With A Blue Dress On."