DEVIL WITH A BLUE DRESS ON
A "Transgendered Adventure" by Web Dazell
"ADVENTURE (noun): an unusual and exciting, often hazardous, experience or activity."
Welcome to the second story 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, as those of you who read "I SHOT THE SHERIFF AND I ALSO SUCKED THE DEPUTY" know, 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 stretch 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: webdazell@yahoo.com. The more (and more detailed) the emails, the more and quicker stories will appear. So now that everyone understands the rules, let's sit back and let the next "Adventure" begin.
OK, before we start with this story 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 gay 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 story 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 men 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 young girl with a hard-edged body and tits that would poke your eyes out. When I'm in one of these moods older women with stretch marks and sagging tits really turn my crank (in more ways than one). And since my wife 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 breasts 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 thick 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 sucking mouth.
Now I've always been amused when I read these stories about how "It was the greatest blowjob 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 time.
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 bag.
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 hurt 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 tits 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 saline.
I know the old 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 smelled before.
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 downstroke.
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 pussy 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 breasts 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 tits 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 paying basis.
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 mark.
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 girls 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 sucked and the one doing the sucking. Eating some guy 's rod is a big kick for most cocksuckers and I 'm no different.
"Some girls 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 man '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, man 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 blowjob 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 loads 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 swallow 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 increase."
"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 phoney 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 wife 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 girl 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 taking flight.
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 tough part.
As good as she was, and she's plenty good, my wife 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 old 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 another prostitute.
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 else.
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 daughter 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 family had all renounced her and, since in their opinion Andi wasn't a proper role model 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 daughter 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 family 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 dramatically.
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 sucked 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 throw.
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 red within seconds. At the top she pinched the head, not hard enough to really hurt 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 sucking a cock for god's sake. And that wasn't really cum 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 thick 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 boy 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 us.
Her broad tongue began to lave my scrotum like a mother cat 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. Thick 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 man 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 breasts rubbing themselves red 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 ejaculate.
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 wife wasn't suffering. Between bouts with my dusky houri I was banging my wife 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 dog to a learned stimulus, but yet it happened, happened repeatedly even in situations where I knew Andi couldn't possibly be present.
In the trashy romance novels my wife 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 girl 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 old 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 dress."
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 tits 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 hurt 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 straied 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 split 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 brown anus, Clenching her butt, Andi had her hole 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 hole 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 pussy 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 cunt 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 pleasure.
She turned her head to look at me. I turned it back down to look at the sofa cushions.
"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 thick fingers, the fake tits; the clues were all there.
As a psychologist I know each of us has a primeval shadowself hidden 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 hidden 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, just more accepting.
Andi and I are still lovers with all that term applies. I've taken her off the streets, found her an apartment and a good paying job as an administrative assistant with a old friend from college. After all his mistress was my secretary for several years so turnabout is fair play. I bring her regular gifts, including Jai Ose, and have even taken her with me to conferences and conventions; the week in Hawaii was paradise. Especially when we lured the leilani into our bed, her pleas of "Hana hou, hana hou" (Do it again, do it again) still ring in my ears
And yes, for the curious of you out there, with the help of Viagra Andi can achieve erection and ejaculation. I know because I've had her dick in my mouth and up my ass on a regular basis and I enjoy it. I've learned to suck cock as well as any glory hole troll and I swallow too.
Does this make me gay? Did I lie at the beginning of this story? No. Because you are what you believe yourself to be.
Despite the disapproval of her family and most of the world, Andi believes herself to be a woman. Andi thinks, like a woman, reacts like a woman, dresses like a woman, lives like a woman, To me she is a woman, my personal "Devil with a blue dress on."