Summer school and risky business as Alex explores life in college and on the streets.
The Greatest Lie
Chapter 3
Town and Gown
WARNING! This story meant solely for adult audiences! It contains scenes of graphic sex and forcible rape described in first person narration by its transgendered, teenage protagonist. If you are not an adult, or if you find this type of material offensive, please stop reading, hit the back key or dispose of this file. You have been warned of the content. If you proceed neither the author nor the site host will be held responsible! This story is purely fictional. All resemblance to actual persons is coincidental.
The Greatest Lie
Chapter 3
Town and Gown
My weekend escapade with my first real lover, Jake, convinced me that I was destined to live as a girl, despite having been born a boy. Unfortunately, it was my male persona to whom the University of Minnesota had extended admission and a scholarship, and I wasn’t quite sure how they would react if I showed up asking for a room in the women’s dormitory.
It was bad enough that I, a product of middle class privilege, had leveraged a Spanish surname into a lucrative scholarship, but to present them with an undisclosed gender reversal might put me sideways with the Admissions Committee and the scholarship people. I needed the dough from the scholarship, because during my senior year I had managed to alienate my parents through some complications arising from my crossdressing habit. With great regret, after I arrived in Minneapolis, I changed back into boys clothing to register as a freshman entering the summer session, and tried to reclaim my male persona.
One good thing about registering for summer school was there were hardly any other freshman around. I got assigned to a single dorm room, and got all of the classes that I wanted. As a freshman, I was quite a novelty among my classmates, who were split between remedial types that were making up failures from the prior year and nerds who were single-mindedly piling up credits as fast as possible.
I was so young that I had little in common with my older classmates and spent most of my time in my room or the library reading and doing homework, dressed en femme. Naturally, I loved studying. I had to, because, typical ambitious me, I had signed up for all upper level classes.
The teaching assistant for my "Gender Roles In Literature" class was Jon, a tall, dark intellectual grad student in the English Department. At the end of the first week of class, he invited me for coffee. By then, I was getting lonely, so I gratefully accepted.
As I usually do when I meet new people, I asked a lot of flattering questions and let him talk about himself. He was from a wealthy family from Chicago. He told me he was bisexual, but recently he had lost interest in sex completely. In a matter of fact manner, as if it were of no concern to him, or to me, he asked "Alex, are you gay?"
Whatever I was, I had grown accustomed to hiding it, and so I replied that I was still trying to figure some things out about myself. He liked that answer, and said he was still trying to figure himself out too.
He was on the Board of the Alliance of Gay, Lesbian and Transgendered Students, and was in charge of a task force monitoring and investigating and reporting to the administration on any harassment of gays on campus. In my situation I thought he might be helpful, so I made the Friday afternoon coffee a regular event, and waited to see if anything developed.
He certainly had the trappings of campus power. The Alliance had an office in the Student Union and Jon had a desk there. Of course, he also had TA’s office in the English Department. In academia, I knew from my dad’s experiences, office space was the talisman of power. It looked like Jon was doing well in that department.
The course work was demanding, and I really wanted to excel. If I had straight A’s, the Scholarship committee might be more forgiving when I tried to change my registration to a girl’s name. I just studied all the time, tried not to think about sex and stepped up my hormones to keep my libido suppressed. The only thing was, by this time, my breasts and ass were getting pretty noticeable. Even wearing baggy boys clothing and my hair piled up in a baseball cap, I still got wolf whistles when I walked by construction sites.
Finals were really hard, and the Gender Roles exam was particularly lengthy. I ran out of time and had to more or less sketch out my last answer. The day after the exam, Jon met me to talk about my answers. "Alex, I could tell you were on the right track on the question about Orlando, but you really never got to the point."
I’m so sorry, I had never had a final like that, with so much to cover. I just ran out of time"
"It’s really not fair, you’re so much younger than the other students. Your other answers were wonderful, but this one was for the most points, and it was not good."
"If only I could have had more time."
"Maybe you can. Come over to my place tonight."
I was pleased Jon was taking such a great interest in me. Was it my mind, or my body, I wondered? I re-read my notes Orlando, and freshened up. If he going prepared to give me another half hour on the exam, I would gladly give him a half hour he would never forget.
Jon had my exam book, partly marked up, but not graded. I sat at his kitchen table and he gave me the test and set a timer for a half hour. I sat down and wrote a brilliant essay, as he paced the room and watched me. When the half-hour was up, he took back the exam.
"I’ll read and grade that tomorrow," he said. "Now, let’s relax," he said as he put on a Tracy Chapman CD and produced a joint and a bottle of Chianti. I hadn’t had a drink or gotten high for months, and I soon had a pleasant buzz. My inhibitions had receded, but not my preoccupation with my performance on the exam.
I got up to pee, and checked myself in his bathroom mirror. Even slightly buzzed, I looked really good. I had on this totally subtle makeup. I added some shadow, mascara and gloss, looked at myself again, and decided I looked gorgeous. I mouthed "Good luck" to my reflection, returned to the couch where Jon relaxed, and boldly sat in his lap and threw an arm around his shoulder. He looked pleasantly surprised.
I made close eye contact and asked "Jon, remember the first day we met and you asked if I were gay?"
He nodded.
"Well, I’m not. But I’m not straight either, and I am so mixed up about myself." I batted moist eyes in his, looking confused and vulnerable.
I wasn’t really confused, but I liked the way it sounded: like I needed his advice. He rose to the bait. "Do you like sex with boys or girls?"
"Both, but when I have sex with girls, I feel gay, and when I have sex with boys, I feel straight."
Jon reflected a moment, looked at me with seemingly clinical interest, and then opined, "In my opinion, you must be a transsexual."
I gaped and asked "What do you mean?" It was feigned surprise. After all, I had spent hours in the medical library at UCLA researching my self-medication. But Jon expounded on the clinical and social aspects of transsexuals, and I responded like one of Dr. Freud’s admiring acolytes. I admitted that I had been cross dressing and taking hormones for months, on my own, and now Jon was surprised and intrigued: his curiosity manifested itself through his hands, as much as his words. They slipped beneath my baggy Golden Gophers sweatshirt and quickly found my satin spaghetti strap camisole.
From that discovery it was only a short interval until he discovered my pert, firm breasts.
Six months of heavy estrogen doses, and large breasted genetics in both my maternal and paternal lines, had produced small but perfectly formed, inverted ice cream cones that jiggled pleasantly but never sagged, topped with silver dollar sized maroon aereoles. I raised my arms, as if in surrender, and he pulled my sweatshirt off.
Jon, the silver tongued pedagogue, was tongue tied with surprise and lust: all he could manage was a husky, "O wow!" before he slid the straps down over my slender shoulders began devouring my breasts. But there, his tongue discovered a mute eloquence, as he licked and kissed me in a frenzy, as I cradled his head like a suckling baby’s.
I slipped my hand between his legs and began massaging his cock through his jeans. In a few minutes he broke his lips grip on my nipples and picked up my 5’7", 105 pound frame and carried me into his bedroom. "You are the most fantastic trans I have ever met," he said. "You can act like a perfectly normal boy, but you have the perfect body of a young girl."
"Thank you," I said "but I’m not quite perfect yet."
"We’ll see about that", he said, and pulled off my pants and began rubbing the front panel of my panties.
My tiny cockette responded with a mini erection that strained against the front of my panties. As he stroked my cockette, his other hand continued to explore my breasts, which now piled up in perfect, soft mounds on my chest as I reclined. I released my streaky blond hair from its pony tail so it would frame my face, and then asked "Jon, what are you going to do to me?" Eight weeks of sexual abstinence had me painfully horny, so I had some ideas of my own.
He responded wordlessly by disrobing, and I wriggled out of my panties and camisole. "Let’s try this for starters," he said as he assumed a "69" position above me.
His body was thin and not too hairy, and his circumcised penis was larger than I had expected. It filled my mouth and nostrils with a slightly mossy taste that was quickly spiced with the pleasant, sea foam of his pre-cum. His mouth took in fully my dainty cock and balls, which he began to suck with great expertise. One of his hands explored beneath my ass and quickly found my hole, and his fingers played and poked there with delightful persistence.
By now, I was taking the full length of his cock down my mouth and throat, my arms around his ass and adding even greater force to his rise and fall over my upturned face. In this position, there was nothing but my gag reflex to stop it from entering fully, and I had learned well how to suppress that. My natural talents soon brought Jon to the brink of climax, but I did not want it that way. I gently braked his thighs with my hands, and gasped "Wait."
He must have guessed what I was thinking, because he rose and lay down next to me. We kissed, mingling the delicate flavors of my little dickie with the meatier stronger flavors of his swollen cock. Then he began a most unequal sword fight with our mismatched penises.
My lubricant was in the other room, and I did not want to break this spell. "Do you have any KY?"
He rolled over and produced a bottle of "Astrolube" and a couple of condoms from his bedstead. "This is better," he said, handing me the lubricant. He deftly slipped on a condom as I lubricated my ass. "Put some on my cock," he advised, and I applied it liberally, with several slippery strokes that made his penis twitch in my hands. Holding the second condom and looking at my tiny cockette and shriveled balls, he said "I’m afraid this isn’t going to fit you."
"I don’t need it," I said, settling face downward on the bed and raising my ass provocatively in the air.
He bounded into position behind me and began testing my anus with his hard member.
"You sure are tight", he said, as his penis rebounded for the third time from his attempted entry.
I reached my hand back to guide him. "Please go slowly," I reminded him. This time, two of the seven inches of his cock entered me, and as the fiery electric charge of pain built in me, I said "Go on", exerting maximum counter-pressure to ease his entry.
Two more inches of pain filled with ecstasy, then two more, and he was in. Sharp pain shot through me from my ass to my head, and my tear-filled eyes were blinded as if by a flashbulb, but agony faded to a pleasant glow of pleasure, just as a flashbulb’s aura disappears.
He gasped "Wow, are you tight!"
I feigned worry for his encased prick. "Are you OK?"
He replied "Are you kidding, I’m great. Are you?"
My voice choked with pain, I replied "It’s getting better. You’re so big!" I knew guys liked to hear that, and he was about average, in my limited experience. The initial moments of anal intercourse are always excruciating for me, until my sphincters relax and my internal juices start flowing.
Jon was a very considerate lover, remaining almost still at first and letting me grow accustomed to his length and width. Gradually, the fires inside me subsided to a smolder of pleasure, and I said, "Go ahead and fuck me hard".
He began probing me carefully as he sought to arouse me with gentle tweaks of my nipples and massaging of my cockette. Gradually, I opened up and he began to thrust in and out with greater energy. He did not possess the superhuman strength of Jake or the animal barbarity of my motorhead rapists, but he was in good shape and was experienced and expert in the art of sodomy.
We were in my favorite position, a prone doggy style, and I responded to his lunges with my own contractions and hip gyrations. I could tell he was approaching orgasm, and I wasn’t ready, so I said "Please slow down," and he did. I wanted to be fucked more but I didn’t really have any great ideas, so I asked him "Do you have any favorite positions?"
He withdrew from me carefully, and said, "Sit on me", as he lay on his back. I straddled his prone body, ass poised above his upright dick, and I impaled myself.
Even in my well lubricated condition, this maneuver took my breath away, as he pierced me from a totally unexpected angle. It felt like a deeper penetration than ever, and he was able to send himself even deeper with up-thrusts of his hips. But now how hard I wanted to be fucked was up to me, and soon I was riding up and down as hard as my weak little thighs could lift me, and repeatedly banging his cock-head from my rectum to my diaphragm. It slipped out with a painful snap, but when it escaped, I aimed my ass and re-inserted him with reckless abandon, for now my rectum was wet and ready.
He stroked my bobbing breasts and cock as I screamed and rode him until I was totally exhausted and glistening with perspiration. As I rested atop his stomach, breath heaving, a little droplet of sweat dripped onto his stomach. My flushed face grew even redder with embarrassment. "I’m sorry, I usually don’t get this much exercise."
He sat up, still inside me, and pulled my legs around his back. "Try this," as he settled me back down onto his prick from a face to face embrace, and kissed my breathless lips.
I felt like my insides were melting; he gently bounced me up and down as I regained my breath. "I love both of these positions," I said. "Can we try any others?" He lifted me, and supporting my back as he went, dropped me into the legs up position for a few strokes. My spine twisted and ached as it recoiled from a few dozen powerful strokes.
Compared to the nurturing position that had preceded it, the legs up position seemed crude, barbaric and uncomfortable--OK for a cautious entry, but cruel for real fucking.
He must have sensed this, for soon he lifted one of my legs over his head to my side, and rode me from atop my other leg. I had never felt so trapped and vulnerable, and his penis found new angles and places to probe and excite me. Finally, he rolled me back over onto my tummy.
"Which one did you like best?"
"This one," I answered, twisting my tush as he thirsted anew. The rotation through the positions and the varied angles that I had been penetrated made me feel both more relaxed and more fully stimulated. He seemed more rested and his movements were even stronger and more confident. Soon, I felt like my insides were boiling again, and his movements grew ever faster and more intense. Finally, I felt him lose control and begin jerking wildly inside me. He had climaxed.
He kept on fucking and stimulating me, but it was no use. Realizing as he drifted into a post orgasmic sleep that I had not climaxed, he whispered "I’m sorry" in my ear.
I responded "That’s OK, you were great."
I had sort of missed the feeling of cum spurting inside me and tickling the walls of my intestines. But I did not miss the ooze of sticky seed dripping down my thighs and forming a cold wet spot beneath my groin, while pinned beneath a snoring body. I enjoyed Jon’s weight atop me. He weighed enough to make me feel subjugated without being suffocated. I closed my eyes and permitted myself a brief fantasy about being his faculty wife, and serving tea to his students. But before long the fantasy had shifted to my blowing one of the students in the closet while Jon pontificated to the others, and then he woke up and pulled out of me.
He rose and flushed his rubber, and then said "Wow, er-ah..."
"You can call me Ally" I interjected
"AH-Allie, I wish I had known you better earlier this summer."
"You could have tried harder", I teased, recognizing secretly that he had been trying, but never asked the right questions.
"My problem was that you are a master, er, a mistress of camouflage." "You mean at pretending to be a girl," I pouted.
"No, at pretending to be a boy," he replied.
"Flattery will get you everywhere," I said smiling. I shivered. Now that I wasn’t warmed up by body friction, it was a little cold. He got me one of his T- shirts. It fit me like a dress. He poured some more Chianti.
"Who is your doctor?"
"I dunno, Student health, I guess."
"No, I mean for the hormones. You must be on estrogen to have developed as you have." He playfully squeezed my breast to emphasize his point.
"I guess that’s me." He was astounded.
I gave him a sanitized version of my acquisition of my hormone stash and assured him, somewhat inaccurately, that I had researched and was strictly following appropriate protocols. He was amazed at my ingenuity, but concerned. "You could kill yourself with estrogen. You really need to be monitored. I’ll find you a doctor through the Alliance."
"Not somebody from the Medical School." I confided my fears about coming out to the Registrar and the Scholarship people before I had an academic track record. "That’s why I was so upset about screwing up the Gender in Literature final."
"You’ve got a point there. But it’s not just making them love you for your grades. We had better make this look like a slow transition, not like something you had decided on before you got here. You are going to have to keep that 'boy act' in practice for a semester or two, to make it look like a gradual thing."
He was going home on break the next evening. "Gotta check in with the ‘rents’", he joked. "Where are you going?"
Mom and dad were going to a conference in Egypt and had half-heartedly invited me, but I wasn’t to thrilled about touring a country were my gender status was capital offense. I wasn’t too thrilled about taking the bus back LA to dodge the motorheads in my neighborhood either. Unfortunately, the dorms were closed, so I couldn’t stay there either. I was temporarily homeless.
"Stay here," he offered, giving me a key.
He promised that when he got back he would try to set things in motion for my transition to a female identity when he got back for Fall Semester. I spent the night with him and made him come in my mouth the next morning. He was delicious. He kissed me goodbye, took off to drop off my exam at the English Department and then left for Chicago in his Miata.
I was delighted to have not only a new lover, but an advisor and protector. I was even more delighted when I swung by the English Department to check the grades in "Gender Roles." I had a 97.
There is nothing so sad and depressing as a college campus between terms. The place was empty except for a few foreign students and people like me, stranded by circumstances, in the unfamiliar situation of having nothing to do. After a couple of days of catching up on sleep and doing some research on hormone treatments of transsexuals at the medical library, I ran out of things to do, and started to feel bored and useless. So I decided to explore Minneapolis.
It was then I stumbled on Hennepin Avenue, a downtown street lined with flop houses, arcades, bars, and late at night, whores. They beckoned passing cars with gestures that ran from the seductive to the outrageous, and they drew traffic jams of onlookers and customers, and only sporadic attention from the indifferent police.
I was fascinated. I spent an evening studying them while nursing cups of cheap coffee at a greasy spoon cafe. The technique looked simple enough: stand by the curbside, baring a stiletto-heeled leg, until a car stopped. Poke a head in the window, negotiate, and if a deal was struck, enter and drive off, to the envious cluck-clucking of the competition. A quarter hour later, the car would return, and the lucky lady would resume her post.
I watched as one girl turned a dozen tricks that evening. Finally, she came in for a coke, and sat next to me at the bar. She asked "Wah wuz you lookin’ at, bitch? Uuah cop?"
"Me, a cop? No way, I ran away from home and I’m trying to figure out what to do."
She looked at my "University High" sweatshirt, jeans and Sketchers. I looked the part, and she relaxed. She was 20 years old: a pretty, busty bronze skinned African American from Memphis.
"What are you doin’ out there?" I asked innocently.
She smiled knowingly and said "Turnin’ tricks, a-course." "
Would you show me how? I’m broke. "
"Show nuff" she said. "But I’m dun t’nite. Made ova 500 dollas. Gonna buy me some ice now, get high t’mara. Meet me here t’mara et 8, and dress nice, know watah mean?"
I knew exactly what she meant.
I woke up the next morning early and began preparing my day of beauty, Hennepin style.
At a cheap Vietnamese beauty salon, I had my hair bleached platinum and corn-rowed. I got a facial, a manicure with nail extensions, painted Valentines Day red, a pedicure to match, and bought the trashiest red spaghetti strap dress and the tallest, strappiest red stiletto sandals I could find. I bought a pair of outrageously big gold hoops and the brightest collage of foundation, mascara and lipstick that my pale complexion could handle. With the latest Allure magazine as my guide, I made my makeup as provocative as I could.
As I dressed, I folded my shrunken scrotum forward over my tiny penis and taped it securely into a compact cocoon. I had bought a box of jumbo sized, winged Tampax panty liners, and I splashed some ancient ketchup from Jon’s fridge on one and put it into my panties. I didn’t want some horny trick to discover my secret while insisting on fucking me: I would tell them I was having a really heavy period, and as you know, I’m a really good liar.
With my veins coursing with an extra large dose of estrogen and speed, I took a cab to meet Daylene for final preparations. The cab was an extravagance after my spendthrift day, but the heels were already killing me, and I planned to be on my feet a long time that night.
Daylene’s eyes goggled when I wobbled into our greasy spoon on my unsteady and pinched feet. "Wo, bitch, ya look hot!" she complimented me.
I replied, "you too. So what’s your secret, Daylene? I want both of us to break your record from last night."
"Jus act happy, y’no" she responded.
"How do you avoid the weirdoes?"
Daylene responded, "there’s a kunvenchun, farm kwipent ‘r somthin. Weirdest thang ‘bout dem is dere axents. Jus look happy an tell’em 50 bucks fer head, hunnerd fer a fuck. Dey all take head."
We giggled. I liked her. We walked out into the muggy evening, found a dark corner and smoked a hit of ice together. It was 9:30 when we took our places on Hennepin, still giggling in the giddy excitement of a speed buzz. At about 9:31, the first car pulled up and rolled down its window.
I must have looked about 13 years old, with my slim legs and arms, wasp waist, my small breasts bouncing subtly as I staggered slightly in my ridiculously high heels. "Get in, little girl, let me take you for a ride" said the middle aged, slightly paunchy Viking sitting high in his Suburban.
I improvised from Daylene’s pitch, in view of my special circumstances. "Fifty for head, twenty-five for a hand job." "How much for a fuck?"
"Can’t, ‘m hav’n my period."
"OK, hop in."
"Where’s my donation?" He handed me a fifty, and I put it in my handbag. My heart was racing, but I concentrated on being happy.
I complimented him on his car, his driving, his sound system, his choice of music (country, yuck!) his leather seats, what good shape he was in. He ate up the flattery. He found a deserted location and pulled over. He reached over the massive center console and slid his hands between my thighs. His rough fingers probed inside my panties and pressed against the tampon that guarded the secret between my legs. He grunted "OK, then give me head."
Now, the console, which had been a barrier to his exploration of my ass, became an awkward obstacle to the task at hand. I kneeled on the seat and over his garage door opener and who knows what else to descend on him from an awkward angle, trying hard to keep from banging my breast on his stick shift, as I pistoned my lips on his prick. He tilted his seat back and began groaning with pleasure.
There was nothing particularly erotic about this front seat encounter. As Garth Brooks droned in the background, the Viking’s eager hands twisted my head and neck into position. I could barely see his penis in the gloom, but I plunged my head into his lap and found it with my glossy lips and wet mouth. He actually tasted pretty good and clean, and his small size presented no challenge for me.
But the awkwardness of his position and his indifference to my comfort placed me in constant danger of banging my head on the steering wheel, and when this happened it yanked my heavy hoops in my ears. My back and stomach ached from arching over the console, and the fifty bucks in my purse seemed inadequate to for all this discomfort. I made a mental note to increase my rates.
Fortunately, he was a horny guy in a hurry and lasted no more that a song and a half before coming in my mouth. I let the cum drip out of my mouth onto him, breathing heavily on his dick to keep it warm and rubbing it into his groin. I was amazed that, after his brief exploration between my thighs, except for the hands he grasped my cornrowed hair with, he had not touched me during the encounter.
We drove back in silence, his shame palpable. My back was killing me, and I was tired.
He didn’t even say thanks when he left me back on Hennepin, feeling used. I went back to the café, to the disapproving glare of the owner, and bought a diet coke and waited for Daylene.
She came back about five minutes later, still bouncy and giggly. "Wassa matter, Al?" she inquired. I replayed my encounter with Mr. Country Music. She laughed and said "Das why Ah recommend a back seat."
"Do you swallow it?" I asked.
She rolled her eyes and chided me. "Din’ch ya use a condom, honey?" she laughed, rolling her eyes at my ignorance. After I had gargled and fixed my lipstick, I went to one of the liquor stores and bought a twelve pack of Trojans out of the fifty. When I got back on Hennepin, Daylene was already gone. I resumed my post, batting my eyes provocatively at the passing traffic.
Trick number 2 was a four door Cadillac, an old guy. He wanted to talk before we went at it. "Are you on break from your school?"
I nodded.
"What grade are you in?"
Christ, this guy thought I was still in high school. I indulged his fantasy. "I’m going into tenth."
"You’re so young, so pretty," he said as he pulled my face toward his lap.
"Just a sec" I said, remembering the rubber. I rolled it on and slipped him into my mouth. An antiseptic taste of latex and talc filled my nose as his cock filled my mouth.
Old guys are nicer, but they take more work, I learned. He built to climax and failed three times, and I swear that when he finally came I thought he had had a heart attack. It had not been very erotic, but pleasantly sanitary. After I finished him, I slipped the condom off and tied the end like a water balloon. No muss, no fuss. Afterwards, he was extra polite, saying as I left him, "Thank you, young lady," and tipping me an extra twenty. Old guys! A little extra effort, but worth it.
I worked my way through the dozen Trojans by midnight, and decided to call it a night. I went to the café, ordered a Diet Coke and waited for Daylene. She showed up, still grinning, at 12:30 and we started to compare notes. She was a little irritated that I had made a hundred and twenty more than she had. "Beginners luck," she said.
I was still pretty buzzed, so I invited her over to Jon’s to finish off some of his booze. We drank and regaled each other with our escapades until 3:00. Eventually, we passed out together in his bed. I woke up with cotton mouth and a headache. Was it all the talcum and latex or the booze, I wondered? I smelled bacon and eggs. "Mornin’ girlfriend" Daylene’s cheerful voice sang out. "Surprise for you, breakfast is served." She brought me breakfast in bed. We shared from the giant plate she brought.
I gobbled the cholesterol-laden meal ravenously. She put the plate aside, and "Honey chile, I see uze got a surprise for me, too." She gently stroked my groin through the sheet. "Ida never known you wazza shemale if Ah hanta slep t’ere." I smiled nervously.
"You won’t tell anyone, will you?"
"Shit no, honey chile, cuz ahm won too!" She slipped down her panties to reveal her own shaved cock, three times larger than my own tiny thing, but stained a darker brown than the rest of her skin by exposure to estrogen.
"Daylene, I’d never have known." I was delighted that my friend shared my secret, and as intrigued by her body as she was by mine. "Let’s take a shower together", I suggested, and she nodded with girlish glee.
Soon, we were soaping one another's breasts and bottoms. She had size "D" implants which I both loved and coveted. I noticed that her 6 inch cock hardened readily when I handled it. "Aren’t you on hormones?" I asked, my fingers grazing her large dark aereoles.
"Yeah, three yee-ahs, but ma docta keeps me kinda balanced, y’know." I admitted that I had had no doctor, and she tut tutted me. "Yo funny, "she said, tracing my pretty chin with her finger.
She kissed me, and I kissed her, and I felt her firm breasts nuzzle my own dainty titties as we settled onto Jon’s unmade bed. As we kissed and cuddled, our cocks rubbed each other and got hard. Though our lips were joined, our eyes met and reached a silent accord, and we switched into 69 and began sucking on one another. Her freshly showered cock tasted divine, and her pre-cum was delicious. I sucked her and fingered her anal ring, and she did mine. Her cock filled my mouth perfectly, and her shaved groin was as smooth as a baby’s. I loved the feeling of a hairless she-cock in my mouth.
Her tongue was exploring beyond my little cockette and scrotum. She rolled my pelvis upward and then began darting her tongue onto my hole. She parted the flesh of my slender cheeks and kissed my stretched rectum like a pair of lower lips, and then tongue kissed inside my freshly scrubbed ass. It was the sexiest thing I had ever felt, and she lingered there long enough to make me writhe with ecstasy.
"Do you want to fuck me?" I soon pleaded.
"Happy to, ho" she replied. Seeing my hurt look she joked "Ah mean, sista ho".
I reached into Jon’s bed stand for a condom and the Astrolube. She ripped the wrapper with her teeth and rolled it on expertly, as I lubed and probed myself with a slender finger. She daubed her cock with more Astrolube and her face took on a harder, more determined look. She put her arms under my thighs and rolled my tush up, pinning my legs helplessly in the air. She fingered my ass and studied my reaction. Her eyes gazed deep into my own, and I could not take my eyes off her striking face, framed by her large nippled, brown breasts swaying above me. I looked at her pleadingly. "Please don’t hurt me."
She smiled and her momentarily tough look warmed with compassionate. "Don worry honey, Ah knows how."
Soon her cock head was pressing against, and was then inside my ring. She eased it in until she saw me wince with pain, and then withdrew her cock and let my rectum relax a few heartbeats before she entered me again. This time she slid in farther until she saw my face begin to contort, and then withdrew again.
I must have smiled as I relaxed, because she whispered "Yor beautiful."
"So are you," I replied, and she was.
She entered again, and this time I was completely relaxed. "Now, did dat hutcha?" she asked.
"Just a little", I replied, as bliss took me over. Soon, we were both uttering girlish cries of joy as the pace of our lovemaking increased. "Can you cum", I asked.
"Ujaly, if I’m doin de fucking," she said. "Can you?"
"Maybe on my tummy," I said, and she immediately rolled me over.
Her dick was less rigid than the guys who had fucked me before, but its greater flexibility made it even more stimulating. I was thrilled by the feeling of her dick in my ass and of the brushing of her boobs on my back. It felt like I was getting fucked by a woman, and this made me feel even more like a girl than ever before: a lesbian femme. This made me very hot, and Daylene’s expert fondling of my cockette made me even hotter.
Suddenly, without warning, I came, a tiny wet droplet in her hand. Daylene felt it and got really aroused herself, and soon her motion speeded up and went out of control, and with a chorus of joyous squeals and cries she came into my still pulsating behind. Then, her breasts slumped even more weightily on my back and I felt the tickle of her long, curly hair on my neck. It was not enough to keep me from drifting off to sleep.
When we awoke, we showered together again and got so horny that we might have made love again, except we had so much to do. We shopped for new clothes, shoes and make-up, and spent hours experimenting with make up and hairstyles. We walked hand in hand to Hennepin, two sistah ho’s on the town.
The next ten days passed quickly. "Tricks all night, kicks all day", Daylene called it.
But I was on a collision course with reality. School would resume in a few days, and my ho’in would have to become, at most, a weekend activity, as my studies would fill my days and nights. And then there was Jon. I really needed and liked him, but I doubt if he would approve of this life style or appreciate sharing me with about ten guys a night. I would miss the wild nights and days with Daylene, and I would certainly miss the cash flow and the thrill of sucking all those new dicks, but this was not the life for a college girl, or a college boy, as I would soon be. Each night of cheap thrills and day of cuddling with Daylene brought me closer to the end.
Finally my last night came. Jon had called to tell me he was leaving Chicago after the bars closed that night and would be up early the next morning. He couldn’t wait to see me, but if he saw his apartment, he would have killed me. Ten days of non stop partying and fucking had left every surface covered with empty bottles, roaches, condom wrappers, and every sheet stained and sweaty. I had to do maid service.
I was crushed that I couldn’t spend the last night out with Daylene. I helped her get ready for the street, I gave her a hug and said goodbye. She smiled broadly, said, "See ya" and sashayed out to Hennepin in her red party dress.
Cleaning the place and running the laundry made me feel a little less guilty, but as I slaved away I thought, "I bet he wasn’t a virgin while he was gone." On the other hand, he hadn’t given over $5,000 of blowjobs, either, I thought as I settled in his freshly-made bed.
I couldn’t sleep as visions of my prostitute’s life of the past ten nights clashed with my life as a college boy, or girl for the coming year. Platoons of the upright cocks of my tricks marched by in a procession of shame mixed with sluttish pride. I was a trannie whore, and those words reverberated in my head endlessly. I massaged my breasts and fingered my hole, trying to bring forth a vision of Jon, or Jake but all I could summon was the cocks of my anonymous johns, now penetrating my ass as well as my mouth.
That was all I was or ever could be: a trannie whore. And my visions of that pathetic life were now beginning to turn me on, as I felt my cockette stiffen. Oh god, what had become of me? I liked being a whore, a piece of shemale ass for my twisted dates to use and throw away like a used Kleenex on the side of Hennepin. I was totally hooked on street life. How would I make it through college?
These thoughts were interrupted by a knock on the door. Why would Jon knock, I wondered nervously. "Who is it?"
"Minneapolis police," came the abrupt answer."
I freaked, horrified at the thought of arrest and embarrassment. How did they find me here, and how did they connect me to my illicit trade of my flesh on the street? I opened, and two plainclothes cops came in. "Sit down, we need to ask you some questions."
I sat down on the bed, crossed my legs demurely and motioned them to the sofa. I had prettied myself for Jon, and I noticed the cops eyeing me appraisingly. "How can I help you?"
"We found this address and phone number on a deceased, and we want to know why." I was bewildered.
"A deceased, you mean a dead person?"
"Yea, a transvestite hooker we found dumped by the river, strangled. We found this address on her body."
I felt as if I were being strangled myself, and covered my eyes and began sobbing. They waited till my initial wave of hysteria passed, and then said "Can you come to the morgue for an ID?"
I nodded assent, dressed in androgynous jeans, T-shirt and sneakers, and went with them to the morgue, now silent in my grief. I reproached myself bitterly for my embrace of the street life and the terrible price it had exacted from my friend and lover Daylene.
She lay glassy-eyed and expressionless on the slab. I hugged her still slightly warm body, but the detectives pulled me away, worrying about disturbing the evidence. "You know what she was up to, right?" one of them said.
I admitted she was a streetwalker, the words sticking in my throat. Then I began sobbing again. "And you knew her how, exactly?"
Grief did not interfere with my mendacity. "I am a college student doing research on sex industry workers, you know, safe sex habits, attachments to boyfriends, that kind of thing. I am going to write a paper on it. She was one of my subjects." As I cooked up this wopper, it occurred to me that it was actually a really good idea, on several levels.
"So you got some notes on this one we could look at?"
"I haven’t typed them up, but I’ll do it right away if it would help you find out who did this."
"That would be helpful, because we don’t have much on this one. Know her name or where she was from?"
"Daylene, from Memphis. About twenty, that’s all I know. Can I go home now?"
They gave me a ride back to Jon’s: thank god he wasn’t there yet. "We’ll be by in a few days to pick up your notes." I promised them they would be ready by Monday. "If the body hasn’t been claimed in two weeks, we’ll release it to you. Otherwise, it gets a John Doe burial."
"You mean Jane," I said angrily."
"Yeah, right," he said as he left.
I was still banging away on Jon’s keyboard when he arrived three hours later. He was so exhausted that he went straight to bed until two in the afternoon. When he awoke I sucked him and let him fuck me, but without much passion or enjoyment.
He asked me if something was wrong, and I said "Yes, someone I know has been killed." Elaborating on the clever lie I had invented for the cops, I told him that I had started to research the behaviors of transgendered sex industry workers, that I had gotten one of them to really open up to me, and she had let me observe and interview her at length. Now, she had been killed, and I was crushed.
He was very sympathetic and comforted me. He promised that if her family didn’t claim her body he would pay for a proper funeral. He was really impressed and happy that I was doing such a socially and personally relevant research project. He promised me he would try to get me a grant through the Alliance to support my work, and he even thought he could hook me up with a professor in the sociology department to get independent study credit.
This was looking like my most brilliant lie yet. The best kind of lie is the one that you can spin into reality: then it can provide a screen for still more secrets. "Behaviors of Transgendered Sex Workers" would be my project: no one else would know that I was both the author and one of the subjects. My sex industry research project would be the perfect way to merge the street life of Hennepin Avenue that I craved with academic research on a politically correct topic. If I was lucky, I might even be able to investigate the murder of Daylene. It would be all the more fun pulling it off right under everyone’s noses. I smiled inwardly. Maybe college wasn’t going to be so dull after all.
Next: Those Happy College Nights
TG XXX MM-style-sex Cross-dressing hormones she-males drug-use teen-age sex prostitution
This is a sometimes violent story with very raw sex scenes. If that's not what you want to read, please do not read this story.
