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                 K R I S T E N' S    C O L L E C T I O N
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Cross-Dressed To Score
by Tom D. (address withheld)

***

I was supposed to take care of Jessica's apartment 
while she was out of town. Her doorman, Raul, was a 
handsome stud, and I was smitten with his looks. When I 
got to Jessica's apartment, I dressed in her things and 
started to do my chores. Raul knocked and I let him 
in... (MM, cd, mast, oral, anal)

***

I have recently had my first experience with cross-
dressing and gay sex. I loved it so much I plan to do 
it again soon.

I am a married man in my late twenties, of average 
height and slim build. My features are rather pretty 
and several times gay men have hit on me, but I had 
always repressed the feminine side of my nature and 
some deep cravings for my own sex. That is, until a 
couple of weeks ago.

It all began when a good friend of ours named Jessica 
told us she'd be out of town for a month and asked me 
if I'd look after her large collection of house plants. 
Since I work in Manhattan not far from her East Side 
apartment and I have a very flexible schedule, I said 
it would be no problem.

When I arrived at her building, I discovered that the 
doorman was one of the most gorgeous men I'd ever seen 
-- a fair-skinned Puerto Rican, maybe 21 or 22, with a 
great physique and, unusual among Latinos, the most 
captivating blue eyes. I couldn't help but stare.

He knew immediately that I was taken with his looks. So 
Raul chatted flirtatiously with me for a few minutes, 
before I excused myself and collected the key to 
Jessica's apartment. "I'll have a break soon," he said 
with a smile. "Maybe I'll come up to help you." 
Thinking little of what he meant and still a little 
thunderstruck by his looks, I simply said, "Sure. I can 
manage O.K., but that would be lovely."

Opening the door to the apartment, I discovered to my 
dismay that the place was a mess. Jessica had left some 
of the windows open, there had been a nasty storm the 
day before, and several plants had spilled on the 
floor, leaving dirt everywhere. I did not want to mess 
up my suit, so I removed my clothes and looked for 
something else to put on.

And then my deeper impulses took over. I could have 
just put on a frumpy sweat suit or the like. Instead I 
wandered into Jessica's bedroom and picked up a clingy 
black tank-top off the dresser. Its thin shoulder 
straps were lined with lace. With my slight stature it 
fit me perfectly. Then I pulled off my under-shorts and 
slid on a pair of black satin panties I found in her 
top drawer. 

My cock hardened as I rubbed it gently thru the thin 
material. The vision of that hunky doorman drifted thru 
my mind, making me incredibly hot. Next I found a pair 
of tight short-shorts, denim with cuffs. I have very 
little body hair, so the shorts and tank-top showed off 
my smooth skin. Looking at myself in the dresser 
mirror, I got very turned on by the pretty young thing 
standing before me.

Jessica's jewelry box stood on the dresser. She has a 
lot of money and she likes expensive jewelry. Opening 
the box, I found her lovely Concord woman's watch. I 
admired its small, round face, etched with delicate 
Roman numerals, set in a gold case, as I strapped the 
thin black leather band to my slender wrist. It looked 
just right.

Next I selected a delicate gold-and-silver link 
bracelet and matching necklace. I added a pretty ring 
with diamonds and sapphires.

Across the bedroom I found a full-length mirror. I 
posed in front of it, dancing with my hips bouncing and 
my hands over my head, excited beyond imagination by 
the new woman I had found inside me.

I might have cum on the spot, but I decided to wait and 
clean up before I jerked off. So I pranced about 
Jessica's apartment, walking like a woman with one foot 
in front of the other so my hips wiggled. It felt 
great, and so natural it scared me. I found it hard to 
keep control of myself even as my hard-on poked at my 
tight shorts.

So distracted was I that when the doorbell rang I 
completely forgot what I was wearing. I absent-mindedly 
asked who it was, and when I heard "Raul, the doorman," 
I simply unbolted the door and swung it open.

My Puerto Rican Adonis stood before me, checking me 
out, when it suddenly hit me that I was in drag. He 
stepped into the apartment and closed the door, and I 
started to stammer an explanation about the mess and my 
suit. It was useless, and I knew it. I hung my head in 
embarrassment.

"It's fine," Raul said, in that soft voice gay men 
often affect. I looked at him, and suddenly I was lost 
in those dreamy blue eyes. My mouth went dry.

"You look great," he continued. "And now I know exactly 
what you want. I like first-timers." I raised a half-
hearted protest, more scared of the passions he had 
unleashed within me than anything else.

But his next action stopped me. He moved closed to me, 
wrapped his muscular arms around my waist, and lowered 
his lips to mine. They were firm and full, and kissing 
him was a sensation more exciting than anything I had 
ever known.

I reached my hands behind his head, parted my lips, and 
welcomed his tongue into my mouth. My knees buckled, 
and Raul held me up as we kissed for what seemed like 
hours. From time to time our mouths parted and he 
nibbled on my neck. His rough, masculine hands roamed 
over my bare shoulders and across my tight ass. As he 
explored my body I did the same to his. It thrilled me 
to run my hands, so petite and feminine with my rings 
and watch, across the thick muscles on his arms.

I led Raul by the hand into Jessica's bedroom. Just 
holding a man's hand, our fingers interlaced, gave me a 
sexual rush.

I pulled off my shorts and panties but left my clingy 
tank-top on. Then, as I sat on the edge of the bed, 
devouring him with my eyes, Raul peeled off his clothes 
until all that remained were his blue bikini briefs. 
His large cock formed an enormous bulge that the briefs 
barely contained. A wet spot from his pre-cum showed 
through the fabric.

As I kneeled before him and eased down his briefs, his 
man-meat sprang free in front of my eyes. His love 
tool, I'm happy to say, was as magnificent as the rest 
of him -- about 8", circumcised, with a smooth crown 
and a thick shaft that tapered a bit toward the base. 
Light brown hair surrounded his heavy balls.

Raul took my hand and placed it on his erection. "Go 
ahead and feel me," he urged. I moved as though I were 
in a dream as I gently pumped his massive cock, so firm 
yet pliant, and fondled his nuts. Was I really playing 
with another man's meat, getting ready to let him fuck 
me?

We were in front of the tall mirror, and I saw this 
very effeminate transvestite rubbing a man's love 
organs. Looking at myself, transformed into a new 
sexual being, I knew I wanted this more than I had ever 
wanted anything.

"Please fuck me," I heard myself beg. Raul drew a red 
condom from his pocket -- he'd obviously come prepared 
for action -- and slid it over the tip of his cock. I 
unrolled it, licking the veiny skin of his prick inch 
by inch just before I sheathed him in latex. (Much as I 
longed to taste his cum, I still had enough of my wits 
to be careful.) 

Next I lubed his tool with a gel he thoughtfully 
provided. He maneuvered me on all fours in front of the 
mirror, and reciprocated my attentions by greasing my 
ass with the gel. As I felt his thick finger ease past 
my sphincter and probe deep inside me, he muttered, 
"Nice, tight fuck-hole. Just the way I like'em." It 
delighted me to know my body pleased my man-lover. A 
second finger soon joined the first, stretching my 
bunghole tenderly.

"We should start slow, so you don't get hurt," Raul 
cautioned. "Let me lie on my back and you ease down on 
me."

I straddled him, and bent forward to kiss him with my 
tongue. Then I reached behind to place the tip of his 
cock against my virgin love chute. As I slowly pushed 
down, my ass resisted for a moment, then suddenly 
opened to let his cock-head enter. I winced at the 
flash of pain, but it passed quickly. Heat began to 
radiate from my ass.

Very carefully I let my weight down, taking a bit of 
Raul's hard penis at a time. Oh, but it was thick -- I 
had never felt so full and satisfied, stuffed with his 
delicious manmeat. I was panting and moaning, and Raul 
was grunting obscenities in Spanish. The heat from my 
ass increased and spread; I felt my whole body was on 
fire with lust. As my ass settled on Raul's hips, we 
both smiled at my successful initiation. I tongue-
kissed my lover again.

When my back passage had adjusted to Raul's member, I 
began to move up and down. I slowly pulled halfway off 
him, then rocked down. After a few of these movements, 
I felt him start to slide more easily, so I picked up 
the speed. I also lifted further off him, until I was 
bouncing the full length of his cock, only its mushroom 
head anchored inside me. 

Sometimes I would slow the pace or settle back on him 
and stop, his full length lodged in my rectum. Then I 
would let my hands wander across his muscular arms and 
sharply-carved pecs, pinching his nipples. Jessica's 
jewelry made me feel like a wanton woman, the wealthy 
slut getting it on with her horny doorman. But in the 
mirror I also saw two gay men pleasuring each other. I 
liked that image of myself, too. Checking my fancy 
watch I discovered we had been fucking for almost an 
hour.

Raul understood that we didn't have all day, so he 
decided to take matters in his own hands -- literally. 
He wrapped his strong fingers around my cock and began 
to pump me to the rhythm of my up-and-down motion.

A churning sensation seemed to well up from my balls; 
my cock, swelling under his touch to a length I'd never 
imagined, turned almost purple. As he squeezed the 
base, I erupted, crying and gasping in ecstasy, gobs of 
white cum shooting across my man's stomach and chest. I 
collapsed on top of him, breathing hard.

When I could see straight again, I kissed him again and 
asked, "How would you like to enjoy my body, amigo?" 
Raul swung us around so that he was behind me. I faced 
myself in the mirror, my pert little rump in the air, 
resting on my elbows. Raul kneeled behind me, pressed 
his stiff cock against my butthole, and mounted me. 
This time he slid in easily, and I took him up to the 
hilt with no trouble.

We made eye contact in the mirror and watched each 
other's expression of lust as he began to fuck me 
again. I lost myself again in those blue eyes. Now he 
controlled the tempo, and it gave me great satisfaction 
to let him take command. He gripped my sides and thrust 
deeply in and out, fast and slow, as he wanted. My cock 
stiffened quickly again as he used my ass for his 
pleasure.

I looked over my shoulder and my man-lover leaned 
forward to kiss me. "Do you like my ass, big guy?" I 
asked in a sluttish, effeminate voice.
 
"Mmm," he grunted back, plunging harder into my eager 
back passage.

Sensing he wanted me to talk dirty, I went on. "Do you 
like fucking a pretty boy with jewelry? Like the rich 
bitch who lives in this apartment?" I imagined the look 
of shock and disgust on Jessica's face if she saw us 
now. "I'm better than she is. She's only got a cunt. 
I'm a boy, with a tight hole and a stiff cock. Fuck me 
like a boy! Ahhh! More. That's it."

With a great, guttural roar that shook the room, Raul 
exploded in my ass, his huge balls slapping loudly 
against my bottom and inner thighs. When he collapsed 
on top of me, I looked one last time at the pretty 
creature in the mirror. My adventure for that day was 
complete.

But I knew it was just the beginning. I told I would be 
back to see him again soon. His passionate goodbye kiss 
made it clear he would always find the time to help me 
clean Jessica's place again.

END

* * * * * * * * * * * * * * * * * * * * * * * * * * * *
It's okay to *READ* stories about unprotected sex with
others outside a monogamous relationship. But it isn't
okay to *HAVE* unprotected sex with people other than
a trusted partner. You only have one body per lifetime,
so take good care of it!
* * * * * * * * * * * * * * * * * * * * * * * * * * * *
Kristen's collection - Directory 41