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.