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Cross-Dressed To Score
by Tom D. (address withheld)

* Cross-Dressed To Score *

***
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...
***

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
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