Dressing Up
by Anonymous
We spent nearly the entire morning shopping at women's boutiques and lingerie shops, and I was looking forward to trying on my newly bought clothes. I was in the privacy of a rented room at a Victorian hotel with my new friend, another young crossdresser, whose femme name was Lisbeth. We met at a local Transvestite convention in Sacramento, where we soon became fast friends. He was great fun to be with; slender, blonde with green eyes, and like me, could easily pass in public as a pretty girl. As we walked around town that day, we looked like happy girlfriends. I stand 5'7" and looked up to him as my beautiful big sister, who walked so tall and gracefully at 5'10".
I was really anticipating coming back to the inn, removing our dresses and slipping into some of the wonderful loungewear we just bought at Victoria's Secret. I loved to dress up in feminine sleepwear. Though it was always such a pleasure to put on lingerie with lots of ribbons and lace, I found myself blushing furiously at the thought of sharing this experience with another crossdresser.
My companion left to change in the adjoining bathroom, and I opened my box of new lingerie. I ceremoniously laid out the pretty things on the bed. I stripped down to the buff and selected one of the sensuous undergarments: a pretty little camisole set. Pressing it to my lips, I revelled in its luxurious feel and fragrance .
I slipped on the lovely garment, evaluating myself in the full-length mirror, noting how the silken, filmy material draped over my curves with provocative sensuality. Turning sideways to view the shiny panties that clung to the roundness of my bottom, I caught sight of Lisbeth as he entered from the next room.
He was all dolled up in a gorgeous satin and lace gown with a sweeping hemline that swirled around his legs as he approached. Standing in front of me with a coquettish smile on his lips, my friend looked really adorable with all the charm of a sweet, good-looking girl in the seclusion of her boudoir.
As we stood facing each other, Lisbeth suddenly put his hand up to my cheek and told me how appealing I was in my negligee. Feeling a bit embarrassed, I laughed at his remark, but felt secretly delighted with his compliment. I turned around in a slow pirouhette to show off my pale peach satin outfit with its flouncy lace peplum, matching panties and a ribbon on the bodice.
"Oh, isn't this pretty!" he said, fingering the ribbon in my long brunette hair.
I felt girlish and romantic as he praised my looks and stroked my hair, but I soon became flushed and self-conscious, when I realized I was getting an erection. I dropped my hands in front of me, hoping he wouldn't notice my nervous excitement. But he saved me from complete embarassment by changing the subject and suggesting we should have something to eat.
He asked me to inspect the house luncheon menu with him. He took my hand and led me over to the bed: a huge old-fashioned one. It had a fancy pink and white canopy and a floral print bedspread with a ruffled lace trim no less!
When I sat down next to him on the coverlet, he moved so close to me, our nylon stockings brushed against each other, making a swishing sound. We shared the single menu and each held a page. He pointed out the possible choices for lunch, and I couldn't help but notice the heady fragrance of his perfume, the way his hair framed his pretty face and the smoothness of his skin. I felt myself breathing too fast and tried to calm down. I pointed to an interesting menu item and began to say something, when he took my hand, demanding I hold still, and reached up to my face to pull a wisp of hair away from my eye.
As I held motionless, he smoothed the errant lock back into place and then kissed my cheek! My heart skipped a beat. All at once I felt a sudden anxiety at being alone with him. I wanted to leave, but dressed in such intimate attire, how could I gracefully make an exit?
He kept gazing at me with such imploring sweetness, I quietly let him stroke my arm and caress the back of my neck. I slowly relaxed. My head bent forward, and my thick dark hair fell around my shoulders. I became more and more sensitive to his touch, so very soft and teasy, as he put one hand around my waist and continued to massage me with the other. Lisbeth's attentions were melting my resolve to leave. I sighed, peered up at him through my lashes and saw him smiling at me.
It came as no surprise when he laid me back against the pillows on the bed. I looked up at the canopy overhead, absently noted the floral design, and then turned my head toward him. Our lips met in a soft, affectionate kiss. It seemed so innocent --- to indulge in this warm touching of mouths. I snuggled closer in his arms, trading more and more kisses. He could tell I was becoming aroused and kissed me more firmly, more wetly. His lips were full like a woman's and his tongue so warm, slowly licking my lips, my cheeks, but always returning to my mouth, the full kiss, again and again. I was captivated and thrilled. For a moment, he took his lips off mine to kiss my throat. Partially released from the spell, I dreamily voiced my concern.
"Lisbeth?... Lisbeth, I think we should stop. I haven't been with a man before, and I think ... maybe I should go."
He ignored my weak protest, telling me to hush. And once again kissed me full on the mouth, coaxing my lips apart, venturing inside my mouth. My lips parted more or less willingly, and I received his probing tongue.
I was nervous and trembly, my fingers shaking, as I reached down and gently caressed the slippery smooth material covering his thighs. My small show of affection clearly increased his ardor. There was no mistaking the hard-on pushing against me, and my curiosity began to overwhelm me. Lisbeth must have read my thoughts. He took my hand and quickly slipped it down, cupping it around his groin, and held it there as we kissed. I tentatively enclosed my fingers around the hard tube of his prick. I could tell right away he liked my hand around his penis. It was such a marvel how it moved and throbbed, as I squeezed and stroked its firm flesh.
Lisbeth reached for the front of my panties, pulling them down, so that he could really get at me. He slipped his hand between my thighs and stroked my cock. I felt a terrible rush of excitement that got me even harder. We fondled each other's pricks, kissing mouth to mouth, sucking tongues and rolling about in our nighties. I urgently rubbed my bare penis against the rigid bulge beneath the sheer nylon and fully expected to come all over the front of his panties with the intense stimulation. But I managed to free myself from his embrace --- just because I had to have a look at the stiff pole he kept poking between my legs.
I knelt between his thighs, my face just inches from his crotch. His knees fell further apart to reveal lacy panties stretched tightly across his stiff organ, so accessible and so curiously enticing. I directed my mouth between the fluffy garters of his stockinged legs and kissed the gauzy silken fabric, tracing my tongue over the smooth outline of his penis. Over and over, I pressed my lips against the warm silky mound, whispering how sweet it was.
He slid his hand under the waistband of his panties and deftly pulled out the object of my desire. His naked cock appeared flush and swollen as he held it in his hand.
"Go ahead," he said softly, "kiss it."
Seeing a drop of glistening sperm on the tip of his beautiful prick, I hesitated. I avoided the drops of semen collecting at its opening and planted a light kiss on the shaft of his penis.
"Lick me, Sara. I want you to lick my come!"
For a moment I stared in fascination as his quivering prick secreted another tiny amount of fluid. I promptly obeyed him and ran my tongue over the tip, licking off the starchy white secretion, rolling it about in my mouth. The taste of Lisbeth's seed seemed to act like an aphrodisiac: I repeatedly licked the head, trying to coax more of the sperm to come out. I ran my tongue along the full length of his shaft, but not quite taking him in my mouth. He rocked his hips up and down, offering his prick to me.
"Please, darling, take my cock all the way into your mouth," he begged, "Suck me!"
My heart was pounding, as I formed my lips into an O shape, fitted them over the bevel-shaped tip and drew him deep into my mouth. He closed his eyes and smiled with the pleasure of feeling my lips around his penis at last, my mouth full of him.
I was enjoying the taste of his penis so much, I slowly moved my lips up and down, giving him the best virgin cock-sucking I could. Again and again, a little harder and faster, I sucked away at his cock, the tip of it going further and further down my throat.
"Suck it, Sara. You love my cock, don't you!"
I could only murmur with delight and increase my licking. I was thrilled with the taste of his penis caught between my girlish lips and serviced him like a lusty chambermaid going down on her master. I felt him start to tremble and shudder. Lisbeth placed his fingers on the back of my long hair and pulled my head closer to his crotch. He made little cries of pleasure: "Oh, honey, ohhh..." Then he arched his back, and his cock immediately blew a surging stream of hot milky sperm into my mouth. I could feel the pulsating gland beat hard against my lips, as I swallowed warm jets of semen squirting down my throat. After a minute I let the limp penis fall from my mouth, but kept my hand on it to examine his darling dick up close.
"Oh, you came so hard, Lisbeth!" I said, touching my lips to the tip of his prick, when a fresh spurt darted into my mouth!
The beautiful girl-boy sat up and nuzzled me all over, kissing my neck and stroking my bottom. He kissed me passionately and pushed his tongue into my mouth, as he massaged my very excited prick through the lacy panties I was wearing.
I was nearly frantic with his teasing and couldn't wait for him to wrap those pouty, rosy lips around me. I moaned with anticipation, as he seized me about the waist and pulled me down onto the sheets.
He covered me with kisses and caressed my body as we coiled about on the bed. Lisbeth gradually worked his way down to my belly and ran his lips over my smooth skin. I could feel his warm breath on my tummy. He untied the satin bow on the slit of my crotchless panties, and my rigid penis poked through between the lace edges.
I became very restless and tried to keep from writhing about on the sheets, until he finally spread my legs apart and bent over me. I loved the sensation of Lisbeth's long smooth hair on my thighs and against my abdomen as he closed his moist lips around my cock.
His tongue went around the tip, slowly, very slowly at first --- and not just the edge of his tongue, but the whole length and breadth of it, soft, warm licking me in slow, great, warm repeated kisses.
I loved the blunt feel of his teeth as his mouth pressed against me. A flush crept along my neck. My lips parted, and as my breathing became heavier, faster, so did his sucking on the pink smooth end of my penis.
My hands felt for Lisbeth's hair, the beautiful soft texture of it, and with the slightest pressure I kept his head, the movement of his tongue and lips paced to the tiny up and down thrusts I made with my hips.
I gave myself to him, pushed myself against his mouth. My face was hot, my prick ached with wanting him. I watched his head moving faster, faster; he was bent over me, his tongue moved faster and faster.
I was almost there, he sucked excitedly at the morsel in his mouth, till my prick stiffened and shot its juice past Lisbeth's tender sucking lips. He reached up and hugged me, and we lay together in each other's arms. Two satisfied damsels wearing lingerie, we drifted off to sleep in feminine bliss.
After the pleasure of love and sleep, I awoke to find Lisbeth kissing my throat and his hands stroking the back of my neck and shoulders. Our parted lips met again, pressing together so warmly.
He cupped his hand around one of my ass cheeks and massaged it with motions that crept ever closer to my anus. I guessed what he wanted and turned on my side to move my butt closer to his roving fingers.
He quickly found the spot, and I felt his finger tickle my opening and then push deeply inside. I surrendered to the startling unusual sensation by making little rocking motions in time to his finger darting in ond out of my anus. As he fondled and fingered my bottom, I kissed Lisbeth all the more fervently for making me feel so weak and yielding in his arms.
"I want to fuck you now, Sara," he whispered urgently in my ear.
"Okay, darling. I am yours." I whispered back at him.
I was completely his now; my cock was taut and hard at the idea of having a penis penetrate my bottom. The sight of Lisbeth's rosy arrow-pointed maleness up and ready between the folds of his gown made me eager to please him.
I realized, with a tantalizing feminine thrill, that I really wanted to be filled up with his prick. I wanted to feel like a woman! So at his request, I eagerly rolled over with my face on the pillow and knelt on all fours, and he threw up the skirt of my camisole, exposing my white rounded buttocks.
Kneeling up he rubbed some kind of cream on the tip and length of his prick and also annoited my tight little bum-hole now quite stimulated and somewhat enlarged by his fingering me. He told me to push my bottom well out behind, with my legs spread wide apart so as to give him every access.
I was so excited at acting out this womanly, submissive role that I wriggled about, pushing my dainty asshole at him, just begging to be fucked.
Now properly lubricated, Lisbeth guided his prick between the lace edges of my crotchless panties right to my puckered little pink hole, and directly I felt the hot head of his cock placed to the opening. I reached around behind me to spread my buns far apart and held very still while his prick gently dilated my opening.
I felt the blunt knob end against the ridges of my anus. It forced them apart and began to enter my hole. I let out a gasp as he stretched me, but gradually my sphincter muscles relaxed, adjusting to his probing penis. Inch by inch, he began moving slowly in and out at the entrance to my anus.
When Lisbeth was convinced I was completely relaxed, he withdrew and lubricated his prick with still more cream, and slowly and carefully pushed his way back in.
"Oh, Lisbeth, I feel your prick. I feel its head going in -- so far up my ass!"
I continued to hold motionless as he worked his prick into me, until I knew he had penetrated me to the hilt, for I felt the soft hair around his prick against my bottom. I soon started to enjoy the delicious sensation of my lover's femme cock inserted in my anus. I couldn't believe I was doing such a thing. I was being fucked by a man and enjoying it!
"Your ass is so soft and plump, Sara. It just sucks in my cock!"
Then holding my hips, he worked his organ smoothly in and out, telling me to push back my bottom to meet each thrust of his prick. As Lisbeth's prick went in and out, my round bottom-hole enclosed it with an avid suction like a girl's wet pussy.
By his occasional sighs and the lovely rhythm of Lisbeth's movements, I could tell he liked his penis up my bum, the soft cheeks of my bottom rubbing against his belly. I pulled the lace edge of the pillow closer to my mouth and started sucking on its scented fabric. I closed my eyes in a dreamy state of womanly passion, and my perfumed hair brushed against my cheek as my whole body rocked to meet his every stroke.
I had my legs wide open. I couldn't get enough of his cock up my ass. I felt like I was all cunt! I gasped and moaned, backing my exposed bottom to meet his thrusts. My own penis was rigid as steel, as I thought how lovely it was to be like a girl getting fucked and fucked!
"I'm a cunt, Lisbeth! I'm a cunt! Fuck me, fuck me!"
Lisbeth took hold of my dangling prick in his hand and masturbated it, calling me a lovely cunt and a sweet girl getting it up the ass! I was on the verge of going out of control: he was stimulating both my anus and penis with such exquisite attention! And I was delighted to be giving him such sweet pleasure with the delicious throbbings of his cock in my bum-hole.
I could tell Lisbeth was nearing the moment of ecstasy, when I heard his deep drawn sighs and noticed his body making little trembling motions. Perceiving by the twitching of my rump that I was about to spend, too, he pumped even faster with his cock.
Overcome with pleasure and nearing his orgasm, my lover gave a sound and shoved even further inside, his belly shuddering against my buns. I knew Lisbeth was coming and pushed my butt far back to hold his prick in my anus. I could feel it throbbing, as it began to toss off with spasm after spasm. His juices shot up me, flooding my anal canal with a warm infusion of ejaculate. My own penis, terribly aroused by the touch of Lisbeth's delicate smooth hands --- and the terrific notion of my insides being filled with hot sperm, pumped its seed all over his fingers.
Fin