My best friend through highschool had gone off to the marines, and instead of paying for a dorm my first year of college, we decided that I should stay at his mother's house. They lived much closer to the city than my family, and this was not very awkward, since I'd been to their house many times in the past few years.
I'd always considered Debbie to be very attractive and enjoyed watching her long legs meet the undersides of skirts most college girls would consider too revealing. Older and wiser, she enjoyed all things feminine, and for this I'd gravitated to her immediately.
As early as I can remember, there has never been anything quite like spreading open the edges of a pair of silky panties with trembling hands and slipping inside them. Before I'd ever even begun to masturbate, I knew the pleasures that came with a pair of stolen hose and garter-belt and had carefully gathered a small collection over the years from clueless girlfriends and unguarded drawers. In highschool I'd let my hair grow long past my shoulders, keeping it soft and curly for the imagined fingers of men who paraded my fantasies at night, holding me down with the heat and force no sextoy could ever deliver.
So when Debbie was at work, what more natural thing than for me to slip into her room and sidle over to her dresser? A velvet black bra dangling carelessly from a drawer made my cock twitch as though it had been licked; what wondeful taste this woman had! When I opened it I was rewarded with exactly what I'd come for: hose piled onto the silky mounds of thongs and panties with a few black and purple slips tossed to the side. I ran them over my fingers, held them to my nose to breathe in the heaviness of perfume and the natural scent of femininity. My now-aching cock was straining against my jeans for me to put some on, so I grabbed a handful, went to her bathroom, and closed the door.
First, I held up a pair of black french-cut panties with scalloped edges and eagerly put my legs through them, relishing the light feel of silk on skin as they slid up my legs to my cock. I slipped on some thigh-high hose next and then a garter belt. My breath was coming in gasps as I snapped the hooks into the fabric of the hose. The transformation from male to female is always smooth, as my body is very trim and slender, and the change is dizzyingly pleasurable. I couldn't wait to look myself over in the mirror, and I hooked the last of the soft velvet bra's hooks into place, its two cups clinging to my skin like mouths. Debbie's breasts were not large, but as the french say: "Anything more than a wineglass . . ."
The image in the mirror made me ooze drops of precum into the black panties, and I lowered them with no choice but to begin caressing myself. Nothing primes the nerves of a feminine boy's cock like the look and feel of lingerie, and once they are on his body, orgasm is never far. I moaned as the slightest touch of my hand wracked even my spine with lust. It was not long before my cock was jetting pearl-white streams down the toilet as I alternately massaged my ass and nipples with my left hand through the windows of silk and velvet. Stripping the undergarments reluctantly, I cleaned up and replaced them all as accurately as I could. Lying in bed that night, I could tell that staying with Debbie was going to be quite enjoyable, and I silently promised not to leave without some souvenirs.
She did not seem to notice anything out of the ordinary for the next few weeks, and I began making my visits to her bedroom drawers a regular part of the day, as it was I who nearly always got home first. It was here that I made my mistake, allowing myself to become lax in the rearrangment of her gorgeous underthings, but instead of confronting me, she did something sly.
Sharing a house means sharing the washer and dryer, and a pile of her clothes was nearly always laying around, stockings and thongs begging to be taken to a closet and massaged over a raging-hard member. I have never done this, however, because I consider it to be a classic mistake amongst transvestites. The laundry is a circuit wherein clothes move. That means the owner is more conscious about the location of these things, as opposed to the bedroom, where a woman considers her silky panties to be safe, putting them out of mind. I have always prided myself on resisting my urges in the laundry-room, but she had gone out of her way . . . There lay, very conspicuously, a pair of exquisitely made panties. The skimpy edges were trimmed in frills and pink lace, as close to a G-string as they could get with just partial covering for her tight ass. I did not think or care about their loss being noticed. I went to my room and immediately put them on, savoring every feel of their smoothness. I did not want to simply masturbate and replace them. I didn't want to ever give them back. So I put my jeans back on and walked back out to finish my laundry, reasurring myself that she had so many pairs she would never notice. Right.
She said nothing of my theft all afternoon but was quiet during supper, and I began to think for the first time that someone had caught me. She asked me how my classes went, whether I'd spoken with any girls. I told her that no, the girls in my class bored me. She seemed to consider this, barely touching her food. I decided, rather cowarldly, to end this awkward scene by taking my dishes to the sink and rinsing them off. That's when I felt her hands slip around my waist and the painted tips of her long nails plunge below my waistline to find the edge of her missing underwear.
"I thought you'd been doing this . . ." she whispered into my ear. What could I say? I only stammered meekly.
"I think I've got some other things in my bedroom that we could have some fun with. Do you think you can do that for me? After all, those panties you're wearing are mine", and with that, she snapped them back lightly against my skin. She began to strut back towards the bedroom in one of her short skirts, not bothering to see if I'd follow. She knew that from here on I'd be pathetically easy to control, and that I'd have no choice but to do anything she asked me for the sake of my own throbbing cock.
When I entered her bedroom she'd already laid out a slutty-looking outfit with thong, garter-belt and hose with matching bra, and some three-inch heels. Her makeup dresser was opened to reveal its rows of cosmetics.
"Don't just stand there, Mark. Put it on."
I have been nude before in front of others (I model parttime for art classes at my college), but never did I feel as naked as I did when I stripped before this older, commanding woman. Even in my embarassing situation, however, the sight of such a slutty outfit made my cock begin to tingle and my breathing slighly faster. I began with the black thong and removed it from the bed, Debbie walking behind me to watch. The feel of its skinny string was indescribably rich, at once invasive yet sexy.
"Slide it up further into your little crack" she commanded.
I did as she bid and felt my cock begin to stir. She gripped one of my asscheeks and whispered: "Now hurry up with the hose and belt."
I needed no second bidding, and in the course of sliding the hose up past my knees I could feel my member rising with pleasure. After I'd snapped the last hook of the belt and picked up the bra, it had achieved full erection and was now standing out from beside my thong. She helped clasp the last of the bra's hooks and whispered:
"Turn around so I can look have a look at my little whore." I turned slowly and let her eyes go down the length of my body.
"My, my, it looks like Mark really loves being turned into a girl. Well, then, you certainly won't mind stepping over here to this stool, then, will you?" I shook my head. For the next fifteen minutes she applied mascara and eyeliner, lipstick, and some slight blush to my soft features, effectively feminizing them to their fullest. Then, she motioned toward the bathroom.
She purred: "You look so pretty in that whore's outfit." I moaned softly as she squeezed the very tip of my penis in her soft hand, leaving a sticky spot of precum. My craving for release was becoming unbearable in the sexiness of her lingerie covering my body, perfumed fabrics awakening wild desires in me. I'd already shaved my legs earlier that day, a habit I'd taken up since moving out. The hose felt incredible against my smooth skin,
Grabbing my hips, she thrust her tongue into my mouth. Kissing those full red lips while dressed like a horny slut had me aflame, my member brushing against her leg, wild with sensitive nerve-endings begging to be touched. She removed her blouse to reveal a pair of petite breasts with large nipples. She guided my mouth to them and moaned softly as I sucked as much of the soft white flesh as I could. I teased her nipples with my teeth and felt her grip the back of my head tightly in reponse. The more of it I gathered into my mouth and sucked, the faster her hands ran up and down my back as she guided us gently towards the bed. She lay down first and spread her legs, hiking up her skirt to reveal her hairless pussy.
"Eat me out, you little slut," she ordered. I began kissing the inside of her thighs and working my way up to her dripping cunt until I was barely grazing her outer lips. I ran my tongue lightly over her engorged clitoris, savoring the taste of her juices as she grabbed handfuls of my hair in delight. She wanted to waste no more time and ground my head in hard so that I was tonguing her pussy in and out, occasionally circling her clit slowly.
"Faster, whore!" she shouted, fucking my face harder with each forward thrust of her hips. I took her clit in my mouth and sucked on it, meanwhile continuing in circles around it with my tongue. This drove her wild, and she began to moan and yell, her orgasm fast approaching. I could feel her juices all over my face and chin; I had never felt a pussy that was as soaking wet as hers. Suddenly her whole body tightened up, and she let out a long scream as her orgasm wracked her in spasms:
"Oh yeah, eat that pussy, you little bitch! Eat my cunt!" she moaned, pulling my hair and digging her fingers into the back of my head. Her climax ebbed through her in visible waves; I could feel each one through rapid tensing of her thigh muscles, gradually diminishing until she lay back, panting and smiling with satisfaction.
"That was good, you little slut. Would you enjoy the same?" My cock twitched at this, and I nodded eagerly.
She motioned for me to lie down, and began caressing the area between my balls and my ass faintly. I had never been touched that way before and let out a long moan.
"Do you like that, sweetie?" she asked, and with that she slowly licked from behind my balls, taking each in her mouth, up to the base of my shaft. I'd been given sloppy blowjobs by inexperienced girls before, and nothing had ever come close to this. She licked higher and higher up my shaft, never touching the head, sometimes sucking softly on my balls and then down behind them. I was in ecstasy. I never knew such pleasure could be gotten without even touching the head, which was now leaking sticky drops of precum into her waiting mouth. I thought I would die if she didn't take the head in her mouth, but she made me beg before she would give me such satisfaction.
"You want me to take it all the way in my mouth, whore? You think what you want matters? You'll do whatever I say, and you won't ask questions." I could only nod agreement. I would've done whatever she asked; my aching cock seemed about to erupt at any moment. I watched her red lips open into an 'O' as she lowered them down onto the very tip and slid them down further, so that half of my 7" were in her mouth. I moaned and writhed as her tongue flicked across the underside of the head, her hand still caressing behind my balls and going up and down the shaft. This continued for some time before she suddenly plunged the entire length into her mouth, making me yell in ecstasy. Suddenly she stopped. I immediately began to plead with her to let me finish, but she silenced me with a slap across the face.
"Don't try to tell me how to give pleasure to my whore!" she commanded, and I lay still. She then ordered me to get on my hands and knees.
"Now slide that thong down." I slid them down to my pantyhose-clad knees and knelt there with my ass in the air. Debbie licked her finger and cupped my now-delicate balls. She squeezed my cock and then traced a path down, past my balls, to my asshole, and I gasped in surprise and pleasure. She began to rub slowly around my tight hole, lubricating it thoroughly before she pressed gently on the outside. When she felt it give slightly she pressed inward until her finger had gone inside. I felt my sphincter spasming around its slight width, adjusting quickly until she felt me completely relax. Then she squirted some astroglide from the bedside table onto her two fingers and slid them both inside. I couldn't have ever imagined that getting fingered would have felt so good. To have someone else teasing your hole is an experiece that, gay or straight, every boy should have. She worked them in and out as I moaned, and then curved them downwards towards my prostate. I whimpered very loudly at this, and begged her to do it harder.
"Is that what my dirty little girl wants?" she crooned. I begged her to finger me harder, that I was her bitch and wanted her to fuck me. Suddenly she withdrew her fingers and went to the closet. I could only gasp and wait painstakingly for the sensations on my extremely sensitive ass to resume. I didn't care anymore about dignity or masculinity or my initial embarassment. Someone had discovered my feminine side and enslaved it, and all I wanted right now was to get fucked hard, to be owned.
"Alright, you little bitch," she said, "I'm gonna fuck you, and I'm not going to stop until I've cum." I turned my head to see that she had donned a big, realistic strap-on with a raised nub for massaging her clit. She spread my cheeks roughly and put the head of the dildo to my hole. Pressing inwards and then backing off, she gradually loosened me further until the head of the slippery strap-on was inside me.
"Ohhhh, yeah" she moaned, as the pressure on her clit increased, "Seeing your tight little cunt all stretched open is getting me all wet." With that she slid it all the way in, giving me goosebumps of pleasure mixed with pain. I gasped and moaned as she waited for me to grow accustomed to the huge cock in my ass. I'd never had anything that big before, and the feeling of fullness I got was indescribably good. I begged her again to fuck me. This time she held nothing back and proceeded to ream my slutty cunt until her hips were slapping against mine. I screamed louder and louder, the rapture of getting fucked like a whore making me ride that dildo hard; I backed up to her until we had fallen into a frenzied rhythm. She withdrew partially and re-angled her cock so that it was pointing towards my prostate and continued pumping into me. The pleasure I received from this made me see stars, and I felt a pressure building in my balls. I knew it wouldn't be long before I'd cum from such a hard fucking.
"Fuck my cunt! Fuck my cunt with that big dick!" I screamed, drunk on the waves of pleasure rocking my body. I felt my cock twitch with the first wave of my orgasm, and I began bucking backwards against Debbie's pounding hips, causing her to moan. Spurts of my cum began streaming out as I gasped and screamed for more. It seemed that I kept cumming and cumming until finally the hot jets subsided and Debbie ground her strap-on into my ass for a few more minutes until she began screaming also. Her climax brought her hips to mine as she clasped my hips and ass, pulling me onto her cunt as her back spasmed and wracked: "Ride that cock, you fucking slut!" she shouted as I moaned and let her take me. When she had finished, she slowly drew out and went into the bathroom. I lay on the bed on my own cum-drenched thong, a warmth and satisfaction coursing through me that no sexual act had ever yielded to me.
When Debbie returned, she was smiling through the sheen of freshly-applied lipstick and had put on the black velvet bra I'd first seen in her bedroom.
"How did you like getting fucked like a girl?" she asked. I told her that it was incredible, and that I'd never experienced anything like it. She looked very pleased, and kissed me.
"I'm glad you like it as much as I do. It's gotten lonely in this bedroom since my husband died, and I've had no lovers since with such an open mind." I let her run her fingers through my hair for a while before she sat up and traced a finger down my cheek.
"Sit up and put this on while I brush your hair." she said, holding out a pink slip. That night we slept soundly together and awakened the next Saturday morning with the entire day ahead of us to screw and buy new lingerie.
Email me if you liked my story. Tell me which parts you liked, and I want to hear your ideas or stories about transgenderism. Sachsa_Kyer@yahoo.com