The author of this story is Jakladd.
Like many cross-dressers, it started early for me. I had been sick and fragile much of my pre-teen years and only returned to decent health around 12. By my early teens I was lithe at 5′ 9″ and barely 130 pounds, too small for masculine activities and babied by my mom.
Dad had given up on a son to pursue masculine pursuits. I had a fascination with my two older sisters’ undergarments which overwhelmed my senses and the times when I was alone in the house I discovered how stimulating it was to put on a pair of sisters used panties.
One particular day I disrobed in my sisters’ bathroom and my teenage cock throbbed as I pulled on a pair of Brenda’s pretty, silky bikini panties. They were shimmering white with pink lace trim and a tiny pink bow in front. It was pure excitement as I felt their silky sensuousness on my boyish manhood & cute little ass.
My erection tingled as I rummaged through a bevy of bras, camisoles, panties, skirts, blouses and feminine clothing. Gathering up a silky camisole I went to my room and pulled out some hidden girlie magazines. With the soft sexy sisters used panties hugging my erect penis I pulled on the silky camisole it made me feel so feminine and I felt dizzy by the whole taboo experience. Never had I been so aroused leafing through the magazines eyeing the naked women in their silky, skimpy attire.
I furiously masturbated when my excited penis then shook with a thunderous ejaculation. I had not cum for a few days and it seemed I had never been this sexually excited. Cum shot out with such force that some of it splattered up in my face. There was cum in my eye and over my nostrils & lips with big gobs of cum all over my sister’s camisole.
My head spun and my breathing and heart rate were accelerated as I luxuriated in this mind bending orgasm. Slowly I came back to reality wiping cum from my face as I experienced the taste and scent of cum for the first time. In a bit of terror I realized that I had soiled my sister’s camisole and sisters used panties with my cum. Washing them in the sink I dried them as quickly as I could and returned them to the hamper, hoping my erotic foray would go unnoticed.
Guilt racked me for days afterwards and it was another week before I got the nerve to try on another pair of panties. With everyone gone in the house, I sneaked into my other sister’s room, Annie’s, and began a spree trying on as many panties that caught my eye as well as bras, skirts, hose. A particular pair of hot pink micro fiber string bikini felt incredible over my privates when I started looking at dresses from the closet.
Finding her yellow & gold spaghetti strap silky dress that I loved seeing her in made my head spin as I never could imagine how exciting it was to be so feminine. Trying it on, it fit wonderfully and my nipples got hard as I felt them through the shimmery material. Wearing a dress made my whole body tingle as I sashayed around her room. Rummaging through her drawers I found some pink stockings that made me breathe in excited breaths as I pulled them up my legs and I felt like a child at Christmas finding all these wonderful feminine things.
With the stockings on my legs I had been longing to try on some high heels. A pair of 5″ silver strappy sandals actually fit me and after fumbling them on I wobbled around her room intoxicated with the taboo excitement of what I was doing. Stopping ever so often to admire myself in her full length mirror my little penis was hard as stone and tingled in the pink sisters used panties. With more confident strides in the high heels I made my way to the bathroom that my sisters shared in between their two bedrooms.
The whole experience of feminizing myself grew as I perused the incredible number and array of cosmetics – lipstick, eye-shadow, eye liner, mascara, foundation, blush, lip gloss. It was mind boggling all the colors & shades of feminine make up art; girls were so lucky to be able to preen and paint themselves pretty like this.
With my hands shaking from excitement, amateurishly I put on vibrant blue eye shadow, mascara, blush and the sweetest bright pink lipstick. OMG I felt & looked like such a pretty girl as I again admired myself in the mirror. Then out of the corner of my eye something caught my attention in the laundry hamper. On top of all the clothes was a flowery pair of soiled sisters used panties. The cotton panel was crusted with what appeared to be a dried mucus substance. Inquisitively I pulled them to my nose; I was not ready for what the scent did to me.
It overpowered my senses as I smelled the intoxicating scent of guttural femininity. If my penis was hard before it was doubly so now as I drank in the sultry sweet essence of my sister’s femininity. My head spun as I fell to my knees and pulled on my excited penis extending from the pretty dress and the soiled panties glued to my nose. Needless to say it only took a few pulls and I ejaculated many powerful ropes of cum over the carpeted bathroom floor.
The sensation of feeling was so intense as I gasped for breath with the aromatic panties still glued to my nose. Setting the panties aside for a moment I got up and pulled the dress off over my head, not wanting to soil such a nice dress with my cum. Gaining confidence walking in the high heels I hung the dress back up and wearing just the pink sisters used panties & pink stockings & heels I returned to the bathroom. I was still hard! My penis was still just so excited and as I saw myself in the mirror I thought I looked hotter than ever. Something about high heels, stockings & panties with a naked torso and chest turned me on no end.
Picking up the soiled panties I inhaled their spine tingling aroma again as I jacked off again as I lay down on the floor. Running my hands all over my body with the fragrant panties draped over my nose I just loved the feeling of the hose on my legs; the high heels made me feel so girlish; my little bubble butt felt divine in the silky panties. It took a little longer but as I mashed the dirty panties into my nostrils I furiously masturbated to another bone shaking, mind bending ejaculation, cum fountain-ing all over my belly and chest.
Laying there with my mind spinning & my heart racing I then realized I had smeared lipstick on the soiled sisters used panties. In a moment of indulgence I wiped up the cum that was all over me with the panties & greedily decided to take them to my room with me. I showered to get the make up & cum off of me. That night I pulled the panties out while I was in bed; with the feminine aroma of my sister coupled with the tangy scent and dampness of my own cum my penis got so hard as I alternatively sniffed them and rubbed my hardness with them.
Another numbing orgasm followed and again I sopped up the cum with the panties. Once more in the middle of the night and again early in the morning I jacked off again with the sperm crusted panties which by morning were still a bit damp with my sperm. Laying in bed that morning with the fragrant damp panties glued to my nose the scent was overpowering; by now the predominant scent was that of my own cum after many excited ejaculations had doused the feminine flowered underwear.
There was just enough of the aroma of pussy seeping through with the cum scent to make my cock ever harder before yet another powerful sperm bath to be sopped up with the panties as I reluctantly pulled them away from my nose to wipe up my excited mess.
With what little rationalization I had left I washed the sisters used panties in my sink in warm soapy water in hopes of cleaning my repeated cum blasts from my sister’s panties. This was also sad in that I was giving up such an exciting piece of clothing that had given me so much pleasure.
The panties were dried and returned at an opportune time to the hamper when my sisters were not in their rooms. Quickly I rummaged through the hamper in hopes of finding another pair of pussy scented panties but disappointment reigned supreme as what few panties were in there were not that pretty and had very little or no scent on them.
My quest was set from then on, always looking in the clothes hamper for pretty panties and especially those sweet smelling pussy mucus scented sisters used panties. With two pretty sisters I was fortunate to fairly often find a fragrant pair of silky panties and I would slip into a funk of unrelenting masturbation, cross dressing and feminine idolization. The laundry room was in our unfinished basement and at the other end of the basement there were several old armchairs, a musty old couch and a lamp.
I could be alone here pretending to be playing video games when I was really looking at pilfered Playboy’s, Penthouse’s, Oui’s, Hustler’s, Cheri & Swank mags. I knew every page, every girl that followed on the next photo spread, every exciting sex scene from the raunchier mags with girls sucking cock, getting fucked and generally getting ejaculated on with cum.
I loved being girlish wearing sisters used panties, camisoles, bras, stockings and heels and masturbating two, 3, even four times a day. The back pages of the raunchier magazine had all the sex ads for videos and phone sex; it was just so exciting seeing the myriad of ad’s with all kinds of sex, gay sex included.
My infatuation with panties, masturbation and all things feminine ruled my world, though I was a good student, however geeky, and I did have a few friends. One was William and we’d at times play video games in the basement on the couch. Inevitably we’d talk about girls and sometimes look at my stash of girly magazines.
One day when we were gawking over the luscious naked women in the pictures my arousal got the better of me & I went to the laundry room there in the basement and rummaged around for a few pairs of sisters used panties, one of which was pleasantly soiled and I took a few long whiffs heightening my arousal even more.
Returning to where Will was looking at the magazines I tossed him a pretty pair of pink panties while I clutched a pair of satiny cream colored string bikini panties. Will looked up at me in amazement but I said nothing but was fantastically excited to be sharing my fetish with another person. Not being able to help myself I stood up & undid my jean shorts and pulled them off along with my boys underwear. Smitten with lust I sat back down and began to look again at the magazines with my hard little penis exposed to my friend.
Somewhat in shock but also very aroused Will unzipped and pulled out his hard penis as well. Soon I was rubbing the sisters used panties over my hardness further exciting me as Will then followed suit. The whole erotic scene of two boys masturbating with girls panties was very quickly too much for us and in no time I was flailing about as I pulled frantically on my penis and huge ropes of cum ejaculated out over me onto my hand, the panties, my stomach & tee shirt.
Will watched in amazement as I came and he soon followed suit ejaculating into the silky panties. We gasped in embarrassment (though we both really enjoyed seeing each other cum) and quickly got dressed. Needless to say after Will left I took the panties he came into and jacked off sniffing another boy’s cum in my sisters panties.
Nothing was said of our little episode when we saw each other but the following Saturday we were alone in the house and playing video games in the basement. There was a little sexual tension in the air due to the previous week’s jack off session. We began leafing through some girly magazines and both were soon very hard.
I planned forhis and before Will came over I had staged some of my sisters used panties in the basement bathroom. Underneath my clothing I had on stockings & panties from one of my sisters. Pulling out the hidden panties I tossed one pair to Will & I took the other, both were soiled with the scent of my sisters. Standing up I stood before him all and took off my tee-shirt & jeans my hard little dick tenting in the panties.
Wow, we were both so hard. Will undid his pants and started jacking off. Pressing my frilly pair of panties to my nose Will got the hint and soon were were both intoxicated by the feminine scent of the panties.
As we lay there on the couch I reached over and placed my hand on his penis. Sliding down I did something I had fantasized about for a long time, I slipped Will’s cock into my mouth. Oh how sweet it tasted and as good I’m sure it felt to Will it sent shivers down my spine and electrified my own hard penis as I began sucking off my best friend. It was heaven and up to this point in my life I had never been so sexually aroused.
As best and loving as I could I sucked and kissed and licked Will’s nice penis which was substantially bigger than my own. Will lay back oblivious to everything except the pleasure I was bestowing upon his penis as he continued to sniff the heavenly scent of my sisters used panties. With more and more cock sucking obsession I continued sucking off another boy for the first time in my life. Finally happened. Writhing and moaning and humping up into my mouth Will then ejaculated many excited gobs of creamy boy sperm into my cock famished mouth.
After tasting my own cum so many times I knew how much I would like the taste of his as I hungrily lapping in every pearly drop of his luscious cum. As he wilted and lay there spent I climbed over him. He lifted me up and felt for my penis sticking out of my sisters panties. Excitedly I humped it into his hand and in very short order began to ejaculate my own sperm all over his tender naked boyish belly & chest.
In stunned silence we gathered our wits about what had just transpired. For me it was a sexual expression that would define my life. For Will however he was very conflicted about what had happened and told me he did not want to be gay and he stopped coming over and hanging out with me.
In the same time frame I actually had a girlfriend, Kelly. She was really not all that cute with glasses & acne and frizzy unruly brown hair but she was a slender girl and just being around her excited me no end. Kelly was somewhat of a social queen and had a special magnetism with boys. She would choose a boy, like she did with me and then quickly move on to another.
Kelly was also very athletic and a star on the girls soccer team. Her parents both worked and her and her older brother both had the house after school till around 6pm. I was mesmerized by her as we would spend time in her room after school. There were a few times she let me feel her up under her shirt and as a boy I cant tell you how exciting it was to be this close to a girl – her scent, kissing her, feeling her up, just being near her.
Being somewhat of a tease she would never let me get too far though she did jack me off a number of times; she knew she could control boys very easily by doing this. The few times she did jack me off was absolutely exciting beyond belief. The feel of her soft feminine hand on my penis made me harder than I had ever been and she really got into it urging me on as she brought me to climax, messing cum all over her hand.
I was totally under her spell and she knew it. In my arousal being with her when I was able to feel her up, just touching her soft little breasts through her bra was a special reward (when she actually let me touch them without pulling my hands away).
Her panties fascinated me me & though I rarely saw more than a glimpse of the waist band one day I slipped my hand into her shorts and touched her pussy through her panties. Fully expecting to to have her pull my hand away she let me continue and I could tell she was getting very turned on by this. With my hand rubbing her through her panties for quite some time I then slipped my hand inside the sisters used panties and actually touched her pussy.
Again she did not stop me and my middle finger slid between her slit and as I continued. Kelly was very excited and my finger slid deeper into her. Soon she was riding my finger oblivious to everything except the pleasure my finger was bestowing upon her. Breathing heavily and shaking Kelly started moaning and whimpering before slowly shuddering and calming down. She pushed my hand away and politely sent me on my way.
Needless to say I was very excited about what had just transpired and was hard nearly the whole way home. A t home I stripped & put on a pair of my sister Brenda’s panties. Then as I was about to masturbate over the incident I brushed my nose with my finger that had just brought Kelly to climax; OMG it smelt divine! Much like the scent I would find on my sisters’ soiled panties it drove me wild with sensory excitement.
With my right hand glued to my nose I had to jack off left handed giving a totally new feeling and heightened stimulation with the pussy scented finger urging me on. Like a rocket I came splattering cum all over me & the sisters used panties. The smell turned me on so much I did not wash my hand for 2 days and must have masturbated 6 times in that stretch. Kelly was at school late for soccer practice Tuesdays & Thursdays and I generally visited her on Monday & Wednesday afternoons before her folks came home. Sometimes her brother was around, sometimes not.
One particular week was a Monday school holiday with no classes & the next day Tuesday I absentmindedly went over to her house, thinking it was Monday. Her brother let me in, looked at me funny when I said I’d just wait for Kelly in her room like she was on her way. I waited quite some time before I realized it was Tuesday and she was at soccer practice.
I decided to leave & went to pee in berbathroom across the hall. Like any boy I left the door open as no one was around and as I finished I spied her laundry hamper. A naughty excitement came over me as I rifled through the hamper in the quest I knew only too well; looking for soiled girls panties. I was not to be disappointed and came upon a cute pair of silky bikini panties, white with small colored polka dots, pink trim and a tiny bow in front.
As I lifted them to my nose I was mesmerized and intoxicated by the scent, it was the divine sultry feminine aroma I knew so well from sniffing my sisters panties. Just then in my moment of olfactory enjoyment Kelly’s older brother was standing there at the doorway.
“What are you doing you pervert?” he bellowed. He was much bigger than me, easily 6 foot and 175 pounds, an athlete at school.
In terror I pulled the sisters used panties away from my nose and stammered incoherent mutterings not being able to explain myself.
“You little fairy. Put em on. Drop you shorts and put them on”, Kelly’s brother demanded as I stood there in shock.
“Do it. Now. Or everyone finds out” he commanded as I hesitatingly undid my shorts, kicked my shoes off and pulled down my shorts and underwear with my shriveled little penis now exposed to him.
“Take your shirt off too you little queer” he shouted, as I trembled.
Meekly in fear I did as he told me and was shaking as I pulled Kelly’s panties up my legs. I avoided eye contact as I stood there naked except for my girlfriend’s panties I had been forced to put on.
“OK you little faggot, time for some fun” he smirked as he was unbuckling his belt and pulling down his pants and underwear, exposing his large half hard cock to me. “Suck it” he commanded as he wiggled closer to me and pushed me down by my shoulders onto my knees. Trembling and shaking I timidly reached up for his cock.
While it was in a way very arousing and my penis was getting hard, this was a forced sexual encounter so it was much different than my encounter with Will that I instigated.