Feminized for the Very First Time: 8 Books Feminization Anthology

by D. L. Savage

  I could tell by the tone of her voice that it was something sexual, and again I felt so lucky that I was marrying a woman who was so open and easy about stuff in the bedroom – the perfect counterpoint to my years of shame and secrecy, even if I still couldn’t tell her everything.

  I did as she asked, walking over, wondering exactly what kind of naughty little thing she had on her mind. But her thoughts soon became clear, as she leant in to kiss me the moment I stood before her, her fingers tugging eagerly at my belt.

  “We’ll have to be quick,” I murmured between kisses. “Jordan is picking me up any time now ...”

  “Oh don’t worry,” she said, tugging my cock free from my pants then falling to her knees before me, looking up at me with those big blue eyes that got me rock hard instantly, “this won’t take long. I just want to give you a little something-something so it’s me you’re thinking about when you’re getting your lap dance ...”

  I watched, transfixed, as she closed her eyes and opened her plump lips, taking my cock deep into her mouth, quickly going to town on it – using all her best moves. Seriously, Jenny gave the best head I’d ever known; always keeping me on my toes with some new trick or tip she’d read about online, always giving it her all, seemingly wanting nothing more than the pleasure and reward of getting me off.

  And tonight it really did seem like she had a few new tricks up her sleeve.

  I groaned, as she began to softly rake her teeth up and down my shaft for a moment, before sucking again tenderly on the head, jacking my dick in time with the motions of her mouth, her other hand cupping my balls, kneading them, bringing me closer and closer to boiling point.

  But then all of a sudden, she did something I totally wasn’t expecting.

  Because the hand that was cupping my balls suddenly slid further backwards, until her fingers were pushing right between my butt cheeks, her fingertip touching right against my butthole.

  I froze, my heart pounding even harder than it had before, staring down at her in a mixture of surprise and ... horror.

  We’d never done any kind of butt stuff - at least this way round - before; only ever with Jenny on the receiving end, and I found myself consumed with all kinds of conflicting new emotions.

  Sure, I’d been curious and played with my own ass a few times in private – nothing major but just a little experimentation. But never with anyone else.

  Maybe it was my weird upbringing, but there just seemed something embarrassing and, I don’t know, submissive about being fingered like that by a girl.

  But at the same time, holy shit, it felt so good, too, as Jenny pushed her finger a little way inside me there, slipping it all the way past the first knuckle into my tight little hole as she continued to suck my dick.

  I let out a loud groan, taken aback by just how damn good it felt, and Jenny’s eyes opened, looking up at me in surprise.

  “Oh, you like that, do you?” she murmured around my cock, those pretty eyes sparkling at me, and all I could do was nod, my knees trembling a little as she pushed her finger even deeper into my ass, another low groan of the purest pleasure escaping my mouth as the sensations overwhelmed me.

  God damn, I felt suddenly right on the brink of cumming, and Jenny could obviously sense it too.

  Very slowly and tenderly she began to fuck my ass with her finger, slipping it deep into my hole, working me there until I was groaning and shivering, not even really sucking on my dick anymore, just letting the head of it rest gently between her lips as she began to focus all her attention on my butt, finger-fucking me faster and faster, slamming her finger deep into my hole until all of a sudden my orgasm hit, so damn powerful it caught me off guard.

  Jenny let out a little moan of surprise as my cum flooded her mouth, my cock pulsing and spurting as she quickly wrapped her lips tight around it, her finger still plunging deep into my ass, milking out every last drop of my huge load.

  When I was totally spent, she pulled her lips away, swallowing with a noisy gulp then smacking her lips and looking up at me with a surprised grin.

  “Wow!” she said. “That was … unexpected!”

  I smiled down at her shyly, my knees trembling a little, my whole body still swarming with an excited energy, my head spinning – totally caught off guard by what had happened, and how powerfully my body had responded to it.

  Just then, I heard the familiar beep of Jordan’s car horn outside in the driveway, and I shot her an apologetic look.

  “I’d better go,” I said, quickly buckling up my pants again, my hands trembling a little, as Jenny pushed herself to her feet.

  “Have fun now!” she said in a cute, innocent voice, like nothing at all out of the ordinary had just happened.

  I felt so strange. I wanted to stay – stay there with her, talk about what the hell had just happened – but instead, as always, I couldn’t find the words, and I just said something totally awkward like, “Thank you,” before racing off out of the room, grabbing my jacket and then leaving the house.

  “Hey buddy!” Jordan grinned as I got into the passenger seat of his car. “You all set for tonight?”

  “Sure,” I murmured, trying to force an excited smile on my face as we drove off towards the city.

  But the truth was, I couldn’t get what had just happened out of my head.

  3

  After a few bars, Jared and I and a bunch of my old college buddies headed to Daisy Dukes – which was billed on the sign as a ‘Gentlemen’s Club’. Jared had been before; he was a total sucker for places like this, but it was the first time I’d ever set foot in such a place, just thinking them sleazy and a bit gross.

  And as I looked around the dimly lit room, with two stages with poles, and a bunch of guys crowded around them thrusting out bills at the greased up dancers, Daisy Dukes did little to change my opinion.

  After grabbing some more drinks from the bar, Jared marched me over to what I guessed was a hostess, a tall redhead who was dressed in some kind of black babydoll lingerie, her bra and g-string visible beneath the flimsy semi-transparent material.

  “This guy is getting married a week on Saturday!” he announced. “He needs a private dance.”

  I felt my face burning with embarrassment, as I just smiled and nodded weakly, knowing there was no chance of escaping it and figuring: hell, it would be better to just get it over early with.

  I watched as she talked to Jared for a moment, he slipped her some money, and then she came back over to me, looking me up and down before purring, “you wanna follow me, sweetie?”

  The guys all cheered and whooped as the woman led me off to a doorway at the back of the club, past the stage, with a red velvet curtain. She held the curtain open for me and I stepped inside a small circular room, lit by soft purple lighting, with velvet benches.

  It was only as I stepped inside and she followed me in that I realized it was her I’d be getting the lap dance from.

  “Take a seat,” she said, nodding at the plush purple bench in front of me.

  I did as she asked, placing my ass down on the seat, sitting there somewhat awkwardly, looking up at her and assessing her properly for the first time.

  She was actually kind of pretty, in a slutty sort of way. Big eyes, big lips, and vampish smoky makeup. Her body was in good shape and her breasts were actually on the smaller more natural side, from what I could tell. Her long red hair looked like it was probably an expensive wig, and if I’m telling the truth, all I really felt as I assessed her was envy.

  If only I could somehow be allowed to dress like that: in slutty lingerie, my long legs shaved, my ass strung up in a cute little g-string, with a long luscious wig and sexy makeup.

  “Now just relax and enjoy yourself,” she purred, as slow, sexy music started to pump out from the sound system and she began to dance, winding her body in time to the beat, spreading her legs wide, and starting to tug at the hem of her cute little outfit, revealing the black g-string beneath, the soft mound of her pussy lips v
isible through the fabric.

  She slowly turned around, now presenting her ass to me, arching her back and bending forward until it was thrust right up in my face, so that I could see the thin fabric strap of the g-string, looking with envy at the way it slid deliciously between her toned butt cheeks, barely covering her asshole from view.

  I knew from hearsay that these places had a ‘no touching’ rule, in the sense that you couldn’t touch the girls but they could touch you if they chose. But it still came as a surprise, when she lowered her butt down and began grinding it against my lap, a jolt of pleasure flashing through me despite myself, feeling my cock hardening a little as she worked it with her buttocks, my eyes all the while fixed on her ass, a strange fantasy playing through my head that it was me dressed up like that, me dancing to the music, showing off my toned slim body in cute sexy lingerie.

  At some point, she tugged the little dress up over her head, now giving me a better view of her slim frame, which – apart from the breasts and slightly wider hips – wasn’t a million miles away from the shape of my own body.

  And I felt my envy and jealousy increase a little; it was so fucking unfair that guys couldn’t wear things like that if they wanted.

  But of course, she had no idea of the strange cascade of thoughts that were tumbling through my head, as she began to jiggle her small perky tits in my face, reaching behind her back to undo the flimsy bra, then shaking them free, pushing them together with her hands as if offering them right up to my mouth, her hard pink nipples tantalizingly close to my lips for a second before she pulled them away, again spinning and presenting her ass to me, back arched, bending forward.

  Only this time, I watched transfixed as she actually slid off the g-string, giving me a full view of her puckered little butthole and her plump shaved pussy lips, sliding the panties down around her thighs, then letting them drop to the floor.

  She turned back to face me, stroking her pussy now, legs spread wide apart as she began to softly sigh and moan. I knew it was an act, she probably did this time and again, and women were great at faking orgasms. But even so, it was still pretty convincing as she started to gasp and shudder, her long slender fingers working her clit, until with a final sigh she slid her hand away.

  I felt relief that the dance was over, but before I could get up from the bench, she squatted down and picked something up off the floor then leant in and stuffed it in the breast pocket of my shirt, before leaning in and whispering in my ear, “A little souvenir, honey,” then kissing me on the cheek, before grabbing the rest of her discarded clothing and heading off through a door I hadn’t noticed, one that must lead to a changing room at the back of the club.

  I sat on the bench for a moment, my heart pounding, before reaching into my pocket with trembling fingers to see what she’d put in there.

  Excitement flashed through me as my hopes were confirmed. It was her g-string! I looked at it for a moment, total dazed, before quickly stuffing it back in my pocket, then making my way into the club again, where Jared and the guys were all waiting.

  They cheered when they saw me, one of them thrusting a glass of beer into my hand, another slinging his arm around my shoulder, as he asked, “So, how was it?”

  “Pretty cool,” I croaked.

  And as we carried on with the rest of our night, my thoughts were never far from that secret scrap of black fabric, hidden in my pocket. That slinky, sexy pair of panties that were now mine ...

  4

  It felt so amazing to finally have my very own pair of panties, and I soon became addicted to wearing them. At first I would just sneak them on for a little while, maybe locked in the bathroom when I was supposed to be showering, but soon a little while just wasn’t enough, and before long I was wearing them every day – hidden beneath my regular boxer shorts, of course.

  I wore them to work, wore them on shopping trips with Jenny, even wore them around the house, washing them in secret at night in the bathroom basin while Jenny was in bed.

  I just loved the way they felt, loved the snug tight feeling of them, loved how sexy and feminine they made me feel, loved having this naughty little secret beneath my everyday clothing.

  But one afternoon, just a few days before our wedding, my secret life unraveled, in a way I’d never expected ...

  We were out at the Mall, Jenny and I, picking up a few last minute things in preparation for the honeymoon. It sounded so awesome – two weeks in a luxury resort in the Bahamas, all paid for by Jenny’s parents – and with the stress of wedding preparations, and of course nerves about the big day itself, I knew we were both looking forward to some much needed rest and relaxation.

  Jenny had her heart set on some new swimwear, and we were browsing though the aisles in her favorite store, but she just couldn’t decide what she wanted, filling a whole basket with brightly colored bikinis, while I trailed behind, as usual wearing my slutty little secret beneath my clothes.

  Now normally when we were out at the shops and Jenny was trying on outfits, I would wait outside the fitting rooms, killing the time by looking at my cellphone, but today as we approached the changing area there seemed to be no attendant at the door, and before I even knew what was happening, Jenny had grabbed my hand and pulled me into one of the rooms with her – a large white cubicle with a full mirrored wall at the back.

  “I, uh, don’t think I should be in here,” I’d murmured, my heart starting to race as I began to realize what was happening.

  “Oh hush now,” she grinned back, starting to push herself back against me, obviously wanting to get it on.

  It had been quite a while since we’d last fooled around – the night of my bachelor party in fact. Things had just been so stressful and busy running up to the wedding, and I knew Jenny had been distracted. But now she seemed hungry to make up for lost time.

  “I’ve always wanted to do stuff in a public place like this,” she whispered, a naughty glint in her eye as she began to rub me through my pants, her fingers working my cock to hardness, despite the terror that was now coursing through my veins at the idea of her discovering my panties.

  “I – I don’t think we should,” I stammered.

  “Come on!” she giggled, her fingers grabbing my throbbing cock, “I can tell you want it. Here, let me try and change your mind ...”

  I watched, frozen, as she dropped to her knees and started tugging at my belt, her face right down near my crotch.

  “No, Jenny, stop,” I murmured, as she began to unbuckle my belt and unbutton my pants.

  “What is it?” she said, confused, looking up at me with those big pretty eyes.

  In that moment, I didn’t know what to do.

  I felt my heart booming in my chest, knowing that there was no way to escape, no way out of this. I’d been utterly careless to wear the panties out of the house like this, I was so fucking stupid, and a part of me knew that there was no escaping the truth any longer.

  I would simply have to admit it, before Jenny’s eager fingers found them herself.

  “I’m, uh, wearing something,” I said timidly, my voice shaking as she looked up at me, totally puzzled.

  And then I did the thing I never thought I would.

  With trembling fingers, I reached down and pushed off my pants and boxers, uncovering my secret beneath ...

  5

  “Is this ... something you like?” Jenny said, finally, her eyes now fixed on my panties, the bulge of my hard just inches from her face.

  “Yes,” I admitted, still wracked with shame and guilt, but at the same time so glad to finally confess – a huge weight sloughing off me as I spoke.

  “I kinda suspected you might,” she added with a strange smile, her pretty eyes flashing up at me with naughty glee.

  “You did?” I said, unable to believe my ears.

  “Oh, come on, Mike,” she giggled. “You’re so much bigger than me. I was wondering why my panties and stockings always seemed so stretched out!”

  “Oh my go
d,” I gasped, unable to believe how well this whole thing was going, how totally unfazed and supportive Jenny was being, and how fucking stupid I’d been to keep it to myself all this time. “I’m so sorry!”

  “Hey, I don’t mind,” she grinned. “And actually?” she added, reaching out her hand and starting to tease and stroke my bulge, “I find it kinda hot.”

  Before I could say another word, she’d leant forward, nuzzling my bulge with her face, her eyes closing and a small sigh falling from her lips as her hands reached around and began cupping my ass, her mouth now running up and down the hot hard length of my shaft through the fabric of my g-string.

  “Turn around,” she whispered, her own voice now trembling a little, and I did as she said, my heart pounding as I displayed my ass to her.

  “Holy shit, Mike,” she giggled. “Your ass is better than mine!”

  It was so crazy to hear her say the words – for someone else to actually acknowledge that I looked as good as I hoped I did in slutty lingerie – and it seemed like Jenny really did like the way I looked.

  I even found myself giving in to my feminine urges a little more, arching my back and pushing my ass out towards her to really show off how fucking good it looked in my black slutty g-string, feeing her fingers stroking my butt cheeks and cupping my balls from behind.

  Then a moment later I felt her lips on my skin, first kissing my butt cheeks gently, before her face actually began to nuzzle behind me there.

  I let out a stifled groan of pleasure, trying to keep silent in case anyone nearby could hear me, as she reached around and took my cock in her hand, tugging it free from the top of my panties, while the fingers of her other hand slid the strip of my g-string a little to one side, just enough for her to actually lap at my butthole with her tongue.