Feminized for the Very First Time: 8 Books Feminization Anthology

by D. L. Savage

  I couldn’t quite believe what was happening, but Jenny seemed totally into it, making small pleasurable sighs of her own as she began to eagerly tongue my ass, driving me wild, each thrust of her tongue sending me closer and closer to the edge.

  I looked over my shoulder, watching us in the mirrored wall: me with both hands pressed against the door to the cubicle, my back arched, my butt thurst out, and Jenny with her face between my cheeks, not even stroking my cock any more, just focusing all her attention on my tender asshole, driving her tongue rhythmically into it as both her hands cupped my butt cheeks, spreading them wide apart.

  I knew we had to be quiet, but my breathing was getting pretty loud as she worked my hole with her tongue, and before long I knew that if she continued like that I might actually come – even though neither of us were even touching my cock!

  And the more I gave myself up to the delicious sensations that were coursing through my body, the more the pleasure overwhelmed me until all of a sudden it reached a crescendo, my body bucking, my knees quaking, Jenny’s tongue thrust deep in my butt as I began to come, my cock spurting out a series of hard powerful jets against the cubicle door.

  As I returned to my senses afterwards, I started to feel a little embarrassed. Was it really very manly for a guy to come like that – for his girl to bring him off just with her tongue in his butt? And wearing slutty panties, no less?

  But the flushed happy look on Jenny’s face afterwards told me everything I needed to know, and just to confirm things, she added with a smile, “You actually just came? Wow! That was so fucking hot, Mike!”

  6

  After I’d pulled up my pants and Jenny had wiped up the mess I’d made with one of the store’s bikinis, we both snuck back out of the fitting rooms like two naughty teenagers, stifling our laughter as the now-present store attendant gave us an exasperated eye roll, obviously having seen couples sneaking in before now.

  But she had no fucking idea just what we’d done back there.

  In fact, I still kind of couldn’t believe it.

  And as we went to a nearby coffee shop, Jenny was brimming with excited questions. She wanted to know everything – how long I’d been dressing, how far I’d gone, whether I’d ever done anything with guys. It was like she just couldn’t get enough, the sheer kinkiness of this new secret part of my life obviously turning her on more and more.

  “Keep your voice down!” I hissed, as she got too excited, just firing off a million questions at me in this crowded public place.

  “Sorry,” she said, dropping her voice back to a whisper and leaning in across the table to take my hand in hers. “But I just want to know everything, Mike. C’mon, you know now that I’m not going to judge. And if we’re about to get married, then I don’t just want this to be your thing anymore. I want to be a part of it too ... if I can.”

  I looked at her, my heart rushing with love and tenderness for this amazing, gorgeous woman who’d just become even better in my eyes – more loving and accepting than anyone I’d ever known.

  And I knew then that I could finally speak the truth. Finally tell her everything.

  I told her all about my furtive teenage years, sneaking panties out of my sister Kelly’s underwear drawer, I told her about the time she’d almost caught me in her stockings and thong, and I told her about my most secret dreams, too – about how much I longed to be fully dressed up, to wear a wig, makeup, heels, a pretty dress, the whole nine yards – but how I’d never gone that far.

  “You totally should!” she beamed at me, again saying the words I never thought I’d hear. “And what about stuff with guys? Are you, like, bi?”

  I shook my head. “No, I’ve only been interested in girls,” I explained. “It’s just the idea of being feminine that gets me off. I just want to be with you, Jenny. That’s not something you have to worry about.”

  “Good,” she smiled. “But the butt stuff – that seems to really turn you on!”

  “I know,” I said, shaking my head as I remembered what had just happened in the fitting room. “To be honest, that was as much of a surprise to me as anyone. Those two times you’ve done stuff to me there? I’d never had anyone touch me like that before.”

  “I’m so glad you’ve finally opened up to me,” she said tenderly, giving my hand a big squeeze.

  “Me too,” I replied, not knowing how to even put into words how much all this meant to me, too, other than to add, “I love you so much, Jenny. I can’t wait to marry you.”

  And as I turned out, our wedding night would be even more special and magical than I could ever have imagined ...

  7

  “You two look adorable!” my aunt Helen gasped, clasping her hands together, a huge grin on her face, a week or so later.

  We were at the wedding reception now, Jenny dressed in the most beautiful white dress, me in a classic black tux, surrounded by our closest friends and family.

  The ceremony itself had gone off without a hitch, the photographs had been taken, the cake had been cut, and the speeches had been made – including a super embarrassing one from Jared, of course.

  Even my mother seemed in a good mood – for her at least – begrudgingly admitting that the venue was ‘rather nice’ and only asking me a few dozen times if I had packed everything I would need for the honeymoon.

  And now, all that was left was for Jenny and I to lead everyone onto the dancefloor, to give the first dance – which was set to Jenny’s favorite song: At Last by Etta James.

  As we made our way into the center of the hall, I could feel everyone in the room watching us, and even though I normally hated being in the spotlight, I didn’t care. Because I was here with Jenny, who was now my wife – and she looked so utterly beautiful; her makeup flawless, her hair amazing, her dress stunning. Sure, I felt a little envious of her amazing outfit, but mostly I just felt so thankful and lucky that she was the person I was to spend the rest of my life with.

  As we began to dance, we held each other tightly, my arm around her waist, her head resting on my shoulder, the soft sensual music flowing all around us.

  “I can’t wait to get you alone later,” I murmured, as we slow danced.

  We had a luxury hotel room booked for one night, just a short distance from the venue, before a taxi was to take us to the airport first thing in the morning. Sure, we wouldn’t be losing our virginities tonight but it still seemed like magic lay ahead of us – our first night together as man and wife.

  “About that,” Jenny murmured back, taking her head from my shoulder to look me deep in the eyes, a naughty little grin curling at the corners of her lips. “I’ve got a little surprise planned for you.”

  I felt my heart start to drum.

  “What is it?” I asked excitedly.

  But she just gave me a wink and whispered, “It wouldn’t be a surprise if I just told you, now would it?”

  The evening flew by – everyone having a great time, laughing and drinking, dancing and eating – and before we knew it, it was time for Jenny and I to bid our goodbyes and make our way to the hotel.

  We dashed out happily to the waiting limo, waved off by our friends and families, and as the sleek vehicle transported us to our hotel room, I wondered again just what the surprise was that Jenny had in store for me.

  She was clutching my hand tightly in the car, and I wondered again if I should just ask her, but figured there was no point – for a start, she wouldn’t tell me, and anyway, I’d find out soon enough.

  Jenny had already checked into the hotel yesterday – it was where she’d spent her night before the wedding, but it was the first time I’d seen the place, and holy shit, it was incredible. Pure five star luxury.

  I looked around me in awe as we strolled through the huge marble lobby, catching warm smiles from the other guests as we made our way to the elevators.

  “Jenny, this place is insane,” I said with a grin as we got inside and she punched the number for our room – the honeymoon suite, up a
t the very top of the building.

  “Just wait till you see the room!” she laughed.

  And she was right. I almost couldn’t believe my eyes when I saw it. It wasn’t even just one room, there was a large lounge area with elegant sofas, huge gilt edged paintings hanging on the walls, and a set of shuttered doors that led to what I assumed was the bedroom.

  “Is our bed through there?” I asked, gesturing to them.

  “Yeah,” she said, “but Mike? Before you go in, I should let you know, that’s where your surprise is waiting. Do you want it now?”

  I nodded and she excitedly took my hand, leading me toward that set of double doors.

  What was on the other side of them?!

  I held my breath as she pushed them open and we stepped inside ...

  8

  “Is that what I think it is?” I said in a small voice, totally shocked, unable to quite believe what I was seeing.

  “It’s yours, Mike,” she replied softly, squeezing my hand. “Do you like it?”

  “I love it,” I gasped, my heart swelling with a kind of excitement I don’t think I’d ever known before.

  Because there laying out on the huge sumptuous four poster bed was a wedding dress. A beautiful white dress that – the more I looked at it – I realized was identical to Jenny’s.

  “I had a second one made in your size,” she explained excitedly. “The woman at the store thought I was totally crazy, but she did it!”

  “Jenny, this is just too much ...” I murmured, still unable to quite take in what I was seeing.

  “Wait, there’s more!” she laughed, rushing over to a case by the side of the bed, bringing out two beautifully wrapped packages. “Go on,” she laughed, thrusting them into my hands, obviously enjoying this just as much as I was, perhaps even more so. “Open them!”

  I tore open the paper to the first package with trembling fingers, my heart again racing as it slowly dawned on me what it contained.

  It was a box for a wig. What looked like a beautiful long blonde wig – clearly an expensive model.

  I almost felt like crying, as I stared down at it in disbelief.

  “Don’t forget this one,” she laughed, indicating the second parcel, which was a different shape – more like a flat rectangular box of some sort.

  Again I tore at the paper, as excited as a kid on Christmas morning, as I revealed a sleek matt black gift box beneath. I lifted the lid and there, on crumpled white tissue paper, lay underwear. The prettiest, sexiest white underwear I’d ever seen. I let my fingers run over the soft sleek fabric, my heart racing, my eyes flooding with tears. It contained a matching white bra and panty set, with a pair of white stockings and a garter belt, too.

  “It’s exactly the same as what I’m wearing right now, too,” she explained with a tender smile.

  “I can’t wait to try them on,” I gasped, already tugging at my belt with one hand and my bow tie with the other, just wanting to immediately get all this stupid manly stuff off me and slip into these amazing items.

  “Well, wait a moment,” she said, hands on hips, her face turning serious for a moment.

  “What?” I said, confused.

  “Do you really want to try on all that cute sexy stuff while you’re still hairy?”

  And I watched, my grin growing even wider, as she pulled a delicate pink razor and a can of shaving foam from behind her back.

  “I thought first I’d get you all nice and smooth,” she teased playfully, “and then of course we need to do your makeup!”

  It was like a dream – a fantasy so wonderful I’d never dared imagine it – as Jenny helped me undress and led me through to the bathroom, then carefully and lovingly helped me shave my body totally smooth, everywhere.

  After I’d shaved, I had a quick shower to rinse off, then she patted me dry with a towel, before helping me rub delicious smelling moisturizing cream all over my body.

  Next was makeup. Jenny had me sit on a stool, as she brought out her makeup kit, forbidding me from peeking even slightly until she’d finished work on me. I didn’t know what she was doing, and as she applied all kinds of things to my face, creams, powers, brushes and pencils, I stayed still, holding my breath, so scared that this was all just a crazy dream and any moment I’d wake up.

  “Can I look now?” I asked, once she’d finished and told me open my eyes.

  “Not yet,” she grinned. “Let’s get your hair on first.”

  She grabbed a small cap made of the same material as my stockings and fitted it over my head, making sure to scrape up any last strands of my real hair underneath, then she took the long blonde wig from its box, shaking it out and running her fingers through it, commenting on how real and pretty it was, before finally fitting it over my head.

  I loved it immediately – the way the hair danced against my shoulders and flowed down my back, so silky against my skin.

  “Stand up,” she said, going and fetching the lingerie as I brought myself to my feet.

  She handed me the stockings, watching excitedly as I slipped them on, savoring the feeling of them as they slid up my totally smooth hairless legs, just the way I’d always imagined and yearned for.

  It felt so strange to be dressing like this in front of someone, but I was glad it was Jenny. She’d given me so much confidence, and I was glad to share this part of my life with her after so long alone.

  Next I pulled on the panties, which were so beautiful – a cute white thong fashioned from some kind of stretchy fabric which perfectly cupped my cock and balls at the front and slipped so snug and tight between my cheeks, sitting just perfectly on my hips.

  Jenny helped me into the bra – a double A cup – which I found actually hugged my pecs really well, the slight puppy fat filing out the tiny cups in a way that almost looked like real breasts, at least from my view of it.

  And as I peered down excitedly at my itty bitty titties, it was so fun to see my new long blonde hair hanging down, too, framing my vision!

  Finally came the garter belt, which I hooked around my waist and fastened to the tops of my stockings with trembling fingers, so eager to see my transformation.

  “Now can I take a look at myself?” I pleaded, hearing that even my voice had changed a little, taking on a softer, more feminine tone.

  “Oh, I forgot,” Jenny laughed. “I got you these too!”

  She thrust a third box towards me. This one wasn’t wrapped up and as soon as I saw the name on the side, I knew what they were.

  “Oh Jenny!” I grinned, eagerly pulling off the lid and staring in at the sexiest white heels, again realizing with a shiver of delight that they were the exact same ones that Jenny was wearing now, only a few sizes larger.

  I sat down again on the little stool by the dresser as she fitted them onto my feet, my body now where it truly belonged: encased in sexy, sensual lingerie.

  Next she helped me into my dress, showing me how to step carefully inside it so I didn’t catch anything, and then pulling it up around my armpits, telling me to breathe in a little as she fastened it at the back.

  “Okay, now you can look,” she said with a satisfied smile.

  I felt my movements take on a new grace as I made my way toward the long mirror on the other side of the room, my hips swinging as I walked; man, I even seemed to be able to walk in heels straight away!

  And when I finally reached the mirror, I gasped in total awe at the amazing job Jenny had done on my make up.

  I looked real. I looked like a real woman – a beautiful, sexy, confident woman!

  She’d contoured my face in ways I’d never even dreamed possible, making my nose thinner, my cheekbones higher and more pronounced, my lips fuller than I’d ever seen them. And the wig was the final icing on the cake. It was perfect: so real, so natural …

  I gave a happy twirl, clasping my hands together, as Jenny came and joined me, both of us staring at our matching reflections in the mirror, both of us smiling. We looked like two women – one tall b
londe, one petite brunette – both of us beautiful and utterly feminine in our own unique ways.

  “I love seeing you like this,” she said gently. “I love seeing you happy.”

  “I am happy, Jenny,” I said, my eyes again brimming with tears, which I had to quickly fan at with my hand, tilting my head back, not wanting to ruin her amazing makeup job. “More happy than I’ve ever been …”

  “Now, I know you look stunning in that dress,” she added, a new playful tone entering her voice, “but I kinda want to take it off you again so that I can show you my last surprise. The biggest surprise of all ...”

  9

  We both undressed each other, taking it in turns to undo our dresses, slipping them off, leaving both of us now dressed in just our sexy lingerie. It was so great to be wearing exactly the same as Jenny, and I loved the look of her cute sexy body in her stockings, thong and bra just as much as I loved catching glimpse of myself in the mirror, trussed up the exact same way.

  But even though we were both girls now, there was no question who was in charge. Jenny seemed take control so naturally, leading me over to the bed and even pushing me back onto it, so that I was lying on my back, crawling over me as she fondled my breasts through my bra, then let her fingers stray further down, cupping my aching cock and balls through my thong for a moment, before pushing herself back up again, leaving me there squirming on my back, desperate for more.

  “Where are you going?” I asked, puzzled, as she turned to make her way to the bathroom, giving me a flash of her sexy pert butt in the process.

  “To get your final present, silly!” she giggled.

  She seemed to spend rather a while in the en suite, so long in fact that I felt my cock starting to soften a little, but the moment she came out again, it swelled once more, my eyes met with a sight I don’t think I will ever forget for as long as I live.

  Because there was Jenny, still dressed in her sexy, slutty lingerie, only now there was one extra addition to her outfit. One rather large addition.