First Sexual Crossdress Experience

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"I'm s-s-s-so sorry John!" she stammered, "Please forgive me!"

"What have I to forgive you about?" I replied quickly, "It's me that should be asking you to forgive me for upsetting you! You weren't to know... and I should've locked the door, or something! Anyway, it's too late now to try and hide anything, and I guess I owe you an explanation!"

"That's alright John!" she replied shakily, "You don't owe me an explanation -- and I'm not upset...surprised and curious maybe, but not upset! It's just that you told me to let you know when I'd finished that paperwork you'd left me, so's you could sign it and fax it through to the solicitors!"

In my haste to get ready, I'd forgotten all about that, and took a deep breath as I walked over to her, to try and explain things and ask her to keep quiet about what she'd just seen.

"Well it's no good trying to hide anything!" I began, shrugging my shoulders.

"You're... not!" she replied with a grin as she nodded her head forward.

I looked down to see my robe had fallen open when I'd shrugged my shoulders, and both my suspender-framed cock and naked tits were now totally exposed again!

"If you want to look feminine, you're going to have to realise that a lady doesn't go around flashing her bits and parts all the time to innocent people!" she said, almost managing to suppress a giggle, "And that eye- shadow is wrong for that colour of foundation! You need a russet eye-shadow -- or something with red or brown in it!"

I was gob-smacked! She'd only just walked in and found her boss wearing women's undies, and here she was now explaining makeup to me!

"Hmmm, I've always wanted to see a guy wearing women's undies!" she grinned, "And if it's any comfort, I think you look really sexy in them!"

"So you're... you're not upset or anything?" I asked incredulously.

"Upset? No! I might even be able to give you some more makeup tips!" she replied.

"Thanks!" I grinned back at her, "I'd appreciate that!"

"Hmmm, at least I now know where to come if I want to borrow some undies!" she joked, "Look how many you have -- you must have twenty times more than me!"

She walked forward and stood gazing into the open wardrobe at my undies like a child let loose in a sweet-shop.

"You're welcome to borrow any of them." I told her, "Have a good look and see!"

"Hmmm, we're the same size as well!" she said as she held a basque up to her and admired herself in the full-length mirror, "Hey... these are really nice!"

"Try some on if you want!" I heard myself saying, "Unless you've got to go home?"

"No, I shouldn't -- besides, you were getting ready to go out!" she replied.

"Awwww, that's okay!" I smiled, "A friend's coming round, but she's not due round for another hour or so, and we'd no firm plans about going out anyway!"

"She?" Anne repeated, "So she presumably knows about you wearing?"

"Well... actually, she's a he -- and he wears as well!" I confessed.

"Hmmm... interesting!" she smiled wistfully, "Tell you what... if you let me try on some of these... I'll do your hair for you and you can tell me all about you and this he or 'she' that's coming round -- deal?"

"Okay, it's a deal!" I smiled.

She immediately busied herself with getting my brushes, combs and hairspray from the dressing table drawer and asked me to turn round to face her.

"Okay... now tell me all about this guy or 'woman' you're meeting later!" she said as she hitched up her skirt slightly and straddled my nylon-clad knees, "I want to know all about her, and what you usually do together!"

"If I did that, I might shock you!" I replied somewhat bashfully.

"So, shock me!" she replied matter-of-factly as she removed the hair rollers from my hair, "I might shock you later when I'm trying on some of your undies!

"I can't see how... but okay, I'll tell you!" I said resignedly.

As she combed and brushed my hair, I told her all about Michelle, how we'd met, what we liked doing together and how I'd become interested in wearing women's undies as a boy, and even what'd happened up in the woods with the guy.

"And what did you feel like, that first time with that guy?" she asked as she sprayed some hairspray on my hair, How did you feel -- being... fucked?"

Hearing her saying the word 'fuck' instantly made my cock jerk and I could feel it starting to stiffen as I explained to her.

"It made me feel very... feminine!" I exclaimed, "And felt sort of... right! Now I come to think of it, it felt like the most natural thing in the world to do!"

"And was this, because you were wearing some sexy undies at the time, or didn't they pay any part in it?" she enquired further in a soft voice.

I suddenly became aware that I'd a massive hard-on and that my erect cock was now lewdly poking out through the folds of my robe for all to see!

"I... I think they made the feelings more intense, but the feelings were very strong and deep-rooted anyway!" I replied slowly.

"Mmmm!" she smiled -- almost ignoring my answer, "Well that's about it for your hair! Now, who's a pretty girl then?"

I smiled bashfully at the word 'girl' and felt my cock jerk again!

"Just pass me your eye-shadow from the dressing table will you, and I'll do that as well for you while I'm here!" she smiled broadly.

I turned and picked up the eye-shadow and passed it to her before she eased my head back to apply it.

"Did it... bother you -- me calling you a girl just then?" she asked quietly.

"No... not really -- I... I just wasn't ready for it, that's all!" I replied truthfully.

"Well it looks like you're ready... for something!" she grinned, pointing downwards and between us at my erect cock with the eye-shadow applicator.

"Oh... that!" I replied embarrassedly, "Sorry about that Anne, I can't help it!"

"Hey, that's okay, it tells me that what we're doing is turning you on! And I simply love those tits! Are they hormones or implants?" she replied.

"Hormones." I replied, "They also soften the voice and round the hips I believe?"

"Hmmm, I've heard that as well!" she said, then added quietly, "You can touch me if you want y'know, John -- I won't bite, and I know you've been dying to!"

As if to substantiate what she'd said, she hitched her skirt up a bit more, settled down slightly, and then every so lightly moved back and forth so she traced the gusset of her panties several times over my extremely sensitive knob-end before lifting off me again. My hands immediately strayed to her naked thighs and I traced my fingers up and down them before stealing to the insides and repeating the strokes.

"Mmmm, that feels... nice!" she cooed, "Don't stop, it's turning me on!"

"I've no intention of stopping." I breathed, "It's turning me on as well!"

"Mmmm! I'm sorry I'm not wearing anything sexy like you have in your collection, but I wasn't expecting anything like this happening to me!" she said, "It's been quite a while since I've worn any stockings -- or sexy underwear!"

"So you like wearing that sort of stuff as well?" I asked.

"Mmmm, yes!" she smiled, "It has exactly the same effect on me as it does on you and your friend, Michelle -- it makes me feel really feminine... and sexy!"

She was obviously giving me the all clear, so I slowly slid my hand up the inside of her thigh and curled my finger under the elastic of her pantie-leg -- intent on stroking her pussy and maybe fingering her!

"Mmmmmmm, that's nice, John!" she breathed, "Pull it over to one side for me!"

My finger hooked once more round the elastic and I pulled the material away from her pussy before forcing it over to one side.

As soon as I did so, she moved her hips forward and manoeuvred around with her hairy cunt brushing my knob- end until she found the entrance to her cunt! Only then did she slowly lower herself down so's my cock slid all the way inside her hot cunt!

"Ahhhhhh, that's better!" she breathed, "Much better!"

"Oh yessssssss!" I breathed back as I gripped her hips and moved them back and forth so's my cock slid in and out of her cunt, the tiniest amount!

I still had my eyes closed and by head back as I felt her hands holding the sides of my face and her lips closing on mine!

Our tongues explored each other's mouths and our kiss became more passionate, our embrace much tighter now as she slowly lifted herself up and down so's my cock slid in and out of her cunt and she steadily fucked herself on it!

"Christ, I've needed this for so long, John!" she whispered against my lips, "It's been ages since I've been with anyone!"

"Mmmmmmm, if you'll let us, Anne, me and Michelle can soon put that right for you!" I whispered back at her, "And boy... could Michelle put that right for you?"

"Oh, and why's that?" she asked, pulling away slightly but still riding my cock.

"Ermm... I'll let her tell you and show you, when she comes!" I smiled before kissing her once more.

"Now what could that mean?" she mused, "You've got me thinking now!"

"All will be revealed when she arrives!" I grinned, "And I do mean... all! Now, come on, go and try some of my undies on while I fix us some drinks, otherwise you're gonna have me coming before I'm ready!"

"Mmmm, we wouldn't want that!" she laughed as she slowly stood up and pulled off my throbbing cock, "And I could sure do with a drink!"

She straightened her skirt as she stood up and back away from me, then leant forward and sucked my cock into her mouth, sliding her lips up and down it's entire length before pulling off and smiling at me.

"Just thought I'd give it a bit of a clean! We can't have your robe getting covered in my juices -- can we?" she said.

"You mean your cunt-juices?" I grinned wickedly to see if I could embarrass her.

"Yes, that's right John -- my cunt-juices!" she grinned back.

With that she walked towards the wardrobe and stepped inside.

"You don't mind if I close the door a bit while I'm changing, d'you?" she asked, "A girl's gotta have a bit of privacy!"

"No, not at all!" I smiled, "But can I just quickly get a skirt and a blouse?"

I went inside and picked a short fawn cotton skirt, and a carmine satin blouse, before giving her a quick kiss and heading back to the dresser for my lacy black bra -- getting a wolf-whistle from Anne as I left the wardrobe!

"Cheeky bitch!" I called back to her.

"John, where d'you keep your panties? I can't find any!" she called as I fastened the clasp on my front- fastening bra.

"I don't use them!" I called back, "Neither does Michelle! We find they just get in the way and we've found it feels much sexier to go without! Besides, it makes it a lot easier to flash at people if you're not wearing any!"

"Hmmm, I think I'll try going without then, and seeing how it feels!" she replied, "It sounds like fun!"

I was sitting down and fully dressed and sipping my drink when she called out that she was nearly ready and could she do her hair and use some of my makeup when she came out? So I told her to use whatever she wanted and to treat everything as her own. A few minutes later she opened the door of the wardrobe and stepped into the room, wearing a frilly red top and a dark blue side-vented skirt that just covered the stocking-tops of her black lace-top nylons!

"Well... what d'you think?" she asked, posing in front of me so's her black suspenders and stocking-tops showed as she twirled round and her skirt flew up.

"Wow! Very nice!" I smiled, "And perhaps this should prove to you that I'm telling the truth?! I uncrossed my legs and splayed my knees to let my cock free so's it pushed up the front of my skirt so's she could see it and my black undies underneath!

"Mmmm, it does!" she grinned, "And perhaps this'll prove to you that I meant it when I said I'll try going without panties!"

She spread her feet and lifted up the front of her skirt to expose her beautifully hairy cunt! It was literally covered in a thick dark carpet of her pubic hair and I could just see her outer cunt-lips peeping through it!

"Oh yessssssss!" I gasped at the sight of her hairy cunt, "Just how I like them!"

"You were right about it feeling far sexier by the way! I feel like I'm more than naked under here -- if you know what I mean?"

"I know exactly what you mean because I feel exactly the same way!" I smiled.

"It feels... naughty!" she replied, "Yeah... naughty! No, lets see about doing something with my makeup and hair!"

As she sat down to tart herself up, I wandered over and stood behind her, my hands straying to her tits and being delighted to find they were nice and firm.

"Is that a gun in my back, or are you just glad to see me?" she asked me in her best Mae West voice.

"You should think yourself lucky it isn't Michelle that was standing behind you!" I told her, "You'd think it was a shotgun -- or more like a blunderbuss!"

"Oh... so she's well-built, is she?" Anne asked as she dusted her cheeks with my compact and then brushed on some lipstick and lip-liner.

"Let's just say that her ... 'attributes' go further than that!" I smiled, "You'll see."

"My mind's working overtime, trying to think what you mean, you bugger!" she laughed, "I can't think what you're on about! Tell you what though... this bloody makeup's the best I've ever used! It must've cost you a bomb!"

"Feel free to come up here and use as much as you want!" I smiled, "And to wear whatever you want of mine as well!"

"That's very kind of you John." she smiled, "Thanks!"

I felt a tickling feeling run across my belly, knowing that Anne would perhaps soon be wearing some of my sexy undies and clothes -- and that they'd be turning her on!

"Right... finished!" she said a few minutes later, "Well... will I do?"

"Oh, will you ever?" I breathed, "C'mon, lets sit down and have a drink."

"What are some of the more sexually daring things you've done, Anne?" I asked her as we settled down with our drinks.

"Hmmm!" she mused, "Not much really... although I've been fucked outdoors a few times! And I brought myself off in a cinema once! Oh yes, and I once sucked a guy off on the back seat of a bus! What about you?"

"Ohhh, the same sort of things -- and ...some others!" I grinned, "Me and Michelle might share some of our more daring things with you one day perhaps -- that's if you want to anything to do sexually with us? I mean, you and me have 'messed about' a bit this evening, but that might be as far as you want to go -- I don't know!"

"I'm not promising anything John, but lets see how I feel when Michelle comes and take it from there, shall we? I might surprise even myself, and join in fully with both of you, or I might not -- I've never been with two guys... sorry... ' girls' before!"

"Well I can tell you this...nobody's gonna force you to do anything you don't want to do this evening -- and that's a promise, Anne!" I told her sternly, "You do only what you want to do, and nothing else! And if you do go all the way, and then never want to with us again -- that's okay as well!"

"Ahhh, that's great John, thanks!" she smiled, reaching across and touching my knee.

"Wouldn't have it any other way Anne, and neither would Michelle!" I replied, "And speaking of which... I think that's her car that I can hear, pulling up outside?"

"Oooo good! Now I can find out what's so special about Michelle!" she grinned.

A few minutes later Michelle walked into the room.

"Hi Michelle, this is Anne, my secretary!" I smiled, "I might've mentioned her?"

Michelle was wearing her usual shoulder-length blonde wig and a skimpy flared printed off-the-knee dress and looked her usual stunning self.

"Oh hello Anne, glad to meet you!" Michelle smiled, "Yes, Suzy has mentioned you!"

"Hello Michelle, John's told me all about you -- well, some!" Anne smiled.

"Oooops, sorry Anne, I forgot to tell you that I call myself Suzy when I'm dressed and made-up!" I explained.

"Suzy...? Hmmm, that really suits you!" she replied, "I was wondering about that earlier actually -- with Michelle being called... Michelle!"

"Well, we were somewhat busy with other things!" I laughed, "Anne accidentally caught me dressing earlier... so I've told her all about you and me, and what sort of things we like doing together."

"And are you okay with that, Anne?" Michelle asked her.

"Perfectly....! Why not?" she replied.

"Ahhh, that's good!" she smiled, "Now we can relax and be at our ease!"

"Anne was telling me earlier that she hasn't been with anyone for ages, and I told her that you'd be the one to put that right for her!" I explained as I gave her a drink, "I mentioned to her that you had some special... 'attributes' but didn't tell her what they are. So I'll let you explain to her, as she's dying to know!"

"Yeah, c'mon Michelle! Suzy wouldn't even give me a hint!" Anne laughed, "I told her it had been a very long time since I'd had some cock, and she told me that you'd be able to put that right for me!"

"Well, I suppose that's true -- in a way!" Michelle blushed, "I suppose what Suzy's referring to, is that I can come six or seven times in rapid succession!"

"And...?" I coaxed her.

"Oh yes, that! And when I do come, I come an enormous amount -- not just the first time -- I come an enormous amount, each and every time!" she explained.

"And...?" I coaxed her again.

Michelle looked across at me with a quizzical look...?

"Show her!" I smiled, "Y'know!"

"Oh yes! I see what you mean, Suzy!" she replied, "Ermm... I think I should show you what Suzy's on about -- rather than try and tell you, Anne!"

Anne was sitting forward with her glass and smiling sweetly as Michelle stood up.

Then her face changed to one of disbelief and total amazement, as Michelle slowly raised the hem of her dress right up to her waist, to completely expose her beautifully thick cock, and it's truly massive knob- end!

"Fucking hell!" Anne gasped in total surprise and sheer admiration, "Jesus Christ!"

"Like it?" I asked her.

"I... I'm fucking sure I'm going to!" Anne finally managed to gasp, "But I'm just wondering if I'd be able to? I mean... look at the size of that fucking knob- end!"

"Well if Suzy can -- I'm sure you can, Anne!" Michelle told her as she lowered her dress and sat back down, "You can find out later if you want?"

"Oh yes, Michelle -- I want!" Anne gasped, her head now shaking from side to side in total disbelief, "Christ, do I want?"

"I thought that because Anne's joined us, we'd not go to the car park?" I suggested to Michelle, "Perhaps a 'walk' through the park later on might be a good idea?"

"You mean after here?" Michelle asked.

"Mmmm, yeah!" I grinned, "There's a double bed over there -- and a nice 'walk' through the park later on as it gets dark, might round off the evening?"

"Hmmm, I agree!" Michelle smiled.

"And do you get really hard every time, Michelle?" Anne asked, still trying to comprehend the special attributes and hidden qualities of Michelle's cock!

"As hard as an iron bar!" I told her, "Each and every time!"

"Fucking hell!" Anne breathed, "This is gonna have to be seen, to be believed!"

"And tried!" I added.

"Oh yes -- definitely tried!" Anne repeated, quickly nodding her head!

"Can we have another drink before we start please, Suzy? Then I think I should let Anne have a 'test- drive' -- before she dies of curiosity!" Michelle laughed.

"Of course!" I smiled, quickly getting up and refilling our glasses.

For the next five minutes as we drank our drinks, Anne asked Michelle about herself and if it was really true that she could come so much in such a short time?

Michelle joked that if Anne was going to think about sucking her off, she'd better like the taste of cum -- because she had plenty in store to give her!

"Let's just say that more than one boyfriend has called me a cum-slut!" Anne replied.