All characters depicted are 18+.  While there is no sex, there are sexual scenarios depicted so this has been marked as mature.

Kaitlyn

You're probably wondering about Kaitlyn.  As I rushed home to start our vacation, I remembered the first time I'd seen her weeks ago.  She was a goddess in human form.  A radiant blend of ethereal beauty and captivating grace that seemed almost otherworldly.  I was smitten.  Never mind she was over 6'/190cm tall and a head taller than me.  Never mind she was over a decade older than me.  Love doesn't care about such minor quibbles.

Keep in mind that I had never had a girlfriend so she was already the most beautiful woman who'd ever shown interest in me!

Her hair cascaded in soft waves, catching the light with its warm, caramel hues.  It framed a face that commanded attention with a presence that was both striking and authoritative, marked by bold, well-defined features that exuded confidence. Her high cheekbones, complemented by a strong jawline, gave her a regal and imposing look. Her eyes, sharp and intense, held a piercing gaze that seemed to see right through to the core of anyone she met, their depth accentuated by arched eyebrows that conveyed both determination and control.  Her lips, full and expressive, often set in a determined line, spoke of a strength that was both commanding and reassuring. The overall effect of her visage was one of formidable power tempered with a warm, charismatic presence.  Only one thing about her fell short of perfection... Her interest in me!  Why was such a beauty dating me?! OK, I know what you're assuming.  And you're wrong!

When Kaitlyn first approached me, I was wary.  I mean, I had just taken over Prestige Global and now some women were suddenly all friendly and nice to me.  However I remember how women really felt.  For example, I was told there was a new secretary with the memorable name of Lilly Breeze just hired to Prestige Global.  She was a very cute girl about my age and I excitedly went over to welcome her to the company.  Before I could introduce myself, she just looked down her nose at me, clearly referencing our difference in height, and went "Eww, no."  As I stood there, my hand outstretched and my face fallen, she was quickly pulled away and I heard the other secretaries saying "Don't you know who that is?"  It was a clear reminder how women saw me when they weren't blinded by my family wealth.

So you can see why I would be initially suspicious of Kaitlyn.  Then I learned that Kaitlyn Delacroix was not some gold digger.  Her family were majority owners in MicroBotix Innovations and she was on their board of directors.  I didn't know much about them other than they were big in medical technologies.  They weren't quite in the league of Prestige Global, but they had significant market share.  Bluntly, she was someone who was rich of her own accord.

We were both at some press conference related to government contracts.  As we waited for the whole thing to get started, I couldn't help but look at her.  Imagine my surprise that she was looking back.  Her gaze was steady and intense, but I could feel the intrigue.  She made the first move, introducing herself to me.  We started some small talk, something about the news, the weather, just banter.  All I could see was her.  So when she casually asked to continue our conversation over dinner, I know I probably looked as off-balance as if she'd suddenly sprouted wings and flew away.  Of course I said yes.

I asked her pretty early on "Why me?"  Her easy, charming smile would've been answer enough.  She just said she liked my eyes, my personality.  But after we'd gone on a few dates, she confessed she really liked that I was 'different' from the men she'd been with before.  She admitted she had been through several relationships with the guys that society expected her to be with and she'd found them all unsatisfying.  They both would try to take charge of the relationship and that always led to conflict.  Softly, I said "I would never do that to you."  Immediately she flashed that mega-watt smile that made my soul happy.  From that point on, the night went like a dream.  She laughed at all my jokes.  She asked questions that showed she was interested in me.  Everything went so well, she invited me to her place after.  I must still be dreaming.  At that point, I was not prepared for the twist the evening would take.

When she invited me into her bedroom, and told me to disrobe while she "slipped into something more comfortable", I was ecstatic!  I was no longer going to be a virgin!  I thought I was going to have sex on the first date!  Suffice I had my clothes off in seconds and was ready for action.  As the seconds ticked away with the initial excitement over and I waited, it was then I started to think about what I was doing.  Some would say I was overthinking.  All my confidence deflated like a balloon the more I thought.  I've mentioned I'm a small guy but, for obvious reasons,  I may have skipped over the fact I'm perhaps not gifted... down there.  Like I'm really small.  No, I'm not giving you precise measurements!  My hands self-consciously moved down to cover my lack.  Suffice to say this was going to be the first time anyone outside my immediate family or my doctor ever saw me down there and suddenly I was full of doubt.  A million horrible possibilities came into my head.  She would laugh and mock me, she would be upset, she would be angry I had wasted her time.  I couldn't let that happen.  I quickly dressed, putting my clothes back on.  I was just grabbing my shoes, intending to make a run for it.  I was ready to head home and admit this had all been a huge mistake.

I was so distracted by my thoughts I was taken completely by surprise when the door opened and Kaitlyn stepped in.  In a polished display of confidence and allure, she strode into the room on a pair of open-toed, stiletto heel black lace sandals.  Kaitlyn loomed over me normally, but this was the first time she'd worn heels in front of me. With me barefoot, I was staring directly into her ample bosom.  Earlier I called Kaitlyn a goddess.  In that moment, it did feel I was somehow in the presence of divinity.  As my eyes scanned down, I grasped why it had taken her a bit of time to get ready.

The lingerie she wore was captivating, the fabric a delicate black lace adorned with intricate patterns hugging her curves with a teasing embrace.  Her hair cascaded down in waves of lustrous golden brown, framing a face that could launch a thousand ships. Eyes, like molten pools of desire, gleamed with a knowing glint that hinted at secrets and pleasures beyond imagination. Her lips, painted a bold crimson, curved into a playful smile that promised both danger and delight.  As she moved towards me, I could see jewelry adorned her neck and wrists, sparkling with diamonds that caught the light and shimmered like stars against the backdrop of her flawless skin.  It was like a moment straight out of a movie.  It was surreal.  It was beauty beyond compare.  It was... About to be the most embarrassing moment of my life.  I could feel something rising up within me.  Something intense and powerful that overwhelmed me.

"Ah... Ah... Uhhghgg... Ooooaaahhh", I squealed a high-pitched moan that a listener would've swore had to be feminine.  My little member spasmed, sending out a weak dribbling cascade immediately visible as a wet spot on the front of my trousers.  In my humiliation, I saw the look on Kaitlyn's face go from practiced seduction to... Well, I didn't know.  There were flashes of different reactions.  Surprise?  Disgust? Curiosity?

While I was still overwhelmed, she stepped forward, pulling me into her embrace.  I tried to tilt my hips back, to keep that wet spot away from her.  Isn't it funny how minds work knowing that was what I was most worried about in that moment?  Didn't matter though because her hand slipped under my bottom and pulled me all the way into a full body hug.  The wet spot was pressed into her body.  Under normal circumstances, I would've been happy to have my faced buried in Kaitlyn's bosom, but in this case my face, my whole body, was burning with shame.  I couldn't believe I'd just done what I'd done.  Surely our brief relationship was now over.  Surely she was about to kick me out of her house in disgust.  You'd think I'd stop trying to predict how things were going to go given how wrong I'd got things so far.  Kaitlyn's reaction was nothing like I'd expect.  She was... Emotional.

"Oh my god, thank you Nicholas.  That is the most amazing compliment any woman could ever receive.  Men can lie, but there's one thing they can't fake.  Now that I know you think so highly of me, I'm sure I made the right decision."  She kneeled down, which almost put us at eye level, and then she kissed me!  The kiss was a breathtaking moment of connection. As our lips gently met, I felt a surge of warmth and excitement. Her touch was soft yet electric, sending tingles down my spine.  She tilted me backwards off-balance and held me there.  Her tongue delicately forcing its way into my mouth.  I could feel it pressing in, sliding over my teeth, teasing the roof of my mouth until finally she withdrew.  It took a moment to catch my breath.

"You're... You're not mad that I just...?", not knowing how to say what had happened.  Let's just say the brain cells were not working right in that moment.  But Kaitlyn answered in a way I never could've anticipated.

"Oh, my little Nikki, I think it's amazing!  Most guys make such a mess.  Shooting big white, thick, gooey strands all over.  It gets into all the worst places!  I so much prefer that you kept it contained and just made a runny little wet spot here."  Her hand slid into my bottoms, and wiggled around on the inside of the spot.  She smiled as her hand came out and she and held it in front of me.  I stared at it for a moment, wanting to apologize.  But as I struggled to think of what to say, she moved her hand closer to my face.  I think I was still in shock.  I started to ask what she was doing... And suddenly Kaitlyn slipped two fingers into my mouth!  Without thinking, I began softly sucking!

"Good boy", she said, gently wiggling her fingers.  I immediately grimaced at the bitterness.  I'd never tasted...  Looking up at Kaitlyn, I saw a look of complete bliss on her face.  I forced myself to continue to suck on her two fingers, focusing on the fact I was sucking my girlfriend's fingers and not what might be on her fingers.  She beamed at me and I just went with it.

After that, we made out.  I was awkward and clumsy, possibly because I'd never done this before!  Luckily Kaitlyn was patient and supportive.  We both remained clothed as she guided me into intense kisses, sensual caresses and deep hugs.  I realized we were making out in a somewhat chaste way like teenagers and I was grateful that Kaitlyn was recognizing my experience and going slowly.  Occasionally her hand would slip into my trousers and gently caress.  When I tried to return the favor, she just shifted or pushed my hand away so I quickly understood and I was very happy to respect her boundaries.  We eventually fell asleep together.  Kaitlyn wrapped her arms around me and was my big spoon.  I slept better than I'd ever slept before.

It turned out that Kaitlyn loved the fact I had a 'quick trigger'.  The way she explained it, with the other men she'd been with sex was painful as they hammered away at her for distressing amounts of time.  She told me how much better than those men I was.  It did make me feel good to hear that she thought I was the 'best' because I was so quick in bed.  But even with all her praise and joy, I worried it was a little emasculating, maybe?

So that's how our date nights went for the next couple weeks.  I was over the moon for the most part!  Not only did I have a girlfriend, my girlfriend was the richest, most powerful and most beautiful woman in the room.  We went to posh parties that most couldn't get into.  We went to concerts and sat in the VIP section and went backstage after.  Everywhere we went, we were together arm in arm.  I could tell people were pointing at us and the men were all jealous of me.  I was on a high better than any drug could provide.  Which was good because it helped balance my concern about what was happening in the bedroom after.

Initially, it was mostly a replay of what had happened the first time.  She'd dance in front of me in some very hot lingerie until I lost control, then she'd squeal in delight and we'd cuddle til we fell asleep.  There was no sex at all.  As the days followed, I started to get a bit put off by some of the things Kaitlyn wanted.

For example, she thought it was really hot when I lost control.  But she didn't want me to keep staining my clothes, so she bought some 'absorbent underwear' and laid it out for me when I went to her place.  At first it was just something like underwear with a little lining.  But after a few nights she was laying out something newer that had thicker padding.  Worse, the underwear started to have things printed on it, like teddy bears and unicorns.  Even though she kept calling it absorbent underwear, to my eyes it looked more like a diaper.  Kaitlyn loved it.  I would slip it on.  She would pat me, front and back, and say things like "Oh, is my little man ready to do some squirties?"  I did once tell her how I felt it was unfair that I was getting mind-blowing orgasms but when we were together, nothing was happening for her besides some kissing and cuddling.  Not a thing below the waist.  She just gave me a little boop on the nose and said she was incredibly satisfied and not to worry.  So we just continued on doing the same things.

Soon she was having full outfits laid out when we'd get back to her place.  There'd be some plastic shorts to go over the diaper and these strange little T-shirts.  I mean, first of all they'd be short enough that they wouldn't reach my shorts, leaving my belly exposed if I lifted my arms at all.  But far worse, they'd have little things printed on them.  I tried to ignore them, they were just childish things like building blocks and teddy bears.  But it was giving me second thoughts about how Kaitlyn saw me.  I mean, we'd still never even had sex.  I was still a virgin!  Was that going to change if she was dressing me up in what I thought was clothing appropriate for a small child?  Kaitlyn would tell me again and again how she loved me, how I was the greatest relationship she'd ever had and she was super happy.  I had to concede in public, my relationship was the envy of everyone.  And look, I might not have been getting sex, but I was getting some of the hottest, most intense orgasms every night we were together.  I didn't want to lose that!  So I kept telling myself I'd maybe stand up to her, I'd make some changes... Tomorrow.  I continued to wear the infantilizing clothes she pulled out, and we continued to do this strange little routine in the evening.

So although Kaitlyn had expressed her preferences on what I should wear, it was a new twist when she started to comment on my appearance.  Kaitlyn suddenly confided to me that she loved guys with long hair, and asked if I'd mind.  I assumed she was asking me to grow my hair out, so I said sure.  But I soon found out that wasn't what she was asking.  I know that Kaitlyn's company, MicroBotix, was working in the field of medical nano-robotics.  What I didn't know and what she confided in me was that with nano-robotics, you could get long hair much easier than growing it out.

"You could come in on a Friday, they'd book you in and by Saturday, you'd have waist length hair."  Of course I said that was far too long for me.  Kaitlyn acted like I was being silly.  "No, no, I was just using that as an example.  Of course you could make it whatever length you wanted."  I had to say it sounded like magic.  Kaitlyn found that amusing.  "You think that's magic?  Growing hair is the easy stuff.  What if I told you that they could go beyond what nature could do?  They could just as easily give you twice as much hair?  The average person has a hundred thousand follicles on their scalp.  You could have two hundred thousand!  It would be the thick, luscious hair most women dream of."  That really did sound like magic!  "Even better," she continued,  "What if I told you they could reinforce your hair with nano-fibers?  It would look, move and feel like regular hair, but it couldn't even be cut with scissors.  You'd need something like an industrial laser!"  I wondered why anyone would want indestructible hair.  "Lots of reasons!  You'd never have to worry about an accident.  And if you styled it, like if you curled it, it would hold the curl forever!  I mean until you straightened it of course.  So low maintenance!"  By now, we were beyond magic.  That sounded like Frankenstein-type stuff, but Kaitlyn told me it was nothing.  "Lots of people had already had it done."  She did admit it wasn't legal to sell yet in most countries, but they were confident they'd get approval in the next few years.

Turns out hair wasn't the only thing.  She mentioned they could do all sorts of things to change people's bodies.  Right away, I asked if they could make me taller.  When she said "Of course", I sat up.  But then she said "But Nikki, you're perfect as you are!"  And she laughed.

"But if I'm perfect, why do you want me to have longer hair?", I countered.  She just giggled and said it would be fun to play with.  I laughed along, but inside I was thinking.  Could I maybe get access to the technology to make me taller?  Wait... If it could grow my body, could it make me more endowed?  I'd started to worry that the reason we hadn't progressed in the bedroom was because of my size down there.  What if I could be bigger?  Would that be a way I could keep all the stuff I loved about the relationship and 'fix' the one thing that wasn't quite as I wanted it?  As I wondered, it suddenly occurred to me...

"If it's so amazing, why don't you get some enhancements?", I asked Kaitlyn.

"Who says I haven't?", she replied with a wink.  Ultimately, I decided to decline her offer to enhance my hair artificially.  I did tell her I'd let it grow naturally for her, but it did get me thinking.

---

It was a couple weeks after that when things finally came to a head.  We'd just had an amazing night out at a Tay Swifty concert.  We came home both all charged up and ready for action.  Kaitlyn was grinning the whole way back home.

"I've got a few surprises for you tonight.  I think you'll love them!", she exclaimed as she went off to change.  I assured her that I would.  By now I had my own room at Kaitlyn's house.  It had been the room she kept for her little cousin when she came to visit back when she was in elementary school so it was a bit girly and juvenile.  All pink and decorated with unicorns and ballerinas.  Now that her cousin was a teenager, she didn't really like the room anymore, so Kaitlyn said it could be mine.  We both agreed it would need to be redecorated, but for now it was just where I kept my pajamas and toiletries given how much time I was spending at Kaitlyn's.  It was also where when Kaitlyn would go put on her sexy lingerie, I'd go put on the outfit she'd lay out for me.  Except this time, things had finally gone too far.

I entered the room to find the usual t-shirt, shorts and 'absorbent underwear'.  Except this underwear was way thicker than any before.  It was huge!  It was like a cloud... It was... It was... It was a diaper.  No hiding it this time.  So thick and padded, I wouldn't be able to walk normally.  That was bad enough.  But the t-shirt was somehow worse.  I'd mentioned how the shirts had started to have childish pictures and emblems.  This one was offensive!  It had a crown on the center, but written around the crown was the phrase 'Preemie Prince'!  I was already feeling quite insecure about my lack of stamina, but this t-shirt was actively calling it out!  This was just too much!  I called out to Kaitlyn and we immediately sat down to have a talk.

At first she didn't understand.  She felt what two people do in the bedroom was between them only.  I believed Kaitlyn when she said this really turned her on and that it wasn't hurting anyone.  So I tried to articulate why it bothered me so much.  I told her that I thought maybe I was being objectified.  That it wasn't me she was in love with.  And I said I was worried that eventually she would tire of it, she'd get bored of the relationship.  I told her I wanted a 'real' relationship based on more traditional values.  Kaitlyn was surprisingly understanding, even though she assured me that people did have long-term healthy relationships with very different non-traditional paradigms.  She did admit that maybe she'd let her little kinks get in the way, and she did respect how I was feeling and was willing to discuss.  When I finally broke down and said it bothered me I was still a virgin, she seemed to have an 'Ah-ha!' moment.  Like she suddenly realized where I was coming from.

"Let's fix that.  Not tonight, I think we've both been pretty emotional tonight.  There is this amazing tropical resort, Lolligag Island.  I think we should both take several weeks off work, head there and just have a fun vacation together."  She giggled.  "And I promise you won't be a virgin by the time we leave."  I was just so happy.  Even though this was the greatest relationship of my life, here we were talking about making it better..  Kaitlyn was still willing to keep everything I loved about her, but address what I struggled with.  I couldn't be happier!  This is how relationships are supposed to be!

She offered to do the planning, book the tickets and resort, etc.  I was just in heaven.  Now I knew that all my problems would be solved in a couple of weeks.  I'd never been to this Lolligag Island.  Never even heard of it before, but now it was going to be the place where everything came together.  I couldn't wait to visit Lolligag Island!