Sissy Perfection

Hello.

I had done just about everything there was to do mature, lesbians, trannies. And several times each variety.

So I thought it was time for a twink.

As with my previous adventures Hong Kong was my hunting ground.

Two, week long trips a year made it easy for me to indulge me desires.

I guess I am pan sexual...whatever that means. I'm open to lots of things, but not everything.

I like to fully crossdress with other of my kind. The classy bourgeois kind, not some hairy dude in a nightie.

I love girl on girl, especially when there is an age difference. Watching a 20 year old beauty succomb to the advances of an elegant, grey haired 60 year old is just so erotic.

So most things but not straight guys. Hairy, muscular, overweight...not for me.

However a fit, firm, hairless twink, why not?

So I placed my order with the agency. I can't remember exactly but it went something like this.

Smooth twink. Under 25. Thin and firm. 170cm max. Ready for some light crossdresser and boyfriend experience. 24 hour incall.

And 2 days later that is what I got.

Day one:

Jason arrived around 6 in the evening.

Let me describe him to you.

Short, about 165-170cm. I found out later that he was 21. Chinese descent. Even, tan skin.

His member was average for his size, so on the smaller side (but I preferred that). And cut.

What was remarkable about him his total lack of body hair...anywhere.

I would describe his face as neutral, not particularly masculine or feminine.

When he rang the room bell I was already in my lingerie. I loved dressing.

I had on a pair of glossy 20 denier nylons, a one piece shaping bodysuit with 6 suspender straps.

Attached to those were seamed Cuban heel little tan nylons with a black welt.

I had a black ankle length silk gown to cover me up.

Jason came in and I offered him a seat.

We exchanged small talk for about 15 minutes. But this story is not about small talk.

I remained seated and asked if he could come towards me.

He came close and I unbuttoned his jeans. He instinctively removed his t shirt.

He must have removed his shoes earlier.

And there he was, just for me.

Now just wearing shiny electric blue Calvin Klein boyshorts.

Ironically they are called boyshorts and indeed a boy was wearing them but they were so obviously designed for women.

After caressing his tight ass and inspecting his small bulge for a few moments I stood up.

For me nothing is better than a handsome cock encased in nylon.

I asked him if he would mind taking his boyshorts off and putting on some tights.

I went through to the bathroom to finish putting on makeup and getting dressed.

Makeup takes time. About 30 minutes later I was ready to slip on my wig. A blond wavy one on this occasion.

Slipping on my stretchy silk 1930's dress was so divine. Of beige colour with a simple black pattern it was my favourite.

I slipped in to my 4 inch pumps. And then I was fairly liberal with the perfume.

On the crotch also. I would ask Justin to do he same. I love the mingling of body scent and a floral perfume.

So I was ready. When Justin saw me he just did a little clap and smiled. That was nice.

I opened some white wine and sat down and lit a cigarette.

I once again asked Jason to come over to me. He stood and for the first time I saw his cock encased in some glossy 10 denier nylons.

I couldn't help but squeeze his butt again. I then sprayed some of my lady perfume on his crotch and derrier.

After massaging his but for a few seconds I took his hand and led him to the bed.

I layed Justin on his back and slithered on top of him.

Our lips met tentatively at first. He seemed horny... unlikely to be as horny as me but he was aroused.

I stretched my arm to stroke his well defined member through his shiny stretched nylons.

It wasn't long before I had moved down and was licking the underside of his member enjoying the mix of his scent with dolce vita perfume.

I sensed it was time to prepare him for entry.

Justin lay on his stomach. With a generous amount of lube I massaged his boy pussy.

It seemed to relax him.

Before long I was fingering him. First one finger then 2.

When I thought he was ready I pulled his nylons back up and prepared myself.

A dab of lube on my cock before slipping on one of the condoms I had placed under my tights.

Then a generous amount of lube on my sheathed cock.

His nylons needs to be ripped to allow me access.

I eased in gently to his whimper.

I was so horny I knew this would no last long.

I slowly increased my pace and about 30 seconds before coming I stopped and let his writhing take me to a long and satisfying orgasm.

It was his turn.

I layed on my back and removed the condom. My dress was lifted up but my bodysuit still attached, my cock pulled out the side of the bodysuit.

He generously lapped up the cum from my cock then came up to kiss me. This wasn't the first time I had tasted my own cum.

Despite what people say it tastes of very little but is slightly bitter.

Now that my lipstick was glistening with my own cum Jason started massaging my pussy with some lube on two fingers.

I love this part...so much expectation.

Before long I had my legs up in anticipation.

Jason lubed his lithe cock before slipping on a condom.

No not one of these stories where every cock is absolutely huge.

I would class his has cut, straight and slightly below average size.

At any rate of would soon be inside me.

The first penetration is always tough. This was no exception.

But the still nylons Jason knew to take it slow.

He went full tilt very slowly then just moved from side to side a little. This loosened me up.

Before long he was pumping pretty hard. It's a great feeling when you are completely relaxed with the whole thing.

Jason unclipped my bodysuit and tore my nylons more as he pushed my legs further back.

Fuck I was enjoying this. Amazing how chicks don't to have sex more often.

Jason flipped me over so I was doggy style on the edge of the bed, knees nearly on floor.

He entered me then pumped hard and fast for only about a minute then came inside me.

He stayed standing and inside me as he caught his breath.

I loved the feeling of his cock twitching as it softened.

The exiting is strange. It's feels great, the semi limp member flopping out but then as air fills the orofice it feels cold...and empty.

I thought he would last for longer being a pro and all but I didn't mind, I was satisfied.

We peeled off the torn nylon and headed towards the shower.

Once the water was the right temperature we lathered each other with soap.

This was so sensual. My makeup did need to be removed however...no worries with makeup remover.

While I was doing that Jason caressed my derrier with his soaped up hands.

By the time I was finished with my makeup he had started washing my cock.

I returned the favour by soaping the lube from his crack. To do this I needed to come in close to his neck.

When I gave some gentle pecks on the neck I noticed our semisoft cocks touching.

Of all the intense experiences this 24 hours would bring that was one of the most memorable.

We then kissed on the mouth, sensually like reunited lovers.

While we were exchanging tongues under the rain shower we tickled each others pussies.

This is one of the great things with same sex sex, the symmetry of the whole exercise is so wonderful.

I am not ashamed to admit that I was feeling a little emotional. I felt the need to serve my companion.

I got on to my knees and took his cock in to my mouth. I managed to get Jason fully aroused but I didn't want to finish him here.

All the soap was long gone. I got up and turned the shower off.

We both dried ourselves.

After a moment of pause I seized my opportunity.

Jason was naked and dry and standing in front of the large bathroom mirrors, leaning in slightly.

I walked up behind him kissed him on the neck.

Without hesitation I dropped to knees (again!) and started kissing his ass.

He was gorgeous, he deserved it.

I wanted to give him analingus,...so I did.

Once I had my fill and I felt his pussy relax we moved through to the bedroom.

We both sensed the need to take our time. He slipped on the hotel silk gown then rummaged for a pair of nylons.

I was chuffed that he took my request through the agency so seriously.

I slipped on a pair of seamed glossy tan 20 deniers and slipped on the matching hotel silk gown. We resumed our wine and each lit up a smoke.

We lounged on the sofa facing each other so we could enjoy our nyloned legs slipping against each other.

After a few minutes of idle chit chat...his career choice, the source of my desires etc. Jason rolled over and bent his ass up to me over the arm rest of the sofa. I massaged his ass for a while before peeling down the nylons so I could resume annalingus.

After a few minutes I started working some lube in to his pussy with one then 2 fingers. I was enjoying the slower rhythm. The need for immediate orgasm had passed and we had time to enjoy each other properly.

After a few minutes of massaging and getting to insert a third finger I took the condom Jason had placed under the right rear thigh of his nylons.

Once it was on my cock I positioned Justin so he was squatting on his knees facing the wall. This way I could fuck him from a standing position while he was kneeling on the sofa. I pulled down his nylons a little more to give me full access.

I adored his position of compromise. After about 10 minutes of mostly slow pumping I removed my condom and spread some lube between his ass cheeks. Then squeezing his ass cheeks together I fucked his crack before spraying my cum on the small of his back. That was a really nice long slow orgasm. It always is the second time.

As I have done before I licked up my cum making sure to get plenty on my lips. Justin retired from his position, pulled his nylons back on and sat down. We kissed so he could clean my cum off my lips. Mutual tounguing resulted in the full exchange of my juice.

I went and lay on my stomach on the bed indicating to Justin that it was his turn. Justin dissappeared to the bathroom and came back with some moisturiser.

Over the next hour I received a fantastic massage of my back, shoulders, butt, legs, arms and feet. Of course he had to remove my nylons once below my back. At the end of this I got a great slow entry by Justin. He spread a generous amount of lube in my crack then with his semi hard he started rubbing between my cheeks. When it was hard enough he would press the head against my pussy for a few seconds then keep slowly fucking my crack.

Each time his head against my pussy he pressed a little firmer. Once he could enter his head in to me he put on a condom. I thought he would just go straight in to it but he was very patient and just dipped his member a little further each time, very slowly and pausing for at least 5 seconds. And in between enterings he would gently fuck my crack. This was actually the best fucking I have ever received and I've had a few.

I was still fully on my stomach and I felt like I was getting more of a rectal massage than an ass fucking. He obviously liked it too because once in to full hilt Justin only pumped slowly for about a minute before coming.

We showerd separetely. Upon exiting the shower I went to get some more tights form my stash...no tan left we were on to black sheers. That would be a little job for tomorrow morning. Not surprising given the pile of torn nylons and wrapping beside the bed.

I slipped on a pair of 10 denier glossy black nylons and got in to bed. Justin was already there on his side also nylon clad. I cosied up to him and spooned. The light friction of my nyloned cock against Justins ass cheeks gave me small hard on. But the time for intimacy was over.

Day two:

When I awoke Jason was already in the shower.

In my mind I made a list of how the day should play out.

Shower, Breakfast, Shopping for nylons, dress en femme, Fuck, Lunch, Relax, Fuck.

I ordered breakfast to the room for the both of us then looked up where I could go to buy some more nylon. Sorted.

I took to the shower after Jason. When I came out he was sitting at the small table wearing the silk gown and his boyshorts. I made myself less than decent in a pair of black silk panties and a pastel pink slip. We ate breakfast talking about nothing in particular.

I excused myself, dressed and went out shopping at the nearest mall. Fortunately it was within easy walking distance. Top hotels tend to attract shopping malls and luckily this one was the right mix of top end and more practical stuff.

Not sure they sell what I wanted in Gucci but there was a Wolford store, perfect.

I got some classic 12 deniers seamless for both of us. Black, tan, navy blue and a dark Brown.

On the way back I came across a lingerie store that had the same kind of boy shorts that Jason was wearing. I thought it only appropriate that I gifted him some more. I bought a pastel yellow pair with a wide silver waist band.

Upon my return I gave them to him. He put them on over the new navy blue Wolfords. I have always appreciated the combo of blue and yellow. Yum!

I also changed in to the pair of tan shiny 20 deniers. Although it was all of 10 am I had a sudden desire to dress up. So I did.

Black, stretchy mini skirt, pink silk shirt, glossy tan nylons I had just bought, baby pink suede heels, full makeup of course, red bob wig, simple clip on shiny ear studs and thick faux diamond bangles, pearl necklace. So that was my secretary look.

He approached me this time. He walked up to me as I had my back against the mini bar. He gently pushed me back to make for me to sit on the benchtop above the fridge.

Still standing Jason but hunched down and started licking the gusset of my pantyhose. He knew full that by proxy he was caressing my balls. As my blood surged I smelled the sensual aroma of Dolce Vita emanating from my crotch. This only made me harder. Jason then tore at my nylon sheath to release my cock. He took me right down to the back of his throat and back for a couple of minutes. I slid off the minibar upon Jason stood up. Approaching orgasm I desired something in my mouth. I slid off the minibar et which point Jason stood up. We tounged for a few seconds before I turned Jason around against the minibar. I pushed him up on the minibar so his feet were off the floor? I slid his yellow boyshorts down to his knees. Just some nylon between me and his pussy. I ripped his blue wolfords and forced my tongue in to him while squeezing his cheeks tight.

So above the mini bar was not the easiest place for this to be happening.

Mutually we made ourselves over towards the bed.

Jason instinctively knelt down on the floor resting his torso on the bed. I could then have access to his ass if I knelt on one knee.

Before dropping a knee I went to the bedside table to get some lube. Walking there I became acutely aware of my pulsating erect cock.

I dropped to both knees to prepare Jason. Once I started doing this Jason reached for my free hand and started sucking on two fingers. That was really nice actually.

Aftera while I eased into Jason's pussy. No condom yet, but just a slow deep rythm.

After a few minutes Jason motioned to change positions. I ended up sitting on the ottoman with my back against the bed. Jason gestured me to spread my legs. He then place a condom on my cock. I almost came right then to his gentle delicate touch.

Jason then got in to position which involved him crouching with his back to me. As he squatted further I had a perfect view of his messy lubed up ass. He lowered more so as to impale himself on my cock. The rhythm started... I loved this position. I think maybe because it was super humiliating for him in some way.

When I was close to coming Jason sat on me and tickled a slow orgasm out of me by just wiggling from side to side and up and down a little. Awesome...it was really slow and constant.

Once off me he lay on the bed to give his knees a rest. He was still erect but I could see that he was puffing a little.

I got in to position to gently lick his balls. I thought he'd deserved something slow from me also. At this he parted his legs to allow me access.

After a while I started sucking his cock and eventually found myself in a 69er position. I had gone limp but I could feel a little swelling returning.

It didn't matter anyway because Jason was more interested in my ass. He found the lube and started tickling me with one finger going around in circles on my boy pussy. After a while of mutual pleasuring Jason gestured me to lower myself on to his face. That meant abandoning his cock as I couldn't reach. Once my height was just right Jason gave me great analingus. Eventually his tongue found its way in to me.

I deserve to be fucked. This would be a straight forward affair, a good old fashioned sidewinder. I relaxed on my right side while Jason busied himself with giving me a slow gentle fucking.

Hugs and showers ensued.

The last act was Something I was not expecting.

Jason went to his carry bag and took out some large plastic sheets.

He skilfully laid them over the bed and tucked them in as if they were bed linen.

He then got 4 towels from the bathroom and laid them on the carpet at the base of the bed.

Lastly he got a bottle of Johnson's Baby Oil from his bag.

I had always wanted to try an oil session but the mess and organisation required had always detered me.

This was perfect, I had someone to do it all for me.

Jason walked over to me and gestured to me with his hand to stand up.

He gave me a little peck on the lips and then undid my silk robe.

With my semi hard member he led me over to the plastic covered bed where I lay down on my back.

We would be naked this time, au naturel.

Jason applied a generous amount of oil on my chest and legs ensuring not to miss ly limp cock.

He was careful not to get any on my face.

The light massaging of oil went down to my feet.

not surprisingly Jason then lay on top of me gently shifting his bodyweight up and down in a slithering motion.

When the oil was evenly spread over both our fronts Jason gently kissed me on the lips before starting the most gentle grinding motions of our groins. We were both soft. it felt divine having someone playing with me like this.

At the first sign of arousal Jason motioned me to flip on to my tummy. he repeated the exercise of oil on my back.

Once applied he gave me a series of pecks on the neck.

His reverse side frotting of his oiled cock and balls on my ass crack was massaging to say the least.

after a couple of minutes i noticed his arousal.

At this he concentrated his hands and fingers on my crack and boy pussy.

before long I could feel his hard member pressuring my hole.

Things were very slippery, entry would not be easy.

Jason had to work harder to gain entry. 4 of his fingers in a tapered formation were requied before he could enter his hard cock in to me.

This entry actually felt like relief. And of course it was all so smooth. After a few minutes of steady action, Jason became harder and longer.

With that he stopped pumping and lay flat on top of me, still inside.

He exited briefly to put on a condom.

Once back inside and on top of me he slipped his arms under mine with my arms down by their sides.

He bear hugged me from behind and started fucking me again.

The only part of his body that was moving were his hips.

Jason penetrated much deeper this time.

The only word I can think of is exhilarating!

I could feel my own cock getting hard as it pressed flat against my stomach.