Ashlyn, ma cherie!

**Kiwi_bloke** · 03-19-2015

This is a story I cooked up for my wife, who is an equal fan of TS/TG as I am, inspired by the awesome Ashlyn Creamher, who has allowed me to print it here for the [hopefully!] enjoyment of readers.

The story is 100% fiction! (dammit)

We were out scouting the op shops when I noticed a young man giving us an intense look. As he appeared to be an employee, I wondered if he thought we were casing the joint or something. The thought that it was our transgender support buttons never occurred to me at the time.

We did see one thing worth buying – a small silver plate listed as silver plate, but which actually had hallmarks for Sterling silver from 1861. Looked like $10 well spent to me.

We went to the counter and the young man came over to serve us. Quite an effeminate-looking young guy, and with a lovely smile.

“I hope you don’t mind me asking, but they are TG support buttons, aren’t they?” he asked quietly.

Upon us answering yes, he quickly said that he needed some support for a transgender matter but had no idea who to turn to as he was from a christian family and working with a load of christians.

We suggested he should come over and see us when he finished work at 5.
Sure enough, shortly after 5, he turned up and we invited him in. He was clearly as nervous as hell, but we calmed him down just chatting about the job and the things we’d found. He laughed with a very feminine giggle when we told him that the silver plate we’d bought from today for $10 was actually worth over $600.

His name was Brett.

After we’d got to that stage I asked how we could help him – by now realising the problem was most likely that he wanted to transition – and sure enough, that’s what he told us. He felt that he should always have been a girl, but his parents wouldn’t hear of it.

At age just turned 16, he hadn’t yet finished his very late puberty – he’d managed to delay it with extreme exercise – and wanted to figure out how to get onto hormones and start to transition.

By now we’d accepted that he was really a she and suggested she should first off get a name she wanted to call herself. She settled on Ashlyn, that being a name that had always appealed, so Ashlyn she became. We phoned Dr Martinique, a French migrant doctor who specialised in transgender matters that we knew through Julie. We arranged to take her to meet with the Dr the next afternoon.

We didn’t go in to the doctor with her, but Ashlyn told us all about it afterwards as she already had her first oestrogen pills to start things off. Obviously, she couldn’t take them home so we worked a plan that she would come to our place each evening to take her pill, then could carry on as usual at home.

It was hard for her living a double life, but there was no alternative.
She gradually got to spending longer and longer at our place every night. Her parents worked all day, then spent all night at the church, so as long as they thought Ashlyn was at the library as she’d told them, they didn’t care.
The oestrogen hadn’t started working but she desperately wanted to start being the girl she was and had secretly bought padded bras and lacy panties.
Even without the effect of the hormones, she had started looking like an attractive young woman rather than boy.

We discussed what she was going to do about her parents as they were going to notice sooner or later as she would sure as hell start growing boobs pretty fast at her age.

I asked if she’d get away with her signing up for a course at MIT and getting board close to Otara – obviously on the understanding that she would board with us. She thought it was possible and started checking out possible courses. Her marks at school had been really good and she’d left at the end of year 12 having just turned 16 after being accelerated through the earlier years. She had thought about nursing, so asked her parents if they’d go along with her studying nursing and boarding with a nice couple with three kids.

As she told us later, they seemed only too happy to see her gone and hadn’t even asked our names. She thought her parents loved their delusion of god more than her, so she determined to follow that path as soon as she could.
We had 6 bedrooms, so there was plenty of room for her and the kids had already spent enough time around here that there wouldn’t be any issues. They already thought she was a girl.

Time went on and Ashlyn became more and more comfortable with herself. She was at MIT, and it turned out to be the ideal place. Along with her, there were two fa’afafine and two other trans students, one M2F and the other F2M and a couple of gays. It was a real rainbow class and she’d already brought some of her friends from the course around for a barbecue.

By the time of her seventeenth birthday, her boobs were starting to really grow and as the padded bras became unnecessary. As it was holidays, she took to walking around braless, and they certainly looked bloody fine from where I saw them. I saw you watching me looking and smiling as you saw me get interested.

One morning, I heard a noise and went to investigate, only to find Ashlyn just getting into bed. Her door had blown open and hit the wall. She was topless.

She smiled at me and I swear she even thrust her titties out a bit.
I smiled myself and just said I was checking on the bang. Ashlyn had already figured that out anyway. I went back to the kitchen, but was reminded of the incident only a week later.

Ashlyn wanted to buy some sexy underwear and the pair of you had gone to get some. She’d spoken about her sexuality and feelings and was now getting to grips with it, she felt. We’d been open with her as well and explained how we’d had sexual relationships with Julie and Dany – and still did on rare occasions!

Again it was early morning, and again there was a thud from Ashlyn’s room. I was more reticent this time and called out softly to ask if everything was alright. Only a slight grunt answered me so I swiftly went to her door.
It was open, but this time, Ashlyn hadn’t even noticed. She was masturbating in her new underwear.

As I turned, she opened her eyes, but I don’t believe she was even aware of me. I was sure as hell aware of her! She looked sensational.

About a fortnight later, I’d been out visiting customers when I arrived home. I’d expected to be a couple of hours, but one had cancelled and the other took 5 minutes, so I was back about an hour and quarter earlier than expected.

When I walked into the lounge I was surprised to see nobody about and figured you were doing washing or cleaning while Ashlyn was at tech.
I walked quietly into the bedroom, hoping to catch you unawares and I sure as hell did.

When I got to the door I stopped and gaped as an electric bolt shot through my cock. Ashlyn was lying spread-eagled on the bed and your face was buried in her cock. I could see you pressing your mouth to her pubes, so you had the whole thing and I could see a big wet patch on your bike shorts.
You were both completely preoccupied with what was going on, and I was quite happy to stand and watch.

You began to rub your clit through your shorts as you sucked and slurped away at Ashlyn’s cock.

From my angle, I could see her balls tighten as she was about to blow her load, then saw them spasm as she sent shot after shot of her come into your mouth.

I could no longer resist, walking over and pulling you off her, immediately clamping my mouth over yours to taste and suck the remaining come out of your mouth. As I did so, I shoved my hand straight down your shorts to your saturated pussy, slipping my finger all the way in as you shuddered.
By now Ashlyn was starting to recover and gave me a wide, dreamy smile as she saw us kissing. Her smallish cock was already beginning to get hard as she watched me fuck you with my fingers.

We dragged each other’s clothes off in a frenzy and I pushed you back to shove my face hard into your pussy. You bucked your hips as my tongue licked you from anus to clit, probing deeply in your pussy as it went.
You were already nearing orgasm, so I slowed the pace, wanting to build you up to a level you’d never been to before.

I hadn’t noticed at all what Ashlyn was doing, being completely occupied with your delicious body, but my naked arse was sticking up in the air and I felt a slippery hard thing touch my anus. It was Ashlyn, who had climbed up behind us and was rubbing me with her dripping cock. I pushed back gently to let her know I liked it as I began to really plunge into your pussy.

Both my hands were playing with your tits as I licked, so I brought one down, all the way down, and around the back, to your anus. It was completely lubricated by both of our juices and there was no resistance as my finger slipped inside you as my tongue flicked your clit hard.

As you began to pant, the cock pressing into my anus began to push a little harder, so I waited to time a thrust and next time Ashlyn pushed, so did I. Hard. Her cock slipped straight into my anus and she began to pound me with it. My own cock was bar-hard, dripping a line of drool all the way to the floor.
As you began to shriek in orgasm I felt Ashlyn thrust herself all the way in and begin to come. The hot spurts were aimed straight at my prostate and my own orgasm spurted out of me like an oil well gusher. We all shouted as one as well all flooded the world with a three-way simultaneous orgasm.
We lay there for a long while, brain dead, consumed with the strength of the orgasms.

Ashlyn began to tell us in a voice cracking with emotion how that had been her first sexual experience with another person. Aside from some mutual masturbation with a gay boy at school, she had never had any sex at all. She had felt like a freak, thanks mostly to her parents, and was scared of intimacy.

She laughed when I said that she appeared to be over that, pushing herself into me!

You leaned over and kissed her and I jumped up to have a shower. You both decided to join me in our huge, double-headed shower and we were soon all soaping each other’s bodies furiously. Both Ashlyn and I were hard, while your nipples were like pieces of flint, even in warm water.

Now perfectly clean, we returned to the bedroom and you re-started the kiss you’d begun to give when we all went to shower.

I put my arms around the pair of you and began to massage both of your breasts – a matching beautiful pair of pairs of little boobs!

You broke off the kiss and looked at each other, nodding briefly, before grabbing one of my arms each. I completely failed to resist and you pushed me back easily to lie on my back. I could feel both of your mouths working on my upper thighs, then begin to lick towards my cock. One of you broke off to tie me.

I was pulling against my bonds as you both began to lick the tip of my cock, and each other’s tongues. In fact, the tongue-licking soon took precedence and you moved away from me to concentrate on each other. Your hand was working flat out on Ashlyn’s cock while she thrust fingers up you and rubbed your clit.

You lay back and spread your legs, mouthing “fuck me” to her.
And she did.

Soon, she was pounding away and I could only watch in awe as you began to orgasm with the pounding of her delicious young cock.

Ashlyn hadn’t come yet and the pair of you untied me. I could see by your glazed eyes that you weren’t ready for any more and I began to kiss Ashlyn.
She began to pant as I started to roll her nipples between my fingers. I alternated between her tits and cock, smoothing her sweet juice all over her breasts and my tongue.

I lifted her on top of me, face up and slotted my cock into the crease of her buttocks. Spreading her legs as wide as they’d go, I slid my cock to a position where it was touching her anus and began to gently rub her balls and cock, which was by now running with fluid.

I began to gently push at her virgin opening and soon felt the resistance begin to disappear and I started to slide into her.

I rocked gently as my cock reached full depth, playing with her now rock-hard cock. I could feel her start to come, splattering semen all over my hand, which I pulled straight to my mouth. The taste of her come and tightness of her anus sent me over the edge too and I splashed what felt like a gallon of come in her.

She came again as the hot semen hit her prostate.

As I collapsed, I felt your lips close over mine and I returned your kiss with my tongue. I dropped my hands to your pussy to feel it saturated with Ashlyn’s come, which was by now drizzling down your legs.

“Clean me up” you ordered and I immediately slid down the bed to meet your pussy that you thrust towards me.

I smashed my face into your pussy, tongue first, scooping a huge tongue-full of come into my mouth and swallowing it with a smile. You groaned in pleasure as I licked deep and hard.

After I’d sucked every drop of come from your pussy, I began to lick your clit and you began to pant, nearing orgasm. A final thrust of a finger into your pussy sent you all the way and you bucked and jerked as another enormous orgasm flooded through you.

Being young, Ashlyn had been watching and getting harder by the second.
I was even recovering a little myself by now and leaned over to stroke her cock.

She said that she just wanted to wank this time while she looked at us naked – she was incredibly horny after watching us fuck and suck.

We lay in other’s arms as Ashlyn stroked her cock faster and faster.
We pulled her towards us so she was touching you with her legs as she wanked. You could see by her face that she was near the point of coming, so we hugged her tight and she began to pump yet another load of come, spurting over your tits and body and mine. We pulled her on top of us so we could all squirm around and mix the come over all of us.

We did not awake until the next morning, when we all shot awake together and began laughing simultaneously at the dried come that had hardened over all of our bodies.

Unsurprisingly, we all wanted more, but nobody had showered so we all decided to have a wank-in and all began to play with ourselves while watching the others.

Within 10 minutes, we’d all achieved another orgasm, both Ashlyn and I splashing come over your tits as you came. True to form, I licked your boobs clean of all come before we went to shower.

After a couple of months of sexual activity with us, Ashlyn had become as naughty as hell and we were constantly finding her naked.

Well, what’s a couple to do but take advantage of it!

On one occasion, you stood behind me, while I fucked her, and whipped me with your riding crop.

We both came, then you quite rightly felt it was your turn, so lay back while Ashlyn and I took turns at licking your face, mouth, breasts, pussy and anus. You were covered in your own juices as we rubbed them into every part of your body.

Both of us would take you right to the edge then stop and you were getting so horny it wasn’t funny – you kept trying to grab a face or hand and thrust it between your legs.

After about 20 minutes we relented and as Ashlyn and you kissed, I licked your clit until you came so hard you nearly broke my jaw.

By now there was nobody could have picked Ashlyn as a trans – she was simply a beautiful young woman who just (fortunately) happened to have a cock.

One Friday, Ashlyn rang me up and said she wanted to cook a special dinner.
We hadn’t realised, but it was exactly a year since she met us and she wanted to show her appreciation with a special celebration.

Dinner was superb and followed by wine and cocktails.

We were all getting horny, just all sitting together on the couch and touching each other gently every now and then. You could feel the sexual tension rising by the second.

As we all moved to the bedroom we began to undress and I had the enjoyable task of removing both of your panties with my mouth. Just as I kissed your pussy on the way past, I quickly sucked Ashlyn’s cock into my mouth for a second.

Ashlyn asked if there were anything she could do that we’d like to try.
I said I’d like to watch her have a wank – with a specific plan in mind – so she settled herself down on the bed and began playing with her cock. We held hands and snuggled as she started to get serious, eventually shooting a load over her tummy.

I scooped up some of her come and rubbed it into your nipples, then proceeded to lick the clean. You scooped up a finger full of come and licked it clean before returning to get another. This time, you slid your finger down to my anus and rubbed her lovely semen into my anus. I loved how slippery it was and tried to squirm into position where I could ram myself onto your finger, but you avoided it easily.

By now we were both horny as hell and Ashlyn had already recovered and was hard again.

I turned you over so your arse was up in the air and Ashlyn and I began to tongue you, licking and flicking. Your pussy was now pouring out juice and you were ready for a lot more.

I helped Ashlyn get into a position where she was lying down so you could climb on top of her stiff little cock. You immediately began grinding yourself into her young body. I could see your anus was glistening with your own juice and the remnants of Ashlyn’s come. I gently moved my cock to right next to your anus and as soon as it touched you thrust backwards, forcing me all the way in.

As I fucked your arse and Ashlyn fucked your pussy, I could feel her cock and mine rubbing together as we timed our thrusts, with only the thin membranes of your pussy and rectum keeping them apart.

Our balls occasionally brushed, sending bolts of lightning jarring through us.
I reach down to touch your clit inbetween the legs and penises that were pounding into you. You gasped as I hit the spot. I directed Ashlyn’s hands to your tits and she began to squeeze your nipples.

As you began to come, I felt Ashlyn’s cock jerking her load of come into your pussy. I could feel the heat of it, and her and your movements had me immediately splashing your insides with a gigantic load.

You actually passed out for a while, a spent unit, filled with come in both sides, pussy anus and nipples throbbing after the hardest orgasm you’d ever experienced.

Ashlyn and I just held hands and watched you as you breathed deeply in an unconscious sleep of the totally satisfied.