Category: Transsexuals & Crossdressers Stories

Milkmaid at the Back Door

by Cumfusion©

This is a sequel to: 'Cherry deflowered at beach party'


After all the guys had done me so forcefully I just felt so thoroughly fucked. Once I had been allowed to get back on my feet and take a few steps all I could feel was this slimy stickiness between my bare thighs. The problem was I just couldn't control my bum any more. I tried hard to clasp my anus but I just didn't seem to be able to stop it happening.

As we made our way over to the barbecue it was obvious, I think, to everyone that cum was visibly oozing from my bum slit. The girls were giggling while swigging Bacardi Breezers from bottles and pointing at me.

"Can't you see zat Carl is leaking?! Has no one got zer ass plug" Helga, our famous Lithuanian Chief Engineer had been walking behind me. She had just fingered my cleft which only made matters worse. "OK I vill go to get somezing"

Susan approached Tom who was starting to cook burgers on the barbecue. I was surprised to see he had got as far as taking his shirt off. In fact he looked pretty good. I just was wondering why a guy who was so fit and muscular looking could be so unmanly in his manners.

"Tom what on earth are you doing in those smart trousers on the beach; you'll ruin them!" she said scolded him as if he was a small boy; she started busily brushing sand off them.

"Oh come on! These have got to come off!!" Mandy was showing signs of alcoholic recklessness already . Without asking him and, assisted by Shirley, she undid his belt and pulled his trousers down. But the way they did it his pants came down as well. "That's better Tom" said Shirley "now you're in the nude just like the rest of us!" then glancing at his genitals and looking around to the others "Hey look! he is not too bad really, is he?!"

"Yea you've got some equipment to be proud of down there Tommy boy, you needn't be so shy you know!" Mandy was indeed nude along with the other girls. They were all flouting their breasts to the guys and to each other. But the only thing was, all the other male party goers were in a sort of 'after fuck' phase. Their now flaccid dicks still looked nice and fat and slimy from fucking my asshole only minutes previously. Seeing them made me want to suck each one of them right then but I was too embarrassed to approach them all together like that.

But now Tom's bum was lily- white and quite hairy. He was obviously not used to showing it publicly. When I saw it first as they pulled his pants down, it seemed so private and yet so irresistible. I had just caught a glimpse of his dark hairy crack, it made my little cock get aching hard. It was almost like it was asking to be fucked!

Then I saw Angie summoning me over with her finger. Who was I to disobey the Office Manager? "Here come and show Tom what you've got!" she said making me kneel in front of him. He was squatting in way trying to conceal his nudity. She started stroking my cock and squeezing my knob right in front of Tom's face. "Come on Tom! He's all ready for you. He's been saving up for you, this is the way he'll be able to give you those 'indentures' you see!"

At first Tom just gingerly kissed my shaft but then he gradually seemed to warm to it. Next he was licking me and further and further towards my knob. It got intensely exciting. Susan, Shirley and Mandy were all crowded round, one of them was stroking his hair. Tom was now sucking me vigorously but Angie had leant forward to hear something Susan was saying. I realised Susan must have been fingering his ass or something from behind.

"He's ready!" said Angie getting up. With the help from the other girls they got him on his back and held his legs apart. The sight just blew me out of my mind! How could these girls know how much a man's hairy ass cunt would turn me on! Mandy was lubing his hole like she had done with mine. She was working fingers from both hands and pulling his fleshy cherry apart so you see his tight pink tunnel. He wasn't much dilated but he looked so ready for my raging cock. Tom's dick was hard. It was quite big too and Susie was visibly shaking with excitement as she fitted a condom over my aching cock From then on I must have been on some sort of 'auto-pilot' although I had never fucked a guy before. I just had to dive into him.

OH WOW HIS HOLE WAS SO FUCKING TIGHT!!! He was HOT too but he was going to get it!! OH BOY I WAS GOING TO FUCK HIS ASS. He was gripping my knob with his cherry. He made a futile attempt to resist but I just had to force my way into him. I wanted to get right up inside, perhaps I wanted to prove something after being so publicly fucked.

His eyes were wide looking at me as I felt his sphincter yield to my stiff little dick. He could never hold out! I looked down to see my rigid little prick disappearing into his virgin man cunt. I got to screwing him like some guys had done to me, I knew it felt good and it made Tom throw his head from side to side in ecstasy. I was sure he'd never been done before and I wanted to give it him real good – but then what was this??

Something was coming up MY asshole and it was FUCKING GIGANTIC!!!! "Vee vill see vat zizz does to you zen!! You vere almost too quick for me but not quite I sink!" Helga had rammed me with this massive strapon! It was only because my asshole was dripping cum and slippery that she managed to get up me with a thing that big! Oh shit I tell you! If I was excited before but I was about a million times more excited now!

This thing! something so enormous! it was inside me. Oh yea really right up inside; I mean well ... FUCKING RIGHT UP MY RECTUM!! GET IT?!!!

Tom lay there utterly passive looking, I had lost the initiative, Helga was in control of me now. She was inside me and in control of what male genitals. Then I got this MAAAASSSSIVE ORGASM, OH SHIT!!! it went on and on, I couldn't stop!! I just got tighter and tighter inside and my little gland went on and on spasming. It was trying to ejaculate and it simply couldn't! Helga had overpowered me and I was shouting out wildly. The girls were kissing me all over.

Suddenly Tom's face screwed up, he cried out, and I saw his cock spurting loads of cum all over his hairy chest, some reached his chin even. I guess my dick may have been just enough to constrict his semen tubes a bit, like you pinch a hose pipe to make it squirt. I milked his cock a bit like Helga had done to get out the last few drops while he groaned and threw his head around. I don't think Tom had ever been so happy. He certainly wanted more later. And, Oh yes, I nearly forgot! I was confirmed in my job!

"Hey Carl what's wrong? The condom's empty!" said Susan eventually after it was over; she was incredulous as she peeled it off my still stiff cock.

"Zat is Vy zer Milkmaid just arrived in time isn't it!" Helga announced in triumph. "You see vith a big sing like zis" she said waving the strapon at us all, "he vas quite unable because I vas in control! – So! Now it is Milking time for you Carl! You have never been milked before huh? Vell zere is always zer first time! So girls I vant him on his back vith his legs right up and apart zen I can get to vork on him!!"

Helga was quite right that she had somehow stopped me from ejaculating into the condom. It must have been the size of that dildo thing. I felt so deflated and emasculated in front of the girls.

But there wasn't really time to feel anything much more as Helga was now fingering my asshole in a very specific way. She had two fingers up me and was doing some thing to my gland. I was going crazy with excitement again. She was stroking me somehow inside and it felt like she was touching the very core of my sexuality. She had total control over me and it felt like there were waves of thrill shooting around my bowels and genitals and they were getting more and more intense all the time. But I was getting frustrated too as I couldn't resolve my orgasm and ejaculate. I was completely under her control.

Then she said something quietly to the girls like 'I think he is ready' anyway I then got the strangest sensation as I felt cum oozing from my cock but I still hadn't orgasmed. I could feel it coming out of my knob. Helga was forcing me to expel my sex juices. There was nothing I could do, she controlled the most basic thing in my manhood.

It was strange but also desperately exciting!! For at least five minutes she went on extracting my juices. My cock wasn't even hard any more, it went pathetically limp as she pulled two fingers along it repeatedly like she was squeezing the last from a toothpaste tube.

When it was over Helga announced triumphantly "Won zing now you cannot fuck zer girls or even any guys because you have been completely milked out!"

Mandy and Susan looked a bit angry about the way Helga had muscled in on me. It was like they wanted to protect me from her "Yea very clever! but we thought you'd be with your mechanics. Where are they? cos that's where you normally get satisfaction isn't it?!" said Susie in a huff.

"Zey are not mechanics, zey are Engineers!" replied Helga indignantly.

"You still haven't told us where they are, we expected them to be here!" Angie replied flicking her hair cheekily.

"In zer Engine Room of course! Where else do you find Engineers?! Come on vee go!" she said grabbing me and bundling me into her 2 seater SUV.

I had no idea where we were going and I was past caring. I had completely lost control of any plan I might have had. Helga was in control and I fell asleep while she drove.

Suddenly I was awakened with noise all around and that smell of oil and seaweed which you get around docks. A big guy escorted us up a gangplank and the next thing I knew we were a ships engine room. There were a lot of guys in boiler suits and some bare to the waist. The shirt Helga put on me for travelling was literally ripped off me and I was carried naked on to a sort of mobile platform. It was very hot and so much noise! These huge engines were as big as houses.

One guy yelled in my ear "You're gonna get fucked!!" With that he produced what looked like a grease gun and after a nod of approval from Helga he inserted the nozzle into my asshole and made me take the entire length of tubing up my bum. Then he worked the lever with his bare muscular arm and I felt myself being filled up with this gel. There was no explanation, I just had to take it. He forced it up my bottom!

These guys wasted no time; in seconds a big hard cock was thrust into my mouth. It was like I had to suck it and boy didn't I do just that. The guy, he was just all muscles and hugely manly – weren't they all?!!! I was strapped down onto the platform with one over my chest with two more holding my legs up and apart. It was clear that these guys, there were nine of them in all, where going to gang my asshole.

They never asked me if I wanted it nor did they give me any chance to refuse. The only thing that distinguished this from gang rape was that I wanted it. And I loved not being asked. I loved the fact that they were in total control. I loved the idea of having my ass fucked by huge virile muscle men. I wanted their CUM! OH MAN! I WANTED THEM!!!

So in seconds that cock I had been allowed to suck was way up my bum. Boy wasn't this guy inside me! His was fucking screwing me all round! Just as well I was strapped down! HE FUCKED ME UP MY BOTTOM!! And just as I felt him flooding up me another equally huge guy thrust his raging cock in my mouth. I only had a few desperate sucks and a quick lick of his wonderful balls, then the first guy had finished ejaculating up my rectum so this second guy (I didn't know any names) drove his dick mercilessly straight up my ass. It felt like one those huge massively powerful pistons had just been plunged rudely into my boy-bum.

In a flash I caught sight of the first guy, his swollen cock flagging and dripping. I managed to signal to him to come over. And even while having my ass pounded I actually got my own way. In a few luscious seconds I licked his swollen slimy hose and sucked out the last remaining drops of cum from his knob. Oh boy it was SO SEXY!! And still I was being rammed harder than ever. Then this third guy just stepped out of his boiler suit revealing his superb nude body, and a truly massive erection pointing straight at me. I took it straight into my mouth just as that second guy was jizzing his juices into me.

There was so little time! Perhaps it was the heat but each guy took little more than two or three minutes up my bottom before orgasming, and these were all raw fucks. Don't ask how I knew they were clean I just trusted in Helga, they were her men after all! Perhaps that's what the grease gun was all about.

So this was the fuck routine: I mean it was an organised gang bang and Helga was the conductor. Like once she realised I wanted suck each cock just after it had come out of my asshole she made each guy present back to me at the right moment. So I got to savour each luscious slimy limp cock just after it had left my ass cherry and still dripping cum. I took each one well in my mouth and worked my tongue around their juicy knobs. I could suck out each guy's last juices and tease their super sensitive tips.

Then immediately I would get the next hard cock. The guy who was next to penetrate my ass cunt. I say 'cunt' as I was beginning to feel really effeminate taking sex so passively like a woman.

They could manoeuvre the platform thing I was on just by operating this big hydraulic ram. They could get me wherever they wanted me so guys could chose their best positions to fuck me. I found the sight of this shiny steel ram gave me a sort of fetish. To me it was like the huge powerful and unstoppable strength that was everything about that Engine Room.

And each fuck felt different and somehow even better than the last. Were they all getting bigger or was I imagining it? Perhaps Helga had organized them by cock size so my anus would get dilated gradually. It would be just like her to do that! But I didn't care I just wanted them all and their cum. Oh Shit!! I really, really wanted it then; I say again, I wanted it ALL RIGHT UP MY FUCKING BUM!!!

Perhaps it was the throb of these huge engines? The heat and vibration seemed to go right through me. Was this real? I began to think. Was I dreaming? All these super fit guys drilling and pumping my bowels with these perfect penises? I just felt so flattered and proud of being wanted by them! To be fucked by real men like these and see their pectorals bulging and their biceps as they forced their spunk up my hungry hole and fertilized my body with their virile sperm, it made me feel so good inside!! I loved the feeling of gradually being filled up deep inside with their manly spunk.

But then finally there was this ninth guy. Helga seemed very proud of him, so she must have saved him to be last. Oh man!! his cock was so curved back towards his belly, it was huge too and as I sucked him he started oozing precum from his knob. But oh boy! when he came up me!! His curved knob was teasing me like hell inside. I felt him drawing it up inside me against my gland and my inner genitals. This was why Helga was excited; this guy was milking me again!!! His was doing my gland and his dick was perfect for it. This was much even better than Helga's fingers. He had me oozing again in seconds I lost all control and screaming out. It didn't know what was happening to me. It was both thrilling and frustrating as, like before, I couldn't quite make it. It was like I was almost getting these endless multiple orgasms which I couldn't quite get over, but then he fucked me OH YES HE FUUUUCKED ME!!!!! It was like HE PUMPED ME FULL WITH GALLONS OF HIS GORGEOUS MAN-SPUNK!!!!

At some point in the proceedings, don't ask me when! the girls had arrived and were watching and videoing close-ups of me getting it. All these guys had done me in about forty five minutes flat and Helga set the seal on things by stuffing a really big anal plug up me. She borrowed a hip length jacket from the guys for me for our return journey. Well not exactly 'return' we went to Susan's flat (apartment).

This time we were in Angie's People Carrier but Helga had stayed behind with her mechanics – sorry 'Engineers' I supposed they would be expected to provide her with some 'servicing' as well, even after all that!

Having that plug up me I couldn't sleep, it kept stimulating me inside and making me feel even more sexy. Shirley told me the guys were 'blown over' by my bum. One said it was the sexiest thing he'd ever seen.

I suppose I'm lucky that my nice big smooth buttocks match my need for anal sex. Tom's were too manly and muscular to attract most straight guys. I suppose my problem is I just like all sex, gay, bi, straight, top, bottom, well not quite 'you name it' because there are quite a few things I don't like, for example anything with violence, extreme masochism and I definitely want nothing to do with child sex.

Anyway when we got back to the flat all the girls, were in a state of wild excitement. It was like this was the climax of their evening. Angie summoned me over a bit like she had done with Tom but this time she and Susan were sitting on the sofa and I was invited to sit on a stool nearby.

"What do think of Susie's hands Carl? They're lovely and soft aren't they?! Not like those hairy mechanics! And we all have all got our nails well trimmed too haven't we girls!" the others smiled shyly. She went on stoking Susie's hand very suggestively all along her fingers. They were actually very nice, the sort of thing I had noticed subconsciously when she had asked me to look at documents back in the office.

But it was all so weird in a way. There was something really sexy about it too. All the girls had stripped off completely naked and were around me caressing my nude body.

Presently Mandy came in all practical as usual and ushered us into Susie's bedroom where she had a bed kitted out with a contraption at its foot. "It's just what we call a Gyney bed darling. It will be more comfortable for you. Its usually used for delivering babies you see!" they all giggled nervously. "And this!" she said waving a large jar "This is the same cream we use to dilate them. It works wonders you know!" It felt cold as she massaged in and around my cherry. "In next to no time you'll be opening right up for us all darling won't you!" she added soothingly as went on rubbing it into the soft flesh all around my swollen anal sphincter.

So there I was with my legs up again. Everyone seemed to want to get at my bottom, well actually my cunt really! Susy was applying cream very liberally all over her pretty hand and right up her forearm even as far as her elbow. Would she really be able to get that far up me?? They all seemed like they were trembling with excitement, I felt that whatever they were going to do to me, there was no way I could stop them. Then in less time than it took you to read that last sentence Susie had started fingering my asshole but not just with one finger, she was pushing several up me at once.

The Engineers had big cocks – didn't they half! and Helga's Strapon! that was even bigger but now Susie's hand! She had formed it almost into a fist by now and was rotating in and around my asshole and at the same time pushing hard into me. I wanted to open up for her, I really wanted to yield but I kept feeling my sphincter trying to contract.

"Just relax darling! You see we've really got to get to the bottom of you haven't we girls?" she said looking around. "You let me in now and I'll see to you inside, you really do need a nursemaid as well as a milkmaid don't you dear" she said smiling. All the time it seemed that her hand was getting further inside me but I must have been very tight as it was nearly half an hour before I felt my sphincter finally yield to the pressure. It was a short sharp pain then this fantastic sensation; it was easily the biggest thing my ass had ever had to accommodate. Her whole hand was now coming right up inside me, I could feel her fingers exploring my rectum.

Category: Transsexuals & Crossdressers Stories