My Brother My Sister

I wrote this story originally under the title “Be Careful In the Park” about an older crossdresser who meets a street gang in a park and gets more than she bargained for. There was no incest in the original version. I like this version better as it includes all my peccadillos: incest, crossdressing, nylon fetish, and forced sex. A warning to those who find those subjects not to their taste.

My God! I was going to get raped by the members of a local street gang of which my brother Tom was a member. I could just make him out in the dim light from the moon. He was not aware of who I was, and that’s understandable given the way I was dressed and behaving. I suppose I had better give you the background so that this story makes sense.

I am a 20-year-old crossdresser. I have been dressing as a woman for five years without my family knowing. There is certainly no way I was going to tell my now 18-year-old brother Tom what I did for kicks. He had grown up rough, and unlike me, who enjoyed a serene, some would say sissy lifestyle, Tom couldn’t wait to join a street gang. While I locked myself in my room trying on makeup and sexy women’s clothes, my younger brother was playing football, sneaking beers, and committing petty crimes with his pals.

I had been sneaking out of the house dressed as woman for about 3 months now, and I always headed to the local park where I was guaranteed of picking up some rough trade; usually older men who would take me in the toilets for a quick blowjob or a quick fuck against the cubicle wall.

Tonight I had walked down to the local park and was sitting in my favourite dark corner, looking for punters who occasionally cruised the park looking for action. I was certainly dressed for action; red Lycra miniskirt, blue and black sequined top, sheer black nylon stockings, sheer red nylon panties, garter belt and black ‘fuck me’ high heels. I had put on my trademark ‘slutty make-up’ and my favourite blonde wig. I looked nothing like my male self, and was confident that I would not be recognised by anyone who knew me casually. I was having a chat with an older man I'd met before, the memories of an earlier visit we had made to the toilet block quite turning me on and hoping we were going to get it on.

Then I saw them, a street gang I had never seen around my ‘patch’ before, but I instantly recognised Tom amongst them. There were six of them and they were all young, fit and no doubt full of the beer they'd obviously been drinking that evening. But I hadn't come out looking for trouble that evening, that wasn't my scene at all, even so I knew I only had myself to blame for the fix I was in. I deliberately hung around this park because I knew Tom’s gang never came here and now my luck had run out.

Unfortunately the street gang now entered the park and my ‘older friend’ just turned and ran. The gang swaggered towards me. I knew I had a few options: identify myself to Tom and live in ridicule for the rest of my life, or chill out and hope they passed and left me alone. Possibly stupidly I lit a cigarette to still my nerves as they approached and instead of passing, the gang veered over to my seat, a voice asking,

"Can you spare a couple of cigs?"

These boys all appeared to be in their teens or early twenties and I knew from talking to Tom that they had a reputation for trouble. As I said, obviously they'd had more than a couple of beers apiece but they did not appear to be over the top pissed. Maybe they would take my smokes and move on. As they came closer I prayed they, and particularly Tom, would not recognise me in the dim light.

One was jet black; he looked the oldest, wearing white rugby style shorts and a black T. The youngest looking was also coloured, more a coffee colour, in his case wearing denim shorts and a polo shirt. The others were white but standing more in the shadow so I couldn't make them out so clearly at that time, but I knew one had to be Tom. I handed over a couple of cigarettes saying I couldn't spare any more and was told.

"No problem."

They stood around to light them and the thought had just crossed my mind that I wouldn't mind meeting one or two of them at a time down here if only they weren’t Tom’s friends Then the oldest asked, out of the blue,

"Do you suck cock u dirty Tranny?" I was taken aback, but it was obvious they recognised me for what I was, a crossdresser or transvestite if you like, and without really thinking I replied,

"It has been known."

There must have been some sort of pre-arrangement between them because the leader pushed a younger coloured boy toward me laughing and saying,

"Well let’s see you then. My friend here has been sporting a hard on all night and he says he will even stick it in a slutty looking tranny like you to get relief."

The young man pushed me to gently my knees, I knew resistance would be futile, my face was just level with his denim shorts, the front of which he was massaging slowly. Judging by the bulge in his shorts I hadn't heard a lie, he had been sporting a hard on all night. As he was pushed even closer he asked,

"Are you sure you don't mind honey?" and turned and laughed to his pals.

Normally I wouldn’t mind at all! It was what I'd come down here for, even though I'd not expected an audience. The other males would be no problem if they wanted to watch; it would just turn me on more. In reply I just licked my lipstick lips nervously.

That was all the encouragement he required and pulling down the zip on his shorts, he pulled out a nice looking weapon, already more than half hard. It was a nice size and shape, cut, about six inches long and the girth was in proportion, nicely coloured to match his skin tone.

He used his hand to move his cock tentatively to my red painted lips where his courage failed and I could see it just start to wilt. My instincts took over and I moved my head forward and grasped an inch or so between my lips, using my tongue to wash round the end. He gasped and he immediately became fully hard, his animal desire taking over as he moved forward, plunging the whole six inches down my throat without warning.

I managed to hold tight as he placed his hands on my head and started rocking back and forth. He must have been playing with it, or talking about it, most of the night as I was only just getting used to it when he pulled out, yelling "I'm cumming," and proceeded to jack off rapidly, shooting over my face, the semen running down on to my blouse. That seemed to decide it for the rest as they all moved forward and one of the white boys dropped his shorts to display a fully hard, slightly larger cut cock, which he poked out at my face.

I was hoping now that maybe all they would do was demand a blowjob each and go on their way. In the dark corner of the park maybe I could get away with that and then make some sort of excuse when Tom came to take his turn. As much as I loved sucking cock there was no way I was going to fellate my own brother.

Normally I do love a cut cock and would need no further bidding to wrap my lips around the cock in front of me and work it, but now I was scared. They were drunk, horny, and trouble. This seemed to settle it for them and I became aware the other lads all had their cocks out, rubbing them excitedly. An older coloured boy made his way forward and pointed his groin at my face.

"How about this then? You fucking tranny slut," he asked.

This when I realised I was in serious trouble. I gasped,

"My God! No!"

His cock was huge, it had to be a eight inches long and possibly two inches across.

"I can’t take that," I gasped.

"Well your going to," he growled.

Without further ado the lads pulled me up and hustled me over to the children's roundabout in the play area. That was all the leader said to me directly for some time, giving others instructions as to what they should do to me, how to place me, how to hold me. The roundabout was one of the old style, solid wood planks, well worn, with a small running board and four metal handles crossing over the top. It was located in an area of the park where the streetlights had been broken and whilst it gave them the privacy they wanted to go about their ravaging of me, I dismally hoped it would assist my disguise and help keep my true identity from Tom and his friends.

Under their leader’s instructions they soon had me spread out on my back between two of the roundabout handles, they pulled my panties to one side and exposed my puckered ass, my sheer stockinged legs where spread wide and my high heeled feet where lifted high in the air. The white boy who'd just fucked my face knelt behind me holding my head up and cushioning it somewhat from the bars. Some of the lads had stripped off their pants by now and it was obvious that they weren't going to leave me alone until they had all had their way with me. I tried to look around to see where Tom was, I just hoped he wouldn’t join in,

One of the boys climbed on the roundabout and knelt with his cock pointing at my face. He was quite dark, only about eighteen but already with a hairy manly chest. He just knelt there masturbating for a while and then I felt a pair of hands start to feel my arse, first gently and then with more vigour. One, then two fingers inserting themselves up my passage. I couldn't see who it was but I prayed it wasn’t Tom. As my arse muscles started to spasm as the fingers withdrew and a voice said "Now!" and I heard and felt someone spit on my ass-bud.

“Natural lubricant,” a sleazy voice laughed. I recognised the feeling of what entered me next, a medium sized cock was pushed deep inside me, and it wasted no time, but started to attack me straight away. In, out, in, out. He was reaching my prostate without any problem. Even though I was being raped, I was going to cum soon if not very careful. I managed to mumble something along those lines in between loosing my breath each time I gasped he rammed his cock in and out of me. I just hoped it wasn’t Tom, ‘please god don’t let it be my brother fucking me,’ I prayed, even though I was now thoroughly enjoying the fucking I was receiving.

“Oh God, I’m going to come,” I uttered, as the intense fucking I was receiving took me over the top.

"That's OK. So am I," laughed the lad kneeling over my face as he sped up the speed of his wrist and with a series of soft yells shot over my painted face and lipstick lips.

All this time the attack on my arse had continued. I heard,

"I'm cumming. God I’m cumming. Here we go!"

I was thankful the voice I heard was not Tom’s, but the attack intensified and with half a dozen sharp thrusts as I felt the cock in my arse shoot inside me. The boy that was raping my arse shuddered a couple of times and pulled out. Lying there catching my breath I was hardly aware as the lads changed places.

Now my head was being clenched more tightly, one lad was standing each side of me holding my now laddered, stocking clad legs back in position and a new weapon was rubbing against my panties that had slid back, and now covered the entrance to my arse. I looked up to see the leader with his huge cock in his hand pointed at my arse, from which his mate’s semen was leaking and staining the crotch of my panties. I started to struggle,

"No, I can't," I said.

"Yes you will, your arse is well and truly lubricated now" he snarled.

I struggled but someone grabbed my high-heeled feet and pulled my legs high over my head exposing my come-soaked panty-clad arse. The lad kneeling at my arse pulled the soaked, slinky fabric to one side and positioned his manhood at the puckered flower. Amazingly, the usual flush of expectation of a good fucking flowed over me and I felt myself relax against my own will. I know what I'd said, but there was no way I could take him. He had to be a ten inches and at least three inches across. A solid black ebony shaft. As his cock demanded access to my hole it seemed to glisten and gleam in the moonlight.

"Right?" was all he said.

"No!" I managed to reply.

It didn't matter. Whatever I said, it didn't matter. He was going to fuck me. He was going to rape me. No one was going to do a thing about it, including my brother who was oblivious to my fate. The other lads that were holding me in position were getting excited now. I could see hands moving, two bodies kneeled beside me, hard cocks were being readied for an assault on my body, but they were all watching the weapon that probed my entrance. He was slow; at least I'll give him that.

He stopped for a moment as soon as he forced it into my entrance, but only to allow me another gasp before starting again on a slow but inexorable voyage of discovery inside me. It never seemed to stop, a little push, stop, pull back, and push again. Each time a greater violation. He punched past my prostate almost without my being aware and still the exploration continued. Deeper than I'd ever been violated before. If I'd not been so excited and scared at the same time, and held so tightly, there wasn't any way I could have withstood the punishment.

I could hear myself letting out little yelps and groans whenever I had the breath, which wasn't very often. Each time I gasped in order to keep breathing, he forced his cock in again before I had time to fill my lungs. It felt as if that monster penis of his was splitting me apart. It wasn't a cock, it was a weapon he was using on me! It stopped. I managed to take a clean breath, open my eyes and look up. The leader was looking down on me his face covered in sweat from his exsertion in my arse.

"I've never had it in a tranny’s arse before. You are one tight bitch!" he laughed.

I was in pain, but such glorious pain. I'd never been so thoroughly possessed before. I knew he was raping me. No way could it be called regular sex. He might damage me but deep inside was a feeling that I wanted more. I just had to have more.

"Get on with it," was all I replied.

With an even bigger grin he pulled back slowly, and that was all my body needed to move on to a higher plane of sexual ecstasy. I must have been a quite a sight, my skirt rucked up, sheer nylons laddered, legs held spread, panties pushed to one side of my open arse that was impaled by a huge black cock.

The two lads who were holding my legs with one hand and their hard cocks with the other decided it was time to get in on the action. One crammed his engorged penis past my lipstick lips and into my mouth, the other was busy stroking his cock and alternately rubbing it on my cheek and in my hair. Someone grabbed hold of my cock and was squeezing it hard each time the unknown assailant rammed his cock in me. ‘Not my brother Tom, please,’ I hoped.

That seemed to be a general signal for the other lads and I felt other hands moving over my body, rubbing cocks on my stocking legs, wanking over my face, and then my hands were grabbed and wrapped around two more throbbing penises. Was everyone going to use me tonight? Which cock belonged to my brother? I was aware of the weapon up my arse as it started to swell and judder, and as it started to shoot I felt the cock in my mouth explode and come filled my throat. I had no choice but to swallow.

The two cocks that I had been forced to wank also ejected their loads, I felt the sticky come saturate my hands. The other lad rubbing his cock on my face shot a stream of come over my eyes, adding to the come already there expelled from the first boy who used me. My mascara was running down my face in a stream of hot semen. The lad who was dry humping my sheer stocking leg groaned at this sight and I felt his cock pulse against my stocking thigh and I then the warm wet feel of come through my laddered nylon encased calf. Finally the young black man that was raping my arse stopped; he withdrew his flaccid penis and looked over his shoulder, smiled an evil smile, and said,

“Here, you can have what’s left of this bitch now.” I looked up in horror realised it was my brother Tom he was talking to.

“No, no more please, I can’t take it,” I whimpered in attempt to put him off .

What could I do, If I exposed my real identity there was a good chance the gang would beat me up and Tom would know my secret and tell everyone. I decided to meekly accept whatever my brother decided to do to me, and hope he didn’t notice who I was under the smeared makeup and ripped women’s clothes.

My brother Tom took his place and lay on top of me.

He didn’t seem to care that my face was covered in come and that I was leaking sticky white semen from my arse. He leaned down and kissed my smudged lipstick lips. I felt his cock stiffen as he pressed against the nylon panties covering my penis. The lads holding my legs, having achieved their orgasms and having no further use for this ‘tranny slut’, had let go of my legs and were stuffing their sticky cocks back into their shorts as they dressed.

Tom reached down and placed his turgid penis against the bulge of my soft cock encased in my nylon panties, oblivious that his was older brother underneath him. He was humping it against my panty cock, obviously too aroused and too inexperienced to try to enter me, he had decided to come quickly against me. I thanked god that it looked like he was not going to fuck me or make me suck him. I had guessed that Tom was still a virgin, and his inexperience and excitement meant he wanted to quickly release his seed and move on.

I realised he was the last in the long procession of rapists that were using my body for their own pleasure, taking what they wanted by force, even though I would have given it gladly one at a time in if my brother wasn’t there. I decided that I could take no more, I was now fully aroused by my brother’s thrusting penis, even though I had been raped in every orifice, was covered in come, my make-up smeared, my nylons ruined, my clothes ripped. I decided to help Tom achieve his orgasm as quickly as possible before he changed his mind and wanted to fuck me properly or worse still he recognised me in the dim light.

I lifted my legs and wrapped them around my brother’s back as he dry humped me through my panties. I pushed up and met his thrusts as his cock pressed against mine through the sheer nylon of my panties. I lifted my head, covered in come and smeared make-up and pushed my lipstick smudged, recently raped mouth against his. I rammed my tongue down his throat and started to dry fuck him earnestly.

Tom’s inexperience was obvious and my brother started to squeal as his cock spasmed against mine, drenching my panties, soaking through to my now throbbing penis, which erupted in unison. I gripped my brother in my embrace tighter as our cocks continued to jet come against each other. Finally Tom lay still, and then pushed himself off me and joined the circle of rapists standing around me.

They were all laughing and looking down at me. There I was, my skirt hiked up, my penis slowly deflating, covered in semen, my clothes ruined. I was well and truly raped by the gang, which had included my brother. The leader of the street gang, the one who had raped my arse with his enormous cock, spoke.

“Come around here again you fag tranny bitch you’re going to get the same!”

He turned his back to me and started walking away with the rest of his gang slowly following laughing and jeering amongst themselves. Tom, my brother the rapist, who had used me last, suddenly broke away from the gang and ran back to me.

‘What now’, I thought. My younger brother knelt beside me, lifted my head and gave me a soft passionate kiss. He whispered in my ear,

“Thanks most exciting experience of my life Sis,” he whispered.

I lay there and couldn’t believe what I had heard. He knew who I was! He called me ‘Sis’!

“Well I guess you are now my older sister now, instead of my older brother; tomorrow you can you can show me what a blow jobs feels like, either that or I can just tell Mom and Dad about your secret. See ya’ later Sis,” he laughed.