To start things off there is something you need to understand. I am bi sexual, but when I am with a guy I am a submissive bottom. I love to pleasure other guys. That's how this experience came about.
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Crossdresser's Rough Sex
I was out for a drink with a girlfriend, catching up on the latest gossip when a voice whispered in my ear
"I can see your knickers."
I spun round and saw a moun5ain of a man, he looked like a chubby lumberjack, all man and really butch. I blushed and panic as no one knew I was wearing panties or stockings. It turned out that when I sat down my pink panties were visible over the top of my jeans.
I quickly pulled my shirt out of my pants to cover my ass but he had already seen my panties. I wasn't sure whether he was going to punch me or put me over his shoulder. As it turns out the latter was on his mind. He turned and left without saying another word and leaving me to explain to my friend what he wanted.
Ten minutes later I was going to the toilet when Mr. Lumberjack approached me and handed me a piece of paper. It simply said that he liked sissy boys and to ring him if I was interested in some fun.
Over the next few days I swapped texts with him, no names were ever mentioned just text sex. He was very aggressive and dominant in his messages, there was no doubt he was in control and my sub side came out and agreed to a meeting.
On the day I bathed, readied myself for a long night of sex and prepared my outfit. I wore a pink Basque with white trim and suspenders attached a silk, white thong and stockings. I put red lipstick on and a little mascara and then waited for him. He was going to pick me up and take me to his place so when I heard his van pull up I grabbed a long coat to cover most of my outfit and ran to the van in my slip on shoes.
As I got into the van he smiled and asked what I was wearing, I just told him to wait and see. He had a t shirt and jeans on, still looking like a chubby lumberjack. He drove us out to a park and parked up. I asked why we were stopping and he told me to get out. I did as he asked and followed him to the back of the van. He opened the doors to reveal an empty van apart from a mattress on the floor.
"Take your coat off and get on the bed."
I slipped my coat and shoes off and threw them in the back. He whistled his approval of my outfit and began to strip off. For the first time I saw him naked and knew he could do anything to me. He was a lot taller than me and far more muscled and toned. He had a slight beer belly and little man boobs developing. There was hair all over his body leading down to a cock that must have been ten inches and rock solid. His balls were tightly packed underneath his dick and waiting to unload into or over me.
I lay on my back on the mattress. He leant over me taking in the view, me dressed in my Basque, thong and stockings, licking my lipstick covered lips seductively. He managed to say one thing before he pounced on me
"You are going to fucking take my cock in every hole bitch."
With that he knelt over my chest and presented me with his cock to suck. I opened my mouth and he shoved the whole of his stiff pole in. I gagged a little but on the next thrust managed to deep throat him, his balls resting on my chin and his pubes around my nose. I felt really slutty being on my back on a mattress in a van with my lingerie on and being face fucked by a huge stranger. I loved every second of it though and wanted more, I was submitting to this man totally.
I tried to relax my jaw as much as possible and try to use my tongue on the underside of his cock to add to the sensation. He carried on forcing his cock in and out of my mouth as though it was a pussy. I was dribbling and his cock was leaking more pre cum than ever. His excitement was building and his thrusts getting harder when he pulled out of my mouth and started to slap his wet cock onto my cheeks.
"You sissy slut, you fucking love it don't you?"
I did and as he carried on slapping his cock on my face his pleasure was obvious. After a few more slaps he got off my chest and moved down my body, lifting my legs he spanked my ass hard, it stung but also felt great at the same time, I decided to play sub for him
"Please spank my sissy ass, I deserve it."
He gave me what I wanted, another hard spank and another and one more for fun. My cock was so hard that I had a wet patch on the front of my thong. I couldn't please myself though until I had pleased him.
He reached back for his jeans and took a little sachet out of his pocket, tearing the top off if it he told me to lift my legs. As soon as I did he moved my thong aside and emptied the sachet of lube onto my ass. Then without warning he pushed a fat finger straight up my ass, and then pulling back he pushed another up me. His rough fingering was a little painful to start with but soon felt nice, his fingers were really thick and stretched my ass nicely readying me for a rough fuck I hoped.
My chubby bear was pounding his fingers in and out of my loosened ass, his cock was swinging between his legs and his balls looked ready to burst. My own cock felt ready to spurt and when he pushed a third finger deep in I came hard, spunk forcing its way out of my hard dick and through the material of the thong. My tight thong dripped cum from the gusset and I was still getting forcefully fingered. He looked at me Cumming and growled at me
"You dirty fucking cunt, you've soaked your thong. You're getting fucked hard now."
With that he pulled his fingers out and lifted my legs over his shoulders. He touched his cock against my hole and in one thrust powered straight into me. I gasped at the force he thrust with even though he opened my hole easily and I felt no pain. I moaned straight away as he wasted no time gaping my ass with a power fuck.
The van must've been shaking as he violated me, balls slapping against me and the sounds of sex echoing through the van. I begged him to keep on fucking me and to use me as he wanted. I didn't have to beg because he was going to anyway.
He pushed in with a hard thrust and then pulled straight out. His big, rough hands gripped me and turned me over, he pulled me back towards him, my ass in the air and then pulled my thong off. As soon as he had it off he pushed his cock straight back in and continued his fuck.
My ass was stretched and used and he had no intention of stopping. Harder and harder, his sweat dripping onto my back, he screwed me. He reached forward and pulled my hair, almost screaming he said
"Fucking take it cunt, you sissy bitch."
My head yanked backward and he laughed, his balls were swinging hard against me and my soft cock was swinging between my legs in time with his fucking. He spanked my ass as he pushed balls deep into me and then the other cheek, always as he pushed into my gaped hole. I felt his cock flex inside me but he didn't cum, I was sure he was close though and decided to help push him to the edge.
"Please cum in me, breed me, I need your spunk."
He laughed and told me to beg more if I wanted his jism.
"Please, please make me yours, I want to be your cum dump."
He laughed again, spanked both my ass cheeks at the same time and carried on fucking me. I started to squeeze his cock as hard as I could with my ass and it proved to be enough. He grabbed my hips and pulled me back as he slammed into me and started to cum. It felt like he was flooding my ass, his cock twitched inside me for ages before he pulled out and told me to turn round.
I turned round to face him and he shoved his cock into my mouth, grabbed my hair and began to screw my mouth. He was using my mouth to clean his cum covered cock. He pulled out and began to piss all over me. His hot pee soaked my face and Basque as he grinned at seeing me covered in his piss and leaking cum from my ass.
When he finished he reached behind him, opened the van doors and told me to get out. He moved out, standing naked in the night air and I followed.
"Strip off slut"
I did, trying to do a sexy striptease and remove my soaked Basque and stockings. Once I was nude, stood bare, soaked, my soft cock shrinking further. He looked me up and down and ordered me to get in the front. He got in started the engine and drove me home naked and used. He dropped me off and I went in, showered and climbed into bed absolutely spent.
In the morning I had a text from my lumberjack. It simply said to phone when I needed my ass breeding. Two days later i sent the text and he and i retutned to the park for him to use me on a park bench.