halloween crossdresser stories

My name’s Julie I’m 24 now, but story about when I was 19. then I was small slim blonde girl ( I wasn’t a virgin, lost it at 14 to our neighbor’s son another story ) 36 cc tits boys loved them. I had become religious and went to church regularly. I started dating Ian he was 2 years younger than me, skinny red head boy. His father was elder in church strict kind of guy ( always felt Ian’s mother was scared of him ). We had really trimmed relationship, all we did was kiss, hold hands and cuddle, although it didn’t stop Ian trying to grope my tits or get his hands up my skirt. But I was trying to be good and always stopped him. A week before Ian’s 18th birthday, he asked if I would let him go further, I said we see I won’t promise. I knew he was sexually frustrated. Anyway after church one Sunday night he borrowed his dad’s car and took me to a quiet car park ( he just turned 18 on the Friday ). I was wearing white blouse, red skirt and had tights on. We started kissing and cuddling ( he seemed in a hurry ). Slow down I shouted at him I promised you a surprise didn’t I. I unbuttoned my blouse, my bra was fastened at front, unclipped it and exposed my large breasts ( his face lit up as if he won lottery ) be gentle I said he begun to caress them, it felt good, then lick them and suck them, I must admit I was getting aroused. Rub my cock he said, only through your trousers I said, it felt hard as if it wanted to rip material to get free. Suddenly I felt his hand trying to slide up my skirt as he sucked me. I put my hand down and stopped it, no I whispered just enjoy my tits. He did as he was told for a few minutes then tried again. Again I stopped him, we kissed a long kiss ( I must admit I was getting turned on ) his hand was trying to get up my skirt again, I stopped him though he had got further up than before. He began sucking my tits again only this time he was pulling my nipple with his teeth, biting me (not hurting me ), now I was aroused. He had stopped trying to get his hand up my skirt, but I was so aroused, I put his hand on my knee, he hesitated, I looked in his eyes and started to push his hand slowly right under my skirt, two fingers touched my pussy through my tights and pants. He was rubbing me gently, digging in as if he was pushing my pants and tights inside me, he knew by my face the groaning that he was the winner here. I stopped him, his face had a look of shit not now. Hold on and put my hands under my skirt and dragged my tights and soaking pants down ( removing them ). I put his hand on my soaking pussy, my hairy bush was dripping. He rubbed my pussy and fingered me, my juices covered his fingers, he licked them. I unzipped his trousers and stroked his cock ( about 6 inches ). I put car chair down and opened my legs. I felt him on top of me and guided his throbbing cock inside me, oh it felt good. I felt him thrust deep in my pussy, slow thrusts and then faster, I was begging him to fuck me hard, my wee legs wrapped round him, I had cum twice when he moaned I’m cumming. Instead of pushing him out my legs stayed wrapped round him, I felt my pussy getting filled, wow he shouted. We just lay their, I felt his cream oozing out of me. We kissed laughed ( a nervous laugh ). We sorted ourselves out and made ourselves respectable and headed back to his home ( my tights in my handbag ) Ian put my pants in his pocket said he will taste them later. We sat in his parents house talking to them for ages. Ian fell asleep on settee, his mother said he looks shattered ( if you only knew I thought where your innocent son been ). Then Ian’s dad said I give you lift home, I said I will get taxi but he said nonsense it’s no bother. I lived 12 miles from them so reluctantly agreed. Surprisingly he talked away to me when he suddenly took detour into the same car park I just been fucked. He parked the car and said he thought I was a wonderful young lady. I said thank you. He put his hand on my knee and started stroking it ( I was nervous ) but smiled. He leaned forward and kissed me, instead of pushing him off I responded to his kiss by kissing back. His hand went further up skirt ( suddenly I remembered I had no pants on, he thinks I’m a slut ) but as our kissing became more intense he reached my bare pussy ( he stopped as he realized I was naked ) he pushed lever and chair went flat my skirt was lifted and my legs pushed apart. heard his zip been pulled down and wow he had at least 8 to 9 inches ( never had anything that big inside me ) he was in and fucking me like a whore with no mercy. If only he knew his son had just been there. I screamed oh I’m cumming. Then felt a load full me again. He wasn’t finished with me yet and ordered me to get naked, I stripped off, his hands were everywhere groping me like a frustrated old man. He stuck his cock in my mouth and made me suck him deep. Omg he was getting hard again, I couldn’t believe it. He turned me over face down, shouting where you want it, I screamed in my pussy, again he demanded where you want it after slapping my bum, again I screamed in my pussy, another slap on my ass, after another 2 to 3 slaps he whispered where you want it. I lifted my head and said in my ass, good girl he said and proceeded to edge his cock in my butt. The pain as inch by inch pushed into my bum, fucking me slowly, I groaned and moaned, you like that he said, stuttering I said yes then after he fucked me deep he groaned and cum in my ass. I dressed, he had a satisfied smile and drove me home my pussy filled my ass aching. That’s our secret he said, I nodded. In next 3 months Ian and his dad fucked me at every chance they got. Then I became pregnant and both of them disowned me, the members of the church were shocked I was pregnant ( unwedd ) and thought I was a slut and ignored me. I had a girl but who’s?This content appeared first on new sex story .com