Written by Bobbie
27 Aug 2010
Lady like clothes
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5 minute read
Lady like clothes by Bobbie
I was at university near a seaside town. I started my first term in September. I was 18. The weather was warm and I decided to take a trip to the beach. I was a skinny kid, five foot eight, with long blonde curly hair and blue eyes. I had been dressing as a girl at boarding school- taking girls parts in school plays. So far I had not worn girls clothes in public- except when my sister and her friend dressed me up some years earlier.
But I liked being seen in my Royal Blue Mark Spitz swimming trunks. They were of sort of satin material and very brief. My genitals are very small and I had to be circumcised for medical reasons. I liked the way my swimming trunks squashed my sex flat. With my very skinny thighs and long slender almost hairless legs, Even with my legs pressed close together, there was quite a gap between my legs. It was very obvious to anyone who stared that there was very little between my legs I felt deliciously girlie when I took my clothes off on the beach in the still warm and bright sunlight.
There were not many people about. I lay on my towel. Looking at the sky and began to doze. Some rough sounding voices awaked me. Opening my eyes, I noticed four scruffy looking men, much taller than me, looking in my direction and laughing. Though my penis is very small- under three inches erect- it was very noticeable when I got a hard on in tight pants or the swimming trunks I was wearing while they were looking at me. Quite often, then in the late 1970s, I would get erections while I was asleep.
Fear concentrates the mind. Though drowsy, I caught something of what they were saying. Three of them were fat, bald and well over 60. The other was around 30, dark haired and swarthy, his vest showing off his muscles. All of them had weathered beaten and tough looking. ‘Thought it was a girl, what a fuckin’ shame.’ Said the younger man, rubbing himself around the crotch of his oily jeans. ‘Might as well be. Look. She’s only got a little cock in those pretty panties an the little bitch looks pleased to see us.’ My heart started to race. I was soon sitting bolt upright, grabbing my jeans and tee shirt as they came closer, encircling me. ‘No need to rush off on account of us.’ Said the younger one, picking up my ruc sack and looking inside. ‘Oh my God,’ I thought, recalling that I had my favourite black bra, panties and black fully fashioned stockings in my bag, in case my room mate found it. ‘Well, well, well’ said the swarthy creep, pulling my intimate items from my bag. ‘Cor, he don’t look the sort to ave a girlfriend, no cock on him for that?’
I was frightened and humiliated, but my tiny penis felt fit to burst and my little balls tingled. ‘I don’t think it’s like that. I think this little bitch wears ‘em.’ They all roared with laughter as one of the fat men snatched the clothes covering my Royal Blue swimming trunks. I folded myself forward, putting my head between my thighs and gripping them with my tiny hands. ‘Skinny little fucker, ent she. Arms like bleedin match sticks.’ Said another fat man, to which the first fat man replied, ‘Yeh, more meat on a butcher’s pencil. But I likes em skinny. Me wife is too fat, Can’t get it up for her, but I am feeling a rise for this little cunt.’
‘Cum orn, let the dog see the rabbit’ said the third fat man, pulling my hair so that I had no choice but to sit up straight. Then hefty clumsy hands were between my legs, groping my tiny prick and crushing my ball sac. While my long blonde hair was being pulled painfully hard, it was all too much. Livid angry faces were glowering down at me. My excitement was too much. I did not want to cum in front of them, but it was just too exciting. The mixture of pain, verbal abuse and manhandling of little sex was too much. The younger guy knew what was about to happen and pulled the crotch of my swimming trunks to one side. As my little cut two and half-inch penis felt the air, it began to convulse violently. I threw my head back, against the will of the man holding my hair.
To the sound of roaring laughter, my tiny penis started to jet. My orgasm seemed to go on for ages, in spite the fact that cruel hands were still crushing my sex. The pain heightened my pleasure.
After my orgasm I wanted to run away and hide, but they carried on groping me. Working my sex really hard, white foamy stuff started to appear out of my slit. What they were doing was a mix of pain and pleasure. They were all wanking me hard, until the younger guy said: ‘Hey stop a minute. There’s no one here. The slut can put on her sexy undies for us and we can have some real fun.
Stripping naked and putting on black satin undies, stockings and suspenders was humiliating, but my prick was again bulging against the tight black satin and lace, when they made me bend over, one holding my bony shoulders, while the younger guy pulled my panties to one side and took my virginity. It was like my bottom was on fire. The pain was horrendous as he called me a filthy slut, filling me with his huge dick. I wouldn’t have known it was possible, but I was cumming very hard, even though my little penis hung limply form the lacey leg of my panties. I felt the orgasm starting under the skin covering my pubic bone, where my balls had gone and hidden.
All of them had me. I did not understand why they had so excited me. It was the beginning of lots of men having me, via these nasty looking men. I dressed ever more seductively and got very excited knowing that men enjoyed having very rough sex with me. I came to love pain and humiliation, as long as I was wearing pretty undies and lady like clothes.