This is a print version of story My first time crossdressing for a friend by deborah_riggs from xHamster.com

My first time crossdressing for a friend

One night when i was 14 i had a friend spend the night, we talked about sex as most guys our age did, and the fact than neither one of us had ever had sex. We talked about the typ of porn we liked as we had found our parents porn stashes and would watch them every chance we got. Then it came up that he had seen a bi vid that his mom had, it was mm/mmf, with one sean involving a guy dressed like a girl and it had realy turned him on. He said that the guy looked hot as a girl, and that he was getting a hard on just thinking about it. I could see it getting hard in his shorts and i was starting to think about us doing the things he was discribing . I had played dress up with my older s****r when i was younger as she didnt want a little brouther, i dressed up a few times on my own after that i loved the way i felt. I told him about playing dress up and he asked what i looked like and i told him i looked like my mom. I was tall and thin long legs and firm round ass sholder length dark broun hair and deep green eyes when im excited. the only thing i didnt have was tits, well and i had a small dick then that was tucked when i dressed up i went on telling him. I didnt know why i had the urge to tell him things i never thought i would ever tell annyone, but it just felt right some how. He told me that if i looked like my mom that i must look so hot all dressed up. The thing that realy got him is when i told him that when i dressed i dressed and ackted just like her including the way she smokes. It wasnt long and he was begging me to dress up, telling me that my parents were out of town and my older s****r was staing next door. after a few min. of him pleading with me i gave in and started for moms room and got dressed up, and did my makeup. i had a black lace braw 38 dd that held two ice bags filled with warm watter that giggledas i moved. next was black stockings and guarders with a pair of 6 inch black heals, fallowed by a black short skirt and a very thin white blouse that you could see my braw threw it. When i was all done i went back to the couch where he was waighting, i light a cigarette and set next to him after doing a littel turne to let him see it all. He was speachless, then he said wow you do look just like her and that i had her act down to a t. He told me that he fantisized about doing thing with my mom when he would jerk off. Thats when i asked him like what he said like her giving him head and then fucking her. I noticed he was even harder then befor, and i asked him if he was hard for me or the idea of me looking like my mom. He answered quick mostly your mom but its still you. Buy this time he was rubbing his crotch and i said damn that thing lookes like its going to rip through your pants. he laught and said it feals like it to and it wont go away. I half joking said i bet mommy could make it go away he said realy. I didnt know what to say i had wanted to try sucking a dick but i was scared that i would be bad at it. I thought for a moment and said whipit out big boy and to my suprise he did. He was about 7 inches long and very thick. I chickend out, and he put it back in his shorts and we down on the blankets on the flor and watched tv till we fell asl**p,i was still dressed.I woke a few hours later to him rubbing my tits and the sound of him jacking off as he was whispering my moms name, and saying how good it felt. I kept my eyes closed just enough for him not to know i was awake, but enough to see what he was doing. He was stroking it just a few inches awaw from my face. after a bit he used his free hand to gently open my mouth and put the head of it in my mouth and started to move it in and out slow trying not to wake me. I had never realy wanted a dick in my mouth till then. I now was so into it after a few minouts i started to suck it. he jumped back pulling it out of my mouth with a soft popping sound. I looked up and asked why he stoped and he said it wasnt right that he shouldnt have done that to me. I told him but you did it any way you had your dick in my mouth and you said you like it. He set there for a minout, and i patted the floor where he had benn, and he slowley moved back next to me on the floor. I opend my mouth and guided the head in and started to suck him. He said my name as i was sucking him and i stoped, and said call me linda dont say that outher name if you want me to keep going and he said ok. I sucked him slow and deep, after a few minouts his dick started to swell in my mouth and i knew from my own that he was going to cum. I stoped and asked him how where he wanted to cum, in my mouth or do you want to fuck me? He said bouth that he can cun 3 or 4 times a night. I smiled and said ok pleas fuck me first, and reached for my purse wich i had put my cigarettes and a tube of moms lube and a condome in it befor going into the room with him. I lit a cigarette and we set next to each outher on the couch, he told me i looked just like her and i said i am her dont think of me as looking like her think of me as being her or i cant do this just call me linda or miss riggs. I told him the more he calld me by her name the more i got into the part, he agreed that it was getting him harder then he had ever been. He then said linda i want to make love to you so bad, and ismiled and we started kissing. I had caught my mom having a few on night stands and knew what she liked and what things she would say to help get the guy off faster, so with that in mind i leand over and started sucking his dick again. he was gently pushing my head down on his dick and soon i felt his balls on my chin and knew i had all 7 inches of it in my mouth and throat.He started to cum and pushed me all the way downas i felt each of 7 hard squirts in my throat then he relaxed his grip on me and i felt 2 more squirts on my toung. It was very thich and salty, and i loved the texture as i swallowed it all down it burnt a bit but i loved my first tast of cum. I set back up and finished my cigarette, im a slut i thought to my self i just swallowed a guys cum and im haveing a cigarette just like mom after giving head.I wanted more, we talked as him and linda and the whole time i could still taste his cum in my mouth. He was still hard and soon he was kissing my neck and telling me he wanted to be inside me so bad it hurt i nodded my aproval and he started kissing me downmy sides and sliped his hands up my thighs and pushed up my skirt and slid my thong down my legs and took them off then tosed them on the floor next to the couch. i was tucked and i looked just like her with a thick patch of hair and it almost looked like lips. He got the condom and i told him what mom tells guys she wanted bear( ive had my tubes tied so you dont need that unless you want to)just to let him know it was ok with me if he wanted to cum in me bearback. I spread my legs wide and lubed my hole and he lubed his big dick then got over me.I reached down and took his hard dick in my hand and put the head right at my hole and said i want you in me, but rember you have to go slow you have a big dick. With that he leand down and sliped his toung in my mouth and pushed fowared slowly, i felt a pop and a sharp pinch as the head sliped in then we stoped for a second to let the pain go away. Then he slowly pushed till it was all the way in. I wasnt getting hard but it felt like i was on fire in my ass and my clit. He moved slowly in and out of me for about 3 minouts and i was kissing him amd telling him how amasing his big dick felt inside me and then i couldnt take it anymore i started begging him as slutty as i could pleas fuck me, fucke me hard and fast. It was a good thing we were alone as i was not whispering, i was screaming and shouting fuck me as he hammerd my ass as hard as he could. A few minouts later he finaly started swelling up and i felt him tens up as he started yelling oh fuck im cumming and my ass got real hot and slippery, as he finished cumming in me he colapsed on top of me kissing me and gasping for air. We laid there for a bit with his dick sti in me half hard and he said he loved the way my tits bounced as he fucked me. I kissed him and said i loved the way his dick felt inside me, and that i wasnt done with his dick unless he couldnt go any more. He said he wanted a lot more but didnt want to use my moms name that we need to come up with a name of my own. We set up and his dick sliped out and i stood up and got my cigarettes and set on the couch with my legs crosed as i smoked my cigarette i thought about names.iI chose deborah from a distant aunt, i took lyn from my best female friends ever and riggs is from the bestguy friend i ever had growing up. He was gay but was the only one who didnt know it lol he is still one of the best friends ive ever had.


thank you hoped you enjoyed reading about my first time. if you liked it let me know and ill wright more.

debby r.


Story URL: http://xhamster.com/user/deborah_riggs/posts/35370.html