I was aware I was interested in different things about sex, & was not put out when I got caught wanking by a girl in the ladies toilets at school and managed to not to tell, if I let her watch me everytime she was around. This lead to me visiting Yvonne's home at weekends & holidays where I stripped off & slowly stroked my cock until shooting into my hand before sharing my jizz with Yvonne. This soon became less exciting & when Yvonne helped me stay hard by removing her top clothes showing me how fabulous her 36B tits looked inside her bra cups + I often saw her pussy through the lace of her panties. It was after a few weeks tossing myself off in her presence I found a black bra Yvonne dropped from her washing basket which I quickly stuffed in my pants and left pretending I had a headache, and I ran home excited. I went to my room,pulled out the item and removing my shirt I awkwardly managed to put it on. My cock felt like it wanted to explode & I came almost before I stroked the shaft just once. I kept that bra hidden from Yvonne for a month or so but she found me,dick in hand & wearing the bra after my Mum let her upstairs & I didn't hear her. I remember standing in front of her trying to speak & explain why her bra was with me, as Yvonne told me to shut-up as she took off her blouse.skirt & tights before removing my jeans & pants making it clear she found seeing me was something she was enjoying,she let me caress her tits for the first time & didn't stop me slipping my hand inside her panties & insert 3 fingers into her hole, & I soon had a tit in my mouth making Yvonne groan with orgasmic exstasy. Yvonne was shaking & pulling me on top of her helping my cock slide inside her & within seconds I filled up her hole. Next day she called me to her house, & as I went up to her bedroom Yvonne said she wanted me to dress in a set of underwear,which didn't shock me, and with her aid I soon stood in a white matching bra & panty set as well as a mid-lenght chifon dress finnished off with a pair of white hi-heel sandles Thinking that was it I tried to kiss Yvonne & get her top up,but Yvonne wasn't done.she sat me on the chair and began to paint my nails with a light red & matched that with lipstick. Then she undressed herself leaving me dressed as a female and she was naked exposing her shaven pussy. She said I was the girl now, & she took a polaroid of me, forbidding me to go near my cock untill she allowed me to. I did as I was told & she made me watch as she got a vibrator to fuck her self,occasionly slapping my bell-end lovingly,and as she removed the plastic tube the last time,made me lay on my front,& slowly pushed it up my ass still vibrating,and went down and slid her mouth over my cock and sucked me with gentlness so I didn't cum, making sure she left my erect rod wet. Until then I had wanted to fuck somebody up the ass,so we swapped and I carefully pushed inside her. Yvonne groaned more & moaned she had cum which got me beyond the line & I emptied my balls into back hole. By the time school went back we both enjoyed being fucked from behind,something we contined. Near Xmas I had my next sex joy, when Yvonne wanted a threesome with another girl, & had already asked her friend Jill round that Saturday, & also told me she knew I crossdressed for Yvonne, & Jill wanted me to be "dressed" so she could see a man in a dress. I was really excited and when the day arrived I had a bath, shave ( chin pubes legs armpits included), & went to Yvonne for help with bra straps,make-up etc. to be given new items including a 36A black bra,extra padding to give my tits proper shape, a pair of lace panties,suspender belt,silk stockings & a knee-length skirt,41/2" hi-heel shoes all black, a white c-thru silk blouse,that showed my black bra through it in a sexy way. I got dressed & Yvonne painted my nails a deep pink with lipstick to match before she got me something I hadn't thought about, a long,wavy wig same colour as my own hair. 7 pm & I heard the door bell, Yvonne went & answered it, returning with Jill,a 19 year old,long blonde hair & a body like a model. I found out later Jill had a 36 28 34 figure & as she entered the room,Yvonne introduced me as "Jayne". Soon the wine was flowing,any embarresment was gone,& Jill's tits stood out of her tight top. Yvonne got things going by taking off her blouse & dropped her dress to the floor sitting between Jill & me gave her space to stoke both Jill's & my inner leg while Jill kissed her lips. I took Jills bra off to release her tits & soon had my mouth licking her erect nipple. As I kissed her tit.Jill had a hand inside my panties,& with my cock as hard as a rock, Jill moved me so she could sit on me & also see Yvonne fingering her cunt, before Jill took over with her fingers,getting me so horny I fired my jizz up Jill. Climing off me,Jill wasted no time before she had her mouth between Yvonnes thighs using her tounge to take Yvonne to new hights of sexcitment a gain & again & again, as well as herself,squrting her juices over Yvonnes face.
A First Time For Everything.