It was a Wednesday evening I had set up three dates with keen admirers. We had been emailing and even exchanging texts for the past week but one by one they dropped out. The best chance seemed a man that got as far as talking to me at around 8.30 for a meet at his flat at 9. I had got home and started to prepare my self to be his girl for the night. We were going to play at his flat, I would arrive dressed and were had discussed the sex, I had seen a photo of his cock it wasn’t too big and I agreed that if he felt like it I would let him fuck me. I was putting the last touches to my make up when he sent a text to say his brother had turned up and the date was off! I was feeling desperate for some male attention; I wanted to be seen, to be touched, enjoyed and used. I wanted to be someone’s slut. I was dressed completely as Jill having bathed and trimmed myself before slipping into all black lace lingerie, black stockings. My lacy underpinnings were hidden under a layered silk and black net skirt and see through black lace blouse. I usually like to wear more colour but my potential lover had requested black. My face was fully made up and topped off with a shoulder length auburn wig. I wore pearls; on my ears, neck and wrists. A black feather boa loosely hung over my shoulders and down my arms. I logged onto the swinging heaven chatroom and switched on the webcam. Within minutes of finding and queuing to join the BI TV room I was sitting virtually with 70 other transvestites or lovers of transvestites. I introduced myself bluntly as ‘looking for cock tonight’. Within seconds the whispers began, it gives me great girlish pleasure to be spoken to the way these men do. The other trannies don’t comment so much as the guys that admire. I happily give out my mobile number and take a few calls from guys that want me to talk dirty to them; I love hearing their breathing as they wank to my voice. I describe what I am wearing. They ask me questions they’d never get to ask normal girls, I love it. I tell them yes I love to suck cock, id love to be sucking yours, oh yes I have my hand in my panties, I’m feeling my breasts I want you to come on me, oh yes baby come on my tits make my bra soggy with you cum, when the phone goes dead I know I have done well. Often this can go on for an hour or more and the keenest candidates live at least 100 miles away. I had two callers cum for me when I got a whisper from some one who was only 3 miles way from me. His profile was blank. I gave my phone number. We chatted on line for a while, he had seen my photos, he thought I looked nice and he wanted to play with me. It was late, after 12 and I was close to giving up on getting any cock tonight. I typed, “Can you accommodate?” “yes but you must be quiet, wife asleep in next room” Fuck, I didn’t believe it, it sounded like the start of a refusal. Another missed opportunity. “That sounds fucking exciting” I wrote,” your wife so close, I’d love that. Me sucking your cock and at any time she could walk in on us. Can we really do that?” Yes she knows what I do, doesn’t like it but we’re almost separated and just live together. I d love to do it I said, It’s a fantasy of mine to suck a husband while his wife watches encouraging me, telling me what he likes and then her making sure I swallow properly when he cums. Maybe she’ll smack my bottom for being such a sissy as to suck her husband’s cock, on my knees in her house. Far fetched I guess? I typed in my phone number. Almost immediately the phone rang and it was him! He gave me his address, I had his phone number, it wasn’t withheld. I was instructed to walk up the side of the house and enter by the sliding patio door from the garden. I knew the address. He seemed OK not pervy or tough sounding, very together and organised. I got into my car in my feminine outfit, it was a warm evening and I didn’t bother with a coat. I took flat sandals but just in case put my 3 inch patent heels in a bag. In my handbag I had a lipstick, condoms, tissues and a tube of KY. Putting condoms in you handbag is a pretty sexual thing to do, it’s a little moment that real, I am a girl going out and I am planning to have sex. I am ready to let him do it. As I drove the three miles I concentrated on my driving. I love driving dressed so late at night. Need to be extra careful though since police and uninsured drivers are the most likely people you’ll run into that late at night. Running my spare hand over my stocking clad thighs, feeling the weight of my delightfully bouncy 38C boobs. Now and again I brush away a wisp of my long hair. I am feeling very sexual. In the mirror I am happy that I look very convincing and certainly send out my intentions. I arrived at the address, parking is limited I wont be able to park right outside and in the early hours I am sure the sound of the car is drawing attention, is his wife a light sleeper? At least he will know I am here. I drive to the end of the road perhaps 150 yards from his home. I applied some fresh lipstick, checked my face and hair in the mirror and then stepped out of the car. Adjusting my handbag and putting the keys inside it I was now vulnerable and also ready to walk brazenly done the street towards the house where a husband was sat at his computer looking at porn and waiting for his slut to arrive while his wife was fast asleep upstairs. I did hope she was a light sleeper, she had heard a car outside and was listening, maybe she could hear the softest of footsteps as I crept to the garden of this house. There was a garden gate, it was ajar but rickety I pushed it open, as he had described there was a patio door and it was slid open an inch, there was a light on behind a curtain. For a moment I thought this could be any of a series of pranks. Lots of men having a sex party with me a victim, it could be a bunch of thugs, it could be a joke and this a random address. However I felt safe I could scream, this was a nice neighbourhood. I tapped on the glass, a girly little tap but it was enough and there he was at the curtain, the glass slid back and he stood back to let me in. It was a small dining room the dividing doors into the living room were closed and obscured somehow so I couldn’t see beyond other than to know it was dark every where else in the house save for the glow of the computer screen (he was watching some real women sat at their keyboards their breasts on show in the SH chatroom) and a small desk lamp. I stood in the middle of the room he walked around me looking at me and expressing how good I looked, I felt so sexy and wriggled and struck poses for him. He stood in front of me and reached out to put his hands on my hips, I reached out and kissed him, he immediately responded and we pulled into an embrace and kissed fully with entwined tongues. I was made up and smooth his chin was stubbly and rough.We rubbed our bodies together I made sure my breasts rubbed against him and he trust his groin at me, I could feel his cock, it was engorged but not hard, yet. I asked about the wife, “be quiet she wont bother us”, I told him I was so excited about her catching me, we could have a cat fight over him, what would she do, cry? Join in; she could be as kinky as him? Tell me that I could fuck him if I wanted, since she was finished with him. Gosh it could go any way, all of them lots of fun for me! He felt me all over, it felt lovely having his hands exploring me, I asked him to feel my tits, my blouse was unbuttoned and my bra encased boobs given a vigorous handling, it was my turn and I went straight to his cock. As soon as I showed an interest in the prize, his trousers fell to the floor and I followed. Straight to the floor on my knees, I knew what to do and having kissed and licked the head took him fully into my mouth. For the third time in two days I was sucking for all I was worth on a man’s cock. I held his hips and sucked, slurped and gobbled him giving a most enthusiastic performance. There are so many things a girl can do with a cock and her mouth, I have sucked enough cock now and seen so many videos that I could go on all night changing position adjusting style and above all being as girly as I can while still looking after the man that has made me feel so special. He was about to cum I felt him buck once and a dribble of the tasty stuff took over my taste buds. He took himself out of my mouth, I stood up and we cuddled a bit more. He turned off the light and there was only the glow of the computer. “Its so sexy knowing your wife is up there, did she like to suck you gorgeous cock as much as me?” I cooed. “Did she let you cum in her mouth?” I asked hoping this would get him going; I was really feeling so sexy and relaxed. I was enjoying the role-play. Being in a house rather than car parking was so much better. Do you want to fuck me? I asked this as I held the back of a chair and leaned forward by bum sticking out as pertly as I believed possible. I was watching the images on the computer screen, those chat room girls sat motionless typing to their admirers real breasts joyfully on show. I found his name was Stewart (from the computer screen) and Stewart was lifting my lacy skirt. He took down my panties I kept them on one ankle, his hands went to my hole and he rubbed me there. From my handbag I got the condoms and lube and he took them from me. He knew what to do and swiftly applied lube around the hole and fingered a little inside me. I felt the cold tip of the condom flapping against my sensitive skin as my rosebud was gently eased open by the head of his cock. Getting the position right was awkward I am tall and my legs being so long made it a reach for him to get the best angle into me, but he was skilful, I am sure he has fucked girls this way before. I was joining his list of conquests and was about to become one of his women. I arched my back and made my legs wider which lowered the target for him and then he was in me. I had his cock fully up inside me and he started to fuck me really fast which was so great. This was the first time I had been fucked properly with a real man in mans clothes with a hard hot cock. Stewart was enjoying the feeling of having his cock stuck up a sexy thing like me but the position wasn’t good. The wicker chair was sliding across the floor, I wanted to scream out like a proper girl having orgasm after orgasm but had to keep it down for fear of the wife asleep upstairs. The chair wasn’t working, he slipped out of me. I got on the floor on my hands and knees. He went into me again easily and fucked me in this position for a few strokes, obviously not comfortable for him he rolled me onto my back, I positioned my skirts and he loosened my blouse completely. Stewart lifted me by my ankles till my now willing bottom was off the floor and he was on his knees as he entered me again. He came out of me and it was my fingers that got hold of him and pushed him back in. I showed him I wanted it; I wanted him to fuck me so bad. We were looking into each other’s eyes as he fucked me some more. We would have been a sight if the wife came in now, I could picture what we looked like him the husband dressed in the shirt he had worn earlier in the day but now pants off, on his knees with this bloody transvestite lying there letting him fuck her/it like a filthy fantasy whore. What did that creature think it was doing giving itself to her bastard of a husband? She might also have found it so deliciously perverted, bringing some of her own wildest ideas into the mix, I bet she has some dildos laying at the back of her knickers draw, that would teach that sissy what its like to take a proper cock. I wanted to be seen and so let out some moans. Imagining her in bed awake now, hearing the strange scuffling down stairs, expecting to catch him wanking over porn. She might never in her worst nightmares expect to see such a scene playout on the dining room floor. I was being fucked properly now; he had a good rhythm and wasn’t popping out of me. I could feel his man bone teasing my sex bits inside and outside, he was holding me properly like a woman at the hips with one hand but alternating between rubbing my tits and wanking my cock. His tummy flesh was bumping against my bottom cheeks. His hands could feel my stocking tops and suspender clips. He pulled out of me and took off the condom. “I want to come on you” he said. “Ok, id like that”. I was still on the floor and he offered me his cock to suck again. It stung my mouth, the condoms I have are spermicidal and the chemical stings my tongue but I blow him good since I want his cum now I am very sexually aroused and giving into abandon now. I am making a lot of gobbling grunting sucking noise and bobbing my head as fast as my girly neck muscles will allow. Stewart pulled out of my mouth with a hand on my forehead to keep me off it. I want to cum over you now, he opened my blouse and I lay back and fondled my boobs while he stood over me wanking himself furiously. I was lying there gasping for him to cum, I was talking as dirty as any of the girls on facial abusedotcom Come on me, cover me honey, spunk on me ,coat me baby. Oh yeah, oh yeah. I wasn’t whispering anymore. Stewart ejaculated over me. The first spurt was a big gloop and landed on my bra, then a series of smaller spurts splashed onto my tummy and into the multiple chiffon layers of my skirt. Monika Lewinsky crossed my mind. This is what the president of the United States did to Monica in that dress, I had fantasised about being Monica L, when that story was news. His sperm quickly cooled and began to run down my skin, I rubbed it in. It crossed my mind he’d like to see me lick it off my fingers. That’s what I did, slobbering at it like a greedy bitch. Then I moved to his cock, I know better than to play with a mans cock when he has just come but I was horny as fuck and got to my knees and sucked him, I could taste the remaining spunk and gobbled. He didn’t want much of this and I let him go. “I want to see you cum now Jill.” I did just that and with about three strokes of my girly little cock I spunked a load with enough pressure for the first glob to land on my own pearl necklace, the dribbles dampened my bra. I started to relax. “Wow you were very excited weren’t you he said. I have had such fun tonight I said, I have been thinking of nothing but this all day. As I was doing the buttons on my sticky blouse we kissed some more. I pulled my panties back up I was very sweaty as it was a warm evening and the sex had been great, added to that my make up was smudged, and I felt covered in cum, there was dampness in my blouse, my panties were soaked with sweat, cum and anal lube. Now where was that wife to complete this tale? Sadly for me she remained out of the way, but did she hear anything? I straitened myself and gave my man a final kiss I told him he had been the first man to fuck me and I would remember him. Sadly I don’t have any contact details for him and may never see him again. I walked back up the alley between the houses and into the street in my sexiest hip-wiggling walk I returned to my car. I enjoyed the drive home; I was aware I smelt of sex, I had a perfume spray in my handbag and sprayed myself. On the way home I parked up and sat in the car a while. I felt so good in my self and my appearance that I decided to go for a walk in the dark. So in the lane along side the local railway station at 2.00am on a Thursday morning I took a long stroll enjoying the feeling in my bottom, my girly little penis tucked in the tight panties, feelings of my breasts moving, the tug of my stockings and evening breeze through my long hair and as fresh air filtered through the delicate fabric of my female clothes dried my sexy sweaty skin. Back in the car I was hard again and before driving off I rubbed myself through my skirt and panties to a second soaking panty orgasm. When I got home I had a lot of work to do. All my clothes now needed laundering to remove the sticky stains from my pretty clothes. I love being a girl especially a sexy playgirl. How sad to put the fresh clean laundered outfits away in a suitcase hidden away in the loft till the next time. Jill Gossard May 2008.