Date: Thu, 13 Feb 2003 00:24:46 +0000 From: stevey Lister Subject: LUCY AND ME I went to stay with my Aunt Lucy for the summer break. Uncle Harry had run off with another woman about two years before and I promised Aunt Lucy that if I could ever help her with anything I would do. She phoned and asked if I could help clear the garage of a load of Harry's old things, she said she couldn't touch his crap without getting angry. I agreed and she offered me bed and board and said she would give me 50 bucks a day. Well who wouldn't want 50 bucks a day for throwing rubbish away. I had not seen Aunt Lucy for about twelve months and as a kid I always fancied her. She was tall with long curly red hair. She had the figure of a Playboy girl and for a woman of 55 she was outstanding. "Stevey... I've got some coffee on the go for you. Come on in and have something to eat too" she shouted from the kitchen window which overlooked the back yard and the garage. I'd loaded shirts, trousers, shoes and coats into the back of her Dodge and was ready to go to the ASPCA shop on the outskirts of town. "Hi Aunt Lucy, I hope I didn't wake you this morning....I tried to be as quiet as possible" she gave me a warm smile and said "It takes a lot more than you banging around in the garage to wake me" and she turned back to the stove and carried on making pancakes. As she turned the hem of her robe snagged on the stove door and it ripped. "Shit" she said almost under her breath and then apologised to me for swearing. I laughed and went to her aid, it was caught and every time she moved it ripped a little more. I grabbed the hem to stop it from ripping more and started to untangle the loose thread that had caught. I looked up at her and was about to speak when I came face to face with the hairiest pussy I had ever seen. She was obviously blissfully unaware that she was on show and just looked down at me whilst I gazed. She turned back to the pancake pan and lifted it off and I unfastened her. I had one huge hardon all the way through breakfast and desperately wanted to see her like that again. Later in the day when I had finished I showered and wanked furiously thinking of that red bush. That night Aunt Lucy poured us both a large Jack Daniels and ice and we sat talking about life, the universe and everything. She was well read and damned intelligent and in the low light of the room I fancied her even more. "So, how comes you've not got a girlfriend Stevey. A gorgeous boy like you should be screwing night and day?" I was shocked at her plain speaking 'cos I'd never heard her speak that way before. "I've had my share of girls" I said defensively and then I opened up more than I expected too, I guess the alcohol loosened my tongue just a tad. "I've had my share of guys too....." It went quiet for a moment and I thought I'd said the wrong thing. She sipped again and looked at me. "It's funny but I always thought you were gay. I used to tell Harry that you were gay 'cos somehow you just don't seem all that interested in girls." I gave her a puzzled stare and asked her to elaborate. "I think you'd look fantastic as a girl. You're almost hairless, your very slim, you have such short cropped hair that I guess one of your Aunt Lucy's wigs would suit you fine and.... yes I guess with a bit of makeup on you'd pass for a little sexpot." Shit. How do I respond to that I thought. I blushed and could feel the blush arrive and announce itself to the world. Aunt Lucy got up and poured another drink for us both and I just sat there almost open mouthed trying to think of what to say. "Do you want to experiment a little....it could be fun for us both you know." "What do you mean?" I nervously asked. "I mean if you want to have some fun, I could make you look like a beautiful woman. Just for fun you understand..." I had cross-dressed on a few occasions and I liked to do it but I had never done this in front of anyone. I really didn't know what to say. "You don't have to. I'm not going to force you." "No....erm I mean yes, we could try I guess". What the fuck was I saying, I was allowing my Aunt Lucy to cross-dress me??? She got up and poured me yet another drink and the effects of these long drinks were to reduce my inhibitions to nothing. She walked to the door of the room and said "Well come on then....there's no time like the present..." and with that she walked upstairs. I followed like a little lap-dog and watched her fat ass wobble as she climbed each step. She opened her bedroom door and when I walked in she was sat on the bed leaning back. "open the closet and tell me what you like." I opened her closet and there were hundreds of dresses and skirts and blouses and....shit there was leather uniforms and a good many Basques hanging there. She joined me and picked out a tight black dress and held it against me. "There, I guess I'd like to see you in this." I stood there with a glass in one hand and an embarrassed smile on my face. "Well, you can't wear it over your clothes so get undressed." I took off my shirt and dropped it on the bed. I kicked off my shoes and I pulled my jeans down and then pulled off my socks. I stood there in a pair of boxer shorts looking somewhat pathetic and she smiled. "Come on don't be shy.... you think I never saw a naked man before. Do you want a hand with those shorts or can you manage on your own?" I thought I could whip the shorts off quick and turn my back to her and then pull the dress on and that would limit my exposure to her dramatically. She was obviously a damned sight cleverer than me. I pulled my shorts down and reached for the dress. "No you can't just wear a dress without some decent underwear..." and she got up and walked towards me. She pulled a drawer open in her dresser and started to search. She held up a small pair of black briefs and held them over my growing cock. She turned back to the drawer and pulled out a bra then another bra and then threw them back in. "I've got just the thing" she said and with that walked over to the closet and pulled out a hanger with a black Basque on it. She walked over to me and held it up against my naked body and then sat back down on the bed. "Come closer" so I did, "No closer still..." and I came a little closer. She stared at my crotch and said "We'll have to do something about that lot." "What lot?" I replied. "I'm going to trim those pubes for you so you don't have a load of fur sticking out of the side of my panties." I wondered what the hell she was going to do to me. She told me to sit down and wait for her which of course like a good little lap-dog, I did. She returned a moment later with a large towel a damp flannel and some cream. "I want you to sit on the bed in front of me and open your legs." I was scared but somehow I was excited too. In fact the excitement was showing. I sat down and leaned back and opened my legs a little. She took hold of my stiffening cock and I almost went through the fucking roof. I watched her rubbing this cream around my cock and balls and eventually around my asshole and then she just sat back and stared at me. "You know you have a lovely cock.... I always wondered what it would feel like to grab a 20 year old's cock. It's a big thing for a woman in her mid fifties to have a naked boy in her room." She was almost laughing and didn't seem able to take her gaze away from my cock. "I'm glad you like it... I always wanted you to see it." I said. "Ooooh you bad boy." A few minutes went by and then she took the wet flannel and started to wash me down. I watched as the hair just fell away. She washed all the cream and hair away and then took the edge of the towel to me to dry the whole area off. When she'd done so she told me to stand near the mirror whilst she dried me off properly with her hair dryer. I stood in front of her mirror and she blow dried my cock and balls and then told me bend over. I bent right down and stood with my legs apart and she dried my ass. She had her hand on my ass whilst she did this and it was warm and soft and beautiful. "You have a cute little asshole. It's neat and clean looking." Stupidly I just said thanks...what a fucking nerdy thing to have said. She told me to sit at her dresser and she took a pair of black seamed stockings out of a new packet and stretched one over my foot and smoothed it all the way up my leg. She stretched the other one over my other foot and smoothed this one up to my thigh too. She then wrapped the Basque around my chest and fastened it at the back. It was real tight and I had to breathe in whilst she fastened it. She told me to stand which I did, and with my cock slapping into her forehead she fastened the stockings to the suspenders. My god I felt so sexy. She then opened the panties and told to put my foot in and then the other one and then she pulled them up. My cock was sticking straight up out of the top of them and she just pushed it back inside and then smoothed her hand over it inside the panties. "Turn around and let me look at you" she said. So I turned slowly and stuck my cute little behind out a touch. "Ooooh that does look nice. It's as smooth as silk." and with that I felt her tongue slide across my ass in a long drawn out wet lick. She pulled the dress off the bed and told me to step into it and she pulled it up and onto me properly. She laughed and told me I looked fantastic and then said it was time for the makeup session. "Sit down at the dresser and I'll continue the transformation in a minute." She took my glass as I sat and went downstairs. I looked at myself in the mirror and rubbed at my crotch and my rock hard cock. She returned a moment or two later with another JD on the rocks and I sipped at it. She applied a foundation and smoothed it into my face gently and with every attention to detail. She put powder on my cheeks and used a fluffy brush to smooth it in. She used a pen on my eyes and elongated the shape of my eyes with it. I was starting to look like a young lady. She applied a lip gloss that made my lips look shiny and a very deep luscious red. A lip liner next which made my lips look pouty and sexy and then she set to work on the finer details such as my eyelashes. "Bitch... you've got much longer lashes than me. I'd kill for lashes like that" she laughingly said in-between sips of her rather large drink. After a while I looked a bit like a panto dame with make up and cropped hair. She went in the next room and came back with two red wigs. The first was shoulder length and very dressy. The second was long with a slight curl to it. She carefully pulled it onto me and straightened it and then brushed it and teased it into shape. My god, I thought, I looked fucking gorgeous and I felt so fucking sexy I just can't tell you. I walked around the room and she brought out some plain pointy toed shoes that had a 2 inch heel. They fit if a little tight and I found that they not me, made me walk more feminine and forced me to wiggle my ass. She hugged me and told me I was beautiful. She held my ass and squeezed softly running her hands down to the suspender catch and then back to my ass. "Shouldn't you dress up now Aunt Lucy?" I asked sheepishly. "What would you like to see me wearing then?" I thought for a while and walked across the bedroom to the closet. I thumbed my way through her clothes and found a long black pencil skirt. I pulled it off the hangar and threw it to her. "Oh... that's rather conservative" she said. "I want to see you how I've fantasised about you for years" I replied with a somewhat naughty grin creeping across my glossy lips. I searched through her blouses and found a sheer white one, you know the sort a woman would wear with a camisole top underneath and a bra under that to protect her dignity. I threw that too her too. She looked surprised. I told her to get some high heeled shoes and asked if she'd any stay-up stockings "Black ones, they must be black ones" I said and she began to oblige. When her clothes were laid out on the bed she looked puzzled at me and asked what underwear she should put on. "Nothing.... black skirt and stockings and that blouse tucked in nice and neat." "I can't wear nothing under that blouse you'll see my.... oh I get it." and she smiled. "Come on.... undress for me." I told her. She kicked her shoes across the room and unfastened her skirt from the side and then unzipped it. She let it drop to the floor. She was wearing black pantyhose and black knickers and I thought her legs were the most shapely I had seen. She unbuttoned her blouse and removed it throwing it to the floor. She had a large black bra on and she unfastened it from the back and like a porn starlet she held the cups in place and then turned to me with a worried look on her face. "Steve.... I don't want you to upset. It's just that I'm 55 years old and my body is not what it used to be.... my breasts aren't going to be what you're probably used to....I mean they aren't pert little things.... and my..." I interrupted her straight away... "Lucy, your a beautiful woman. You have a fantastic figure and whatever shape or size you are - you are 'my' Lucy now..." I walked over to her and looked deep into her eyes. "Lucy you are 'my' beautiful young woman...." and whilst still looking into her eyes I pulled her hands away from her bra and it fell to the floor. Her breasts were huge and hung low like all the women I wanked to on the internet and in porn movies. Her nipples were dark brown and oval shaped and .... well the only real way I can describe them is that they were the size of side plates. She was looked fantastic. I cupped one breast in my hand and she gave a sharp intake of breath and held my hand and squeezed it onto her breast. I sat down on the bed and picked her bra up off of the floor and held it. I quite deliberately looked at the label to see what size she was - 44EE.... wow! She leaned down and pulled off her pantyhose and told me she didn't have the nerve to take off her panties. I switched off the main room light and switched on just one bedside lamp. I could still see perfectly well as I turned to walk back to her. "Let me help you then." With that I gripped both sides of her panties and slowly and gently pulled them down. Once more I gazed at that beautiful red bushy pussy and I could almost smell the heat coming from her. Her breathing had increased and I couldn't believe it but she looked shy. This once confident woman who so seductively licked the cheek of my ass was now looking shy and apprehensive. "Beautiful" I said as I looked at her hair. "What's beautiful?" "Your pubic hair... it's so full and red and ... well beautiful" she pulled away and said that she hadn't waxed for a while and she looked embarrassed. "No... I don't like a woman to be all trimmed down there. I like a hairy woman, I really do it turns me on somehow... I hope you don't shave your armpits" and she looked slightly shocked and lifted both arms up. There was a mass of curly red hairs under each arm. I stood up and held one arm in the air and pressed my tongue into her hairy armpit and licked. I tasted the sweat and the odour of perfume. With my free hand I held her breath and the looked her in the eye... "You are so sexy, but I want to see my fantasy girl all dressed up now" Her confidence flooded back and she pulled on the stay-ups and smoothed them in place she turned to get the dress off of the bed and I saw her big ass and my cock almost burst through my panties. It was big and pear shaped and soft looking. It had two lines where her panties had been and it wobbled a little as she moved. She caught me looking at her ass and said, "I suppose you like a fat ass too?" "Yes I do. I love the thought of having something substantial to squeeze and... to bury my face into." She just smiled and pulled the black pencil skirt on. Her breasts swung from side to side as she wiggled the dress into position. Just the sight of these huge natural breasts swinging made my cock twitch and my determination to fuck her strong. She put the blouse on and faced away from me as she tucked it in and fastened it right up to the neck. She put a pair of patent leather black stiletto heeled shoes on and leaned down to the mirror to adjust her hair. I came up behind her and slipped my arms around her waist. I could feel her breasts with every move she made. I hugged her tight and then walked over to the mirror to look at myself. I thought I looked gorgeous and the only thing that gave the game away was the large bulge in the front of my black skirt. As I was admiring myself I saw her turn to look at me and with the bedside lamp behind her and to the side I could see the most wonderfully large breasts as plain as day through the sheer blouse. I turned to look at her and she spoke softly. "Well... what do we do now?" "I've no idea. What would you like to do." "I guess we go and pour another drink downstairs" she said, and off we went. I walked in front of her and held the stair rail tightly in case my new high heels proved to be a problem. I walked into the room and over to the drinks cabinet and lifted the bottle. I turned to watch her walk into the room and was mesmerised by the size and shape of her breasts and the way the swung heavily from side to side as she walked. She came straight over to me and asked why I wanted to see her dressed this way. I told her I had gotten a fantasy from years before when I was about ten or eleven and I'd stayed with her and Harry on a superbowl weekend. I told her how I had watched her undress through the crack of their bedroom door and how I had been fascinated by 'full-figured women ever since. She had been dressed much the same way then and I'd imagined what her tits would look like under a sheer blouse. I sat down and automatically straightened my skirt pulling it down slightly as it rose up towards my stocking tops. She was looking at my legs and kept telling me I looked so sexy. "So why do you want to see me dressed as a woman? Does it really turn you on." "Hell yes... I went to college with a transvestite years ago and we made love lots while he was dressed as a woman. I think it was the only way he could manage a hard-on actually." "What about Uncle Harry...?" "You must be joking, Harry was boring....wham bam thank you Ma'am and turn out the lights, that was Harry. It was only when he left me that my fantasises came flooding back, I'd lay in bed masturbating thinking about Suzy's cock inside me whilst running my hands up and down his fishnets..." "You know this morning when you caught your robe on the cooker.... I saw your pussy whilst I tried to free you - did you know?" she looked horrified at first and almost dropped her drink. "You're joking right?" "Nope.... that was what kept me going all day... I'd have died a happy man if I'd seen nothing else in my life." "You dirty little girl... come here" I got up and walked over to her. She playfully smacked my tush and said that if I continued to look at her pussy she'd punish me properly. I crouched in front of her and she held my face and kissed me - just a peck at first and then a full-on frenchy. I smeared lip gloss on her and she smeared it on me, I guess I looked a bit like a slut when we'd finished. She tidied my make up for me from the usual supply of goodies in a woman's handbag which was at her side. I sat back and just stretched both hands out and held her breasts. Her nipples had grown long and hard and I massaged them through the blouse... "I used to fuck Suzy you know? I fucked her like she was a real woman, we used to have this strap-on thingy with a big fleshy cock attached to it and I used to stick it up his ass and fuck him like a girl... I enjoyed that so much, it's like having so much power - you guys are lucky to have a cock" By this time I'd run one hand up her skirt and was gently caressing her pubic downy forest. I ran a finger over her lips and they were warm and wet and she jumped ever so slightly and moaned quietly. "Was that a hint? Do you want to fuck me like a woman?" I asked whilst running my finger up and down her gash. She opened her legs slightly to give me a little more access and I inserted a finger slowly. She moaned a little louder now and I reached under my skirt and pulled my panties aside allowing my cock to spring free. I fingered her softly whilst drawing the foreskin of my cock back and forth slowly. My finger penetrated ever onwards until I was deep inside her. I drew back and used a second and third finger and she groaned out loud. My god I thought, she was loving every minute of it. I was wanking a little faster now and reached further underneath my crotch and tickled my anus with my index finger - that turned me on. "Yes... I want to fuck you like you was a girl... I want to do it now..." and she stood up sharply and my fingers bent upward and fell out of her moist pussy. She started to walk away and had a pained expression on her face... "I want you now don't just sit there....I'm not kidding - get upstairs quickly" I followed her with my cock swinging in front of me. I wobbled on my high heels as I made my way up the stairs. When I got in her room she was throwing clothes out of the bottom drawer of her dresser and then pulled out a quite normal sized strap-on cock. She wiggled out of the pencil skirt and frantically pulled the straps over her legs and pulled it tightly into position. She adjusted the waist strap and pulled it tight. I just stood there. "Bend over" she said in a very commanding and hurried tone, so I did as instructed. She came behind me and lifted my skirt over my hips and then yanked at my panties. She put one hand on my back and pushed me further down until I was nearly bent double and holding onto the dresser. I waited for a minute and in the mirror watched her squeeze a large mound of KY onto her hand and I felt it slap against my ass. "hey that's fuckin' freezing... you could have warmed it up first..." she laughed out loud and heartily and then massaged the jelly around my anus. She inserted one finger and stuck it in and out and then two fingers and then three... "I thought I'd get my own back on you - you little lesbian you". Aw heck it turned me on being spoken to like that and I guess I knew what it was like to get fingered now. I watched in the mirror as she squirted some jelly on her plastic cock and wanked it up and down so it was covered and then she turned her attentions to my asshole. She put the head of her cock against my hole and pushed and it went straight in. She pushed a little harder and I could feel it going further and further until I felt her belly against the cheeks of my butt and then she began to fuck me like I had fucked so many girls and guys before. It hurt in a nice kinda way. "Take your blouse off now I want to watch your tits bounce." She unfastened it and left it on so that only every now and again did I catch a glimpse of her nipples. Her cleavage was large enough to fall into and I wondered if I'd get chance to get my dick between them mounds of flesh. She put her hands on her hips and opened her blouse and kept fucking me. I watched her tits swing and jiggle and bounce all over the place and then she pulled the blouse off. I straightened a little more to watch her. She reached around underneath me and took hold of my cock, she didn't so much wank me as just hold on to it and keep stuffing that plastic toy up my ass. I couldn't believe it but without wanking I could feel that I was about to ejaculate. She held her hand over the tip of my cock as I came again and again and she laughed almost hysterically. She unfastened the cock from the harness and pulled away from me, "Stay there, I want to see that thing up your asshole...." I felt so fucking vulnerable bent over a dressing table in my Aunts bedroom, wearing a full face of makeup, a tight figure-hugging black party dress, black stockings, high heeled shoes a wig and a Basque. My ass was in the air and I had a dildo stuck right inside me. "Don't move I'm gonna take a picture..." "WHAT!" "It's ok, I've got a digital camera we can look at the picture later and erase it if you want me too" I was now too fucking drunk to argue so I just stood there whilst the flash illuminated the room and my ass a good few times. She put the camera down and slowly pulled her plastic dick out of my ass, and when it came out she licked my asshole and squeezed my balls tightly and pulled them down. She sat on the corner of the bed open-legged and when I turned around she was masturbating, I sat in-between her legs watching, smelling and wanking myself. She lifted her legs up onto the bed and I was staring at a big wide open pussy and a tight little asshole. I licked at her asshole over and over again and this seemed to do the trick. She had three fingers of one hand inside her and her two middle fingers of the other hand working that clitoris well. She began to buck like a pony wearing its' first saddle and her back arched over and over again and then she sat up and grabbed my head and pulled it into her soaking pussy. "drink it..... lick it you little bitch" she screamed and I felt her pussy squirt her lady-cum all over my face. It was hot and sweet and sticky and I licked it up like the good little lesbian I had become. I licked at her asshole and then back to her cunt. I stuck a finger into her asshole knuckle deep and wiggled it around and she twitched and jerked and thrashed about and whilst all this was happening her great tits swung all over her chest. I was about to cum again - I had not actually stopped wanking since I crouched down between her thighs and I climbed onto her and hitched my skirt up over my waist and she cupped her breasts together with both hands and I shot a long stream of white sticky cum all over her tits. I collapsed at the side of her panting and sweating and looked at her. She was starting to giggle like a schoolgirl. "Wow, that was fantastic - we gotta do this again darling" she said, and then she took me by surprise - clever bitch that she was. "When a guy shoots a load on a girl on a porno movie and she licks it off herself or even better her girlfriend licks the cum off of her tits.... does that turn you on?" "Too right it does, it's nasty but so fucking sexy..." "Well I think that too. Seen as your my little girl and some dirty boy has cum all over my nice floppy tits I want you to lick it up" "But.... but that's my cum on your tits..." "I know it is, and when you've licked the last bit up you can spit it into my mouth and I'll swallow it." She held her huge juggs up and I began to lick my own cum off of her tits, the sides of them and those huge dark brown nipples. I never realised what cum tasted like and I now know why so many gays and gals like it! I saved the best bit 'till last. There was a big pool of cum in her belly button and I slurped it up like a slut. I leaned over her and she opened her mouth wide ready to receive it. I spat it at her and she swallowed it whole and then laughed. She fell asleep after our little bit of fun and games and I undressed and showered, I was covered in sweat and cum and was hot and out-of-breath. I cleaned up and dried off and went back into her room. She was just waking. "Awww I thought we could shower together...." she said in a mocking voice. I lay next to her with just my towel wrapped around me. I lay back and she got up and went for a shower, I watched as her ass jiggled as she walked to the door... "Don't go away now..." she said with a smile. She returned about twenty minutes later with a towel wrapped around her waist. Her long red hair now looked black and longer as she dripped her way across the room. She sat at the dresser and dried her hair and her towel dropped away showing her back and buttocks - she was a beautiful woman and I wanted to be her beautiful woman again and again and again....