Sex has, and still is something that I have always enjoyed. Learning to give pleasure to others as a teen cock slut was an exciting revelation and progressing through to someone who became more bisexual, a transvestite and more dominant personality, the years have been both exciting and satisfying. When a friend read some of the entries from the Naughty' diaries that I've kept over the years and suggested that I should share a few of the stories of my adventures' on Nifty , I didn't realise that they would receive such a response. I have had some great emails, which have led to a few equally salacious tales of other people.
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I do enjoy hearing from readers especially if they enjoyed reading of my salacious past experiences. So feel free to mail me Centaur356@proton.me
This is the diary entry from how I first started to dress in the marvellous feminine clothes that I tend to turn to now and again.
At the age of 17 living away from home because I was in college I had experienced things that most guys of my age had never even dreamed of, with men, lots of them and women too. So, I wasn't the shy reclusive type, if there was sex anywhere in the offing I wanted it and quite often got it.
With the summer holidays arriving I was looking forward to spending my time having lots of fun' and especially as I knew that I'd have the house to myself as my family were going away on holiday and I didn't want to go to some holiday camp at the other end of the country. But, my plans were shattered a little at the start when I got home on the Thursday evening and found that I had lost my house keys!! What to do? I ended up going to the next door neighbours a woman named Caroline and her husband Donald in their mid 30's, a couple that I thought were a bit boring and staid, at least that's the impression I had of them, although I didn't really know them that well. I went to them to ask if I could use their phone to phone the holiday camp where my family were. Caroline was quite nice invited me in and tutted, gave me a cup of tea and something to eat and then let me use the phone. It seemed to take ages to get hold of my mother and she said that she'd put a spare key in the post for me although it would take a few days to arrive and as it was a Bank Holiday it would probably be the Tuesday before it arrived. I suggested that she mail it to Caroline and Donalds' house because I wouldn't be able to get in. As I was suggesting that Caroline said, why don't you stay here for the weekend we've got a spare room and it'll save you having to go and find somewhere to sleep. So, that agreed I stayed.
Over dinner that evening Donald said that they were going to a fancy dress party on the Saturday night and I could stay in the house or I could go with them. Well, with dreams of lots of sexy fun shattered a little I agreed and then they explained that it was a Vicars and Tarts party at the friend of theirs who lived on the edge of town in a big house. So, we had to sort out what outfit I was going to wear and Caroline suggested that because I was a slim build why didn't I go as a Tart !!! Not really my idea of a good plan but when she took me upstairs and showed me her wardrobe with lots of cosplay (they'd call them now) outfits in it I finally agreed. Now, I had in the past once when I was with a female had my cock stroked by her with a pair of her panties and it had felt fantastic having the material caressing my shaft and I must admit when Caroline showed me a full French maids outfit complete with underwear suspender belt stockings etc I got a distinct tingle in my groin. The only problem of course was finding a pair of shoes for me, but she said that we'd probably be able to find something the following morning in a charity shop in town.
The next morning she took me into town and we trawled charity shops until finally she found a pair of black high heels that although tight fitted me and we went back to the house. After lunch, Donald was at work, she suggested that I go and try the outfit on so that she could see if it fitted properly incase she had to alter it a little. I went up into the bedroom that I was using while she went to get the outfit. When she came into the bedroom with the outfit in her arms and laid it all out on the bed I was in my briefs. She'd thought of everything even down to some padding for the tiny white lace bra. She showed me it all and then left me telling me to get into the outfit. I'd never dressed in feminine clothes before but knew how to get a woman out of them so I had a pretty good idea and it didn't take me too long, but the sensation when I slid the stockings on and attached them made my cock surge and by the time I had them on and was about to slip into the white lace panties I was rock hard and the panties were so tight that I had quit a bulge and was feeling amazing already. By the time I managed to get into the frilly short petticoats and then the maids dress Caroline was back and helped to zip that back of the dress up for me then she fussed around me then she sat me down did my makeup and turned with a shoulder length dark wig in her hands and slipped that onto my head. By the time she was finished and turned me towards the mirror to look at the result I was amazed, I looked like a girl, or a tarty French maid as was the intention. When Caroline knelt infront of me to put the high heeled shoes on me I had my hand on her shoulder to steady myself and with her down there right on a level with what I knew was a throbbing erection under the skirt I looked down at her in a new light, with a sexual feeling and as I looked at her I could see down the top of her blouse and I could see her deep cleavage as she had quite large breasts. I was a bit surprised because I'd never looked at her in that way before but wow did I get an urge right then. But of course I couldn't do anything she was my next door neighbour and what if she objected!
When I'd got the shoes on properly she showed me how to walk in them, and after a lot of wobbly walks I began to get the hang of them and she taught me how to as she called it , `strut my stuff' like a female. Which I must admit felt very exciting, the feeling of the stockings brushing against my legs as I walked and the underskirts plus of course the way that the lace of the panties rubbed along my hard cock as I moved, I was almost dying for her to leave so that I could make myself cum. Eventually, after pinning the dress in at the waist a bit she told me to take it off and she'd go and adjust it downstairs while I got changed back into my male clothes. As I slipped the dress and petticoats off I made sure that I had my back turned to her so that she wouldn't see my erection straining against the panties and as soon as she walked out of the room I pulled them to one side wanked furiously until I erupted, all over the full length mirror on the wardrobe infront of me. It was only afterwards as I was cleaning the mirror that I realised that maybe she'd been able to see my reflection in the mirror and might have seen my bulging panties. But too late then anyway I was satisfied for then. I got out of the underwear and folded it then got dressed again and by the time I got downstairs the dress alterations were nearly done.
The following night we all got dressed up in our respective outfits, Donald as a vicar and Caroline , wow, she looked superb as a tart. Short shiny flared skirt fishnet stockings the lot and definitely looked at her in a new light especially when she was so close to me doing my makeup , she smelled delicious. I walked into the lounge wearing the maids outfit and even Donald said, `wow'. Which I must admit made me blush. Off we went to the party me sitting in the back of the car and I must admit spending most of the trip looking down at the short skirt pulled up over my thighs showing a bit of stocking top and feeling myself hard in the panties and sort of hoping that I wouldn't disgrace myself by cumming while wearing the panties at the party !!
Got to the party and all went well, some superb outfits and sexy one's too among the women, plus there were a few guys dressed as tarts and a few women dressed as male vicars. I saw Caroline talking to a guy in his 40's also dressed as a tart and after a while she came over with him and introduced him as Charles then she left us. Strange I thought, although I found out later her reason for leaving us. Charles was nice , chatted about this and that and all the time looking me up and down and I got that feeling, he fancies me'. We both went into the kitchen to get some top ups for our drinks, although I was a bit tipsy already but didn't care and after others in the kitchen went back to the party he put his hand on my back and said, how would you like a walk in the garden for some fresh air', as he said it his hand slid down to my rear thru the skirt and I got his drift' and feeling nice I said, why not' and we left the kitchen by the back door. Quite some garden, huge but that went with the big house and it's surroundings. We walked down the garden and as it was summer and warm and calm it felt lovely tapping down the path in our heels hearing that click clack and knowing what I thought was going to happen. There was large circle of hedges part way down the garden a distance from the house , it had a paved area in the circle with a water feature in it and a bench and Charles suggested we sit and enjoy the evening more.
I sat down next to him and as soon as I did his arm went along the back of the bench behind me and he said quietly, you look so sexy in that outfit, good enough to eat'. I gave a little giggle almost and said, do you think I'd taste nice if you ate me'. With that his other hand came down onto my thigh thru my skirt and stroked it and said, I bet you'd taste fantastic and I'd love to taste you' with that his hand slid down onto my stocking'd leg and without even thinking like the needy slut I was I opened my legs for him. He didn't waste much time, his hand slid between my legs and up slowly under my skirt to my panties. When his warm hand settled on the bulge in my panties I sighed and leaned back into his arm and he said, ooooooh how lovely, so hard already just like me' and pulled my hand across to where he'd pulled his skirt up too and placed my hand on his bulging panties too.
I of course gave it a soft squeeze and he said, mmmmm you like this don't you? I'm so glad'. I just murmured , yes'. That was enough for him his fingers slid under the edge of my panties and at the same time he leaned over and kissed me on the lips, not a soft kiss either tongue in my mouth and hand up behind my head. I responded as my body wanted to and I returned the kiss as his hand eased my panties aside and released my rock hard cock into his hand. I nearly erupted there and then but managed somehow to hold back. When he broke the kiss he looked down and said, oooooh how lovely, so big and so hard. Ooooh I want it, can I'? I knew what he wanted and I put my hand on the back of his head and gently pushed him down so that he was leaning over my groin and without a pause I was in his mouth and pushing up towards him and groaning. He went at me making very wet and loud slurping noises and I was bucking up towards him each time his head went down on me, but then suddenly he stopped and said, no wait, lets go further down the garden away from the house'. Made sense we were a fair distance from the house but someone else could still have caught us. He took my hand and pulled me up off the bench and led me with my skirt hooked up because my cock was still out of my panties and led me down another path . He obviously knew that garden well from the assured way he led me meekly until we moved thru some like conifers and there was another bench where he crouched down infront of me, lifted my skirt and pulled my panties right off and then sat me down. As soon as I was seated he put his hands on my knees and spread them wide apart and then went to town on my cock again. I was delirious it was heaven , warm evening out in the open and being pleasured by someone who knew what he was doing and enjoying it especially as I so wanted it. As he devoured me slowly he put his hands under the back of my thighs and lifted them up slightly that gave him access to my balls and he licked kissed and sucked on them so tenderly before going back to my cock again. Then he really did make me jolt, his mouth slid from taking me deep until just the head was in his lips and his tongue caressing me then he licked all the way down the sides to my balls and then under them and suddenly his tongue was lapping at my rosebud hole and I groaned and even shuffled forward a little more, bad girl eh!
Realising that I liked the feeling he pushed with his hands on the back of my thighs lifting me higher and then he buried his face under me and I felt his tongue go inside me, it was like he was fucking me with his tongue and I was so turned on I couldn't stop myself from groaning again and I even said, `Ooooh god yes, oooh fuck me'. I think that was what he wanted to hear although he didn't stop for a few minutes but then suddenly his tongue was gone and he was standing up. At first I thought my words had taken it too far but then he lifted his skirt and pulling down his own panties he released his own cock, about six or seven inches long but definitely hard and gosh so thick. For a second I thought, I'll never be able to take that but of course I knew that I would and wanted to.
He took my hands and pulled me up and turned me round then told me to kneel on the bench which I did and heard a shuffle and the click of his heels as he moved behind me. My skirts were lifted up over my waist and I felt the warm air on my rear and the tingle of it touching my wet hole then I felt his hands on my hips and the heat of his cock head touching me. I got myself ready then he pressed against me. Because he was so thick at first nothing happened just the pressure of him against me then as my body relaxed a little more, my eager boy pussy opened up and the head slipped inside me and I heard him give out a little groan of pleasure. Oh yes I wanted it, wow did I want it, the illicit way that it was happening was so exciting and I pushed back against him, at first nothing happened then I felt him slowly not so much pushing into me it was more as if my pussy was sucking him in and I was floating and tingling all at the same time. He paused and eased back a little and then pushed against me again and more slipped into me. I adjusted my position to be able to take him better and then it happened without warning. I felt a jolt go thru me that seemed to travel from my inside up my back and back down to my cock and suddenly without me being able to stop myself I was cumming . I could actually hear it splashing onto the bench and stone slabs. At the same time he started to move slowly in and out probably encouraged by my inside muscles gripping and relaxing around his thick cock. I heard him say quietly and hoarsely ooh yes perfect, now I don't have to worry about you' and he started to move in and out with more relish. As my orgasm passed although it didn't really pass as such because the tingles went from my cock to the centre of my body deep inside where I could feel the mushroom head of his cock stroking me. I was being taken' like a female, not like a submissive guy but as a female and dressed like one too. And, I was to be honest loving every stroke and every second of it. Being dressed too was a whole new sensation.
I eventually heard his breathing getting a bit ragged and from his movements I knew from experience that he was close and thinking back now it was like a girl that I said, yes daddy go on fuck me cum in my pussy please'! He didn't need much more encouragement and he gripped my hips and really went to town on my boy pussy pounding me and grunting as he did so , then suddenly he pushed in really hard and I felt his body go rigid behind me and then began to shake and there it was, his hot cum poured into me and feeling the sensation my head started to spin so much I thought that I'd faint. He held himself deep inside me then he slid back and gave a final push before sliding out of me again and I felt the sudden coolness of the air around my wet open hole. He got his breath back and I couldn't move for a few minutes I was still thrilling from the feelings inside where he'd been. But then he took me by the waist and slowly helped me up from the bench and turned me round and said, my oh my what a delicious sissy you are, I've got to see you again' and with that he took me in his arms and kissed me tenderly on the lips. I slid my arms around his neck and revelled in the unexpected new sensations, I could still feel the buzz and the thrill of the stockings brushing my legs and the petticoats stroking my thighs as I pressed against him.
I was surprised when he let me go and reached past me and picked up my panties, I hadn't realised that he'd taken them off and he handed them to me. As I went to pull them on I gave a little giggle, a girlie giggle, and he asked what was wrong and I told him that I could feel his cum running down my legs. He immediately reached in the little pocket on his skirt pocket and pulled out a folded hankerchief and told me to turn round and like a gentleman he wiped my pussy and the backs of my thighs saying that I couldn't go back into the party like that, which made me giggle even more. Gosh I found that I was really acting like a girl already.
We got back into the party and mingled as if nothing had happened but as I talked to people I was still buzzing inside. When it was time to leave Caroline found me and asked me to help her because Donald was so drunk he could hardly walk, so we went to find him. As we were about to leave Charles came up to me discreetly and pushed a piece of paper in the pocket on the little white lace apron on my outfit and then turned away . I saw Carolines eyebrows lift but I just shrugged as we manhandled Donald out the door and down to the car. Fortunately Caroline could drive and in those days breathalysers were few and far between so there wasn't much need for it being a problem.
We got back to their place and somehow I remember managed to get a very wobbly legged Donald up into the bedroom and onto the bed. She asked me to help her get his trousers off and as I did so the fact that I was undressing a guy suddenly made my cock start to harden but of course Caroline being there stopped anything else from happening and she thanked me and I went along the landing and into my room to get changed out of the outfit.
I stood for ages infront of the mirror looking at myself delaying taking off the outfit that I realised was changing my life even after such a short time. I had the skirt up and was rubbing my cock thru the panties when the bedroom door opened and Caroline came in. I quickly dropped the skirt hoping that she hadn't seen and she said, I thought that you'd need some help with the back zip on the dress. I hadn't thought of that but I did then. As she came into the room I saw that she'd got ready for bed and was wearing a nightie and negligee that although not see thru didn't leave much to the imagination as she stepped up behind me and undid the zip for me and helped me out of the dress and petticoats. As I stood there in the bra and panties and suspender belt etc she said, did you like Charles'? I blushed and said, yes he was nice'. Then she sort of dropped the bombshell and said, when you were trying on the outfit initially I saw how hard you got in the panties and how big you were and as I know that Charles likes girls and guys as well and loves guys who dress up, I thought he'd like you'. I just stood there with my mouth open embarrassed until she said, it's ok, I know that you are gay, or at least bi. Donald and I saw you and another guy up in the woods about a year ago when we were doing the same as you two were doing , fucking, although Donald didn't recognise you.' I was horrified needless to say, but she added, don't worry it's our secret just between you and me. I know that Charles is bi too and thought that you'd enjoy his company. I saw you both disappear into the garden did he treat you well'. I blushed again until she said, I can see from your face that he did, he's got a lovely thick cock hasn't he even though it's not very big'. I found myself nodding and she said, it's ok don't worry it's our secret'. Did he fuck you, I bet he did' . Once again I nodded and she gave a little chuckle and said ooooh how exciting'. Then I saw that she was looking over my shoulder at the reflection of my front in the mirror and said, ooooh you must have found it exciting being dressed and being fucked, I wish I'd seen it, did you cum'? I nodded and she said, do you like women too I bet a lot of women would love to get their hands on that' and nodded at the reflection of my panties swollen rock hard into a large bulge with the talk and the memory of what had happened. She suddenly said, as I know your secret can I tell you one of mine'. I was speechless I didn't know what to say so I just nodded. And she said, I've always wanted someone with a big cock and I have a fantasy of someone like you dressed and taking me on the bed' and with that she reached round me and cupped my cock thru the panties! I jumped at her touch but I couldn't deny that her words and the feeling made me horny. As she squeezed me thru the lace her body was against me and I could feel the heat and smell her perfume and I felt myself getting lost again and when she said, can I see it please' I just nodded and watched as her fingers delved under the edge of the panties and pulled them to one side so that I sprang out. I felt her breath when she gave a little gasp and immediately wrapped her fingers around my shaft and said, ooooh I wish that you could make my fantasy come true'. I really was lost then and wanted to but I said, what about Donald' and she said, ooooh a bomb wouldn't wake him, never does when he's as drunk as that' and she started to stroke my cock slowly as she held it firmly. I sensed a movement behind me and in the mirror I saw her negligee slide down to hang on the arm that was wrapped around me, then she fumbled again and I realised that they were both held just at the neck with ribbons as her nightie slid down onto her arm too and I felt her naked against my back. She knew from the jerk in my cock that she'd got me and said, `come here' and holding my cock she turned me and pulled me across the room to the bed. It was then that I saw her properly, breasts firm but so large that they had a droop to them, nipples and aureoles so pink and obviously aroused, and oh wow, the first time I'd seen a totally smooth shaved female pussy.
We got to the side of the bed and she let go of me long enough for the nightie and negligee to slip to the floor and then she reached out and slipped the panties off, threw them across the room and pulled me onto the bed with her. She just laid back threw her legs open wide and reached out her arms towards me and said, `come on, I want to be fucked by a big cock on a girly guy' which strangely sent a thrill and tingle thru me and I know that I felt it in my cock, or maybe it was the fact that I had a woman naked lying there infront of me begging me to fuck her! I know that I didn't hesitate I felt as if I had never been more aroused in my life the way that the evening had gone. Infact I could still feel the tingling in my boy pussy from Charles and needed so much to cum, what could be better than a hot willing pussy to slide into .
I crawled across the bed until I was kneeling between her knees and with her legs wide open I knew enough to know how aroused and horny she was when I looked down at her, her nipples were hard and pointed there was a flush of pink from her neck to her cleavage but most of all it was her pussy. It wasn't just a smooth mound with a slit, her pussy was almost open and I could see in the light the moisture that was there, oooh so inviting. I shuffled forward up between her thighs and as I got closer she brought her knees up and spread herself even wider. I looked down at my cock which was rock hard and I must admit dripping precum onto her mound and then down at her pussy and I distinctly remember that my heart was pounding. I had never met a woman or anyone for that matter who wanted it more , no that isn't right, someone who wanted ME more. I looked up at her face and saw that she was looking first at my face then down her body to my cock which seemed to be bouncing and she said a bit breathlessly, oooh go on come on don't be afraid, it's our secret and I want that thing so much'. So, I put my hand on my cock and pushed it to point it down towards her pussy, which was a bit difficult because I was so hard, but leaning forward and adjusting myself a little bit the head touched her. I rubbed it up and down the wet slit and felt her move up against me and she said, put it straight in, even though it's big I know I can take it'. So, with the head just resting against her and held there I leaned over her put my hands either side of her body and then pushed. Wow, she was right she could take me and so easily too, but then she was so wet that it slid in easily. I got about half of my cock inside her and felt her try to lift up towards me then she reached down hooked her hands in the suspender straps and suddenly pulled me down and it all went in until I was pressed against her. She gave a groan and said `oooh how lovely. I could see in your eyes when you went out of that kitchen with Charles that you knew what he was going to do to you and knew that you wanted it. Now fuck me as well, fuck me hard like men have fucked you'.
Oh wow, such dirty words from a woman who normally seemed to prim and proper. But in my state how could I resist. So, leaning over her I started that all too familiar pistoning movement that men had done with me and each time I drove inside her she lifted up to me arching her lower body. Then her legs suddenly went up in the air and wrapped around me for a few minutes pulling me against her and we were, well we were like two animals in heat pounding against each other. So quickly I could feel an orgasm building up inside me and thought, gosh what if I cum inside her and get her pregnant how would she explain that. But I couldn't have pulled out if I wanted to the way that she had her legs wrapped around me and suddenly , I don't know how long we were locked together I felt it happening and managed to gasp, `I'm going to cum' she didn't say anything but nodded her head and at the same time clasped her hand over her mouth, I guessed to stop herself from making any more noise. Then it was there. It was like a volcano erupting from deep down inside me. I pushed down with my hands on the bed so that my arms were straight, I arched my back so that my lower part was rammed right against her and my cock was in as deep as it would go and then I burst. I know she felt it because her eyes suddenly flew wide open and I heard a smothered moan from under her hand and she went crazy. Bouncing herself up and down like on a trampoline, writhing her hips, pulling back then slamming against me again as my cum shot out and coated her insides. My head was spinning, the sweat was pouring off me and I thought that I was going to pass out, the feelings were so intense as I shuddered to the finishing line. I was almost done and could feel the tingles in my cock slowing down when she suddenly gave out a long cry thru her fingers and I felt her pussy seem to tighten around my cock. I'd had sex with females before but mainly girls my own age but I'd never seen a woman cum before it was really something. It was like a milking machine must have been on my cock the pressure she was exerting was so strong which seemed to keep me locked inside her until as quickly as it happened she suddenly stopped and her body flopped back onto the bed although every now and again a shudder when thru her.
When she finally unwrapped her legs from around me and allowed me to kneel upright and my cock almost sprang out of her wetly because I was still hard, young and horny does that . I just knelt there panting for breath as she dropped her hand back down from her mouth onto the bed and gasped for breath too. Then she sat up leaning on her arms, looked at me and said, oh god that was amazing I haven't cum like that for so long. Wait here a minute'. She slid off the bed and went out of the room, she was only gone for a few minute and when she came back in still with that sexy flush on her skin she came over to the bed, put her hand on my shoulders and with a movement that surprised me she spun me round until I was lying on the bed and then before I knew it she was straddling my thighs and sliding her soaking pussy down on my cock again. When it was right inside her she said, I was just checking that Donald was still out for the count. Now I'm going to fuck you'. With that she leaned over me with her hands either side of me her nice boobs almost above my face and started to ride my cock hard, almost without any thought for me. I'd been fucked by guys hard like that before but never thought that a woman could feel that she wanted to do the same thing. She was almost like a thing possessed bouncing up and down so hard that it actually hurt me, although it was a rather nice hurt.
Just as I thought that she'd never stop she suddenly sat bolt upright and gave out a long moan and then it happened she squirted from her pussy and it splashed all over me. She pushed down really hard, slapped her hand over her mouth again and gave out a muffled scream then was grinding herself down on me so hard.
After she'd finished' with me she got up and it was almost as if she was treating me as someone to be used, she told me to get off the bed which I did and she went over to a cupboard and got some clean sheets out, she quickly and efficiently changed the bed leaving me standing there. I say standing I was like a wet rag exhausted, how could she be so active !! when the bed was made she got a towel dried my body off and told me to get some sleep and then she left the room leaving me there, to be honest feeling used', not a feeling that was new to me but certainly not being used by a woman. I stripped off the rest of the underwear and got into bed and I was so tired out that I went off to sleep.
It was the Tuesday before the mail arrived with my keys to the house, So, on the Monday as soon as Donald had gone off to work Caroline told me that she'd keep my secret about liking cock but it would be nice if I could satisfy a few of her needs now and again. Being a horny teenager of course I agreed but asked her `how' (naively) and she told me that she wanted me to come and see her while I was on holiday from college and dress for her and give her my cock. So it began, each day while my family were away when Donald had gone off to work I'd go round to their place get dressed in various sets of underwear and outfits and we'd romp on the bed. Oh come to think of it, it wasn't just the bed it was the kitchen, the dining table, up against the wall in the hall , on the stairs, wherever she wanted it.
The benefit for me was that I got to empty my sac every day, although so much I ached some days, she was damned insatiable. Plus, she took me out on a couple of days and bought a dress and some blouses skirts and underwear, so that by the time my family came back from holiday I had quite a collection that almost filled an extra suitcase when I went back to college. So, that was the start of my selection of outfits and proved to be a real bonus in my sexually charged world plus I found that men liked me to wear an outfit now and again, although I only every found a couple of women who liked it until I got married in later years and found my wife who was bisexual loved the fact that I could dress for her and act like a female with her but with the real thing under my skirt instead of a strap on that she'd had from one or two of her female friends.
Did I respond to Charles's note? Yes of course I did and when I was home from College it wasn't just Caroline that was being pleasured, it was me being thoroughly fucked by Charles.....many many times