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My first foray in crossdressing Pt.1

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By *s.Kerry OP   TV/TS  over a year ago

Blackpool

My first foray into crossdressing 'fully' came about when my wife and I were invited to a ‘Vicars & Tarts' party by friends. We had always been pretty open minded about sex, albeit not swinging or anything, so we decided to go for it full on, shaving myself all over and buying a wig etc and even having a few test runs of me fully en femme when the kids were at school. My wife actually said she found it a turn on to see me dressed like that and a couple of those test runs ended up with us on the bed.

Anyway the big night arrived, and with the kids off to their grandparents for the night I got changed and we tentatively went out to the car feeling very anxious about being seen in public by neighbours etc but at the same time quite excited about the whole experience. We had a great time at the party, in fact my appearance even drew a few compliments from other guests, one other party goer even being brazen enough to run his hand up and under my all too short skirt! After a lovely evening though we went home although my wife insisted I kept my stocking's on when we went to bed ~Smiles~

I continued to dress at times at home, sometimes on my own, and sometimes with my wife present, and we even managed a few very tame pictures which we sent off to a firm that advertised in processing XXX pictures, there was not a viable alternative apart for a Polaroid camera at the time, although ours were not XXX by any means.. I even kept a special favourite of mine with me most of the time, I can’t explain why, and it was this that led to my first experience with another guy for quite some time although this was unknown to my wife..

Part of my uniform at work was a jacket, I was then and still am a PSV driver, and whilst sitting in the canteen one day chatting to one of the guys I reached in my inside pocket to get my diary and accidently pulled my picture out as well albeit I rapidly stuffed it back in hoping the guy I was talking to had not seen it.. He had though as he asked if that was a picture of my wife!! Somewhat red faced I admitted it was actually me thinking it wouldn’t be a problem as the guy that asked was well known as being gay, which incidentally I didn’t have a problem with although some did, but when he asked to see it properly I hesitated for a moment before taking it from my pocket and handing it to him.. I was dressed in a short white nightie and panties but was taken aback a bit when he actually complimented me on how good I looked, explaining afterwards that many gays found a t.v. attractive.. Nothing much else was said at the time as we both had to leave but several days later he asked me if I had any more pictures he could look at..

I slipped a few more in my jacket, in an envelope his time, the next time I went to work as our paths frequently crossed at changeovers etc and the next day we did indeed meet.. Out of sight of the passengers on of course I gave him the envelope and he took my pictures out and smiled, once again before complimenting me on how I looked in the various pictures.. I explained the inherent difficulties of having a young family, which he knew I had of course, and spending time dressed as in the pictures to which he replied if I ever wanted time to dress I was welcome at his house.. Somewhat taken aback I murmured something along the lines of “Are you serious” to which he simply replied “Very” before once again our duties took over and we went our separate ways..

A week or so passed with nothing more really being said as other guys were always around when our paths crossed until when we were on our own one day he mentioned his offer for me to dress at his house explaining he had already looked and we were both off on the same day the following week.. As my wife worked, and the kids would be at school I thought what the hell it would pass a few hours, the thought he was gay not even entering my mind.. The following week I turned up at his house with a small bag containing just a few basic things and he showed me to the bedroom telling me I could change in there whilst he made us both a coffee.. Somewhat sheepishly and rather embarrassed after changing I went downstairs to join him in the lounge.. “Wow” was all he said as I sat down opposite him.. Unbeknown to me however he had a fetish for lycra etc and as we chatted and drank our coffees he asked whether I might ‘model’ a leotard style item for him sometime to which I replied I would next time I went there, if it was ok for me to do so of course.. Nothing sexual happened at all on that occasion however on the next, when ‘modelling’ the leotard things did indeed progress..

When I arrived at his house the next time he again said I could use the bedroom but would I mind putting on what he had left on the bed.. Intrigued I went upstairs and there on the bed was a lycra leotard and leggings.. I did my make-up, which was very basic at the time, put my wig on then donned the leggings etc, aware of the bulge that showed through them despite the outfit being quite restrictive, before joining him downstairs.. There was no need to ask if he was horny as the bulge in his trousers gave that away as he stood up to join me and began rubbing his hands all over me, rubbing my cock through the lycra as he did so.. He started asking me if I had ever sucked another guys cock before to which I replied yes of course (As you will have read if you saw my original post of “How it all began”) and without further comment he sat down again and took his cock from his trousers beckoning me to join him on the settee.. Kneeling so he could continue to grope me and stroke the lycra encasing me I took his cock in my mouth and sucked him until with a groan he came in my mouth.. Cleaning ever bit of his cock, which I must say was significantly bigger than mine, I sat back.. Thank you was all he said as leaving him I went upstairs to dress in my male clothes before joining him for a coffee prior to leaving..

We got together virtually every week after those initial visits, one week I would dress en femme, at which times at first nothing sexual happened, and the next I would dress in Lycra for him when I always ended up sucking him.. Despite the fact he was nearly ten years younger than me I always seemed to take the more submissive role, a fact that has remained with me till this day, albeit our ‘relationship’ never progressed beyond me sucking him for a couple of months until he announced he had bought a special outfit which he wanted me to model for him..

To be continued..

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By (user no longer on site)  over a year ago

Great story

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By *ooner1969Man  over a year ago

birmingham

Great.. more please!

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By (user no longer on site)  over a year ago

More please.

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By (user no longer on site)  over a year ago

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By (user no longer on site)  over a year ago

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By (user no longer on site)  over a year ago

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By *AM2214Man  over a year ago

Manchester Area

can't wait to hear more !??

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By *s.Kerry OP   TV/TS  over a year ago

Blackpool

Thank you for all your comments. The next part will be up this coming weekend x

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By (user no longer on site)  over a year ago

Bookmark for later reading

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By (user no longer on site)  over a year ago

Looking forward to reading the rest of this one.

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By (user no longer on site)  over a year ago

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By *s.Kerry OP   TV/TS  over a year ago

Blackpool

My sexual ‘relationship’ with Tom continued for some years, and even to this day we are friends, albeit in a platonic way now of course as we live some 300 miles apart now, but I digress.. I arrived one day only to be told the special outfit he wanted me to ‘model’ was in his bedroom so after doing my make-up etc I went through to see what it was, knowing of course it would be Lycra, but what I wondered would be special about it.. It was in actual fact a full body suit, a gimp suit I imagine in today’s language, with a zip at the back.. Slipping it on I soon realised why he considered it special, not only was there a hole for my cock to go through but I was also ‘forced’ to display my bum.. Zipping it up with some difficulty I went downstairs to re-join him his open mouth sufficient for me to know he loved the look.. I myself felt quite conscious of the fact my cock was on display as he had till then never seen it but it didn’t seem to faze him as he stood and moved to stand alongside me so he could feel me all over and stroke the material.. I could tell he was getting incredibly horny as his breathing was getting heavier and heavier then breaking away momentarily he stripped totally which was rather unusual as it was normally just a case of whipping his cock out for me to suck..

Pushing me towards the settee Tom gently pushed my head forward so I was bending over with my hands on the settee.. Then I saw a flash and realised he had taken a picture, with I was to later find out, was with a Polaroid camera he had recently bought.. It didn’t really bother me as it was from the back and as it was to later transpire picture taking became a regular part of our meetings although the full reason why will become apparently later in the story.. I sensed him behind me again as he started to stroke and caress the material of the outfit, his hand occasionally slipping between the cheeks of my arse and probing gently at my hole until I once again felt that cold feeling as he pushed lube in me and I knew what was going to happen.. With two fingers still pushing in and out of my hole he leaned forward and whispered in my ear “I love buggering straight guys” and without any further warning I felt his cock pushed roughly into me and he began riding me, I hadn’t seen him put a condom on although as I felt later when he cum he had done, but for the first time in over ten years since my meetings with my Asian guys I felt the sense of being ‘used’ as he rammed in and out and I thoroughly enjoyed it, his earlier words running through my mind.. Finally I felt him shudder and knew he had cum his cock buried deep in me..

After he had withdrawn and cleaned himself up he asked if I wanted to cum but I didn’t albeit I can’t explain why and that was to be a pattern for the years I met guys both as T.V and occasionally as a faggot/sissy.. As we sat with our coffees prior to me leaving and having a chat he apologised for using the term ‘buggering’ but he enjoyed using that rather than ‘fucking’ so from then on he always buggered me and with a cock of the size of his believe me I was well and truly buggered..

As I mentioned earlier Tom never wanted to have any sex fun when I was dressed en femme, it just wasn’t his ‘thing’ however one day when sitting there chatting he asked if he might take a couple of pictures of me dressed and could he show a friend of his.. I was unsure at first but as I felt ‘disguised’ if you like when wearing make-up etc I finally agreed so he did so and after showing them too me I decided he could indeed show his friend.. Nothing more was said for a couple of weeks until after donning his favourite outfit and being well and truly buggered once again and we were sitting with our coffees.. Producing a Polaroid picture he said “This is my friend and he would love to meet you one day” and taking the picture I couldn’t believe my eyes, it was an Asian guy and he must have weighed at least 20 stone.. (I should explain at this time I lived near Gatwick Airport at the time and our meetings took place in Crawley which was a satellite town really built as Gatwick expanded and did actually had a very large Asian community) Continuing Tom said discretion was a must for this guy as he was married etc and of course his wife did not know of his bisexuality as I was to find out was the case with many in the Asian community.. I can’t explain the attraction but confessed to Tom I would like to meet him but I was worried as to what he might expect and what Tom’s ‘involvement’ might be.. Tom explained he would be present but wouldn’t join in at all so after further discussion it was arranged that should he be free he would join us at our next meeting which of course was my dressing en femme day..

I arrived at Tom’s and went to get dressed, the idea being I would be ready when the guy arrived as he had no wish to see me as a male at all, which of course was quite understandable, and re-joined Tom downstairs until there was a knock at the door.. Tom answered of course and in walked the Asian guy, and I must admit he looked a great deal bigger that in the picture but not one to judge I accepted his peck on the cheek as he sat down to join us for coffee.. This was the first time of course I had actually met any guy fully dressed as a T.V knowing sex fun would definitely be on the agenda and indeed it did as not long after joining me on the settee his hand was wandering under my skirt roughly squeezing my cock through my panties.. Tom explained I never wanted to cum when I met him but didn’t know if this might be different to which I said I did not want too so the guy took his hand away before whispering in my ear to stand up and bend over.. I assumed my usual position when I was buggered by Tom and before long I felt my panties being pulled down and fingers probing at my hole.. This guy was huge and of course his hands were too and when he had just two fingers inside me finger fucking me I felt stretched to say the least but when I felt his cock slipping inside me I was in heaven.. He like Tom liked the rough approach and as Tom looked on he pounded in and out of me, my pleasure non-existent as he used my arse as a fuck hole to simply relieve himself in.. My legs started to buckle with the force of him fucking me and I felt his two strong hands grasp my hips to steady me until with a groan I felt the familiar feeling of a guy cumming inside me as he rammed deep into me (He too used a condom of course) then as he pulled out he gave my arse a hard slap before disappearing to clean himself up.. Pulling my panties up I turned and smiled at Tom before sitting down

gently on the settee again..

“That’s a good little white bitch you have there Tom” was the guys first comment when he re-joined us for coffee, to which I blushed with a mixture of pride and humiliation, my only thought being was this guy going to want to meet me again which as if reading my mind he continued “I do hope you will let me visit again Tom?” Glancing at me and seeing the look on my face Tom replied “Of course”..

To be continued..

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By (user no longer on site)  over a year ago

Oh lovely story very nice thank you

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By (user no longer on site)  over a year ago

Love the story

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By (user no longer on site)  over a year ago

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By *s.Kerry OP   TV/TS  over a year ago

Blackpool

Thank you all.. Working on writing the next part over the next couple of days x

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By (user no longer on site)  over a year ago

Beautiful story so far, please keep going

x

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By *rendababeTV/TS  over a year ago

richmond

wowe great to then xxxxxxxxxxxxxxxx

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By *s.Kerry OP   TV/TS  over a year ago

Blackpool

I continued to meet guys at Tom's for several years after that. Most coming from adverts in various gay papers available at the time, plus we ventured out to some local 'cruising' places as Tom was, as I mentioned earlier a confirmed voyeur.

My meetings with the Asian guy were really the highlights I would say and although he fucked me in Tom's presence we also met away from there which came about after he mentioned, not in front of Tom, he wanted to explore more perverse sex acts.

All I knew about my Asian guy was that he was some sort of businessman but apparently well off as our first meeting away from Tom's was in a hotel and not I hasten to add some cheap place. He gave me a note with the details as he left Tom's after fucking me and the instructions were clear including what I was to wear etc. My wardrobe was rather limited though and I could not fulfil all he wanted as I waited nervously in the room for him to arrive. He was clearly annoyed but I tried to explain why I wasn't as he had instructed which seemed to appease him a bit but only briefly as before long I was over his knee with my skirt around my waist being spanked and with hands like his believe me it hurt! After that without ceremony I was told to kneel on the bed on all fours as he proceeded to rip my tights and yank my panties down in order to finger me. As I mentioned before his hands, along with him, were large and it didn't take long for him to open me up ready for his cock. He mounted me and began to fuck me, I was simply his fuck hole and he used me as just that, ramming in and out till with a grunt I felt him cum. After he withdrew I sat on the bed waiting for his return from the bathroom as I knew from our previous conversations I was never to be in front of him other than en-femme.

On his return he sat down as he said he wanted a chat with me. He was clearly a man used to being obeyed but the subject he brought up knocked me for six at first. "I want you to be my bitch. In return I will provide you with various outfits to wear and treat you well in but you will be mine and mine alone and will not meet anyone else, Tom excluded as he introduced us, without my permission. What do you think?" I was a bit taken aback as I said but managed to murmur "May I have a few days to think about it please as it's a big commitment" He nodded his agreement and got up to leave before turning as saying "If I agreed at our next meeting at Tom's I was to call him ‘Daddy’ and we could take it from there" My mind was all over the place as I got dressed normally and packed my bag ready to go but memories of my first encounters with Asian guys, albeit as a male, kept flooding back and the feelings I got from those encounters too. Leaving the hotel my mind was made up already though but I will write about my life with my Asian Daddy separately.

So here was I, in a fortunate position, although some of you might have different views, of being buggered on a regular basis by Tom and others, being fucked by my prospective ‘Daddy, but also enjoying a ‘normal’ se life with my wife, which included as it was then called ‘wifeswapping’ etc.. It was in fact during one of our wifeswapping meetings that my wife saw me, at the other woman’s invitation, sucking her husband’s cock and her comment of “You have done that before” leading to a long conversation with her afterwards at which time I confessed to my meetings with Tom.. I was fortunate though in that whilst she might not totally agree with it she was happy for me to continue providing she was not expected to be a part of that side and in many respects it made our marriage stronger as I was no longer having to lead a secret life as it where..

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By *ammyTV/TS  over a year ago

manchester

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By (user no longer on site)  over a year ago

When do we get the other story

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By *s.Kerry OP   TV/TS  over a year ago

Blackpool

Phew give me a chance

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By (user no longer on site)  over a year ago

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By (user no longer on site)  over a year ago

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By *es for funMan  over a year ago

port talbot

Love this keep it going babe x

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By *dsindyTV/TS  over a year ago

East Lancashire

Wow...lovely xx

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By *issystaceyleicsTV/TS  over a year ago

leicester

Amazing story!! Was there ever a part 2? Xx

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By (user no longer on site)  over a year ago

Great story

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By (user no longer on site)  over a year ago

Just read this all through and really enjoyed it x

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By *eathersarahTV/TS  over a year ago

warrington

Great story x

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