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Ladyboy Switch

By newwriter

submitted August 28, 2006

Categories: Tranny/Shemale

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If you’ve read my previous posts you will be aware that I love cocks – sucking them and having them up my arse. I have been straight for most of my adult life but the last 18 months I have been on a huge cock binge.

I am messed up with how I feel about this. I still love looking at women. I love tits and arse. I like the soft feel of women – kissing them and feeling their bodies. I don’t look at men in public and get turned on – men with clothes on do nothing for me. Put me somewhere that I can see those same men naked however and something changes. I don’t really understand what happens to me.

I guess in simple terms it is this – I am a cock pig. The cock is the most exciting thing in the world for me. I love having it in my mouth. I love having it up my arse. I love seeing and tasting the cum that comes out of it. All cocks are good but as the last 18 months have gone on, size has become more important.

There are probably two reasons for that – the big cocks make the sex feel more like pornography (and a cock pig wants to feel like he is a slut in a porno film); and as time has passed my arse has stretched to the point where it needs at least an 8” cock to get some degree of satisfaction.

It is a sad fact of life that if you take massive cocks, fruit, dildos, fists and other assorted items up your arse two or three times a week for more than a year, your arse will stretch. Putting a small cock up it becomes less and less satisfying – for both of you. Nobody wants to fuck a sloppy arse that doesn’t hold their cock nice and tight and I don’t want somebody fucking me that doesn’t give me some of the delicate mix of pain and pleasure that makes fucking so damn good.

I have remained very fit since a weekend orgy where I paid twenty male prostitutes with big cocks to fuck me senseless. I am now down to 88kg (190cm tall) and run every day to stay very fit. I work out three or four times a week and are stronger now than I was when I played rugby at 20. My muscles are hard and tight but there is a limit to how tight you can keep an arse that has been abused as much as mine has in the last 18 months. I believe I am a great fuck – I know how to milk a big cock with my arse and get very few complains from the guys that fuck me – but small dicks just don’t do it for me (or for them). I will suck cocks of any size – they all taste good and the cum tastes great and different from every cock regardless of size – but I won’t waste everybody’s time by allowing somebody with a cock smaller than 6” to fuck me.

I still hang out at nudist beaches and suck a string of cocks in the bushes. I love the feeling of allowing a bunch of guys I don’t know to use my mouth to just shake off a load. If they want to abuse me and call me a slut, all the better. It’s true. I love the degradation I feel when I am just a method of extracting cum from cocks.

It’s getting harder to keep this lifestyle anonymous however. I have seen guys I sucked (or guys who have fucked me) walking in the street in the city. They look at me in my suit and we share a brief awkward glance. I assume it goes no further – most of these guys are straight and don’t want anybody else knowing they queued up for a guy to blow them on the weekend – but I feel a little guilty and my macho professional persona is broken down each time it happens.

I can’t mix the two personas – the urban professional and the cock slut. In my mind they must be separated but it is becoming more and more difficult. I have moments when I think I might just throw in one or other life and switch totally to the other. Problem. I can’t give up cocks and I like my normal life. What is the solution?

I have been toying with transsexuals for a few weeks now. I enjoy checking them out on the net. I can get excited enough to have a strong wank looking at pictures. I have paid a couple of transsexuals to have sex with me – picked one very sexy looking woman up off William Street but the sex was awkward. He / she had a small cock and couldn’t cum. I struggled to keep a hard on but ended up fucking her and leaving.

I then found a TS with a larger (7.5”) cock in the paper and she (I have now decided that I should use the female pronoun) liked topping. Again, the sex was OK only. I enjoy kissing women but this girl would have none of it. So it was neither one thing or the other – it wasn’t filthy sex pig stuff where I was degraded and slurped up cum; and it wasn’t straight sex where I got the comfort of kissing a female and felt her tender bits. It had enough promise to pursue though and I kept searching the web for sites with TS. About a month ago, I figured it out. I found a site (www.asiants.com) that features Asian TS (or, as they are called – ladyboys). There are beautiful creatures here – women who have stunning faces and bodies and, in many cases, big cocks. Cocks that work. There is lots of video of ladyboys blowing big loads of cum.

I was hooked. I spent two weeks going over the forum, downloading video and pictures, wanking myself silly with dildos up my arse and a healthy does of amyl up my nose. These girls were beautiful and they had the thing I need most in sex – beautiful cocks that blow beautiful cum.

I looked at TS from South America but it didn’t work – the cocks were consistently big but the women were not beautiful. If I want big cocks, I will just find myself men. I was looking for the mix of female beauty and the cock – and this really worked best with the Asian ladyboys. Specifically with Thai and Filipino girls.

Thailand clearly is the place to go. Ladyboys are all over Asia but there is really only a bar culture where finding them is easy in Thailand. Now that I am a devotee, I will be holidaying in Phuket and other Thai resort islands in the future but for my first trip a weekend in Bangkok seemed the easiest way to try it out.

I worked out that Nana Plaza was the place to go and I booked a room at the JW Marriott, which is just a few minutes walk away. The hotel is terrific and, although expensive by Bangkok standards, bloody reasonably priced by world standards. I got to my room at around midnight and quickly showered, splashed on some after shave and wandered out. I knew that the bars mostly closed at 1am and I needed to get a move on.

I had drunk a few beers and wines on the plane and had a bottle of amyl and some Viagra in my toiletry bag so I would be right when the time came. The bar I was heading for was Casanova. From my research it was clear that this bar had the biggest girls (tallest and largest tits) with the biggest cocks. If you want to fuck these girls then the other bars may present better options but for somebody like me who wanted to suck and be fucked, Casanova was the place to go.

I followed my plan to the letter. It was a heaving mess in the bar at midnight. Girls pushed themselves at me when I arrived (after my last four months of exercise and gang bangs I am pretty toned don’t look half bad – if I do say so myself) and I had to stay tough. I asked them all to leave me alone and requested the mamas an to come over for a drink. When she arrived, I told her exactly what I needed.

I won’t mention any of the girls’ names from the weekend. Suffice to say they were all beautiful and none disappointed. I got just what I asked for in each case. If you want to give it a try, there is plenty of information of individual girls on Asian-TS. She was out of action the weekend I was there but for my next trip I am definitely going to get together with Nancy. Check out her photos and videos – she is stunningly beautiful and has an enormous cock. She cums in buckets and blows it miles. THE best sexual package I have ever seen. Next time.

I told the mama san that I wanted the best and biggest top in the bar. She told me the price and asked me where I was staying. I told her I would buy the girl a couple of drinks, pay her bar fine and then take her to my room for a “long time”. Short time, although I never tried it, means a room near the bar for 1.5-2 hours. Long time means your hotel room until lunch time the next day.

Strangely, my girl really wanted to go down to breakfast with me on Saturday morning and the hotel provided two breakfasts free with the room. Obviously I wasn’t the first guy to bring an lb back to my room.

We spent a few minutes finishing off our drinks and then the girl came over. She was gorgeous – 175-180cm tall and with beautiful tits. She was a strawberry blonde and had a beautiful smile. Her English was almost perfect and she was very friendly. She was wearing a white micro-mini skirt. Incredible package.

We shared a drink and she grabbed me on the cock – I was hard and the pre-cum was beginning to stain my jeans. I guess with the bar shutting in 30 minutes we didn’t have much time to waste but on Saturday night the same sort of thing happened so I assume it is just a very forward environment.

You know as well as I do that my best work is done on the wrong (or right) end of a cock and I am not usually aggressive in this sort of situation but this girl was beautiful and I wanted sex with her so I was more forward than usual. I reached under her skirt and felt her cock. I would guess it was semi-hard but it was big. Certainly bigger than mine (I am 7”).

We drank two drinks and I discussed what I liked and what I wanted to do. I asked her if she was OK with kissing clients. She didn’t answer – just leaned over and gave me the best tongue kiss I have ever experienced. I took that for a yes. I told her I was a newbie but that I liked sucking cocks and being fucked. She grabbed my cock and gave it a squeeze. She whispered that she loved fucking big guys and that she was going to give me more cock than I could handle that night.

I knew for a fact that she was wrong about that (I have been professionally fucked by 20 big-dicked guys for a full weekend but she didn’t need to know that and I appreciated her sentiment). This girl liked to look beautiful and liked to fuck men with her big dick. What a mix.

She asked me if I was really staying at the JW and she was very pleased when I confirmed that I was. I remember when I was in Jakarta about ten years ago that the girls (real girls) that I met in bars were so pleased to spend a night in a five star that they would throw the fucking in for free. I assume there was an element of that here. The girls obviously like trying on the luxury for size – seeing how they look when they are made up to look beautiful in a fancy hotel.

We left the bar just before closing and walked back to the hotel. If you are interested, the whole thing (drinks, bar fine, girl for the night) cost less than A$150. The hotel was cool with us coming in at 1am and we went straight up to the room. I told her to grab a drink out of the bar and relax for a few minutes. I went into the bathroom and gave myself an enema by removing the shower head and shoving the pipe up my arse. After about five minutes and three loads, I finally leaked clear so was ready.

I was going to ask her to do a strip for me but she launched right into it so I just lay back on the bed and enjoyed the show. These girls love the way they look. I believe a lot of them recognise they have only a few years where they can make money this way and a lot either just go back to their earlier lives or have an operation to remove their cocks and live as women. There is a market for post-op girls but I cannot for the life of me understand the attraction.

Anyway, I grabbed a Viagra tab and snorted some amyl and watched the show. When the amyl started to kick in I removed my clothes and lay on the bed rubbing my rock hard cock. When she was naked, her cock pointed pretty much straight out and was about 8-9” and nice and thick. It had a big purple helmet and I wanted it bad.

After about ten minutes she came over to the bed and tried to suck my cock. I told her not until much later. I told her she was in charge. I wanted her to treat me tough. Fuck me hard and tell me what to do. She had the cock and she was to use it on me. It turned out she was a great actress or a dominatrix in the making. She slapped the top of my head quite hard and told me to get on the floor. I did as I was told and she sat on the end of the bed. She told me to suck her cock. I dived into the job. The cock was beautiful. It was long and thick and as I sucked it got harder and harder. Forget any stories about ladyboys struggling to get hard – this girl had a rock. I gave the job my best attention – deep throat, ball swallowing, licking the slit, running my lips up and down the length of the bottom-side of her cock. It was magnificent. The taste was the best I had ever sucked and when I looked up and saw the beautiful face and perfect tits above me I was in heaven.

She had stamina to go with the rest of the package and although I gave her cock the full treatment she refused to cum for twenty minutes. My cock was leaking pre-cum like mad and I used it to lube her balls and arse. When I started to rub her arse, she demanded that I “Get my tongue in there”. She turned around on the bed and knelt with her arse pointing at me. Her cock was pointing out and this beautiful arse was sitting right in front of me. I pulled the cheeks apart and dived in with my tongue. I know this sounds weird but her arse tasted magnificent. I had tongued a lot of arseholes in my time and there was something hot about the shitty, sweaty taste that a man’s arse gave off. This was different – it was incredibly sweet.

I went at the arse for ten minutes and my cock just kept weeping pre-cum. She moaned relentlessly. I think she enjoyed the rimming more than the cock-sucking. Finally she said the words I had been dreaming of “Now I am going to fuck your arse”. We swapped positions. I knelt on the end of the bed and she stood behind me with her beautiful cock in her hand. I rubbed my pre-cum in my arsehole and took a deep toot on the amyl. I said “Fuck with me with that beautiful cock. Fuck me hard”. Whilst I was getting ready, she pulled a condom on to her rock hard cock.

She grabbed my arse cheeks and spread them wide apart. She spat into my arse and then said “Get ready, pussy boy. I am going to give you the fuck of your life”. Then, without further ado, she pushed her cock up against my hole and pushed firmly. When she had confirmed that she was on target she rammed her cock deep into my arsehole. I felt her nuts slam up against my arse and gave a little cry – “Oh that feels good. Fuck me baby”. She did. She went at it like the best top I had ever taken. I have had bigger but nobody had fucked me harder or longer than this girl. She was a stallion. She called me pussy boy and told me how I had a sloppy arse and that I was lucky she had such a big cock. I loved it.

I screamed “Fuck me; fuck me; fuck me”; “I love your cock”; “I want your cum”. After about 30 minutes (I am not exaggerating – this girl had been sucked off and fucked for a total of at least an hour) she told me it was time for me to catch her cum. She said “This is only the first load and I want to see it on your face. You can swallow the next load but this one decorates your face”. She pulled the condom off and I turned around and lay on the bed. She sat on my chest and pulled her cock an inch or two away from my mouth. I tried to reach my face forward and take the tip in my mouth but she slapped the side of my face with an open hand and I lay back down again.

Then heaven. She blew gallons. Huge ropey streams of cum all over my face and neck and up into my hair. She kept pulling and it just kept coming. When I opened my mouth, some slid in from my top lip. It was the best tasting cum I had ever, ever, ever swallowed. I tried to put a hand up to try and get some more in my mouth but she told me (gently) “No. I want you to cum on yourself and then we can share the loads”.

I wanked myself for about thirty seconds before letting off a monster blow myself all over my chest and stomach. She took my hand away and finished the job by pulling my cock slowly until there was no more to come out. Then she did the most beautiful, sexy thing I had ever seen. She lay on top me (with our cocks touching together) and we hugged and kissed covered in our cum. She licked my face, captured great gobs of her cum and then put her tongue in my mouth.

It was the most sensual kiss I had ever experienced. We had my hot cum swimming around between my stomach and chest and her gorgeous breasts and stomach. We were sharing her cum in passionate orgasmic tongue kisses. It was incredible.

Am I getting soft? Am I losing my edge? Yes I am. This was heaven. We lay together like this and kissed and touched each other for thirty minutes at least. It was the most incredible feeling I had ever experienced.

I loved the fucking. I loved rimming and sucking. But what was different from men that I had fucked was that I got to satisfy another urge. I really wanted to hug and cuddle this beautiful woman and kiss her. It was the perfect combination.

In case you think I am getting too soft, the rest of the evening was more of the same. She cam three times before breakfast and gave me a quickie before she left after. I was fucked in every imaginable position. I got to swallow a load of her beautiful cum. We kissed. I sucked. I rimmed. We hugged. I even got to fuck her. She loved it and told me it was “good for a man to fuck a woman – it can’t be all about taking”. All we didn’t do was sleep.

One thing we did that really enjoyed was shave each other. We took a razor and went over every centimetre of our bodies from waist to upper thigh and shaved it totally smooth. We giggled as we did it and I kept taking her cock in my mouth and giving it an affectionate suck without her getting hard. I love the feel of being smooth.

After sleeping from 13.00 to 20.00 I backed up again at Casanova. From my pre-trip research, it was clear that I was a butterfly – somebody who liked it from two girls at either end. I had planned to try two different girls for my threesome but the Friday night girl had been so good that I couldn’t imagine finding somebody better and decided I would just add another girl to the mix.

When I got to the bar, I asked to see the same girl again. I told her straight away that I wanted a third member to our party tonight. I explained that it had nothing to do with her – she was brilliant and I wanted her there again but I only had one more night and wanted to try a threesome. I had read that some girls don’t like being part of a threesome and it was suggested that I ask her to select the third girl. This sounded like a good idea to me so I did just that.

I told my Friday night girl that it would be impossible to find somebody as beautiful as her and as good a fuck but that she should choose somebody who liked topping and would give me good fucking. I never considered that the there could be the same sort of gentleness after the sex that I had experienced the previous evening when there were two girls fucking me at either end so I really just wanted a big cock and a nasty attitude. A third girl was chosen and (I am not kidding or exaggerating about this) she was as beautiful as my Friday night girl. It turned out she had a slightly smaller cock but the same capacity to blow and fuck like a champion. As we were starting earlier, we shared a few drinks in the bar and did some fondling and the girls made promises of a night of fucking I would never forget.

When we finally got back to my room it went much the same way as the previous evening except I was serviced from both ends. We started at 22.30 and did not sleep. I must have taken six or seven loads of the sweetest, tastiest cum. The best news, the girls were friends and happy to share me – after each fuck session we lay together and kissed and hugged.

In fact, rather than the cock pig I was when I was being fucked by men, I was a sensitive thoughtful bottom who laughed when somebody dangled a semi-hard cock in my face and enjoyed having foreign objects pushed against my arse. The sex was hard but great fun. The Viagra kept it edgy and the amyl meant I went at the sucking and rimming with a mad passion but the post-orgasm fun was a new dimension altogether.

When I bottom for a gang of blokes they want to degrade me, make be bleed, hurt me – and I can’t pretend that I don’t love that whilst it is happening. My normal self goes somewhere else and I become this pig who just thrives on the degradation. I want to swim in cum. I want my arse stretched. I want to be hurt and degraded.

When I was fucked by these girls, I still love what the cocks do for me but I don’t have any post-coital guilt. I feel good about myself. I know I am a bottom but I am doing it for different reasons. I can’t explain it any better. I guess I am a mixed up fucker. It’s early in the piece but I think I have decided I want the ladyboys to be my future. I am thinking of moving to Thailand – probably Phuket but I am yet to finally decide – and making this my future. I realise sex is a huge part of my life. I can still find local gays (with some big, big cocks I am told) if I feel like some pig sex but I want to explore the world of ladyboys more fully.

I don’t want to get married or shack up or even have a girlfriend. If I continue to find that the girls are as affectionate as the two in Bangkok I can enjoy that feeling as much as any more serious relationship.

Right now, it certainly feels like a better way to live my life than on the wrong end of men’s cocks, fists and dildos. My next step is a two week holiday in Phuket and then I will make a decision. I will keep you posted.


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