I visited friends in NYC to join them with their NYE celebrations. I arrived on the 27th and settled in for a few days relaxation before the big night in the Big Apple. This was also time to get preened, waxed, painted, plucked and quaffed in preparation. My costume for the night will be Alice in Wonderland, one I have worn many times before.

The big night arrives. I spend a good 3 hours with my girlfriends getting ready. There’s lots of laughing and mucking around. Also there is a lot of excitement. We all know that for a hot looking sissy a night like tonight usually means getting laid.

We’re going to a party on the Upper West Side that my friends say will be a riot. It will be a mostly gay affair. When we arrive at about 10pm it is packed and there is even security which is reassuring for us sissies. We all look fantastic. I have on 6 inch black heels, full makeup and a flouncy petticoat under my Alice dress that makes my figure look perfectly triangular. My girlfriend Tiffany is dressed as a sexy schoolgirl. She’s a TS and on hormones and looks sensational, completely passable and feminine. Both of us look hot.

It’s a huge double apartment overlooking Central Park. We merge and mingle with the crowd. As anticipated it’s a mostly gay scene which was cool - these parties usually rock. There’s plenty of dancing and carrying on. We make quite an impact as we walk through. I get lots of attention from the boys. A few pat my ass as I walk past. All in good fun.

I walk into the kitchen and standing by the sink is a fairly ordinary looking tall man of about 6 ft 3. He’s smiling directly at me and says something like “woah - hold on - look what’s just walked in!”. I glare at him and walk past. He bursts out laughing. His friends seem amused. I’m thinking “what a dead shit”. I walk back out and go and tell Tiff. She says not worry and we both decide to have a dance.

Later on I’m taking a rest from dancing (it’s very hard in 6 inch heels and I think I hurt my foot). I’m sitting on a huge sofa with about two or three others. There’s still plenty of space. Suddenly the guy from the kitchen plonks right down next to me, still smiling. “What’s happening?” he says. I don’t say much but then he surprises me by apologising for being a dick and goes on to to tell me what the joke was. Seems he had some bet with his friends. I’m not really convinced and tell him so. He keeps talking. After a while I’m still listening. He’s sounding a lot better. He’s an intern at some hospital in Queens. His name is Jake. He’s 29, sporty and says he’s ‘straight’. Like I said before, he’s pretty ordinary looking, but as I look at him more closely I see he’s quite muscular and well groomed. He’s got a silver chain around his neck, and his chest hairs are poking out the top of his shirt. I don’t find him attractive though (I’m not really that attracted to men - it's mainly ther cocks I want) but I’m sensing that he wants to try something on with me and that excites me.

We keep talking and topping up our drinks. After about an hour he’s laughing away at something and then his hand is on my knee. I look at him and he winks. “You said you were straight!” I say. ”I am” he says. “Mostly”. I’m gazing at him and he smiles sweetly and I suddenly feel a warm rush of affection mixed with lust. He must have as well because we suddenly embrace and kiss passionately. My hand is now on his thigh and I slowly stroke my way up towards his crotch. I reach his groin and open my hand, resting on his very hard manhood. We kiss again. My hand is holding his cock through his jeans and squeezing gently. He’s big and thick. My heart jumps a beat. His hand slides under my dress and travels up my stockinged legs to my panties. My prick is hard as nails and has unfurled itself from between my legs and is standing to attention poking out from my panties (damn I should have worn my gaff). He smiles. I playfully slap his arm. “Not here” I say. I stand up, a little wobbly and holding his hand, pull him up. “Let's go somewhere quiet”.

Tiffany has been watching me and she runs over and whispers to me asking where we are going. I giggle. “I don’t know - somewhere private”. She says the bathrooms are a no go - big queue. She says that the roof is open and that to try there. Jake and I walk to the lift. In the lift we kiss more, his puts hands up under my dress around my ass. We arrive at the top. Well not quite. We still have to walk the last flight of stairs. I walk in front and he has both his hands on my ass squeezing playfully.

The roof is huge. There’s lots of sofas, pot plants and party lights. There are screens with light shows and movies and there is music. This gig is so well organised! We walk to the back corner, there’s a single sofa and no one is here.

I sit down. Jake is towering in front of me looking down. He seems edgy. His big cock is clearly defined in his jeans and is exaggerated by his arms akimbo posture. I reach up and rub it softly with one hand gazing into his eyes. He moans. I slowly unbutton his fly. He is running his hands through my wig. I’m hoping it doesn’t fall off! As I undo the last top button, his jeans fall open exposing a very large cock peeking over the top of his CK undies. As I stroke it through the undies I notice a drop of glistening precum appear. I am so horny for this guy now.

I lean forward and pulling his undies down I get a good look at it now. His cock is big and thick and slightly curved backwards. I’d guess about 9 inches long, cut, the shaft is rippling with veins and it has a huge glans. The glans alone would run for nearly 2 inches down the top of his cock. It gently throbs with his pulse. Holding his shaft near the base I softly kiss the head. He shudders and suddenly grabs my head and tries to pull me onto him. I pull my head away and stop. He gets the message and lets go of my head. I do a look around and see nobody is paying any attention to us. His back is to the crowd anyway. I return to kissing his cock. I extend my tongue and lick his member all over so it’s wet with saliva. With my mouth open I descend on his cock head, taking about 2 inches in my mouth. He smells musky and tastes a bit like soap. At least he cleans himself down there. My hand is sliding up and down his shaft as my mouth slides up and down in time. My other hand is rubbing my own cock through my panties.

One of my special talents and loves is deep throating cock especially big and fat ones. Now that I have warmed him up it’s time to take all of him. I tilt my head forward with my jaw extended and open my mouth. His cock slides in about half way. He gasps - he knows what I’m going to do. I pull back and take him in again. This time his glans is pushing at the back of my throat. I feel a powerful gag reflex coming on. I stop and grab Jake’s thigh to steady him (if a guy forces you at this point you’ll puke for sure). We both stay motionless. After a few seconds the gag reflex passes and I slowly descend further. Now I stick my toungue out. Another gag reflex comes on and I stop again. My throat opens up. I pull my tongue back and Jake's cock goes in deeper. I’m breathing loudly through my nose. I continue. Slow is key here. Now I am nearing his balls and his shaft is much thicker at this end. My jaw opens wider and then he’s all the way in. The last few inches requires the cock to bend a little as it goes down your throat so there is always a little more resistance than before. I stop again. “Fucking awesome!” he cries. I look up - which is difficult as I can't bend my neck with that monster down there. I can’t smile either. I swallow a few times and the peristaltic wave of my throat massages his cock. He groans again.  Now that my throat is used to him, I can start to really throat fuck him. I pull back and grab his shaft with my left hand. Now I take the whole cock in in one go. As I pull my head back, I grab the shaft and slide it along following my mouth. When his cock is completely out of my mouth my hand slides over his glans. Then my mouth goes back, following my hand down the shaft. This is so hot! My thumb has worked it’s way through his undies and is now pressed gently on his asshole. He looks puzzled for a moment. I press it in and he shudders again. If we had more time I’d like to pound that ass which I am sure is virgin! Jake’s legs start shaking visibly. I know I’m having the desired effect on him. I keep sucking like this for a few minutes increasing the pace. Now he is also thrusting and its banging my tonsuls. My jaw is aching like crazy. I look down briefly and see a pool of slobber on the ground and realise it is coming from my mouth!

Jake takes command and pulls my head off his cock and motions me to stand up. He grabs my waist and turns me around but I resist. I want something else first. I turn around and holding his waist guide him around and push him into the sofa. I’m standing in front of him now. He responds by running both his hands up my legs, meeting at my panties. He grabs my cock through my panties roughly. I lift my dress and he pulls my panties down a little and lunges at my cock, taking as much as he can in one gulp. He’s struggling as he simply has no idea what to do. It’s sort of cute to see guys clumsily give head. I hold my cock for him while he does the best he can. I thrust a little and he gags instantly. Anyway it still feels good and the sight of a straight looking guy on the end of my boi clit is so erotic.

Jake looks up and says “I want to fuck you”. I am so horny now and I want him in my ass so badly too. He stands up and forcefully pulls me to the sofa and bends me over the armrest. He leans close to me and kisses me hard and then positions himself behind me. I look up and ask if he has a condom. He doesn’t, the dope. I reach over to my bag and rifling through it quickly pull one out. I sit up and he faces me with his cock. I quickly open the pack and roll it on. I turn around and bend over again. With both my hands I reach back and pull my panties down to my lower thighs. I wiggle my ass at him. He laughs nervously.

Jake presses his cock head against my ass. I can feel him jerking himself off. It all goes quiet. I wait and nothing happens. I look around and he looks back sheepishly. “Oh” I say looking at his limp member. Turn around I demand. I pull the condom off and take all of his semi hard cock back into mouth. After a few seconds he his hard again. I quickly put another condom on him. I spit as much saliva into my hand as I can and apply it to his cock, the rest I dab on my ass and bend over again. Now he wastes no time and pushes his cockhead into my ass. His glans penetrates almost immediately, stretching my asshole unbelievably. I reach back and hold his thigh to make sure he doesn’t plunge in too quickly - I need to get used to him there. The pain is intense. We wait a moment longer. Then I gently pull his thigh towards me and he pushes his cock all the way in. I can feel his hairy ball sac on my ass. God he’s huge!

There’s some commotion going on on the other side of the roof. Jake stops, looks up and seems to panic. I look back around and tell him to ignore it and just fuck me. He refocuses and starts to pump. He leans over me again and roughly kisses my neck. Then he presses my shoulders down hard so that my ass is pointing straight up. He’s holding my ass cheeks tightly, each hand full of my flesh. Now he’s really pounding me. Fuck! - it hurts like hell. My ass feels like it is being split open. I can feel his cockhead pressing on my upper organs. My asshole is on fire. My whole body lifts off the armrest with each thrust which is accompanied by an involuntary primal grunt from my mouth.

Jake’s persona takes on a new form. With every thrust he’s saying something like “take that you fucking whore” or “your ass is mine you slut” or “you fucking dirty bitch”. I’m a bit shocked. I don’t actually enjoy being verbally abused like that. But I love being fucked hard and I’m not about to interrupt this ecstasy. My sphincter is gripping his shaft tightly which he clearly feels, so he draws his cock almost completely out with each stroke, maximising the effect. He fucks me like this with increasing force for a few more minutes. I try and jerk myself off but my cock is flaccid - for me this is usually the case when you have such a huge cock in your ass. I can’t take too much more though.

He’s groaning is increasing in frequency so I know he’s close. I push him off me and quickly turn around, sitting back on the sofa. I want him down my throat. I rip the condom off and he thrusts his cock back into my mouth, holding my head and pumping forcefully. I push him back a bit and retake control by holding his shaft and sliding up and down in time with my mouth. He is groaning very loudly now. His hands clench my shoulders violently. His cock swells in my mouth. He’s going to blow. All goes quiet. His whole body tenses. Suddenly I feel a big shot of warm cum hit the roof of my mouth and the back of my throat. He lets out a throaty loud grunt. I moan with delight. This is the best bit. I keep my mouth still, with just his cockhead in my mouth and I quickly pump his shaft with my hand. More cum shoots in with each spasm. Jake groans again. I swallow one mouthful with a gulp. More is coming. It’s salty and slightly sweet. I open my mouth and he obvioulsy enjoys seeing it full of his semen. He pulls away from me and takes hold of his cock and furiously jerks off so that the last spurts of his cum dribble on my nose and cheek. He’s done. I hold his cock and gently suck the last big drops appearing at the tip.

Some of his cum is still on my lips and tongue. I stand up and we kiss. I push some of the cum into his mouth. He recoils and spits it out. I chuckle. He quickly puts his cock back in his pants, does up his fly and adjusts himself. I do the same, grabbing a tissue from my bag to wipe the cum off my face. We stand up and walk back to the party which I do with some difficulty as my asshole is still on fire and my rectum feels like it just had surgery. I reach around and touch my asshole to check and it is raw as an open cut.

Downstairs Jake disappears back to his mates. Tiffany is nowhere to be seen. I check my phone and there are a few messages from her checking up on me, bless! I message back all is well. I leave the party soon afterwards and meet up with Tiffany at a nearby bar. She’s there with a young guy she also met at the party. When I got back to her apartment I started this article as I didn’t want to forget any of the detail. What an incredible sissy experience!

I've been teaching my girlfriend how to use a photographic studio. The thing is she refuses to have any part of her body in any shots! She is so paranoid that one of friends or family in Bangkok will recognise her.

So when we set up a shot it usually involves me getting dressed up in some sissy outfit, with my cock bulging in some new sissy panties she has just bought me. I pose in various postures that eventually lead to me bent over or on my back with my legs apart, spreading my ass cheeks. This is where she leaves the camera and hastily penetrates me. After working up a pounding steam, she comes - slowly injecting her load deep into my ass. This is when she returns to the camera.

We have been playing this game for a few months now so I have quite a few shots of my creampied ass. I will share these very soon, but for now here is a sample of her handiwork.

 On this occasion my girlfriend really unloaded up there. While lying on my back her load continued to slowly dribble out. I was ordered to stay where I was, making sure my panties were not getting in the way of her shots.

Well this was unexpected too. I went down to Pattaya from Bangkok thinking I'd like to check out the ladyboy scene. Never been there before and was very curious.

I was called over to a bar by a breathtakingly beautiful. tallish, slender girl. I stopped for a drink and a chat. She was both sexy and dreamy at the same time. She had small breasts in a push up bra, and was wearing a mini skirt just covering her big hips and ass. When she leaned forward I could just make out her white silky panties. Her name was Darae.

Well not long after I was in a 'short time' room with Darae who promised me something that none of the other ladyboys could offer. I must say I was mesmerised.  We kissed and caressed each other on the bed for what seemed like ages. Then she undid my shorts, pulled them down and lowered her mouth on to my very hard cock. I am not huge but I am not small either (about 7.5"). She took me in her mouth and down her throat in one go! God what an amazing feeling. She worked on my cock for some time, bringing me close to orgasm and then backing off each time. Finally she stood up and with her hands invited me to approach her crotch.

I knelt in front of her and stroked the bulge in her sexy panties. Her cock must have still been folded between her legs - and she was clearly uncomfortable. Impatiently she unfurled it and it hung out to the side of her panties. Crikey. It was a snake. I'd seen pictures of a TS called Long Mint and Darae had a similar sized cock. She wasn't hard yet but she wasn't far off. I looked up at her and she said "I told you I had something special". No joking.

Well I wasn't going to rush with that thing. I continued to stroke her balls through the panties and she started moaning. Those panties were so cute on her. White silk with lace trim. From behind her ballsack was bulging the crotch but not showing through. I parted them briefly to peek at her asshole which was clean, puckered tight and smelt like jasmine. Her hips were curvey and feminine and the contrast of that bulge, the silk and lace and her jasmine smell was sublime.

Her cock was fully hard now and pulsing. I licked the head teasingly when suddenly she grabbed the back of my head and forcefully pushed it into my mouth. I took about half the shaft in and there was still plenty of length left for me to wrap my hand around it. Sliding my mouth up and down while using my hand as well seemed to do the trick as she was moaning and groaning so loudly I was sure there'd be a knock at the door any moment. 

I was learning how to do this better each time and also learning to really appreciate it. My jaw was aching. She was ready to deploy that thing elsewhere. I moved onto the bed and assumed the position on all fours. I knew this was going to hurt a lot but I was also excited. She didn't waste any time. She lubed up my ass, gently inserting one, two then three fingers in and pumped them for a moment. Finally she very deftly put a condom on and pressed her cock into my asshole.

I reacted badly. It stung so much I grabbed her arm and yelled stop. She said "no problem baby, we can go slow". She stopped there for a minute or so. I was masturbating myself and she helped by squeezing my balls from behind. The pain lifted slowly and she started to thrust gently. Although it felt like she had a lot of her cock in me she actually didn't because for the next minute or so, on each gentle thrust I felt more of her go inside. She asked me cheekily if I wanted all of it. I said yes - of course. Well I got all of it. Honestly I swear I could feel some internal organ being bumped and dislodged each time she thrusted.

Her thrusting got more powerful till eventually all that could be heard was the fast rythmical slapping of her thigh on my ass. Her moaning increased to a crescendo and she quickly withdrew leaving the condom in my ass while she came all over my cock and balls. She scooped a little up on her fingers and rubbed it around my lips. "Nice?" she asked. I nodded.

A moment later she was ontop of me and working her hands around, put a condom on me and basically sat her asshole on my cock. I went straight in, full length even though she was very tight. It must have hurt her. She started pumping me and said to me "you come now". This wouldn't do. I pushed her off me and turned her over and quickly entered her from behind. She yelped! It was amazing. As I was thrusting her I could still feel my own ass tingling and occasionally pinging pain inside. She started rubbing her own cock again and it was hard almost immediately. 

She rolled onto her back, put her legs up in the air and invited to take her this way. I climbed on and thrusted away. When I was about to come she pushed me off her, tore the condom off and jerked me to climax, aiming my cock on her prone asshole. I blew my load all over it while she was furiously masturbating. 

When I was spent she pulled me on top of her and pushed all of her unprotected cock back into my ass. This really shocked me - and it hurt even more than before.  But she was strong and she gripped me so firmly I couldn't really break free. Serioulsy I felt I was being raped! She rolled me over and pinned my arms behind my head, pulled my legs up and pushed them almost all the way behind me. At the same she was madly pounding my ass, very quickly and very roughly. Everything was a blur. I tried to push her off but she had me pinned in such a way that I couldn't get any purchase to move myself. Suddenly she let me go, pulled her cock out quickly and positioned herself over my face. She came again. I was angry but I wanted to taste her none-the-less. I pulled her towards me and was rewarded with the last few spurts in my mouth. It was enough.

What an experience. I chastised her about the virtual raping but she laughed and said something to the effect that I wanted it.  Probably I did but maybe not like that. 

I have just had another mindblowing experience with a ladyboy. This time there are awful grainly pictures to go with the story - mostly of me sucking her cock and copping it up my ass. Just writing it now - will post soon!

x 

I have always been excited by lingerie, especially the feel of my cock and balls in it. I have stolen panties to wear while masturbating and even bought lingerie outfits to play with at home. Being a bit of a photographer I quickly discovered that I coud dress up and photograph myself.

What I didn't realize till recently was that I was turned on by other TV/TSs too - the more passable the harder I would get. I didn't think much more of it though. I'd never have considered myself bisexual. But then, not long ago things changed completely. I had an unexpected torrid but brief affair with an astonishing lady-boy.

I met her at a Thai takeaway joint. She was serving behind the counter and frankly I thought she was a she. She obviously had an eye on me because she came over to where I was sitting and introduced herself. Her name was Yindee. She wasn't short - probably 5'10". She was of slight build but had large breasts which she was clearly proud of. I could tell this by the way she would lead with them when she turned her body. She had long black hair, immaculately groomed; big lips, high cheek bones and beautiful skin. She had hips too but her ass was flat. I thought this was odd. We had a little chat - she was so sweet and kind. We agreed to meet up later. When she left she gave me a little peck on the cheek. Watching her walk away I suddenly noticed while staring at her ass that she was a he. I was genuinely shocked. 

When we met up a few weeks later, we had a drink and ended up back at her flat. We kissed and played around for quite a while and we were both getting aroused. Then she did something I was really not expecting - she insisted on crossdressing me! Of course I was keen as I already had a fetish for panties but I'd never had a full transformation. She started by choosing her sluttiest outfit, with gaudy tiny pink panties, lace top stockings and suspenders. Then full makeup, a pink wig and heels. After admiring her creation by making me parade around the loungeroom (while taking a few clandestine pictures on her iphone), she drew me towards her and firmly pulled my head down on her elongated and strangely crooked stiff prick. She was still wearing panties so I wasn't sure how big it actually was - but when I got closer I could see it was huge - thin but long. I'd never sucked a man's cock before but I guess I knew what to do. I licked up and down the shaft wetting it with my saliva before taking the head in my mouth. Slowly I took more in till eventually it was on the way down my throat. It was ironic really because I'd many times tried to force my own cock down girl's throats before. Now it was my turn. I manged to resist the gag reflex long enough to get more than 2/3 of her cock in. I was actually deep throating, taking the shaft most of the way in and out rythmically, up and down along most of the rod. She said something in Thai which was obviously an expression of surprise. As she was moaning she was fingering my cock, balls and finally my ass. She licked her thumb and pushed it up my ass. I looked up at her and she winked. I sensed a change a pace.

Suddenly she stood me up, bent me over, pulled up my skirt, parted the pink panties and drove her tongue deep in my asshole. It took my breath away but before I could get used to this I felt the head of her cock pressing on my anus. Involuntarily I was puckering it tightly shut! She pressed a little harder. I was really scared. Finally my anus surrendered and opened. With one hand she softly rubbed my cock through my panties while at the same time slowly pushing her cock up my ass. She was gentle but it hurt like hell. By slowly rocking her hips she inched it in further and eventually she had the whole thing in there. It felt like I was impaled on a fence post. Gradually the pain eased and she started to pump me. At this point she whispered in my ear that she loved New Zealand men! She then proceeded to fuck my virgin ass harder and harder and to be honest I loved it.

Finally, she withdrew from my ass and motioned me to lie on my back.  Accompanied by loud moans and very slow deliberate strokes with her hand, she blew herself across my stomach and face. I've really never seen so much come - really a small river of it - certainly more than I would have imagined possible and certainly much more than I had ever produced. My face was half covered as well and some of it had even found its way into my mouth. It gathered in big pools on my belly and then spilled onto the floor. My ass was stinging like mad but I was more fascinated by the come sea. I was staring down at it on the floor when she tapped me twice on the knee and motioned with her head to pay attention. It was not over yet.

She addressed her mouth to my cock which by now was aching from being hard for so long. She masterfully fellated me and I could have come right there and then but she had other plans for it. She held it in her hand and positioned me behind her, all the time gently jerking me onwards. Without really realising what was happenning I was already penetrating her asshole. Her ass felt gritty but surprisingly tight. It was quite a sight. She was on all fours, polka dot panties pulled to the side and my cock planted right in her ass. It was an unfamiliar view - because I could clearly see her cock bobbing between her legs and her ball sack bouncing left and right.

But my god did she squeal! I stopped - thinking I was hurting her but she angrily shouted "fuck me, man". I pounded away for a few minutes - she knew I wouldn't last long. Then she pulled herself off me, turned around and held her lips just an inch from the tip of my cock. She looked up at me and smiled cheekily. I'm sure I didn't disappoint her as I unleashed a mini torrent of my own. She clearly enjoyed being comed on. She moaned and groaned, licked and cooed. I felt oddly proud of myself.

It was extraordinary, unexpected and completely mind blowing! 

BTW: we were safe. 

PS: I've had quite a few messages asking for more accounts. I will endeavour to record a few more of my adventuures with Yindee.