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!