So there I am analysing myself in front of my hotel room mirror, for a final check that I am ready to greet my man when he knocks on my door. With an excited nervousness running through me from the pit of my tummy, fuelled by the uncharted experience I was about to have with a top male for the first time, I do my final checks. Hair, coffee brown, shoulder length combed straight, check, Full makeup bronzer, blusher, foundation, mascara, eyeliner and of course pretty pink lipstick all in check and a flutter of my false eyelashes for good measure. Perfect, no sign of my male persona anywhere, except perhaps my small bulge at the lower centre of my dress, well, I was excited. So there she was looking back at me in the mirror, familiar eyes with a new look, a dirty slut that had been deprived for so long was finally going to go all the way. I gave one final pose for sassiness in my leopard print mini club dress being stretched at the breasts to accommodate my 34DD silicone bra infills. The bottom of my dress stopped just shy of the top of my super smooth silky black self-hold-up stockings, running down to my feet. My feet were hugged by some black high heeled peep toe shoes with my toes squished together showing just three of my toes at the narrow opening. Well, I had painted my toenails pink after all to match my nails, would be a shame to waste that especially if he’s into feet.
So a final message on my phone he’s in the hotel car park right now. My hotel room and floor number details had been sent in a text reply. He knows where I am now, no backing out of this. A dimer of the lights was in order to create a more sensual and exciting mood. Only the sound of the lowered hotel room T.V churns out music, a hip-hop music channel goes through some old chart toppers. Wait! that’s not the only sound, all of a sudden my fucking heart is racing, those damn gimmicky rabbits fucking like there’s no tomorrow comes to fruition in my mind, it kind of matches the speed of my pounding chest knowing that any minute now he will be here… “knock, knock ” , he’s here. Just go to the door and be the filthy Tgirl he’s expecting you to be, I tell myself.
The filthy tgurl knew she was ready, she’d been ready for so long in her mind to let go and be herself. Slowly she opened the door and stayed slightly behind it as he squeezed through the gap as soon as he could. Young Jess, the tgurl, could see and feel his large presence, as described he was a tall but tubby older Italian gentleman. Though not clean-shaven as his picture had suggested, never the less he was who he said he was and he was here stood in Jess’s hotel room. Jess closed the door and latched it back across. The moment she turned around his bag had already hit the floor and he’s right up against her fem body, pinning her to the door with authority, ready to take his filthy whore. Jess feels his big hands grab her soft waist on either side, so tight it hurts a little at first. Then he leans in with his body and his face, his eyes looking into hers, a look as if to say, “now I have you” lasted a few seconds. Jess realised all the cock teasing texts she sent had gotten to him. Jess switches her eyes down at his lips as his gaze was one with deep ownership written in them, too much to keep the eye contact. Jess was about to greet him and introduce herself by name and that she’d be his gurl for the night. But then before she could willingly give the final go-ahead for him to take her, he goes right in, in mid-speech, he just couldn’t wait. He French kissed Jess with a lot of lust and passion, then in one movement moves her to the sidewall. His tongue was still deep in her mouth with his heavy breathing. She wondered how far down her throat he wanted to be. But of course she was extremely excited, he wants the hotel whore badly, he really does want her. Jess felt exhilarated and her heart actually slows the nerves a little but her beats per minute had increased tenfold. Her cheeks blush with the shyness of being manhandled that way, his heart too would be pounding as his dick began to swell, all of the hotel whores tricks of masquerading her male persona had worked perfectly, her perfume was drifting deep into his nose. Jess was going to get the fuck of her life from this raging bull she’s just allowed to unleash on herself.
The initial kiss left jess feeling amazing and very lustful, the ice was well and truly broken. Sex was the only thing on their minds, filthy, raw, dirty hard sex that no one would ever know of but those two, the moment was theirs to enjoy. The Italian man, who still hadn’t introduced himself, gave jess the kind of look powered by deep lust, his manhood continued to swell as he couldn’t believe his luck with the bombshell tranny. A tranny worthy of the title too, though she really was just a convincing crossdresser who went above and beyond to please men.
Jess toyed with the man and pushed him back a little with a flirtatious “come get me stair in her eyes”. She then sat legs crossed on the double bed while he explains to her that he came right from work to be there.
‘is it ok if I didn’t shower yet’ he says in his strong Italian accent.
‘of course, your fine as you are’ Jess replied. Her eyes opened wider momentarily at the thought of a sweaty man being all over her.
So he continues to unbuckle his belt and remove his clothes with his pants left on, a large guy, hairy belly very sexy thick legs waited to be kissed and squeezed. However, he has a kind and rounded face, but those eyes of his do not display that. Jess can see he has one thing on his mind, to satisfy his sexual need and the sooner the better, his actions were fast and rushed in order for him to be back on her as soon as possible. That cock bulge Jess could see was still yet to grow fully. She guessed he is in a state of a semi as they say, and of course, Jess was in anticipation as to see exactly what it was she would be dealing with when he had gotten fully erect. Jess surprised herself, as she felt hornier than ever and yet her own boy-clitty has not even entered the semi stage. It was new for her, a different kind of feeling she’d never had before, wanting him, needing him yet she was not hard. Her ass, however, was clenching into her knickers tightly, and she felt all her arousal come from her sensitive smooth anal ring. She’d never been so fem around a guy in her life, that moment was the beginning of the end of Jess’s erections for erotic play, she would soon know the full extent of her fem sissy ways and how much they had taken permanent effect on her mind and body.
The horny gentleman finally advances towards Jess. She lay on her back as he crawled over the top of her. She rubbed her feet, now free of the peep toe heels, over his balls still in his pants, to entice his dick to go fully hard. And it works almost right away like a wand casting a spell. The result of this was what she wanted, however, be careful what you wish for came to mind as he grew to be huge. Jess just wanted to stare at it and take it in so to speak, but he pushed her head back onto the bed. His head came in line with hers and as he did earlier, he kissed her mouth. One hand reached up and around her thin throat with one of his fingers reaching up over her chin and lips. The other hand again grabbed harder than before on her soft waist. Jess let out a small “ouch” as he pinched her with his grip, now she felt totally his, stuck underneath him right where he wanted her. The large Italian man kept kissing and kissing with his tongue shifting his saliva into Jess’s open mouth, whilst rubbing his fully erect cock over her balls and near that very sensitive asspussy. She made it easier for him to rub her there, as her legs reach up and around his waist in a lock position exposing her butt crack to his shiny leaking helmet.
‘What’s up sexy whore, what’s the matter?’, he said to Jess with a sinister grin on his bearded face, whilst still on top of her. He could see the slight hesitation in her eyes, brought on by how big his manhood was, and the damage he could do with it, or better yet, the kind of deep pleasure it could summon.
His unshaven face has only slightly annoyed Jess as her only request was for him to be clean-shaven. In-between kissing and rubbing, Jess replies, ‘nothing’ Though her thoughts were shown in her eyes immediately after getting a glimpse of his size. Jess’s subtle eye contact was her tell tail giveaway that his manhood was definitely large and the largest she’d ever been invited to play with. Of course, she had prepared to engage with a man and she was ready. Her usual routine of light plays with her dildos and toys before the meet was just as important to her as being his “girl” visually or “sexy whore” as he put it. Her dildo is a good plaything of hers and a good 12 inches with average girth, though the length was still yet to be mastered completely.
A stinging sharp slap came from nowhere across Jess’s soft immaculate makeup brushed cheeks. This was a kink not brought up when the pair were sexting their likes and dislikes upon arranging the meet. Yet here he is with those big man hands one of which is still on her scrawny throat, but the other now inflicting sexual pain across her face rather than his grip on her waist. Unexpected and un-wanted the slaps were, but that was the point, he was in control now, so what is a girl to do when her man is laying with his full body weight on her engaging in naughty fantasies? Well if he’s happy and wants it this way, Jess let it be, it’s a new experience, after all, she said to herself. Just indulge in this, for now, she keeps telling herself, her submission to him had taken hold, her upper body lay limb at his mercy.
The Italian man enjoyed seeing his femboy take that pain as she looked into his eyes, now with a different tone, as in please stop you bastard. Jess had had enough, her face stung and buzzed out. With Jess’s stern look her nails dug into his back to try and give the same instruction, what a useless attempt she made to try and dismay him. Mainly because he enjoyed it but also because he slapped her even harder and then he held her wrists together above her head with just one of his hands. At least he has stopped slapping her with the grip he had, She thought as a tear slipped to the side of her eye and down the edge of her face, dragging with it some mascara. Though it was not an emotional tear, more a watering of the eye from his sharp domineering slaps. This man had clearly seen jess as nothing but a worthless whore for his own pleasure. What else was she supposed to be, dressed the way she was?
The other hand now finally released Jess’s throat and he moves his pants to one side to allow his bare cock that has started to produce lots of pre-cum to touch her tight dry asspussy. “Fuck” is what Jess is thinking, he doesn’t know her butt hole needs lube for a smooth comforting fuck. Her eyes glance towards the lube bottle she had left on the side table by the bed. She isn’t sure if he saw it there when he came in or he is inexperienced with tgirls. Then just as that thought was passing in her submissive mind, there he goes. He guides his massive self-moist dick right into her quivering asspussy, all the way in, in one movement as if she has a real female pussy. That training with her dildo all went out the window as she had never felt such a wide girthed cock enter her like that. It came with such thrust and determination of complete hardness and unstopped force. Though his length was long, she did feel his balls hit her smooth ass cheeks and thank god she thought, as her ass and what felt like her tummy was now full of this Italian man’s throbbing dick. Jess’s ass, as soon as he was in fully, clenched up tight around him almost asking him to not push again, though his pre-cum turned out to be the best kind of lube. He held it there for a moment as Jess had to let out a moan, which was mostly for shock, but he enjoyed the sound she made before thrusting out again. Jess’s pre-cum marked ass was empty for a split second, then…
‘arrhh fuck, fuck, no, no, no, hmmm, oh my daddy, your too big for me’ Jess said arching her back and head back so as to allow the dick that needed her to shunt in easier.
There he is, he is fucking the hotel sissy faggot. Faster and harder now with each stroke and jess can’t help but wonder what kind of night they were going to have together. Multiple strokes coming hard and fast deep every time he goes in and balls slapping on her relentlessly, a string of pre-cum linked between his balls and her ass. Nice big balls too, they complement his size and Jess imagen them to hang very low with a full white warm thick sticky load waiting to be shot out and end up god knows where. Jess lay on her back in dreamland as he rocked her body and mind on the edge of the bed. His hands now try to feel under her leopard print mini dress and lift it across her fake tits. He held her tight like he wanted to make passionate love to a wife, or even conceive with her, or was it just deep lust to fool around with the forbidden fruit? Lots of kissing and intense stares at one another continue while he keeps his dick hard fucking the slippery tight naughty ass. They both begin to sweat as the heat builds up between them, Jess feels a bead of his sweat drip on her bottom lip from his forehead, then 2, 3, 4 drops land. As it streams down his face on top of hers, he notices Jess’s face scrunch up with pleasure and pain, her nice teeth exposed to the sweet droplets, her own forehead beads with sweat too, sitting there waiting to be rubbed off. While he’s pounding his tgurl whore like a b**st he goes at her again, a huge slap to her face runs her makeup and sweat everywhere. It happened the moment she looked into his eyes again, his response as if to say don’t look at me like that bitch. Jess had never felt a buzz like it, even her nipples felt every rub of fabric on her bra. His face is frowning and his mouth open like he’s about to unload with every thrust something Jess had no control over and they hadn’t discussed bareback sex at all.
‘don’t slap me, don’t slap me’ Jess said during her moans of pleasure, adjusting to the large bare cock in her.
‘you are beautiful sexy whore shut fuck up and take how I fuck’ He replied, looking at her light she was less than human.
at that moment her request was answered and he even went up another gear with his fucking thrusts, which she hadn’t expected from her initial judgment of the man, she didn’t give him enough credit, but he was surprising her with his skills. Jess simply wasn’t sure he could fuck this good and hard upon her first impressions when he walked in. Though she knew to expect more slaps, however, he didn’t see it through. She knew her original thought of being fucked like a wife or potential breeding partner was quickly subdued to how she analysed his words in nanoseconds, he fancied the whore yes, all her hard preparation work had paid off, but he viewed her as a whore, a sexual object. Perhaps she had taken on the girl in his wild fantasies, so whatever he had fantasised about she guessed he was going to do to her, regardless of what her requests were.
Rest bite finally came, ‘god I needed it’ Jess said to herself, but now he had arched up and out of her, he stood by the edge of the bed where another glance of his big weapon still stood strong. He pulled his tranny whore towards him, Jess enjoyed this with her legs still parted for him, being manhandled this way was cute and she felt very fem, well as fem as can be expected on top of being fucked raw by an Italian stallion. As he got her in position he entered her again and fucked her ass from his standing pose. Jess was still on her back and now her stocking trembling legs were placed closed over one of his shoulders. She felt a run of liquid tracked from the top of her ass downwards right down and around her asspussy. She was partly worried he’d cum, but no way, not still being that hard and not even giving any sign of ejaculation. The run of liquid was simply ass sweat and pre-cum. We were both hot and wetter now, the very reason he’d changed position. No sooner can Jess feel her asspussy lips beginning to swell and jump with the smallest sensation, he enters her again. The head of his dick pushing slightly in an upwards, now towards her tummy or belly button though not that far inside. Jess’s ass slaps against his thighs repeatedly and she feels more relaxed somehow and allows him to do his thing, while she covers her boyclit with one hand and the other hand holding her right ass cheek slightly to the side, to allow clear access.
The strangers had been fucking for around 20 minutes at this point, hard and fast at it. He’s no sign of stopping either. Good thing too Jess thought, as he’s now really hitting her g-spot, making her moan louder now. Jess was worried a bit about the other guest next door hearing as she caught herself off guard from her own noises. The door connecting the two rooms is locked and she hears a guy knock on it from the other side. Whether this is to keep quiet in a subtle way or can I join, they were not certain. However, the lust for sex and this amazing new experience for this guy was overwhelming and he didn’t bother to acknowledge the other tenant’s remark, he needed his fantasy fulfilled after all.
After a few minutes, the rest bite did come as he went into the connecting toilet and washed his face. Jess had poured a glass of water for them both from the dressing table where she had done her makeup with a nice big mirror in the middle of it. She stood there, he had finished his water quite fast, Jess wanted to actually rest a little more and didn’t swallow it all too quick. Well Her mistake thinking she had a say in this matter. Her Stallion grabbed her and turned her around to face the mirror. Her water spills as he takes her, they both know what’s about to happen. He bends his hotel whore over and in a quick motion to stabilize herself her hands brush over the desk and knock over in a sweeping action all her lady things. The impatient man is in her again in moments, but softer this time, he looks at her through the mirror and asks, ‘you like cock, yes you take it like good bitch’.
That broken English accent gave her chills and excited Jess to smile at him, his hand now squeezed her bum cheeks and he moves them in a circular motion while 3 quarters of his meat is inside her ass. Then just as Jess thinks he is tired, the same thrust full forces came like he’d just walked in again, fresh as a daisy. Hard ass destroying strokes hit her ass, she was looser now and in full swing, somewhat wider and more accepting of his girth. Lots of pre-cum gushed around Jess’s hole and inside her ass. She could hear the sound of his dick thrashing her good along with his panting for breath. He was an a****l with a prize catch, Jess was out of his league in any other social situation and he knew it. Of course Jess is all too happy taking it, moaning louder and more frequent now, and this is the wall between the other guest next door, but fuck it, she deserves her man to use her now, and this is what she’d been asking for in none stop texts, a craving in her was becoming satisfied.
‘fuck me, fuck me, fuck me harder! give it to me, oh yes, all of it now, yes right there. uhh yes, yes, yes, fuck that pussy’ Jess shouted to him, losing herself completely, void of her surroundings she moaned so loud in the feminist way she could.
Jess was stood legs apart looking into the mirror when he asked her to turn to look at him while he does as I instruct. This man didn’t want to even settle for a reflection of Jess’s eyes in the mirror, he wanted them directly on his, to peer into her soul. So the whore did so, she turned, they lock eyes and continue to fuck with power and egos growing. Jess knew he’d had no real care for the mess of her make-up, in fact, it may be a turn on for him, a statement that he’d been with her. Then slowly the door hand to the door that connects the rooms begins to turn downward and for a moment its reality that seems to hit Jess’s face. A few thoughts of “what if it’s not locked”, “what if he makes a complaint”, “what if what if”. Her ass tightens up very tight with this feeling of anxiousness, her man’s dick slows but still needs to be rubbing inside her. They both notice the handle moving, and almost as if in slow motion it reaches its full movement and thus comes a relief, the door is locked, and they are fine to continue their naughty session of sex.
The slowest withdrawal he’s yet made from her ass reaches its completion on exit and she knows he’s still hard, just from the amount of her asspussy rubbing and gliding along his hard long thick penetrative dick. The Italian man needs to ensure all his efforts were lasting as if to wipe all that pre-cum inside her or simply to enjoy that moment a little longer. Though he had no reason to stop, they had all night long to get through yet. He was more refreshed, she was just wondering now what position does he permit Jess to take? Well as she found out it involved being on her knees this time.
He instructed the messy fuck doll to the floor, so she sat with her feet returning under her ass cheeks as if to start worship. Well yes, she was in a way going to worship, to worship what this man had been using to give her what she needed. She was now to respect his cock with a sensual blowjob. Jess was gagging to thank him this way for that amazing session, though she was hoping not to end it all yet. Then he advances towards her with his solid wet cock and for the first time Jess get a good look at this b**sts cock, and fuck it is huge, not a monster cock or a BBC, but a thick uncut 9 inch long masterpiece of a sex stick. As expected from the slaps on her ass, the balls hung low and heavy, Her immediate thought was to lick them, feel their weight on her tongue and weigh up how long he had not ejaculated for. 1 day, 2 days, 3 days…a week maybe? It was wishful thinking from a cum hungry slut that Jess had become. Then as he took the final step to place it by her messy face, the scale of that dick’s head was larger than she could of hoped and had seen before, strong large wet shiny bellend looking at her with as much domineering presence as the guy’s eyes and stature. She looked up at him and he looked down at his whore. she was to do her best. She wanted slow and sensual but his dick was too impressive, and Jess simply couldn’t hold back the urge to suck it with passion, and to take those flavours into her lipstick smudged mouth, no wait, not just the mouth, but down into her throat too. So Jess did, she sucked so much on his dick it would have been tighter than when inside her asspussy. She wanted the full embrace of this man. He let out a moan and started to breath heavy as she was working her big lips and tongue around his bulging head and shaft. Even more, pre-cum now oozed out and she could swallow and play with it as she wished. Jess was in control now, but her eagerness was showing and she had to go deeper and deeper.
Deep throat it was then. His girth and head stretched her virgin throat but it was well oiled by now and she had taken him in. Pride brought about a smile on Jess’s face, it was going to be her mouth alone that would do the work of taming this b**st. Faster and faster, deeper and deeper she sucked. No cock had ever tasted this good, this manly, this ready. He let out a big loud moan, and she knew that, that was the sign of what was an injection of 4 full bursts of his warm thick sticky seed. She didn’t stop sucking and each batch of cum ejaculated right at the point where his dick was deepest in her skinny throat. However, on return, Jess could taste it all and tried to savour it. The feeling of his fast hard ejaculation down her throat into her tummy was the best moment of all, and the look on his face seemed to agree that it was for him as well. Jess carried on cleaning his cock up while he was in ecstasy, she showed him she had swallowed all of his man spunk. He stood Jess up and just looked at her closely as if to say she’s a guilty fed sissy. What happened next, however, was a shock. He’d taken a big grip to Jess’s throat again and another harder slap than ever to the same side of her red face. Then the most degrading thing of the night happened, this naughty stallion spat into Jess’s face and pushed her to the bed. He quickly got dressed and gathered his things leaving some money behind, he muttered something under his breath as he walked out the door.
Sat there in disgust of his last actions he was a guy who used his tranny whore, perhaps it was this stallion’s first time and when he was done he was done, no conversation to be had after 1 hr of amazing sex. Perhaps his kinks were rough with a sickening worthlessness Jess only wanted in role play. Then She suddenly recalled it, what he’d said when he left, “your beautiful” It was a little comfort but still, they had arranged to stay the full night and be more involved, though he was just there, for one thing, fucking his girl then leaving. Typical she thought. Then her hotel room door unlatched, Jess heard it open, is he back? Did he forget something?, does he want more? No, it’s the guest from next door. Jess just got caught with her pants down at her ankles sat on the edge of the bed, her makeup a mess, hair all over the place and she stunk of the smell of sex. Now there’s this tall black guy just looking at her in shock. Jess had to wonder if he was thinking the same as her, when they looked at each other in the eyes, her boyclitty responded.