Steve loved to watch porn. Like most guys, he got a thrill from watching great-looking girls being fucked by hung studs and doing all the things he dreamed of doing. Sadly, his wife was very vanilla in her tastes of late. He remembered the times before the kids were born, when she used to love him going down on her for hours and enjoyed having her sexy little ass fucked. Those days were long gone though, her sex drive through the floor. He still loved her dearly, but sex for her meant stripping off, a cursory tug of his dick to get him hard, then bracing herself while he fucked her. The quicker he came, the better for her. Even these sessions were becoming less frequent now.
So Steve watched porn and even hired the occasional escort to help him live out his fantasies. He would never consider having an affair, so most evenings, after his wife had gone to bed, he surfed the net, looking for interesting porn to jerk off to.
Steve became something of an aficionado of what he considered to be great porn. The girls had to be hot, of course. But they could be young, older, slim, chunkier, blonde, brunette, whichever took his fancy on any given night. The guy, well, he didn’t really care much about how he looked, as long as he had a nice big cock and came a lot. He liked to see a good stiff cock get jerked until the cum erupted and sometimes, he accidentally strayed on to gay sites when he entered “big cocks spurting cum” into the search engine. He’d watch the close-up videos of cocks but wasn’t interested in seeing guys fuck each other. He wasn’t homophobic in any way, it just didn’t do much for him.
But it was on one of these sites, he stumbled across something he hadn’t seen before. It was a close-up of a nice big hard cock, a girl’s hand wrapped around it, jerking it seductively. The pop shot was massive and the girl’s hand was covered in cum. The camera panned out and it turned out to be a hot transsexual, wanking herself off! She licked her own cum off her fingers while cum still leaked out of her cock. This was a bit of a “Crying Game” moment for Steve. He wasn’t shocked about the cock, more that it was attached to such a hot looking ‘woman’. He watched that video over and over, jerking himself off to it, timing his cumshot with hers. It became a firm favourite and it led him to search for more transsexuals jerking themselves off.
Wow, he had no idea of the Pandora’s box he’d opened. There was tons of Trans porn available to look at. Solo jerking, Trans girls being fucked by guys, Trans girls fucking guys and girls, even couples. He especially liked to see Trans girls cumming hard, and although he wasn’t really into seeing guys fuck each other, this was different. He loved anal sex, he loved big cocks shooting huge loads of cum, so watching a guy fuck a ‘Tranny’ (please excuse the word, but it’s used a lot on porn sites) was a natural progression. At least, it was in Steve’s slightly twisted mind!
One of his favourite scenes was where a sexy, slim trans girl was sitting on a guys cock, bouncing up and down on him as it slid in and out of her ass. The camera then pans around to the front, as she lifts off his cock, leans forward, and unleashes a big cum load into the guy’s mouth. He slurps it up eagerly, licking her big cock clean, then she turns around and wraps her lips around his cock. After a minute or two of sucking (Steve thought, if it was him, it would be a second or two…) the guy in the movie returns the favour with a big cumshot of his own. All over the pretty trans girl’s face. Oh boy, that was another favourite, watched over and over again.
After a week or so of watching trans porn and dreaming of actually fucking one himself, Steve was getting the urge to meet with another escort. He visited many large towns and cities in Britain in the course of his work, so there were plenty of girls to choose from. He was searching on a well-known purple website for a girl close to an area he was visiting in the next few days on business. He never played too close to home, for obvious reasons. When he was entering the search criteria, location, can they accommodate etc., he saw one field he’d not noticed before. There was the usual ‘Gender’ ‘Male’, ‘Female’, ‘Couple’ options but there was also a ‘Trans’ box that you could tick. Hmmm, thought Steve. I wonder…
He ticked the box after selecting ‘Female’ but was very disappointed to see only one result. This lady was in her fifties, and not what he had in mind at all. But then he thought, hold on a second. What if I select ‘Male’ and ‘Trans’? What a surprise! 35 profiles appeared, most of which had pictures of extremely hot looking girls. Steve was like a kid in a sweetshop – so many girls to choose from! Not being completely wet behind the ears, he quickly sorted out the ‘too-good-to-be-trues’, the obvious fake pics and the £300 per hour merchants. That left about 5 profiles that looked promising and displayed a phone number to call.
Wow, he hadn’t been this nervous since asking out the pretty girl dancing with her friends at the school disco, but he managed to do that then (she said yes!) and he was determined to call one of these amazing looking trans girls now. Shaking slightly, he picked up his phone and very carefully entered the number shown. Barely hesitating, he pressed send and waited for the ring tone. He didn’t expect to be lucky with the first number, and sure enough, it rang and rang. So he moved on to the second one. Same result. He was starting to think this was a bad idea, but on the third number, it only rang a few times before a seductive voice answered “Hello?”
Resisting the urge to hang up immediately, Steve cleared his throat and said “Hi, is that Rose?” “Yes, darling” came the reply, “How can I help you?” Steve muttered something about her ad and asked if she was free on Thursday at around, say 2pm? “Yes, darling, that would be fine. Text me when you’re near and I’ll give you the full address. See you Thursday, darling”. A text followed immediately with the first part of her postcode, so Steve went straight on to Google Maps to look at the area. It was a part of the city he was visiting that he didn’t know that well, but he knew it was a nice part of town. As he was searching to see if he could find any reviews of this girl, he noticed his hands were still shaking. He did find one review and it was very positive, so he was full of optimism and found himself looking forward to Thursday. His cock was already twitching with anticipation. He decided he would resist the urge to jerk off before Thursday, but still looked at some more Trans porn, to further whet his appetite.
Thursday eventually came and Steve drove to see his client. He knew he’d be finished by about 12 and he only had one thing on his mind. He sent a text to Rose to check she was still OK for 2pm. She replied straight away with “Yes, darling, I’m looking forward to meeting you. Text me when you’re close” Perfect! The client meeting dragged on a bit and Steve left his office just before 12. Just time to grab a quick bite, freshen up, then drive over to Rose’s apartment. At about 1.50pm, he pulled over and sent Rose the text. “I’m quite close, please text me your address when you’re ready.” Being a bit of a softy, he’d bought a small bunch of flowers to take to Rose. He liked to make a good impression with a lady he was meeting for the first time, and felt no differently about meeting an escort than if it was a blind date. The text popped up on his phone with the full address, along with the line “Come straight here, I’m ready for you now”. His heart started beating a little faster now and he realised he was very close to her apartment already. His car was safely parked, so he decided to walk the rest of the way, literally a few minutes. He got to the apartment block and pressed the buzzer, his heart thumping. The door opened and he strode into the lobby, straight up to the lift and pressed the button. As the doors opened, his head was spinning, was he really about to meet with a transsexual girl? And suck her cock? And fuck her? He’d never suffered from performance anxiety before, but he was beginning to doubt whether he’d be up to the ‘task’ ahead. Before he knew it, the lift stopped and he walked towards her apartment. The door was ajar, so he knocked gently and walked straight in. The sight that greeted him made his jaw drop!
Rose was so convincing, so facially pretty, slim, fragrant, Steve thought he’d made a mistake and found a hot female escort. Well, that’s OK, he thought, she’s gorgeous, I’m going to enjoy fucking her. But then he looked down at the pretty panties she was wearing under her basque and was certain he saw a bulge. Rose greeted Steve with a juicy kiss on the lips and a hug. She was so natural and relaxed, Steve relaxed a bit too. She smiled at the flowers and took them from him gratefully.
“Shall we do the paperwork first, darling?” asked Rose. Steve handed over the £150 fee for an hour of Rose’s time and already thought it was going to be his best investment so far this year! “The shower is in there, Darling” said Rose, pointing to the open bathroom door. “Would you like me to join you?” OMG! Yes please! thought Steve. Without sounding too eager, he actually replied, “Sure, if you like.”
He quickly stripped off, turned his phone on silent, and stepped into the bathroom in just his boxers. Rose was already in there, checking the water temperature. She started to undress and Steve was transfixed, watching her beautiful lingerie drop to the floor. She had her back to him and as her panties fell around her ankles, Steve already felt his cock getting hard. Rose turned around to face him. Steve’s jaw dropped for the second time as he looked at her stunning body. Her boobs were beautifully done, her make up flawless, her tummy taut and flat, and, yes, the piece de resistance, her cock, flaccid but quite large, hanging between her legs.
Steve slipped his boxers down to reveal his already erect cock. “Mmmm, that looks big and tasty” purred Rose, seductively. “After you” she said, motioning to the shower. Steve stepped hesitantly into the bath and moved towards the stream of water. It wasn’t too hot, to his great relief, and he wondered what was going to happen next. It didn’t take long to find out. Rose got into the bath behind him, squirted some shower gel into her hands, then proceeded to reach around and rub it into Steve’s chest. Her hands wandered down and Rose soaped all around Steve’s tummy hips and groin. She paused when her hands clasped around his now fully erect cock, leant towards him and whispered into his ear “I love your big hard cock Baby, I’m going to suck it until you cum over my tits” Wow, this girl doesn’t hang around, thought Steve.
As she was whispering in his ear, she pushed right up close behind him and he could feel her cock growing stiff already. Rose started soaping Steve’s ass and naughtily inserted a finger as she did so. Steve nearly came on the spot, this was by far the horniest thing he’d ever done. He let the water rinse the soap from his body, then turned around to see shower gel dripping sown Rose’s tits. He felt it was his duty to soap them up and enjoyed the feel of her fake tits and hard nipples. Rose reached down to stroke Steve’s cock again, commenting on how hard it was. Steve decided he had to feel a dick in his hand for the first time and reached forward, gently grabbing Roses’ growing cock. It felt so strange in his hand, but so good too. He jerked her nervously and Rose giggled a little. “Don’t be too gentle with it, Darling.” Steve smiled and started jerking her cock harder and faster, feeling it grow until it was fully erect. What an impressive sight it was too. Long, thick and hard, as well as being perfectly shaped. If anything, it was even better than the trans cocks Steve had watched in the porn movies.
Rose now backed away a little, pulling Steve closer to him. She crouched down and kissed his belly, then took his cock in her hand and licked the shaft, All the way up to his knob, which she licked lovingly, then wrapped her lips around it. In one smooth stroke, she took Steve’s entire length right into her mouth and throat, no gagging, just beautiful smooth strokes. In and out of her hot mouth, Steve was writhing in ecstasy, telling himself not to cum too quickly. Rose grabbed both his ass cheeks and pulled him into her mouth, faster and deeper with each stroke. Steve started to moan and Rose, being a pro, knew what was about to happen. “Baby, cum on my tits” she said, softly. She pulled Steve’s twitching cock out of her mouth and jerked him hard, aiming for her chest.
“Oh fuck me!” shouted Steve, as he unleashed 3 days worth of spunk all over Rose’s tits. He spurted so hard, some hit her face too, and she giggled as she continued to wank his cock until no more cum oozed out. She rubbed his shiny knob all over her cum covered tits, then kissed Steve’s cock as she stood up. Steve was feeling weak at the knees, but had the presence of mind to kiss Rose before she wiped her face, tasting his own cum for the first time. Rose just smiled and kissed him back passionately. “Have you been saving that up for me, Sweetie?” she asked. “That’s the biggest load I’ve seen for a long time!” Steve’s chest puffed out with pride as he heard this, imagining himself to be some kind of stud! They rinsed themselves off and Rose handed Steve a clean, fluffy towel to dry himself off with. He unsteadily climbed out of the bath, dried himself a little, then followed Rose into her boudoir.
It was tastefully decorated, nicely lit and had a huge bed in the middle of the room. Steve thought to himself I bet that bed has seen some action, but said nothing. Rose offered Steve a chilled bottle of water, which he gratefully accepted. Rose wandered in to her kitchen as Steve dried himself thoroughly and tried to compose himself a little. She returned with a vase containing the flowers Steve had thoughtfully bought for her and she placed it on the windowsill.
“Was that your first Trans experience, Baby?” asked Rose, her beautiful feminine voice teasing him slightly. Steve thought for a moment and decided there was no point in lying. “Yes Honey, I’ve never touched a cock before, never jerked one and never tasted my own cum before, either.” Rose giggled and said “Wait till you get my cock in your mouth and feel me cum, it will blow your fucking mind!” Steve’s cock started growing again as she said this. He loved to hear dirty talk, and coming from those sweet lips made it hornier than anything he’d ever heard before.
Steve and Rose lay on the bed side by side, both naked. Rose absent-mindedly stroked Steve’s head and she asked “Would you like to explore my body some more?” Steve felt like a dog, panting with his tongue out but tried to stay cool. “Yes, please, Baby” he replied. Rose turned on to her tummy and Steve climbed on top of her, so he was straddling her legs. He made a vague attempt to massage her shoulders, then abandoned this idea and decided to kiss her instead. Her skin was soft and smelt delicious. Steve marvelled at how this person, born a man, could have transformed herself into such a feminine, sensuous woman. His kisses moved down from her neck, shoulders and back, down to the small of her back. His hands were softly kneading her ass cheeks and Rose was squirming slightly, enjoying his strong but gentle hands exploring her. He kissed her butt cheeks gently and ran his tongue along her crack. Rose moaned again, encouraging Steve to explore further. He gently parted her ass cheeks and pushed his face between them, taking in the musky scent, rubbing his pursed lips up and down her crack.
Then, he decided to be bold. This was a dream come true with a beautiful trans girl, so he wasn’t going to waste the opportunity. He stuck his tongue out and licked the inside of her cheeks, tracing the shape all around her tight little ass hole. Then, tentatively and gently, he tongued that sexy hole, pushing into it, feeling it give a little as his tongue moved forward. Rose was moaning now, loving the attention. Steve didn’t know what to expect as he did this. There was no real taste, just a delicate smell of sex. “Oh Baby, fuck my ass with your tongue” moaned Rose, breathlessly. Steve thought this sounded like a capital idea and proceeded to move his tongue in and out of Rose’s tight anus, deeper with each push and faster as the tempo of Rose’s moans grew. Steve’s cock was fully hard again and he was dying to replace his tongue with his cock, but Rose had other ideas.
“Slow down a bit, Baby, we have plenty of time.” Steve felt a bit embarrassed, like he got carried away with the moment, but Rose was sweet, knowing she had to guide this ‘noob’. She turned over and lay on her back. Oh My God, thought Steve. I must have been doing something right! Rose’s cock was now fully erect, a magnificent sight with her foreskin stretched half over her knob. “Suck me, Baby” purred Rose. Steve’s head was spinning as he took this beautiful, erect penis nervously into his mouth. He was overwhelmed by the smell and the taste of it, as well as the size. It was as hard as any cock he’d seen in the porn movies and bigger than his own cock and Steve felt it deserved his best efforts. He may have been a novice sucker, but he’d seen enough porn to know what he was doing. Plus, he knew what he liked when being sucked, so he tried his best to combine all this and was determined to give Rose the blow job he possibly could.
When his lips wrapped around Rose’s cock, he felt her foreskin fully retract as he took her length into his mouth. He held it deep inside his mouth for a few seconds, then slowly pulled it out. He ran his tongue all around her shiny knob, using the tip of his tongue and the underside of it before pushing it back into his mouth. He let it touch the back of his throat, and realised it wasn’t making him gag at all. He started to bob his head up and down as Rose sighed with pleasure. “Oh Darling, you are a natural at this” she said, encouragingly. Steve smiled to himself, pleased that he was doing ok. His own cock was fully engorged again and ready for more attention. Steve span himself around so now Rose could reach it with her mouth. They moved into a side by side 69 position and Steve gasped as Rose took his cock into her mouth. They sucked each other in a gentle rhythm, Steve’s hands exploring Rose’s tight ass hole as they moaned and writhed around the bed with pleasure.
Conscious of the time, Steve decided a breather was necessary. He really wanted to fuck Rose now, so they released each other’s cocks from their mouths and Rose reached down to kiss Steve on the mouth. “Baby, that was amazing, but now I want you to fuck my ass!” Jesus, thought Steve, this is really happening! Rose jumped off the bed and grabbed some condoms, some lube and a towel. She also had a large yellow dildo on her bedside table, which she picked up and handed to Steve. She applied some lube to her anus, opened a condom, handed it to Steve and said “Pop this on the dildo, Honey, then stretch my ass ready for your big cock.” Steve dutifully rolled the condom on to the yellow dildo, all the time thinking this was too good to be true. Rose got onto her knees, her ass pushed upwards and pushed a finger into her ass. Steve took the invitation and lifted the dildo up, placed it against her ass hole and pushed gently. After a bit of adjusting the head of the dildo penetrated Rose’s puckered hole and she let out a little moan. Steve pushed it in deeper before letting it slide out, then pushed again, a little deeper. Before long, the full length of the dildo was inside Rose’s ass and she was squirming with delight. She took another condom and tore the wrapper off. Steve, eased the dildo out, dropped it on the bed, rolled the new condom onto his fully erect cock and positioned himself behind Rose. This is it, he thought to himself. Rose reached back and applied a bit more lube to her asshole and some onto the tip of Steve’s cock, which was practically bursting out of the condom now. He shuffled closer to Rose, held his cock in position, then pushed slowly. The dildo had done the trick, preparing her anus perfectly. Steve’s cock slid in to her in one fluid motion. Rose let out a deep moan and Steve couldn’t help himself “Oh my fucking god!” he exclaimed as the sensation of fucking this beautiful girl’s ass overcame him.
He pushed in and out with long, deep thrusts, his hands on her hips, hearing the delighted moans and sighs of Rose, who pushed back on every thrust. She was enjoying this as much as Steve was! After a few minutes, Steve remembered that Rose had a big hard cock swinging between her legs! He reached forward and around her hips and took her dick into his hand, trying to stroke it in time with his thrusting. Rose squealed again as he did this, saying simply “Oh, Baby, yes.” Almost without warning, Rose eased herself off Steve’s thrusting cock and ordered Steve onto his back. “You’re gonna love this, Baby,” said Rose, as she positioned herself on top of Steve. She guided his cock back into her ass and sat down fully onto Steve, his cock fully penetrating her and they both let out a huge moan of pleasure. Steve could now easily reach Rose’s cock so he could wank her as she rode him.
This experience had been even better than Steve had imagined. He felt he had been so lucky to have found Rose, who seemed to instinctively know exactly what Steve wanted. Not only was she pretty, with a stunningly hot body and a lovely big cock, she was sweet and sexy in equal measures. The sight of her riding him, her stiff cock in his hand and watching his own cock sliding in and out of her tight ass was getting too much for him, and he moaned “Oh my god, I’m close to cumming again.” Rose smiled, and said “Not just yet, Baby. Me first.” Steve’s eyes widened as she lifted herself off him, shuffled herself towards his face and started stroking herself hard. She slipped a pillow under Steve’s neck and said, “Come on Baby, you know you want this!” and held her throbbing cock up to his mouth. Steve opened his mouth and Rose popped her knob inside it, stroked her cock again and groaned loudly as she unleashed a massive spurt of cum all over Steve’s tongue. His reflexes took over, and he swallowed hungrily, as another spurt followed and another. Steve counted them, five in all, so much cum in his mouth as he struggled to swallow all the pungent, slightly salty liquid being pumped into him. It tasted amazing. Rose was shaking a little from her massive orgasm, and Steve gently licked the last few drops of cum from the end of her cock, the way he liked it done to him. Rose shuffled herself back a little, then leaned forward and gave Steve a full-fat kiss, pushing her tongue into his mouth, tasting her own spunk, sharing the taste.
Steve’s condom-covered cock was twitching like crazy now, ready to blow. Rose was kneeling between his legs, so she reached down, ripped the condom off and quickly wrapped her mouth around Steve’s glans. Steve, head propped up on the pillow, was able to watch his cock slide in and out of Rose’s mouth and the sight was too much for him. He warned her he was about to erupt, expecting her to pull back and finish him by hand, but she kept on sucking. She moved a finger down to his anus and slipped it inside him and that tipped Steve over the edge. He felt like his cock was exploding as he emptied his balls into Rose’s mouth. His head span and his heart was beating out of his chest and he easily matched Rose’s five spurts. She was looking him in the eye as he came and he would never forget the sight of her lips wrapped tightly around the base of his cock. Some cum dribbled out of the corners of her mouth, but she swallowed most of it. Then, when his cock had stopped twitching, Rose came up for air, still smiling, and leant in for another full-fat, cummy kiss. They laid on the bed for a few moments as they recovered from this marathon session. Steve did manage to say something and he held Rose’s hand. “Um, will you marry me Baby?” he asked politely. Rose giggled and said “Sure, Honey, what day is good for you?” “Are you free tomorrow?” he asked.
They laughed and kissed playfully as they cleaned up and got dressed. Steve felt like he’d been on the best date of his life and Rose teased him about their forthcoming “wedding”. Steve knew this had been no ordinary encounter. As he put his watch back on, he saw that it was nearly four o’clock. He had spent almost two hours with this lovely girl and felt a bit guilty, so much so that he asked her if he should pay more as he’d run over by so long. Rose replied “Honey, I was having such a good time, I didn’t even notice. You can make it up to me on our wedding night!” She followed this with a big smile and another kiss.
“Will I see you again, Steve?” she asked.
“Are you free tomorrow?” he asked, in reply.