A Pleasant Surprise

A Pleasant Surprise

A romantic transgirl adventure

Chapter 1 by RisisWrites RisisWrites

“Thomas Edwards?” the teaching assistant droned in that exquisitely dull monotone that only disinterested TA’s seemed to be able to produce.

“Here!” Tom replied, perhaps somewhat overcompensating for the complete lack of attention he’d been paying with an overly enthusiastic response. Maths was not his forte, and his attention had wandered less than thirty seconds into roll call, in mere anticipation of the boredom that was inevitably to come. Bored out of his mind as he was, Tom almost missed his best friend Josh whispering to him from the next desk over.

“Dude, there’s someone looking for you!”

Tom pushed his long brown hair out of his eyes and gave Josh a blank look, Josh was always trying to make the most mundane news as dramatic as possible.

“Yeah? And who could that be?” he replied dryly, straightening his glasses unnecessarily.

“Ellie Addison” Josh answered, suddenly grinning from ear to ear.

Tom looked disbelievingly at his friend. Everyone knew Ellie Addison, she was quite possibly the hottest girl on campus. Officially, she’d never had a boyfriend, but there were rumours that occasionally she zeroed in on certain people, guys, girls, there didn’t seem to be a pattern and… well the rumours weren’t specific. But the people she picked always seemed to drift along on cloud-nine for the few days after Ellie had singled them out.

With all of this running through his mind, Tom whispered furtively back to his friend, “You’re sure? Where’d you hear this?”’

Impossibly, Josh’s smile widened, “She asked me where you were now, what class you had next and how you usually got home. Odds are she’ll be waiting for you after the tutorial. “Josh’s smile shifted to a slightly curious look before leaning in closer and whispering, “You do know about… you know she’s trans right?”

Tom nodded numbly, even though she’d moved towns after high school, the news had followed her, everyone knew that Ellie had, only a few short years ago been Eddie. Tom wasn’t sure that would have bothered him, even if she hadn’t been the hottest girl at their Uni. It’s not like anyone would have guessed. If the local gossip hadn’t revealed Ellie’s past, people would be entirely ignorant of her ‘assigned at birth’ gender or her deadname.

“What does that even matter dude, you’ve seen how hot she is, even if half the rumours are true…” Tom trailed off, if half the rumours were true, he was about to have one of the best afternoon’s of his life. Tom just hoped that Josh wasn’t messing with him…

The rest of Maths tutorial passed in even more of a distracted blur than usual. Tom was only taking this subject so that he could spend some time with Matt, and it happened to fit nicely into his timetable. So he was able to fully occupy himself with daydreaming about what Ellie might have in store for him.

Even still, an age seemed to pass before mercifully, the TA dismissed them. Leaping to his feet, Tom rushed to be the first person out of the room, pushing past his classmates until he reached the door, but something stopped him and only a few metres short of the door he froze. Tom’s brain caught up with him and he remembered how very out of his league Ellie was. What was he thinking?

Slowly the rest of the class filed past Tom, some of his classmates giving him weird looks as they passed him in his frozen contemplation, until it was only Josh and Tom left in the room.

“You okay dude? I thought you were excited?” Josh asked, looking concernedly at Tom.

“I- I was, then… I mean… I’m me and… she’s Ellie Addison.” Tom muttered dejectedly.

Josh clapped him on the shoulder and smiled, “Look, you’re no jock with oversized bulging muscles, but you’re not the worst looking guy and you’re funny. Chicks love that. Chin up, I’ll see you tomorrow.” Josh opened the door ahead of him and headed left, off towards where the buses would whisk most of his fellow students off across the city to their various homes.

Allowing himself to feel somewhat reassured by his friend’s pep talk and reasoning that if Ellie had asked after him she had to at the very least be somewhat interested already, Tom arranged his features into the most charming smile he could manage and pushed open the door to see-

Nothing.

No one was waiting for him, the corridor was practically deserted. Face reddening in embarrassment, Tom walked off sullenly towards his car. Josh must have been messing with him again, although this was an unusually cruel prank from his best friend. Tom was in such a mood and so lost in his thoughts that by the time he got back to his car he completely and utterly failed to see the smoking hot girl lounging casually on the hood of his beat up old ford.

“Hey Tommy”

One hand on his car door handle, Tom’s head snapped up at the voice and his mouth fell open at the sight of the girl sitting cross-legged on his car’s bonnet. Her long shapely legs led into a perfectly toned body, including her unquestionably full and generous chest. Her stunningly beautiful face was framed by gorgeous long curly blonde hair. Her outfit consisted of a very short pleated black skirt and white blouse which looked to be stretched to breaking point over her killer figure. Ellie Addison sat with a mildly amused smile resting on her features.

“Picture would last longer you know” she said quietly with a giggle as she slid down off of Tom’s car.

“Uh- well- I-um” Tom stuttered, struggling to form a cohesive thought, let alone a cohesive sentence.

Ellie paced the few steps required to close the distance between them and stood barely a foot in front of Tom, effectively pinning him with his back to the car. She gently placed a hand over his mouth to silence the stream of stuttering that Tom was doing his very best to make coherent.

“Now… I know what you’re probably thinking… What is happening right now?” she said, favouring him with a beaming smile. “Just how’d I come to have, not just A blonde bombshell, but THE blonde bombshell sitting on the hood of my car?” Ellie leaned in ever so slightly, as if confiding a secret with him, whispering in his ear, “The answer is simple, girls like me… we tend to have a lot of trouble meeting people, cause most people are too scared to approach us and those that do, are probably only interested in us... in the bedroom.”

As she spoke, Ellie slowly slid her other hand up until it was resting gently, but firmly on Tom’s chest. “So what I do is, I approach people I like the look of, and I see what happens. Sometimes nothing happens, whether it be because we’re really not compatible the way I thought we were” she said, leaning in further, “Other times I make a good friend to hang out with and sometimes… well you’ve probably heard the rumours…” Ellie trailed off, leaning back slightly as if gauging his reaction.

“Obviously, I can’t just demand we hang out cause that would be terribly rude of me, but-“ Ellie trailed off, leaning in again until her hair brushed against his face and Tom could feel her breath on his neck. Ellie gently slipped a piece of paper into his top pocket and whispered in his ear “This is my address and I’ll be free in about an hour. I just might see you there, who knows?” she said, shrugging mysteriously. With that, Ellie planted a kiss firmly on Tom’s cheek, turned on her heel and began striding away.

Tom’s brain only began to actually start working properly when Ellie’s swaying ass was very nearly out of view. Shaking himself physically, Tom pinched his hand not-so-gently.

“Definitely awake” he murmured quietly to himself as he slumped into the driver's seat of his car, the after effects of having Ellie’s body so very close to his still clouding his brain, making it very difficult to think. Eventually, he had the presence of mind to slip the piece of paper Ellie had placed in his pocket and read it, if nothing else to prove to himself that what had happened hadn’t been some kind of hallucination. Sure enough, written on the paper, was an address for a house in the upscale part of town. Looking at his watch, Tom came to a decision.

One hour… That left him with just enough time to get home, take a quick shower, get changed and find his way to Ellie's house. Tom turned the key in his car, the old ford rumbling to life as Tom put it in gear and drove like hell.

Tom pulled into the driveway of the address that Ellie had given him; he'd been around the block twice already, trying to work up the nerve to park, telling himself that he was just making absolutely sure that the number was correct. Finally, deciding that he was wasting fuel, Tom pulled into the large ornate driveway and parked as far out of the way as possible.

Tom stared in awe at the size of the place as he walked up the path to the front door. Knocking on the door, Tom wiped the palms of his hands on his jeans. Back at home, his nerves had almost gotten the better of him several times and in a particularly strange moment of panic he’d almost considered wearing a suit, but common sense had finally prevailed and he was wearing a more casual jeans and t-shirt, under his warm coat.

The seconds dragged by, Tom was just on the verge of walking off and assuming he’d been given the wrong address when Ellie swung open the door smiling and Tom had to actively concentrate on not letting his draw drop. Ellie was dressed simply, in a snug fitting white and red sundress. But the way the dress started very late on its way up her legs and stopped very early after it had technically done its job in covering her chest, showed off an eye catching amount of cleavage as well as every other delightful curve Ellie had to offer, and those were both numerous and delightful.

Ellie’s smile seemed to grow watching Tom’s gaze drift slowly up and down her body, “I could grab you that camera if you want, or you can come inside” she quipped, putting her hand on her hips and leaning casually against the door frame and gesturing for him to head inside, “Up to you.”

Some of Tom’s senses returned to him just quickly enough to make a witty retort. Stepping past Ellie on his way inside he remarked, “The rumours said you were hot, they failed to mention you were funny too.”

Ellie laughed, the mere sound making Tom’s stomach do backflips, “Oh so I didn’t completely melt your brain with the dress? I’ll have to try harder next time.”

Closing the door behind him,, she took Tom by the hand, pulling him deeper into the house. “Come on, I’ll give you the tour later… Well, if you want the tour and I haven’t scared you away by then” she elaborated, gesturing around the admittedly impressive living room, “My room’s out the back.”

Tom allowed himself to be dragged on, but his brain was working overtime trying to take in both the fact that the most beautiful woman he’d spent any kind of time being near was holding his hand, the high ceilings, expensive looking art and the very fancy looking rooms he was being dragged through. “Some place you got here.” He managed to comment at last.

“Thanks! Well, kind of. It’s not really mine after all. My Dad does fancy things with computers” she explained, “I don’t mean to brag on his behalf, but you can tell from the house he’s not completely rubbish at it” Ellie said with a smile over her shoulder.

“You can say that again.” Tom murmured as he was dragged past room after room after room. Finally they came to the back of the house with a door labelled simply, Ellie.

“Home sweet home,” Ellie said, opening the door and pulling Tom gently inside, “It's the smallest room in the house, I picked it cause it felt more… normal, I guess.” For the first time since Tom had arrived, Ellie seemed a little unsure of herself, waiting for his reaction.

Tom smiled, looking around,“Nah I get it, andI like it. I’m used to being cosy at home, so the rest of the house was a little overwhelming anyway” he said, waving his hand dismissively.

Ellie brightened at the compliment, “I’m glad you agree. Well now that you’re here… whatcha wanna do?” she asked, pulling herself a half step closer to Tom and snaking her other arm around the crook of his elbow.

Ellie’s bright blue eyes bored into him curiously and Tom felt a sneaking suspicion that he was being subjected to some kind of test. Having Ellie standing so close to him again was not doing wonderful things for his concentration. Nonetheless, not wanting to seem too eager, nor entirely uninterested, Tom used the hand that was still holding Ellie’s to point at the Xbox he spied, sitting in the corner of the room. “Why don’t you show me what games you’ve got on that thing and whether you’re any good at them?”

Ellie’s almost perpetual smile broadened into a grin, “Oh you’re so on.” She gave Tom a gentle but forceful enough shove to push him over onto his back, landing comfortably on her bed and into its mountain of pillows. Ellie quickly fired up the Xbox, grabbed some controllers and threw herself down next to Tom.

It turned out that Ellie was very good and Tom spent the next hour cheerfully losing round after round at whatever game he nominated. Over the course of the hour, Ellie seemed to scoot closer and closer, until it came to be she was laying back, one of her arms tucked through his comfortably with her legs lying across his lap.

“You have got to be cheating.” Tom complained, as Ellie thrashed him in yet another round.

“You just wish you had these mad skills.” Ellie retorted as the game scrolled through their scores for the round. For the first time since they’d sat down, Tom glanced across at Ellie, and noticed properly for the first time that the hottest girl he’d ever spent any kind of time with was now draped very casually across him.

Ellie looked away from the TV, noticing him noticing her and smirked, “I swear to god, if you want that camera dude, just ask.”

Tom gave her a weak smile but his earlier bravado deserted him and he suddenly felt very unsure of himself, “I- Ellie…”

Ellie shifted her weight, moving so that all of a sudden she was settled comfortably kneeling across his body, straddling his waist. Moving with a slow but steady pace, she snaked her arms around the back of his neck, resting her forearms on his chest as she leant in closely. Her weight was largely resting in his chest now and leant in and whispered quietly, her face only a few inches from his.

“Would you like me to kiss you now Tommy?”

Time seemed to stand still for Tom, a few short hours ago it had just been just another boring day and now here he was, in the bedroom of one of the hottest girls he’d ever met, being asked if he would like her to kiss him. Tom smiled a slow smile, drawing confidence from Ellie’s calm and comforting demeanour, the smell of her perfume filling his nose as she waited patiently for his answer. Looking up into those bright blue eyes, Tom felt something relax inside him for the first time all afternoon, “I think I’d probably be pretty stupid to answer any other way now wouldn’t I?”

The glint in Ellie’s eyes was intoxicating, “Good answer” she said simply before closing the remaining space between them and pressing her lips firmly against his. Tom had kissed a few girls before, he’d even had what he’d considered to be some pretty good kisses. But all those paled in comparison to that kiss he received from Ellie Addison. Tom’s brain briefly misfired at first contact with the soft perfection that was Ellie’s lips. Luckily his instincts carried him through the few moments with a complete lack of thoughts travelling through his brain. And so it was somewhat of a surprise to himself that he found himself kissing her back for all he was worth. Seemingly without any conscious thought on his part a small moan escaped his lips.

Smiling into the kiss, Ellie took one of Tom’s hands in hers and blindly placed it firmly on her lower back. Taking the hint, Tom moved his other hand up to get tangled in her hair, tightening his grip slightly, pulling Ellie down towards him.

As they kissed, Tom let his hand wander slowly down Ellie’s back until it was resting gingerly on her ass, his fingers resting on the edge of where her dress ended. Ellie responded by grinding lightly on Tom’s lap in approval and taking this as permission to be a little bold, Tom let his hand slide just a touch further down Ellie’s round ass until it slipped underneath her dress and he squeezed the bare skin of ample behind.

His boldness earned him a soft moan from Ellie, “Someone’s getting brave.” she quipped, taking the time to lean back a moment and give him a smirk. Tom could feel something hard against his stomach and realised with a start that it must be a bulge from Ellie’s underwear. Tom wasn’t too surprised, his own cock was straining visibly against the material of his jeans.

Ellie slowly tugged at the hem of Tom’s shirt before pulling it up and over his head without resistance. Ellie placed both hands on his chest and gazed deeply into his eyes. “Now listen a moment, if I make a move you don’t like, you tell me to stop, okay?” Tom went to nod but Ellie gently placed a hand on his check to stop him, “I mean it! I know you’re mainly thinking with your dick right now, but please talk to me if you’re uncomfortable, I promise I won’t be offended, I just want you to be honest and comfy and have fun.”’

When he nodded a second time, this time after a short moment’s contemplation, she smiled that beautiful smile of hers. “Well in that case, give me a hand with your belt.

Fumbling to comply, Tom undid his belt and no sooner was it loose than Ellie had his jeans and underwear sliding down his legs and onto the floor. Tom’s hard cock bounced to attention as soon as it was free and Ellie stared admiringly at it. “A little bigger than average, but nothing I can’t handle.” she said with a confident smirk.

Tom smiled slightly, finally sensing an opportunity to score a point in their verbal contest, “Now, If you wanted a camera- oh shit.” Tom’s jest was cut short as Ellie placed one hand firmly at the base of his cock before unceremoniously taking the head into her mouth and gliding smoothly down about two thirds of its length without pause or hesitation.

The moan that this sudden effort drew from Tom made him blush fiercely, but Ellie didn’t pause to allow him to recover. She bobbed up and down his length, settling into somewhat of a rhythm as she worked his cock skillfully. Tom’s breathing began coming in ragged breaths as Ellie worked. He let his head fall back onto the bed sighing pleasurably, “Jesus christ Ellie, where did you learn to do this?”

Ellie blushed and made a popping sound with her mouth as she let Tom’s cock slide out of her mouth. As she spoke, she continued stroking his cock with her hand, not giving him even a moment to get used to the sensations flooding his body. “Lot of practice with a dildo, some experience with guys.” she said with a shrug, a grin forming on her lips, “One thing I do know from the latter, is that you’ll love this.”

Without another word, Ellie plunged his cock back down her throat, sliding smoothly down the entirety of his length before bottoming out with her nose pressed firmly against his groin. Tom moaned deeply as he managed to prop himself back up on his elbows to look back down at Ellie as she looked up at him. Her eyes watering slightly with the effort of holding the entire length of his cock down her throat and after what Tom felt like a small age, Ellie gave him a wink before slowly letting it slide from her mouth, sucking in a huge lungful of air. Tom was left panting, but for an entirely different reason.

“That was astonishing” he murmured groggily.

“I thought you might like that,” she said with a smile before resuming her steady pace from before, while Tom could only nod faintly in agreement.

Apparently satisfied that Tom had been sufficiently impressed, Ellie seemed to quit playing around, increasing her pace on Tom’s cock. The only sounds in the room were the regular wet slurping sounds coming from Ellie’s mouth as she worked furiously on Tom’s cock and the quiet moans he made became increasingly regular and increasingly less quiet as he slowly began to feel his orgasm build.

Tom managed to stutter out, “El-Ellie I’m getting c-close” and as if that was the signal she had been waiting for, Ellie used the hand that wasn’t holding Tom’s cock to start massaging his balls gently. The unexpected, but pleasant sensation drove Tom over the edge and with a loud grunt, he started to pump his load right down the back of Ellie’s throat, legs twitching uncontrollably as the most intense orgasm of his life ripped through his body.

Ellie held on determinedly and after what seemed like an eternity to Tom, Ellie allowed Tom’s cock to slip from her mouth and with a visible effort, swallowed down the load of cum Tom had just deposited down her throat.

“I gotta say-” she said, crawling up to lay against his side, her chest pressing comfortably against his, “that was extremely hot. And secondly- fuck that was a lot of cum, you been stockpiling or something buddy?” She asked jokingly, playfully poking his deflating dick.

Tom blushed deeply, suddenly becoming aware that he was completely naked while Ellie was still very much clothed and draped very intimately down his side. “That was um- that was amazing Ellie. Thank you” he murmured quietly.

Ellie giggled, “Hey don’t mention it, I enjoyed myself too you know.” Looking into his eyes, Ellie slowly leaned up and kissed him once more

Ellie’s lips moved slowly in time with his, still firm, but more sensually than their first kiss. As she pulled away, Ellie nibbled gently on his lower lip and Tom opened his eyes to see Ellie’s blue eyes gazing deeply into his own. “Congratulations Thomas Edwards, you’re a first.”

Tom fronted up at her in confusion, “A first? In what?”

“Well, you see,” Ellie explained, adjusting her dress slightly where it had ridden up, “I’ve had a number of guys- and some girls, over before. A few of them got, if I do say so myself, the special treatment you just received.”

Tom blushed and murmured, “Yeah… that was pretty special alright.”

Ellie grinned down at him and continued, “Others did what you did at first and suggested something more… casual, and we hung out, had a good time but didn’t go any further” she explained, “None so far, have managed to squeeze both into a single afternoon quite so seamlessly.” Ellie looked past him for a moment as if distracted, “So I can’t help but think, that maybe that might mean something.”

Looking back down at him and fixing him with the full power of her piercing blue eyes, Ellie asked a surprising question, “Would you like to go out sometime?...” Ellie seemed to trail off and lose confidence towards the end of her sentence, “like a date… like a date date, with me. Out somewhere, dating.” She finished all at once in a rush, as if saying the words quickly made them easier.

Tom thought briefly about their afternoon, the easy banter they’d shared while gaming and the chemistry they seemed to have physically. There really wasn’t much decision to make. “I think I’d like that.” He said simply.

Ellie frowned a little at him, “And you wouldn’t have a problem with people knowing you were dating a trans-girl?” The surprise in his eyes must have given her cause to elaborate, “I know you might not care, otherwise you might not have let me stick my tongue down your throat quite so enthusiastically just now, but do you care at all what other people might think? Some people at school…” she trailed off, leaving unsaid what some people at school might think.

“Fuck those people,” the venom in his voice surprised even Tom, “I had just about the best afternoon I can remember having in a long time and um… I’m not just talking about the blowjob” he said blushing, ”I mean you’re a lot of fun to be around too. I’d love to go out sometime.”

Ellie beamed down at him and gave him another peck on the lips, “You know just what to say to make a girl feel better you know?” she said laughing.“Speaking of feeling better,” Tom said, remembering that Ellie had basically been the only active participant this whole time, “Would you like me to make you feel better… physically?” He asked, blushing red.

Ellie laughed again, “You know you’re adorable right?” Ellie took Tom’s hand in hers, “I appreciate the offer, but this was all on me. You have to earn any more of this” she said, running his palm gently down over the top of her dress, across her chest and down her side. “This is just to drive you crazy in the meantime” she teased, smirking at the hungry look in Tom’s eyes as he felt her up through the fabric of the dress.

“You know you’re an awful tease right?” Tom complained as Ellie rose gracefully from her position next to him and stretched.

“Yeah, but I’m also very much worth the wait” she replied easily, watching Tom as he slowly gathered his clothes and slipped them back on. “Now, sad as what you're about to hear is, I actually have a lot of classwork to catch up on, you’re welcome to stay and hang out. I’d hardly kick you out after inviting you over like this, but you’d have to let me work, interested?”

Tom grimaced at the mention of classwork and remembered his own pile which was still waiting for him at home. “I’d love to, but my own pile of assignments is calling. Can I ah… grab your number though?” he asked, suddenly nervous.

“Nah, I played games with you all afternoon, sucked your duck then asked you out, but you can’t have my number, that’s going too far.” Ellie replied sarcastically, gesturing for Tom to hand over his phone.

“Alright, alright, no harm in being polite,” grumbled Tom, surrendering his phone. When she handed it back, he noticed the contact name she’d set for herself was ‘THE blonde bombshell.’ “Not just a little bit cocky?” he asked, raising an eyebrow.

“You tell me, was the blowjob the best you’ve ever had or was it the best blowjob you’ve ever had? Feel free to answer in your own times” she replied, folding her arms and smirking.

“Okay okay! You win Blonde Bombshell, you win” Tom answered, raising his hands defensively, which Ellie used as an excuse to run her hands around his waist, pulling him in for another quick kiss before taking his hand and lending him back through the house. As they made their way back to the front door, Ellie glanced occasionally back at him and smiled, almost as if to remind herself he was still there.

Finally making it to the front door, Ellie leant down ever so slightly to kiss Tom once more, “Have a good afternoon now, try not to miss me too much.”

Tom grinned back up at her, “Yeah yeah, I’m sure I’ll struggle on somehow.” He pulled her in for a hug, which she warmly reciprocated, wrapping her arms around his waist. Tom was simply enjoying the kiss, the novelty of Ellie being so close to him still far from having worn off when he felt one of her hands slip down his waist to grab teasingly at his ass. Tom jumped slightly in surprise, only pressing himself more firmly against her as Ellie giggled, breaking the kiss.

“See you soon Tommy” she murmured, giving him a small wave as she pulled away from him. Tom returned the wave before slowly making his way down the short flight of stairs from the door. Ellie disappeared back inside the house, swinging the door shut behind her.

As he climbed into his car, Tom thought to himself that he was fairly certain that he’d probably end up struggling not to miss her after all.

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