A Pleasant Surprise Pt. 07

Author's Note: All individuals depicted are over 18, this is an adults story concerning adults.

The rest of the week passed slowly for Tom, until on Friday night when he found himself parked outside Ellie's house, a bag of clothes and other essentials in his hands and making his way up the stairs to Ellie's front door.

Their school schedules had made it impossible for Tom and Ellie to hang out after school any time that week, but Ellie had proposed they spend the weekend at hers again as her Dad was out of town again this weekend.

-E: so... if we've got the whole weekend to ourselves... I was wondering...

-E: you remember we talked about you trying anal maybe?

-T: That I do

-E: still interested?

-E: tom?

-T Sorry, Yes! I'm still interested, just you know... Slow, right?

-E: of course babe! we'll take it nice and slow <3

The appointed day now arrived, Tom admittedly, a touch nervous rang the front door bell and was almost knocked off his feet when the front door swung back suddenly and Ellie leapt into his arms. Ellie was dressed simply, but with a figure like her's, booty shorts and a tank top looked damn good.

"You're here! I missed you" she said, clinging fiercely to him, "It feels like forever" she mumbled.

Tom smiled to himself, pulling her against him, "I missed you too gorgeous."

Ellie sprung apart from him and ushered him inside, "Soo, I took a liberty and I'm hoping you're okay with it." Ellie said, leading him quickly through the house and back towards her room.

"A liberty?" Tom asked, "What do you mean?"

"Wellll, we've had a bit of a week, what with getting official and all last weekend, you getting slightly beatenb up, meeting my friends, it's been a big week! So I thought..." she trailed off as she opened her bedroom door. Inside there was a table which was overloaded with a stack of pizza boxes, a box of garlic bread and a bottle of wine. A projector was setup in the corner of the room and Ellie's bed and was piled high with pillows and blankets. "...move night?" she asked with a big cheesy grin.

Tom looked down at her with a grin of his own, "You set all this up? This is amazing!" he said with a laugh, "Why is there so much pizza?"

Ellie blushed, "I didn't know your favourite flavour and I got carried away..." she admitted. "It'll be good for leftovers," she said, with a dismissive hand gesture. "Do you like wine?" she asked hesitantly.

Tom shrugged, "Not really? But-" he began to say, but Ellie cut him off.

"Thank god, I don't either, I just thought it was kinda romantic" Ellie said in a rush, "I have some other stuff in the fridge." Ellie looked around the room, looking for anything out of place, "Do you like it?" she asked at length.

Tom pulled her in for a kiss, placing his hands on her waist. After a long moment they broke apart, he looked up at her and whispered, "I love it, this is so thoughtful, thank you."

Ellie looked down at him and smiled, "I'm glad" she said, before leaning down to give him another kiss. Pulling away again, she went to go back through the door, "I'll grab some... less sophisticated drinks, you make yourself comfortable and think of something to watch."

"Will do" Tom murmured to himself before turning back to the bed and negotiating his way up the enormous mound of pillows to find somewhere comfortable to sit. Just as he managed to wedge himself into a kind of pillow nest, Ellie returned with a variety of drinks in hand.

"So, what're we watching?" she asked, pouring him a glass of something which smelled powerfully alcoholic.

Tom wracked his brains, trying to think of a good movie, "Pirates of the Caribbean?" he asked questiongly.

Ellie nodded enthusiastically, "Oh my god, I love those movies! I haven't seen them in forever, plus..." she trailed off looking slyly at Tom and handing him his glass, "I know a good pirate related drinking game."

Tom laughed and took the drink proffered drink, "If it's everytime they say "Arr" we are going to get absolutely plastered" Tom observed as Ellie gracefully climbed the pillow fort with a drink of her own and settled in amongst the pillows, snuggling them comfortably together.

"Kinda the point" she said shortly as she pulled up the movie, "I wouldn't complain if I were you, I get very wanting of make-outs when I'm drunk" she said with a sly smile.

Tom raised his hands in acceptance, "By all means then" he raised his glass in a toast, "To getting plastered."

Ellie mimicked the toast giggling and started the movie, "Now - you have to take a drink whenever Jack Sparrow says "savvy," you have to drink whenever anyone mentions the black pearl, you have to drink whenever anyone on screen drink, also..."

Tom paled slightly as the list of things requiring a drink expanded and resolved to take small sips...

————————————————————

Tom woke groggily, the last thing he remembered was putting on the 3rd Pirates of the Carribean movie, "At World's End" and stumbling back into bed with Ellie. He also remembered wearing a scarf around his head like a pirate and Ellie trying to convince him to teach her how to use a sword. Taking note of his surroundings he could see there things were considerably less neat and tidy than they were last night. His and Ellie's clothes were strewn across the room and Ellie's bra was hanging from the ceiling fan. Ellie herself was pressed comfortably up against him and he had one arm draped lazily across her chest. Tom reasoned that they must have fallen asleep spooning, but although they were both naked with the exception of their underwear, Tom noted with some confusion that Ellie was wearing one of the spare pairs of his underwear he'd packed and he was wearing a lacy thong which were nestled between his cheeks. Tom was surprised by how comfortable he found them and the feeling of the silky material against his skin.

He must have made some small movement because a soft groan escaped Ellie's lips and she shifted slightly against him, wriggling her ass against his crotch. "Ohhh God" Ellie murmured painfully, "I have regrets" she said, turning slightly to face him, blinking groggily.

"We drank much too much" Tom agreed, kissing her affectionately on the forehead.

Ellie forced her eyes open and squinted up at him, "How bad's your head?" she asked.

Tom smiled, "Not bad actually, I don't have a headache I just feel like crap" he admitted, rising to lean on his elbow.

"Can I be a total bitch and ask you to get up and make coffee?" Ellie asked, "Assuming you know how to make coffee?" she added, almost as an afterthought.

"You're not a bitch, you're my gorgeous girlfiend, and I definitely can make coffee" he replied with a soft laugh. Slipping out from underneath the covers, he tugged on a hoodie from his bag and trudged into the kitchen, and started searching through cupboards for coffee making things. "Best boyfriend ever" he heard Ellie call faintly from the bedroom. Several minutes later he returned to the bedroom with coffee only to find Ellie turned over and fast asleep again. Suppressing a laugh, he set the coffee down next to her bedside table and went back out to the kitchen to see what food was in the fridge.

Sometime later, Ellie crept out of the bedroom, still in his underwear but with the addition of an oversized t-shirt. "I smell food" she mumbled as she came down the hall cradling her coffee, "Did you go out?" she asked, but stopped short when she finally made it to the kitchen.

"I hope you don't mind... I cooked some of the food you had in the fridge" Tom explained, gesturing to the selection of plates covered in aluminium foil to keep them warm. He began removing the foil as he talked, "Bacon and sausages are traditional hangover cures and I made scrambled eggs because that seemed the safest option."

"You made all this?" she asked, as Tom turned to grab some cutlery from the drawer, Ellie noticed the thong Tom was still wearing, "Are those mine?" she asked curiously.

Tom turned back around and traced her gaze, "Oh! I- I woke up with them on and then kinda forget, I- I'll go- I'll get changed" he stuttered out and began to move back towards the bedroom but Ellie grabbed his arm.

"No wait! They look good" she said appraisingly, "they show off your ass" she said running a hand over it appreciatively, finishing with a slap.

Tom jumped slightly at the slap and blushed deeply, "Oh... well thanks" he mumbled. "Here" he said, handing her a plate and serving some of everything.

"This looks really good too" she continued, looking over the spread of food Tom had made before pulling him in for a kiss. Ellie's lips were warm and "Like really good, this was really nice of you" she murmured as they separated.

Tom scratched the back of his head, "Well, after last night I figured you would A, appreciate it and B, deserve it, after you put on movie night" he said.

Ellie pulled up a stool from the kitchen bench and began digging into breakfast, Tom made himself a plate and joined her. After finishing her breakfast, Ellie moved so she was standing opposite him across the kitchen bench facing him, leant down on her elbows, her head in her palms. "So," she began, "Are you still keen for today?" she asked.

Tom nodded, as he finished the last of his own breakfast, "Yeah, I'm um... a little nervous, but I'm still excited to try, what did you have planned?" he asked, but Ellie shook her head.

"I'll take care of the itinerary, your job is to relax and enjoy yourself, what I will tell you is that we're going to start with a massage," she said, fixing him with a seductive smile, "because you really seemed to enjoy that last time and then we'll start small and work our way up" she finished. "If at any time you want to tap out, just let me know." Ellie explained, "But I think you're going to be surprised by how much you enjoy it," she said with another smile.

Tom smiled back, feeling himself relax with Ellie's reassurances, "It sounds like you've really thought this through" he replied.

A flicker crossed Ellie's features and she broke eye contact, "Yeah.. I have... my first time doing anal was much less... romantic, I guess you'd say, so I've throught about what I would have wanted my frist time." she explained, before shaking herself out of her reverie "But that's a story for another time, what I want you to do, is go amuse yourself for 20 minutes or so, I'm going to get setup."

"You want a hand?" Tom asked, getting to his feet as Ellie headed back to her room.

Ellie turned to look at him over his shoulder as she walked, "What'd I say your job was?" she asked rhetorically. Tom followed Ellie as she made his way back to her room and watched as Ellie took a duffel bag out of her closet before heading off to the bathroom, "I'll call when I'm ready!" she called over her shoulder, before closing the door behind her. Tom settled down on the bed, took out his phone and pulled the blankets back across himself, wondering all the while what Ellie had in store for him.

Almost exactly 20 minutes later, Tom heard Ellie's voice call him from down the hall and he climbed out of bed and made his way down the hall. Standing in the doorway of the bathroom, Ellie was dressed in a partially transparent, lacey robe over a black string bikini. "Ready for you" she said in a sultry voice, before beckoning him inside.

The bathroom had been transformed, the lighting was dimmed and candles were spread out across the room, casting shimmering flickering light over everything. The spa bath was full with warm bubbly water and in one corner of the room a sturdy looking massage table had been set up. Finally, Tom noticed, a line of butt plugs and dildos, arranged in increasing size order, was arranged neatly on a shelf.

"First of all" Ellie murmured in his ear as she closed the door behind him, "Take off all your clothes, the spa is first." Obediently, Tom stripped off the hoodie and underwear he'd been wearing as Ellie shrugged out of the robe, showing off her delicious curves.

"You look really great" Tom mumbled, slightly tongue tied with nerves as Ellie gently took his hand and led him into the almost scalding hot water. Tom took a seat on one of the spas edges and Ellie followed him in.

"I had to dress up for the occasion didn't I?" she asked with a giggle as she settled herself on Tom's lap, straddling him. "Besides, I can see my efforts are being appreciated" she murmured as she leaned in, taking his rapidly hardening cock in one hand and stroking it gently.

Tom let out a small moan at the contact with his dick, before the sound was muffled by Ellie's lips delicately pressing against his own. Tom's senses were on fire and he let his hands roam over Ellie's gorgeous body. Tom placed one hand over the knot which held Ellie's bikini top in place, "You mind if I?..." he asked, gazing up at her.

Ellie shook her head with an amused smile as he pulled gently on the string, releasing her luxuriously soft and perky tits, "I didn't think the top would last long around you" she murmured as she leant back in for another kiss. As Ellie continued stroking his cock ever so gently, Tom took a handful of her boob in one hand and massaged it eagerly.

"You're so beautiful" he murmured, pulling her close and she smiled into the kiss, giving his cock a squeeze.

Once Tom's cock was well and truly hard and Tom himself was thoroughly aroused, Ellie pulled back and reached for a bottle of lube which Tom hadn't noticed until just now. "We're going to start with some fingers to warm you up" she explained, coating her fingers in what looked to Tom like an awful lot of lube. Ellie moved close to Tom again, seating herself next to him and resuming her slow stroking of his cock. "Ready?" she asked looking deep into his eyes.

Tom nodded and felt himself tensing up as Ellie slid one hand slowly towards his ass, "Hey hey" she whispered, leaning in close to him, "Just try and relax, it's going to feel a little weird at first, but I promise you'll soon start to love it" she said reassuringly before kissing him again. Tom naturally closed his eyes as Ellie leant in to kiss him and he felt himself begin to relax despite himself. After a moment he felt a gentle pressure against his asshole before Ellie's finger slid inside him. Tom gasped and squirmed slightly at the strange sensation before Ellie's finger curled and a wave of pleasure surged through Tom, causing his eyes to fly open and his whole body to twitch.

"And that's your prostate baby" Ellie whispered with a big grin, "Feels magical huh?" she said, giving his cock another squeeze with her other hand.

"Fucckk" Tom muttered, as he adjusted to the feeling of having something inside him, "I was not expecting that."

"You had no reason to know how good it would be" Ellie said with a sly smile, "But based on your reaction just now, you're really gonna love getting fucked" she said, emphasising her last point by slipping another digit in to join the first. A small moan escaped Tom's mouth as he felt his ass stretch slightly to accommodate Ellie's second finger. Ellie began planting a series of kisses down Tom's neck as she slowly fingered his ass, eventually adding a third finger to join her other two.

"Enjoying yourself?" Ellie asked softly as she watched Tom twitch and squirm, "You're taking to it pretty quickly I must say."

Tom nodded eagerly, "Mmmmmm, yes" he muttered, before looking almost forlornly at Ellie as she withdrew her fingers from him.

Ellie giggled slightly at his reaction, "Oh my god, you love it don't you? You just look like I took something away from you." Tom blushed deeply crimson and went to say something but Ellie shushed him and smiled. "No no, it's not bad, I love you're enjoying yourself" she said reassuringly, "and don't worry, I have something for you."

Ellie rose gracefully from the spa and went to collect the smallest butt plug, about 4 inches long from the shelf. She made her way back to the spa and began lubricating the plug thoroughly, "Can you bend over the edge for me? We're going to let you get used to the size of this while I give you that massage" Ellie said, climbing back into the spa.

Tom maneuvered himself so that he was bent over the edge of the spa with his butt above the water. He did his best to relax as he felt Ellie gently apply pressure to his hole with the toy until it reached its widest point when it slid smoothly the rest of the way in one quick motion. Tom let out a loud moan as it slid in unexpectedly and he felt his ass stretch to accommodate the plug's girth.

Ellie giggled at Tom's reaction, pulling him back into the tub to sit on her lap as she gently massaged his shoulders and chest from behind, "There's nothing quite like watching someone get plugged for the first time" she whispered in his ear.

Tom felt the toy shift inside him as he settled on Ellie's lap and failed to suppress another moan at the amazing sensations that motion produced. As Ellie worked his shoulders, he sat back and enjoyed the feeling of tits pressing into his back and her hands on his body. Tom also felt her own cock stiffen through the fabric of her bikini bottoms, "You're enjoying this too I see" he commented, somewhat lost in the sensations.

"I enjoy treating you... Plus I love having my hands all over you" she admitted, stroking her hands up and down his sides. "Want to get on the massage table for me?" Ellie asked after a moment.

Tom nodded and they both rose, Ellie took his hand and led him over to the table, before grabbing a towel and drying him off. "Lie down for me, you're going to love this" she said with a grin. Tom lay down on the table, putting his face through the hole and his arms by his sides. After a moment he gasped as he felt Ellie pouring warm oil over his back and spreading it out across his entire back. "The warm oil feels really good," he murmured, almost to himself.

"Well, after a warm spa, I'm hardly going to use cold oil am I?" Ellie commented, as she poured some extra oil across his legs and across his ass. When Ellie began massaging, Tom couldn't help but sigh contentedly as he felt all the tension drain out of his body. She worked over his shoulders and back, easing tension out of muscles Tom hadn't even known he had.. Ellie worked her way gradually down his back and even across his ass, before rubbing down his legs too. It could have been 10 minutes or 10 hours, Tom wouldn't have known or cared. As Ellie finished with his legs and feet, there was a pause and Tom simply lay there, relaxing.

After a moment, he felt Ellie take ahold of the putt plug which was still nestled inside him and gently draw it out, inch at a time. Tom couldn't help but let out a long, drawn out whimper as he felt the plug slide slowly out of him, as he quivered at the pleasure that emanated across his body. Tom idly noted an almost empty feeling at the loss of the plug, but didn't have long to dwell on it before he felt the rapidly becoming familiar sensation of Ellie gently inserting something into his ass. This new plug was much longer and girthier than the last and Tom moaned loudly as he felt his ass struggle to accommodate the plug.

"Good boy" he heard Ellie whisper quietly before he felt her clamber onto the massage table with him, hovering over him on all fours, "Here's your reward" she said, before lowering herself onto him and sliding her body slowly against his. Tom moaned again as he felt her large, perfect breasts slide up his back, slicked with oil, before slowly sliding down his back again.

"Fuck Ellie..." he muttered, "That feels..." he trailed off, at a loss for words.

"Perfect?" she suggested, grinding her hips over his ass, causing the plug to shift inside him and force another moan from his lips.

"Does it get better than perfect?" he asked, "Cause that" he mumbled.