Chapter 7

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 beaten 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.