tagFirst TimeAnnie's Gift

Annie's Gift

byChiara23©

As always this story is exclusively my property and may not be republished or redistributed without my permission. Any resemblance to people or places living, dead or non-existent is merely a coincidence.

-

Greg sat in his bedroom with his cellphone in his hand. It was his eighteenth birthday and he was as nervous as hell. In his other hand was a crumpled scrap of paper with a name and phone number on it. He'd carried that little flimsy in his wallet for four years, waiting for this day to arrive.

Greg was a tall, lanky guy, he wasn't heavily muscled but he had a wiry definition and strength. His dirty blond hair was cut short and slicked back. Girls always fell in love with his gray-green puppy-dog eyes and long lashes.

Even though he was a good looking guy Greg had never had a girlfriend all through highschool. He'd patiently waited until today to see what would happen. Greg was so worried that he'd be rejected that his stomach was in knots.

'God man you'll never know unless you call her!' he thought to himself. Greg took a deep breath to steady his jittery nerves. He looked at the paper and started punching in the number.

The phone rang three times then a woman answered. "Hello? Hello!"

Greg quickly pushed the end button on his phone. He was shaking even more now, it had been her. He recognized her voice instantly. That sultry voice of the girl who'd captivated him at his cousin Chiara's four Christmases ago. His phone rang and he jumped, dropping his phone on the floor. Greg scooped it up and checked the screen. It was her, she was calling him back.

---

Annie was out at dinner with her boyfriend Phil. To say she was beautiful would be a gross understatement. With her long raven hair, flashing black eyes and well toned, statuesque body she was a masterpiece of feminine excellence.

They'd just gotten their entrees when her cell rang. She looked at the screen but didn't recognize the number.

Out of curiosity she answered the call, "Hello? Hello!" She looked across the table and gave Phil a perplexed look, "That was weird, no one was there."

Phil laughed and winked, "Another secret admirer babe?"

Annie barked out a laugh, "Not that I know of. I'm going to call the number back, hold on."

---

Greg gulped and answered his phone, "H-hello?"

There was that voice again, "Hi I just got a call from this number? Is there anything I can do for you?"

"A-Annie, Annie Montgomery?"

"Yes that's me, who's this?"

Greg stammered, "Uhm, Annie? It's ah me, Greg. Greg Lanceri? I don't know if you remember me?"

"Greg? Little Greg from Christmas at Kiki's? Oh my God, it's been forever! How are you sweetie?"

"I'm okay, uhh I just turned eighteen and I called to say hi like we planned?" Greg said in a shy voice.

"Listen honey I'm right in the middle of something, can I call you later?"

Greg was crestfallen, he felt like he was getting the brush-off. "Uh sure okay. Talk to you later?"

Annie's voice sparkled over the phone, "Definitely sweetie! Just give me a bit okay?"

"Okay bye."

---

Annie looked at Phil with a Cheshire cat grin. "Wow, I thought he would've forgotten about me by now."

Phil shook his head with a wry grin, "So what was that all about babe?"

"Remember when me and Marc were at Kiki's for Christmas? Well I met her little cousin Greg. He was such a sweetie, fawning all over me and just being so cute. When they left I slipped him my number and told him to look me up when he got older."

Phil grinned at Annie, "So let me guess, he's older now? Like legal older?"

Annie laughed, "Apparently so Phil. What am I going to do? I promised him I'd show him a good time when he got legal. I don't want to disappoint the poor kid."

"So don't," Phil replied. "We're secure enough that this won't be an issue hon. I totally trust you and know you'd do the right thing with him. Go out with him, have fun, then show Greg a good time. You have my support on this okay?"

Annie was a bit dumbfounded, she hadn't expected Phil to go along with this that easily. "You're okay with this? Seriously?"

Phil chuckled, "If I'm okay with you and Chiara fooling around, why wouldn't I be okay with you giving this nice kid a special birthday present?"

Annie's jaw dropped and she was stunned speechless for a second. "You know about me and Kiki? How long have you known?"

"I've known for a while baby, it doesn't take a brain surgeon to figure it out. Every time you two have a girls night you come home flushed and smelling like sex."

Annie laughed until she was breathless. The other people in the restaurant were giving her and Phil funny looks.

"And here I thought you had no idea about us!"

"To be honest Annie I think it's pretty hot. You know how bad I had it for Kiki. To see you two together would be totally awesome!"

Annie gave Phil her Cheshire cat grin again, "If you're a good boy I might be able to swing it babe."

---

It had been two hours and Greg felt like shit. He should've known that Annie was going to dust him. He was almost in tears he was so mad at himself.

There was a soft knock at his door and his older sister Yvette poked her head in, "Hey Greggie, everything okay?"

"Fuck off sis I'm not in the mood." Greg lashed out.

"Hey whoa! I was just making sure you were okay. I heard you cursing and muttering and I thought I could maybe be an ear for you."

"Sorry 'Vette, I just had a lousy phone call and got dusted." Greg said dejectedly.

Yvette smiled sympathetically at Greg as she sat beside him, "Lemme guess, Annie?"

Greg wiped at his eyes, trying to stem his tears. "Yeah, I called her like she said to and she blew me off."

Yvette hugged Greg and rested her head on his shoulder. "A lot can change in four years Greg, she might be married, have a boyfriend. Who knows?"

Greg hugged his sister back, "You're probably right, it was stupid of me to hope she meant it for so long. Thanks sis."

Yvette kissed his cheek, "I know it hurts little brother. Been there, done that."

"Yeah but I waited for her, I never dated or anything! I feel like an idiot."

"Remember Robbie Ford? Remember how bad I had it for him, and he didn't even know I existed? Annie wasn't like that, I think she liked you. She'd be dumb if she didn't at least call you back." Yvette said as she gave him another hug.

Greg's cell rang. He checked it and whooped with glee. "It's her! It's her!"

Yvette laughed at him, "Well answer it dummy!"

"Uh hello?"

"Hi Greg, it's Annie. Sorry I didn't call you sooner but I was out to dinner with a friend."

Greg was vibrating with excitement and had a wide grin on his face, "That's okay Annie, I'm glad you were able to call back."

"So now you're all grown up I guess? You must be a lady killer by now." Annie said with a chuckle.

Greg blushed and his sister stifled a giggle. "I'm not much of a lady's man, I was too busy getting good grades."

"I missed you at Chiara's wedding last summer. I thought for sure you'd be there."

"I wanted to go Annie but I was up north on a tree planting crew." Greg replied.

"That's too bad, I was reserving a slow dance for you sweetie."

Greg laughed, "Aww man! I was up to my neck in mosquitoes and deer flies!"

"So what are you doing next weekend?" Annie asked slyly.

Greg got all nervous again and Yvette was turning blue trying to hold back her laughter.

"Uhm, well nothing I guess."

"Well if I recall I promised to take you out and show you a good time when you got older. How about dinner and a movie or whatever else you'd like to do?"

"Uhh, sure yeah, that'd be great!" Greg replied as he blushed again.

"Great! How about seven thirty at 'El Stavros'?"

"Yeah sure, seven thirty at 'El Stavros' would be great!"

Annie laughed, "Okay honey I'll see you Saturday night then."

Greg hung up and looked totally stunned. Yvette finally released her pent up laughter.

"Oh my God! I never knew you could blush in so many shades of red!"

"She's taking me out. She wants to go out with me and do whatever I want." Greg said in a soft voice.

Yvette gave Greg a big hug and kiss on the cheek, then mussed his hair. "See? Annie didn't forget you. So dinner at 'El Stavros' huh? That's a swanky place, she must be wanting to impress you!"

"She said we could do whatever I wanted..."

"I think I can guess what you want to do, the way you've been since you met her!" Yvette said with a giggle.

Greg chuckled, "Hey a guys gotta have a dream ya know."

"More like a wet dream, and yours is six feet tall and gorgeous."

"Can I help it if I've been obsessed? I think I've got good taste personally."

Yvette tousled Greg's hair again, "Well if I were into girls I'd be into Annie too. She's pretty hot little brother. Just don't burn yourself out before Saturday okay?"

---

Greg lay awake most of that night. All he could think about was Annie and how nice she'd been to him. That kiss she'd given him at Christmas kept playing through his mind over and over. She was the first girl he'd ever kissed and it had almost blown his socks off. Then he had found that little slip of paper in his pocket. With those few simple words 'Call me when you're eighteen, Annie.' and her phone number. And now she wanted to go out with him! Saturday couldn't come soon enough!

---

Greg was working with his Dad at his contracting company to make some money for college. It was hard work and his Dad didn't play favourites, Greg had to work just as hard as the other guys.

Greg was busy framing with another guy.

"Hey! Greg pay attention man!"

"Huh? What?" Greg said as he looked around.

"Jesus man what's your problem? You just about nailed my hand to the stud!"

Greg's dad saw what happened and suggested that maybe he should help the electrical guys. That was fine until he almost electrocuted himself.

"Greg come here!" his Dad called.

Greg walked over to his Dad, "Yeah what's up Dad?"

His Dad pulled him aside, "Listen, I don't know where your head is today but I don't need you causing an accident and you hurting yourself or someone else. Go home and get your head screwed on right and come back tomorrow okay?"

Greg hung his head, "Sorry Dad, I'll be okay tomorrow, I promise."

Greg drove home and went straight to his room. He went to his dresser mirror and pulled the picture of Annie and him that his cousin Chiara had taken at Christmas off of it.

'God she's gorgeous! And she wants to see me. Boy did I ever look dorky back then.' he thought to himself. Greg took off his work clothes and sprawled on his bed with the photo. He stared at it for a few minutes and felt himself getting hard. Greg slipped his hand into his boxers and slowly stroked his growing cock.

Greg moaned and tucked his boxers under his balls then began stroking himself faster. "Oh fuck Annie, the things I wanna do with you. I've waited so long."

He squeezed his erection and pumped it faster. His eyes closed and his hips began to buck.

"Hey Greg what are you...oh shit!"

Greg jumped in surprise and tried to cover himself up, "Fuck Yvette! Ya ever think about knocking?"

Yvette giggled, "Thinking about Annie huh?"

Greg stuffed his raging hard-on back into his boxers. "So what if I am? Is it any of your business?"

"It is when I catch you jerking off. Don't be embarrassed little brother, it's not like I haven't seen a cock before. As a matter of fact if you get lucky Saturday I think Annie will be most impressed!" she said with a sly grin.

Greg blushed and grimaced as his hard-on strained to get free. "And how would you know?"

"Trust me, I've seen my share."

Greg was feeling very uncomfortable with his sister talking about seeing cocks and saying his was big. He'd been so close to cumming and his balls were aching for release. Greg squirmed in discomfort.

"Jesus sis can you get the fuck out of here so I can finish? I'm dying here!"

Yvette smirked at Greg, "Go ahead, don't let me stop you. I'll be downstairs."

As soon she she left he stuffed his hand into his boxers and yanked out his cock. Greg started stroking himself again. He closed his eyes and squeezed himself as his hand jackhammered on his cock. Greg's breath was coming in short strained gasps. He felt his balls tighten and his cock throb then huge ropes of cum jetted from his cock, landing on his stomach and crotch.

Greg moaned with relief, his hand gently stroking as his member diminished. He wiped himself down with his boxers then went and had a shower to clean the rest of the cum from his body.

Yvette was sitting in the living room when he came downstairs. "Feeling better now?" she asked with a giggle.

"Yeah, sorry for freaking out on you." he replied with a sheepish grin.

"You were right I shoulda knocked first Greggie, so what are you doing home? Shouldn't you be at work?"

Greg grimaced, "Yeah but I almost nailed a guys hand to a board then I just about electrocuted myself."

"Holy crap this Annie thing is really getting to you isn't it?"

"All I keep thinking about is how bad I'm going to screw up if we do have sex. I don't want Annie to think I'm some kind of loser."

Yvette gave him a hug, "Do you want me to set you up with one of my friends so you can have a test run?"

Greg shook his head, "Thanks 'Vette but Annie was the first girl I kissed, and if she's willing she'll be the first girl I have sex with."

"Aww you are such a romantic Greggie. If it happens I'm sure Annie will do right by you." Yvette said as she gave him another hug.

"Thanks sis you're great." Greg replied as he hugged her and kissed her cheek.

---

Saturday took forever to arrive but Greg managed to get through the week without mishap.

He was standing in front of his mirror, checking and double checking himself.

There was a soft knock at his door and Yvette slipped into his room. She looked him up and down and whistled. "Wow Greg you look great! If Annie's not impressed she's blind."

"You really think so 'Vette? I just want to make sure that I look my best."

"Trust me Greggie, I can think of at least three of my friends who would kill to have a date with you if they saw you right now."

Greg blushed a deep red, "Really sis? You're not just saying it to get me going?"

"Greg, if I weren't your sister I'd kill for a date with you. You look totally hot little brother."

"Thanks sis, I guess I'd better get going, I don't want to be late to my first date."

Yvette gave Greg a hug and kiss, "Go have fun, you'll knock her panties off!"

Greg laughed, "I sure hope so Vette."

---

Annie pulled into the parking lot and got out of her car. Several men within eyeshot of her got whiplash from watching her. She'd gone all out for Greg, she was wearing a short strapless, slinky black dress that hugged every curve of her body perfectly, and garters with silk stockings.

Her hair was done in a french braid with little rhinestones in it. She'd decided not to wear a bra or panties. Annie's large breasts stood firm and proud on her chest, almost spilling out of the top of the dress.

She went into the restaurant and was taken to the best table. Every mans eyes were on her as she made her way to the table, hips swaying seductively. She sat down and ordered a bottle of expensive champagne.

Greg arrived and walked into the restaurant, the maitre'd asked him what party he was with.

"Annie Montgomery please." Greg said nervously.

"Right this way Sir."

When Greg saw Annie he forgot to breath for a second. She was even more beautiful than he remembered. He gulped in some air and soldiered on.

When Annie saw Greg coming toward her she stood up and hugged him, giving him a slow kiss on the lips.

"Wow! Greg you look great! It's been way too long sweetie."

Greg couldn't help but blush, this gorgeous woman was all his for the night. "H-hi Annie. You're like wow!"

Annie laughed and did a little pirouette for him. "You like?"

Greg's eyes popped when he caught a peek of garter. "Holy! Uhm Annie you did all this for me?"

"I sure did, I promised you a good time and that's what you'll get!"

They sat down and the wine steward came over and opened their champagne, pouring a small amount into Annie's glass. She tasted it and nodded, the steward poured them each a glass then left.

Annie gave Greg a mischievous grin, "I can't believe you haven't had all sorts of girls hanging all over you Greg, you're way too hot for them not to notice!"

"Well there were a few girls who liked me but I want to get into a top university so I didn't do any dating." he said with a blush.

Annie leaned forward, giving Greg a good look at her cleavage and whispered, "So I guess you're still a virgin then?"

Greg blushed even more as he looked down at his plate.

Annie laughed and grinned, "Oh sweetie we are just going to have so much fun!"

---

After dinner they went out to a movie, Annie snuggled up close to him, pushing her breast against his arm. Greg was so distracted by Annie's boob and his hard-on that he couldn't remember most of the movie.

"Having fun Greg?" Annie asked when they got out of the movie.

Greg nodded, "Yeah Annie, I really appreciate you taking me out. It's been a lot of fun."

"My pleasure sugar, but the fun has only just begun."

She drove them back to her place. When they got in Annie grabbed Greg and planted a slow sensual kiss on him. Greg instantly got another erection.

When she was done her lip lock Annie smiled and winked at him. "Are you sure you've never been out with a girl? 'cause that was a pretty good kiss there buster!"

Greg blushed and grinned, "Okay so I may have made out with a few girls under the bleachers at school."

"Well tiger, we can do more than make out if you want."

"A-are you sure?"

Annie gave him another slow kiss, "Greg, I promised you a good time and I meant it. I never make a promise I can't keep. I'll go get us some wine, make yourself comfortable baby." Annie said as she went into the kitchen.

Greg wandered around her living room, there were some pictures on the shelves, he looked at them and saw that they were pictures of Annie and a guy. They seemed happy, there were pictures of them at a beach, at Chiara's wedding and riding dirt bikes.

Annie returned with two glasses of wine and handed him one. "Busy being curious sweetie?"

"Uhm who's the guy in the pictures?" Greg asked.

"That's my boyfriend Phil," Annie said with a smile and chuckle.

"Boyfriend? Oh my god! He's gonna kill me!"

Annie chuckled again and caressed his cheek, "It's okay sweetie, he knows about tonight. In fact he told me I had to keep my promise to you."

Greg looked incredulous, "You're sure he's not going to hunt me down?"

"I'm positive Greg, he told me to give you the best night of your life and I plan on doing just that." Annie said as she gave Greg another steamy kiss.

Greg's knees got weak as she kissed him, he knew she was going to have sex with him and got all flustered. Annie's tongue darted into his mouth and wrestled with his.

His hands slowly slipped down her back and cupped her firm ass. He could feel Annie's garter then realized that she wasn't wearing panties. She pushed her breasts into his chest, poking him with her erect nipples.

"God Annie, I've waited so long to do this. Ever since you kissed me you're all I've ever thought about."

Annie smiled at him and pecked him on the lips. "Well to tell you the truth I've been waiting for you to call. You made a very good impression on me at Kiki's."

"Really? Looking back I thought I was just a dorky kid who was infatuated with you!"

Annie gave him another hug, "Not according to me, you were a very attentive young man who made sure his date was well taken care of. Some day soon you're going to make a girl think she's an absolute princess. And tonight I'm going to make sure that you know exactly how to do that."

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