*Author's Note - This story is a sequel to my other story: "Sydney and Harry's First Time". While you don't have to read that story to understand this one, it will give you more context for this tale.

One afternoon Sydney and Harry were spending their time together at the bike shop. However as they were talking with one another, suddenly walking into the bike shop was Olive, Emmy, and Sophia. Immediately the three girls with smiles on their faces said together, "Hi Harry." Harry then said, "Hey ladies." Harry not wanting to take Sydney away from her friends, touched her hand and said, "Text you later." Sydney with a happy smile said, "Okay." The three girls then feeling happy for Sydney (realizing what Harry's hand touching meant) all said, "Bye Harry!" Then as soon as Harry was gone, the three girls all sat in front of Sydney as Olive said, "And he's gone. Okay, spill! How long have you two been holding hands?" Then Sophia said, "Have you two had your first kiss?" Then Emmy said, "Did he take you on a romantic date yet?" Then Sydney with a smile said, "Well yeah, we held hands, kissed, and had a romantic date... while naked in my house for nearly an entire day!"

The girls all had excited looks on their faces as Olive said, "Oh my God! You mean you two actually..." Sydney nodded her head as she said, "Yeah. And it was like... the most amazing experience of my life." Then Sophia said, "Oh God, tell us everything." Then Emmy said, "The more details the better!" Then Sydney with a giddy smile said, "Well actually... I think I kind of want to keep the details to myself for awhile. It kind of feels more special if only me and Harry know the details of what really happened the first time we did it... along with the other ten times we did it afterwards." Then with wide eyes, an excited Olive said, "Ten times!? Come on Sydney, you can't tease us like that!" Then Sophia said, "Yeah, how else are we supposed to help you and support you as friends if we don't know everything about your love life." Then Emmy with a straight forward tone said, "And also we just want to know the details so it'll fuel our horny fantasies we discuss during our next sleepover."

Then Sydney looking a bit caught off guard said, "Oh yeah. Sorry, I had to bail on our last two sleepovers." Then Sophia said, "It's okay. We know you just wanted some more Harry Time. You have a happy relationship and a hot boyfriend. That's nothing to feel bad about." Then Emmy said, "Besides, you may not be part of our Amiga Sleepover Time anymore, but we can still have some fun Amiga Hanging Out Time." Then Sydney said, "Yeah, but I still miss hanging out with you girls." Then Olive said, "Yeah. Sorry you can't have both Harry Time and Amiga Sleepover Time together." Then Sydney's eyes suddenly lit up. Sydney then sat silent for a moment, but then said, "Wait. What if we could merge them together. I mean... maybe I could invite Harry to have a sleepover with the four of us and... maybe we'll see if Harry is willing to share his affection he has for me with my three best friends."

Then Sophia said, "Whoa. I mean are you suggesting we see if Harry wants to do... a fivesome with us?" Then Sydney said, "I guess. I mean... my first time making love to Harry was so wonderful and magical. I just want my three best friends to experience how it felt with me. And I know Harry would do anything for me. Plus, we're teenagers now. Teenagers are supposed to do something super wild and crazy and dumb just once in their life. So what do you all think?" Then Olive said, "Well... it would be nice to see how sex feels like with a boy surrounded by supportive friends I trust." Then Emmy with a straight forward face said, "Plus Harry is sexy, and it be the hottest and sexiest thing ever imagined!" The three girls then looked at Emmy with strange faces, as Emmy said, "What? You know you're thinking it too." Sophia and Olive both turned their faces as they tried to hide their slowly growing grins.

The next evening: Sydney, Olive, Emmy, and Sophia were all sitting around Sydney's room wearing bath robes talking. Then the four heard a knock at the window. Sydney opened the window, and saw Harry outside on the tree fully dressed. Harry then stepped into the room as Olive, Emmy, and Sophia with big smiles on their faces said, "Hi Harry!" Harry smiled as he waved and said, "Hi amigas. Man, thank you for inviting me to your sleepover with you all. Sorry if I over-dressed. So are we gonna play some games or something?" Then as Sydney took Harry's coat off of him she said, "Well actually... we were hoping you'd play something better than a game with us." A curious looking Harry then said, "What do you mean?" Then Sydney held both of Harry's hands as she said, "Harry... you know I love you right?" Harry nodded his head as he said, "Of course. And I love you. I'd do anything for you Sydney." With a smile on her face Sydney said, "Good. Because... I also love my three best friends here. And we do everything together. And... I feel bad that none of them have gotten the chance to feel the kind of pleasure we've had together. So I was wondering if... maybe we could all make love together tonight."

A surprised looking Harry then said, "Wait. You mean a fivesome... between me and all of the amigas?" Then Sydney put a hand on Harry's cheek as she said, "Please Harry. Do it for me. Do me a special favor by helping me do a special favor for my special friends, my special boyfriend." Harry then looked at Olive, Emmy, and Sophia and saw the nervous but still excited looks on their faces. Then Harry looked into Sydney's eyes and said, "Sydney... I told you I would do anything for you. And what you asked doesn't change that. So yes... lets do it." Sydney smiled as she immediately helped take Harry's shirt off. A now shirtless Harry then said, "So... how should we start this?" Then Sophia said, "How about with starting to make a huge tent in your pants?" Then Sydney, Olive, Emmy, and Sophia immediately took off their bath robes, showing they had no clothing on underneath. Harry then suddenly felt a huge bulge in his pants develop as he looked at the four naked teenagers in front of him.

As Harry began to stare at the four amigas, Sydney had her hands resting on the sides of her upper legs, as she tilted her head to the side slightly with a big smile. Olive meanwhile bent her arms and put hands on her hips, while spreading out her legs a bit, and smiled with bold confidence while winking at Harry. Emmy meanwhile turned her body slightly to the side, while putting one hand on her firm Latina butt, while putting her other hand right below one of her breasts, as she puckered her lips. Next to her friends, Sophia meanwhile brought her pointer fingers from both of her hands to her vagina, and began to gently stick her finger nails into her vagina, while biting her lower lip and smiling at Harry. Harry meanwhile was taking the time to examine each girls' hidden features. Harry noticed how Sydney's breasts were firm with big round brown nipples, while Olive had slightly smaller but bouncier looking breasts complete with bright pink nipples. Emmy meanwhile had the smallest breasts but were still very firm, complete with tiny little erect brown nipples. Sophia though had the largest breasts, and seemed to have had hers the longest as they were already starting to sag just slightly, but her nipples looked very firm and erect as well.

Harry also took notice of each girls' vagina, with Sydney having an adorable clean shaven light brown vagina, Olive having a smaller more pale and hairless vagina, Emmy having a small pale brown vagina with tiny little black hairs coming out, and Sophia having many little dark hairs coming out of her wider vagina. Harry also looked at each girls' face, as he noticed how Sydney had a warm comforting smile, Olive had a very bold excited smile, Emmy had a nervous but excited smile, while Sophia had a very eager smile. Harry then grinned as he pulled off his pants, and threw that in the air as he said, "Catch!" Olive reached out and caught the pants. Olive then smelled them briefly, as she had a naughty smile on her face. Then Harry took off his underwear and threw that in the air as well. Then Sophia reached out and caught the underwear. Sophia then brought the underwear right to her nose and smelled it as she said, "Mmmm. Heavenly." Then Harry with a big grin said, "Okay Amigas. I'm all yours."

Then all four teenage girls got on their knees as they crawled towards Harry. Then each girl reached out and put a hand on Harry's penis. As the four underage girls each began to rub his penis, Harry moaned as he felt twenty female fingers all gently fighting to rub every area of his penis. Then all four girls brought their faces near each other and they all stuck out their tongues. Soon the four tongues of the four girls were all licking every area of Harry's penis. Harry moaned as he felt so much pleasure overtake him. Then Olive got bold and pushed forward and shoved all of Harry's hard penis into her mouth. As Olive began to gently suck on Harry's hard member, Emmy and Sophia got behind Harry and began to lick his butt, while Sydney got under Harry and began to gently lick his balls. Harry moaned from feeling even more pleasure now. Then Olive pulled her mouth away from Harry, as Sophia took her turn to suck Harry's penis, while Olive tried licking Harry's butt. Then eventually the girls all moved away from Harry as they stood up.

Sydney then pushed Harry onto her bed as she turned to look at Olive while saying, "Olive, you've been my best friend longest. Care to be first?" Olive smiled as she said, "I'd love to." Then Olive got on top of Harry as she placed Harry's penis near her youg vagina. Olive then bent her knees, lowered her body down... and then had Harry's penis enter her. Olive moaned loudly as she said, "Oh God! Oh wow! Wow! Just wow!" A smiling Sydney then said, "That a girl Olive. However... lets make this hotter for Harry." Sophia and Emmy both laid at Harry's side, and each girl guided a finger from Harry's two hands to their young vaginas. Harry then stuck his fingers into Sophia and Emmy's undergae vaginas and began to drill his fingers back and forth giving them pleasure. Sydney meanwhile moved her face towards Harry's and kissed him on the lips. Then as Olive's bouncing and Harry's thrusts began to get more intense, Harry said, "Oh God. Olive, I'm about to cum." Then Olive said, "Me too. Here we go." Olive began to bounce on Harry harder and harder as she said, "Yes! YES! OHH! OOOOOHHHHHHHH!" Then Harry yelled, "OhhhH!" Then just after Olive orgasmed, Harry orgasmed as well, shooting his full load of semen deep into Olive's thirteen year old body. The two shook for a moment, but then Olive got off Harry as she said, "Wow. Mmm. Harry, that was amazing."

Then as everyone moved their bodies around, everyone began to crowd around Emmy as Sydney said, "Okay Emmy. It's your turn." Then Emmy looking a little out of sorts said, "Me? But I thought Sophia would... I mean... I'm not ready." Then Olive said, "Emmy, it's okay. I didn't feel completely ready either but it was great." Then Emmy looking nervous said, "But what if I get... what if I might..." Then Sydney said, "Shh. Emmy, it's okay. We're teenagers now. Everyone expects teenagers to do crazy and stupid stuff when they're young. So lets make the one crazy and stupid thing you do the most memorable and amazing thing you've ever experienced." Emmy then took a deep breath and said, "Okay. Harry... hit me with your best shot." Harry smiled as he crawled on top of Emmy. Harry then pushed his penis into Emmy's thirteen year old vagina, causing Emmy's eyes to suddenly get wide as she yelled, "Ohhhh!" Emmy then wrapped her arms around Harry's back tight as Harry began to thrust his body up and down on Emmy's young Latina body. Emmy's body began to bounce as well as he spread out in all directions as she yelled, "Ohhhh! Mmm! YES! OH GOD YES! OOOHHH! OOOOOOOOOHHHHHHH!"

Meanwhile Olive and Sophia brought their faces to Harry's butt and began to lick it again. Sydney meanwhile laid her hips near Harry's face and directed Harry's face towards her waist. Then Harry moved his tongue down and stuck it into Sydney's vagina. Harry then began to lick Sydney's underage vagina while still thrusting his penis deeper into Emmy. Then Emmy suddenly felt herself orgasm as she said, "Oh God! Here it comes! Here it comes!" Then Harry moved his face up as he said, "And here I come!" Then Harry let go and let himself orgasm inside of Emmy. Harry and Emmy both shook their bodies together as Harry let his large load of semen and sperm shoot deep into Emmy's young Latina body. Then as Harry pulled out, Emmy looked into his eyes and said, "Was I good?" Harry then briefly kissed Emmy's two nipples and said, "Girl, you have nothing to be ashamed of."

Then Sophia pushed Harry down on the bed and said, "Okay. My turn!" Sophia then got on top of Harry as a smiling Harry said, "My, my girl, you are aggressive." Then Sophia with a big grin said, "I always know what I want and I always know exactly what I'm doing." Then Sophia instantly put Harry's penis into her young vagina. As Sophia began to bounce on Harry and ride him she said, "My, my boy, your dick sure know how to get hard again fast." Then Olive smiled as she said, "Well he's got lots of help tonight." Then Olive got on top of Harry's face and put her small pale vagina right over Harry's face. Harry then stuck his tongue into Olive's underage vagina and began to pleasure her again. Then Emmy got behind Sophia, and brought her fingers down between Harry's legs and began to touch his balls, gently stroking them. Harry in turn, brought hand over to Emmy's light brown colored vagina, and inserted his finger deep into her, pleasuring her body again. Meanwhile Sydney got in front of Olive and stuck her clean shaven vagina also close to Harry's face. Harry then moved his tongue back and forth, using it to pleasure both Sydney and Olive's different colored vaginas back and forth. Harry then said, "Oh God, it's coming. I'm gonna cum! I... OHHHHHHHH!" Then Sophia yelled, "OH GOD! OOOHHHHHHH!"

Then all of the girls began to moan loudly as well from the pleasure they were feeling. Then in an instant: all five teenagers orgasmed at the same time. Emmy released her female fluids onto Harry's hand, Sydney and Olive got Harry's face very wet, and Harry shot tons of his sperm into Sophia's body. Eventually all five teenagers moved their bodies and laid down together. Harry then said, "Oh God. Okay, now I'm too exhausted to get hard again. But ladies... that was a ton of fun." Then Sydney said, "Agreed. Thank you Harry for giving my three best friends a chance to share in what we both experience." Then Sophia said, "Yes. I got everything out of it that I wanted to." Olive grinned as she said, "I'm sure that we are all gonna carry a part of that experience with us for the rest of our lives." Then Sydney looked down as she said, "Well... all of our bodies got pretty messy tonight. So I'm gonna take a shower." Then Olive said, "Oh, you want me to join you?" Then Sophia said, "Or maybe have all of us join you?" Sydney then saw Harry wink at her, as Sydney said, "Well... why not?"

TO BE CONTINUED... IN A BRAND NEW STORY:

FOUR AMIGAS, FOUR UNPLANNED PREGNANCIES (just browse my profile to find it)