It was a cool summer evening in Miami, Jane went out with her friends to a few bars and arcades to have fun. Jane was a tall beautiful brunette with a nice rack and a nice ass. She had gone to the beach with her friend, dateless, shockingly. Her friend Eriana, a seemingly short brunette, brought along her main squeeze for the weekend, Ryan. Their whole vacation Eriana had been getting hit on by all the guys on vacation, even some girls! Jane on the other hand, was trying purposely to avoid the attention. Any attention like that made Jane uncomfortable. She was there to have fun and enjoy the beach. She wasn't trying to hook up with every guy she met.
They all went to an arcade around 8:30pm. While Eriana and Ryan sat in a photo booth making out and being sexual, Jane was playing games and having a good time. She walked over to the snack counter and ordered a coke slushie. Little did she know her crush, Matt, was also at the arcade with some friends.
Matt was a 6'2" brown eyed, brown haired guy who was covered in tattoos and had a lip ring. He was hanging out with some friends who recently graduated, and whom had set him up with another girl on the trip. He personally cared nothing for the bimbo, but if he didn't find someone of interest on the trip, he didn't want to go home without getting laid.
Matt got in line behind Jane to get a slice of pizza and immediately recognized her as being a local person in his town back home. He didn't remember her name, nor had he ever spoken to her before, but he'd always thought she was a cute girl that he wanted to meet and get to know, but never got around to it. He figured he was there why not now!
By the time he'd gotten up enough courage to say something to her, she was heading off to play skee ball. He quickly followed her acting as though he was already thinking about playing it. He got in the lane two over from her watching her play, seeing she was pretty good at it. He wasn't so bad himself. He glanced at her noticing how beautiful she was.
She was wearing black vans, short tight fitted jean shorts with a tight black undershirt and a very flowy Bad Religion crop top, which was his favorite band. She had her long dark brown hair down and pulled over one shoulder. He thought she was the most beautiful girl he's ever seen and he noticed his pants starting to get tighter.
He fixed himself so she wouldn't notice his hard on and walked over to her with a smile, "I see you're pretty good at this game. Wanna play me?" Jane was completely caught off guard but quickly replied with a "sure". "Well what are the stakes? My name is Matt by the way."
Jane giggled a little while she thought about what she wanted if she won. "Well...I'm not sure. What do you want, Matt?"
"Hmm, well first you could tell me your name. And If I win, you get to take me out for ice cream."
"Oh really? Well if I win you can take ME out for ice cream and also if you lose, you have to wear this on your head!"
Jane quickly pulled out a squid hat she won from a previous game. It was bright green and had long tentacles that hung down. "My name is Jane by the way."
Matt looked at the squid hat, then at Jane and her beautiful body. He thought either way he had a date with this girl. "You've got a deal pretty lady!!" Matt quickly put two tokens in Jane's game, then in his. With a few balls in the 10 point slot and one in the 50, by the end of the game Matt hat 80 points. Jane got one in the 100 slot, and a few in the 10 making her points 140.
"Looks like I won, squid boy!" Matt smirked at Jane's comment and allowed her to place the ridiculous hat on him. "Wait right here, I've got to go tell my friend I'm leaving." While Matt stood waiting on Jane to return, his 'date' came up behind him and started flirting with him. She wrapped her arms around him and tried to kiss him. "Whoa, back off. What are you doing?!"
"I thought we were on a date Matt? Are you woosing out?!"
Matt pushed her off of him hoping Jane hadn't seen. "I didn't want to be on a 'date' with you. And as far as I'm concerned, you're on a date with Brad." Matt pointed over at the guy she'd been making out with all night. She gave him an 'eat shit' look at walked off.
Matt started to look for Jane, and when he finally found her she was still talking to her friend. He was relieved she hadn't seen the ordeal he had just went through. "You ready to go beautiful?"
Blushing, Jane replied, "Yes, I'm ready. And thanks. That's the second time you've complimented me tonight."
Eriana stood up and walked over to Matt handing him something and whispering, "You look familiar, but take care of Jane. She's a virgin!"
"ERIANA!! Oh my god. Pay no attention to her, she's drunk." Jane put her head in her hand and walked off embarrassed.
"Haha, don't worry, I'll take real good care of her." To Matt's surprise, Eriana had handed him a condom!
He walked outside where Jane was waiting on him and led her to his car. They both hopped in the car and went on their way. "So where do you want to get ice cream at sweetie?"
"I'm not sure. Anywhere I guess." They made there way to a Marble Slab where Jane got Cookies'N'Cream and Matt got Strawberry.
While Jane ate, she got some on her chin. "Matt, can you hand me a napkin please?" Matt looked up at her with ice cream all over her face and laughed. He gave her a devilish grin, and a smirk, then leaned towards her and licked straight up her chin until his tongue met her lips. He quickly pulled his tongue back in his mouth and pressed his lips against hers for a few seconds then sat back and stared at her. She was staring at him with big eyes and almost looked like she was shaking!
Matt was unaware that Jane had a crush on him back home and his kiss made her very aroused. "You still need a napkin?" Matt asked in a very conniving tone.
"Ahem....um....no. That worked." Jane looked away and continued to eat her ice cream. To break the tension, Matt figured he'd do the same so he spread some ice cream on his lower lip and leaned towards her.
"I made a mess....dang!" Jane looked at him and giggled wiping the ice cream off with her hand.
"Whaaat? That's no fair." He sat back in his seat disappointed while Jane stared at him. She leaned in towards him and pressed her lips hard into his.
He felt a bulge start to rise in his shorts as he sat there in shock. "I'm not in the mood for strawberry" Jane said with a smirk.
Matt was so aroused he could barely stand it! As they finished their ice cream he asked her, "What do you want to do now, baby?"
"I don't know....it's only 9:15....wanna go for a swim in the pool at my hotel or something? It's right up the road." Luckily Matt had left his swim shorts on and agreed to go with her.
They arrived to her front beach hotel and went up the her room so she could change. He went and sat on her bed while she fumbled around in her bag for her swim suit. As she found it, she put it on in the bathroom and came back out and handed him the aloe. "Will you please put this on my sunburn? It's killing me!"
Matt took the aloe almost instantly. He had been wanting to touch Jane's perfect body all night. He massaged the aloe on her upper back and worked his way to her lower back. "It's only on my upper back and shoulders. Thank you!" Jane took the aloe and brought it back into the bathroom.
Matt followed her closely and when she turned around they were face to face. He couldn't stand looking at her gorgeous body and not being able to touch it. "Jane, you're beautiful. I just have to have you!"
Jane blushed and pressed her body into his and wrapped her arms around his shoulders. "Well Matt, if you treat a lady right you just may get what you want." With her body perfectly smashed into his, he could feel her hard nipples pressed into his chest. It was turning him on so much, and it was clear to Jane how aroused he was due to the fact that he was stabbing her in the thigh with his boner.
She let go of him and slowly moved around him and towards the door. "Are you coming or what?!"
Under his breath Matt replied, "I'd like to be CUMing in you...."
"What'd you say Matt? I didn't hear you."
Matt walked up closer to Jane, smacked her juicy ass and replied, "Nothing." As they got in the elevator Matt gave Jane a very seductive look and as soon as the doors closed her he pushed her against the wall and pressed himself into her.
She looked up at him so innocent and tried to get away from him. "Baby, why are you pushing away?"
"I don't know...I'm just not ready for all this...I want to go swimming, that's all."
Matt looked at her and smiled, "Okay Jane. Sorry if I made you nervous." He leaned closer, gave her a small kiss on her cheek and backed away. Just in time for the doors to open where a family was ready to enter the elevator.
They got off and went around back to the pool around. It was practically deserted except for a couple that was packing up to leave the area. "I want to go to the hot tub first, if that's okay."
Matt followed her into the room where the hot tub was, and quickly dropped his towel and got in. "Dang this is really 'hot and steamy' if you catch my drift." Matt said it in such a sly way Jane was actually amused by his sexual reference.
She slowly got in the pool of bubbly hotness stopping to get use to the temperature. Matt noticed her chill bumps and the fact that her nipples were almost tearing through the fabric of her top, and as usual, his dick began to swell. "Just do it real fast. It's painful at first, but once you get use to it, it feels amazing." Jane stopped and stared at Matt, then snickered. "Get your mind out of the gutter, Jane, and get in this hot tub with me!!" Jane laughed and continued into the tub slowly letting the water cover her legs, then her stomach. Finally she was tired of waiting so she went in completely and let out a moan when the hot water covered her shoulders. "Hey, don't do that too loud. People will think we're in here fucking."
Jane looked at Matt raising her eyebrows up and down and started scooting towards him playfully. "Don't do that Jane, you're going to make me horny!"
"Oh I am? What are you gonna do about it?" Jane scooted close enough to Matt that her nose almost touched his. She rubbed her hand up his thigh and against his bulge. When she felt it she quickly brought her arm back in and sat back.
"Well, you were curious as to what would happen if you got me horny, and my dick gets bigger just when I look at you." For some reason that flattered Jane in the sweetest way and she leaned over and kissed Matt.
He put his arms around her and pulled her closer, kissing her non stop. Jane ran her hand up his thigh and untied his swim shorts. She pulled them down far enough that his dick shot out straight. Her eyes grew bigger when she saw the size of it, and got a little nervous. Not knowing what she'd started, she definitely didn't know what to do next. She looked up at Matt waiting for him to make the next move. He grabbed her hand and placed it on his rock hard dick. She wrapped her hand around it and started moving her hand up and down until she got the hang of it. Matt leaned his head back and closed his eyes. Her soft skin against his hard on made him let out faint moans.
His breathing got heavier as he was close to releasing himself into the hot tub, but before he had a chance he made her stop. He grabbed Jane by her hips and pulled her on top of him. He looked into her eyes and pulled her in for a kiss. He looked away from her and down at her chest, staring at her hard nipples through the fabric. He wanted so badly to grab one and suck the other, but didn't want to make Jane nervous. Her touching him was one thing for the virgin, but if he started touching her, new emotions and feelings would devour her.
"Are you sure you want this baby?" Jane looked into his gorgeous eyes and nodded. She untied her top and held it in place over her perfectly large breasts.
"I'm not sure what I'm supposed to do, so you'll have to show me." With that bit of permission, Matt took full advantage of it and quickly removed her top from under her hands. He pulled her arms around his neck and buried his face in her chest. He kissed everywhere his lips landed until he met with a nipple.
He licked and sucked on her nipples until she pushed away. "Why'd you stop me baby?"
"I don't know...I'm getting nervous...what if someone comes in?"
Matt looked towards the door, then back at her half naked body and down at his uncovered dick that was pressing into the front of her swim suit bottoms. "You're right....we need to bring this party up to the room. He quickly lifted her up and pulled his shorts back up. He grabbed her top and shoved it into his pocket and took a towel and slowly wrapped it around her unclothed tits. Giving each one a kiss before fully covering them, making sure to keep her horny until they were in the room.
They went up to the room and placed a 'Do Not Disturb' sign on the door handle. Making sure she was still interested, he asked, "Now where were we?" Jane took his hand and led him to her bedroom. She pulled off his soaking wet shorts and shoved him onto the bed. "Mmm I like it rough baby." Matt said with an evil smirk. Jane did a sort of 'strip tease' when she removed the towel, grabbing her breasts and massaging them up and down. "Hey that's my job!" Matt said while he started jacking himself off at the sight of her. Jane snickered and slowly removed her bottoms.
She got on top of Matt, feeling his dick pressing hard on her inner thigh. He grabbed her by her hips and slammed her over to the side of him and rolled over on top of her. As she giggled with excitement he began to kiss her all over starting at her forehead, down to her lips, and around to her neck where he bit down hard. She took in a deep breath and spread her legs out and wrapped them around him. "I can tell you liked that, huh?" Jane looked up at him with glazed over eyes and slowly nodded. He leaned down and bit her neck again, this time she moaned and dug her nails into his back. Matt thought to himself, if this turns her on that much, imagine what she's going to do when I go down on her!
Matt started kissing slowly down her body until he got to her perfect tits where he started licking one, then bit down on it. Jane moaned louder and pushed her hips up into him. He felt her starting to breath heavier and he knew she was almost ready to let him in. He worked his way down her stomach kissing and licking her. He kissed each of her hip bones and the top of her mound. He could feel her tremble with each kiss he placed on her body. He licked the outside of her slit slowly going farther in each time.
She grabbed the sheets tightly as he stuck his tongue farther inside of her. He worked his way to her 'pearl' and started to press his tongue harder on it and pushed his fingers inside of her. She squealed and pushed him away. "Did I hurt you baby?"
"No....I'm just getting too excited." Jane sat up and looked into his eyes. "I'm ready to give it up to you, Matt, but I'm nervous like hell!"
"Don't worry Jane, I'll be gentle." He slowly pushed her back down and got on top of her massaging one of her tits with his hand.
He felt himself getting harder and harder knowing he could cum right when he entered, but he took the chance. He remembered the condom he had, but he didn't want anything between them when he took her virginity. He rubbed her with his fingers once more to let her know he was about to enter. He put his tip in and slowly pressed into her until he was fully in. He almost came right away when he felt her warm moist walls surrounding his throbbing dick. She moaned and began breathing heavily while he thrust himself inside of her over and over, harder and harder. She started screaming his name and scratching his back as he fucked her harder and faster.
He could feel her starting to move underneath him so he slowed down and started going inside of her deeper. He could feel her tight pussy contract around his dick as she started moaning and screaming his name. With the excitement of her orgasm he couldn't stop himself from releasing inside of her. He started ramming her harder and harder until he couldn't anymore. He pulled out and rolled over next to her. Their heavy breathing intertwined with one another. Jane grabbed his hand, rolled over, and put her head on his chest. He rubbed his fingers through her hair and laid still. "How was your first time baby?"
Jane replied, "It was amazing, Matt. I couldn't have asked for better, or with any other guy. You're amazing, and honestly, I've been wanting to lose my virginity to you for a while...I see you around town and you're just so sexy!!"
Matt laughed and kissed her forehead. "Jane, you're beautiful. This was honestly the best I've ever had. Will you be my girlfriend?"
Jane had tears of joy in her eyes and yelled, "Yes!!! I will!" She leaned over and gave him another kiss and fell asleep in his arms.
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