Amanda takes it deep

It was new years eve. The place was a nightclub, with modern dance music playing very loud in several different areas within the club, each with a different theme. It was almost impossible to talk in most areas, but there were some out of the way areas where it was possible to have a conversation, at least if you stood very close to someone and talked into their ears.

Amanda was there with her girlfriend Gabrielle. Amanda was a virgin, Gabrielle was there to support her friend to find a guy to help her with this problem. They were both 21 years old, and the opportunity to become a woman never came up for Amanda. Amanda was very petite, not much over 5 feet tall. Tonight, her heels added 5 inches to that. She was dressed in a tight short one-piece, black and white patterned, with a low cut that revealed her DD sized cleavage. At first glance most people would assume that she had her breasts were enhanced, but no, they were all natural and very firm and perfectly shaped, the kind of boobs you'd see in a centerfold.

Amanda and Gabby were talking a break from the dancing and having a drink, and two guys walked up. They introduced themselves David and Adam. Good looking guys, both were clean shaven, well built guys with nice smiles. They were both about 6 feet tall.

They made small talk. The girls already had drinks, they did too. "This place is awesome, especially on new years eve." Adam said. "After we finish our drinks, would you like to dance with us?" Adam was looking mostly at Gabrielle, so it seemed like they would be paired up.

"Sure, we'll dance." Amanda said, she looked straight at David and gave him a smile. They continued sipping their drinks through another song, and then walked towards the dance floor.

The four of them danced together for 4 or 5 songs, they were getting sweaty. The went back to the table. Amanda said to David "Let's go find a place that we can actually talk." They told their friends that they would be back, and went to find a quieter area and sat down next to each other.

"On a night like this probably everyone in a place like this on a night like this wants to get laid, I know that's why Gabriella and I came tonite, what about you?" Amanda asked.

A bit of a surprise question. He answered. "Well yeah, I guess so, like everyone else, especially the guys."

David said to her "I have a problem, and I think it's probably best to bring it out in the open right now before we go any further."

Amanda looked concerned. "Oh no, what is it?"

"Don't worry, it's nothing bad, but some girls just can't deal with it, so I thought I better just tell you now. I'll just say it.... I have a really big penis. It's like twice as big as average, I measured it once and it is almost 11 inches long." he said.

Amanda was shocked. She didn't even know how to respond. Maybe it was a joke? She was a virgin, and had never even seen an erect penis before, except in pictures. She didn't know really how big they should be. Since the subject of her virginity hadn't come up yet, she didn't know what to say.

She kept her composure though, and raised her eyebrows. "Wow.... that's pretty cool I guess. So what's the problem? I thought all guys wanted to have bick dicks?"

David continued. "The problem is, basically it's just too big for some girls, and so neither one of us has any fun. It hurts her, or she just doesn't like it. Tonight is a special night, new years eve and all, and I really want to start the year out right with a girl who I match up well with. I don't want to do any more of these one night stands."

Listening to him, Amanda felt like this was a good opportunity to tell the truth about her virginity to him and see where it went from there. It seemed like at least he wanted the same things she did, a long term relationship with someone who matched well.

"Well....OK I have a bit of a sexual secret too. Are you ready to hear mine?" she asked.

Her response was a bit surprising to him. "Sure, let's hear it."

She told him "Mine is real simple. I'm a 21 year old virgin. I have never even seen a man's penis first hand. I don't know if this is going to work, because I don't even know if your penis is too big or not, I have no idea if it's going to hurt."

"Oh boy, I'm sorry I had no idea. I just told you my thing that assuming you were like most other people our age. I don't know what to think." he asked.

They both sat there for a minute, it was an awkward silence.

She decided to go for it. "Well I really want to lose my virginity tonite." she said. "That's why we came here, to find a guy to help me out with that. I'm just done with it, I need to move on to the next chapter in my life. I know everyone has a lot of fun in bed with each other, and I think I'm missing out. Life is to short to deny yourself things like that." she said.

"You're absolutely right. it is a lot of fun. You are missing out." He chuckled a bit at his own joke, she did too.

She continued. "But this is what I think. You don't have anything like a robo-cock or anything, do you? I'm pretty sure vaginas are made to fit pretty much any size penis out there. I'm thinking that it will probably fit just fine, maybe a bit of lubrication and a couple more drinks would help. There's no reason I can think of that you can't pop my cherry. You really don't have anything weird, correct? You were born with it?"

When David heard that, he felt some stirring down below. This was exactly the kind of girl he was waiting for all his life.

"Oh yes, definitely I was born with it. It's all natural, not even circumcised. I remember in gym class in high school looking at other boys units and thinking that maybe I had something bigger than average, but I never did any plastic surgery or anything." he said.

She said "Well as far as my virginity goes and all...I'm thinking that I really need a guy to show me the ropes. Honestly I know very little about sex. My parents were no help at all. Sure, I've talked to some friends about it, and I've Googled all kinda things and seen various types of porn that were all pretty much disgusting, but I'm a newbie, and I need someone to really get down and dirty and do a 'show and tell' kinda thing. I need someone to be my sex teacher."

David was flabbergasted listening to her, but he tried to hide it. "Well I'm sure I could do that. Sounds kinda like the sex role playing games couples play. They might do a Doctor and Nurse role play, or in this case Teacher and Student. Sounds kinda kinky, but it's almost like we are not actually role playing, I am the teacher, you are the student, for real."

"Exactly. I'm feeling better and better about this the more we talk, but the more I think about it the more scared I get. But seriously, I think we should just do it. What do you think?"

"Sounds like a plan to me. It's already 1AM, last call is going to be soon." He said.

"David, before we go any further, let's make each other promises. I know you really want to get laid tonite, and so do I. If we go any further with this, then let's promise that we will have sex tonight, go all the way. There's no turning back, this is the start of a new chapter for both of us. Deal?"

He stepped into his teacher role. "OK student, your homework for tonite is to fuck your teacher. Your teacher will give you lessons on how to do that, and he promises to fuck you. Deal." he said, with a big grin on his face.

She laughed nervously. "Great, I feel so good about this. I'm going to start my new sexual life with a guy with a huge penis, and you're going to start your new sexual life with a virgin girl, teach her the ways of the world."

"My apartment is not far from here, we can use that as the classroom, you can teach me" she said, stepping into her student role.

"I think we need to go find our friends and tell them what's going on." he said.

Promise me you won't post anything about our deal on Facebook." she said to him, smiling.

"Ha ha....no definitely not. Teachers aren't allowed to be friends with their students on Facebook." he said, smiling.

They both pulled out their cell phones and texted their friends. She told Gabriella that she'd be going home in David's car, don't wait up for us. He told Adam the same.

They got in his car, and she navigated him to her apartment. There wasn't a lot of talk during the ride home, they were both a bit apprehensive about what was about to happen. She put her hand on his thigh, which gave both of them some comfort.

It was about 2AM when they got to her apartment. She offered him a drink, he took a glass of water. They were both very horny at this point, no sense in small talk.

"OK teacher, my bedroom is down here." She pointed.

"Class begins!" he said, laughing.

They walked into the bedroom and stood next to the bed and gave each other a hug and started kissing deeply. His hands pulled up her dress and he grabbed firmly onto her butt, she pulled him close.

"The first thing to do is get undressed. Clothes just get in the way."

She raised her hand. "Teacher, will you help me take off my dress?

"Of course I will.". He was grinning ear to ear. This role playing was going to be fun.

He pulled her dress up and over her head and took a step back. She was standing there in bra and panties. "Wow. You are unbelievably beautiful, he said. I love your body already, even though I've hardly touched it."

She reached behind her back to unhook her bra.

"Here, let me give you a hand with that. He reached around her and unfastened it. Her double-Ds were awesome. Nipples were poking out. He stepped back and looked at them, lifted them up a bit with his hands underneath, brushed his fingers over her nipples. "Wow...those are the best breasts ever. I've never seen anything that beautiful, even the playboy bunnies don't look that good."

She blushed. He pulled his shirt over his head. He was a muscular guy, he had some chest hair and almost a six-pack. He continued getting undressed, kicked off his dockers and pulled off his jeans. They both stood there naked from the waist up, gave each other another hug and french kissed for several minutes, their hands all over each other's bodies except the genital areas.

He stepped back. "Like I said, clothes just get in the way, let's get naked."

They each pulled down their own undies and stood there looking at each other. It was a full moon night, and the moon was shining through a picture window there in her bedroom. He could see that her pussy was completely shaven. She could see his cock, it was not was not fully erect yet, but getting there.

He spoke first. "Wow, I don't think I've ever seen a girl completely shaved like that, except in porno movies. That's cool."

She replied "Well since this is the first time I've ever had sex, me and Gabrielle were talking this week and we thought it would be fun to get brazilians together, so we made an appointment at the salon. It hurt a little, but I kinda like the way it feels."

She had been staring at his cock nonstop since he took off his boxers. She couldn't take her eyes off it. "Um...Let's talk about the elephant in the room.... that thing of yours is huge. I think I need to measure it to see if you're telling me the truth about your eleven inches. Let me go find a ruler."

He blushed. "I'm pretty sure that's what it is, I measured it a couple years ago. But maybe it's smaller now."

She stepped out of the bedroom and came back with a ruler. "OK teacher, let's see what you've got."

He was smiling ear to ear, and was a bit nervous now. "OK but before you measure, rub on it a bit to make sure it's fully standing at attention."

She walked over to the nightstand and turned on a lamp and set the the ruler down, then got down on her knees in front of him. She gently took a hold of it and looked at it carefully all over. "This is way cool, I feel kinda jealous that I don't have anything this cool to play with."

She pulled back his foreskin and looked around the head, then gave it a kiss. Her hands started rubbing his balls. By now he was fully erect. She was starting to think that this might not be a good idea, his penis was a lot bigger than she ever imagined, now that she was up close and personal with it. She had a small dildo vibrator that she played with sometimes, it was only maybe 3 or 4 inches long, and she never even put it all the way in. That wasn't even close to the size of David.

She looked up at him. "Is that enough rubbing? Is that as big as it's going to get?" she asked with a grin on her face.

"I think so, you can measure it now." he said.

"OK here goes. They say men always lie about the size of their penis." she picked up the ruler and placed it on top of his unit, pressing it down to the base. The tip went all the way up to the 11 ½ mark. "Wow, it does look like you were telling the truth. Eleven and a half. All I can say is, this thing is huge, I've never seen anything this big, even in porn." She smiled up at him.

"What do we do now, teacher?" she winked at him, looking up at him while holding his cock against her cheek.

"What some girls like to do is to give the man a blowjob. That means sucking on his cock." He said. This was going to be fun.

"I think I can do that. How far down should I suck?" she asked, again with a wink.

"As far as you can works well for most guys." He said.

She opened her mouth and deep throated him as far as she could. She massaged his balls at the same time. This was by far the best blowjob he'd ever gotten, he couldn't believe it. This girl had never even seen a cock before? She was sucking like an expert. But honestly he had to make it stop. The last thing he needed right now was a premature ejaculation, and this girl was just too good and would make it happen.

He reached down and pushed her head a bit away. "Amanda, that feels awesome, but I have to stop you, it feels TOO good. Why don't you lie up on the bed and let me inspect your pussy to be sure you are a virgin like you said. If we're going to do inspections it should go both ways."

She sat down on the edge of the bed next to the light, which was still on. She smiled at him and spread her legs, not saying a word.

He got down on his knees and looked closely. He took both hands, and using his fingertips spread out her labia as far as he could. There it was, the hymen, the proof that this was virgin territory.

He looked up to her. "Looks like you were telling the truth about that.....you are definitely a virgin, I can see it right here."

"See what?" she asked, playing the dumb blonde. She knew exactly what he was referring to.

"It's what they call the hymen, it's a little membrane that covers up the inside of your vagina. If you weren't a virgin it wouldn't be there anymore.

"Hmmmm... ok. So I guess that's good, proof that you will be the first penis to go in there?" she said.

He continued playing his part. "Yup, that's right. Now the next thing is I need to get your pussy ready for my cock." He put his index finger in a bit. I can feel it's not quite ready, it needs to get nice and wet and slippery so my cock will slide in."

"Really? I can feel it getting wet, it's not wet enough?" she asked.

"Nope, not quite. The way we do that is to give an orgasm to the girl first, before we have sex. Let me ask you, Have you ever had an orgasm before?"

She looked up at him, continuing to play the part. "No, I am a virgin, how would I do that?". In fact she had done a lot of experimentation down there with her fingers and mini dildo, and knew exactly how to bring herself to orgasm, but she thought it best to play the part for now.

"Well....let's give it a try, I'll do my best to give you your first orgasm. This is called cunnilingus, girls like it a lot, and it is the best way for us to bring girls to the big O."

He picked her up and put her down in the middle of the bed, spreading her legs. He looked again, it was almost like a dream, there she was.

He licked all the way from the base to the top of her lips. Her juices were flowing, and tasted sweet. His tongue felt so good to her. She had used her fingers many times to bring herself to orgasm, but this was completely different. His tongue was warm and wet, it felt so good. She knew this would not take long to bring her to orgasm. He started working his tongue all around, and sucked on her clit with his lips, faster and faster.

Then it happened, it came up on them both more quickly than they expected. She wrapped her legs around his head and squeezed him tight. His mouth was pressed hard against her pussy, he couldn't even breathe. She squeezed him even harder, he could feel spasms and feel juices flowing into his mouth. The best orgasm he'd ever felt, right up close in person.

She let go of his head and lay back. He told her "It feels like your pussy is all good and ready for my cock now, It's nice and wet. Are you ready to take the next step and put my penis in there?" His cock was so hard it was almost painful. It needed pussy.

"I think so, teacher. What should I do now? I heard there are a bunch of positions for this." she asked.

"The best one is the good old-fashioned missionary position, at least the first time. Some people call it boring, but it works very well, and we can always experiment later with other positions. Basically you can just lie back and spread your legs, I'll come up between your legs and put my penis into your vagina. Pretty simple really."

She spread her legs wide again. She had a good view of his cock, it just looked scary, now that this thing was close to happening.

"David, are you sure that thing is going to fit in my vagina? Seriously, I don't even understand how it can fit. I put my fingers in sometimes and it's even tight for that, how is it even possible to put something that big in? It's not going to hurt, is it? I heard that it might hurt the first time, even with a normal sized dick."

He lied to her. "Oh no, you'll be fine, don't worry about a thing, it'll fit, it won't hurt. Like you said back at the bar, vaginas are made to fit penises of any size and shape."

He knew from experience that there would be some pain for her, between breaking her hymen and his huge cock, but the last thing they needed now was for her to stress out about it. He needed her to relax.

He still played the part. "Just spread your legs and relax, I'll put it in, we'll have fun."

She tried as hard as she could to relax, she closed her eyes and mentally loosened up her pussy.

He looked at her and thought to himself "I can't believe this is happening, here is a gorgeous virgin girl naked in front of me with her legs spread wide, clean shaven with DD's and she wants me to pop her cherry. How lucky could I possibly get?"

He came up between her legs, his hands on the bed. He gave her a deep kiss and rose up a bit, looking into her eyes. "OK Here we go. I think you're going to like this."

His cock head was pressed against her entrance, it knew right where to go. Everything was very wet down there. She looked into his eyes. He started pushing in, very slowly. She whimpered a bit, the feeling was intense. His cock was only an inch or so inside, but she already started to feel him filling her up. It was much better than she thought it would feel.

He continued to push in. All girls felt tight to him, due to the size of his penis, but this one was incredibly tight. Even though it was so wet, it was difficult to get it in. He pushed in a couple inches, slowly. He knew there would be an obstruction soon. Then he felt it... his cock was pressed up against her hymen.

He stopped pushing and kissed her again deeply. He knew that he'd have to distract her a little from the pain she was about to feel. "How's that feel, is it what you expected?"
She smiled. "Wow, a lot better than I expected, it feels great! And you're right, it doesn't hurt. But I heard that it hurts some girls, and not others, I guess I'm lucky. I was a bit scared but I think this is going to be OK."

It seemed like she was relaxed, and this was probably as good a time as any. He pulled out just a bit and pushed hard through her barrier with a quick thrust of his hips.

She screamed. "Owww! Fuck, that hurt. Jesus Christ, I didn't expect that."

She was wincing in pain. He stayed still, letting her adjust. At this point he was still less than half the way in. He waited.

Her breathing came back down to normal, she opened her eyes and looked at him. "Man that was crazy. It really hurt but not much anymore. I can see now why you said some girls can't take your huge cock, I feel completely filled up."

He smiled. "Amanda,.we're not done yet. The good news is that you are no longer a virgin, I've broken through and made you a woman. But I'm not even close to all the way in. Take a look." He raised up his chest so she could look down. He hadn't moved at since he broke her hymen, it was clear that he was not all the way in, there was at least 6 inches to go.

"Holy shit, no fucking way, I can't believe this. Are you serious? I feel totally filled up! You think you can put that whole thing in? I thought you were all the way in already. This is crazy. I don't know how I could take any more than that."

He was starting to feel disappointed that he wouldn't be able to fuck her like he wanted to. "I understand, babe, I guess I was asking too much to think that a virgin pussy could take it. This might take a bit of practice. Do you want to just stop now? We can try it again next week if you want"

They were still lying there, his cock halfway in, another 6 inches to go.

"Dude...absolutely not. We promised each other we'd have sex together, and we're not done yet. A promise is a promise." She said, shaking her head. "I can take it..... I think"

He smiled. "You're right, I have a lot more to give you, let's give it a try. Hold on to something."

She reached down and slapped his ass, grabbing on. "I'm ready. Give it to me."

He pushed ever so slowly, sliding it in to her never-before visited tunnel. He didn't stop. Deeper and deeper, one inch at a time. He felt her cervix. He continued until he was all the way in, stretching her just about as far as she could stretch. Her eyes were tightly closed, head to the side, grimacing with a mix of pain, pleasure, wonderment. His massive cock filled her completely. The feeling was incredible. Then the pain had now turned into an aching feeling, which turned into a desire for even more.

She opened her eyes and looked up at him and smiled a bit. "Is that all you've got?" she asked, with a bit of a grin.

"Yup, that's it. Your pussy feels so awesome, I've never felt anything as good as this." He said.

"I totally agree. I feel so lucky to have you take my virginity, your cock fits me perfectly. I am very glad that I decided to take a chance on you, yours is the perfect cock for my pussy."

His cock was still buried in her pussy, balls deep. He went back into teacher mode. "So, the next step is what we call fucking. You just lay back and enjoy while I go in and out."

"Ooooh sounds like fun." She was still a bit nervous but ready for her first fuck.

He pulled almost all the way out, just till only the tip was still in, then thrust it slowly all the way in. He thrust more, gently and slowly, all the way in and out. The feeling was unbelievable to him, almost all the other girls he'd fucked it was impossible to go all the way in and out, sometimes it just wouldn't go in as hard as he could push, other times it hurt her too much. Amanda's pussy was just perfect, by far the best he'd ever felt.

He picked up the pace a bit, and pumped in and out at a good clip, she could feel him bottoming out on her cervix with every pump and it felt so good. The pain was completely gone, she now just needed more, she needed him to fuck her.

"That feels really good, is that as hard as you can do it?" she almost begged him for more.

He picked up the pace another notch. His balls were slapping against her ass, her whole body bouncing along with his pumping.

She could feel an orgasm coming on, she started screaming loudly and dug her nails into his back, wrapped her legs around his back. He pumped even harder, and could feel her pussy contracting on his cock, almost too tightly for him to continue fucking. But he tried his best and fucked her as hard as he could, she was still screaming but he felt his balls tighten, it was past the point of no return. He injected at least 6 or 8 loads deep inside of her, falling down on top of her and breathing very hard, his heart racing.

David rolled over, lying on his back catching his breath. She lie there, the feeling of her union with him was better than she ever imagined. He was her man. Now.

"David, thank you ever so much for doing this, I really enjoyed it, and I am so glad I am not a virgin anymore. I do think this is an excellent start to the new year. What do you think, do you want to be my boyfriend?" she asked.

"I should be thanking you. This was the best sex I ever had. Definitely yes, I want to be your boyfriend. Let's get some sleep and do it again in the morning before breakfast. I can't wait.

They fell asleep in a spoon position. The sun was rising, the start of a new year