Virgin Role Playing - Session 02

My name is Bob. My wife Lucy and I like to do some role playing to spice up our sex life. I wrote about our previous episode, "Virgin Role Playing - Session 1" Here is our next session, the opposite roles.

Him: Bob is 40 year old virgin. He really wants to have sex, but is very shy and doesn't know how to bring up the subject. Her: Lucy is a 38 year old "Mom I'd Like to Fuck". She especially likes to teach guys sexual techniques.

Scenario: She know he is a virgin. She gets horny and teaches him the ropes.

---------------------------

It was a Saturday night. Lucy and Bob had a lazy day, didn't do much of anything and were now hanging around watching whatever was on TV and working on their second six-pack between them.

She was flipping channels on the remote, and the playboy channel came up with some soft-core porn. She paused there for a while, they giggled together watching it.

Lucy paused the DVR. She thought this would be a good time to initiate their pre-arranged role playing agreement.

"You're still a virgin, aren't you?" She winked at him when she asked that, and he picked up the role-playing cue.

"Yeah, I know, it's pretty embarrassing, but I don't know why, it just never happened. I wish it would happen some time, but at this point I can wait I guess." he said.

"There's no time like the present, lets just take care of that problem right now."

His face turned bright red. Could this really be his lucky day? He could feel his unit coming to life under his jeans.

She had on a t-shirt with the collar ripped apart down front a few inches, and the bottom of the shirt cut off too, exposing her belly button. She was dressed like trailer trash. She was actually a professional woman, went to work dressed in business suits, but today she was chillin.

She had no bra on, so the view of her cleavage and her nipples poking out through the cotton. After she said that, he had a hard time keeping his eyes off her Double-D's.

Bob stammered. "Um....I guess so. I have always wanted you to teach me, I bet you know all about it."

"OK then. Let's get this party rolling." She un-paused the DVR, and the soft-core played on, along with the cheesy background music that those flix use.

"One simple rule. You have to do whatever I say. Some of the things I tell you to do might sound disgusting or you just don't want to do it, but trust me, you'll end up enjoying the whole experience" she took control of the situation. "Feel free to ask me any questions as we go along. agree?"

"Yes, I agree. I will do everything you tell me to do." he said.

"OK, first step: Take off your clothes. Clothes just get in the way of things. I can see your unit bulging out there a bit, I think it needs to be set free."

He wasn't sure he was quite ready to go this fast, but he had agreed to do what she asked, so he took off everything. She was right, his unit did need to be set free, it wasn't completely hard, but it was about halfway there, sticking out as he stood there naked, curving down a bit.

"How about you? Are you going to strip naked too?"

"In good time, my boy, but you're going to have to wait a bit for the good stuff."

"I'm going to teach you all the steps you have to do to have sex, ask any questions you think of."

She was role playing really well, starting her instruction.

"Sex is pretty simple really, the guy just puts his penis into our vagina until he cums inside of her. That's all you need to do if you want to make babies, but that's not really that much fun especially for the woman, but we expect you to give us some satisfaction too."

She was standing there in front of him while talking. She reached down and held his cock in her hand, which was now fully erect.

"Wow" she said. I didn't have to do much to make you hard. I'm still fully clothed! I really like to play with cocks like this."

She got down on her knees in front of him, still holding his cock in her hand and looking at it.

"Seriously, I am pretty sure this is the biggest cock I've ever seen, and definitely quite a bit bigger than any I have ever touched. I'm a bit scared to let you put this monster in my pussy. I don't think it will fit."

Bob knew of course that that wasn't true, his cock was maybe a bit bigger than average, but it fit just fine into her pussy, where it had been thousands of times by now. But her role-playing was awesome, he was really enjoying what she was saying, his cock was super hard now in her hand.

He was about to say something in response, but she deep throat-ed her in one gulp, and held it all the way in. It took his breath away.

Her hands played with his balls, and started bobbing her head up and down, making sloppy noises.

She knew from experience that he wasn't going to be able to take much of that, so she stopped and stood up, planting a deep kiss.

"So, you're all ready to go, it looks like. Your cock is very hard. Are you ready to put it into my vagina?" she asked.

"I guess....." he started to say, but she interrupted him. "Not so fast! It's not your turn yet. I still have all my clothes on, and my pussy is not even wet yet! Your cock is not even going to be able to get it in there."

She continued. "It's the man's responsibility to give the woman at least one or two orgasms before sticking his dick in. Because it feels so good to him when it's inside, that he maybe won't be able to control himself and he'll cum too soon, and then it'll be over."

"And you don't want that...she'll be disappointed, and your sex life will suffer, she'll go find a man who can satisfy her. So I'm going to teach you how to bring a woman to orgasm."

Awesome. This is what he really wanted her to do. How many men get lessons on this subject? Most women just expect that you can do it, they don't teach you.

"First step, take off her clothes, one piece at a time. Touch and kiss everywhere, lightly and gently."

Bob took the opportunity and kissed her deeply, running his hands through her hair and around her back under her skimpy shirt. He took her shirt off first, he lightly touched her nipples, and noticed that they were starting to stick out at attention.

"My nipples need more attention, give them a kiss"

He took her hand and led her back over to the couch and sat down with her. She leaned back and he gave each of her nipples a kiss, then sucked on them gently. He heard her breathing more heavily, and heard some faint moans.

"mmm baby, you are doing good, keep doing that you are making me wet. I still have some clothes on." she said.

Bob got down on his knees in front of her, and unbuttoned and unzipped her trashy cutoffs. She raised her butt up a bit, and he pulled them off. Now she was wearing only some red panties.

"Bob... you didn't get all my clothes off yet. Come on, you can do better." She raised up her butt again, and he removed the last piece.

Now there she was in front of him, entirely naked. Her legs were spread in front of him, he stared at the object of his desire with anticipation. She was unshaven, had a nice mound of curly brown pubic hair, matching the hair on her head. He could see her lips opening up a bit.

He looked up at her. "I'm not sure what to do down here. I've never seen one of these in person before."

"OK, let me show you." She spread her legs as wide as she could, and brought her hand down and spread her lips. It was all pink in there. He could see the inner lips, and a little nub up near the top of them.

She pointed to that nub. "See that? That's my clitoris. Some folks call that the love button. It's very sensitive, and if you touch it a bit, it'll make me cum. So go ahead, take one hand and spread apart my lips like this, take the other hand and rub very lightly on my clit."

He followed her instructions. "Ooooh. Right there. you found the spot. Keep doing that." She started moaning louder and louder, leaned back and arched her back. "Don't stop. Keep rubbing. Please don't stop"

He kept rubbing with just the index finger, very lightly, but faster and faster. Then she started screaming and slammed her legs together, both of his hands between them. He was a bit afraid that he had hurt her, but he looked up at her and there was pure pleasure on her face, not pain. She opened her eyes and smiled at him.

"You did it, Bob, you gave an orgasm to a woman for the first time. You should be proud of yourself!"

"But we're not done here yet. That's what they call a 'clitoral orgasm' where the woman cums when her clitoris is contacted. The next step is the G-Spot orgasm. Let me show you how to do that."

She spread her legs wide again and brought her hand down and put her middle finger into her vagina as far as it would go.

"OK so I've got my finger up inside, there is a spot a couple inches up, at the top of my vagina which feels a bit different. It's hard to explain exactly, but you can feel it. Give it a try, feel around in there."

Again he followed her instructions. He put a finger inside, and she felt warm and slippery. He felt around some more and sure enough, like she said there was an area that felt a little different. "Right there. That's the spot. Just rub on that some more. Maybe use your thumb to rub on my clit a little bit too while you are doing that."

This was awesome. She was telling him exactly what to do, and it was working. It was obvious that she was going to cum again. Things were getting very wet and slippery down there.

After only a minute or two of fingering her G-spot, she came again. He could feel her pussy squeezing his finger really tight, and it was very intense. Soon, just like the first time, she looked down at him and smiled.

"Wow. Dude, that's #2. Amazing."

"But there's a third way to make a woman cum. You know what that is?"

"Um, I'm having a whole lot of fun down here, I can't think very well though, I have no idea." he said.

"There's lots of names for it, the scientific name is 'cunnilingus'. Or you could call it 'dining at the Y', 'eating her out', 'carpet munching' or hundreds of other slang terms. Basically, you just go down there and lick me all over. Go for the clitoris. Suck my cunt lips. Stick your tongue up inside. When you hear me moan, keep on doing that thing a little more."

"You can't really do much wrong down there, we love it when you lick our pussy. It makes us cum."

So Bob jumped in with both feet. He started licking all around, then sucked on her clitoris. While he was sucking on it, he put a couple fingers up in there. This seemed to send her over the edge. Her hips were jumping up and down, he had a hard time keeping his head in the right spot. Another orgasm was coming, obviously.

And cum she did. Her legs clamped down on his head and squeezed him in there, almost suffocating him. But she eventually let up, and he came up and gave her a deep kiss.

"Oh my god baby, you are so good at that. I'm really surprised, most guys need a lot of practice but you made me cum on your first try." she said.

"So now you have fulfilled your obligation to bring a woman to orgasm. Not only once, but three times!"

Bob smiled. "That was a lot of fun for me too, I'm glad it worked for you. Thank you very much for showing me what to do, I had no idea how it works"

She smiled. "Well, there is one more type of orgasm for a woman that I need to teach you. Are you ready?"

"Absolutely. Anything. My dick is so hard right now it almost hurts. Just tell me what to do." he pleaded to her.

She got off the couch, grabbed a couch pillow and lay down on the carpeted floor, placing the pillow under her head. She spread her legs wide.

"The last type of orgasm for a woman is called a vaginal orgasm. That's when a man fucks her hard and it makes her cum. The only trick for you is to try not to cum yourself before she does."

"It's OK if you do cum first, You've already satisfied me by giving me three orgasms, but this last one is kinda like the icing on the cake."

"So, come on up here and put that huge cock inside me, all the way in. Let's see what you can do."

"I know I've been telling you what to do up till now, but now it's your turn to be in control. Use my pussy, take me like a man. Fuck me as hard as you want, my pussy can take it."

Her hands were resting down on her thighs, She took them and cupped them and opened up, as if she was handing him something. In between her hands was her beautiful vagina, lips opened up and glistening with her juices.

He came up between her legs and gave her a kiss. "Thank you for giving me your pussy" he said. "You're welcome. Now please return the favor. I need that huge cock of yours." she replied.

His cock was just at the point of entrance. It knew exactly where to go, as if guided by an invisible hand. The tip went in. She held her breath, she was a bit scared because she knew how bit it was.

He took control of the situation. He held the tip in, and looked into her eyes. "You sure you're ready?" he needed her permission.

She finally let out her breath and relaxed. "Yes, I am. Do it." she whispered.

He thrust it all the way in, without stopping. She let out a gasp, and a bit of pain showed on her face. It felt so awesome all the way up in her pussy, he could feel her cervix pressing against the tip of his penis.

He kept pressing hard, and looked in her eyes. "Thank you again. Your pussy feels unbelievable. I never imagined it would feel anywhere near this good."

"Well, the feeling is mutual. I'm glad it fits all the way in, I feel so filled up"

He remembered what she told him, he really wanted to give her the "icing on the cake" with another orgasm. But he knew he could do it. He started thrusting in and out. It felt so good. Apparently it felt really good to her too, as she was thrashing about pressing on his chest, her head going side to side. "Fuck me, fuck me, fuck me FUCK ME" she said, over an over.

After only a few minutes, the icing on the cake came. He could feel the muscles inside her pussy squeezing really hard on his cock, making it almost impossible to continue thrusting. It was just like he had felt with his finger earlier, but since his cock was a lot further up inside her it was much more intense.

He slowed down a bit, but continued thrusting gently. She lie there with her head to the side, eyes tightly shut, taking the punishment of his big cock.

Once he felt that she had recovered at least a little bit from her orgasm, he stepped up the pace and fucked her even harder. He reached over and grabber her ankles and pulled them up in the air, allowing him to pump even more deeply into her cunt. The feeling was over the top for both of them.

Then all the sudden, he stopped. He had a brainy idea. He now had the power. "Why not give her another, just for the fun of it?" he thought.

So he withdrew his cock, and buried his mouth into her pussy. He found her clit, which was now very erect, with his lips, and sucked hard on it, while flicking it with his tongue. It only took 30 seconds of sucking, and she came one more time. She screamed and thrashed about, but didn't say anything, she no longer could even say a word.

It felt really awesome to make her cum like that so many times. He felt like a real man.

So now it was his turn. Before she even had recovered from her orgasm, he came up and rammed his cock back in as hard as he could. He started thrusting really hard. In and out. In and out. His balls were slapping against her ass, but then he could feel his balls contract, and he knew he was going to shoot his load into her tight pussy.

But before that could happen, one more time for her! He felt her pussy contract on his cock again, and arms and legs were everywhere. His ejaculation lasted a dozen pumps, it's like it never stopped.

He collapsed on top of her. She wrapped her legs around him, and held him tight. It felt so good to both of them to hold each other after cumming so hard.

He pulled himself up and withdrew. He could see a lot of his sperm flowing out of her, mixed together with her pussy juices.

Lucy & Bob's role playing adventure was over. They had really enjoyed themselves. This was definitely an adventure that they would continue, along with the previous reverse role position.

They would now have to think about new roles to play.