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The Bad Girls Club, Chapter 7

"Holly gets introduced to the pleasures of womanhood!"

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"You made the right decision coming to me to be your first, Holly. If you'd gone to one of the other boys at school, they wouldn't have appreciated what they were being given.

"They would have just taken your cherry in their own bumbling, amateurish way and been done with you, breaking your heart and leaving you crying.

"But I am not like that. I want to protect you and keep you safe and happy. I know the gift you are about to give me. I appreciate you for the beautiful, wonderful creature you are. And I won't just use you and cast you aside, my sweet young beauty."

"Ohhh Jaaamesss ..." she said, her knees getting weak both at my words and my actions.

"No, my dear, when I am through with you today, I will own you. I will be all you want and all you need. I will take care of you, princess, and I want you to be mine and mine alone.

"I do not like to share my toys and will not share you. Will you be mine alone, Holly, my sweet? Will you pledge yourself to me alone for as long as we are together?"

"Oh, Yes! Yes, James! Oh, I want to belong to you! Oh, please make me your girl! Please! I want to be yours and only yours! Please!" she cried.

I stood up and took Holly in my arms. I still continued to play with her pussy, but at the same time, I kissed her. When she kissed me back it was no ordinary kiss. This kiss had true meaning behind it.

I have been kissed enough to know the difference between a "thank you" kiss, a "goodnight" kiss, and a kiss that means "I have feelings for you". This kiss wasn't any one of those.

This was an "I give myself to you wholly and completely – I surrender to you" kind of kiss. The kind that makes you know the other party is yours totally. An ownership kiss. Holly was telling me in no uncertain terms that she was mine for the taking.

Well, such a gift should not go unclaimed. I turned us both around and gently set her on my bed, laying her back. She automatically spread her legs wide and held her arms out to me, inviting me to partake of the feast before me. 

But rather than just rush into the act itself as any schoolboy would, I wanted to show her she was something to be savored and enjoyed ... a banquet, not a brunch!

So instead, I knelt down on the floor between her spread legs and inhaled her sweet, musky perfume deeply. I licked the large wet spot on her panties to get my first taste of her honey.

Then I reached up and began slipping her soiled and soaked panties from her hips and uncovering the treasure that lay beneath.

I slid her panties down her legs until they came off and I brought them to my nose to inhale her scent again. She watched me smell her this time and it made her whimper with need. 

"I will be keeping these as a memento of today – the day I took possession of you. And whenever you come over you will see them and know you belong to me," I said.

"Really James? You are really gonna keep my panties? Oh God, that is so hot! I'm glad I wore my good ones then!" she said.

I hung the soiled panties on the corner bedpost and turned back to her. She lay there watching my every move and I got closer to her steaming hole, spreading the lips and peeking into the wet pink heaven inside...

"OH GOD JAMES!" she squealed as I fastened my mouth over her leaking pussy. My tongue wasted no time in plunging into those dripping pink depths and began its search for every pearl of sweetness it could find. 

Holly had gotten a brief introduction to what I could do with my mouth the last time when she came to my office that previous Monday. I was sure she remembered the way it made her feel too – it was probably part of the reason she was here now.

But this time I didn't have to rush and I didn't have to worry about someone coming in and catching us. So I was able to pull out all the stops and show her what I could do! Needless to say, she was completely overwhelmed by the sensations coming from her virgin pussy.

Instinctively, Holly reached down to push me away just as she would if I had started tickling her. But I wasn't tickling her, I was devouring her. And she wasn't going to get rid of me so easily. 

She writhed and squirmed, thrashing her head around and clawing at the bedsheets. To look at her, you would think she was either possessed or going through some sort of seizure. But I knew what was wrong with her, and I was going to make sure she got the proper "cure" for it!

I have always been kind of proud of my cunnilingus skills. I'm certainly no professional pussy-eater, but I've never had a woman complain that I didn't get her off or that she wasn't happy with how I ate her.

I love the smell, taste, and feel of a woman's pussy and I have had a lot of really good times nestled between a happy woman's thighs.

Now I was nestled between Holly's thighs showing her what I had learned. And she was quite impressed with my skills judging from the gasps, cries, and squeals she let out. 

I knelt there between those pale, creamy thighs happily munching away at her sweet, juicy peach for several minutes, in no particular hurry to stop. I was enjoying driving this young virginal woman to heights of pleasure she had never experienced before.

Suddenly, but not unexpectedly, I heard that special sound I had been aiming for. The joyous sound of a woman at her end.

"OH FUCK, JAMES! OH GOD, I'M CUMMING! I'M CUUUMMMINNGGG!" she screamed.

She slammed my head into her crotch and clamped her legs together as if she was trying to snap my head off my shoulders. I was prepared for her as she clamped down on my head.

I quickly shoved two fingers up inside her curling them around her pubic bone and rapidly fingerfucked her – adding one more level to her distress and causing her to squeal again in surprise.

Holly offered up her juices in abundance ... I don't think even she realized how hard she could cum given the proper motivation! Although in reality it only took her a few moments to finish, I'm sure it felt much, much longer to her.

But at last, the spasms and contortions faded and she lay panting and leaking her juices onto my bed. I sat on the bed next to her as she recovered watching her and stroking her sweat-dampened hair. She opened her eyes to see me next to her and smiled weakly. 

"T-That was ... amazing!" she whispered.

"Shhh ... just rest, honey. That was only the beginning. Just an appetizer – we haven't even gotten to the main course yet!" I said, smiling.

"Well, I hope the main course is as tasty as the appetizer was! I'm starving!" she said, continuing with the food references.

"Better get in the middle of the bed then, we wouldn't want you falling out of bed at a crucial moment!" I said. She moved into the middle of the bed and scooted up a little higher as well.

She lay there on the bed watching as I got undressed now. She had yet to see me naked since all we got a chance to do Monday was for me to eat her pussy and make her cum once.

So I was curious how she would react when she saw what I brought to the party. And I was sure she had been told I was "huge" by Heather and Kim but huge is a relative term. I wanted her to see what she was up against for herself.

I took off my shirt and my pants and stopped at my boxers. I was already fully hard from playing with and eating her so I was quite "prominent" already. I saw her eyes get big just looking at the lump in my shorts!

I moved closer to the bed so she could get a better look. I dropped my boxers slowly letting her see an inch at a time. At first, she saw the head of my cock and she was fascinated, staring at the purplish mushroom cap.

"Have you ever seen a guy's cock before?"

"No. I mean I might have seen my father's when I was very little. But he left when I was only a year old, and I haven't seen any other guys," she said quietly.

"Well, there's nothing to be ashamed about Holly. In fact, I think it's wonderful that you have saved yourself like this. Most girls your age act as if their virginity is something they need to get rid of as soon as possible – like a cold or something. They go with the first guy who shows any kind of attention to them and gets that annoying virginity thing out of the way.

"But that's not the way to approach your first time and I am pleased that you have held onto yours. I am also quite honored you want me to be the one you give it to. It is a special thing to be given such a treasure and I want you to know how important this is – to both of us," I said.

"Thank you," she said, blushing from the compliment.

I finished removing my boxers and Holly looked at my cock with wide-eyed wonder. "Oh my God James!" she gasped. "Heather and Kim said you were enormous, but I had no idea! I don't think that thing is going to fit in me!"

"Relax, Holly sweetheart, It will fit. Pussies are remarkable things – they stretch to amazing sizes. Remember babies come out of there and if a baby's head and shoulders can come out of that hole, then I can certainly fit in it!" I smiled.

"I never thought of it like that. But I've never had anyone – or anything as big as you in there."

"Don't worry sweetheart. I know you are a virgin and I will take it nice and slow and tell you everything I'm going to do before I do it so you will know what to expect. You trust me, don't you?"

"Yes, I trust you, James. Thank you for taking it slow with me."

"Of course honey ... I want this to be as special for you as it is for me. I want you to enjoy this –  after all, I do want to do this again, you know!" I said, smiling.

With that I climbed into bed and moved into position over her she looked up and I saw the anxiety and uncertainty in her eyes. This was a very big step for her and I would have to treat her like the delicate flower she was.

I lowered my mouth to hers and kissed her again. "Now, just relax sweetheart and let me do all the work, you just lie back and enjoy this okay?" She nodded her head.

I reached down and took hold of my hard cock. "First I have to lube up my cock a little. You are plenty wet already but I want to make sure I am ready," I explained.

I began rubbing the head of my cock up and down between her slick lips, coating the head with her juices. "How do you like that Holly?"

"It feels nice. Thank you for explaining things to me, James. It makes me feel better when I know what you are going to do." 

I smiled at her again and rubbed my cock up and down her wet slit until I was sure it was properly lubed then I lowered my hips a bit and ran the length of my shaft between her lips to coat it as well.

This caused Holly to moan a bit feeling the velvety skin with its veined surface running up and down her virgin pussy.

"Ohh James, that feels really good..."

"Oh, it's going to get much better here in a bit my dear," I assured her.

After three or four passes, I was satisfied I was ready to go. I drew my hips back until my cock was at her pussy entrance. "Okay, honey, I'm ready to go. Are you ready?"

"Y-yes ... I think so..." she said. I don't know whether she was trying to convince me or convince herself of the fact, though.

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"All right then here we go, nice and slow..." I started to push into her very gently, only a bit at a time. At first, she didn't seem to mind it but when my cockhead began spreading her opening I could sense the change in her.

"Oh, James! Oh, I feel it! I feel you spreading me ... opening me!"

"Yes, just let it happen, sweetheart, you can do it. Just relax and let your pussy accept me," I coaxed her. By now my cockhead was really opening her and she was beginning to doubt her abilities.

"Oh God Oh you are so big! Oh, I don't know if I can do this!"

She began to gather big handfuls of the sheets in her fist and clench them tightly. She wasn't trying to move away, but I could feel her moving around under me trying to find a position that would allow me to get in easier.

Suddenly there was a pop and she gasped "What was that?"

"Take it easy honey, that was just my cockhead slipping into you. I'll wait here a second or two to let you get used to me inside you before I proceed."

"I'm sorry I'm such a baby about this James, but..."

"Shhh," I told her. "It's perfectly all right. This is the first time you've done this and you don't know what's going on. I understand perfectly. Your mom probably hasn't even had 'the talk' with you has she?"

"No, Mom doesn't want me to be around boys so she doesn't feel she needs to have 'the talk' about sex with me. I don't have anyone to tell me what's going on, what I should and shouldn't do or feel ... it's all very strange."

"I'm sure it is, Holly. But you don't have to worry with me, sweetheart. I will explain things as we go and I will take it as slow or as fast as you need to. I want you to enjoy and understand what is happening. I want you to have fun with this because sex should be enjoyable.

"It shouldn't be scary or confusing. I don't have any children myself, I've never been married. But if I did, I would want to talk with them about all this so they knew what was happening to them."

"I appreciate you taking your time with me, James. I'll bet you would be a wonderful father. I wish you were my father. You kind of are you know, being principal at school – you are like all of the kids' fathers in a way. And for those of us who don't have fathers, you are the next closest thing."

"Well thank you, Holly. And yes, I do think of you and all the kids at school as my kids in a way. I want to protect you and keep you from getting into trouble. I want to look out for all of you and if you have a problem, I want to try to help if I can. Now, are you ready to continue?"

"Yes." Holly prepared herself for more, spreading her legs wide and pulling her knees up to give me more access.

I began pushing again and my cock slipped another inch or so into her.

"Ohh Jaaames ... Ohh, you are stretching me so wide! This feels incredible..."

A bit further and I felt her hymen and I stopped. "What did you stop for? Is something wrong?" she asked, raising her head off the pillow.

"No, nothing is wrong. I've reached your hymen. It's a thin membrane covering your vagina. You'd call it your cherry. I need to get through it to go further.

"Now, this might hurt a bit, I won't kid you. But once it's done, the pain will go away and you will be ... a woman. Are you ready?"

Holly grabbed a pillow to bite into and held it close then she nodded. But I had a better idea.

I took the pillow from her and set it aside then I laid down on top of her and she put her arms around my neck. "This is such an intimate and important step for you. It should be shared intimately," I explained. She smiled gratefully.

I held her tight and whispered in her ear. "Are you ready?" I felt her head nod and she gripped me in readiness.

I thrust my hips forward and I heard her whimper and squeeze my neck tightly. I felt her hymen tear and I moved forward into a place where no one had ever gone before.

"I'm sorry," I said, holding myself still for a moment. Then I moved forward and pushed deeper into her. I knew it hurt, but I knew that soon the pain would fade to be replaced by a pleasure she had never known.

She held me tightly for a couple of minutes but, as I knew it would, the pain began to lessen and her whimpers slowly turned into something more pleasurable.

"Ohh, James! Oh God, I feel you moving inside me! Ohh I feel so full and yet it feels so good!"

"I knew you would like it once we got past your cherry. Do you want me to go deeper now?"

"Deeper? You can go deeper than this?" she asked incredulously.

"Yes, honey, I can go deeper. You have about half of me in you right now."

"HALF? You are only halfway in? Oh God!" she gasped.

I chuckled a bit at her reaction. "Well, a little over half maybe but yeah, I still have a ways to go before I'm fully inside you."

"Oh, God! I'm already so full..."

"Do you want me to stop here, then?" I asked.

I don't think Holly wanted me to think she was afraid or "chickening out" as the kids put it. So she summoned up her bravery and said. "No, I want to go on. I want to see if I can take it all. I know Heather and Kim took all of you and I want to be able to also." 

It was a pride thing – she wanted to be able to compete with the other girls, fearing I might like them more if they could do more for me.

She had to be able to match their abilities even though this was her first time. It was the same with boys. No one wants to be thought of as a wimp or a scaredy-cat, or a weakling. School reputations are on the line here. So I completely understood.

"All right then we will keep going. But you let me know if it starts to hurt too much," I said.

I knew she would push herself probably a bit too much this first time, showing me she could handle it, so I kept a watchful eye on her reactions, and the first sign of wincing or pain I would stop. The pain from breaking her hymen had faded by now so that made it easier to judge her tolerance.

I pushed in deeper and she moaned as she felt me stretching her wider and further than she'd ever been stretched before. Holly arched her back as she cried out with unbridled passion.

"Yes! Oh God, yes, James! Oh God, it feels so incredibly wonderful! Oh, push deeper! Deeper! I want all of you! I want all of that enormous cock! Ohhh, Yesss!"

I will admit she felt pretty damned good herself. I had only been privileged to take one other girl's cherry, back when I was with my first girlfriend.

She and I were both virgins and neither of us had a clue what we were doing, to be honest – only sheer animal instinct told us what to do.

But we managed, somehow, to enter the world of adulthood on that old blanket on the beach. She moved away with her family after that summer but I never forgot her or how she felt around my young eager and inexperienced cock.

Now many years and many women later I was reliving those wonderful days again with Holly. She was every bit as tight as I remembered and I hoped she was enjoying her first time as much as I did back then.

I pushed in once again but this time I felt resistance and I knew I had reached the bottom of the young girl's well. Correction – the young woman's well, because Holly was most certainly a woman now.

Feeling the tip of my cock touch her cervix made me look down and I noticed my cock was almost completely enveloped in Holly's tight pussy. Only about an inch remained outside – a pretty respectable feat for her first-ever cock.

"That's it, Holly. You have all of my cock, honey." I didn't want to tell her there was still more of me to go, so I chose my words carefully. I didn't want her to feel bad for not taking me completely in.

"I have all of you? Really? Oh, this feels amazing! God, I am so stretched ... so full!" she said.

I stayed buried deep inside her and holding her for a few moments until I felt her pussy loosen a little, getting used to my size. She was still tight as a vise, but at least once I started moving inside her she could enjoy it without much discomfort.

After a bit, I felt it was safe to start moving in and out and get on with the actual fucking. I raised up so I could see her face, "Are you ready to really fuck now? I mean that IS what you came to see me for right?"

Holly giggled, "Yes James I want you to fuck me. I want you to fuck me like you fucked Heather and Kim. I want to feel the way they say they felt when you fucked them. Make me feel like that. Please make me feel like that James."

I started slowly, drawing back until only the head of my cock was left inside and then pushing forward equally slowly. She needed to become familiar with the sensations she would be feeling when we fucked and I wanted to make sure she was ready for me.

She moaned as I pushed back into her and her moans increased in pitch and volume as I went deeper. But after a couple of strokes, she knew what to expect and she settled into what was going on. 

I began to move faster, and soon I was in a regular steady rhythm. Holly was moaning and crying out as my thrusts got slowly harder and more forceful.

She seemed to be thoroughly enjoying herself and it encouraged me to feel free to fuck her like she wanted — like an experienced and very horny woman!

I pushed deep into her once more and held myself there I grabbed her by the hair and pulled her head up to look at me.

"Okay slut, now that you have been broken to the saddle, so to speak, are you ready to be ridden like a real horse? Are you ready to be fucked like a woman and see what Heather and Kim were raving about?"

"Oh Please, James! Please fuck me like you fucked Heather and Kim! I want to feel that way! I want to feel what it's like to be fucked good and hard. They told me how wonderful it was and I want that too! Please, please fuck me!"

She practically sobbed as she spoke.

"All right then, but you'd better hang on to something – it's going to get kind of wild here in a second," I warned her. I watched as she grabbed up a couple of handfuls of bedsheets and got herself ready.

I drew my cock back and then I let go. I slammed into her at full speed and full power. Instantly I drew back before she could even gasp a response and slammed into her again. I fucked her hard, fast, and deep without giving her a chance to catch a breath or rest. 

"OHMYGOD! Oh, Fuck! Oh! Oh! Oh!" she cried out when she was finally able to get enough breath to make sounds. She couldn't do much else except hang on and ride it out like a bronc rider in the rodeo. Only this ride lasted a lot longer than eight seconds! 

I pounded the young girl's tender cunt like I wanted to punch a hole in her. If she wanted to be my slut she would have to get used to being ridden and ridden hard. I didn't want to hurt her but I wasn't taking it very easy on her either.

She was a woman now and she would have to learn to fuck like a woman. This was going to be part of her education she couldn't get in the classroom.

I knew that in just a couple short years, she would be leaving high school and leaving me behind. I wanted her ready for whoever might take over my job as her main fuck partner.

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Written by Master_Jonathan
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