Lucky Guy Pt. 07

Jamal had taken a paddle and was whipping Jeong ass very hard. As soon as he finished turning her ass very red, he got between her legs and licked her ass and pussy. You could see the juices on the edge of her pussy.

Edgar was kneeling and fucking Annie slowly. She had her head back and was moaning. I placed my hard dick in Eva's mouth and let her suck on it. I wanted to pace myself as I wanted to get to Annie and Jeong before ejaculating on Eva as a finish.

As Eva was sucking me, I had her vibrator turned on low. I asked, "Can you have an orgasm on that speed."

"Yes, it feels wonderful. I probably would anyway because my L is allowing me to suck his penis. Thank you."

"I want you to please the other Doms also. That will also please me."

"Yes my L. Anything."

I was watching Jamal huge dick slamming in and out Jeong's small pussy. I couldn't believe she took it so easily.

I motioned to Denise. "I want you to show our appreciation to Denise for taking care of us."

"Yes my L. I will do my best."

Denise spread her legs, placed them at shoulder width to Eva and pressed her hips forward. Eva licked and sucked on Denise's pussy. I watched this until Jamal came to me and whispered, "Fuck Jeong while you slap her ass, pinch her tits and nipples. She likes pain with her pleasure. Time for Annie to take this." He grabbed the largest penis I had ever seen. The veins were as large as the veins in athlete's arms. It looked menacing. I wasn't sure Annie could take it except I just saw a much smaller woman do it.

So I went to Jeong as Jamal moved to Annie. Edgar moved to Eva. I watched just long enough to see Jamal slip that slab of meat into Annie beautiful plump body. I could tell he was taking it slowly.

I slapped Jeong's ass hard with my hand and said, "Do you think you are worthy to have me fuck that nasty Korean pussy?"

Jeong had a dark complexion and her whole body was the same very light mocha color. She said, "I could never be worthy of Principal Lance's attention but I am begging for it."

"I am going to punish you for being a teasing slant eyed slut while I fuck you."

"Yes Principal Lance. Do whatever you want to me."

I could tell that talking in a demeaning manner to her was a turn on. I slipped my dick in her pussy that was still wet from the fucking Jamal had given her. Much to my surprise, she was tight even though I easily slipped to hilt on one push. It felt good.

I slapped one ass cheek and then switched to slap the other. Her ass was already red from the whipping Jamal had given her. "You are one nasty bitch. You really like this. Don't you?"

Jeong said, "Oh yes Principal Lance. Anything you want to do to me."

I reached around her to hold her steady and slammed my dick as hard as I could into her. I could feel her ass against my stomach. I reached around her while holding it there, took a nipple in each hand and squeezed as hard as I thought I could. I knew this was going to leave her nipples bruised. Much to my surprise she moaned in pleasure and I felt her pussy contract. Her pussy muscles were squeezing my dick. It was like nothing I had felt before.

As she released, I slapped her ass again. I said as menacingly as possible, "You must have fucked a lot of men with that nasty pussy for it to be able to clamp down like that. You have one practiced pussy, don't you?"

"Yes Principal Lance, I have fucked a lot of men for my master. I love to pleasure men. Please make me hurt some more."

Again, I got as deep as I could but I didn't want to pinch her nipples again so I reached around with both hand and took the lean meat on either side of her clitoral hood between my thumb and index finger. She knew what I was going to do and said loudly, "Yes do it. Hurt me." I squeezed as hard as I dared. Her pussy began to contract, her hips shuddered, her breathing picked up and she began to cry with ecstasy. I reached around her body to rub her breasts soothingly as I made gentle movements in and out of her vagina.

Her breathing became a little more controlled and said, "Thank you Principal Lance. You have been so generous with this unworthy Korean slut."

"You are a very good slut. That is your reward for pleasing me."

I kissed her on the neck as I removed my dick from her pussy. Edgar took my place.

I looked at the beautiful plump baby that had managed to take half of Jamal's dick. He saw I was ready and he slipped his dick out and said, "The plump bitch is all yours."

I knelt between her legs and kissed her nipples and asked, "How was he?"

"Big, but after I got used to it, it felt good. But I am looking forward to having my Principal Lance's dick in me."

"You have a beautiful body Annie. I am looking forward to this."

With that I entered her soft fat pussy. "Oh Annie that feels so good. You know I am partial to soft fat pussies."

Annie looked at me a little worried. "Did he make me lose?"

"No, it feels perfect." I alternated between feeling her big G cups and her soft round ass. She was thrusting her hips up with each stroke in. I tried to keep a slow pace. I wanted it to last as long as possible knowing that I wanted to give Eva my cum. She closed her eyes and I could tell that she was enjoying that I was watching her breast rock from side to side as we moved together. I could also feel the orgasm that was almost continuous.

I then realized that Edgar was standing above us and that Jamal was untying Jeong.

I pushed in one more time, kissed each tit and said, "Thank you, that was wonderful."

I looked at Edgar and whispered, "We don't deserve to be this lucky."

He said, "You got that right."

By the time I got back to Eva, Jamal and Jeong were there. Jamal asked, "With your permission, we would like to show you how to treat this nasty dirty slut whore that likes cum on her."

"You have my permission."

Jamal said, "Fatty place your lips around the tip of my dick. Jeong is going to beget an orgasm from me and I want you to catch all my manly sperm but swallow none. Understand bitch?"

"Yes Master Jamal."

Eva took the tip of his penis in her mouth as Jeong took some lotion and slide her hand up and down his shaft. Her hand would not even reach around it but with only a little coaxing he shot his load into Eva's mouth. She held it there until Jamal said, "Open up, I want to see that you have it all." Eva opened her mouth and the cream liquid coated the inside of her mouth with gummy strains glistening between her lips and teeth. Jamal continued, "That's a good oral slut, now mix in your saliva and force it out of your lips. I want to see it run down your chin onto those lovely breasts."

She did exactly as he instructed. I raised the vibrator to medium. I could see the orgasm and I thought it would be continuous until Edgar and I did the same as Jamal.

"Ok Edgar, you and Annie do the same." Edgar put the tip between Eva's lips as Annie stroked him to orgasm. Eva opened her mouth and you could see her body shake from the orgasm as she showed us that he had caught his sperm. She pushed the watery cum out the side of her mouth and onto her chin and chest.

"Now it is time to take your L's nectar." I turned the vibrator to high, placed my dick between her lips and had Denise stroke me to an orgasm, I lowered the vibrator to medium as she opened her mouth to show me she had caught my cum. Again, I could see the shudder but this time Jamal held her by the arm for some support. I turned the vibrator off for the first time in over twenty minutes. She slowly closed her mouth, smiled at me as she let the juices slowly exit the sides of her mouth and dribble down her chin and onto her now wet breasts.

She was wet from sweat, had cum on her face and chest and the paint was running in rivulets down her perfect breasts. In short, she was the most beautiful creature I had seen. I lifted her up and into my arms and squeezed hard.

She whispered, "You are going to get as nasty as I am."

I laughed, "Promise me that it is forever."

She smiled at me, hugged me back, "Do you really mean forever?"

"Yes but pretend I didn't say it."

She said, "Ok." We kissed for an extended period. I could see that Edgar and Annie were also embracing.

Denise was holding a tray with bottles of water and shots of tequila. So we sat and drank water and did the shot. Denise asked, "That was awfully intense. Are you guys going to do the Anal Class?"

I looked at Eva, who said, "I was promised a butt fucking tonight." She placed her hand on my genital and said, "Are you up to it?"

"Denise one more bottle of water, another shot of tequila and onto the butt fucking."

Denise smiled, "Good. I would have been disappointed otherwise. What about you two?"

Annie said, "If Fatty's butt gets fucked tonight so will mine. Although I have never considered it before this; if my BFF wants it so do I. Edgar?"

Edgar smiled like a Cheshire cat and said, "I have been trying to figure out how to ask for that for a while and my good luck is that you are asking me. Hell yes I want to fuck that big beautiful butt."

Denise asked Eva, "You are awfully messy. Do you want a towel to clean up a little?"

Eva looked at me and said, "Principal Lance wants me to be humiliated and this is very humiliating."

Denise said, "Ok then let's go to the Anal class room." She led us back to the sitting room where we did the oral class. It still had the soft narrow benches that could be tilted. Now they were laid flat, we sat drinking our second bottle of water.

Stanley and Angela were talking. Angela was still wearing the bustier but had taken the legging off, leaving her nude from the waist down. Stanley was now nude. Eva was only wearing cum, sweat, running paint and the thigh high garter stockings that by now were full of holes. Annie was still wearing the tattered shirt, a little running paint although most had been rubbed onto others and nothing else. I noticed all the button were torn off my shirt and I decided it was not needed. Edgar also decided the shirt was unnecessary.

Denise came back with one more shot and another water each. Edgar raised the glass and said, "Here is to breaking some anal cherries tonight."

Angela said, "Here, here. It looks like you have all had a good time at our party." Angela had a folding chair that she placed between the two couples and sat. Angela was certainly older and had some wrinkles but still was very sexy. It is likely she was never pretty like Eva but had big boobs which I guessed had been augmented and a big fleshy ass. She had a middle age spread around the gut which the bustier mostly hid.

Annie said, "We certainly have Mrs. Samford."

"Annie, in my house it is Angie. The Mrs. Samford is for work only. I am so glad the four of you found each other. I really meant to introduce you but it looks like it happened anyway. You were the only ones that hadn't been to one of our parties before."

I said, "Denise has taken care of everything. I would really like to give her something extra."

Denise said quickly, "Oh I have gotten my reward." She looked at Eva and smiled.

"We are going to do one thing to start the class but then we are going to chat. Denise get us lube and plugs for these two girls. What we are going to do in to try to get you relaxed with an anal plug before we let these nasty boys put their big things in you. I want to show you though that these plugs can be comfortable."

She got up and bent slightly showing us a red jewel lodged in her anus. She slowly slides it out. I was surprised at its size. It was six inches long and at least two inches in diameter. She held it up and said, "I have been wearing it all night. It feels good in there to me. I wear one many times to work and to business meetings. In fact, when we met Saturday I had a smaller one than this. But I love anal. My only point is that this is mental. If you think it feels good it will. I promise you it will make orgasms more intense if you like it. I am going to show you how to insert it. But know the first time it will hurt. I want you to insert it, accept the pain and if you relax as we chat then we will move to more. If you can't abide it, then say so and just fuck. If you fight it, you will never be able to do it. Understood?"

Eva said, "Yes, let's continue." Annie also shook her head.

Angela took a tube of what was called man grease and dip out a generous amount between her fingers and said, "I know it say man grease but anyone can use it. Well you can figure it out. I use a different product now but this is the best for newbies."

She placed a foot on the chair, inserted two fingers with the grease as far as she could into her bum hole, her labia were extended and spread as she lifted her leg to the chair and slowly inserted the big plug until it was securely situated. "The shape secures it as long as you get it all the way in. The natural reflect is for the anal muscle to try to push it out. Think relax. If you just forget it is there the pain goes away and it stays." She twirled showing us how secure it was.

"See. This first time I want the guys to do it for you. But first guys kiss your partner and tell them you want this."

I took Eva in my arms kissed her deeply and said, "Fatty I want you to try this for me."

Eva said back, "Yes my L."

"Ok girls stand and place your foot on the bench. Guys take some of the grease in your middle finger and find her bum hole. Slip first one finger in and kiss her as you do that."

After we had done this Angela continued, "Now take two fingers with the grease on them and insert them slowly into their bum hole, kissing them as you do this."

After we had this done Angela said, "Now take the plug off the trey Denise is holding, dip it into the jar of grease and slowly slip it into your girl's hole while kissing them. Girls look at the plug and you will see it is much smaller than the one I have in."

I took the plug which was about four-inches long and an inch in diameter. It didn't have a jewel on the end but had an oval flange. I dipped it in the jar of grease reached around Eva and found her rosebud with my thumb. I slightly inserted my thumb to make sure I had the right spot. I took Eva in my other arm, drew her close to me, placed the tip where my thumb was and pressed forward just a little. I looked over and saw that Edgar was at about the same spot. I couldn't believe it but I was getting hard again.

Eva whispered to me, "Push it further. It is okay." So I pushed in about two inches and looked at Eva's face. I could see no strain on it. I looked over her shoulder to see what I was doing to her but was still holding her close to me. I pushed a little more and all but the widest part was impaled in her ass.

I said, "One more little push. This may hurt a little but then it is in."

Eva said, "Go ahead." I pushed it in all the way. I glanced over at Annie beautiful butt and saw that she had taken it also. Eva whispered to me, "Not too bad. I just need to get used to the feeling but not bad at all."

Angela said, "Good job guys. You did that like experts. Denise get us all a shot of tequila and more bottles of water. Sit down girls and let's talk. How does it feel?"

We sat on the bench, while Angela sat in her chair. Annie said, "It feels fine. There was a little pain to take the first part but now it just feels a little funny."

Eva shook her head, "Same here, I think it is just a matter of getting used to it."

Angela said, "Good, you are both going to be able to do this. The few women who haven't been able to do it, fought it from the start. Now tell me how you have enjoyed our party?"

Eva said, "It is the best party I have ever been to. I have had so many orgasms I lost count. I can't believe how organized this has been. I learned a lot."

Angela looked at Annie, "Me too but this is the first sex party I have ever been to. Edgar and I have done a few, ah, provocative things but nothing like this."

Edgar said, "How did you know we would like doing this?"

Angela smiled, "Annie just had the vibe of a submissive. Besides she is sexy as hell and it was hard for me to believe she wouldn't want to use that." Annie face turned red, embarrassed by the compliment.

Denise came with five shots. I raised the glass, "Here is to our very gracious host. Angela you and Stanley have been so good to us."

Angela raised her glass and nodded with a smile. We put our shot glasses on the trey. Stanley came up and Angela said, "Just in time. Girls it is almost time for the real thing. How does it feel now?"

Annie said, "I hardly even know it is there."

Eva said, "Me too."

Angela said, "Denise take the chair and place a mat down for me. Guys move the bench apart just a little. Stanley and I are going to use a mat between you so you can see what we are doing."

Angela said, "Now girls take the small vibrator from Denise. Guys fondle their breast and kiss them until they have an orgasm. When you have the first orgasm straddle the bench, place the vibrator between your clit and the bench and bend over."

So Eva took the vibrator and placed it between her legs. I kissed and fondled her breast. She had a small orgasm, straddled the bench with her ass easily accessible and wide open to me. I knew what Angela was doing.

Denise handed me and Edgar a squeeze bottle with lube in it. Annie was now in the position. Angela continued, "Pull the plug out, take the bottle of lube and stick the nozzle in her ass and squeeze as much as possible into her hole. It won't hurt them." After we had done this Angela continued, "Now take some grease and rub it on your penis and watch what Stanley does. Stanley slow not your normal ram it in."

Stanley said, "Yes Mistress." She got on her hands and knees where we could all see her. Her fleshy tits were hanging almost to the floor. Stanley got hard watching Annie and Eva masturbate and open their asses for him to see. He pulled the plug out, placed some grease on the tip of his dick and slipped the tip past her sphincter with no resistance.

Angela said, "Guys you will not be able to slip it in as easily as Stanley did. The girls' tight anal muscles will try to keep you out even though they will try to relax. But push in but go no further than what Stanley is doing. Let them get used to having just the tip in."

I positioned my penis at her rosebud and pushed forward a little. I could feel the resistant of the anal ring. Angela said, "Girls relax but think about how it feels to use the bathroom, that will relax the sphincter muscle."

Suddenly, I felt the resistant abate so I pushed to this first position. Eva made just a little flinch but made no sound. I could hear the vibrator running. I looked over at Edgar and he had the tip in Annie's ass also.

Angela asked, "Girls relax as much as possible. When you think you can take more say so."

Annie said, "I am ready."

Eva said, "Me too."

Angela said, "Girls put your hand on your guys hip and control how quickly they push forward. Guy squirt some of the lube from the bottle on her anal ring before you move forward. Stanley, I want all that dick. Denise hand me my vibrator." Denise handed her a rabbit about nine inches long. As Stanley pushed forward she let the vibrator bounce on her clitoral hood.

I squeezed the lube on the hole that held my penis. I pushed forward about an inch. Eva stopped me but only for a moment, she pulled me forward another inch. I squeezed some more lube on the spot. I was making a mess on the bench. I looked over at Edgar, who had a longer dick than mine and he was half way in. Eva had taken her hand away inviting me to move forward. I did and this time she didn't stop me until I had all but an inch in.

Eva asked, "How much more is there?"

I answered, "About an inch."