A Ring Named Ezzie Pt. 10

As she rubs my asshole she looks at me, and Karen, not Mistress says. "I know this is virgin territory, but rubbing a guy's prostate is supposed to feel really good for him." She holds up her lubed finger. "It's about that deep. I want to try and make you feel really good. Just say the safe word if you have to." She pauses for a moment. I say nothing, and Mistress is back. "Worm, I am going to finger you ass and make you cum so hard." She concentrates on rubbing the head of my dick, and she slips her finger slowly up my ass. God that is odd, maybe full, I am not sure. It's not painful, but I wouldn't say it's good. Wait, what was that. I look down, and she is smiling. She flicks her finger inside me. Oh shit I felt that.

She has a big smile now. "Oh I think you like this?" She flicks her finger inside me a few times and I feel my dick jump. She giggles. "Oh you do like it." She pulls her finger back a little and kind of wiggles it around right at my asshole. She pulls her finger out, and she reaches for the lube. I drop my head back. I can't believe that it felt good. Ugh. What is that? I look down and it looks like she is holding a wand. I feel my ass stretch around something, and it pops in. She lowers the wand, and it pushes something against where she was rubbing.

"What the Fuck?" I moan. It's a vibrator. Jesus Christ.

Karen strokes me harder and faster. "Oh you definitely like this." I can see her lifting the wand up and down making it vibrate right against, I am guessing my prostate. When it hits me it kind of tingles through me, and my dick jumps in pleasure. After a few ups and downs she holds it down so it stays buzzing against me. She starts stroking me faster.

I can't help it, my whole core shivers. Karen drops her mistress voice. My Karen is back. "Come on Ben cum for me. I am not stopping until I make you explode. Give it to me Baby. Come on cum for me. Let it go Baby. Give me your....."

" AARRGGHHHHH. FUCK!" It feels like I am trying to shoot my stomach out of my dick. I literally explode. The first shot lands on Karen's face.

She lets out an "EEEEIIIP" in surprise but never stops. Three more shots follow that end up all over me and her, then I just ooze a lot. I don't think I have ever cum so hard or so much before. She keeps stroking me a little more softly until my body jerks from being so sensitive. She doesn't say a word. She stops stroking me, and slowly pulls out the wand. I feel my body relax.

Karen gets up and disappears into the bathroom. The door never closes so I hear the water running in the sink. She comes out with a warm, wet washcloth and washes the cum off me. When she is done she drops the cloth on the floor and leans down over me.

She starts talking sweetly like Karen to me. "Did you like that? It looked like you really did?"

"That was very, very different." I say. "You read that in Cosmo?"

"Like women have their G-Spot, they call this the man's P-Spot. How to find it, what it feels like, how to stimulate it. It was all there along with pictures and diagrams. They were right too. It said you would cum hard." She says with a giggle.

She stands back up, and slips back into Mistress as she pulls my legs back down and clips them in. "Now for the main event, Worm. I am going to fuck you, and fuck you until I am exhausted from cumming so much. She grabs a bottle of lube and pours a liberal amount on my softening hard on. She takes her gloved hand and starts rubbing it in. "Come on Big Boy wake up. Don't you want to wake up? Don't you want to fuck your Mistress's tight little pussy?" She gets me hard. "There you go. What a good boy."

She reaches down and carefully wipes the excess lube off my groin with the cloth off the floor. Leaving my dick shiny with lube. She must see the confused look on my face, and she laughs. "Did you think this was lube? Oh no Worm, it's a numbing lotion. You asked a few weeks ago, What if you wanted to have a marathon sex session? Well now we are going to have one, once that all dries and absorbs into your skin. After all, I don't want my parts numb."

She walks into the bathroom with the cloth. "Seriously Ezzie, you couldn't have warned me?"

Ezzie answers with her relaxed voice. It seems she enjoyed my P-Spot orgasm too. "I asked you, Do you want me to ruin her surprise? You said no. She isn't going to hurt you. Karen thoroughly read the label. It's not totally numb. It's meant to reduce your sensitivity to make you last longer." Says Ezzie.

"Whose side are you on here, Ezzie?" I half laugh in my head.

"Oh don't be a baby. She tried it on herself the other night. It definitely dulled her sensitivity, but it only lasted about 20 minutes. She is actually looking forward to climbing on top of you. She is enjoying herself. Now play along with the woman you love." Says Ezzie.

"Yes Ma'am, or should I call you Mistress?" I ask.

"No you should call me Princess Esmeralda!" She says giggling.

"Yes Princess Esmeralda."

Karen comes out of the bathroom with just her gloves and mask on. "You made a mess of my body stocking. I should punish you, but I have to admit. Riding your hard on sounds like fun too. I will make you a deal. If I can orgasm three times before you do. I will punish you with pleasure. If not, well I will use my crop on you." She says with a smile as she straddles me.

I swear for the next 30 minutes she takes charge. She bounces on me, and she orgasms. She grinds on me, and orgasms. She leans forward and puts her nipples in my mouth and orgasms. She spins around and I get to watch her ass bounce up and down on me, and she orgasms.

She finally falls forward between my legs breathing and gasping heavily. "Oh wow. That was Amazing." She lays there panting. I get a birds eye view of her red and swollen pussy. Her lips are partially open, she is soaked, and I can see some wetness just oozing out of her.

She turns around and smiles at me. "Now comes your pleasurable punishment." She says as she reaches down off the side of the bed where she has been keeping things out of sight. She comes up with a tube and her crop. "Do you know there are very few sex toys for men." She says as she sits on my thigh randomly slapping my body with the crop. Not hard enough to hurt, but a gentle sting. "But the writer of the Cosmo article mentioned buying this for her research for the article to use on her boyfriend. Only she doubled down and used it with the prostate massager. I thought that could be a bit extreme."

She holds the end up so I can see it. "They model these after porn actresses. I looked through a bunch to find one close to me. Do you think it looks like me?"

"Very close Mistress." I say.

She tilts it up and pushes the hole open and pours in some lube. She then rubs her lubed fingers around the pussy lips and rubs in the lube. She pours some lube over my hard on and pushes me into the toy. "Oh wow." I say.

That feels kind of nice. It's a soft spongy squeeze on the head of my dick. Little by little deeper and deeper she pushes me in. Wow I am surprised at the feeling. Whatever bumps etc they have inside this thing actually feel nice. Once she has it worked in, she starts faster strokes.

"Oh it looks like my little Worm likes this toy. Maybe the author of the article had it right." She lowers her hand under my balls and feels around. Oh No. Yup, there goes her finger up my ass. I just moan. "Tell me Worm, do you like what I am doing?"

"Yes Mistress." I say.

She smiles down at me. "Use your words Worm. What am I doing to you? What do you like?"

Ugh she is turning the tables on me. "Mistress I like you jerking me off with the....Fuck! Oh Jesus!" The toy starts buzzing.

Karen laughs. "Oh you like the vibrator I see. Use your words Worm."

I can't help keeping my body still. The pleasure just keeps increasing. "Mistress, I like you jerking... me off with the vibrating toy. Oh wow. And fingering my ass and prostate."

Karen has a huge smile on her face. She shoves the toy down on me and reaches up to pull the lace mask off her head. I can see it in her eyes. She is my Karen again.

She reaches down and continues stroking me inside the toy. My hips are spasming. "Look at me Benjamin." She says softly. I look up at her. "Cum for me Baby. I am not stopping until you do. I want you to see stars. I can feel you flexing inside you. Cum for me Baby. Fill my rubber pussy with cum. Do it Baby."

I am literally panting. I am rolling and jerking my hips. Then it happens. It almost feels like a cramp, and then I explode and cum. I scream out. "Ffuuccckkk!"

Karen keeps stroking me and flicking her finger. All I can do is beg. "Please. Please stop. Please."

She pulls out her finger, and pulls the toy off me. As she does a blob of cum drips out and lands on my stomach. She giggles and tips it upside down to keep the mess in it. She puts it aside, pulls off her gloves and works on releasing the restraints.

Once I am loose she crawls up beside me and rolls me to her with my head on her chest. She runs her fingers through my hair. "Ssshhh, breathe. Just breathe. That looked like you really enjoyed that Ben?"

"Uh huh." Is my only response.

She giggles and just continues to hold me to her and run her fingers through my hair. It takes me a moment, but I finally speak. "You read that in Cosmo? What is Cosmo? Womens porn?"

She laughs. "They have some very educational articles sometimes."

"So does Playboy & Penthouse." I say.

She slaps my arm playfully. "And naked girls!"

I push myself up and crawl up so my head is near hers. "I love you." I lean in and kiss her. She wraps her fingers back in my hair and holds my head as we kiss.

We break the kiss and she nudges me back down. "This is my weekend." She says softly. "And I want to lay here and hold you." I snuggle back against here chest and we cuddle. Next thing I know she is standing beside the bed waking me up.

Rise and shine sleepy head. We have dinner plans and you need a shower. I look up and she is wrapped in a towel, fresh from the shower. I just groan. She grabs my arm. "If I promise to wash your back, will you get up?" She asks, and then laughs as I start getting up. "Remember, Washing Only."

I step in the shower and she gets in behind me. I step under the spray and turn to her. She has a loofah all soaped up and ready and she starts washing me. I am covered in soap from my shoulders to my knees, and my dick is waking up. She giggles. "Spin around and tell Little Ben he is in a time out."

"Hey!"

"I told you. Wash only." She starts scrubbing my back. She gets down to my ass. "So how was my finger and the toy in your bum?" She asks.

"It was very odd going in. I won't say it hurt, but odd. Your flicking finger and the toy. That was really different and good." I say.

She wraps her arms around me from behind and hugs me. "So we should hold on to those toys for another time maybe?"

"Sure I would try it again." I say as she hugs me tighter.

She lets me go, and sighs. "Oh I am covered in soap."

I spin around. "I can help with that."

She holds her arm on my chest. "If you help it will turn into you assaulting me." She laughs. "Rinse and get out. I have plans for us."

"Party pooper." I say.

Karen points to the curtain. "Out!"

I reluctantly step out, and when she opens the shower curtain to step out, I am holding up a towel for her. She steps up and turns her back to me. I wrap her in the towel and start groping her chest. She steps away laughing. "See, I told you, assault." She says as she walks out of the bathroom.

I see her gloves and fishnet hanging over a towel rack to dry. I see the toys on the vanity on a towel. I see now the wand has an angled bend at the end, maybe 45 degrees and a small egg on the end. I laugh in my head. It felt bigger. Then I think of fucking Karen up the ass. That must have been worse for her. I mean I know people do it all the time. I am not huge, but I am bigger than the egg. I table that for now, but I do want to talk to her more about it.

I walk out and whistle as she is standing there in her bra and panties pulling her jeans up. She smiles at me and turns to pull a sweater on. I throw back on my clothes I left by the door. With some fresh body spray and deodorant. I am sitting on the bed tying my shoes when she comes close to me. I reach out and grab her hips and pull her to me. I pull her body to my head and breathe in.

"Ah my favorite spot." I say as I breathe in and smell her perfume, while looking up at her from between her boobs. I then try slipping my hands up under her sweater. She laughs and pulls away. "Stop! Put on your shoes."

"You can't blame a guy for trying." I say. She smiles but stays out of reach.

I drive us to a restaurant she directs me to, and as we walk in Beth & BJ are at the bar. The girls squeal and hug. They then step off to the side, and start whispering and giggling. As I shake hands with BJ, I ask Ezzie. "Ezzie, what are the girls whispering about."

"They are comparing notes." Says Ezzie.

"What do you mean comparing notes, Ezzie?"

"Beth and BJ were across the hall from you and Karen today in the hotel. Karen and Beth planned this together when Karen told her about it being her No Saying No weekend and the strip joint." Says Ezzie.

"Did Karen tell her Everything?"

"Yes Ben, everything. Karen and Beth share everything with each other." Says Ezzie.

I look at BJ. "I think we have been set up." I say. He looks at me confused. I keep talking. "Hotel room, fishnet body stocking, gloves, mask, restraints, and a very um personal exam?"

"Oh shit. We were!"

"Ok. We are big boys. We can take it. We will just file this one away for another time. Revenge will be ours." I say with a laugh. We both laugh and the girls look at us. "The guys have compared notes too. It seems you girls did some shopping together." I say with a smile. I would love to say more but there are tons of people around.

They come over to us and hook their arms in ours. Beth looks at BJ. "Any complaints?"

"No Mistress." BJ says quietly with a smile.

Karen looks at me. "And you Worm." She asks lovingly.

I laugh. "No Mistress."

Karen pats my arm. "Good boy."

We sit and enjoy dinner and drinks. BJ and I talk a little shop. He shows me a document he is working on showing Cohen at the Old Boys Club for lunch, and the next day big buys or sells happening for one stock or another. He sends me the document, and promises to keep track of future stuff. Now I need to get the member or guest list at the club and compare members vs stocks. This should be no problem with Ezzie. I don't necessarily want to nail Cohen. I want to know his secrets so I can duplicate them.

I show everyone the info for the Christmas for Kids charity, and tell Karen we are going. She gets all excited.

BJ is reading through some of it, and looks at me. "Can you hold a table for my firm? I bet I can get it approved, and network with some people there."

How had I not thought of that? These are pricey tables. They should be well off people. Ezzie could influence a lot of people to give me their Real Estate work, BJ their financial work, and for that matter any HVAC stuff I can send to Mr C. Holy Shit this could be Huge. I email Natalie and tell her I need her to hold a table for me for BJ's firm and to send me any forms for it to be filled out.

Both Karen and Beth are now giddy about a formal black tie event. I get a quick text response from Natalie.

NAT - If I am doing you a favor and holding my last table, I need a favor from you.

ME - What favor Nat?

NAT - is your friend handsome?

ME - What?

NAT - Is he handsome?

I hold up my phone and snap his picture, and send it. BJ stares at me. "Did you take my picture?"

"Yeah Natalie is asking me for a favor to hold the table, and are you handsome?" He looks at me. "I don't know BJ."

A moment later...

NAT - I will hold it if you both agree to a Blind Date Charity Auction for young bachelors and bachelorettes. 12/20 there is a Christmas for Kids sponsorship for a Holiday Play in town. You both agree to Dinner and the Play that night for the winner of the Blind Date/Silent Auction Winner and you have a deal. The tickets are provided and the entrees are covered by Mel's. You pay the rest of the tab.

I stop and think. My last class is a few days before that. I have no good excuse. I groan and hand BJ my phone. "Seriously!" BJ says.

Beth is reading over his shoulder and giggles. "Our men are going to be Auctioned off for a night on the town."

I am just shaking my head in disbelief. Why can't I be there in person? I could have Ezzie stop this. Fuck!

Karen laughs. "Oh come on. It's for charity." She then starts singing the old song. I am just a Gigolo.

I look up at BJ as he hands me the phone. "Fuck It. Why not? It's for charity." He says.

Beth joins in with Karen singing. Oh god. They are never going to let this go.

ME - OK Natalie. You have a deal.

We go back to the hotel, and the girls tell us to wait in my room. Karen grabs her bag and heads to Beth's room.

Fuck it. I did agree to the No Saying No. I am not even asking Ezzie. A few minutes later the girls come back in the bikinis and cover ups from the July 4th weekend. They are walking proud and sexy with the cover ups hanging open.

"Karen, I have no suit." I say. Both girls pull tiny Speedos out from behind their backs.

Beth has a huge smile. "You boys can wear these and a t-shirt."

I sigh. "Ok fuck it. Let's go." I get up and grab mine. Right there I pull off my pants and pull it on.

Ben has a button down shirt on. "I'll be right back." He takes the Speedo and heads for his room. Just a few minutes later he is back in a t-shirt, Speedo and sneakers.

The girls pull their covers closed and we walk to the elevator. The pool & hot tub area is empty. I walk over and turn on the bubbles. BJ and I are in the hot tub. The women are taking their time. I think they want to make an entrance, and god do they.

They both have on sexy tiny bikinis. Fuck they look great. Both BJ and I say "Wow!"

The girls giggle and walk up to us. They both put their hands on their man's chest and push us into a seat. They both then kneel and duck their heads in the water, and come up. They push each other's hair back and kiss. They stand there holding each other's head, and reaching their other hand down just under the water to rub the other's ass. They break the kiss and turn to us.

Both BJ and I are dumbfounded. I find my voice. "God you are both so sexy and beautiful."

"Jesus yes." Mutters BJ

They both walk up to their man and sit in our laps. Karen holds my head and kisses me. It's a soft, sensual kiss that goes long enough to be more than a kiss. She pulls back and just smiles at me as she grinds her ass into my lap.

She turns and looks at Beth. "Oh Ben is very happy."

I can see Beth wiggle on BJ. Beth smiles at Karen. "Let's swap and see who is happier."

I can see the sparkle in Karen's eye. "Good idea." Ben and I are just staring at each other. We can't believe our luck.

"Ezzie, are you sure Karen wants this?"

"Yes Ben. She is very excited. Her feelings have changed about another man since you had sex with your parents." Says Ezzie.

Beth comes to me and jumps on me straddling me. She holds me back against the edge of the hot tub and kisses me hard. It's a very different kiss then the one Karen just gave me. She grinds her pussy against me as she does. She breaks the kiss and we notice Karen is sitting on BJ's lap and they are just watching. Beth giggles. "Karen, I think Ben & BJ are equally happy. What do you think?"

Karen spins and straddles BJ like Beth is on me, and she kisses BJ. Like Beth she kisses BJ long enough to be more than a kiss, but it doesn't look as hard. Karen pulls back from the kiss, but makes a point of continuing to hump against BJ. "Beth, I think you are right. I think they are equally happy. Maybe we should get a hands on comparison."