My Apprentice & I Have a 2nd Outing

Cassy was fairly ill the day after we went to the club, she really overdid it, lots of booze, lots of fondling, dancing, kissing, cumming and that was just at the bar.

We chatted every night that week and it was surprisingly about how things work in the bar scene rather than how she was going to try to reconcile with her husband. That was her choice and I really liked having her with me and taking her under my wing.

She did confide in me that she lost her virginity to Brent (her husband) and I replied that I was upset because I wanted it. We had a good laugh and she said that I was the first woman she ever kissed and fondled like that night at the bar and after the bar. I told her that I so enjoyed it and really wanted to take it to the next level and we should next time we go out.

She said she needed to think about it but admitted the thought did arouse her.

One night that evening her toned changed and she asked "I want to ask you about something, it's something I've been curious about for a long time."

"Sure hun, you can ask me anything." I was quite nervous about what she was going to ask but she already knew pretty much all of my history.

"Your belly button piercing looks so sexy, did it hurt to get it?"

"Yeah it did, but I love it, you would look so good with yours done too."

"Not with my c-section scar, I don't have the body you do after 2 kids."

"Hun, you have a great body and I have seen it all, you're going to get it done, my treat."

"All right fine, Friday night Brent is picking up the kids, we can go then."

"Perfect! Dress sexy because I'll get Dwayne to drive us and then we'll go to the bar."

"Christy! I don't know if I can do that again."

"Don't worry I'll take care of you, just like last time, okay?"

"Fine, I don't know how I let you talk me into these things."

"I'm not, I'm simply telling you what you already know you want to do!"

Friday comes, Dwayne agrees to drive us before he goes to his weekly poker game. I've gone with a blue and black backless dress, no bra of course because that would just show and since my period is over, no underwear. My dress is short and on the way to pick up Cassy I can see Dwayne looking at my bare legs, my dress is slide up quite high.

"Watch the road and stop trying to see my pussy, what are you 12 years old?"

We get to Cassy's house and she meets me on the stairs, she looks stunning! Her hair is nicely curled, she is wearing a tank top with spaghetti straps and a short leather skirt, so hot.

"Are you wearing a bra?"

"No, you would just take it off me."

"Are you wearing underwear?"

"Yes, I feel more comfortable with-"

"Cassy! You're lucky I don't rip them off right now and throw them in your neighbor's yard!"

We both laugh and get into the back seat of Dwayne's car.

"Okay ladies, what bar are you going to?"

"Not sure yet hun, drop us at the mall."

"The mall? Why the mall?"

"Because we want to go to the mall, ple-ase!"

"Okay, Okay."

Cassy and I act like teenagers in the backseat giggling and taking selfies of the "before picture" as we call it. I take a picture up our skirts and show her my bare pussy compared to hers covered with lace and cotton.

"Now which one would you rather see?"

"Well if I was a guy-"

"Cassy, you're not a guy, I'm asking which one would YOU rather see?"

She lets out a deep sigh "The bare one of course."

All through the ride I see Dwayne checking the rearview mirror, but he's not looking at me. Then I catch on, he's looking at Cassy, he seems quite interested in her new attitude and how sexy she has dressed.

We finally get to the mall and as we get out of the car I say "Thanks hun."

"Are you coming home tonight?"

"No, don't plan to."

"Okay...do I get a kiss?"

"Not from me."

Not that I was hinting at this, but Cassy goes up to the driver's window and plants a big wet kiss on Dwayne's lips, "There's your kiss!"

We walk away, laughing at that, a week ago she would have never have done that!

We make our way to the tattoo shop and Cassy tells the guy there that she wants her belly button pierced. He tells her to pick out the one she wants and he'll get everything ready.

There are a lot to choose from and she decides on a nice barbell style with a heart on the end, very classy I tell her.

She lies down on the table and he puts the freezing spray on her area and then the alcohol and she holds my hand, tight, very tight!

She closes her eyes as the needle goes through one side and out the other, the tattoo artist slips the jewellery in place and I admire it, wow so gorgeous!

Cassy looks down at it and is quiet for a while.

"What do you think hun?"

"Um, I...like it...no...I love it!"

"Okay great, don't go swimming for at least 2 days and don't take it out or change it for at least a week."

That is one thing off our list of things to do, now to the bar!

We get to the bar, it's about half full already and a lot of really cute guys. I realise that I am very horny, our adventure last week really turned me on and I didn't get a release because of my goddamn period. Tonight will be different, but this is about Cassy first I think to myself.

"No reason why I can't have fun after she's taken care of, it's allowed. Of course I will take care of her and this will be a night she will always remember," I promise myself.

I am looking at myself in a mirror on one of the pillars and a cute guy walks up to me and smiles, I decide to start a conversation with "Does this bar make my ass look fat?"

He looks at me, obviously no idea how to answer, shrugs his shoulders at me and walks away.

"What the fuck did I say?"

Cassy is laughing hysterically but says "Christy, you asked that guy if the bar made your ass look fat! What does that even mean?"

"I need a drink, I don't know, shit!"

We find a table and have a seat, surveying our options, looks good a large amount of good looking guys and gals here, this is going to be a good night.

"Christy, what if a guy tries to pick me up and take me home?"

"Then you're going to get laid tonight hun!"

"Will you come with me?"

"Hell yeah! Threesomes are incredible, you'll see"

"So we're having sex tonight?"

"Yes, if we don't have sex with guys, you and I are going to sleep together."

"Now I need a drink, this is a lot, but it is getting me wet!"

A couple of young guys come over with slicked back hair and buy us some drinks. We chat with them for a while and they slowly lose interest and wish us a good night.

"What's wrong with them?"

"Did you really want to sleep with some greasy young punk?"

"No I guess not, you have a bitch side to you?"

"Hey it's my body and so far you are the only one in this bar that has seen in and has touched it, my body, my choice."

"Right my body, my choice"

"No, in your case it's your body and my choice!"

"Christy!"

A few guys have stopped by and chatted with me, most of them took it as an invitation to touch my bare back. Some have really rough hands like sandpaper, no thanks!

One cute guy "accidentally" grazes my breast and I just look at him.

"Sorry, I didn't mean to do that."

"Well if you're going to do it, do it right!" and I pinch his nipple, hard.

He laughs and pinches mine, not as hard, actually felt quite nice, I like him!

Cassy is also talking to a guy, he's quite cute and she is all smiles, her sexy legs crossed and she is showing a lot of leg, she's nailing it!

My new friend buys more drinks and is rubbing my bare thigh, I don't let on but he is getting me pretty wet, but I haven't decided if I am going home with him or not. He leans in and kisses me, I kiss him back, he is a good kisser, his hand travels up my skirt and he has learned that not only do I not have any underwear on, but my bare pussy is quite wet.

He looks around and says he has to go to the washroom and will be back. Not sure what happened there, was he disappointed I was wet or did he not like my kissing?

I look over at Cassy, she's sitting on the guy's lap now and shouts across to me "You scared him!"

I'm looking around for him and spot him in a heated argument with a woman, guess he wasn't supposed to feel me out or kiss me in her eyes. Cassy's man has had 2 buddies join them and she points to me. They come over to me and introduce themselves, "I'm Christy, nice to meet you!"

These guys are well put together and very well dressed, cute as hell.

We make small talk, they both can't decide where their eyes should be either on my legs, between my legs or on my boobs, but apparently eye contact is out of the question.

Cassy is making out big time with her man, she's doing well, now I have to decide what to do with the other 2.

I stand up to adjust my dress and stumble a bit, shit a little embarrassing, then I realise I've been sitting for a while and have had probably 5 or 6 drinks. One of the guys puts his arm around me and asks "Are you okay love?"

"Yeah, just not so stable on my feet as I thought!"

We are standing close to each other talking to the other guy, he puts his arm around me and rubs up and down my side, very soothing. The patience of his friend has worn off and he walks over and kisses me full open mouth, full tongue and his hand cups my breast. The other guy has his hand on my ass now as I make out with his buddy.

We all sit down and one of the guys asks "Do you ladies have another friend you could call to join us?"

"Why hun?"

"Well, just that there are 3 of us and only 2 of you, would be better if the numbers were equal."

"My dear, I am thinking about the same thing you are thinking about, it's not a problem."

The guys look at me puzzled, Cassy looks at me puzzled. Shit, do I have to explain it to everyone? Apparently, here I go: "There are 5 people here, we all want to have sex, right?"

Everyone agrees.

"You are concerned that there are more guys than girls, right?"

The guys all agree, Cassy is silent, afraid of what she knows I am going to say next.

"Think of it like this, 3 cocks, you guys have 3 cocks, we each have 3 holes, we can make this work!"

Everyone gets very excited, the guys are trying to figure out whose place to go to while I sit back and enjoy my drink. One of the guys has his hand way up my dress, so turned on.

Cassy is sitting in silence, she looks at me and smiles. She is nervous because she knows this will be her first time with a guy other than her husband, maybe her second and third time as well and probably just as nervous as she knows it will be her first time with another woman.

On the ride to the house I whisper to Cassy "Are you okay with what is going to happen here?"

"I think so, just a lot to process, you know I haven't done anything like this before, actually nothing except with Brent. Fuck!"

That may have been her first ever F bomb, I console her, "I'm here and it's going to be great, we're about to have a great evening,, just stay with me."

"That's the other thing, I have no idea how to have sex with you, I mean I want to, I've thought about it and I really want to but how?"

"When the time comes just do to me what I do to you and think about what turns you on and go with it."

She nods and looks me dead in the eyes "Christy, I am so glad you are with me for this, god I love you for that."

She reaches up and kisses me on the lips then opens her mouth around mine, we make out in the back of that cab, her hands all over my bare legs and breasts, she is getting me so wet. The car comes to a stop and we all enter the house, I hold Cassy's hand.

It is a nice house, very clean, not how a bachelor would keep a house, so there must be a woman involved somehow, but that would even the numbers!

"Are you ladies okay, did you need water or anything?"

"No hun, we're good for now!"

You can sense the anticipation as the guys are definitely ready to go and so am I, but I need to make sure Cassy is good.

"I'm going to go and start with those 2, you join in when you are ready okay?"

"Mm-hmm, I just need a minute."

I sit between the 2 guys on the couch and start feeling their cocks, one is quite large the other is about average, I can't wait to get them out. I motion to the third guy to come over to me as I unzip his friends' pants. Their hands are in my dress all over my breasts as I am slowly jerking them off, they are both rock hard. I put a foot on the coffee table as the third guy approaches me and I look down, he gets my meaning and moves my dress up to my waist. My pussy is now on full display for all to see. His tongue hits my clit. I moan partly in surprise, partly in pleasure.

I feel the hands all over my body and a tongue on my pussy, a cock in each hand, I am so turned on, so stimulated.

I ask Cassy "Are you going to join us or should i fuck all 3 of them myself?"

Without hesitation Cassy comes over and kneels in front of one of the guys, the one she was making out with at the bar and starts sucking his cock. He pulls his pants down and lifts her skirt, I see his hand disappear into her underwear.

The other guy on the couch that I was stroking is now standing in front of my naked, he pulls my dress off over my head, I pull him closer and put his big cock in my mouth. Just in time to catch some of his precum.

The guy who was giving me oral now is naked also and standing in front of me, shit I am so wet, he is so hard and this cock in my mouth is delicious. I feel his cock penetrate me slowly, so good he is excited and giving me a good pounding. I am moaning quite loudly, I want to see what Cassy is doing but I can't, one cock in my mouth and another in my pussy.

It doesn't take long for him to shoot his load deep into my pussy, a nice big load of cum, I look back at him to see his face in ecstasy as his orgasm subsides.

He stands me up and kisses me, certainly able to taste his friend's cock and precum on me but he doesn't seemed bothered by it. Then he drops to his knees and his tongue is back on my pussy, I lift my leg onto the table to give him full access and I feel some of his cum escape my pussy, he licks it up. His buddy has his hands on my ass and then I feel his tongue on my asshole, then it is in my ass. I can't believe the feeling of this as I cum and cum hard, his face is going to be covered in his own cum and my pussy juice and he keeps going. Behind me the guy alternates between tongue fucking me and biting my ass, I cum again, so stimulated.

The guy in front sits down on the couch, he is hard again, I straddle him and put his cock back inside my pussy. The guy who was behind me pushes me down into his buddy and I feel his finger on my ass, then he slides very easily into my ass, he's lubing me up!

I lift up on the guy I am on top of and he starts fucking my pussy, then I feel the cock slide into my ass. I had been double penetrated before and absolutely love it when I am this turned on. I feel a cock in my pussy and in my ass, they are fucking me so good. Hands are on my hips and breasts, I have no idea whose hands are where and I don't care, those cocks feel so good in me, I have a really big orgasm.

I must have clenched my ass because not long after that he holds deep inside my ass and I feel him throb, oh so much cum. The cock in my pussy is going double speed now and I rub my clit and cum again, then he cums and cums and cums, my pussy is full, so full of 2 monster loads of cum.

Finally I look over at Cassy. She is on her back, has a leg on her guy's shoulder and is moaning as loudly as I was. He is pounding her really hard, I can imagine her pussy is getting sore. Then his face tells the story, he's about to blow his load and holds deep inside Cassy and I watch her face as she is now filled with cum.

I go over to her and start licking her pussy, god is she wet, and holy shit did he ever cum a lot in her. She moans as my tongue hits her sensitive clit, then I suck it and I feel her cum on my mouth, I continue to lick, she stops me and whispers to me that she wants to try. Before I know it she is between my legs and starts assaulting my pussy with her mouth, feels so good, cum is running freely into her mouth from my pussy.

I slide under her and pull her on top of me in the 69 position. Now cum out of her pussy is running into my mouth, she is licking my clit, I am sucking hers. Then she starts sucking my clit and teases it with her tongue, feels incredible and I know she learned that move from me! We cum on each other's faces a number of times, before she is winded and lies on me.

She gets up, her face covered with my pussy juice and several guys' cum "Holy shit you have a lot of cum in you!"

"We both do hun!"

Our mouths meet and we taste the cum on and in each other's mouth. I think about how erotic this must be for her, tasting pussy for the first time, a pussy that has had action, a lot of action in the last few minutes and making out with her sister in law. That thought gets me really wet and I start cupping her breast and rubbing her clit, and rubbing it hard. She is moaning very loudly and having a lot of trouble concentrating on my kiss, her grip around my neck tightens, I know she is going to cum, I know how to make her orgasm like she has never done before, but I wonder if I can make her squirt. She breaks away from the kiss and is moaning a lot leaning back into my one arm as I wrap it around her and grab hold of her breast and pinch her nipple between 2 fingers, she's not going to hold on much longer. I reach down and bite and suck her neck, she lets out a loud moan, I rub her clit harder trying force her release.

"Fuck Christy, keep going, fuck, Christ-"

I feel it before she does anything, I hear her moan and exhale, not only is she orgasming, she is squirting all over me and the floor, I don't let up, I rub her and she continues to squirt.

Eventually she pushes my hand away, must be too sensitive now, she turns around and collapses onto the couch.

"Good god Christy, what the hell was that?"

"You squirted, like really squirted, the mother of all orgasms!"

"I never felt anything like that before, I'm so shaky, god will it ever stop?"

"Why would you want it to?"

I kneel beside her and we kiss, very passionately, she is very shaky!

Then I feel one of the guys behind me lining up his cock with my pussy and another is behind Cassy. They seem to be waiting for us to be ready, how thoughtful!

I spread her ass cheeks apart and give him a full view of her pussy, it is pretty red and still creamy, so delicious looking and he slides right in. The guy behind me spreads my cheeks and slides into my pussy, so much saliva and pussy juice and cum, and now a hard cock in me, feels so good.

Cassy's guy is going nice and slow, she's probably tight and he's enjoying it. My guy is far less patient and fucking me hard, the slapping sound of our skin meeting is quite loud, my moaning is just as loud, Cassy looks over at me, he is fucking me really hard, she holds one of my bouncing breasts and we kiss again. I don't know if I have ever been this turned on before, so many orgasms already, getting the shit fucked out me, a full view of Cassy getting nailed, her hand on my breast and her tongue in my mouth. I cum at the thought of this and then I feel my man cum, and cum, finally it subsides and his limp cock slides out of me.

Cassy's guy is still going to town on her and she turns around to him and asks "Are you close?"

"Yeah babe, real close!"

"Finish in her!" And Cassy points to me!

He pulls out of her and in an instant his cock is in me, his buddy's cum still dripping out of me, still as warm as his body and now he is fucking me, but not for long, he cums, and cums a lot, these guys have or had so much cum.

I sit down beside Cassy and survey the situation, I must have at least 5 loads in my pussy running out, we are both sitting in a pile of her squirting, cum is still running out of her pussy and the guys are all spent. Cassy leans down and starts licking up the cum leaking out of me, overstimulated is the only way I can explain how I felt at the moment. I feel her ass as she is doing that and tease her asshole, she pulls away. Guess she isn't ready for that, but I will get her there!