Christy Gets an Apprentice

Cassy and I were sister in laws and we couldn't be more different: I am a tall, busty blonde, very outgoing and quite experienced sexually. She is quite short, brunette, breasts on the smaller side and married the only guy she had ever had sex with. She was very conservative in the way she dressed and acted and chose to be a stay at home mom. The way I dress is provocative and I love having my own career and being able to support myself. The truth is, the only thing we had in common is that we married brothers.

The brothers were also quite different but a strong family resemblance was shared. I married Dwayne, average height, not athletic, not hung, fairly average all around but I fell in love with him because he has a huge heart, always doing thoughtful things and that got me.

Cassy married Brent, significantly taller than his brother, athletic build and I found out that he has a big cock, but that is a different story that I wrote about already.

Most Sundays we would go over to their parents' house for dinner. Brent and Cassy would bring the kids so it was great to see them. I always felt like an outsider as Cassy and our mother in law got along great. I figured it was because she gave them grandkids, something I couldn't do because of Dwayne's low sperm count, something I had no control over.

I dressed "too sexy" in the eyes of our mother in law, in fact I once heard her refer to me as a tramp. To top it all off, she was appalled by the fact that I had my belly button pierced, just not something a lady should do.

I made the best out of it, often trying to spice things up a bit by doing things like giving Dwayne road head as we drove there and coercing him into having sex in his Dad's office (more than once I lost my underwear there, never finding out what happened to them).

We were all pleasant to one another, at least to each other's faces, and we all adore the children, sometimes I still think of them as my own, or at least the closest thing that I will have to my own.

One Sunday we were headed over to my in-laws and of course Dwayne had cum in my mouth and we headed inside the house in a very good mood and very proud of ourselves, mainly because the week before he hit the curb when he was cumming and cut his cock on my tooth from the impact, he didn't find it nearly as funny as I did. When we got in, it was unusually quiet, almost eerie. The other adults are sitting in the living room in silence, Dwayne sensed it too and said "What's going on here?"

Brent replied "I just told mom and dad that Cassy and I are separating and I asked if I could stay here for a while."

My heart sank, I never dreamt that a couple like them would split. I always thought of them as a stereotypical "perfect family", he was the breadwinner, she was the stay at home mom that ran the household and they always seemed happy together.

Cassy got up off the couch and excused herself and left the room. I followed her to our father in law's office. I was a little disappointed in myself thinking that just last week I had lost a thong in here having sex with Dwayne and wondered if I could find it, pretty insensitive of me, needed to snap out of it.

"Cassy, I am so, so sorry to hear that. I know we haven't ever been close but I want you to know that I think of you as a sister and if I can do anything for you and the kids, even just to have someone to talk to, I am here for you."

She lost control and was openly sobbing now. I hugged her and told her she didn't have to put on a brave face with me. She hugged me tight, I think she really needed a good cry. She thanked me after composing herself and we rejoined the group in the living room. The rest of the visit was tense and Dwayne and I were silent on the way home. I started to cry in the car, thinking shit my period is coming, goddamn hormones.

A couple days pass and I haven't heard from Cassy at all so I send her a text to see how she is doing. She says she is struggling and seems overwhelmed but trying to stay positive. I said okay, we need to go and have a bit of a girl's night. She is hesitant because the last time we went drinking was probably her bachelorette party but in the end she agrees.

The next night I am getting ready to pick her up, my period is still with me and my boobs are bloated, "Like they aren't big enough already?" I think to myself as I throw my bra down in disgust, it is not comfortable at all. Looking at my clothing options and spot a black dress that I recently got, I should say a backless black dress, it's perfect since I already decided no bra. Trying not to think of the fact that I have to wear underwear today, something I very rarely do going to the bar.

I head over to Cassy's house, Brent has already picked up the kids and took them out for supper. She looks stunning: her shoulder length hair is curled, her makeup is very tastefully done and she has a beautiful dress on, just above her knee. I look her up and down and stop and focus on her chest.

"What's the matter?"

"Take the camisole off."

"Without it my boobs will be on display."

I just stare at her as if to say "And? We are going to the bar, remember?"

She sighs and slips it off, she is wearing a conservative bra, need to get her a pushup bra or 5. I make a note to myself, but even with that her cleavage looks great! I give her breasts a squeeze and tell her she looks amazing, she looks at me puzzled and follows me out the door.

We go to a bar I know that is very popular and play great music. The bouncers let us in right away and Cassy says "How come we didn't have to wait in line or pay a cover charge?"

"Because we are dressed like this, they want women like us in there!"

Her eyes widen but she follows me in. We find a table with a couple of high stools and decide this is our home base. We sit down and she is trying to pull her dress down, she is losing the battle.

"What's the matter?" I joke at her.

"My dress rode up and barely covers my legs," then she looks over at me and follows that up with "Christy, yours is up even higher and I can see your underwear!"

"And that hun, is why we won't be paying for our drinks today."

Her mouth is hanging open trying to process what I just told her.

A couple guys walk up and introduce themselves, young guys probably looking for cougars or MILFs as they would call us, but quite polite asking if we would have a drink with them.

"Sure hun, we just got here and that sounds nice."

The waitress stops at our table and sort of recognizes me "Vodka/7?"

"Yes, please, Melissa!" She is a young woman and university student, incredibly sexy and she is definitely wearing a pushup bra getting a lot of attention from not just me.

"What would you like dear?" she asks Cassy, who doesn't even know what to say.

"I'll have the same." She did some quick thinking there.

The guys talked to us for a while, which really didn't do much for me but they were nice and wished us well.

A short time later a middle aged man comes up to us and asks me if I would like to dance.

"No thanks, just enjoying having drinks here with my sister."

"Can I join you ladies and buy a round or 2?"

Most people know if is a weakness of mine when a guy refers to me as a lady, I really like it since I usually get called a slut, a tramp, or a fucking bitch and none of them meant to be in the good way.

"Sure hun, we'd like some company, right Cassy?"

"Cassy?"

Oh shit, does he know her, this is about to get really interesting.

"Mm-hmm"

"Is that short for Cassandra?"

Wow, if he is trying to flirt with her and that is his best line, it's no wonder he is here alone.

"No, it's short for Barbara."

I spit my drink laughing so hard, I did not expect a witty response from her much less a sarcastic one. I think Cassy or Barbara is getting a bit drunk and I like her!

The guy walks away, I try in vain to apologise, he either can't hear me or is ignoring me but holy shit that was really funny and totally unexpected. She stands up in front of me, clearly wobbling, she's past tipsy at this point and says that she couldn't resist. I told her I was mad at her for making me waste my drink, she was quick to point out that we didn't pay for it.

Then she stands silent in front of me, I really don't know what to expect out of her, maybe she's going to have a breakdown about her separation.

"Christy, you know, I've...I've always been jealous....of...your...your...your...tits."

I look at her in complete shock, she is quite sexy herself and I had no idea she was jealous of me, or them.

"Cassy you have great boobs too, so nice and round and firm."

"No Christy, yours are so much bigger than mine and I heard Brent tell Dwayne that he loves looking at them."

I am quiet, I don't know what to say, her husband likes my breasts better? God I have always thought he is really attractive but had no idea he thought about me that way.

My thoughts are interrupted as I feel hands on my breasts, I look to see that Cassy is cupping my breasts and leans in to kiss me, like a real deep kiss. She is such a good kisser and her hands feel great on my breasts, I hold them there as we kiss for several minutes.

When we finally break our embrace we finish our drinks and head to the bathroom, I'm pretty much holding her up, she really has a low tolerance, going to have to work on that.

We finish relieving ourselves and checking ourselves in the mirror. I'm trying to adjust my breast in my dress, there is no support, like none. Cassy looks over at me and is able to see clear down my dress.

"You're not wearing a bra!" She pretty much announces to the whole bar.

"Yeah? Well you are!" I walk over to her and pretend to hug her but undo her bra at the back and slide the straps off her shoulders and remove it from her dress, handing it to her.

"Put that in your purse, you don't need it."

Once again she just looks at me, but does exactly what she is told. I pinch her nipple, they are very large compared to her breast side, must be from breastfeeding I think to myself.

We head out of the bathroom and there is a bachelor party that has just arrived. A couple of the guys stop in front of us and ask if we would do hooter shooters for them.

"What's that?" Cassy asks.

The guy is looking at her as if she was 2 heads for not knowing that.

"Of course we will, she just didn't hear you"

He nods and puts an arm around each of us and escorts us over to their table.

"What do we do now?"

"Just follow my lead and do what I do."

On the table beside the guy who is obviously the groom as he has been given a shirt that says "At the End of my Single Life" to wear sits a tray full of test tubes filled with different coloured liquids.

The guy who introduced himself as the best man (Derrick I think was his name) motions to the tray and I shout over to him "Sex on the beach".

"Gladly with you!" He jokes, yeah smooth move Christy order something with an easy sexual innuendo, then he hands me a test tube.

"Are you ready?"

"What do I do?"

"Just hold this between your boobs and I'll take care of the rest, okay?"

Cassy nods as I slip the test tube between her boobs, thankfully I removed her bra already. She presses her breasts together and holds the drink in place, I can just see a little bit of the top of the test tube sticking out.

"Don't let it fall."

"I got it, but what now?"

My lips are on her cleavage as I pick up the test tube and swallow the shooter in one gulp. The guys all cheer and whistle, god that was fun!

"Now it's your turn, do exactly what I did, okay?"

I position another shooter between my breasts and Cassy hesitates for a minute, but only a minute and then dives in, I felt a little wet as her lips hit the top of my breasts. She scooped up the drink and pounded it back but lost her grip on it and the tube went crashing to the floor.

"I've never done this before, but I love it!"

I take the groom by the hand and position him behind Cassy.

"You put the shooter between your boobs and he's going to hold it for the guy, okay?"

"What are you going to do?"

"I'm going to do a line too!" I get the best man and move him into place behind me.

"Don't squeeze my boobs too hard okay?"

"I won't, this is awesome!"

I motion to Cassy to grab a shooter and put it in place, she does and the groom has a firm grip on her breasts, she gasps at first, I can't see for sure but it looks like he is pinching those big nipples between his middle and pointer fingers. One of their buddies steps up and grabs his shooter and knocks it back like a pro. Cassy and everyone cheer as she puts her arms around him and gives him a real passionate kiss. Wait, who is this chick and what happened to Cassy?

We did about 10 or 15 shooters for the guys then there was a break in the lineup so I went over and did another off of Cassy's breasts and made sure I got my kiss from her!

"My boobs are so sticky!"

"Mine too, but doesn't it feel great?"

"It sort of does!"

The groom holds Cassy's hand and he sits down and invites her to sit on his lap. I sit down beside the best man.

"You are so gorgeous, how are you not taken?"

"Actually, I'm married hun."

"What would your husband say or do if he knew what was going on here?"

"I don't know, probably get in line for a shooter!" We have a good laugh and he is rubbing my thigh, high on my thigh, almost under my dress. I reach down and kiss him, his hand is on my ass and I feel it slip under the backside of my thong and he grabs both of my ass cheeks at the same time.

I look over and Cassy is in a heavy makeout session with the groom, his hands disappear under her dress, yeah she's okay I think to myself.

I crouch down in front of the best man and unzip his pants and pull out his cock. It's big and it's cut and it's shaved and it is maybe the most delicious cock I have ever seen. Immediately I start sucking it and playing with his balls, first cupping them and then squeezing them.

His hands are inside my dress with a firm grasp of my breasts, it feels great. My head is going up and down very quickly on this cock, almost taking the entire thing in with each gulp. He moves a hand to the back of my head, I quicken my pace and then I feel the first spurt of cum hit the back of my throat, then another, another big one as I massage his balls. That gorgeous cock just came so much, and I loved it as much as he did.

The groom comes over with Cassy on his arm and tells the best man that they are getting ready to go to the strip club, Cassy sees him zip up his pants and looks at me with a WTF just happened look.

I don't make her ask "I gave him a blow job, he had a big cock!"

"I gave the groom a handjob," Cassy fessed up, "We were kissing and his hand went up my dress and his finger was in me and I just wanted to and I did it! He got me so wet!"

"Take your underwear off."

"What? Christy, why?"

"Just do it, trust me."

She slides a pair of lace boy cut panties off, I feel the crotch, yep she is definitely wet. "Put these in the groom's pocket, give him a kiss and wish him well with his bride!"

She giggles and does exactly what I told her to and then comes back over to me.

The bachelor part has left and we are having some drinks and I look over at Cassy, she is a different woman than we we left her house: her hair is down her bra is off, her large nipples are trying to poke through her dress, her underwear is with some guy far away from her by now, and there is a large cumstain on the skirt of her dress. She is pretty drunk but keeps on smiling, she looks like she is having the time of her life!

A favourite song of mine comes on and I grab Cassy by the arm and almost drag her onto the dance floor. I never thought of her this way before but the way she is moving, she is so incredibly sexy, this is the Cassy I don't think many have seen before, I may have unleashed an animal. We dance very close together and I spin her around and put my arms around her just under her breasts, we dance very close like this for a while, she feels so good against me. I slide her hair away from her neck and give it a bit and then some nibbles then I suck it, even over the music I can hear her moan.

It's getting pretty sweaty so we break apart and continue our sexy dance, guys seem to have circled us, one guy is behind me, his hands on my hips and I press my ass into his cock, it's impressive. He smells good, he feels good, I'm just going to rub his cock a while longer with my ass and see if I can get him hard. The song changes, it is a slower melody and I adjust my hip movement. His hands are on my breasts now and he is kissing my neck, so turned on, I reach around and grab his ass, very firm he is in great shape. I look over at Cassy, she is dancing with at least 2 guys, her arms are around one and another is right behind her, they make a Cassy sandwich, she's good!

I look back at the guy behind me and see his face for the first time, he must be about 6'6" cause even in my heels I am looking up at him. He is bald, short goatee, and his black skin glistens in the light of the dance floor. He seems to really like my breasts as he hasn't let go of them for quite a while, his grip is nice, I decide he can hold them as long as he wants. I reach up and kiss him, our mouths open and his tongue is instantly in my mouth, a massively large tongue, that would feel so good on my pussy I think to myself, fuck I have my period, son of a bitch. He breaks the kiss and whispers in my ear "If you keep this up baby, you're going to make me cum!"

I moan, his words make me wet, I think if I was ever going to have sex on my period it is now, "let's see if I can, let me know how I do, l?"

He takes one hand off a breast and I feel it on his crotch, then I feel it, the it, I look down to see the head of his cock peeking through the zipper of his pants. He lifts up the back of my dress and puts the head of his cock between my ass cheeks and under my thong strap. My crack is soaked with precum, he isn't going to last night I realise. We continue our passionate kiss, one of his hands are on my stomach, he is sort of playing with my piercing while the other is fondling my breast, I quicken the pace, then I feel the warmth of his cum on my lower back, I moan, he tightens his grip, his cum is all over my ass and legs and I'm sure dripping on the floor. Once his orgasm subsides I turn and face him and look at the bead of sweat on his gorgeous face, he felt amazing and there wasn't any penetration. He wipes the last bit of cum off his cock and feeds it to me, tastes so good, I lick his fingers. He zips up and one last kiss before he leaves the dance floor. I didn't want him to leave but then I remember Cassy, shit where's Cassy.

Then she bumps into me.

"Christy! Who was your friend? He looked hot!"

"I never got his name but, yeah he was!"

"I need a break, so many guys had their hands on me, I'm not sure how many I kissed but there was one for sure, someone else was pinching my nipple, this isn't anything like dancing I've done before, so much better."

Cassy has crossed the line, she is really drunk now and I think that is enough for her for one night, time to get her home.

She leans in to me and gives me a very passionate kiss, holds my breast and whispers in my ear "thank you for the best night of my life, I love you!" Better than your wedding night, or when your kids were born? We should have done this a long time ago!

"We should go home and continue the party"

"You're the boss, love, I'll follow you anywhere!"

Shit, how did we get here? Did we drive? God I am drunk, she is super drunk, where's an Uber?

Finally I ordered an Uber.

"Our ride is 8 minutes away hun"

"Great! Shit, I think the groom came on me," Cassy says, just noticing the stain on her dress.