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.