You are about to fuck your sissy for the first time...

Over that last several months I have spoken with and emailed over 20 women, all of whom are married and all of whom have asked for assistance with fucking their sissy husbands for the first time. I have collected the various points, advice and suggestions in the post. 

Some wives like to treat this as a honeymoon, or a dirty weekend away. One particularly adventurous couple discussed their plans with me over several weeks.

She wanted to treat him like a virgin and he was keen to experience the entire female journey. He went shopping for a new outfit with Nicole (my sissy husband).

 

The sissy gurls discussed the husbands outfit heels and skinny jeans, should she take the role of a city girl? Sassy and big sunglasses?

Corporate secretary girl?  This felt closer to the fantasy the sissy gurls wanted to create, but was still not fully inline with the sissy husbands wishes. Nicole and the husband, wanted to make this so special so right that it would be a memory that the wife and husband shared for ever, something secret something special and something they would only know.

The final outfit they selected was the perfect mix of prim and proper lady of the house mixed with the city chic of girl about town.  

The sissy husband wanted something cute, girly, sexy and grown up they stumbled across perhaps the most adorable babydoll and matching thong by Victoria secrets, paired with strappy heels the outfit was perfect.

 The sissy gurls purchased several other lingerie sets for the special night. 

While I met with the wife and discussed how she felt and what she wanted from the experience. I reminded the wife that she should treat herself also. She should revel in her femininity and only if she chooses to take on a male role, to do so. We discussed her wearing a strap on for the entire time and being 'manly' but in the end she had no desire to be the 'man'.

I shared the image below with her and suggested she outline the story to her sissy husband and from the moment she wanted to press play on the role that they would both hold character and play out their assigned roles. The image began to excite her and she spent hours imagining the evening the two women in the photo might have.

We discussed the rules she wanted to set her sissy husband. It was agreed that they were both bi and that her husband would be taking his first lesbian strapon cock.

I suggested several strap ons to the wife.

From double headed straponwhich I have used and find a little uncomfortable, however I do feel this along with the harness makes for a much more realistic fuck.

To realistic monster cocks. I do recommend girls buying a realistic cock - get your sissy to learn every vein and ripple on your cock. 

 

This is my current fave, it is realistic the texture is much more in keeping with real skin and the cock ejaculate, it comes with a small bottle of fake cum. It smells like real cum and has the same texture, the taste is a little sweeter than real cum. but seeing cum on his sissy lips is such a turn on, highly recommended. 

The last cock is a feeldoe. Very popular among my lesbian girlfriends. This one in particular vibrates and has ridges that flick your clit as you fuck your sissy gurl or lesbian girl.

We discussed roles and language, this I found to be the most surprising element, the wife felt embarrassed and the sissy husband was unsure what was sexy and what was not. The below points were outlined for them a little fun evening spent with Nicole, S/he in doggy position with an ipad to record our comments while I slid in and out of her sissy asspussy with my strapon.

For the sissy gurl

1. moan when I enter you
2. call me your mistress
3. tell me how big my cock is
4. gasp, sigh, yelp, pant, moan and purrr
5. tell me how deep inside you feel it
6. when I pull it out, wiggle your hips at me and beg me to put it in again
7. reach down with your hand to feel the point where I enter you, the girth of my shaft stretching you wide
8. squeeze your hole around me and tell me you want my cock
9. beg your mistress to allow you to suck a real cock 
10. tell her you want to be a girl 

For the mistress / wife

1. say something like “Oh yeah!” when you enter him
2. call him your “little bitch” and other names - whore, slut, fuck toy.
3. tell him how big your cock is and how small and tight his pussy is
4. whisper, shout, give orders, tease
5. humiliate him and tell him his sissy clit is tiny and your cock is huge
6. tell him how deep the shaft is inside him
7. pull it out occasionally and don’t put it back in until he wiggles his hips at you and begs you to put it in again
8. reach around with your hand to feel his cock and balls, telling him that today he’s the girl and his asshole is a pussy
9. fuck him until his anus gapes but don’t make him come until he is hysterical with desire, begging, saying things he never thought he’d say 
10. ask him if he is a girl
11.  ask him does he want a real cock 
12. does he want to suck cock

I suggested spending the week leading up to the event that teasing him would be fun. I suggested she should send her sissy husband images and messages, the messages would be questions that he would have to answer, as the girl and if he did not he would be punished in some way. I had them place a score card in their home on the fridge.

These are some of the images and messages she sent (do note the name she gave her sissy husbands alterego is Lisa):

Hi Lisa, darling don't you love the her lingerie, they are both so so sexy. Which girl would you like to be?

Yes Mistress her lingerie is stunning, I so want you, please Mistress, please wear a similar outfit when you take me, please.

You want me to wear lingerie?

No Miss, I want you in the tux, I want to be the girl Mistress

You are such a whore Lisa 

Lisa can you imagine being fucked so hard you squeal and your breasts bounce?

Yes Miss, I want it sooo much 

Do you think it is hurting her

Yes Miss, I sooo hope so, it soo mucb better if it hurts a little

Giggle Lisa you slut

Oh my god Lisa look at his cock it is incredible! I bet you wish you had something like that pushed between your legs or lips

Miss, I am not sure I want a real cock in me

Oh Lisa don't be such a bore all girls are cock hungry, especially when the cock is so wonderfully big

But Miss 

Shut up, sissy bitch and tell me how much you want his cock

Miss can I ask, have you ever had a cock like that?

Yes Lisa

Did it hurt? Did you like it? 

Yes Lisa it was wonderful, you can never truly understand how wet a girl will get when she knows that monster is waiting at home for you. Oh Lisa darling trust me you will learn to love a mans smell, his taste and that feeling of satisfaction as he slides into you.

Lisa which girl would you want to be and why?

Miss the girl in the middle, because she is the most exposed, the cutest and somehow I feel she is the most slutty - sooo blushing right now Mistress. I want to be her because I think she gets fucked more often then the other two and she likes it Miss.

 Finally Lisa we are truly starting to see the real you

 Lisa sweetie I want you to imagine you are the pretty blonde maid in this .giff tell me how you would feel.

Miss, I would be in the moment, my entire body tensing and releasing as he enters me, the feeling of fullness and the ache when he is gone, I would be gasping and moaning, my breasts would bounce and their pull on my body would highlight his thrusts.

 Wow Lisa, are you sure you have never been fucked by a man before? You seem to have a natural understanding of what is happening.

Yes Miss, I so want to be her, a real girl, full of cock

 How does this make you feel Lisa?

Submissive Miss 

Really, why?

Becuase it, well, I well sooo blushing Miss, becuase I imagine you are the women in the tux and I am her bitch Miss 

Yes Lisa you are my Bitch and you will be my true bitch when I fuck your cute sissy ass

 Lisa how satisfying is this?

Oh Miss soooo much so.

Do you love me Lisa

Yes Miss, ofcourse I do

Really Lisa

Yes Miss 

Enough to accept I need you to help me when I am being fucked by a real man Lisa

MISS

Lisa calm down, all girlfriends help each other out

MISS

Lisa don't make me spank you

Yes Miss, but, Miss 

No buts Lisa you have to understand a girl has needs and you just don't fill me in the way I like to be filled.

Miss I can try harder 

Lisa sweetie, your tongue is amazing and I do love kissing you, why don't we kiss while I am being fucked just like in the giff I sent you

Miss please

Bitch don't waste my time your a sissy what did you expect?

Lisa suck my cock bitch

Yes Miss