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My Cute Husband- Part 4

Okay, so a whole bunch of people have asked me what was next and where are you guys now in the relationship. I guess I kinda of left everyone hanging.
Well, we talked again at breakfast and tried to figure out where we wanted to go with this. We talked over a few options such as sissifying him or maid training. But I didn't really want that even though he seemed willing to do anything at this point. I told him what I really wanted was for him to be my sometime girlfriend. I mean he is my best friend and why not also my best girlfriend? We talked long and hard about all the possibilities and any repercussions with family and work. Jessica decided it being Sunday, that he would continue to dress and wanted me to teach him what I could about makeup, etc. So we spent a quiet afternoon with him dressed in a nice skirt and sweater with light makeup. His boobs were still firmly attached by the way and he seemed to be getting used to them. We just spent a great day together without any tension or disagreements. He even offered to make dinner. That was sweet of him but the dinner.....
We went to bed early and cuddled for quite a while. I began to feel up his boobs, kind of a new sensation for him even though they were silicon forms. He began moaning anyway. Things got hot and heavy pretty quickly.
What came next floored me. He said "I really wish that you could **** me like a woman". Whoa!
Here is a new level...... I said, "What do you mean exactly?" Jessica said " I wish you had a penis and that you could **** me". I told him that we might just see about that. We finished off for the night and went to sleep, each in our nightgowns.
In the morning, Jessica nudged me and indicated she needed to remove her boobs before going to work. Smart *** me said "Why?"
Anyway, we removed them and the nail polish on his fingers and he hit the shower.
When he came back he started for his briefs in his drawer. I asked him what he was doing and he said getting dressed. I said "No Jessica, you wear panties!" He said he couldn't wear panties to work and I asked why not. He couldn't really answer that, so I gave him one of his pairs and he put it on, got dressed and went to work. He had forgotten that his toes were also still polished. Oh well.
I went to work, but all morning I kept thinking about him wanting me to **** him. I needed to check this out, it could be a near addition to what we were doing. I took my lunch break at home and got on line to see what I could get to make this happen. Found a few sites and was amazed at what was offered. All kinds of possibilities. Through it all I finally settled on a 6 " strap-on with a little gizmo on my end to spark me too. I ordered it rush delivery!
The package came Friday and I got the mail first. I went to the bathroom to check out the new toy. Getting it out of the package was ridiculous but I did and there I had a life-like **** with straps. I had to try it on and ******** in about two seconds and had that puppy on and strapped down. I posed in the mirror and said "Oh yeah!"
Jessica came home about an hour later. i had ordered Chinese food so we didn't have to cook. I told Jessica if he wanted a special evening to go get a bubble bath and get dressed properly. Like an express train going by a station, his mood went from confident stud to mesmerized zombie. I said, "Jessica? Did you hear what I said?" He just nodded and left.
I gave him about an hour, drinking wine while I waited, then went up to the bedroom. There on the bed was Jessica, dressed out in a white peignoir and robe. He had on his boobs and wig and had tried his own makeup. He would get better. His nails were done and I detected some of my perfume. I told him he looked great and that I appreciated his effort. He just nodded, apparently the normal response now. I said, "Jessica, give me a minute to get ready and I will join you."
I went into the bathroom and ******** down to nothing. I put the strap-on in place and walked in. The zombie's eyes lit up! I move closer and without saying anything he grabbed by penis and started kissing it! He did a great job and then started to suck on it! It was amazing, almost a conditioned response, but I had not conditioned him. After about 10 minutes I asked him if he was ready. He just nodded, of course! I had him get doggie style on the bed and lubed him up a little. "Jessica, are you ready?" What else, he nodded. I gently pressed the tip of my penis onto his bud and pressed. He moaned and I pressed a little harder and then pop, it was in. He let out a long, low moan.........
We started a rhythm like he does me and soon we were both moaning, the little gizmo on the end doing it's job. It wasn't long before I climaxed and he shot his load all over the bed. Neither one of us had ever had a rockin' explosion like that! We collapsed into a spoon with me still in him. We whispered for a while about what we did and should we do it again. We agreed it was great and Jessica said he enjoyed being the woman and wished we could go further. I asked him if he would like to take female hormones. He said, " Oh yes!" I figured it was just the heat of the moment and since I had to pee, I said " I can help you!" I turned him over and sat on his face and began to pee. He eagerly began to drink! I said, "Jessica, my pee is full of female hormones and I am going to make you a woman!"

Chapter 5?
Linda9231974 Linda9231974 36-40, F 27 Responses Jan 15, 2013

Your Response


******* hot!!!!

didn't read it all but that is your own thing and let the masses sleep

Wish I could find someone like you to do that to me

This is your most amazing story and thank you so much for sharing. In our lifestyle my Wife/Mistress L both feel that strap-on sex is the most intimate thing a loving couple can ever do

If I could, I would have just came!

Coolest couple ever. How were you able to climax with the strap on? Do you have a link to share?

There is a secret little nobbin on the back side that takes care of things

what a wonderful story this is!!! Wished there were more women out there who shared your thoughtfulness!!!

Wonderful story, Linda

Linda, please do let me know when you post Chapter 5 ... Chapter 4 sounds so much like my wife and me! ;-)

Already have 5,6, and an update on the page

Thanks Linda. I\'ll look for them ...


I have only dressed in lingerie but your stories are making me want to get completely turned feminen

Wow, what a story!

Wow that was a great story

Wow is this going the way you want it?

Thats the way good little sissy should be treated, right!

You have a wonderful imagination, you haven't missed anything and have a masterpiece painted with words. Love the way you share.

Why thank you sir!

That's "M'am" to you!

My sincere apologies! Had I done my homework better I would have known that.
Thank you M'am!

they all want ot be called madame, Feminization is os popular these days we could work around the clock

1 More Response

I'm always open for suggestions of being more feminine.

So erotically hot!
Such a sexy start to a full start to feminization!

They might have been diluted, but it probably made you feel better. You could have him grow breasts, they will not go away once they have been formed.

We have talked about maybe getting some herbal hormones

They work--can get consumable or use lotions to massage into breast--body lotion with fenugreek, hops, red clover, saw palmetto worked for me. Real hormones will also shrink the balls Did you enjoy feeding him some hormones like that?

Yes and I was surprised how eager he was. He really seems to want to experience being a woman, if only part time.

some women get a high about dominating a man like that. do not use real hormones if this is to be a part-time thing even the herbs will cause real breasts to grow--they will not disappear

Okay, I would be talking to him about it anyway, It will be our choice together, the way we do anything.

How would you feel if he actually grew breasts?

Something more to play with.

As in *** torture?

No, something to squeeze and suck on

You are an incredible woman! Damn is he lucky!

I don't think sHE will content HErself of part time especaillyy after such and exquisite experience sHE will certainly want much more, there so many stories like yours out there and in the end many end up by the new GUrl want more and wanting to live totally female, and I do understand that, Because we female seem to have more sexual intensity. It seems at least that your strap-on will have to do OVER TIME. sHE,ll be more and more on HEr 4's take-up the female position while you be more and more in the male position with your strap-on

I really like the way you think, I never been in such exatcy on EP

Thanks so much, glad you enjoyed!

10 More Responses

Shaving must be a drag for him. So maybe the next step is lazer treatment for all body and facial hair.

Take his masculinity away by making him get snipped. Tell him, "good girls do not produce *****."

Also, has he tasted his own *** yet? Have him jack off onto your strap-on an then suck it clean while he's on his knees in front of you.

Wow, I like those ideas, especially the one about him sucking his own *** off my strap-on. Good job inkspell!

Wow that's a hot story especially making him not wear boxers I'd want that done to me

I could help you if you want.

How's that?

I could give you suggestions or commands if you want.

I'd love that

So how many pairs of panties do you have?

2 More Responses

Awesome Linda ... and I am sure that you hubby, Jessica, is a happy camper too! ;-) The only thing I would suggest is get him started on hormones, be they by injection, patch or pill. My wife was supportive and encouraging of the idea for me and we did and I couldn't be happier.

If all this is true your husband is one lucky fella!

This is all true I am happy to say and have enjoyed the journey immensely. Not sure where we will wind up, but here we go. Part 5 now up, hope you enjoy.

You go girl!! Loved it!!

Great stories, can't wait for part five..........

wonderful ;-)

Thank you

I somewhat understand the thoughts in Jessica's head. I've told my wife that I'd like her to be able to do to me what I do to her. We haven't tried it yet. Wierd thing though, I don't desire to be with a guy at all. I find guys somewhat repulsive. As you've mentioned in your story, I always thought it would be fun to be my wife's girlfriend for a day. But I would be her lesbian girlfriend at that.

That is exactly the way we are. He is exploring womanhood, but just with me. You should convince your wife to "do" you. It is a wonderful leveling experience