Helping My Wife Pt. 02

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

As we come up from under the table the men say goodbye and thank us for the weekend.

With cum on my face I expect my wife to suggest we go to the ladies room again to fix my lipstick, but instead says, "I won the bet, instead of going to the ladies room why don't we slowly walk thru the lobby before taking the elevator to the room."

As I take my walk of shame I get a lot of looks and a few whistles. To add insult to injury my wife waits for a crowded elevator to take us to our floor..

We get back to the room and start packing, but I can feel my wife's brain trying to think of embarrassing things for me to do.

I ask. "Why can't we just finish packing. The limo is picking us up early. We can have a nice quiet dinner and you can decide how you are going to spend your $20,000 bonus."

'Yes we can finish packing and have a nice dinner. But you lost the bet fair and square."

'Not really fair and square, you have way more experience sucking cock than I do."

"Stop whining like a sissy. I will give you an easy task. Call your young boyfriend Jim and have phone sex with him."

"Is that all?"

"Don't interrupt me. Have phone sex with Jim. He's 19 years old it shouldn't be that difficult to make him cum. If he asks, and I am sure he will, tell him about our weekend. Try not to hurt his feelings. After he cums I want you to cum into your cum glass and drink it."

"Is that all? Do you stay up at night thinking of kinky stuff."

I pick up the phone and call Jim. "Hi honey, how are you doing?"

"Jessica, I was just thinking of you"

"What have you been up to?"

"Getting ready for a party tonight at a friend's house. What about you?"

"Getting dressed, have dinner plans with Brianna's mom. Are there going to be any pretty girls at this party?"

"Not as pretty as you."

"Oh, you are so sweet. Do you want to know what I'm wearing?"

"Yes"

"I am lying on my bed wearing matching pink panties and bra. Wishing there was a certain young man with a big cock lying besides me."

"Wow"

"Jim, is your cock hard?"

"Yes."

"Why don't you stroke that cock and tell me what you would like to do to me."

"I would love to suck on your tits while my fingers play with your pussy"

Now I am getting turned on. "Oh, that feels good, my pussy is so wet. I have two fingers playing with myself. I wish you were here fucking me. Play with your cock, I want to hear you cum."

I could hear Jim's breathing pick up, finally I hear him scream, "I'm cumming."

As he cums I take my cock out of my panties and start stroking. I yell."I'm cumming too.", and I cum into the glass my wife had given me.

Before I hang up the phone with Jim I ask him. "If some girl gets you excited at the party tonight I want you to excuse yourself, take a picture of your dick and text it to me."

Jim say ok, and as we hang up I tell him I can't wait to see him.

"How was that." I ask my wife.

'That was great, I video taped the whole thing. Now let me get a picture of you raising that glass of cum."

I do as I am told, then ask. "Any more requests dear?"

"Not for now, let's relax then get ready for dinner. But I do believe our bet has another 18 hours."

"Yes it does."

"And I do believe my little sissy husband loves when I tell him what to do. From now on you will call me mistress and you will be my sissy slut."

"Yes mistress."

"Very good, one more thing. Smile and drink that glass of cum."

I do as I am told as my wife snaps a picture.

To be continued

12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
7 Comments
MergenHnMergenHnabout 2 months ago

Why is everyone always trying to turn a normal man into a sissy and make him gay? Why did the husband become a woman who could accompany him as he was

deidracowendeidracowenabout 2 months ago

Great story! I enjoyed it. I have dated real chicks and guys out in public. A lot of the wild stuff in this story and other really happens.

ManningDP69ManningDP692 months ago

At this point, I'm wondering why you are helping your wife she doesn't deserve to be called one. Divorce the bitch and move on with your own life.

AnonymousAnonymous4 months ago

Sorry, but this story is crap.

pantylvr2pantylvr25 months ago

Both chapters so very hot. Can't wait for more

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

The Deal Freddy's wife convinces him to dress up and go clubbing.in Transgender & Crossdressers
Weekend Getaway Surprise Wife hopes to turn husband into a sissy.in Transgender & Crossdressers
Becoming Ashley A man embraces his feminine side when encouraged by his wife.in Transgender & Crossdressers
Substituting for My Wife I substitute for my wife with her boyfriend when she's away.in Transgender & Crossdressers
A Harmless Favor A young wife assists her young husband to become a sissy.in Transgender & Crossdressers
More Stories