A Tale of Two Sissies

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"Is your wife mad at you?"

"Oh hell yeah. Madder than a wet hen. Is your wife mad because you became a sissy?"

"I think she's more disgusted with me than angry. I know Tom is fucking her like I never could so, in that regard, I think she's happy."

"Honey, I wish Linda would take a lover. Tell me, do you get to suck Tom's cock often?

I had to chuckle. "Yeah. Almost 5 times a week. He's the man who made me what I am now."

cindy grinned. "And tell me, jennifer, what are you now?"

I had to think about my answer. "I guess you could say, I mean outside of the obvious sissy, I'm Tom's cock sucker."

cindy got excited. "Baby girl, tonight if they do take us to the Eros Club, you'll have more cocks sticking in you than you can count. I hope you've been fucked in this soft round pussy." As cindy said that, she let go of my boner and placed both her soft hands on my bare bottom.

"The guys are gonna love taking your cherry, baby doll."

I shivered at the thought. "Will it be safe?"

"Yes dear. Don't worry. They have big strong and well hung bouncers," cindy giggled. "I know. I've sucked two of the men off after hours."

"Did you mean that when you said my dick was too small to be sucked?"

"If you mean sucked by me, baby girl, yes. I love sucking cocks but dicks like yours, no offense, but they just don't do it for me."

I looked down at my boner and nodded. "I get it. Really."

"Do Tom and Cindy allow you to have sex with anyone."

"Never. Cindy would never stand for me being with another woman and Tom says that I need both their permission just to masturbate."

"Oh, baby. That's harsh. You don't need my permission, I mean if you want to, you know....."

"You mean masturbate?"

"Yes, if you need to."

"We just met, cindy. I don't know if...."

"We've emailed so many times, baby. We're like sisters. If you need something to pique your interest, Let me help."

With that said, cindy stood up and wiggled out of her pants. Turning this way and that, she displayed her sexy body which, in her light pink panties, was arousing.

I couldn't help myself. Like I was trained, I knelt on the floor and looked at my sexy friend as I masturbated.

cindy, still helping me keep the mood, came to me and pulled her panty down in front. Her dick was a little bigger than mine which did not surprise me. Like me, she was freshly shaved.

She took her dick and rubbed my face with hit causing me to moan."Can I, please."

"Can you what, sweetie?"

I tried to get her in my mouth much to cindy's amusement. "Please cindy. Let me suck you." Finally, she allowed me to suckle her dick while I jerked mine off.

She was more like Tom than I could believe. When I said I was gonna cum, cindy insisted I catch it in my hand.

I groaned and spasmed and filled my little hand with my orgasm.

"Now eat it, jennifer. A good sissy puts that shit back from where it came."

"You girls get your lunches here. We're going out. You two are not to leave this apartment until it's time to go to the club."

"Yes, ma'am," cindy called out to her wife.

cindy and I snacked and talked and got to know each other. It was a pleasant afternoon.

When Linda, Cindy, and Tom returned, we all sat around. By then, I'd put some panties on under some Spanx and a white camisole top.

"jennifer," Linda got my attention. "Tom tells me that it was he who made you what you are today. Did he really make you wear panties and suck his cock in front of your so-called friends?"

"Yes ma'am. Tom knew more about me than I did."

My wife Cindy asked cindy what type of man she preferred.

"Miss Cindy," she began with a sideways look at Linda to see if it was okay for her to speak the truth. A slight nod from Linda and cindy continued. "My preference is a well hung gentleman who treats me like a lady. I like him to wine and dine me, then take me to his place and fuck me. In his bedroom I become a real cock slut."

"So," my wife asked," You wouldn't suck a little dick like jennifer's?"

"Oh, heaven's no ma'am. I already told her I wouldn't. She did suck mine though. I hope that doesn't get her into trouble with Mr. Tom."

Everyone laughed.

We spent a couple hours chatting and Linda told us we were to get ready for our night out.

cindy and I went to her room and as she began rooting through her clothes, I opened my suit case that Tom packed. I wondered what he thought I should have.

"Oh my God," I gushed. "Look at what Cindy and Tom bought me."

I pulled out a little black pleated "A" line skirt. It was short like skaters wear. When I held it up to show cindy, she gave me a beaming grin. Baby girl. Half of your bubble butt is going to hang out. Better wear some sexy panties. Better yet, a thong would show off your asset better."

I rummaged through the clothes and found a thin white thong. So thin, my privates would be seen if I didn't sit lady-like.

"cindy. I can't wear my hose with this short skirt."

"Why not?"

"Duh, because the tops will show."

"And they would make you that much sexier, baby girl."

"But I'd look like a slut, cindy."

"You would, jennifer. That's the look we are both going to have. Just a word of caution. Stay away from the bull dykes. They'll eat your lunch, girl."

cindy suggested that she apply my make-up. Though I thought it over done and made me look cheap, cindy was pleased with my look." Smart and slutty. Or as cindy said, "Sassy and Sissy." A sultry bitch ready take on a real man."

That shook me. Before then, I hadn't considered being with anyone but Cindy and Tom. But they brought me here and they knew cindy and Linda had planned a night out at some sex club for me.

All of a sudden I panicked. I rushed into the living room and ran to Tom. "Please, sir, please don't make me go to that club. I want to stay with you and Cindy. Please," I begged through tears. "I'll be good. I promise."

He took pity on me. "Baby girl, it's time for jennifer to spread her wings. After tonight you'll be in your element, I hope anyway. There's a whole new world for you to explore, baby. Men will lust after you. They'll seduce you, allow you to worship their cocks. And face it, jennifer, you do enjoy my cock."

I was kneeling between his legs with my head on his tight stomach. "But I want ot be with you," I sniffed.

Tom ran his fingers through my hair. "You do now. But if you go out with cindy and follow her lead, do what she tells you to do, act like the woman you are, you'll see that you were made for more than one cock. Promise me you'll try."

The room was quiet as Linda nd Cindy waited for me to answer. "I promise I'll try, sir."

"Good girl. Now run along and get ready. We called an Uber for you two bitches."

I returned to cindy's room where she was putting on her finishing touches. "What about a top, jennifer?"

I searched my bag but didn't find one I thought went with my look. "Here, girlfriend, try this one on," cindy smile handing me a white, off the shoulder lacy top.

"Adorable," she clapped when I'd put it on.

"Really. You think so?"

"I know so, bitch. Let's blow this joint."

I hugged Tom good bye not knowing that it would be days before I'd see he and Cindy again.

"Be a good girl," he said patting my bare bottom.

cindy and I rode the elevator down, climbed into the Uber and were off to a new adventure; new for me anyway.

I hope to get the next chapter out before the New Year My new "friend" is keeping his bitch busy with other things. Merry Christmas all.

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ryanlvr7ryanlvr7over 1 year ago

I wish my wife would find a real man to seduce her and awaken her sexually in a way I never could in 32 years of marriage. I’d love for her and her lover to feminize me. My little 4.5 inch clit was made for panties. I’d love to be turned into Ryanna full time and go out with other girls like me.

BCaSoHBCaSoHover 1 year ago

Love the build up.

Praying for a cock and cum filled exhibitionistic climax.

Can't wait!!

cdCindy1cdCindy1over 1 year ago

Fantastic story, sissy Jennifer. In case other readers don't know, I am the "cdCindy" that Jennifer writes about in this story. I am so flattered that she has included me in one of her stories.

I can't wait to read what happens next.

Thank you Jennifer (Johnnie).

Hugs & kisses,

cdCindy XOXOXOXOX

88girfriend88girfriendover 1 year ago

Nice. Sissy storied are fun.

liz33ndliz33ndover 1 year ago

loving this, great start for a new sissy

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