Play Date for Sissies

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That was a mistake. Right there in the food court, daddy took me over his knee and spanked me in front of hundreds of onlookers.

I learned my lesson well. Daddy had no real sense of humor and would not hesitate to mete out corporal punishment whenever, where ever. He told me while spanking me that he would tolerate no such disrespectful behavior.

I think it was knowing that they cared about my comportment and would take corrective action should I stray that made me feel loved by my new mommy and daddy. I became more lady-like which pleased them both to no end.

One night with mommy and daddy, each holding one of my hands and both reassuring me that I would be fine, they walked me into a tattoo parlor. When we left, I had a bar-code tattoo on my neck up under my shoulder length hair. Under that were the words property of Lois and Herb and their phone number.

I was officially owned. And even though the tag was painful, I rewarded daddy with a slow, wet blow job on the drive home.

We settled into a peaceful and satisfying life together and I was secure in the knowledge that they would always take care of me as though I was their little boi. I trusted them both.

"Herb," mommy said to daddy one night during a commercial. "We simply must share our good boy with Tom. I know Tom has his own sissy and maybe we should invite them both over for a play date."

I was sitting on the floor between mommy's open knees while she brushed my long hair. I had by now accepted her insistence that I wear panties and a cute top when at home with them. She toyed with the idea of painting my finger and toe nails. We hadn't done that yet but I trusted her and if that's what she wanted to do, then so be it.

"You know Lois, that's a good idea. Tom can bring jimmi with him and we can let the two sissies have their fun."

"We'll have to get you made up pretty johnnie. jimmi will be and I think you should be too."

The day I met Mr. Tom and jimmi was the day I really came into myself as a sissy. Mommy was very excited as she applied my eye liner, mascara, and heavy lip stick. "Bright red for my baby boi," she said while fussing over me.

"What to wear, what to wear," she mused as she went through my clothing. "Since you bois will be playing in the yard I think your cute swim suit would be appropriate johnnie."

She helped me into the one piece. It is white with a thing bottom and high-cut sides that show my hips. She had me put on my black high heels and brushed out my hair.

"Let me look at you. Very pretty johnnie. You're a beautiful little girl."

I felt that way too. I mean not thinking I was pretty but mommy and daddy had me feeling so feminine and acting very lady-like. I wanted to be their good girl.

"Do you think jimmi will like me mommy?"

"Yes baby girl. I think you two will hit it off nicely. If you play nice and behave, we might, now don't get overly excited but we just might let you two suck each other off. But you have to be on your best behavior and be very polite to Mr. Tom."

"Yes mommy. I promise."

When we got downstairs daddy and Mr. Tom were already having drinks. Sitting on the couch was a pretty boi like me. He was dressed for Easter Sunday church, I think. Mr. Tom had him wearing a white with flowers dress, little white shoes with white ankle socks which had pink trim around the tops. On his head was a very nice bonnet. His make-up was done perfectly.

When mommy took me by my hand over to meet him, jimmi stood up and curtsied. "Hello Mrs. Grammercy."

"Why jimmi, don't you look sweet. Mr. Tom has trained you well. I'd like you to meet johnnie. johnnie, this is jimmi. I want to see you welcome him as I told you would be nice."

I was peeking around mommy's gown, shy. But mommy pulled me around and I went to jimmi and kissed him on his lips real quick as mommy said I should.

"He's a little over-dressed Tom, for a play date. Did you bring anything else for him to change into?"

"They'll be in your yard right? I'll have the little cock sucker take off his dress and shit and let him play in his underwear. The little slut likes showing off. Don't you cunt?"

"Yes sir daddy," jimmi said enthusiastically.

"You bois go outside and play. Remember, we'll be watching so no fucking up."

"Yes mommy," I said taking jimmi by his hand.

"What do you want to do," I asked.

"I don't know. What do you want to do?"

"We can play in the pool if Mr. Tom says you can."

jimmi asked and Mr. Tom gave him permission to play with me in the pool.

"johnnie," I heard daddy call. "Help jimmi out of her dress boi."

"Yes sir daddy."

I unbuttoned the back and pulled the straps off his shoulders. The dress zipped at the waist so I lowered that. When the thing fell in a pool around his feet, I was amazed at how sexy his underthings were.

The semi-transparent, high waisted panty had a lacey band. The thong back let me see how very sexy his bottom was. Before I did anything that might be considered rude, I took his hand and we splashed into the pool.

"You girls stay in the shallow end," mommy called.

We giggled and splashed each other. Once, jimmi tried to pull my swim suit off and we tussled about with me tugging at his panties. We laughed so hard we became breathless. Standing in waist deep water we caught our breath and spontaneously hugged.

His hand found my bottom and my hand his dick. I was surprised that his dick was bigger than mine. "He must measure at least 5 inches," I thought.

We looked at each other and we both knew what we wanted. I looked toward mommy for permission to continue. She smiled and nodded.

Our mouths came together in a passion filled, tongue dancing kiss that lasted a long time. Our dicks rubbed together. jimmi's finger went under my suit and he poked at the opening in my bottom.

I was excited and scared at the same time. Not having my bottom penetrated before by anyone other than mommy that time, I quickly knelt and began kissing his dick through the nylon panty.

"Will you look at those two faggots," I heard Mr. Tom exclaim. "jimmi has never had any other dick but mine in her mouth before today."

"johnnie has never been fucked either," mommy told him. "Today might be a first for our baby bois."

"No getting off without asking for permission first," daddy reminded me.

"Same for you jimmie," Mr. Tom agreed.

We stopped what we were doing and I took his hand in mine and we walked over to our owners.

"Please daddy and Mr. Tom," I begged. "Please let me get off and let me get jimmi off too."

"Later girls. Kindly remove the rest of your clothes and assume your positions," daddy said.

We skinned out of our clothes, me, my swim suit, jimmi, his pretty panties. Then we both sat at our respective daddy's feet beside their chairs.

jimmi and I looked at each other as the adults made small talk. "I think johnnie would suck you off first before jimmi finished Herb," mommy bragged on me.

"My little jimmi can suck the chrome off a trailer hitch," Tom said to laughter.

Daddy decided we would be tested. "johnnie will suck you off, jimmi, me. Lois will watch and use a stop watch to see which girl is the better cock sucker."

I was directed to Tom and told to get his cock out. "Fuck that pulling out his fly baby boi. Take his pants off," mommy instructed me.

I did and saw his cock. It was as big as daddy's and my mouth watered. "Looks like you have got yourself an eager cock sucker Herb."

"That little mother fucker was born to suck cock Tom Just you wait."

With both men now completely naked, I watched mommy shed her clothes too. Her wide hips enticed me. I couldn't help it if I still wanted pussy. Mommy had trimmed her bush and her labia were prominent as was her large clit. She turned and bent over to pick up the stop watch. God her ass was beautiful. I had the sudden desire to kiss it, make love to her bum. Maybe one day. A girl can hope can't she?

The contest wasn't suspenseful. I had Mr. Tom pumping his load into my tummy in no time. I finished sucking him until he was limp and jimmi still hadn't coaxed daddy's sperm from his balls.

"2minutes, 38 seconds," mommy crowed.

"I guess my little sissy needs more practice," Mr. Tom said with some disappointment.

"Come here johnnie. Show jimmi how it's done."

I crawled to my daddy and jimmi made room. I took his place on daddy's cock while jimmi caressed my back and bottom.

I heard him ask, "Can I daddy?"

"You need to ask his mommy and daddy first. If they say you can, it's okay with me."

Mrs. Grammercy, Mr. Grammercy, can I please fuck johnnie?"

Daddy spoke first. "No. He's a virgin and I want to break that fat ass in myself."

"What are you waiting for,?" Mr. Tom asked.

"Look Tom. You treat your sissy the way you want and I don't interfere. Let me train my boi my way."

"No problem Herb. I was just asking."

"Tom," mommy said. "Herb wants to bring her along slowly. I mean you see how well she sucks a cock right? Well, we want her to be able to take lots of cock in her pussy and we want her to want them. johnnie is going to make a fine slut."

"Ugh, I'm cumming you cock sucking faggot," daddy said. "This little mother fucker knows how to please cocks Tom. I may take him on the road."

"Whore him out?"

"You bet cha. this sweet boi can make his new mommy and daddy a lot of money."

"Now Herb. You'll do no such thing. johnnie is ours and I won't have you whoring him out. She's our sweet girl and I want to keep her that way."

"Yes dear," daddy chuckled. "You know what they say Tom; happy wife, happy life."

I was hearing all that while finishing what jimmi started. Daddy had enough and pushed me aside. "Go on and suck each other johnnie. Show her how a cock should be sucked."

More giggling from jimmi and I as we hugged ourselves in position to suck one another.

Lying on my back, I was aware that mommy was filming us. Two naked bois slobbering all over each other's crotch. His dick was bigger than mine but not nearly as big as daddy or Mr. Tom. I was able to swallow it without gagging.

His lips felt wonderful on my dick. I really could tell what his technique was but it felt good to me. I came quickly as usual and jimmi stayed with me until my dick shrunk back to my 1 1/2-inch softness.

I knew jimmi would cum soon. He began to fuck my mouth. I held on to his sexy bottom and let him take his pleasure until his watery, thin sperm gushed from the slit and spit his love juice in my mouth.

He ejaculated more than I did but again, not nearly as much as the real men did. All in all, it was a satisfying experience and I hoped mommy and daddy would schedule more play dates for us.

I cooked a meal and jimmi got clean-up duties. Full and happy the adults let jimmi and I watch as they double teamed mommy. Daddy fucked her pussy and Mr. Tom let her blow him.

The night ended with mommy feeding jimmi his daddy's cum from her mouth and me lapping at the present my daddy left for me.

It was a fun day and just before I fell asleep between mommy and daddy, I knew I was home with people who love me.

As always, comments and email are appreciated.

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4 Comments
liz33ndliz33ndalmost 2 years ago

i liked this story what a way to keep a story interesting, it will be great to read on both of the sissy progression. maybe boobs and piercings, love the authors style. 5 stars

AmberFountaineAmberFountainealmost 3 years ago

The childhood I wished I'd had. I was in my thirties before I was given the full sissy treatment.

Harry_BallsackHarry_Ballsackalmost 3 years ago

That was a fun story. I like the pace and it kept me entertained. Keep up the great work

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