Play Date for Sissies

This author imagines a lad being claimed and groomed by an older coupe and schedule a play date for her.

It's no secret that I'm not much of a man. As a matter of fact, I have always been considered a sissy. I mean even my parents knew what I was going to be when I grew up. Dad hated it. Mother nourished it.

So it was that by the time I became an adult I was fucked up in my head. I felt the same way about women that other young men do but was never able to act on it. I wasn't built the way a guy should be to pick up women. My height was a mere 5'5". My weight was only 118 pounds. My hips were wider than my shoulders and my fanny a bit too fat, too round for a guy. But the thing that was really under developed was my thing. My penis. My "Pussy flap," as dad called it. Nearly 4" hard, I was ridiculed and teased throughout my life by those who saw me naked.

The exception was mom. She said it was cute and I needn't fret about trying to meet a nice girl. "Who wouldn't love you,? she would say. "A cute boy like you. You'll find someone johnnie. I just know you will. And whoever that might be, I'm sure he will make you happy."

And then she'd wink at dad.

When I graduated from high school and told my parents I had an interest in going to college, mother was all for it. Dad on the other hand growled, "If that cock sucker wants a higher education, let him pay for it himself. I'm not paying so he can go off and learn how to be a fucking homo."

So, instead of furthering my education, I moved out and with a small stipend from my mom rented a room in the DC suburbs.

I led a lonely life through my early 20's. Moving from one job to another I was barely making my rent on the one room above the garage of the mid 30's couple who owned it. I'd found the rental in the local free community newspaper.

Mrs. Grammercy was much like my mom. She worried about my comfort, whether I had enough to eat, things like that. Because she was so nice, I would help her with her flower beds on weekends and do other odd jobs for her just to be in her presence. She would tell me funny stories about their neighbors while we pulled weeds and she and I would giggle. She was pleasant to be with and I enjoyed her company. Most of all, I trusted her.

Mr. Grammercy wasn't at all like dad. He was friendly, maybe a little too friendly at first. Sometimes when I'd be on my knees, my bottom raised as I tended Mrs. Grammercy's gardens, I would turn and catch him staring at me with a strange look on his face.

I'd been working as a stock boy in a department store and at nights would clean the local laundromat, mopping, cleaning lint traps, wiping down the machines. I was only making $4.50 an hour at both jobs and had only little left from my rent to buy food. Forget clothes. I sold my 14 year old Toyota Camry because I couldn't afford the insurance or up keep. The walk to my jobs wasn't too long, maybe a couple miles.

Mr. Grammercy offered to give me a ride to work one day and I found out why he'd look at me the way he does.

We'd only just left the block when he placed his right hand on my thigh and began to run it up and down. "You know johnnie, you're a pretty boy. I mean for a guy, you're sexy. See what you do to me?"

With that he placed my hand on his crotch and I felt his erect penis. "This is your fault baby boy. I think you may want to help your Mr. Grammercy with it."

Fortunately, we were at my job and I hopped out thanking him for the ride.

"Think about what I said son. Trust me. I could make things easier for you."

My mind wasn't on work that day for sure. I messed up the count in men's shirts and my boss yelled at me. All I could think about was what Mr. Grammercy did and what he told me. I wasn't like that. I wasn't that way. Regardless of what dad thought of me, I just didn't think I was a sissy.

So why did what Mr. Grammercy made me do make my little penis stiff?

I went through the motion at the laundromat that night and crawled into bed. My thoughts went back to the ride to work and I slept restlessly.

The next morning Mr. Grammercy again gave me a ride to work and again he placed my hand on his cock. I left it there but did nothing.

As the weather grew warmer, Mrs. Grammercy and I planted, weeded, and cleaned out a place for a small vegetable garden.

"johnnie, it's hot out here. Too hot for you to be wearing long pants. Why don't you go and put on some shorts?"

I explained to her that I didn't have any shorts and that I was alright.

"Nonsense. Come with me."

I followed her up to her bedroom and watched as she went to her chest of drawers and rummaged until she pulled out a red pair. "We're about the same size," she smiled. "See if these will fit you."

I tried to refuse but Mrs. Grammercy would have none of it. Swatting my bottom, she told me to go into the bathroom and slip them on.

Mrs. Grammercy is sweet and kind and I trust her. So I did what she wanted me to do.

They were tight when I buttoned up the sides and my boxer shorts stuck out the legs. When I showed Mrs. Grammercy, she went to another drawer and took out a pair of Mr. Grammercy's white briefs. Holding them up to my waist she chuckled, "These are way too big for you johnnie. Let me think."

She took a few seconds and looking me over made a decision. "You'll simply have to wear mine," she said handing me a pair of white bikini panties. "These will do and it will be our secret. Now hurry along johnnie. We have much to do."

I felt embarrassed but I knew in my heart that Mrs. Grammercy was trying her best to be kind. And I did trust her. I sighed and did as she told me.

If I said her panties didn't feel nice, I'd be lying. The fact that she had worn them, her pussy had been where my penis was now, excited me. This was as close to a pussy I'd ever been. I had to wait out my little boner. To rid myself of it, I thought of my dad. What would he think if he saw me? It worked and my little dick shriveled up where the little bump longer showed.

We went back to work on her gardens.

"You know johnnie, Mr. Grammercy and I never had children. You're like a son to us."

I didn't know what to say but thank you. She made me feel welcomed and happy. I liked her and trusted her.

When I wasn't at work, I tried to be helpful while trying my best to steer clear of Mr. Grammercy. Still, every day he'd offer to drive me to work and every day I'd end up with my hand on his privates. It became routine. So routine that I just accepted it and began to grab his penis as soon as we fastened our seat belts. That seemed to make him happy.

And me hard.

I think it was the way he used me, took pleasure from me without asking or reciprocating. There is something highly arousing being used by a superior person that excited me. I had no real desire to do anything with his cock but just the act of him wanting me to touch it, hold it, squeeze it, well, you had to be there.

One hot July Saturday, after we'd weeded and watered her gardens, Mrs. Grammercy thought it would be a grand idea of we caught some sun. "Let's change into swim suits and catch some rays johnnie," she said with enthusiasm.

I knew if I told her I had no swim suit what was going to happen. I was right.

She insisted I wear one of her two-piece swim suits. Handing me the black bottoms she told me that no one would know and not to fret.

Trusting her, I once again did as she instructed. Once again, my little thing grew stiff thinking about where her pussy had been.

She had changed into a red two-piece and we went out to the back yard and laid out on beach towels.

Mr. Grammercy came around and saw what we were doing. "Let me put some lotion on you Lois," he said going to retrieve sun screen.

I lay on my back and watched while he applied the lotion on Mrs. Grammercy. What I hadn't expected was when he stood over me and said it was my turn.

"Um, er, no thank you sir. I'll put it on myself."

"Nonsense johnnie. Let Herb do it. After all the work you've done with me, it will relax you," Mrs. Grammercy said.

"Lay still boy. Let me do this for you."

I shivered when his hands, covered with the cool lotion hit my shoulders. He rubbed me softly.

"I love the way his buns hand out from the bottom of your swim suit honey," he said to Mrs. Grammercy.

"Yes Herb. He does look cute in it, doesn't he?"

I felt his hands move down to my legs and he started applying lotion to my ankles. Then my calves. Then my thighs. I stiffened when his hands began to massage the part of my ass that was not covered. "Lois, this boy's bottom is as soft as a baby's butt."

I looked at Mrs. Grammercy for help. She was smiling sweetly. "Let Herb have his fun johnnie. It will be okay. I promise."

I trusted her. So, when Mr. Grammercy said I should turn over, I did. I was erect and they both noticed. My face was red with shame and Mrs. Grammercy did nothing to help when she said, "johnnie must like his bottom rubbed Herb. You should see that cute bottom in panties."

Mr. Grammercy was straddling my torso now. His big hands rubbed lotion on my chest and he smiled down and pinched my nipples. I squirmed but he held me where I was. "He has no hair on his cute body," he told his wife. "But look how hard his nipples get when I play with them."

I raised my arm to hide my eyes feeling shame but also turned on. "Look at his tiny erection Lois. I bet it's not as big as my thumb."

"Let him show me johnnie. We're private here. No one but us three will know."

"Please no.." I pleaded as Mr. Grammercy pulled my swim suit bottoms off. My boner stuck up in all its 4" glory.

"See. no bigger than my thumb and johnnie has no hair."

"Oh God, no" I whined as he pulled on my dick.

With the lotion on his hands, Mr. Grammercy's soft handling of my privates felt nice. Very nice.

Of their own accord, my hips began to rise and fall with his motions as he slowly jacked me off. When he stopped moving his hand, I continued to fuck up and down. My orgasm was the only thing on my mind.

Mrs. Grammercy turned on her side so she could watch. "I bet he's a quick shooter," she said.

"Please don't," I said through gritted teeth.

"Shhh johnnie," Mrs. Grammercy said. "It's okay baby. Trust me."

Mr. Grammercy removed his hand just as I was about to cum.

"My turn son," he said smiling as he pulled his trousers off.

I couldn't look away. His cock was huge compared to mine. His big balls hung low and heavy. Black curly hair framed his manhood the way I could only wish mine did.

Mrs. Grammercy came up beside her husband smiling down at me. She had removed her swim suit and was as naked as her husband and I were.

Mr. Grammercy moved slowly kneeling over me so his cock was pointed at my mouth.

Mrs. Grammercy was down low by my feet. "Mommy is going to suck your little dick johnnie. Mommy wants you to spurt in her mouth baby. Daddy wants you to suck his big cock and he wants to spurt in your mouth. Now be a good boy and do as mommy says. Trust me. It will be fun and make you feel good too."

I opened my mouth to protest but before I could get a word spoken, Mr. Grammercy slid his cock in. "That's it baby boy. Suck him johnnie. Suck daddy's nice big cock while mommy tends to your little one."

I moaned when I felt her lips engulf my dick. Mr. Grammercy, daddy, liked the way my moaning felt on his cock. "That's nice boy. Suck it. Suck daddy's cock you beautiful little fairy."

He pumped his big cock in and out of my mouth and I was getting into it. What with mommy making me so excited with her mouth, I tried to do the same things to him that she was doing to me.

"Oh yeah. I knew this kid had a cock sucker in him."

"He doing good then,?" Mrs. Grammercy asked.

"He was born to suck cock Lois. I swear this can't be his first one."

"Feed him your balls dear. I know how you like to have them kissed and licked."

Daddy took his cock out of my mouth and positioned his balls in their place. I immediately opened wide and lavished his scrotum with licks and kisses. I was into what I was doing and I felt good. I felt wanted. I felt at peace.

But mostly, I felt sexually aroused.

Once again his cock found my opened mouth and daddy pushed in until I gagged. "Fuck his mouth Herb. Fuck his pretty cock sucking mouth. Pump your load down his cock sucking throat. Make him your bitch. Make him our sweet little sissy bitch."

Then she went back to sucking me and I groaned and came.

Daddy announced his eminent orgasm with a growl. I felt his cock widen and tasted my first load of sperm. Unlike me, daddy's cock pulsed several times as he fed me my reward.

I didn't find the taste repulsive at all. To the contrary, I found it savory, a little salty and tart. Daddy's sperm was easy to swallow and I made sure I got all that he had to offer.

"Like a duck to water," daddy smiled at me. "You're gonna make us a very nice sissy, johnnie."

When he'd finished, Mrs. Grammercy took his place and for the first time in my life, I saw a pussy up close, just before she sat on my face. "Use your tongue baby. Lick mommy good.

She taught me the proper way to eat pussy and let me suck her fat clit until she clenched her thighs and came. Mrs. Grammercy squirted her orgasm which covered my face and ran down my neck.

She and I were both panting when she rolled off and lay beside me. "Baby boy, you have no idea how fucking good that was for your new mommy," she said while licking her juices off my face and neck.

We hung out naked for the remainder of the afternoon. I became very acquainted with daddy's cock as I knelt in front of him and sucked him off again. Mommy played with my butt, sticking a finger in me making me cum just as daddy came. Both noticed the high-pitched squeal that came from me when my dick shot a load between daddy's feet.

"I think this boy is really going to enjoy being fucked honey," mommy said. "She is going to be our good sissy."

Later that night they invited me into their bed and I watched daddy fuck mommy and learned that boys like me will never ever get that privilege. "Little dicked boys clean used pussies and cocks johnnie. Lick daddy clean and then suck his cum from mommy."

What can I say? I trusted her.

We all slept in until late Sunday morning. Over coffee and toast mommy asked me how I felt about the events of yesterday.

"You seemed right at home sucking daddy's cock baby. Did you like it? Did you enjoy it?"

I thought about that question. Did I like it? Did I enjoy it?

"Mommy, it was okay, I guess. I mean I didn't hate it and I liked making daddy feel good, just like I made you feel good."

She came to me and kissed my cheek. "My precious baby," she said with more meaning than my own real mother had ever said. "You move your cute little bottom out of the garage and sleep with us from now on."

And just like that I learned I did have a place in life. I was useful. I was wanted.

We settled into a comfortable routine. Most mornings we'd leave early so I could suck daddy's cock for him while he drove me to work. When I'd get home, mommy would be in a robe, a night gown, or dress and waiting for me to kneel in front of her and get her off with my mouth. They let me pay half the rent I had been paying and I slept with them, I ate with them, I watched tv with them, we did everything together.

Mommy and daddy taught me a lot about myself those first weeks after I became part of their family. I learned what a sissy is and that I had all the makings of being, as daddy said, a top-notch sissy or lady boi. They explained it so clearly that I just knew they had to be right.

They told me I was responsible for making them feel good. My mouth was the object of desire for both mommy and daddy and for others as well.

That was when they decided that they should claim me as their own. "It makes perfect sense," said mommy. "Trust me johnnie. If you're out there on your lonesome, some mean man may claim you, take you home and make you do all kinds of dirty and nasty things. He might even hurt you."

Daddy Herb taught me that men, real men have cocks, not tiny little pee-pees like mine and that nature had made me special. "Look son, you're a freak. Now that's not bad. What I'm telling you is that both men and women have need of your special gifts."

"Gifts daddy?"

"Baby boy, you are sexy. Sexy, sweet and polite. Your mouth is the perfect receptacle for cocks and Lois says you're a natural muff diver."

"What's a muff diver," I asked, pulling my mouth away from his cock.

"johnnie, a muff diver is a pussy eating son of a bitch. A real connoisseur of cunnilingus. See, that question proves what I'm saying about how sweet you are. You're so new, so fresh, so innocent that guys would line up to stick their cocks in you. That's why you should stay with me and Lois."

I got out of the car and went into work, the taste of daddy's sperm still in my mouth.

When i returned to my new home mommy wanted to make me understand what I should consider my new life. I was slurping her gash as was routine while she went over the fine points of being claimed.

"But I have parents mommy," I said.

"Yes you do johnnie. But you also have a new mommy and daddy if you give yourself to Herb and me. Oh yes baby. Lick mommy's pussy on the outside. Suck on my fat pussy lips. That's it, that's it. You're doing mommy so good. Now suck my clit like it's daddy's cock. Mmm, my but you have a mouth on you."

Both convinced me that I'd be much happier if I would let them claim me as theirs.

It was not all peaches and cream you understand. There were rules which, if broken, came with spankings. There was to be a dress code, one which would remove all doubt from those who see what I really am.

I was sad when mommy explained that she would never again suck my wee-wee. "Bois such as you johnnie, need to get themselves off. It just isn't proper for me or daddy to do that for you. But you must promise mommy and daddy that you will always ask for permission to beat off. Promise?"

I made that promise with the understanding that their permission would not be rubber stamped. Sometimes they would deny me orgasms just because they could.

It seemed that every day when I'd get home from work there's be presents for me. A negligee, panties, new shoes, sexy tops. Mommy even took me shopping for new clothes.

I began to wear to work those clothes mommy bought me and experienced what daddy had warned me about. Mr. Stankly, my manager would grab my bottom and tell me it was an accident. Once he cornered me in the stock room and tried to get me to suck his cock. "Those pants johnnie. They make your fat ass look so damned sexy," he said putting my hand on his cock.

"When I got home I told mommy and daddy what happened. Mommy was upset that Mr. Stankly would try to make me do nasty things in a stock room of all places. Daddy chuckled and gave me a, "I told you so".

It was settled that I would quit my job, sue them for maintaining a hostile work place and live with mommy and daddy.

I would assume the household chores and mommy was teaching me how to cook and how to be a grand hostess.

I felt like a child with them. I really did. Daddy was much taller than me and when we'd go out he would always hold my hand. I felt safe with him. Even when he got angry with me. Once, he said I got too rambunctious at the mall, wandering off. Both he and mommy decided that it would be a good idea of I wore a harness when out with them; the kind parents put on toddlers.

We got lots of looks when we'd go out. I'd be wearing my bib shorts, a ruffled top, pink sneakers with my white anklets with the roses on the top and my harness with mommy or daddy holding the leash. Just to make them laugh, I would pull against the harness and leash as though I was trying to escape.