Coach

by Gingerfred Man

 

Chapter One – A Tough Job, But….

 

You probably think I have the best job in the world. And you’re right. But it’s not always easy and there are headaches. The stories I could tell you!

I mean, sure, being a trainer of sissies sounds glamorous and everything and the perks – all those sweet, young asses wrapped around my cock – are great. But there are headaches too.

The parents! Sometimes they can be difficult. Like they know how to train a sissy! If they did, why did they come to me? I don’t even deal with the fathers anymore. They were the worst. Always complaining about their sons being feminized too much or not enough. I think they were jealous. Of their sons, not me. They were the ones who wanted to get into pretty dresses, get on their backs and have me fuck their asses. But that’s not for me. I’m no queer.

Let me tell you a little about myself. My name is Walter McDonald, but no one calls me that. To everyone I know, I’m "Coach."

I did all the macho stuff growing up – played football, spent four years in the Corps (Semper Fi, my brothers), then went to college and taught high school kids for six years. Even did some assistant football coaching. I liked how I could get kids to do the right things – things that were best for them – by setting a good example and being strict, but fair.

I guess I would have kept doing that for my whole life if Mrs. Peters hadn’t come along.

Tommy Peters was a second-string running back on our team and I was his position coach. Mrs. Peters noticed the way I led the boys and that I had a nice rapport with her son. That gave her the courage to invite me to their home one day and ask for my help.

"Coach McDonald," she said, "my Tommy’s a good boy, but he’s very unhappy. Nothing has seemed to work, so last week, I took him in for a battery of tests, including the Gingerman Test."

I remembered reading about that test in the educational journals, but couldn’t quite place it.

She continued, "Tommy scored extremely high in the Gingerman Test, which means he is surely a sissy, but I can’t get him to admit it or do anything about it. I know he’ll never be happy trying to pretend he’s a man. But he won’t budge, because he’s afraid of what people will say and do about him."

Even then, I understood that if God made you a sissy, you’re a sissy and that’s all there is to it.

"Coach, I’m a single mother and I’m desperate. I need you to convince Tommy that he’s a sissy and help transition him to his new life."

I protested. "But Mrs. Peters. I don’t know the first thing about sissiness or clothes or hair or even accessories. All I know is what men like in women."

Mrs. Peters met my objections, "That’s all you need. You’re smart and kind and Tommy trusts you. Oh, but the bad news is that I can’t pay you."

That was OK with me. Money was no big deal, but I did want what was best for the kids.

"I can, however, give you some of the best sex a man ever experienced, starting right now."

<Gulp> I was terrified of her. Was I ever that young and inexperienced? I stared. She lifted her skirt, revealing black garters, black stocking tops, pink panties and an excellent pair of thighs. She grabbed my hand, led me to her bedroom and we fucked as if we were possessed for a good three hours. In every orifice. With great expenditure of fluids.

Then I set out to earn my fee.

The next day, Mrs. Peters (by then I was calling her Linda) arranged for Tommy to be home alone waiting for a repairman who had never been called.

I knocked. He answered and his face lit up when he saw me. He invited me in.

We sat in easy chairs facing each other. As always, I was direct and truthful. "Your Mom and I have been talking about you, Tommy."

Tommy became very wary. "What about?"

"She thinks you’re living a lie and she’s worried."

Tommy was very frightened. His eyes were wide and began to fill with tears. "Coach, I…."

"Don’t be afraid, Tommy. I would never tell anyone anything that would hurt you and I would never think less of you. It’s never a sin to be what you were made to be. Do you trust me?"

The fear evolved to indecision, but he managed a, "Yes, Coach."

"Then tell me."

I waited.

He began to sob.

"It’s OK," I said, and held out my arms.

He left his chair and actually sat in my lap, sobbing into my chest as I rocked him and patted his back.

Through his sobs, he managed to say, "I am a sissy. I’ve always known it. But I was so ashamed. I wanted to be like everyone else, but I also wanted to wear panties and nighties and pretty dresses and <blush> make love with boys. And men."

Through his tears, the little teaser actually batted his eyes at me when he said the "and men" part. So I did the only thing I could.

I kissed him.

He really liked that. He kissed back as if he were starving and I was an ice-cream sundae.

Before I knew it, his pants were off and I had my hand in the back of his pink panties.

Nothing in my life to that point had prepared me for that. I thought I only liked women. Little did I know that sissies were women, only better.

The little scamp was so steamed up that when I put my middle finger into his tight hole, he squealed and came hard, filling his panties with his hot spunk. We were still kissing and he was panting and gasping when he broke our liplock and got on his knees in front of me. Frantically, he pulled down my pants and underpants to my knees, not even bothering with my zipper. My cock was outrageously hard and shiny with my sticky gunk. Tommy handled it as if it were a sacred relic, then swallowed the head as he caressed my balls. I have a rather large penis with a long, fleshy foreskin, but Tommy got a large part of its territory into his sweet mouth. I had never been so sexually charged up. I looked into his loving eyes as he slurped my meat and just lost it. I winced in erotic torment, then released my hot cum into Tommy’s hungry throat. Tommy swallowed, purring and giggling with pleasure, then spread his cummy tongue all over my aching balls.

Oooohhhhhhhhhhh. I was hard as diamonds again in seconds.

Tommy stopped slurping my testicles, got up, walked to the couch, and eased down his sopping panties, revealing his cock to me for the first time. It was beautiful and startlingly large. Almost as big as mine, with a lovely foreskin and pointed, rather than mushroomed tip. It looked incredibly delicious. Tommy then lay on his back, and raised his knees, exposing a very fine-looking, pink, puckered bottomhole. As if I didn’t know what he wanted, Tommy moaned, "Fuck me, Coach. Please fuck me!"

Goodness!

I joined him on the couch, lying on top of him and kissing him sweetly. I wet two fingers with saliva and entered his anus with them. I wanted to loosen him a little, but he was very impatient. I entered him with my penis, as gently as possible. He whimpered and squealed from joy, not pain and when I was all in, we began a motion that pleased us both greatly. His mother was a very sexy woman, but sex with Tommy was heaven on earth. The frantic, hungry kissing made it even better.

We fucked for the finest 12 minutes of my life, then my lovely Tommy’s eyes widened and he came and came and came. His huge tool spurted cum all over his belly and onto mine. This excited me so much that I joined him in bliss, cumming so hard that I couldn’t focus my eyes for several seconds.

We kissed some more and I was truly in love for the first time in my life. A few minutes later, Tommy excused himself and was gone for a good 30 minutes. I was getting worried, but when he came downstairs, he was wearing beautiful make-up, pink, stay-up stockings, a pink baby doll nightie and pink mules.

"Tommy!" I said.

Giggling, the beauty said, "Please call me Cheryl, Coach."

And that’s what I’ve called her ever since.

 

Chapter Two – Ryan

That was twelve years and 83 sissy trainings ago. My darling Cheryl lives with me and shares my life. She’s also my partner in what has become a professionally rewarding, as well as very lucrative. business. Cheryl and I have become world-renowned as the greatest sissy trainers in history. It’s widely said that I have a gift for recognizing sissies and for bringing them out into the world in their true nature.

Modestly, I must admit it’s true. Still, Cheryl and I have great integrity in our work. We don’t force any boy to become a sissy if he isn’t one already. Mothers have brought me eight non-sissies for training and were somewhat angry when I told them the honest truth about their sons. They just weren’t sissies.

Now it’s my theory, and I’m an expert, that every boy has some sissy in him. By the time they’re men, they’ve almost all suppressed it. I know for a fact that every man secretly wants to see what it would be like to suck a cock and swallow cum. But we can’t turn everyone into sissies now, can we? You are or you aren’t. And no one can tell like I can.

That’s why about ten years ago, Cheryl and I began charging a separate fee for evaluation – usually $5,000, plus expenses and other considerations. We charge a lot more, usually $50,000 to $75,000, plus expenses and other considerations for complete sissification, but we’re the best.

Cheryl does a great deal of the mothering and teaching about clothes and stuff. I take them to sissyhood in their minds and spirits.

The best way to explain would be for me to tell you about Sally, my latest little sissy girl.

With Sally, as always, I asked the inquiring mother to come in without the child for a discussion of procedure, fees and such.

Cheryl does our marketing and it’s no wonder she brings in so much business. She is an exquisite beauty. Twelve years of hormones, little touches of surgery and a great deal of knock-down-drag-out fucking have made her into one of the most beautiful women on the planet. I’m completely in love with her and she with me. She has a fantastic figure, accented by the tailored suits that make her look like every businessman’s fuck dream. She has killer legs and wears four or five inch stilettos almost all the time. Her C-cup titties are my favorite pillows and I drain her clitty, often with my mouth, several times each day. I am truly the luckiest man on earth and would be completely faithful to Cheryl if my business didn’t require me to have tons of sex with tons of people. Cheryl has her "friendships" with other people as well. But we are still madly in love.

Cheryl was looking particularly edible the day she escorted Sally’s mother, Mrs. Wills, into my office. I love her in black stockings and those sexy, towering sandals she wears and she knows it. I love when she paints her toenails bright red and I can see them right though the sheer, black nylon. Oh my. I knew I would be sucking those little piggies later that day until she was cumming a spermstorm. But for then, I had to put my work face on.

Mrs. Willis was a moderately attractive woman in her late thirties. She was wearing a skirt, stockings and heels, which I appreciated. I’ve never asked, but I think Cheryl tells the mothers to dress like that when they see me.

She had nice make-up on, but her tears had streaked it.

I greeted her warmly, gave her a tissue and sat across from her. Cheryl left us and closed the door. I waited patiently for Mrs. Willis to gather herself and speak.

Through her sobs, she began. "It’s awful, Mr. McDonald. Ryan is out of control and so miserable.’

"Please, Mrs. Willis, call me ‘Coach’"

"All right, please call me ‘Susan’"

"It’s more professional if I call you ‘Mrs. Willis.’"

She nodded. "I’ve had Ryan tested, you know. He’s an out-and-out sissy. But he’s fighting it."

"Those tests can be wrong, Mrs. Willis." I could tell you some horror stories.

"But Ryan was always a sissy. He played with dolls and read hair and fashion magazines. I even dressed him as a girl now and then until he was eleven and he loved it! His little willie was hard as bricks whenever I put panties and petticoats on him. Then he just decided he was through with sissiness and has been a little creep for the four years since."

"So Ryan is 15. It’s good you brought him to me. He’s almost too old for a full conversion."

Mrs. Willis’ eyes filled with fear.

"I’m sure that if Ryan is a true sissy, Ms. Peters and I will be able to bring him to his destiny."

Mrs. Willis sighed with relief. Then I explained about our fees and such. She stiffened a little at the price, but I knew she would pay and told her we required half up front.

She asked, "But what are those other considerations you discussed in your fees?"

"An excellent question, Mrs. Willis. The reason why most sissy interventions fail is that they are performed by women. A sissy needs two things to go from a he to a she – tough love and lots of cock."

Mrs. Willis blanched a little. But listened.

"A woman is usually incapable of giving tough love and never capable of giving lots of cock. If we accept Ryan for the program, I’ll be fucking his little bottom and pretty face several times a day. He’ll be cumming ten or twelve times a day from stimulation by me, himself, our other sissies and the nice boys and men I will match him with for more ass and face fucking. It will rid him of the spermy juices that make him aggressive and boyish and will make him docile and girlish. How do you feel about that, Mrs. Willis?"

She was mildly surprised at my frankness, but I was sure it was nothing that she hadn’t considered. Then I told her something she surely hadn’t thought through.

"As to those ‘other considerations,’ I will also be fucking your ass and face whenever you come to my office to discuss your son or visit him. Beginning today."

I loved that moment about my job. It’s the real test of commitment by a mother. And the docility we require in them for our approach to work.

Mrs. Willis blanched again. She shifted in her seat. Seeing I was serious, she looked down and said to me in a small voice, "OK."

I stood. She stood. I held her hand and led her to a bedroom connected to my office. The walls were filled with pretty pictures of the sissy girls whom Cheryl and I made happy and successful.

Mrs. Willis removed her dress. She had very nice lingerie and a good body. Over the years, I’ve had some really fat, woofie mothers, wearing horrible underwear. But it’s an important part of the trust we must build, so I fucked them anyway. And often.

Invariably, on return visits, they were slimmer, better made-up, and wearing very sexy lingerie.

Anyway, I removed Mrs. Willis’ panties, placed her on the bed on her back and kissed her, stroking her clit to five earthquake orgasms. I could see that she enjoyed my approach thus far.

Then I removed my clothes, flipped her on her stomach, and licked out her delicious, apparently virgin asshole for a good half hour. One must never rush rapport-building. By that time, she was begging for cock, so I eased it into her pretty little pink rosebud and was delighted when she squealed with pleasure. Mrs. Willis was very hot and her ass put on a great housewarming. I was the first lucky visitor to go through that door and she welcomed me with body and soul. About thirty strokes in, she screamed in orgasmic fury and shook so hard, I was a bit concerned, though not enough to stop. She did it again at 70 strokes and that was all it took for my balls to explode with hot, manly spunk into her naughty pit of heavenly pleasure.

When she was able to catch her breath, she turned and devoured me with kisses, ending up on her knees with my poop-flecked cock three-quarters of the way down her esophagus. When I blew another hot load into her face, she screamed in erotic fury. She was so nice that I went down on her and ate her pussy to three more shattering explosions.

Believing that we now had the necessary rapport, I asked Mrs. Willis to bring Ryan to me in two days, for his assessment. He would not need any personal items, as Ms. Peters and I would supply what he needed if the assessment proved favorable. If it did not, he would be dismissed and sent home.

Mrs. Willis, who was by then, I was afraid, completely in love with me, left reluctantly, but two days later dropped Ryan off at the appointed time.

Ryan was a surly piece of work, all right. I loved a challenge. There was good sissy material there, I could see. He was good-looking and slim. Not too tall and not too short. But with an attitude.

I addressed that right away. "Welcome to our home, Ryan," I offered. "You’re a lucky boy. Your mother loves you very much."

The little creep sneered, but said nothing.

"You and I will be working together to make your life a thousand times better," I said. "But you must do everything I say and immediately."

He actually laughed at that. I let it go, then gave my first order. "Ryan, I want to examine you. Remove all your clothes and stand before me naked."

The little punk spat a "Fuck you" at me.

Exactly what I had hoped for.

Moving swiftly, I overpowered him completely, stripping him naked, even removing his socks. Despite his desperate resistance, I sat and flung his naked body over my knees, took a moment to admire his fine, plump bottom, then administered a really severe spanking.

He was crying and screaming for his Mama, then begging for his life. Just when his tender globes were fiery red and he believed he would expire, I stopped. He kept sobbing and whimpering, expecting more. But I just let him lie across my knee to see what he would do. After a minute or so, he stood up, sneaking a fearful look at me. He flinched when I reached in a nearby drawer and extracted a jar. This time, when I told him to come to me, he complied immediately. He stood in front of me, naked, whimpering and sobbing, but his cock was half-stiff, another very good sign. I told him to turn away from me and, of course, he did.

I considered his buttocks. Nicely tanned, but no bruising other than his teenage dignity. They were plump and pretty and apparently in need of cock.

He was sniffling in fear. I opened the jar and spread the contents, a cool, soothing cream, on three fingers. Then I gently touched his sore, right globe and softly rubbed the ointment in. He gasped with pleasure and visibly relaxed. Except for his cock, which I could see in a well-placed mirror had risen to its fullest height and was throbbing madly as I fondled his bottom.

Another good sign.

He had a lovely body and his prick was thin, but long and pretty, with a thick, long foreskin. I soothed his other sweet cheek with cool aloe. He liked that very, very much and his prick was in great distress. It went to Code Red when I rubbed the cool cream into the inner folds of his bottom between his cheeks. The young beauty began to spasm and spurt his boyish cream in hot, thick ropes, gasping with pleasure and sobbing with embarrassment and fear of further corporal punishment.

Instead, I drew him to my lap (I ruin more trousers that way) and held his quivering, naked body. He was still a little scared, but with some encouragement, cuddled nicely.

"I know you didn’t mean to spray all that nasty boy’s cream on my carpet. You’ll never be punished for doing what you must."

He gave me a sweet little smile, then cuddled some more. He really was beautifully charming.

I took his half-hard doodle in my hand and began to fondle the foreskin to maximum effect.

"Do you see how nice things can be if you do as you’re told and surrender to your own nature?"

That was a big concept for a young person to grasp, but he liked what I was doing, so he agreed.

"Are you going to defy me again?"

"Oh, no sir!"

Rub, rub.

"Call me ‘Coach’"

Rub, skin, tickle, rub.

"Yes, Coach."

Frig, caress, rub.

"Did you like when your mother used to dress you as a girl? Honest answer."

Pet, touch.

He hesitated, then said, "Oh, yes, Coach. Very much."

"Would you like to wear girlie things and do girlie things again?"

He wrestled with his feelings and said in a very small voice, "Yes. But…."

"No buts, Sweetheart. Just let Coach and Miss Cheryl help you."

Something seemed to leave him then. I had seen it before. He relaxed and surrendered to the pleasure I was giving him. Just as he was about to cum all over himself and me, he reached up to kiss me. I kissed him back and milked him all the way to Paradise.

I dismissed him then into Cheryl’s care and waited for her report.

 

Chapter Three – Ryan Meets His New Sisters

Cheryl took the naked young Ryan away, I left my office to work out, and I didn’t hear about him until later that day.

Cheryl stopped in my office around six that evening. She gets twice as beautiful every day. I couldn’t discuss the Ryan case until she and I had shared a slow, delicious fucking of Cheryl’s perfect hindquarters. Cheryl liked me to suck her toes sometimes after vigorous coitus and I would run through a wall for her. So I was ingesting her little piggies when she told me about our latest boarder.

Cheryl knew that assessment was my department, so she asked what I thought first.

I took the most beautiful small toe in the world from my lips and said, "Definitely a nancyboy!" Then I resumed my delicious task.

"Mmmmm. That’s nice," my life partner said. "You’re right again. That was an easy $5,000, but we’ll have to earn the rest, of course."

Cheryl was right. We had a lot to teach the little sissy. How to please men was my department. Walk, talk, fashion, coping, and relationships were Cheryl’s. It took time to produce an A-list sissy. And lots of cock.

She was wriggling and wiggling from the sweet torture, but told me about what she had observed with Ryan.

"I think he’ll get along fine with Lindsay and Taylor. When I left them, Taylor was sucking his cock and Lindsay was licking his butthole very nicely."

Good work, I thought, but kept sucking the pretty toes of the most beautiful woman on earth. Lindsay and Taylor were the other two sissies we had in residence at the time. They were happy to have a new sister. Such sweet girls! They deserved all the good things life would bring them.

When Lindsay arrived three months prior to Ryan, she was a nasty, brutish, creepy boy named Jack, who actually tried to punch me during our first meeting. I, of course, gave him a sound thrashing, followed by a spanking that reduced him to tears. He wouldn’t even respond to me when I rubbed the soothing cream on him, although it did make him cum. They always cum, even the hard cases like Jack. It took two weeks before he would sit on my lap naked and let me masturbate him to heart-pounding cums. Another week before he kissed me – I always let them decide when to kiss me. And another two weeks before I fucked his sissy ass. After that, of course, he was mine forever and had become the one of the girliest sissies we ever had. The tough guys always turn out that way.

When Taylor arrived two months prior to Ryan, she was the complete opposite of Lindsay. She practically jumped on me and begged me to make her a complete woman. When I first asked her to undress for me, she even skinned her foreskin back to show all her pink parts, then spread her cheeks to show me her hot, tight hole. She was the only new sissy I ever fucked the first day. I had to. She was so randy she would have asphyxiated if I didn’t. When Ryan arrived, Taylor and Lindsay were having the hottest sissy love affair I had ever seen. They were in each other’s panties practically 16 hours a day. Of course, I fucked them both at least twice each day. Which I would also do for their new playmate. Now you know why I work out so much. And abstain from alcohol. And get eight hours sleep each night. All those demands, plus the mothers and my darling Cheryl! I told you this was a tough job.

We don’t give a sissy a girl’s name or refer to her in feminine pronouns until I’ve fucked her. Which, with Ryan could happen very soon. Usually, I like to give it a week or so. Let them suck me off. Suck each other off. The sissies do not fuck each other’s pretty bottoms. That’s just for men to do for them. But that leaves a lot of other delights to explore. And they explore them.

We usually all have dinner together at 7, but it was pushed back to 7:30 on Ryan’s first night. Cheryl had ordered Chinese and Lindsay and Taylor were setting it out when I arrived in the dining room. Ryan was setting the table and seemed very happy. He had obviously had his tires thoroughly rotated, but I think he was extra happy for some other reasons. He was wearing silky white stockings, a small white skirt, a pink top and a pair of pretty, white, three-inch stiletto sandals. His face was beautifully made up and he had a big smile on his red lips. He was also flirting with me, bending over to pick up imaginary utensils he allegedly dropped and flashing his stocking tops and panties at me.

Lindsay and Taylor chatted happily. They loved Cheryl like a second mother, as our girls always have. I’ve never underestimated Cheryl’s contribution to our partnership. She’s really more valuable to full sissification than I am. I charm the mothers (and fuck their hot asses) and train the girls to love men properly. But Cheryl makes them into girls. And gives them the tools to sustain their femininity.

Lindsay told us about a date she had had with Kenny, a young man on my very short list of boys good enough to date our girls. We have no secrets and Lindsay was telling us about how Kenny made her cum three times in ten minutes by sucking her balls and licking out her pretty hole. We knew she was bragging a little to impress Ryan, but that was Lindsay. You had to love her.

Taylor was talking about school and how she was teasing poor Mr. Lowe, her biology teacher. "I just don’t get that stuff," she said, "but I told Mr. Lowe that there were some things about biology that I could teach him. He laughed at that good naturedly, but since then, I’ve been sitting in the front row and giving him a nice view of my panties, stocking tops, garters and thighs. Do you and Miss Cheryl think I should let him <blush> fuck me, Coach?’

Lindsay and Ryan also leaned forward to listen to our answer. That was an easy one. Cheryl answered. "Of course, Honey. If you want to have sex with a nice man, go ahead. It’s fun, you’re good at it, and it seems to be what you were meant to do. If it improves your grade, all the better."

Perfect answer, I thought, then added, "There’s nothing wrong with using your tongue and your bottom to get what you want. It’s what makes the world go around."

Cheryl and I just love giving our girls a firm basis in morality.

"But remember," my darling partner added, "only nice men and boys. Leave the jerks to the ‘vanilla’ girls. They seem to like that kind."

More wisdom!

We have lots of laughs and fun at our house too. Not just fucking. But the girls and Cheryl are always looking to get my pants down and my cock out. They know I don’t do group things – One girl at a time gets all my attention and all my sweet cream. So any time I’m alone with one, I’m pretty much going to end up fucking her. I didn’t want to initiate Ryan yet, so I sent him off with his new sisters to the big, king-sized bed all our sissies-in-residence have always shared. We’ve had as many as five and, for very brief periods, as few as one, and even none, in our happy home. That bed could tell some stories.

When the girls have done their homework and are ready for bed (usually around 9 p.m.), they always come by in their tiny nighties to kiss Miss Cheryl and me goodnight. I always seem to end up giving one of them a little extra good night send-off. That night, Cheryl, who was also in a very skimpy, luscious nightie, took Lindsay and Ryan off for some instruction in oral sex. You’re not born knowing how to give a world-class blowjob, you know. The instruction is very hands-on and mouth-on. Lindsay’s skills were already superb and Cheryl’s were the finest on earth. They would get and give some head-exploders that night, I was sure.

Just so I wouldn’t be lonely, I would be spending the night with Taylor. I almost always slept with my darling Cheryl, so that was a real treat for Taylor. And me.

Taylor had been taking some hormones, definitely optional in our program, and her titties were just budding. I love that stage of titty birth! The nipples are hyper-sensitive and the girl loves whatever you do to them. I decided that I would focus on her sweet titty bumps that night and make her scream and beg for every bit of titty love I could muster. And every drop of my manly goo.

I like to leave the girl’s lingerie on during sex, but prefer to be naked myself. I love feeling their cool silk and warm flesh against me. Taylor was in white that night, including long, silky stockings that showed her pink toenails through the filmy teasers. The naughty girl had omitted her panties and I could see her fine pricklet poking out from under the hem of her fluffy nightie. I am the luckiest man on earth! I stripped to the hairy buff and Taylor wanted to swallow my meat right away. Young people can be so impatient. I picked her up and carried her to my bed, kissing her lips as I transported her.

Her lovely young breasts were heaving as I laid her on her back on the bed and kissed her mouth. I caressed her thighs, her knees, and her calves. Then I lifted her pretty nightie and caressed her soft, down-covered tummy, kissing her passionately all the while with lips and tongue. By the time I had lifted her nightie from her puffy nipples, Taylor was frantic with sissy passion. She knew I was going to torment her senses and she was eager for the ordeal.

I lightly brushed Taylor’s left nipple with the tips of my fingers. Taylor arched her back and, her little cocklet, yet untouched, exploded thick, rich cum globbies. Wow! She was ready!

Pressing my advantage, I kissed her left nipple lightly, giving it tiny licks throughout her blaster of an orgasm. Then I slathered some of her girlish cum on my fingers and licked it off, sighing deeply at the rich taste of my favorite nourishment. But I didn’t lap up all her cum. Some I applied to each of her nipples with my fingers, then teased the ultra-sensitive points with my cummy fingertips. Taylor whimpered and sobbed in sweet agony. After several minutes of this delicious torment, I began to kiss her right nipple as I stroked her tender young foreskin up and down. Up and down. I can be naughty too and I wanted to warm my sweet girl up, making her cum and cum some more without the use of my overworked cock.

I got my wish. And so did Taylor. Nipple kissing, with simultaneous prickie tickling can only lead to some cums to put down in your scrapbook. Taylor was quivering, then squealing in intense orgasm before I could even get to the other nipple. I corrected that, of course, giving the other my full attention and bringing her to a third visit to heaven.

"Oh, Coach!" Taylor gasped, "I love you! I love you! Please fuck me now. PLEASE!"

I guessed she was ready.

Taylor has one of the best sissy asses we have ever had in our happy home. It’s plump and pink and her rosy hole almost drools in welcome to her male friends.

Her wrinkled hole was so pretty that I had to kiss it. And lick it, as I tickled her balls with one hand and skinned her prickie with the other.

Taylor is very anal. In a good way. A cock attached to a nice man is always welcome in her hole. Sometimes I looked at Taylor and cried. She was so suited for the wonderful sissy life. She would be so happy and would make those around her even happier.

That night, it was my turn. The little sweetie was squealing in sissy rapture as I brought her to yet another cum-blaster. As she was spasming, I stuffed her pooper with a big piece of Coach meat.

Oh, it was good. Taylor was beautiful, hot and very enthusiastic. She got all the cock she could handle that night and we slept the sleep of those with clear consciences and empty ball bags.

The next morning, I dreamed that an angel was sucking my cock. I awoke and discovered it was true. Under Cheryl’s careful direction and Lindsay and Taylor’s rapt attention, Ryan was sucking his first male organ. And it was superb.

I really enjoyed it. Cheryl had taught the new sissy well and I smiled at Cheryl to show my admiration. She smiled and nodded back.

Ryan was in his nightie, but still looked more like a boy than a girl. Transitions take skill, time and practice. I vowed to give the new sissy lots of cocksucking practice. He was getting better by the second. I encouraged him with smiles and compliments and his eyes smiled back at me.

I felt the rumbles and told the boy that I was going to gush a big load into his wet mouth. "I want you to swallow it all. Just don’t panic and swallow a little at a time. You’ll be fine. You’re VERY good at it. Oh, I think that was….OH!!"

As advertised, I blew big gushes at the sweet sissy. He almost panicked and gagged just a little, but I talked him through it and he recovered very well. It was a very intense load. I was very proud of Ryan and Cheryl when Ryan opened his mouth to show me that the cum had melted in his mouth, not in his hands.

I drew him to me and kissed him as Cheryl and his new sisters applauded. Maybe I wouldn’t wait a week before I gave Ryan a buttful of what he needed most.

 

Chapter Five – Ryan Becomes Sally

Ryan was such a nice sissy. Why should I deny him full sissiehood? Especially since, when he kissed me goodbye as Cheryl was taking him to register in school, he asked me if there was anything special he would want me to bring him home from school. I stroked his ass and said, "I think it’s attached to you, Sweetie. And I’m sure it’s special."

Ryan kissed me with lots of tongue, then toddled off with Cheryl, Lindsay and Taylor to school.

Our girls are always reluctant at first to enroll in school as girls. They know how cruel their peers can be. But it’s well known at our high school that anyone who messes with the sweetest sissies alive has to answer to me. Or even worse, to Cheryl. As a result, the kids who would harass our girls leave them alone and the ones who spend three hours a day wanking themselves thinking about one or more of the girls feel free to worship them, either from afar or up close and personal.

That morning, I was grateful to see them all go. I love having a few minutes to myself now and then and my ballbag was on E.

I read the paper leisurely and had three cups of coffee. Then I decided that I would take a shower and get things done. I stripped and got into our big shower, letting the warm water relax me. I lathered my hair and my eyes were covered with soap when I felt a soft hand on my cock and balls. I knew that touch anywhere. Cheryl was back and had joined me in the shower. I kissed her, rubbing my soapy hands on her perfect nipples. She gasped and dripped goo from her thick, stiff clitty. The naughty girl said, "My bottom feels so lonely. Can you help?"

I believed I could. I soaped my fingers and used them to loosen and lube my darling’s love tunnel. Cheryl truly loves sex and it’s such a delight to please her.

I was hard and randy and entered my favorite spot with eagerness and love. Cheryl never tires of my cock and I never tire of giving it to her. I fucked her beautifully, skinning her pricklet to two cataclysmic blasts, then gave her one of my own. Did I mention that I’m the luckiest guy in the world?

As we dressed, sneaking little kisses as we did so, we discussed business. "How did Ryan do at school?" I asked.

We, of course, registered him as "Sally," the sissy name his mother had given us. After I punctured his pooper, he would be she and Sally forever. But schools don’t understand such things.

"He was a little scared, like they all are, Coach. But those lusty looks from boys, male teachers, and even the principal, were good for his morale. I think he’ll have more cock than he can ever handle. Carefully regulated by us, of course."

Of course. We take care of our girls. "He looked very hot this morning. I’ll say he gets asked out three times today."

Cheryl giggled. "I say four. If I win, you’re my love slave for 24 hours."

"I’ve been your love slave for 12 years," I said. Then I proved it.

When the girls came home from school, it was clear that everyone expected me to initiate Ryan. As a benevolent dictator, I serve my people’s needs and wants. I hadn’t cum in almost four hours, so I was ready to give our new sissy what he needed most. Hot cock injections.

Ryan looked at me sheepishly as Cheryl, Lindsay and Taylor disappeared. He was a little scared, even though the other ladies described my fucking as heavenly. Which I’m sure it is.

The sweetie was in his light, daytime make-up and school clothes, four-inch heels, tiny miniskirt, tight blouse, and black, silky stockings. He looked completely porkable!

I took him to the small bedroom adjoining my office and asked him to strip to his panties, stockings and garter belt. He did so with a lot of teasing and nervous giggling. Oh, he looked good!

I stripped naked and contemplated what was about to happen. I do love the virginal sissies. And the ones who have had their sissy bottoms fucked a thousand times. I love sissies!

Ryan sissied over to me and sat on my lap. He kissed me lovingly and we darted tongues. When the little darling rubbed his pantied bottom against my big, manly package, I wanted him very badly. We kissed and fondled each other for some time. Then I lovingly carried him to the bed and laid him on his back. I smothered his body in kisses until he was wiggling and squealing with pleasure and spurting his sissy cream.

Then it was time for Ryan to lose his bothersome virginity. No matter how gentle I am and how much lube I use, it always hurts a little. I’m just too big for those tight, little holes.

But that day, Ryan was ready. I licked his pretty pucker for quite a while, making him cum and cum, almost draining him of his delicious goo. When I thought he was ready, I cranked Ryan’s legs back, put them on my shoulders, and, knowing that faster is better, pushed past Ryan’s defenses and began to fuck Sally. Sally howled in pleasure and pain. She screamed with the pain of rebirth and the pleasure of what sissies adore – men’s cocks in their sweet bottoms.

She was an erotic treasure. Eager to please and completely enraptured by my loving attentions. The little sweetheart grunted and gurgled. Somehow, she still managed to repeat, "Fuck me, Coach. I love you, Coach! Fuck me!"

I was half in love with Sally myself. She was a fantastic piece of ass and made cum like a sperm factory. Her arms were wrapped around me and she was stretching her lips to kiss me. I leaned forward and as our lips met, I felt the first warning sign. Sally licked my lips and I felt the second sign. When she whimpered, licked my tongue and made another astounding cum, my whole body convulsed and I blew a gutful of manly cream into the sweet, tight passage.

We came together. Sweaty, spurting, trembling, bathed in cum. Loving each other. Adoring the feelings we brought out in each other. Sally was a girlish treasure. What a waste it would have been for her to remain Ryan.

As Sally’s anal muscles rejected my softening cock, Sally eyed it like the little sexual predator she was becoming. My manly muscle was limp and soaked with cum and anal juices, but Sally took into her mouth and sucked it as if it were a Bit-O’-Honey. She tickled my balls as she was fellating me in exquisite fashion and in record time, I was stiff and ready to stuff once again.

As I spooned behind Sally, she turned her head for a sweet kiss. Then she gasped with 100% pleasure this time as I stuffed her love hole. It was fantastic – without the tension of the first go, Sally was able to feel every protoplasmic cell I entered her with. She came three more times. Where was it all being manufactured? Although the last was a watery trickle and she didn’t even get hard. But it still knocked her into a semi-coma.

I gave an excellent accounting of myself and concluded with a spectacular, spermy spurt.

That about did Sally in (thank goodness). And we kissed and hugged until it was time for Sally to get the smell of sex off her before dinner. If she didn’t, the others would all want to fuck and I’d never eat. A man has to keep his strength up so he can work, you know.

When I re-introduced my new love partner to everyone as Sally, they all congratulated her sweetly. Then asked her for details. Cheryl, Lindsay and Taylor are such girls!

During dinner, Taylor announced that she would be welcoming Mr. Lowe to her sweet pussy the next day. "He said he wants to keep me after school tomorrow because I’m going to be naughty."

We all laughed. Cheryl said, don’t forget to put the K-Y lubricant in your little, heart-shaped sissy purse. Men in heat forget things, you know."

Wise advice. And very true.

 

Chapter Six – The Pinch Hitter

After dinner, I took Lindsay in my office bedroom and fucked her royally. An hour later, I did the same for Taylor. Then all three of my little sissies kissed Cheryl and me and went off to their big king-sized bed to spurt sissy cream all over each other.

Cheryl and I lay in bed cuddling and reviewing our days. She said, "It’s hard on you when we have three sissies in residence, isn’t it?"

She knew me so well. I stroked her fat, pink cock as I said, "It is, Sweetheart. But it’s my job and they need lots of cock if they‘re going to be properly sissified. I only feel bad about it when I think I’m neglecting you."

Cheryl is such a doll. She kissed me and said, "We can always bring Brad in."

Good idea. Brad is a young man who helps me out now and then when we’re crowded or Cheryl and I want to take a vacation or something. He’s the nicest young man and the brother of Elise and Jill, two of my all-time favorite sissy girls. They’re in their 20’s now and happily married. Brad has been sort of a part-timer for us for about nine years now. He has a really big cock, he adores sissies and they swoon for him. Not as much as they love me, of course, but some.

I’ll admit though that I’m reluctant to call Brad because a) we have to pay him a "sissy consulting fee, although the only real consulting occurs when he asks the girls whether they want his cock in their mouths or their sissy bottoms and b) I’m jealous when someone else fucks my girls, even when it’s Brad. There’s no reason to be, I know. The girls still worship me, I know. But I’m 44 and I could see a time when Brad would be the primary cock giver and I would be his backup.

"OK, Cheryl," I said, "I’ll call Brad tomorrow. But I can still bring it, you know. I’m not getting old."

Cheryl giggled. "I know that, Coach. I just don’t want to see you overworked. And I want more of this big cock in my pooper."

With that said, she straddled my hips and sat on my rammer, shoving it inside herself to our mutual delights.

 

Chapter Seven – Pro Bono

As Cheryl took me to a better place, I remembered the last time we had a sissy drought instead of overbooking. That was a scary thought. It was eight years ago. We had just graduated three tender lovelies and the house was for just Cheryl and me for the first time since we had begun our business. We took two weeks in Aruba, checking our messages frequently to see if any mothers had called. All business is cyclical and that was a down cycle. Two weeks after our vacation, we had no takers, despite Cheryl’s intense marketing efforts.

During that period, Cheryl was gone more than usual and I had hours on end some times with a full ball bag. Sometimes I would look at the pictures of some of our graduates and <gasp> wank my willie as I remembered the good times.

Would I have met Ginny if things were busier then? Probably not.

Ginny was my only "pro bono" project. And the only one I volunteered for, rather than being approached by a parent.

One afternoon during the "big drought" period, I really noticed our paperboy Alex for the first time. I had always said hello to him and paid him and everything, but Alex had always been in the background. When I noticed him, I saw someone who would make a very pretty girl. And he had some sissy characteristics that made him a borderline sissy at least.

It was wrong. It was unprofessional. But I was horny and my ego needed a boost. I invited Alex in while I looked for his money. I paid him then asked if he would like a cold drink before moving on. "But not if it holds you up on your route," I said.

Alex smiled. It was a beautiful smile. "Oh no, Mr. McDonald. You’re the last house on my route."

"Call me Coach," I smiled back, then watched as he drank his Coke.

I drew a breath and took the leap. "What color are your panties, Alex?"

Alex paled. He looked at me, wanting to claim that he didn’t understand the question. But one look at me told Alex that deception was futile.

Alex trembled very badly, then said, "Blue."

I sat in my easy chair, looked into his pretty eyes and said, "Let me see them."

The poor little sissy began to vibrate. But he lowered his trousers just low enough to let me see the blue.

I sat back, completely relaxed and confident now. "Take off everything except the panties and sit on my lap."

The lad was furiously excited. And completely terrified. But he did as I said.

Alex had a beautiful body, with creamy skin, a pretty little cock pushing mightily against his lacy blue panties, and painted, pink toenails.

When he sat on my lap, I circled him in my arms and told him I understood everything. He began to sob, so I kissed his neck and cheeks, reassuring him of his value as a person and telling him about the kind of life he could lead with my help.

He kissed my mouth and I slipped him my tongue. He returned the favor with his delicious licker and when I reached into his panties to cuddle and fondle his pretty little jewel, he shuddered, gasped, squealed loudly and ejaculated a quart of hot, sissy sperm. .

I licked his thick cream off my fingers. It was very tasty! And watching me lick and swallow it made Alex thick and hard all over again.

I drooled when I saw that pink little treasure. I kissed him deeply and asked him to stand in front of me. Then I began to lick his darling balls with slow, wet laps. He squealed in sissy ecstasy, then blew four thick, sticky ropes, just from me licking his tee tees.

I gave him no respite, licking his hot, throbbing shaft and kissing his pink mushroom until he was hard and moaning once again. Then I began an agonizing oral assault on his penile nerve endings. He whimpered and sobbed that he loved me, then gave me the greatest present in the world – a gallon of hot sissy juice, right down my eager throat.

My own throbber was quite stiff and aching by this time and my little virgin was in a furious dither to pay me back. He sank to his knees and helped me pull off my pants and boxers. Alex kissed the tip of my cock, then giggled when a big spurt of appetizer jumped out at his lips. I was very excited. Alex took all of me that he could inside his eager mouth and sucked and licked with passion and natural skill.

I encouraged him with endearing words and little hints on proper cocksucking. He was an apt pupil and after five or six minutes, I moaned with joy and released all the previous, frustrating weeks’ tensions into Alex’s lovely, sissy mouth. The beauty gobbled down my cum and kissed my cock and fondled my balls until I was stiff enough to penetrate iron. Then he begged to be fucked. Unprofessional as it was, I granted his request. I lubricated him with K-Y, making him gasp and pant as my fingers massaged his tender prostate, then capping his cocklet with my mouth as the anal torture drew a spermstorm from him. I swallowed the creamy nectar, then mounted him, pushing my thick business asset all the way into his love hole, ignoring his screams until they became squeals of rapture. The poor, over-stimulated darling came twice more as I fucked him, not getting hard either time, but almost fainting from the force of his feelings. When I blasted my hot, sticky load into the greatest place on earth, Alex was gone and Ginny was mine forever.

I hugged Ginny and kissed her perky nipples. Miraculously, she came again, drooling watery goo from a completely limp, but gorgeous clitty. Gasping, panting, Ginny said, "I love you, Coach. Nothing in my life has ever been half as good as what we just did."

"I love you too, Sweetie. And I’m going to make sure that you get what you need to make you happy." Then we kissed some more, she sucked me off in a fond farewell, and left.

I trained Ginny unbeknownst to his parents, over Cheryl’s very sensible objections, which was the only substantive disagreement we ever had. She was worried about the repercussions if Ginny’s parents found out. She was right of course, but like all men, I was thinking with my cock.

Cheryl eventually knew I wouldn’t back down, so she helped me by giving Ginny a full program of sissy instruction whenever Ginny could get to the house and I wasn’t fucking her. Rare moments indeed. I was hooked on that girl!

Of course, soon after, we were back to capacity again and I had to bring in Brad. I wasn’t giving Ginny up, however and still haven’t. She’s 21 now, living on her own full-time as a girl and very happy. She has around five adoring boyfriends, all of whom have proposed to her, and she may accept one some day. Meanwhile, Ginny’s parents are delighted with her transition and her happiness, but they still don’t know about me. Or so I believe.

I spend one weekend a month with Ginny at her place and I look forward to it greatly. Brad fills in for me, even with Cheryl, which makes me jealous, but I am sort of cheating on Cheryl with Ginny, I guess. Cheryl acts a little pissy right before I go each month and then lays it on very thickly about what a dreamy weekend she and the girls had with Brad. But I guess I deserve it. I don’t care. I want my cock in Ginny’s sweet pussy.

 

Chapter Eight – Teacher’s Rights

The next day, Brad arrived at 7 a.m. and gave Taylor, then Lindsay a good shagging as I got Sally’s day started off right. Then I introduced Sally to Brad. She batted her eyes at him and they ended up in a knock-down-drag-out fuck that almost made Sally late for school and sent her off with a squishy butt and cum dripping down her thighs. She came by and kissed me and told me she loved me, so I knew I was still the Man.

Brad’s assistance left me with plenty for Cheryl, so I gave her two good tosses, one in the morning and a taste of afternoon delight.

Lindsay and Sally got home on time, but, as she had warned us, Taylor was staying after school with Mr. Lowe and being naughty.

I made love to Lindsay, then Sally before dinner, feeling a lot less pressure now that Brad was around. He would be joining us for dinner, then taking Lindsay and Sally to heaven when their homework was finished. I was going to make Taylor happy before bedtime.

Taylor showed up at five minutes before seven and barely had time to clean up before we sat down to share tacos. She had the look of a thoroughly fucked sissy and we were all eager to hear about it. Sally was sitting next to Brad and giving him a very nice handjob as Taylor told us about Mr. Lowe’s biology lesson.

"He was so nervous," she began, "about some silly rule against teachers fucking students. I mean, who makes these rules?"

Good point. It was ridiculous. Students want to fuck their teachers and vice versa. Why fight it? Teachers are paid so little. If we want to get good teachers, we need to let them fuck their students. Simple economics.

Taylor continued. "He was like some little boy or something. I figured I would have to take action if I wanted to get my pooper porked. We were in a basement room that no one knew about. There were a couple of desks and some chairs. I got up on a desk, lay on my back, shimmied down my panties and said, "See anything you like, Mr. Lowe?

"Mr. Lowe’s eyes got wide and his bulge grew. My legs were spread and my pink package was there for his admiration. I made sure that he could see my bottomhole too. It all looks better framed by black stockings, doesn’t it? Thanks for the tip, Miss Cheryl.

"I don’t know if Mr. Lowe was expecting to see one of those hairy, pussy things, but if he was, he recovered nicely.

"He pulled down his pants and stepped out of them. We girls have it so much easier. We just lift our skirts and voila! When we’re done, we flip our skirts down. Nobody knows if we have panties on or not. Anyway, Mr. Lowe sat me up and began to kiss me very sweetly, then very hotly. He’s a good kisser. With his left hand, he reached under my blouse and rubbed my right breast. I’m just beyond an A-cup now and growing, you know.

Taylor smiled teasingly at me, then at Brad, whose pecker was about to explode from Sally’s adoring manual attentions.

"Then he grabbed his big, hard cock and, as he was kissing me, rubbed its drooling head against my little mushroom. Mixing our juices. Kissing. Stroking my sensitive little nipples. It was so dirty and exciting that I felt those little rumbles, then the big roar and, squealing like the sissy I’ll always be, I began to spurt my cream all over Mr. Lowe’s cock. It was heavenly!"

Brad groaned at that point and doused Sally’s hand with his thick, rich goo, which, I of course have never tasted and never will. Because I’m not gay.

Everyone giggled and Taylor continued.

"Mr. Lowe was very excited, but he seemed to calm down at that point and start acting like a dominant man, instead of some guy seduced by a sissy. I like when men dominate me. Especially when they’re big and just a little rough and forceful."

The girls all nodded in agreement, except for Sally, who had locked eyes with me and was slowly licking Brad’s cum from her palm and each finger. She was also batting her big, liquid, lined, mascaraed, shadowed eyes at me. I love my job!

"When Mr. Lowe took over, I became what I like being best – the helpless little girl, whose man is about to fuck her and make her his little sex toy. All of us sissies want that and I was getting it this afternoon. I’m not sure whether Mr. Lowe had ever had anal sex before, but he knew he couldn’t just stick it in me. He wetted two fingers with saliva and eased them into my tight hole. I moaned and whimpered with encouragement as he slid them in and out, kissing me and praising my beauty. It was very nice. He wasn’t aiming for it, I don’t think, but every now and then he clipped my prostate, and that was extra-special. I squealed every time he did it, but I’m not sure he made the connection. He was pretty sexed up. I groaned out to him to look in my sissyish purse and he did, finding the K-Y, thank you, Miss Cheryl."

Cheryl smiled at Taylor. Where was Brad? Oh. He was on his knees under the table sucking Sally’s pretty cock in return for the favors just received. We are very fair-minded in our little family. Long erotic tales tend to bring out our passions. Oh, my. Lindsay had slid under the table too and was extracting my tosser so that I would enjoy Taylor’s story more. I felt her warm, wet mouth on my big boy and settled in to really listen.

Taylor continued. "Well, Mr. Lowe, oh, Miss Cheryl, it’s so nice of you to suck my clitty like that. You’re the best auntie a girl ever had. Ohhh. Mr. Lowe put some lube on three fingers that time and I was ready for a telephone pole by the time he withdrew the fingers and lubed his cock. I lay on the desk and he stood between my legs. I begged him to fuck me. ‘I need it really badly,’ I said. Men love to hear that, but it was true. He slid in me easily and fucked me gloriously. You should try Mr. Lowe, Lindsay and Sally. Oh, Miss Cheryl. That’s so nice. Anyway, I was really the helpless little girl, since Mr. Lowe was off in Fuckland, pounding me so hard and hot that the principal, his mother and his pastor could have walked in and he wouldn’t have noticed. It was excellent! I felt my tingles in my tummy, then bigger warnings. I whimpered, then squealed, then screamed when I came, which ignited Mr. Lowe and made him give me as big a load of manly goo as I ever remember. It’s still oozing out of my butt now, but I think I have to stop this story, because Miss Cheryl, I …Oh….SQUEALLLLLLLLLLLL!!!!"

Taylor climaxed, which set me off, dousing Lindsay’s pretty face with man cream, which set Sally off, making her squeal almost as loudly as Taylor had.

What a bunch we were.

We cleaned up and sent the girls off to do their homework, a prerequisite for further fun.

At bedtime, Sally came by in the prettiest little purple nightie, so naturally I had to fuck her to three screaming cums. Brad slept in my office bed and took care of the girls in sequence, finally sleeping with Lindsay as Taylor and Sally cuddled in their room and I gave Cheryl proof that I could still work all day and love her all night.

 

Chapter Nine – Dating and Interviews

Dating is inevitable for our girls. They love Cheryl and me dearly (and probably Brad-the-cum-machine too), but young people want to exchange slippery cream with people their own age.

Lindsay had been having a pretty regular Friday and/or Saturday night thing (no dating on school nights) with Kenny. Poor Kenny was helplessly in love with her and must have spent hours each Lindsay-less day wanking himself as he dreamed of their dates.

Taylor began dating a little later than Lindsay. She claimed to prefer men, but I think she preferred anyone who has a cock and treats her right. She was dating three different boys and driving them all half mad with desire for her.

That’s another difficult part of my job. I have to interview all the boys who want to date our girls and make sure they’re suitable. Not many are, believe me, and they don’t always take rejection well.

During Sally’s third week with us, she told Cheryl that she liked a boy named Mike and he had asked her to go with him to a movie. Cheryl informed me, then she set up an interview for me with Mike.

Mike was very nervous and worried when he came in. I like that. I don’t want these guys to be cocky. They’re the ones who will hurt the girls or break their hearts.

"Mike," I said, "Tell me about yourself."

Mike said, "I really like Sally, Coach. She’s funny and beautiful and smart and really cute."

A good sign. He liked talking about Sally more than himself. I pressed on. "That’s very nice, but what about you?"

Mike’s nervousness eased a bit. "I like school and do very well. I love my parents and even my brother and sister. I play football and the clarinet and I want to be an architect some day. And I really like Sally, Coach."

Hmmm. The boy had obviously spilled a lot of seed thinking about Sally. "You do know that Sally has a cock and balls just like you."

"Sure, Coach. Everyone at school knows that. That makes her ten times more exciting."

"And do you want to suck that cock and lick those balls until Sally spews her sissy cream all over your face?"

Mike gulped and said, "Of course, Coach. Who wouldn’t?"

Good answer. "And do you want her to suck your cock in those pretty lips of hers until you cum, moaning and gasping, down her throat?"

Mike’s trousers bulged at the thought. He gasped out, "Very much, sir."

"Have you ever fucked a sissy’s sweet bottom, Mike?"

That made Mike’s drawers even more crowded. "No, sir," he admitted.

"Then take those trousers off and we’ll discuss it."

Mike hesitated half a beat, then, desperate to fuck my darling Sally no matter what the cost, he made himself naked from the waist down. He was a beautiful young boy of around 16, with a fine, fat cock and darling legs. "Now the rest of the clothes," I said.

He did so and stood before me, a naked young Adonis. I know, you’re thinking, "This Coach guy is gay!" Well you’re wrong. I just appreciate beauty and Mike had it. Plus, I needed to show him I was in charge so he treated Sally right. And I wanted to show him some nice technique. And, I thought he was cute. Oh, I’m sorry. Was that last one out loud?

I looked him over carefully. He was afraid, but his cock was rigid against his belly. I touched it. He jumped a little, but when I began to massage it expertly, he leaned into my hand.

"It’s different teasing someone else’s cock. Note my technique."

My technique had him panting and gasping for breath.

I handled his balls with my other hand, talking to him about how Sally’s pleasure was more important than his own. His own at that moment was quite evident and as I stroked and spoke about Sally and him making love, he whimpered a little and tried to warn me, but launched huge globs of his boyish cream into the air. I milked his balls, draining them exquisitely. Then I began to lecture him on anal matters and how to take Sally to paradise through the rear entrance. I lubed my finger as I spoke, then entered him. My fingers were clearly his pretty little bottom’s first visitors. I found him deliciously tight and his pole rose to its former splendor. When I spoke to him of the delights of the prostate and began to massage his, he cried out and came again, harder than the first time and with a moist look akin to love in his eyes.

Well, we weren’t having any of that nonsense. This was merely instructional on Sally’s behalf. And if he enjoyed it, well, that was a bonus. Still I wasn’t sure if he were right for Sally. Then I was.

"May I give you a little relief, Coach? You seem a bit excited."

That was a tiny bit cheeky, but truth is always a defense against slander and my trousers were severely tented. I guess maybe I was thinking about one of my girls or something. Certainly not of Mike. Because I’m not gay. Did I mention that?

I pulled my pants down and Mike gasped when he saw my big prong. He skinned it up and down very sweetly. Thank goodness he didn’t try to kiss me or anything. I mean as practice for Sally. Which was why we were there. Instructions. Practice. Cumming hard into Mike’s warm, boyish hand. Oh, Mama, that was good! In a strictly professional way.

We cleaned up and put our pants back on. I told Mike he had passed the screening and could show up at 6:30 on Saturday, in a coat and tie, with flowers for Sally. They could have dinner with us, then retire to Sally’s room for some fun. But he had to leave by eleven, as Sally needed her sleep. [And the rest of us needed details].

Mike was overcome with joy and I hustled him out of there before something embarrassing for both of us happened. Wouldn’t want that.

I told Sally the good news that evening, just as I was entering her tight hole with my cock. She spilled her sperm instantly from joy and gave me the fuck of her life in gratitude. I love my job.

 

Chapter Ten -- Mike’s Lucky Night

The word got out at school, I understand, about Mike’s upcoming date with Sally, and all the guys were jealously teasing Mike about not doing anything they wouldn’t do. Then they would go home, I was sure, and whack their weenies raw thinking about what a date with Sally would be like.

Sally was in a wonderful mood that day. I fucked her before breakfast and Brad took her to wonderful places right after breakfast. Sally’s Mom came by for a visit and an update on Sally’s progress. I was true to my word and gave Mrs. Willis the fucking of her life. It was a real pleasure because she had taken the time to make herself attractive and had lost at least five pounds. I was wondering if Mr. Willis had noticed. Just another little perk from the McDonald-Peters Sissification Institute. I gave Mrs. Willis an excellent report on her Sally and they began the process of bonding as mother and daughter.

Tough love and lots of cock win again. Maybe I should put that on a logo or our business cards.

Sally spent about three hours getting ready for her date and wouldn’t even let anyone give her an orgasm after noon. It was dangerous to leave sperm in a sissy that long, but Sally knew her own mind. She wanted to be frantically randy for her date. How many women would do that?

Mike arrived exactly on time, dressed as ordered and carrying lovely flowers for Sally. She looked delicious in her pretty pink mini, white top, tan stockings and pink, four-inch stiletto sandals. Her hair had gotten long enough to wear a ribbon.

Sally kissed Mike sweetly, on the mouth, in thanks for the flowers. That’s why I told him to bring them. It was the first time Sally had kissed a boy and she and Mike were already half in love.

We had a nice healthy dinner of Kentucky Fried Chicken (original, of course) and all the fixin’s. As you may have guessed, cooking was not something we wasted much time on. And when you’re fucking eight or nine times a day, calories melt away.

Conversation was lively at dinner as always, but everyone tried to make Mike feel welcome. Lindsay may have tried a little too hard, by running her stockinged toe up his leg until Sally made a nice interception by sitting between them. Taylor and Lindsay’s dates wouldn’t be along until 7:45, so naturally, Lindsay was horny.

Sally and Mike helped with the dishes and excused themselves before the other dates arrived. Brad had the night off, so Cheryl and I enjoyed the delights of the empty nest until Lindsay and Taylor returned with their dates around nine thirty. Lindsay and Kenny used my office bedroom, Taylor and Greg used the guest bedroom and Sally and Mike were still making squeals and bumping noises in the big sissy bedroom upstairs.

At eleven, the boys left, kissing their girls with gratitude and hopes of future love.

We all gathered in the sissy room for a complete debriefing. The ladies were in nighties and stockings. I was in the original me. Cheryl sucked my cock, to show a bit of ownership I imagine, as Sally told us about her date.

"Mike was like, so nervous. But so was I, you know?"

Cheryl stopped sucking and said, "Sally. Speak as if you have a brain. You are not a valley girl." Then she recapped my throbbing prick. Mmmmm.

"Yes, Miss Cheryl. Mike was even nervous about getting undressed, so I asked him to undress me first. He took his time, kissing my neck and telling me I’m beautiful."

Taylor and Lindsay, who were absently fondling each other’s doodles, said, "Ooooooo." That’s what sissy girls want from men. Patience and attention.

"When he had my blouse and skirt off, he was nearly overcome with passion. He pulled his tie and jacket off, then his shirt and pants, followed by shoes and socks and I had my first totally naked boy."

I knew what Mike’s naked body looked like. I pictured it in my mind and, coincidentally, I came very hard into Cheryl’s sweet mouth. That Sally could tell a story all right. Cheryl chuckled a little at the timing, but I’m sure she knew it was just a coincidence.

Sally continued. "I lay on the bed in my stockings, heels, panties, bra and garter belt and Mike got on top of me. He was kissing me very sweetly with his mouth and tongue and I liked him on top of me like that. Then he unhooked my bra. I was embarrassed because I’m the poor relation on titties in this house. But Mike didn’t mind one bit. He kissed and darned near worshiped then for a long time. As he was doing that, he reached in my panties and pulled out my sore, rigid clitty. I hadn’t made sissy cream in HOURS and my clitty was very needy. I asked if he would kiss me ‘down there’ and he almost elbowed me in his haste to kiss and suck my little girl. Men are funny that way, aren’t they?"

We were all listening, but Taylor was sucking Cheryl’s doodle and I had a mouthful of Lindsay, who spoke for all of us, by saying, "Ohhhhhhhhhhhh."

Sally said, "Well, I was so hot that a couple of kisses on my clitty head and some very nice ball sucking by young Mike and my goo was flying. He was in heaven, watching it spurt. And I needed that one. I felt like a sissy again. When we’re unmilked, all that boyish juice attacks our femininity, right Miss Cheryl?"

"Aaaaaaaaaaaaaahhhhhhhh," Cheryl said, and doused Taylor with her sticky cream.

Sally said, "We just had the most fun after that. I sucked him three times. His cum is delicious. And he was still able to fuck my sissy ass twice. His balls almost exploded when he came in my bottom the first time. He’s a natural sissy lover. And you trained him, Coach. Thank you, so much!"

Lindsay exploded into my mouth just as Sally finished her story. Sally waited until I had lapped up all of Lindsay’s precious juice and had kissed Lindsay lovingly. Then Sally got on all fours and waved her gorgeous bottom at me. What could I do? I fucked her. She squealed and screamed and came twice. What messy sheets. And we do our own laundry.

We all kissed and hugged and Cheryl and I went to bed. The girls were at it for some time, I believe, but that’s to be expected from pretty babes with adolescent boys’ sex drives.

 

Chapter Eleven – Employment Opportunities

That takes us up to last night. I don’t know what the future will be like, but I feel really good about Lindsay, Sally and Taylor. Soon, they’ll be well-equipped for independent, useful, happy, sissy lives. Cheryl and I will always be their friends and confidants.

Cheryl and I love each other deeply and I know that deep down she doesn’t really mind my weekends with Ginny. I’m just following up on a pro bono project, right?

How much longer can I do this? Good question. Fucking eight or nine times a day may get more difficult when I hit my 50s. But Viagra has kept Hugh Hefner going well into his seventies.

I’m not sure how much longer I can count on Brad. Sometimes he talks about moving to the other coast and maybe starting up his own sissification institute. He’s a nice young man, and a great sissy lover, but I don’t know if he has the charisma you need for this profession. And he doesn’t have Cheryl.

If he moves out, which seems inevitable, would you be interested in filling in for Brad when we get busy? I mean, he probably makes $30,000 to $40,000 per year and it’s all nights and weekends, except when Cheryl and I take vacation. So you wouldn’t have to give up your day job. Let me know, OK?

 

 

 

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