Becoming Jerry's Master

The third of three parts you may enjoy this chapter more if you've read the first two parts.

Jerry was a mess. Some of the cum he was supposed to be licking up was on his chin and lips. His bra was around his waist. His panties and slip on the floor by his feet.

"Straighten yourself up, Jerry. You look a mess!" You chide him as you fetch a towel from the "powder room" off the kitchen. You towel the sweat from your body and run your fingers through your hair as you go to find your clothes. When you return to the kitchen Jerry has straightened himself up and looks absolutely silly. You smile. "You were wonderful, Jerry! It was really great for me. Was it good for you?

Jerry dropped his eyes to avoid yours. He was blushing. He was unsure if he wanted to tell you just how good it made him feel.

"You were magnificent, Jerry. Really! I mean it. Being with you is so good. I want it to be good for you too. Was it? You gently stroke his chin and look him in the eye. They were dry. He smiled.

"I've enjoyed every minute. When you're in my mouth it's almost like there is nothing else in the world. Your cock is so silky and hard and I can feel the heat. Time is meaningless; it's just my mouth and you, so perfect."

"That's just how I feel, Jerry, and next week will be even better!"

"There can't be a next week." Jerry stuns you.

"Why? What's the matter?" Your chest tightens and your stomach churns as you try to remain calm.

"I'm so sorry. I'm leaving town on business Monday and won't be back till a week from Friday. I don't want you to get mad. It's not my fault, I can't help it."

"Damn it, Jerry, you nearly gave me a heart attack. Of course, it's not your fault. And I'm not mad. But you deserve a little punishment for scaring me like that."

"What kind of punishment." There was a hint of excitement or maybe fear in Jerry's voice.

"Nothing extreme, Jerry" You assure him. "How about you go shopping on your trip and bring back some sexy stockings and a garter belt to add to your wardrobe? And some lip stick; something really bright, you have to wear your bra and panties when you go shopping too. How does that sound, Jerry, fair?"

"I think I can do that," he smiles. "You will be here in two weeks won't you?"

"Without a doubt." Jerry grins as you walk to the front door and let yourself out. The ride home was filled with questions about what to do to fill the time before your next session with Jerry. That and how to get Jerry to give up his "cherry." One of those questions might already have been answered. There was another car in your drive. It belonged to Louise. Not too unusual, Louise was best friends with your wife Katy before she decided she want a little on the side from you. All these years and she never let Katy have the least bit of a clue but once or twice a year she got what she wanted. Was this to be one of those times?

You open the side door and announce yourself, "Is everybody decent?"

"You dirty old man," Katy laughs as you give her a peck on the cheek.

"What on earth do you think we'd be doing you pervert," Louise taunts as she gives you a friendly hug and kiss. If she only knew just how perverted you'd become since your last "fling."

"Well you could have been in the middle of hemming a skirt; I wouldn't want to embarrass you."

"You wish you unrepentant letch you," Katy scolds.

"He's not that bad, is he? Louise asks in wonder knowing all the while just what I'd do to her right now if given the chance.

"You should see his collection of Playboys," Katy blurts unexpectedly, they go back to the fifties for god's sake.

"Most of them were my Dad's, Katy, you know that. Besides, you know I haven't looked at them in years." You remind her defensively.

"You still have them." Katy continues.

"I think they're harmless," Louise tries to cool things down, they're better than a husband who is out chasing skirts, don't you think?" That was surprising, coming from Louise. She winked at you when Katy wasn't looking. "Get your jacket, Kiddo; I think there's a dress out there calling my name."

"This might be a better week than I thought." You said to yourself as they drove out the drive. The rest of the day was spent thinking about how Louise was going to arrange getting into your pants. She was the one who arranged things so that she would be alone with you for a few hours. The first time she took advantage of your mother-in-law's illness. Katy was gone for the week and Louise turned out to be irresistible. The next time Katy's sister was having her second child and she asked Louise to cook you a meal or two and make sure you didn't leave the house a mess. If she only knew what the two of you cooked up in her own bed! Another time it was a tree limb brought down by a storm that needed cutting up. Or her gutters needed cleaning or a bush dug up. Through all the years they were shopping buddies, they volunteered once a month at a soup kitchen, they played tennis together. One year they were in a bowling league. If the mood struck them they would pick on you, that know-it-all female teasing that drives men nuts. And you took it because she was the best piece of ass you ever had or ever will have and so far, knock on wood, she kept the dirty little secret.

You cleaned the kitchen, put a load of towels in the washer, picked up the papers in the family room and vacuumed. You fell asleep watching a recording of your favorite team and lost track of time. "Hey, dirty old man, where are you, your wife needs help. She bought a new nightstand. It's heavy and you have to bring it in and put it together." Louise and Katy had returned.

The box wasn't all that big but it weighed sixty-five pounds. You brought it in and took it straight to the guest room. That was the only room that needed a nightstand. Katy and Louise were in the family room sorting out their other purchases. Some blouses, a skirt or two and the inevitable dresses that needed hemming. You excuse yourself and go to the garage to see if there is something to occupy your time while they have their hen fest. Half an hour later after organizing the work bench you go back in and find them having coffee at the kitchen table.

"Why do I always end up with a chore when you two go shopping?"

"It's not Katy's fault!" Louise explains. "Besides it's not every time; I was looking for an entertainment center and she saw the perfect night stand. I'll bet you can put it together in a jiffy."

"You'll need the practice." Katy adds, "Louise bought the entertainment stand and FedEx will deliver it by Friday. You can put it together Saturday morning."

"But what about work." You object half heartedly, "what if something comes up?" Something definitely was going to come up; Louise would see to that! You let them convince you that it will all work out knowing full well what was really on Louise's mind.

"If work calls you've still got Saturday after noon." Katy offers.

"But I thought you volunteered me for the garden club plant sale?"

"I did but Louise and I agree this takes precedence, her sister and brother-in-law are visiting next week and she doesn't want her house to be a mess. Besides, they usually have so many helpers they just stand around and gossip. When you two are done you can show up and help with the clean-up."

"But.."

"No arguing lazy boy, it's all planned." Katy scolds. Louise winks. You feel a woody coming on and excuse yourself.

The following weekend you leave Katy at the plant sale and head on over to "help" Louise. When you arrive there are three boxes on her garage floor. The lightest is 125 pounds. "How the hell am I supposed to carry these boxes Louise?" She is already in the garage reading the instructions. Even in a sweat shirt and jeans with her hair tied up in handkerchief she is sexy as hell.

"One piece at a time, lover boy, one piece at a time and when we're done I've got another piece you can help with." She winks again and you open up box one. After assembling the nightstand the week before you decide to follow the instructions and save as much time as possible! Working together you easily handle the larger pieces and make quick work of the project. Louise misses no opportunities to brush up against you hinting at what awaits. The assembly process proceeds quickly and as you finish placing the shelves Louise excuses herself to "get more comfortable."

When she returns she is wearing heels, stockings, garter belt, panties and a matching bra. "Like what you see, lover? Katy helped me pick these out, what do you think?"

"You look good enough to eat!" You stammer.

"I thought you'd say that," she purrs.

"Katy never wears anything like this, it's all flannel all the time with a robe and those fuzzy slippers."

"I know; you poor boy you, it's a shame. That's why I like to see you once in a while," She rubs your cock through your jeans as she purrs in your ear. Let's get you out of these right now! Her hands unbuckle your belt and slides your zipper down, your jeans fall to the floor she pulls your sweatshirt over your head. She pulls your mouth to hers and explores your mouth with her tongue. "It feels like you are glad to see me she teases as she grips your cock through your plain tightie-whities." She uses both hands to scratch your chest and pinch your nipples as she drops to her knees and pulls off your shoes and socks. Almost naked she leads you into her bedroom turns and embraces you. After a long passionate kiss the two of you fall to the bed, kissing and groping like two teenagers in the back seat of a car. Your hands search for the hooks on her bra but the silky material on her back offers no release, You roll on your back and pull her on top of you where she straddle your legs and grinds her pussy into your still trapped cock. She places her hands on your chest and pushes away kneading your tiny tits as she does.

"You are such an awesome lover, Louise, why don't we do this more often?" You pant as she works you over.

"Because Katy would start to figure it out, lover boy! Besides, I only really get into my slut mode once In a while and you're such a good learner. I wouldn't want to break in somebody new." Your hands were busy massaging her ribs and chest looking for the hooks that would free the mounds of pleasure half hidden in the cups of her bra. Suddenly you notice a ribbon between her breasts; instinctively you bite it and pull it half way down. Kissing the gap between the cups you find two firm breasts with swollen tits just begging to be adored. You work your magic from first one to the other and back.

"I told you that you learned fast! You know just what I like and you aren't in a hurry." She panted as the bra falls away. You roll her to the side and work your way down her belly as you stroked her thighs. Your cock was more that ready having had no use since you last saw Jerry. Did you save yourself on purpose? Was it a mistake? Could you control yourself? You pull her panties to one side and kiss the full beaver you find above her vulva. Louise was old school, natural, at least between her legs. She reminded you of the first pussy you ever saw. Before you learned just how sweet they were. Sweet Sally Mae, your prom date and your first fuck. A summer romance that lasted until you both left for different schools. You exchange a few letters, you knew it was over but you could never forget her.

"Get those panties off, lover. You can't eat pussy properly with those in the way. What are you thinking about, get to work." Louise knew what she wanted and wasn't bashful about keeping you on track. You slip her panties off and crawl between her wide open thighs kissing the tops of her stockings, licking her taint, nibbling on her pussy lips teasing her. Forcing her to beg for what she knew you knew she wanted. "What are you waiting for? You know what I like! Get that tongue busy a little lower. Kiss that sweet little rose bud. You know you want to."

It was almost always like this, you tease as she urges you on. You kiss all around her sensitive bud waiting for her to get impatient. "Get that tongue to work, buster, don't tease me any more, lick my ass right now get in there like you know you want to."

It was time, four or five long strokes over her hole and then a little tongue fucking. You savor the sweetness of her ass. She must put some honey in there you think again, no one else is as sweet or as clean; she even smells delicious! Your cock is still hard, wanting attention, could you control yourself. "Higher now lover, that was lovely but my pussy is getting jealous, get me ready, I want you in me!"

You gladly move up to her pussy, long slow licks from the lower reaches to her clit. Swollen up too; like a little penis it begs to be sucked. "I want you now; I need you in me, fuck me lover, fuck me now!" As you enter her sloppy pussy her legs wrap around your hips and pull you so deep inside you swear you can feel her cervix! You pull slowly out and she pulls you back in. Slowly you think, make it last. You pull almost all the way out; she pulls you back so hard you swear you heard your back crackle! Out and in, out and in, over and over, she's nearly there, you can't wait any longer. She knows. "Do it, fill me up, give me all of it. Empty your balls in my pussy lover! Do it, do it, do it! Now, do it!" she urges excitedly.

You arch your back one last time and drive your cock home without the aid of her insistent legs. Once, twice, three times you spasm. She's panting heatedly, "Give it to me lover, let it all out!" Then the throbbing takes over as cum trickles slowly out and your cock withers, exhausted you slump into her waiting arms. She kisses your forehead. "That was special, lover, as usual. If we did this every week it wouldn't be as good. Now you know what to do, clean up that mess so we can go help Katy. You never liked this part before Louise, now you almost look forward to it, she has two or three little orgasms as you clean her well fucked pussy and you get a large helping of her juices mixed with yours. Finally she taps you on the top of you head. "I think we're done, lover, let's get dressed.

Louise ended your love fest abruptly. "Nice job, lover, but it's time to go. Katy will be waiting."

With both hands grasping her hips you look up over her wild bush and complain, "Just a few more nibbles, you taste so good I don't want to quit."

"You've done your usual great job of satisfying my itch, lover, but don't ruin it now. You know I can only take so much," Reluctantly you back away from her pussy. It could be another six months or more till she needs you again.

For the next six days your thoughts alternated between your memory of fucking Louise and the prospect of fucking Jerry. If only Katy was like Louise. She was once but now she'd only give it up once in a blue moon. She was always too tired or had a headache or had just given herself a facial. In the old days she would get dressed in a sexy nightie and curl up next to you on the couch. Sometimes she would rub your crotch to get you going but for the last few years the spark was missing. You didn't go looking for Louise, she found you. Maybe Katy knew. Wouldn't that be wild? Was Louise Katy's pinch hitter? One thing was for certain, Katy didn't know about Jerry.

Saturday morning arrived and it was a beautiful day. Brilliant sunshine; not a cloud in the sky, low in the sixties but the promise of mid seventies by noon. It was almost a shame to waste indoors; this day was made for eighteen holes of golf!

As usual you arrive at Jerry's at eight am. He greets you at the door wearing his new stockings and heels and who knows what under a shear robe. His lips are a ruby red you've never seen before, his eyebrows appear to be plucked and there's a hint of foundation on his face. He takes you by both hands and whispers hoarsely "Kiss me Fred; I've been waiting two weeks for you to come back to me! Have you missed me?"

Jerry seemed to be in touch with his feminine side! Maybe today is the day he gives you his cherry. You look him straight in the eye. With a wig he wouldn't be half bad. Your lips meet, he lets you take control. You give him a little tongue. His hands find your belt buckle. "We've got to get you out of these." You let him strip you and lead you to the couch. He kneels between your legs and starts massaging your thighs. He looks into your eyes.

"Have you missed me, Fred?" He sounds needy; like a woman unsure of her man.

"I can't tell you how much." You lie just a little. You did miss him; just not as much as you should have.

He starts massaging your balls. Gently he pulls and squeezes as he licks his lips. "Have you been saving your cum for me?"

You lie again, "I haven't jacked off even once!"

"Your wife still won't let you have any?"

"She's as cold as a popsicle."

"Poor baby!" He sympathizes not knowing about Louise. His lips surround the tip of your cock and gently suck. You know he is enjoying himself. He licks, he sucks, and he nibbles. It's all about your cock. He loves it. He kisses between your balls and then sucks first one and then the other. You spread your legs and then pull your knees up to your chest. He's licking lower than ever before. "You really do have a sweet ass, Fred. Does this feel good?"

"You know it, Jerry; I can't explain how great that feels."

He kisses your balls and licks your shaft. "Do you still want to fuck me, Fred, or should I just suck you off like before?"

"Do I want to fuck you Jerry?" You pant. "I want to bury my cock in your tight pussy. I want to fill your pussy with lots of cum. I want you to know what it's like to be a woman!"

"Show me what it's like, Fred, kiss my tits, suck my tits, and make me feel you're your woman." He joins you on the couch, you kiss his neck, his shoulders and finally suck one of his tits into you mouth.

"That's it Fred, suck my tit. It feels so good. Suck my tits and rub my clit!"

You know what he wants, he told you two weeks ago. Are you man enough to take his cherry and make him a woman?

You rub his "clit" just like you did Louise. It feels so sexy through his lace panties.

"Kiss my clit, Fred, you know you want to." There it is: Jerry's challenge. You knew it was coming. You've been playing the part of "Master Frederick." You've been in charge or thought you were. Jerry is becoming more and more like a woman. Leading you on, letting you take charge but Jerry has a plan too! He strokes your cock as you kiss his tits. He strokes your hair and purrs, "Kiss my clit lover. Your cock is ready to take my cherry!"

You moan as you suck on his hard little tit. You feel his "clit" through his panties. It's almost as hard as yours! Your hand abandons his clit and strokes his tummy. He arches his back when your fingers slip under his panties and feel the coarse hairs of his bush.

Jerry whispers again, "Kiss it, Fred. Kiss my clit. My pussy is all yours if you just kiss my clit!"

You know you want Jerry's ass! Fucking Jerry has always been the goal. Your cock is telling you to kiss his clit. Kiss it and take his ass! Your brain is working over time. Will kissing his clit make you a cock sucker too?

You feel Jerry's hand rubbing your balls. Your cock is urging you on. "Kiss it, Fred! Kiss my clit and my ass is all yours!" Jerry gently pushes your head away from his tit. "You want my ass, Fred! You want to empty your balls in my ass and all it takes is one little kiss!"

Jerry's hand is wrapped around your cock. Pulling and squeezing as he whispers, "Kiss my clit now and take my ass, Fred!"

You never imagined it would come to this. Jerry is your cock sucker, your cum slut, your bitch in heat. He pushes you towards his "clit" urging you to kiss it and take his cherry. Your lips are just inches from his cock and you realize you want it. But you're Jerry's master; he's the cock sucker, not you! You close your eyes as your lips touch the tip of his cock.