In Which Timmy and Tammy Get A Baby Sitter

The first person that Carolyn told about her new baby and (she was almost certain) sissy husband was her close friend Mysti. Mysti was in a happy and successful Dominate / submissive relationship with her husband Aaron. They had been married for over 5 years now and both were happy with the relationship. Both were successful in their personal lives and few outside a couple close friends know that the hard charging owner of his own advertising firm was, in fact bisexual, delicate and feminine while at home. Carolyn had been one of the few to see him in dresses and skirts at home folding the laundry or washing dishes.

Mysti, she knew was an open and warmly loving Dominatrix that was never interested in the all too often physical side of a Dominate / submissive relationship. She did not believe in spanking or bondage or whipping unless it truly was needed to reaffirm just how much she loved and understood her husband. Then, when it was needed she brought out the paddle, took him over her lap and spared no energy spanking him till he was a crying, whimpering, runny nosed little boy again. He was then kissed, cuddled and forgiven of his misdeeds.

She also had a Masters in Business from Whorton and made almost as much money as her husband as a day trader working from home from a computer with multiple screens and a number of flowing charts that, as far as Carolyn knew, could have been in Chinese. The bottom line was that neither Mysti nor Aaron were even close to the average IQ and that made them perfect for what she had in mind. It was time for Timmy and Tammy to have his first baby sitter and maybe his first Lover. In short it was time for Timmy to learn to be a true pleasure giver and for Tammy to taste a mouthful of sperm and the penetration of a Lover.

With all that in mind, it was natural that Carolyn would choose Mysti to be the first to share her secret life at home.

"Diapers? Real diapers?"

"Yup, Attends, size small and they look just like Pampers and feel so close that he will never know the difference. I know and you will know because we have actually changed real babies but for him there is no difference. And bottles and even baby food for special snacks"

They were sitting in a Starbucks a couple miles from Carolyn’s home having Cappuccino and Carolyn was sharing.

"I have got to see this. It sounds so warm. So maturnal... SO KINKY!!!"

"I have no problem with that and Timmy has no say in the matter but, and it is a big but, I have already decided that anyone that actually sees my baby has to be ready to help with basic child care. That means that I expect you to cuddle him, kiss him like a baby, hold his head in your lap and giove him his baba and, of course, if he is wet and you are the one that is close or holding him then you will be expected to change him."

"Does he poop in his Pampers?"

"No. Never. We have Potty Time for that. He is only allowed to wet his Pampers."

"Then I very much want to see your new baby and I have no problem with helping or even baby sitting if you are not home." Mysti thought for a second then sipped her Cappuccino and said, "What about Aaron?"

"What about him?"

"Well, he is bi and we both know he is feminine inside so he may make a perfect big brother or even lover to your Tammy’s sissy side."

"I have thought about it and I really don’t have a problem with that as long as your Aaron is very delicate and loving when we choose to let them cuddle or even have Aaron mount and mate my Tammy."

"How do you think Aaron will react to changing wet diapers?"

"Are you kidding, my little Amy will love that part of being Tammy's Lover and cuddle partner.. ... Under close adult supervision, of course."

"Of course." And both women giggled at the thought.

It was three days later before all the schedules could converge and a full day off could be worked out. Timmy was told only that he was about to have his first baby sitter and maybe, if all went well, his first sexual experience with another male. In essence, he was, if all went all, about to loose his virginity and maybe more.

The day before Mysti came to visit and then again that morning Mommy had reminded timmy that today was to be a special day for him and if he was a good boy he would be rewarded but any misbehavior would be handled right on the spot. Timmy did not want another spanking so he was very submissive when Mommy got him ready for the visit.

He was freshly diapered in extra think cloth diapers with some frilly sissy diaper panties fresh from the adult baby site on E-bay. He was dressed in a pink onezee with care bares and Barbi on it and on his feet were pink laced sockies. Around his neck was his favorite passy on a pink ribbon. There was no doubt about who he was and what he was expected to be.

Mysti arrived at just a minute after 10:00 AM and it was Carolyn that opened the door and invited her in. As soon as the door closed the ladies hugged each other and kissed, sharing tongues and hot breath still sweet from coffee that morning. They hugged again and both know that today was going to be a fun play day for everyone.

Misty was taken to the Nursery where Tammy was working on a complex software problem Timmy had contracted to solve. In the background the television had Doodlebops singing and dancing.

When the door opened Tammy got up and went to his Mommy. She hugged and kissed him warmly and, still holding his hand, introduced him to his new baby sitter. Timmy had known Mysti for some time, several years but then Mommy had never told him just who was coming over and who would be his new sissy sitter.

Mysti broke the tension by reaching for the sissy baby saying, "Come here, darling, let me give you a nice hug and smooches."

Tammy came to her and she folded him into her embrace then kissed him fully, deeply letting his mouth feel the difference between the two women and to learn how to kiss his new sitter.

After the kiss she said, "Such a sweet baby you are. I can tell we are going to be great friends." Now get to a break point, darling, it is almost time for your baba and I need to know if you are wet yet."

Being a sissy, being a baby were central to Tammy and timmy both but no one, not for very long, can actually live in fantasy land and not become psychotic. Not if they have a real adult inside as well as the pre schooler in pampers.

"About, maybe, 15 minutes, aunt Mysti."

"That’s fine, darling. But no longer."

"Yes, Ma’am."

It was just 20 minutes later when Tammy came into the living room to find Mysti and Mommy chatting from comfortable and close positions. Mommy in the big chair and Mysti on the couch.

"Come to me, darling." Mysti said and Tammy cuddled up beside her. She slipped an arm around the sissy baby and held him close them laid him over so that his head was on her lap. Quickly Tammy rolled over on her back and Mysti filled his waiting lips with a baby bottle full of Boost. While Tammy took her baba Mysti and Mommy continued to chat about the newest health club and the latest Dr. Phil with out missing a beat. It was clear the Mysti was more then just comfortable with timmy or tammy depending on the mood.

While Tammy suckled Mysti casually, softly rubbed her tummy then slipped her fingers all the way down between the sissy’s legs feeling the diaper. Still dry. But then she would have to be with that erection bulging and thrusting against the diaper. The baby needed a milking as much as a bottle.

"We’re not going to be changing this one any time soon." She told Mommy.

"Is he a little excited?" Mommy giggled and Mysti just grinned. Mommy moved to sit on the other side of her friend and they kissed and Carolyn slid her fingers up and down the front of Mysti’s tight blouse. Even through the fabric of the bra she could feel that Mysti was more then just a little ready to nurse a baby. The nipples were full, hard and pressing against her fingers.

After another kiss Mommy told Mysti, "Why don’t you go take a hot shower and we will meet you in the bedroom."

"Sounds good to me." The baby was sat up and Misty moved to the shower. Tammy had her head laid back on his Mommies lap and the bottle was slipped back in his mouth.

The bottle was empty almost before they heard the shower start running and Mommy took her baby to the bedroom.

Timmy was laid on his back on the big bed and the onezee was removed and then the sock came off. All he had on was his overly thick diaper and the frilly diaper panties that would keep them from leaking.

Timmy was taken to the attached bath where the shower was running and his teeth were thoroughly brushed then he was told to sit on the bed and suck his passy like a good boy.

Mommy took the time to strip off her clothes and lay them on the laundry hamper and by then the shower had stopped and Mysti, warm, steamy, with nipples fully erect stepped from the shower and into the waiting towel that was being held by the naked Carolyn.

The kiss they shared was hot with desire and Mysti took the time to fondle her lovers bottom kneading the firm muscles and then stroke the back of her neck before letting her go. "My turn for the shower and baby is in the bedroom waiting for you."

Mysti walked into the bedroom and took hold of both timmy’s hands then asked, "Do you know what you are expected to do now, darling?"

The passy fell from his lips and he said, "Yes, Ma’am. I’m going to pleasure you."

"Verry good," Mysti said as she laid back on the bed with two pillows under her head. The baby was laid down beside her, Then he was positioned and then he started to nurse on her full, firm breasts. The breast filled his mouth and his tongue caressed the succulent nipple and the thick flesh that surrounded and protected it. "Your Mommy is right, you are a wonderful and oral baby."

Timmy started to slide his hand down her hips in the direction of her most delicate place but she caught his hand and said, "No, darling. After I have had my fill of your nursing you will lick me, suck my clit, pleasure me with the same sweet kisses my breasts are getting."

After just a couple more seconds Mysti felt the desires start to build and she slid her own hand down between her legs. Parting her female delight with expert fingers and then swiftly finding her own pleasure center. In less then a dozen slow, penetrating strokes she was wet and the tender walls were beginning to swell.

Mysti was ready.

"All right baby. Time for you to go lick me till I tell you to stop."

Timmy kissed her nipple good bye, kissed her tummy as he shifted position and, after a few seconds his mouth was over the vaginal opening and he was laying between her legs with his knees on the soft stool that Mommy had put at the foot of the bed. Timmy was comfortable, balanced and in just the perfect position to provide oral pleasures.

His lips sealed over the already wet and swollen vagina and his tongue was ready to find and lick the waiting clit when he felt fingers on the back of his neck and Mommy’s whispered, "Good boy... Mommies precious baby ... do a good job now, darling."

Mysti’s own juices were flowing freely trying to lubricate her from the licking, sucking tongue and lips of Timmy as he worked hard to pleasure her. The bed was already wet from the mix of juices and his salivating lips as they dripped from his mouth. He gasped and licked and slid his tongue in and out, back and forth until Mysti could simply not hold back any longer.

Her knees came up off the bed and she locked her ankles as the first spasm of her first orgasm shook her to her core. She grasped Carolyn in her arms, hugging her tight and screaming her release into her shoulder and she second shudder swept through and over her and then, Oh GOD Then it was coming on again, faster then the last, stronger and with no possible escape from the torturous friction of that overpowering tongue.

Mommy felt it coming too and she pressed a hand hard on Timmy’s neck and the back of his head driving his laps and mouth tight to Mysti’s dripping, throbbing, pulsing pussy.

Mysti was so lost in her body and it’s release after release that she did not even know she was calling out wordless screams and whimpers. Almost baby talk and babbling until it was over. All over and she lay spent, exhausted, totally fulfilled. She let her legs collapse on the bed and just lay still panting.

"Go give her kisses, baby boy."

Timmy slid up beside the exhausted baby sitter and kissed her full on the lips. Mysti responded with kisses of her own then she wrapped her loving arms around the good little baby and held him close until she drifted into a light doze.

Carolyn was anything but unaffected by her friends sexual pleasures. In fact she was aroused to the point of auto erotic orgasm. She was about to climax with out the need of any kind of touch. Oh she was so ready, so completely full of her own desires.

Timmy was gently turned toward her and taken into her arms. "My turn, darling. Just like you did with your baby sitter."

"Yes, Mommy." He said as she lay back, propping her head on the pillows and waiting for him to get into position.

In just seconds she felt the lips kiss her pussy, the tongue penetrate her, the teeth softly nibble and the first tug of suction and then it was far too late for her to stop even if she had wanted to.

It was her first cries of delight and complete release that actually woke Mysti and she reached over then took her friends hand. Reassuring her with touch and caress.

Timmy did not feel Mysti stir on the bed. The first time he knew she was awake was when he felt her strong fingers on his neck and heard her softly spoken words of guiding, reassurance, and coaxing. She felt so much like Mommy but completely different. In that moment he knew that she loved him for who he was, all the sides of him, just like Mommy did.

This time it was Mommy that was asleep. Totally spent and holding the baby in her arms while Mysti rubbed his back, the back of his legs and his feet whispering words of pleasure, praise and comfort while the baby was held by his Mommy.

Once more Timmy was being held with the head in a lap, taking a bottle as the women took turns holding him and taking much needed showers. This time, though, there was one small difference, Timmy felt the pressure start to build at last and in one movement the bottle was replaced by his thumb and he sucked deeply.

"Ah, how sweet. And about time, too I think. Go on darling, I have been waiting for you to need a diaper change."

Timmy sighed softly, squirmed on the couch and Mysti put her hand between his legs feeling his diaper get both warm and so very heavy. Such a soaky wet baby.

"This one needs a diaper change."

"About time. Usually I change him three or four times before lunch."

"Where do I change him?"

"Nursery has a changing table. Take your time. Go with Mysti, darling she’s going to take care of you this time."

Timmy waddled, heavy diaper drooping between his legs behind his baby sitter to the nursery then he lay down on the changing table. Mysti saw that everything she could want was on the shelves below the actual table. Diapers. Plastic panties. Powder. Baby oil. Even a couple dildos, a vibrator and a strap on to be used as a special treat.

Timmy lay on his back, legs slightly spread and with his head on a soft pillow till Mysti put a passy in his mouth, kissed his forehead and chin and said, "You are just the sweetest and most adorable baby I have ever seen. ... Now lift up." Timmy lifted his hips and the panties came off and went straight into the diaper pail. He really was completely soaked and if she did not move quickly she was going to have to mop the floor a bit.

Six over sized diaper pins were quickly removed and the thoroughly soaked, soggy diaper was tossed into the diaper pail. "I had no idea one diaper could get so wet." She said as Timmy lay still and smiling on the table.

She used baby wipes to be sure that he did not have any chance of getting a diaper rash in front then had him bring his knees to his chest and washed his bottom.

With a finger caressing his bottom she asked, "How often does Mommy use a dildo on your sissy bottom, darling?"

"Couple times a week... When she wants to remind me I am her sissy or when I have been very good."

"I think you have been very good today. Do you take it on your back or on your tummy?"

"On my tummy like if a boy friend were to Make Love to me or mount me."

Her fingers moved up to his penis and she stroked him till he was fully erect then she started to apply the creamy baby oil to the throbbing shaft. "Do you cum when Mommy lets you have your special lover?"

"Yes. Mommy makes sure I make a number three every time I am in sissy play."

"What if Mommy and I got you a real boy friend? A real male for you to cuddle and have mount you? Would you like that?"

"Would he know I am a baby too, not just a sissy?"

"Yes, of course. He would be very gentle and very patient. He would hold you and kiss you and give you your bottle but you would have to be ready to pleasure him like you did Mommy and me and then, after that, you would be put on your tummy and taken like a real sissy needs to be taken. Would you like that?"

"Would it hurt?"

"No darling. Not at all. I have someone in mind that is a bit smaller then you are," she squeezed his penis to reinforce her meaning. "Smaller around and not quite as long so it should feel wonderful for you to have him take your ass and sissyify you."

With one hand she picked up the softest of the three dildos from the shelf and laid the tip against tammy’s mouth. His tongue licked out and started to caress the pretend penis. Once it was wet and dripping she slid it deeper into his mouth, all the while slowly stroking the little boy. "You like having a penis in your mouth?"

Rather then try to talk he just smiled and nodded his head up and down. He was sucking and his cheeks were moving in and out as Mysti moved the dildo in and out in a slow, natural motion. "Is it wet enough?" Again he nodded his head, yes.

The dildo was taken out of his moth and tammy started to turn all the way over but Mysti stopped him and laid him back on his back then she raised the sissy’s knees and held them back against his chest.

She stopped stroking just long enough to put a few drops of KY on the dripping wet phallus then it was pressed against the waiting rosebud of his rectum.

Tammy felt the tip touch his ass and he shivered. Mysti moved up so that she was still in total control but now tammy could wrap an arm around her hips and be holding her for what was about to happen. What she was not ready for was how fast her little sissy had his release.

The tip of the soft, plastic boy friend was just barely starting to slide in. Maybe just past the head and she felt him start to quiver. He was almost out of control.

Rather then force it deeper she started to turn it with her wrist, sliding it back and forth over the delicate nerves of his bottom. Her other hand stroked, firm, solid strokes that never moved past the head of his quivering erection.

"You have sucked your boyfriend and you can taste him still ... He is hard again, wanting to take you, starting to mount you. ... Mommy and I are there and we are holding you. You are a natural sissy. Don’t..." And then it was past her control as the first jet of sperm was released. She pushed the dildo in a bit further and tightened her fingers on the now dripping penis.

The second throb sent a bit less sperm and more shaking, "Goooooood girrrrrrl ...... Goooood babyyyyyyy......"

The third throb brought only a few drops of cum but he was still throbbing from his release. His right arm was tight around her hips, holding her, hugging her. "Precious baby... Give me every drop little lovvvvve. Every drop."

"He stopped quivering and Mysti took the dildo out then kissed his wet, drooling lips. "Very good, darling. Mommy and I are proud of you."

Neither had noticed that Mommy was watching from inside the door so Mysti was a bit surprised when a baby bottle was put into her hand. Mommy kissed her Lover’s cheek, hugged her and let her put the bottle into Timmy’s mouth. Even though he was almost asleep from the release he started to suck the nipple. Mommy took the bottle and Mysti took time, moving slowly, to wash the sperm from the big baby. This time it was a Pampers that went under his hips, his soft penis was laid flat on his pelvis and then the Pampers was pulled tight to his tummy. Six tapes were pulled tight and Timmy was diapered again.

Both women knew that orgasm, especially in an adult baby is only half the equation so timmy, the very sleepy and weak timmy was led to the bed, laid down and cuddled, stroked, massaged by both women till he was sound asleep. By the time he woke up it was time to start lunch.