Sissy for Mommy's Nipple Cream Ch. 06

"But I don't have any more time," Jaime sobbed. "Yesterday Darnell was telling me about another girl he met at the club. She sounded like a total slut, and she was dancing all up on him like she owned him, and he said that she had a big rack, and I don't know what to do!"

Julia paused a moment, choosing her next words with great care.

"You know sweetie, she may have bigger breasts than you, but I'll bet there's something you can offer Darnell that she won't."

A glimmer of hope sparkled in Jaime's eyes as she looked up at Julia, eager to know what she could possibly offer.

"Men are obsessed with anal, but most women aren't willing to go there, especially with a well-hung stud like Darnell."

Jaime's eyes went wide. "You want me to let him fuck my ass? He'll split me in two!"

"Not if I help train you first," Julia replied with a mischievous wink. "I doubt there's anyone in the state that knows more about taking big black cocks up the ass than your dear old mom. I'll be your teacher!"

Jaime was still hesitant, but as usual Julia wouldn't take "no" for an answer, and a few reminders that she had to do something to keep her man away from that floozy at the club eventually brought the reluctant sissy around.

Soon Julia had procured her latest set of tools for feminizing her daughter, a series of anal plugs and dildos in varying sizes. That morning, Julia loaded her tits up with BBC cream, popped a few titty skittles onto each to keep Jaime's girly hormones surging, and called her into the living room for her afternoon feeding. Jaime skipped into the room eagerly, but paused when she saw the array of neatly ordered toys on the coffee table. Her hormone-addled brain filled with questions, but then Julia's cream-covered tits caught her eye and Jaime suddenly remembered how thirsty she was. Besides, she thought to herself, mommy would tell her everything she needed to know. All she needed to do was be a good little sissy girl. Shaking away the questions, she resumed her skipping gait over to the couch and gingerly lay her head down in Julia's lap.

As Jaime begun to nurse and lick the glaze from her heavy tits, Julia stroked her daughter's blond hair with one hand while reaching the other down below her daughter's skirt. She has grown to enjoy playing lazily with Jaime during their long nursing sessions, running her fingers up and down the cool steel of her chastity device, gently rolling her trapped balls back and forth in her massaging hand, and probing at her sissy hole with fingertips lubed up by the steady stream of pre-cum she produced. If Jaime had been particularly good, Julia would sometimes even escalate the tender massage into a more rigorous milking, pushing her fingers in deep to massage Jaime's prostate and provide her some relief. She loved the feeling of closeness she shared with her daughter in those moments as her feminized body convulsed with pleasure in rhythm to her probing fingers, never for a moment breaking concentration on suckling from her breasts.

But this time as Julia slid her fingers in and out of Jaime, she carefully held back, slowing her pace whenever she felt her daughter begin to tense in anticipation of climax. After half an hour Julia's mighty mammaries were both finally emptied and Jaime's belly was filled with warm milk, thick cum, and a handful of pills, but Jaime still lay in Julia's lap, nuzzling into her now empty breasts as she struggled to reach climax. By the time Julia slid her fingers out after one last edging stimulation, Jaime was mad with lust, and she looked up at Julia with disbelief as she moved to stand up.

"Now then," Julia began before Jaime could complain, "I believe you should be nicely ready for the first step in your anal training. Be a dear and bend over that chair for mommy."

As Jaime moved to comply she saw Julia pulling on her strapon harness and slotting in the smallest dildo. She rubbed the dripping pre-cum from her hand up and down the shaft as she approached, then firmly grasped Jaime's hips with both hands.

"This one is a bit small, not much larger than your little clitty, but don't worry dear, mommy will help you train your sweet little ass in no time. Just relax and try to think of how much you enjoy mommy's fingers milking you."

Just as Julia had hoped, Jaime was horny enough in that moment to try anything. She bent over a little further, pushing her ass out and up in the air, and closed her eyes, humbly presenting herself to be fucked. The first thing she felt was gentle pressure as the head of the small dildo pressed against her, but that lasted only for a moment as the shaft was only a little larger than the fingers she was used to accommodating. Even with Julia moving slowly it didn't take long for the entire dildo to bury itself in Jaime's backside. Julia leaned forward, causing her rubber cock to shift slightly inside her daughter, and wrapped her arms around her in a tight hug.

"Oh Jaime, I'm so proud of you sweetie," Julia whispered in her ear as she slowly ground her hips around and around, eliciting deep moans of pleasure. "Now just relax and let mommy give you a good fucking."

Julia kept her hands planted on Jaime's hips as she steadily picked up the pace until her firm breasts were bouncing and clapping together with each thrust and beads of sweat began to rain down on Jaime's back. Although the dildo was relatively small, the sensations of it pounding in and out of her helpless sissy hole felt like waves of rolling thunder to Jaime as she struggled to hold on. Although the sensations were powerful and exciting, they were different than the slower prostate massage that Jaime was used to from her milkings and she still found herself unable to climax. Finally Julia grunted as she reached a climax of her own from rubbing herself against the base of the dildo and pulled herself free before giving her daughter's exposed ass a playful swat. Exhausted Jaime collapsed to the ground as Julia went back to the coffee table and returned with a pair of butt plugs.

"These will help you to stretch out between sessions dear," Julia explained as she slid the smaller of the two in. She had hardly begun to push when Jaime's eager ass squeezed and sucked it right in. "Goodness, what a little butt slut you are!" Julia teased as she easily removed the smallest plug and replaced it with the first. "Already graduating to the next size up! At this rate your hot little ass will be ready for Darnell's cock in no time." Jaime smiled at the thought as she lay on the ground recovering, concern over the orgasm she never quite managed lost in a sea of bliss as she daydreamed about offering her deepest self to her big black daddy.

For their next anal training session that afternoon, Julia dressed for a workout, wearing tight yoga leggings, a heavy duty sports bra, a headband and of course her strapon harness now sporting the next dildo up. Jaime tried and failed to suppress a girly giggle at the sight of her mom's outfit and continued to laugh as Julia gave her best Jazzercise instructor impersonation cheering her daughter to "really take that cock deep" and to "pump out of few more reps." The humor helped Jaime to deal with the size upgrade. It had only looked a little bigger than the first dildo, but the effect of increasing girth was deceptive, and in spite of the butt plug she'd worn throughout the day Jaime felt as if it might be too much for her to handle.

Just when it seemed impossible to continue, Julia reached forward and slid two fingers into the side of Jaime's mouth. Jaime was surprised, but her instincts reflexively made her begin to suck and swallow, rewarding her with the gobs of BBC cream Julia had doused her fingers with. The sweet creamy taste instantly soothed the sissy, helping her to relax her body and accept that she was being fucked. Soon she was even grinding back against Julia with every thrust, asking her to fuck her harder as she again pursued the elusive analgasm. Her quest was again in vain as she was still stranded on the plateau of pleasure when Julia finally pulled out, but in truth Jaime didn't mind. She felt as if she'd had a breakthrough, and she knew she'd get to cum before too long from her breast-pumping that evening.

Once Julia gathered herself she kneeled down to inspect Jaime's hole and saw that it was gaping back at her, a bit reddened but in decent shape.

"Stay right there darling," Julia instructed Jaime, "We need to do a little aftercare to keep you in top shape."

Julia grabbed her tub of BBC cream and began to rub it into Jaime's ass, focusing mostly on the reddened areas, but also pumping some inside with her fingers. At first Jaime was upset to be "wasting" real men's cum without even tasting it, but as she felt the cool soothing tingles of it rubbing into her sissy hole she purred with contentment.

Julia and Jaime's anal training sessions continued in the same way for days, gradually stretching Jaime's capacity until she was finally able to handle Julia's largest dildo just in time for Christmas. The girls gleefully went shopping together for Darnell's present and had it wrapped and waiting for him under the tree when he came over for a bit in the afternoon.

As usual Jaime met him at the door with a kiss, planting her lips on his while his hands roamed over her body. It wasn't uncommon for Jaime to drop right to her knees after that for a blowjob, but today she eagerly pulled her boyfriend into the living room and presented him with her present while Julia looked on with a bemused smile and a glass of wine from a chair in the corner.

"Oh don't mind me," she offered as Darnell settled into the couch, "I'm just here to watch."

"Okay. Look shawty, I uhh, I didn't know that we were doing gifts or nothing," Darnell apologized as he turned the present over in his strong hands.

"Oh, that's like totally fine," Jaime assured him as she curled up next to him on the couch. "This is just a little something, maybe you can give me something bigger in just a bit."

Darnell wasn't quite sure what to make of that, so he went ahead and unwrapped his present. Inside was a small box with a bottle of lube. He looked down at it in confusion for a moment before looking up into Jaime's waiting eyes.

"I thought maybe we could use it for..." Jaime drifted off for a moment before finding the nerve to continue, "for our first time."

"Our first time? You mean you wanna take me like that?" Darnell nodded meaningfully at Jaime in mild disbelief.

"Mmhmm," Jaime answered as she nodded enthusiastically, "Quit being such a gentlemen and fuck my ass already."

A scramble of frantic motion ensued on the couch as clothes flew off and Jaime flipped onto her back holding her ankles up by her head. Darnell positioned himself in front of Jaime and began lubing up his stiffening member before suddenly remembering Julia and turning around to see her watching with a smile.

"Oh, don't mind me dear," she said between sips of wine, "I'm just here to watch, it's not every day a mother gets to see her little girl be made a woman."

"Just remember Darnell is my man mommy, don't try anything funny," Jaime said with all the sternness she could muster as she lay on her back presenting her already gaping hole. "Now fuck me daddy, I need to feel your big black cock inside of me!"

Darnell had hesitated before at the oddity of being watched by his girlfriend's mother, but there was no way he was turning that down. He put one hand on Jaime's shoulder for leverage and used the other to guide his now rock-hard manhood to her hole, then began to push. Jaime's eyes bulged slightly as Darnell's well-lubed cock slipped past her defenses and stretched her even further. She'd thought that Julia's largest dildo had been plenty big, but now she saw that Darnell was even larger. Her breath started to come more quickly as she started to panic. The fleshy rod pushing inside of her felt softer and warmer than the dildos she was used to, but at the same time she was struggling with it's sheer size and she began to panic.

But Julia had been watching for just this moment and rushed over to her daughter's side in her moment of need. She leaned over and kissed her deeply, distracting her in the critical moment as Darnell slowly forced his full length into Jaime and waited. The girls' kiss continued for a long minute, their tongues dancing in tandem as Jaime's body stretched to accommodate the massive intruder. Finally the kiss broke as Julia pulled away and whispered to Jaime, "You did it sweetie, mommy is so proud of you."

Jaime opened her eyes and looked up into Darnell's, feeling a proud sense of accomplishment and a pleasant sensation of utter fullness that sent tingles down into her cage. The two smiled at each other as Darnell began to pull out and thrust back in, only a small amount at first but rapidly building up to his full length as Jaime's body opened fully to accept him. Although she'd never been able to climax from Julia's anal training, it was radically different having a real man's cock pounding her ass, and when Darnell finally came with a deep grunt, Jaime was instantly launched into an orgasm of her own that sent little streams of her cum dribbling down from her cage to mix with the thick globs of Darnell's cum seeping from her ass.

As she laid back in reverie from the mind-breaking orgasm he'd just given her, Jaime looked up into Darnell's eyes and in a tender voice said for the first time, "I love you."

Darnell looked back down at Jaime with a series of conflicting emotions running over his face before responding, "Alright, cool. Thanks for the gift shawty, let's do that again soon." Then he started gathering his things and headed out.

Julia was shocked and ready to comfort Jaime, but apparently her daughter was too high from her first real analgasm to notice that anything was amiss. Instead they simply lay together on the couch enjoying each others presence as the cuddled together and eventually Jaime began to nurse. Julia reflected on how far agreed she'd gone to keep her daughter, but as she looked down at her sweetly nursing from her breast she couldn't help but feel that it had all been worth it. And Jaime did seem truly happy. Maybe everything would work out in the end with Darnell, but just in case it didn't Julia knew that she'd have to guide her daughter through one last transformation to keep her happy forever.