The Submissive Babysitter Pt. 04

When May got Shannon's text she felt butterflies in her stomach. She knew what a slut she had been the last time she had babysat, but she had fantasized about it everyday since then. She was actually grateful to Shannon for teaching her how to suck cock properly, and though she had a hard time admitting it even to herself, she really enjoyed pleasing both Shannon and her husband by sucking Brad's cock the way she had been taught.

May's boyfriend Winston was certainly happy with May's increased interest in sucking his cock, but May was disappointed again and again as he would always cum too quickly. When he fucked her it was almost worse. He was eager, but passive...boring. May tried to encourage Winston to take charge, but he just didn't seem to have it in him.

'Come by tomorrow, won't you May?" Shannon's text read. May's hands shook a little as she quickly texted back confirming she would and asking what time. The response came quickly, "Good girl. 8pm. Wear something nice."

May read the text so many times in the hours before the appointment. She knew 'good girl' was a silly affection, but it still made her smile when she read it. Then, in reading the 'wear something nice', she would feel her heart beat a little faster. What did Shannon expect? Something pretty? Something...slutty? She tried on many outfits and wondered if Shannon was purposely keeping her off balance.

May's fantasies of that night somehow featured Shannon even more than her husband. May was sure she was not gay, but...she couldn't deny she found Shannon sexy. Or that she got excited just by the idea of pleasing her. In fact, she got more excited remembering Shannon's good night kiss than she did when Winston pushed his skinny cock into her.

May knocked at the Taylors' door a little early. In fact she had arrived 20 minutes early and had been walking around the block. For just a moment after she knocked, May thought of turning and running away, but when the door opened and beautiful Shannon was there, wearing a simple, classy white dress and smiling down at her, May felt warm and happy.

As May entered Shannon eyed her up and down. May had chosen a simple white top that was tight around her small tits, and a short tartan skirt that showed off her bare legs. The heels she wore were not high, but May walked a little awkwardly, as she was not used to wearing heels at all.

"Hi May. Don't you look pretty?" Shannon cooed. As May teetered in Shannon added, "I've been thinking about you."

May felt her face redden as a warm feeling washed over her. Could Shannon tell that May had been obsessing about her...fantasizing about her?

"Thank you. Ummm...you too" May said feeling like she might melt into the floor. She felt herself getting lost in Shannon's stare, "Should I...check on Nancy?"

Shannon smiled with a glint in her eye as she poured two vodka tonics, "Nancy is with her father, at her Grandma's house. They are away for the weekend, so it's just the two of us."

May smiled back and took her drink. Unsure of what to say she mumbled, "Oh...thank you." She returned Shannon's toast and drank.

"Are you still seeing that boy May?"

May took a big sip of her drink. She knew alcohol could impair her judgment but she wanted to calm down. "Winston? Ah...yes...I..." May blushed anew.

"And you showed him what a good cocksucker you've become?"

May took another drink and looked down at her feet. She was excited to be alone with Shannon, and to have a 'mentor' to talk about such things, but a deep shyness was ingrained. She explained haltingly that she had shown Winston but he just couldn't last. She blurted out that his cock was also a bit...'lacking'.

Shannon smiled warmly as she listened to the teenager. She asked May if she enjoyed it when Winston fucked her. May stumbled in responding but finally admitted, "He is finished quickly and it's...not as exciting..."

"Not as exciting as...?" Shannon pressed.

May realized she was thinking of sucking Brad's cock while Shannon watched but she answered, "Err...well there was...another boy..." May told Shannon about the time she fucked Winston's friend Harold at a party. Shannon got May to admit that fucking that boy was more exciting than Winston then pushed May on why.

May took another drink and realized she had finished it as Shannon poured her another. "I...I think because it was wrong and...Harold took control...I just had to...let it happen."

"Mmm..you're a pleaser aren't you May?" Shannon said stroking May's hair. May nodded, somehow feeling happy that Shannon saw that.

"Do you ever smoke weed May?" Shannon asked sweetly.

May nodded even though she had only tried once, a couple of puffs. Shannon lit up a joint and inhaled deeply as May watched. She passed it to the young girl. May tried to emulate Shannon but choked on the smoke.

Shannon smiled, stroked May's hair then took the joint back. After inhaling deeply she leaned in towards May who sat still as Shannon pushed her lips against hers. May could smell the mix of weed and Shannon's perfume as she allowed Shannon to gently blow smoke into her. She felt light headed but she wasn't sure if it was the weed or the excitement of Shannon kissing her.

"Thank you." May said breathlessly.

Shannon repeated the ceremony but this time they lingered when their lips meant, Shannon's tongue exploring May's as her hand stroked May's bare leg. May closed her eyes and let the feelings wash over her as she could feel her wetness build.

Shannon pulled away and put her hand under May's chin. "I want to teach you to enjoy getting fucked even more than you enjoy sucking cock."

May nodded earnestly even though a shiver went through her imagining Shannon fucking her with some kind of dildo. She took another drink to help steel her nerves.

"Do you trust me May?" Shannon asked, looking May in the eyes.

"Yes." May answered quickly. "Yes Mrs. Taylor."

"Good girl." Shannon answered. May once again felt a warm feeling run through her. "I invited a friend to come over shortly. He has a lot of experience and can teach you a lot. I will be here the whole time. Does that sound nice?"

May was trying to keep up but nodded as she processed. Shannon's hand stroked May's leg and May felt herself get wetter, "You liked sucking Brad's cock while I watched didn't you?"

May did, and she also yearned to please Shannon. "Yes...yes Mrs. Taylor...very much so."

"Mmmm..." Shannon answered. "It's always more exciting when...it's a little 'wrong' as you said."

May nodded eagerly and finished her drink.

"I want you to stand up and strip for me May." Shannon said matter of factly. "Show me your beautiful little body."

May hesitated a moment then stood. She wondered for a moment if she could really go forwward with this, but even as she wondered she bit her lip and kicked off her shoes. With shaking hands started to pull off her top. Standing in front of Shannon in her bra, she looked down at Shannon and felt like just looking at her made her feel better. The reinforcement of seeing she had all of Shannon's attention, knowing that she was making Shannon happy boosted her confidence. May unzipped her skirt and slowly lowered it while keeping Shannon's stare. May felt awkward knowing that Shannon would see the wet spot in her panties, but it also excited her to be exposed like that.

"Ummm...everything?" May asked meekly.

Shannon smiled and nodded. May unhooked her bra and set it alongside her skirt and top. Her small tits were now on display for Shannon who looked on approvingly. May took a deep breath, put her thumbs on either side of her panties and slowly lowered them until she was completely nude, standing before a Shannon still wearing her white dress. May instinctively put her hands in front of her body but Shannon calmly told her to put her hands by her side and May obeyed. Finally Shannon stood and told May how 'lovely' she looked. She put her hand on May's arm and lightly brushed it along her body as she walked behind May to see her backside. May felt her wetness drip a little down her leg, something she had never experienced before. Shannon gave May's bum a little squeeze then finished circling and stood before May

She put her hand under May's chin, looked her in the eyes and asked, "Are you going to be my good girl?"

May surprised herself with a moan, then assured Shannon that she would be. Shannon smiled and answered, "Ian is going to love you May. And I can assure you that you won't find his cock 'lacking'."

Shannon handed May a small silk robe, yellow with flowers and told her to put it on before her guest arrived. May had just slipped it on when she heard the doorbell. She looked in the mirror on the wall and couldn't help but think how sexy she looked. Shannon kissed her hard on the lips pulling her hair just a little. "Here we go." she remarked.

Ian was a muscular white guy, almost twice May's size. He wore faded jeans and a white t shirt with a large tattoo on his left arm. May stood quietly to the side while Shannon greeted him with a giggle and a kiss as she welcomed him in. While Shannon and Ian chatted a bit about a band he had seen, May looked on, feeling intimidated, excited and a little left out. She was grateful when Shannon turned towards her and said, "Ian, I should introduce to you May who has been waiting patiently for you."

May stepped towards him and began to awkwardly put out her hand when Shannon added, "May, tell Ian why you're excited he came.."

May stopped and looked at Shannon, confused, her heart beating fast.

"Go on May, don't be shy."

May eyes looked towards Ian but could not meet his eyes. She could feel the heat from her cheeks and she spoke quietly, "Nice to meet you Ian. I'm...excited to have you...fuck me."

Shannon and Ian both smiled broadly. "That's my good girl." Shannon cooed.

Ian put out his big hand and when May took it he pulled her closer to him. "Don't you look delicious," he said. "Wrapped up like a pretty gift." he added as he ran his hand down the side of her robe. May could feel herself getting wetter again. This huge guy was really going to fuck her? With Shannon right there watching?

Shannon reached around May's waist from behind and kissed her neck. "She really is something special." Shannon said softly, her breath in May's ear. May felt more wetness drip down her leg.

Shannon whispered even softer into May's ear, "May I unwrap you for our guest?" May let out a soft moan and nodded and Shannon reached to untie her robe, then slowly peeled the robe off her small body. May stood there naked between fully dressed Shannon and Ian. She kept her hands to her sides so they could see her.

"Mmmm...beautiful." Ian evaluated. "And you certainly seem eager."

May's head was spinning but Shannon continued to push her control of the situation. "May, why don't you show Ian what a good cocksucker you've become?"

May felt a mix of shame and excitement in being called a 'cocksucker', but the thought of not complying didn't occur to her. She was committed to pleasing Shannon, and she was very curious what Ian's cock would be like.

May dropped to her knees and looked up at Ian, then tentatively unzipped his jeans, and pulled them down. When she pulled down his underwear his large white cock sprung out and brushed against her face. She took it in her small hand and paused a moment to admire it. Ian's cock was longer than Winston's, Harold's or Brad's, but it also had a lot more girth. She guessed it was twice the circumference of Winston's. She wondered if it was even possible that he could fit into her. At the tip was a big pink head, very different than Winston't uncircumsized cock, or Harold's small tip. Without thinking May lightly licked the tip of Ian's cock. Ian moaned and grabbed her hair. May felt powerful being able to get such a strong reaction so easily from this big guy, and took more of his cock into her mouth, looking up at him to see the intense reaction he had.

Ian moaned loudly which encouraged May to take in even more as she tried to follow Shannon's direction on how best to suck cock. Ian's cock seemed to grow even bigger, filling her mouth. May looked over for Shannon and was gratified to see her smiling down, clearly pleased. Feeling more confident May tried bobbing her head to push his cock to the back of her throat. Ian seemed to grow hungrier with this, as he placed his hand on the back of her head and started to push himself in deeper. May choked but tried hard to continue, knowing how much she was pleasing both of them.

Suddenly Ian pulled out. May wondered for a moment if she did something wrong, but she was quickly picked up by Ian and tossed onto the couch. May had never had a man handle her like this and she was instinctually aroused. Ian positioned her on all fours and May felt very exposed, and intensely excited. She had only ever been in a position like this for Harold, and that had been so fast. Ian took his time, putting one finger into May then another as May whimpered.

"Jesus, she is soaking!" Ian said to Shannon. Shannon walked behind May and very lightly stroked her back then along she ass cheek. May wriggled and moaned with excitement.

Shannon then grabbed each of May's ass cheeks and spread them, "And look, she even has a pretty asshole."

May buried her face in the couch cushion, feeling mortified as she felt herself dripping into Ian's finger and down her own leg. She raised her ass higher still, signalling she was at their mercy. Ian was now pushing his fingers in deeper and circling, giving May sensations she had never had, even when playing with herself. She could feel an orgasm building. She'd only had two, both alone.

"Please...don't stop." she moaned into the couch.

Cruelly, Ian stopped moving his fingers and just left them soaking in May's pussy.

Shannon taunted, "Louder May...Ian can't hear you like that."

May moaned, then lifted her head and said loudly, "Please Ian...please fuck meeeeeee..."

Shannon giggled as Ian positioned himself behind May, grabbed her hips and pushed himself inside her.

"God you're tight...I'm gonna have to go slow."

May's eyes widened as she moaned loudly and she wondered if there was really more for Ian to push in. She was not sure she could handle it. Shannon came over and knelt so she was looking directly into May's eyes as she took her hand. With Shannon there, May's confidence built instantly and she could enjoy the intensity of her feelings.

"Such a good girl May...look at you."

May thought she must look like such a slut naked, bent over on the couch with her ass raised and this huge white guy pounding her. His body slapped against her again and again while May bit her lip and took everything he could give. May looked up at Shannon and came closer to climax. When Ian pushed in deeper still she squeezed Shannon's hand and let out a guttural scream "I'm...mmmmmpphhh". May closed her eyes and lost herself in the sensation. She had given up control completely and now she gave herself to the intense pleasures. Ian showed no mercy slapping into her ass, pushing himself deeper still.

"Who's my little slut?" Ian asked.

May moaned loudly and Ian spanked her ass cheek. "Tell me!"

"I am!" May said loudly.

"Louder!" Ian commanded.

"I AM!" May shouted as Ian continued to push in and out mercilessly. "I'm your little slut."

Shannon smiled down at May and stroked her hair, which was damp with sweat. May felt a deep connection with Shannon, something beyond what she had experienced with Winston. To her surprise she could feel another orgasm building and when Ian told her what a good slut she was, May thanked him and while looking into Shannon's eyes, lost herself again. "Ohhhh....FUUUUUUUCK!" she exclaimed as she closed her eyes tight.

As she finished cumming again, Ian pulled out and said it had been a long time since he had had such an eager slut. He spanked her hard on the ass and walked in front of May. May opened her mouth, expecting she would be face fucked again as she stayed bent over the couch. Instead Ian started to jack his big cock off just in front of her fresh face. "Tell me you want my cum!" Ian ordered.

May paused for a moment then played back what she was told, "I...I want your cum! Please?"

Ian stroked faster and May looked up at Shannon wondering if there was something else she should do. Suddenly Ian started to shoot gobs of cum into young May's face, eyes, forehead and hair. May was grateful she had please Ian. She had seen facials in videos, but never even imagined doing it with Winston. May stayed in position as Ian moved away from her and Shannon handed her a small towel.

"Why don't you clean yourself off and shower," Shannon said softly, "then we'll see what else we can teach you."