Gay stories: Rachel Babysits Jacob – Part 2
“Rachel! Mrs. Turner said she wants you to babysit Jacob again.” Yelled her mother
up the stairs. It was early morning on the Saturday of Memorial Day weekend, and Rachel was up in her room, lying in bed, relaxing after her early morning jog. Like all of her jogs, Rachel wore her super tight and short running shorts, partially for the comfort they offered, but mostly because she loved showing off her cute, tight little 17 year old butt. She would typically lay in her bed, and lock the door behind her so she could masturbate after all her morning jogs, but her mother’s announcement definitely floored her.
“Yes, she said she and her husband will be gone until late Monday night, and needs someone to babysit the whole weekend, she would like you to come over later this afternoon.”
“Yes, I would love to do it!”
“Ok, I will let her know.”
It was no secret that Rachel enjoyed her previous experience with Jacob very much, and that it had fueled many of her masturbatory exploits afterwards. Rachel returned to her bed, locking the door behind her, her mind racing with images of adorable little Jacob, and her panties soaked with a combination of her sweaty butt cheeks from jogging, and the cascade of sexual juices now flowing from her moist, beautiful vagina.
While laying down, Rachel began rubbing her hand teasingly over her sports bra, tickling her now rock-hard nipples. Her other hand was slowly slipping into the waistband of her running shorts, making its way to her dripping wet love hole, covered with the silken material of her Victoria’s Secret panties. She began rubbing her nipples and sensitive little clitoris, as images of Jacob’s naked little body flooded her mind. She was moaning in pleasure as she was reaching closer and closer to the sweet release of orgasm.
She reveled in recalling the feeling of Jacob’s soft, silky boy butt cheeks in her lap; the feeling of his warm butt hole wrapped around her finger as she prodded closer and closer to his sweet spot; the feeling of his tiny little sphincter constricting tightly around her finger as his adorable little boy penis spasmed in her other hand, and began spewing its clear, immature boy goo all over her fingers; the sound of little Jacob moaning her name as all of this happened, and his exasperated breathing afterwards.
Rachel had reached the edge, she grabbed a pillow to put in her mouth to conceal her screams, because she knew this was going to be an intense orgasm. Her cute little butt cheeks tightened up as she thrust her hips up towards the ceiling, and screamed loudly into her pillow as her vagina began squirting copious amounts of fluid all over her bed for nearly a minute and a half.
That was definitely one of the most pleasurable orgasms Rachel had ever had, and certainly the first time she ever squirted. She had heard stories about that, from her friends and on the internet, but she had no idea how insanely good it would feel. Much more than satisfied, Rachel collapsed back into her bed, breathing heavily, and smiled at the thought of being alone with that sweet little boy all weekend, and how much she was loving her life right now.
After recovering from her amazing orgasm, Rachel cleaned up her mess and then took a quick shower and headed downstairs for breakfast.
“Are you excited to babysit Jacob again Rachel?”
“Definitely, that family is super nice, and he is just SO CUTE!”
“Well I’m glad you like it, I’ll drop you off in a couple hours. Since it’s for a whole weekend,
you should go pack a few things, don’t you think?
“Definitely.” Rachel ran upstairs to start packing her suitcase, but not with exactly what her mother had in mind.
Hidden deep in her closet, Rachel had a few sexual “toys” that her and her boyfriends had enjoyed using in the past. She thought maybe little Jacob would enjoy being handcuffed to the bed, as she devilishly tickled his little penis with a feather duster. But then again, what if he doesn’t, she thought. However, she thought of how Jacob is just a little 10 year old boy, and he would do whatever she told him, as a devilish grin came to her face. She began packing her handcuffs, whips, sexy panties and lingerie, among other things. Her pussy was sopping wet as she was packing everything away, thinking of all the things she would do to that sweet little boy. As she went downstairs with her large suitcase, her mother became rather curious.
“Why such a large suitcase for just a weekend?”
“Oh, well, I wanted to bring a lot of… activities, for Jacob.” She replied, with slight panic in her voice.
“Oh, ok. Well, do you wanna get going?”
“Yes please!” Rachel and her mother packed the car and started driving towards Jacob’s house. “Now rachel, don’t go doing anything crazy with that boy.” Rachel looked over at her mother slightly nervous. “Ha, just kidding, have fun kiddo!”
“Oh, I will mom!”
“Here we are! I will come pick you up Monday night, and you can call me if anything happens!”
“Ok mom, love you.”
“Love you too, see you soon.” Rachel approached Mrs. Turner’s door with her suitcase and rang the doorbell.
“Hi Rachel! Oooh, what a big suitcase, you must have all sorts of fun activities in there for Jacob!”
“Oh yeah, for sure Mrs. Turner.”
“Come in, come in, and please call me Tiffany. Now, I know you probably weren’t expecting this, but Jacob has a little friend staying over for the weekend. He’s a little younger than Jacob, 8, and his name is Brody. Now of course I will pay double for this, but if you don’t want to I understand.”
“Oh, no, I would love to babysit both of them!” Rachel’s mind was churning wildly with all sorts of crazy new plans she could do with now two little boys!
“Ok, great, well I think the two of them are up in Jacob’s room right now, I trust you know everything to do, so I will see you Monday.”
“Ok, see you then, Tiffany,” Rachel smiled to Jacob’s mother as she walked to her car.
Rachel set her suitcase down in the living room and decided to head upstairs to see what the two young boys were up to. Rachel approached the door to see it was closed, but decided to just walk in anyway. She opened the door, and was greeted with quite the unbelievable sight. Jacob was standing over another little boy laying on his bed, whom Rachel assumed was Brody, rubbing his hands over the little boy’s naked tummy.
“Rachel!” Exclaimed Jacob in a mixture of excitement, and nervousness. “Wha-what are you doing here?”
“Well, I thought I’d come here a little early to spend more time with you. What are you doing?”
“We-we were playing doctor. I just had a checkup, and Brody wanted to know what it was like.”
“Oooh, can I watch?”
“You want to watch?”
“Well of course Jacob, you little cutie, and your friend there is a really cutie too!” Rachel looked over the young boy laying on the bed. He was noticeably smaller than Jacob, and his legs were bent at the knee, giving Rachel a pretty view up the leg holes in his little gym shorts. The boy’s thighs looked so small as if Rachel could wrap a single one of her hands entirely around them. Rachel could see a look of embarrassment and shyness on the young boy’s face, something she wanted to clear up right away. Rachel walked up to the bed to talk to Brody directly.
“Well hi there little guy, you must be Brody.” Gleamed Rachel with a seductive smile.
“Hi.” replied Brody in a shy little boy voice, his silky little tummy still entirely exposed.
“Ooohh, you’re so cute Brody, can I get a hug?” Before waiting for a reply, Rachel picked the small boy up, and holding him up with one hand covering more than the entirety of his little tushy, the small boy melted in her embrace like a little baby. Rachel put the boy back down on the bed, anxious to see these two adorable little cherubs “play doctor”.
“Rachel.” whispered Jacob, tugging on her shirt to get her to come down to him, so he could whisper in her ear.
“What is it Jacob?”
“I…I wanted to show Brody the special stuff you did to me, you know… here” Jacob was pointing to his little boy crotch.
“Oh, well I’d REALLY like to see that!” Smiled Rachel, and Jacob returned to the bedside and replaced his hands on Brody’s smooth tummy. Jacob’s hands began nearing the waistband of Brody’s shorts, but he was stopped by Rachel.
“Wait, did you check Brody’s little butt yet Jacob?”
“What do you mean? The doctor didn’t check my butt.”
“Oooh, well it looks like I’m just gonna have to check both of your little butts, aren’t I.” Smiled Rachel, winking at the little boys. “But first, I just have to grab something from downstairs.” Rachel left the room and headed downstairs, but of the course the boys quickly followed suit, Jacob anxiously awaiting the impending orgasm, and Brody just following out of curiosity.
“What’s in the suitcase Rachel?” Asked Jacob.
“Ohhhh, just a few toys.” First, rachel pulled out her naughty school girl outfit.
“You… you’re gonna wear that?” Asked Jacob.
“Mhm, but first you little boys gotta put on these.” Said Rachel, holding up two blindfolds. She tied them around the boys’ heads and began stripping. Soon, she was standing completely butt-naked in front of two little blindfolded boys.
“Give me your hand Jacob.” Jacob extended his hand out, which Rachel grabbed, and placed on her inner thigh.
“Wha-what are you doing? What is that?”
“That’s my thigh Jacob. Do you want to touch me everywhere?”
“Ye…yes please” Gasped Jacob, swallowing hard, unable to comprehend what was happening.
“Ok Jacob, get ready.” Rachel guided his little hand towards her sopping wet vagina, and, grabbing one of his fingers, inserted into directly into her slit.
“Wha-what is that?” Stammered Jacob.
“That’s my vagina. You’re inside of my vagina right now.”
“I.. I am?”
“Mhm, do you like it?”
“I sure do!” Jacob’s statement was verified by the tiny little bump Rachel saw growing in the little boy’s soccer shorts. Although they were in the middle of the living room, the front door was locked behind them, and all of the windows were closed, so Rachel wasn’t too nervous.
“Well here, let me help you out Jacob.” Rachel reached forward and lightly grasped Jacob’s little package, and started caressing it while continuing to stroke Jacob’s finger inside of her vagina. The little tyke’s pee-pee quickly stiffened to full 4 inch throbbing erection as the toddler began moaning and cooing in pleasure. Much to the poor boy’s dismay, Rachel removed her hand from the boy’s willy and removed his finger from inside of her.
“It’s Brody’s turn, ok Jacob?”
“Ok.” Pouted Jacob, obviously saddened. Rachel walked up to Brody, who, as far as she knew, had no sexual experience whatsoever, and she LOVED IT. However she did notice that the little boy’s instincts took over, and there was a tiny little bump forming in the boy’s shorts.
“Hi Brody, do you want me to touch this?” Asked Rachel, closing her hands around the little boy’s stiffy, and briefly brushing her thumb over the boy’s sensitive little head, teasingly. Brody jumped in shock, completely unprepared for the feeling.
“Ok boys.” Said Rachel, “I’m gonna get dressed in this little schoolgirl outfit, then you boys can take off your blindfolds, and we can go up stairs, ok?”
“Ok!” Shouted Jacob, Brody was still too shy to say anything. Rachel took one of the boys in each of her hands and walked them up to Jacob’s room in her super sexy outfit consisting of a short skirt with lace undies, boots with long socks, and a very revealing blazer and heavy makeup. Once in the room, Rachel locked the door and sat on the bed.
“Ok boys, time to check your butts! Jacob how about you go first.”
“Jacob, has your mother ever leaned you over her knee to spank you?”
“Yes, I hate it!”
“I know, but, will you lean over my knee like that? I promise I won’t hurt you.”
“Ok.” Jacob went towards Rachel, who picked him up and leaned him over knee. Rachel was quickly reminded of how little this boy really was when his teeny weeny toddler tushie was over her knee, and his feet couldn’t even touch the floor! Even all of his weight resting on rachel’s knee didn’t seem like much. He was of course only a 4 foot tall little 10 year old boy. Brody was standing nearby, his little penis growing along with his horniness, though of course he had know idea what it was. Rachel looked down at Jacob’s little tush staring up at her.
Each of his little butt cheeks were distinctly outlined by his super shiny dazzle soccer shorts, and by the fact that the material was clinging tightly to his cute lil butt crack, surely giving him a somewhat uncomfortable wedgie. Rachel gingerly placed her hand on the boy’s butt, though he still flinched from the familiar situation of his mother spanking him. Rachel began rubbing his butt cheeks, and was still in absolute love with the feel of those two silky mounds in her hands, covered by swishy athletic shorts, and especially the adorable little crack between them.
“Brody, do you wanna come feel Jacob’s butt, it’s really soft!”
“O..ok.” Brody cautiously walked up to Jacob and placed his hand on his butt, and rubbed it like Rachel was. At first, Jacob thought it would be awkward to have his friend fondling his butt cheeks, but he found the new feeling exhilarating, and his little chub was growing against Rachel’s leg as a result.
“Ooohh.” Moaned Rachel, “It looks like a certain little boy is ready for his treat.”
“Mhm.” Cooed Jacob. Rachel slipped her hands into the waistband of his little soccer shorts and pulled them down.
“Woah Jacob, boxers?”
“Yeah, my mommy makes me wear these now, after I made milky in my undies.”
“Awww. When did you make milky in your undies?”
“That same night after you showed me that special stuff. It was in my dreams, I imagined you doing it to me again, and it just… squirted out, and my mommy found it.”
“Awww. thats adorable sweetie.”
The sight of a little toddler in boxers was a whole other level of cute, and Rachel barely kept from creaming herself right there. The boxers were clearly riding up into Jacob’s lil tushy crack.
“Aww, do you have a wittle wedgie baby? Let me get that for you.” She neared her thumb and pointer finger to the tantalizing little hole between the boy’s cheeks, and gingerly picked the fabric away. The heat emanating from Jacob’s tiny little prepubescent bubble butt was intensely erotic.
“Ohhh, you have such warm wittle buns baby.” Cooed Rachel as she continued stroking her hand up and down along the crease of the toddler’s lil bottom. She finally slipped his boxers off, leaving his bare bum open to be seen by Rachel and his friend Brody. Rachel spread his adorable little cheeks wide, exposing his anus.
“Brody, do you wanna touch his butthole?”
“Ok.” Again, Brody walked up and placed a finger near his butthole, and tried sliding it in.
“It’s weally warm!”
The sensation was surreal to Jacob, and he desperately wanted an orgasm. He began humping his groin into Rachel’s leg like a little puppy, and Rachel was overcome with a sense of love and desire for this boy.
“Here, this might help.” Rachel reached into her pocket and took out a bottle of lube that she had grabbed for this moment, and squeezed some out onto Jacob’s little butt hole.
“Ok, try it now.” Brody was now able to insert his finger into Jacob’s butt, and that familiar, amazing feeling, was building in Jacob’s little testes, but this time much stronger. Jacob was humping wildly on Rachel’s knee as Brody was tickling his butt hole. Rachel didn’t want this to end that soon though, and so, again, much to Jacob’s disappointment, Rachel grabbed Brody’s hand away, pulled up Jacob’s boxers and shorts, and took him off her knee.
“NOOOOO Rachel! I need it SOOOOO bad!”
“I know baby, but you’ll be ok, and I promise, the longer the wait, the better it will feel.”
“Yes, I’m going to make you feel super good this weekend.”
“Ok Brody, it’s your turn, come here.” The little boy walked towards Rachel, and she picked him up just like she did Jacob and placed him over her knee. If Jacob was like a baby on Rachel’s knee, then this little boy was like an ant. He seemed to weigh half what Jacob did,and while Jacob was wearing regular sneakers, this little boy was wearing velcro sneakers that lit up every time he walked. His adorable little butt was smiling up at Rachel the same way Jacob’s did, with each of his cheeks glistening in the glow of his soccer shorts.
“Well Jacob, since Brody got to feel your butt, it’s only fair that you get to feel his.” Jacob was hoping she’d say this, he eagerly placed his hands on Brody’s butt cheeks and vigorously began rubbing the tiny little cheeks. Out of his own lust, Jacob ripped Brody’s shorts down, which revealed something shocking. The poor little boy was still in pull-ups, and all the excitement made him pee! He began crying in Rachel’s lap, and her heart instantly melted.
“Oooohhh, sweetie, it’s ok.” She picked the boy up and put him down, “You have nothing to be embarrassed about.
“That’s not twue,” Said Brody, still crying, “Jacob won’t be my fwiend anymore now.” Before Rachel could say anything, Jacob put his arms around Brody and hugged him tightly.
“I love you Brody.”
“Wea…weally?” Asked Brody, still sniffling.
“Mhm.” Answered Jacob, kissing him on the cheek. Brody Wrapped his arms around Jacob and hugged him in return, now crying out of happiness.
“I love you too, Jacob.” Rachel was in absolute shock from the scene that just played out in front of her, but eventually came back to.
“Do you need a new pull up?”
“Yes please, they’we in that bag over thewe.”
“Ok, lay on the bed and I’ll take care of you.” Rachel slipped his wet pull ups off, and he drew his heels up to his cheeks. Rachel became extremely horny at the sight of the boy’s cute little butt crack leading up to the teeny little acorn between his legs. Jacob grabbed one of his pull ups and handed it to Rachel. She asked Brody to raise his butt up and she slipped the new pull ups on, but just before they were all the way on, she gave the little boy’s head another quick little tickle between her fingers, hoping he would become a horny little boy. It definitely had the desired effect, as Brody’s hands quickly went to his pee pee, and slipping one under his pull ups, was desperately trying to recreate the feeling Rachel just gave him.
“Aww, I’m sorry, but not now sweetie, soon I promise.” Said Rachel, pulling the boys hands away, leaving as a sad a look on his face as was on Jacob’s.
“Jacob,” Said Rachel, “How about you continue playing doctor with Brody, and I’ll watch. Don’t forget to check his butt though,” Said Rachel, smiling and winking.
“Ok!” Jacob ran over to Brody on the bed.
“Brody, will you lie on your tummy for me? The little tyke rolled over and Jacob quickly placed his hands on the butt of Brody’s new pull-ups. Rachel was in heaven, she was getting a free strip show from these two little boys, and she was sopping wet. Jacob slowly pulled Brody’s pull-ups down, revealing the boy’s little white tushie. Jacob then spread his cheeks and grabbed the lube that Rachel had used on him. He poured a little down Brody’s butt hole, and shoved it in with his finger. Brody was definitely moaning and instinctively humping the bed as Jacob explored his rosebud.
“Don’t let him finish yet Jacob, flip him over.”
You heard her Brody, flip on your back.” Brody flipped over, and Jacob quickly returned his hand directly to Brody’s penis, which was now a full blown 2.5 inch erection. Knowing exactly what to do, Jacob sat up behind Brody on the bed, had him sit up also, and poured the lube over Brody’s erection. Rachel was watching with intense excitement as Jacob stroked Brody’s little cock clumsily. Very soon, Brody’s eyes were closed, his breathing was heavy, and he was humping like a wildman into Jacob’s hands, Rachel knew he was very close.
“STOP!” Screamed Rachel, and Jacob quickly threw Brody’s penis from his hands.
“Come here Brody, she said, I want your first time to be amazing. Can you sit on the floor over here, on your heels, with one butt cheek on each heel?”
“Ok.” Brody sat on his heels just how Rachel instructed, with one cheek on each heel, and Rachel sat down right up behind him. She reached her hand around to his front side and liberally applied more lubrication to his entire undercarriage, and lovingly embraced his baby pecker.
“Ok Brody, now, can you spread your butt cheeks super far apart with your heels for me, as far as you can get them. Brody did this, and Rachel began fondling his little wood with one hand, while gently fondling his practically nonexistent testicles with the other. The little toddler’s miniscule buttcheeks were pressed firm against Rachel’s inner thighs.
That, combined with the feel of the boy’s slippery little snake in her hands, and the sound of his innocent little pigeon coos were driving her absolutely bonkers! When the boy’s erection was officially throbbing, Rachel began properly stroking the sweet toddler. At the top of each stroke, Rachel, would pinch the boy’s soft, circumcised little head, because she knew very well how nuts that would drive the boy. After about 15 strokes, the boy was in hysterics, whimpering and moaning, and Rachel knew one more stroke would throw him over the edge.
She wanted to give him a treat though, so before the last stroke, she, without warning, jabbed her thumb straight up the boy’s wide-spread butt hole, directly hitting his prostate. At the same instance, she gave the little boy one last tug, and he went absolutely ballistic in her arms. Obviously there was no liquid, but the boy’s penis began spasming forcefully.
As soon as she saw the boy was orgasming, she resumed tickling his butt hole, but she removed her hand from his penis and began tickling the insanely sensitive underside of Brody’s baby little pee-pee head with her pointer finger in a “come hither” motion. The boy’s orgasm seemed to last forever as he thrashed violently in front her, and his penis convulsed nearly twenty times as she continued tickling his supple butthole and precious little glans throughout the entire experience. Jacob looked on knowing all too well how amazing that felt, and wanting so desperately to feel it himself.
“How was that Brody?” Asked Rachel, as the boy was laying back in her lap, barely conscious and panting heavily.
“A…amazing!” Said the little boy.
“Well, I’m glad you liked it, but I’ve got a lot more to show you this weekend.” Smiled Rachel.
“Is..is it my turn Rachel?” Asked Jacob.
“Woah, hold on there lover boy. You’ve already experienced my hand stuff. You’re ready to level up, sweetie.”
“Really, you mean…?”
“Mhm.” Moaned Rachel, placing Jacob’s hand near the fringe of her skirt. Jacob continued up and found his hand again laying against Rachel’s supple pussy, except this time covered by her silky laces.
“But not now!” Scolded Rachel, slapping Jacob’s hand away. We have to eat dinner now. Jacob was practically in tears, unable to believe how cruel and teasing Rachel could be. Jacob was now almost violently horny, and he really needed to cum.
“I’m not hungry! I want to squirt again!”
“Aww sweetie, come here.” Said Rachel. She embraced him in a loving hug, and moved her hands to his little butt cheeks, and gave a quick little poke to his butt hole through his shorts.
“Just be patient sweetie, I promise I will blow your mind, but later, we must eat now, ok sweetie?”
“Ok boys lets go eat.” Said Rachel, again holding one of them in each of her hands and walking them downstairs.
“What would you boys like to eat?” Jacob knew how he wanted to answer that question, but decided to hold his tongue in fear he may not receive any “gifts” later.
“I want lasagna.” Said Brody,
“Oh, of course he’s satisfied.” Thought Jacob to himself.
“Yes, I would love some lasagna too Rachel.”
“Ok boys, I’ll get right on it, play nice, ok?” Smirked Rachel, easily sensing Jacob’s obvious jealousy.
“So, did you like that Brody?” Asked Jacob
“It was awesome!”
“Well’ I’m glad you liked it bud.” Smiled Jacob, leaning in to give Brody another snuggle.
“I really want to feel that too Brody, but as you saw, Rachel just left me hanging. Do you think you could help me out?”
“What do you mean?”
“Well…” Jacob grabbed Brody’s hand and placed it on his erection, “Will you just…squeeze?” Brody began squeezing Jacob’s willy, and it was actually feeling really good, as Jacob started squirting a little bit of precum into his boxers. Brody remembered how Rachel teased his head and wanted to do the same thing for Jacob, so he started teasing his head through his shorts. Jacob was very close to release, unfortunately the little boy was too inexperienced with his sexual feelings, and he couldn’t keep himself from moaning out loud. Rachel quickly came out of the kitchen to end the activity.
“Guys, I’m really sorry, I just want to do something REALLY special for both of you, but I really want you to eat first.”
“Ok Rachel, we’re sorry.”
“It’s ok, the lasagna’s almost ready boys, just sit still, ok?”
After what seemed like an eternity, Rachel finally came out of the kitchen with lasagna.
“Ok, lets eat.” They all devoured their lasagna as fast as possible, as they were all honestly dripping with the desire for orgasms. After dinner, they all went straight back up to Jacob’s bedroom to continue the night’s activities.
Rachel grabbed Jacob’s hands and put them on her butt cheeks, she then put her own hands on Jacob’s butt cheeks and pushed him close into her.
“Hump me baby.” Commanded Rachel, and the sweet toddler complied instantly, grinding his little boy meat into her skirt.
“Do you want to put it in me?”
“Say you want to put it in me.”
“I want to put it in you.”
“Say where you want to put it.”
“I want to put it in your pussy!”
“Oooh, ok, well come over here on the bed then lover boy.” Rachel took Jacob to the bed and began slowly stripping him butt naked as he dry humped her body.
“You want it baby?”
“Well before you can get it, you have to do something for me.”
“You have to put it in his butt.” Said Rachel pointing to Brody.
Other Chapters: Rachel Babysits Jacob
- Rachel Babysits Jacob - Part 2