The MILF Mentor

©️ JRydher, JRydher1 2023

This is somewhat of a sequel to "A MILF is Born" in that it is the continuing adventures of MILF, Raquel "Rocky" Miller. All characters in this story are fictional and at least 18 years of age.

~~~~~~~~~~~~~~~~~

Billy Tilson was an 18-year old high school senior. He was a decent looking kid, who got good grades, had some close friends and desperately wanted a girlfriend to lose his virginity with. He was tired of jerking off to porn movies and magazines. He wanted the real thing, but he was shy around girls, even those he was friends with. Jennifer Adams was one of those girls. Like Billy, she was 18-years old; she was a sweet, pretty girl, with a beautiful smile, a beautiful body, and even more beautiful heart. Billy had a huge crush on her, but couldn't work up the courage to ask her out. Plus, he was scared he would lose her friendship.

Billy spent most Friday and Saturday nights delivering pizza for a local chain. It helped pay for the gas and insurance on his car, and kept him from thinking about how he would rather be out on a date. One of his regular clients was Raquel "Rocky" Miller. While Billy had a crush on Jennifer, he lusted after the busty blonde divorced mother of three.

Rocky had recently learned what a MILF was and fully embraced the notion that she was looked at as a fuckable mother. She had a gorgeous face and killer body, and loved her newly found sexual freedom and confidence.

An intern at her company, a hotel maintenance man, and the lifeguard who first called her a MILF were the initial beneficiaries of Rocky's emboldened sexuality. She also had an occasional fuck buddy, her friend and neighbor, JR. She gave her body completely to JR, including her ass, but they both wanted nothing more than an occasional roll in the hay.

One of Rocky and her kids' weekly traditions was to get pizza delivered on Friday nights. She would let her two boys and one girl select what they wanted, even if it made for a terrible combination, and she would have Papa's Pizza deliver it. The delivery guy was pretty impersonal and didn't care about his job or getting the pizzas there in any decent time. Then one day, a new delivery guy, Billy, showed up at the door.

Rocky could tell Billy was a sweet kid who always seemed nervous around her. She figured it had to do with raging hormones. One day when her kids were at Rocky's ex, she ordered pizza early in the day with a 7:30 pm delivery time. When she got home from work she changed into yoga pants and a jog bra to have a strenuous home workout. She lost track of time when the bell suddenly rang at 7:30 on the dot. Billy was always prompt in making his deliveries.

Rocky answered the door in workout outfit and was greeted by a gawking and nervous Billy. She hadn't realized she had sweated through her bra and her large nipples and areolas were fairly visible.

"Hi Billy...are you all right? You look sweaty and it's cold out there."

"I'm....ok, Mrs. M," Billy anxiously answered.

"Come in a minute and at least let me get you some water."

"Oh...okay."

"Have a seat and take your jacket off." Billy did as he was told and Rocky got him a glass of cold water. She felt his forehead to make sure he wasn't feverish. The sensation started to get a rise out of Billy's cock.

After he had some water and began to relax, Rocky asked him, "Are you feeling a little better?

"I...I guess so."

"You seem a little anxious tonight."

"Do I?" Billy nervously responded.

"It's me, isn't it? I make you nervous."

"No...no. Why would...would you make me nervous?"

"Because I'm a MILF and you have really built me up in your mind like a lot of other guys." Billy's mouth dropped open in response to Rocky calling herself a MILF. "I think I know how we can get you to be at ease around me," Rocky added.

Rocky pulled her bra off, exposing her luscious, full breasts to Billy. "Give me your hands, Billy." The teen nervously reached out until Rocky grabbed his hands and placed them on her breasts. "Go ahead and squeeze them, Billy. It's all right." Billy squeezed Rocky's gorgeous melons and let out a moan. He massaged and kneaded them as Rocky noted how hard and how large Billy's cock looked through his pants.

"Now take your mouth and suck on my nipples. You can do it gently or hard. You can nibble on them with your teeth too." Once again, Billy did as he was told. He felt precum oozing from his cock and moistening his briefs. His breathing staggered when Rocky unzipped his jeans and pulled them and his underwear down far enough to release his cock."

"Wow, Billy. You are huge," she said as she began to stroke Billy's thick and long shaft. She placed a kiss on the tip and then started stroking him with a regular rhythm. "Oh yeah, Billy. Your cock is so big and beautiful. I'm going to keep stroking you until cum all over my titties and then I'm going to eat your cum. Would you like that?"

Billy gulped and said, "Oh, yes, Mrs. M."

"Just call me Rocky from now on. I take it you're a virgin."

"Yesss," Billy was barely able to respond.

"Okay. We have some work to do. You're not just my pizza delivery boy any more. You are now also my student. Next time you're here....."

"Next time?" Billy interrupted.

"Yes, next time you're here, I'm going to teach you how to eat pussy. You do that right and you can have any girl you want." Given his inexperience and thought of eating out Rocky's pussy, Billy started to grunt and large shots of cum blasted from his cock, landing all over Rocky's tits. She aimed his cock at them to be sure she was covered with his ejaculate.

"That's a lot of cum, Billy. Mmmm." Rocky licked the remainder off of the head of Billy's cock and then kept her word; she licked and ate every bit of the cum that had landed on her tits. Billy almost came again just from watching her.

"There, now you can go bac to work and relax," Rocky said as she finished ingesting the last of Billy's cum. She helped clean Billy up and sent him on his way with the memory of a lifetime.

~~~

As promised, Billy's next trip to the Miller household included lessons on how to eat a woman's pussy. With Billy pressed for time, Rocky wasted no time. She greeted Billy at the door with no clothes on. She then grabbed Billy by his growing erection and led him into the living room. Rocky sat on the couch and instructed Billy to kneel on the floor in front of her. She scootched forward and said, "I'm all wet and ready for you, Billy. Go ahead and use your tongue on my lips and clit." Billy nodded in agreement and immediately plunged his tongue into Rocky's pussy. "Ahhh," the MILF sighed.

Billy used his tongue all around Rocky's labia, then began to flick Rocky's clit right at the spot that she indicated for him.

"Mmm, that's it. Yes!" Rocky groaned. After a few minutes, Rocky was squirming on the couch. She leaned forward and alternately sucked and licked each of her nipples, pausing only to tell Billy, "Put two fingers in my pussy and fuck me with them." Billy stuck his index and middle fingers inside of Rocky and, with no hesitation, banged her pussy with them.

"Oh fuck, that's it. Right...there...ye..yessss." Moments later, Rocky was on the verge of an orgasm. She screamed aloud, "Fuck me harder, Billy", The teen sped up the thrusting of fingers while he tortured Rocky's clit once again with his tongue. He could taste Rocky's juices start to flow and felt the burst of her full-fledged orgasm.

Billy surprised Rocky by adding a third finger to his vaginal assault, which caused Rocky to throw her head back from the feeling of pleasure. Her breasts heaved up and down and were glistening with sweat.

"Stick one in my ass," Rocky suddenly screamed out.

With three fingers from his right hand occupied with her pussy, Billy stuck his left index finger into Rocky's ass. That finished the MILF off; her orgasm intensified and her juices squirted on to Billy's face, the couch, and the carpet. Billy continued to keep Rocky over the edge for several more minutes until finally Rocky grabbed the back of Billy's head as the last of her juices flowed from inside her pussy.

"Stop, please. I can't take anymore," Rocky pleaded for the first time. Rocky was breathing hard when she said, "Billy...that was fantastic. I don't orgasm like that with guys who have experience with oral sex."

Billy blushed, smiled, and said, "Thanks. I don't know what I would have done if you hadn't told me what to do."

"Well, you are a natural, Billy, and you deserve a reward for that." Rocky reached down and undid Billy's pants. She worked until she had pulled his semi-erect cock out from his underwear and stroked and sucked him to full hardness. She rubbed his hardon all over her nipples and slapped her tits with his huge cock. Then she deepthroated him over and over again, stopping just short of letting him cum.

"Now, instead of a gold star, you get to fuck my tits and cum all over my face, " Rocky said. Billy took a deep breath as Rocky placed his cock between her moistened tits and began fucking his dick with them. After being so close to cumming during Rocky's blowjob, it didn't take much time for the first spurts of Billy's ejaculate to hit Rocky in the chin. She then aimed his cock at her face and jerked the rest of his cum all over her beautiful cheeks and mouth, and across her nose.

"Your cum all over my face means that you got an A+ for eating my pussy," Rocky said and winked at her star pupil. As she wiped her face off, Rocky said, "My kids will be with me the next two weeks, but the Friday after that...you get to fuck me." Billy's eyes widened and he sported a shit-eating grin. Another memorable Friday night was in the books.

~~~

The three weeks couldn't go by fast enough for Billy. He had trouble concentrating at school, work, and at home. He nearly broke his dick off masturbating multiple times a day just thinking about fucking Rocky. When the day arrived, Billy made his regular pizza delivery and found the front door was already open.

"Hellooo," Billy called out.

"I'm in here," Rocky said in a somewhat strained voice. When Billy entered the living room he saw why she sounded odd. She had a dildo in each hand and was fucking her ass and pussy simultaneously."

"Holy fuck," was all Billy could manage to utter.

"Nice to see you too, Billy. Would you like your cock to replace one of these?" Rocky answered back. Billy nodded his head in the affirmative. "Good. Now take your clothes off so I can suck your cock and get you ready. Billy disrobed as fast as possible and Rocky deepthroated him as soon as his erection got into sight. She spit all over the head, shaft, and balls; rubbing her saliva all over his hard cock with her lip, tongue, tits, and hands. She pushed him down on to the couch and without hesitation, took his cock into her pussy right down to the base.

"Play with my tits, Billy. They're yours tonight. Squeeze them, slap them, grab and twist my nipples...oh, fuck yes...I love your cock. Take control of me Billy. Bite my nipples...suck on them, stretch them with your mouth until I scream." Billy did as he was told; as Rocky rode him, he squeezed Rocky's large tits. He tweaked and bit her nipples and then sucked on them, stretching them out until Rocky did indeed scream out in ecstasy. When Billy bit down hard on her right nipple, Rocky shuddered and her juices flowed out like a river, covering the teen's thick cock.

Rocky took a moment to recover then lifted herself off of Billy's cock. "Time to change positions. Spoon me on the couch and slide your cock inside. You can hold on to my tits for better leverage. Billy laid on his side on the couch and Rocky laid down in front of him. The teen inserted his throbbing cock into Rocky's drenched pussy and started to thrust. Just as she suggested he grabbed on to her right breast tightly. The move enabled him to increase the speed of his thrusts inside of her.

"Cum in my pussy, Billy. Fill me up with that big cock." Rocky's words acted like a match lighting a fuse inside Billy's cock. He let out a deep groan and shot several streams of sperm inside his MILF.

"Wow....Rocky...thank you."

"No, Billy...thank you. That was fabulous." The teen grinned from ear to ear.

The two sat and relaxed for a bit until Rocky noticed that Billy was seriously hard again.

"Billy, text your boss and tell him you have a flat and you're fixing it. It's time for your next step with me. I want you to fill my ass with your cum." Billy mouth was agape, but he quickly texted his boss and watched as Rocky got on all fours in front of him and urged him to embed his cock in her ass. He felt his head push past her rectum and inch by inch of his shaft get enveloped by her ass until she had all of him inside of her. "Oh my God. Your cock is so fucking big. How does that feel, Billy?"

"Amazing."

"Damn right it does. You're balls deep in my ass and now you're going to fuck me until all of your cum is inside my tight hole." Billy felt precum already leak inside of Rocky's rectum as he began ramming his cock inside of her. She reached below and played with her clit as Billy's thick erection spread her anus wide.

"Squeeze my tits, Billy. Billy reached around Rocky and grabbed both of her breasts. Harder Billy...squeeze them harder." Billy, with Rocky's nipples pressed into his palms, squeezed her tits as hard as possible. Rocky let out a guttural moan in response. Billy's balls and hips continued to slap into Rocky as his cock pummeled her ass. His breathing started to change and Rocky knew he was about to unload his cum.

"Do it, Billy. Cum in my ass. Make my ass yours." That finished the delivery boy off, he grunted again and again and one load of sperm after another filled Rocky's ass. When she knew he was almost done ejaculating, Rocky slid off his cock and took it directly from her ass into her mouth. Billy's eyes opened wide in disbelief as Rocky licked and sucked out the rest of his cum. She deepthroated once more to swallow whatever cum he had left.

After cleaning up, the two sat down to quickly share some pizza and soda. They chatted as they did so.

"So, Billy is there a girl that you really like?"

"Well, there's this girl Jennifer that I have known since I was eight or nine."

"Tell me about her."

"She's really pretty and super smart. She's funny and really sweet. Sometimes, I think she might like me, but then I think it's my imagination."

"Or maybe not, but there's only one way you're going to find out."

"I...I just don't want to be turned down. It would be crushing."

"Billy, I'm afraid that's the price of admission. We all get scared; we all get rejected at times. If you never take a chance, you'll never enjoy life to the fullest that you can.

"But, it's easy for you. You're so beautiful..." Rocky put up a hand to stop him.

"Thank you, Billy, but looks aren't everything and I have made more than my share of bad decisions, and I have the divorce papers to prove it. But, you won't know if Jennifer likes you back unless you take the risk. And, let me tell you, the reward is so worth it when things are great. Like that ass fucking, hmmm?"

Billy laughed. "I know you're right. I'll try to work up the nerve."

"That's a start. And, though I know you have to leave, I'm not letting you leave without feeling good. So, now you're going to fuck my face. I want you to make believe I'm Jennifer. I want you to take control of me, to dominate me. She sounds like the kind of girl that wants you to hold the back of her head while you slam the back of her throat with that big gorgeous cock of yours. Now, get up and fuck my mouth until you cum down my throat.

Billy was as hard as he had ever been, once again driven by Rocky's words. He got to his feet as Rocky dropped to her knees. He slowly put his cock in the MILF's mouth and started to thrust back and forth. Rocky grabbed his cock and took it out of her mouth.

"I said fuck my face, Billy. Make me yours...grab my head and fuck my face." Once again, Billy inserted his cock in Rocky's mouth and this time he roughly grabbed her by the hair and started thrusting back and forth. He could feel the head of his dick banging against Rocky's throat as he started to pick up steam. Rocky's eyes began to water but she was thoroughly enjoying herself. She kept one hand on Billy's hips for balance and rubbed his balls with the other.

Drool and precum seeped out of Rocky's lips as Billy continued to slam all of his cock inside of Rocky's mouth. He was moving at incredible speed when he suddenly stopped and unleashed another torrent of cum as if he hadn't cum in a year. Rocky's eyes went wide this time as an incredible amount of thick fluid shot from the head of Billy's erection. Exhausted, Billy slumped down to the floor. Whatever cum Rocky was unable to swallow, flowed out of her mouth and all over her tits until she looked like she had been rolling around in a bed of cum.

"Holy shit, Billy, you nearly drowned me," Rocky said and the two laughed hysterically until Rocky, now exhausted laid down on the floor and dozed off. Billy showed himself out, excited to see what his next visit would bring.

~~~

Two nights later, it happened. Rocky received a text from Billy one late night.

"Hi, Rocky. She said yes! :-) Thanks for the encouragement". Billy finally found the nerve to ask Jennifer out and she had accepted.

"That's fabulous, Billy. I'm so proud of you! I want to meet her.

"What?"

"I would like to meet her."

"Um, could we wait for a bit on that. I really would like to go out with her first."

"Of course, I completely understand. But, I want to meet her before you fuck her...actually, you can fuck her here when the time is right. We'll say you're house sitting for me."

"Um...okay." Billy was clearly overwhelmed by Rocky discussing the future before Billy even had one date with Jennifer.

"Looking forward to it. In the meantime, you just imagine how you're going to fuck Jennifer in her mouth, her ass, and her pussy. You're going to make her yours so that she's begging you to fuck and cum in every hole of hers. I bet you're hard as a rock right now. Go jerk off and blast your cum everywhere."

Billy texted back, "Well, I have to go now. See you soon.", and then he went and jerked off to Rocky's image.

~~~

That weekend Billy and Jennifer had their first date at the movies and went for ice cream afterwards. There was some awkwardness between them as you would expect with a first date, but at the end of the night both were happy and they kissed good night.

Billy called Rocky rather than texted when he got home. "Hi."

"There you are. I've been so anxious waiting to hear from you. How did it go?"

"Pretty well. I was really nervous, but the movie was funny and we kissed good night. I think we will definitely go out again.

"Of course, you will. And, then there will be a third date and that's the one where you will fuck her." Billy nervously laughed. "I'm serious. You know the third date is the one so-called sex date.

"Nothing like putting pressure on."

"I'm sorry. I didn't mean to make you feel nervous, but you've got this Billy. You have fucked the hell out of me in every way imaginable and you had really built me up in your mind."

"I suppose you're right."

"Of course, I am. Are you alone."

"No, but I am in my room."

"Good. I want you to hear you masturbate and cum for me. Will you do that?"

"Sh..Sure." Billy held his phone to his left ear and started stroking his cock with his right.

"Imagine that's my mouth deepthroating you, Billy. Does that feel good?"

"Oh yes"

"I'm playing with my clit, Billy. It's swollen from thinking about your big cock fucking my pussy. I wish your cock was inside of me now." Billy let out a deep breath and as precum started to flow from his cock.