Summary: Young stud fucks MILF in all 3 holes on a hot summer day.
NOTE: This is a 2014 Summer Contest story, please vote.
Note 2: All characters are above 18 years of age.
Thanks to MAB7991, Robert and Goalz86 for editing this story.
My best friend’s hot mom
My best friend’s mom is hot, I mean HOT, and she knows it. She walks around in bikinis that show off her long legs, tight ass and big tits; she also often wears pantyhose and short skirts that make us all drool. All of Barry’s friends call her MILF, which makes Barry very upset, and every one of us has huge cumshots coming out of our cocks when we fantasize about her.
For me, this summer fantasy became reality.
Barry’s mom, Sandra, asked me if I could help them build a new shed for their backyard. Of course I agreed for the following reasons:
1. He paid me a lot of money to do this.
2. That’s what I do, make stuff, and I can make stuff cheaper and faster than companies can.
3. I will be near her house every day for about three weeks.
4. I wish I could fuck her…though that still seems like a distant dream.
She suggested I start the second week of July, and she was thrilled that Barry and his dad (the idiot who divorced Sandra a few years ago…no one could figure out why) went on a two week trip. Of course I agreed and took several photos of her every day until I started working on her.
When I came up with the design for the shed I saw her every day for a week before work started. Every day she would suggest changes and ask me to bring back different designs. Every day she would wear a sundress, or a t-shirt and shorts that almost no adult should wear except her. It was like she was laughing at me for letting her take it despite always dressing like that…which I believe was frustrating to her jealous ex.
Anyway, we eventually agreed on a design, and as I left he said, “I’m really looking forward to getting to know you better, Evan.”
“Me too.” I nodded, realizing my answer made no sense.
She flashed a bright, knee-bending smile and said, “As you know, it’s supposed to be a hundred degrees all week.”
“I’ll dress properly,” I shrugged.
She winked, the first sign that she had some ill intentions, “I’m not sure I would do that.”
Then Barry came down and we went out to party the last night before his trip…ignoring the fact that I still wished I could fuck his mom after he left.
I arrived at 8 a.m. the next morning as scheduled and was greeted by Sandra, who was wearing a robe and had obviously just gotten out of bed. I could see ample cleavage and briefly fantasized about opening her robe and devouring her right there. That said, I wanted to take my time to make sure I was correctly reading the many signs that she was interested in me… if I was wrong, it would be a shame and probably end the friendship.
She sent me back to where all the stuff had been the day before and I got to work. I was a few hours old when she came out to see me for the first time. Wearing a two piece bikini that showed off every curve of her perfect body, my cock immediately awoke in my shorts.
He asked: “How are things going?”
I replied: (As tempting as it was, I ignored the words “coming soon” and instead used the word my dad always used when asked similar questions, “slow and steady.”)
He said, “Go swimming, come with me if you want.”
“Not now, ma’am.” I shook my head, knowing that if I did, I would be ruined for the day.
“It’s Sandra,” he corrected. “My mother is a woman.”
“Of course, Sandra,” I nodded, watching as she turned around and dove effortlessly into the pool.
I was distracted for the next half hour as I tried to work while the most beautiful mom in the world swam nearby.
When she came out, it was like everything was in slow motion, like that scene from the 80s classic movie “School” when Phoebe Cates comes out of the pool. My cock got hard again and she grabbed the towel and asked, “Would you like some lemonade?”
“Sure,” I agreed, hoping she would be back outside and really thirsty. This time I also took the time to take off my top, revealing my very curvy upper body.
I worked for a few minutes until she came back with a glass of lemonade. She was also wearing a two-piece swimsuit and complimented me, “Looking nice.”
I joked, “How can you tell, it’s just a few scattered pieces of wood?”
“I didn’t mean the shack,” she said matter-of-factly, then turned back to the pool with a smile and sat down on a lounge chair.
I reluctantly went back to work. I hadn’t worked for two minutes when he called: “Evan, dear, can you come and help me?”
“Of course,” I replied, wiping my hands on my shorts and walking over to her.
When I approached her, she was applying lotion on her body. She asked, “Can you apply some lotion on my neck and back?”
Every teenage boy dreams of putting sunscreen on a hot woman. Of course I said, “Of course, I’d love to do that.”
She handed me the lotion, sat down on the floor and I sat down next to her. “Can you please take off my bikini top as well? I don’t want to have any stains on my face at my niece’s wedding in a few weeks.”
I wondered what she could possibly be wearing that caused such tan lines, but like any horny guy I agreed, “Of course.”
The bikini fell easily to the side and I could now see the edge of her sexy breasts. I thought about going bankrupt but decided to continue playing as I felt the inevitable coming. I covered her neck, shoulders and back thoroughly with lotion, massaging gently. She let out a slight moan as I lowered myself right above her ass.
Deciding to continue the slow seduction we performed on each other, I asked, “Aren’t you also worried about the tan lines on your butt?”
“Should I be like that?” she asked playfully.
“Just asking,” I replied, trying to flirt, “I’m honestly not sure what proper tanning etiquette is.”
“Better safe than sorry,” she replied, and surprised even me by lifting her hips. I watched as she pulled the rope, exposing her tight ass.
“Agreed,” I managed to mumble away, my imaginary mother now naked in front of me.
“Can you work on my torso area too?” she asked.
“If you insist,” I agreed, my already hard cock demanding release in my tight shorts. Although I am a confident man when it comes to women, I felt my hands shake as I poured lotion on her ass and began rubbing it in. Put lotion on thighs.
Just as I was about to finish she said, “My butt is going to explode, I hate the tan lines there.”
“This is so embarrassing,” I quipped, working the lotion between her ass cheeks with my fingers. I would love to slide my fingers from between her ass cheeks to her backdoor, or try to slide it into her pussy through the little window between her legs… I can’t see her pussy, but I could really reach it if I had the courage to take the risk.
As I thought about all the things I could do with my best friend’s mom, she ended the brief moment of teenage fantasy with a simple, “Thanks, honey.”
I was brought back to reality and stuttered, “N-no problem.”
I stood up, stared at her naked beauty for a while, then went back to work, stroking my cock.
I spent the next hour working out and trying not to spend too much time staring at the near naked perfection.
At about eleven she put her bikini top and bottoms back on and returned home without saying a word. I was disappointed because I never got to see her rack or her pussy fully. I thought a woman like her would cut or shave her hair, but there is the odd surprise.
The sexual tension was already high on the very first morning and it was clear that we both wanted the same thing. I worked steadily for the next hour, overcoming my sexual frustration and was about to go buy something for lunch when she returned, wearing a sundress and five inch heels in the heat today, as well as pantyhose. Although she is a beautiful woman, I have always liked the fact that she often wears pantyhose or even jeans around the house.
“I’m going away for a while,” she announced.
“I see,” I nodded and asked, “Isn’t it a little hot wearing tights?”
“Isn’t it a little too hot to wear a shirt?” he replied.
I laughed, “I just wore it a few minutes ago. I was going to get something to eat and most restaurants have no shirt and no service rules.”
“Such a shame,” he shrugged. “I’ll be back in a few hours and I left my phone number on the kitchen table in case you need me.”
“I should be fine,” I shrugged.
“I mean anything,” she repeated, emphasizing the word “anything.”
“Good to know,” I nodded in response, the chess game of sexual seduction continuing.
I saw him leave and followed him a few minutes later.
I didn’t see her again the whole afternoon, which ended about five o’clock. I went in and found her sitting on the couch, her feet in socks on the table, her toenails painted purple and very attractive, and she was watching CNN.
Hearing my voice she turned back and asked, “Is this the day over?”
“I think so,” I replied, still focusing on her long legs and beautiful feet.
“Why don’t you sit down and take a tour?” he offered.
“I’m dirty and sweaty,” I replied, not wanting to ruin her white furniture.
“I’m sure you are,” she quipped, a statement dripping with sexual innuendos.
“I need a shower,” I admitted.
“I think there’s one upstairs,” she smiled mischievously.
“You?” I joked.
“Actually, I have two,” he added, “although the room upstairs has better water pressure.”
“That’s good to know,” I nodded.
“Go take a shower,” she ordered, “and I’ll order some food. I don’t like eating alone, and Barry’s been out all week…it’s pretty lonely here.”
I agreed, the offer was too good to refuse, and the possibility of something happening in the future was increasing. “Of course, although I don’t have any clean clothes.”
“I’ll get you something,” she said.
I started to walk toward the first-floor bathroom, but she repeated the advice: “Go use my shower.”
“Okay,” I agreed, my cock fully stiff in my pants again, filled with anticipation.
I went into his room, went to the bathroom, quickly took off my clothes and jumped in the shower. I had only been in there a few minutes when I heard his voice. “Like the water pressure?”
I froze, ironically I was lathering up my cock at this point. I finally said, “Yeah, it’s pretty powerful.”
“It’s steamy in here, you’ll like it hot,” he teased, flirtation dripping from every word.
“I do,” I replied, which made it easier to flirt with him since I couldn’t see him.
“Do you need any help?” she asked me while she was taking a bath with me but unfortunately she was no longer wearing panties which shocked me.
I put my hand on my cock and I was amazed again… now I was living out my naked MILF fantasy… she was completely shaved and even more perfect than I had imagined.
“Is this for me?” she asked, looking at my fully erect, still throbbing eight-inch cock. “It’s bigger than I thought.”
I couldn’t speak. I wanted to say something witty, as I would to any teen slut I fucked and dominated on a regular basis, but I was speechless.
“I’ll take your inability to speak as a yes,” she smiled as she got down on her knees and took my cock in her hand.
I gasped…my long standing fantasy was finally coming true.
As if he read my mind, he asked, “I’m sure you’ve been fantasizing about this moment for quite some time, haven’t you, Evan?”
I stuttered and said, “Yes-yes.”
“Have you had any fantasies about it?” she asked, moving forward and taking my cock in her mouth.
I sighed and said, “Forever.”
I had never had sex in the shower before, but it was so exciting watching her boobs move up and down on my cock while the water stream fell on us.
Sadly, when the fantasy came true and her mouth was so pure and perfect, I only waited a minute before I warned, “I’m coming.”
She responded by pounding faster and taking all eight inches of cock deep. It was too much and I blew my load down her eager throat. She didn’t slow down until every last drop was taken. When she was done, she stood up and said, “What a delicious appetizer.”
Before I could say anything, she came out of the bathroom and said, “I left some clothes for you to wear.”
“Uh, thanks,” I said, confused by what had just happened, and she left just as I came away with her.
I took a quick shower and headed out. The toilet has a speedometer…nothing else. I shook my head in amusement, dried myself off, and put on my bathing suit, leaving nothing to the imagination.
When I got out, I couldn’t find her anywhere. Finally, I walked out and saw her back in the pool. She motioned to me, “Come and take a dip.”
I joked, finally having regained my old confidence, “Oh, I think I’m planning on doing more than just dipping, I’m planning on doing some deep drilling.”
She smiled and said, “I hope you will not just talk and do.”
I got in the pool with her and kissed her passionately. She responded, thrusting her tongue into my mouth and her hand went straight to my already stiff cock.
I started grabbing her big breasts through her thin bikini top. After kissing, I sat down on the edge of the pool and ordered, “Suck me.”
“Didn’t I already do that?” she asked shyly.
“I want to see those sexy lips worship my cock,” I said looking at her.
“You are a very naughty boy,” she joked as she pulled down my swimming trunks.
“You’re such a sexy slut,” I countered, confident that this abuse would turn her on.
As soon as my bathing suit came off, she gobbled up my cock, bobbing it up and down like so many teenage girls trying to impress me. The difference was that she didn’t close her mouth, she didn’t slow down, she took my whole cock into her mouth.
As she sucked, I told her, “I plan on making you my personal MILF sex toy all summer long, my slut.”
“Mmmmmmmm” she moaned on my cock, not slowing down at all.
After a few minutes of watching my mom fantasize about sucking cock the way I imagined she would, I ordered, “Naked.”
She pulled my cock out of her mouth and quickly removed her bikini top and bottom, throwing them both at me… with a sly smile.
I went back into the pool and picked her up, slowly lifting her onto my cock.
“Oh my god, you’re so strong,” she giggled as I picked her up, gasping as she realized what I was trying to do as I positioned her awkwardly on my cock. “Oh fuck, I love a man who takes charge.”
“I love a beautiful woman who knows her place,” I replied, slowly sliding my cock into her, the water acting as a great defensive barrier against me entering her body.
“Do you think I’m beautiful?” she asked, smiling.
“You are the hottest woman I know,” I replied, finally sliding my mushroom top into her.
“Ohhh,” she moaned as I entered her. “I’ve wanted you all along.”
“I know,” I replied triumphantly, before adding, “I’ve been fantasizing about this moment for a long time.”
When my entire cock was inside her she moaned, “You know how many times I have pleasured myself when you were done, I wish you would have come quietly to my room and taken me.”
“A lot like I thought,” I joked as I grabbed her in my arms and started fucking her.
“God,” she moaned, “You are so powerful.”
I kept fucking her, even though she was having a hard time holding on, trying to impress her. After fucking her for a few minutes she started talking dirty to me: “Fuck me, I love your cock”, “Fuck my pussy”, “Fill my pussy with that big snake of yours”, “I can’t believe we’ve been waiting so long” and “Oh my god, I love your big cock.”
Having my fantasies come true was amazing, but hearing her talk so dirty was even more exciting.
Finally, my arms burning, I slid off of her and she whimpered, “No, keep fucking me.”
Deciding to let him do the work for now, while also wanting to see those tits bounce, I ordered, “Put me on top of you as I got out of the pool and sat down in a lounge chair.”
She got out of the pool, stared at my engorged cock and joked, “If I ride you, I think the whole neighborhood will hear me scream.”
“Then let the whole neighborhood hear you scream,” I shrugged.
“You’re such a dirty boy,” she smiled, coming over to me and sitting down on my cock.
“You like that too,” I said, smiling, “don’t you?”
“God yes,” she moaned as she swallowed my cock.
“I want to see those tits bounce,” I ordered when my cock completely disappeared inside her pussy.
“Are you a boob man?” she asked, grabbing them and leaning forward so they pressed against my face.
“I’m a man with tits, pussy, ass and legs,” I replied, taking her erect left nipple into my mouth and slapping her ass. “Now ride me, my slut.”
“Yes Sir,” she moaned when I bit her nipple and she started riding my cock.
I moved from left to right, focusing on the nipples, then leaned back and ordered, “Sit up straight, I want to see the body move.”
She smiled and said, “That’s very well said.”
I smiled watching her ride and bounce. Her breasts were full and moans of pleasure came from her pouting lips. There is nothing sexier than a woman’s pursuit of pleasure. Her eyes showed hunger, her mouth showed pleasure, her body surrendered to desire.
Her moans continued to get louder, and as I began to move down on her, I knew she was close to cumming.
When I first saw her act she yelled, “FUUUUUUUCK, YESSSS.”
“Come on, my slut,” I grunted, preparing myself for her.
“God, yes, Evan, I love your cock,” she declared loudly.
“I like my own personal sex toy,” I replied.
“Oh yes, let me be your slut,” she moaned loudly, her breathing becoming erratic.
Wanting to fuck her to orgasm, I grabbed her with all my strength, flipped her over like a rag doll, and grabbed her ankles. As she lifted her legs high in the air, I plunged my cock back into her pussy.
As I reached new depths inside her hotbox, she cried out, “Oh fuu …
I obliged and hugged him.
“Oh fuck, yes, hit me,” she continued, breathing heavily.
“Are you close?” I asked, even though I knew the answer.
“Ready to explode,” she groaned.
“I’m going to get in that slut box of yours,” I warned, curious to see her reaction.
“Yes baby, fill my hole with your cum, baby, I want it so much,” she replied and I loosened her ankles. She wrapped her legs around me and tried to pull me in deeper.
I pulled back, wanting to climax with her at the same time, and then demanded, “Come on, my slut, come to me.”
His hand slapped her clit, and a few seconds later she screamed so loudly that not only her neighbors realized, but even dead people woke up, “Yeah, you’re talking bullshit.”
“Come on, slut,” I growled, spurting my cum inside her, thinking to myself that I really was a bastard.
I ejaculated inside her and she shook with her orgasm. “Oh, fuck, you’re so good,” she moaned.
“You’re not bad yourself,” I smiled, pulling away from her and watching a mixture of her and my cum ooze out of her pussy.
“Fuck” was all she could say as her body recovered from the orgasm. Finally, when my cock had calmed down, she said, “Maybe we should continue this inside. I’m worried the neighbors might wonder if I’ve been murdered.”
“Or a complete mess,” I quipped.
“Either,” she smiled and stood up.
“You’re so sexy,” I said, her body was so amazing.
“Same for you,” she smiled, placing her hand on my chest.
