\ As always, thanks for reading. If you want to read the whole thing, feel free. But if it’s too long for your liking, skip to:
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//
“Why don’t you stay for dinner, Coach?” Rebekah asked me. “Yeah, Coach!” Her son, Cooper chimed.
It had been about three weeks since Cooper’s mom and I hooked up for the first time. And after that, every week like clockwork, when I would go to her house to give her son a baseball lesson Ms. Ward would find a way to me stay. The night always ended the same—with Ms. Ward and I fucking each other senseless while her son slept obliviously down the hallway. We hadn’t put any labels on anything yet, but I was certainly enjoying her company.
So when Rebekah invited me to stay for dinner, you’ll understand that eating food was the furthest thing from my mind. “Yeah, that sounds great!” I responded. Rebekah gave me a knowing smile.
She made parmesan chicken and it was absolutely delicious. “Would you like another plate, Coach?” Rebekah inquired.
I smiled and held onto my stomach. “I couldn’t. I feel as full as a tick Ms. Ward.” It felt weird calling her “Ms. Ward” but it would have felt weirder calling her Rebecca in front of her son, who I didn’t think had any clue I was fucking his mom on a weekly basis. Had to keep up appearances.
It was a late dinner, as my lessons with Cooper usually went to 8 pm. “Alright, mister,” Rebekah said to her son. “Up to bed, it’s a school night.”
“But mooooom!” Cooper protested.
“No buts, mister! I tell you what, you go take a shower and when you’re done, I’ll let you watch one episode.”
Cooper said goodbye to me and raced up to the shower before his mom could change his mind.
“He’s a good kid.” I laughed.
“The best.” She confirmed. “So, the season is almost over. Do you . . . plan on continuing to give private lessons?”
I caught on pretty quick. This was Rebekah’s feeble attempt at trying to define our relationship. But I played along.
“Well I will be pretty busy with my second year of law school. But I suppose I could keep giving lessons to my favorite kids.”
“What about for your favorite Moms?” Rebekah teased.
“Them too.”
“Them!?” Rebekah sounded surprised.
I only smiled and winked.
“Well, I guess I shouldn’t take it too personally, Coach.” She said.
I was being mean, but I wanted to see if she’d just come out and say it. There was a brief moment of silence.
“I mean, we do have a little bit of an age gap, don’t we? You’re 23; I’m 37. It would be weird for a stud like you to be hung up on such an old lady.” She stated.
After the hours of hot fucking and lovemaking that we had engaged in over the last several weeks, I was surprised she couldn’t tell how crazy I was about her.
“I’m jealous of you, you know.” Rebekah said. “Still in school, I mean. Sometimes, I wonder if I would be where I am today if I’d had a little more fun in College. But I had to be the perfect little student for my parents, and when I met my hus— my ex, I fell hard. I wouldn’t want to keep you from what I feel I missed out on.”
Jesus Christ, she looked beautiful, sitting there feeling sorry for herself. Rebekah was 5’5 with long brown hair, 34DD breasts, high cheekbones, and beautiful brown doe eyes. She didn’t know that she put the girls I went to school with to shame. I felt my cock begin to harden down the right leg of my shorts. I’d be pitching a tent here pretty soon. I caught her eye, and smiled at her.
“Believe me, Rebekah, it’s not all it’s cracked up to be. It’s really a means to an end for me—I’ve always wanted to be a lawyer.” I said.
She answered, “well it’s too bad you haven’t already graduated. You could help me with the mess I’m in now!” It’s true, I hadn’t taken family law, so I was pretty useless when it came to giving her any advice on her divorce. We laughed, and I reached out and touched her hand.
I opened my mouth and made a suggestion. What if we experience what’s left of my schooling life . . . Together?”
“Ryan, I have a kid. I have a job.” Although Rebekah had been a stay at home mom for the last 10 years, during her divorce she had decided to get a job teaching again for the upcoming year. She didn’t want to have to solely rely on her ex-husband’s alimony.
“If we did though,” I started, “what would you want to do?”
“I shouldn’t say anything.”
“Come on!” I pled.
“Well, I’d want to have a lot of sex. I was practically a virgin when I got married. I’d want to experiment with it—different places, different ways and means, different people . . . more people.”
I nearly spit the water I was drinking when I heard he say she would be down for a threesome or more.
“Well I know several guys who would give up their right nut to bed you.” I teased.
“Ryan!” Rebekah slapped my arm in mock disgust, but didn’t move it.
“Have you . . . experimented much?” Rebekah asked.
“Oh yes, but a gentleman shouldn’t tell.”
We both looked up at the ceiling as we heard a shower start.
************** Sexy Stuff Starts Here ******
“Well maybe I’ll have to force it out of you!” Rebecca quietly exclaimed, and jumped on my lap in my kitchen table chair. I could feel the heat between her legs warming my cock as we began to make out.
“We have to be quiet so we can hear when the shower stops.” Rebekah said. “But I need this dick back inside of me, right now.”
Rebekah’s lips were divine as they fell onto my own. Her breath tasted like dinner, but I’m sure mine did as well. Our mouths opened and began to enjoy the company of each other’s tongues.
She giggled.
“What?” I asked between kisses.
“You want me. I can feel it.” She smiled, finally realizing that there was no other woman for me.
Rebekah reached down, crossing her arms and grabbed the bottom of her top, then in one smooth motion lifted it off of her. Clad to her full breasts was a shiny red bra. I smashed my mouth back against her lips as fondled her breasts through the silk armor containing them.
God what a woman. We kissed as she straddled and ground her hips against mine. Without looking I reached around Rebekah’s back with one arm, caressing her tits with my other. I found her clasp and released it. The bra only came free once I released me grip on her people-pleasing breasts.
She leaned her back against the table and gave me a little shimmy. Her fair skin accented her pink nipples perfectly, as she lifted one to her mouth and took it into her mouth, maintaining eye contact with me the entire time.
My need for her turned primal as I took her other breast into my mouth and sucked and massaged her nipple with my tongue. My cock strained against my shorts, and against her ass.
The woman’s desperation was apparent. She moaned into her breast at the movements my tongue made against the nerves on her nipple. I release her nipple from my mouth and then slowly kissed upward to her clavicle.
Rebekah lifted my shirt over my head , and her hands caressed, grabbed, and clawed my chest and soldiers as I continued the onslaught of my mouth onto her chest. Our staggered breathing filled the air, but we were careful to listen for the shower so we knew when to stop. She touched and lightly pinched my nipples, making me throb underneath her.
Rebekah then stood up and slid her jeans and silky red panties off in one fluid movement before sliding my dish away and sitting on the table in front of me with her legs spread. She sat completely naked in front of me now and I was so hard I thought my nose might start bleeding.
I dove face first between her legs and began lapping at her nectar like it was a Turkish delight. She tasted aroused, sweet, and tangy—and her moans only served to urge me on.
While I ate, I slid my shorts and underwear off, feeling the warm kitchen air around my upright and exposed cock. Finally undressed, I kissed up Rebekah’s body and found her lips, making her taste what I tasted.
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“Fuck me.” She whispered.
And I obeyed.
With Rebekah on the table, I stood and spread her thighs before teasing her entrance with the hard bulbous head of my cock. Then I pushed inside.
Fuck it felt good. Her flesh and mine, were one. Joined at the waist and drawing in each other’s breaths in fluid motion. How a 37 year old woman managed to be so tight was beyond me.
Rebekah quietly gasped between thrusts. She knew as well as I did that that she might give us away, so I held my hand over her mouth as I began fucking her in earnest where we had just eaten.
The kitchen table was shaking under our activity, and I let my hand drop from Rebekah’s lips. I lowered my lips back to her breasts and sucked in earnest while We fucked in her kitchen. Her quiet panting in my ear spurred me on as she repeatedly sheathed my spear. With a free hand I began stroking Rebekah’s clit as I fucked her. “Fuck your cock feels good!” She moaned her breath. “Oh God, you fill me up so good!”
My mouth returned to her breast as I licked, sucked, and fucked my player’s mom. “Oooooohhh, you’re such a fucking — oh, yes! Don’t stop, don’t fucking stop, Coach! Harder!”
I obeyed, and the table groaned under our fucking. Her pussy felt so fucking silky and smooth and warm. I knew that I had to control my thoughts and breathing in order to last.
“Faster you bastard, fuck me faster—make mommy cum! Make mommy cum!” The panting in my ears gained volume, but I didn’t care. I would fuck this woman until my legs gave out if I had to.
Then. Fortuitously, she came. Hard. She bit down on my shoulder as I bottomed out and held her hips to mine, squeezing as much of her ass as I could grasp while she spasmed. And God was it a long one. I had never made a woman climax for so long before.
As her climax ceased, so did the running water. We hadn’t been going at it for more than 15 minutes but it felt so much longer. I was sweating, Rebekah was glistening. We rushed to put our clothes on. My dick frustrated that it hadn’t had its own release yet.
Cooper came downstairs and saw me, fully dressed, thankfully. “Oh hey Coach. What are you still doing here?” I’m glad he didn’t yet recognize the smell of sex either.
“Oh, I uh, figured I’d watch that show with you and then head out, if that’s ok with you?”
“Yeah, sure!”
We watched some Star Wars cartoon show, and when it was over, Cooper’s mom took him up to bed. Rebekah texted me and told me to stick around.
I waited maybe another 30 minutes, just scrolling on my phone when a text popped up. From Rebekah.
“My room.” It said.
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I already knew the way. As I quietly climbed the stairs, my cock twitched in anticipation. When I opened her door I was treated to the vision of Rebekah naked and sprawled on her back with her legs spread. But what really made my dick flex was seeing where her fingers were. There on the bed, sat this beautiful, sexy milf, and she had two fingers inside of her asshole.
She was moaning loudly too. I guess Cooper was asleep. I could see the bottle of lube on her bedside table and that her fingers were covered in lubricant as she slowly plunged two fingers up to her second knuckle.
I was completely at attention, closed the door and walked closer to her as she opened her eyes, looking at me.
“I’ve only ever used fingers before, but since we’re experiencing college together now, I figured anal was on the table.”
I swear she was speaking in tongues, and I stood there staring at her fingers, prepping her ass for me.
“Fuck me in the ass?” She asked.
What a gal. I knelt on the bed in front of her, and leaned forward. She began kissing my neck as my dick rested there against her ass. She whispered, “come on, Coach. I could tell from my question earlier that this isn’t your first time. I bet mine feels better than whatever slut you had last time.”
I roared and grabbed the lube, applying it generously to my aching cock. There was no way I would last long. It had been ages since I was last in the tightest hole.
I returned my focus to between her legs, and lined the head of my cock up to Ms. Ward’s virgin asshole. I paused.
“Put it in my ass, Coach. I want this. Please!” She begged.
Her words awakened the animal inside of me and I watched as my dick pressed against her rosebud. Rebekah took a deep breath as her hole slowly opened for my cock. Before long, she had taken the entire tip. I held her there, and told her to take another deep breath. Only after her breathing normalized did I start to inch forward, more of my cock disappearing inside of her. It was so incredibly hot watching her face as more of my cock claimed her tight ass.
“Ooooohhh FUCK!” She cried when I was about half way in.
Her mouth stretched open and she stared into my eyes as I kept slowly pushing inside of her. Pause. Breathe. Push. Repeat.
About 5 minutes later, I was all of the way inside of her. Her tight sphincter spasmed around my tool, so tight.
“Oh my God it’s all the way in my asssss.” She moaned through gritted teeth. We kissed and rocked, the motion allowing me to press centimeters further into her without withdrawing.
She was in a little bit of pain, I could tell. I didn’t want to to do anything without her telling me to. Her hand lay pressed against my chest as if telling me to wait.
As we continued to lightly rock, I saw her eyes roll back. “Ooohh. Ok, I think I’m ready. Fuck my ass, Coach.”
I slowly slid my cock out a few inches, her ring clinging to my shaft as it moved, attempting to milk me.
“Ooooohhh,” I watched Rebekah’s thighs shake as she moaned through clenched teeth. One hand moved to her clit and I leaned down to suck on her massive tits once more to help distract from the invader in her ass.
Her groans grew more relaxed, and I began to pick up the pace of her ass fucking. The noises, like tiny whimpers drove me wild. Her mouth in a permanent “0”, her brow furrowed in both concern and pleasure, and her eyes struggling to focus on me as they repeatedly looked to the sky prayerfully.
“Ryan.” She whimpered, “tell me I’m yours.”
I groaned and flexed my cock in her tight entrance. “You’re all mine, Rebekah!”
“Say it again? Oh-my-god-it-feels-so-!”
“You’re all mine, Rebekah!”
“Yeah? You like fucking my tight little asshole, you lucky bastard? I never let my ex-husband near it—I must have been saving it for you. Now tell me you’re all mine! OH FUCK!”
God, this woman was a crazy good fuck.
“I love it. Your ass feels so fucking good., Rebekah. It fits me perfectly!”
Rebekah stopped me by putting a hand on my chest. “I want to change my position.” She pushed me off and turned around onto her hands and knees. I followed suit and squatted on the bed above her ass, then slowly put myself back inside of her. I reached for more lubricant and squeezed, causing the fluid to spill all around where my cock connected to her backdoor. Every new thrust brought in more lubricant, helping to comfortable increase our pace.
Soon I wasn’t doing anything at all. Rather, Rebekah was fucking me! I watched in awe as she panted around my manhood. She was clearly feeling it, as there were no more sharp intakes of pain or deep breaths—only sex and desire. She was fucking me harder than I expected she would be able her first time, and I began to meet her movements.
“OH MY GOD, RYAN! I’M FUCKING CUMMINGGG!” Liquid ejected forcefully onto Rebekah’s sheets from her pussy as she came hard while rubbing her clit. As she came, her asshole spasmed violently on my cock, and I was undone. I grabbed her hips to still her, pushed in as deep as I could reach and unloaded.
I called out in prayer and to Rebekah as I unleashed a torrent of white, hot, cum inside Rebekah’s bum. As our orgasms faded together, we both collapsed into the bed. Me on top of her, my spent dick slowly softening inside of her enough to withdraw.
I shouldn’t have, but I fell asleep in Rebekah’s bed. She woke me up the next morning before her son woke up and I snuck out.
Source: reddit.com/r/gonewildstories/comments/t84cj8/my_anal_virgin_milf_exgirlfriend_let_me_be_the
That mom passed “the bar exam.”
Takes me back to my first time.