My high-school girlfriend Elaine was cute and sweet, but the problems in our relationship started when I met her mom.
We both grew up in the same small Eastern Pennsylvania town, but he was from money and I wasn’t. While I did drills, he mostly partied. However, whenever possible Craig would include me — especially because lots of the girls see the uniform and get wet, and he could thus score by being “the friend of the cadet.” We had a reasonably decent wingman system (pun intended), which worked out up until senior year when he got serious with what is now his wife.
Mrs. Georgia James.
She was blonde and curvy, with rosy lips, hips to die for, and heaps of Southern charm. The definition of a MILF, and boy, did I want to F.
Elaine never realized how much I wanted to fuck her mom, but she could tell something was wrong. For me, it was like all other women ceased to exist once I saw Mrs. Georgia James’s wicked smile and sultry walk. I fucked Elaine hard in the dark, pretending she was her mother, feeling ashamed even though the fantasy made me come harder than I ever had before.
Elaine and I broke up when I went to college, and I fucked plenty of other girls, but no one ever lived up to the fantasy of Georgia. I liked to imagine her on her knees, sucking me off, or riding me so hard those big tits bounced. Sometimes I fantasized about coming home for break and seducing her. “I need a young stud to keep up with me,” she’d say in that sweet Southern accent, and then she’d ride me until my dick exploded and my lungs gave out.
I never saw her in my hometown again, but senior year, I ran into Georgia in the city. She was walking down the street, all swinging hips and honey-colored hair, and when I realized it really was her, I walked straight into a light pole.
She frowned at me. “Chester? Is that you?”
“Mrs. James,” I said, struggling to regain my composure. “What a surprise to see you here.”
“I have a business meeting,” she said. “Oh, that’s right, you go to school here.” She looked me up and down, and her eyes widened a little at the sight of my newly defined pecs and arms. I’d taken up crew during freshman year and was now built like an athlete.
“Yes, ma’am, I do.”
Her smile tilted into that wicked angle I knew so well. “As polite as ever, I see.”
This was my one chance to live out my greatest sexual fantasy, so I mustered up my courage, winked, and said, “I always aim to please the ladies.”
She looked taken aback, but only for a moment. Then she smirked and stepped closer. “Is that so? What a kind young gentleman.”
She was only a foot away from me, close enough that I could see down her silky top. Her bra was pink with ribbons, and the sight of all that creamy skin plumped up by it got me hard. When I looked into her eyes again, I knew she could tell where my thoughts had gone. Her manicured hand rested on my chest, and then she trailed her nails down my shirt front to my belt buckle, lingering there.
“You’re all grown up,” she said, briefly dipping her fingers low enough to brush against my denim-covered dick. “What a delightful surprise.”
My dream was coming true: Mrs. Georgia James had just touched my penis. “I am, ma’am,” I said, “and I’d be delighted to show you exactly how grown-up I am.”
She pulled out one of her business cards and scribbled something on it. #203. “My hotel room,” she said, passing it to me with a wink. “Be there at eight.”
As I watched her saunter off, those wide hips swishing, I nearly whooped with joy. Georgia James, sexiest MILF alive, officially wanted my dick.
I spent the rest of the afternoon stressing out. What was I supposed to wear? Should I bring anything? If this had been high school and I’d still been courting Elaine, I would have shown up with flowers for the house. Was there etiquette when it came to fucking your ex’s mom?
In the end, I put on blue jeans and a button-up shirt and brought a bouquet of daisies. Maybe flowers were overkill, but there was no way I was going to mess this up.
I knocked on her hotel-room door exactly at eight, and it opened to reveal her dressed in a white robe. She tugged me into her room, laughing when she noticed the flowers.
“That’s unnecessary, but thank you, Chester.” She looked around the room. “Unfortunately, I don’t think I have anywhere to put them.”
Well, shit, flowers were a dumb choice. I ended up filling her ice bucket in the sink and stuffed the flowers in it, then turned around, anxious to get the party started.
While I’d been tending to the flowers, she’d stripped off her white robe and now stood in a pink bra-and-panties set. Her breasts nearly spilled out of the ribbon-edged cups, and she cocked her hip like a woman confident in her body. I gaped, taking in all those soft curves. “I’m a lucky man,” I said at last. “You look amazing.”
“I know,” she said, flipping her hair over her shoulder with a grin. “Now get over here and show me what that muscular young body can do.”
She didn’t have to tell me twice. I crossed to her, picking her up off the ground as I kissed her. She squeaked, then wrapped her legs around my waist, grinding against me as I carried her to bed. I tossed her down, then stripped off my clothing as fast as possible.
She sat up to run her fingers over my abs. “You look good enough to eat.” Her hand trailed lower, reaching my erect dick. She wrapped her fingers around it and stroked, then lowered her head and slid her lips over the tip. She took it deep, sliding her mouth up and down like a pro while her hand fondled my testicles.
“Holy shit,” I said.
She drew back to frown up at me. “Language, young man.”
“I apologize, ma’am. Your mouth is getting the best of my manners.”
She laughed. “I’m just kidding.” Then she set back in, working me over.
She drew back to suck her finger, then reached behind my testicles. I tensed when her finger brushed my asshole.
“Never had a woman rub your prostate before?” she asked. “Oh, honey, let me show you how to live.”
I tried to relax as that wet finger circled my ass. Then she pushed in, and it was a weird feeling, but her finger was small and delicate, and it wasn’t painful. A few inches in, she crooked that finger forward, and I damn near lost my mind.
“Sweet baby Jesus,” I said as she caressed a spot inside me. “Holy hell.”
She kept gently prodding inside my ass as she returned to sucking my dick. I was so keyed up, I started thrusting into her mouth, about to lose control. She moaned around my dick and reached down to finger herself.
I refused to humiliate myself by coming before she did, so I pulled back. Her finger slid out of me, and her mouth released my erection with a soft popping sound. “Delicious,” she said.
I stripped off her pink panties and bra and pushed her back down on the bed, then joined her. After a few long, sensuous kisses, I started working my way down her body, kissing all that soft skin. Her nipples were big and rosy, and she squirmed when I sucked on them hard. Her perfectly manicured nails sank into my hair as she guided me the rest of the way down to her pussy. Holy hell, older women were sexy. No timidity, no questions — just a hot-as-fuck cougar who knew what she wanted.
I ate her out enthusiastically, licking deep inside that wet, decadent pussy. She was drenched for me, and I worked two, then three fingers into her body, pumping them in and out slowly as I nuzzled her clitoris. Her thighs squeezed around my ears, and when I looked up, she was arching her back, sticking those big, beautiful breasts into the air.
I dipped further back and licked her asshole, and she gasped. Since she liked that, I toyed with her anus with a finger while licking through her cunt. She shivered and moaned, and then her thighs clamped hard around me as she shook through an orgasm.
“Oh, my word,” she said as she came down from the high. “That was good.”
“We aren’t done yet,” I said. My cock was almost painfully hard, and I stroked a hand over it before retrieving a condom from my discarded jeans. I rolled it on while she watched, propped up on her elbows, and then I leaned forward and picked her up.
She squealed in surprise as I’d hoped, then wrapped her legs around me. Her wet cunt pressed against my cock, and her hand dipped between our bodies to maneuver the tip inside. Once she’d positioned me, I bent my knees and thrusted up, jerking her body down at the same time.
She made a low, guttural sound and clawed my shoulders. “More,” she demanded.
My thighs burning, I gave my dick to her over and over again, bouncing her roughly. It was a hard position to maintain, requiring strength and balance, which was exactly why I’d chosen it. She wouldn’t be used to men her age carrying her around like this, which meant this college guy could give her something no one else could.
As she moaned and tightened her legs around me, I walked her back toward the wall. When her shoulders hit it, her eyes fluttered closed, and I knew she loved this kind of primal domination. I gripped her plump ass and started bucking hard, fucking her a few inches up the wall on every stroke. Her hair tangled as she thrashed her head, and her eyes were squeezed shut in pleasure.
I was ready to come, but she had at least one orgasm left in her, so after fucking her against the wall until my legs started shaking, I carried her to the bed and tipped her back. She was lying down with her legs on either side of my hips while I stood at the side of the bed, still buried inside her. I fucked into her, using those luscious hips for leverage. Once she was moaning loudly on every stroke, I reached forward and rubbed her clitoris hard and fast. She came with a scream, and the feel of that strong pussy clenching around me over and over again sent me over the edge. Come poured out of me in hot spurts, filling up the condom.
I collapsed over her, still pumping. She sifted her nails through my hair, looking drunk on the pleasure I’d given her. “Now, that was an experience,” she slurred.
I grinned. “One benefit of fucking a younger man — this experience is far from over.”