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Going Down Madison's Avenue

"My virgin experience with another woman"

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Author's Notes

"My first story. I'm not a writer. <p> [ADVERT] </p>Please be gentle with me."

When I arrived for my tennis lesson, I was surprised to see a beautiful woman who I’d never seen before. She couldn’t have been more than mid-20’s, her silky black hair swinging in a ponytail while she collected balls from her previous lesson. She was about my height, 5’6” with much longer, more slender legs and narrower hips. Her arms were sinewy, her B-cup breasts accentuated by her form-fitting lycra top. I couldn’t help noticing her sports bra wasn’t enough to contain her taut nipples. Her smooth, tanned skin made my mouth water.

“Mrs. G! When I saw you on the schedule, I made the pro swap lessons with me so I could see you!”

I couldn’t hide my confused expression.

“It’s me, Madison.”

“Madison?” I remembered an awkward seventeen-year old girl who was friends with my younger son in high school. 

“I know. I’ve swanned,” she said with a coy smile and a curtsy.

“I didn’t recognize you without your pink and blue hair.”

“Yeah and my zits and scrawny body.”

“I always adored you, Madison.”

“I guess I was a late bloomer like you!” 

She was picked on a lot in school for her punk clothes and hair. She was very skinny, without any of the feminine curves from puberty. Her parents were going through some marital issues to boot. Even her mother picked at her constantly, telling her how ugly she was, how she wouldn’t amount to anything. I was a later bloomer myself so I had a lot of empathy for her. My son included her in his group of friends. Still, they were kind of cold and sarcastic with her. Whenever she came to our house, I made a point to compliment her. She’d come in the kitchen and we’d talk and talk. I encouraged her. I told her about my delayed development. She was clever and creative. She read a lot which isn’t something kids her generation do much anymore. She was fascinated by my early years when punk was still new. It’s weird to think punk was more acceptable when I was young. We were the outcasts then. I tried to make her feel cared for in a world which obviously was very hard on her.

“What are you doing here?”

We caught up while hitting balls back and forth. She’d lost touch with my son in college. During the week she commuted on the train to work for a renowned ad agency in downtown Chicago. She was teaching tennis on weekends to earn a little extra. She’d moved back to the northern suburbs, living with her parents to save some money.

After a while, she came over to my side of the court to give me some pointers. She’d position my hands and hold my arms and hips to guide me through the right strokes. I have to admit something electric shot through my body every time she touched me. I was so scared she would notice. Could she feel it too? 

I should say I’ve been (mostly) happily married to my husband for thirty years. I’ve never been with a woman, or even thought about it. Until recently. Every marriage has its ups and downs. It wasn’t all my husband’s fault. Yes, he had a new boss who was making his life miserable. I was going through menopause which was almost like the roller coaster of puberty or pregnancy. At times horny. At times hot and sweaty. I didn’t get wet like I used to which made sex painful. For some reason, I found myself drifting to online lesbian erotica. Reading stories excited me in ways I hadn’t considered. I got bolder, starting to chat online chats with women. Often my chats led to mutual masturbation. At least I thought they were masturbating. I knew I was. That was all fantasy.

“Would it be OK if I call you sometime?” she asked me after the lesson was over. “I miss our conversations. You made me feel so special during a really awkward time in my life.”

“Sweetie, you're not that awkward girl anymore. You must get plenty of attention from boys now.”

“I know I’m not ugly but it’s not like I’m really what boys like. They want bigger tits and blonde hair, not a skinny athlete. I’m too butch for boys and not butch enough for girls!” she laughed. 

“You’ve matured into a spectacular woman.” Could she see me blush?

We texted over the next few weeks and I took more lessons with her. Everything seemed fun and flirty. But she was my son’s age. What could she possibly see in this fifty-plus year old with cellulite thighs and a bulging tummy? After every tennis lesson with her, I couldn’t contain myself on the way home. Before I left the parking lot, I’d hike my tennis dress up over my wide hips and narrow waist. I’d slip my hand inside my lycra shorts, my fingers pulling apart the flesh of my pussy until they were coated in my juices. Then I’d massage my clit on the drive. A few guys and even some women in pick-up trucks had a pretty good view of what I was doing which turned me on even more. I always climaxed by the time I pulled into my garage.

Then I took the plunge. My husband was going fishing for the weekend. I texted her a glass emoji with a date and time.

I was outside saying good-bye to my husband when she pulled up. She’d come straight from the courts, her hair pulled back, her tennis outfit accentuating her lithe body, I couldn’t help but look her up and down with those delicious long legs exposed to the short hem of her tennis skirt. My husband noticed, too.

“Hi Mr. G,” she said. “Have a good trip.”

I asked Madison to wait for me by the front door.

“Who’s that?” he whispered to me.

“Billy’s friend Madison from high school.” 

“I don’t remember any of Billy’s friends looking like that.”

“Don’t be a perv!” I said with a playful punch to his stomach.

He shocked me with a sexy, deep, warm kiss, his hands roving my backside. I wrapped my arms around his neck. We kissed a bit more.

“What was that?” I asked him.

“You know how I like an audience.”

“We’ll have to try more of that when you get back,” I said. One of our few “kinks” is a little friendly exhibitionism. It had been awhile.

I offered Madison a glass of wine. We sat out by our pool in the backyard with a few snacks I’d made.

“Wow, you and Mr. G. still know how to go hot and heavy,” she teased.

“It’s not what you think. He’s a bit of a show off.”

“Like how?”

“Maybe after we finish the bottle,” I said, taking a gulp to build up my courage.

She told me how she always thought we had the model marriage. I’d forgotten about a Halloween where I dressed up as Debbie Harry from Blondie and Brian was one of the bandmates. We played Blondie music. My boys were mortified. Madison said she thought we were the sexiest couple she’d ever seen. She even implied she might have fantasized about us. I was shocked!

“I’m so embarrassed. I shouldn’t have said anything,” she backpedaled.

“Sweetie, you have no idea how flattered I am,” I replied, placing my hand gingerly on hers.

“You mind if I take a shower?” she asked. “I’m still sweaty and gross from being on the courts all day.” If she only knew how her musky scent drove me wild. 

“Of course. Go ahead,” I lied. I really wanted to plunge my tongue between her thighs to taste the fragrance of her unwashed pussy. “I’ll fix us a little dinner.”

I’d prepared a salad and baked salmon ahead of time. While I put the plates together and set the table, I imagined her in the shower. I desperately wanted to see her, the water cascading over her body. I concocted a story in my mind. I would bring her some fresh towels. I could sneak in and put a few fresh towels on the vanity. We had a thick shower curtain so I wouldn’t be invading her privacy. That’s what I would tell her if she reacted badly. 

I heard the water running and the door was ajar. I hesitated outside the door, my heart racing. Would I really do this? What was I expecting to happen? I mustered all my courage. I knocked and entered without pausing for her to say anything.

“I brought you some…” but I couldn’t finish my sentence. 

Madison sat on the edge of the tub, the hand-sprayer pressed into her pussy and her other hand furiously stroking her clit.

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“Oh my god, I’m so…” I dropped the towels on the floor and hurried out of the room. I tried to collect myself in the kitchen. Completely flustered, embarrassed, aroused, confused. 

“I’m sorry, Mrs. G.” she said, standing, wrapped in a towel, a puddle forming around her feet.

“No, I should never have…”

“Thinking of you in your Blondie costume, seeing Mr. G. kiss you like that. It just brought back so many memories. I had the biggest crush on you. It’s not the first time I masturbated in that bathroom imagining what it would be like to be with you.”

I stood silent, paralyzed by the feelings her confession aroused.

“Oh my god, I’ll go. I’ve ruined everything. I can’t believe this happened.”

“Wait,” I said. My mind went blank. My body took command. I walked over to her, hugged her and kissed her. My first kiss with a woman. Her lips greeted mine without surprise. No awkwardness. Two pairs of moist lips slightly parted, certain of what to do. Soft. Sensual. 

“I never realized how much I wanted this, too,” I whispered.

Madison took immediate control.

She pressed me against the kitchen counter and lifted me up. She was so strong. She kissed me more deeply, passionately. Our tongues danced. Her towel dropped to the floor. She grabbed my legs and guided them around her waist. She kissed my neck, stroked my hair, her hands roved across my back, my waist and hips. We breathed fast and furious, our kisses desperate.

She pulled off my t-shirt. My bra fell with a snap of her fingers. She peeled off my shorts and underwear. I’d never had someone take control of me like this. She slid onto one of our barstools and laid me flat on the counter. My feet naturally rested on her shoulders when she buried her face between my thighs. The feel of her lips on my pussy, the way she sucked the folds of flesh, the way she moved her tongue, the shape of the movement, the rhythm of the various pressures and speeds. Women always say they’ve never experienced oral sex the way another woman can give it to them. I finally understood. 

Her hands gripped my ass, holding me slightly in the air so she could devour me. Her nails dug into my flesh. She sensed my impending climax and bit the inside of my thigh to cool me off. The thrill and the pain were potent. Then she’d blow kisses and lick me to soothe where she’d bitten me. Then she’d start all over, working her tongue inside my pussy and over my clit. Wave after wave she brought me to the edge, only to shut the door until I begged her, I tried to wriggle free, I screamed for her to let me cum.

She suddenly stood up, her face close to mine, a mischievous, satisfied smile on her lips. I lifted my head to kiss her. She pulled back for an instant, then pushed forward to meet my kiss, thrusting two fingers inside me at the same time. I didn’t expect the sudden penetration. Our mouths were tangled in passion, the scent of my juices on her lips. The sensation launched me over the edge, my pussy clenching around her fingers, squeezing her inside me. 

She kissed me tenderly, bringing me down from my high, my breath slowing.

“You were ready for a release,” she said with a laugh.

“I’ve been imagining this moment since our first lesson,” I told her, stroking her face.

I sat up on the counter and led her to the bedroom, our feet sinking into the plush carpet as we walked hand-in-hand. We laid snuggling on the bed, stroking each other. She confessed more about her teenage fantasies of me. I confessed to her about pleasuring myself on my drive home from our lessons. I confessed I’d never been with a woman. She promised it would come naturally.

“Where did you learn to take control like that?” I asked.

She told me the story of an older woman who became her girlfriend senior year in college. Her first real love.

We kissed again. She guided my face to her small, pert breasts, the perfect mouthful. Her back arched when I took her hard nipples into my mouth. Her chest heaved when I massaged her, pinching, rubbing, softly stroking. I kissed her rock hard tummy. I kissed her smooth, shaved pubic mound.

She used her legs to flip me over, then lowered herself onto my face, reverse cowgirl. 

I tasted a woman for the first time. I was intoxicated. 

My nose nestled between her firm ass, my mouth and tongue worked their way over her pussy and clit. She pressed herself harder into my face, massaging my breasts and stomach. 

Madison undulated her hips. I met her rhythm to sweep my tongue along her slit. She rubbed my clit with her thumb, teased my pussy with her fingers. I had difficulty concentrating on giving her pleasure with the pleasure she gave to me.

Then she leaned forward, bracing herself on my thighs, her nails once again digging into my soft flesh. She ground her pussy over my mouth, harder and faster. She instructed me on what she wanted, telling me how much pressure, how much speed. We were in perfect synch.

“I’m going to cum,” she cried.

“Mmmhmmm,” I replied into her pussy.

“No, I mean, get ready. I cum a lot when I cum.”

“Mmmhmmm.” I wanted nothing more than the power to make her climax, to know I could bestow the gift of orgasm to her.

Suddenly I was drowning. She lifted her hips to let me breathe. Streams of tangy fluid erupted from her. My face, my neck, the bed, everything was getting soaked. I opened my mouth wide, desperate to drink as much of her nectar as I could. 

I thought squirting was just some fantasy men created. This juice wasn’t thick. It smelled earthy, unlike any fluid I’d smelled before. I swallowed and swallowed, my hands gripped on her hips. I couldn’t suppress a laugh from the pure joy of such a novel experience.

Her arms buckled, collapsing her over my legs. She rolled over, her feet resting beside my head. She stroked my legs, teased her fingers through the wisps of my unshaved pussy.

“I warned you,” she laughed. “I didn’t freak you out, did I?”

“Are you kidding? That was incredible. Can you teach me how?”

We took a pause to remake the bed and clean ourselves up. We snuggled on the couch, naked under a blanket, drinking wine and talking and talking. Touching and stroking. Kissing.

“I want to do something special with you,” Madison said.

“What we did wasn’t special?”

She led me back to the bed. We sat with our legs wrapped around each other, kissing and sucking each other’s necks, breasts, nipples. 

Then she pushed me back onto the pillow. She laid in the opposite direction. Our legs were scissored. And she started to grind again.

She took my toes into her mouth. I did the same to her. My hands ran along those long, tanned legs of hers which I’d dreamed about so much. Her fingernails scratched along my thick thighs. 

Our slits rubbed against each other, slipping, sliding. The sound of our wetness colliding filled the room. Our scent filled the air. I didn’t have the same fluidity of motion she did, the way her hips rolled to press herself into me. I tried to match her. She began to grunt, a squeaky, throating, animal sound like when she’s hitting a tennis ball during a match. The beasts in us took over. Our pelvises thrusting to slap into one another, to slide and grind. The sensation was incredible. Our juices coated the inside of our thighs, oozed down to our asses, leaving a small wet spot on the fresh sheets. 

Her grunts grew louder, faster, matching the intensity of her hips.

The bed rocked.

Then she bit my ankle. I kissed her calf. We came together.

We barely slept or bathed for the rest of weekend. We ate and drank and fucked. We didn’t make love. We fucked like animals. We fucked with the desperation we may never see each other again. Sadly, I did not achieve my first squirting orgasm. I did get to drink several of Madison’s. Don’t ask me how I cleaned the house before my husband came home. I thought our scent was embedded in the walls and carpets.

Madison introduced me to so many new avenues. My first time with a woman. My first time with someone so much younger. My first time with someone who was friends with my son. My first time cheating on my husband. My first time understanding the true meaning of “guilty pleasure.”

Published 
Written by StephMom
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