Losing My Virginity to My Older Neighbor
Tags: Short Story, Sex, Erotica, Literatura, Fiction

Photo by Sharon McCutcheon

I was nineteen when I lost my virginity. It was also the day that began my love for older women. Nancy lived next door. Blonde, slender, busty, and a fifty-eight-year-old divorcee. She took the time one afternoon to teach me about sex and completely rocked my world.

That afternoon was hot as I vacuumed our pool. It was the summer between my freshman and sophomore year at college and other than trying to rekindle what I had with my high school girlfriend, the summer had been a complete flop. That is, until that day when Nancy called me over to where she lay sunning herself on her patio.

She lay back on a chaise lounge in a barely-there bikini. Her large breasts were straining the tiny leopard print bikini top and the small triangle between her legs was so small it was evident that she was completely shaved. I tried to avert my eyes out of politeness but eventually my hormones got the best of me. Awkwardly, I stood over her drinking in her entire body. From her beautiful smile down to her long tan legs, she was hot for any age; let alone for being in her fifties. Despite my best effort, my cock was starting to harden instantly.

Nancy had been reading a book and sipping on a cocktail when she called me over. “It’s too hot for work, don’t you think?” She asked as she lowered her sunglasses to pear over them at me.

Even her opening line sounded like a line from a porno, but I didn’t care. My eyes were glued to her body.

“It looks like you’re enjoying the afternoon,” I tried to think of something cool to say but failed miserably as I shifted awkwardly above her.

My friends in high school had always picked on me about my hot neighbor. To me, she had always been just Nancy. To my friends, she was the hot older chick that lived next door to me.. As I stood there on that hot summer afternoon, I could finally see what they had always been saying. She was smoking hot.

“Maybe we should go inside where it’s cooler,” Nancy offered slyly as she pushed her sunglasses back up and gave me a wicked smile. I could feel her eyes undressing me as they scanned up and down my body behind her sunglasses . I also knew what was on her mind and as I stared down at her. Her advances weren’t lost on my as my cock thickened in my shorts.

“Lead the way.”

Nancy swung her long tan legs off the chaise and offered me her hand to help up. As I did, she brushed against me with her ample breast and I felt it’s firmness. I’d had some experience with girls my age but up to that point, it had been limited. Nancy’s breast felt firmer than most of the short list of girls I’d gotten that far with. As she turned and headed for the backdoor, my eyes locked on her swimsuit bottom. The thing strap of the thong was wedged deep in her ass. The sight of her voluptuous hips swaying and the slight jiggle of her ass as she walked made my cock unspring the rest of the way. I was hoping I was reading the situation right as I followed her.

Inside, she leaned against the counter and took off her sunglasses. Her dazzling blue eyes seemed to pierce me as a sly smile broke across her face.

“I saw you in your hot tub a few weeks ago with that girl,” Nancy began.

Blushing, memories of that night came flooding back. Heather and I had come close to losing our virginities. In the end, she had said she wasn’t ready and had given me a hand job as I sat on the edge of the hot tub. We hadn’t realized that we had a witness.

“You did?” I croaked as I tried to look away from Nancy. She was staring intently at me.

Then, she took a step toward me. “I most certainly did. You have a big cock, you know?” Nancy was pressed against me by the time she finished her question.

“Kinda,” I replied.

“How big is it? I haven’t met a guy yet that hasn’t measured it.” She bit her lip sexily waiting for my answer. Her voice was barely a whisper and sultry. “It looked like eight.”

“Seven and three quarters,” I stammered. Her perfume was intoxicating and she was dangerously close.

“That three quarters makes all the difference in the world. Trust me.”

My cock was growing even more as she spoke and her sultry voice had me panting. Then, she leaned in and kissed me. “Mrs. Pemberton,” I whispered as she pulled slowly away.

“Nancy.”

“Nancy. What’s going on?”

“You are a virgin, aren’t you?” My face flushed as she asked me point blank what I had been dreading to confess.

“Yes.”

Nancy kissed me again. “Do you want to be?” She whispered as we parted.

“No.”

She took my hand. “Then follow me.”

I didn’t respond as I followed her through the house and up the stairs. My eyes were glued to her bare ass with the thong string buried deep in it. In her bedroom, she made sure the curtains were closed and no one would pry; especially my parents if they came home early from work. As she turned to me, Nancy pulled the string on her top and the tiny triangles fell loose. Pulling the other string over her head, she stood topless in front of me. I stared at her bare breasts in awe. Large, firm and capped with hard red nipples, they looked inviting. Her thong was next and in a second, Nancy stood naked in front of me and I saw for a fact that she was completely shaved. My cock was throbbing in my shorts.

My clothes were next. Nancy helped me out of my shirt, and she struggled to get my shorts down over my erect cock. As I was bared, Nancy lowered herself to her knees and studied my cock as she hefted it.

“You are big. Very big,” she told me before plunging my cock into her mouth.

Her warm wet mouth felt incredible as she worked my cock in and out of her mouth. Her hand reached up and cupped my balls as she moaned and stroked me between her lips. Nancy only did it for a minute before she pulled me out of her mouth and smiled up at me.

“Nancy,” I croaked as she stood and moved backward onto the bed. She pulled me toward her as she lay back and spread her legs. My mind was racing as my cock throbbed painfully.

Her cunt blossomed open. Small, pink and perfect, it glistened with her excitement as it spread open. Nancy pulled me over top of her and took my cock as she guided it into her. In a split-second, I was no longer a virgin. Her hot wetness enveloped me as I sank into her and she sighed. I was holding myself off her as I lodged my cock deep inside her.

“You feel so good,” Nancy cooed as I began thrusting. “So big.”

Looking down, I watched my cock impaling her as she clung to my arms. She was arching her back off the bed as I pushed deep inside her. It took only a minute for the inevitable to happen. As I thrust, the waves of pleasure started pulsing through me. My hips started thrusting harder as I gasped and my orgasm started to build.

“Oh God,” I groaned as I thrust into her.

“Go ahead,” Nancy coaxed me softly knowing my orgasm was imminent. She reached hand up and tenderly stroked my hair.

With a loud groan, I came inside her. Thick ropes of cum spurted from me and filled her as Nancy lay under me moaning. When I finished, I collapsed on top of her gasping as she continued stroking my hair.

“That’s what I expected,” she whispered to me as I finally looked up and saw her smiling at me. “Now move off me. Give me a second.”

Rolling to my side, Nancy pushed herself of the bed and I watched the sway of her ass as she walked into the bathroom. A minute later, the toilet flushed then I heard the water running in the sink. When she came back to bed, she was still smiling.

“That was quite a load. I had to wipe four times,” she told me as she lay against me and stroked my chest. “I made sure to wash myself too. But you shoiuld know, a man should never leave a woman unsatisfied.”

“What do you mean?”

“It’s not all about your pleasure Sweetie. Here,” she rolled onto her back, “use your mouth. I cleaned up well for you but stay high. Concentrate on my clit.”

Guessing her meaning, I moved between her legs. Nancy’s cunt was indeed clean without a drop of my spunk that I had shot into her. Nestling between her legs, I dipped my tongue furtively into her folds and tasted her sweetness. Her musky scent excited me, and I began to get hard again as I started lapping at her. Nancy’s hips moved in rhythm with my tongue on her clit and she moaned as she wound her hands into my hair to pull me in deeper. When her thighs clamped around my head, I knew she was coming. She arched her back and cried out as she climaxed, and I tasted a sweet gush of liquid in my mouth. It was the first time I had ever made a woman climax. It felt powerful and exciting.

“Very well done,” Nancy complimented with a sigh as she relaxed back onto the bed, and I felt so young and inexperienced compared to her.

My cock was hard and pulsing again as I looked up at her over her mound. Her large breasts were heaving.

Nancy pushed me backward with her hand then I watched as she rolled over and thrust her ass back toward me. Guessing her intention, I took her hips in my hands, I probed my cock into her wetness but failed to find her opening. Nancy reached between her legs, grasped my cock then guided me into her. From behind, I sank fully into her again.

“Fuck me,” she moaned, and it sounded guttural. Obeying her command, I started slamming my cock into her. Nancy was moaning and crying out as I pounded my cock into her. “Don’t stop fucking me,” she commanded.

I was hoping I could hold back. When Nancy came again, her entire body spasmed. Convulsing in front of me, and Nancy screamed as she climaxed. I was driving me cock into her hard enough I could feel my balls hitting her clit. Her cum coated my cock as I dug my fingers into her soft ass and fucked her even harder. My orgasm wasn’t far behind hers.

“I’m coming!” I announced as my cock pulsed with each hard thrust.

“Come with me,” Nancy pleaded and as I drove my cock savagely into her, I felt her pulsating around me.

“Oh God,” I groaned as I came again and released another stream of cum deep inside her. Nancy was panting and clawing at the bedding as she came with me.

Our mutual climax was hot, sensual and utterly amazing as we came together then collapsed on the bed in a tangle of sweaty satisfied flesh. I was gasping as Nancy pushed several locks of blonde hair from her face and smiled at me. She looked radiant.

That started our ritual that summer. Whenever my parents were gone, I was at Nancy’s and spent my time learning about sex and making love. There wasn’t a part of Nancy I hadn’t come in or on by the end of the summer. My ability to stave off my orgasm had grown, and I had become a more adept lover. The only problem was I was no longer interested in girls my own age. Nancy had shown me that older women were far more sensual, sexual and experienced. She had not only taken my virginity but had changed my outlook on women.