My First Cougar: Never Forget Her


I had just graduated from high school and was spending the summer before college driving down the west coast from Portland to San Diego. I picked up odd jobs along the way for gas and food and finally found myself in the sleepy little town of Cambria.

I landed a gig at a Bed and Breakfast at the beach and basically did anything that needed to be done, from minor repairs to delivering room service to the guests. The owners were in their late 40s. Rich was a corporate mucky muck in San Francisco while Teresa ran the B&B.

A New York City native, Teresa was a tough cookie and ran a tight ship. The B&B had been her grandparents and she was fiercely determined to maintain the standards set up generations ago. Rich saw the B&B as the investment it was yet didn’t have the passion for the property.

You could tell she was lonely, often hanging around the office long after her desk was clear. It was on those occasions that we would end up chatting about this and that. “Rich is a good guy,” she would ultimately confide in me, “He just spends long hours at work and is too tired to drive down for the weekends.”

She didn’t notice or didn’t care how young I was. And while I took charge in my constant fantasies about her, I had never been with a married woman. I’d never been with an older woman. Truth be told, I had never been with any woman, but that’s not something you go around telling women, especially one who seems to be flirting at every opportunity.

One night as I was cleaning up the shop, enjoying beer number two, she came out front and sighed, “I wish I would have met you when I was younger.” I don’t remember exactly what I said next since my sudden stiffness sucked any breath right out of me.

I gulped hard and licked my suddenly dry lips. She lifted her beer bottle, clicking haymana escort against mine, “We would have had a lot of fun together if we had met at 18.”

Now I do distinctly remember this moment because as she smiled at me, her beer bottle raised, she tongued the rim, never once breaking eye contact. I could barely breathe. Having fantasized about this every night in my mind, I had two thoughts, “Is this really happening?” and “God don’t let me blow this.”

I knew where this was leading and I kept telling myself “Remember, you want this woman!” I broke away from her gaze and dropped my eyes to the pale skin of her breasts just visible above the curved neckline of her top. I just stared, wondering how she felt and tasted. I felt my ears get hot and red.

While her smile was more than memorable, her deep green eyes were mesmerizing, practically begging me to fuck her. She reached across, brushing the hair from my forehead, tracing her fingers down the side of my face and along my jaw. I reached up, took her hand and brought her palm up to my lips. Her taste made my insides flash hot.

Never looking away, she stood up, grabbed my hand and walked toward the office door. This was my opportunity to finally experience the woman I had been dreaming about all summer. I pulled her close, kissing the tip of her nose, then leaned forward and kissed right below her ear. I felt her body press into mine, a feeling I wouldn’t soon forget.

Her body felt good against. Lost in the feeling, I suddenly felt her hand along my lower back, then sliding lower before she grabbed my ass and pulled me closer. It made me wonder if she hadn’t thought of this before, as she no doubt knew what she was doing. She tilted her head back, an invitation I couldn’t turn down. I kissed keçiören escort her neck slowly from chin on down to the top of her chest. She whimpered and I felt her body melt into me. Inexplicably, thoughts of her husband crept into my mind, resulting in my pulling back.

As if reading my mind, she reassured me that no one would find out, that this was something we both wanted. She knew we had both shared thoughts neither of us wanted public, and this would accompany them. She ran her hands through the hair right above my ears and pulled me in for a kiss. Her lips were open and her tongue met mine with a ripple of pleasure.

She slipped off her shirt, no bra to be seen, revealing beautifully shaped breasts. I must have looked as goofy as I felt, staring and gawking at her body, not to mention rubbing the obvious hardness through my shorts. We kissed again, her hand brushing against my solid cock as we did. She whispered that it had been some time since her husband had been so hard. Reaching under the band of my shorts, she ran her cool fingers up and down my shaft barely skimming the taut skin. Feeling me throb, she whispered, “Let me take care of you.”

She stood and stepped out of her skirt. She had a great body, neatly trimmed in all the right places. She reached for me, yet kept just enough distance. She insisted she just wanted to rub my abs, it was all I could do just to hold off spilling my seed. I could smell her love juices as she stood in front of me and held my head to her breasts. “I’m gonna cum, baby.” I croaked out with a throat dry as the desert.

She knelt in front of me, tracing her tongue down the center of my chest as she did while her other hand cradled my balls confidently. I let out a world class moan and she leaned back, giving kızılay escort me an amazing view of her gorgeous breasts, sparkling with beads of sweat.

I watched and shivered as her fingers, nails bright red and shiny, stroked me, hypnotizing me. Up and down, twisting, tapping, wagging. She worked my cock until I could no longer resist, surrendering into her hands. I moaned yet again as my I unloaded at last. Teresa spread her arms, arching her back, catching my load on her breasts. It was a sight I will never forget.

My mind was lost in the moment, though I continued thrusting into her hands. Nearing the end of my orgasm, I felt her mouth slide onto me. I felt my eyes roll back in my head as she milked me … every drop being licked or sucked from my once-raging hard on.

I finally opened my eyes as she crawled up to sit on my lap facing me. We held on to one other, my cock pressed into her lower belly “What about you, baby?” I inquired, running my hands up and down the damp skin on her back. I wanted more and she knew it.

“Next time,” she smiled back.

This event, and many others, continued over the remainder of the summer. We enjoyed beers after the day’s work and I listened to everything from things needing fixed at the B&B to the beach town’s no-good mayor ruining the place for the locals. After which, we would fuck each other silly. We laughed and played like we were kids. She not only taught me the finer aspects of fucking, she also taught me how to go down on a woman – an education which continues to pay dividends long after our summer together.

I didn’t think much about it then, but looking back I understand the attention she sought. Not only for someone to listen, but for the physical side of life surely missing with Rich. I was as supportive as any wet-behind-the-ears young cub could be, but aside from the sex, there was little we truly had in common. By the time summer was over we were both ready to move on. I never saw Teresa again, but I still stiffen up a bit when I find myself thinking back to those shared summer moments. I’ll never forget her.

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