I had one of my most memorable sexual experiences soon after I turned 18.
My sex partner was one of my motherís friends, Theresa. She was a petite blond woman of about age 28. Athletic and carefree, she was the outdoorsy type of hippy girl common in rural northern California in the 1970s. She wore tie-dye shirts, leather sandals and denim skirts and she frequently smoked weed and drank wine with my mother who sheíd been friends with for several years. Theresa lived across town from us in a small rented house and during my teen years she was a frequent visitor to our home. Sometimes Theresa served as a babysitter by staying overnight when my mother was out of town on work or school related projects.
Whatever the occasion, I always liked Theresa and her friendly ways. She could be relied on to bring a sunny, carefree attitude with her wherever she traveled. As an artist she was creative and always looking for new ways to see the world around her. She was also a bit of a joker and very uninhibited in her approach to life. I knew she was a bit of an exhibitionist by the way she dressed and the way she comported herself. What pleased me most about her, though, was that I could sense she liked me as much as I liked her. Although separated in age by 10 years, we had an unspoken secret friendship that was deeper than anyone really realized. I never let on to anyone how much I enjoyed Theresaís presence in our home.
Another aspect of Theresaís visits I enjoyed was admiring her tanned legs and shapely rump. As a horny teen, I was not always careful where I stared and Theresa frequently caught me glancing at her legs or waist. I never felt ashamed, though, because I knew she didnít mind my roving glances. She always grinned at me with sparkling eyes whenever she discovered my wandering stares.
One summer night when my mother was out of town, Theresa was again babysitting for our family. After my younger brother and sisters were put to bed Theresa and I found ourselves alone in the living room. We sat together on the couch in the darkness watching TV and killing time while the crickets chirped and bullfrogs croaked in the warm night outside. A warm Calfornia night. There was not much interesting to watch on the tube so we mainly spent the time chatting and enjoying the evening. As usual, I couldnít help but admire Theresaís legs as she curled up near me on the sofa.
After an hour or so of small talk and dull television Theresa said she was bored asked me if I wanted to share a bottle of wine with her. I was surprised and flattered by her question. This attractive older woman was not commanding me like some child under the thumb of a babysitter but rather she was actually asking me if I wanted to participate in an adult activity with her. I grinned and nodded eagerly and she got up to retrieve a bottle of California chablis from the kitchen. Her skirt rode up when she stretched to retrieve two wine glasses from an overhead cupboard and I admired the better view of her thighs.
Smiling, she motioned me to follow her down the hallway to my motherís expansive bedroom loft at the far end of the house. It was the perfect place for us to be alone because it was dimly lit and furnished with several comfortable lounge chairs as well as a king size bed. An outdoor hot tub waited on the adjoining deck. Theresa locked the door behind us and paused to light some candles in the darkened bedroom before she sat down next to me on one of the lounge chairs. The flickering candles created a cozy atmosphere as she worked to uncork the bottle of wine.
As I reclined on the lounge chair I continued to admire the view of her legs as she carefully poured us both a full glass of wine. She handed one of the sparkling glasses to me and continued chatting. Entranced by the atmosphere in the bedroom, I sipped my wine while and listened while she talked her art projects. Despite my attempts to stay focused on her face, my eyes soon began creeping up her legs to the edge of her skirt. Her legs were utterly intoxicating to me. No matter what I did, my eyes kept returning to her thighs and I soon found myself hoping that Iíd catch a glimpse of her panties that were tantalizingly just out of sight. With these thoughts running around my mind it wasnít long before I emptied my glass and held it out for a refill.
Theresa smiled at my youthful impatience and leaned forward to refill my glass. As she did I caught a brief view down her blouse and glimpsed her frilly bra in the candlelight. I felt a bigger thrill race through my body as she crossed her legs, forcing her skirt to ride even higher up her thighs. I felt a bit flushed and hot and I began to gulp my new glass of wine even faster than the last one. It wasnít long before I consumed another refill and the alcohol began to blur my thinking.
Theresa drained her own glass of wine and then paused to suggest we take a dip in the hot tub. It sounded like a great idea to me. Without waiting for my response she stood up and began undressing herself. I grinned at her blunt openness but that was the way she was. With the effects of the wine running around my brain I sat there rather stupidly as she proceeded to wriggle her skirt off and casually stepped out of it. She shrugged off her blouse and then she hooked a thumb through her panties and drew them downwards. Her bare pussy was only a few feet from my face as she stood there shedding her clothing.
I was bewitched by the sight of her but when she turned and asked me to unhook her bra I had the presence of mind to stand up and comply with her request. As I unsnapped the clasp from her back I felt a surging sexual thrill to be helping undress this attractive older woman in the privacy of a locked bedroom. I wasnít quite sure where this was going but I was definitely going to be interested to find out.
Totally nude, she stood there waiting for me in the flickering candlelight while I began fumbling with my own clothing. I felt no embarrassment to strip in front of Theresa because we both had known this moment would eventually arrive. It was only a matter of when. In fact, it felt like the proper thing to do and I felt very pleased and fulfilled to share my nudity with her.
When I was finally naked we grabbed our wine glasses and headed for the darkness outside the patio door. Although my head was a bit woozy from the wine, my heart was pounding as I felt Theresa take my hand for guidance as we fumbled our way around in the night searching for the tub. She giggled as we accidentally bumped into the patio chairs and potted plants that cluttered our darkened deck. Hand in hand we gradually found our way to the tub and opened the lid.
I was reluctant to release her hand but once we were seated in the water together, she scooted close beside me and I could feel the her legs and hip touching my side. We continued sipping our wine and chatting quietly as the hot water swirled around us. The effect of the wine and hot water working together left me feeling even more woozy as Theresa scooted even closer to me. Soon she was facing me and straddling my legs.
I felt her both her hands on my thighs. They rested there briefly but then moved to my penis and she gently began to massage it. Despite the effect of the wine, it didn't take long for me to get fully hard in response to her touch. As I hardened I felt her began slowly begin exploring my length and stroking gently. She smiled at me wordlessly and carefully watched my facial reactions as she squeezed, stroked and massaged my unit. I heard her sigh under her breath as she stroked. Soon her other hand went to work on my balls and I was breathing heavily from the pleasure of all her fingers working together. My heart was pounding as I reached out and began massaging her breasts and she sighed again. Her experienced hands gripped and squeezed me until my heart was fairly fluttering.
In a moment, though, her hands left me and I was surprised at the sudden termination of the pleasure. Theresa wasted no time in rising out of the tub and stepping to the deck while beckoning me to follow. I was disappointed at the interruption but she led me by the hand through the dark maze of our deck and in a few moments we had returned to the flickering candlelight and stuffy warmth of the bedroom. I followed her obediently into the dim light of the bed chamber and she left me standing near the large bed.
In a moment she was at my side again, drying me tenderly with a soft cotton towel. Afterwards we sat close together on the edge of the bed and our mouths locked together, tongues exploring eagerly, and my hands found their way to her breasts. I rubbed them gently as her hands returned to my groin and began massaging me again. I rapidly began to lengthen under her touch and she eagerly gripped it as it filled her hands. In a few moments it was throbbing and stiff under her fingers.
When it had stretched out to its full size Theresa slowed her massaging and released me. Then she stood up and faced away from me as she bent over the edge of the plush king size bed. Placing her hands and elbows on the bedspread, Theresa spread her legs wider and crouched with her ass pointed toward me, waiting for me to join with her. This was an invitation I couldnít ignore and so I stood and moved behind her with my rigid erection practically pulling me forward. I placed my hands on her hips and fitted my boner behind her butt cheeks. As she felt it probe around her rear, she dropped her shoulders lower and arched her back to provide me better access.
I was fairly new to doggy style but I simply guided myself into her rear and began to push. Theresa didnít flinch as my cockhead accidentally brushed her anus and she waited patiently until I corrected my aim and the head found her moist pussy. It wasnít easy to push at first because my cockhead was flared out so wide but after a few gentle thrusts I felt more wetness as real penetration began and I returned my hands to her hips. I gripped her waist more tightly as I began pushing deeper and deeper inside her. She accepted my thrusts and after about a dozen tries I was fully inside. I could feel my swollen balls begin smacking against her vulva as I stood behind her and humped.
I could feel the friction of my cockhead dragging on her internal muscles with each withdrawal and she sighed each time I thrust to full penetration. Over the next few minutes I continued humping her until I was panting heavily and sweating in the dim light. The wine I had drunk now became a benefit because I didnít get overexcited. Perhaps that was part of her plan. As I continued humping, Theresa remained bent over to compliantly accept my thrusts. Seeing her in that posture only caused me to hump faster as my mind filled with one primal desire: inseminate her as fully as possible.
Soon I felt the warmth and pressure in my balls and my shoulders grew tense as I prepared to cum. I clutched her hips and pulled her fully onto my boner as I felt the tingling sensation fill my groin and my semen began rushing out. I held her there as my throbbing boner squirted pulse after pulse of hot sperm into her pussy. When my spasms began to slacken I felt the muscles of her pussy quiver and grip my shaft tightly and she gasped as her body trembled in orgasm. I continued to clutch her hips and hold her steady until she sighed and relaxed a bit. It was over.
We remained joined together for a few more moments enjoying the sensation of my cock plugging the slick flood of warm semen inside her. When I began to soften I withdrew from her and we both collapsed onto the bed beneath us, spent. We lay there next to each other through the night, dozing together. We ignored the semen that continued leaking from her pussy although it dampened the sheets and our legs. I actually felt proud to have created such a flood for her. When I finally pulled the bed covers over us, I saw that my once proud boner was sagging downward and my still tingling balls hung limp and empty.
We repeated our joining again early the next morning before my siblings awoke. I had a bit of a headache from the effect of the wine but Theresa soon made me forget about it. When we emerged from my motherís bedroom later that morning, my brother and sister never questioned what we had been doing together or why Theresa and I put my motherís bed sheets in the washer.
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