Virgin Sex Stories

Babysitter's Clogs


Now that clogs were back in style this past summer, I'm reminded of an early sexual experience. It was near the end of summer. I was in seventh or eighth grade and had just biked home from swimming practice. My dad worked in the city and my mom was away for the day, so Stacia, our babysitter, was there to take care of my baby brother. Stacia lived behind us, one house over. I had a mad crush on her, but she had just finished high school and I could only worship her from afar. Here dirty blond hair and her throaty voice made her seem wild and untamed to me. I was always flustered around her, with conflicted feeling of lust, embarrassment, and awe. We were about the same height. However, she always wore a pair of brown, wooden clogs with three inch heels, so it felt like she towered over me. Clogs were pretty popular back then and quite a few girls wore them to school. Stacia's clogs had the highest heels, though. Anyway, I'll always associate brown, high heel clogs with Stacia and a wonderful, early sexual experience. Stacia was in the living room watching a soap opera on tv. I came in all excited and nervous and stammered out a hi. She smiled up at me. "My, don't you look cute in that skimpy, blue speedo suit," she teased. I turned red and stared down at her clogs. In my rush to get home to see Stacia, I had simply put on my t-shirt and biked home, instead of changing. I only wore my speedo suit during practice because I was self-conscious about the way its tightness and lack of material accentuated my crotch. My penis, which was semi-hard with the anticipation of seeing Stacia in her high heel clogs, withered to nothing. Noticing my embarrassment, she assured me that she was just kidding and then complimented me my on my tan to change the subject. I knew I had a savage tan and beamed proudly. She leaned forward, resting her elbows on her knees. "Take your shirt off. Let me see your tan all over," she in a hushed, wicked tone. I shook my head shyly and continued to stare at her clogs. "Come on. What's the big deal?" she said as she stood up. I've seen you in your speedos at the pool. Pretend we're at the pool. I dare you to take off you sneakers and t-shirt." I continued to stare dumbly at her clogs, but was slowly getting excited at the prospect of being almost nude in front of Stacia. I had been swimming hard all summer and was quite proud of my body. A surge of hormones and I kicked off my sneakers and pulled my t-shirt over my head. Standing in my near nakedness, I felt a flood of warmth enter my loins. My body quivered with the anticipation of a stallion about to mount a mare. I was aroused. "Mmm," nodded Stacia appreciatively. "You have a nice, firm swimmer's body. If only you were bit taller," she added, wistfully. I protested immediately that we were about the same height and it was only because she was wearing high heel clogs that she seemed taller. She laughed. "So you noticed my high heel clogs. You've only been staring at them since you came in. Anyway, the heels aren't that high." She sounded a little defensive and was pensive for a moment. "Here, see for yourself." She kicked off her clogs and motioned for me to try them on. I became very excited at the thought of wearing her clogs. Because she seemed out of reached, I must have subconsciously fixated on her clogs and now was my chance to experience a part of her: to wear her high heel clogs. I eagerly slipped into her clogs. The clogs felt wonderful. The insoles were padded making the clogs luxurious. The height of the heels created a padded arch that pressed deliciously against the soles of my feet. Best of all, I now towered over her and felt bold and daring. I knew my erection was a prominent tent pole, pushing against the tight fabric of my speedos. I proudly faced with my feet slightly apart, my hands on my hips, and my cock straining for release. "All it takes is a pair of high heel clogs, and you turn into a little tiger." She looked up at me slyly. She placed her hand on my chest and my breathing became audible. "Speaking of little tigers..." She suddenly reached down and grabbed my balls aggressively. I gave a yelp of surprise, which pleased her greatly. In a flash, she undid the string of my speedos and worked the bathing suit down to my knees. She encircled the base of my cock with her hand and took my dick swiftly into her mouth. The warm, moist sensation of her wet mouth and flickering tongue quickly overwhelmed me with pleasure and I came in body shaking spurts. She got up and ran to the bathroom. I heard the toilet flush. When she returned, I was still standing there in her high heel clogs. My speedos were now down by my ankles, but my dick was still waving in the air. She was amused to see it still hard. "What am I going to do with you?" she teased. "You come like a flood and you're still hard. Well, we'll just have to stuff tiger back into your speedos." She pulled my speedos up and awkwardly covered my hard cock with them. "Can I have my clogs back?" Everything had happened so quickly and I was reluctant to let the experience slip away. "Can I wear them a little, I mean. Can I try walking around in them." I felt like a little kid asking that, but she nodded understandingly. She took me by the hand and led me to the dining room, which had a wooden floor. It was then that I knew I'd always love the wooden clomping sound of clogs. I was wobbly at first, but then I got the hang of it. We didn't say anything. Eventually, I sadly returned the clogs to her. We both tacitly understood that we would not breathe a word of our experience to anybody. Stacia turned on the tv and sat down on the couch. I awkwardly sat down on the opposite end. Stacia casually propped her legs up on my thigh and gently rubbed my cock through my speedos with her clogs. I began to caress the clogs and her feet and then started to rub the clogs vigorously against my cock. She encouraged me to come again and soon my speedos turned to water. It was then that she kissed me tenderly on the lips. She told me to clean up and to stay in my room because my mom would be home soon.

I only saw here one time after that before she left for college. She called me over from her backyard and we went into the den of her house. I was pleased to see that she was wearing her high heel clogs and was hoping for a similar sexual experience. We both sat down on the couch and I awaited with giddy anticipation for her to rub her clogs on my erection. She noticed my excitement and said that she just wanted to talk about the other day and why it happened. I was disappointed, but also curious. She explained to me that she thought I was a sweet, shy kid and she wanted to be my first sexual experience, especially when she saw me in my tight speedos. She had only planned to caress me with her hands until I climaxed, but feeling my excitement and wanting to surprise me as much pleasure as possible, she impulsively decided to suck me. She also admitted to being pleased at how much I enjoyed her clogs and couldn't resist rubbing them against him, even though she had only planned to make me come once. Aware of my sensitive ego, she admitted she was tempted to now "fuck my brains out," but she thought it would be best to not have any further sexual relations. I was crestfallen and it showed. To cheer me up, she took off her high heel clogs and handed them to me. I brightened immediately. As before, she kissed my tenderly on the lips. "Whenever you slip my high heel clogs on," she whispered in my ear, "I want you to think of me and how I couldn't resist just stroking you, but had to have you in my mouth."

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