When I was in my late teens around 19 years old, I mowed lawns for money like many boys my age did. We had a very lower middle-class upbringing, so to have money I had to earn it on my own. I worked hard and built up a fairly sizeable clientele. This however was strictly a summer time activity, but it kept me busy. Every year I added on to my business taking care to do my best job for my existing customers. I had one particular client with a big house along with an equally large garden. They were an older couple who paid well but were very demanding. The woman actually knew my parents and worked in the same office as my mother as a secretary in her office. One summer I was mowing their grass and the lady, who when I was around appeared to like to sit on a garden chair and watch me work. I always felt self-conscious in case that I wasn't doing a good job and she would give me a hard time about it or tell my parents. She would give me directions about how she wanted things done and of course I followed her instructions in agreement or not.
On one particular day when I was finishing up, she called me over and asked if I wanted to have a glass of lemonade and to rest for a minute before I went home. I said sure as it was a warm day and I was very hot and sweaty. After emptying the last of the grass clippings into her compost container and loading my mower and rakes into the back of my truck. I headed over for my lemonade. She watched me walk over with a dreamy half smile on her face never taking her eyes off of me. Her scrutiny always made me self-conscious. My usual work outfit was a pair of cut down Levi's jeans, Nike training shoes, and a T-shirt but I rarely wore the shirt. As I walked up, I noticed she was wearing a sun dress and with the sun behind her I could see almost through it. From memory I am sure that my mother said their names were Michelle and Jerry. She was at guess late 50's or early 60's in age, but in very good shape. Like any boy my age I was horny all the time and noticed her ample breasts swaying in her dress without the restriction of a brassiere. Her nipples were erect and quite obvious. I furtively looked her over trying to be discrete, but getting an eyeful. She made small talk as I drank my glass and I noticed her looking at the bulge in my jeans. I was sweaty and dirty. While making small talk she suggested that I should come inside and shower off before leaving.
"My, you have managed to get more of the garden on you than in those council bins dear boy, come inside and use our shower George," she said.
"I really shouldn't thanks, I can just use the hose," I said.
"Don't be ridiculous, I insist."
Michelle wasn't the type of woman that you argued with and I certainly wasn't going to start. I knew her husband was home somewhere so wasn't all that concerned. I just assumed she was trying to be nice.
"OK I sure appreciate I said.
She got me a big soft towel and showed me to her bathroom in the master bedroom. In my limited experience it was huge. A big stand-up shower with clear glass and a bench in it which I had never seen before. It smelt like perfume and face powder. I closed the door and stripped off my shorts. There were mirrors over the sinks, in front of a vanity unit, as a well as a floor length one on the door. Basically, mirrors everywhere. I could see myself front, back, and side, which was a first for me. I still have that image in my head, my thin suntanned body, contrasting with my skinny lily-white arse. I stepped into the shower and started washing my hair and soaping my body. I had my eyes closed as I rinsed my hair and thought I heard something, but didn't pay any attention. All of a sudden, I felt a hand on my back which startled me and made me jump. I opened my eyes getting soap in them, but in the quick glimpse I saw Michelle naked next to me in the shower.
She noticed my discomfort and said, "Hold your head back and I will rinse the soap out of your eyes." The shower had a hand-held attachment which she started up and held my head rinsing my face and eyes. I could feel her big breasts against me and was actually trembling with fear and excitement.
After rinsing my face she said, "Let's make sure you are all clean shall we, just relax darling." She soaped up a loofah, which was the first one I had ever seen, and started scrubbing my back, a bar of soap in her other hand. The rough feel of the it on my back and soft soap was soothing and I finally started to relax. I was completely freaked out by her being there not to mention I knew her husband was around and the thought of him catching us was in my mind. My cock was partially erect which I couldn't help and she laughed saying, "my, such a big boy after all, we had better not miss this."
She reached down, soaping my cock. The feel of her hand on me all slippery with soap in the warm water almost made me cum on the spot. My cock, although almost hairless was about 7 inches when erect even then, which I knew because I stroked it, measured it, and played with it almost nonstop.
She pushed my hair back out of my face and looked deep in my eyes and said, "I am going to teach you how big boys play", and kissed me full on the lips. She pulled my hand to her breast and I felt its weight, squeezing her gently and running my hand over her nipple. It was hard and erect just like my cock which she stroked and rubbed on her smooth pussy. I could feel her hard clitoris against my cock as she rubbed it and moved her hips. I didn't know what it was, but I knew it felt good against my straining cut cock. Holding my arse in both hands pulling me to her she humped me slowly with my hard cock sliding over her pussy and clit never entering her just sliding between her wet lips. God, it felt great. I thought I was going to pass out. She shuddered as she achieved her orgasm, her hips jerking forward against my hard cock, I started to cum as well spewing on her hard clit and wet pussy lips. My white seed dripping from her smooth lips to the floor of the shower. My cock jumped and jerked spewing like it would never stop. I felt like I came a gallon it was so intense. She held me tightly until her breathing returned to normal.
Michelle whispered huskily in my ear, oh thank you baby," and kissed the side of my face. She reached down fingering her pussy and let out a couple of more shudders. She brought her fingers to her lips covered in cum and tasted it spreading some over her lips. She kissed me deeply, her tongue working inside my mouth, I could taste her pussy and me cum in that kiss and surrendered to her passion. We soaped each other and towelled off drying each other with the big soft towels. I played with her big breasts and nipples drying them and sucking each in turn. As she dried me off my cock started to get hard again, she kneeled down at my feet drying my legs. She kissed my cock, licked the drop of cum at the head, sliding it easily into her mouth she sucked me, head bobbing. She stood up and told me to finish drying off and meet her in her room. I quickly dried myself and walked into her room completely nude my cock swaying as I walked. I felt great as I walked through the door until they sight of her husband sitting on the edge of the bed staring at me stopped me in my tracks.
At first all I could focus on was his face and hair. He had a wig on, auburn, longish 60's style, full make up, lips painted with red lipstick. In retrospect, he was probably going for Ann Margaret, and actually wasn't too bad looking. Even though old enough to drive for all intents and purposes I was a boy and the strangeness of how he looked left me completely in shock. I don't think I had ever even heard of cross dressing at that age. I stared at him up and down, he had on a nice bullet type brassiere, stuffed full, a sheer chiffon nighty, shear panties, nylons, garters, and what looked like high healed slippers with a fluffy ball on the top. He had his legs crossed and hands behind him with his chest out. I could tell he was rather pleased with himself and my reaction.
Michelle said "Oh there you are dear, say hello to our guest." He said, "hello young man come sit here next to me", and patted the bed. I was frozen in place my cock shrinking with fear, but a gentle hand from his wife got me moving toward him. My mind was racing and I couldn't do anything but do what was asked. I sat next to him on the bed and covered my cock with my hands.
He smiled and said, "no need for that and lifted my arm and set my hand on his nylon covered thigh. "Don't you love the feeling of a smooth silky thigh," he whispered, moving my hand up and down along his thigh. I watched my hand moving up and down like it belonged to someone else, but I had to admit it felt great. I still remember he smelled like perfume and powder. I squeezed his thigh and he drew a sharp breath. His wife climbed on to the bed completely nude and watched us casually fingering herself.
He said, "now just lay back." I was at a complete loss, my fear of being caught with his wife had been replaced by a kind of slack jaw astonishment to what was actually happening to me. I scooted up on the bed and laid back resting my head on Michelle's thigh. He reached for my cock and I noticed his meticulously painted nails as he gripped and stroked my cock. I was so nervous I almost couldn't tell he was stroking me. He stroked me for a few minutes cooing "just relax you are perfectly safe with us; this is how adults play." I closed my eyes trying to relax as he stoked my cock and balls gently. I was worried I wouldn't get hard again until I felt his tongue on my cock, licking the head, along the length, and my balls. His warm mouth and the cool air were really electrifying and I soon began to stiffen. He took my cock in his mouth sucking my hard cock all the way down. His wife idly played with her pussy running her hands through my hair and over my arms and shoulders. I could feel his throat as he swallowed me and he didn't seem to have a gag reflex at all. The feeling was glorious and I unconsciously began to move my hips fucking his mouth. I could feel his hands on my hips running them over my tight stomach and chest as he sucked me.
He whispered, "what a beautiful boy," and lifted my legs up spreading them. I didn't know what he was doing, but soon felt his tongue on my balls, gently licking his way behind them on my sensitive smooth skin until I could feel him licking my asshole. At this I almost bolted, but was curious as well. The feeling was incredible and I spread wide for him and he slipped his tongue inside me. Michelle massaged my legs as I laid there spread wide open.
