Young Gardener

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.

She said, "isn't he delicious," and her husband just grunted in response as he worked his magic tongue. She turned my head and spread her legs sticking her smooth pussy in my face. "Lick me softly honey," she said and I licked her smooth pussy lips, tasting her juices. She spread her lips, exposed her hard clit, this was the first pussy I had seen up close, she whispered instructions to me in a husky voice, how to lick it softly and gently, licking her lips on both sides then flicking my tongue over her pearl, and back again. Her hips undulated and she had me hold my tongue still against her as she rubbed herself on me. Her husband was sucking my cock in long deep strokes as he watched me learn how to lick his wife's pussy. I was out of my mind and as she started to shudder and spasm in my mouth with a huge orgasm, I let go shooting jets of cum into her husbands' mouth. He kept sucking and swallowing and I thought surely, he must drown with the volume of my hot copious cum. Michelle's juices and my own saliva covered my mouth, lips, and dripped from my chin. She tasted wonderful. Jerry her husband or whatever he likes to be called when in full lady attire held my cock in his mouth sucking gently as I softened, making sure to suck out every last drop of my seed. He stood up and lay down on the bed next to his wife and they kissed a long deep kiss. I lay there completely spent, my body at ease and relaxed.

I heard Michelle ask him softly, "what do you want do next sweetheart?" He said, "I am feeling a little empty darling." She reached over to their end table next to the bed and opened the top drawer. She reached inside and pulled out a strap-on dildo. I had never seen one before and this one was black and big, bigger than me. I watched closely feeling a little inferior and wondering if she was going to come at me with that thing.

"Excuse me baby," she said, and I moved to the foot of the bed as she kneeled and put it on.

This was years ago so it was a fairly complicated rigging that went with it. When she was ready, she told her husband, "Assume the position your bad little girl."

Jerry eagerly rolled over on all fours with his face in the pillow and his arsehole in the air. She knelt behind him and started slapping his ass cheeks.

"You are a bad, bad little girl, mommy didn't give you permission to suck that boys cock and swallow all his cum, did she?"

"No, mommy," he said in a little scared girl voice. She hit him hard enough to leave a pink hand print. She spanked him again and again. I could see his cheeks getting pink through his sheer panties and was wondering how long this was going to go on. She moved over and removed a jar of Vaseline from the drawer and took a big glob, pulled down his panties, and worked it into his smooth arse hole. I was completely freaked out, but fascinated at the same time, and moved around so I could see everything she was doing. She looked over, smiled, and winked at me as she put the head of the dildo to his asshole. I smiled back like a dumb struck idiot, and she leaned in steadying the dildo with one hand and slowly pushing the stiff member into her husband. I could see him shiver and tense up as it stopped a little way in then she pushed hard and it disappeared all the way in. I thought he would scream, but he just grunted as she slowly started fucking him. She had one hand on the base of the cock and the other holding his hip.

She whispered, "beg for it you sissy slut, beg for momma's big thick cock."

He grunted and said, "oh please fuck me momma, I need it so-oo bad." She started picking up speed and I was amazed that he could take big cock all the way up his ass. But what had my attention was how she looked fucking him, her tits bounced and swaying as she humped his arse. Her nipples hard and her arse flexing with each thrust. I could see she was grinding the base of the dildo into her clit as she pumped and was breathing harder and harder. I could not stop myself and I positioned myself next to her so I could suck her hard nipples as she fucked him. She gasped as my mouth covered the one closest to me. I sucked it in and out like her husband had sucked my cock. I had my arm across his back holding myself in position and my hand holding her breast to my mouth. God, she had beautiful breasts and I can still feel her nipple in my mouth when I think of it. She took her free hand and reached for my cock. I moved so she could stroke it while I sucked her big breast. She was breathing hard and getting close to her orgasm I sensed. I was already in tune with her sensuality.

She started whispering to her husband, "Mommas going to cum in your sissy pussy baby." Her voice wavered as she thrust and surrendered to her need.

He said, "cum in me momma, make me your sissy." She shuddered and thrust hard as her body was wracked with wave after wave of orgasm. I was kneeling next to her watching as her body shook and breasts bouncing with her climax. Jerry knew how to surrender to her lust completely. Her body finally calmed and she lay forward on her husband's back holding him tight, dildo buried inside him. She stroked my cock as I knelt next to her then guided me behind her. She guided me and placed the head of my cock to her lips and I slid right in. She was dripping wet and I could see her juices on the inside of her thighs. Her pussy was warm and felt like heaven. I still remember how natural and perfect it was as I slowly fucked her. Her head lying sideways on her husband's back, eyes half closed, and a smile on her face. Michelle was here physically, but mentally she was far, far, away. She told me much later where she went, but that as they say, is another story completely. I was revelling in the feeling, slowly sliding in and out of her, feeling her around me, along the entire length of me, her soft cheeks against my hips as I buried my cock in her as deeply as I could go, slowly withdrawing it just to plunge it in again. I continued this way slowly for as long as I could. I wanted it to last forever, but all too soon I felt my excitement get the best of me. I slid in as far as I could and held completely still as my cock jumped and squirted deep inside her. My hands on her hips, my cock pulsing as her inner muscles squeezed the cum from me. I swear my eyes rolled back in my head.

When I opened them, she was staring at me smiling. "That's my good baby boy," she said. I pulled my cock from her and lay down on my back. She turned around on all fours, dildo hanging between her legs and slowly licked the white drops of cum from my shrinking cock. Jerry positioned himself between her legs, moved the dildo out of the way, and put his mouth to her pussy sucking my seed from her. I closed my eyes and drifted off to sleep as she licked and suckled my cock.

My dreams that night was more erotic and bizarre than my normal. Little did I realize that my real life was going to be more interesting than I could even have dreamt of.

The next day dawned like any other except, with the morning sun shining in my window. I was still on top of my covers completely nude. I looked down and smiled as I thought about how tired I must have been. I looked over at my open bedroom door and tried to remember if I had got up for some reason during the night. I didn't remember unlocking my door much less opening it. I was pretty groggy so I dismissed the thought. I jumped out of bed and threw on my Levi shorts and a sun hat and headed down stairs. My mother was always away to work by the time I woke up and usually left a note with errands to be done or what I was supposed to eat for lunch. Today's note just said, "Lunch is in the fridge, have a wonderful day," with lipstick lips where she kissed the note. The thought of her going to work and speaking with Michelle was definitely heavy on my mind. One slip from her and I would have to face the music when my mother got home. I had no idea what I would say or what excuse I could use. I ran scenarios over and over in my head, "Geez mom, I don't know how it happened, she told me to take a shower and the next thing I knew she had my cock in her hand and her big tit was in my mouth. It was completely accidental!" Explaining how I accidentally had sex with her friend and her bizarre husband wasn't something I was prepared for. What was really bothering me most was how much I enjoyed every bit of it. I fixed myself some breakfast wondering what I would do for the rest of the day..............Not much so I just lazed around for most of the day.

When I came home, my mother was home starting dinner, she still had her work clothes on, covered over with an apron, which suggests she had obviously just not been home for long. "What's for dinner?" "I am going to fry some fish."

"Sounds good, I'm going to take a shower before dinner," I said and headed up the stairs.

"I had lunch with Michelle today and she had a lot of things to say about your little visit yesterday. We can talk about it at dinner."

I froze half way up the stairs and I had a feeling in the pit of my stomach like I had just started the big drop on a roller coaster. I got a hold of myself and went up to my room closing the door quickly. Pacing around my room, my mind racing, I finally laid down and tried to calm down. What was I going to say if she told her everything, I asked myself over and over again? I finally calmed down and figured Michelle had more to lose telling all than I did... I grabbed my dressing gown went out in the hallway to the bathroom to get my shower. Once inside the bathroom, my mom's nylons were hanging all over the place and I took them off the shower rod and hung them on the towel rack. As I was moving them, I stopped and felt the silky material against my hand. Since my episode with Michelle the material had taken on a new and exciting feeling. Putting my hand inside of one I rubbed it against my cheek enjoying the feeling. I put it to my nose and even though they had just been washed as I breathing in slowly, I caught the familiar scent of my mother's perfume and powder. It was the smell of safety and unconditional love although I didn't know it at the time. I only recognized the feeling of peace and contentment it brought. Of course, it was only a minute before I decided to run my hand over my chest and body. Feeling the material brought back images of Michelle in her lingerie and my cock began to rise. I ran my hand down my stomach over my smooth penis and balls relishing the feeling. I gripped myself softly and stroked. Closing my eyes and losing myself in the feeling of lust. I was lost in my fantasy and near orgasm, a big drop of precum dripping from my cock when there was a sharp knock on the door.