Raised to be a Cuckold

My mother was never discreet about her relationships. Her lack of discretion got much worse after I'd returned from college for my summer break. She was an attractive lady with a pretty face, curvy body, and wonderful personality. That summer, I learned she was the type of woman who could sleep with any man she wanted to. She rarely brought the same man home twice. For those three months, there was a constant parade of tall, fit men in our home.

Our home was small and had very thin walls. When I'd arrived home that summer, I found my bedroom had been rearranged so the head of my bed was against the same wall as my mother's bed. Nearly every night for those three months, I would lay in my bed listening to her crest in one orgasm after another on different cocks, night after night after night. It was torture.

Unlike my mother, I was far from desirable to the opposite sex. I was still 100% a virgin. I was short and skinny like my father. My skin was fair and my body hair was light blonde and sparse. Being 19 years old, my sex drive was off the charts. And my mother was the star of nearly all my masturbatory fantasies.

It took me a few weeks to work up the courage to peek in on my mother and her friend one evening. I'd listened to have one unusually loud orgasm and her friend didn't sound like he was going to finish anytime soon. Wearing only my briefs, I tiptoed out of my room and down the hall. I quietly got on my knees outside her bedroom door and peeked inside. I didn't have the best view, but what I saw forever changed my fantasies.

My mother was naked and on her back. I could see one breast and one leg along with the side of her face. Between her spread thighs was a man sawing his long, thick cock in and out of my mother. He was tall and fit. He had a heavy 5 o'clock shadow and his body was deeply tanned. My hand slipped into my underpants while I watched that man fuck my mother. I played with my small, skinny penis for a short time before I decided I was pushing my luck.

Very quietly, I crept back to my own room. Before climbing back into my bed, I stripped off my briefs. That night I laid naked in my bed, on my back with my legs spread wide, just like my mother was. I masturbated in time to the man's thrusts into my mother. Of course, I didn't last nearly as long as he did. I had finished, was wiped clean and tucked into bed long before he exploded inside my mother.

Shortly after that night, my mother began introducing me to every man she brought home. Shaking the hand of the man who would be fucking my mother that same night was surreal. Not long after that, my mother had me say goodbye to them too, even if that meant waking me up while I pretended to be asleep. On those nights, she would gently wake me up and I'd have to shake the man's hand and tell him it was nice to meet him. She would be wearing one of her many nightgowns that left her immense boobs unsupported. None of her nightgowns extended beyond midthigh. A few nights I could have sworn I saw the light from the hallway glisten off moisture on the insides of her thighs.

After my mother walked her friend out, she would return to my room and tuck me in before kissing me on the lips. I knew she sucked their cocks. I'd heard the sucking sounds through the wall and many of her friends even commented on her sucking skills. When she began giving me those goodnight kisses, I knew she hadn't washed her face or brushed her teeth. She would lean down and kiss my lips, whisper, "Goodnight Sweetheart." And kiss me once again. The taste of their cocks as transferred from her lips to mine. And that taste always left me rigid, even if I'd already played with myself.

After bringing two men home with her one evening and introducing me to both of them, I listened to them both have their way with mother. They went at it, off and on, for almost two hours. When they were finally finished, my mother guided them both into my bedroom while I pretended to be asleep. She woke me up with a gentle touch on my shoulder. Opening my eyes, I saw my gorgeous mother standing beside my bed in a deeply cut, upper thigh length, completely sheer white nightie. Standing on either side of her were the two men who had just made love to her.

My penis was perfectly stiff when I reached up and shook the hands of the two men who my mother had just fucked. As usual, my mother walked them out and then returned to my room. Instead of kissing me goodnight, she pulled the covers away from my body and without mentioning my underpants around one ankle and my hands on my bare erection, she climbed into my bed and laid on her back.

Looking into my eyes, she whispered, "I don't want to sleep alone tonight."

Reaching over, she took hold of the hand I'd been stroking my penis with. She slowly slid it across her stomach. She paused and while staring at me, slid my hand even lower until my fingertips encountered her well-manicured pubic hair.

I laid there beside her, she was on her back with her knees bent and her legs spread. We were looking into each other's eyes while she guided my hand lower and lower. When my fingertips felt moisture, I whimpered softly, "Mom..."

Our noses were nearly touching when she whispered, "It's okay Julian. We both know how badly you want this."

My first and middle fingers slid along either side of her thimble-sized clit, we both moaned softly. She guided my fingers to draw circles around her clit. From time to time, she guided them down lower until they slipped into her well-used pussy only to return to her clit.

"Julian, your fingers are covered in the cum of the men you just met."

Rolling my hips back, I kept my little hard-on well away from her hip. My fingers slipped beside her clit and down toward her gooey and gaping hole. Biting my lip hard, I whimpered, "It's so slippery."

"Yes, it is. I'm slippery with the cum of those two men. Have you enjoyed listening to men fuck me, Julian?"

A soft moan slipped out, "Yes."

"You like to lay in here, listening to me cum on a man's cock, don't you? You lay in here and play with your little penis while I'm being fucked, don't you?"

I whimpered softly, "Yes."

She turned her head back and forth so the tips of our noses brushed against each other. I felt her warm breath on my lips when she spoke, "Julian, Sweetheart, I have another date tomorrow night. It is with Rodney, you've met him before. He is extremely well-hung..."

My fingers were dripping with slippery cum while she continued to guide my touch. She had me moving my fingers in circles around her clit at a calm pace. Her hips had begun to grind and hump against my fingers.

"Tomorrow, we won't look for you so you can greet him. And I won't bring him in here so you can say goodbye. Julian, I'm giving you an opportunity. If you want to hide in my closet and watch me get fucked..." She paused as she lowered my hand so I could slide my fingers in and out of her sex. "Baby, if you want to watch, tomorrow is your chance."

As she uttered that last word, my mother crested in an orgasm on my fingers. Her body twitched and spasmed. She tossed her head from side-to-side on my pillow. She moaned deeply and kept my hand pressed firmly against her well-used pussy until the wave of pleasure had passed. She turned her head, kissed me gently on the lips, then rose up off my bed and made her way to the door.

While she left me laying there with cum-covered fingers and a raging erection, she said, "Your bed is too small for both of us. I'm going to sleep in my own room. Goodnight Sweetheart. I love you."

After she'd left me alone, I moved so I could lay on my back in the middle of my bed. What I encountered made me even hornier. I was laying in a wet spot. A warm, slippery wet spot in the middle of my bed. While I masturbated my skinny, pale penis with one hand, I reached down with my other and ran my fingers through the large mess I laid in. I guessed it was a mixture of my mother's juices and the cum of two men.

I ground my naked bottom into the slippery wet spot and jacked my penis off at a quick pace. At the same time, I slowly raised my other hand toward my lips. It was covered in the gooey proof of my mother's lovemaking earlier that evening. As those two fingers entered my mouth, I tasted cum for the first time. The cum of not one, but two other men and my mother. I would have reached down to scoop up more, but I was far too excited and wound up cumming all over myself.

I thought I had been quiet, but when my mother called out from her room, "Julian? Are you okay?" I knew I hadn't been successful.

I tried to sound normal when I answered, "I'm okay, Mom. Goodnight."