My best friend's mother

By Jaymes Ryan

Published on Sep 3, 2004

Transgender

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Disclaimer: This story contains explicit sex acts between a minor and an adult. Don't read it if it may offend you or if it is illegal for you to.

My Best Friend's Mother (F^b 1st anal tg)

I lay on my back and opened my legs wide and she lowered herself down, her full hips between my outstretched young thighs. Her hairy cunt bone sank down onto my penis and balls and pubic bone and she fucked me with it, grinding into me with a passion. 'Bone fucking', she called it. It was my first time. I surprised myself by rubbing back up into her, raising up my pelvis and rubbing my stiff little rod and my tight little balls into her fat dripping snatch. I wrapped my legs around her waist and she just had her way with me as I moaned and felt her big soft breasts weighing down on my smooth chest. And her rigid protruding clit rubbing down my genitalia and poking into my little hole like a slippery, slippery dick.

"Are you my little boy, pussy girl?" she breathed excitedly. "My little slutty boy with the pussy bottom.."

"Do you like me to fuck you little slutty boy?"

"Oh yesyesyes...."


When I turned twelve I joined my best friend, Jerry, and his parents for Easter vacation on a small island off the coast of Costa Rica (where we lived). We stayed at their apartment right on the water near the dock and spent the days on the beach and on their boat. I only wore my Speedo style white swim suit and never used sunscreen, so by the end of the week I was burned like a lobster and hurt like hell. Friday afternoon Jerry's father had to get back to his business unexpectedly and was going to take a small plane so he took Jerry along for the thrill of it leaving me and his mother alone for the weekend.

She was an attractive, sandy blonde, well bred New Englander with round hips and full breasts that I took special notice of as we circled the island in the outboard motor boat. I inevitably found myself sneaking looks at the plump bulge in between her thighs.

Until then I was only familiar with my little sister's bald little pussy and pink vagina from when we used to shower together. This lasted until I was caught examining her 'noony' closely as we searched for her penis. We finally found her peehole and satisfied ourselves that this was it. And that's when our mother came in. Mother decided that from now on my sister had to wear panties when we showered together. Once wet the panties were transparent so her vagina might as well have been naked, but the panties did give the message that our fingers should stay out of there. I guess Mom didn't think it mattered that my little penis and balls were naked for my sister to see. At that age, what my sister called my 'thingie' wasn't much bigger than a really large clitoris. I would wag it around for her, dancing and poking my pelvis suggestively in and out, bump and grind, until my pecker grew stiff and pointy. My sister giggled appreciatively at my antics which just made it all the more fun.

Mrs. Benson's pussy seemed much more interesting than my sister's little noony. I could sometimes make out the cleft of her plump labia when the suit was wet and even see the texture of her pubic hair curled up under the clinging fabric. Once she pulled herself out of the water after taking a spill water skiing and her bathing suit was pulled up. As she raised a towel to dry her hair I saw that her bikini bottom had shifted so that one of her pussy lips was caught outside of the elastic hem of the crotch. My peter got stiff and real itchy as I stared at the fat cunt lip just hanging there and little droplets of water still in her pubic hair. I thought she saw me looking, but she didn't say or do anything at first. Then she looked over at me. I immediately looked away awkwardly and she adjusted her bikini while still watching me. I saw that my young penis was poking a tent out the front of my bathing suit. I quickly tried to push it down and pressed my knees together, horribly embarrassed. She seemed amused by this and embarrassed me further by asking me if anything was wrong. She made like to reach over to see and just smiled when I hid my little package with my hands and turned away red faced.

Anyway, Mrs. Benson really liked me a lot and encouraged her son to spend time with me. She thought I was really bright and even offered to my parents to pay to send me to a prep school in upstate New York. My Mid-Western parents were not near as well off as the Bensons and they didn't think much of the idea of me going off to boarding school, especially on someone else's dime.

So it was evening and we were alone in the apartment and my sunburn hurt so much I couldn't stand it. I couldn't even take off my bathing suit it hurt so much. Mrs. Benson got some salve and tried to rub it into my skin but it hurt too much. I was in such pain that she went to her dresser and got some pills out of a prescription bottle and gave me one.

"How much does it hurt?"

"A lot."

She gave me another. Then I lay down still wearing the Speedo swim suit. Soon the light in the room had dimmed with the sunset and I wasn't aware of the sting of the sunburn any longer. I felt numb, like I was floating in a dream, and forgot where I was.

And then it was dark. A kind of nausea had awakened me. I got up and couldn't get my bearings. Dizzy and uncoordinated, I felt like I was going to throw up. Light streamed out through the slightly opened bathroom door, so I weaved my way over and opened it.

My face was twisted in panic as I entered - and saw Mrs. Benson standing nude in front of the mirror above the sink putting on face cream. I didn't much notice the towel near by or the tall drink with ice cubes or the cigarette balanced in the ash tray. My eyes stared at her, but my mind didn't make the connection - that, after all this time of peeking at the secret parts of her body, here she was at last, standing completely naked right in front of me. Her white breasts stood out clearly from her suntanned body and a patch of pubic hair forested the mound where my gaze always drifted.

"Mrs Benson, I...I..."

"Why Ryan, what -?"

She was startled, and I was so out of it and nauseous that I didn't even act embarrassed at seeing her naked. I just went straight to the toilet and tried to puke. But, I couldn't. Mrs. Benson hurriedly put on her short bathrobe.

"What's the matter, Ryan. Are you sick?"

"I...I...I gotta go -"

Suddenly I felt it at the other end and tried to pull down my swim suit frantically. Mrs. Benson came over and helped me and I got my butt on the seat just as the loose bowel movement came.

She took my swim suit to the sink and washed it out with shampoo and discreetly turned her head, I guess not to embarrass me, although it didn't matter to me given the dopey state I was in.

"I guess two was one too many."

"Yeah..."

I felt like I was in some alternate reality. And as soon as my sickness began, it was all over and I felt wasted. I wavered a little on the seat and spaced out.

It reminded me of my first nursemaid somehow, an overwhelming feeling of memory and emotion.

Mrs Benson turned on the shower.

"Come on, let's wash you."

She gently led me over into the shower and I just stood in it dreamily as she picked up the bar of soap.

"You poor boy. I guess that was a little too much for you, huh? Don't worry, just relax, it'll be alright. Just relax. Relax and enjoy it."

She soaped me from the head down and her hands did feel good as they washed down my stomach and and down my back to my bottom at the same time.

"Now isn't that better?"

"Mmmm..hunnn..."

Then I felt soapy fingers manipulating my young penis and a slippery digit sliding between my buttocks.

I sighed, and was transported into a sense memory. I was a baby toddler being washed after dirtying his diaper and was getting all cleaned up. My knees got wobbly and I got kind of giggly in my throat and began sinking down to the wet tile shower floor.

"What's the matter?" She sounded really concerned.

I looked up at her with a lopsided grin and went kind of limp. Mrs. Benson helped me down to my knees, then I lay my head down on the floor - but left my bottom sticking up and opened it to her gently massaging finger.

"You silly boy. You like that, don't you? Don't you?"

I did. I wiggled my bottom and thought about my nursemaid, Dolores. Her white uniform and the smell of Palmolive soap on her dark Latin skin. She always made me feel so good. And it was she who was rubbing my bottom with Vasoline, not my best friend's mother. I opened my legs for her and it felt even better as her finger made little circles around my bud, and gently pressed on in. The sensation was deliciously overwhelming. I jerked my little butt backwards and impaled it - and gasped in pain! The vast size of her finger intruding in that tight little canal took my breath away

It immediately stopped. Her finger slowly slid out and my asshole quickly squeezed tight.

I lifted my head and softly moaned. I couldn't help myself. I didn't feel stoned and uncoordinated anymore. I was living in my subconcious and giving in completely to erotic sensations that I didn't understand. I completely submitted to her. Just like with Doloras.

Mrs Benson lifted me up to my knees and brushed the shower water across my back rinsing the soap suds. As she reached around me her robe fell open and I saw before me her breast, her soft white breast and large brown nipple, right in front of my face. The aureole of her nipple was tight with goose bumps and little hairs ringing` it. Gazing into the comforting female flesh I saw freckles and vague traces of blue veins within. I don't know what made me do it, I just wasn't myself at the time, I would never do something like that, but my lips leaned forward and took her nipple into my mouth.

She stiffened, suddenly, as I sucked gently like it was the most natural thing in the world. First her nipple got hard like a nut and then, as I continued sucking, it gradually softened and swelled full. I felt her body relax and her breathing deepen. I don't think I would have ever stopped if she hadn't finally pulled it slowly out of my mouth. It just jiggled there all puffy and nice. Then her other breast was pushed up to my cheek and the nipple moved around till it was in my mouth and I contentedly continued where I had left off. This time she cuddled me into her soft white breast and I reached up to feel it as I sucked. Her fingers stroked my ear and then felt down my back.

"That's a sweet boy."

Her hand went down lower, reaching in to touch my stiff dick, just grazing it lightly, scratching the underside, from my scrotum forward, making it jerk a little bit in response. Her nipple swelled full in my mouth as I felt those same fingers slip beneath my testicles which were now shrunk tight together in their sack like a hard little half sphere. She pressed up and gently rubbed my balls making them hurt exquisitely, pushing them up harder until they disappeared into my groin. I moaned as I sucked, and moved my pelvis around like I used to do for my sister, but real slow this time, sitting on the palm of Mrs Benson's hand. The tip of her finger slipped up into my rectum and that was just the icing on the cake. It hurt so good that I didn't notice her fat pink and brown nipple slip out of my quivering lips.

Now she began to rise and her hand left my pleasure place leaving it empty itchy and hard. My cheek moved down the smooth skin of her stomach to the ticklish curly hair growing up from her warm moist center. The overwhelming womanly fragrance brought back Dolores to me stronger than ever and I felt like I was living a true memory. The odor was so familiar and yet distinct, excitingly different, as the soft furry mound pressed into my mouth and I sucked on it lovingly like it was a juicy ripe peach. She stood over me and guided my head with her hands pulling me firmly into the warm pillows of her thighs as she adjusted her hips and knees to insert her wet nether lips better into my mouth.

"Oh, suck it, baby..." she breathed.

The wetness was thick now and I obediantly sucked harder.

Her index finger and middle finger slipped down between my lips and her fleshy grown up 'noony'. They opened into an inverted 'v' spreading her pussy lips apart to reveal the delicious hot crimson flesh behind. I felt a fat, firm little sausage poke determinedly into my mouth. She pushed it into my lips, back and forth, out and in, rocking on my face. My penis bobbed with little spasms as her girl thingie fucked my pliant lips. And, mmm,`` did I suck until she jerked and ejaculated thick creamy cum all over my mouth and whole face.

"Oh god, Ryan, oh god!"

She was moaning and gasping and almost suffocating me, rubbing her slimy cunt all over my lips and chin and nose. God that goo tasted good. And smelled like heaven. But she didn't stop, not for a minute. Her clit stiffened, longer and narrow, and it poked all the way out of its sheath as she frantically screwed my compliant lips. I could hardly keep my lips tight enough around her thrusting fuck stem as her pubic bone pounded into my nose hurting me and making it impossible to breath - and she came again, in gushes! This time it came from way up inside her and the come was thin and watery, not thick and creamy, as she spurted and spurted and spurted. She gasped and cried out loud. For a moment I thought she was peeing, but as I sucked it up and drank it spasm after spasm, it didn't taste like pee at all. It tasted like ambrosia.


Later she put a lace pair of panties on me and one of her camisole tops and we went to her bed. It wasn't long before those panties were down around my ankles and she was fucking my now not so tight little ass hole with her big hard delightful clit. After that I was unable to resist doing anything she desired of me.


I think that was the first time I ever came, you know really squirted something out of my penis. And I loved it. I loved it when she sucked my slender member into her warm wet mouth and moved her tongue all over it. The rough tip pressed at that sensitive spot where the bony penis muscle meets the underside of the swollen glans. As she rubbed with her tongue she sucked the head of my penis until the exquisite sensation rolled in waves out over my whole body. Her finger penetrated deeper into my hole and rubbed the back end of my squirting rod, and it felt like all of me was welling up to pour out into her hungry mouth. It was too much for me to handle. I lost all control and spasmed and wiggled and jerked my bottom onto her finger wildly until I collapsed exhausted.

I was out of my mind, trembling, panting. Never had anything come close to that feeling. As the waves of pleasure subsided, I looked at her, and realized that all I wanted was more. "Won't you please do it again, Mrs Benson?"

She just smiled as she stroked her creamy pussy, moving her fingers in and out and around the swollen labia. And put her sticky fingers into my mouth.

"Of course, sweetie. I'll fuck you again."

And to my delight she did.

*********************** I guess it was my nursemaid who predisposed me to be so horny and satisfied to have an older woman use me for her sexual pleasure. At least in my fantasies...

All rights reserved 2004 Jaymes Ryan jayryan90028@yahoo.com

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