Masturbating with Mom’s Panties

Masturbating with Mom's Panties

Late physically and emotionally developing and still a virgin, yet, quickly sexually blossoming and maturing, at 19-years-old, Joe is finally, sexually coming of age.

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Author's Note:

Something that happened more than thirty-years ago, this true story was written for Joe. He wanted me to tell everyone what happened to him the first time that he had sex. Indeed, the story is about his first, sexual memory that he had with not only his mother, Samantha, but also with his mother's best friend and coworker, Carrie.

He always had an erection whenever around them. He never had sex before, other than with his horny hand. With them continually sexually teasing him, it was sexually appropriate and seductively befitting that his first sexual experience should be with his mother and her best friend.

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If it wasn't bad enough that Joe had orangey, red hair and freckles, his friends constantly teased him by calling him Howdy Dowdy, Alfred E. Newman, and/or Carrot Top. Long, lush, red hair looked sexy on a woman, especially on a tall woman with long legs, big tits, and a shapely ass, but not so much on a man and definitely not good on Joe. Instead of being accepted as just another one of the guys, standing out, with his orangey, red hair as his flag of shame and his beacon of embarrassment, his flaming, orange hair didn't help him meet with their approval.

If only he knew that when he matured that his hair color would change to a darker hew of red. If only knew that he'd find the most beautiful, redheaded woman who, love at first sight, was physically attracted to him because of his red hair. If only he knew that he'd meet and marry sexy and shapely, beautiful Veronica, finally, he'd be glad that he was born with red hair.

Wanting to continue the lineage of redheads by having a brood of children with red hair, Veronica loved her red hair and was searching for her perfect, redheaded mate to marry. Tempted to travel to Ireland to find a redheaded man there, had Joe not been a tall, lanky, redheaded man with freckles, she may not have been attracted to him. She may have not found her perfect man. She may not have married him. Fortunately, for Veronica, she found her man in Joe.

Yet, what did he know? Sexually innocent, he didn't know anything about women. Just 19-years-old, he was too busy masturbating himself to realize anything other than his own self-deprecation. With his mother's best friend, a regular, overnight house guest, he was too busy trying to see his MILF of a mother and her sexy, best friend, in their sheer and sexy nightgowns, topless and/or naked.

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Not having any friends, Joe was a loner and a loser. Even though her loved playing basketball, he didn't play on a team. Instead, he shot baskets alone. When others enjoyed the community pool during the hot summer, he shot baskets.

He started shooting free throws from the foul line and had a more than ninety percent percentage of making shots from there. Then, wherever the ball landed, he shot from there. He had a more than a seventy-percent percentage of making a basket from anywhere on the court. Only, with him not much of a team player, never comfortable passing the ball as a way to move the ball down the court, he was content shooting baskets alone.

Yet, slow to sexually develop, where most young men start masturbating years earlier, Joe didn't start playing with himself until after he graduated high school when he turned 18-years-old. From that moment forward, finally finding something to do that sexually pleasured him, his self-abuse of his big, rock-hard cock was constant and continual. Now that he knew how to relieve his sexual frustration and horniness while sexually exciting him, Joe was always masturbating while imagining his mother and her best friend naked and having sex with them.

When he wasn't masturbating himself, he was walking around with a noticeable erection. Whether a picture or a word, the slightest erotic thought made him hard. As visual proof that Joe had a big cock, with them always staring at his erect prick, his mother, Samantha, and her best friend and co-worker, Carrie, unmercifully teased him about him always being sexually excited. Continuingly walking around with an erection as his personal badge of honor, yet, instead of being proud of his big dick, him having a throbbing and pulsating, never ending erection embarrassed him.

Unable to help himself, Joe always had an erection, especially in front of his mother and her best friend. His mother, Samantha, and her best friend, Carrie, were always sexually teasing him by calling attention to his huge erections. His MILF of a mother and her sexy best friend were quick to call undo attention to his stiff prick by pointing to it, laughing at him, and even reaching out their manicured fingers to playfully grab the head of his big dick. Seemingly, they found it sexually exciting to tease such a shy and sexually inexperienced, young man.

Not having a father to tell him about the birds and the bees, and not yet knowing how to take care of his erection to make it go away, sometimes, he made a mess of his underwear. Seemingly having no control of cumming, he routinely ejaculated in his pants. Instead of masturbating himself to relieve his sexual frustration, he stuck a wad of tissue in his underwear and allowed himself to cum naturally.

He continually awakened with wet dreams and made a mess in his pajama bottoms and sometimes his sheets. Finally, just by him touching himself, fondling the head of his cock, and stroking himself to relieve the pressure of his throbbing and pulsating prick, he learned to cum naturally in a tissue instead of in his underwear or in his pajama bottoms. That was the beginning of him masturbating every day, multiple times a day.

Finally, a new world of masturbation and all things sexual opened up for him. He felt free. He felt empowered. Becoming a man, he finally had more control of his body.

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If it wasn't bad enough that I was always sexually excited enough to have a constant erection, my mother and her friend made matters worse by deliberately, sexually teasing me. They flashed me upskirt peeks of their panties and down blouse views of their bras. My mother greeted me every morning with a full-bodied, chest to pelvis, hug and a kiss on the lips. When she wasn't deliberately walking around me in her bra and panties, topless, and/or naked, she wore her sheer, low-cut, sexy nightgowns without having the modesty to wear a robe over them.

Always dressing and undressing with her bedroom door wide open, as if waiting for me to walk in her bedroom and fuck her, she was an incorrigible exhibitionist and an incestuous slut. Her best friend was no better. Ready to give me a striptease show whenever I was looking, she allowed Samantha to lead the sexual way with me.

Whenever her best friend arrived for a visit, which was nearly every day, taking her cue from Samantha, she greeted me with a full-bodied hug and a kiss on the lips. In the way that my mother rubbed her big tits against my chest, with Carrie a small breasted woman, she reached around me to pull my hands down and around for me to cup and feel her sweet ass. With her proud of her shapely ass, on several occasions, instead of rubbing her frontside against my frontside, she deliberately rubbed her backside against my frontside.

With me their sexual victim, to write that Samantha and Carrie were exhibitionistic whores would be an understatement. They took advantage of my sexual shyness and naïveté. As soon as they hugged me, between the feel of their sexy and shapely bodies and the scent of their alluring perfumes, not taking much to get me sexually excited, I had an immediate erection.

They didn't help me by rubbing up against my throbbing and pulsating cock while kissing me. Instead, they continually sexually teased me by intentionally trying to get me sexually excited. Surprised that I didn't strip them naked and have sex with them, in the way that they continually, sexually teased me, it would serve them right if I had stripped them both naked and fucked them. Yet, it would only be a matter of time before my mother and/or her best friend would dare to have sex with me.

In the way that my mother crossed all of the incestuous lines by flashing me her sheer and sexy nightgown clad, underwear clad, topless, and/or naked body, she clearly wanted to have sex with me. In the way that my mother's best friend, sexually teased me, she obviously wanted to have sex with me, too. With me barely nineteen-years-old, little did I know that both women were ready to suck me and fuck me. Looking back, in hindsight, both women were ready to do whatever it took to help sexually and emotionally develop me.

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Whenever they sat across from me in the living room, they sat with their knees parted just enough to show me their bright, white, bikini panty covered crotches. As if they were Sharon Stone in Basic Instinct, they'd slowly and deliberately, sexually cross and uncross their long and shapely legs numerous times while continually and deliberately flashing me their panties. When my mother sat across from me to watch TV in her sheer, short, and sexy nightgowns, she'd sit with her knees parted enough to flash me her naked, blonde, trimmed pussy.

Seeing my mother's naked pussy and Carrie's bright, white bikini panties was plenty enough to give me an erection and cause me to masturbate. Causing me to have, yet, another erection, by bending at the waist in front of me to expose their panties, they squatted down in front of me to pick up something they had deliberately dropped. They continually flashed me their panties in upskirt peeks. Not done sexually teasing me, they wore low-cut tops with their low-cut bras or without wearing a bra.

While waiting for me to make my sexual move in touching them and feeling them, they continued sexually teasing me. When not bending at the waist and/or stooping in front of me, they leaned over me to give me downblouse views of their low-cut bras, their long, sexy lines of cleavage, and/or their naked breasts. Wanting to make me sexually excited enough to cause me to have an erection, they'd hope to make me erotically excited enough for me to make my sexual moves on them.

Masturbating every day, numerous times a day, I masturbated twice every morning and twice every evening. I masturbated over imagining my mother stroking my cock and sucking my cock. I masturbated over fucking her. I masturbated over Carrie stroking my cock and sucking my cock. I masturbated over fucking her, too.

When I wasn't masturbating over imagining my mother naked and having incestuous sex with me, I masturbated over imagining my mother's best friend naked and while imagining her having forbidden sex with me. Suffice to write, I was always masturbating. Instead of cumming in my mother's willing mouth and in my mother's wet pussy, I ejaculated my seed in a tissue. Instead of giving Carrie what she sexually wanted, fearing she'd reject me, I continued denying her the pleasure of my young, hard, naked body.

Then, whenever I saw something that I shouldn't see of my mother and/or her best friend in a downblouse view or an upskirt peek, I masturbated again. If only my mother, Samantha, knew that I played with himself while holding, touching, feeling, and sniffing her used panties, she'd be mortified and I'd be embarrassed. Yet, as if I was a car thief wiping away my fingerprints from a stolen car, I was careful to wipe away the load of cum deposited in her panties with a tissue. I'd stealthily return her panties to the laundry basket after cumming in them.

Fortunately for me, oblivious to me using her panties to masturbate over her, my mother hadn't noticed the cum in her used panties and/or caught me cumming in her panties while holding and sniffing her panties, yet. It would only be a matter of time before my mother and/or Carrie caught me masturbating. Perhaps, if they caught me stroking my cock, that would get the ball rolling. If they caught me masturbating and cumming, perhaps, I'd finally find the courage to touch them, feel them, and fondle them.

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My sexual nightmare began when my mother asked me to retrieve her boyfriend, Keith's, watch that had fallen behind her bed between the mattress and the headboard. Only, unbeknownst to her and to me, Keith had set a trap that was intended for my mother. Sexually naughty of him to do, he had installed two pairs of handcuffs behind her bed. Locked and spring loaded, they were triggered to close and lock should anyone stick their hand behind the bed. I was the unfortunate victim of Keith's sexual joke of my mother's intended bondage.

Something that my mother wouldn't think was funny, if she was handcuffed and trapped on her bed, she'd panic. She'd have to wait hours for her boyfriend to arrive home and unlock her. With her handcuffed to her bed, she'd be unable to use the bathroom. With her feeling helpless, something that she hated feeling, she'd be angry that Keith had handcuffed her to her bed without her consensual permission. Matter of fact, when she discovered the ruse, a strong, executive woman in management who never wanted to be a victim of bondage, she broke up with him immediately.

No man was going to sexually dominate her by handcuffing her to her bed. Once she was helpless, what was to stop him from calling a few of his friends to have sex with her. She imagined three or four of his friends gangbanging her. She imagined being forced to suck their cocks and forced to allow them cum in her mouth. She imagined Carrie being forced to gangbang his friends, too.

"How dare you attempt to handcuff me to my bed. Don't call me. Don't write me. Don't text me. We're done. Get the fuck out of my house," she said tossing him a paper bag with a few of his personal possessions.

Then, when he took a step forward, she slammed her front door shut in his face and locked it.

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I was relaxing naked on my mother's bed and masturbating myself while holding and sniffing a pair of her used panties when she called me and asked me to retrieve Keith's watch from behind the bed. As soon as I hung up the phone and reached my right hand behind her bed, with a resounding 'click', the handcuffs locked around right wrist. I reached back behind the bed with my left hand and, with another resounding click, my left hand was handcuffed to her bed, too.

I struggled to free myself but to no avail. With the handcuffs locked to the back of the bed, I was trapped. I could only move my hand a few inches, as far as the handcuff would allow. I couldn't hide my mother's panties beneath her pillow. I couldn't return the tube of lube to the nightstand drawer. I couldn't return the box of tissues to the nightstand. I was totally helpless and vulnerable. I couldn't even pull a sheet over me to cover my nakedness.

Naked and with an erection, embarrassed as much as I was sexually excited, I had to remain there until my mother arrived home from work. After having seen my mother topless and naked numerous times, forced to return the sexual favor with me handcuffed to her bed, my mother would finally see me naked. She'd finally see my big, erect, cock. Only, as embarrassing as it was sexually exciting, she didn't arrive alone. Never going anywhere without her, she arrived home with her sidekick, her best friend, and coworker, Carrie.

As soon as I heard the front door open and close downstairs, I readied myself for the inevitable. Helpless to cover myself, my mother was finally going to see me without my clothes. She was finally going to see me naked. She was finally going to see my erection.

Even though I was panicking because I was trapped, I couldn't wait for my mother to see me naked. I couldn't wait for her to see my big, erect cock. I wondered what her reaction would be to seeing my big dick. Would she look? Would she stare? Would she look away? Would she reach out and touch it, fondle it, and stroke it? Would she suck it? Would she fuck it?

I didn't know. I had no idea. With my mother an incestuous whore, I hoped that she'd do all of those things but hoping that she had the keys to the handcuffs, I hoped that she'd unlock me first. I'd love to touch and feel my mother while she touched and fondled my naked prick.

'Oh, my God, I'm so sexually excited that my mother is finally going to see my naked, erect pick,' I thought. 'I only wish I wasn't handcuffed to her bed. I wish I was free to strip her naked, too.'

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In the way that my mother routinely exposed herself to me by walking around me in her sheer, low-cut, sexy nightgowns without having the modesty to wear a robe, I've always wanted to expose myself to her. She was unembarrassed and unashamed to show me her underwear clad, topless, and/or naked body. In the way that she walked around me in her bikini panties and low-cut bra, topless, and/or naked, my mother was finally going to see me without my clothes. Only, not having the courage to show her my naked prick before, I had no choice today but to grin while baring it.

Wanting to give her the most sexually arousing view of my naked prick, before I was handcuffed, I was glad that I had quickly stroked myself to a bigger erection before I was handcuffed. I was glad that I stroked myself faster and harder but held myself back from cumming. With me having a full erection, especially emboldened with the thought of her walking up the stairs, I wanted my mother to see the full length and girth of my big, erect, naked cock.

After all of the times that she exposed her naked ass, her naked tits, and her naked pussy to me, I couldn't believe that I was finally going to expose my naked prick to my mother. Only, embarrassed for her to know that I was masturbating while holding and sniffing her panties, I wished I could have hidden her used panties. I wished I could have put the lube away. I wished I could have returned the box of tissues to the nightstand. I wished that I could have covered myself with a sheet.

'Oh, my God,' I thought to myself. 'My mother is finally going to see me naked. She's finally going to see my stiff prick. Again, I wondered what her reaction will be to seeing my naked, erect cock. Would she look in curiosity, would she stare in sexual arousal, or would she look away embarrassed at seeing me naked?'

Wishing that I could hide her panties under her pillow, nonetheless, I was as sexually excited as much as I was embarrassed that my mother would see my naked prick but also that she would finally see my big, erection. Then, when I heard her and Carrie talking downstairs in the hall, I had an immediate and throbbing erection. Both my mother and her best friend would see me naked. They'd both would see my big, erect, naked prick. I didn't think that I could get any more sexually excited but with both Carrie and my mother seeing me naked, I was even more sexually excited.

'Oh, my God. This is unbelievable. I couldn't have planned this better had I tried,' I thought. 'Only, I wished I wasn't handcuffed to her bed. I wished my hands were from for me to touch and feel my mother and Carrie while I imagined them fondling and stroking my naked cock. Nevertheless, I was so sexually excited to finally show them both my naked, erect prick,' I thought.

'Finally, both my mother and Carrie are going to see me naked. In the way that I wondered what my mother's reaction would be to seeing my naked prick, I wondered what Carrie's reaction would be to seeing my naked cock. Again, I wondered if she'd look in curiosity, if she'd stare in sexual arousal, or if she'd look away in embarrassment.'

While waiting for them to come upstairs, I wished I could stroke myself to a bigger erection. Only, with both my wrists handcuffed to her bed, I couldn't. I'm glad that I already had an erection. Moreover, with the thought that Carrie would see me naked and with an erection, too, I was glad that I had a pulsating and throbbing erection for her to see.