My Second First Time Without Regets

My Second First Time Without Regret

My second chance for a do over without having regrets.

A dick flashing exhibitionist, Jerod, deliberately dick flashed his mother, his sister, his sister's friends, his aunt, his grandmother, his girlfriend's mother and her friends, and his girlfriend's daughter and her friends. Jerod has dick flashed every woman that he knows.

My name is Jerod, and I just turned 65 years old. Getting old fast, I remember being 35 years old. In my heart, I still feel like a much younger man. Yet, with me now older, weaker, and feeling tired and dizzy all the time, I'm unable to do the things that I used to do and loved to do.

"Happy birthday to me," I said out loud while laughing while celebrating my birthday alone.

I'm tall, 6' 4" tall, and thin, 170 pounds, with salt and pepper hair with piercing, blue eyes. I've been skinny my whole lift. Even though I look 10 years younger, fifty-something instead of sixty-something, unable to buy alcohol even when I was 21 years old without an ID, a curse then that's now a blessing, I always looked younger.

Yet, with my bad knees, bad back, and an irregular heartbeat, needing to slow down and take it easy, as if happening overnight, feeling tired and cranky, I'm beginning to feel my age. Sadly, like everyone else, suddenly feeling as if it's happening overnight, I'm slowly growing old. Every day I have a new pain and a new ache.

Even though I always took care of myself with exercise and not smoking and being careful about the amount of scotch that I drank, it's not easy growing old. Yet, better than dying, which I don't recommend either, I don't recommend growing old. No longer able to do and enjoy the things that I easily did in my youth, growing old sucks.

# # #

Something that I'm proud to have accomplished, a huge accomplishment, I have a black belt in martial arts. Sadly, no longer able to challenge younger men to show them that I still have it, I no longer train for the next dan. Instead, I stay away from the dojo. With me no Kung Fu master, I'll never be a Shifu.

Sadly, something that I've done for thirty-years, martial arts and MMA fighting are for younger men and no longer for me. Yet, even though I'm older, I'm still able to defend myself. Knowing all of the pressure points of where to strike and how hard to depress and/or hit, I'd make short work of anyone who dared to try to take advantage of me.

'I must warn you that I'm a black belt,' I imagined saying to anyone who dared to bother me on the street.

Something that I needed to say so that I wouldn't be charged with assault, in the way that an MMA fighter, a professional boxer, or professional wrestler must confess in advance before they beat the crap out of anyone.

'My hands are licensed as dangerous weapons,' I imagined saying while holding up my hands for them to see.

# # #

When thinking back, haunted my memories of them, I have a lot of regrets, and most of them are sexual. Indeed, something that most men have, I regret all of the missed opportunities of my youth, most of them sexual. I wished I knew then what I know now. If I did, I would have had sex with every woman that I know.

I wished that I had the confidence to show my interest by taking the next step with a woman who made the first move. One of any number of women could have been the one to have made me happy, given me children, and stayed with me to help raise our family. Now, just faded memories, I wonder where they all are now. I wonder if they regret not having had sex with me as I regret not having had sex with them.

I wondered if they're married. Probably, they are. I wonder if they have children. No doubt, they do. I wonder if they're divorced.

I wonder if they think of me in the way that I think of them. Yet, not to be, I wish that I had made a life with this one or with that one. Alone and lonely, if I enjoyed a relationship with any one of them, it would have been better than what and who I have now, nothing and no one.

Yet, as shocking as it's true, and something surprising to know, I've come to realize something I didn't know until much later in life. Many women over the age of 50 years old are whores. When men are masturbation machines and sexually maturing from 18 years old to 30 years old, women don't show their true colors for their wants and needs for sex until they turn 50 years old to 70 years old. That would explain why the elderly, especially women, have so much sex in nursing homes.

'No longer having to save it for anyone, who knew,' I thought? 'If I knew that women that age were whores, I would have dared myself to take advantage of that fact. Fuck younger women, I would have solicited and had more sex with older women.'

Forget about dating younger women and women my age, wasting my money wining and dining them, and taking them to movies, I would have dated older women. I would have dated women my mother, my aunt, my mother-in-law, and my grandmother's age. If I had dated older women, with most older women whores, I'd be guaranteed having sex without having to spend a dime. I regretted all of the older women in my life who made a pass at me that I didn't respond back.

'What was I thinking? Sex is sex, no matter how old the women are,' I thought. 'There are plenty of attractive, sexy, and shapely women over fifty.'

In the way that older men love younger women and are attracted by their beautiful looks and their shapely bodies, a two-way street, something that I never knew, older women love younger men. Younger men can easily get and maintain an erection whereas too many older men usually have a limp dick. Younger men can go all night to give them multiple orgasms, whereas older men fall asleep after cumming one time and long before satisfying the woman.

In hindsight, confusing me, and with me a good-looking man, so many women, especially older women, made the first move to seduce me while expecting me to respond in kind. Yet, with me shy and lacking experience, thinking back, without any exceptions, I could have had sex with every woman, younger, my age, or older than me, especially with those women older than me. I wondered how different my life would have been had I had sex with this one or with that one, and/or if I had committed myself to this one or to that one.

'Too late now. Having nothing but regrets, I missed out on all of the fun,' I thought.

# # #

Yet, most times, what stopped me from acting on the sexual opportunities presented were those that my MILF of a mother, June, my sexy, older sister, Christine, my aunt, Gloria, and even my 65-year-old grandmother, Mary, offered me. With me a testosterone filled, horny, young man, I discovered masturbation at 18 years old. As soon as I did, and not having a woman to satisfy my horniness, always stroking my prick, I became a masturbation machine. With five times my record, normally, I'd cum three and four times a day, every day.

Something so forbidden for me to do, daring myself to do so, I deliberately allowed my mother, June, to catch me masturbating several times. The first time that I did, curious for her reaction to her seeing my naked, erect prick, as nervous as I was excited, I couldn't wait to dick flash her. Giving me even more to masturbate over, whether she looked, stared, or looked away, I'll be masturbating over my mother seeing me naked for the rest of my horny life.

Something that she always did, with her barging in my bedroom without knocking, as soon as I heard her climbing the stairs to deliver my laundry, I quickly stripped myself naked. I couldn't believe that I was going to do it. I was about to dick flash my mother.

Then, once naked, I donned my headphones. I fell back on my bed, closed my eyes, and stroked myself to a big and hard erection. As soon as I saw her feet beneath my bedroom door, I let her know that I was playing with myself over her.

"Oh, mother, I'd love to make out with you while touching and feeling you through your clothes. I'd love to slowly undress you. I'd love to strip you naked while touching and feeling your naked body everywhere," I said.

I stroked myself faster. I stroked myself harder. Determined to cum for my mother as soon as she opened my bedroom door, I wanted her to see me cum.

"Then, I'd love to finger your pussy while licking your pussy," I said. "I'd love to eat you mother. I'd love to give you an orgasm with my fingers and my tongue. I'd love to watch and hear you cum."

Vibrating the whole house, I stroked myself faster. I stroked myself harder. I continued masturbating over the thoughts of seeing my mother naked and her having sex with me.

# # #

I continued my masturbation dialogue for the benefit of my mother.

"I'd love to make love to you, mother. I'd love to fuck you fast and hard enough to give you an orgasm with my cock. Then, I'd love you to blow me. I'd love to watch you stroke my cock while sucking my cock. I'd love to cum in your beautiful mouth and watch you swallow my cum," I said loud enough for her to hear through my closed bedroom door.

Surprising me, instead of scurrying away, she silently and slowly opened my bedroom door without knocking. As soon as she did, instead of admonishing me for masturbating over her, and immediately leaving my room, she put her laundry basket down and remained in my room. I slitted open my eyes enough to see her standing by my closet door. She stared at my naked prick as if she had never seen an erect cock.

Seemingly, my mother loved seeing my naked prick as much as I loved showing her my big dick. Then, shocking me, she did something that I never expected her to do. Cupping them in her hands, she touched her double D cup breasts through her nightgown while fingering her erect nipples and continuing to stare at me stroking myself. Something that I wished I could do to my mother, I watched her fondling her breasts while fingering her erect nipples.

Then, with her not stopping there, the first time seeing my mother's naked cunt, shocking me as much as she excited me, she lifted the hem of her nightgown to expose her brown, bushy pussy. Obviously, with my dialogue making my mother sexually aroused, I watched her finger her pussy. I couldn't believe that my mother masturbated herself to me, stroking myself. I always wondered if my mother played with herself and now, I knew that she did.

While regretting that I didn't, I always wondered if I had made a move on my mother, if she would have had sex with me. In the way that she fondled her breasts, fingered her erect nipples, and masturbated her pussy, I would have loved to have fondled my mother's naked breasts, fingered her nipples, and masturbated her. Yet, not to be, I never acted on the opportunity to have the incestuous sex with my mother that she presented me.

# # #

Then, blowing my mind, the next morning when I brought my mother up a cup of coffee and her morning newspaper, as I did every morning, she was always in bed watching the news. I opened her bedroom door without knocking. Only, this day was different. Instead of her in bed, she stood beside her bed naked. She had removed her nightgown. She returned the favor of me seeing her naked by allowing me to see her naked.

The first time seeing my mother naked, unable to stop staring, I stared at her enormous, double D cup, naked breasts. I stared at her erect, symmetrical, brown areolas and her dark brown nipples. I stared at her bushy, black pussy. I stared at my naked mother.

Not protecting her modesty by covering her nakedness with her hands and/or with her forearms, she stood with her arms by her side. She stared at me in the way that I stared at her. She wanted me to see her naked.

Something that I wished I had done, I regretted not walking to her. I regretted not touching, feeling, and fondling her naked breasts while pinching, pulling, turning, and twisting her erect nipples. I regretted not fingering her naked pussy. I regretted not taking her in my arms and kissing her while reaching behind her to feel and squeeze her naked ass. Yet, this was my mother and not some whore that I picked up at a bar and asked home.

Filled with regrets, I always wondered if I had pulled down my pajama bottoms and exposed my erect, naked prick to her, what would she have done. Would she have taken me in her hand and stroked me? If I had put a suggestive hand to her shoulder, would she have moved to her knees, and taken me in her mouth. Would my MILF of a mother have blown me?

Would she have sucked my cock while I fondled her naked breasts and fingered her erect nipples. Would she have allowed me to cum in her mouth and swallow my cum. After she blew me, I wondered if she would have allowed me to finger and lick her pussy. Then, I would have loved to have made out with my mother while making slow, passionate love to her before fucking her.

# # #

Like mother, like daughter, my big sister, Christine, always barged in my bedroom without knocking. In the way that I dick flashed my mother, daring myself to do so, I couldn't wait to dick flash my sister. Curious for her reaction to her seeing my naked prick, I waited until I heard her talking and laughing in the hall outside of my room with her two friends. A three for one dick flashing surprise, I dared myself to dick flash all three of them.

As my mother always did, I knew that my big sister, Christine, would enter my bedroom without knocking with her two friends, Vivian, and Carol, in tow, to borrow my records. As soon as I heard my sister open her bedroom door and heard them in the hall talking and laughing, as if my clothes were on fire, I quickly stripped myself naked. As I did with my mother, I did with my sister. I donned my headphones, fell back in bed naked, closed my eyes, and stroked myself to a big and hard erection.

As soon as she barged open my bedroom door without knocking, I slitted open my eyes to stare at my sister and her two friends. Instead of immediately leaving my room and closing his door behind them, as if hypnotized by the sight of me naked and mesmerized by watching me stroking my prick, they stood frozen. Instead of looking away, they stared at me masturbating until my sister yelled for our mother.

"Mom! Jerod exposed himself to my friends and I. Pervert," she said, throwing a pillow at me. "What the fuck is wrong with you? Cover yourself," she said, throwing a pillow at me.

Yet, instead of leaving my room and closing my door behind them, Christine still remained there with her two friends, Vivian, and Carol, while the three women stared at my erect, naked prick. If only they had allowed me to stroke myself a little longer, I would have loved to ejaculate a load of cum in front of them. Instead, I quickly tried to get dressed. Yet, when my mother came up to my room, instead of admonishing me, she came to my defense.

"You should knock the next time, Christine," said my mother. "Everyone out. Give Jerod some privacy to get dressed," she said.

My mother turned to look back at me. She smiled while staring at my naked prick. Again, she liked seeing my naked, erect prick as much as I loved showing her my big dick.

# # #

Then, there was the time with my aunt, Gloria. An exhibitionist, she always flashed me. When she wasn't showing me her panties, she showed me her cleavage and her bra. While regretting that I didn't, had I made a move on her, now that I know that women her age are whores, I suspect that she would have had sex with me.

I remembered the time when we went to the beach together. With my aunt doing all of the cooking on the grille, every time she leaned forward, her bathing suit top fell open with her. Unable to stop staring, I stared at her C cup, naked breasts, and her erect nipples.

She caught me staring. When she did, she looked up and smiled at me. Then, she looked down at her exposed breasts before looking up at me again.

"Do you like my tits, Jerod," she asked? "Do you like your aunt's big breasts?"

Stunned that she caught me staring and asked me if I liked her tits, all that I could do was to nod my head.

"I love your tits, auntie," I said. "You have beautiful, big breasts."

With the two of us alone and further back from the beach while everyone else was in the water, and too far away for anyone to see us, I should have reached my hand inside of the top of her bathing suit. Knowing that this was something she wanted me to do, I should have felt her naked breasts while pinching, pulling, turning, and twisting her erect nipples. I should have removed my cock from my bathing suit, stroked myself to a big and hard erection and dick flashed my aunt.

Then, as if she had read my mind, she said what excited me for her to say and to want to see.

"I can see your big bulge in your swimming trunks. I've given you an erection," she said with a laugh.

She smiled at me.

"Show me your cock. I want to see it. In the way that I showed you my naked breasts, I want to see your naked prick," she said.

Not having to ask me twice, I pulled down my bathing suit. As if my cock was a Jack-in-the-Box with a spring on it jumped out of swimming trunks. I quickly pulled up my bathing trunks before anyone saw me. Giving me something else to masturbate over, I'll be stroking myself after seeing my aunt's naked breasts, showing her my naked prick, and imagining her naked and having sex with me.

# # #

My grandmother, Mary, was as big of a whore as my mother, my sister, my sister's friends, and my aunt. Whenever I mowed her lawn, she greeted me at the door in her short and sexy, low-cut nightgown. Leaving nothing to the imagination, I could clearly see through her sheer nightgown as if she was naked.

I could see the size and the shape of her humongous, naked breasts, her big, brown erect nipples, and her bushy, brown pussy. Then, when she turned the other way, I saw the size and the shape of her big ass along with her ass crack. Seemingly, my grandmother was an exhibitionist, too. Giving me more to masturbate over, with me a masturbation machine, in the way that I continued to masturbate over my mother, my sister, and my aunt, I'll be masturbating over imagining my grandmother naked and having sex with her, too.

Then, after I mowed her lawn, with me hot and sweaty, she made me homemade lemonade.

"Before you get perspiration stains all over my furniture, Jerod, you must shower," she said. "Get undressed and I'll get you a towel."

As soon as I entered the bathroom, stripped myself naked, and turned on the water, my grandmother entered the bathroom. She sat on the closed toilet and opened the shower curtain enough to see me without my clothes. I couldn't believe that my mother's mother stared at my naked prick in the way that my mother, my sister, my sister's friends, and my aunt never removed their eyes from my big dick.

"Don't turn off the water," she said. "I need you to help me in the shower so that I don't fall," she said.

'What? Seriously,' I thought? 'Blowing my mind, I couldn't believe that I was about to see my grandmother naked. I couldn't believe that she wanted me to help her shower. I couldn't believe that I'd be touching and feeling her naked body everywhere while washing her.'

Instead of leaning inside to wash her naked body with a warm, wet washcloth, I couldn't believe my grandmother wanted to shower with me. From that day forward, every time I mowed her grass, we showered together. Even though we never had sex, I not only saw her naked but I touched and felt her elderly body everywhere that a grandson should never touch and feel his grandmother.

Unbelievably, every time I showered at my grandmother's house; she took a shower with me. I stood behind her while holding her. With my erect penis resting against her ass crack while she hung onto the pole, I helped wash my grandmother's naked body.