My Many Missed Sexual Opportunities

Missed Sexual Opportunities

I have regrets over missed, sexual opportunities.

Yet, interestingly enough and understandably, the sexual opportunities that I most regretted not taking are those that had to do with incestuous sex with my blood related relatives or forbidden sex with my in-laws. My missed sexual opportunities and sexual frustration started with my mother, Caroline, my sister, Flora, and my aunt, Thelma. I could have had sex with all three of them.

My name is Freddie. After celebrating my 21st birthday at a strip club with my friends, I arrived home drunk. Thank God my friends drove me home and I wasn't driving. I said a quick hello to my mother, Caroline, and my aunt, her sister, Thelma, who was visiting, and headed upstairs to my room. There every night drinking coffee, smoking cigarettes, and chit chatting, and with my aunt living only a street over, my mother's youngest of six sisters by twenty-years, visited every night.

As soon as I entered my room, I closed my bedroom door. Something that I always do, sleep naked, I stripped off my clothes and, not even bothering to pull down the covers, I flopped back on my bed because I was shot. It felt so good to be home. It felt good to be naked.

My hand quickly found my naked penis and I stroked myself to the drunken memory of a stripper giving me a lap dance arranged by my friends as my birthday gift. Sexy and shapely, the stripper was a good looking dark haired woman with big tits. Normally, not allowed to feel a stripper's breasts in a strip club but I was in the VIP room with her.

She allowed me to feel her naked breasts while she stroked and sucked my cock. My friends paid extra for me to cum in her mouth and I did. I'll be masturbating for the rest of my horny life after having sex with a stripper, her blowing me.

With my room spinning, I hoped that I didn't get sick. Unable to finish masturbating myself, not long after I closed my eyes and started to fall asleep, awakened by their noise, I heard my mother and my aunt talking and laughing as they walked upstairs. They never come upstairs together.

Then, I heard them walking down the hall towards my room. My aunt has never been in my bedroom. Suddenly filled with sexual anticipation, if I remained naked my mother would not only see me naked but my aunt would see my erect, naked cock, too. Having already dick flashed my mother lots of times, I'd love to dick flash my aunt. I wondered what her reaction would be to seeing my naked, erect prick.

Would she look? Would she stare? Or would she look away in embarrassment and in shame. There was only one way to find out and that was not to cover myself with my bedspread.

Still horny after that stripper gave me a lap dance and blew me, again, with my mother having seen me naked before, I wanted her to see me naked again now. I loved showing my mother my naked cock. Now that she was here outside my bedroom, I wanted my aunt to see me naked, too. Curious for their reactions when barging in my bedroom without knocking and seeing my naked, erect prick, my aunt seeing me naked would give me plenty to masturbate over later. I couldn't wait for my Aunt Thelma to see my big dick.

# # #

Planning to deliberately flash them, again, with my mother never knocking but just barging in my room, if I didn't cover myself with the bedspread, they'd both see me naked. Something that I'll be masturbating over for the rest of my horny life, I wanted my aunt to see me without my clothes. I wanted her to see my erect, naked cock.

Knowing that she was coming up to my room to deliver my laundry, I've allowed my mother to see me naked several times before when deliberately allowing her to catch me masturbating. Especially with her looking, it's exciting to show my mother my big dick. Then, when she touches herself when I'm stroking myself with my eyes closed, clearly, my mother wanted to see my prick as much as I wanted her to see my prick.

As soon as I heard my mother and my aunt climb the stairs while loudly talking and laughing, I quickly stroked myself to a big and hard erection. I wanted them to see my big dick. As if there was a drumroll of sexual anticipation going off in my head, I not only was going to flash my mother my naked prick again but also, I was going to flash my aunt my naked erection, too.

Only taking me a minute to get hard, with me filled with excess testosterone at that age, I always had an erection. Nearly as stiff as steel, my erect cock was so hard that I couldn't even bend it forward. Proud of my big dick, I couldn't wait to see their reactions from seeing the sheer size of my erect cock.

Then, when I heard them walking down the hall, I closed my eyes and pretended that I was sleeping. This time, instead of my mother barging open my bedroom door without knocking, my aunt barged open my bedroom door without knocking. I slitted open my eyes just enough to see them watching me from my doorway. Not turning on my bedroom light, the light from the hall was plenty enough for them to see that I was naked.

"Look, Carrie," said my aunt. "Freddie is not only naked but also, he has an erection." She looked at her sister. "He certainly has a big dick. With my husband always drunk, it's been a long time since I've seen an erect prick," said my aunt.

I watched my aunt and my mother stare at my erect, naked cock. Then, surprising me, not expecting her to do what she did, my aunt stepped in my room. If that wasn't enough, as if she was about to pray, she knelt beside my bed. While looking back at her sister and smiling, she stared down at my naked, erect cock.

"I love his big dick, Carrie," said my aunt.

My mother stared at her sister wide eyed.

"Thelma. What are you doing," she asked? "Let's go."

Then, shocking me and something else that I'll be masturbating over for the rest of my horny life, my aunt took me in her hand. She fondled the head of my prick with her fingertips while my mother watched with sexual arousal. Then, she slowly stroked me before leaning forward to take me in her mouth.

Something else that I'll be masturbating over for the rest of my horny life, my aunt was blowing me. Thelma was sucking my cock while stroking my prick. She wanted me to cum. She wanted me to cum in her mouth.

"Thelma," said my mother in a loud whisper! "Thelma! What are you doing? Don't do that," she said. "Stop! That's your nephew. Stop! You'll wake him."

She continued stroking my cock while sucking my prick as my mother watched her sister blow me. Then, she removed my cock from her mouth, stood, left with my mother, and closed my bedroom door behind her. Even if only briefly, I couldn't believe that my aunt not only saw my naked, erect prick but also, she stroked, and sucked my big dick.

When I felt her removing me from her mouth and standing up to leave, I regretted not putting a heavy hand to the back of her redheaded, pretty head and forcing her to continue blowing me. I regretted not cumming in my aunt's mouth. I regretted not forcing her to swallow my cum. I regretted not shooting a second load of cum all over her freckled, pretty face. I regretted not giving my aunt a cum bath and seeing my mother's sister dripping with my cum.

# # #

The next day, something that I do every morning, I deliver my mother her coffee and her newspaper. I never bother knocking first because she's always in bed watching the news on TV. This time when I opened her door, she wasn't in bed.

Instead, shocking me as much as she sexually excited me, she stood by her nightstand while facing her open, bedroom door. She had removed her nightgown. My mother was naked. I couldn't believe my eyes. Clearly, she must have been sexually aroused seeing me naked, while watching her sister stroke me and suck me last night.

The first time seeing my mother without her clothes, all that I could do was stare. I stared at her huge, double D cup, naked breasts. I stared at her symmetrical, brown areolas. I stared at her erect, brown nipples. I stared at her black, bushy pussy. As if I had never seen a naked woman before, I continued staring at my naked mother in the way that unsuspecting women stared at my naked cock when I dick flashed them.

Instantly, I had an erection that tented my pajama bottoms. Figuring that she would, she made no move with her hands or with her forearms to protect her modesty and cover her naked breasts and/or her naked pussy. Instead, she stood there with her arms by her sides while staring at me staring at her. Knowing that I was coming to her room and opening her door, my mother had deliberately flashed me. She wanted me to see her naked as much as I loved seeing her without her nightgown.

Surprising me, not saying anything, she didn't admonish me for opening her bedroom door without knocking and catching her naked. While thinking that she would, she didn't ask me to leave. With sexual arousal taking control of her face, she seemed to enjoy me seeing her without her nightgown as much as I loved seeing my mother naked. Again, something else that I'll be masturbating over for the rest of my horny life, I couldn't stop staring at her naked breasts and her naked pussy.

'This is not just any woman that I'm seeing naked, I'm seeing my MILF of a mother without her clothes,' I thought.

Instead of stepping in her room to touch, feel, and fondle her naked breasts, instead of kissing her while reaching around her to feel her shapely, naked ass, all that I did was to stare. In the way that my aunt had her way with my naked body, I regretted not having my way with my mother's naked body. I regretted not pushing down my pajama bottoms to show her my erection. I regretted not putting a gentle hand to her shoulder as a not so subtle hint for her to move to her knees and blow me.

In the way that my aunt stroked me while sucking me, I would have loved for my mother to stroke me while sucking me, too. I would have loved to put a gentle hand behind her black haired, pretty head and cum in her mouth while watching her swallow my cum. I would have loved to push her back on the bed, mount her, and make out with her while making love to her before fucking her. I regretted not fucking my MILF of a mother fast enough and hard enough to give her an orgasm with my cock.

Alas, the innocent dope that I was, all that I did was stare. Stunned, in the way that my mother has seen my naked prick many times, in the way that her sister saw my erect, naked prick, I couldn't believe that I was seeing my mother naked. With my mother staring at me with sexual arousal, no doubt, while waiting for me to do something, and me staring at her with sexual excitement, she finally said something.

"Freddie," she said. "I'm getting dressed," she said while still not making any move to cover her nakedness.

She was waiting for me to touch her tits, feel her tits, fondle her breasts, and finger her nipples. She was waiting for me to cup her pussy and finger her pussy. She was waiting for me to take her in my arms, and kiss her while reaching around her to feel and squeeze her naked ass.

# # #

I wished I had put a hand to the back of my aunt's head and forced her to continue blowing me. I wished I had put a hand to the back of my mother's head and had her blow me, too. I wished I had touched, felt, and fondled my mother's naked breasts. In the way that my aunt, her sister did, I wondered if my mother would have blown me. While masturbating myself, I imagined feeling my mother's big, naked breasts. I imagined having sex with my mother.

From that day forward, every time my aunt came over, I imagined kissing her and making out with her while feeling her breasts through her top and bra. I imagined sticking my horny hand down my aunt's top and feeling her naked breasts while fingering her erect nipples. I imagined sticking my erect cock in her mouth and having her blow me while my mother watched. Then, I imagined sticking my erect cock in my mother's mouth while my aunt watched. Alas, I never did any of those things.

With my big sister just as bad as my mother, my sister, Flora, always barged in my room without knocking. God forbid I opened her bedroom door without knocking, I'd never hear the end of it. As many times as I've masturbated in front of my mother with my eyes closed and my headphones on, I allowed my sister to catch me masturbating, too. Interestingly enough, instead of immediately leaving my bedroom and closing my door behind her, my mother and my sister stayed to watch me stroking my cock. Seemingly, they both enjoyed watching me masturbate myself.

With my eyes slitted open enough to see them staring, I've seen my mother touch herself. I've watched her fondle her double D cup breasts through her nightgown while fingering her nipples. I've watched her lift the hem of her short nightgown and expose her black, bushy pussy to my horny eyes, while rubbing her clit and finger fucking her pussy. Tempted to open my eyes and watch my mother masturbate herself, not wanting her to know that I had deliberately allowed her to see me stroke myself, I didn't dare.

Like mother, like daughter. My sister did the same, too. Barging in my bedroom without knocking and, instead of immediately leaving my room when catching me masturbating, she stayed while staring at me stroking my erect, naked cock.

In the way that my mother felt her breasts through her nightgown, my sister felt her D cup breasts through her nightgown, too. Then, she lifted the hem of her short nightgown to rub and finger fuck her brown, trimmed pussy. In the way that I watched my mother masturbate herself with my eyes slitted open, I watched my sister masturbate herself, too.

# # #

With me having become quite the exhibitionist, I loved dick flashing unsuspecting women. While knowing that my sister and her two, 24-year-old friends, Carol, and Vivian, would be soon barging in my bedroom without knocking to borrow my records, I quickly stripped myself naked. I donned my headphones, closed my eyes, and fell back on my bed. Wanting her friends to see my erect cock and watch me masturbate myself, I quickly stroked myself to a big and hard, throbbing erection.

Not having to wait long, I heard them outside of my bedroom door talking and laughing. Then, my sister opened my door without knocking. I pretended that I was unaware that they were standing in my bedroom staring. While continuing to stroke myself in front of them, I slitted open my eyes just enough to see the three of them standing in my room and staring at my naked cock while I stroked my erection.

"Pervert," said my sister while pretending that I was the pervert and she wasn't. "How dare you masturbate in front of me and my friends? What's wrong with you? Cover yourself," said my sister, throwing a pillow at me. "You're such a sick bastard to expose yourself in front of your sister and her friends."

Then, she screamed for my mother.

"Mom! Freddie's a pervert. He flashed my friends his naked prick," she said. "He masturbated himself in front of them."

My mother rushed upstairs to see my sister and her two friends standing in my room while I quickly tried to dress.

"It's not my fault. I didn't flash them. They barged in my room without knocking," I said.

My mother turned to the three women.

"Everyone out. Give him some privacy," said my mother. "You know better than not to knock, Flora," she said my mother to my sister while staring at my naked prick in the way that my sister and her two friends stared at my big dick.

Again, giving me even more to masturbate over, I stroked myself over my sister and her two friends seeing me naked and masturbating. Already, I've dick flashed five women, my mother, my sister, my aunt, and now my sister's two best friends. I couldn't wait to dick flash more women.

# # #

Again, like mother, like daughter, my sister, Flora, continued barging in my room without knocking. As if they wanted to see me without my clothes, sometimes, she'd have two other of her friends with her, Anne and Gwen, barging open my door to borrow my records. Whenever my sister had her friends over, knowing that I would deliberately flash them, I remained naked in my room on the chance that they barged in my bedroom. My sister wanted to see my naked cock and her friends wanted to see my naked prick, too.

I listened to them talking and laughing about seeing my erect prick as I was excited as over them seeing my big dick. I lost count how many times I masturbated over my mother, my aunt, my sister, and her friends seeing me naked. I love exposing myself to women. I only wished that I had more women to show them my erection. I only wished that, in the way that my aunt did, they'd take me in their hands before taking me in their mouths.

Yet, God forbid if I opened Flora's closed, bedroom door without knocking, I'd never hear the end of it. Especially if I caught her in their bra and panties, topless, and/or naked, with her slapping me, kicking me, and pinching me, I'd have holy hell to pay. Yet daring myself to do so, biding my time, I'd love to return the favor and barge open my big sister's and/or my mother's bedroom doors while hoping to catch them were topless or naked. If I caught my mother naked again or saw my sister without her clothes, I'd do more than just stare.

With only a 15-year difference in our ages, my aunt, who has always been sexually attracted to me, has never seen me without my clothes until that fateful day when I was drunk and naked. Yet, I've seen her B cup, naked breasts more than once. We used to go to the Bella Vista beach, at Canobie Lake in New Hampshire with my aunt and her family. The first time that I saw my aunt's tits was when I was 18-years-old. With her bathing suit top falling wide open with her, she leaned over the barbeque in her low-cut bathing suit.

'Oh, my God. I'm seeing Aunt Thelma's naked breasts,' I thought. "I love her tits and her erect nipples."

I lost count how many times I masturbated over seeing my aunt's naked breasts. Whenever she leaned over me to serve me a drink or food, she deliberately flashed me her naked breasts the entire day. Then, surprising me by catching me not only looking but staring down her bathing suit top, she smiled up at me. Then, she looked down to see what I was seeing.

"Do you like what you see, Freddie? Do you like my tits," she whispered with a laugh so that no one else would hear?

I nodded my head and smiled up at my aunt while I sat there staring down her opened bathing suit top in shock. I couldn't wait to masturbate over seeing my aunt's naked breasts later. I saw the entire shape and size of her naked breasts. I saw her symmetrical areolas. I saw her erect nipples.

Then, even after catching me staring, she looked up at me smiling while making no move to close her bathing suit top. In the way that I loved flashing my naked, erect prick to unsuspecting women, she deliberately flashed me her naked breasts. My aunt wanted me to see her naked breasts as much as she wanted to show me her naked breasts. I masturbated over seeing her breasts for years and still do. She had such shapely breasts with big nipples.

I've even seen my aunt's naked, red, bushy pussy and her shapely, naked ass. Every time she came over my house, while wearing her short, flared skirt, she danced to music in the kitchen while I'm sitting at the dining room table. Whenever she spun around, and with her wearing pantyhose instead of panties, as if she's Marilyn Monroe standing on a subway grate, her short skirt rises to her waist. She flashed me her naked pussy and her naked ass. I've lost count how many times I've masturbated over seeing all that I shouldn't see of my aunt.

# # #

Just as I regretted not having had sex with my sister, Flora, and her two friends, Vivian, and Carol, I regretted not having sex with my aunt and my mother. Only, my regrets continued with my mother-in-law after I married. With her always deliberately flashing me after I deliberately dick flashed her, I regretted not having had sex with my MILF of a mother-in-law, Charlotte.