Stepmother Plays Truth Or Dare

Stepmother Plays Truth or Dare

Stepmom, Maureen, plays truth or dare with her daughter, Colleen, her sister, Eileen, her niece, Erin, her mother, Mary, and her stepson, Brian.

Author's Note:

Even though a stepson is not blood related to his stepmother and his stepsister, because they all live under the same roof, sex between them is not only considered inappropriately forbidden but also incestuous.

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Stepmother Plays Truth or Dare

Looking back, my biggest mistake was to agree to play Truth or Dare with my horny stepson. What was I thinking? Playing that game opened the door for inappropriate sex.

Playing that game changed everything. Dramatically changing our mother and son relationship, we'll never be the same. Only, to my defense, I had never played the game before.

I didn't know much about the game, especially the rules of play of Truth or Dare. Adding to the inappropriateness of playing the game, I had been drinking. We all had been drinking and drank a little too much.

Turning sexual, the game quickly got out of hand. We just didn't play a game of Truth or Dare; we played an X-rated version of Truth or Dare. Just thinking about it, embarrassed then but having no regrets, I'm sexually aroused now. I'm glad that Brian suggested that we play that game.

###

It all started innocently enough on one bright and sunny morning. It was a big day for my stepson, Brian. It was his birthday. He turned twenty-one-years-old today.

I baked him a cake, had his birthday card, and a stack of gifts in the living room. As if he was 10-years-old again, when I first started caring for him just before his father died, I blew up balloons and printed out a Happy Birthday banner. Just as my 30th and 40th birthdays were big deals, his 21st birthday was a big deal, too. No longer a boy, today, he was a man.

I invited my sister, Eileen, my niece, Erin, and my mother, Mary, over to celebrate his birthday later tonight. With him being a lover of games, board games, card games, and video games, I hoped to keep him home and safe with me by playing games with him. Instead of him going out drinking with his friends, I volunteered to play any game with him that he wanted to play.

My friends took me to a CFNM (clothe female, nude male) strip club on my 30th birthday and again on my 40th birthday. While kissing me, French kissing me, hot strippers felt my breasts through my clothes, unbuttoned my blouse, and lifted my bra to fondle my naked breasts while fingering and sucking my erect nipples. My breasts are two of my erogenous zones. After having too much to drink, I'm unashamed to admit that I had more than one cock in my hand and in my mouth those nights.

I'm just glad that our friend, Patricia, doesn't drink. We were all too drunk to drive. She was our designated driver.

'Those were the days,' I thought.

It seems so long ago when I turned 30-years-old. Then, feeling sad about turning 40-years-old, I'm not looking forward to my fiftieth birthday, five-years from now. Except for my stepson, no one wants older women. With him sexually attracted to me, my daughter, my sister, and my mother, he's sexually attracted to older women with big breasts.

###

"Happy Birthday, Brian," I said as soon as he emerged from his bedroom.

As is our family tradition to do, I sang happy birthday to him.

"Happy Birthday to you. Happy Birthday to you. Happy Birthday, dear Brian. Happy Birthday to you," I sang.

Even though he waved a hand at me, I knew he enjoyed me singing happy birthday to him.

As he always does, difficult not to notice, making my nipples erect and my pussy moist, with me horny and sexually frustrated, he sported his morning wood, an erection that tented his pajama bottoms. Impossible not to notice, in the way that he stared at all that he could see of my naked breasts and my naked pussy through my nearly transparent nightgown, I tried my hardest not to stare at his erect cock. Yet, with it throbbing and pulsating, in the way that he talked to my tits, I found myself talking to his prick.

'Oh, my God,' I thought. 'His cock looks so big. I'd love to take that monster in my hand before taking it in my mouth and in my pussy.'

Glad that he doesn't sleep naked, I don't know how I'd react if he emerged from his bedroom wearing nothing but his smile. I sometimes masturbate over imagining him walking around the kitchen with his naked erection. I imagine him leaning over me to serve me coffee with his big dick only inches from my mouth. He wears a T-shirt, pajama bottoms without underwear, and his Ugg slippers.

With it hot in the apartment, I never wear a robe over my nightgowns. I only wear a robe over my nightgowns in the winter. I hate wearing robes and I never wear panties to bed. Moreover, with me no longer having a man in my life to wear my sexy nightgowns for, I wear them for my stepson. He likes seeing me in my short, sheer, and low-cut nightgowns as much as I enjoy him seeing me in my sexy nightgowns.

###

On this special day, I smiled, walked to him and, pressing my big D cup breasts against his muscular chest, I wrapped my arms around him and hugged him. With him 6'3" tall and me 5'9" tall, glad that we weren't the same height, instead of impaling my crotch with his erect cock, he impaled my tummy with his big dick. Something that I'll be using my pink bunny vibrator and big, black dildo over later tonight, it felt sexually arousing being dry humped by my stepson's pajama clad cock.

Then, when I stood on my tippy toes and leaned into him to kiss him on the cheek, catching me off guard, he turned his head and kissed me squarely on the mouth. The first time I kissed my stepson on the lips, not ready for what he was about to do, he surprised me. Yet, because it was his birthday, I allowed him to kiss me on my mouth.

Not wanting to make him feel uncomfortable by rejecting him, I put my arm around his neck and I returned his kiss with my kiss. Only not stopping with just kissing me on my lips, he tried to part my lips with his tongue while reaching his hand down behind me. Again, taking me by surprise, something that I never expected him to do, he lifted the back of my short nightgown to my waist.

Then, he cupped, felt, fondled, and squeezed my naked ass. I couldn't believe my stepson was groping my naked ass while trying to French kiss me. Stunned that he kissed me and tried to French kiss me while feeling, fondling, squeezing, groping my shapely buttocks, I pulled away from him.

"Brian," I said! "Jesus! What the hell are you doing? How dare you grope me like that? Oh, my God," I said, fluffing down the back of my nightgown. "That's not appropriate."

He looked at me deflated.

"Sorry, mom. With this my 21st birthday, no longer a boy but a man, I wanted you to be the first woman that I kissed. The guys are taking me out to a strip club," he said with an excited laugh.

I laughed, too.

"Well, kissing me is one thing but trying to French kiss me while groping my naked ass is something else," I said with a laugh. "Your celebration is premature because I'm not one of the strippers," I said with a chuckle. "I don't appreciate you lifting the back of my nightgown and groping my naked ass," I said with another laugh. "I'm so embarrassed."

I lied that I felt embarrassed when I was sexually aroused.

###

Something I always knew, since he turned 18-years-old, my stepson is sexually attracted to me. How could he not be? I'm hot, if I say so myself.

He's always staring at me while undressing me with his eyes. Giving me something to masturbate over, sometimes when I'm sexually aroused, unashamed to admit, I've deliberately flashed him. I've flashed him upskirt peeks of my panties, up nightgown peeks of my naked, red trimmed pussy, down blouse views of my cleavage and bra, and down nightgown views of my naked breasts and erect nipples.

Most times, wanting to be comfortable in my own home, I've unintentionally flashed him upskirt peeks of my panties, up nightgown peeks of pussy, down blouse views of my bra, and down nightgown views of my breasts. With him always looking, I know that he masturbates over me in the way that I pleasure myself while thinking of having sex with him. Yet, as long as we don't act on and go through with our forbidden, sexual desires, pleasuring ourselves in private is our release of our emotional tensions and sexual frustrations.

One day, when he stood in the doorway of the bathroom talking to me, as he usually does, he saw my naked breasts when my towel slipped down to my waist. Drying and brushing my hair, I had both of my arms over my head with a hair dryer in one hand and my brush in the other. It took me a long minute to retie my towel, cover my naked breasts, and reclaim my modesty.

"Oops," I said. "Don't look at mommy's tits. That's embarrassing," I said with a little laugh.

###

Only, instead of not looking at my naked tits, making my nipples erect and my pussy moist, he stared at my exposed tits. He stared at my naked breasts as if he had never seen a woman's naked breasts. He stared at my exposed tits in the way that I stared at his naked, erect cock whenever I caught him playing with himself.

In the way that I masturbated myself over him seeing my naked breasts, I'm sure he masturbated himself and still masturbates himself over seeing me topless. With him rattling the windows, while mumbling my name, I've heard him masturbating over me. Checking the history on his computer, I know something that he doesn't know that I know. He enjoys watching stepmother, stepsister, step aunt, and even step grandmother porn videos. Gross. I can't believe he masturbates over imagining having sex with me, my daughter, my sister, and my mother.

A masturbation machine, he masturbates every morning and every evening. While bringing up his laundry and unable to knock on his bedroom door with my arms full, I push his door open with my foot. With him wearing his headphones while watching a porn movie, I've caught him masturbating and have seen his erect cock more than once. He has a big dick, more than 7" possibly as big as 8".

Quite the shocking surprise, I've found my used panties under his pillow several times. Yet, giving me more to pleasure myself over, the fact that my stepson masturbates over me makes my nipples erect and my pussy moist. No doubt, he'd love to have sex with me as I sometimes would love to have sex with him. With him jerking off so much, I wouldn't be surprised if he's still a virgin.

Admittedly, I've always been a bit of a whore and a big tease. Calling my bluff with me being a cock tease, my virginity ended on my prom night when I was 18-years-old. I not only gave my first hand job and blowjob but also, my date, the captain of the football team, fucked me in the back seat of his dad's Lincoln Town Car. After having sex with dozens of men later, not how I had planned it, here I am a 45-year-old widow with a daughter and a stepson.

###

This was it. Having raised him for the past twelve years, my stepson was now a man. I only wished his father had lived long enough to see his son as the tall, handsome, and muscular man that he has grown to be. Yet, I feared him going off with his friends to a strip club and drinking. In the way that his dad was killed in a drunk driving accident, I didn't want to see that as his son's reality, too.

"Brian," I said.

With his erection distracting me, I paused to gather my thoughts. I had a difficult time talking to him while he still had a huge, throbbing, and pulsating erection. I couldn't stop thinking of him kissing me on the lips, trying to French kiss me, lifting the back of my nightgown, and groping my naked ass. With my nipples one of my erogenous zones, if only he had felt and fondled my breasts while fingering my erect nipples through my nightgown, I may have moved to my knees and sucked his cock.

'Happy Birthday, Brian,' I imagined saying. 'Now that you're a man, mommy's birthday gift to you is blowjob. Not considered a blowjob unless you cum in my mouth and I swallow your cum, you may cum in mommy's mouth and I will swallow your cum,' I imagined saying to my stepson.

Now that I thought of sucking his cock, I couldn't remove the thought of myself kneeling in front of him. After seeing his naked, erect prick several times, I imagined stroking his cock while sucking his prick. I imagined him cumming in my mouth and me swallowing his cum. Then, I imagined him bending me over and fucking me from behind while fondling my naked breasts and pinching, pulling, turning, and twisting my erect nipples.

'God, what' wrong with me,' I thought? 'I'm such as whore. How dare I imagine blowing my stepson? How dare I imagine him fucking me?'

###

"I know it's a rite of passage to want to go out with your friends and get drunk but," I said with a pause.

'Mommy wanted to give you a birthday blowjob,' I wanted to say but I didn't. 'If you stay home, I'll not only suck your cock but also, I'll allow you to have your way with my naked body. Would you like that, Brian? Would you like your stepmother to blow you and, after you cum in my mouth and I swallow your cum, allow you to fuck her?'

Only, I didn't say none of that either.

"I planned a birthday party for you with presents," I said instead.

I knew telling him about birthday presents would get his attention. Brian liked receiving gifts as much as he loved buying gifts for everyone.

"If you stay home with us tonight, I know how much you like playing games, I'll play any game that you want, even Risk, Dungeons and Dragons, or those violent video games that you enjoy playing," I said with a laugh.

I hated playing Risk and Dungeons and Dragons because they took hours to play. I disliked the violent video games that had now become sexual in content. Making me feel uncomfortable, when playing them with him, truth be told, they embarrassed me as much as they sexually aroused me. Playing some of those X-rated video games made me horny.

I invited my sister, Eileen, my niece, Erin, and my mother, Mary, and, of course, my daughter, Colleen, who still lives with us will be there, too. Five women to celebrate Brian's birthday should be fun. He loved his stepsister, his step aunt, his step cousin, and his step grandmother as much as he loved me. Judging him by the porn videos that he watches, he's as sexually attracted to all of them as he is to me.

With him undressing us all with his eyes, he sexually looked at them in the way that he sexually looked at me. I dare say that if he could have an orgy with his stepmother, stepsister, step aunt, step cousin, and step grandmother, he would. Further, unashamed to admit, if I could have sex with my stepson, I would, too.

###

Glad that he decided not to go out with his friends to a bar or to a strip club, I told him that I'd do anything that he wanted on his birthday. As soon as I told him that, I imagined him making out with me while feeling me through my clothes. I imagined him slowly undressing me and stripping me naked.

Then, I imagined him stripping himself naked as if his clothes were on fire. I imagined being in bed naked with my naked stepson. I imagined him making himself comfortable between my long and shapely legs while fingering my pussy, fondling my breasts, pinching, pulling, turning, and twisting my nipples while masturbating me and giving me an orgasm.

Then, I imagined him licking me. I imagined him eating his stepmother's cunt. I imagined him giving me a second orgasm with his fingers and with his tongue.

I imagined him moving up to me, mounting me and making out with me while making slow and passionate love to me. Then, I imagined him humping me faster and harder. I imagined returning his fast and hard humps with my fast and hard humps.

I imagined him fucking me fast and hard enough to give me a third sexual orgasm, this time with his cock. Finally, I imagined moving halfway down the bed and taking his erect prick in my hand before taking his big dick in my mouth. I imagined blowing my stepson. I imagined stroking his cock while sucking his prick.

I imagined him cumming in my mouth and me swallowing his cum. Then, I imagined him exploding a second load of cum all over my freckled face, in my red hair, and all over my naked breasts. I imagined him giving me a cum bath and me dripping with his cum.

###

Ready to start the birthday party, my sister and my niece were first to arrive with my mother not long behind them. My 42-year-old sister is as tall as me but instead of having red hair, she has black hair with blue eyes and C cup breasts. The contrast between her pale skin, dark hair, and blue eyes is quite appealingly attractive.

My 21-year-old niece, Erin, not as tall as us, has strawberry blonde hair and green eyes with D cup breasts. She's very beautiful. My 5'6", 67-year-old mother has grey hair, and huge double D cup, Irish milkmaid breasts. With her looking like an older version of me, no doubt, when I'm her age, with my breasts sagging down like her breasts, I'll look just like her.

Our favorite gathering place, we all congregated in the living room. I opened two bottles of wine, a Merlot, and a Chablis, and poured everyone a glass, except for Brian who preferred a beer. The five of us sat on my huge couch that took the entire wall while Brian sat in his reclining chair across from us.

Sexually teasing him by deliberately flashing him, I sat with my knees parted just enough to continually flash my white panties beneath my short skirt. Making herself comfortable, and with us cut from the same cloth, my sister did the same thing. She sat with her knees parted just enough to flash her step nephew, her panties beneath her short skirt, too. With both of us exhibitionist whores, and with men thinking that they're at the right place and at the right time, we loved flashing all that unsuspecting men love to see.

With both of them budding exhibitionistic whores, too, my daughter and my niece wore blouses that were low-cut. Every time they leaned forward to take a sip of their wine; they gave Brian down blouse views of their cleavages and their low-cut bras. My mother no longer caring how she sat, as long as she was comfortable, had her knees parted plenty enough to not only flash Brian her granny panties but also, her pussy mound, her camel toe, her pussy slit, and her gray patch of bushy pubic hair through her bloomers.

###

"Well, Brian," I said. "Have you decided on a game that we all can play," I asked?

He smiled. Not even having to think about it, he said what he wanted to play.

"Truth or Dare," he said.

I looked at him with confusion?

"Truth or Dare? What's that? Is that a game," I asked?

My daughter and my niece laughed.

"Yes, mom. It's a game," said Colleen.

I looked at my daughter with curiosity.

"How do you play it," I innocently asked?

My niece smiled at me. Sitting at the edge of the couch, she leaned forward to look at me while giving Brian a great down blouse view of her long line of sexy cleavage and her low-cut bra.

"The player whose turn it is decides to either answer a question, truth, or perform a task, dare. If the person chooses truth but refuses to answer the question truthfully, the consequence can be a dare agreed upon by the group," said Erin.

Sounding simple enough, ready to play the game, I nodded my head to show that I understood the rules.

"That sounds like fun," I said.

Eager to play the game, Truth or Dare sounded like a harmless game to play and a good and fun way to pass the time. Better than playing Risk, Dungeons and Dragons, or one of his violent video games, I had no idea that this game was so disgustingly and immorally sexual. So, now that I know how sexual the game can be, all the time that my daughter, stepson, and niece have been playing Truth or Dare, they've been having random sex with their friends or even with strangers.