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Since you two have gotten older, the sleepovers and spending every waking moment together have gotten a little rarer. Not wanting to violate the terms of the bet I played dumb before getting up to go to bed.

As I laid there I wondered just what in the hell Steven had planned for tomorrow. Sunday The next morning I got out of bed only to relieve myself, after which, I had planned on more sleep.

On my way back to the bed I looked out my second story window down into the back yard. I audibly groaned as I saw Steven following my mom around like a lost puppy.

Sunday was the day mom would clean up around the house and mess around in her flower garden. Steven did his best to hide it but every time mom bent over his eyes were glued to her ass.

Mom motioned for Steven to help her move a pretty large planter. Steven happily grabbed one side and they moved it about twenty feet.

As they sat it down mom stumbled backwards and fell flat on her ass. They both laughed loud enough for me to hear through the closed window.

Steven helped mom to her feet and started to brush some grass off of her back. In a particularly daring move I thought, he began to lightly brush the debris from her backside.

To my surprise, mom didn't say a word as my friend's hand slid over her backside. After moving another planter Steven did a stupid Hulk Hogan pose I guess as a way of telling mom he was strong.

Mom squeezed his bicep before giving him a look as if to say "not bad. Mom stared for a moment before going back to her work. I watched a few more minutes until I saw Steven leave through the side gate, but not before getting a big hug from my mom.

The rest of the day went by uneventfully until about seven when I got a call from Steven. I ain't helping you one bit. Just come to terms with losing.

You scared that I might actually score with your mom? I was sure he didn't have a chance so I finally relented to his demands.

At least this way he couldn't say I did anything to sabotage him. After hanging up the phone I walked downstairs and into the kitchen.

I grabbed a bottle of water from the fridge when I heard mom ask who I was talking to on the phone. I debated saying anything further but I figured it'd be better to get my "chore" out of the way.

And he wouldn't shut up about how pretty you looked at dinner last night. Having fulfilled my duty I just nodded and went back up to my room.

She didn't seem too overly excited to hear Steven's comment I thought. Man that extra money is gonna be kickass I thought. Monday Since it was summer I was in the habit of sleeping until noon.

After stumbling around for a while I made my way downstairs. I was just about to take a big drink of orange juice when I heard the front door open.

I heard mom's voice first as she was telling someone to come on in. I heard Steven's voice so I darted for the stairs before they could see me.

I stealthily got as far down the stairs as I could without being seen. I just had to know what he was up to now. He and mom were sitting at opposite ends of the couch.

It looked like they'd been running again. The T. If exercising can get me looking half as good as you I'd be satisfied. I rolled my eyes as he continued to pepper little comments throughout the conversation.

He was certainly persistent, I thought. My leg is killing me right now. I took a massage therapy class last summer at the health club.

He wasn't actually lying either. He really did take the class, but only because there was a girl he liked also taking the class. I don't know Steven.

I'll be alright; I'm just a little sore. I was glad mom seemed to be reluctant to accept Steven's offer. But he was like a dog with a bone.

Where do you want me? Steven smiled and pointed to a spot on the floor. Mom got up and laid down next to the couch.

Steven's eyes lit up as my mom stretched out before him. When mom went running she wore spandex shorts and a sports bra covered by a muscle shirt.

Steven took a moment to stare at mom's body laid out in front of him but he didn't waste much time. He started with mom's shoulders, slowly massaging the tense muscles.

Mom turned her head away from my direction, and with the T. Steven just smiled and worked his way down her back. Once he got to her lower back Steven used his elbow to apply pressure to mom's tense muscles.

The pressure caused mom to lift her head and turn it toward me again. I was not surprised to see her smiling. Who doesn't like a massage?

Steven looked at mom's ass for a few seconds and I wondered if he was going to be that daring. His common sense must've kicked in because he went to her calves next.

He used both hands to cup mom's lower leg. Once he got to the bend of her leg he used his thumbs to massage the tight tendons before doing the same to mom's other leg.

The son of a bitch looked around for a moment as if he was trying to decide something. Slowly he began to work his hands up above mom's knee.

At first nothing seemed to be amiss, but as I continued to watch, his hands crept higher and higher. It was hard to tell from my vantage point but his hands had to be very high up my mom's leg.

I was so intently watching Steven's hands that I'd forgotten about mom. I looked at her face and realized that the smile she had earlier was gone.

Her eyes were clenched tight and her mouth was slightly open. Just as I was processing what was happening she raised her head and said something to Steven.

I couldn't tell what it was but he smiled and then helped her up off the floor. They sat back down and continued watching T.

After nothing happened for a while I went upstairs for about an hour. When I came back down Steven was gone. After what had happened I was curious as to what exactly mom was thinking.

I had ten Benjamins riding on this bet after all. Report Story. Login or Sign Up. Literotica is a trademark. No part may be reproduced in any form without explicit written permission.

Password: Forgot your password? She will occasionally let a button "accidentally" come open when he is around if she's had a couple of beers, but voluntarily showing a breast or her pussy is too much for her.

She knows it is a turn-on for me, but it is very difficult to get past her modesty. But give her credit: she didn't try to back out of the bet.

The evening before I claimed my winnings, I talked to Frank about my plans, and he was more than willing to help out. I started off the evening by taking her to The Melting Pot, a fondue restaurant here in Richmond.

It is very nice - dark and romantic. We were seated in a booth in a small room. It was early enough that we were the only ones in the room.

After we had ordered our first drink, I told her to unbutton another button on her dress. This would open it to just below her breasts.

Since I had vetoed any underwear, when she did she was more exposed than she ever had been in public. She sat up straight to keep the dress from opening too much, but as we ate and drank our wine she relaxed and seemed to forget about how exposed she was.

She was sitting leaning forward a bit with her shoulders sort of slumped, and the view was wonderful. I could see some of both breasts, nearly to the aureole.

Before desert arrived I told her to unbutton one more button. Her dress was now open to well below her breasts.

When she sat up straight you couldn't see much. But when she would lean forward to take a bite of desert it would fall away from her body and I could see most of both breasts, including her nipples.

The drinks and wine had had an effect, and she soon grew careless, leaning forward and allowing me to enjoy the view. I told her I loved the way she looked, and to keep sitting that way.

She was embarrassed, but did as I told her. Our waiter arrived to clear the desert and offer us an after dinner drink.

When Bonnie saw him she gave a little start and straightened up. With him standing right there I said, "Bonnie, tell Aaron what our arrangement is tonight.

She looked down at the table and said, just as I had made her agree before we left home, "I have to do whatever he wants, whenever he wants, with no argument and no hesitation.

He grinned as he began to understand. This was what she had been afraid of. She said, "I don't think I can do this.

You have to do it. You made the bet, now it's time to pay up. Aaron won't mind, will you? Bonnie looked at me and asked, softly, "Are you sure about this?

She took a deep breath, closed her eyes, and slowly did as she was told. The top of her dress fell forward again and gaped open, and we could both see her breasts right down to the nipples.

What a turn-on! You are going to have to pay a penalty to remind you not to hesitate when I tell you to do something this evening.

Unbutton another button. The dress was now unbuttoned clear to her waist. Now open the dress and give Aaron a good look at what you were embarrassed to let him see the first time.

He had already seen her breasts, but actively showing them to him was a very big step. Glancing around the room to make sure there was no one else who could see, she opened it briefly, the immediately closed it again.

Do it again, but this time hold the dress open until I tell you to close it. She closed her eyes again and parted the material, letting her gorgeous tits spill out.

I need you in my pussy. I'm so fucking hot for you. He now held me by my hips and as he entered me, he would pull me back towards him — with his thumbs he would pull my ass cheeks apart.

As he pulled out he would squeeze them together. His paced picked up and I could tell that he was going to come.

I hoped that he would soon have me on my back, huge cock in my pussy and me with my legs in the air squealing as I approached orgasm.

His thrusts became harder as he began slamming his cock into me. He was soon riding me so hard that I would squeal with each thrust — I knew that I'd feel it tomorrow.

It seemed like an eternity that he power fucked my ass. I squealed and writhed uncontrollably as I struggled to endure his powerful anal thrusting.

He would pull out and ram his huge cock deep into me. I didn't know how much more I could take. He kept riding me hard and pushed me over the brink.

His cock exploded up my ass — a veritable river of semen was injected into my ass. I gasped in disbelief as come was injected in powerful jets.

Now in all aspects I was no longer an anal virgin. When he finished, he remained mounted, but his cock softened quite substantially. Do me in the ass some more.

You are so fucking huge, but it doesn't hurt. It feels so good. My cunt is dripping wet. You fucking me in the ass is such a fucking turn on.

It feels so good when you ass fuck me. You didn't spank me — you whipped me and it really fucking hurt, but it gives an edge to the fucking that I'm taking in my ass.

I'm so horny and my pussy is dripping wet. Will you please fuck my pussy. Ass fucking only. I'm going to fuck you in the ass until you can't walk properly.

I'm going to whip your ass, fuck your ass, come in your ass, rest in your ass and fuck your ass some more. I'm not going to let you touch your pussy and I'm not going to let you come.

He knew that he could fuck my ass as much as he wanted without ever bringing me to orgasm. He was going to ass fuck me and make me so horny.

He was going to break me. He started to rub my clit in firm circular motions which caused my body to twitch involuntarily.

Then I felt it. His cock began to grow. After his powerful orgasm, his huge, thick cock shrunk quite a lot.

It became soft and relieved the strain which allowed my asshole to shrink and relax. Now I could feel his cock getting thicker, harder and longer.

Without even moving it, I could feel the head moving deeper and deeper into my asshole. The increasing thickness was stretching me. His clitoral assault increased in intensity — he was rubbing harder and faster which caused me to writhe involuntarily.

The more that I writhed and quivered the bigger and harder he got. I was on the brink — gasping, squealing, grunting, writhing and squirming.

Suddenly he stopped. Please I'm so close. Please bring me to orgasm. I'm begging you — please make me come.

With the leather strap, he slapped my ass really hard about five times and then began to ride me again. I screamed with each heavy whipping.

His huge throbbing cock buried so deep into my vitals was slowly pulled out. Inch after throbbing inch of thick, woman taming man meat was pulled out of my ass until only the huge head remained up my ass.

He then began to slowly wiggle it a tight circle. I don't know why but this was driving me through the roof.

I was panting and grunting uncontrollably as my body trembled and quivered. He held my tits and twiddled my erect nipples as he began the long journey to bury his cock in me.

Over and over again he stroked me — slowly at first and then faster and faster until he was riding me hard. He was slamming his huge cock into my ass so hard that I was being knocked forward with each thrust.

I had to hold onto the headboard so as to weather the anal assault. My cunt was so wet from arousal that I was screaming and begging to be fucked in my pussy.

Suddenly he again exploded in my asshole. Powerful jets of semen were injected deep into my helpless asshole.

Again his cock shrivelled. He remained mounted and after a brief spell he began to caress my cunt. He would run his fingers along my slit — never touching my clit.

He would slip his finger into my dripping cunt and then back along my slit. I was so horny that I was trembling and in tears begging him to let me come.

I need your cock in my cunt. I'll do anything for you if you please fuck my cunt. You can spank me, but please bring me first. Please I'm begging you.

Whip me, beat me, do what ever, but please make me come. I will however beat your ass as punishment for trying to bribe me.

I was so desperate for an orgasm. With each orgasm, he was taking longer and longer to come. He was riding my ass longer and longer which made me hornier and hornier.

My ass was so tight with his huge cock inside me that every time he came, his cock exploded even though with each orgasm less and less semen was injected into me.

By now my innards were filled with so much come that I had an overpowering need to eject it. Once again he exploded in my ass, his cock softened, but this time he dismounted me "I have to take a leak," he informed me.

I was thrilled as I thought that I would have the opportunity to masturbate myself to orgasm. My thrill was short lived when he commanded me to stand at the end of our canopy bed and then proceeded to tie one arm to each of the bed posts.

When he was finished, my arms were spread and tied to the tops of the bed posts and my legs were spread and tied to the base of the bed posts.

He began to stroke my clit again ever so gently; driving me wild. I stood there all tied up spread-eagle helpless and fully exposed to his every whim.

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She laid out the clothes I was to wear. Pretty easy I thought until I realized there were no shorts or socks. Yep, you guessed it, just a skirt shirt and shower shoes.

The skirt she had purchased earlier looked a little like a kilt but it had a zipper on the left front leg and the shirt was more like a white see through silk wrap with arm holes.

She led me to the garage and had me get in the passengers seat and off we went. She took me to a seedy adult book store and headed straight to the counter guy.

She knew that she needed to buy tokens and with a knowing nod that she gave the counter guy she led me through the store and she made me browse slowly paying special attention to the magazine rack with gay magazines.

I was pretty confused by now and all the sexual visuals even the gay ones were getting me hard and the skirt was looking like a pup tent.

Then we headed towards the dildo area paying special attention to the strap-on dildos. Because I was dressed in a skirt and nervous as a cat on a hot tin roof I was too stupid to realize what was going to happen and just exactly how many notches she was going to kick it up.

She just appeared to be browsing and that was making me as uncomfortable but she kept picking up the different dildos and handing them to me and asking how I liked this one, or if I liked the color, or if the size and shape of this one was too much and so it went like this for what seemed like forever.

The whole time she kept rubbing them up against my face and putting them to my lips and I was really getting stressed out by all the guys looking and snickering at me as she asked these questions about plastic cocks and I was getting red as a beet.

She finally decided on one and made me take it to the counter and purchase it and telling me loud enough for everyone to hear that I had made a great selection and how much fun this one will be.

She then led me to the back of the store in video area and we went into a video booth locking the door. She dropped some tokens in the machine just like she knew what she was doing and I thought this was going to be fun as she made me stand up and remove my skirt.

She sat me back down and kneeling in front of me she started to rub my cock and I rolled my head back against the wall and moaned as I was getting really hard.

I began to realize we were watching a bi-sexual movie with guys getting their dicks sucked by other guys and with me getting my cock rubbed and sucked in a booth naked except for my shoes my cock was as hard as it has ever been before.

She looked me in the eye and told me that this was her bet and I had to due what she wanted or the game would be over for ever.

Like a dummy thinking with my little head I just nodded and said "yep". With this confirmation she raised her hand to the wall and for the first time I noticed the glory hole in it and she stuck her finger through it and waved it around for a second and pulled it back out.

Well I knew it was a glory hole and what it was used for but I didn't know any of the etiquette and was startled when a cock started poking its head through the hole right next to my ear.

She reminded me that a bet was a bet and I had to kiss and fondle the cock staring me in the face until she said to stop. Ok now the demons were rearing their ugly heads and I wasn't sure if I could cross that threshold.

I was mortified and I can't begin to tell you how scared at that moment I was. Keep in mind I am a large heterosexual, chauvinistic, male and at my age married as long as I have been to the same woman I had never even tasted my own cum, let alone the thought of being close to another guy or near his cock.

Now I knew one of my worst demons and fears was about to come to bear and it was time to put or shut up.

I swallowed hard and reached out to grab this average sized cock and as I touched it my mind raced with a million thoughts about the size, the shape, the color, texture, and most importantly the hardness.

Then I thought this guy was crazy for sticking his cock through the wall because he had no idea what was on the other side and what might happen to it.

Well he was safe and I was going to prove it. I could feel how hot my face was and how excited I was getting as I began to slowly rub this strange cock.

My wife started telling me what she wanted me to do to this cock and I began to follow her directions hoping she would let me get off soon as my balls were starting to ache.

I have to tell you that I was amazed how natural it became for me to fondle and rub this cock and watching it leaking its pre cum was making me want to lick it off just like an ice cream cone.

So I did! As my tongue touched the head at the piss hole I became obsessed with getting it in my mouth and as I licked the shaft up and down I wanted to get in my mouth and as far down my throat as I could.

As I was licking this foreign cock I could not believe how good this cock felt and how the warm soft texture with soft hair surrounding it was just making me go farther down the shaft until the head hit my gag reflex.

I would pull off it and swirl my tongue around the soft bulging head and then I would lick up and down the shaft feeling the veins bulge and throb as I would fondle it.

I was beginning to moan and I could feel myself getting lost and absorbed with this cock as I kept trying to deep throat it.

The sequence of events that happened next are so comical and amazing that it is hard to believe. My wife stood up and while leaning against the wall she began to feverishly rub her sopping wet pussy.

As she started to have an orgasm and fell against me, this accidentally forced his cock all the way down my throat causing a flurry of comical activity.

She was wedged against the wall and me in an awkward position and couldn't move and I started to gag while trying to get off this cock impaled in my throat and she was pushing against me harder and she went out of control with one of her biggest orgasms and this was just as the cock in my mouth started to twitch.

I knew what was coming and try as I might I just couldn't stop it. He started to cum in buckets right down my throat and as I began to choke I felt like I was going to die right here in a queer video booth with a cock in my mouth.

I finally pushed off the cock as it shot its third round right into my eyes with the fourth round hitting me in the nose and chin.

Well my wife began screaming with laughter at the site of this and fell to her knees in tears at the magnitude of the orgasm she had and the sight of her man with cum all over his face and dribbling from the corner of his mouth.

My mind raced with what just happened and my fear of tasting cum was now over. She began to recover and started kissing me and licking the freshly deposited sperm from this strange cock off my face and rubbing my cock at the same time.

After a few minutes the curiosity got the better of me so I decided to do a little spying. I crept up to the wall that separated the living room and the kitchen.

I got as close as I could to the doorway that led into the kitchen. From my vantage point I could see the entire kitchen in the reflection on the patio doors.

Mom was standing at the sink while Steven was sitting at the table. As mom went about her routine Steven was devouring her with his eyes.

They made small talk and every once in a while Steven would comment on how nice she looked. Mom would smile brightly as she went about fixing dinner.

Eventually mom got the pasta noodles off the stove and took them over to the sink to drain the water. Steven walked up behind her and looked over her shoulders.

Mom looked back over her shoulder at Steven. It was a funny look that I hadn't seen before. It didn't look like she was mad at all.

It was like she didn't quite know what to say. Steven dialed it down a bit and sat back down at the table. Mom went to the fridge to get the salad out.

As she bent down Steven's eyes were glued to her ass and legs. It was hard for me to tell in the reflection but I didn't see any visible panty line.

There was no way my mom was walking around the house without any underwear I thought. A little while later mom finally called me for dinner.

I sat down at the table and smiled at Steven. With me in the same room his little game wasn't going anywhere. While mom went to the stove Steven gave me a hand motion as if to say get lost.

I gave him a funny look. I knew that if I wanted to win the bet I had to not get in his way, so reluctantly I got up and grabbed my plate.

Stacy, I'll keep you company. I told mom I'd be careful and then walked back to the living room. As I ate and watched T. I would hear the occasional laugh.

Nothing was out of the ordinary until I heard my mom yelp as if she'd burned herself. I quietly reclaimed my place by the entrance to the kitchen.

In the reflection I could see that my mom had spilled some of the pasta sauce down the front of her dress. Steven had reached over and used his napkin to clean my mom up a bit.

To the untrained eye it looked like a simple act of kindness, but to me he was feeling up my mom. As he got lower on her chest my mom was looking intently at Steven.

I half expected her to say something as his hand went into her cleavage, but she remained silent. After a few tense minutes mom brought her hand up and moved Steven's hand away.

Steven just smiled and went back to his pasta. Mom fanned herself with her hand for a moment or two. She must've gotten hot after cooking dinner I thought.

After a few minutes I noticed that they were sitting kinda close to each other. I couldn't tell if it was mom or Steven that had slid there chair over but someone had.

I stood there for about fifteen minutes while they ate. That was awesome Ms. It looks like you really liked it judging from how much you got on you.

I hadn't noticed but Steven had some white sauce from the pasta on the corner of his mouth. As I watched, my mom licked her finger and used it to clean Steven's mouth.

Unbelievably, after she wiped his mouth she licked her finger clean. Steven didn't see her do it but I had.

What in the world was she doing? Well, Steven was like a child to her anyway, so no big deal I reassured myself. After finishing my dinner I brought the plate back into the kitchen and sat it down on the table.

Mom and Steven were over by the sink washing dishes. They didn't even know I was there as they talked and laughed. I had to hand it to Steven. It was only the first day and he'd gotten further than I thought he would.

I still wasn't worried though. Flirting with my mom was one thing, but actually sleeping with her was a pipe dream.

About an hour later I heard mom telling Steven goodbye. She walked over to the couch and sat down beside me.

Since you two have gotten older, the sleepovers and spending every waking moment together have gotten a little rarer.

Not wanting to violate the terms of the bet I played dumb before getting up to go to bed. As I laid there I wondered just what in the hell Steven had planned for tomorrow.

Sunday The next morning I got out of bed only to relieve myself, after which, I had planned on more sleep. On my way back to the bed I looked out my second story window down into the back yard.

I audibly groaned as I saw Steven following my mom around like a lost puppy. Sunday was the day mom would clean up around the house and mess around in her flower garden.

Steven did his best to hide it but every time mom bent over his eyes were glued to her ass. Mom motioned for Steven to help her move a pretty large planter.

Steven happily grabbed one side and they moved it about twenty feet. As they sat it down mom stumbled backwards and fell flat on her ass.

They both laughed loud enough for me to hear through the closed window. Steven helped mom to her feet and started to brush some grass off of her back.

In a particularly daring move I thought, he began to lightly brush the debris from her backside. To my surprise, mom didn't say a word as my friend's hand slid over her backside.

After moving another planter Steven did a stupid Hulk Hogan pose I guess as a way of telling mom he was strong. Mom squeezed his bicep before giving him a look as if to say "not bad.

Mom stared for a moment before going back to her work. I watched a few more minutes until I saw Steven leave through the side gate, but not before getting a big hug from my mom.

The rest of the day went by uneventfully until about seven when I got a call from Steven. I ain't helping you one bit. Just come to terms with losing.

You scared that I might actually score with your mom? I was sure he didn't have a chance so I finally relented to his demands. At least this way he couldn't say I did anything to sabotage him.

After hanging up the phone I walked downstairs and into the kitchen. I grabbed a bottle of water from the fridge when I heard mom ask who I was talking to on the phone.

I debated saying anything further but I figured it'd be better to get my "chore" out of the way. And he wouldn't shut up about how pretty you looked at dinner last night.

A costume reveals a new woman, and the bet is on! The Bet A bet gets out of hand. Getting Even It all started with a lap dance. A Lost Bet Sister humiliates brother, but he gets his revenge.

Transformation Ch. Teacher Poker Teacher's poker lesson backfires. Texas Hold Em Wife loses at poker, so they take turns to poke her.

Poke Her Poker A Mom must pay off a poker bet. Big vs. Biggest College girl and guy make a bet over size. Photo Session Ch. Lost Wife in Poker Game Couple sets up friend for the fuck of his life.

Lost a Bet He lost the bet, but I have to pay the debt. Dear Prudence Another dangerous wager on fidelity. Bet You My Wife! Becoming Her Bitch A simple bet changes everything.

A Neighborly Bet A neighbor bets that his wife will sleep with me. Car Trouble! Jenny makes a bet with her uncle to fix her car. Hot Tub Wager Two couples in a hot tub having fun.

Higher or Lower Siblings play a game of cards for money. I Bet My Girlfriend Poker games gone wrong as my shy gf is the prize.

Wife Becomes Fuck Slave A bet leads wife to become a fuck slave and be used. BabySitter Bet Babysitter is used to settle a friendly wager.

A Sure Bet Girl is taken by the men she trusted most. It Was in the Cards The weekly poker game gets spiced up. BunkBed Lost bet lets roomate fuck girlfriend on the bunk above.

A Lost Bet Ch. The New Neighbors Neighbors move in and take possession of couple next door. One Drink Too Far Man makes a bet with his wife, then loses.

Up for Auction Watching my wife and mother sold off for charity. Strip Poker Gone Wild A story of his wife, her best friend, and him.

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