Category: BDSM Stories

The Anal Cherry

by That_Guy71©

My wife and I were avid sports fans. We had met in college and followed basketball very closely. She could hold her own in ANY sports bar when it came to stats, the draft and quite often she could predict who would be in the play-offs.

We had been out to a party one evening. It was a huge client and we were celebrating a recent victory in court. I was struggling to walk much less drive, so my wife took the keys and got us home safely.

She seemed a little upset with me. As we drove home, I tried to start up a conversation about basketball; something I hoped would keep her mind off topic.

"I like the Timberwolves for the playoffs this year." I said.

She said nothing.

"I think they will destroy your Warriors early in the playoffs." I said smugly.

She smirked, "If the Timberwolves make it passed the first round, I will let you fuck me in the ass."

I got a little sober hearing this and viewed it as a chance to engage her in a conversation that I had wanted to have for quite some time.

"So my Wolves just have to survive the first round?" I asked.

"Yup" she replied.

"An' I get to take you in the ass if they do?" I asked with a hint of hopeful in my voice.

"Uh-huh" she replied - without taking her eyes off the road.

She glanced over at me, "What do I get if they are shut out before the playoffs even start?"

"I will be your slave for a day." I said - without thinking (and assuming sex was still the topic).

"HHmmmmmmm" she replied.

She stuck out her hand and we shook on it. Then she laughed.

"You know they just lost their starting forward, right? He was arrested for assault." she said.

"FUCK" I mumbled.

"Playoffs start next week Dear... Shall I make my list of demands now or would you prefer to be surprised?" she said in a smartass tone.

"Its not over yet..." I blurted out.

She smiled smugly as we drove through the country side.


We had gathered up all the usual things for the playoff game. We grill and have drinks, some snacks and we try to enjoy ourselves.

At the half, my Wolves were down by 22 points.

"They BEAT these guys in the regular season..." I kept telling myself.

At the end of the 3rd quarter, they were down by 13. My wife kept rubbing it in.

"As my new slave, I WILL demand perfection and attention to detail... or there will be HARSH punishments..." she would mock me.

With 3 minutes left in the game, they were down by 8. THIS was a nail biter.

"Your term as my slave will begin at 9am tomorrow morning... and last until 8:59am the following day." she stated - as if they had won.

With 2 minutes left, they were down by 10.


I tried to remain calm and confident on the outside.

With 30 seconds left, they were down by 5 points. BOTH teams looked winded and tired.

The ball was thrown in and stolen. A jump shot from the 3 point line... BOOM!!

"Down by TWOOO Honey... do you prefer KY Jelly or Baby oil?" I started in on her.

She stopped and looked at me cold.

She broke her stare when the ball was stolen and my Wolves tied the game with seconds left to play.

"WOOOO HOOOO!!" I yelled.


Overtime was the most likely outcome at this point. I was more comfortable about THAT than I was about thinking what she had planned for me.

"Double or nothing?" she challenged.

We shook.

"YOU Dumbass!!" I thought to myself.

With only 5 seconds left in the game, the Wolves had to throw it in and the other team would have the ball.

The whistle blew...

I could FEEL my heart beating.

Their Forward sprinted to the far end of the court and with less than 1 second left, he heaved the ball at the goal.



"FUCK!!" I blurted out.

My wife tackled me on the couch and was laughing uncontrollably...

"I OWN YOU!!" she yelled out. "You are MINE... for 48 hours..."

"Starting NOW or starting at 9 in the morning?"

"Well... Not really a lot I can do to you while you are at work... so starting NOW." she responded.

"Wait here... I will be right back." she said.

I turned the TV off and started cleaning up. From the end of the hall I heard her voice, "You can come to the bedroom now Slave..."

"OK" I played along.

"WHAT?" she yelled.

"Common SLAVES will address me as Ma'am or Mistress!!" She hissed.

When I entered the bedroom, she was wearing a leather corset, knee high boots and was holding a riding crop.

"KNEES" she snapped.

I knelt on the floor.

"There are going to be some new rules for the next 48 hours. Violate them and you will face the consequences." She stated.

"Is that clear?" she asked.

I nodded.

"I SAID IS THAT CLEAR... SLAVE?" She yelled.

"Yes Mistress!!" I replied.

"Better..." she spoke calmly.

"Now... for the next 48 hours, THIS is what I expect..." she began

You will face me when speaking to me.

You will address me as Mistress or Ma'am.

What I say is FINAL.

Punishments are to my discretion.

Protests and complaints will ADD time to your current sentence of 48 hours.

You will be naked at all times in the home UNLESS I deem otherwise.

"Any questions, SLAAAVE?" she asked playfully.

"No Mistress." I responded.

"GOOD... Now get up and get those clothes off." she demanded.

She shackled my wrists to the bed. She tied my ankles to the footboard and then she left the room.

She returned to the room with a plastic grocery bag and she dimmed the lights.

She ran her fingers over my cock and balls. She moaned as she traced the outline of my manhood. I heard some wrinkling of the bag and then the stinging cold of a frozen bag of veggies on my erection.

Her laughter followed.

"Mistress... I do not like this." I said desperately.

"Then you will not like what follows SLAVE..." she responded in a calm voice.

I heard more rustling of the bag.

A metallic "CLICK" filled the air.

"What was that? I asked.

"MISTRESS" I blurted out...

"THIS is the part you are not going to like..." she stated.

The cold bag was removed and she pulled my cock outward. She lifted my balls and clamped some kind of device around the bottom of my bag and the base of my shaft. Then (with a loving touch) she guided my cock into a plastic tube and I heard a "CLICK" followed my a deep throated giggle.

"There WE go..." she said condescendingly.

She cleaned up the small mess on the bed, put the veggies back in the freezer and returned shortly. I was still tied to the bed.

She lit a few more candles in the room and removed her boots. She stood at the end of the bed on the bed between my legs and turned away from me so I could stare at her ass.

"Too bad about your gambling problem... SLAVE." she started.

"THIS (she then smacked herself on the ass) could have been yours..." she hissed.

She then lowered herself onto my face and coached me on how to satisfy her. The first orgasm came quickly. The second orgasm took a little longer and was more intense. The third as fast and she pulled my hair while she ground her hips against my face.

She was panting as she pushed herself back from my face.

My cock was aching for release. She could see the torment in my face and in my eyes.

"I'm tired... tomorrow YOU have a busy day... so lets get some rest." she told me.

I cleared my throat. She looked at me (expecting a complaint of some sort... or a protest).

"Good Night Mistress" I said in my best delightful voice.

She untied me, rolled over and went directly to sleep.

I tossed and turned all night.

At 8 am she woke me up and led me to the bathroom. I had about 4 or 5 hours of sleep. She put a dog collar around my neck and locked it in place. Then she used another lock to attach a small chain to the collar. The chain was wrapped around the toilet and (you guessed it) attached with a third lock.

"Take these" she ordered.

It was a few laxatives.

"I want ALL of your body hair OFF by the time I get back from the store." she barked.

I nodded.

A "POP" filled the small room as she smacked me on the ass. She gave me a scornful look. "You just added 4 hours to the clock!!" she said harshly.

"Now... Do you understand that I want ALL of your body hair removed before I get back from the store?" she asked again.

"Yes Mistress" I said submissively.

"Thhhhaaaaaats BETTER..." she said (indicating that her satisfaction was MY reward).

She sat me on the toilet and instructed me to watch as she got ready to leave.

She put on some lipstick and little eye liner. Then she pulled her hair back in a pony tail. She sprayed a little perfume on her body and neck. Then she pulled on some old faded cut-offs that allowed her ass cheeks to peek out when she bent over just right. After those, she pulled on an old white tank top that showed off all of her curves.

She didn't wear any panties. She didn't wear a bra. She KNEW that made me hot.

She put on a ball cap and winked at me in the mirror as she blew me a kiss. She turned to walk out and stopped.

She turned and pulled a bottle of nail polish off of the shelf.

"I want your toe nails painted too!!" she said.

Then she left.

My cock ached inside of this shell I was wearing.

"Stupid fucking bet..." I kept telling myself.

I used up an entire package of disposable razors while I was in the bathroom. She had left detailed instructions and a few hair removal products for me to use. I soaked in the tub afterwards and then applied some baby oil before drying off.

I sat on the toilet and painted my nails. I have to admit that I loved the way my skin felt. I finished my nails and used the polish remover to touch up a few mistakes. After the first layer dried, I applied a second coat.

I had just finished putting the bottle down when my phone chimed. "Be home in 5 minutes ~ M"

I inspected my body real quickly.

I saw her perfume on the counter and sprayed a little on my neck and wrists.

I sat on the edge of the tub as she entered the room. I pointed my toes towards her and sat with my knees together.

She smiled with approval as she unlocked me from the collar.

She attached a small leash to my collar and led me into the bedroom.

Laid out on the bed were women's clothing.

"Put these on." she snapped.

She handed me some black satin bikini panties. As I pulled them up she giggled to herself. She opened a package of stockings and handed them to me. The garter belt followed.

I saw bags from Shoe Carnival and JC Penny's too.

She put me in a pair of open toed 3" Heels and then had me walk around the house while she laughed.

I was getting the hang of things when the doorbell rang.

"OH FUCK" I thought to myself. Neither of us had heard the Fed Ex driver pull into the driveway.

"Go answer the DOOR!!" she laughed.

"Yes Mistress" I replied.

By the time I got to the door, the driver was in his truck and gone.

"WHEW" I thought to myself.

A large box was on the doorstep. It was addressed to:

"Mistress Avalon"

"This is part of the bet?" I asked myself.

As I walked back into the living room she gasped, "Ohhh GOOD... Its here."

"Open it SLAVE" she ordered.

I pulled the box open to reveal a strap-on dildo.

I froze in my heels.

She got up from her chair. Her nipples were hard and I could tell she was excited. She smiled at me (the kind of smile a doomed man might get in prison).

She walked behind me. I could feel her fingers on my skin.

"A Slave's job is to serve their Mistress... In any and ALL capacities. I think its clear that your role has become a little more defined." she stated.

"Yes Mistress" I replied.

She reached down and cupped my ass cheeks.

She leaned in closer and whispered in my ear, "I cannot WAIT to tear that ass up."

"Yes Mistress" I whispered.

She changed sides and whispered in my other ear, "I'm going to enjoy taking your anal cherry. I'm looking forward to owning your manhood and turning you into my bitch."

I started to shake.

She stepped back and rubbed my ass some more.

"DAMMMM... Maybe I should just take it RIGHT NOW..." she said loudly.

She slowly walked around me (like a lioness circles their prey). She looked me in the eyes and pulled the harness out of the box.

"Follow ME SLAVE..." she ordered in a hushed tone.

"Yes Mistress" I replied.

In the bedroom she had me help her put the harness on. We adjusted the straps until everything felt right. She put the "cock" in the locking device and walked around the bedroom for quite a while. She kept making comments about how she felt so empowered and how she was going to enjoy being my first.

She took me to the bathroom and had me put on some lipstick. Then some eyeliner and mascara.

"Stand up and bend over the counter" she ordered.

She applied some "Anal Ease" to my butthole. Then she read the label: "Needs a few minutes to activate."

"So WHAT can we do while we are waiting?" she asked.

Before I could respond, she barked out, "Kneel"

I knelt before her. She held my chin in her hand. She held the base of her cock in the other. Our eyes locked and at that exact moment, the exchange of power was complete. Without a word I opened my mouth and closed my eyes.

She guided her cock into my mouth with "porn star precision". I felt the head of the cock rub the roof of my mouth.

Mistress hissed as I wrapped my lips around her cock.

"Thaaats IT... make it feel GOOOOOOOOOD for me..." she hissed at me.

She held the back of my head and fucked my face while she kept repeating "Ohhh YEAH and "FUCK YES..."

Her nipples were hard. I could smell her arousal.

"You LIKE my cock SLAVE?" she would ask me from time to time.

I would nod.

"I sure like the way you look from up here... I'm going to need you to lose a few more bets..." she would tell me between heavy breaths.

My ass was starting to tingle. She checked her watch and stopped her blow job.

She had me rise and follow her into the bedroom. My wrists were tied to the headboard and I was bent over at the waist. I could hear her moving around behind me.

"Here's a little added bonus... because you suck a mean cock without being told to do so." she said in a husky voice.

I felt a glob of lube getting rubbed up and down the crack of my ass. She rubbed some on her cock and then wiped her fingers on a towel.

I was weak. I hadn't eaten anything all day.

I felt the head of the cock rest against my anus. I tried to relax.

Her hands gripped my hips. Silence filled the room.

She pressed against my anus and I felt it open up and take her inside of me.

Mistress squealed with excitement.

I felt her move her feet and adjust her grip. She pushed in a little deeper.

"OHHHH FUCK YES." she said.

She pushed in a little deeper and let out a grunt.

I was panting. I was excited but NOT as much as she was. She reached up and grabbed the collar around my neck. She moved her hips in and out slowly with short strokes.

"YES... THAAAATS it... " she would encourage me.

"THATS what I want to see... a Bitch that knows how to take a cock!!" she whispered.

Then her rhythm got faster...

Her strokes got longer... and went deeper inside of me

She started going faster and harder against my body.

The sounds of skin slapping on skin filled the room... the remarks slowed down and were replaced with grunts and heavy labored panting.

Mistress's grunting got louder and her breathing got harder and harder...

Then (out of nowhere) she thrust into my ass harder than ever before and screamed out, "OHHHH SHIIIIIIIT..." as she exploded into an orgasm that made her body twitch and bend with uncontrollable convulsions.

When she had finished, she pushed her cock all the way in and lay on my back. I could feel her rigid nipples against my skin and her sweat was dripping onto me.

She slipped her cock out of me slowly.

"THAT was amazing..." she said.

"Thank you Mistress." I said, accepting the compliment.

I heard a drawer open.

Mistress walked in front of my face and held up a butt plug.

"Kiss it!!" she demanded.

I put my lipstick covered lips on the tip and kissed it.

She put one hand in the small of my back and used the other to push the butt plug all the way in.

"There we GO... A perfect fit!!" she said.

I heard the harness hit the floor.

My hands were still tied to the bed.

She untied my wrists and put me on the bed. She tied me spread eagle on the bed and then removed the device from my cock and balls. My cock sprang to life.

"Tomorrow... while you are at work... and your panties keep rubbing against your balls and your cock I want you to remember what happened here." she said, "because it is going to happen a LOT more often in the future.

Written by: That_Guy71

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Story Tags: strap-on, mistress, anal, anal sex, femdom, gambling, slave, bdsm

Category: BDSM Stories