Alex wakes up back in his bed. Another day, another loop.
I popped up out of sleep and looked over at the clock. 6:53. Damn May 12 again. What is this the thirty-seventh time? Thinking about the loop before, “holy fuck that was intense. Maybe call out sick today,” he said softly. His mind raced as he thought of what happened in the last loop. Trying to wrap his head around it. He sat up to hear the keys at the door. “Alex, are you here? I need your help with something.”
Knowing where this is going to lead and still trying to wrap my head around the last loop, I reach for my phone. I quickly typed to my boss that I’m not feeling well and will be taking the day off. Pulling the phone done I hear Mrs. Tomas closer. “Alex my boy, are you here?”
“Just give me a moment,” I called back as I swung my legs over the end of the bed. Let’s get this over. “I will be out in a moment.”
“No need Alex,” her smooth older voice said at the door. Seeing her leaning against the door frame I pulled the blanket over my naked crotch. “No need to cover up Alex, my boy. I have seen the naked body before.”
“But, but,” I started to say as she walked across my small bedroom. As she did, the long black jacket dropped behind her. Underneath she didn’t have much on. Only a black leather harness. One made just of straps. Starting with a collar with a small metal O. The leather straps then crisscross over her upper body until they worked their way around her large breasts. At each change another small O ring. They weaved across her full body midsection and wrapped around her waist. A set of O rings, front and back, hung down to each leg. There, the black leather attached to a double harness hugging each thigh. Black thigh stockings and low heels completed her outfit. “Mrs. Tomas,” I said, the words not coming.
This was a bit of a change from the other loops. She was always bossy and strong willed in them. Even the ones I flipped the switch. Today she is seductive and so damn sexy.
“Call me Mommy, Mommy Tomas please,” she responded back to me. She stepped out of her heels and climbed onto the bed behind me. Her body pressed onto my back. I can feel the heat from large breasts. “Relax and let Mommy Tomas take care of you my dear Alex.” Her hands reached over my shoulders, and she gently used them to caress my chest.
Her soft hands were like magic. Removing all the stress at the moment. “That is a good boy,” she whispered softly in my ear. Her breath on my neck. “Relax like a good boy for me.” Her body shifted to the left behind me. Her left hand drifts lower as her right caress my neck. Working its way up to the short hair at the back of my head. Softly rubbing her hand there as her left hand moved over the bulge under the sheet. Her hand moves to it. Caressing the bulge. Making it bigger.
“Mrs. Tomas, I mean Mommy Tomas, what are you doing,” my words with a bit of confusion. She never cared about my pleasure before.
“Why teasing you, my boy. Don’t you want Mommy Tomas to stroke your big young cock. Maybe caress those balls between your legs. Let this cougar provide her cub with pleasure.” Her hand slipped under the blanket and grabbed onto my hardening cock. As the sheet fell to the floor, she got her first look at it this loop. “What a magnificent piece of manhood you have there, my good boy.”
I took a deep breath in. Letting the pleasure relax me. Fuck her hand feels so damn good. “Oh yes Mommy Tomas that feels so good.”
Her hand worked over the top of my shaft. Up and down over my sensitive cock head. “I know it makes my boy feel good. Does he like it slow like this? Only working at the top or should I switch it up?” Her hand moved up and down faster, stroking my few lengths. “Or like this, faster and faster.” I moan at her question. “I think my boy likes both but the faster seems to drive him wild.”
She pushed me back down onto the bed. Her mouth lowered over my nipple, and she licked it until it became hard also. “Look at me getting everything hard on you. You are a pleasure of desire.”
Hands now back together working my cock and balls. Stroking, grabbing and fondling them. I stretched out as the pleasure built in me. My desire was so intense. Not thinking it could get higher, until it did.
Her head lowered, closer and closer to my dick. I can feel her warm breath on my flesh. My body so horny from her stroking me I hoped she would wrap those thick lips around it. Like I made a wish, she did. Her mouth locked around the top half of my dick, and she sucked and sucked hard.
There was no bobbing of her head up and down on my meat stick. Only fierce, hard sucking. Working hard to draw out my juices. Her tongue flicked at my tip. Her hand squeezing my full balls. She was possessed. Wanting no more than to drain me. Then to suck my soul out of my body and she was close. I was not going to last.
My ass tightened as I started to moan,” Mommy, yes Mommy.” Then it was all over. My seed ejaculated into her warm loving mouth. Squirt after squirt she took each and every drop. When I had nothing more she kept sucking. My tip is now so sensitive. Making my body buck. Not knowing if it hurt or felt way too good. “Please Mommy, please,” I begged her.
Her head pulled back and looked up to me. “Was that too much my good boy? Cause Mommy Tomas really enjoyed taking the creamy goodness inside.” Her smile grew as we locked eyes. My head dropped her gaze and dropped to the bed, temporarily defeated. “Too bad your dick is all drained. I would love to have had it inside me. I’m all worked up now and need my own release.”
She sat up at the end of the bed and crawled forward. She hovered over my head and then lowered on my face. Even drained, I knew what to do. My tongue darted free from my mouth and found her wet honey pot. Like a greedy bear, I devoured her.
“Oh god!! That is amazing. Not as good as I bet your dick but a girl will take what she can get.”
What she doesn’t remember is that these loops have done something. Has my cock gotten bigger, maybe. After so many loops it may have. What I can say is whatever power is behind these loops it made me last longer and let me recover much quicker. I’m always ready for the next kinky experience. So as I stroked my manhood back to life, my tongue brought her to her first orgasm. Her juices flowed freely, covering me. I thought,” damn I just did the sheets.” Then remember tomorrow will be all different anyway.
Her body shifted forward and she rolled off my face. Now free I spoke up. “Mommy Tomas, my cock is ready to be ridden, if you still want to.” She looked back over her shoulder and licked her lips. Without a word she turned and positioned herself over it. Lowering it down so her dripping pussy was just touching. She moaned as she rubbed into my head. Letting it find the right place and then she lowered onto it.
Her pussy was warm and tight. I would have thought tighter but I’m seeing she is a cougar on the prowl. Wondering how many others she made visits too.
“Oh my god, you are so big.” She moved from her knees to her crouching on her feet. Her hands on my chest as she started pumping up and down on me like a piston. “Yes, yes. Stay just right there.” Her hair flowed down over her face. “I’m going to cum,” she cried out. Her second orgasm hit her quickly. I could feel her pussy walls pulsing around my shaft, raising my own lust.
Her pace slowed as she came again. Sliding back onto her knees she started to grind her hips into me. “Fuck you are hitting the right spot.” Her words came out quick and labored.
My own body being pushed to that edge by her fucking. “Yes Mommy, just like that.” And then our orgasms lined up and fireworks happened. But if us came. My stick shot a thick stream deep into her as her pussy wrapped around it. Her body gave way and fell into mine. Her large breasts on my naked chest. Our body heat mingled as my arms wrapped around her back.
She slid from my gasp and face down next to me. Her body is still breathing a bit heavy. A thought crossed my mind. She fucked my ass so many times on other loops, I think it would be fair play to fuck hers. I shifted and moved from her. She looked over but didn’t say anything. I let my body slide off the bed onto my knees. A quick shift and I was behind her. Her ass in the perfect placement as it hung over the edge of the bed. I raised my hands and spread her ass cheeks wide.
“What are you,” was all she was able to get out. What cut off was the yelp she made as my tongue hit her anal rim. “What the hell,” she asked, biting her lips. Her hand looked back to see my face buried in her ass. She tried to push up but her own body made her stay to experience this sensation.
My tongue licked around in circles and then back and forth. Finally push past and licking deeper. She reached back and hands pulled at her own ass cheeks. Hoping I would go deeper.
As I worked her over, I stroked my dick making it hand quickly. It was ready and willing to be used again. Hearing her sweet moans again. I thought she was ready. Pushing up from my kneeling position, I got to my feet and set up behind her. I reached over to my nightstand at the end of my bed and grabbed the lube. A little squirt on both my dick and her hole, a quick stroke and it was ready to break down the back door.
I pushed in slowly. Letting her get used to the fit. I pushed deeper and deeper and then smoothly, pulling back just the tip remaining. Then doing it all over. She moans deeper with each thrust. As I quicken my pace she becomes louder. “Oh my. Fuck that dirty hole. Yes, yes make me your ass whore. Please don’t stop.” Her words of begging for more as I pound her ass.
As she starts getting louder and louder, I reach up to her head. My fingers first weave into her curly hair, pulling it back to me. “Fuck,” she yelled. “Give me that big thick cock. Keep fucking me. Yes yes!! Harder harder, please fuck me harder.”
She turned into a needy fuck machine once I plugged her ass with my fat cock. Driving her deeper into her ecstasy. I turn her head. She looks back at me with her big brown eyes. They pleaded, pleaded for more. “You want more Mommy. You want more of my fat cock pounding your hole?”
“Oh yes please. Please use my hole however you want.” Her words came out broken as she took it. My hands reached a bit more forward. Fingers exploring her face. Finding her mouth, I inserted two fingers from each hand. Her mouth opened for them. Then I pulled them wide and her head back. This arched her back letting me go even deeper. Her mouth started drooling even more, coating my fingers. She mumbled something into my fingers, but the words made no sense. That was until her body told me what she said. She was cumming again. Seeing her body so deep in her bliss, got me excited.
I pumped her a few more until I let my own orgasm take over. Pushing into her deeply, I let my juices flow. Her body racked within its own pleasure, I didn’t know if she felt my juices in her. I slowly pulled back out of her tight hole. I flipped her onto her back. Seeing her eyes glazed over. Her pointing finger went to her lips and she bit down on it as she smiled up to me. So fucking sexy.
I lifted her left leg up and pushed her right down. My dick pushed back into her new slick hole. “Oh yes baby, fuck this sexy milf.” Reaching down with my free left hand I slapped her tits.
“What do you say,” I questioned in my deeper dominant voice.
“Please fuck this sexy milf. Please fuck her good.” And I did. My dick ramming deep into her. Fucking her faster. Her hands reached down and grabbed the sheets. “Oh god yes.”
Not done with breaking her, I reached over to the nightstand and pulled the wand from the draw. As the sound of the tool clicking to life, she looked up. Her head was back and eyes closed until then. A bit of trepidation crossed to them. That was until the sweet hum of the wand worked its way to her aching needy clit. At that moment we both knew this would break her.
Orgasm after orgasm I coaxed from my landlord. “Does that feel good l,” I questioned her.
“It feels so amazing,” she whimpered. “My body is one big explosion of pleasure.” Words coming out broken. “Oh god, please give me more. I’m coming again. Please don’t stop. Fuck me. Fuck me please.” And then her body came again. Her legs are shaking as her body bucked. Then it was over, and she collapsed into the bed. Her body laid in a motionless state. Her breathing is hard but softened with each minute that passed.
Her body was done. She was broken and could take no more. I gave her ass one more pump and pulled out. Putting the wand to my hardon, I let the vibration coax out my own orgasm. A half a minute later my dick tightened and then a stream of creamy jizz came shooting out. My load delivered onto her thick round tits. After the last drop, I dropped to the bed next to her.
We laid there in silence for a few minutes. Her fingers gently rubbing my forearm. She finally said,” damn you broke this MILF. I don’t think I’m going to move for days.” Her head tilted over to look at me.
“Well that is a good thing right,” I questioned back with a smile?
“Normally, but I have to do some errands out in Pleasantville later. I’m in no shape. My holes are still pulsing.”
I looked over to see it was no five minutes to nine. I just used and abused this needy whore for two hours, damn. “Well, you can stay here as long as you like. You own the building.”
She laughed. “What time is it?” When I told her, her head shot up. “Two hours, fuck.” Then a pause as she lowered her head. “Don’t you have work?”
“I called out sick before you came in. I’m good.”
“If you are free,” a pause in her voice. “Maybe you can pick up those things for me.” I could hear how her words drifted. How tired she is and just want to sleep.
“After that fuck it is the least I can do.” I had nothing else to do since I was supposed to be at work. Plus, these loops have not had me visit Pleasantville yet. I pushed off the bed and reached for my phone. I had a message from my boss - feel better. Opening the screen and pulling up the notes app, I handed her the phone. “Type in what errands you need done.” As she took my phone I stood. “I’m going to take a shower. Hangout as long as you want.”
I walked out of the bedroom naked. Into the small hallway and then into the bathroom. I finally got to brush my teeth and then shaved. The water was warm at that point so I hopped into the shower. Just letting the water cascade off my body. Feeling the muscles started to relax. I wet my hair and then shampooed it. Letting it sit as I cleaned the sweat and her juices from my skin. Rinsing off, I grabbed the towel and dried my body. I wrapped it around my waist and headed back to my bedroom.
Mommy Tomas was fast asleep. I was next to my bed in a few steps. I pulled the blanket at the foot of the bed up around her, covering her in her own little cocoon. I picked up my phone and found three errands. I read them over as I got dressed.
First was the pharmacy at S-Mart. She had three things to get there. She gave me the information I would need to pick them up. I pulled out the top underwear, a black pair. Then stepped into the jeans on the floor. Buckling the belt I looked over the second one. She ordered some clothes from a boutique on Walnut Street, Her Little Spot. Ask for Cherie. I pulled one of my tee shirts from the draw. This one concert tee from the indie band Dinosaur Jr. I got some socks and my black Vans and headed out to the living room. Looking back at the sleeping firm on my bed.
This was the first time in all the loops she was dominant. I wonder what changed. Did the powers even out the flow of top and bottom in each flow. It is over my head. I’m just along for the ride and boy it has been one fun ride so far.
I sat on the edge of my oversized chair. This thing will pull you in and not let go. I pulled up my sock and tied the Vans. Then I checked out the last errand. A new pair of glasses at the Eye Hut on Main Street. All pretty simple. I grabbed my light black jacket and keys and headed out.
Traffic was not so bad getting out of the city. I wondered why she shopped out here. There are plenty of closer places. No big deal. I had a day of adventure ahead of me. I pulled into the parking garage and locked up my car and headed to my first stop.