My name is Luke. I am 21 years old and a student at UCLA. After a long day of studying and boring lectures, I’m officially on Spring Break! I’m done with school for a week. I am looking forward to spending time with my friends in Mexico! I quickly get my bags in my dorm, already packed, and I head home back to San Diego. My family won’t be there. They’re on a cruise island hopping throughout the Caribbean. I was a little jealous and upset that my parents forgot to invite me. I quickly got over it when my friend Jacob invited me to Cancun to stay at a resort all week for break. I planned on going home for the weekend to do a couple of chores and get ready for my trip next week. My parents want me to mow the lawn, wash the cars, and paint the shed in the backyard before I leave for Mexico. I honestly don’t mind because I haven’t been back home in months and I’m getting paid to do it. Good money too that I could use for my trip.
I arrive home a few hours later. I unload my car and walk into my house. Felt good to be back home. I quickly grab a snack from the fridge and I get straight to work. I washed both of my parents cars. I mowed the lawn until the sun went down. By the time evening came, I did the front yard of the house. Tomorrow I would finish the rest of my chores. As I put the lawn mower back in the garage, I heard a car coming by. I turned to get a look. The car was a new Corvette Sting Ray convertible. As the car drove by, I looked at the driver. My eyes widened. The driver is a woman. She is drop dead gorgeous! She looks to be in her mid-late thirties. She’s blonde and has on what looks to be a sun dress. When she drove by she saw me standing on my driveway and waved. I waved back but by then she already drove past. She turned into a house two doors down. I never seen her before and I wondered how she was related to Mr. Jones, a widower who lived in that house two doors down. Then I remembered that my mom told me that Mr. Jones moved to New York about two months ago. This lady must be new. I watched as she parked her car and walked toward her front door. She stopped and looked in my direction. She started to walk towards me. Shit! I don’t know what to say!
She approaches me. “Hi how are you? You must be Luke. Your mom has told me so much about you.” She extended her hand and I shook it. “Nice to meet you ma’am.” She introduced herself to me as Violet Taylor. I offered her to come inside for a glass of lemonade, which she gladly accepted. We talked for about half an hour. I told her about school for me and that I’m on break planning to head out on a trip soon and doing some house work before leaving. She then told me about her story.
“Well Luke, I’ve been here in California for about a month. I moved from Boston to start a new life out here in the West Coast. It’s so much better here in Cali. The weather, the people, and just life in general.” She told me that her husband is in the Navy and is overseas and that moving to Cali would increase her chances of seeing him more often as his military base was here in San Diego near the Pacific.
I was bummed when she told me she was married but I shouldn’t have been surprised. She is super sexy. She is slightly tan with curly blonde hair that extends to her lower shoulders. She wore a teal sun dress that was designed with all kinds of light colored flowers. When she wasn’t looking at me, a couple times I stared at her open cleavage which revealed that her breasts were probably around DD cups at least! They’re amazing! I just imagined myself kissing each nipple and pla-“Luke!”
I was quickly brought back to reality. Mrs. Taylor was looking at me. She caught me staring at her tits! Fuck!
I apologized for losing focus, using the excuse of daydreaming. Mrs. Taylor just smiled and continued to talk. “My husband won’t get back for about another six months so I live here by myself working part time from home.” I was curious if she had kids so I asked.
“Do you have kids?” She replied.
“I have two boys. My oldest is Joseph. He’s 22. My youngest is Danny. He’s 19. Both are in college in Florida.” I was surprised. Her children were around my age and she looked so young! Mrs. Taylor could tell I was confused about her age.
“If you’re shocked that I have older kids I get that a lot. I’m 44 years old. Been married for 24 years.” I was surprised and turned on when she told me this. I was hitting on a MILF! Smokin hot one too!
“You look great for your age Mrs. Taylor.” She smiled. “Please call me Violet.”
“Sure thing Violet.” She stood up and shook my hand again and told me it was a pleasure meeting me. We exchanged numbers and then she left.
That night I went online on my laptop. I went to xnxx.com and looked up milf porn. I tried to find a porn star who reminded me of Violet. The closest one I could find had similar features with breasts and butt size. I watched as the the woman oils her tits and rubs her clit moaning. She begs for a nice big fat cock in her mouth and pussy. I started to jerk my cock as it started to get hard. I am a solid 7 1/2 inches long with some nice thickness! When I’m fully erect, a man comes out and starts to rub her ass. When her pussy is lubricated, the man takes out his dick and slips it into her. He started to fuck her hard causing her to moan loudly. I imagined I was fucking Violet like the man in the video. I started to get a feeling of pre-cum as the man fucked her faster. Eventually she got up and and bent down. She opened up her ass cheeks and begged the man to stick it right into her ass. Once they were both lubricated the man slipped into her butt hole with little difficulty. He started to fuck her ass as her loud dirty talk and moans increased. My cock couldn’t take it no more. My semen flew and shot into the air. I shot multiple ropes of cum onto my bed! Each shot was more powerful than the previous one. Once I cleaned up my mess, I laid in bed thinking about Violet. I kept thinking about fucking Mrs. Taylor hard in the ass. Anal sex happens to be a major fetish of mine. Shortly after, I fell asleep.
The next morning, I woke up and ate a quick breakfast. I planned on finishing the lawn and completing the shed by late afternoon. Around 3:30 in the afternoon, I put the lawn mower and paints in the garage. I was done. My flight down to Mexico is tomorrow afternoon and I now have some free time of my own. I thought about visiting Mrs. Taylor. I started to get horny again thinking about her. Suddenly, my phone started to vibrate. I smiled. It was her. She wanted me to come over for lunch. I replied back telling her I will be there. I grabbed my car keys and drove to the local grocery store to pick up some desert.
I drove to Mrs. Taylor’s house and rang her bell. She opened the door and greeted me.
“Hi Luke come in.” I stepped inside her home and smelled fresh pasta cooking in the kitchen. The food smelled great. She guided me to the living room and told me to watch some television until the meal was prepared. I just flipped on the news. It was the first channel that popped up. I honestly wasn’t paying attention to the tv. All I could think about was Mrs. Taylor. Today she wore a purple blouse that exposed a lot of cleavage, with a black mini skirt. A little while later, Violet called me to the table. We ate and talked. Soon after desert, Violet went to do the dishes while I sat in her living room waiting for her to come by. I started to hear weird grunts and moans coming from her kitchen. I got up to see what was going on.
Violet was sitting in a chair holding her stomach.
“Is everything ok?” What’s wrong?” I asked. She just looked up. She didn’t look too good.
“I’ve been having some cramps lately. It’s been killing me. I haven’t been able to go to the bathroom in a few days.” I asked her about prune juice and she told me she didn’t have any. I quickly got my keys and ran out the door and drove to the nearby pharmacy to pick up some prune juice and laxatives, seeing if that could help. About 20 minutes later, I was back with two jugs of prune juice. I served Violet a cup worth and went to find her. She was in her room. “Violet, I ran and bought you some prune juice.” I heard some groans. “Come in,” she told me. I opened her bedroom door and found her lying flat on her stomach on her bed. She had a king size bed. Her room had a huge painting of a beach and a bunch of picture frames of her and her family. Mostly her husband. I gave Ms. Taylor the prune juice. I was debating on whether or not to give her the laxatives I had in my pocket. The pharmacy ran out of the powder lax that comes in bottles. The only kind they had was called Glycerol, which is a lax pill that you plug into your rectum. Basically anal pills. I was super nervous to ask. I finally had the courage to ask. I waited for her to set down her drink.
“Um…Violet. If you’re dealing with constipation, you could try laxatives.” Violet’s eyes widened. “That’s a great idea. I never thought of that. Did you purchase some?” My heart was beating like hell and beads of sweat started to form on my forehead.
“Uhh…I tried to get you some…the pharmacy only had this.” I took out the package of the Glycerol I had in my pocket. Violet just stared at the pills. Then she looked at me.
“Luke…I don’t know how to say this without making this so awkward and weird. But please…I need you to help me insert the pills. I can’t tell you how much pain I’m in. I can give you some gloves.” My jaw just dropped. My dick starting to harden rapidly. I sort of panicked and I felt my knees start to shake. My reaction of panic left Ms. Taylor saddened and embarrassed.
“I’m so sorry Luke….I’m just so desperate.” My hormones started to come and I found my voice. “No no Violet! I’m willing to help you. I was just a little thrown off that’s all. This is perfectly normal. You’re sick and you need me to help you. So I can help you.” Violet’s face instantly lit up.
“Thank you so much Luke. I don’t know how I could ever repay you.” I was just thinking of all the positions that me and Ms. Taylor could be fucking in, and I quietly chuckle to myself. That’s definitely a way she could repay me.
“Should we get started?”
Violet slowly sat up.
“You don’t have to turn around or feel uncomfortable. I’m just going to pull my skirt and panties down just enough so you can insert the pill.” With that, she bent herself over and pulled her skirt down and then her panties. I instantly felt a drop of precum soak my boxers. My cock was twitching trying to be free and escape my pants. My boner at this point was so hard and my balls were so blue, it hurt. Violet looked at me. She caught me staring at her ass. I saw a hint of a smile on her face.
“Luke I have a box of gloves in my kitchen next to the sink. Go ahead and grab a pair.”
I didn’t care about dirtying my hands and I wanted to feel how tight her asshole is without any gloves.
“Violet…if you’re in pain you need this pill now. With or without gloves, I can do this. Don’t worry about me.” She was so shocked she didn’t know what to say.
“Uhh…well uhh…if you say so…”
I went to her bathroom to wash my hands quickly.
I came back and opened up a pill. Violet sat back up and bent her body over with her ass up high in the air.
“Whenever you’re ready Luke. Take your time.” I took a few quick breaths. My hands started to shake.
“Ok…here we go.” I put one hand on her butt cheek and rubbed it up and down her ass. She jumped a little and actually let out a huge moan. Her body was so sensitive to the touch of my warm soft hand. I lined up the pill with her ass hole. Her anus puckered up as I started to insert the pill slowly into her ass. When the pill was in her butt, I pressed my finger slightly into her anus. Violet jumped a little again. To make sure the pill was all the way in, I stuck my finger completely into her ass and left it there.
“Umm…the instructions read that I should leave my finger in there for about 10-20 seconds to make sure the pill stays in.” Ms. Taylor just nodded and held her head down on her pillow. I was surprised she believed me. I just made that up. As soon as the pill was in her ass, the directions read to release and let the pill settle. I just loved the feeling of her warm tight anus wrapped around my finger.
About 30 seconds later, I finally released my finger from her ass. Ms. Taylor lays back down in a huge sigh of relief.
“Thank you so much Luke! I can feel it working already.” I just smiled and went to wash my hands again.
I went back to Violet who was sitting up.
“I’m going to the bathroom now.” I nodded. “Let me know if you need anything else.” She walked up to me and hugged me.
“Luke you’ve done so much more than enough. I appreciate your help and kindness to me.” With that, she walked to her bathroom and closed the door. I stood in her room waiting. I finally decided to go back to her living room to wait.
I grabbed my phone in my pocket and unlocked it. My notifications were completely filled! My friends were trying to get ahold of me via text, social media, and voicemail. All were discussing the trip to Mexico. I just didn’t want to deal with it at the moment. I just sent one giant group text saying I was busy and we’ll discuss the trip later. With that, I turned off my phone and waited. 10 minutes. Nothing. 15 minutes. Nothing.
About 30 minutes of waiting, I went up to her bathroom door and knocked. All I heard were groans. Again.
“Violet, what’s wrong?” She opened the door her face all sweaty.
“Luke…it’s not working. I’ve been sitting on the toilet for half hour trying to relief myself. Nothing worked. I even tried pushing it out…really hard! For the last ten minutes. Now the pain is starting to come back again. I just can’t FUCKING take a SHIT!!!” I was surprised by her sudden burst of anger. She saw my reaction then started to apologize.
“Don’t apologize Violet. I can understand what you’re going through. I just wish their was something else I could do.” Ms. Taylor started to tear up and went to her bed and laid down.
I watched as she continued to groan silently. And then I came up with the idea. The most brilliant idea of all! My most perverted idea of all.
A few weeks ago, I watched this porno. I was having this mad lust and fetish for grannies. More specific, grannies that love anal. I ended up jacking off to this crazy video of this granny who loved double penetration.
The story of the video goes…a granny walks to her fridge to get some prune juice. She freaks out when she realizes she has none. She calls up “The Prune Brothers” to bring some more prune juice for her constipation and her mad urge of the need to “take a shit.” The Prune Bros. show up, two men in milk delivery uniforms, and deliver the juice. She thanks them for the juice but they don’t let her have it. Frustrated, she begs for the juice. She’s so desperate and horny, she rips her shirt off revealing her breasts and gets on her knees unbuckling both mens’ cocks. She sucks both while they pour prune juice in her mouth and down her tits. She eventually starts to fuck both of the men and begs for one thing: Anal!
“Stick that cock in my ass.” She knew that if they could fuck her ass, she could take a shit easily. Sure enough, after being fucked deep and hard in her pussy and especially her ass, the video ends with her running to the bathroom to take a shit.
I knew that if I could fuck Ms. Taylor hard and deep enough in her ass, I would be able to clean out her bowels and she’d take a huge shit in no time. Just by looking at her face, I knew she was desperate. I didn’t even hesitate this time to ask. My idea was just too great for her to say no. I was almost positive she would agree. I could feel it in my balls. No seriously, my balls were just boiling with cum just waiting to be drained.
“Violet, I have another idea. You probably won’t like it. I promise you it will help and you can poop in no time. I just hope that if you don’t like the idea, our friendship isn’t ruined.” Violet sat up.
“Luke at this point I’ll take any idea! I just don’t care anymore! The pain is too much to bear. Please help me!” I sighed…”Ok so maybe the pill didn’t work properly. Maybe I didn’t insert it far enough. But we can do the pill again…this time my fingers won’t be sticking the pill up your butt.”
Ms. Taylor’s face was clearly confused.
“What would you use then?” I just eyed her and our eyes met. My eyes pointed down and immediately she knew.
“Luke…Are you suggesting anal sex?”
With courage I said, “Yes I am. But only for medical purposes. If I can insert my penis just far enough into your butt, it’ll clear out your bowels in no time. You’ll be sitting on that toilet soon. I know that this makes me sound like a disgusting pervert, but I hate to see you like this. I would love to help you, if you’ll let me.”
Ms. Taylor was just wide eyed and her mouth was open. She didn’t know what to say. I instantly regret even asking.
“I’m so sorry…that was just a stupid gesture. I feel like an idio”-I stopped mid-sentence when Ms. Taylor got up, pulled her skirt and panties completely off, and bent over on the edge of her bed.
“Luke I said I was desperate…so if you think this idea will work, I want your cock and that pill FAR up my ass! Like right now!!”
I had no time to react or to think about what Ms. Taylor just asked me to do. I just unbuckled my pants and took them off. Before I yanked my boxers off, I realized we needed lubricant. “Violet, do you have lube by any chance?” Her next action left me so shocked, I just started to stutter. Violet got up, pushed me hard onto her bed and yanked my boxers off and threw them across her bedroom floor. She started to jerk me. Hard! It almost hurt as she took long giant strokes up and down my cock. She spit into her hand and rubbed me hard. She even started to lick the tip of my cock like an ice cream swirl. She had a little pattern going. Spit, stroke, lick. Spit, stroke, lick. I was in utter shock, it took me a few minutes for me and my hormones to realize that Ms. Taylor is giving me a crazy blow job!!
By the time I realized and came to the conclusion that this was my reality at the very moment, my cock started to twitch and was about to erupt just as Violet’s tongue went to lick my cock.
“Violet I’m going to cuuahhhh….” Violet just opened her mouth wide as ropes of my jizz just kept coming out. Violet couldn’t take the amount. She started to choke and spit out my cum. She spit it out into her hands and rubbed them together like she was washing her hands with soap. She took my juices and with one hand rubbed my shaft up and down and the tip of my cock as well. The other hand she started to finger her ass, trying to make her anus as slippery as can be. When she finally felt she was well lubricated, she got back down and bent herself over her bed, her ass high up in the air.
“Does this answer your question?” I just didn’t know what to say. I started to laugh nervously. “Uhh…yeah. Was NOT expecting THAT…at all! I meant actual lube or maybe some oil…but this..that will work.”
Violet showed no sign of expression on her face that she just sucked my cock to an orgasm and basically cheated on her husband. Her face just looked sweaty from the intense BJ and all she wanted right now was not to be fucked, but to finally relieve herself and take a shit she has been longing and desperately needing to take.
“Ok Luke…I’m ready. I hope you are.” Without waiting or hesitating, I got up behind Ms. Taylor and leaned on top of her. I grabbed my cock and rubbed it up and down between her ass cheeks trying to get as much of my semen on my cock as possible. Doing this, Violet started to relax and was actually starting to get horny. She started to moan as I rubbed myself up and down her ass. When I felt my tip slide easily into her ass, I reached out to her night table and took out another pill. I licked the pill and slowly pushed it into her anus. Violet kept moaning. I then pushed my cock slowly into her ass hole. As my cock entered her ass, Violet let out a huge gasp.
“Luke this hurts! Slow down! You’re too BIG!” I did as I was told completely stopping. My cock was about half way in her ass while I waited for her to adjust. As we waited, we just talked! She asked how I was feeling and I asked the same. She tells me how she has time off from work and plans on relaxing. She asked me what I was going to do this week and I told her about my trip to Cancun and what I was going to do over there. All this was happening…and we both forgot that I was inside her. The only reason we stopped talking was because Ms. Taylor felt my cock shrinking inside her ass. I quickly pulled out and tried to insert my cock in again. I wasn’t getting hard quickly.
“Luke do you need me to stroke your cock again?” When she asked I started to get hard again…but I knew what I needed to do. I pulled Violet up and pulled her blouse off.
“Luke what are you-“ CLICK! I unclipped her bra and turned her around. I pulled Violet in for a kiss. At first it was only me kissing her but I then felt her kissing me. Our tongues danced and fucked in each other’s mouths. I played with her nipples, which were pretty large. Her tits were amazing without a hint of sagging! My cock was super hard again and Ms. Taylor ended the kiss as she felt my cock near her crotch. She got back down.
“Ok Luke…let’s get this going. Just stick it up all the way in my ass…I don’t care HOW much it hurts. I’m in enough pain already. Stick that cock in my ass!!” I obeyed and aligned my dick with her ass. As soon as my tip was touching her asshole, I took a deep breath and pushed my cock deep into her bowels. I held her as she screamed from the intensity of the pressure of my deep thrust. I kissed her neck from behind as she started to calm down.
“Ok Luke….I’m ready.”
I started slowly as I pushed back and forth. I felt some object touching my cock every time I pushed into her. I realized the object was the pill, which was stuck inside her ass and wasn’t budging. I started to pump in and out harder and harder into Ms. Taylor, trying to push the pill up her butt. It worked. As I was fucking and demolishing her ass, I couldn’t feel the pill anymore. Violet was just screaming and grunting.
“Arghh…ahhhh…uhhh Fuck! Luke keep errrrrrr uhhh…fuck my ass!!!! Ahhhhhh….oh shit!!!”
I was getting hornier by the second! I still wasn’t close to cumming because of my insane orgasm that Ms. Taylor gave to me earlier.
“Luke I’m cumming!! Ms. Taylor came so hard while I was fucking her ass as hard as I could, she squirted! Like everywhere! She rubbed her pussy as her orgasm started to settle. I got a little exhausted from the intense anal work out I had. I pulled out of her behind and laid on the bed.
“Quickly get on top of me. I need a new position.” Violet quickly stood up on her bed and sat down on my cock. She gasped and quickly stood back up.
“Wrong hole haha.” My cock went into her pussy which felt tight but a little more spacious. Violet positioned my cock with her ass and sat down into it. I wrapped my arms around her back and pushed my face into her tits. She moaned loudly as my cock smacked up and down her ass. I kissed each of her nipples which were both hard. I started to get the feeling of cum again. Mrs. Taylor rode hard up and down my shaft.
“I’m going to cum soon.” When Violet heard that, she pushed my chest down. She took control now as she bounced herself up and down my cock.
“Oh yeah Luke…just like that!” She bounced harder and harder. My cock was about to explode!! I quickly grabbed Violet and started to pump in and out of her ass as hard and deep as possible. Violet was screaming again as her second orgasm hit hard and this time I felt her juices drip everywhere on me! That was enough. I wrapped my arms around Ms. Taylor and fucked her until my orgasm hit. It was one intense moment that I’ll never forget. I kept pumping my cock hard and deep into Violets bowels until my orgasm hit. When I started to spill my loads into her bum, I pushed deep into her anus as humanly possible. I held my cock far deep in her ass as I unloaded my semen into her. We both screamed from the ecstasy of that intense moment.
“Oh my God Luke!!!”
It took a couple minutes for my cock to shrink and pop out of Ms. Taylor’s ass. As it did, my jizz started to trickle out.
Violet got up and bent herself over me and squeezed and pushed her ass as more jizz poured out of her onto her bed. Then suddenly, she screamed.
“I gotta take a shit!!!!” She jumped up and kissed me, thanking me for the help as she ran to her bathroom. I just chuckled. I grabbed my clothes and left. I texted Violet thanking her for the meal and hoping she felt better. Once I got home, I began to pack for my trip. I had a flight to catch tomorrow. I also booked an extra airfare ticket. I had an idea that I hope would work out.
END OF PART 1