Summer Chores: The Wine Delivery

I woke up and headed down to the kitchen to get some breakfast for myself. Being a Thursday, I had the house to myself. Mom and dad were at work, my sister was out running around with one of her friends and I was able to sit, relax, dream of Lisa and worry about what job I'm going to get back at the university. I only had a week left before I had to head back to college to start my sophomore year. I rounded the corner to the kitchen to be surprised by my mom standing at the fridge.

"Hey honey." Mom said as she took the water pitcher out of the fridge. Mom was supposed to be at work. My mom was pretty good looking. Not what most would call hot but she was fit, average breasts and dark hair. She had a nice shape that seemed to fit her body. Just enough ass to make you take a second look. Mom was wearing a cover for a swimsuit that looked like a sundress.

"Lisa and I are headed over to one of her fiends' place for a ladies only pool party. Don't tell anyone I played hooky today." She said smiling.

"Ok. But I'm sure nobody uses the term 'hooky' anymore." I said jokingly.

"Well.. whatever the term is you all use, I'm not at work." Mom laughed. "Don't get into too much trouble today," she said.

"Nothing for me to do to get in trouble around here." I replied.

"Sure there isn't," mom smiled as she walked closer to me. She had a devilish smile on her face.

Mom and Lisa had been exposing me to the sexual experience of a lifetime this summer.

"I got myself into some trouble this morning." Mom said as she reached up under her dress and pulled down her panties.

Mom handed them to me as she said, "Here. Put these on and wear them today. If you still have them on later, maybe I'll reward you."

I noticed her panties had a small wet spot on them as I took them from her.

"I've been excited all morning. I'm sure it'll feel good against you." She added. "Go ahead, put them on. Now!" She ordered.

I dropped my gym shorts and boxers right there. My dick had started to harden by this time and mom noticed.

"Oh. You're liking this huh? Try not to cum in my panties until I say it's ok." She said as I started to put them on.

Her panties were bikini style and a bit cheeky. I slide them on and pulled them up. I could feel the warm, wet spot from mom as her panties pressed against me. It was rather difficult to keep my dick inside the panties because of the style and size.

"I like they way they look on you. You can't take them off until I tell you to. And no jerking off today." She said as she headed to the door. "Talk to you later sweetie," she added as she left.

Well, I was not going to get much done now. I headed to my room and sat down in my chair to process what had just happened. I could feel moms panties trying to turn into a thong because of the cheeky cut. Normally, this would be uncomfortable but simply having my mother's fresh, wet panties on made me horny as hell.

After trying to watch some TV, I thought, 'fuck it, I'm going to jerk myself off hard'. I pulled up the picture of mom and Lisa together after our threesome. Both women had amazing breasts that sported slight stretch marks. They also knew about my fetish for armpits so they had raised up their arms for a clear shot. Lisa's armpits were smooth and shaved clean. She always kept herself up. Moms armpits were also clean shaven but she has a bit more texture and honestly, I preferred more texture to armpits. The taboo of staring at my mother's armpits while I cum made it much more intense for me. I propped up my laptop and pulled my dick out the side of moms panties. I had just started to stroke enough to get my precum all over my hand when a call came through my computer and cell phone. It was mom. I put everything on hold and answered.

"Hello?" I answered.

"Hey honey." Mom said. "Hey boy!" I heard Lisa yell from the background.

"Tell Lisa I said hi." I told mom.

"Ha ha. Ok then." She said as she repeated what I said to Lisa.

"So, us ladies need some more wine. Could you run to the liquor store and get some for us. We'll give you some cash for your time if you deliver it. Please?!" Mom begged.

"Ok. Fine. Text me what you want specifically." I caved.

"I will. You'd better be following my instructions still. 'Click'" mom said as she hung up.

Well, this is going to be interesting, I thought to myself. I have to go to the liquor store and drop off alcohol to their pool outing while wearing my moms panties. Oh well. At least I had on basket ball shorts and a t-shirt. It'd be nearly impossible for anyone to notice. I grabbed my keys, wallet and headed out the door.

As I got into my car and started to the liquor store, mom's panties that started to feel a bit tight. They started climbing into my ass and that put extra pressure on my dick as I was driving. While it was a bit uncomfortable, it was a constant reminder that I had moms pussy soaked panties pushing against me. I had to try my best to focus on the road to prevent having a massive hard-on as I got to the state store.

At the store, I grabbed the wine that mom texted me about and headed to the checkout. Half way there, with my hands full of wine, I felt moms panties start to slip up my crack again and the front of her panties start to shift from being so tight. When I stepped up to the register, I felt my cock slip out the side of the panties. It was an odd feeling as I was standing there trying to pay for my wine. Somehow, I got through with my wine, composure and without being noticed. Now, all I had to do was get to the pool party and make it home.

I pulled up to the house where mom and Lisa went to the pool party. I grabbed the box of wine bottles and headed in. There were only 4 women there including my mom and Lisa. 3 were floating in the pool and one was in a chair sunning.

"Special delivery!" I yelled playfully as I sat the wine down on the table next to the pool. "Need anything else before I go?" I asked.

"Could you run in and get the wine opener? It's in the drawer next to the sink. Please?" Asked Marybeth. She was the one who owned the pool. Marybeth is the same age as mom and Lisa but she's got a bit more weight on her. Don't get me wrong, she's not fat but she does have some thickness to her. Her tits are a bit big and her ass is still round. She's also got pretty deep red hair.

I entered the kitchen and found the wine opener. I looked out the window at the four women in bathing suits. Mom was wearing a very conservative 2 piece suit that still covered her stomach. Lisa was wearing a one piece that had the side open. Marybeth didn't care and was wearing a normal 2 piece bikini. The lady in the chair sunning I didn't know. She had on another 2 piece bikini and was also fairly standard.

I walked back to the pool and found everyone out sitting around on their lounge chairs. As I walked up, they all held up their glasses and playfully said, 'I'll take another glass pool boy!'.

I laughed and opened a bottle for them. As I started walking around the table to pour each a glass of wine, they started talking again and I could feel moms panties starting to pull on me again as a I moved. By the time I got to the last glass, my dick had fallen out the side and the back had turned from cheeky to full on thong. Feeling the head of my dick move against my gym shorts, in addition to having moms panties on, was starting to get me going. It didn't help having 4 beautiful women in bikinis around me. Once I sat back down, I was a bit relieved. I wouldn't mind so much if it were only Lisa and mom but I had no idea about the other two ladies.

"If you ladies don't need anything else, I'll head back home." I said eagerly.

"Don't be silly. We don't mind having a young, handsome pool boy here." Marybeth said.

"I'm so sorry. This is my friend Sarah." Marybeth said as she introduced her friend.

"Hi Sarah." I replied.

"Hi. And thanks for the wine delivery!" Sarah added. "Hey, I have a question. If you don't mind entertaining this old lady... do you think my legs are smooth?" Sarah raised her leg towards me.

"Ah shit. Here we go again. You won't give it up will you Sarah?!" Marybeth replied in a joking way.

"What?! I bet he'd give us an answer that would be unbiased." Sarah replied. "Go ahead, feel my leg. I won't bite. I want to know if it's smoother than Marybeth's!"

Trying to hold my laugh in at these bickering women was difficult. Apparently, Sarah was the one in the group who was really concerned about her looks. Not wanting to be a jerk, I obliged. Honestly, I didn't mind. Truthfully I wanted to feel her legs anyway.

"Yeah. Your legs are a tab bit smoother than Marybeth's. What are you all debating? Some sort of lotion or something?" I asked.

"No, she thinks money fixes all things. Sarah went and had laser hair removal. She wants to be super smooth for her husband." Marybeth added as she rolled her eyes.

"I tried it on my legs first. Then I went and had hair removed from my armpits and my... other area." Sarah replied as she held up one arm.

I was in total shock because here is a beautiful woman showing me her armpit, which I have a major fetish for, and she doesn't even know it. My dick started to stir and then I could feel my moms panties again. Talk about a domino effect.

"I'm sorry. You probably don't care to hear about girl stuff." Marybeth butted in.

"Sarah put her arm down. "That's the reason he could give us an honest answer."

"Uh.. about what?" I asked.

"Who's smoother!" Sarah asked.

"You know, maybe he should compare our armpits. It'll be easier to notice a difference." Lisa said as she smiled at me. She knew full well what she was doing. Lisa has been using my fetish all summer to get whatever she wanted.

I looked at her and she kept smiling. Then mom added, "yeah. I just shaved this morning, maybe you can compare hers to mine." She said as she held up her arms. She looked at her pit and felt how smooth she was. Mom looked at me and glanced to Lisa smiling. This was going to be interesting as I could already feel my dick starting to thicken even more.

"Great idea!" Added Sarah. She raised up her arm and placed one hand behind her head. "Come tell me who's pits are smoother. I know that the laser treatments are better." She said confidently.

"Might as well start with me." Marybeth said as she raised up her arms also.

Nervously, I walked over to Marybeth and looked at her armpits. I could feel my dick pressing against my moms panties. My only hope is that my dick wouldn't slide out the side of moms panties that had a fairly narrow front.

Marybeths armpits were clean shaven and smooth. Her skin was slightly darker in her pits and her arms had slight stretch marks. Overall, she was pretty damn hot.

"Go ahead, feel them. I won't bite." She said.

"Yes ma'am." I replied as I reached up to feel her underarm.

"Pretty smooth" I replied.

"I'm next" mom said.

I walked over to mom. She couldn't wipe her smile from her face if she wanted to. Her and Lisa knew I had a fetish for armpits and mom also knows I'm wearing her panties. Mom looked at her armpit.

"And??" She asked.

I looked at moms armpits. Her pits were smooth and a little lighter in color from the rest of her skin. I felt moms armpits also and her pits were damp from sweat but that made my hand glide across her skin giving her a silky feel.

"Are they kissable?" Mom asked.

"I believe so." I replied.

"Well then.. prove it. Kiss my armpits and tell me if they're smoother than Sarah's." Mom demanded.

"Oh. That's hot and dirty!" Marybeth said, "you'll have to come back here and see if mine are also!"

I looked at mom, who was trying to hold in a laugh, and reluctantly leaned in to kiss her armpit.

"Don't forget to use some tongue." Mom added.

I kissed moms armpit and give a small lick as I did. Her pits were smooth and the sweat added a salty flavor. Her underarm was soft and warm.

I stood up and said, "those are pretty smooth also."

Marybeth yelled, "not fair... you have to kiss mine now also."

I walked over to Marybeth as she held up her arm. I leaned in to kiss Marybeth's armpit and could feel moms panties start to ride up my crack again. Marybeth's underarm was also smooth, a bit salty from her sweat and warm. Being a bit chubby, her pits were somewhat bigger and softer also.

Lisa added, "now it's my turn!"

I walked over to Lisa as she held up her arms.

"Are mine as kissable?" She asked with a grin.

"I'll see." I said.

I leaned in to kiss Lisa's armpit. Her armpits were well kept, shaved and smooth. As I planted my lips and licked her pit slightly, I could feel her warmth and taste her sweat.

As I was there, Lisa whispered in my ear, "You didn't address me as mistress. You need to be punished."

That made me tingle. I felt my dick leak some precum into moms panties, which were barely holding my throbbing hard cock in at this point. Lisa smiled at me as I stood back up.

"Now, for the test, how are mine?!" Sarah asked as she placed her hands behind her head exposing her armpits.

I walked over to Sarah and looked at her armpits. Sarah's underarms were smooth and nearly flawless. She still had a slight texture to her armpits but there was no difference in skin color. Her pits glistened from the thin amount of sweat. I leaned in and kissed her pits as I also licked them a little. Her skin was silky smooth, salty, soft, warm and all around amazing. As I stood back up, I felt my dick slip out the side of moms panties.

"Oh. I must have won!" Sarah said as she saw my dick pressing against my shorts. "My pits are so smooth, I've turned this young man on. Wanna kiss them again?" She teased.

"Uh." I started

"Lick her pits clean!" Demanded Lisa.

I leaned over and started licking her armpits when I felt Sarah grab my cock through my shorts.

"Ooh. He's firm." Sarah said. She was fondling me and making me really turned on as I licked her armpits clean.

I stood up and my cock was creating an obvious tent in my shorts.

"Why don't you take those shorts off and show us what you have there?!" Sarah asked.

Before I could tell her no, mom added in, "go ahead. Take off your shorts baby."

I was hesitant and mom knew why.

"Take them off now!" Lisa ordered.

"Uh. Ok." I replied.

"That's not how you address me!" Lisa stated.

"Uh. Yes mistress." I responded.

"Oh. This is getting good!" Marybeth said excitedly.

I placed my thumbs in my shorts and also grabbed my moms panties to take them down with my shorts. Hopefully, nobody will notice if I'm carful.

"Just the shorts honey. Leave your panties on." Mom said.

Completely mortified, I dropped my shorts leaving moms panties on. They were climbing up my ass and my cock was hanging out the side. I was still standing next to Sarah who still had her arms up flaunting her armpits at me.

"Oh wow. Look at that. Who's panties are those?" Lisa asked.

"My mother's, mistress." I replied.

"I told him to wear them today. I had rubbed myself off this morning with them on and made them wet. I figured he could keep them warm for me." Mom said.

"Well, my pussy is all wet now." Marybeth said.

"Put your dick in my armpit." Sarah said.

I put my cock in her armpit and she closed her arm down. It was an odd warmth and feeling. Her pit was definitely smoother than the rest. Sarah raised her arm back up and my cock came free.

"Thanks for getting my armpit wet." Sarah said as she rubbed my precum in her pit.

"Those panties look good on you." Lisa said. "I think you should keep them on all day."

"Hey Lisa, make him masturbate for me." Sarah said.

"Damn, this is making me so fucking wet!" Marybeth added.

"Start jacking off. But don't cum." Mistress ordered.

I grabbed my cock and started stroking slowly. I had to be careful because I was so horny to begin with. I couldn't stop staring at Sarah's amazing armpits. Every time my hand moved up my shaft, I ran my fingers over the head of my penis allowing my hand to get soaked in my natural lube. It wasn't long before I was lubed up to the point here you could hear me stroking. I was getting close.

"Ok, stop!" Lisa demanded.

I stopped right then and let go of myself. Sarah grabbed my hands and started to lick and suck on my fingers.

"Mmm. You taste good." Sarah moaned.

"Come here and let me feel you!" Marybeth ordered.

"Lick her pit clean." Mistress Lisa said.

"Yes mistress!" I replied.

I walked over to Marybeth as my dick swung side to side and dripped my clear pre-cum all over. Marybeth laid back her chair slightly to more of a sunning position. She grabbed my cock and started stroking it slowly as she raised up her other arm. "Lick me clean like Lisa said."

"Clean her before she makes you cum." Lisa said.

I started to lick her armpit. I ran my tongue through her armpit and savored her saltiness. Marybeth started to stoke me faster. The more I cleaned her armpit, the more tuned on I got. I was really close to blowing my load when I felt her stop.

"Now my other pit!" Marybeth demanded.

I walked to the other side of her chair and started licking her other armpit. Her skin was not as smooth as the other women but she was soft. She didn't start jacking me off this time.. I felt her moving more though.

"Mmm. This is so hot. Why didn't I think to let a man do this before. Oohh." Marybeth said.

That's when I noticed, she was rubbing her clit. I kept licking her armpit and would stop to gently suck on her skin. Marybeth was rubbing her clit in circles and started to speed up. I kept working her underarm.

"Grab her breasts and rub her nipple!" Mistress said.

I grabbed her breast and felt her nipple through her bathing suit. I made three circles around her nipple when she tensed up.

"Uhh. Uh. God. Damn. Uhhh." Marybeth grunted.

I kept doing my motions until she stopped. Sitting up, I noticed I had made a puddle under her from my own cock dripping precum.

"Lick my fingers clean!" Marybeth demanded.

She placed her hand to my face and inserted one finger in my mouth. Her pussy lube coated my lips and tongue. She tasted good. I was craving more from all of this.

"Well. I need to cum also. What else does he do?" Sarah asked Lisa.

"Whatever you want him to." Mistress replied.

"Have him lick my hairless pussy." Sarah said as she took off her bathing suit.

Sarah was the most flawless woman I've ever seen that was in her 50's. She scooted to the edge of her lounge chair and opened her legs to show the smoothest pussy I've ever seen in person. I kneeled down and gently licked around her lips and then ran my tongue slowly up her slit barley touching her. Sarah then grabbed my head and pushed my face into her as she started to grind her pussy on my face. It was all I could do to keep trying to lick her clit. My face was soaked from her pussy in no time and I felt her tense up as she wrapped her legs around my head. She came hard and fast while staying nearly silent.

"Somethings never change. Has a guy ever came before you?" Mistress asked Sarah.

"Haha. Nope. I'm lucky I guess." Sarah replied.

"Hmm. Maybe." Mistress said with a grin.

"Might as well come here and clean your mother's underarms. You are wearing my panties after all." Mom said as she raised up her arms.

I went over to mom dove right in.

"Mmm. This is good." Mom said.

"Rub your mother's clit and make her cum." Mistress said.

I reached over to moms pussy and pulled her bathing suit to the side. I was still licking and sucking on her armpits as I slide my finger into her pussy. Once my fingers were good and wet, I started rubbing my fingers up and down her slit. Mom started to moan and she grabbed her breasts. She started to tug on her nipples as I continued sucking on her armpit and rubbing her clit.