I was 19 worked at a grocery store in a small town. My bitchy boss Mary was always a drag. Her square face would bark out commands and I began to hate her. However, she did have a beautiful daughter named Michelle. Michelle had perky breasts, a plump butt, and a well-toned body from her years of college soccer. Michelle would always use her 24-year-old sex appeal to flirt with all the male customers. I would ignore the two only to get away from the boss.
Things changed when Michelle and I had a lunch break together. She had just broken up with her boyfriend and was feeling frisky. The verbal flirting already had my erection straining against my blue jeans. She leaned over the table and gave me a perfect view of her gorgeous cleavage. She half-jokingly stated we should play “I’ll show you mine if you show me yours”. I immediately stood up and struggled to take out my 9 3/4 inch penis (Seriously, I was hanging at six inches by the eighth grade). She was taken aback by my willingness coinciding with my length and girth, but I could tell she enjoyed my showing.
She reached out and grabbed the head; she tightly squeezed it making me flinch. She pulled me closer and encircled my scrotum with her fore finger. She released her penile death grip and gently rubbed my largest vein. A smile emerge from behind her full lips.
“Holy shit! That’s huge! You’re so much bigger than my ex. He was like four inches and very thin.” She wanted me inside of her and said that she needed to be stretched for once in her life. The vixen then let go of my junk and started slowly massaging her breasts underneath her shirt. After a quick flash of her perfect little melons, she invited me to her house the next day. She left the break room and winked at me while I tried putting everything back in place.
The rest of the day I could not get the image of her pink nipples emerging from her black lace bra out of my head. I also had an erection going that some customers gave an odd glance at. I even believe that Mary took a peak and gave a look of disgust, because she soon sent me to the back to break down the pallets of stock.
I never had sex before and needed to buy protection for my visit. After work I purchased a package of Magnums from a gas station and went home to try them on. They were tight but would get the job done. Later that day I went to a pharmacy to run some errands. I noticed that they carried condoms called Magnum XXL. I proudly purchased them from elderly female cashier that seemed surprised that someone actually needed them and thought I might be doing a prank. I went home again and they were just right, still a little too snug maybe. They’re the biggest condom on the market though so it will have to do.
The next day her mom was gone and we had sex on the mind. Michelle gave me a ride in her white Nissan and kept on grabbing the bulge in my shorts. I would gently massage her breast and told her we were going to have a fun day. I had to admit that I was a virgin and her prior experience would be needed. She explained that with my cock, she would have to learn something new also.
Michelle had long, yet beautiful brown hair and eyes that could be described as the beauty a blind man would see if he could look up at the blue summer sky. I am 6 feet 2 inches and weigh 226 lbs. I am pretty toned and quite strong. I am not the best looking guy, but I’ve got good qualities besides my huge cock.
On the way she needed to buy gas. While I was pumping she came out and began hugging me. Across from us, a teenage couple was returning to their car. Michelle decided to lift up my shorts, allowing my soft 6 ½ inch dick to fall out. She then grabbed it and gave a little holler at the couple. The guy thought it was hilarious and the girl yelled, “Good luck with that.” I was embarrassed, but Michelle’s kinky side was alluring.
The house she lived in was huge. I could see why Mary never gave the employees a pay raise!
Once in her room, she disrobed as quickly as possible and wanted my dick within her. Yet, I had to stand back and admire the beauty. I stared at her amazing 23 year body. Her pale white skin was much darker than mine and had a total lack of hair down there. Her breasts were so perfect; it was like her bra never came off.
As I started to undress she began to insert her finger into her vagina, seemingly preparing it from the incoming assault. I slipped on my Magnum while watching her play with herself.
“I still haven’t gotten over just how big that dick of yours is. How did you find condoms to fit it?” Michelle teased and giggled. I joined her on the bed while laughing, my spear standing at full attention.
She had to help me work in my large cock by guiding it with both hands while in missionary position. Slowly I worked my dick into her, stretching her shaven vagina far past what her old boyfriend could have done.
“Ugghhhh! Fuck! That’s sooo big. Please go slow. You’re so much bigger than what I’m used to.” Michelle begged, but still used her legs to push my butt in more.
Being my first time, and her beautiful body and cock worshipping, I did not last too long. This was not a problem however, because she could not handle the girth in the beginning. When I pulled out in only five minutes she let out a moan, kissed my lips, rolled off my condom, and gently massaged her vagina.
“Look how much you filled that big ol’ rubber. Wow! That’s a lot of cum! I’ve never seen so much before I think…” She took the rubber that was still covered in her plentiful juices and examined it before throwing it in the trash. Her doing that already had me at full hardness again.
The second time was a much greater success. I was able to pick her petite body up and managed to get every inch in her tight pussy causing her to orgasm.
“Ooohh fuck! I think I can feel that big thing in my throat!” I felt Michelle’s pussy contracting on each inch of the massive intruder. It took some manuevering to manage to fit the entire thing in such a snug hole. Michelle wasn’t even sure she would be able to fit all of it.
As soon as my erection slipped out of her I would slam it back in. I would pay close attention to her and made sure she enjoyed it as well as I did. Her toned body would tighten and breasts quickly jiggle to a halt when her cunt could not handle it. Her body was moist after she reached her orgasm and for the second time I filled the condom with cum.
It was an amazing 45 minutes of love-making as Michelle guided me in the right direction and helped me prolong our physical connection. Michelle collapsed on top of me while we talked and tenderly kissed one another.
This time Michelle took off the condom for me. Her eyes slowly scanned the entire massive specimen before taking it off. She took her time to peel it off while her mouth hung open.
“How could you cum this much a second time, big boy? You realize this is more cum than my ex-boyfriend ever shot, if you combined like weeks.” Michelle continued to play with it in her hands, she was obsessed.
“I can’t believe this actually fit in my poor little pussy!” She looked down at her puffy opening.
“Me either!” I smiled and gave her perfect ass a squeeze, “but I’m happy it did!”
We both laughed and then agreed that a shower was needed after the hard workout. We would soap each other up and gently rub the suds off. My balls were still tender from my expulsion, but I was still partially aroused.
Michelle turned away from me and I aligned my dick with he butt crack. I would slowly bend my knees up and down to feel softness of her silk-like buttocks against the length of my sturdy meat. I knew that ass play was out of the question. No girl deserves such a large rod in such a cute rump. We kissed and fondled each other for quite some time. My dangling meat would polish against her firm stomach as I pulled her closer. I was yet again rock hard, impressing Michelle. I was rubbing my cock and balls against her wet body. Michelle was still hurt a tiny bit from my larger cock.
Unknown to us, but her mother had come home about 4 hours early. Mary came into the bathroom to talk to Michelle when she heard her dainty daughter with a man’s voice. Next thing I know she whipped open the curtain and stared me in the eyes and made her way down to my monster-sized aroused organ. I could see her eyes widen and a beginning of a smirk, then she cupped her hands over her mouth in shock.
Michelle leaped out of the shower and grabbed the only towel as she tried to talk to her mother. I looked over and saw Michelle fumble with the towel and expose her tits because she was so nervous. My erection now throbbed as I saw my new girl holding her breast in the fluffy white towel. All I could do was turn off the water and let my schlong stand at attention. However, Mary never took her eyes off my glistening protruding member.
Michelle quickly realized her mother’s interest. Through compromise, Mary said she would not fire me if I had sex with her!
“I saw your bulging package yesterday, I was sickened by the sight, but if my daughter liked it, well then I want a try. Maybe he can learn something from me.” She was very attractive for an older woman, and thick in all the right places. I could tell she had really large tits. I thought “why not?”. It had been some time since my previous romp. Even though I hated Mary, maybe fucking her would be great?
Michelle helped me get hard outside of her mom’s room and gave me a little kiss on the cheek. “I’m sorry my Mom is sooo fucking weird. I can’t believe she’s making you do this… but I kind of get why.” She squeezed my dick and smiled, trying to get me more comfortable.
I lightly slapped her ass and prepared myself for the worst. I was like a football player walking down the tunnel… with his cock out. I opened the door to find Mary lying in the bed completely bare. I did not need the assisted arousal once I focused on Mary’s 36 Ds. She looked a little thinner without her clothes and had very large nipples. She had some stretch marks and a somewhat dimpled ass, but the attitude in her face was a turn on. She gave off an aura like she was going to show me a real woman. I reached for my condoms, but she told me she had her tubes tied a long time ago.
This just got a lot better. I get to fuck this hot older woman raw? I was back to throbbing. It even got Mary a little worried.
Unlike her daughter, I went full boar on her. I bent her over the bed and quickly shoved the fat head in causing her to squeel. Before she could process what happened I sunk in a few more inches.
“Ooohhh God! That’s sooo fucking thick!” Mary screamed so loud that Michelle must’ve heard it. “You’re so much bigger than my ex-husband… He’s got like four inches and thin.” I giggled to myself at her saying almost the same thing her daughter did about her ex-boyfriend.
I gripped her wide ass while shoving in another two inches, which must be in virgin territory for this older woman. I started to feel her walls contracting on my me while she orgasmed.
After her first orgasm, she closed her eyes and gripped the bed. Mary turned back to face me with a exhausted but big smile on her face.
“You’re fucking incredible. I should hire you just to fuck me with that huge cock of yours everyday. You don’t have to worry about being fired anymore. We’re good.”
“We’re good, huh?”
I was not done, in fact, I looked to be the biggest I’ve ever been. Probably around 10 inches and incredibly thick. Plus, I still haven’t cum, and I wanted to cum raw in her balls deep. Before she had a chance to recover I started shoving more cock inside of her.
“Fuuuuck! Wha-” She didn’t have a chance to finish her sentence before I shoved in another inch. She was now taking almost of it and loving it, dripping wetness onto the bed. With a final push that faced a lot of resistance, I got my cock fully inside the older woman. Which made me feel accomplished after doing the same to her daughter earlier today.
My orgasm came out of nowhere and I found myself hosing cum while grinding against her backside. She joined me in orgasm, feeling the lava hot cum fill her completely.
Mary started getting up, but I pushed her onto her stomach so she was in prone bone position. She had been a bitch to me in the past, so I decided I was going to try ass play with her. I straddled her thighs and she then gingerly set herself for doggy style. In one fluid motion I slammed my cockhead into her fat ass. She let out the loudest scream I had ever heard. It was an extremely tight fit and my shaft hurt in doing it. I heard Michelle’s quick jaunt down the hallway and she flung open the door. Michelle looked at her mother’s red face and followed it back to her ass. “I am glad he tried it on you mom, I guess you did teach him something.” Michelle left and I attempted to continue with the butt sex on her mom.
“Oooohh fuuuck my asss!” Mary now loved the monster cock in her ass. I was now balls deep and giver her full length strokes before smashing into her big ass cheeks. They jiggled with each penetration, I loved gripping them while fucking her hard.
I grabbed onto her ass while exploding rope after rope deep inside her bowels. It felt like the biggest release of the day even though I’ve already cummed multiple times. Mary’s asshole was gripping me hard and almost sucking the cum out of my balls. I saw her butt cheeks flex as she crushed my cock while she climaxed.
I was still hard, and seeing how much I made her asshole gape and the amount of cum leaking out, I needed to fuck again. I did her doggy style and I lasted quite some time.
Mary moaned and yelped, but never told me to stop. I ended up going for an additional 45 minutes out of spite. Whenever I felt like cumming, I would look down and think of her being a bitch to me at work. I hoped that Michelle would not be jealous that her mother had more orgasms and got additional time. Once I ravaged her hairy vagina she came and screamed aloud. I release a hefty dose of semen again deep into her cooter. Mary looked at me with her brown eyes and told me how great the experience was. She began to kiss me on the mouth. I never intended to do anything but please her pussy, but for some reason I partook in her actions.
Michelle later came in to deal with my despair. However, she found us cuddling and collapsed on my other side. The two beauties, in their own right, compared notes on their experiences. Michelle said I could only get better through experience and the cupped and jiggled my balls while giggling at her mom, almost taunting her that she owned this new treasure.
“I am always willing to help accept with the butt sex.” We both laughed. Yet I am sure Michelle would not entirely like that.
These women were crazy, but I just laid there nude, appreciating the situation. Mary stated, “You left your boyfriend and now found a real man.” I said, “That I found a great new girl with a hell of an accepting woman for a mom.” Michelle said, “Hey Mom, get your big tits out of here so we can fuck again.” I was definitely not ready for that so I practiced my oral skills on Michelle. Mary soothingly squeezed my testicles as she arose from the bed to get dressed. While Mary clasped on her immense bra, she commented on Michelle’s clean shaving saying, “I might have to try your hair style honey.” In my mind I agreed, because it was a jungle down there.
Mary then knew I was a man and allowed me to see her daughter. She told us to play it safe and only have sex in her house. Of course she would have to check in every once in awhile to see if I was packing her daughters groceries properly. I was allowed to stroll through the house completely nude whenever. Mary and Michelle both became household nudists when I was over. I believe that Mary always wanted to have sex again. However, I would only tease her by swiping up against her, grabbing her tits from behind and living temporary hand prints, fondling Michelle in front of her, placing my meat on her shoulder as she sat in a chair, or joining her for a break in her hot tub. She must of felt horny when I stripped off my shorts to get in the warm water, but respected her daughter enough to not act on her emotions.
Mary even had me take out my package when some of her older women friends were over for someone’s birthday party. Michelle was not there, and Mary then went onto bragging about she took my beef for 1 ½ hours giving me the best sex of my life. I only showed those horny housewives what I had and avoided any physical contact. I saved the true passion and sex for the amazing Michelle. After a while I had to change jobs, because our interactions became awkward when I had to be with Michelle and Mary around the co-workers. I believe that Michelle’s real beauty is within and the gateway to her beauty can be seen through those wondrous eyes.
After the fantastic sex brought us together, we bonded emotionally and intellectually. We could not be separated and our love grew larger everyday. I have other stories of Michelle and I that I may one day write of. The two women never interacted with one another, only with me. If I was never blessed with such hefty genitals, none of my adventure would have happened I would have nothing to share. Luckily Michelle and Mary open to me writing this.
Hooray, I am not a complete failure!