Misery
written by:
jwdoney

This is a work of fiction and does not portray or depict any person real or imagined and no insult is intended to anyone, anywhere. Any people, places, products or events mentioned are done so without permission or endorsement.

My name is Joshua and I am a 19 year old college sophomore home for the summer break and I am staying with my dad and his girlfriend for the summer. My mom passed away when I was 12 and it took years for my dad to get over the loss, but last year he started seeing Brandy, a gorgeous blonde who could easily be a supermodel. I met Brandy when I came home for Winter break and she has a daughter about my age who also goes to college. My dad is well off, he hates the word ‘rich' and has 2 houses, a condo, several cars and a very successful company he runs. It irritates my dad that I went to school on a scholarship as he easily could have written a check for my entire tuition, but I did take the car he gave me for graduating high school. This story isn't about my dad's money, at least not directly, instead it is how everything unraveled in possibly the hottest summer I have ever experienced and I'm not talking about the temperature outside. Brandy's daughter is named Elizabeth, and while I have not actually met Liz yet, I have seen pictures of her and we are friends on Facebook. She is very pretty... ok, she is hot, just like her mom, and blonde as well.

I had barely pulled in front of my dad's mansion... er, house, when a man dressed in a crisp suit appeared and greeted me politely and began unloading my stuff. I was trying to get him to let me help when he stood a little straighter and held his breath as he looked past me over my shoulder. I lost my own breath when I turned and saw Brandy standing there naked with a big smile on her face. I blinked several times and realized she wasn't actually naked, but about as close to it as possible as her ultra-skimpy pink bikini barely covered her important parts. The man resumed carrying my stuff into the house and Brandy said "Thank you Charles" as she came closer and pressed her mostly naked body against me and gave me a hug that would have restarted a car in a junkyard. Brandy gave me a long kiss full on the lips and said "Welcome home baby" and I gasped to catch my breath as she stepped back as if to remind me she had almost nothing on. For a 39 year old woman, Brandy looked 25 and had a killer body and I secretly envied my dad as she was smoking hot. 5', 11" without the 4 inch heels, Brandy had long smooth legs, a slim waist and hips, flat stomach and a full, firm, large chest that was easily 34D.

Brandy backed up another step and asked "What do you think of my new bikini?" and I tried to suppress a smile as I stared at her perfect body. The thin pink strings met at the tiniest of triangles that barely covered each nipple and exposed all of her firm globes, and the bottoms dipped so low it was clear she was clean shaven. I slowly let out my breath and said "It's very nice Brandy" and she beamed and pressed close for another long kiss on the lips. I felt my cock stirring and panicked as the last thing I needed was to get hard around my dad's girlfriend, smoking hot babe or not. Brandy took my hand and said she had a surprise for me but she needed me to do her a favor before Brian (my dad) got home. I almost stumbled when I got a look at Brandy from behind and my cock stiffened as all of her body was visible minus the thin string across the middle of her back, the ties around her neck and the thong snug in her firm ass cheeks. Brandy said she had a couple of the rooms in use as she got her clothing business started and until Charles moved everything I would just stay in Liz's room tonight. I wasn't really listening to Brandy as I followed her into the house captivated by her body and trying to will my increasing erection to subside. The house was nice and cool and Brandy's nipples perked right up forcing the tiny triangles to stretch to contain them.

Just as Brandy spotted my erection tenting my shorts a beautiful dark haired woman came up wearing a tight short black skirt and half t-shirt. She was holding two cold water bottles and smiling and Brandy almost jumped in front of me facing the woman as she approached us. Brandy hissed "Don't move" and backed her thong covered ass against my stiff cock as the woman said hello and Brandy introduced me to Carmen. I took the water bottle from Carmen as Brandy shifted her butt against my crotch causing my erection to push against her ass from behind. Carmen was about 30 and beautiful, clearly Hispanic with long black hair and a shapely body. I didn't understand the short skirt and half tee but it looked great on her so it was all good. Brandy wiggled her butt against my cock some more as Carmen asked what I wanted for dinner and I swallowed and said "Any... anything's fine" and Brandy laughed and said "Tell Andre to plan for steaks on the grill." Carmen nodded to Brandy then gave me an "I'll fuck you later look" then smiled and walked away and I was sure I imagined it until Brandy said "Wow Josh, she really likes you." Then as if things could get any more surreal, Brandy moved away from my crotch, turned to face me, and put her hand on my bulge and said "Oh my, are you ok?" She held my cock through my shorts for several seconds and I mumbled "I'm fine" as Brandy squeezed once, then let go and said "Ok, let's see about that favor before your dad gets home."

Brandy went over and waited by the stairs as I drank the entire bottle of water and was wondering where to put it when Carmen appeared. She took the empty bottle and said "steak is good, but maybe you want some Mexican later?" I gasped and she glanced over at Brandy who suddenly seemed interested in staring at her fingernails. Carmen moved closer and kissed me passionately so that I lost my breath and she said "Maybe you get lucky tonight." And I'm pretty sure it wasn't a question. Carmen walked off and my cock was now rock hard and likely to tear thru my shorts and there was no way to hide it as I went over to where Brandy was still intently studying her nails. Brandy sighed and said we had to do something about that before I passed out and by the time I realized what she was talking about she had my hand and was leading me up the stairs. We went down one of the hallways and into my bedroom and sure enough there were racks and piles and boxes of clothes everywhere. She said she needed me to try on a few things before she submitted them to production and with a wink she said if I did a good job she would keep my dad busy so Carmen could take me around the world.

Yes, she actually said that.

My cock was throbbing and straining my shorts and underwear and Brandy would steal a glance now and then but mostly tried to ignore my erection. She handed me a small pair of blue swim shorts and said "Let's start with that" and I gasped and she said "Relax, it's not like I'm gonna seduce you." Brandy was staring at me and said "Oh... ok I see" and I blinked and said "What?" and she looked down at her nearly naked body and the pointless bikini and said "I did that? I excited you?" I gasped again "No... I... Uh..." Brandy looked mad and said "Oh, what... I'm too old, I'm not pretty enough for you?" and without thinking I blurted "Brandy you're fucking hot, I'd kill to fuck you." After a long moment Brandy smiled and said "That's sweet honey, thank you" and she said "Ok, try those on and we'll get started." Happy the tense moment had passed I hurried into the bathroom before I remembered I was 9 inches rock hard about to try on a small tight pair of shorts. I got undressed and was standing there completely naked except for socks when Brandy came in and asked "What's taking so...?" and gasped "Oh wow, I see..." Brandy shuddered causing her breasts to strain the tiny bikini to its limit and she said "Baby, you ARE just like your father!"

I blushed and had no place to hide, she had seen everything and to make matters worse was still wearing the skimpy pointless pink bikini that showed just about all of her body. Brandy let out a long slow sigh and said she had an idea but I could never tell my father about it. My heart raced as she took my hand and led me out to the crowded bedroom turned storage and let go of my hand to go over and lock the door. Brandy said we would just wait a few minutes for me to ‘relax' and in the meantime she would try a couple of things on and I could tell her what I thought. I was confused; she was ok with me being naked and stiff in the locked room with her? Was that the secret we would keep from my father? Brandy fussed around looking at things hanging from a rack then slipped a hand around my shaft as she passed by me to look into some boxes. I swallowed as her warm fingers encircled my throbbing cock and she asked "You ok? Do you need a minute?" I moaned "I'm alright" and she let go of me to rummage through some boxes. Since I had pulled up in front of the house Brandy had been practically naked so I don't know why it further excited me when she stopped messing with the box and smiled at me as she untied her bikini strings and let it drop. Her large breasts were now completely bared and my cock twitched as she untied the back and said "Ok so what do you think?"

I gasped "Uh... they... they're amazing" and she laughed and said "No, I'm talking about this" and she held up a flag striped bikini top. Even as my cock pulsed and I could feel my blood pressure in my neck Brandy pulled on the flag bikini top, adjusted her load into it, and then asked "There, how's it look?" I said "Wow" and she smiled and said "Alright, now the bottoms" and even as I hoped she would do it, Brandy pulled at the strings and the bits of material dropped and exposed her clean shaven pussy lips. I was almost shaking with desire and it took my last bit of willpower to remember this was my father's girlfriend as she remained bottomless and said "Now where were they?" she said "Sweetie, look in that box please?" and I somehow managed to walk over to it and take the lid off and look inside. There were panties, bras, bikini tops and bottoms, even a pair of shorts, but I didn't see the match to her flag bikini. Brandy said "Josh, you ok?" and I swallowed and said "Yeah, fine" and she crowded past me to look into the box and I froze as my cock slapped against her bare back, thumped against her hip and poked against her firm ass. Brandy laughed and wiggled between my naked body and the box and both of us froze as my cock finally slapped against her butt cheek and ended up almost perfectly placed against her ass.

Brandy giggled "Sorry" and moved so that my cock stood proudly up and out as she said "I can't find the bottoms." I was swaying and close to my limit and Brandy shrugged and said she would try something else and I could only stare as she pulled off the flag bikini top and was now completely naked the same as me. Brandy touched my cock with a couple of her fingers causing it to twitch and she said "Still hard." I don't think it was a question. She said she would try something else and moved naked over to a rack with various items hanging from it. She said she needed me to do something for her and I was in a haze and numbly shuffled over to where she was standing. Turning to face me Brandy asked "Josh, hold these for a minute so I can decide?" and it didn't make sense but I took both of her breasts in my hands and held them firmly. Brandy said "Oh, um... ok" and a few seconds later she said "heh... sweetie, I was talking about these" as she held up bikinis on two small hangers. I let go of her breasts and blushed, my cock twitched and throbbed, and Brandy handed me the bikinis and smiled as if all of this were a normal thing. It was really difficult to concentrate with her completely naked body full on facing me while my enraged cock pointed at her and I held up a pair of bikinis. She was so close to me and I just wanted to touch her and I was swaying...

Brandy said "Josh, don't move honey" but I was losing my struggle and dropped the bikinis, put my hands on her hips, and pulled her close to me. I saw red and pulled at her until my cock was trapped between our bodies and out lips met and she mumbled "We shouldn't" even as her lips parted and our tongues danced. I kissed her neck and made my way down to engulf her full breast, teased her nipple, and then we kissed again. She said "you can never tell anyone" even as I fumbled my cock against her warm entrance and poked my tip inside her. It felt warm and tight and amazing and we fell to the clothing covered bed as she gasped "Fuck me" and I moved her so that I was atop and inside her on the bed. I began to stroke deep inside Brandy and she moaned softly when the door rattled and my dad asked "Brandy?" We froze and Brandy whispered "Shit" as I started to pull out and she wrapped herself around me to keep me inside her whispering "Wait!" there was another rattle and a knock and my dad shouted "Josh? Brandy?" and this time I pulled out and hurried into the bathroom to fumble my clothes on. I had barely gotten dressed when I heard my dad say "Hi baby" and then my dad asked Brandy "Where's Josh, I have a surprise for him?" I stepped out of the bathroom and said "Hi dad" and was surprised to see Brandy fully dressed in shorts and a t-shirt. My dad gave me a huge hug, somehow not noticing my bulging shorts, and he dragged me downstairs apparently oblivious to whatever Brandy and I had been doing in the room with the door locked. Carmen winked at me as my dad led me out to the front driveway and sitting there was a brand new SUV... with a gorgeous redhead leaning against it.

I was still staring at the redhead when my dad said "Well, what do you think?" and I tore my eyes away from the beautiful redhead and looked at the SUV and said "It's great dad, thanks." He clapped me on the back and laughed "Son the truck IS yours but I'm talking about Rachel." The redhead smiled and stood away from the SUV and said "Hi Josh, I'm Rachel" and I was confused. Rachel was maybe 23 or 24 and a stunning knockout, no disrespect to Brandy or Carmen, but Rachel was beautiful. She was tall and shapely and pretty and I turned to my dad and said "Wait, how can you give me a person? No offense Rachel." Rachel laughed and said "None taken" and my dad said Rachel worked for him and saw pictures of me and wanted to meet me so he decided to bring her home for dinner, like a date.

Really? A date?

Brandy's face was a cross between jealous and surprised, and maybe a little bit confused, and I went to greet Rachel with my hand out and she pulled me into an amazingly breathtaking kiss. By the time we parted I was gasping and she said she wanted to be clear, meeting me had nothing to do with furthering her career, but now that she had met me in person, she would quit if she had to. My dad said "Whoa, lets' not be hasty, you're one of my best account reps, take it easy" and then Brandy hissed "I need to talk to you" and dragged my dad away from us. Rachel said she knew I might be having a hard time with this. Meeting like this, and she would go if that was what I wanted, and my heart raced as I said "NO" maybe a little too loudly. Charles was transferring some stuff from my car to the new SUV and stopped to stare, as did my dad and Brandy, and Rachel blushed. She said "You're ok with this? And I asked "Uh yeah... wait? What exactly is ‘this'?" Rachel smiled and said we could hang out, maybe hit the pool, have dinner, and if I was lucky we would see where things went. I laughed and she looked at me funny and asked "What?" and I swallowed and said "Wait, you were serious?" Rachel took my hand and led me away from the SUV and Charles and said that sure it seemed strange to me, but for weeks she had seen my pictures in my dad's office, heard all about me, then she laughed and said "Duh, were friends on Facebook" and she pulled out her phone and showed me her profile.

She was one of those people who instead of a photo have a picture of a car, a flower, whatever, but sure enough, ‘Rachel Winters', profile picture of a waterfall. I took out my phone, loaded FB and found her profile, scrolled down a bit and said "Is this true?" and she laughed and said "What, girls can't play videogames?" I smiled and said "Not girls who look like you." Rachel kissed me and when we parted she said maybe I would get lucky after all. My dad came over with Brandy behind him looking seriously pissed and said Rachel was staying for dinner and even if some people didn't like it, she would be going to the lake with us this weekend. Then after a glare at Brandy he smiled at me and asked "I assume you're ok with this?" Rachel took my hand and I said "Uh yeah". My dad walked off and Brandy said "I need to talk to Josh for a moment, Rachel could you wait inside?" Rachel smiled and walked with my dad talking about accounts as Brandy led me down the driveway and into one of the garages. Not a word was spoken until Brandy opened a doorway into a cool air-conditioned stairway and led me up to a loft. She locked the door and went around and drew the blinds and said "I think we were in the middle of something?" as she pulled the t-shirt up and off and exposed her bare breasts. My mind was racing as she struggled the shorts down... no panties... and said "Take me."

Despite better judgment, I was getting hard and she was the epitome of the term MILF, so I stripped and kissed her as she pulled me towards the bed. I greedily engulfed each of her large breasts in turn then kissed my way down her stomach before she stopped me and said we could do that next time, we had to hurry. Even with my stiff cock inches from her welcoming pussy I froze and asked "next time?" and Brandy smiled and said "Sweetie, we have all summer." I moved closer with my blood boiling and poked against her warm wet opening and she welcomed me as I slipped inside her. I wanted to savor every second and Brandy said she was sure I wouldn't hear it very often, but I needed to hurry up and fuck her, we didn't have long. I wasted no time pounding into her as fast and hard as I could and Brandy was gasping and panting as I stroked inside her. I thought of everything sexy and erotic I could but finally focused on first seeing her in the tiny bikini and my balls tightened. Brandy gasped "Give it to me, cum in me" and I exploded deep inside her tight body as she gasped "Keep going, I'm there" and a few seconds later she whimpered through a muffled orgasm. I was drained and felt completely sated as Brandy said she hated to do it but we had to clean up, get dressed and get back.

I was struggling with my thoughts and she kissed me and said I could not dwell on it as her and my dad had an understanding and she would explain later. I was pulling on my shirt when I stopped and asked if she had planned all along to sleep with me and she shrugged and said "Not on the first day." I blushed and sat down and she said "Compliment Josh, it's a compliment." Then she said "Honey, focus or he'll know." I nodded and she said this was gonna be a busy summer for me and I frowned and she said besides her, I had Carmen, Liz and now Rachel and I stared at her wide eyed and open mouthed and she laughed. My mind was swirling... Brandy, Carmen, Rachel... Liz? I asked "Liz" and she shrugged and said she was almost positive Liz would want me the minute she saw me, Rachel or not. I was in a daze all the way back to the house and I saw my dad and Rachel out by the pool and Rachel was in a blue bikini and looked fantastic. Next thing I knew Carmen practically pounced on me and said she needed to show me something and the way Brandy was laughing told me Carmen was up to no good.

... To be continued...