Fantasy Actress Roleplays

[Krishan202]

As graduation day approached, I was one of the fortunate students to have a full-time job waiting for me at a real estate development company I had interned with for two summers. Even better, I didn't have to start work until the Tuesday after Memorial Day, and that would leave me a week of doing nothing but sleeping in and catching up on sleep I had lost over the past four years. It really didn't matter whether I'd lost sleep due to studying or attending an all-night beer-pong party, I needed to sleep about 14 hours a day for a while to catch up.


My mom and dad had recently retired and were travelling quite a bit, so living at home right after graduation would allow me to save up some cash and, as an only child, have the house to myself. My dad, retired from a career as the chief , and my mom from a lucrative career in commercial real estate leasing, did quite well for themselves and our home was perched on a hillside overlooking the city. They had a huge patio area, complete with swimming pool, hot tub, and built-in cabana style bar, that cantilevered out over the edge of hill and provided a spectacular view of the city.

After graduating on a Saturday, it was the setting on my parent's home where they hosted a party to celebrate with friends and family on Sunday afternoon and evening. It was a  party complete with dancers, music, and drinks with little umbrellas. New friends, old friends, family and a whole host of my parents' friends partied the night away; including the Mayor and his lovely MILF wife who always managed to drink too much and say some funny shit she probably shouldn't say.



The next morning, I was snoring away in a fog when I thought I dreamt someone was tapping on my bedroom door. It had to be a dream, there was no way in hell someone would wake me up at all on the morning after my graduation party. The dream continued and became very real when I felt a light shaking, looked up out of one partially-opened, hangover laiden eye, and saw my mom standing next to my bed.

" You need to get up," she said gently.

After making some incoherent mumbling sounds, I finally was able to peel apart my alcohol-parched lips and say, "Why, is the house burning down?"

"No silly. It is 9am and you promised Trisha you'd be over to their place by 10."

Trisha was the wife of Mayor; the current Mayor of our city. I had no idea what my mom was talking about, but there was no way in hell I was going over there that early in the morning; I doubt very much Trisha was in any better shape than I was given how much she had to drink the night before.

"What are you talking about, Mom?" I asked with an angry voice.

"Don't get all bent out of shape with me! You told the Mayor & Trisha you'd gladly help them with some work today for which they'd gladly pay you. In fact, your exact words were 'Sure. I'll see you at 10. The extra cash will really help until I start my job.'"



"Oh shit. Okay. I have some foggy recollection of that." I rolled over, buried my head in my pillow and blew off a litany of swear words aimed at myself for my own stupidity. I finally dragged myself out of bed, stumbled into some shorts and a t-shirt, and headed downstairs. I love my mom; she greeted me with an extra-large cup of morning joe and a peanut butter and jelly breakfast sandwich.

"Here you go, BJ. Don't let Trisha drive you crazy with her non-stop gossip."

"Whatever. At least I'll pick up a little cash. Those people have money, so I am hoping they pay me well."

As I drove over to her home, helped by the sudden onboarding of caffeine, my hangover cleared enough for me to think it wouldn't be a bad day to catch a few glimpses of Trisha. She was well-known around town as being heavily involved in many high-profile non-profit organizations and community groups. However, amongst the younger male crowd, she was most famous for being arguably the hottest MILF in the city. The Cole's never had children so her body didn't suffer the consequences. Trisha is not skinny, but carrying a healthy chunk that is topped off by tits in the B range; if I was in a betting pool I'd say 33b.

As I pulled up to the driveway entrance of their lavish home (some would say mansion) I pushed the button on the call box at the gate. A pleasant female voice answered, "Hello, Brian is that you?" Brian J is my real name, but no one who really knows me calls me anything but BJ (a nickname that was quite valuable growing up I might add).

"Yes. It's BJ. I'm here at the gate."



"Okay, drive up to the garage at the side of the house and I'll have someone meet you out there."

I drove through the U-shaped driveway, past their beautiful home, and pulled up outside a 4-car garage. One of the garage doors started opening and out walked woman. She showed me into the house, offered me a bottle of water, which I gladly took (still dehydrated from drinking the night before) and then walked me out to a pool house in the backyard. Keeping in mind the fantastic yard at my parents I grew up with, this place was right out of a magazine. Large pool with natural waterfalls in a garden setting, a hot tub, and a few king-sized cabanas. There was no other furniture or pads on the cabanas and I quickly found out that my first job was to empty out the stuff from the expansive pool house to get the yard ready for a summer of parties.

As I cleared out the pool house, I realized it had a steam room, a dry sauna, a bedroom, bathroom, small kitchen, and even a little bar that had a service window opening out to the pool deck. Hell, this place was like its own little house. "What a great place to grow up. Think of all the chicks I could've brought back here," I thought to myself.

Once I was done, I refilled my water bottle from the refrigerator water-dispenser and sat down on a comfy chair in the pool house. A few minutes later, the same woman who greeted me, came waddling back to the pool house. She inspected my work and then asked me if I wanted a sandwich. I gladly accepted and she brought me some more cold water, a sandwich, and some chips. The pool deck was the perfect place to relax and enjoy lunch. However, still no sign of Trisha and that was supposed to be one of the perks of agreeing to work here.

Once I finished work, the woman returned again and led me back into the garage. After opening two of the doors, she had me back out a large, black Mercedes sedan and a white, Cadillac Escalade SUV; what a fucking nice ride the Caddy was. A staircase leading to a large attic lowered out of the ceiling and I could tell my next assignment wasn't going to be as fun as the last.

Leading me to what seemed like a large office just inside the home, I was shown stacks of boxes of books; enough to fill a college library. And, you guessed it, they had to go up into the attic. Books, not the lightest of cargo, have got to be the worst thing to carry up flimsy stairs and into the attic. At 6' 2" and 200 pounds, while the weight wasn't the biggest issue, squatting in the attic, carrying heavy boxes, made this seem like punishment.

As I begrudgingly started moving the boxes, I realized that maybe I was being punished by this woman; my task master. I couldn't figure out why the first couple hours of the day, when it was still reasonably cool, I worked outside and now, as the heat of the day increased, I was working in and out of an attic that felt like it was 120 degrees. And, still no sign of "Trisha."

As I was chugging down one of my many cold bottles of water, in between hoisting boxes, I saw my task master walk out to her car and drive away for the day. I guessed this was my last job of the day and set out to finish. I grabbed my last box and headed up the stairs. As I came down out of the attic, satisfied I didn't need to go to the gym for a few days, the door opened to the house and out walked Trisha, finally. And boy was it worth the wait.

She was wearing a short skirt and a cleavage-revealing, scoop neck t-shirt that was so tight it looked painted on her gigantic tits. She was amazingly beautiful. She gave a little laugh and said, "Look at you, Brian. You're a mess. You've obviously worked very hard."



Glancing down at myself, I realized I had picked up my share of cobwebs in the attic and my shirt was completely soaked through with sweat. What hair I had was tossed all around and equally covered in cobwebs. "Hi, Trisha. Yes, that was quite a task. But, I'm all done and it was a great workout."

"Thank you so much. My lazy husband couldn't have moved one of those stupid boxes. Come here. Follow me inside." I gladly followed her plump little ass and swaying hips into the house and down the hallway into their spacious kitchen. I was pleased to accept an ice cold beer from the fridge and sat down at their bar.

We chatted a little bit and then she asked, "Hey, do you need to run off right away?"

"Well, no, why, Trisha?"


" Trisha. please call me BJ. No one that really knows me calls me Brian."

"BJ? I'll bet that nickname was popular with the girls, huh?"

"Um, uh, yes," I said awkwardly laughing.

"Anyway BJ, I just got a call from a place downtown and a new chair I ordered is in. Could you go with me in my car to pick it up and bring it back? I'll pay you extra."

"Oh, you don't have to pay me extra. I'd be glad to help."

"That is very sweet. Here, follow me. Let's get you a clean, dry shirt before we go" We went up the stairs and down a long hallway and into their bedroom. I was nervous. She went into a large walk-in closet and came out with a t-shirt. "Here, take your shirt off," she said as she walked away into the bathroom.



I pulled off my wet t-shirt just as she came back with a small bath towel. She walked right up to me and started wiping the sweat off my bare chest. "What the fuck? I am standing, without a shirt on, in the Mayor's bedroom, and his wife is wiping the sweat off my chest with a towel," I thought to myself.

"Wow, no wonder you handled those boxes so well. You're in amazing shape," she commented.

"Thank you. I try," I said.

As soon as she declared me clean enough for the new shirt, I put it on and we headed back downstairs. I was still lost in the feeling that this hot MILF had just wiped me down. Fortunately, during that whole episode, my cock didn't bulge out too far.

She grabbed a red plastic cup off the counter, tossed me the keys and said, "Do you mind driving? I hate driving our SUV. It is too fucking big. Not to mention, if you drive I can have a cocktail."

"Sure," I gladly accepted! If only my friends could see me now. Fresh off being half-naked in the Mayor's bedroom with his hot wife, I was driving her around town in her bad ass SUV while she, illegally, sipped on a margarita.

We chatted about school and my upcoming job and then she asked me, "So, BJ, what do people around town think of me?"

"Oh, I don't know. I haven't been around much so, I've never really heard anyone say anything," I said dodging the fact that I knew most women couldn't stand her.

"Okay. Fair enough. What do guys your age think of me," she asked, increasing my anxiety?

"Um, well. We think you're pretty cool. I mean, you're the Mayor's wife."

"I don't want to only be the Mayor's wife."

"Oh yeah, I didn't mean it like that. I mean, you help a lot of people and do a lot of great things, too," I said in fine recovery.

There was silence for a little while and I noticed she was kind of studying me quietly. "Do guys think I'm hot?"



Fortunately, I did not jerk the car off the road and crash it. My heart was beating fast enough that I certainly could have. "Um, well, I guess I never really thought about it, but yes, I think people think you're a good looking woman."

"What about you? Do you think I'm hot?"

The sweat returned to my head as bad as it poured out when I was in the hot attic. I couldn't figure out if this was some kind of trap conversation I'd gotten myself into or what. I was panicked and trying desperately not to show it. Finally, before I passed out from anxiety, I heard my voice, almost like an out of body experience blurt out, "Hell yes! I think you're very hot."

"Wow. That is really nice to hear coming from such a handsome, well-built, young man like you. I do my best to stay in shape." She turned her head to glance at herself in the mirror on the sun visor and said, "Turn right at the next street. The place is right there."

We arrived at the furniture place without any further conversation. We loaded up the chair hopped back in the Escalade and headed back to her house. The conversation on the way home was about the chair and why she loved this particular antique. I asked as many questions as I could think of in hopes to stay away from more conversation like on the way to the store and I was thankfully successful.

I carried the chair into her living room and placed it in the spot she'd carefully thought through. She offered me another beer, so I took my place at the bar on a stool and chatted with her; trying hard not to stare into her ample cleavage. I flexed my neck to both sides, a habit I have when my neck is stiff or sore, and that prompted her to ask, "Are you sore from all the work I had you do?"

"Oh, just a little stiffness in my neck," I said.

Before I knew it, she had come around the counter and was standing behind me and started massaging my neck and shoulders. As she rubbed my back, she would lean in and brush her breasts against my back. I was sure she was doing it on purpose, but I wasn't about to move. After about 5 minutes, and a hard on beginning to push out my shorts, she stopped, came around the counter and said, "Did that help?"



"Yes, yes. That felt great," I said as I flexed my neck some more. I sipped my beer, glanced up and noticed her nipples were popping out of her shirt. Clearly she enjoyed giving me the massage as much as I enjoyed getting it.

"Listen, I'll bet you're hungry. Why don't you stay for dinner?"

"Oh wow, dinner with the Mayor and his wife. That would be fun, but my parents are catching a red eye tonight and I said I'd grab dinner with them and drop them off at the airport."