My girlfriend, Anna, a full time escort, helped me find my way out of a financial hole by taking me on as a ‘duo’ partner and helped me back to solvency. It was a shock to me that I so naturally fell into it. In fact, I never really had much of a sense of my sexuality until that first time when Anna and I worked for Tom, who went on and on about how beautiful I was.
It wasn’t that I didn’t know I was pretty but I didn’t realize how sexually attractive I was to men. It got me to see what was one of my hidden super powers. Hidden even from me. I had also never had sex with a complete stranger. That wasn’t the only first…there were plenty that day, hehe. But the point was that something was awoken in me that lay dormant for all of my adult life until that night.
This was something I would never, never have done if it weren’t a necessity but at least it was a good time to do it because I was unattached and not working a regular job. When Anna handed me the thousand in cash at the end of the evening I was sure I’d be doing more, at least for the immediate future.
Anna called me two days after seeing Tom in the hotel and offered me another job with her at the same hotel, different guy. “He’s sort of a fetish freak who thinks that having fun always means having two girls. I’ll warn you he likes girl on girl action so I always plan on putting it in at his direction. Are you alright with that?”
“Are you a good kisser?” I joked.
“Very good, let’s hope you don’t like it too much.” (Insert mutual laughter here) “one more issue will be costumes. He likes role play and the girls to be dressed in character. He picks the role and we do the rest.”
“What did he pick?” I asked.
“The farmer’s daughters. It’s a classic men’s fantasy. Very tight jean shorts, plaid shirts tied at the midriff, bare feet and maybe straw hats. Definitely either ponytails or pigtails.
“I think I can handle that. Why don’t we skip the hats and concentrate on the hair?”
We didn’t have long to prepare but, then again, the look was minimal anyway. He wanted us later that night so basically we pulled the pieces from our closets and she picked me up at eight. “His name is Dennis, he’s forty-eight, he’s sweet but he likes to be immersed in the moment and the spontaneity of the sex. He’ll role play from the moment we walk in the door so he’s looking forward to having his farmer’s daughters. I’ll be Annie and you’ll be?” “Daisy sounds good to me,” I said.
Later that night..:
“Who is it?” Dennis said through the door when we got to the penthouse.
“It’s Annie. You met me at my daddy’s farm. I know he run you off but I just had to see you one more time ’cause you said I was pretty.”
He opened the door and we took off the trench coats we wore to get through the hotel lobby. “Oh ya, I remember you Annie but who’s your lovely friend here?”
“This is Daisy, she’s from down the road and she wanted to take a trip to the city. I told her you was a swell guy who said I was pretty.”
We played it up as very sexy but clueless, inexperienced farm girls. We circled around him while he fondled our asses and we brushed against him with our tits. “Oh, Dennis! Daddy won’t like that,” said Anna and we both giggled.
We went way over the top with the stereotype but he ate it up. “Well, Daisy, I think you’re real pretty too.” I giggled some more. “You think your daddy would mind if I kissed you?”
“He might mind but I wouldn’t,” and he French kissed me with both hands cradling my rear.
“Oh,” I purred, “that makes me all tingly.”
“I’ve got more where that came from,” replied his dirty little mind.
“Hear that, Annie? He’s got more,” I said, getting into the nutty character.
He took Anna and repeated the kiss. She pretended to be surprised. “Dennis!!! What are you doing? You know my daddy won’t like that! Even though I kinda like it…”
“Annie, have you ever been, shall we say, serviced by a man?”
“Well, one time in my senior year of high school we went to the gas station and Jimmy asked my daddy, but sort of looking at me, if he could fill her up. Daddy got out of the car and chased him all the way down the street and that ended that. I never figured out what it was all about.”
“Take off your shorts, Annie, sit on the barstool and I’ll show you something I think you’re gonna like.”
“Oh, I don’t know,” she teased, crossing her legs.
He smiled, walked up to her, uncrossed her legs and helped remove her shorts. Sitting her back down he went to his knees and pleasured her. Remembering her earlier instruction I went over to her and kissed her passionately. He looked up and asked me to open her shirt and suck her nipples which I did. We hadn’t really gone there last time but I was liking it. She was soft and fabulously beautiful. I could see why she was so successful at this.
“Daisy, sit and spread those sexy legs and I’ll make that farm pussy hum.” Off came the shorts and down he went. “Mmmmm, Mr. Dennis. That feels better than a Friday night hayride.” He asked Anna if she’d like to have a taste and then she ate my pussy as well. “Mmmmm, uhhh.”
“Well now, I gave you two a good time. How about you girls return the favor.”
“What do you want us to do?” said an eager Anna.
“I’d like you and Daisy to suck my cock. Put it in your mouth and pretend it’s dessert.” We obliged him with a monster head job, licking in tandem and occasionally stopping to kiss each other which he loved. When he’d had as much as he could without shortening our playtime, he said, “Okay, now I’d like you pretty fillies to face the bar and stick those fine asses out so I can give you a present.”
He fucked us in turn, never staying in one pussy too long. While he did so he reached up and removed our shirts, then grabbed on to our tits for momentum. “You sweethearts have the tightest pussies this side of the Mississippi. Know what though? If you’ve grown up on the farm like I did you know what a hogtie is. I have some rope and I was wondering which of you would like to have some fun and let me hogtie and fuck you?”
“I’d do it,” Anna said, running interference for her newbie friend. “That would be great. Let’s go in the bedroom and we’ll do it!” he said as chipper as if he’d suggested we go get ice cream. I had gotten a taste of bondage at the last job but she jumped in. Maybe she was taking one for the team…or maybe she really enjoyed it.
Dennis hogtied her face down on the bed, her arms tied back and her ankles cinched back to that with her thighs open. Once secured, he rammed his cock in her, starting a blistering fuck that seemed to go on forever.
The intensity with which he fucked her both scared me and excited me. I mostly watched, unable to turn away. The whole bed shook as he laid it to her helpless pussy. “Oh, shit”, I said under my breath.
“Would you like some of this, Daisy?” he asked.
“Yes,” popped out before I could edit my thought. “But without the rope,” I added, “do me doggie but fuck me hard.” I don’t know where this bravado was coming from but I’d suddenly taken charge of the situation.
“I like that, Daisy.” I had briefly lost my Daisy persona with my instructions..
“Oh, Dennis,” I said, trying to recapture my character, “I get real intense like that when I want something.”
“And you want me to fuck you?”
“Oh fuck, yes sir,” I said ultra sexy, “I wanna feel that nice cock of yours slamming my rear just like a fence gate on a windy day.”
The last vision drove him nuts and he took hold of my hips, flipped me over on the bed and began to fuck me like a maniac, hesitating only to get a handful of my hair or slap my ass. Anna, still hog-tied, watched with helpless amazement at the girl she thought she knew. But, hey, even I didn’t know I had this inside me.
Then there was a knock at the door and Dennis asked “Who is it?”
“Fred, from housekeeping with your extra pillows.”
“C’mon in, Fred,” said Dennis, suddenly making me self-conscious of my current position. Really? He was inviting this hotel employee in while we’re having sex?
“In here, Fred. Just put them over there,” he gestured towards the dresser. Fred’s eyes widened considerably when he saw the debauchery in progress. He started to leave when Dennis asked him if he’d like to stay and watch. “Just pull up a chair over there, I think you might enjoy this. Better yet, drop your trousers and help me. I’ve got more pussy than I can handle.”
Fred was like a deer in the headlights. Likely he couldn’t comprehend this course of events in his otherwise banal day. Staring at Anna, tied up and easily accessible, he instinctively went for his belt and stood in front of her and pulled down his pants and underwear, revealing a partially erect dick. Anna didn’t protest. He went ahead and pushed it in her mouth and she sucked him while he moved it back and forth. In the midst of his excitement he unintentionally gagged her a couple of times. In the meantime, Dennis continued pounding away at me.
“How’s that working for you, Fred? Isn’t she something?” Dennis bragged. All Fred could do is smile and nod. It was surely the best tip he was ever going to get. Dennis liked to talk. “These are my little farmer’s daughters. That’s Annie sucking your cock and I’m riding Daisy. Girls, if you haven’t figured out by now, this is Fred. He takes care of things for me. Daisy, you do have some serious tight pussy. Oh fuck. Uhhhhh.”
I looked over just as Fred rotated the bound Anna from stem to stern and, after lubing up her pussy with his tongue, dropped his cock into her cunt like a pile driver. He went at her nonstop and didn’t pull out until it was time to release his cum. I looked back and realized both of us were watching Fred ravage her. It was turning me on and I know it was turning Dennis on because he ratcheted up the energy. I reached back and massaged myself to climax and two seconds later Dennis shot his cum up my back and a second later Fred, with audible delight, pulled out, spun Anna around and splashed his wad all over her face. OMG.
Suddenly it was all over. Dennis was untying Anna and I was cleaning up in the bathroom. Not a word was spoken as Fred slipped out of the penthouse and we all got dressed and back out to the living room. Then…
“Well, Anna, Daisy, I want to thank you for driving into town and spreading your beautiful legs for a city slicker.” He made his thank you speech with us on either side of him. “As a token of my appreciation I wanted to give you a little parting gift,” and he handed Anna a wad of cash that we ended up counting in the hallway before we left.
As we went out the door, Dennis said, “And Anna, next time please, I beg of you, bring Daisy here along with you. She’s a sweet piece of prime real-estate.” And he slapped our rears as we left.
“Well, you’re a big hit,” said Anna, as she counted the money. Passing us in the hallway was Fred who took one long farewell look at our asses as we got on to the elevator. As the door closed Anna pulled the crotch of her short shorts aside and flashed her pussy at Fred. “Remember me,” she said in her sexy voice as the door closed. We laughed all the way down to the lobby, slipping on our coats to cover our farmer outfits.