The Awakening of Angie Ch. 05

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‘Three Times A Lady' by Angie.
4.4k words
4.79
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5

Part 5 of the 9 part series

Updated 06/11/2023
Created 11/25/2021
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Over a period of time working the floor at The Pleasure Palace strip club I had gotten many, many offers for sex OTC, meaning 'outside the club'. I was always wary of these offers even though we were usually talking substantial sums because I could get fired from the club if found out and you were vulnerable to who knows what out alone. I never went for it. Still I felt like I was steering into the unknown and my senses were on high alert.

One day three guys came in late in the afternoon and sat next to the middle of the runway and the first time I danced near them they filled my G-string with cash and asked me to stop by when I was done. They never took their eyes off me and when the song ended I walked over and sat at the table. There were introductions all around and it turned out they were all roommates, I'm guessing around 25 to 35.

They handed out copious compliments that I was by far the hottest girl on the day shift or any shift and I was, in fact, the reason they had come in this particular day. While they were talking I used a move I'd learned from one of the other dancers, putting my hands on two of the guy's thighs next to me and running my fingers back and forth, encouraging one of them to take me private.

Turns out they needed no encouragement.

"We came here today", said Sam, the oldest one, "because we talked and I know this is a little weird but we all agreed we want you to come to our house and would be willing to pay you well for your time."

Now I know how this sounded; three men obviously wanting to have a complete sex romp with me in a private home. Hmmmm. On the surface it screamed absolutely 'no' but Sam put it so charmingly and up front that I listened. One of the things I had wanted to try anyway was multiple partners and this certainly fit the bill.

"Jazmine, we want you to take on all three of us together for two hours and we want liberal privileges as to what we want to do but if at any time you get uncomfortable with anything we will stop whatever it is. We're going to want to role play a bit, or maybe you handle two of us while one watches or however it naturally flows. Oh, and this is important. I need to know you're comfortable with anal too. We will have outfits for you to wear and for that we'll pay you fifteen hundred for the two hours."

I was stunned at what this might entail and more than a little worried but, surprising myself, right away I questioned the amount. "Considering what you're asking, fifteen hundred sounds low. Make it two thousand and I'll start to think about it." I put it at an amount I was sure would end the conversation.

But they were so excited that I might say 'yes' that one look between them was enough to get a go ahead on my price demand. "Let me consider your offer for the rest of my shift today and I'll give you an answer but let me ask you, why me? You could find a much cheaper escort to do all the things you want."

"First of all, other than a lap dance none of us has ever paid for sex or do we have sex with anyone other than our girlfriends. We didn't even come up with this idea until over dinner last night when we were talking about the sexiest and most beautiful women we've ever seen. That's when Cory (pointing to one of the other two guys) suggested you and then, comparing notes we realized that we all felt the same way. The times we've been here none of us can take our eyes off of you, but we decided we wanted more of an experience than a VIP dance. We're not just asking anybody, we're asking you. We want something we'll never forget."

I took a cell number from Sam and told him I'd text an answer by ten that evening. They all thanked me and walked out. On the way Cory slipped a fifty into my G-string.

The rest of the day I ran it through my head, at times thinking it was crazy but other times how it turned me on that I was considered that desirable. In practical terms I'd be fucking three guys and I wanted to try it. Maybe I'd be overwhelmed and unable to handle it or maybe I'd love every minute of it. They were three pretty good looking guys who wanted to have me at any cost. I felt hotter than shit.

My husband, David, and I had dinner, talked about his job (he didn't want to talk about mine), what friends we might hang with on the weekend and other assorted minutiae. For the first time I could see that my full out adventure with sex and my home life were clearly at odds and the compartmentalization was getting emotionally harder to handle. I just craved being the object of lust and when I was home it felt like being on hold till my hunger could be satisfied again. Maybe there really was such a thing as nymphomania.

At about 9:30 I went upstairs to the bathroom and texted Sam: 'Yes, I'll do it but these are my terms. I want $3,000, has to be a weekday, no cameras, no anal.' I was a little skittish about the anal just because David and I had only done it once.

Sam immediately replied, 'Agreed to price, day and no cameras but must have anal. One more thing, Tim's girlfriend found out about this and wants to watch.'

I wasn't completely comfortable with the anal idea but this was about stepping out of my comfort zone. I decided I really needed this to happen now and it was all about risk. I couldn't seem to price myself out of reach so I texted back that I wanted half in advance by the Tuesday before (delivered to me at the club) and I agree to anal and everything stated, even Tim's girlfriend watching.'

'Agreed,' he quickly texted back. 'How about next Thursday at 1pm? We'll provide directions and we need your clothing sizes.'

I texted back my sizes and put my phone down. I started imagining what this would be like and before I had left the bathroom I'd masturbated to climax. Just then David passed by the closed bathroom door asking if I'd "fallen in."

i had upped the stakes. i was exchanging money for sex. There was no other way to put it. i was now officially a prostitute, and a high priced one at that. i was out of my head excited.

I had a week to wait and all I did was anticipate going there and getting my brains fucked out of my head by some very horny guys. I wondered who wanted this more, them or me? I was turned on by the thought of a foursome. I was hot to be their dress up doll and make their fantasies come true. I imagined them jerking off just thinking of doing me. It was strangely empowering.

When Thursday came around I was nothing but raw nerves but I also knew by now that once I was there I'd lose myself in all of it. I already told the strip club I'd be off that day and I left for their home at 11:45am per the directions Sam texted me. Sam offered drinks beforehand if I came prior to the agreed upon start time.

Once I got to the neighborhood I realized these guys had money to burn. The house was huge and in a very exclusive part of the city. Maybe I should have said five thousand?

Sam answered the door and with a hug invited me into their home where I said hello to Cory, Tim and his girlfriend, Tina. Tina was a stunning blonde with a killer athletic hardbody, beautiful legs and a great personality who somehow was down with what they were doing. There had to be some kinky there for her to be an interested voyeur especially when it involved me fucking her boyfriend. One look at her and I suddenly wondered about the idea of sex with another woman.

By the time I had downed the second martini I was pretty loose and ready to take on the boys. Sam led me to the bedroom and showed me the outfits they had laid out on the bed, carefully chosen based on their collective fantasies. "We're leaving it to you which outfit you choose but we reserve the right to direct the action each time you come out in a new one. You can do any hair and makeup you wish in the ensuite. Personally, I'm partial to you starting with the schoolgirl look."

He patted me on the ass and went back out to the living room. I slipped out of my dress and into the white blouse, short pleated plaid skirt, and white tennis shoes that comprised the schoolgirl look, even doing my hair in pigtails. I looked so incredibly fucking hot. Also, for each look there was a corresponding name that I would use and it and the general setup were written out and placed next to the costume. Not surprisingly this one said "Britney".

SCHOOLGIRL

"Hi, guys," I said naively when I walked out, "the principal told me I should see a couple of the players because you needed inspiration for the big game tomorrow night." I was totally into the role play. "How can I help?"

"Britney, why don't you come over here and sit on my lap and we'll explain what would help the team," Sam said. I walked over and sat on his lap and felt his erection already. "The guys on the team need some help getting it 'up' for the game (I giggled) and wondered what you could do", he said as he unbuttoned my blouse and fondled my breasts. At the same time, Cory came over and pulled out his hard dick, asking me to suck it for good luck. I took him in my mouth and he throat-fucked me while Sam felt me up, his hand traveling down to my panties. Sam carefully removed my top and already pulled down my bra to cradle my tits.

Tim hadn't made a move yet and I wondered if that was because he was self conscious with his girlfriend being there.

Between the martinis and the role play I was already wet and waiting for Sam and I didn't have to wait long. While I continued to suck off Cory, Sam stood me up, dropped his pants, lifted up my little plaid skirt, pulled down my panties and made his way into my pussy from behind. Probably realizing he was going to have to pace himself for 2 hours he took it nice and easy, each time pushing it deep and holding it there. He would pull out sometimes and run the head of his cock up and down my crack or slap it on my ass. Tim still hadn't moved but now I noticed out of my peripheral that Tina was playing with herself while she watched this.

As soon as Tim saw what Tina was doing it was like a green light and he stood up, walked over and pulled out his cock and now I was sucking both of them while Sam continued from behind. "I think you're really showing school spirit," he said. Meanwhile, looking up from my double blowjob I could see Tina really going at her snatch and watching her got me even hotter.

Then the three of them began to rotate around to fuck my pussy or shift their cocks to my mouth. I underestimated Tim's initial reluctance because when it was his turn to enter me he put on quite a show. When the other two saw how he was going at it they each got hold of one of my pigtails and held me down bent over the back of the couch while Tim blasted me so hard it literally took the wind out of me.

Saving himself for more later he pulled out and sat back down in the chair, still stroking his cock. By now Tina had already come once or twice. I took this as the sign to change clothes and went back to the bedroom.

So that was round one and, truthfully, I was enjoying every minute of it.

"Which outfit?," Sam called to the bedroom.

"Beauty pageant," I called back. Then Sam poked his head in and asked if it would be alright to add Tina into the mix. "She's getting crazy turned on and begging me." "Sure," I said without hesitation, "now it's thirty five hundred".

"Agreed"

BEAUTY PAGEANT CONTESTANT

I walked out in a very small yellow bikini, pink 7 inch patent leather heels and a white sash reading 'Miss Fuckable' on the front and 'Amber' just after that. I stood in the classic pageant pose in front of the boys sitting on chairs in a row like judges except all of them had stripped down completely. Well, Tina kept an open blouse, bra and panties on. Across from them was an overstuffed chaise lounge chair which is where I figured I'd end up eventually, but first...

"For the first round, Amber," said Sam, "we just want you to pose for the judges (now including Tina). You need to impress us with how fuckable you look."

Here I relied on my recently acquired stripper skills and backside up I bent over and put my pussy right in his face and ran my hands across my thighs. Then I moved down the line of chairs, ending up with Tina who under breath said, "Oh my fucking lo..." and trailed off. If Tina was going to officially go from spectator to participant my new goal was to get her to want to fuck me too. I wouldn't have far to go.

"That's very persuasive, Amber," said Sam (All of the roommates were sitting with dick in hand and Tina had her hand down her panties). "For the second round we have the Q&A and you will take a question from each of us and take as long and as detailed a time as you feel necessary." I took that to mean as much dirty talk as would make them get off. I sat on the end of the chaise to field their questions.

"Amber," said Cory, "I love shower sex, the feeling of the water hitting me and seeing my girl all wet gets me naturally horny. How would you handle me in the shower?"

"Well, Cory, I love shower sex too. I'd let the water from the shower head hit my pussy directly, getting me in the mood. Then I'd go down on you, licking your balls and up and down your shaft while you watch the water drop from my tits. Then I'd turn around, put my hands on the far shower wall and with water running down my back I'd beg you to fuck me and fuck me good until I'd turn back around, squat and take your cum all over my face. And what better or cleaner way to take a facial than in the shower? Good for the skin. Sort of a win, win!"

Everyone laughed but Cory who was seriously stroking his cock through the whole story and was seriously intent on getting at me.

Sam was next: "Amber, what do you think would turn me on the most and how would you do it?"

Of course, it hit me right away. "I think I have what you want but to begin with I'd make you earn it by making you eat my sweet pussy until I came two or three times. You would be instructed to flick my clit and tongue fuck me until I told you to stop. And then I'd ask, 'have you been a good boy?' And, of course, you would say 'yes' (everybody laughed again) and then I'd give you your treat. I'd turn around, lower my bikini bottom, spreading my butt cheeks until you were face to face with my pretty little pink asshole and then I'd say, 'rim me delicately with your tongue and then fuck me in the ass and cum while you're at it." I couldn't believe how easily the words came out of my mouth.

Well, I thought he was going to jump me right then and there. I don't think he even realized how hard he was jerking off. I placed a single finger on the head of his dick and said, "Easy does it now. You'll get your chance". I thought he was going to explode. I was loving this so much it was scaring me.

Then Tim said, "Amber, what could you do that would make me so insane I'd want to nail your beautiful ass?"

I looked him in the eyes, locked in, just him and I for about 2 minutes or so and then I started playing with my pussy, never taking my eyes off him.

"Before I did anything else I'd start by eating out your girlfriend's pussy right in front of you, only stopping to tongue those delicious nipples that I can see through her shirt." Tina, without a thought, pulled off everything. She was, apparently, all in.

It was quite apparent that Tina had been on the minds of the other guys. All eyes were on her when she got completely naked. They'd thought about this before.

"While you watch I'm going to fuck your girlfriend and if you're a good boy I'll let you fuck both of us, but you have to be a good boy and not touch yourself the entire time I'm fucking Tina. Okay?"

Tim was petrified/excited but so caught up in what I said that he stopped playing with himself. I could even make a man want it so bad he'd stop touching himself. Then the Q&A was over. I suitably messed with their heads in ways they didn't see coming but couldn't resist. It's what they were paying me for.

"And that concludes round two," said Sam, "The next and final challenge is the 'demonstration' round. "You've showed us the goods and told us what you would do to us and now we need a personal demonstration as to why you should be crowned 'Miss Fuckable'."

First I got Cory to remove my bikini and pageant sash and then lying on the chaise with my legs spread wide I held out my hand to Tina and she came to me and started licking and sucking every inch of my body. I let myself be dessert and Tina dove in head first and when our tongues connected all you could hear were the guys jerking off.

Then I stood up and motioned Cory to lie back on the chaise and I mounted his cock as Tina got between us with her tongue on my clit and played with my nipples. I asked Tim to bring his cock over and I took him in my mouth and swallowed it up to the hilt. I knew what would happen next and it did. Sam came behind us and I felt him lube my anus and in a second he had entered me backdoor. I was taking double penetration and effectively fucking all four of them at once. It was an unbelievable feeling and thanks to Tina's agile tongue I was orgasming like mad. The simultaneous stimulation of all the parts of my body was overwhelming.

This went on for awhile, how long I don't know, until Tim couldn't hold it anymore and shot his load down my throat. Cum dripped from my lips, over my chin onto Cory's chest as he kept my pussy occupied. He and Sam were working me over like this would be the last fuck of their lives. The next move was Tina's. I thought she'd go sit with Tim while the 3 of us finished business but instead she straddled Cory's face and with my cum soaked lips I sucked her gorgeous little tits. Cory, still fucking me with a vengeance, lit into her nicely positioned pussy. I was concerned about Tim. He had to sit there as his roomie ate his girlfriend but Tim calmly came over and deeply kissed Tina while she was being serviced by the two of us.

Sam finally withdrew from me, walked around and stuck his cock in Tina's mouth and she and I tag teamed his member as he groaned with delight. "Suck me good, girls." Pulling his dick from her mouth he picked Tina up and leaned her over the chaise, going K-9 on her while Tim still watched. Cory then got up, moved me in the same position opposite to Tina and stuck me from behind while Tina and I, facing one another, started passionately kissing. Then like we were at a dance, the boys changed partners and I had Sam in me.

Then Tim reappeared, apparently recharged, and slipped his dick between Tina and I so we went at it. He was hard again and ready for more. Our tongues went in unison across his shaft, occasionally pausing to kiss one another.

It was clear Cory had more than a passing fancy for Tina because now he was hammering her pussy, forcing all sorts of sounds to come out of her. Like at a dance, Tim cut in and pounded his girlfriend like he was defending his turf. She was squealing with every thrust.

And on a dime, Sam put a hold on everything saying, "Alright, let's let Jazmine make the final change of the afternoon. It's almost 3."

I went into the bedroom and the final outfit was a high school teacher's very traditional white blouse, mid-calf skirt, matching blazer, glasses and there were instructions for wearing my hair pinned up. My role name was Miss Adams. The name did not seem made up so I thought one of the guys must have had a boner for a Miss Adams.

HIGH SCHOOL TEACHER

I came into the room with a surprised look on my face. Everyone was dressed. "What are you kids doing in the teacher's lounge after hours?" "It was Sam's birthday," said Cory, "and there was only one thing he wanted so we thought we'd help out, Miss Adams."

"What in the world would you need out of the teacher's lounge?," I asked teasingly.

"You," said Cory.

"Oh...," I said very sexily. "Well, if he wants me you guys are going to have to make me", I said smiling at Sam, "I don't do that kind of thing!"

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