Cindy's Bikini - College Age Hooker

Shawn had to have known who he was. How he could have arranged this I don't know. But his 'daughter of a co-worker' comment was way too coincidental. Whether on purpose or not, I was faced with fucking my dad's boss. I decided to take the initiative. Letting him take the lead could only result in me doing more debasing things with him. I wanted him to fuck me as soon as possible, which didn't come out like I wanted it to in my head. Without being prompted, I stood in front of my dad's boss and pulled down my thong, exposing my pussy to him.

"I like the initiative on this one. So she is just a regular girl in town huh? Wants to fuck some strangers without anyone knowing and make some money doing it?"

I kept eye contact with him and took off my bra. I was remembering last time I saw him I was visiting my dad at the office. He remarked how I was growing into a fine young woman. Little did we both know then that he would end up balls deep in that woman a few months later.

I took him by the hand and brought him to the bed and laid him down. His cock was pointing straight up. I stood on the bed directly above him. My naked body was now in full view for him. I slowly lowered myself and positioned his dick into my pussy. The man that once threaten to fire my dad unless he cut his Christmas vacation short was now fucking me. I put my hands above my head, arched my back to stick my chest out, and started riding up and down on the penis inside me.

"Is there any way I could find out who this slut is? She is the best fuck I've had in months. I would love to know."

As I was humping his cock in anticipation of getting creampied, I realized how vulnerable a position I was in. Shawn could easily confess my real name and I would now have to secure the silence of my dad's boss. The idea of him fucking me while on a conference call with my dad or sharing me with all of his coworkers gave me a sinking feeling. But Shawn didn't do that.

"Can't do that sir. Just enjoy what you have now on top of you."

For a moment I was thankful of Shawn until the truth that I was fucking this guy in the first place due to Shawn put any thanks I had for him out of my head. My dad's boss started exploring my body with his hands. I was hiding nothing from him but my face. As his hands squeezed my bare ass, I remembered dad mentioning his boss would be coming over for dinner in 2 weeks. For that whole meal I won't be able to think about anything but what his dick felt like when it came inside me, which it did while I was having that weird thought.

"Fucking hell yes. Take all of that cum into your pussy you slut," he yelled while inseminating me. I will also be thinking about that as well.

He pushed me off of him, got dressed and left. 'See you in two weeks,' I thought to myself. 'I hope you enjoy my mom's baked potatoes as much as you liked fondling mine while fucking me.' After the door closed I looked at Shawn to see if his reaction would give me a clue if bringing my dad's boss to fuck me was on purpose or not.

"I really liked the initiative you showed with that old man. I think we have found your kink." He said nothing else to me that made me understand his motives.

Figuring staying would only yield more insults, I got dressed and left the hotel room. Pussy filled and another stranger sexually satisfied. But he wasn't a stranger though.

I laid in bed that night, with my pussy likely still holding the sperm of my dad's boss, thinking. Eventually I will reach the end of this roller coaster of sexual favors. I'll move on from this town and my many sexual partners. I'll find a new boyfriend and eventually get married, maybe have kids with him. Will I eventually tell him about this? Would any man stay with a girl that fucked as many guys as I have in such a short amount of time?

Lingering on that question over the next couple of days, it was time for me to put out again in the hotel room. This time I was told ahead of time what to expect. A party of 8 guys would be joining us. They are throwing a bachelor party for their friend who will be getting married in a couple of days. They wanted to give him one more night of fun. Fun meaning cheating on their soon to be wife by having unprotected sex with a hooker. The groom isn't aware of this and my job is to convince him to fuck me as his friends expect him to offer up resistance. No sex means no money and I'll be that much further away from completing this agreement with Shawn.

I wore something different than my usual underwear. I wore a button-down shirt and a skirt along with a floral bra and a white pair of panties. I was hidden in the bathroom when the crowd of guys came in, led in by Shawn.

"Alright, let's have the groom sit here on the bed."

The groom started to realize what this was and protest.

"Guys, I told you no strippers. I promised Nancy we wouldn't have any strippers."

"We didn't get you a stripper," one of the men said to the still confused groom.

I took that as a cue to start. I walked in and immediately made eye contact with the groom. I walked towards him slowly feeling up my body with my hands. I stood right in front of him and continued to feel up my own body. I stopped suddenly then grabbed his hands and put them on my breast over my shirt.

That finally woke him up and he pulled his hands away.

"Woah, guys. I am not doing this."

I put my finger over his mouth and got real close to his face with my lips. I needed this guy to stay if I was going to make tonight not be a total waste. I could easily see Shawn making up some bullshit about how because I lost this client I need to fuck ten more strangers. No. This groom was going to cum inside my pussy tonight.

I backed away and reached under my skirt and pulled my panties down and handed them to him. He didn't object or say anything at all at this point. I turned around and placed my ass on his lap while bending over. I started rubbing myself up and down on his lap, with my skirt lifting up more and more until my whole ass was on display and likely some more as well if he was looking close enough. I turned back around to face him and sat on his lap, with my tits a few inches from his face. I humped him a few times getting my tits closer and closer to his face. Finally I looked at him and started unbuttoning my shirt.

After getting half the buttons undone, my bra could start to be seen. I reached behind my back and undid my bra. Using a trick I learned a couple of years ago I pulled my bra out of my shirt, putting my cleavage on display for the groom and his friends. I grabbed his hand again and this time placed them on my butt over my skirt. He started to talk again, but I covered his mouth with my hand. I gave my hand a kiss, then gave his cheek a lick. He kept quiet when I lifted my hand away. I then lifted my skirt up, resulting in his hands resting on my naked ass where they stayed for a while.

I started undoing more buttons while keeping my shirt together as to not reveal my naked tits, yet. Once they were fully undone, I started up humping him again. Each hump risked my tits coming free from my shirt. When I knew they were about to spring loose, I grabbed his hands from my butt and placed them on my now fully exposed tits. The group of guys who had been oddly quiet now gave a cheer. I kept my hands on top of his to prevent his from moving them. I let him enjoy the feeling for a while before I got back up and fully lost my shirt. I was now standing in front of 8 strangers fully topless and a short skirt being the only thing keeping my pussy hidden.

I turned around, spread my legs a couple of feet apart and slowly bent over. When I was fully bent, the bottom of my skirt was barely keeping my pussy hidden. That was until I flipped it up, showing off my babymaker to everyone in the room. Holding that position until the cheers died down I removed the skirt fully. The groom, I think finally relaxing, clapped his hands.

"Okay, okay. That was awesome. Thanks guys. And thank you miss. That was very erotic. But I think it's time we got going."

The groom started to get up but a friend pushed him back down on his chair.

"We told you, she isn't a stripper."

Before he could try and understand what was going to happen I sat back down on him, facing away. I grabbed his hands again, and after a quick feel of my breast, I led them down to my pussy. I directed a couple of fingers to start rubbing me up and down my vaginal lips.

Again, he started to object, "Woah! I am not cheating on Nancy tonight."

I interrupted him with a large moan and actually risked speaking out loud.

"Oh god your hands feel amazing. I really need your dick in me!"

I quickly got off him, licked his fingers that had just been fingering me, then pushed him off the chair onto the bed.

I jumped on him and started undoing his pants. He continued to speak objections but didn't actually try and physically hinder me.

"Guys, I can't do this to Nancy. We've had some fun, let's call it here and never speak of what happen, okay?"

His friends didn't speak up, instead letting me continue getting his pants off. I managed to get his fully erect cock out. I could start to blow it, but I had him right where I needed him, so I went for it. I got my hips over his cock and pushed down taking almost the entirety of his length at once.

"Ohhhh...." I let out a moan that wasn't for show. I wasn't enjoying the idea of fucking this soon to be groom but all of the sexual teasing I had done culminating in taking his cock all at once was a lot for me to endure

I started moving myself up and down on his cock. I wasn't out of the woods yet. He could still end things without cumming which the clients could argue means I didn't fulfill my end of the del. I grabbed his hands yet again and put them on my bouncing tits.

"Okay, fine. I'm fucking her. But I should really have a condom on at least right?"

The guys started rooting for him. "Fuck her good! Knock her up! Cum in her, get that slut pregnant!"

He looked at me very worried. "Are you telling me you aren't on birth control?"

I followed the directions Shawn gave me before he started selling my body and shook my head no.

"Oh shit, oh shit, oh shit, oh shit!" he yelled before cumming inside the 2nd to last women he would in life. I clapped for him as well. I had heard so many stories of douchebags fucking strippers right before their wedding. Inevitably someone will talk and the bride will find out. I felt like I just ruined a bride's life.

I dismounted the man who laid on the bed trying to understand the ramifications of what he had just done. It was tempting to try and tell him I was on birth control, but that would only risk what I've already done. I started to walk to the bathroom when someone grabbed my hand and pulled me in. I was then met with the hand's of several men groping me all over. Oh shit, I just did a sex show for 7 grown men who were now expecting their own attention. I wasn't ready for this. I looked over at Shawn, surely they didn't pay for this. He met my eyes, smiled, and nodded. That fucker had roped me into another orgy. How many of these guys were married? How many would leave here tonight thinking they impregnated me? I've had a lot of people fuck me lately, but tonight would add 8 to that list which was a lot. I've read forum post online about girls in the thirties stressing about having body counts that high. I was going to reach that in a single god damn night.

While I may had been in charge when I fucked the groom, that was no longer the case. These guys were going to treat me as a fuck toy, directing me however they wanted. All while Shawn watched of course. I quickly was back on the bed with my ass in the air and had a dick in my pussy within seconds. I expected someone to come around and put a dick in my mouth but that never happen. It seems all of these guys wanted to save their cum for my pussy. The latest guy finished, smacked my ass and then another took his place. I wasn't even able to see who was fucking me. My pussy was an ATM for their cum and they were lined up to deposit. Load after load was pumped into me. They didn't talk to me or engage with me. After each one would, as far as they knew, impregnate me, I would get an ass slap followed by another man looking to become a father. Over the next hour I counted 15 different ejaculations in me. Eventually some guys started leaving while I was still being fucked. Finally a man came inside me and I wasn't immediately fucked again. I was able to turn around and saw the 7th man putting his pants on and leaving.

I have had sex with grown men before, but never this many at once. My pussy was as sore and overflowing with cum. It wasn't an exaggeration to say it was gushing when I finally stopped getting fucked. The maid might get pregnant just touching these sheets. After recovering for a bit, I got up to clean myself up before heading home. I found the groom sitting by himself, still looking dazed. We both got fucked pretty good tonight. Again, I wanted to reassure him that despite his sperm resting in my womb currently (along with all of his friends), he wasn't going to get my ass knocked up. But Shawn was in the room so I gave him a reassuring stroke on the chin with my finger. I got cleaned up best I could, got dressed and left. Ten guys had now paid to fuck me and I just half way done.

I asked for a week off. I could almost swear I was leaking jizz for three days after that gang bang. Seven days later, feeling recovered, I suited up in the hotel room in my usual black underwear and mask and awaited the next customer. Shawn assured me this wouldn't be another orgy, but just one person. He wouldn't give me more details than that. When the door opened I heard the voice of a woman and a familiar face walked in. It was Gina, a friend I've had since freshmen year of high school. She was always a quiet girl and never had a lot of friends. Ashley and I considered her one of our closest friends though. Was she here to fuck me? Again, I highly doubted that it was by chance that Shawn brought her to me today. But how would Shawn know that my old friend wanted to have sex with a woman? I never knew she had any inclination to. She had limited interactions with boys. An odd date here and there but never a relationship.

I was now faced with having to have lesbian sex with yet another of my friends. The first and numerous being with Ashley. In this case, however, she seemed to be seeking it out. Shawn introduced her to me, despite me knowing her.

"This is Gina. Gina, this is the nameless friend you will be with tonight."

She shyly stuck her hand out and I shook it. Shawn calling me a 'nameless friend' further led me to believe he knew what he was doing.

"Gina is looking to express some feelings she had for a long time and never has been able to act on. She has an interest in girls but none of her friends share that interest."

She doesn't know Ashley that well then, I thought thinking to all the times Ashley put too much effort into our coerced lesbian sessions.

"She wanted a safe environment with no judgments. Also she wanted to be with a woman her age. Gina, as we talked about, your friend will be keeping her identify concealed and will not be talking. She can shake her head yes and no. You can ask her to do whatever you like. I will be leaving you guys to your privacy."

Shawn told Gina one last goodbye before exiting.

I was surprised by Shawn leaving as he indicated he would be watching all sessions. But there was no way a girl like Gina would allow something like this to be watched. I think Shawn was willing to forgo watching if it met me having lesbian sex with another friend.

Gina finally spoke up. "Wow, you are really good looking. Sorry if that sounds weird, I'm really nervous. I've never done anything like this before, with a woman or a man. I've been tempted to ask my friends if they would be willing to try this, but they are pretty inexperienced when it comes to sex stuff so they wouldn't go for it I'm sure." If only you knew how experienced your friends actually are I thought.

"Ummm, I have one weird thing. I asked Shawn and he said it would be okay. Please don't think I'm a pervert but I wanted to record this on my phone..."

I knew I couldn't argue this point. Shawn would use this to claim I didn't do everything the client asked. I was masked anyway so it wouldn't matter. It wasn't like Gina was going to post it online anyway. But knowing my friend would have a video of us having lesbian sex, and likely using that video for her own pleasure... was weird. I shook my head to indicate it was okay and she set up the phone on the night stand to face the bed.

"I don't know how to start. We could kiss, or I could take off my clothes since you are already in your underwear. We could wait and just sit. What do you think? Oh right, you can't talk. Or don't talk? I'm not sure."

Gina was rambling which was common for her when she got nervous about something. Usually this would be about a test but apparently it applied to having sex with me also. Gina was never going to take charge which I knew meant I was going to have to make the first move in fucking my old friend.

I walked up to the still rambling Gina and kissed her on the lips. She tasted like the raspberry lip gloss she often applies. She put her arms around me and we embraced for a minute, lightly kissing each other. I then stepped back and guided her hands over my body. First feeling my neck and shoulders. Running her hands along my sides and to my hips, and then letting them rest on my butt. Gina was heavily breathing already and very pink of the face. I looked her in the eyes and gave a reassuring nod. She loosened up a bit and enjoyed the feeling of my butt in her hands.

"You are very beautiful." She told me.

I gestured to her to indicate she was as well which she seemed to understand. I continued the tour of my body and brought her hands to my breast, although still contained in my bra. Again, Gina was very nervous but seemed to be enjoying herself and the feeling of my boobs.

While she was groping me I thought about what I should do next. Even though I was acting as a hooker paid to fuck, Gina was my friend and I wanted to help her. I went to her neck with my lips and started slowly kissing and nibbling on her ears. Based on her breathing this was very erotic for her and she ended up with her hands back on my butt. After a little while I turned around and pointed to my bra strap.

"Oh, of course," Gina said and easily unhooked it.

I grabbed the front of the bra, holding it in place. I turned around and let it fall off, revealing my breast to my long time female friend. She stood and stared before quickly looking away ashamed. I grabbed her head and positioned it back to looking at my breast. I wasn't going to let her feel any shame. She stared for a while before I got closer to her and guided her to feel my breast again, but without a bra in the way.

Gina was very delicate feeling them, which was nice. I let her slowly run her finger all around my nipples and feel the softness of my boobs. Gina has rather small A-cup breast herself so I don't think she has ever seen naked breast as large as mine in person, let along felt them up.

She suddenly stopped. "Oh, I guess I should be taking things off as well. I'm not as good looking as you are, sorry."

I responded to this self-put down by kissing her again.

"Thanks," she said after our lips separated. "I know I shouldn't talk about myself like that."

I didn't need for Gina to get fully naked for this. But I knew if I tried and stopped her from undressing she would take that to mean I didn't want to see her naked. Which was true, me not being a lesbian, but she would think it was for other reasons having to do with how she thought she looked. She took off her blue jeans and sweat shirt and stood in her plain bra and panties. She looked like she didn't know what to do next, so again I approached her and kissed her, but also feeling up her breast through her bra. I really wanted for her to feel desired. I went further and slowly reached back unhooked her bra. Once it came undone, she backed up, took it off and I saw my friend's naked breast for the first time ever.