Hiring Cindy

Chapter 3: The Trip

The second month started off where the first had left off. I had her wear more and more sexy outfits around the house. Transparent nightgowns, tiny dresses, extremely small shorts and shirts, and so on. And, of course, I had her spend more time naked, had her give me a blow job every day or two, and let her masturbate for me on the fourth day. One day I had her suck on my cock while we were watching TV. I had her strip and kneel on the carpet while I stayed sitting on the couch. Something about that really turned me on...

One night in bed after I allowed her to masturbate briefly, I pulled a dildo out of my nightstand and handed it to her. I instructed her to get up on her hands and knees and fuck herself with it. She gave me a quizzical look at first, but moved onto her hands and knees. She slowly slid it into her pussy, and started moving it in and out. After a while, she started to get more excited and began thrusting back to meet the dildo and moaning louder and louder until she came. I was incredibly turned on, and had her suck me off again.

On one Thursday night I asked her to tuck me in as usual. I had her strip naked, and I left my boxer shorts on while she straddled me. After a while I had her pull off my boxer shorts and suck on my cock with her ass sticking up in the air next to me. I started rubbing her ass again while she sucked, and started teasing her pussy. After a few minutes I actually started massaging her clit. She made a very excited noise around my cock and started to thrust against my hand. She was writhing around in a very excited animal way. I brought her to orgasm right about at the same time that I came in her mouth.

Finally, that Sunday morning, I had her come into my room naked and wake me up by sucking me off again. That was rapidly becoming my favorite routine... When I was hard, I pulled her up on top of me. My cock directly touched her pussy for the first time and I think we both felt something exciting. She slowly rubbed her pussy up and down on my shaft, getting very wet. After a minute I told her to slip me inside of her. She did, and I easily slid all the way in. We fucked like that until we both came and collapsed in the bed. That night I let her sleep in my bed with me and we fucked again in the middle of the night.

The rest of the month was wonderful. It was essentially more of the same. I fucked her whenever I felt like it, sometimes in bed, sometimes bent over the dinner table, sometimes in the pool. Wherever struck my fancy. I had her naked a lot of time around the house, and sometimes I noticed that she would be naked, or put on a see-through nightie or similar when she was just lounging around the house without me asking. I think she was starting to enjoy being naked, and I certainly was as well.

A couple incidents that I found particularly excited included one night that I made her kneel on the table and masturbate for me while I ate. When she got close to orgasm I told her to take some of the mashed potatoes and rub them on her tits. Then I told her to get down on all fours. She did, and then I had her rub them between her ass cheeks and finally on her pussy. It was very exciting seeing her behave so wildly, and I think it turned her on as well because she had quite a loud orgasm.

Another thing of note is that I had her make a special 'costume'. It was basically just a string that went around her waist and a square of cloth that hung in front covering her pussy (most of the time). For some reason that outfit really excited me and I was always touching her ass when she wore it.

We also spent a lot of time just doing normal things around the house. We were starting to get quite comfortable with each other, and maybe she was just playing the part, but I started to feel like actual romantic feelings were starting to develop between us.

Mid way through the third month I decided that we needed a vacation. I settled on Costa Rica, which she was very excited about. I packed her bag for her and didn't let her look inside, and we headed off to the airport. When we got there we checked into our hotel room, had dinner out, etc.

On the first morning we decided to head to a particularly isolated strip of beach we had read about. We had to drive along a lot of dirt roads and whatnot to get there, but when we did it was worth it. White sand, blue water, perfect weather, and not a soul around. We started walking down the beach, her wearing a bikini, but after a while I said that since no one was around I would like for her to give me her bikini. She was hesitant for a second, but then she took it off and handed it over. It was very erotic seeing her naked outside in such an amazing setting, but we were both reasonably sure that no one would see her.

After we had walked for a ways we put down our towel and swam for a while. I left her bikini and my swimsuit up on the towel. It was exciting to be naked, and far away from our suits outside.

When we got back to the towel, I started kissing her and we fucked. She was on top. While we were in the midst of it, a boat came into sight going along the shore. I don't think she saw it and I didn't say a word, we just kept fucking. As the boat got closer, I could hear it. She didn't turn around or give any sign that she heard it, but I think she must have. In fact, I think she started to fuck me harder and get louder as the boat got louder. It was out a little ways, so I don't know for sure that they saw us, but they could have if they were paying attention. As the boat started to disappear to the right I came inside of her and she came a second later.

The next day we went to the main beach. I had her wear her sexiest bikini even when we were walking out through the hotel lobby. She looked great, and got stares from all the men we passed on the way to the car. When we got to the beach we sunned first for a while, and then went for a swim. There were people everywhere. When we were out in the water I pulled her against me and started kissing her. She slipped her legs around me and pulled close. To her surprise, I reached around her and untied her top. She let me pull it off of her reluctantly. The nearest people were a little ways away so they probably couldn't have noticed anything. Then I untied the ties on the sides of her bottom and pulled it off of her. She crushed up against me harder now that she was naked. We could see lots of other people, but I don't think they could have seen anything below the water line. As we made out I rubbed her tits and squeezed her ass and she started to slowly grind her pussy against my cock through my suit. After a few minutes, I grabbed her hand and slipped it inside of my suit and she started to massage me. I whispered in her ear telling her to pull my suit off and hand it to me. She did, and then we embraced again. It felt amazing to have her naked body pressing up against mine while we could see other people. I kept molesting her and she kept rubbing my cock. Then I grabbed her hips and pulled her pussy on to my dick and slipped inside of her. She was a little surprised, and nervous about doing this in a public place, but she started to slide up and done on me none the less. As she got more aroused she started to make muffled moans. Eventually we came, and I think some people heard her and looked over, but no one could have seen anything, they probably guessed what we were doing though.

After we came, I handed her back her suit, and I slipped mine on as well. Now that a couple of people seemed to have noticed that something was up she had more trouble getting the top back on without being conspicuous, but she did her best and we went back to the towel. As we got out of the water a handful of people were clearly watching us, and she seemed pretty self conscious. When we got back she whispered that she wanted to go now. I said not just yet. I gave her a towel and told her to wrap it around herself and slip her suit off beneath it. She did her best to be discrete, but a couple of guys were clearly watching. I think that one of them got a good glimpse of one of her breasts when she slipped the top off. I was starting to get excited again seeing other people watch her, but we packed up and left.

On the way back in the car I ordered her to take off her towel and suck me off while I drove. Once we were driving, she complied, and I came in her mouth. I didn't let her put her towel back on until we entered the little town. We walked back up to the room, and at least a couple people took notice of the beautiful woman that appeared to be wearing only a towel....

That night we went out to a club. I selected a very short, very see-through dress for her. At first she said that there was no way she could go out in public wearing that, but I assured her that it was a more relaxed culture down here, and picked out a fairly conservative black set of bra and panties for her to wear underneath, and some high heels. She agreed, but clearly wasn't happy about it.

When we walked out through the lobby, everyone stopped and started at her as she went by. I was very proud of the catch I had. She looked absolutely stunning and everybody knew it. You could clearly see her underwear through the dress. We got out to the car and drove to the club. When we went in everybody stared again, much to my satisfaction. I was hard already.

We drank, and talked, and I kept noting everyone checking her out. She loosened up a little bit as the booze kicked in. After a while I asked her to dance for me. She complied and started dancing in front of me while I sat on one of the couches. As it went on the dance got more and more sexual and I was really starting to get aroused watching her showing off in front of everyone. After a while I pulled her on to my lap and started kissing her. I reached around and cupped her ass while we made out. She seemed put of by that at first, but eventually relaxed and started kissing back in earnest.

Then I instructed her to go into the ladies room with her purse, take off her bra, and come back out with it in her purse. She looked stunned that I would ask her to do that. She protested that she could get arrested. I told her that first of all it wasn't against the law to be topless in Costa Rica, but secondly, no one would ever turn in a pretty young lady like her for sharing too much of her self like that. She didn't want to do it, but I flatly told her that this was one of the times when she needed to put my desires first and earn her money. I said that in fact, since she had resisted my order, she would also have to change into the other pair of panties I had hidden in her purse. She looked mad, but got up and headed towards the ladies room.

When she came back out, she looked stunning. Her breasts were clearly visible, and everyone in the club noticed what she had done immediately. The new panties were much smaller than the first pair as well. They were small in the front and just a thong in the back. Anyone who wanted to could get a great view of her ass or tits through the dress. She looked petrified, but she walked back over to me and sat down. I asked her to go get me a drink from the bar. She got up and went over to the bar while all the guys were checking her out. At the bar she had to lean over the bar so the bartender could hear her and the back of the dress rode halfway up her ass. I was in heaven, and a lot of guys were openly ogling her.

When she got back I sat her on my lap again and started kissing her. I slid my hand under the back of her dress and was caressing her ass openly. She was very uncomfortable with the situation, but started rubbing her pussy against me anyways. I was getting very hard, and after a while I whispered in her ear that she was a very good girl, and then we got up and left. She got a lot of attention again walking through the lobby, and when we got back to the room I bent her over the desk and fucked her hard from behind. She was very wet when I slipped inside of her, so maybe the whole experience wasn't all bad for her either....

The rest of the month was pretty uneventful. I continued the same sort of thing. We slept naked together every night, and sometimes I would fall asleep with my hand on her tits and pussy. We had a lot of sex and blow jobs and whatnot, and exciting outfits of course. One day I made her go grocery shopping wearing a tight, white, narrow band top, an equally tight and narrow miniskirt with nothing underneath, and a pair of white platform boots. She looked like a total slut wearing it, and when she got back I fucked her from behind again while she was still wearing the outfit. I also had her put on a really short, slightly see-through nightie and a very hot white pair of panties one day and answer the door when we ordered a pizza. It turned me on, but the guy just stared, accepted the money, and left. She seemed really horny afterwards.

At the end of the third month, as I had promised, we talked again about her list. I brought it up, and she said that of course she had been thinking a lot about what she would and would not be willing to do with other men, and she was not at all comfortable with the idea.

I asked her if she hadn't ever fantasized about being with random men or multiple men at one time.

She said that of course she had fantasized about it, but that fantasy and reality were very different things. She said that she really wanted to continue to stay with me, and she was very happy with the situation, but that she was very afraid of what I might make her do with other men if we continued the arrangement.

I said that the idea of other men seeing her body, touching her, and her touching them was very exciting to me, and that I would have to end the arrangement if she couldn't accommodate that desire. She looked scared, but I backed off a bit and suggested another compromise. I suggested that for the next 3 months I would agree not to ask her to have sex with anyone other than me, but I said that that was all I could commit to. I might ask her to be naked in front of men, touch them, let them touch her, or maybe even go down on them. But, I reminded her of how I liked to take things slowly, and I said that since she can leave at any time, why didn't she just stay as long as she was comfortable?

She agreed, but was clearly distracted and a little bit divided for the rest of the night.