My life changed recently and I’m still trying to figure out if it’s for the better. My name is Don and I’m 18 years old and fresh out of high school. My grades weren’t good enough to get me a scholarship and my parents make too much money to qualify for government money. So after I graduated I started looking for a job that pays better than the burger place I was working at. That when I saw an ad in the paper for a driver. The job description was interesting because it required a confidentiality contract be signed upon employment plus it offered benefits. The next day I called the number on the ad, Gina answered the phone. She told me that several people were interested in the job. She also stated that it had unusual hours so room and board was included in the job. She also reinf***ed the need for discretion and that if I was unwilling to sign the confidentiality contract I need not come in for the interview. I quickly informed her that I was a hard worker and that I knew the city well and had a clean driving record. She invited me over for an interview the next day at 2 P.M. I was to be the last interview of the day.
I arrived ten minutes early. When Gina came out to get me I was instantly aroused by her, she oozed sensuality. Gina had nice firm breasts somewhere between a C and D cup, and curves in all the right places. Her height made her a slightly intimidating at the same time. She invited me into her office and there was a woman there with a legal document for me to sign before the interview could begin. Once I signed, the woman (Samantha, I found out her name later) left. Gina told me the position was for a driver so I had to have a spotless driving record, test for d**gs every three months and I had to know my way around the city. I had to answer questions on how to get to different location around the city at different times of the day. The last place she asked me directions was to my house. She grilled me for what seemed like an hour only to tell me she had one of those GPS navigators. She just wanted to see if I was lying to her about my city knowledge. She asked questions about my habits and if I had a criminal record. She had me lined up to have a d**g test done the next morning before she would tell me if I got the job or not. She also wanted a fax from my insurance company to confirm I did have any vehicle citations.
I went to the clinic as required and gave my sample and it tested clean like I knew it would. When I was giving the official paperwork I was given a card that told me to report with the results. When I arrived at Gina’s office I was reminded that confidentiality was still in play. She then informed me that she ran an e****t service for shemales. I was to drive them to their clients, usually hotels and pick them up when they were done for the night. The blank look on my face made her laugh and ask if I knew what a shemale was. I told her I did. Then she informed me that all the women in the house were shemales to include her. That is why she needed someone that was discreet. "You are the only one that met all my requirements, that and the fact you are cute didn’t hurt either."
I told her I would love the job but I couldn’t tell my parents I was moving out of the house to go living at an e****t service. She told me that she had another business too as a front; it was a clothing store for women. I told her I would take the job and she told me that I would start tonight and she would take me to go get my things from my house so she could meet with my parents in case they had any questions.
My parents were glad that I landed a job so fast and were grateful that Gina was willing to give the job to someone straight out of high school. It didn’t take my long to pack up my belongings and load them into Gina’s vehicle. When we were safely away she started telling me the rules of the house. The first was that the girls were very easy to arouse so if I got one of them aroused I had to help them with that arousal. So I was to keep the bathroom door locked at all times when I was in there, if I didn’t I was going to have to pay the price. Next I was to respect their privacy, I was only allowed in their rooms if I was invited. The girls made the money so I was to be courteous at all times to the girls. If I broke the rules I would have to pay the consequences. If at any time I refused then my employment would be terminated and I would have to leave the house.
When we got to the house I was introduced to all five of the girls. I had already met Samantha; she seemed very sweet and easygoing. Mandy was a lot like Gina in that she could wear a garbage bag and still be sexy as hell. Grace had a professionalism to her that made it seem like this was all just a formality that she was uninterested in. Daniel must have been the resident princess. When she was introduced she made sure to let me know I was just hired help. The last girl introduced was Tabitha. The other girls laughed as looked scared by her. She was very tall, easily topping 6 feet, she reminded me of an Amazon warrior that could snap me in half. I was intimidated by her to say the least. By looking at them you couldn't tell that they were anything but beautiful women. I was told that Mike, the other driver, was out and I would be introduced to him later. Gina then made it perfectly clear that I was to not get the girls too aroused and to keep the bathroom door locked if I knew what was good for me.
My room was next to Mike’s room in the renovated basement. There were three bathrooms in the house, 2 upstairs and 1 in the basement with us. There was a theater in the basement with surround sound and there was free Wi-Fi for everyone to share. While driving the girls to their clients I was able to get to know them a little better. They were all very nice once I got to know them. Tabitha still scares me a little but I know she’s a very nice person. They all wanted to know if I had a girlfriend and if I was going to bring her around to the house. I told them I did have a girlfriend and that I wouldn’t be bringing her by the house because she was the jealous type. Samantha seemed disappointed by this bit of news. I had the feeling that she was interested in more than just friendship.
I was there about a month; I had the night off and was getting ready to surprise Cindy, my girlfriend, when it happened. I had made reservations at a nice restaurant. I was getting ready to shower and shave when I realized I forgot my towel. I ran to get one and hurried into the shower, forgetting to lock the door behind me. When I got out of the shower I noticed that Samantha was waiting for me with my towel in her hand. She was grinning like the cat that ate the canary. She told me to get dressed because I was hers tonight. I was trying to tell her that I had plans for tonight when I had on my pants she grabbed the waist and dragged me to Gina’s office. When we got in there Samantha told Gina that she went to use the bathroom and I was in there talking a shower. Gina said you knew the rules about getting the girls aroused and you failed to lock the door to prevent her from coming in. When I started to protest, Gina informed me that if I broke the rules I would lose my job and have to leave the house. She also told me that as cute as I am if I didn’t want to be used by the girls I should double check the door on the bathroom. Besides it was better Samantha used me first. She also told me that she was going to be using me for her pleasure anyways so I should get used to it. I didn’t want to lose my job and home, so I went with Samantha to her room. She made sure to take me through the TV room where some of the girls were watching TV. Tabitha said "You go, Samantha, breed him well."
When we got into her room she locked the doors and told me I should make my call now to cancel on Cindy. I told her she wasn’t expecting me. Samantha took charge at that point, telling me to get undressed because she wanted to see me naked some more. When I was finished she whistled, telling me to turn around slowly for her. I felt like a piece of meat but I did it. Then she walked towards me and kissed me full on the mouth. It started as a passionate kiss but quickly turned into pure lust with her tongue forcing its way into my mouth. I still couldn’t believe that she wasn’t a girl. Everything about her said female: the smoothness of her skin, the softness of her lips all told me this was a woman. When she pushed me on the bed is when I knew for sure that she had a dick. She was on top of me between my legs when I felt it for the first time. I started to panic thinking of that thing invading me. When she saw that I was panicking she told me to relax and that she would be gentle with me. She took off her shirt slowly, seductively. Her breasts were a work of art. When she removed her bra I couldn't help myself, I had to touch them. They felt so good and Samantha was enjoying my touch because she started moaning and told me to suck them. I didn’t need to be asked twice. I started on her right breast and continued to play with her left. When I let go of her breast to move to the right she took off her skirt and panties and staring me in the face was her 8” cock. She pointed it in my direction and stroked it a couple of times. When she placed her hand on the back of my head I knew what was expected of me so I slowly moved forward and kissed the tip. She encouraged me by telling me that I was doing a good job when I took it in my mouth. Until then I had never done this before. I just did to her what I liked my girlfriend to do to me. It wasn’t as bad as I had thought it would be but I didn’t find it pleasurable either. A strange sense of pride took over me when she started moaning with pleasure at the job I was doing. She was really excited because it wasn’t too long before she grabbed my head and rammed her cock down my throat and came. I thought I was going to die when she pulled out of my throat and kissed me deeply, thanking me for the wonderful job. She was teasing me, telling me I must have lots of experience doing that because I was great. I turned several shades of red from her comment.
She told me to lay down with my legs over the bed. I again did as she told me and she took my knees and placed them over her shoulder. She just looked at me with a smile on her face and told me she was looking forward to this since the first time she saw me. In one graceful movement she took me completely in her mouth. My cock was easily 7” but it was thicker than hers and she took it like it was nothing. My head was spinning from the pleasure she was giving me when I felt something cold and slippery being applied to my asshole. When she put the first finger in me I thought I was going to cum. She had other ideas and slowed her pace to prevent me from coming. When I had settled down she started working her finger and my cock in unison. Without warning she added a second finger and kept the pace. Just when I was getting ready to come again she stopped everything. Samantha really knew how to prolong pleasure. It was pure torture being so close to orgasm and not being allowed to finish. When she started up again she added a third finger. I didn’t know what she was doing but all of a sudden I was seeing stars and nearly jumped off the bed at what she was doing with her finger. That is when she stopped again. I couldn’t take it any more I was begging her to let me cum and that I could take it anymore.