I was starting my second year in Jackie's boutique. Dave had accepted an overseas job that would last 2-3 years. I couldn't go: it would be extremely dangerous for both of us if I were found out. He had been away 2 months, but I wasn't missing him as much as I thought. He was really just using me when his real girlfriend wasn't available.
Working for Jackie was pleasant and educating. She is a very attractive tranny, 45 yrs old, of French-Canadian descent . She was about 5-8 and very full -figured. She turned heads where ever we went. Older men eyed her with obvious longing. Her shop was a very high end boutique, selling women's fashions and lingerie. Prices ran from $1000 to $25,000. She was open five days a week, from 11-6, by appointment only. Her clients where older men shopping for the wives and mistresses. Some older women shopped to impress younger lovers. We had a private lounge with dressing area for custom modeling. Jackie had a luxurious office in the back with a shower and Jacuzzi, and a day lounger. Jackie would assist the clients and have me bring items as needed and wrapped items after the purchase.
Jackie had a business partner who ran a similar boutique in another city. She would send one of her assistants over from time to time. One girl, a pale Nordic girl, came by often, I noticed when she and Jackie talked, they often looked at me.
A couple of weeks later, I was giving Jackie her morning blowjob. I usually come in around 8:30 to do this and whatever other training she requires. She has a nice cock, not as long as Dave's, but much thicker. I would suck 20-30 minutes, but she would always stop before she came. I never knew why. This morning, she ordered me to turn around. she raised my skirt and started teasing my ass hole with her finger.
As I moaned, she said, " I want to fuck you."
I said, "Oh, yes! Please!"
She fingered my hole and very lightly lubed me, just barely enough to let her get in. She knows it hurts me, but she won't fuck me otherwise. I reached behind me to spread my cheeks. I could feel the head straining at my hole.
She said, "Beg for it!"
I cried out, "Push it all the way in! Fuck me hard! Please, I want it, now!"
She grabbed my hips and forced her way in. She fucked me fast and furiously. The pain was rough, but I was turned on: I had a cock in me, again! She was fucking me harder than she had ever done before!
She fucked my for nearly 20 minutes before she emptied her load in my ass. She never came in me since the first time she fucked me. She usually fucked me a few minutes and had me suck her clean. She pulled out and said, "I want to see you clean yourself." I reached behind me and scooped her cream from my ass with my fingers. I slowly licked my fingers clean while looking into her eyes. She said, " I love watching you do that! It always makes me so horny! Get over here and suck me clean!"
I took her in my mouth and started sucking and licking. She moaned and said, "That feels sooo good. Don't stop!" I kept at as she was enjoying it more than she ever had before. My jaw was starting to hurt and I glanced at the clock. I had been sucking her for over an hour! She was rock hard in my mouth! She saw my glance and said, "Don't worry, no appointments till 2." I started sucking again, but she stopped my and said, "I want to fuck you again!" She had never fucked me twice before! I turned around, but she told me to lie flat on my stomach on the day bed and spread my legs wide. She lay on me as she mounted me. I was still sore from the first fucking when she started thrusting again. This was going to hurt more, but the feel of her cock in me felt wonderful.
She kissed my neck and reached around to grab and pinch my nipples.
I yelped and she said, "Good, We understand what I want, don't we!"
I said, "Yes, ma'am."
I could feel her hips grinding against my bottom. I love how that feels. I couldn't move beneath her as she fucked me slow and deep. This is my favorite position.
As she ground into me she said, "I came to soon last time. I intend to take my time and thoroughly enjoy you. We have all morning."
She had already fucked me longer than Dave had ever fucked me and seemed to be fucking me even longer.
She varied the pace. Sometimes she would go slow. Other times she would pound me as fast as she could. She would bite my neck and ears and pinch my nipples during the poundings.
I was starting to get very sore. Since she doesn't use lube, the pain was getting greater. It wasn't fun anymore, and she still didn't seem to be ready to cum!
She whispered throatily in my ear, "What's the matter, dear? I've only been fucking you an hour: surely you can take another hour! After all, This is what you really want. And it feels soooo good to me. You want me to be happy don't you? After all, what does your tattoo say? Always open, Always Yes? Now be a good girl and tell me you want more!"
With tears streaming down my face, I said, "Please, fuck me as long as you want."
I geared myself for more pain. What had come over her? This was a different Jackie from what I had seen before!
I don't know how long she had been pounding me when I heard the office door open, I hoped Jackie would stop, but she just kept pounding into me.
I heard a voice a voice say, "Oh My! I'll come back later!" I looked up: it was the pale Nordic girl.
Jackie said, "You're early, but, come on in and have a seat. I shouldn't be much longer. Angie, this is Tracy. She will be working with us, now. She used to work for my partner, Elena. Please excuse me while I finish."
She then pinched my nipples hard and started pumping as hard as she could and I soon feel her relax as she loosed her load in me. She lay across me for a few minutes, not moving.
After she rolled off me she said, "Tracy, be a good girl and lick me clean while Angie cleans herself. Then both of you can go home, Be back in the morning fro your new training."
To be continued....