Rachael Ch. 04: The Test

I moved next to her and she reached down and felt my still erect penis, smiling she reached into a bedside drawer, took out a foil pack and popped the contents into her mouth. Next, she moved her face over my erection and then pressed the condom over me with her lips, completing the dressing with her fingers. Swiftly then she mounted me like a cowgirl would a horse. I slipped easily up inside her and for the second time in my life started to have intercourse with a real woman.

She was in control of the situation and I had no intention of changing that. She rose and fell, wiggled and rode, pinched my nipples and had me pinch hers. She leaned way forward, and I could feel her rubbing her clitoris on my groin, it was very hot and sexy. Her breasts were in my face and I took one in my mouth and began to suck on the nipple.

She said, "take as much of the breast in your mouth as you can."

I did what she asked and felt her orgasm all the way down to my toes. I massaged her breast with my mouth, sucking it all in and squeezing it with my lips. Repeatedly, she rose up and down, rubbed on me and moaned each time I squeezed her breast. This was totally insane. I didn't know what else to do and it was obvious to me that I wasn't going to last much longer.

She knew exactly where I was always. She would stop movement surrounding my hard penis and just sit there, pulling on a nipple or pressing one of hers into my face, giving me time to recover. I didn't know what was going on, but she did. She finally moved off me, said it was time for me to learn how to fuck. I just grinned.

"This is work she said, the better you do this the more money we can make. It's important that you retain control of your orgasm. The longer you last the more the woman will enjoy it and have multiple orgasms of her own."

"First position is the missionary position. Approach this from the pussy eating activity. Go down on me and lick me a little, then rise and move to suck my breasts. Once the lady has had a tremble or a small orgasm the clitoris should be left to cool off so coming up to the breasts is a natural move. Suck each of them and let her feel your body between her thighs. If she knows what she is doing, she will lift her knees and push her pelvis up to meet you. If not, you must help her. Gently lift her thighs or knees up to tilt the vagina into a receptive position. Sometimes you will be able to just slowly move in, and sometimes you will have to hold yourself steady for the initial penetration. If the lady knows what she wants she will put it in for you, let her. Now just ease forward and find the entrance. Sometimes it's easier to come up on your knees and look down, learn to find different ways to enter her. Now push into me."

I did what she asked me to do and once inside I pushed as far as I could go. She lifted her knees to my sides, and I felt us line up better and I went deeper into her.

"Stop, do not move," she said.

I froze, almost afraid to move. It felt so much different from the cowgirl ride I didn't know what to do.

"Sliding in and out will increase your desire to cum and we don't want that right now. If you stay still you will give your partner the feeling of fullness that she desires after the tongue orgasm you gave her a few minutes ago. She feels satisfied at this point so leave it that way. Do not be surprised if she has another orgasm when you penetrate her."

I stayed still and could feel her massaging my cock with her vaginal muscles. I cocked my head and looked at her quizzically. "Caught me, didn't you?" she asked.

"Yea," I replied, "I like it."

"You feel very good inside me and I like this too. It's my favorite part of sex. Pull out now, slowly and go down on me again. This will cause another larger and more powerful orgasm."

I did as she said, and I could feel her spasm long and hard shortly after I tongue fucked her and licked her clitoris. I was still erect and very hard at this point, I wondered where she would take me next.

"Time is important here, you must give her enough time to want you again. Some ladies are quick to want you in them after a big orgasm and some don't want you in them at all. You must figure that one out the first time on your own. The easiest way is to move up into penetration position and start to enter her again. Look for signs of rejection or, "I have had enough," hand signals. Be aware of what she wants, don't just push into her and think you are doing the right thing. This is not about you and your dick, this is about her body and pussy."

I did what she said and moved up over her again, she reached for me and just held me in her hand. Obviously, that was a no push sign. I held position and nibbled a nipple that was still hard.

"Lay down beside me and cuddle me," she said.

I did what she wanted, and she looked at my erect penis that she was still holding.

"Do you masturbate?" she said.

"I don't like to, but I have done it."

"Some ladies like to feel a man orgasm either in their hand or in their mouth. Very few of them that we see here want you to cum in their pussy. Remember that and always ask her where she wants it when you can't hold it any longer. Learn to feel the signs of impending release. Know what to do when you get beyond the point of no return. It's important for you to be in control of your dick. That's about all you can hope to control in real life.

She reached for a jar of ointment and opened it up. Next, she removed the used condom and taking a dollop of the cream, she put it on my hot penis and began to coat it. The cream melted quickly and became very slippery and she was soon stroking my very slippery penis. She watched me closely and would stop and say, "Close your eyes and feel this, how does it feel to you?"

I would try to sense my arousal and tell her where I was. I wasn't used to doing this and it was hard to tell what was going on. She would take me to the edge, and I would stop her, so she could tell where I was, then after a bit she would do it again. The amount of time she stroked got shorter and shorter as I got closer and closer to an explosion.

Finally, I said, "Don't touch me, I don't think I can stop if you do that again."

"Do you want to cum?" she said.

"I want to please you," is all I could say at that point. I was doing my best not to cum and it was almost painful. She stopped and left me alone, bringing her attention to my nipples and lips. She kissed me lightly and said, "I really am having a good time with you."

I could only nod my acceptance. I wanted to jack off so bad and I knew that I needed to prove my worth. The pain went down a little and so did my erection.

She made note of it and said, "I think you have learned a lot today." Then she quickly moved on top of me and swallowed my dick into her hot throbbing pussy for the culmination of my lesson. I didn't last too long and as I pumped and pumped into her, she seemed to glow more brightly. She lifted and I could see what seemed like oceans of white cum dripping out of her pussy onto my belly, it was magnificent. She went down and licked all of it up and then moved to my lips, pushed her tongue into my mouth and fed me my own sperm. I was shocked but soon realized that it was tasty, and I licked her tongue clean.

"I think you are ready for Madame," she said.

Madame Silver was entertaining someone when we went back downstairs, and Lisa left me at the bar to have a drink and relax a bit from my lesson. I got a glass of red wine and tried to collect myself, reflect on what had happened and wonder about what would come next. I finished the wine and had started a second glass when Lisa returned and sat next to me.

"Madame will be out shortly, are you ok?"

"I am a lot better than ok," I replied.

"Good, I enjoyed you and I look forward to our playing some more. It's easier for me to take a shower, douche and be ready for my next client, not so easy for you to perform that quickly." She said.

"That's for sure," I replied. "I feel refreshed, but I am not sure I could get aroused too quickly."

"It's ok, I don't think Madame is going to want to see your dick hard, she probably has something else in mind."

We waited, the wine was wonderful, and I felt both aglow and refreshed. Finally, Madame emerged from her office with a gentleman, kissed him farewell and walked to the bar. She had a bit of a glow about her too.

"Such a delightful man," she said as she watched him go out the door.

She turned to us and said, "So, you two had a bit of a tryst?"

I nodded, and Lisa said, "We had a wonderful fuck Madame, and she will be a great partner if you approve."

"Thank you, Lisa, you can return to your room or the selection room, have a good evening."

Lisa smiled and said, "I already had some fun, time to work."

Madame took me by the hand, and we walked to her office, she fixed me another glass of wine and I sat down on the velvet-covered sofa. She sat down across the coffee table from me and said, "I know you have been fucked before, do you have problems with anal sex?"

I replied that I didn't, and until tonight had never really known anything else.

"Good, and we know from Lisa that you can function as a male partner as well. I would like to test your ass out before I agree to a working contract with you. Are you up for that after your time with Lisa?"

I said, "Yes, I think I am ok, my male parts may be a bit tired, but the rest should work good."

"Let us return to the bedroom and continue your audition," she said.