Willy and her Friends_(2)

When I started college, my sister Wilhelmina, known as Willy, was going to an expensive and exclusive girl’s high school. You might remember from Willy and the Hand Job that my sister had convinced me to teach her how to give a hand job. She later had me do the same for a friend of hers named Dixie. Dixie was so impressed that she had been talking up the experience around the school. Now my sister was getting requests from other girls at the school.

There were a lot of international students at Willy’s school from lots of different cultures. Girls had heard Dixie’s story and wanted some instruction of their own.

“Some of them have never seen a guy’s thing, a lot of them are virgins and they want somebody safe to show them. Dixie has convinced them that you’re the guy. I’m thinking we can make some good money off this situation,” Willy said in my room a few weeks after Christmas.

“What do you mean, make money?” I asked.

“Look, Tim, you’re good looking, friendly, a good talker and have a great dick. I’m gonna tell them fifty bucks apiece, no matter what they want. I know they’re good for it. I’ll promise to stay in the room to make them feel safe and you do whatever they want and I collect the cash.

“What about pregnancy? That would be very bad, Willy.”

“ I guarantee everybody you touch will be legal and on the pill.”

“OK, set something up and we’ll see how it goes.”

My parents were thrilled that Willy was making so many friends and that she and I were getting along. Willy told them she was hosting a study group, which was true in a way. They made no comment at all about the trail of girls in and out of the house every Thursday night.

Dixie was our first customer the first week of school in the spring. She had filled out some since our session last year, but was still very slight with a very flat chest and her mousy hair was cut better but still pretty lank and unattractive. Still her money was as good as anybody else’s, plus she had set all this up for us with her talk around the school.

“So, Dixie, hi again, how’s your year been? I see you cut your pigtails, what would you like to learn this year?” I asked, sitting in nothing but a flannel robe belted at the waist.

“Well, Tim, you were so good last year about showing me the way to give a hand job. I’ve practiced on a few guys, but nobody’s ever put it in me, and I’ve never used my mouth on a guy, just my hands, so maybe those things this year,” she said. She stood looking at me, pulling down the hem of her skirt and squirming with embarrassment. I turned to my sister.

“What do you think Willy, is she ready?” Willy looked at Dixie and motioned her over to where she was sitting on the bed. She put her hand up Dixie’s skirt and probed for a little while.

“Her hymen is gone.”

“Horseback riding,” Dixie said.

“She’s a little dry, but we can help that,” Willy said. With her hand still up Dixie’s skirt she pulled Dixie’s shirt up and sucked on her nipples, one side then the other. Dixie squeaked a little and seemed to relax. Willy pushed her back on the bed, face up and her knees in the air.

“She’s still a little dry, maybe if you show her your dick.”

I got up, unbelted my robe and stood between Dixie’s knees with my hardon sticking straight out toward her. I stroked it a couple of times to get it to full size.

“Oh, that did it,” Willy said with her hand still in Dixie’s panties. “She’s oozing now. I think you can give it to her now.” Dixie looked a little frightened and Willy held her hand.

I stepped up to the bed between Dixie’s knees. I crouched a little bit and rubbed the head of my dick in her slit. She squirmed and pushed her hips up toward me. I kept rubbing until I was good and lubricated from her juices. I put my tip against her opening and pushed, very gently. The head popped into her nicely, oiled by her juices. A little squeak and a sudden sharp intake of breath was her only reaction. She squeezed Willy’s hand harder.

“Is she OK?” I asked. Willy leaned over Dixie, kissed her on the mouth and whispered to her.

“Yeah, but go slow, she says she afraid she’ll split.” I moved into her very slowly, a tiny fraction of an inch at a time and pulled out after every advance. She seemed to relax and lubricated even more. After about a minute I was all the way into her. She kept squeezing Willy’s hand for comfort. I kept up medium strokes making sure not to hit her cervix or hurt her in any way. She was starting to respond, twitching and grunting as I went deeper. Willy was French kissing her and playing with her tits. As her arousal rose toward a peak, Dixie kept lifting her head up and looking down at her crotch, trying to figure out what was happening to her body. Finally she came, whimpering, twitching and squeaking. I could feel her little snatch gripping my cock. It was hot enough that I felt my balls start to churn.

“Watch his face and feel him way up inside you, he’s going to fill you up with cum, this is the best moment.” Willy said in Dixie’s ear. I put my hands under her ass, lifted her hips up pushed all the way in and came hard. I pushed and pumped and when I was done, I dropped her hips back on the bed. She lay there gasping for breath and leaking cum onto the sheets. I put my robe back on and sat back down.

Willy knelt next to Dixie’s head and masturbated herself to orgasm.

I helped Dixie get dressed and got her coat on. Willy stashed Dixie’s cash in my night stand and we were done for the week.

*********

The next Thursday, Willy knocked on my door and I ushered in Willy, Dixie again and a little Indian girl with a little blue dot on her forehead, wearing a beautifully colored sari wrapped around her.

“Tim, this is Chitaili Mustafi, we call her Chi-Chi. She is completely inexperienced and wants some basic instruction.” Willy said. Chi-Chi was very pretty, the delicate fine features of the Indian subcontinent. It turned out she was from Bengal.

“Chi-Chi, this is my brother Tim. He’ll show you whatever you want to know. I’ll stay here in the room so you feel safe. He won’t do anything without your permission and cooperation, so just tell us what you have in mind and we’ll get started.” Willy said.

“I am engaged to a man in India who is much older than me. I have never met him, but he is a friend of my father. I have stayed pure so that I will not be disgraced at my wedding. But I don’t know what he will want me to do, and I don’t know how it will feel. Since I will not be going home for several years I have decided to advance my knowledge in this area. I have heard my friends talk about a climax that is extremely pleasurable and I wish to know that sensation and to know what a man will want from me in a marriage.” She had a beautiful melodious voice but seemed embarrassed and very ill at ease. I looked at Willy.

“I think she should start with you first. If that goes well I can get involved.” I said. Willy nodded and guided Chi-Chi next to the bed. She helped her unwrap the sari which was several yards long. She wore a little training bra and white panties underneath.

“I want you to remove your underwear,” Willy said.

“But then all of you will see my shame,” Chi-Chi said fearfully.

“There is no shame, it is part of your body that God made.” Dixie told her.

Apparently convinced, she shucked out of her bra and panties and lay back on the bed with her knees open.