Willy and Her Friends
Introduction:
Willy suggested charging her friends for instruction from me. We held weekly study sessions.
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. Her little bush was untrimmed but clean.
“I’m going to touch you down there and help you learn to do it yourself.” Willy told her.
“Will this ruin me for my husband?”
“No, there will be no sign at all, no matter how often you repeat this.”
Willy slipped her hand up between Chi-Chi’s legs and very gently began rubbing. The little girl opened her eyes wide and twisted her hips just a little but made no objection. Dixie stepped over and rubbed Chi-Chi’s tits.
“You should stroke your nipples,” Dixie told her. Chi-Chi took her word for it and began tweaking her nipples which rose nicely. After about a minute, she lifted her head toward Willy.
“I think I need to go to the toilet.”
“No, you don’t need to pee, that’s just your lubrication starting. That is something you will need for your husband, It is also needed for your climax, which will be coming soon. I can feel you becoming aroused. Put your hand down here where my finger is and rub very gently to give yourself pleasure.
It took a little while for Chi-Chi to get the hang of it, but soon she was rocking side to side and making little moaning sounds.
“I think it was better when you were touching me,” she said to Willy. My sister put her hand back in Chi-Chi’s bush.
No more than two minutes later, Chi-Chi clamped her legs together, trapping Willy’s hand between her thighs. She rolled back and forth, arched her back and whimpered quietly. Her eyes flew open, her tongue stuck out and she collapsed back against the pillow.
“That was so wonderful, why do women not do this all the time? Is it dishonorable?”
“No, there is no dishonor and no one will know. You must practice at home so you can become skilled on your own.” Willy reassured her with a final light flick of Chi-Chi’s erect clit.
“Is this what my husband will do for me?” she asked.
“Usually not, the man has his own pleasure and he will expect you to help him with that, rather like the way I just helped you,” Willy explained.
“How will I do that, I don’t know what a man will like,” Chi-Chi said.
Willy looked at me and I nodded.
“Tim will show you how a man is made and what he would like you to do.”
I stood up, unbelted my robe and stepped over to the bed next to Chi-Chi. I was already hard from watching the three girls. Chi-Chi flinched away when I got close.
“Don’t be afraid, it won’t hurt you. Dixie was still sitting next to Chi-Chi and stroking her hair. “Watch me.”
Dixie took me in her hand and started stroking and squeezing my hard on. It got very hard indeed.
“Put your hand around it just like I’m doing, and rub it a little bit. This is what a man likes.” Chi-Chi very gingerly put a hand on my dick.
“It is very strange, both hard and soft at the same time. Is this correct?” she asked as she stroked up and down in a very delicate and pleasant way.
“Yes, that is very good. He is close to his climax which is different than yours.” Willy said. “He will produce much more fluid than you. We’ll let Dixie show you the end.”
Dixie took over the hand job. She had gotten very good and within a few seconds I pumped my load into her cupped hand. She had Chi-Chi put her fingers in it.
“It is like soup, warm and smooth.” Does it wash away?”
“Yes, you can wipe it away of just wash it off. It is important that the man does not put it inside you unless you want to have a baby.” Willy explained.
“Inside me! How could that be? That enormous thing would never fit in the opening between my legs!”
“You will be surprised someday. Your juice will help it fit and you will like it very much inside you. You are not ready, but someday you will see.” Willy said “But now your lesson is at an end.”
We watched with interest as she wrapped the sari around her again.
“Here is the money I agreed to pay you. I am very pleased with this lesson, I hope I can come back another time. Thank you for inviting me.”
Dixie put her fifty bucks in the kitty too.
Willy and Dixie played with each other until both were satisfied and our weekly session was over.
**************
A couple of Thursdays later Willy came home with a girl she introduced as Butterfly McQueen. Willy introduced her and sat on the bed.
“Her real name is Ellen, but we call her Butterfly because of the movie, you know.”
“I’m happy to meet you, Butterfly,” I said, wearing my flannel robe. She was a pretty girl, slightly built with milky white skin and black hair cut very short, almost like a skull cap. She had grey eyes with black eyebrows and perfectly straight white teeth. She was wearing a knee length skirt with thigh high nylons, heels and a black silk blouse.
“What brings you here tonight, Ellen?” Willy asked.
“Chi-Chi told me that Willy can do wonderful things for a girl,” Ellen said in a breathy little voice.
“Did she say anything about me?” I asked.
“Yes, she said you could show me how men are made and what they like. I don’t have any experience with that. I’ve never even seen a man. She said Willy could get me ready for a man. I’d like her to do that for me.” She glanced over at Willy and showed her the tip of her tongue.
“Sure, I can do that, Butterfly. Come over and sit next to me. As soon as Ellen sat down, Willy started on her.
“I love your blouse, Butterfly, why don’t you take it off for me?” Ellen unbuttoned it and carefully folded it and set it on the floor. She also removed a little light blue B cup bra. She had very nice little tits with nice dark nipples shaped like cones. I felt my dick beginning to stir. Willy put a hand behind Ellen’s head and pulled her face in and kissed her hard for a long time. I could see their tongues writhing against each other. When they broke the kiss, Willy lowered her head and sucked on Ellen’s nipples, one then the other.
Butterfly was squirming in her seat, but holding Willy’s head against her chest. Ellen started squeezing Willy’s tits through her t-shirt. Willy promptly stood up and peeled it off. When she sat down again, she pulled Butterfly’s face against her chest and coached her on how to suck her tits. I’d never seen Willy’s nipples so erect.
Soon Willy put a hand up Ellen’s skirt and started stroking and rubbing. Another minute and she had Butterfly’s skirt off and her thong pulled aside. Ellen was making little groaning noises and twisting her hips against Willy’s hand. Then they got serious. Willy pulled off Ellen’s thong, pushed her onto her back with her feet in the air. Willy knelt on the floor and put her face in Butterfly’s snatch. The sucking and licking noises as well as the expression on Ellen’s face was getting me seriously hard, but nobody had asked for me yet.
Willy had two fingers up Butterfly and was still licking her clit. I could see her oozing girl juices glistening in her bush. Willy was relentless and finally Ellen reached her climax. Her feet in their spike heels waved in the air, her hips bucked upwards and from my seated position I could see her little asshole contracting and pulsing with her orgasm. Her O face was wonderful. Her eyes rolled back, her tongue stuck out and she gasped for breath; she never stopped rolling her nipples.
That orgasm was Willy’s signal for a change. She stood up and shucked out of her pants and panties. She knelt on the bed above Ellen’s head, bent down and fed one of her tits into Butterfly’s mouth and started sucking on Butterfly’s nipples at the same time. They kept this up for a few minutes, then Willy started crawling further down Ellen’s body until the two had each other’s heads clamped between their thighs.
Every few minutes a tremor would go through the pair, all those tits, thighs and buttocks jiggling as one or the other had another orgasm. They stayed locked in this sixty nine position for what seemed like hours but was probably only ten minutes. I looked like I had a tent pole under my robe. Finally Willy uncoiled from that knot of lust and sat up with her back against the headboard.
She coaxed Butterfly into a sitting position between her legs with her back against Willy’s chest and her knees raised. In this classic reach around position, Willy could manipulate Ellen’s nipples or masturbate Butterfly at will. She proceeded to do that several times. She started biting Butterfly gently on the neck. Every couple minutes Butterfly would get off again, digging her heels into the bed, grunting in her throat and convulsing as she came. From my vantage point and her knees up, I could watch her pussy and sphincter pulsing. Her contractions were forcing a dribble of juice into her bush.
Finally after another shattering orgasm Butterfly just collapsed, slumping back against Willy and starting to snore softly. Willy carefully wiggled out from under Butterfly without waking her. I walked over to the bed and unbelted my robe.
“My God, Tim, you’re huge!” Willy exclaimed.
“I really need some relief, Willy,” I said. I looked at Ellen laying spread-eagled on her back on the bed, the girly juice oozing out of her snatch.
“Would she mind if I stuck it in her, do you think?” I asked. Willy looked at Ellen for a moment, then at me.
“No, I’d love to watch that, but she’s out cold, so she can’t give you consent, so it would be wrong. I’m sorry, I know you’re in distress, but that wouldn’t be right.
I’ll tell you what would be OK, though, you could stick in me. She knelt up on the bed and put her ass up in the air just in front of me.
“I though you preferred your own team,” I said.
“Well, I do love the girls, there’s no doubt, but I still need some wiener once in a while, and you’ve certainly got plenty available.”
I couldn’t see anything wrong with this logic. I stepped up to the bed and shoved my cock into Willy all the way to the balls in one stroke. She was as wet as any woman I’d ever been with. I almost came immediately but slowed my stroke and concentrated, since I didn’t want to finish in my sister. I was saved when Ellen stirred next to us on the bed. She got her eyes opened and watched intently as I rammed in and out of Willy.
“Is that what guys wants, a girl on her knees with her ass up?” she asked. “How does he finish?”
“It’s kind of like when you finish but with a lot more juice,” Willy told her.
“Where do you want me to put this?” I asked knowing I couldn’t wait much longer.
“Well, not in me for sure!” Willy said. “How about on Butterfly?”
“Will it hurt?” Ellen asked.
“Oh, no, it’s kind of like having a cup of warm soup splashed on you. It cleans right up and doesn’t stain or anything. You’ll be fine,” Willy explained.”
“Would you like Tim to fuck you before you go?” Willy asked Ellen. “You said you wanted to know how men were. Don’t be afraid of the size; as wet as you are, he’d slide right in.”
“No, I don’t think so, I’d rather be with you again,” Butterfly said shyly.
I could see she had fallen for Willy in a big way, but I still needed relief.
“Go ahead Tim, you can finish on her.”
Ellen laid her head in the small of Willy’s back, watching me plunging in and out. Finally I couldn’t wait any more, I pulled out of Willy with a wet pop and blew directly onto Butterfly’s head. I kept pumping until that whole short little haircut was saturated with cum. It looked like she had grey hair. All three of us collapsed in a heap and slept for almost an hour.
When we came too, we got Ellen on her feet. Willy took a shower with her and I helped her get dressed. As she was leaving, she opened a little clutch purse and took out a hundred dollar bill and handed it to Willy.
“I think I got two sessions worth tonight. I hope I can come back again some time.
“I’d love to see you again,” said Willy, I noticed Ellen didn’t even glance at me. As it turned out, although she came to several more sessions, I never did get to fuck Butterfly McQueen.
**************
Things went along like this pretty smoothly for a whole year, clear through the Christmas season. Willy spent some of our stash on presents for the family, but we were still doing very well, with several thousand dollars stashed away.
Early in April things changed, a lot. Willy brought home a girl named Valerie Behr.
“Tim, this is Valerie, she’s a freshman at State. She’s an A+ student, the captain of the tennis team and her class president.” Willy said. She couldn’t take her eyes off Valerie and it was obvious why.
“I’m happy to meet you Valerie, I’m Willy’s brother Tim.” I said.
“I know, I saw you around a few times last year before I graduated. You picked up Willy from school once or twice, and I’ve seen you at your shop, my dad brings his Mercedes diesels in there for service. I’ve been hoping to meet you, and when some of the girls at school talked about your study sessions, I asked Willy to invite me.”
Valerie was really stunning. About five seven and a hundred thirty, she was perfectly proportioned, wide shoulders supporting a big high rack, a tiny waist, long straight legs and an ass like a couple of soft balls. Her shoulder length blonde hair framed her face and showed off her blue eyes, tiny nose and rosebud mouth. She wore very restrained makeup that was very skillfully applied. After the yearlong parade of nervous and mousy girls, Valerie looked like a super model. She was wearing tight white jeans and a sky blue fuzzy sweater. Her ass rolled and strained in those jeans as she walked and her tit jiggles just slightly under the sweater. Her athletic development showed in her carriage and movement. The heels brought her about up to my chin.
“So what would you like to do tonight Valerie?” Willy asked. I really hoped she wasn’t just there for Willy. That had happened with other girls several times already. My hopes were answered.
“Really I’m here about Tim, I don’t think I need much instruction,” Valerie said with a sidelong glance at me.
“Usually, the way we work it is that if a girl wants Tim, I get her ready for him,” said Willy. I glared at her. What she really meant was that she got a piece of every girl that showed up no matter what she was there for.
Valeria was very bold. She walked over where Willy was sitting and pulled her to her feet. Valerie was a good five inches taller than my sister.
“Well, little Willy, if you think you can get me ready for Tim, let’s see what you’ve got.” She unbuttoned Willy’s shirt and unhooked her bra. She tweaked Willy’s nipples, took a step back and looked at Willy’s fabulous rack.
“You know, a plastic surgeon could fix that up for you. I could give you a card if you like.” Willy looked at her in shock.
“What do you mean? Fix what?” Willy wasn’t used to her tits being criticized.
“Well, look, your tits are not exactly the same size and your left nipple isn’t right in the center. Here, let me show you.” Valerie pulled the sweater over her head and since she wasn’t wearing a bra, the resulting tit drop was a wonderful thing to see. She was right. She did have a slightly bigger and more perfect rack than Willy. It was a little more solid and higher up on her chest, so that her cleavage started almost at her collarbone. There was not a hint of sag. Valerie leaned down and toward Willy until their tits were rubbing against each other. All three of us starting getting aroused. Valerie peeled off her tight jeans, revealing a pair of Hello Kitty underpants. She pulled down the underpants to reveal a smooth shaven snatch with a tiny clit already erect. She stroked it a few times, then returned her attention to Willy.
She pushed Willy back against the wall and slipped a hand between her legs. Willy moved her legs apart slightly to give Valerie better access. Valerie rubbed Willy hard and fast. Very gradually Willy started to respond. She brushed her palms over her suddenly suspect nipples. Her breathing got faster and shallower, her mouth gaped open, her tongue lolled out and her legs started to shake spasmodically.
Then abruptly, as Valerie continued her assault, Willy’s knees buckled and she slid down the wall like a cartoon character. For a moment she sat on the floor twitching and gasping for breath. Then Valerie helped her to her feet and pushed onto her back on the bed. She bent over and kissed Willy hard for a long time. Then she climbed on the bed, straddled Willy’s head and very slowly and gently lowered her pussy onto Willy’s face.
Now Valerie was on her hands and knees facing me and having her snatch licked and sucked by Willy. She gave me a big smile and motioned me over. I realized that Valerie had never seen my dick and might be unprepared for what she was offering. I closed the robe until I was next to the bed, then I unbelted my robe, dropped it to the floor and stepped up to the bed with my hardon sticking out like a Billy club. She smiled again and parted her lips slightly and showed me the tip of her tongue. Over Valerie’s back I could see Willy rubbing furiously on her own pussy. Valerie opened wide and laid her tongue over her lower teeth. The head of my cock has been described as the size and shape of a quail egg.
I laid it on Valerie’s tongue. She squeezed her lips over it a few times then moved her head forward to take some of the shaft. Her beautiful blue eyes were turned up to me and never broke eye contact. She had about half of it in before she gagged a little. I figured that was about as far as I was going to go, but she had just been resting. She opened her mouth so far I could see her tonsils. I pulled her head forward and I felt my tip against the back of her throat. Her tongue was licking the underside of my balls, her lips were working on my shaft pulling it deeper and deeper in.
I was starting to feel dangerously close to a climax so I pulled back a little.
Just about then Willy finally got herself off, humping and thrashing. She never stopped eating Valerie and all that activity brought Valerie to her orgasm. Her hip bucked down against Willy’s face and she lurched forward against me. Suddenly her nose was pressed against my belly and the head of my dick was all the way down her throat. I could see a bulge in her throat where my tip was. It was too much for me and I held the back of Valerie’s head and I blew and pumped until I was dry. I slowly pulled my dick out of Valerie’s face. She looked up at me with cum dripping off her chin and smiled again. She gave me five minutes to get reloaded.
By the time I was ready again, Valerie was lying flat between Willy’s legs eating her out. Valerie looked back at me, slapped herself on the rump to tell me what she wanted. I pulled her hips up to a doggy position, knelt up behind her and shoved my dick into her. She was as wet and smooth as an eel. I fucked her hard and fast for a long time. I could reach down and fondle those magnificent tits.
Over Valerie’s back, I could look into Willy’s eyes which looked almost deranged with lust. Her jaw was clenched, her teeth were bared in a snarl, her beautiful tits were jiggling in the most wonderful way. She was clutching handfuls of bed covers, twisting and thrashing side to side under the attack on her clit. The noises coming out of her throat sounded like she was speaking in filthy tongues. Valerie finally got Willy off in a wild noisy climax. Valerie came soon after. The feeling of her pussy squeezing and gripping my dick made me cum for the second time.
Willy climbed unsteadily to her feet and tottered off toward the shower.
“Care to join me?” She asked Valerie.
“No, I’ll wait,” Valerie said.
It took Willy ten minutes to get clean and Valerie and I chatted all that time. Finally it was our turn in the shower. Valerie and I soaped and washed each other exchanging compliments and caresses. After we were clean dry and dressed again. Valerie said:
“I’d like to come again some time if that’s OK.”
“Sure, you’re welcome anytime,” Willy told her.
“I wasn’t talking to you, I was talking to Tim.”
During our chat, Valerie had told me that she was the only child of Anthony Behr of Behr Mercedes and that she would inherit when he retired and that she could get me a management job in the garage there. I took the job and Valerie and I dated exclusively for more than a year before we decided.
“Willy, I want to use my share of the study group money to buy Valerie a ring.” She didn’t argue much, she was a little jealous that I got to fuck Valerie and she didn’t.
“Tim, I don’t want you fucking your sister or those friends of hers, anymore,” Valerie had insisted when I proposed. I agreed, it had been all Willy’s idea anyway.
“What about you fucking women?” I asked reasonably.
“I don’t really go for women that much.” She said.
“You could have fooled me with what you did to Willy!” I said.
“I was just using her to get to you.”
