Enjoying My Sister and My Stepmom

We discussed many things, including Cynthia, who would be coming to stay the following day. Mommy was complaining bitterly about her.

Apparently, all had changed when Cynthia realized that Mommy wouldn't have much money. Their everlasting friendship seemed to end overnight and now Mommy hated the idea of having to see Cynthia at all. "I now realize she had no intention of inviting me to New York," she said resentfully.

Then, suddenly brightening up, she said, "I hope you're going to get sexual payments from her, as you're now getting from me. I know you've always had the hots for her." As she said that last telling phrase, her fingers of one hand started lightly playing with my member.

I was embarrassed by the suggestion that I fancied my sister, but only said, "I would never be able to get her to agree to anything."

"Your sister used to tell me everything. She is not as experienced as you think," said Mommy and went on to explain:

"Even when Cynthia was at school, her breasts were big for her age. However, her nipples were even larger than you'd expect for breasts that size. More than that, all nipples are erogenous zones, but Cynthia's are ultra-sensitive.

She discovered it the first time she allowed a boy to get his hands under her bra. She couldn't control herself and found she was trying to rip his pants off when your dad came home earlier than expected and Cynthia and the boy had to pull themselves together. She never allowed a boy passed what she called "first base" again."

"She's not a virgin now of course. She lost her virginity to an old rich guy in Paris. She said it was a half-hearted affair. He didn't even take her bra off so intent was he in fucking her. I don't think the sex was up to much and she hasn't had sex since. She says she's saving herself for some unmarried rich New York stock broker. She must be sex-starved at the moment."

Her idle fingers playing with my penis had caused it to thicken up again.

"I'll tell you what," she said conspiratorially, "I'll persuade her the first day that she can get some of what she wants by giving you a handjob."

She continued, "The second day I'll up the ante to a blowjob."

"The third and final day we'll get her to give you a blowjob, but naked. It'll be up to you then to get her to a fuck position. Once she wriggling underneath you, impaled on your big boner, she'll be begging for mercy. Do you agree with the plan?"

I groaned as my ejaculation sent a jet of cum in the air. The combined effect of Mommy's gentle finger ministrations and the thought of fucking my sister had been too much for me.

"Guess that's a "Yes" then," said Mommy smiling.

In the evening, to show my appreciation for the plan, I decided that it was time I gave something to Mommy. She lay back on the bed, smiling with her legs open, as I went to work with some oral pleasing.

With my nose buried in her light curly ginger pubic hair, licking her clitoris and sucking the little organ, I soon had her juices running.

I slurped happily as I attacked her genitalia with my tongue. Moving her labia lips aside with my lips, my tongue rasped her clitoris hard and I forced my tongue into her vagina.

Soon Mommy was mashing her sex organs against my mouth and I felt a sense of unselfishness as her orgasm engulfed her.

However, her sexual moaning had had the effect of re-engorging my penis.

Reaching again for the cords, I tied her hands to the bedrail, this time with no objection. I had her in a doggie position with her ass in the air and she expected normal sex, but then realized my other intentions as I began working her sphincter with my oiled fingers.

Mommy cried out, "Oh no, you're going to fuck Mommy in the ass you teenage brute!"

I thought this was a bit over-melodramatic even for her. I knew from Dad's notes that she was no anal virgin and pretty soon I was fucking her in between her buttocks.

"FUCK MOMMY IN THE ASS YOU HORNY BASTARD!" she cried as she relished my hard thrusting into her anal sheath.

She was loving it, thrusting back at me. I grabbed her auburn hair and pulled it back painfully which made her thrust back even more.

In the end I stopped moving my hips. I just held her hair as she impaled her asshole back onto my boner until I could stand it no longer and my cum exploded sending jizz spurting up her ass.

She was orgasming as I finished and I reached around her to squeeze a nipple and massage her clitoris as she shuddered to her climax.

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The following day, Cynthia arrived. She looked more gorgeous than ever.

She was dressed in jeans that emphasized her great ass and a loose-fitting t-shirt that failed to hide her breasts that had clearly grown even bigger over the last two years. Her blonde hair was cut short which allowed her big blue eyes to dazzle.

"Hi Billy," she said with a half-smile. "I really just want to check that everything is OK for my University studies."

She had hit the key point immediately and I took a deep breath before I gave her my answer.

"Yes and no," I said ambiguously. She looked concerned.

"You're my sister and I certainly intend that you must go to University. However, I haven't quite worked out the finances yet and I think you'll need to work for a year first. I'm pretty certain I can afford to pay for all your University fees at that point. Of course, it will have to be a local cheap University so that the fees are manageable."

"WHAT!" She looked daggers at me. If looks could kill my death would have been immediate and painful.

"YOU FUCKING MISER!" she screamed at me, then stormed out of the room.

Mommy winked at me and followed her.

Two hours later, I had pretended to leave the house, but in reality had sneaked round the back, as arranged, so I could hear their conversation through an open window.

Cynthia had obviously been largely calmed down.

"Alright Mommy," I could hear her saying, "so what do I need to do?"

"Look," said Mommy, "you know your brother has always had the hots for you."

"I know nothing of the kind," said Cynthia indignantly.

Mommy laughed. "Well I remember poor Billy refusing to get out of the pool. You were standing in a bikini between the pool and the picnic lunch. You and I both knew that he had a big erection that he was scared we'd see. Your dad couldn't understand why Billy wasn't hungry, but you knew you were causing it and you continued to stand there."

Cynthia laughed, "We'll I suppose I knew."

I seethed. I remembered clearly that humiliation and the fact I was starving of hunger. What I hadn't realized was that Cynthia had done it on purpose.

Mommy continued, "Just use your brains. A little handjob will take you a long way."

Cynthia was aghast at the thought of giving me a handjob, having to touch my cock, but Mommy continued to work on her. After another half an hour I knew what to expect.

That night I was in my room just in my boxers. It was another warm night and I was about to open the window a little wider when Cynthia knocked on the door.

As I said, "Come in," Cynthia opened the door and walked in, carrying a box of tissues. She had on a blue baby doll nightie that immediate sent my cock into full boner mode.

"Billy," she said in a low voice, "I'm so sorry I shouted at you. I know that managing the finances is not easy, but I do so want to go to University this autumn. Is there anything I can do to help you reconsider?"

I knew from my overheard conversation that this was a speech worked out between the two women. I was also expecting her next action which was to place her hand against the bulge in my boxers.

I decided to play the daft boy. Gulping in feigned surprise I whispered, "I don't know what you mean."

Cynthia looked gorgeous as she bit her lip in annoyance, grasped my boner harder in my boxers and said, "My fingers can be nice to you if you're nice about my University start date."

I looked at her and gasped, "OK!"

Pulling down my boxers, I stepped out of them as she said, "but don't touch me."

As she brought her hands around my boner she gasped and stared in surprise at its size. She didn't say anything, but just started jacking me off.

Her cool fingers felt delicious round my hot man meat as she said reassuringly, "Just relax, you're going to enjoy this."

I had the impression she'd never done this before and was relieved that Mommy had at least told her about the importance of the helmet, otherwise I think we would have been there all night.

She started making comments in a way that suggested further coaching by Mommy. "You like your sister's fingers round your cock, don't you Billy?"

"Oh yes!" I groaned.

"I bet you've always fantasized about your sister jacking you off, haven't you Billy?"

After a couple of minutes she found that by concentrating solely on my helmet, she had me groaning continually. She was getting good at this, so much so that my orgasm erupted with hot jets of cum spurting all down the front of her baby doll nightie.

She shouted, "Uuuurgh!" and tried to hold my cock away but only succeeded in receiving a gob of cum in her face.

Jumping back, she staggered out into the bathroom.

Ten minutes later Cynthia reappeared round my door wearing a clean pink baby doll nightie and a very tight smile. "Why didn't you tell me you were cumming?" she asked through clenched teeth.

"I didn't know I was supposed to." I explained looking very naïve.

"OK," she said with a heavy sigh, "Good night Billy," and grabbing the unused box of tissues she walked back to her room.

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The following morning at breakfast, with the three of us sat around the table, I said to Cynthia in a voice which I hoped conveyed that I had spent a lot of time considering the matter, "A University start date of this September is fine."

She looked pleased until I added, "at a local University of course."

There was silence round the table until Mommy winked at Cynthia, then put her hand on Cynthia's and said, "I want to talk to you about a few things later, Cynthia."

Cynthia looked mollified by this and we carried on in silence until I walked out.

An hour later, I had again pretended to leave the house, but in reality had sneaked round the back to listen in.

Mommy was sounding very reassuring, "So, that's great, last night you were obviously very persuasive, but clearly you will need to go further for New York. It has to be a blowjob."

"WHAT! YUK!" Cynthia was clearly not impressed with the suggestion. "He might cum in my mouth."

I could imagine the look of disgust on poor Cynthia's face.

"Nonsense," said Mommy, "you just need to be more careful than last night and tell him to tell you when he's cumming."

"Anyway," said Cynthia, with desperation in her voice, "he's huge. It's not natural."

"Do you mean he's got a big cock?" said Mommy with a half-laugh.

"No," said Cynthia in a loud voice, "he's got a very, very big cock."

"Alright, calm down," said Mommy soothingly, "you don't have to swallow his whole cock. Just concentrate on the knob bit at the end. It's really the only part that matters."

The conversation continued with Cynthia raising objections and Mommy encouraging her to think about it, until it finished with Cynthia saying, "Ok, I'll give it a go."

That evening was a repeat of the previous evening with Cynthia knocking on my door, then entering. She was wearing the pink baby doll nightie that she had changed into after I had ruined the blue one. She was again carrying a box of tissues.

As she approached me she said in a low voice, "I really want to go to New York. Please consider it."

As she said it, she put her hands down to grasp my cock again through my boxers, but this time I took a step back and held my hands up.

"No, Cynthia," I said in a voice that I hope conveyed reluctance, "I know what you're offering to do, but the New York course is just too expensive."

Cynthia stepped forward after me and firmly grasped my boner. "What if I were to use my mouth," she hissed.

I looked astonished and flummoxed as I responded, "Gosh, well I don't know."

I then took a deep breath and said, "Well I suppose I could look at the figures."

Cynthia smiled as she lowered my boxers, but said in a slightly steely voice, "Good, but remember, you mustn't touch me and for God's sake this time tell me when you are cumming."

She pushed me until I was sitting at the end of the bed and knelt in front of me.

"I certainly will," I gasped, as her melting mouth opened and sucked in my helmet.

Oh fuck, this was heaven. She didn't have Mommy's subtleties of using her tongue, or of grasping my balls, but to have achieved a lifelong ambition of being sucked off by my sister was ecstasy.

Following Mommy's instructions, she concentrated on the mushroom head. Her lips slid backwards and forwards over the head to the rim and back to the red eye at the very tip.

She may not have done a blowjob before but she learnt very quickly. The rhythm was just the right pace, not too fast and not too slow. The pressure of her lip sucking was perfect.

My boner seemed to grow in her mouth as her sensational sucking of my glans was bringing me to a higher and higher peak.

I had to fight hard to stop myself from grabbing her head and fucking her mouth fiercely.

Suddenly I could hold back no longer. I felt my jizz surging up my cock and into her mouth. Unaware, she carried on sucking me as spurt after spurt jetted out.

After about the third spurt I groaned, "Sister, I'm cumming!"

Too late, she dragged my cock out of her lips. A rope of cum spurted onto her face as she exclaimed,"Aaargh, that's disgusting!"

I could see her clean nightie covered with cum stains as she rushed to the bathroom and I could hear her retching in the sink as she frantically washed my cum out of her mouth.

Half an hour later a clearly annoyed Cynthia stepped back into my room, with yet another clean baby doll nightie, this time green, trying to preserve a half-friendly face. "You never told me you were cumming!" she spat out.

"But I did," I said, with a hurt demeanor, "when I was cumming I told you I was."

"You were supposed to say it before you were cumming." she hissed, trying not to lose her temper. She didn't want to upset me after what she'd been through to gain my approval to New York.

"Well, you didn't say that," I said, with a hurt look.

We both said "goodnight" as she closed my door carrying the box of tissues.

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The next morning I was just finishing my breakfast when Cynthia joined me. She looked at me expectantly with a questioning expression on her face.

"Look Cynthia," I said in a serious tone, "New York is very expensive."

"You promised to look at it," she said with a hard tone.

"I have," I said, "but I could only afford to pay for you in New York if I sacrificed other important things."

I was hoping she wouldn't ask me what important things I was referring to, and she didn't.

"Does what I did for you count for nothing," she said, contriving to sound hurt. "You know I did it because I love you."

"If you loved me," I said directly at her, "you would be naked when you sucked me. We would also kiss each other lovingly beforehand, like other boys and girls do."

She looked quizzically at me and asked in a hard tone, "Would you agree to New York if I was to do that?"

"It would certainly make my sacrifices more worthwhile if I can come to your room tonight on that basis," I said as I walked out of the room.

An hour later I was listening to Mommy and Cynthia again.

"What if he tried to touch my breasts?" Cynthia was asking.

I could hear Mommy's response, "You could keep your hands over them while you blow him. When you're kissing, you could hold them then as well. If he's like most men, his hands will be grabbing your ass."

"He could go berserk," Cynthia said with a worried tone.

"You're joking," said Mommy, "Billy wouldn't have the nerve. Anyway, your room is next to mine. At the first hint of trouble that you can't handle, all you need to do is call for me and I'll burst straight in."

"That's true," said Cynthia reassured. Then with a laugh in her voice she said, "Hey, it looks like I'm going to New York after all."

"And I'll be able to visit you," said Mommy.

Cynthia suddenly sounded reluctant, "Well not in the first semester of course, but after that who knows."

Although I couldn't see her face, I could feel Mommy seething.

Later in evening I prepared myself. I put on my boxers, then applied oil to the front of my legs. Not enough so that they glistened, but sufficiently to give them a slippery quality.

Leaving my room, I was on my way to my sister's bedroom, when Mommy stepped out of her room, put a hand on my arm and whispered, "She's still a bitch. I want to hear her screaming."

I knocked on my sister's bedroom door to hear a confident command of "Come in."

As I entered, I could see the underused box of tissues on the side of the bed. Cynthia was standing there looking at me. She had on the clean green baby doll nightie from the end of the previous night. She clearly intended that it would stay clean as she said, "Promise me that you will not cum in my mouth."

"I swear I will not cum in your mouth," I said in the formal voice of a courtroom witness, knowing my intention was to cum in another orifice entirely.

She was looking gorgeous. Her blonde hair fringe was just above her big baby blue eyes. Her luscious lips were slightly pursed as if she was about to do something that was necessary but slightly distasteful.

She turned to face the other way as she lifted the nightie up over her head, just leaving herself in a pair of matching green satin panties. My mouth went dry as she carefully peeled these down exposing her magnificent bubble butt.

She turned round with her hands covering her breasts. Even so the sides of her full breasts peeped out around her hands. She had a light covering of blonde pubic hair that drew the eye at the top of her long legs. As she slowly walked towards me I backed away, as if very shy, until my back was against a set of drawers.

She stopped in front of me and, still clutching her breasts, awkwardly leaned forward to execute the kiss we'd agreed on.

I whispered, "Congratulations, you're going to New York", then reached my hands around and grasped her delicious bubble butt, pulling her into me. My oiled left leg slipped between her legs, separating them and I could feel her genitalia on my leg.

She gasped, feeling mixed emotions. She must have been feeling elation at my words of confirmation of New York but concern at her position on my leg. She would have thought that it was the warm evening that had caused my leg to slip between hers. Having now secured her success she would not want to rock the boat by complaining about our kissing position.

Because she was holding her breasts, it created a space between us so that my boner was not pressing against her. This, combined with the fact that at this stage I was careful not to try and rub her sex, persuaded her to continue to join in our kiss.

If she hadn't had much experience of blowjobs, she was certainly experienced in kissing. Her wriggling tongue explored my mouth, licking the sensitive areas. She sucked my tongue into her mouth and teased it with her own tongue.

She was concentrating so much on fulfilling my oral requirements that she didn't notice as I began to pull her buttocks backwards and forwards. Slowly but surely I felt a gradual moistening of her sex, until with a start she came to and pulled back from me.

With stage one over; we walked together towards the bed. She was still grasping her breasts and I wondered if she'd considered how she was going to manage the tissues when I ejaculated with the blowjob. In the event I would never know, as instead of sitting on the bed I pushed her down on it and fell on top of her.