Chapter 35: The Coupon
It was late on a Thursday evening in the middle of January when I got a phone call. "Jeff, could you please come spend the night?" Jess asked me.
I thought about it, and decided, 'Why not?' Jess had not asked me like this before, and the thought of that beautiful, mature woman asking me to spend the night with her had me quite hard.
Jess met me at the door with a smile and a big kiss. She helped me undress right there, and led me upstairs. She stopped me before we entered her room and asked me, "Do you remember what you got Michelle for Christmas?"
"An MP3 player," I said.
"What else?" Jess asked with a smile.
"A gift certificate entitling her to a night with you and Rachel," I replied.
"Almost," Jess said. She handed me the coupon that I had given to Michelle. It said that she was entitled to a night with Rachel and Jess who would give her a sensual massage, followed by a night of any type of sexual activity that she wanted.
"So she cashed it in?" I asked.
"Yes, she did," Jess said. "Tonight."
"Then why did you call me?" I asked, confused.
"We gave her a massage," she replied. "We both pleasured her. Since she was entitled to any type of sexual activity, I asked her what she wanted. She wants you." With that, Jess opened the door, revealing Michelle in bed, naked, glistening with oil, sweat and sex. She was sitting up against the pillows, her legs spread open, her fingers playing with her pussy.
I walked to the bed and sat down next to her. I was actually quite nervous. I asked her, "Are you sure about this?"
She nodded shyly and said, "Look, I'm not like Rachel or Jess. I don't like pain. I don't like embarrassment. But I've seen you fuck them. I've seen the way that you make them feel. I want that."
"But you've got other boyfriends," I said. "Older guys."
"I know, but they don't make me feel like you make Jess and Rachel feel," she said. "The sex is nice, but it's just nice. I want more. I want to explode."
"I think you are expecting too much," I said. "Rachel and Jess get off because I am feeding their kinks. It might not be the same for you."
She pulled my head towards her and kissed me gently on the lips. She pulled away, leaving her hand behind my head, and with a smile she said, "I'm willing to take that chance."
She kissed me again, harder, more passionately. Her tongue played with mine and she pulled me over on the bed so that I was half lying on her. My hand reached up and cupped her breast, squeezing her nipple gently as my other hand twisted in her hair and pulled it tightly.
I realized what I was doing and pulled away, saying, "Sorry. I'm so used to being with Rachel and Jess."
"That's OK," she said. "A little pain I don't mind, just don't bring out the whips."
"Damn!" I exclaimed regretfully, then laughed with her.
I noticed Rachel and Jess sneaking out of the room. "Hold it!" I told them.
I turned to Michelle and asked, "Do you want them to leave?"
Michelle looked at them and shrugged her shoulders. "I don't care," she told me.
I turned back to the women and said, "Stay. Kneel." I pointed my hands to either side of the bed and they came over, one on each side of the bed, and knelt down with their chins on the bed.
"Good, I might need you later," I told them. "But for now, I'm going to have some fun with my big sister."
"And I with my little brother," Michelle said in a giggly tone of voice. She pulled me back into a kiss and I forgot about Rachel and Jess as I explored my lovely sister. I kissed her for a long time before moving my head down her body. I explored her breasts with my tongue and fingertips, enjoying the way I could make her pink nipples stand up, the area surrounding them crinkling into ridges. I kissed and licked over her stomach, tasting her sweat and the massage oil that had been used on her earlier.
I moved down to her smooth pussy and looked up at her questioningly. "I know you like your ladies bald, so I had Rachel shave me again."
"Mmmmm," was my response as I buried my face in her. She tasted so sweet, so fresh. I spent a long time slowly licking her up and down, delving my tongue in deeply, then allowing it out to play with her clit.
I felt like I could have gone on all night, but Michelle was moaning, begging, yelling, saying, "Please Jeff! Please little brother! Please fuck me! Please fuck your big sister!"
Who was I to refuse? I moved back up her body, biting her nipples on my way up. I kissed Michelle, and just when I was going to reach down to position myself at her entrance, I felt another hand on my cock, pointing it where it wanted to go.
I was looking into Michelle's eyes as I slowly pushed my cock into her. I loved the way that her eyes got big as she felt me filling her. When I was all the way in, she moaned, "I feel so stuffed! You have such a nice cock, Jeff!"
My cock swelled even more, along with my big head. I loved that I was pleasing my sister so well. I started rocking in and out slowly, but soon Michelle was demanding more. "Harder" and "Faster" were the two words repeated most often, along with much unintelligible grunting.
Finally, Michelle began groaning and whining as she approached her orgasm. She was panting and her chest was heaving, and it was so sexy watching her face that I knew I would not last long. Luckily, I didn't have to, as she screamed and came, her clenching pussy sucking the cum right out of my cock.
When my cock was finished spurting, I collapsed on top of her, breathing hard. A thought came to me and I said, "It's probably a bit late to ask if you are on the pill."
Michelle laughed, her pussy doing interesting things to my deflating cock. "Oh, I could just see it now. 'Mom, Dad, I'm pregnant, and Jeff is the father.' That would go over well! Yes Jeff, I am on the pill!"
I rolled over and fell onto my back next to her, laughing and trying to recover. I felt the bed move and heard Michelle's gasp just as I felt a mouth engulf my cock. I looked down and Rachel had my cock in her mouth as Jess was cleaning up Michelle.
Rachel popped my cock out of her mouth and said, "All clean."
Jess picked her head up and told her daughter, "It will take me a little longer to clean Michelle. Jeff left a big mess in her."
Rachel smiled at me and started sucking on me again. "I thought that you said I was all clean," I said.
"You are," Rachel replied after removing my cock from her mouth. "But you don't think that one time is going to be enough for your sister, do you? I'm just helping you get ready."
It didn't take Rachel very long to accomplish her mission, at which point Michelle pushed her out of the way and started sucking me. It got even better when Rachel donned her strap-on and started fucking Michelle from behind. I managed to cum once in Michelle's mouth, then again up her cunt. Before we fell asleep, Jess tucked us in and she and Rachel left the room.
I woke up before Michelle in the morning and just lay there watching her for a while. I could not believe that I had fucked my sister. I'd had wet dreams about her, but I never really thought it would happen. Even while I was playing with her and Rachel, I didn't know if we would cross the line. Now we had, and I can't say that I was sorry. I just didn't know where it would go.
Michelle opened her eyes and saw me watching her. "Good morning, little brother," she said sleepily.
"Good morning, big sis," I replied, kissing her gently. "Did you have fun last night?"
"Mmmmm hmmmm," she purred. "I think it was the best present I ever got."
"But now what?" I asked.
"Now we go on," she said.
"What do you mean?" I asked.
"You are so cute," she said. "You can completely dominate a woman, including one twice your age, but you are so unsure of the little things. We go on. Nothing changes. Except that every now and then, I'm going to want you to fuck me. And if you ever want to fuck me, just ask. Otherwise, everything is the same as it was yesterday. Simple."
I kissed her again and thought, 'I guess big sis knows best.' As she was going to take a shower she said, "Maybe next time you'll do my ass?"
It was a good thing that Rachel chose that moment to come in and see if I needed anything, because I did.