My Step-sister Pt. 05

Wednesday morning I went into Chrissy’s room after our parents left for work. Chrissy is my step sister and we have been playing sexually for two months. We started by watching each other masturbate then pleasing each other both manually and orally. When I went into her room, she was still in bed. I lifted the covers and climbed in next to her. I wrapped my arm around her chest and cupped her c-cup breast as my hard on pressed into her butt.

Chrissy moaned and stretched and moaned awake. I ran my hands over her body as she came alive. She had been sleeping naked as always. She turned over and got on top of me. She put her tits in my face and wiggled back and forth slapping my face with her awesome boobs.

“Morning!” she sang cheerily. Then she jumped off the bed. “Gotta pee.” she said and raced off to the bathroom.

When she returned, I was laying on the sheets stroking my very hard dick. Chrissy sat next to me and grabbed my dick. “What should we do this morning?” she asked with a mischievous smile on her face.

I pulled her knee so her right foot was now between my knees. I licked my fingers and then put my hand between her legs and began stroking her lady-parts.

“I showed you my unique, fun technique for jerking off. What do you do that I don’t know about?”

Chrissy jumped off the bed and went to her dresser. She grabbed a small round hair brush. I guess it was for curling her hair but I’m not sure. It had a long narrow handle that was tapered at both ends. It was not very thick, maybe 1/2 inch thick in the middle and about five inches long. She sat down in her little padded chair. She had this odd chair that was like a wing-back chair only down-sized. I guess it was for a c***d, but it was not super small, kind-a 3/4 size. Anyway. She sat in the chair and put her knee over one arm. She looked me in the eye and then put the handle of the brush in her mouth to moisten it.

She then smiled at as she slid the handle into her pussy. She rubbed her clit with her right hand and moved the brush in, out, and around with her left. After a few minutes of this, she started rubbing her slit fast and furiously. Her eyebrows furrowed and she shut her eyes tight as she leaned forward and spasmed in orgasm. God it’s hot watching a woman masturbate!

This was a long time ago and I have been with almost 30 woman since Chrissy and I were in high school. But I have never been with another woman who could cum as fast and easily as Chrissy. She was a lot of fun to watch and to be with partially for that reason and partially because she was so open and honest about her sexuality.

After her orgasm, Chrissy leaned back and smiled at me and said, “I’m not done yet step-brother.”

She pulled the brush from her vagina and brought it to her mouth, inserting the entire handle in her mouth tasting her juices. Her right hand was still rubbing her clit and stroking her pussy. To my surprise, she brought the brush back down between her legs. She pushed her butt off the edge of the chair and leaned back, then inserted the handle into her anus.

“Ohhh” she groaned. She resumed stroking her clit and pistoned the brush slowly in and out of her butt-hole. The brush and her fingers slowly picked up the pace. I had been slowly masturbating but now I got off the bed and went over to Chrissy. I knelt in front of her for a close-up view of her anal stimulation and started stroking faster. We were both heading for our orgasms. Chrissy was now pulling the handle out so the thickest part was just on the outside then she would shove it back in.

My orgasm was approaching and I stood so I could spray my seed over Chrissy’s heaving chest. I started to cum and as my semen started to splash over her tits, Chrissy squealed and came with me. As we calmed down, we looked into each other’s eyes and smiled. Chrissy leaned forward and sucked my dick briefly into her mouth tasting the last of my cum. The she stood and gave me a peck on the cheek.

“I have a test.” she said and then she ran off to the bathroom to clean up and get ready for school.

I know there were dildos in those days, but I had never seen one. Watching her put an object in her orifices was a big turn on for me. I knew Chrissy and I would be fucking before too long. It was just a matter of time. Now I had anal sex to fantasize about as well.

Two days later it was Friday. We had pep rallies in school every Friday. In the fall it was for football games. Now it was December and this rally was for the ice hockey team; I played on the first line as a left winger. I was not headed for a college scholarship, but it was my third year on the team and I was one of the better players.

The pep band was playing and the cheerleaders were jumping around – their boobs hoped up and down and occasionally then kicked up their legs to show their blue panties. While I was not really a rah-rah type of guy, I did enjoy having an excuse to stare at these hot girls and their bodies. One of the cheerleaders was Suzie who was a short blonde with big tits; I had a wicked crush on her for the last three years.

Then I felt a hand on my arm. Chrissy leaned in spoke directly in my ear. With the band playing loudly in the huge high school foyer, no one could hear her but me. “I’m on the pill.” She said.

I turned and looked at her and she was smiling and her eyes sparkling with excitement. “I started a month ago and now we can fuck without worrying about pregnancy.” Then she leaned in and whispered in my ear. “You better come home after your game tonight.” Then she walked away.

Hockey is big in my city and we had a good crowd at the game. We won and exciting 3-2 game with a goal in the final two minutes. In the locker room we were lively and excited; the season was underway, we won our game, and it was Friday night. In the shower my friend Roger said to the team. “There is a party tonight at Suzie’s place.” Roger was our best player and he went on to play D-1 in college. Suzie was one of Roger ex-girlfriends. He was a stud and dated a girl for a month or two then moved on. Suzie and Roger are still friends and she is a friend of mine as well.

Roger looked right at me. “Are you ready to party Greg?”

I hesitated then said, “I think I’m gonna lay-low tonight.” This was unusual because I always showed up at post-game parties.

“Lay-low my ass.” Roger said. “You are going to fuck that step-sister of yours.”

I did not say anything. I turned into the shower spray, afraid that I might be blushing. Roger continued. “I see the two of you whispering with each other in the hallway and eyeing each other across the cafeteria. I think you two are doing-the-nasty.”

I smiled to myself but didn’t say anything. When I turned my shower off and started to head out, Roger followed me to the lockers. “I’m on to the two of you.” he said low so only I could hear.

When I got home, Chrissy was wearing ribbed white tank top and a short pleated skirt. Holy shit she looked sexy. The tank top was sheer enough that I could see the outline of her areolas through the material. In addition, her nipples were poking little tents in the puckered fabric. My dick was getting hard already.

She got up from her chair and walked over to me. Her tits swayed beneath the thin fabric. She stood right in my face. “Hey little brother.” she cooed (she is a few months older than me). I grabbed her and pulled her to me. I kissed her on the lips passionately. She returned my kisses and as we kissed I ran my hands over her tits and gently pinched her nipples which became hard as pebbles in my fingers. Then I ran my hands down to her ass and grabbed her butt through the pleated skirt.

“I saw you looking at those cheerleaders.” she said. “They clearly turned you on so I got out my pleated skirt for you.” Fuck, this girl is SO SEXY. She loves to turn me on; I love to return the favor. I pulled her skirt up and grabbed her ass. She was not wearing panties. Today, going panti-less is a thing, but back then, I had never heard of it – but I liked it.

I scooped Chrissy up and carried her to the couch. I laid her down and fell on top of her. We continued kissing and my hands roamed over her body touching her tits, her stomach, her legs, her pussy. Then I started moving down. I lifted her shirt and sucked her tits one at a time. The I continued down and dove under her skirt and started licking her pussy. I went up and down, left and right. I would flick the base of her vagina then go up one side sucking her labia. Then I’d flick her clit a few times before going back down and up the other side, then back to her clit. Her juices were flowing like crazy soaking my cheeks and chin with her delicious fluids.

Finally I zeroed in on her clit, I flicked it with my tongue over and over. When the clit stood-out proud, I could tell she was about to cum. I sucked her clit in and out of my mouth quickly with forceful suction. Then, as her orgasm started, I added my top teeth to her stimulation. This seems like it would be a bit painful, and maybe it is, but it makes her cum like crazy.

As her orgasm was calming down, Chrissy said “Fuck Me Now!” This was the moment we had been anticipating for months. All of our masturbating, petting, and oral sex had been leading to this moment.

I picked Chrissy up and carried her to my bed. I pulled her skirt off and got between her legs. I placed my dick at the entrance to her vagina and gently pushed in. Oh my God she was tight. I could barely get an inch of my dick in her narrow opening. She sucked in her breath and put her hands on my hips indicating that I should go slowly. I backed out, pushed in, backed out, pushed in. Each time I was going a mere millimeter further inside of her smooth vagina. Her tightness felt great, but I could tell it was a bit uncomfortable for her.

I could only get about two, maybe two and a half inches inside of her before she would wince. So I stayed at that depth and moved in and out, slowly going a bit faster each time. I was getting ready to cum. Not wanting to thrust too hard in my final moments, I pulled out and rubbed my dick fast and hard over Chrissy’s clit. As I started to cum, I bathed her clit and outer labia with my seed. This triggered her orgasm and we both moaned in our orgasmic bliss.