My Step-sister Pt. 05

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On to penetration, and girls sharing secrets.
3.7k words
4.63
23.7k
32

Part 5 of the 10 part series

Updated 09/26/2023
Created 06/02/2023
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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.

I put my spermy penis back into her vagina and went deeper than before; about four inches in.

I fell on top of Chrissy and kissed her cheek. My dick softened and I went a little deeper but it was getting too soft and slowly shrank and fell out. Chrissy put her hand to her pussy. She smeared my cum into her labia then inserted two fingers in her vagina. "How far in did you get?" she asked.

"More than half way." I replied (I'm about 7.5 inces). "It felt great."

"Well, it hurt a bit. At first there is an uncomfortable pressure." Chrissy said. "We'll just have to keep practicing until we get you all the way inside." She said then kissed me with a twinkle in her eye. Chrissy and I fucked almost daily for the next two weeks until I could sink my dick all the way inside her comfortably.

She loved to try new things: me on top; Chrissy on top riding me; me fucking her from behind; or me standing on the floor fucking her from behind as she knelt on the bed (my favorite, especially when I stuck my thumb in her ass to boot). Chrissy's favorite was when she sat in her low chair and I got in front of her on my knees and fucked her. We could kiss, I could easily pinch her nipples (which she loves) and she could watch my dick going in and out of her pussy. She loved this and even trimmed her pussy hair short with clippers so she could more easily watch me entering her slippery vagina. Also, I would tell her when I was close to cuming and she would rub her clit furiously and we often could cum together this way, which was pretty amazing.

We also did not give up on oral sex. Often I would lick Chrissy to orgasm then fuck her. She was especially sensitive when we did this and often she would cum again in just a minute or two. Sometimes I would fuck her then pull out and cum in her mouth. The chair was great for this as I could just stand up and shove my dick in her face. Chrissy would suck me hard and moaned as I blasted off in her mouth. I gotta say, there is probably no better feeling than cuming in a girls mouth when she is into it and sucking hard.

Just before Christmas, Chrissy told me to come home after my hockey game without showering. I thought this was a strange request but did as she asked. She stripped me naked and started sniffing me. We kissed then she kissed my neck. I could hear her sniffing in my scent which seemed to turn her on. She licked my nipples then looked up at me, "Mmmm, salty!" she said.

She licked down my torso then took my dick in her mouth. After sucking me for a moment, she went down and licked my shaft and down to my balls. As she licked my balls, her nose was in my fragrant crotch. She breathed in deeply through her nose and looked up at me. "I love the way you smell." Chrissy said.

For some reason, this turned me on immensely. When she started sucking me again I grabbed her head and fucked her mouth rapidly and came in her mouth in no time. I was so turned on that I picked her up and threw Chrissy on the bed and started fucking her. I didn't even go soft. I pounded away and Chrissy was more vocal than she had ever been, "Yes Greg, fuck me, fuck me hard."

I kissed her and I could taste my salty sperm on her lips. We were both crazed with lust. In only three or four minutes I started cuming again. As I was cuming I rubbed my pubic bone against Chrissy's clit and she started cuming with me. This was the most pure, a****l lust and simple quest for an orgasm I had ever felt. We both seemed to feel that way. God it was awesome.

A few days after Christmas, on Friday, night Suzie the cheerleader had a party at her house as her parents were away. It was mostly the hockey team and a bunch of girls. I went with my teammate Roger (who used to date Suzie). When I got there I found that Chrissy was already there. I guess this should not have surprised me as she and Suzie were friends. The party was fun and I had had a couple of beers (the drinking age was 18 at the time so I was not even i*****l). I had to pee so I went to the bathroom but found it was locked. I went up stairs to find another bathroom. When I finished peeing, I zipped up and turned around to see Suzie standing in the bathroom behind me.

"Um, hello." I said. Suzie took me by the hand and said, "Come with me."

We went into her bedroom and she sat on the bed and patted the space next to her. I gotta say, this was a dream come true. I had had a crush on Suzie for three years. She was super-cute; she is very short, maybe five foot one, with big D-cup breasts. She is a cheerleader and I loved watching her do her cheers and stunts with her tits bouncing around. She was the girl who could give me the accidental boner in school. Suzie leaned over and started kissing me. She was a bit of a hockey groupie and had dated my friend Roger and fucked one or two other hockey players. If I was her next victim, I was all in.

We were making out passionately for a while then I did what I had been thinking about for so long. I caressed one of her big tits in my hand. When Suzie moaned, I knew I had free rein. I felt her big tits and got rock hard. Suzie's hand went to my crotch and felt my hard on. "Oooh, we have a big one here." she said then undid my snap and zipper. Suzie reached into my underwear and pulled my dick out the top. My dreams were turning into reality.

After stroking me off for a few minutes, I think Suzie sensed that I was not going to last too much longer. She slid off the bed and yanked off my shoes then pulled my pants and underwear off. Then, the girl I had fantasized about for three years, took my dick in her mouth. "Oh fuck!" I said and fell back on the bed. Suzie expertly sucked my and jacked my dick with her hand. She kept her hand just below her mouth and moved her head and hand in unison. It felt like I was going eight inches down her throat. I did not last long. I started thrusting and came so hard I saw stars.

When I was finished, Suzie took my hands and pulled me up. She gave me a light kiss then said, "Put your pants on, we should go downstairs." I stood but instead of putting my pants on, I pushed Suzie back on the bed.

"Oh, what are you doing?" she said with surprise.

"I'm returning the favor." I said.

I unsnapped her jeans and pulled them off along with her panties. Suzie giggled and then as I kissed and licked my way up her thigh she started to moan. When I got to her crotch, I was blown away by her musky scent. I went in and started licking her pussy. She tasted amazing. I was so turned on. I had been making Chrissy cum several times a week and I knew something about licking pussy. After licking her gash and sucking on her labia, focused in on her clit, flicking it with my tongue then nibbling on it with my lips and gently with my teeth. In no more than three minutes Suzie was gushing and thrusting her hips. Then she moaned loudly and her body was racked with spasms and she orgasmed.

When she calmed down I pulled Suzie up and kissed her with my sloppy face. She laughed then wiped my wet cheeks with her hands. Then she said, "Chrissy told me you were a great pussy licker."

I was stunned. I had not told any one about Chrissy and me and I assumed she hadn't either. Suzie saw the sock on my face. "Don't worry." she said, "Your secret is safe with me." She kissed me then we got dressed and went downstairs (one at a time).

As the party was winding down, Chrissy asked me to take her home. On the drive home Chrissy reached over and started rubbing my crotch as I drove. "So..." Chrissy said, "Can we fuck when we get home or are you too wiped out from Suzie's blow job?"

"What the fuck is with you woman and your over-sharing? Why are you talking to each other about your sex lives?"

Then Chrissy explained how Suzie had confronted her in a manner similar to how my teammate Roger had announced that he thought I was fucking my step-sister.

Suzie had said to Chrissy, "I see how the two of you act around each other, so flirty, so familiar, so happy in each other's presence. I know you two are having sex."

Chrissy had broken down and admitted that indeed we were. About how we started out masturbating in front of each other then pleasing each other orally then, recently, fucking. Then they started comparing notes; what they liked to do to boys and what they liked boys to do to them.

Chrissy said that Suzie had put it to her directly, "I might have to try Greg out."

Chrissy then responded. "Go ahead, I don't think you will be disappointed."

So that's how my adventures with Chrissy and Suzie began. But there was a lot more fun to be had with both of them -- and Roger too..

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ScottishTexanScottishTexan11 months ago

It was good right up until you foreshadowed Roger joining in for a foursome. I've got a bad feeling about this. 😕 You've already had Greg cum inside his own mouth. I can easily see how you're only a half-step away from having Greg suck Roger's cock or vice versa.

And what the hell was going on with all of the censorship? You used i*****l for illegal? You’re writing a story about people fucking each other but you’re censoring certain words that aren't even vulgar? How stupid is that idea? You’re lucky that I didn't drop another vote of one here. 2/5

AnonymousAnonymous11 months ago

Good story. I have a feeling there will a 3some coming up soon. Can't wait for part 6

AnonymousAnonymous11 months ago

Pretty good chapter but the ending feels like the beginning of some swinging/swapping/cuck shit is about to happen. 3/5

MikeOrMikeyMikeOrMikey11 months ago

5 Stars.....another great installment.

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