A Surprising Tryst with Stepsister

My dad had moved to another state and as such, I only was able to visit during the summer months. After some time, my dad finally met someone and they got married when I was 17. I met her and her daughter, who was a year older than myself, only briefly that summer before I traveled back home.

The next year, they were moved in and now I really got to meet my new step family. They both were overweight and very self conscious. I wont say that I am, or ever was a top male specimen, but I feel I was at least a good average. And now being 18, I was very outgoing, them not so much. I tried to be friendly, but it was to no real avail that first year, things were rough.

I almost did not come back the following year. But decided I would give one more try.

When I arrived, my stepsister was not there. She was out for the first two weeks that I would be there. Forgot what it was, but some sort of vacation with her girlfriends.

When time came for her to come back, I was sort of dreading it. But when she made her appearance, I was astonished. She was still slightly heavy, but over the past year, she had lost over a 100lbs. She was wearing a skirt that fit her nicely, a loose shirt and flat shoes. She was not a "knock out", but she was cute and having lost that much weight, she really did look good. I was amazed and happy for her, but I still did not know what lay in store for us as to how we would get along.

Even though we were both now adults, our parents still wanted us to go out together to the mall for a "family" summer shopping trip. That just meant we all went to the mall together and split up as soon as we got there, agreeing to meet back up at a certain time.

When it came close to the arranged time, it was just her and I. We were sort of quiet with each other, then I offered to buy her a drink while we waited for my dad and her mom to show up. She seemed surprised but agreed, and after I came back, we began to talk and suddenly, we were ok with each other.

The summer flew by, it was just a couple of weeks before I would leave. We were upstairs in her room talking about I don't know what and she asked me if I would rub her shoulders, sure, ok. No big deal.

As she lay next to me and I rubbed her shoulders and neck, I began to go ahead and give her a back massage as well. Still, no real big deal.

But as I continued to rub, her body attitude shifted and the air became charged. We had quit talking. It was just me rubbing her back, her letting out little moans. Then I slowly rubbed down her sides and back up again, I got lower and lower, but finally I got to a point where I just didn't think I could go past without really causing an incident.

To my surprise, she turned her head slightly, looked at me, "Why did you stop? You can keep going."

With that, our breaths became raggedy, quick, and shallow. I let my hands go in front and I began to squeeze and kneed on her tits. She began to moan and then she rolled over and pulled her shirt off, giving me free reign.

"Go ahead, suck on them." She said.

Without further ado, I kissed her first, then dropped my mouth over first one and then the other tit. Running my tongue over each of her nipples, them getting hard so I could nibble on them ever so slightly. This went on for about 20 minutes I guess. I think she came.

But she didn't want to risk going further, not yet. So, our last two weeks before I went home, every night I gave her a massage that ended with me sucking on her tits. I was definitely going to come back the next summer.

The next summer arrived and as I knew I would, I came back. I didn't really know how things would be. Would she have second thoughts about what we did? Would there be awkwardness between us now? I was excited because I hoped to continue, I had hopes of maybe going a little further that we had. But I didn't want to push.

When I arrived, there was no awkwardness and we got along just fine. We talked about things that had taken place for each of us. But after about two weeks, I was really frustrated, nothing had happened and no overtures were made. As I said though, I didn't want to push; I was uncertain of the outcome if I tried.

Then finally, she came to my room which was in the basement. As we talked about things, she lay down on my bed, which was little more than a twin mattress.

She looked at me and said, "Would you rub my back? I've missed your massages."

Without any hesitation I spoke up, "Sure."

I hurried to be next to her, reaching my hands to her back. I began with her shoulders as I did the very first time I did this.

Her eyes closed and both of our breaths began to be short, shallow, and rapid.

Slowly down her sides, up the middle, shoulders, then back down the sides, lower with each pass. As I started on her sides for about the fourth time, she lifted herself slightly up and my hands slid under her to her tits. There was no fighting a bra as she did not wear one this night. I was able to grab a full breast in each hand, tweaking each of her nipples.

She began moaning softly and she rolled over. I lifted her shirt up and off, bending down I began sucking on each of her nipples one at a time.

Then I felt it; her hand reach to the front of my shorts, she grasped my cock by the outline of it, she began to gently squeeze it.

She opened her eyes as I moaned a little, "I'm ready for you, please, do it. Fuck me."

I slid her shorts and underwear off, then took mine off, but I didn't just thrust into her, I wanted to taste her. I kissed her body all the way down to her pussy. As my face got to her pussy, I inhaled the scent of her musk, spread her legs apart and ran my tongue up and down the outside of her pussy lips.

She grabbed my hair, "Oh God that is good,"

She was pushing her pussy into my face as I licked. I finally let her push me down and my tongue speared into her pussy and as my mouth covered her completely, I sucked and nibbled on her pussy lips as I alternately thrust my tongue as deep as I could, in and out.

After a few minutes of lapping her pussy lips and clit I was partially satiated, but now my hunger grew for something more. I wanted to feel her pussy wrapped around my cock.

I got to my knees, lifted her legs up, put the head of my cock at the entrance of her pussy and looked at her.

"Yes, yes. Please, do it. Put it in. I want it." She panted.

I slowly pushed into her and we both groaned with the feeling; her with me filling her and me with the sensation of her pussy enveloping my cock in her wetness.

Slowly at first, I let every inch of my cock push into her, then ever faster I began.

She started to whimper and put her arm over her mouth, biting into her arm to keep from screaming out too loud. As I continued to fuck her, I began thrusting faster and harder, she knew I was close, as was she.

"Pull out, cum on me, please don't cum inside."

In frustration, but not wanting to go against her wishes, I made a couple more thrusts into her and pulled out, just in time too as I began to shoot my cum all over her and the bed.

She reached down and grabbed my cock in her hands and began to milk me. I was shaking and shivering with the explosion that had overtaken me, I lay down next to her, kissing her as I did so while she still stroked my cock.

She looked at me with a drowsy smile, "That was so good."

"Yes, it was." I replied. I then bent down and licked her tit that was closest to me.

"I hope we can do it again?" I asked.

She smiled. "Yeah, we'll do it again."

And we would do it again; almost every night. She would even sleep with me. I think our parents were willfully blind. As long as we were not caught in act, nothing was happening.

Sadly, I could never get her to suck on my cock. She tried it once and her gag reflex was so strong, she got sick. That was disappointing, but all in all, ok.

As time wore on, I finally got her to agree to let me fuck her ass.

When we would have sex prior to this, I would always ensure to lick and rim her ass. When I fucked her from behind, I would make sure to use my finger in her ass. She resisted at first, but began to enjoy having my finger or thumb in her ass while I fucked her doggy style.

Having licked and sucked on her pussy for some time, fingering both her pussy and ass, I turned her over and began to fuck her from behind. As now was usual, I started to work her ass with my thumb as I fucked her pussy. I could feel my thumb pressing into her on my cock between the thin skin between her pussy and ass.

"You're wet as can be, let me have your ass." I pleaded.

She groaned and grunted as I continued to fuck her, "No, you're too big. It's gonna hurt."

"I'll take it slow," I told her, "you're wet enough we don't have to use lube. I want to actually cum inside you."

"Ok, but if I tell you to stop, please, stop."

I pulled out of her pussy, put the head of my cock up to her ass and slowly began to push in. As my cock began to push into her ass further, I got harder and bigger. She buried her head into the pillow and finally, I was in. I sat there for a moment, then slowly, I began to move in and out, getting her used to my cock in her ass.

Then I began to go harder and faster. I was fucking her ass like no tomorrow now, Her head was still buried in the pillow, but even so, I could hear her groans and muffled screams. She never told me to stop though, so I kept on.

"I'm cumming!" I yelled.

I grabbed her hips and pulled her to me, and I began to cum into her ass. With each burst, I thrust forward, letting her ass milk my cock of its cream. Then ever so slowly, keeping my cock in her ass, I lay atop her.

Her breath was ragged as I kissed her. "Thank you, that was so great."

She smiled at me weakly, "I'm glad you enjoyed. You can still use your fingers, but you can't fuck me there again. It's too much. I wanted to let you do it once, and it felt good you cumming in me. But you can't cum in my pussy, you know that."

Disappointed, but satiated, I agreed.