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Introduction:

Edited and reposted version of Step Sister Surprise.

Growing up I always knew that I was hypersexual. As soon as I hit puberty, I couldn’t walk down a hallway at school without catching sight of sexy classmate and getting hard. I always ended up rushing to the bathroom for relief.

It didn’t help that I was surrounded by gorgeous women at home. I had two stepsisters that were absolute bombshells, Kelly and Ashley. Kelly had long brown hair that fell past her shoulders in silky waves. She had beautiful hazel eyes that drew your attention as soon as you looked at her face. At 5'6" and 115 pounds, her frame was slender, but her 34c tits and amazing bubble butt gave her the right amount of curves. Ashley was a few inches shorter but matched Kelly's build very closely. She had short cropped black hair that fell just down to her neck. Her skin was also paler than her sister's.

Ashley was the sit-at-home-and-sketch artist type, while Kelly was more outdoorsy. Years of soccer and volleyball had toned Kelly's muscles and tanned her skin to a beautiful bronze. Ashley's skin was also looked delectable though. She had covered herself in amazing tattoos that always peaked out of the skimpy outfits she would wear around the house. They offered a fierce contrast to her porcelain complexion. There personalities were very different, but it never seemed to stop them from getting along.

My senior year in high school we were all living with our parents. Ashley was 23 and pursuing an apprenticeship as a tattoo artist at a shop close to home. Kelly was 20 and had decided to continue living at home while she went to a local college. Neither one of them saw the need to take on a rent payment while setting themselves up for a career.

I was coasting by in my last year of high school. To be honest I was regretting the lack of sex I'd had over the past four years. I couldn’t seem to get the attention of any of the girls at my school. Every time I tried to talk to one, I would get so self-conscious. I either didn’t say anything for fear of judgement, or I said something so stupid it justified my fear.

I didn’t think I was bad looking. I was 6 foot tall and weighed 170 lbs. I had decent muscle tone that could trick you into thinking I was athletically inclined. I had blond hair and green eyes. My mom and her friends always assured me that once I got a little older, and the girls were easier to talk to, I would be a real heartbreaker. Unfortunately, that made a shitty reference when breaking the ice with coeds. Needless to say, I had continued my tradition of masturbating three to four times a day to relieve the tension.

I woke up one Saturday morning and headed downstairs to see what the family had in store. "Good morning, Tommy", my stepmom said as the smell of frying bacon seduced my stomach. She was wearing tight beige capri pants and a button up blouse. She left the top two buttons undone revealing just a hint of cleavage poking over the tank top she had on underneath. Her sandy blond hair was drawn back in a ponytail. The last few weeks I had really started to see how sexy she was. At 34 her body was in better shape than any of my friend's moms. Her breasts were easily a 32F. She had long tone legs and her ass had the perfect amount of fat.

We had an amazing friendship for a stepmother and son. My birth mother had divorced my father when I was only six, splitting my time between two houses. When my father remarried, Lisa brought two daughters along to live with my dad. After the first few months, she had won me over with trips to the movies and surprise toys. We have been close ever since.

"Morning Lisa. You guys got plans today?", I asked taking a seat at the kitchen table.

"Me and John are going to meet some of his friends from work to play golf. Are you going with Ashley to the art walk downtown this morning?"

"No. I think I am going to play halo with Mike later."

"Are you sure? You might meet a cute girl."

"I'll take my chances at the loss," I concluded.

After I had eaten breakfast, I went back to my room. I was pleased to know that I had the house to myself this morning. Kelly, being the last family member home, had soccer practice that morning. I waited another hour or so, and after my sisters left and my parents said goodbye, I broke out my lap top and started looking through my favorite porn sights.

I picked a video where a young-looking guy was getting his dick sucked by a milf. She was blowing him with serious motivation. Every few seconds she would deep throat his cock and gag thick saliva all over his shaft. I was ten minutes into the video when I got a wicked idea. Pressing pause, I stood up from the computer chair I had been using at my jerk off station (or desk, if you're a fucking prude) and made my way down the hall to Kelly's room. I wasted no time diving into her underwear drawer and finding a pair of black silk panties. They were boy shorts with a cute lacy back. I headed back to my room with my new prize in tow. I hit play on the video and watched as I slowly rubbed the silky material across my throbbing rod.

The texture was so smooth, and every time it completed a voyage across my cock, precum would drip down my shaft to be cleaned off with the next swipe. The milf in the video continued her oral assault, and I started to envision Lisa giving me the same great treatment. I had never fantasized about her before and my breath caught in my throat at how erotic the mental image was. The blood in my cock surged towards the tip, and I had to stop for a few seconds to let my dick throb. I was amazed at how turned on I was by this new fetish. I took Kelly's panties and wrapped them around my dick and slowly began jerking. I felt a tall wave of cum churning around inside my balls. I let my head roll back and closed my eyes envisioning Lisa gagging a thick layer of spit on my cock and stroking me with her hand at the same time.

"I'm gonna cum in your mouth Lisa," I whispered with my eyes still closed imagining her presenting me with her open mouth. The silky fabricate made one last brush against the glans of my tip and I exploded. Rope after rope of cum shot out of my cock and across my hands and chest. It continued pulsing for what felt like and eternity. I finally came back to my body and realized I still had the panties wrapped around my cock in a death grip.

"Is this what you do when were gone!?"

The shout drew my gaze instantly to my bedroom door. Ashley was standing there staring at me. I guess in my heated state, I hadn’t heard her come home. I was frozen. I had no idea how long she had been watching me or what she had heard. "I swear if those are my panties, you're dead,” she growled. She stalked crossing the room in three strides. Grabbing a fold of the panties that were peeking out of my hands, she briskly pulled them from my cock, still sensitive from its recent climax. The sensation caused me to moan slightly. She either didn’t care or didn’t notice. Upon realizing that they weren't hers, she returned her gaze to me. I finally realized that I was naked with my torso covered in jizz. I got up and found a towel laying on my bedroom floor to cover myself with. I finally found words after what felt like years of shocked silence.

"Ashley look you can’t tell anyone about this. I was really horny, and I lost control of myself." I was about to have a nervous breakdown. Did she hear me whispering my fantasy about her mom? If she did, would she tell? I didn't know how I would face my family if that happened.

"That doesnt mean you can just rummage through our underwear. Did you get these from Kelly's drawer?"

"Yeah," I replied shamefully.

"Well get them from the hamper next time. You have no right to invade other people's living space. How would you like your privacy violated like that?"

My mind was blown. My first thought was you watching me shoot cum out all over the place felt pretty violating. I stifled that comment though, not the time to start a new argument. Was she only upset that I had snooped through Kelly's room?

"You’re right." I replied, the words almost a question. "Are you not mad that I used her panties to jack off?" I asked really confused.

"Little brother everyone masturbates. It's not unusual to experiment with new techniques. I don’t want you to feel ashamed about your sexuality. Just so were clear though, use dirty panties so that they come back clean and you don’t have to go through our rooms."

I was shocked. I felt horrible. I looked at Ashley and didnt know what to say. We had never been really close since we had such an age gap. For her to have taken a moment like this and made me feel secure with myself was too much to bear. I couldn't help but make her elaborate on one thing though.

"So you don’t care if I use your panties to masturbate?"

She sighed "look high school is tough. I’m sure you're really horny and that you can barely make it through the day without running to the bathroom to jack it." Boy did she hit the nail on the head there.

"I can’t even tell you the things I did in high school to get off. If it helps you get all that out of your system, then sure you can use my panties."

I immediately wondered what she meant by what she did in high school. The final pep talk she gave not only helped to reinvigorate my self-esteem but also emboldened my penis to begin making a resurgence.

Ashley looked down and noticed that the towel I was wearing was beginning to tent. She giggled and turned around to leave. As she made her way to the hall she said, " Don't move until I get back." She made her way down the hall with Kelly's panties still firmly in her grip. I waited a few seconds then decided to wipe my love stains off my chest. I was finishing wiping down the mess when a red object flew into my vision. It hit my chest and fell to my cock. It hung there strangely, and I noticed it was a thong.

I looked to my door and saw Ashley standing there grinning. I noticed that she wasn’t wearing pants. I followed the long line of her ivory thighs accentuated with sensual colors from her tattoos and realized she was wearing the panties I had stolen from Kelly. I felt my face flush as my gaze returned to her.

"I decided that I want to watch you just once. Call it payment for the panties."

I was stunned but also rock hard as I looked back at her. I dropped the towel and grabbing the new pair of panties began stroking myself slowly. As horny as all this was making me, I decided speaking may only jeopardize the opportunity.

I watched Ashley in my doorway. She slowly walked over and lay down on my bed. She watched me rubbing the tip of my cock with her panties. I was leaking precum already. She slowly started to run her hands over her beautiful legs. I didn’t know if she was putting on a show or getting turned on herself.

I felt my balls pushing cum into my engorged rod. She spread her legs so I could see where the underwear was pulled tight against her pussy lips. She rubbed the shiny material right where a wet spot was starting to form. I moved closer feeling my orgasm building. Stopping for a second, I got on the bed kneeling between her ankles. I continued to watch her rubbing her mound. She hooked one finger under the crotch of the panties and pulled them sideways, revealing her shaved mound. Her lips were a dark shade of pink and dripping with juices.

The sight was too much. I groaned and unloaded my seed. It launched from my cock and splattered the black silk guarding the mound of her beautiful cunt. I continued pumping as shot after shot splashed her lips and thighs. Ashley legs began to shake, and a moan escaped her.

"So fucking good you naughty little boy!!!," she shouted before rocking her hips in an involuntary orgasm triggered seemingly only by the sight of my performance and warm kiss of my ejaculate.

I stopped rubbing myself. I was both shocked and in love. She must be way hornier than I am if that little stimulation could cause that much pleasure. I couldn’t believe that Ashley would let me do something like that to her. This was my first real sexual experience, and it was already to bizarre to contemplate.

"Hello, I'm home" I heard from the living room. Kelly's soccer practice was apparently over.

Ashley smiled knowingly and stood up from my bed.

"This can be our little secret, okay? And don’t worry I won’t tell my mom you whisper her name when you cum."

She did hear. I was beyond caring at this point.

"Besides" she finished "Its not like I don’t think of your dad when I masturbate." She quickly left my room and ducked down the hall to hers. I finished wiping myself off and threw on a pair of gym shorts before laying down on my bed. What the hell had just happened? I looked at my floor and saw the red thong. I had a feeling things at home were going to get a lot more fun.

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