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Come along on a trip with a young man as he becomes a man with the help of his stepsister, her college roomate, and an amazing mature woman that takes them all under wing and helps guide them though young adulthood.
She (21) is three years older than I am (18) and went off to college while I was still in high school. I had caught glimpses of her before, but of course, I just kept my mouth shut and dreamed about it at night. She had grown up beautifully in college, now at 5'8" 115lbs with long blond hair, blue eyes, a very shapely curve to her body and nice tits. She was and still is what every man growing up dreams of having as a wife someday.

I am home on leave after basic training, AIT, Airborne, Air Assault, and Pathfinder schools, and getting ready to ship out to my first duty assignment overseas. I had been back home for about two or three days at this point, and she (Stepsister) got into a big fight with her current boyfriend/whatever he was and needed to get some of her stuff out his place to take to her new apartment Mom and Dad helped her rent for her Senior year at college so she did not have to stay at the dorm. I of course drew the short straw and had to help her move into her new place.

The move out was uneventful, up until the end and they got into it again and I stepped in and pulled her out of the house, and we got in my truck and left for her new place. It was June and hot, so it was not fun getting all her stuff and the new bed up to the second floor of this apartment she rented. We just dumped most of the boxes about where she thought she wanted them and made sure the bed was on the frame and box spring. She decided we were done for the day and went to get a pizza to pay for the help.

When she came back, she had a large pizza and twelve pack of beer with her...Nice! Sis was looking out for me. So, we sat there on the couch and ate pizza and drank a few beers and caught up a little. She had a ton of questions about me being in the military and what it was like, etc... I answered them and we just kind of sat there recovering from the move and the heat for a while. I figured it was time to get going and took the trash over and dumped it, as I turned around she was sitting there crying...(I was guessing at this point, give her a hug and tell her everything is going to be fine like a good stepbrother and I can get the hell out of here!)

I went over and sat next to her on the couch and put my hand on her back and said, “Don’t worry about that loser jerk. If he could not see he just made a huge mistake with an awesome woman, he did not deserve you anyway”. I was proud of myself for coming up with that on a spur of the moment as a young, dumb, and full of cum guy just out of basic.

She put her head on my shoulder and gave me a hug. I was starting to get uncomfortable now, she just kept hugging me. We must have sat there for a good ten minutes or so. I was getting uncomfortable because her left breast was pressed up against my chest and at some point, she had taken off her bra so I could feel her now hard nipple on my chest and it was starting to get me aroused.

I was trying like hell to think of anything but her boob and nipple pressing on my chest, but it was not working, and I could feel my cock starting to grow in my pants. I figured oh great, now she is going to freak out and cause a big issue because I was getting hard hugging her. I was looking for a way out, without letting her know I was getting a hard on hugging her, and then it happened. She let go of me with her right arm and laid her forearm right on my crotch and of course right on my growing cock.

When this happened I kind of flinched and braced for impact; figuring I was going to get slapped or punched for getting a hard on while my stepsister was hugging me. I think I ran though about ten different excuses in the second or two it took for me to realize that she was not yelling and screaming at me or throwing punches. I relaxed a little and opened my eyes to look at her, she was sitting there with those big blue eyes looking right into my soul and I noticed she was gently rubbing my pants too. At this point I felt like a deer in the headlights and did not know if I was supposed to run or strip down and have fun.

She could tell I was confused and a little apprehensive and she said, “you know it is ok if you think I am cute and have thought about having sex with me, right? We are not really related. Your mom and my dad got married, but they did not have us together, they did not even adopt us…” (Good Point.)

I of course was speechless at this point; I had dreamed of this happening since I met her when we were younger...but never thought it would ever be anything more than a good fantasy to dream about. I was still not sure though; she was way out of my league and not a girl I would have approached on my own even if we were not related in some way.

She could tell I was still worried, so she made the first move. She slid her hand up and put it in my pants so she could feel my now fully erect cock (that was straining against my underwear and pants to get out) in her soft and warm hand.

At this point I figured if she is touching my dick, then what do I have to lose. I told her “I used to sneak a peek every chance I got and had spent more than a few nights laying there dreaming about how amazing it would be to have sex with you, not just look at your beautiful body and have to dream about it.”

While still looking me directly in the eyes, she moved in closer and started kissing me. I was all in at this point and took her head in my hands and began to kiss her like I had never kissed a girl or woman before in my life. I put all of my passion, excitement, and happiness into it and just enjoyed it for everything it was. It might be all that I got, but I wanted to know what it was like to just fully express your love to someone.

We sat there for quite a while, her holding on to the head of my cock and kissing each other very passionately. She then moved away a little and asked me “how much sexual play have you experienced since she left?” While she was asking me this, she was taking off her shirt and showing me her beautiful full breasts that both had extremely hard and erect nipples on them. This was the first woman that was older than me I had been with and the first time I had seen full grown D cup breasts as well.

I stumbled a little in my answer while looking at her full beautiful breasts in front of me. She laughed a little and said, “you like my boobs, do you?”

“yes” and then I continued with my explanation of the sexual exploits I had to that point. It mostly consisted of feeling breasts, I got to finger a few girls and even got to lick a pussy once. I had my cock licked a few times and a quick blow job, but not to completion.

She moved in closer again and started to unbutton my pants and told me, “I will make sure you have a very enjoyable experience this time”.

I leaned back and she pulled my pants and underwear down, so they fell to the floor and she looked at me and said, “he is quite a bit thicker than I remember the last time I saw you…” She then started to rub my now throbbing cock with her soft warm hands. I was sitting there hoping this was not going to end abruptly, she was on her knees and bent over me slightly, so I decided to go for it and put my hand on her butt and started to caress it. I had watched her strut this thing as a cheerleader at our high school for three years, that was torture. She stopped for a second and pulled her skirt up so I could see she did not have on any panties and then went back to stroking my cock.

This was all so amazing to me I just decided to go with whatever this was and see where it went. I slowly made my way down her beautiful butt to the point where I could just reach the lips of her pussy and slowly moved my hand over closer to her. I was surprised to find that she was already wet, and she pushed her hips back towards my hand and said, “go ahead you can play with her if you want to”.

I slowly and gently spread the lips apart and inserted a finger into her, she moaned a little and told me to keep going. I then realized she was now licking and taking the head of my cock into her mouth slowly but deeper each time.

She stopped for a second and said, “let me know if you think you are about to cum.” So, I agreed, and we continued to explore each other in a very intimate way.

It was not long, and I could tell I was about to cum, so I told her I felt like I was about to let loose and she took one hand, grabbed the base of my cock, and squeezed very hard. It was amazing, she was obviously very experienced at sex as I came back from the edge and we continued to play with each other, each time I got close she would grab me again and we could continue. I cannot remember how long we played this little game of pushing off me cumming, but at some point she decided she wanted to let me cum and I told her I was about ready again and she just kept moving her head up and down on me and it felt like I exploded with the force of a water cannon in her mouth.

She just kept moving up and down on my cock and I could tell she was swallowing every drop of that massive load of cum I had been dreaming of giving her for years. I also noticed that she was now dripping wet to the point that there was a small puddle on the couch under where her pussy was, and my hand was completely soaked with her. When she was satisfied that she had taken all of me, she slowly turned and sat back down on the couch and kept running her fingernails up and down my cock.

She looked at me and asked, “how did you like that?”

“That was amazing and even better than I had ever dreamed of”.

She smiled at me and asked, “are you ok with how wet I get?”

I told her I thought it was amazing, and I loved it. She then took my drenched hand and moved it up to my mouth and said “taste it...”

I did and it was not what I thought, it was strangely sweet and a little bitter at the same time and had a very erotic fragrance to it that I liked very much.

“I figured out when I was younger, that if I got really turned on by a guy, I could do this…” She explained that she would even do this sometimes if she was not playing with a guy in a sexual way. I was amazed by her beauty and how honestly, she was talking with me about very personal sexual things.

We sat there on the couch for about twenty minutes and then she got up and went in and put on a pair of panties, came back out and brought me another beer and slice of pizza.

“you better fuel up, we are not done yet, I have wanted to do this with you for a long time and I am not going to let this chance pass me by”.

So, I sat there naked in front of my stepsister eating pizza and drinking beer, and occasionally, rubbing my hand on her leg, or one of her breasts, or on her beautiful stomach and hips. When I was done, she stood me up, hugged me, and grabbed my cock again and said, “come with me...”

She led me into the bedroom and asked me, “Do you want to fuck me, or make love to me?”

I told her, “both, but mostly wanted to make love to her if I could only do one”.

She winked at me and said, “good answer bro. We will start with that and see where we end up”.

I was nervous again and she could tell I was getting a little tense, she told me to lay down on the bed and we would talk first. So, we laid there, she had my head on her legs and I was rolled over slightly so I could see her and of course her love mound and belly. She had a very neatly trimmed little mound of blond hair right on the top of her little girl, but it was short and expertly trimmed. She still had on her panties that were blue and just thin enough that you could see thru them to the beautiful outline of her clit. She just let me relax and get in the mood again. We started talking about everything under the sun including how we had both wanted to do this years ago, but this was much better and worked out great for both of us.

The talk naturally turned to sex and what I wanted to experience as she was curious, so I told her I really like it when I was able to lick those girls before and she got a wry little smile on her face and said, “That is good, would you like to do that with me?”

I said, “of course I want to, but did not want to do something she was not comfortable with”.

She looked at me and said, “I am comfortable doing anything you would like to do with me, anything at all...”

I looked her in the eyes and moved over so I could get my face between her legs and told her, “tell me to stop or change something if you need me to do something different ok? I want to enjoy this as much I am.”

She just looked at me and said, “do what you have been dreaming about”.

She still had her panties on, and I told her to leave them on, I slowly spread her legs apart and could see her beautifully shaved pussy peeking tough the see though material on her panties. I moved closer taking in the beauty of it and slowly rubbed my nose and then my lips across the thin fabric that was covering her lips and teasing her clit.

She looked at me and said, “I knew you were kinky, even if you will not admit it to anyone. You like smelling me, don't you?”

I was embarrassed and got a little red in the face, she said “Don’t worry. I think it is extremely hot that you like the way I smell and that it turns you on”.

I continued rubbing and licking her pussy though her panties for a little while and then started to pull them off. She raised her hips and I slid them down. She was already very wet again and there was a little string of her wetness that formed and stretched out as I was pulling them away. I stopped and brought my tongue up to it and got it in my mouth. She tasted amazing! I continued to pull her panties off and then sat there for a minute and gazed at them as they were soaked in her amazing tasting fluid. Her beautiful pussy was laying there, and I was a little mesmerized by it, a woman’s fully developed lips and the now swollen clit at the top was an exceptionally beautiful sight. I sat her panties on the side of the bed and moved her legs a little further apart again and she started to rub her clit a little. I moved my face closer and extended my tongue out and met her fingers with a lick. She put one of them into my mouth and then the other. I licked them both clean and moved closer again so I could finally put my tongue on and in to her beautiful, glistening pussy.

She moaned a little as I started to swirl my tongue around her swelling clit and asked me if liked how it tasted. I was too busy to answer her, but she guessed the answer as I really got into licking her pussy. We laid there twisting and rolling together as waves of pleasure hit both of us on regular intervals, I continued to live out my dream and put every ounce of love I could into making her feel like she was the most beautiful and sexy woman in the world.

Something clicked in my head and I moved my hands up to her nipples and began to rub, twist, and roll them in my fingers slightly. Not trying to hurt her, but to hopefully increase her pleasure. I am not sure where that idea came from, but man was I right. Not awfully long after I started doing that, she began to get into a rhythm with me and started pressing her hips into my face harder and harder. She was now telling me to pinch her nipples harder and harder as she was moaning in rhythm with her thrusts into my face.

I am not sure how long it was, but eventually her entire body tensed up and she let out a long moan as a gush of liquid entered my mouth. I drank it down quickly and noticed that it was also a little creamy and tasted amazing, it tasted like her. I kept licking and swirling my tongue as she would tense up and then relax every few seconds. For the first time in my life I also saw her pussy grabbing at my tongue with each wave of pleasure she was having. I was in disbelief that I could do this to her. She was completely engulfed in pleasure and an utterly amazing woman. She started pulling on my shoulders and asked me to come up and lay next to her.

We laid there for a few minutes, I still had a fully erect cock and was leaking all over her new bed, but I did not give a damn. I knew she had really enjoyed me licking her pussy and we just kept touching each other and occasionally, she would roll over and kiss me and run her fingers across my shaved head.

Eventually, she looked me in the eyes and said, “that was the most intense orgasm I have ever had I just want to hold on to it for a little longer. Thank you for that!” I was incredibly happy with myself; I had just given my stepsister the best orgasm of her life…I guess I am going to burn in hell now…but at least she would be right there beside me, right?


2019-12-12 15:38:36
Great story and I am definitely looking forward to your upcoming additions to their adventures together.

Dudley DowrongReport

2019-12-05 03:15:52
Good all around job!


2019-11-27 21:27:11
Athletic guy with a huge thick 8 inch c*ck.. Looking for GIRLS ONLY to have fun and get naughty with.. I am also very dominant and open to being a master to any girls... Intellectual guy can hold a great conversation.. Hmu on KiK.. Atz_717


2019-11-26 13:28:55
Thank you for the feedback and votes everyone.


2019-11-25 21:44:06
You write very well, both in the mechanics (grammar, spelling, punctuation) and the important parts of story telling. As this develops, spend a little more attention to character development, which will add depth to your story. You have talent, keep writing because the more you write the better you will get. Best wishes.

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