My first time all began with my step-sister Shannon.
As I approached my 10th birthday, my Mother got married for her second marriage, to a guy named John. I never knew what drew her to him as he just seemed to be an always angry drunk that floated around from construction job to construction job never really lasting for very long at one job or another. Of course, it was always the employer’s fault (like getting drunk at lunchtime should be ok). I perceived him as a huge loser but, my Mother saw something different. What my Mother saw completely baffled me.
He wasn’t particularly nice to anyone. He managed to be married before my Mom to another woman and had three daughters. He sued his ex-wife for custody of the girls but 2 of them told the judge that they did not want in any way shape or form to have to live with their Father. The judge then awarded custody to John of his oldest daughter, Shannon.
Shannon was a couple of years older than I. Funny thing though, as rough as John was to me, my Mother was equally as rough to Shannon.
Life went on like that for a couple of years. Mom disliking Shannon and John disliking me. If John gave me some hideous chore to take care of my Mom would respond in the same fashion with Shannon.
Shannon was an attractive gal for her age. She was close to 5’8” with long slender legs and small ‘C’ cup boobs and a firm ass. Shannon liked to wear these floor length silky nightgowns at night to sleep in. They had a V neckline and looked so very delightful on her. Shannon had long light brown hair that parted on the corner of her head and combed over. She was very much the ‘girly girl’. She didn’t like getting sweaty but, she did enjoy laying out in the sun and since we lived in the South the warm sun was all year round. During the day, Shannon liked to wear very short shorts (some might call them ‘Daisey Dukes’). Her choice of top varied depending on her mood. If she was going to find time to lay out in the sun, then a form fitting tube top. However, if she thought she was going to be spending most of the day doing chores then just a random tee shirt. To me, no matter what she wore I liked her and was attracted to her.
I, on the other hand, was a plain ole horny boy. I stood about 5’6” and weighted in about 195 lbs. I was as average as one could be. When I showered coming from PE I noticed that most, if not all, the other boys were more endowed than me. I found John’s porn stash and masturbated to the pictures and stories that I read. In the bottom drawer of his night stand, I found Playboy, Penthouse, and my personal favorite Hustler. Hustler’s photos were much more graphic. They included guys coupling with gals (no penetration of course but those big dicks were only an inch or two away from a mouth or pussy). I also discovered Penthouse Forum. Well crafted stories of sex. Kind of funny that I started out playing with myself after John fell asleep from drinking too much. Mom was still out working (She sold Real Estate). I would sneak into John’s nightstand, grab a magazine, and head off to the bathroom to jack off. I wasn’t shy or sneaky about it and Shannon occasionally teased me a bit about what I was doing with the porn.
As I approached my 12th birthday, with Shannon being 14 already, Shannon asked me something that changed my thinking entirely about her.
She asked, “How would you feel if I looked through the Hustler magazine with you one night?”
I was stunned. While I would admit that I was a horndog up until that very moment I had not even considered Shannon as a potential sex partner. I fantasized about the girls in my class at school, the girls at my church, and the sisters of my fellow little leaguers. All of whom I felt were completely out of my league. I did not have much confidence when it came to gals. Sure, Shannon and I lived together for a couple of years. Swam in the pool together and went down to the beach together but to me she was just my “step-sister”.
After that question, I had a hard-on for Shannon constantly.
A couple of nights later, John called and said he was having a couple of drinks with his pals from work. This usually meant that he would be there until the bar closed at 2am and then drive home blind stinking drunk. Again, Mom was out showing real estate and called to say that she was going to go out to dinner with her customers and would most likely be home about 11ish.
That gave Shannon and I the opportunity to look through the Hustler magazine together. Shannon had her long night gown on and she told me to just put a pair of boxer shorts on with no underwear.
Again, I was a bit stunned, yet I did as I was told. We got the magazine together from John’s drawer and went to the family room where we could sit on the couch next to each other thumbing through the magazine. Before we even sat down, I was getting a hard on. Shannon looked at the outline of it in my boxers and said, “Wow, it doesn’t take much to get you going does it?” I just hung my head as it was embarrassing to me. I didn’t understand at that minute that she was not trying to embarrass me. To her it was something she liked when a guy showed interest in her quickly.
Shannon and I looked thru the raunchiest porn magazine we had ever seen. This issue of Hustler had pictures of 4 couples. One couple was all white. One couple was all black. The other two couples had one black person and one white person. Looking at the pictures had me make a wet spot on the front of my boxer shorts. As we were looking at the pictures, Shannon’s hand moved over to my thigh. When she did that, I was worried that I was going to cum right then and there. No one female had ever touched me on my thigh that close to my hard cock ever before in my life. Shannon began rubbing my thigh up and down. After several minutes, of what seemed like sexual torture she moved her hand over to my cock out lining the whole thing from outside my boxers. I almost couldn’t take it any longer, so I tried to touch her.
I pulled the strap off her shoulder exposing one of her breasts. It was so beautiful. Soft, pert, and with a pink areola with a small but hard nipple about the size of a pencil eraser. I leaned in to start sucking her beautiful boob all the while Shannon was now grasping my cock and rubbing it with firmness.
I had a very difficult time keeping focused on Shannon’s breast. While I was sucking her breast, Shannon using her other hand slipped her other should strap off now exposing both of her beautiful breasts. Shannon’s breathing was very sporadic with several moans escaping her lips. I was in heaven.
At some point, the magazine fell to the floor. Shannon pulled the elastic waistband of my boxers down exposing my hard cock to the open air. She moved my head off her breast while she lowered her head down to my cock. I’m sure that I lasted less than 2 minutes once her mouth engulfed my cock. I knew I couldn’t hold out any longer and told her that I was going to cum. She just kept sucking not minding my question at all. I leaned my head back on the couch, closed my eyes, and came hard. Quite possibly the hardest I had ever cum in my entire young life. For a moment I was seeing stars and felt very light headed. Shannon swallowed every drop. She came up from my crotch and kissed me intertwining our tongues. I could taste the saltiness of my own spunk still on her tongue. In my head, I thought that it was weird to taste my own cum but as horny as I was I would not complain at all for fear of screwing up my chance with Shannon.
At that point, Shannon told me to get off the couch, so I could learn how to please a woman with my mouth. She hiked up her nightgown to reveal to me she was without panties. My cock began to stir once again. She told me to put my mouth gently on her pussy. I hesitated for a moment taking in the musky aroma of her love hole. After a few seconds, I leaned into her twat and began to lightly lick and suck. I ran my tongue around this hard nub that I found at the top of her pussy slit. Shannon was moaning with her breathing inconsistent. She told me to not focus on her clit. I had to ask what a clit was. She took her hand and pointed to the hard nub that I was licking and sucking on. She told me to flick my tongue in and out of her pussy, so that’s what I started to do. She began moaning louder and squirming her hips. She then orgasmed once, then a second time, and finally a third time. I was smiling while I was licking her. Three orgasms on my first try at oral sex.
Shannon then wanted me to put two fingers into her while I was licking her. She wanted my hand to be palm up so the fingers could get her ‘G’-spot. She told me to rub my fingers that were in her, like I was summoning someone to come over. As I did that, Shannon really started making noise. She was balling her fists up and almost yelling. She made me very happy that I was doing things right. Once again, she came all over my face. I didn’t really know what to do so I sucked the wetness up as fast as I could and swallowed.
Shannon told me to ‘get naked’ because now we were going to fuck. Shannon was still horny, but then again so was I. My mind was reeling with the idea of fucking my step-sister. She was 2 years older than me and none of my friends from school were even acknowledged by anyone two grades ahead of us. Yet, here Shannon and I were getting ready to take my virginity. Take? Hell, I gifted it willingly.
Shannon pulled her nightgown completely off and I was already naked. We moved off the couch to the carpeted floor.
I climbed on top of her and began to try and stick my dick into her. After two or three missed attempts a frustrated Shannon reached down between her legs and took hold of my cock. She pulled on it a couple of times making sure it was hard enough.
“I’m going to put you inside of me, try not to cum too fast. I want more than a couple of in and outs.” she said with a deep rasp to her voice.
When I felt my cock go inside of her I pushed as deep and as hard as I could. She reminded me to slow down or I’ll cum too fast and our delightful paring would be over. I followed her direction. I pulled out slowly and slid it back in slowly. I could hear her moaning again and her breathing get low and inconsistent. I was enjoying what I was feeling around my cock. Her youthful pussy was grabbing my cock and giving me sensations that I had never felt. It took all I had to keep focused on what I was doing to my step-sister. She screamed out that she was CCCUUUMMMMMMIIINNNGGG!!! When I felt her cumming again I felt my balls tighten up and my cock spewed all my seed into her. Neither one of us had even thought about protection from getting pregnant. However, that was the least thing on my mind. I came in her without any warning. She moaned and scratched her nails down my back causing me to cum again.
SUDDENLY, we heard a car door close in our driveway. Someone was home. We frantically uncoupled, grabbed our clothes and the magazine and ran as fast as we could to our own bedrooms. I ran into our parent’s bedroom to put the Hustler back. Then, as the front door was opening, I went into my bedroom. Shannon was in her bedroom with the door closed. I slid on another pair of boxers with a plain white tee shirt. I tossed my other boxers into my hamper. I put deodorant on trying to hide the body odor that I might have had.
I heard my Mother yell for Shannon and I to come see her. I went out to the kitchen where Mom was standing with a doggy bag in her hand from the restaurant that she had dinner at with her customers. Mom was all happy because she made a big sale tonight. She asked if John had come home and I told her he was at the bar drinking with his work buddies. She shrugged her shoulders not allowing him to affect her mood.
Mom asked where Shannon was. I tried to cover for her saying she went to bed a little earlier as she wasn’t feeling well. To cover any smell from the family room I said that she had gotten a little sick in there and I tried to clean it up.
It seemed like Mom bought all of it. She went down the hall to her bedroom and closed the door saying she was heading off to bed. I sighed deeply thanking my lucky stars that she apparently bought my excuses.
The next morning, Shannon just smiled at me and I smiled back. She leaned in to my ear and whispered that we still have some more teaching to do. I was getting hard again and off to the bus stop we went.
Our sexual pairing only increased until my Mom and John divorced. Shannon was suddenly forced to move out. The night she moved out I sat in my room crying. Without realizing it, I had fallen in love with Shannon. I did everything she asked and listened and tried to do everything she taught me. I did not tell anyone what developed between Shannon and myself. Not one friend had any idea of what was going on between us as we were very careful not to be caught. However, two things occurred t me after she was gone. First, we never used any type of protection, so we dodged a HUGE bullet. She didn’t get pregnant and didn’t even have a close call. Shannon was diligent about tracking when her period was due (and yes, we still had sex during her period. I just didn’t go down on her at that time of the month.) Second, when she moved out we never saw each other again. Here I am now at 55 and I have not seen her since she was forced to move out. I don’t know where John and Shannon moved but to me it was like they moved to another planet.
That was my introduction into the sexual world. I felt very flattered that I had such a wonderful teacher and even to this day I use all that she taught me to please my partner. My only regret is that I’ve never had the opportunity to THANK her for being so patient with me and being such a wonderful instructor.
Rated 80 % |