Jill Jacking Jack (Hers)

I've always been very personally active sexually. Masturbation and mutual masturbation are among my favorite things to do. My world has always kept me so busy and focused that I never felt I had the time to devote to a relationship, until now.

Jack (as I'll call him here) is my brother's best friend. They have always been friends since we all were born and raised in a small town. Being a few years older than them I watched with a more mature knowledge of the changes boys encounter at puberty. At this time I was masturbating regularly to relieve the sexual desires I was encountering becoming a woman. The boys in town never showed much interest in me, but I knew I never showed them much either. My brother's friend Jack was really the only boy I knew well, before college.

College was a different story. Here I met a man who taught me how to be a woman and how to pleasure a man. The guy was so sensual and completely void of inhibitions. It was he who taught me how to stimulate a man. We enjoyed four years of a sexual relationship, but little more than that. It was an experience that built my sexual self confidence.

I never in a million years thought I would get involved with Jack. We got along fine, had some fun whenever he and Jim would stop by. I never looked at him sexually; he seemed more like a cousin I guess...

That weekend they came by late changed everything. They stop in whenever their crew changes let them go home. It's a long drive so my place is a way point for them. They're usually here today and gone tomorrow. This time they stayed on at work an extra week and by time they arrived here it was late Friday and they were beat! They smelled pretty bad too. I made them shower and let them get to bed for some much needed rest. I went to bed too, nothing else to do.

The next morning I began a usual routine for my Saturdays. Cup of coffee, light breakfast, shopping, home work and R&R. Entering the kitchen of my little apartment I glanced toward the couch in the living room and was reminded that I had quests. Jack was still fast asleep and I realized it was early for him so better be as quiet as possible. I began to put the coffee on but accidentally made a sudden, loud noise. I looked toward Jack to see if it woke him. This is when I saw something in him for the first time. He had been lying on his side, back toward me. The sound I made caused him to roll onto his back and there it was... He had a boner!

My first reaction was a girlie giggle under my breath and a thought to turn away. I looked at his face to see if he might be waking up, nope, still sleeping. He was still under the sheets, and was wearing dark coloured underwear but his penis was still pushing proudly upward! This was neat. Like I said, I watched these boys grow up. I have to admit masturbating a few times to the thoughts of their budding masculinity. These memories were flooding back. I could feel myself getting wet. I stared at Jacks tenting situation from behind my kitchen counter, in case he woke up I could easily avoid detection. He startled me then as he turned again, this time facing me and flipping the sheet off. Now I could see his erection sans sheets but still beneath his shorts. It appeared average size but what matter, it's something I hadn't encountered or enjoyed with a man in some time.

As I looked on at Jack, he seemed to be slowly rocking back and forth. His penis was protruding so close to the top of his shorts I figured it would surely reach out the top. He was thrusting in his sleep. I wondered what he was dreaming about. I watched him for several minutes as he slowly and slightly humped the air. His erection strained to extricate itself from his shorts until, WOW! He just came! I saw it clearly, although not much cum, his cock twitched and a big wet spot appeared at the end of it! I carefully tip toed closer to see and sure enough, a little bit of white wetness was filtering through the material of his underwear. He rolled onto his front... I panicked and headed for my bedroom. Holy shit, I thought! That made me so horny! I took a shower and got out of there as soon as I could. I had to get some food and other things but all the while I couldn't get the thought of Jack and his penis out of my head. Visions of college and all the stroking I had done. I was missing that, and missing something else in life it seemed. I made a conscious decision to confront jack and openly ask him to have some fun with me. Perhaps we could enjoy each other once and move on like it never happened or better yet, maybe we could do it more often.

I arrived back home, climbing the stairs to my apartment and stopping on the landing to get out my keys. I glanced over through the window next to the door and there, before my eyes again, was that boy, this time with penis in hand! My immediate thought was to catch him. I fumbled with the keys and finally forced them into the door. By time I got in Jack was covered by the sheet. I realized any accusations might affect my further plans so I just kept quiet and never let on I had seen anything. I did however have a plan to keep him uncomfortable and in a position to be taken advantage of. I told him to put ALL his clothes ready for washing, which I didn't mind doing for the boys. He protested but I convinced him to wear a towel until the laundry was done.

When I returned from putting in the laundry I actually expected to either find Jack 'jacking' on the couch or at the very least he would be busy in the wash room. I was surprised that he was just sitting there watching TV. This would require a direct approach and no hesitation. My brother would be home sometime after all, which, since we're all adult didn't matter other than the awkwardness it might create if he caught anything happening.

I simply went into my room and stripped down to my underwear. I called Jack into my room and propositioned him. He readily agreed, although he didn't say much. I told Jack to lie back on my bed as I lay beside him facing him on my side. I dribbled oil over his body. He is very toned. His chest and abs are wonderful. I rubbed him over gently caressing every inch of the front of his upper body. Slowly I worked my way down to his thighs, torturing him with slight brushes of his engorged cock and balls. He was full of cum and we both knew it wanted out BADLY! His cock emitted a steady stream of clear, slippery fluid that I worked in with the oil, making a frictionless lube to best tantalize with. Soon I could sense he needed immediate attention or I'd inadvertently lose him. I began to slowly caress his hardness just as I had been instructed years ago. Men don't seem to change as I looked into Jack's eyes seeing a distant ecstatic look of pure pleasure.

When light touches stimulate an engorged penis you can feel everything going on inside it. Every twitch is sensed, each throb expands your slight grip, and every vein can be felt beating with the vigor of a raging heart. Jack was on the way. I could feel it coming through my fingers. He began to grow some more. Who would think these things could swell so much! As his breathing approached heavy, deep pants and near gasps, his cock burst forth with its first release. I figured there would be lots but had no idea he was this full! I remember usually there being a first spurt of quite a bit then a few drizzles and dribbles after that, but not this guy. He literally shot a solid stream right up to his chin not once, not twice but three times before his ejaculate finished. I've heard girls call this the 'baby maker'. It was thrilling for me. I feel so powerful making this happen. It makes me very horny for a return favour, which Jack expertly accomplished.

Perhaps another story.