First Jack Off Session

By Kyle Guy

Published on Aug 31, 2022

Bisexual

Controls

This story is completely fictional any references to names, places, situations are made up.

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This story is about being in my adulthood and sharing with my dad about my first time I masturbated.

One summer afternoon you and mom ran to Costco and a few other errands. My sister was at her friend's house and I was home alone. I was 14. It was hot out and the air conditioning was on. It felt great in the house. Nice and cool. I had on black mesh soccer shorts and boxers underneath.

For some reason, as soon as you and mom pulled out of the garage and I heard the garage door close, I went down to the family room and looked through the magazine rack between the couch and your recliner.

Looking through the various magazine titles, I found a Victoria's Secret catalogue. I pulled it out. I knew there were lots of bra and panty photos with models tight bodies but I had never looked through it before.

On the cover was some blond model with a loose flowing shirt, she was kneeling on a wet sandy beach with a bright bikini on. Very modest shot actually. But when I got to the underwear section there were much better photos.

I felt my big boy cock getting hard in my loose boxer shorts in my gym shorts. I'd never really noticed my cock hard before except when I woke up. But I never did anything about it. I didn't know I could.

Because my big dick was making a tent in my shorts I decided to go to my room. (I didn't know my cock was big at the time). I had only ever seen your dick soft when I was little and I showered with you and I thought mine was about the same as yours, dad. I figured they were all standard, cock sizes. I had never looked in gym class I was too scared to peek at my friends.

Once in my room I started flipping through the bra pages. I noticed there were only like four or five models. One model had bigger breasts than the others. They were so full and her waist was so tiny. I liked how her torso widened and her voluminous boobs floated up in various lacy bras. I couldn't tell if I could see a shadow of her nipples through the lacy patterns but I thought I could. I thought they showed that shadow intentionally. I thought the bra was built like that for her husband to see through to turn him on, for situations when a woman was wearing only a bra and panties in her master bedroom in anywhere USA and was feeling sexual. Where adult married people touched each other and a man would feel his wife's breasts over a lavender lacy bra, where he could see her nipples. He would take his large warm hand and feel the large side of her breast contained by this purple undergarment holding the weight of her smooth but heavy breast, a sexy toy really. I thought of your large tan hand and your gold wedding band feeling that large swath of side boob from a smooth arm pit around to a large nipple and then I imaged your broad tan chest no shirt.

I didn't imagine mom at all, but because you were my ideal male role model, I pictured you playing with this bra'ed model. Before I knew it my right hand was in the waistband of my shorts and boxers playing with my hard dick. I didn't really notice what my hand was doing, it was just natural. Rubbing my hard boy cock up and down the shaft. My light blond (at the time) pubes on my young ball sack we're rubbing the loose cotton fabric inside my boxers and making a chaffing sound against the not so soft mesh Umbro shorts.

Next in my mind I pictured the buxom bronzed model still in her periwinkle bra and panties pressing her large breasts against your bare tan chest in the privacy of your own middle class bedroom in anywhere USA. Maybe on a water bed, what could be more racy! And I imagined that a couple likes to enjoy sex together often. I pictured you two standing and kissing sloppy open mouthed kisses, her breasts on your chest pushing and flattening. Wanting you desperately and feeling your large pecs against her big sensitive lace encrusted boobs, you feeling that glorious swath of side boob with your hands, rubbing and squeezing like a man would do to a huge set of knockers.

I pictured your tan torso contrasting with white briefs, Champion brand. It reminded me of a rectangular glossy postcard mailer ad that we got addressed to "Resident" that had a photo on one side of a tan broad chested man that resembled you, in tight white briefs toweling off his wet hair standing in front of a row of metal gym lockers. The back of the post card offered the closest Champion store, an outlet mall three towns away. For some reason I swiped it from the kitchen table's pile of mail and slipped it in my book shelf between a science book and a Star Trek The Next Generation novel I started but never finished.

I don't know why I took that mailer of the man in white briefs with a champion logo but now vigorously beating my meat in my shorts it made sense. It was the American ideal. A strong jockey male resembling my dad on the post card. What I should aspire to become from a boy to a man, and now the other piece of the sexual puzzle, the model in the lavender bra and panties was the ying to my Champion briefed daddy model's yang. Two straight, possibly married people ravaging each other's bodies. In their American underwear. Wholesome and naughty at the same time.

Before I knew it I was exploding a load in my shorts. I did not know what to do. I did not know what it was. It felt so strangely new too me I was beyond surprised and I didn't know what happened. Shooting my load, masturbating for the first time was wonderful but confusing and surprising. I still didn't understand what had happened. I liked the act of rubbing my cock and imagining this couple more than the orgasm itself that I didn't know was coming. No pun intended.

I knew I couldn't wait to do it again. And I did later. But first I didn't know what to do with the mess in my shorts. It was wet and clear-ish white. I kinda remembered a book you and mom made my sister and I read and ask you guys questions titled "What's happening to my body?" But I didn't correlate this to that for a few days.

Anyway I grabbed a Kleenex and did a poor job of wiping it off me and my boxers. I had a wet glob in my shorts. After a while, my cock went down to normal and I went to the book shelf and pulled out the postcard ad and looked at it next to my lavender lace model. The scale of size of the people pictured was roughly the same and they looked like a good looking couple. Like they might go together.

I imagined her pressing her big boobs against his muscular chest, breast to pec, nipple to nipple, lacy bra on his lightly hairy tan chest and I got hard again. I started stroking my wet cock again, this time expecting to shoot a load.

I even pressed the postcard jock daddy to the magazine model so they paper images would be smashed together and I couldn't see either of them, and then I pulled the pages apart slowly to peek at the two of them touching and slowing pull them apart so I could actually see them again.

It wasn't long before I shot again. This time I wasn't surprised and I appreciated the feeling of release when I exploded another dose of boy juice still in my shorts.

This time I knew enough to undress, wipe myself off with Kleenex and put on some clean boxers.

It was awhile before anyone else came home. I slipped the postcard jock back in its hiding spot and ran down to return the VS catalogue to the magazine rack between Golf Digest and Home and Garden where it was filed before.

I went back to my room and messed around with some Legos while I sat on the carpeted floor of my room in the air conditioning unaware that the innocence of childhood was over. Unaware that what really turned me on was the Champion model's chest, hairy body, naked nipples, rippling muscled arms and shoulders, thick neck and 5 o'clock shadow. Unaware that the model not only reminded me of my dad - my average American role model - but that I specifically desired my dad's body and men who resembled him. Unaware that I didn't need large breasts or lacy bras or skinny waists or vagina to turn me on. Just another dude with another hard cock. I wouldn't figure this out until much later.

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