Double or Nothing
I was a late-bloomer as far as masturbating goes...I tried it twice in junior high, but it didn't go well-the first time I stroked for about half an hour before giving up, and the second almost resulted in me getting caught. So close a call made sure I didn't try again for years...
I was 21...seriously, 21...before I tried again. I was with a girlfriend at the time, and we had had sex many times, and she had given me at least a hundred great hand-jobs, but I never really tried it myself, until one night. She had been stroking and sucking me for almost an hour, but was too tired to continue. I told her there was only one thing left to do, and I took myself in hand and began masturbating. She said "THIS I have to see!" and not knowing she was being sarcastic, I turned on the light, and let her watch me make myself cum for the first time!
Though that was the first, it was by far not the most memorable...I had 2 other occasions that will permanently stick in my mind...The first of which was at one of the renaissance festivals in California...after-hours I wanted time to myself, so as is my habit, I took a walk in the woods. I eventually found a nice spot, and when I was sure I wasn't near any campers or picnic areas, spread out a blanket and had a little "me-time." What I didn't know was that even though the nearest campgrounds were way off, a lone hiker had likewise taken a walk...and was spying on me!
I was caught up in the moment at first, but she stepped on a twig, and before I knew where she was, I was on my feet, dagger in one hand, eating knife in the other, "third weapon" in full view. When I saw it was her, I relaxed and put the knives down, and was about to put my pants back on, when she showed me her sketch book...
She was an artist at a local college, and was interested in doing an unconventional piece, but couldn't ask any of her friends...she asked if I would "pose" for her. Being an artist myself, I obliged...first was my back against a tree ("Ulysses and the Mast"- a great painting), and the second, well, she wanted me doing what I had been doing before...I laid back down, found a suitable pose, and she made sketches of me while I masturbated. They were roughs, but they did make for a decent sculpture later. No, we didn't have sex, but she did cut me a check for $50...not bad for something I was doing anyway!
The second, and most memorable, was the first of two times I played Strip Poker with my friend Samantha and some of her friends...I don't really remember how she talked me into it, but I guess on some level it sounded like fun...even after she told me about the "special rules" they used: On the way there, Samantha asked if I had ever played before (which I hadn't), and if I knew the basic rules. I did, but she told me they played a "riskier" version...Double or Nothing.
Here's how it goes: as normal, all players try for the higher hands (5 card draw), and the person with the lowest hand removes an article of clothing. Okay, normal game so far. Where the difference lay was in the final layer...once down to your underwear/panties, instead of removing them right then when you lost again, you could stay in one more hand...If you had the highest hand in that final round, you got to put your pants back on (bra for ladies). If not, you paid for that extra chance...the poor person who lost would move their chair to a spot where all could see clearly, and in full view of all present, become completely naked and masturbate to orgasm.
When Samantha told me this I almost wimped out, but since I never backed down on anything before, I went though with it.
The game went well...I was at my best that night. One woman didn't take the final chance, content to only go naked, but watched as one man and two women made the final try and lost.
My feelings were mixed when I was down to my BVDs. I knew there was no way I'd win that last hand, but there was Samantha, bare-chested...though I'm not normally into large busts, hers were absolutely beautiful...she had no problem seeing my erection through the glass table. Though I knew the price, when I had a hand so bad it could be called a foot, I HAD to play that last round...if I didn't, my penis would burst!
Sure enough, I lost again. Not only did I not win, I had the lowest hand twice in a row! So I moved my chair, and with the others, and especially Samantha watching, I took my manhood in hand started satisfying the ache that had begun. The best part was that Samantha was watching every stroke, knowing that I was looking back and forth between her eyes and those perfect breasts of hers, and could tell that I wished that I was in her cleavage instead of my hand...she had never even seen me with my shirt off, and there I was, erection in my palm, and semen running along my knuckles. I leaned back and relaxed, and heard her whisper in my ear "Don't worry, that won't be the only time you cum tonight..." I looked up in disbelief, but she rubbed her finger along my shaft, and winked as she licked the semen she had wiped off. I got to watch as she eventually lost (again, wishing it was me instead for her finger...). And afterwards, when we got back to her apartment, she kept her promise...she gave me the best blow-job I had ever imagined getting.
I did play one more game the next month, but it was more of the same...only that time there were fewer female players, and most of them didn't go Double-or-Nothing.
So ends my memorable moments in self-enjoyment...I hope you all have at least as many interesting tales one day...And for those wondering, there is a version of Strip Poker that is even more for keeps, though I never played it myself...or party host told us of a swingers' group that does... Okay, you'll need a long couch...and a strong dose of willpower. Be careful of the order you lose in...it'll come back to haunt you...Play Strip Poker like normal, but as each person loses, they sit on the couch, starting at one end, sitting in the order they lose. The fun begins when all other players have lost, and there is one distinct winner...who, after winning, also strips, or at lest removes any pants or underwear if he/she hasn't lost them.
Why is this seating order important? Because that's what order you're pleasured in! The first person to lose, male or female, turns to the second, and must perform oral sex on them, male or female, until ejaculation/orgasm. Shortly afterwards, the second person has to go down on the third, male or female, and the third on the fourth, on until the line reaches the winner...who receives oral satisfaction, but does not have to give it to anyone. The first person who lost would have given someone pleasure, but would have gotten none.
The risk in that game is, for a male, that if you lost somewhere in the middle, you could wind up getting sucked off by a great-looking and orally talented woman, then immediately after cumming yourself, have to take into your lips the guy sitting next to you, not stopping until his semen is in your mouth...
Needless to say, you won't find me playing that anytime soon...