TS: M[17]+F[17]. I stopped a game of strip poker from going too far and got to date the girl who would have lost the game had I not intervened. | 2016

This is tame by most of GWS entries. If you're looking for fappage, pick another story.
tl;dr: I stopped a girl from losing strip poker, she remembered it when I got home from college, we made out and got to second base a few times. The end. (Burner account for obvious reasons.)
 
All this happened, but the narrative and dialogue are from memory. So the actual sequence of events and things people did/said are representative. I'm no court steno, and I didn't capture it on video. Use your imagination and fill in the blanks. The story:
Senior year of HS, I was in a play. The worst production of the Merchant of Venice ever staged, to be precise. We sucked, the set sucked, the sound sucked, the props sucked, the costumes sucked. It just sucked. But we had a great time doing it despite how awful it turned out. At least three different romances started and/or ended during rehearsals, and one girl (not the one in this story) went through the entire backstage crew.
I was Antonio. The girl who played Portia was rather stunning, but in a non-obvious way. By that, I mean she had relatively large breasts on a small frame, which I suppose is stunning enough for some men. But she also had a huge head of wildly unruly hair that was always frizzy. Between her chest, which drew attention away, and her hair, which concealed, most guys never realized that she had a very pretty face. More of an elegant classically beautiful face, really. Not the typical "cute" face that seems to be a mandatory requirement for popularity.
Anyway, the last curtain fell, the (VERY polite) applause died away, sets were struck, and it was time for the cast party. My parents had a stock room for their business. It was a huge open space, perfect for parties. Being good sports, they let us use it and even supplied snacks and a couple of six-packs of beer (which was roughly half a beer per teen, and I suspect a deliberate way of tricking us into not bringing alcohol of our own and therefore not getting drunk).
Unfortunately, despite the "copious" amounts of alcohol, the party sucked even worse than the play. Drama nerds are not equipped to be party animals. We act in plays because the personalities of the characters make up for the lack of our own. After an hour or so of lame music, awkward dancing, and clandestine make-out sessions by the two couples still together at the end of the production, things pretty much petered out.
Until some idiot said "Hey! I brought cards. Who wants to play strip poker?"
Surprisingly, all the girls said yes. Even the ones we wanted to lose. And by "lose" I mean "win" because we preferred them with their clothes ON. But better still, the two or three girls we REALLY wanted to lose, as in "lose at poker so we see them naked" also said they would play.
We had too many people to play all at once, so we made up a tournament-style game where guys were allowed to start with ten clothing items, girls twelve. Three groups played until half the players in their group were down five items. Then those people were consolidated then broken into two more groups and played until they were down to three items. And finally, those losers would play one epic hand until everybody had lost except for one person who would be the "winner" of the tournament. That meant that we'd see at least four people totally naked, hopefully not all dudes. But probably all dudes.
It was soon clear that "Portia" would never be featured on Legends of Poker. She lost her first two hands immediately, landing in the semi-finals with (to everyone's surprise) a 50/50 mix of male-to-female. Shortly thereafter, she was down to bra, panties, and one sock and waiting for the rest of the games to finish. The finalists settled down in the center of the room, three dudes and two girls: Portia, and one young lady of "substantial proportions" that everybody was hoping was a card sharp.
The first round was dealt. Portia asked for three cards, despite several other girls coaching her. Cards down, she had the worst hand (something like a seven over a two). Sock off. One more hand, and it was going to be boobies- quite possibly the first (and for some probably the only) boobies they would see in real life. To everyone's surprise, she survived several more hands, and it was one of the boys who was down to near-nekkies.
This was it. Chances were, somebody was going to have to strip off completely and wait for the rest of the game to end. Cards dealt, hands examined, discards made, and replacements distributed. And Portia's hand was lowest.
A hush went out over the crowd. The boobies that were in the top ten of "boobies I want to see" list of every boy in the school were about to be revealed.
Portia blushed and then started to look like she was panicking. Trembling, she reached around behind her and ...
... and that's when I panicked. Fearing my mom would stop by with more chips and find a bunch of naked and near-naked teenagers, I yelled "Game Over! Everybody get dressed!" Then I threw a coat over Portia's shoulders, lifted her up, and gently led her to her pile of lost clothing.
There was a lot of grumbling, but everybody complied. Which was good, because about five minutes later my mom stopped by with more chips. By then, the party had completely disintegrated, and all that remained was for the kids to call their parents for rides and/or drive home themselves. When her ride arrived, Portia ran up to me and gave me a quick hug and then whispered "thank you SO much" in my ear.
I got tremendous amounts of grief the next few days in school. But it really didn't matter because I had asked for, and received, early graduation so that I could accept early admission into the Nuclear Engineering program at a moderately prestigious university in the Mid-West (where I joined Navy ROTC and then ended up spending most of my 20 years on nuclear subs, but that's another story). I pretty much forgot about Portia, the strip poker game, the party, and the suck-ass play the first day I arrived on campus and realized there was a distinct difference between college coeds and high school girls.
The end of May brought my first semester in college to a close, and I headed home for a short break before I had to report for Navy boot camp. When I got there, my brother and sister told me that Portia had been calling for me for the last couple of weeks, wanting to know when I got home.
I called her home number and asked for her. She was out, but her mom practically screamed "Oh! It's Antonio!" and then went on to tell me how much her daughter had talked about me the last few months. And then really quietly, she said "and she told me how you rescued her that night, and I just can't thank you enough." And then she started crying. Eventually I managed to end the conversation gracefully and hang up.
Portia called later that afternoon and asked if I wanted to come over and hang out for a while. I had nothing better to do, and so I accepted. To be perfectly honest, I was actually looking forward to seeing some of my old nerdy friends. Eating right, learning about this mysterious "hygiene" thing people were talking about, and working out with the ROTC detachment (I wasn't an official middie due to my early admission), I had gained about 35lbs of muscle and lost about 10lbs of acne. I was also a lot more mature (I thought), and confident (I was pretty sure. maybe.)
When I got to her place, I was swarmed by her parents, who apparently thought I had already graduated and was the admiral in charge of the entire Navy. "Hanging out" turned into "dinner with the 'rents," so we didn't have a lot of time alone. Portia looked really good. She had had her hair straightened at a salon, and the effect was dramatic. She was wearing a peasant blouse and jeans, which complemented her figure quite well. I stayed a while after, had a beer with her dad (who waited until wife and daughter were gone to tell me how grateful he was for what I had done, and how much he respected my decision to serve, etc.) Portia walked me to my car. I asked her if she wanted to go hike Sugarloaf (a local hill with mountainous aspirations) the next day. She said sure, and then stood on her toes to give me a very nice kiss goodbye.
I picked her up the next morning. It was still pretty cool in the hills, so we walked about two thirds of the ridge line before taking a break. This was the traditional picnic spot, with good reason. On the western side, the granite fell away in a huge cliff that we locals called "half dome" for its resemblance to the feature of that name in Yosemite. The view was spectacular. You could see three ski areas in 270 degrees of uninterrupted horizon. I turned back to comment about the panorama to Portia...
... and found that there was a very different seat of peaks on display. Portia was naked from the waist up, with her shirt tied by its arms around her middle and her bra somewhere I couldn't see it.
Instantly, she wrapped her arms around her chest, turned bright red (everywhere, it seemed), and started to giggle. I didn't exactly know how to respond, other to splutter, say things like "uh" and "um," and turn red myself.
"I took my shirt off like ten minutes ago," she said, still giggling. "You were so busy picking out a good trail that you never looked back." I spazzed out some more, threw out a few more "ums" and "uhs," and finally managed to get out "why did you, uh?"
"Well, that night you stopped everybody from really embarrassing me. The whole school would have talked about how they had seen my tits. So I figured you were the one person there who actually deserved to see them. And so you did. And now turn around so I can put my shirt back on."
[Author's note: I told you this was a pretty tame story.]
Portia had packed a nice picnic lunch, so we spent an hour or so up on the top of the cliffs, enjoying the view (of mountains and forests only). Neither of us mentioned the earlier partial nudity, although I did get caught in a furtive glance at her chest (I was just making sure she had put her bra back on. For academic reasons. Honest!) which made both of us blush.
I eventually manned up and made a move to start a make-out session, which went fairly well until I got cock-blocked by a family of hikers who arrived just as I was about to start unbuttoning Portia's red-and-black checked flannel shirt. We disentangled ourselves, packed up the remains of lunch, and ceded the picnic area to the family. Their timing was both annoying (things had been going well) and fortunate (they didn't stumble upon a naked wrestling session), but that worked out well too because we had something to laugh and grumble about on the long hike down the "mountain" and back to my jeep. At the very least it prevented that awkward post-giggity silence that sometimes occurs during a "walk of shame."
We agreed to meet at her house the next day while her parents were at work. Her expression made it very clear that we had only pressed the "Pause" button that afternoon.
I got to her house the next afternoon. We goofed around, watched some TV, shot some hoops in her driveway, talked about school and stuff for a while. Eventually, I must have gotten "that look" in my eye, because she took me by the hand and led me down into her basement. They had a rec room down there, complete with faux-wood panelling on the walls, a couch, a pool table, and the ugliest shag carpeting you have ever seen, a-la 1960's Better Homes and Gardens.
Portia pulled me down onto the couch next to her, and we immediately hit "Play" on the VCR in my brain. After some hot and heavy smooching, I made my move toward her shirt. No objections. She even lifted it up and over her head for me. And she was wearing a front-fastening bra- the universal green light for unwrapping the presents! I saluted the quarterdeck, asked permission to come on board, and undid the clasp. And then tried to undo the clasp again. And again. And then admitted defeat and asked her to do it.
She did, then got embarrassed again and hid them behind her arms and blushed. I said something like "it's OK," and then just went back to making out. Pretty soon, she opened up and wrapped her arms around me. I sneaked an occasional glance down at them. They weren't the first breasts I had seen (I'd been at college for almost five months, and the guys I spent the most time with were training to be naval officers). But they were definitely the nicest. Gravity hadn't touched 'em, and they were both large and shapely with nicely upturned nipples. I've always preferred small boobs, but hers set the bar high for every "chesty" girl I've been with afterward. Eventually, I even got to play with them a while. To paraphrase Borat, "very niiiice."
Everything was going swell, and I was even considering a run at third base, when I heard a car door slam up on the driveway.
"Oh shit! My dad!" hissed Portia. Then she grabbed her shirt and ran into the basement bathroom.
I tucked my own shirt back into my pants, counted to 32 in binary to help reduce the swelling in my jockies, and then smooshed my hair back into place as I heard the screen door open and shut. Her dad appeared down the stairs shortly thereafter, and then he shook my hand and said hello.
I stuttered something about us playing some pool (no balls on the table, sticks still in racks on the wall), told him Portia was in the bathroom, then stood there awkwardly. He said I should come up later and have a beer, and then turned to go.
But just before he started up the stairs, he glanced over at the couch and paused. I followed his gaze to see a single bra cup sticking out from the cushions. He noticed me noticing him notice. We broke eye contact immediately, and he said something like "see ya" and went up the stairs.
Portia came right out of the bathroom, shirt on but seriously titswiggly due to the lack of a bra. She whispered (loudly- is this something ALL women do? Don't they know that people can hear them three counties away when they whisper?) something like "whew- I can't believe we didn't get caught!" And then I pointed at the poorly concealed brassiere. She started freaking out. Her mom would kill her. Her dad would kill her. They would take turns killing her, and then kill her together. I told her to calm down and just act natural, and everybody would pretend it never happened. That's how my family treated everything, and it worked for us.
Then she got an idea. Slipping into the laundry room, she grabbed a different bra from a dirty-clothes basket, took off her shirt, shucked on the bra, got buttoned up, and then led me upstairs.
When we got upstairs, she told her dad she had "let me win" (causing his eye to open wide until he realized she meant "at pool") and then said he should play me since winner-plays-challenger. Then she told him to get me a beer while she re-racked the table. We went downstairs again, played a couple of rounds of pool while drinking our beers. Her dad saw that she "still" had a bra on. She "noticed" the one sticking out from the couch cushions and said "oh, has this been here the whole time? I'm so embarrassed!" and then ran into the laundry room with it. I shrugged, avoided eye contact, and (intentionally) lost another game to her old man. I'm pretty sure he knew, but at least Portia's quick thinking made it hard for him to know for sure.
We made out a few more times before I had to ship out. Never got past 2nd base, but if you have to be stuck in a strictly waist-up situation at least it's better to have top-quality bases, er- boobies, to play with while you're there. She did actually put her hand down my pants and grab my junk once, but only for a second before she said "I have to stop now, because if I go any further I won't be able to stop at all!" We'd talked about it, and she wanted to remain a virgin until she was married. I said I would respect her wishes, and we'd just enjoy what we had already done before until I had to go into the Navy. A couple of weeks later, I went in, and that was pretty much the last time I saw her except a couple of "guess who I bumped into at the mall" types of encounters over the next few years. Then she met some guy and got married and moved away.
 
So, not a lot of gonewild in there. But it was a pretty memorable time of life. If nothing else, I learned that being a nice guy doesn't always mean you'll finish last. It didn't quite get me laid, but I got to fool around a few times with a pretty girl who thought I was something special, which was a lot better than the few fumbling acts of intercourse I had previously experienced. [edit: should have proofed before hitting "save."]