My first true sexual encounter was with a girl, I’ll call her Anne, first letter of the alphabet. She eventually became my second affair, so the preamble is important. We met one summer during grade school, we belonged to the same country club – 18 holes, two swimming pools, a dozen tennis courts, even a couple squash courts. We’d been on the same swim team, played junior golf in the same mixed foursome once in a while, even had squash lessons together one summer.
One border of the club, where the line of tennis courts was laid out, bordered on a residential neighborhood, with the typical McMansions, big back yards, extravagant decks, some with pools, play sets, and so on. The houses didn’t have fences, due to homeowner association rules or it ‘simply wasn’t done around here’, I don’t know. Those along the 4th hole of the golf course, their yards abutted the fairway as this type of arrangement does. But the group of houses by the tennis courts had long rows of dense evergreens and other shrubbery to create some sort of privacy, who wanted to look out their back yard and see acres of cyclone fences surround the courts?
Anyway, Anne and I didn’t really socialize in grade school or high school. We were friendly during the summer as our social circles were smaller and intertwined, but we had different friend groups in school, never really saw each other in a school of 2000 kids.
I was skinny, braces, mostly caddied and tried to play squash and swim. A total dork. She too was awkward and scrawny, straw-like reddish hair, glasses, was a pretty decent golfer, though, how she could hit a ball that far was beyond me. There was nothing going on for either of us all through HS. She seemed to have dated some guy in the AV club but not really sure. As I said, the school was big.
But then after senior year in HS, found myself at the pool after caddying 18 holes that morning, had changed into my tank suit. These were the days when Speedos were still in vogue, all the guys wore their skimpy low slung Speedos all day without thinking anything of it. I’m sitting at a table having a Coke and this really nice looking girl in a one piece suit and shorts over it walks by. Slender but firm figure. Nice tan.
She looks at me and calls me by name. WOW it was her! The classic ‘ugly duckling filling out’ scenario. No glasses, much better complexion better, hair looked great. And the tan, it looked amazing.
We started talking. Her brothers were playing a doubles match, asked if I wanted to keep talking while watching. Sure, I had nothing else going on. I put a t-shirt on, you couldn’t walk around shirtless outside of the pool area, and walked down the line of courts with her. Turns out they were playing on the very last set of courts, and clobbering their opponents – the match was already into the second of best of three sets.
We talk about the houses, next to the courts, I admitted that when I was young I had snuck into some of their yards just to see. She admitted that she had too, with a couple of her friends. She got animated explaining how they thought they were going to get caught, one would stand lookout while the rest dodged between the bushes, and then the lookout would army crawl, to the bushes, to stay out of sight of any adults who might be looking.
She described her favorite, “The best one is this one with a kids playhouse and lawn maze right by the edge of the property! We snuck in there several times, we were always afraid we’d get caught and our parents would be furious, but it was so fun!”
After her brothers were done with the match, the court emptied out, and it was just the two of us, talking. “We should go see if that house still has the lawn maze!” We walked down to the end of the courts and quickly dashed behind the bushes, both the playhouse and lawn maze were still there. The backyard was huge, had to have been 150 feet up to the deck of the house, and plenty of trees in between. Remarkably secluded.
We giggled, wondering what it was like to grow up in a house like that.
We looked around for a bit, and decided that the house was empty. No signs of motion, the doors were all closed, furniture was stacked up against a fence, no lights on. We ducked into the playhouse, there was a table, a bench, and seats built into two corners. Roomy for kids, a little cramped for us.
I sat on one of the corner chairs, she sat on the bench across from me.
Had the opportunity to really look at her, she looked so sexy. I was pretty sure she had no idea how hot she really was, not with her ‘ugly duckling’ history.
She looked at me back at me. “If you sit over here, you can see the water hazards out on the course.” Well, of course I took her invitation. The bench was small, our hips were lightly touching each other. Looked at each other, and it suddenly got silent, and the electricity magnified significantly. I don’t remember who leaned in first but we met in the middle, started kissing.
First it was just our lips, then tentatively light probing with our tongues, and then we went nuts. Trying to press our mouths hard against each other, we couldn’t get enough purchase, so our hands, then our arms came into play, pulling each other close. We made out for I don’t know how long, until our bodies started to tire from the awkward twisting from our sitting next to each other.
She squirmed around a bit, put her legs over my legs, and then I pulled her up onto my lap. This was much better. Her arms around my neck. My arms around her waist. Became very conscious of her breasts against my chest. And my cock, it was definitely aware of the heat as well, although there was no room for it to grow, squished into my tank suit and her on my thighs.
We took a break from making out, she played with my hair, my ears, tracing her fingertips over my face and mouth.
I explored the small of her back, her hips, her waist, her stomach, wrapping my hands around her just below her rib cage, acutely aware of her breasts not that far from reach. I didn’t dare stare at her chest, but I wanted to, to see if I could see her nipples. I started kissing her again, and then as I pulled away, I tried to glance down without her seeing me.
But she caught me!
“You can look if you want. It’s OK, I want you to.” She leaned back away from me, stuck her chest out for me. “Do you like?”
I was stunned, didn’t know what to say. I could see her nipples poking through the thin nylon of her tank suit, and felt myself surge down below. “Oh yes. Yes, very much.”
My hands were still wrapped around her sides, and I was even more aware now how close I was to being able to touch her curves. I squeezed her with both hands, and I somehow knew she was thinking the same thing I was, what if I was to move my hands up? So I did, just a bit, sliding my open palms to just under her breasts, to see what her reaction was.
I expected her to push away, to decide that ‘you can look but you better not touch’, but she didn’t. Instead she took a deep breath and gave the slightest moan. I squeezed her again, and then she gave me the go-ahead. “You can keep going, if you want.”
OH MY GOD! A half hour ago I had just finished caddying, and now I’m about to hit second base? Who could have guessed?
Not wanting to waste a minute, I did as she asked, sliding my hands up over her mounds, slowly, waiting for her to change her mind and stop me, but she didn’t. She began breathing harder. As my hands covered her, she reached forward and began kissing me again, way harder than before.
After a minute or two, it became evident that this position was also awkward, and she got up, turned to face me, then put her legs under the table and sat on my thighs, straddling me. This was much better, we could kiss hard while I touched her. Heaven lasted forever, it seemed.
Finally we parted lips, she leaned back and I began playing with her nipples through her suit. She turned red for a second, then said, “Maybe this would be easier?” and suddenly slipped the straps off her shoulder, pulling her suit down to her waist. Yes, her tan was amazing, highlighting her white breasts, firm small B-cups, with hard pink nipples. I instinctively squirmed, my cock had to stiffen, but couldn’t, there was no place for it to go, with it begin tucked down into my tank suit, and her sitting on my lap. “Better?” she asked, with a shy smile. “I wanted you to see me for a while now.” I cooed back, and played with her tits for a bit, but my discomfort was becoming evident to her. “Are you hot? Let’s take YOUR shirt off!” Without warning, she pulled my shirt off, and pressed her bare chest against mine. While so erotic, it was too much, and my erection was becoming downright painful.
“What’s wrong, you look really uncomfortable?” She was a bit puzzled that I suddenly wasn’t ‘into’ this as I was a moment ago.
“Ummmm, it’s getting uncomfortable down there,” and I nodded down to my lap. “Oh my god, you’re getting hard!”
“Uh, yeah. Actually, not ‘getting’. I’m completely hard.”
Her face broke open with delight! “Because of me? I love that!” She stood up, stepped out of the bench, and then knelt down, putting her hands on my thighs.
Once guys became teenagers, we learned to keep our cocks pointed down and tucked into our tank suits, it was universally regarded as uncool to have a visible ridge off to the side of your Speedo when walking around the pool. And if one got an erection, it was time to find a towel or to jump in the pool and cool off.
As a result, while my cock was pointing down, it was also nearly completely hard, and thus trying to point straight out, a tent pole in the thin fabric of my suit. She looked down and said “That looks really uncomfortable, can I help?” and without asking more, she touched the bulge and helped it move to the side so it could stretch out.
She looked up at me with a smile. “That’s for me!” and squealed. “I want to touch it!” She began running her fingertips along the ridge, pointing out at my hip. “You’re really hard!” I sat there dumbly, not knowing what to do.
It didn’t take long for her touching to bring me to the point where I realized I was going to have an orgasm. “Ummmm, this is more exciting than you probably realize.” I tried to warn her. “I’m so glad! You can see how excited I am!” and she pinched her nipples in response.
“I mean, well… REALLY exciting…” and without warning, began to groan. “You mean you’re going to ejaculate? You’re going to orgasm? Oh my god yes, I want that to happen!” She grabbed the shaft between her thumb and fingers, and began to pump me more. I started to breath harder, my legs straightened out.
“I want to see, ok? Can I see?” I nodded dumbfoundedly.
She tucked her fingertips inside the waistband and tugged it down to the base of my shaft, exposing my dick but not my balls. It sprung out, pointed straight out. She started stroking again, watching intently, occasionally looking at me, and then back at my dick. It didn’t take long before I went rigid, from the back of my neck to my heels, and she knew I was about to come. I moaned, long and low, and started to spurt, all over my stomach, as she squealed.
“That’s for me! That’s because of me!” she whispered in happiness.
She kept pumping, until there was no more to be milked. She sat back on her heels, wiping a couple of errant drops off her hands onto her shorts.
“Oh my god, that was so cool! I’ve never seen that happen before!” I leaned back on the bench, against the edge of the towel, still speechless.
“I don’t think I can walk for a few minutes. I can barely talk!” I grinned. “I don’t know what to say.”
“I think we have to clean you up. That’s a pretty big mess.” She looked around the playhouse. There was a counter with play dishes, and a towel on top of them. She used the towel to wipe me off. “We can’t leave this for kids to find.”
“Why not leave it outside, get it a little dirty, and let it rain, and their mom will probably throw it, all muddy, in the wash.”
“Good plan.” She finished wiping me off, then pulled my suit back up, and watched as I adjusted my shrinking cock back into it’s ‘down’ position.” As I did so, a couple more drops leaked out. “Wait, let me get those.” and she used a corner of the towel to wipe the tip of my cock off, and stuffed it back inside again. “We’d better get going, I’m sure my brothers are looking for me after their match.”
I pulled my shirt on and then longingly watched as she maneuvered her straps back on her shoulders. She shook her shoulders at me, jiggling her tits at me, laughing. We then squeezed out of the playhouse, and she dropped the towel on a patch of dirt by the side.
“Next time, we’ll have to bring a rag of our own,” she added. I was again speechless, at her casual mention of ‘a next time’.
The End
Source: reddit.com/r/gonewildstories/comments/cgxd6v/my_second_affair_part_1_strangers_backyard_long
Such a hot story. You captured the not so innocent teenage excitement perfectly.