Chapter 62: St. Martin, Part II

May 28, 1993, St. Martin, Leeward Islands, Lesser Antilles

“I’m not sure this is such a good idea,” I said to Samantha as we cleaned up after dinner.

“Why?” she asked.

“The scope of dares is pretty limited. I mean, what are you going to dare each other to do?”

“Things with you, I guess.”

“Exactly. And that bothers me more than I thought it would.”

“You don’t want to play?”

“I’m just wondering how quickly it would escalate. And what might happen.”

Samantha smirked, “Oh, I’m sure you know what might happen!”

“Yes, and that’s the issue. Look, I’m not saying I won’t do anything with anyone, but the dares could escalate VERY quickly, and I expect they would, if you think about it.”

“So then what?”

“I don’t know.”

“What if we kind of modified it? Where each person asks a question and we go around the room and answer.”

“Safer,” I said.

“And we play follow the leader?” she giggled.

“That’s dangerous, too.”

“I suppose. How about this? We ask two questions, then I do something like kissing you. Each girl has to follow or is out of the game. That lets everyone stop at whatever limit they want.”

“And just how far do you plan to take this in public?” I asked.

“As far as it will go!”

“And you would have sex in front of the other girls?” I asked.

“I did in front of Ellie!”

“Sure, but I think you’re starting to veer out of control here.”

“Oh sure, BE the adult!” she said reprovingly, but with a smile.

“Yes, that’s part of being responsible. Would I LOVE to have a wild orgy with eight willing young women? Absolutely! Is it a wise idea? Probably not.”

“So what limits would you set, as the adult in the room?”

“Second base, I think. Anything beyond that should probably be in private, though I guess you and Ellie being in the room together isn’t a big deal because we’ve done that before.”

“So no orgy?” Samantha smirked.

“Is that what YOU want?” I asked.

She shook her head, “No. I’m kind of trying to find YOUR limits. They seem pretty wise all around.”

“Second base in front of everyone. Anything else would need to be in the bedroom, and would need true consent.”

“Second base is just touching, right? And under the clothes is OK?”

“Sure. Being naked on the beach or in the pool is one thing, but in this kind of situation, it’s too risky.”

“How did you learn the limits?”

“Long, hard experience and a lot of mistakes,” I said. “And even with your plan, I’m still a bit concerned about you setting this up; especially given everything we’ve talked about.”

“You really are trying to protect me, both from myself, and from the world.”

“That IS what I signed up to do! But I also don’t want to be overprotective. That would be just as bad as giving you complete freedom.”

“But you do give me freedom!”

“Yes, but within limits. I just set the limits wider than most parents, though not so wide as your dad did.”

“And you expect me to live within those limits after Monday?”

“I do. We all have to live within our limits. Why do you think I’ve been so cautious about this weekend?”

“Do you just want to forget this, then?”

“Within the limits I set, I’m OK with it. Beyond that, it has to be between me and the girl.”

Samantha smiled, “OK.”

When we finished cleaning up the kitchen, she gathered the girls in the great room. I wasn’t surprised to see Maria absent. I had fully expected her to go off on her own and do her own thing, whatever it might be. I only hoped she didn’t get into any serious trouble.

“Does anyone know where Maria is?” Samantha asked.

“She said she was going to a bar. She found the taxi phone number by the phone.”

Samantha frowned, but then explained the change in the game plan.

“Oh, sure!” Liz laughed. “You got yours!”

“It’s not like that,” I said. “It’s about keeping control of the situation. Remember the conversation in the car?”

“Does everyone agree to those rules?” Samantha asked.

There were nods of assent.

“First question,” Samantha said. “When was your first real kiss? I was seventeen!”

Everyone else ranged from thirteen to seventeen.

“Second question,” Samantha said. “Have you let a guy touch your boob? I have!”

Liz laughed, “Obviously! And yes, but only over my shirt!”

“I have!” Ellie giggled. “Obviously!”

Only Louise hadn’t, which also didn’t surprise me, and other than Samantha and Ellie, only Justine admitted to allowing a guy to touch her inside her shirt.

I looked around the room and realized that with the exception of Samantha and Ellie, and perhaps Justine, the girls were all virgins. That also didn’t surprise me given that they all went to Catholic school. The usual time for ‘Catholic Girls’ to have sex was when they went to college, and I’d run into several girls like that. That changed the character of the game, and I was VERY glad I’d limited the activity.

“Now it’s time for follow the leader!” Samantha said. “But, you can only do what I do!”

“Spoilsport!” Liz giggled.

Samantha came to where I was sitting in a comfortable leather chair and plopped in my lap. She put her arms around my neck and gave me a nice, soft, closed-mouth kiss. She got up and I nodded my approval at her restraint. The other girls came to me one-by-one and did the same, though Liz parted her lips slightly, inviting a better kiss. When she got off my lap, she stuck her tongue out at me, but then smiled. I just smiled. Louise was a bit shy, but she kissed me willingly.

“Question three,” Samantha said. “Who was your biggest crush?”

“Samantha, be careful about names,” I said. “You wouldn’t want guys talking about what they did and who they did it with!”

“I’m just asking about a crush,” she said. “But I won’t ask about anything with names that might be, uh, too revealing! My first crush was Bobby Matthews when I was twelve! He was sixteen and a hunk!”

The girls all gave names which I didn’t recognize, which made sense because they seemed to be guys either from school, church, or the girls’ neighborhoods.

“Fourth question! Has a guy, besides your doctor, seen you naked after you got your boobs?”

“Like, completely?” Rebecca asked.

“Answer how much then,” Samantha smirked. “Everything!”

“Me too!” Ellie said.

The only one besides those two who admitted to being seen naked was Justine, which also was consistent with what was said earlier.

“Next follow-the-leader activity!” Samantha said gleefully.

She came and sat in my lap and we exchanged a very nice French kiss. When she got up, Ellie gave me one as well. After Ellie, Liz plopped into my lap and gave me a searing French kiss.

“Time!” Rebecca laughed. “Come on, Liz! Leave some for us!”

Liz reluctantly got up and the other girls took turns kissing me. Louise went last and her kiss was tentative but very enticing.

“Question five! Have you ever seen a guy naked? I mean other than kids you’ve babysat!”

The results of that question were similar; though Mary joined Samantha, Ellie, and Justine in saying she’d seen a guy naked.

“Mary, how?” Rebecca asked.

“My brother’s friend was getting out of the shower when I walked into the bathroom! He had forgotten to lock the door! I was thirteen and he was sixteen.”

“What did you do?”

“I screamed and ran out of the bathroom!” Mary said, giggling. “I don’t think I’d do that now! He was cute!”

The girls all laughed.

“Question six! Tomorrow, we’re going to the secluded beach. Will you go totally naked? Topless? Or suit? Steve, answer first!”

I chuckled, “Naked, IF everyone agrees that’s OK. But if one person objects, then I’ll keep my suit on.”

“I’ll go naked!” Samantha said. “And I’m OK with Steve being naked. Obviously!”

The girls laughed.

“Same here!” Ellie said.

“Me, too!” Justine said.

“And me!” Liz added.

“Uh, topless, I think,” Mary said. “But it’s OK if Steve is naked!”

“Of course it is!” Liz laughed. “YOU get to see everything!”

“Liz,” I cautioned, “no pressure, please.”

“Sorry.”

“I, uh, think naked,” Rebecca said. “And I’m OK with Steve being naked!”

“I’m not sure,” Louise said. “I’ll go, and I’m OK with everything, but I think I’ll wear my suit.”

“That’s fine,” I said. “Do what you feel comfortable doing.”

Samantha came over to me and sat in my lap. She took my hand and slipped it inside her t-shirt, pushing it up until I cupped her braless breast. We French kissed and I gently squeezed her breast and tweaked her nipple. After a minute or so, she got up.

“Make sure you tell Steve over or under your t-shirt, or you can drop out. Nobody will tease you! I promise! Right girls?”

Everyone nodded.

Ellie was next and whispered ‘under’ in my ear. I slid my hand underneath her t-shirt and then down inside her bra to cup her small breast as we French kissed. After a minute she got up and was replaced by Liz who also said ‘under’. I slid my hand under her t-shirt and found her bra hanging loosely over her large firm breasts. Once again, I got a fierce kiss from her and she moaned softly as I kneaded her young flesh.

“Liz!” Rebecca protested again when the kissing and touching went longer than she thought was OK.

Liz broke the kiss and put her lips by my ear, “Do you like them?”

That was one of those questions which had but one answer. Liz was the biggest of all the girls, not quite rivaling Cindi, though she was thinner and less curvy, making her look bigger. There was no doubt the breasts were nice, and despite my predilection for smaller ones, I DID like them.

“Yes,” I whispered.

When she got up, Mary and Rebecca followed, but both said ‘over’. They had moderate-sized breasts that felt nice through their t-shirts and bras. Unsurprisingly Justine said ‘under’ and I cupped her very, very small breast. She was so small she didn’t need a bra, and reminded me of Hope who had been four years younger.

The last to sit in my lap was Louise. She didn’t say anything, just kissed me, so I simply slid my hand gently over her t-shirt-clad breast. It felt PERFECT. It was the exact right size, shape, and feel, and I longed to slide my hand inside her t-shirt and bra and get my hand on it. When she broke the kiss, she was breathing hard and got up and went back to her spot.

“Question seven! Have you ever rubbed yourself to orgasm?”

There was lots of giggling and blushing, but all seven of the girls admitted to having done so.

“Question eight! Is anyone going to confession after this weekend?”

“No!” came the chorus from the girls, followed by laughter.

“I need to ask Steve something first,” Samantha said.

She came over to me and put her lips by my ears, “OK if we touch YOU this time? And you can touch us, too?”

I considered, and decided.

“Yes,” I whispered back, “but be careful how you say it.”

She nodded and stood up.

“This time, it’s touch below the waist. You can say over your shorts, over your panties, or skin. AND, you can touch Steve if you want. But only do this if you REALLY want to. Nobody will say anything if you don’t!”

Samantha took my hand and pulled me up standing. She smiled impishly and pushed her hand inside my shorts and stroked a few times, causing me to rise to attention. I slipped my hand into her shorts and under her panties and gently fingered her clit. We French kissed for about two minutes until she broke the kiss and breathlessly stepped away.

Ellie was next and winked at me, so I repeated what I’d done with Samantha with her. She broke the kiss after about thirty seconds and whispered, “Put your finger in me,” then kissed me again. I did as she asked and enjoyed the tight grasp of her labia while I massaged her clit with the heel of my hand. After two more minutes she shuddered and broke the kiss.

“Whoa!” Liz gasped. “Did you just have an orgasm?”

“A small one!” Ellie said with a big grin.

I raised my finger to my mouth and licked off the familiar taste.

Liz stepped up to me and looked me in the eyes, “You can touch me, but what do I do?”

“Just explore, but don’t squeeze too tightly.”

Liz slipped her hand inside my shorts and she tentatively ran her fingers along my shaft. I pressed my hand inside her shorts and panties and discovered she was shaved bare! We started kissing just as I found her clit and she squeaked and jumped when I pressed the tip of my finger against it. Her hand closed around my shaft and she gently stroked me as we kissed and I rubbed her gently.

“Give someone else a turn!” Justine laughed after about three minutes.

Liz reluctantly released me then leaned forward, “Can I come see you later?”

I nodded and she smiled and stepped away. I put my finger to my mouth and got just a hint of a strong tangy flavor that I hoped to taste directly later that evening. Liz was replaced by Justine who wasted no time in getting her hand in my shorts and giving me permission to touch her. We kissed deeply and it was clear she had done this before, as she had exactly the right grip and speed to make me feel VERY good. I did the same for her, making sure I pressed my finger further down to rub it along her labia. When we broke the kiss I once again licked the juices from my finger.

I waited, and Mary came up to me, “Uh, just over my shorts please.”

We kissed and I felt her hand exploring my shaft through my shorts and I rubbed her gently along the seam of her jean shorts. She gasped at the first press on her clit and I continued apply light pressure through the stiff material while we kissed and she held her hand firmly against my shaft.

Rebecca was next and she gave me permission to touch her over her light cotton panties, but slipped her hand inside my shorts and briefs. “Sorry,” she whispered then kissed me softly. When she broke the kiss, I said, “Don’t apologize. It’s OK!”

She smiled and stepped away. That left Louise, and I wasn’t sure what she would do. She’d only let me touch her breasts over her t-shirt, so I wasn’t surprised when she gave a simple head shake. I gave her a big smile and winked at her. She smiled back, obviously relieved.

“I’m going swimming!” Samantha said.

“Bathing suits?” Liz asked.

“Yes,” Samantha said. “Let’s keep it safe for everyone. We’ll be at the beach tomorrow!”