Chapter 9: Cherries Jubilee, Part I

June 1981, Milford, Ohio

On Saturday morning, Stephanie and I woke up at our usual time. She pulled me out of the room and we swam our laps naked. Afterwards, we showered together, making sure we were clean all over, then dressed in shorts and t-shirts and ate breakfast. We cleaned up the kitchen and I checked to make sure we had all the things we needed for Stephanie’s sundae treat. Once I confirmed that, we went to sit in the living room to wait for her friends.

“We really need to use the king-sized bed, so we’ll have to wash the sheets and stuff when we’re done,” Stephanie said.

“How late are the girls staying?”

“They could spend the night, if you wanted. But I’d rather sleep just you and me in your bed.”

“I sure wouldn’t mind sleeping in a bed with all three of you, but you and me in my bed is perfect, Squirt.”

Around 9:00am, I saw Shelly and Trish walking down the driveway.

“Big brother, just remember that they’re both virgins,” she said, going to the door.

“I hope they know they don’t have to do anything they don’t want to. You did tell them it’s OK to change their minds, right?”

“Yes, Big Brother. They want this!” she said, opening the door for her friends.

“Hi, Trish! Hi, Shelly!” Stephanie said, letting them into the house.

“Hi, Stephanie!” they said together.

“Hi, Steve!” Shelly said with a big smile.

She was a short, compact brunette with big brown eyes and very nice curves.

“Hi, Steve!” Trish said with an even bigger smile.

She was a tall blonde with bright blue eyes, thin, but with large breasts.

“I think we’ll swim first!” Stephanie giggled. “Naked!”

She wasn’t wasting any time! I waited to see what her friends would do. This would give me a good idea of how comfortable they were with the situation. I was a bit concerned with the fact that both girls were virgins, but it seemed like my sister knew that I needed reassurance.

Both girls giggled and blushed slightly and started taking off their clothes. Stephanie quickly stripped, and I followed her lead. Both Shelly and Trish stopped to stare at me when I dropped my briefs. Trish’s eyes went wide and Shelly smiled and licked her lips. They both finished undressing.

I had seen both girls in one-piece bathing suits, but now saw their gorgeous young bodies in their full glory. Shelly had small, firm breasts topped by tiny nipples, a flat stomach and a dense tangle of brown pubic hair. Trish had long legs, sparse blond pubic hair and large, firm breasts. I was going to enjoy whatever it was they wanted to do!

We dove into the pool and immediately I was attacked by three naked, nubile nymphs. I moved slowly towards the shallow end, reaching a point where I could stand. When Trish got close to me, I grabbed her and pulled her tightly against me, feeling her large breasts crushed against me. She giggled and squirmed, which only made it feel better. Shelly and Stephanie came to help and when I had the chance, I let go of Trish and grabbed Shelly, pulling her tightly against me, feeling her compact body against mine. Both these girls were going to be a lot of fun!

The horseplay continued for about twenty minutes, but I was careful not to grab Stephanie. I knew that she had talked to her friends, but I wanted to take every opportunity to tease her, and this was a good way to do it. I could tell she was getting frustrated when I didn’t grab her when I had the opportunity, so the next time I had the chance, I simply stuck my tongue out at her and smiled.

“You’ll pay, Big Brother!” she giggled.

“Bring it on, Squirt!” I challenged.

She laughed and said we should get out of the pool.

“Dry off and follow me,” Stephanie said.

We all grabbed towels and dried off, then followed Stephanie to my parents’ sunken walk-in tub.

“We all need to rinse off the chlorine!” she laughed, turning on the shower.

Everyone dropped their towels and got into the large tub. There was quite a bit of giggling and bodies rubbing together. After everyone had rinsed off, Stephanie turned off the water, and we dried off. We walked out into the bedroom.

“Steve, sit on the loveseat,” my sister commanded.

I sat down as instructed. Stephanie sat on my lap, took my hand and put it on her firm breast then gave me a deep French kiss, our tongues dancing lightly around each other. She broke the kiss and got up. She nodded, and Shelly took her place. I cupped her small breast in my hand and we kissed, her full, soft lips parting and our tongues touching lightly. After a minute, she broke the kiss and got up and Trish took her place. I cupped her large breast and our lips touched, parting slightly, allowing our tongues to twist and turn around each other. After a minute, she got up.

Stephanie told us to wait and left the room. She came back with a jar of fudge sauce, a can of whipped cream, and a jar of cherries.

“Steve, you know what to do!” she giggled, getting into the center of the bed.

I chuckled, “I certainly do. One ‘Stephanie Sundae’ coming up!”

She propped herself on her elbows so she could watch while I put fudge, whipped cream and a cherry on each breast, and did the same for her pussy, but used three cherries, just as I had with Jennifer. I knew Stephanie and Jennifer had talked and that my little sister would know what I meant with the three cherries. She smiled when she saw that.

I got between Stephanie’s legs and saw Trish and Shelly move to her sides. I bent my face down to my sister’s pussy and got the cherries in my mouth. I ate them and watched them each eat the cherry from my sister’s breast that was nearest to them. I began licking the fudge and whipped cream and saw Trish and Shelly were doing the same thing. Stephanie started moaning, and I made sure to run my tongue over her clit while I was cleaning the ice cream toppings from her pussy. I looked up and was pleased to see the girls gently sucking on Stephanie’s nipples.

I looked up at Stephanie’s face and she nodded. I moved up to kneel between her legs and pressed my rock-hard dick against her pussy, slowly entering her, while she watched. The girls stopped licking and Stephanie laid back. When I fully entered her, I covered her body with mine. Stephanie wrapped her legs around me and we began moving together.

“Wow!” Shelly exclaimed. “He’s really fucking you, Stephanie!”

“I told you!” Stephanie gasped.

Our lovemaking was moderate in speed and force, and her heightened excitement led to a fairly quick, moderately strong orgasm. We continued moving, building our pleasure. As she got closer, Stephanie began moaning continuously.

As her breathing picked up, she gasped, “Fuck me, Big Brother, fuck me hard!”

We sped up and a minute later I groaned and pushed deep into her and fired jet after jet of cum deep into her pussy. When the first spurt splashed over her insides, Stephanie groaned and I felt her pussy spasm around my dick. We kissed softly several times and then I pulled out.

“That was so cool!” Trish said.

Stephanie got up and she and I went to the shower to rinse the stickiness off our bodies while Trish and Shelly washed their faces at the sink.

“Thanks, Big Brother,” Stephanie said, then whispered, “Who first?”

“Let them decide, Squirt.”

“Let’s have lunch and then you can have your two cherries!” Stephanie said with a silly smile.

Everyone put on just their shorts and I followed three beautiful young women, watching their bouncing breasts to the kitchen. Stephanie got out the cold cuts, cheese, mayonnaise, and mustard. I got out the chips and pickles and got everyone a drink. We each put together sandwiches and grabbed chips, pickles and our drink and sat down.

“Stephanie, how many times can he go? I mean, he already did it once with you,” Shelly asked.

“I think he’s managed six times in the same day with the right encouragement,” my sister said. “But that’s cumming six times, so if you want to give him a blowjob, that counts. I think you can safely count on four before you have to go home tonight. Who wants to go first?”

“Steve should pick!” Trish said with a smile.

“Yes, Steve should pick!” Shelly agreed.

“Oh sure, so I have to be a bad guy to one of you two!” I chuckled. “Do either of you NOT want to go first?”

They both shook their heads.

“Then the only way to do this is random! Stephanie, get a deck of cards, please.”

She went to get a deck of cards and came back and handed it to me. I shuffled the cards a bit and then fanned them out on the table in front of me.

“Each of you draws a card. Highest card goes first!” I said.

The girls looked at each other and then each slid a card out of the deck. Shelly turned over the Jack of Diamonds and smiled. Trish turned over her card and showed the King of Hearts.

“Trish is first!” Stephanie said, getting up.

“Wait, Squirt — what about birth control?” I asked.

“I’m on the Pill!” Trish exclaimed.

“Me too! We went to the clinic together!” Shelly added. “And that was in January!”

I grinned. I sure was not minding being set up like this!

The other girls got up and followed my sister down the hall, and I followed them. They walked into Stephanie’s room and Stephanie turned down the bed. She put a soft towel on the bed like she had for her first time, though I doubted this was going to be kept. I was sure that was only to prevent sheets from getting stained.

“What should I do?” Trish asked.

“Well, you need to take off your clothes first!” Stephanie giggled.

“It depends on what you want,” I said. “If you’re on top, you can be more in control.”

“No, I want to do it just like you did with your sister,” Trish said.

Trish took off her clothes and got into the bed.

“Uhm, I think you need yours off too, Big Brother!” Stephanie smirked.

I took off my clothes and got into bed next to Trish. She turned on her side to face me.

“Trish, are you sure you want Shelly and Stephanie in the room when we do this?”

“Yes! Shelly and I want to see each other. That was our agreement.”

“OK. I just wanted to make sure. You know this might hurt a little bit the first time, right?”

“Yes. Can we stop talking now?” She giggled.

I moved my head forward and our lips touched. She parted her lips and our tongues touched, gently twirling around each other. I ran my hand up and down from her armpit to her thighs. Our kiss intensified, and she moved to her back and pulled me towards her. I broke the kiss and moved down so that I could kiss her substantial breasts. She was tall and thin, but her breasts were large, close to Debbie’s in size, which meant she was probably a D-cup. I licked and sucked her nipples, and she moaned softly.

I slid further down, kissing as I went until I came to her sparse blonde pubic hair. I looked up at her and saw she had her eyes closed and had a small smile on her face. I moved between her legs and continued kissing all the way down her labia. She smelled of roses with a slightly musky hint. I gently pressed my tongue between her labia and licked her softly from bottom to top.

“Oh!” she exclaimed as I grazed her clit.

I took that as an invitation to gently suck on her clit and run my tongue around it.

“Oh! Oh!” she moaned. “Right there!”

I continued licking and sucking her button and less than a minute later, she bucked her hips and moaned. I ran my tongue up and down her pussy to catch the gush of liquid that had flowed with her orgasm, then pressed my tongue into her opening. I felt her barrier and probed gently, but she didn’t flinch at all. I moved on top of her, resting my dick against her labia.

I kissed Trish softly on the lips and she opened her eyes and nodded slightly.

“Just put your legs around mine, however feels comfortable,” I said.

Trish wrapped her long legs around mine, just below my knees. I made sure I was lined up and pushed gently forward with my hips. Her labia slowly parted as my glans moved into her, and I felt the tip of my dick against her hymen. I bent down and kissed her, pressing my tongue into her mouth at the same time I pressed against her barrier. It only took a slight increase in pressure to break through and Trish grunted into my mouth. I kept kissing her as I pushed all the way in, her tight, silky tunnel gripping my dick firmly.

“So cool!” Shelly said. “He’s all the way in you, Trish!”

Trish broke the kiss.

“I know,” Trish gasped. “Oh God, this feels so good! It didn’t really hurt at all, just some pressure.”

I lowered my body onto hers, loving the feel of her rock-hard nipples pressing into my chest. I began sliding in and out of her, and Trish started moaning. After a dozen or so strokes, she began to move her hips, raising them to meet me. She slid her legs further up so that they were wrapped around my thighs.

“Oh ... oh ... oh ... oh!” she gasped, squeezing me tight as her pussy spasmed around my thrusting dick.

It didn’t take long before she had another small orgasm and her breathing grew more and more ragged. I increased the pace, sliding in and out of her hot, slick tunnel. Trish kept moving her hips to meet me, grunting each time I pushed all the way into her. Suddenly, she hugged me very tight and thrust her hips up hard.

“Ahhhhh! Yes! Ahhhh!” she groaned, gasping for breath.

I continued thrusting as her pussy spasmed hard around my dick and her body shuddered. A few more strokes and I pushed hard and fully embedded myself in her and fired several spurts of cum deep into her pussy. When our orgasms passed, Trish moved her legs around my butt and squeezed me tight against her. She started grinding her pussy against me and had another small orgasm a minute later. We relaxed and held each other as my erection subsided and my dick slipped from her no longer virgin pussy.

“Wow!” Trish said when her breathing had recovered somewhat.