Striding away purposefully, Donna’s graceful figure receded from view as she walked from the dock through the parkway along the harbor. I watched her gorgeous butt sway lazily until her form became obscured by the trees in the nearby park.

‘Did she at all times walk like that,’ I thought, ‘or did she know I would be watching her until she was out of my sight?’

Back on my boat, I reflected on the incredible weekend I had shared with her to that point. As satisfied as I felt, my cock stirred in anticipation of seeing her again that evening.

I stowed her bikini after breathing in one more scent of her thong. The lake had washed it, but I could still detect the faint musky aroma of her arousal. I smiled to myself and looked forward to being with her again later, providing that the little plan we hatched would come to fruition.

I ducked my head into the cabin. The steamy scent of our Sex had all but dissipated on the trip back, but I opened the side hatches to make sure. No more than a few minutes later, my buddies called from the dock entrance, so I walked over and ushered them in.

“Right on time!” I welcomed them cheerfully as I swung open the gate. They greeted me and thanked me for the invitation.

Once we boarded the boat, I stowed the cooler they had brought, and asked, “Ready to get under way?”

“Aye aye, Captain!” they said in unison.

I fired up the engine and released the moorings, and we headed out toward Lake Michigan. As we cruised out of the harbor we fell into easy conversation.

Brian asked me how the week had been going so far, “Has it been boring out here all by yourself?”

“Not too bad,” I fibbed. “I always manage to entertain myself.”

Dan took the opportunity to dish out a dig. He made a whacking off motion and said, “I’ll bet you and your left hand got along swell.”

“We always do!” I laughed and added, “Just like we’re on a honeymoon!”

We continued with lewd and crude guy talk and cruised around Lake Michigan as the sun began to dip behind the skyscrapers of Chicago. After a while, we entered the locks and watched with wonder at the monumental engineering feat that lowered us six feet down to the river’s level. When the inner gates opened and the lock tender’s horn blew, we tooled out of the locks and into the Chicago River.

The guys were in awe of the tall buildings flanking us on each bank and the many ornate bridges we cruised under. We shared a few Adult beverages and worked our way up around Goose Island, then back to our dinner destination at the City Tavern along the Chicago River Walk.

I glided up to the pier and a dock boy jumped up to catch the ropes that Brian and Dan tossed him. He deftly tied us off and I tipped him on our way off the boat and to the nearby tables.

Seated at a waterside table, my friends perused the menu while I scanned the area looking for my girl. The guys and I had just ordered our second round of drinks and placed our orders for steaks, when I noticed my sexy Donna strolling along the highest terrace, even with the street. She was accompanied by a curvaceous brunette that I knew must be her friend, Brenda.

‘One of my buddies may be in for a real treat,’ I wondered.

I surreptitiously watched them over Dan’s shoulder as they descended to the table area. Donna caught my eye and winked quickly before pretending not to see me.

I watched her motioning to the hostess. She seemed to be asking if they could sit at one of the tables near us and I covertly watched as she gracefully lowered her sweet derriere onto a seat not far from our table. I also got a nice eyeful of Brenda’s ample and shapely butt as she took her seat facing away from me.

The girls were decked out in little black dresses and looked like they were ready to break some hearts that night. Whether I had already known her or not, Donna would have captured my attention. Her pinned-up hair highlighted her graceful neck, and I momentarily became lost in thoughts of kissing her there.

She caught my eye as I stared at her, fantasizing about her. She briefly smiled back before lowering her eyes shyly. She squirmed in her seat and glanced at me once more before returning her attention to her friend.

I thought if she was getting wet between her legs due to our mutual desire. I guessed she was, because I was swelling to hardness just looking at her and had to squirm in my seat, too.

Brenda was quite an eyeful herself. A little taller than Donna and bigger all the way around, she had a voluptuousness about her that oozed sexuality. Her LBD showed quite a bit more cleavage than Donna’s version, and it hugged her hourglass figure nicely.

Donna and I exchanged more furtive glances throughout the meal, and tiny smiles, too, but we both tried to remain attentive to our dinner partners. So far, our little plan was falling into place. We were seated with our respective guests at tables not far from each other.

The steaks and sides soon came, which were delicious. Then, another round of refreshments, followed by another. The guys were in a partying sort of mood it seemed, and the conversation was light and full of laughs. The time was nearing when Donna and I would hatch the next part of our little escapade.

———————————

Donna had told me earlier that day at breakfast that her friend, Brenda, had split up with her husband the prior year, and predicted that Brenda would be even hornier than her usual self this evening, which was at all times Horny.

She added that her friend was basically a nymphomaniac, which was probably why her first marriage hadn’t lasted. She also advised me that Brenda had met her own husband, Gerald, so she would have to act like she didn’t know me when she was with Brenda. She confided that, as much as she loved her dear old friend from school, Brenda was exhausting to be around.

“Every time we’ve gone out,” Donna told me over coffee after breakfast that morning, “she has put pressure on me to pick up some guy and go home with him so that she didn’t have to feel bad about leaving me to go off and do the same thing!”

“Really?” I mused.

“Yeah. I would play along and flirt with the wing man of whomever she set her sights on, but that always put me in an awkward position when I had to let the poor guy down after Brenda took off with her latest prey to go fuck his brains out.”

“And how about you? You never went home with a guy yourself?”

“I honestly never felt the urge,” she said quietly. “And if I did, I never acted upon it.” Then she placed her hands over mine at our table and added, “Until last night, with you, that is.”

Hearing about Brenda’s many sexploits, and knowing what horn dogs my buddies were, helped us to conceive this crazy scheme. If it worked, she and I would be Free to be with each other much earlier that evening, our mutual ulterior motive.

———————————

I broke from my reverie of that morning’s conversation with Donna, to hear the punch line of some dirty joke Brian was telling. Dan was howling with laughter. I had no idea what Brian had said.

I changed the subject and grabbed their attention by saying, “Hey guys, don’t turn around, but I think I know one of the ladies seated at a table nearby.”

Dan stole a peek anyway and Brian leaned in toward me, saying “Do tell, do tell.”

“I’m pretty sure I went to high school with her,” I fibbed, per the plan I had made with Donna. “Dang, boys, she was Hot then, but she’s even hotter now!”

“Which one?” Dan asked quietly, “the blonde or the brunette. They’re both pretty Hot.”

Brian clumsily pretended to drop his spoon and snuck a peek as he retrieved it.

“You can say that again,” he said as he returned to his seat. “Especially the brunette! Did you see the tits on that one?”

“The blonde is the one I know,” I told them.

“Yeah, she’s pretty Hot, too,” Brian opined.

I wondered to myself, ‘If you only knew, buddy.’

Instead, I said, “Looks like they’re wrapping up dinner. I’m gonna go over and say hi and see if she remembers me. If you’re lucky, you might get introduced to the brunette she’s with.”

“Saving the blonde for yourself, Jimbo?” Dan teased.

I gave him an exasperated look and again, wondered to myself, ‘You bet, buddy. I’m keeping her all to myself!’

I approached the table where the two girls sat and spoke to Donna when they both looked up at me. “Hi, Donna?” I asked, acting as if I was unsure. “Donna Meyer?”

Donna feigned a quizzical look, while out of the corner of my eye, I noticed Brenda looking me up and down.

“Yes?” Donna replied questioningly.

“I thought that was you. It’s Jim. Jim Hart!”

As planned, she pretended she didn’t recognize me. Brenda continued to size me up.

I stammered on, “We went to high school together. We were in marching band togeth…”

“Oh Jim! Jim Hart! Of course! Now I remember. Wow, Jim! It’s been a while!”

“It sure has,” I agreed, thinking of how long the several hours since I’d last saw her naked seemed. Now it was Donna’s turn to look at me appraisingly.

“Jim, how have you been? It’s really good to see you again,” Donna said, then she added slyly, “My how you’ve grown from the gangly band geek I knew!”

I stung from the opinion, not appreciating her improvisation, although I had to admit it was convincing. She had no idea what I was like back in high college. We had only first met last night, but I played along anyway, replying, “Late bloomer, I guess?”

“I’d say,” she said teasingly.

Donna introduced me to Brenda who gave me a seductive stare as we shook hands. I wondered to myself, ‘This one looks more insatiable than Donna, if that’s efficient!’

I pressed on per the plan and said aloud, “I thought I recognized you and had to see if it was really you!”

“It’s really me!” she said musically. “It’s very nice to see you again, Jim. What brings you here tonight?”

“I’m here with a couple buddies,” I replied, to which the girls peered past me and over to my table where my two buddies sat, staring dumbly back at them, their jaws slack and tongues practically wagging.

Brenda remarked, “They’re kinda cute.”

“They’re good guys, too. I can vouch for them,” I said and added, “How about we join you for an after-dinner drink? Catch up on old times a little, and maybe make some new friends?”

Donna looked over at Brenda, whose bright smile and enthusiastic nod indicated she would welcome the business and the attention of my friends and me.

“Sure! Sounds fun!” Donna said. “Call your friends over and you and I can catch up!”

I returned to my table and said to the guys, “Right this way, gents. There are a couple of attractive women right over there, who want to have a drink with us.”

They both leapt to their feet, practically knocking over their chairs in the process, and followed me over to Donna and Brenda’s table.

I made sure to grab the seat closest to Donna while Brian and Dan sat down on either side of Brenda. We went through introductions and then ordered a round of tequila shots, a little inside joke between Donna and me.

The conversation flowed easily, punctuated by a lot of laughs. Brenda was warming up nicely to my friends, who were in turn very attentive to her, while Donna proceeded to fill me in on everything that had happened to her since high college, as if we really were old college chums catching up.

Our heads were close, in our own little world at the table. It was nice to learn more about this sexy and fascinating woman. She shared how she had become Donna Potelkin. She had married for stability and security but had to sacrifice fun as a priority since then.

As she spoke, she reached over under the table and started caressing my plump member through my shorts.

“Nice to get away for some real fun now and then,” she said softly and squeezed my girth.

I grew within her grasp as she covertly massaged my crotch under the table. She smiled knowingly when her caresses made my rod grow long and hard from her soft touch. She trailed her nails along it’s length, sending electric sparks through me.

“You know what I’d like to do right now, don’t you?” she asked demurely.

“No, but I know what I wish you could do right now,” I replied.

“Guess,” she said.

“Hmm,” I pondered. “Maybe crawl under the table, like in the jazz club last night?”

She looked at me mischievously and replied, “You guessed it.”

Then she leaned in close to me, licked her sexy lips, and silently mouthed the words, ‘I want your cock.’

“I would Love that,” I said quietly. “Except for the fact that there are video cameras all around here, and there are no floor length tablecloths like they had at the club.”

“You’re right,” she admitted. “I guess I’ll just have to wait, but I’m not sure how long I can hold out.” She squeezed my thick member under the table and squirmed in her seat, giggling.

Our attention was diverted to the trio seated across from us when Brenda boisterously laughed at something Brian had said. I noticed how her ample breasts jiggled when she chuckled.

She lifted her empty glass and asked, “How about one more, guys?”

“Sure!” they guys said in unison. They looked over at us questioningly. Brenda had a sly smile on her face, like she was up to something.

“I’m in!” Donna replied. Then, to Brenda across the table, she said, “But you know what happens to us girls when we drink tequila, don’t you?”

Brenda chuckled softly and replied with a devilish grin, “It makes our panties fall off, that’s what!”

She looked at each of the guys flanking her with a sly smile. They leered back at her hungrily. I noticed that Brenda’s hands appeared to be under the table and moving over the laps of my friends.

I caught the waiter’s attention and ordered another round of tequila shots. While we waited for them, I asked Donna a question I already knew the answer to. “So, are you ladies staying downtown?”

She replied, “No. Actually, we cabbed it here from the Northside. I’m staying at a hotel on Diversey, and Brenda lives near there.”

“Well, what do you know about that?” I asked in mock surprise. “Diversey Harbor is where we’re headed after this. How about we all cruise back to the Northside on my trusty boat when we’re done here?”

Now it was Donna’s turn to act surprised while Brenda’s face lit up at my suggestion.

“You have a boat here?” Donna asked, knowing full well that the boat I had fucked her on earlier that day was sitting right in the river nearby. She was a pretty good little actress.

“Yep, there she is,” I said proudly, gesturing toward my humble craft.

“I think that could be fun!” Brenda cried. Then, looking at Donna, she asked, “What do you think, honey?”

Donna pretended to think about, giving that distinctive gesture of pressing her manicured nail lightly against her lower lip, then she replied, “I guess it’d be okay. These guys look safe enough. I’ve known Jim for a long time, and he says his boat is trustworthy. So, let’s do it!”

“Let’s do it!” the guys said in response.

The drinks arrived and we downed them with Brenda’s toast, “To a special night between new friends! Let’s do it!”

I paid the check for both tables to everyone’s surprise and began ushering the group toward the boat. Brenda and Donna excused themselves to go to the ladies’ room while Brian, Dan and I waited onboard.

“Holy shit!” Brian exclaimed while they were gone. “How about those tits and that Ass on Brenda?”

“Yeah, smokin’ Hot!” agreed Dan, then added, “And she looks like she’s ready for some action!”

“Looks like it and acts like it!” Brian heartily agreed.

I replied, “She’s sure does, but I gotta admit, I’m more attracted to Donna.”

“That works out perfectly, then,” Brian said. “We won’t have to fight over Brenda!”

“I wonder which one of you studs will be going home with Brenda tonight?” I pondered.

“Maybe both of us!” Dan offered.

“Kinky, man!” Brian declared. “But hell, buddy, I guess there’s a first time for everything!”

Just then, we spotted the girls sashaying back toward us. I secretly hoped my friends would have as good a time with the voluptuous Brenda as I knew I would have with the petite Donna.

“All ready to set sail, Captain?” Brenda asked.

Donna asked with a wink and mock salute, “Permission to come aboard, and to have fun, sir!”

“Permission to come aboard, and to have fun, granted! Welcome aboard!” I exclaimed.

The guys each held out a hand to help the ladies get on board. I thanked the dock boy who had arrived to cast off lines and we were soon on our way up the river. Donna cozied up next to me at the controls while Brenda nestled in between Brian and Dan on the wide bench seat in the stern. Dan handed out refreshments to everyone and sat back down next to Brenda.

As we slowly meandered north along the shoreline, giggling and “mmm’s” from Brenda reached my ear from the rear of the boat. Glancing back now and then, I saw her kissing Dan, while Brian leaned into her and rubbed her thighs. A bit later, she was making out with Brian while Dan was digging into the cooler to set up another round of tequilas.

“You guys want one?” Dan asked me.

I looked at Donna, who shook her head slightly, and I replied, “No thanks, man. I’m driving, and Donna is my copilot.”

Donna snuggled up against me and we heard the clinking of glasses from the stern. Then Brenda toasted, “To panties coming off!”

Soon, more moaning could be heard behind us, and we looked back to see Brenda laying across the laps of my friends. Dan was kissing her while her legs splayed across Brian’s lap. His hands were roving over her legs and disappeared under the hem.

Donna and I exchanged a knowing glance and she said, “I think she likes your friends.”

“Yeah,” I agreed. “And they seem to like her!”

“Things are working out better than we hoped,” she said conspiratorially.

I pulled her in close, lowering my mouth to hers, and we exchanged a tender kiss. When our lips parted, we glanced back at the other three, who had stop fondling each other and were now looking at us with wide grins.

“Ooh la la!” Brenda said. To the guys she exclaimed, “It looks like we’re not the only ones who are gonna have special fun with new friends tonight!”

I gave a sheepish grin and Donna looked at Brenda with feigned exasperation.

“I’m allowed to have a little fun, too, aren’t I?” Donna asked with a pout.

“Or a lot of fun if you like,” Brenda replied, glancing mischievously at my tented shorts then back at the two of us. “A LOT of fun, girlfriend!”

She laughed musically and sat up. Lifting her knees, she gracefully twirled on her butt to switch positions and laid her head on Brian’s lap as her legs alighted onto Dan’s.

Both of my friends looked overjoyed as they turned their attention back to Brenda. Brian slid a hand under her back and brought her lips up to meet his, while his Free hand cupped her breast. Dan sighed contentedly and began massaging her calves. Soon he reached under her dress and began caressing her thighs, while using his other hand to fondle her other breast.

Amidst her sighs of encouragement, both men moved to lower her dress front. She gave no resistance but a low purr in Brian’s mouth as his mouth covered hers in a deep kiss and she writhed at Dan’s touch down below. They fondled Brenda’s exposed breasts to the sounds of her delighted mewls.

Donna looked up at me while I slowly tooled along the shoreline. With a mischievous grin she moved her hand down the front of my shorts to feel my hard tool pulsing through the material.

“Watching them is getting me Hot again,” she confided.

“Me, too,” I agreed. “I can’t wait to get you alone.”

“I can’t wait that long,” she said and began to slowly lower my zipper. I offered no objection as she slipped her hand into my open fly and began to massage my hardness.

“Mmm, that’s what I want,” she purred and then worked my stiff member out of its confines until it was proudly protruding.