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A memorable double date involving Martin, Jeri, Jill, and Sylvia.

Spankmasters
May 15, 2024
15 min read
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Weekend Details: 21st to 30th June, 1974

More appealing ways to spend your Saturday mornings than letting your mom and ex-girlfriend in turns suck your cock exist.

A brief explanation: Following Anne's directions, I asked Heidi Forster out on a Friday - we had sex. Saturday saw me with Betty Payton, same story. Making new acquaintances seemed less challenging than I had anticipated.

To arrange a meeting between Heidi and Joann, I introduced them post-sex. Blonde and busty, with luscious lips, Heidi was renowned as the most attractive student in our class. Passionate about science and sex, she quickly gained Joann's approval.

Betty and I had a brief affair, but she soon moved on to more adventurous encounters. She was petite, shapely, carrying generous breasts. Her nose might not have been perfect, but she remained very beautiful. She shared tales of dating and how it failed due to my inability to fill the 'boyfriend' role. Eager to rekindle our romance, we discussed getting back together.

I divulged everything: my connection with my mother and Felicity, the explorations into my sexual desires. Her curiosity piqued, she demanded more details, even insinuating involvement in my quest for Sylvia.

At her request, I dined with Betty on Monday, along with her mother. Though unfamiliar with the amica familiae tradition, the conversation about my mother and Felicity fascinated Betty.

I mentioned finding Betty a 'companion,' and after dinner, I took advantage of the situation. Starting with her mom, I took pleasure upstairs, while Betty did the dishes.

Once satisfied, I rang my mother on the bedroom phone - ladies only! I presented her with an offer: becoming a 'sort of relative' for Betty - the same as my intimate relationship with Felicity. Her response: her husband Tony (friends of the family) had always wanted to 'enjoy' her.

Thus, my mom secured her status as a semi-amica familiae for Betty. Instructing her on proper technique for blowjobs, that Saturday morning was a professional tutorial. Being there, I benefited from unsolicited but invigorating sex.

"Swish your tongue around the cock's tip," my mom instructed Betty. "Yes, exactly like that. Observe how it affects him."

"There are many approaches for inspiring pleasure. Just running your tongue up and down. Really blow on it. Hum while his cock is within your mouth."

"What's your take on her performance, compared to Tony and Martin?"

"I can't take both Tony and Martin's entire length into my mouth," Betty admitted, "nor has my throat accommodated Martin's large penis."

"What you need is practice in swallowing." Mom was a pro at doing so, allowing me to become deeply ingrained in her throat without choking or gagging. Eating things up and down, she guided Betty. Regardless of success, I was amazed by her efforts.

Happy to have discovered this newfound freedom, Betty embraced it fully - no longer wearing clothes. "I've gone naked for the past five days and have no plans to start wearing them again." She giggled.

"Rules have been set," my mom stated. "Clothing is not a necessity. Sex is available to her at all times, without restrictions on who or when you request, order, or simply suggest." Betty elaborated, proudly.

"Wow," I told them. "That seems a bit excessive."

"It wasn't my idea; it was Betty's," replied someone.

"I acquired this knowledge from a book titled The Tale of O. You should read it."

"I've never heard of it, but I'm certain Felicity has."

"Hey, how's Heidi doing? Have you seen her lately?" We weren't particularly close friends but were friendly. We were all in the same class.

"We've had some amorous encounters this week," I said. "She's having her SMQ measured today."

"Wow!" exclaimed someone. "When can I have the same experience?"

"I'll ask Felicity to arrange it."

"Just to update you, Martin," said our mom. "Jeri's plane will arrive around noon. She does have a brief two-hour meeting at 2 PM. She should be ready to go by 6:30 PM."

"Amazing. Thank you for maintaining a clear schedule for tonight," I expressed.

"She's excited about meeting you. She's looking forward to... exploring this connection."

"Carnal awareness: the pinnacle of experiences."

I quickly unlocked my car and was quickly naked inside my place. I was in anticipation of a speedy hookup with Zoe. However, she wasn't there, so I turned it into a solo event...in Sylvia's memory, of course.

After lunch, I thought about joining Heidi for part of her testing.

In Joann's office, I found the three of them. Joann was dressed, wearing a lab coat, while Felicity was topless, only wearing a black garter belt and stockings. Heidi was clad in lacy lingerie bra and underwear. Her face exuded great satisfaction.

She glanced my way and said, "Eight-three-three, darling!"

"Eight-hundred and thirty-three?" I inquired. "That's the superhero range."

"As predicted," Felicity said, "Your manhood is a constantly pointing e3 detector."

"It's always aimed the right way," Joann agreed.

"We go to considerable lengths to identify suitable candidates for our experiments," commented Joann. "But all we really need is to recruit every one of your girlfriends."

"I've had a request from Betty," I mentioned. "Inquiring if she can be evaluated."

"Absolutely!" Joann exclaimed. "We intend to. Let's have her in next week. Tuesday seems to work for us," she continued.

"So, Heidi," I said. "I'm glad you finally agreed to go out with me."

"I could tell you wanted me," she said. "How did you know?"

"Because you're a woman," I realized.

"Ah, I didn't realise my preferences were so..."

A stunning young woman with beautiful, dark skin and an afro entered the room. "You called for me, Joann?"

"Yes," replied Joann. "Martin, have you met Barbara Brown?"

"No, I haven't had that pleasure yet," I answered, feeling a tad disappointed that I had to wait for next week.

"A pleasure to meet you, Martin," said Barbara. "But, um, I was supposed to show Heidi around the lab today."

"Indeed," said Joann. "Let me introduce you. Heidi, this is Barbara Brown, one of our newer researchers. She's been with us not quite a year."

Barbara expressed, "Yes, I joined this place about 11 months ago."

"So, Joann, you called me in to show Heidi the lab? Is there more to it than that?" I asked.

"No," said Joann. "But considering your current sexual escapades, I imagine her visit may involve some... additional activities."

Joann teased, "I never knew Heidi was so attracted to women."

"Yes, she enjoys both sexes; she prefers girls, you could say," said Felicity.

"I've fucked quite a few guys," added Heidi. "But everyone with a cock and balls wants to fuck me."

"And I'm certain many women would want to as well... including us," said Joann and Felicity, laughing. "And speaking of dating, Martin, you're going out with my daughter tonight, right?"

"She's invited me to Sylvia Raleigh's piano recital," I remarked.

"Jeri is very excited," Joann stated. "I can see all the moving pieces in this plan, Martin. Are you sure this is what you want?"

"I've heard your opinions. But I'm willing," I replied.

"Absolutely, I understand that. Any rushed or impulsive decisions, or simply unwise choices might lead to disastrous consequences. I totally concur with you; I just don't think it applies here. Sylvia and I are longtime friends. Inevitably, social interactions are part of the relationship. Showcasing our support at such an event as this recital is what friends do."

"Do you think there's a chance of... getting lucky?" inquired Joann.

"Not a chance!" Martin responded. "In fact, turning up with a date relieves the stress."

"It seems like a solid plan," Joann acknowledged.

"Consider this," suggested Felicity, "in romantic tales, the central character is usually the love interest."

"So?" asked Joann.

"So, no plan can withstand the challenges it encounters."

Coming from my locker, I found a sports coat and necktie; two ladies helped me dress up adequately. "You look sharp," they mentioned.

My destination was Jeri's address, which I had written down along with the directions provided by her mother. It was in an affluent area of town, and the penthouse offered a spectacular city view.

Jeri herself was charming, with blonde hair and radiant blue eyes, streaks of freckles across her cheeks. Our first kiss felt like sharing a passionate moment, despite our limited acquaintance.

"Believe it or not, I've been waiting for this moment for quite some time," I shared.

"It's been three weeks since we met," she refuted.

"Lust isn't always patient," I stated.

"You're right," she agreed with a grin.

Dinner was at a small bistro close by, and then we made our way to the concert hall.

"I've not met Sylvia personally," Jeri stated, "though I know her parents. I've also met Sylvia's teacher, Beverly. Do you understand Beverly's background?"

"Only that she was a concert pianist. I suppose she's retired now, looking rather young for it."

"Exactly. She must be in her early thirties now. Her story's sad. She was a superstar pianist in the sixties, named Beverly O'Connor. She married a French millionaire, possibly Pierre or Jacques..."

"A French name, surely," I added.

"Incorrect. Nonetheless, she met a gruesome demise. She was kidnapped for ransom. Her millionaire husband tried to save her but perished in the process."

"That's heartbreaking!"

"Yes, it is. Now, Jaguara, a superheroine, rescued her. Along with her companions, Birdwoman and Golden Girl, that's how Felicity and Jeri's mother met Beverly."

"And she established a close bond with Mrs. Raleigh."

"Exactly," Jeri rejoined.

We arrived at the arts center and headed towards the auditorium. "This recital has attracted quite the crowd, don't you think?" I remarked.

"Due to Beverly's reputation, she hardly goes out in public these days. I'm not sure if she'll perform herself," Jeri responded.

"Though she's a sex symbol, and if her young pupil's attractive, it's not surprising."

"A superb wager," I concurred.

"I believe they're... starting," Jeri whispered.

"Sylvia's over there." I noticed Jill, a redhead seated in the middle of the front row, and showed her to Jeri.

We found unobtrusive seats in the eighth row on the left.

The crowd clapped and cheered as Beverly and Sylvia entered the room, each making their way to the piano with grace. The first was a stunning, copper-haired virtuoso in a shimmering green dress, the second a young and beautiful teen in a tight-fitting, revealing black dress. For many, it was their first encounter with Sylvia, and she left an unforgettable impression.

Jeri leaned over and whispered in my ear, "Pardon me while I fantasize."

"You think she's attractive?" I responded in a hushed tone.

"Apparently I'm not the only one fighting the urge to give in," he confessed.

Beverly introduced the evening's performance list, once again drawing applause from the audience. Sylvia took her seat and began to play.

She started with Chopin - Fantaisie Impromptu, Opus 66, then moved on to Rachmaninoff, Piano Concerto Number 3. After that came Ravel, Gaspard de la Nuit, and lastly, Liszt, La Campanella.

As she stood to take a bow at the end of the first half, it seemed like she was looking in our direction. Had she noticed me in the audience?

It was time to make a move - just a simple hello, some complimenting on her performance, and introducing her to my date. That was the entirety of my strategy.

We got our drinks and apps, waiting our turn in line. My heart was pounding, but my usual anxiety was nowhere to be found. I was in control. As we neared Sylvia, I readied myself.

I took her hand for a brief moment.

"I thought that was you, Martin," she mentioned casually. "It's nice of you to come."

"I couldn't miss it. You were amazing."

"Thank you," she replied. Then she shifted her gaze to Jeri. "And who might this be, Martin?"

"Jeri Lear, Sylvia. Jeri, this is Sylvia."

"A pleasure to meet you, Sylvia," Jeri said with a small smile. "And what a fantastic performance!"

"Thank you," she responded. Her eyes seemed to focus on Jeri. "By the way, Jeri, are you by any chance the daughter of John and Joann Lear?"

"That's correct."

"My goodness! You look exactly like your mother," Sylvia remarked.

"And you look like your father."

Sylvia looked back and forth between Jeri and I. "How can we have not met before now?"

"Bizarre, isn't it?" I said with a chuckle. "But it's great to finally meet you."

Sylvia turned to Jeri. "You're very kind. [And here's the compliment] You're one of the most beautiful women I've ever seen. Now that we've met, I hope we can get to know each other better."

I couldn't tell if there was any sexual tension, but it was definite between them.

"You're very kind," Sylvia said to me. "And if I may return the compliment, you are one of the most beautiful women I've ever met. Now that we've met, I hope we can become better acquainted."

My heart raced. I had been hoping that my reluctance to chase her might result in a change in her perception of me. I looked into her beautiful eyes and imagined kissing her, but hurriedly tried to put that thought to rest. I couldn't possibly become involved in an affair with Sylvia, no matter how much I found her attractive.

We ate dinner with Jeri and Jill afterwards, Sylvia's girlfriend. I hadn't introduced myself to Jill yet, so I did so, and presented Jeri as well. She seemed nice but didn't appear overjoyed at our sudden inclusion in their plans.

As Jeri and Sylvia talked, I tried my best to hold back the hope that something unexpected would happen between us. The thought of being with both ladies was one I could not entirely shake - though I knew that could only lead to disaster. My mind wandered back to Felicity's warning that hooking up with Sylvia would be detrimental.

As the evening progressed, Sylvia and Jeri continued to exchange stories about their families, and discussed how strange it was that they had finally met.

Sylvia looked at Jeri, "I've heard such interesting stories about you, Jeri. Here we are, meeting in the flesh at last."

"Interesting stories? What were they?" She asked with what seemed like a mysterious smile.

I couldn't help but wonder what they'd been talking about, as something noticeably significant had clearly passed between the two of them. I couldn't wait to find out.

In that moment, in that place, it felt completely opposite. Making love to Sylvia—for the first time of many—would be the greatest experience of my life. Though I had faith in my friend's advice, I began to worry about having sex with Sylvia. I wanted it desperately while being fearful at the same time.

I seemed to have disappeared from the conversation in my thoughts.

"Martin?" Jeri said. "Were you listening?"

"Oh, yes. Go on."

Sylvia looked at me with a playful grin. "Jeri and I have plans to continue the celebration later—in bed. And I'm guessing you and Jeri have an exciting night of intimacy planned as well."

I was stunned. "That's true," I replied.

Sylvia and Jeri conferred for a moment. I couldn't tell if Jill was completely on board, but she Beamed at me cheerfully.

"How about a swap?" She suggested, joking. "What if we switch partners for the night, just for fun?"

The possibility of swapping partners was completely unexpected. It contradicted what Felicity had previously warned me to avoid. But how could I refuse?

Would I trade partners with Jill, spend the night with Sylvia while she was with Jeri? Absolutely! Oh, yes! Oh, fuck, yes!

I gazed at my date. "What do you think? Would it bother you?"

"It wouldn't bother me in the slightest," she replied with a smile.

"We'll make up for it later," I said.

"We will," she agreed. "Soon, very soon."

"It's a deal, then," said Sylvia. "Shall we go?"

I'll never forget what happened next. We headed outside to our vehicles, my TransAm beside Sylvia's Delta 88 convertible. Sylvia opened the passenger door, and Jeri climbed in. Sylvia joined her on the other side, leaned in, and kissed Jill.

"Goodnight, my darling. See you in the morning, or when you two finish," she said, then the two drove off together. I stood there in shock instead of helping Jill into my car. I quickly realized how inappropriate my behavior was and opened the door for her.

This turn of events shouldn't make a difference. Jeri and I were set to have sex. Yet, in that moment, my mind processed the realization I'd be having sex with Sylvia.

But then... everything changed abruptly. Jill and her girlfriend had pulled another switcheroo.

I couldn't let this deter me from living out a minor fantasy, at least. And there were a few reasons to avoid taking Jill to the Manor. Sylvia had no idea of my plans there. Alternatively, I didn't know how to explain all this to Felicity.

So, it was off to my childhood home, to my former room. I parked my TransAm in the back and let Jill and I enter the house through the back door. I quickly discarded all my clothes, following my rule.

"Even if you are an impatient one, you're quite an open book," Jill observed.

"This requires some explanation," I said.

She studied my erection and added, "I think explanations will be kept to a minimum."

We started toward the stairs. I realized we wouldn't reach my bedroom when I spotted everyone else up, watching TV in the living room.

They saw us and stood to greet us. It must have been unexpected to see us come in so suddenly.

"This is Jill Cannady, isn't it?" asked Mom. "We met you at the Raleighs' house."

"Yes, that's right. Jill Cannady. Nice seeing you again, Mrs. Donovan. Mr. Donovan. And hi," I said casually.

"Hi, Mr. Donovan," said Betty.

"What brings you here so late?" asked Betty.

"Sharing our plans," said Jill.

My parents couldn't miss the fact that Betty was also naked. They showed mild surprise but looked at us.

"We saw you two going in here," Mr. Donovan mentioned.

"We'd just ascended the stairs," I updated them. "Apologies for disrupting the film."

Stepping into the bedroom, Jill quickly shed her clothing. A blow-up poster of Sylvia adorned one wall that piqued her interest, as did a smaller photograph on the adjacent wall. Another one was on my desk and yet another on the bedside table.

"None of those are me, huh?" she teased.

I retrieved a few photos of her from a box beneath my bed and presented them.

"Masturbation? For little ol' me? That's quite flattering. It seems you've contributed a lot of semen to Sylvia, going by how many of those photos there are."

"What can I say?"

"Say nothing. We share that. I've been masturbating for her daily," I admitted.

"What do you mean, 'jilling off'?"

"Exactly! I'd like you to eat my pussy, my dear. Would you be so kind?"

She was usually easy to persuade, so I wasn't anticipating a rejection. I'd been meticulously practicing oral sex recently, and had some fresh tricks I was eager to use on Jeri's vagina. Her tame reactions helped me to try these out on Jill. She was so lively and squirmy that it was a challenge to hold her down during the act.

"Oh my god, you're fantastic at that, Martin!" she cried. "You'd almost think you were a woman!"

She came strong and sprayed my mouth with her nectar. Her taste was delectable, and I had difficulty consuming it all.

She was in good spirits afterward. "I'm famished. I need a snack."

Luckily, I still had an erection. "And your snack is eagerly awaiting you as well."

She regarded my penis quizzically. "Have you mistaken me for someone hungry? I mean, I'm starving."

We headed to the kitchen. She made plans to put her clothes back on.

I challenged, "Is it necessary?"

We dined on Cheez Whiz and Ritz crackers. She consumed the entire can.

I grinned suggestively, "I've been thinking about what I'd adore to do to that delectable vagina of yours... but with another appendage."

Perhaps I wasn't clear enough, as it appeared Jill comprehended my meaning.

"Hmm. Presently, I'm not in the mood for a cock. I was pondering... perhaps my 'sister' should join us?"

"I mean Betty, but she's not my sibling."

"Forgive me. You and she look just alike. Who is she?"

"She's my parents' partner living with them."

"Ah! The elusive unicorn."

"Yes, and previously my girlfriend."

"'Curiouser and curiouser,' Alice remarked. Would you like to inquire if she's available to please you both?"

"It certainly can't hurt if she's still conscious."

She indeed seemed conscious, as the room held light under my parents' door and the sounds of devotion emanated from within. I rapped softly and peered through a crack in the door.

They noticed my presence and stared at me. Not my father, as his face was buried in my mother's crotch. Betty said "Hi", but her attention remained focused on her bouncing.

"I'm sorry to intrude on your intimate moment," I apologized, "but my companion has requested the presence of my 'sister' to make our meeting a threesome. But since you seem to be quite busy..."

"Relax, sweetheart!" she cooed. "I'll take care of Tony myself. Go and enjoy yourselves."

Betty dismounted Dad's pelvis and my mother took over. He appeared content, knowing he could breathe.

We sprinted up the stairs together, Betty in the lead. Upon her arrival at my bedroom, Jill and she embraced in an ardent kiss. And so, the scene unfolded. We had started engaging in sex, but I was gradually relegated to the sidelines.

At some point, I relaxed on my lounge chair and simply watched. If no one else would look after my penis, I would have to do it myself.

However, it's not the most awful situation to be in - to sit and gaze at two sizzling teenagers having lesbian sexual intercourse while you masturbate.

They went on for so long that my eyes struggled to remain open. When I awoke again, they were still fucking like rabbits. And now, it was Jill and my mother. Betty lay next to them, asleep.

I dozed off again, and upon waking, it was Betty, Jill, and my mother engaged in a tranquil chain link.

The rest of Sunday continued in a similar vein, like a private girls' club. I started to wonder if Jill wasn't interested in guys at all. However, the positive aspect was that I managed to complete my self-pleasure tasks much faster.

Towards the end of the day, when everything quieted down, Dad prepared burgers for everyone.

"I suppose I should take my date home at this point," I said, after we had all finished eating.

"Oh, Betty can take me home. Right, Betty?"

"As long as I can find my clothes, I will, of course. It's a shame about my streaking record, though."

"How about you wait until the night to do it?" I suggested. "Then you could do it naked."

"It would be more challenging with my breasts, but if you can manage it, so can I."

Jill then exclaimed, "One thing, could you drive me to Beverly's? I've been staying there with Sylvia quite a bit recently. And that's where my car is."

They departed, and I told my parents about the peculiar circumstances of the day.

"So, you still haven't slept with Jeri?" Mom inquired.

"No, not yet. And it's unclear whether Jeri told her anything about me."

"And it appears that Betty might not be returning tonight."

"But she's without any clothing... so... never mind."

"It seems like these girls' priorities might not involve you that much-which is a good thing."

"Let's hope so. In any case, I have a meeting with Felicity planned for the early hours of tomorrow morning."

"Lucy," Dad warned, "you've got some explaining to do!"

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