The Circle Ch. 03

Story Info
Escalation to second base and keeping Alice satisfied
3.6k words
4.7
32.1k
17

Part 3 of the 52 part series

Updated 06/07/2023
Created 11/22/2015
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Chapter 03 – Escalation, second base, and satisfying Alice

Jim took Monica to a major league baseball game in the city, followed by dinner at Benny's Sports Bar, and then a slow drive home along the picturesque waterfront. He played the perfect gentleman at her home, ran around the car, and opened the door for her. As she emerged from the car, she flowed into his arms.

The kiss between them might have appeared to be automatic, but it wasn't. Both Jim and Monica had thought of little else since the end of the ballgame. One kiss became several, and then Jim walked her to her front door, bid her goodnight, shared one more kiss, and left.

Matt and Sheila also had a fun afternoon playing photographer and model. They went to the coastline, but instead of swimming spent hours as Matt posed Sheila, and took a thousand photographs of her. Sheila relaxed from her ice princess visage, got into playing model, and did everything from hamming it up with funny faces to looking as sultry and sexy as she could. She even made a few wardrobe adjustments to tease the camera, without every really displaying anything vital. The date had been just the right touch to appeal to her ego, draw her out, and put her at ease that she was liked without conditions.

Over dinner at a little bistro, Matt downloaded the pictures to his laptop computer and together, sitting closely side by side, they went through the hundreds of shots and picked the best ones. Matt assembled a small album of the best and most liked, and emailed them to Sheila. Sheila displayed no reticence about the date or being close to Matt.

After dinner, Matt drove her home. Sheila said, "Come in for a while."

Matt balked, "I don't want to be an inconvenience or anything."

Sheila insisted, and soon they were again side-by-side on the sofa in her family room watching some television and talking about the photo shoot.

Sheila whispered to him after a lull in the conversation, "Do you like me?"

"God, yes. Why would you ever think I didn't?"

"Because you haven't tried to kiss me."

Matt's answer to her statement was to slowly take her face in both of his hands, turn her towards him, and lay one hot seductive and smoldering kiss on her lips that lasted well over two minutes, including the little side excursions to kiss her eyes, nose, ears, and cheeks. Sheila purred.

When he stopped, Matt stood suddenly and fanned his face. "I think I better be going, otherwise I'm going to be in trouble here. Thank you for a fun day – one of the best in my life. I really like you."

Before Sheila could even open her mouth to protest, he bolted down her hallway and out the front door.

Bob's date with Zoey was also a bit unusual. He started at eleven in the morning with her, and they drove to the lake and then slowly around the huge perimeter, stopping at every antique and junk shop along the way, and there were a lot of them. Zoey was enthralled that Bob even liked that kind of thing, not realizing that he'd seen the backgrounds in many of her online photos that showed many carefully selected relics of early North America and even some Native American art and crafts.

Zoey and Bob lingered over what started as an early dinner. Somewhere in the discussion, Bob let it be known that he was working on distilling the ten secrets to life, love, and happiness.

Zoey pleaded, "Oh, come on, you have to tell me now that you've confessed to your intellectual hobby. What's your list?"

"They're not in any order, except as I thought about them or wrote them down, and I'm not finished yet. The first is to love and care for others, friends and family. Relationships are key." He explained about the constellation of friends.

Zoey pondered that and said, "So I could claim that you, Jim, and Matt are in my constellation on the male side of things."

"Yes, and Monica and Sheila would be on your female side too. I like the idea of the three of you being in my constellation. I hope you realize that the three of us are really taken with the three of you."

Zoey blushed at Matt's admission, but diverted the conversation by asking, "What's next?"

Matt held up two fingers, "You have to have clear goals in the important areas of your life – relationships, career, recreation, health and fitness, sex, and your creative side. The goals should inspire action to achieve them in the timeframe you want."

"Next, you have to believe in yourself and your capabilities, and not take in negatives. Attitude counts for a lot. You need to be creative and never stop learning. You need to worry the details, and you need to focus your efforts, time, and money on your goals and not get distracted too much. You also need to live in the Now – not let the past bog you down, or worry too much about the future."

"As of today, I've added another. You have to communicate effectively and efficiently in both directions – receiving and emitting. To do that, we need to learn to hear or read between the lines about what motivates others, and what makes them happy."

Zoey smiled, "You made me very happy today. How'd you know I'd like antiquing?"

Bob smiled, "I looked at the backgrounds in many of your online photos."

Zoey said surprised, "You studied me?"

"Intensely. I want to know everything there is to know about you." He looked embarrassed. He admitted that Bob and Matt did too.

"You like me?"

"A lot."

Sitting next to each other in a booth at the restaurant made it easy for Zoey to throw her small body into Bob's arms. The kiss melted the nails in his shoes, and clearly signaled that she liked him. He was glad she'd initiated the kiss.

Despite the possibility of further 'action,' Bob ended the evening early, dropping off Zoey at her home, but sharing several more really hot kisses on her doorstep.

Two evenings later, in the park, Bob said, "Next step, we rotate dates again. I talked to Alice on the phone today, and she confirmed this was the next step."

Jim and Matt listened attentively.

"This is hard, man," Matt protested. "I could have made out with Sheila for hours. I can assure you that this ice princess is melting."

"As I could have with Zoey, but we have a more lofty goal that we should not get distracted from. Remember to focus. We each want all of them, if I can put it that way."

* * * * *

Sheila hugged a pillow to her chest as she sat on Monica's bed, "Oh, I didn't want to stop. Matt kisses divinely. I bet he's a fabulous lover too."

Zoey had been stretched out on her back on the floor in the middle of the room. She sat up, "You mean you're ready to make love to him? You've only been on two dates with him, and one of those was all of us together."

Sheila laughed, "The thought crossed my mind. Remember, this is the 'new me.' I keep saying to myself, 'I am not an ice princess. I am open and receptive to the pleasing advances of men I like. I don't want to die a spinster.' I really am trying to change."

Monica said, "Well, I liked Jim, and he behaved like a perfect gentleman. I was so surprised when he took me home, kissed me goodnight, and left. If I'd been a guy I would have been all over me. I had my green light shining high and bright."

Two days later, Jim's call to Zoey for a date left her speechless. She said to him, "Errr, I sort of thought maybe Matt might call. This is unexpected."

Jim said, "Well, I know he liked your date and he said he had a lot of fun. I thought we could too, and I have a cool place to take you where I know you'll have fun. Matt is calling Monica to see if she'd like to go out this weekend. By the way, Bob is contacting Sheila. We like each of you – a great deal and want to get to know all of you really well."

"Oh. I don't want to upset Matt, but if that's accurate then sure, I'd love to go out with you." Zoey did like Jim, and the idea of dating both men at this stage had appeal to her. If the three men wanted to date her, so much the better; and if they wanted to date her friends that didn't disappoint either so long as no one got jealous or angry.

The other calls from the men had similar results.

Jim took Zoey to an early dinner, and then to a most unusual shop calledPainting With A Twist. The store teaches people to paint with acrylics, having a teacher on a podium at the front of the room. Each person gets a canvas, and a paper plate with large globs of primary colors on it, along with black and white, and the teacher explains how to mix the paints to get the desired effect in a painting and teaches about brush strokes. Everyone paints the same thing. The paints dry quickly, sometimes aided by hair dryers, and you can take the completed painting home at the end of the two-hour evening. There were about thirty people in the class.

Zoey was jumping around with joy at the opportunity to do a two-hour painting. She'd painted before, but never in this casual and fun setting. A bottle of wine between the two of them helped the evening pass too.

Jim's picture was obviously amateurish, but showed potential for him as a future artist. Zoey's was beautiful, and something anyone would be proud to display in their living room.

As they carried the paintings to the car, Jim slipped an arm around Zoey's shoulders. She looked up at him with a huge smile.

"I had fun. This was a very innovative date," she praised and put her free arm around his back and hugged him.

Jim nuzzled into her hair and kissed the top of her head.

As they got to the car, Zoey whispered, "My lips are down here."

They set their paintings on top of the car. A fraction of a second later Zoey was in Jim's arms, and the pair rained down kisses on one another.

Jim said, "Come on, let's go somewhere where we can be alone." Although his statement had been made with authority, he listened and watched for any signal that might telegraph Zoey's unwillingness to make out. There were none, and he even got a smile of approval.

Ten minutes later, Jim pulled up at the end of a dead end street in Zoey's neighborhood. He'd cased out the place in the daytime. Only a few houses were near; plus a few buildable lots. He thought the place safe, almost dark, and would appeal to Zoey since it wasn't far from her house.

Zoey apparently got into the spirit of the night rather quickly. As they made out, and Jim copped a feel of her breasts; Zoey suddenly pulled away. She said, "This is in the way. I like what you're doing." She pulled her light blue top over her head leaving her in just her brassiere. A moment later, she'd removed that too.

Jim worried that things had taken such a giant leap. He'd hoped for a good make out session, and to cop a few feels of Zoey's breasts through her clothing. Getting to see and freely play with her breasts was beyond his expectations.

Jim felt, licked, sucked, lapped, tongued, and pinched Zoey's breasts and nipples as they kissed. Their sexual temperatures were rising. At one point he was sure that she'd had some kind of climax or orgasm from his ministrations. He made sure to keep all the action above her waist despite her suggestive writhing.

They spent an hour petting. Zoey got brave and had started to rub Jim's cock through his pants. The hardness there was impossible to ignore.

To keep things under control, Jim thought of his time with Alice the night before. She'd asked that each man take her individually for a change, thus they had really made love and had a highly passionate time together.

The passion Jim and Zoey shared stopped suddenly when the residents of one of the nearby houses drove down the street towards their house with their high beams on, lighting up the dead end and their car. Zoey dove for cover, laughing at their predicament and rapidly struggling back into her shirt.

Jim announced, "I guess I should get you home. It's getting late."

Zoey looked sad at having to stop. She stuck her bra in her purse as Jim drove home. The goodbye kiss held great promise.

Two nights later, Bob waxed eloquent about his date with Sheila. "My God, she's got the greatest set of boobs I've ever made love to. She was so passionate and with it, I thought for sure we'd end up having sex, but then she sort of put the brakes on. I didn't mind at that point because I was sure we'd passed where you two were with your dates. Turns out that wasn't the case with Zoey."

Matt said, "I had the same experience with Monica. After our ten-mile run, we took showers at her house before going out to dinner. She went out of her way to be sure that I saw her naked, even giving me a not too subtle smile. She's gorgeous. Later, when we were making out, I also got to feel those luscious breasts. We spent over an hour making out. I think she wanted to give me a hand job, but I sort of ended things so I didn't get ahead of everyone. Man that was hard to do."

Bob said, "Maybe I'll be the lucky recipient of that hand job. I'll be asking her out next. Matt you'll be calling Zoey, and Jim you'll be dating Sheila.

Jim asked, "If you had to pick one as your long-term girlfriend right now, who would you pick?"

Matt struggled, "I can't. I like all of them ... and I include Alice in that list too, even though she's more of a cougar to us. I'm falling for all of them."

Bob nodded, "I'm in the same boat. Maybe it's too early to tell."

Matt reminded them, "Don't forget, we're meeting at Alice's on Friday night as usual."

* * * * *

"I feel a little slutty," Sheila admitted to her friends with some embarrassment.

"But you had fun," Zoey reminded. "You said Bob was attentive and made out in a way that turned you on. For that matter, I gather each of our dates got to about the same place and we were pretty happy."

Sheila pouted, "I was happier as an ice princess."

"You weren't," Zoey insisted.

Sheila shook out her long blond hair, "You're right. I loved it. I wanted more, but we stopped. Actually, I stopped it"

"Why?"

"I was afraid I'd end up going all the way."

"Fucking him."

"Yes, damn it, fucking him. I was so worked up I played with my dildo in bed for an hour after we got home. I think my parents even heard me. I came about six times."

"The next time we're with the guys we should be prepared to reward their tenacity for dating three ice princesses. Although, with our new resolutions we've been pretty liberal in letting them get to second base with us."

Zoey smiled and said in a dreamy tone, "I'd enjoy any of the men. I want to be with any of them in a carnal way." She laughed.

After a silence, Sheila said, "Do you suppose that's what they're doing?"

"What?"

"They're working the three of us up together ... keeping us at the same level more or less ... so that ... so that ..."

"So that, what?" Zoey asked.

"I don't know," Sheila said. "So that ... they fuck us all on the same night. It's like they each want a relationship with each of us though. I think they're interested in us for more than sex and making out. Look how attentive they've been, and careful of our feelings and not moving too fast."

Monica said, "Wow. Where'd my friend the skeptical Sheila go? And to go on the record, I wouldn't mind making love with any of them either."

Sheila said, "So you'd like being a girlfriend to three guys, who each have three girlfriends of which you are one?"

Monica laughed, "So long as I get some good loving, I don't think I'd mind."

Sheila smiled, "I bet Jim calls me for a date very soon. Moreover, I bet Zoey hears from Matt, and Monica, Bob will ask you for a date. That's the next rotation, which is back to where we had as platonic dates a few weeks ago."

Monica said, "I don't care who it is. I'm going to reward their good behavior and perseverance with us."

Zoey said, "Are you going to fuck him?"

"Maybe. Maybe not. We'll see how the date and the evening go. I don't plan on being a pushover, nor do I plan on remaining an ice princess. I'm struggling to find a middle ground that's more in the pushover side of the scale."

Two days later the dates Sheila had predicted had been arranged. The girls gave much less flak to the three men seeming to understand the dating pattern and perhaps the motivations of the men.

* * * * *

They were all nude. Alice sat on the sofa holding Matt and Bob's cocks in her hands and slowly fondling them and masturbating the two men. She had a leg slung over each of their knees totally exposing her pussy to anyone interested to play with it. Jim sat on the floor between her legs and had his tongue flapping intensely at Alice's pussy, both thrusting into her opening and lapping. Every time he touched her clitoris she jerked.

Alice said, "I know you'll hate my next recommendation, but no intercourse on your next date."

"Why? What's that accomplish or not accomplish?"

"They have to be craving the kind of sexyou want with them, not whatthey want; so you need to keep raising the sexual temperature with them a little more. Don't rush for home plate. The next date should take you third base – action below the waist, and even oral sex, but stop there. Besides, you're going to be on couple dates."

"How should I turn her down if my date wants to fuck?" Bob complained.

Alice thought a moment and then leaned over and inhaled his dick until her nose pushed against his mons.

She pulled off and said, "Tell her that you're worried about moving too fast in the growing relationship you have withall of them. Since you each want a piece of each of them, be sure to emphasize that you wantthem to feel comfortable with the way therelationships – plural word – are developing. Get them thinking like a horny group of girls who aren't afraid to have sex together."

Alice added, "You could also tell them you respect them, you want to think about it, you want them to think about it, you didn't bring a condom – but you'd better just in case, you don't want to play the three date game – or is it four, and you want to get to know them better."

Alice continued, "The idea is to let them come up with the idea for group sex or swapping when you're all together. If you raise it, you just become a pervert with weird group sex fantasies. If they do it, then it's a romantic time with the three of you."

Jim looked up from between Alice's legs, his face dripping with Alice's pussy juice. His fingers were still stroking her slit. "Should we do a group date again?"

"Oh, good idea," Alice said. "Yes. Without making a big 'do' about it, try to introduce the idea of group romantic activity. For instance, if you're at the beach, you sometimes change around whom you're with and kissing or petting. Do some subtle touching of breasts or intimate parts where it's obvious the others can see you. Show that you're not embarrassed in the least. Make it fun for them too. You might even do a little two-on-one on one of the girls and see how she and the others react. Go slowly though. Stop the moment you sense a negative reaction from someone."

Alice paused, reached down and pushed Jim's head from her pussy, "Now, no more cunnilingus."

Jim looked up, "Huh?"

"I need a cock or two in my cunt ... and later I'm going to introduce you all to a new skill you must have to be consummate lovers: eating cum from a pussy." Alice pointed at her sodden cunt, and had a positively devilish grin on her face as she lay back to allow Jim to position his cock at the entrance to her smoking hot tunnel.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
3 Comments
AnonymousAnonymousover 8 years ago
Garbage by an inept and talentless writer !

One of the worst ! "1*" !!

arrowglassarrowglassover 8 years ago
Love the way you are doing this!

Just waiting for Ch. 04.

AnonymousAnonymousover 8 years ago
good story

Good progression of the plot so far. I think the guys' names have gotten mixed up at a few points in this chapter, also in chapter 2.

Share this Story

READ MORE OF THIS SERIES

Similar Stories

Pool Boy Pool Boy in the rich part of town.in Group Sex
Pushing Boundaries Strip Poker on Roommate Bonding Day.in Group Sex
High School Harem Ch. 01 Horny teens explore their sexuality and each other.in Group Sex
Bosom Buddies Ch. 01 A nerd befriends the 5 hottest girls in school.in First Time
High School Harem Pt. 01 I'm the only guy in an all-girls school...in Erotic Couplings
More Stories