Sisters, Friends, and Lovers - Book One
Copyright© 2025 by Wolf
Chapter 20: Planning Ahead
Erotica Sex Story: Chapter 20: Planning Ahead - Steve is surprised/shocked! The two girls he’s dating are sisters! A threesome forms then a third sister joins. Friends arrive causing additional loving and sexual relationships. He hides nothing as his sphere expands. He involves guy friends to help out with his ‘harem’. A wedding and highly sexual five-day ‘reception’ cap off the story, along with the perfect living situation.
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Consensual Romantic BiSexual Heterosexual Fiction Incest Group Sex Anal Sex Exhibitionism Masturbation Oral Sex Voyeurism
With the exception of eating out one night, Jane and I duplicated Monday night the rest of the week until I departed for Boston on Friday afternoon. During that time, we grew a lot closer and revealed more and more about our hidden selves to each other. Certainly, by the end of the week, we both knew we wanted to remain in each other’s lives for a long time if not forever.
As I had with Fran, Sheila, and Ally, I held off saying ‘I love you’ to Jane. We used the ‘L’ work about what we did or thought about something, but not about each other, for instance, we made love, we loved our time together, and we loved learning about each other with each minute we were together. That said, I realized I’d been developing the same deep feelings for Jane that I had for the girls up north.
Before I left on Friday, we planned out the following week. I’d be in New Jersey for Monday and Tuesday, fly with Jane to Atlanta that night, and spend the rest of the week there until flying home on Friday afternoon.
Monday evening, I also explained that I needed to do a Team Building dinner with the heads of the various TCI projects in New Jersey. Jane also thought that’d be a good idea. She had needed to get together with one of the other senior women managers at TCI, Pam Goodwin, who I’d met on my first day there, so she arranged that for the same night. As I had the week before, I’d stay with Jane while in New Jersey, and we’d share a hotel room in Atlanta.
The arrangements made and schedules coordinated with the help of Jane’s secretary Marge, I headed home Friday afternoon, again to a hero’s welcome by Ally, Fran, and Sheila. At Newark airport, I bought them all ‘I love New Jersey’ t-shirts and coffee mugs that brought a laugh from everyone when I presented them in a ‘formal’ ceremony with the girls lined up on the sofa.
Ally and Fran had made a slow-cooked beef stew that melted in my mouth; it was delicious. After dinner, they pulled me into the bedroom so they could show me how much they’d missed me. They’d apparently been slow-cooking all week awaiting my return despite Aidan’s visits.
During the week I had talked to each of them daily, and sent them at least one daily photograph, usually a selfie of me in a meeting or sitting with a pile of paper around me or on my laptop. A few of the shots the previous week included Jane, one in her genie outfit as she sat cross-legged on her modern sofa looking very sexy and loving. Without intending it, I think the girls had become a little competitive with Jane, probably because Jane was an unknown entity and was having an unknown impact on me.
Saturday morning, we lazed around the condo. I went out with Sheila to the local wine store to pick up two cases of what we called ‘give away’ wine, bottles of good wine that we brought as gifts to the various dinners, picnics, and barbecues that our friends hosted. We were going to the Dunns for dinner and playtime that evening, so taking four bottles was in order, particularly since there were four of us that usually drank.
Saturday afternoon, we drove out to Farborough, Massachusetts, and the Dunn’s beautiful home. We were surprised to also find Dave and Jean Henson and Sean and Rita McCoy at the Dunns. I guess deeper friendships had developed when we’d all been together at our apartment than I realized.
With six guys and seven women in the house, the place buzzed like a beehive with conversation and activity, and just like a junior high prom the men and women clustered in separate circles, in this case the men were in Chip’s family room in front of large TV, and the women were in the kitchen where Gale presided over dinner arrangements. Everyone was happy and glad to get together.
I maneuvered over to Aidan. “Have a good week?” I gave him a smirk, because I knew he’d stayed with the girls on the nights I was away, and according to them there had been sufficient sex to wear him out and keep the females satisfied.
Aidan blushed. I could tell he still wasn’t comfortable talking about sleeping and having sex with my partners. “Uhmmm, well, yeah, it was a really good week. I assume one of the girls told you I spent four nights at the condo with them.”
“I heard that you were actually having problems keeping the three of them happy,” I teased.
“Oh, shit. Really? Which one didn’t I make happy? I’m pushing myself, and even trying some of the techniques you and Lyle showed me about Tantric sex and pacing myself and everything, but they’re hard to do, particularly when all I really want to do is ... well, ... make love with each of them in a really consuming way. I’m trying hard with every one of them.”
I teased him, “Oh, I know and that’s why I always try to give them at least ten times as many orgasms as I have.”
Aidan squeaked, “Ten times? My God, I had no idea...” He balked, “I only ... oh, I’ll have to work on that.”
“Oh, each of them, Sheila especially, has come to expect nothing less during our evenings. I’ve actually mastered the skill of bringing two of them off simultaneously. I haven’t gotten all three of them to cum simultaneously, but I’m working on it.”
“Man, you are my new idol.” Despite Aidan being near my age, his social age seemed to be further behind, thus I felt he looked up to me and even attributed some characteristics to me that a younger brother might give an older brother. Occasionally, in talking with him, I even felt like a supportive parent coaching a young adult.
It felt fun to have a brother again; my own brother Doug, older by four years, lived outside of Chicago and rarely visited or called. I wondered what Doug would think when he learned of my living arrangements. Funny, but I never had the feeling of looking up to him. He was way beyond where I was growing up, so we almost had separate lives.
I thought about Aidan’s remark and stopped teasing, “Aidan, don’t make me an idol. I’m your friend. I’m always willing to share my knowledge and experience with you, and I hope you feel the same in supporting me.”
Aidan said in a serious tone, “Oh, I know, but you set me up with your partners – you want me to have sex with them and keep them happy, and I do try to do that and not trample on your toes. You know I love all the girls.”
“I do, and I am grateful that you aren’t trying to drive a wedge between them and me, particularly when I have to travel so much for a while that I can’t spend the time I want with them.”
Aidan nodded, “I saw a picture of the woman you’ve befriended in New Jersey – Jane. She’s beautiful and sexy.”
“I’d like to bring her home with me some weekend. If I do, I’d be counting on you to be around to help keep her and my partners happy. I might even borrow Dave, Chip and Sean, too. Jane’s never been in a group sex situation, and the idea scares her a little. You and the others don’t have a chest-thumping ego, so you’d be non-threatening to her; I’m sure she’d like you a lot. She has a hard edge from fighting her way up the corporate ladder, but she tells me that I’ve helped her soften that severity in her style in many ways. I have a difficult time seeing that side of her, because she melts like warm butter in my presence.”
“Do you love her like Fran, Sheila, and Ally?”
“Things are heading in that direction.”
“Will the girls be jealous?”
I responded, “To be sure, you’ll have to ask them, but I think in the way people might expect a lover to respond, the answer is no. We all want more time with each other, but I don’t begrudge them the time with you, and I don’t think they resent the time I spend with Jane, even as we have sex together. To think that way you have to see the bigger picture of the long-term relationships and how they interplay. I think the Law of Karma comes into play too; Jane and the girls know I would never do anything intentional to hurt them. If I did, I know it would cycle back and hurt me in some way. If I unintentionally do something, they each know that I will go out of my way to make it right and to mitigate any pain or injury.”
“Isn’t everyone like that?”
“I wish.” I’d seen enough crumbling relationships to know that there was a lot of bad karma being spread around.
Dave had come over and joined us, and he’d listened to the last interchange. He added, “When Jean and I raised the girls, we tried to teach them not to be jealous of what other people had or did. It’s a non-productive emotion, plus it’s passive. We do better to take some kind of action if we see that kind of situation – either distance ourselves or get more involved in some positive way.”
Aidan asked him, “What takes the place of jealousy as an emotion?”
Dave said, “Well, one can practice compersion. It means feeling happy that your friend has or did something that made them feel good.”
I added, “That’s why I’m not jealous of you having sex with the girls. I know that each of you will get pleasure and joy from the act, and even develop a closeness to each other than will double those feelings. Because that’s what I want you all to feel, I don’t mind your interaction with each other because I feel a secondary happiness that I did a good thing for each of you in asking you to be there for them.”
Aidan said, “That’s sort of like altruism.”
I hemmed and hawed, “Altruism to me is unselfish or selfless concern for others. When I asked you to be with my lovers, I was being selfish and acting in my own interest. I wanted to feel good knowing that Ally, Sheila, and Fran were taken care of and able to get a healthy dose of sex from someone they like. Thus, I felt good by that request. I also didn’t want the girls going out with just anybody, or hanging out somewhere they might meet somebody that doesn’t think the way you do about driving a wedge between them and me. So, I acted out of my own self-interest.”