Sisters, Friends, and Lovers - Book Three
Copyright© 2026 by Wolf
Chapter 52: Disapproval
Erotica Sex Story: Chapter 52: Disapproval - 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. The author has a quite a few other books/series you might also consider, including collections to save you money.
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Fa/Fa Consensual Romantic Lesbian BiSexual Fiction Incest Gang Bang Group Sex Orgy Anal Sex Cream Pie Exhibitionism Masturbation Oral Sex Voyeurism
I’d been working in my assigned conference room for a couple of hours when Brenda came in with an extra cup of coffee for me. After making sure I could talk for a few minutes, she sat down.
Brenda asked, “I have three candidates for the Saturday party as guests, and I wanted to run them by you before I started my little seduction to see if they’d like to join us for some sexual debauchery.”
I said, “You speak with certainty as though they won’t be shocked and raise a ruckus when you ask them to go to a swinger’s party.”
“I’m pretty sure about them, that is that they are players of some kind. They each have low ego needs, so that makes them my kind of person – like you, yet they give off vibes of enjoying sex and having a playful attitude about life.”
“Do I know any of them?”
“You’ve met all of them, and that’s why I’m here, to get your assessment of them. They’re Dana St. Germain, Rob Oakley, and Ed Trout.”
I quickly responded, “Rob and Ed are both nice guys and would fit in well. I’m sure you, Marge, and Jane would enjoy a romp with each of them since they’re both hunks. I have no negatives on either of them. Dana is gorgeous; I’ve wanted to just take pictures of her all day long she’s so pretty. She’s model quality, and certainly, in my book, highly desirable.”
Brenda laughed, “That’s exactly what Marge and Jane said about the three, so I’ll see if I can ask them. The fact that YOU are highly fuckable will probably be sufficient to lure Dana into coming; just be sure you save some time to give her the Big Steve Experience on Saturday night. Now that I mention it, I’d like the Big Steve Experience on Saturday night, too, but if I can get that tonight or tomorrow, I’ll reluctantly relinquish my Saturday time slot to some other slut like Dana.” She actually giggled.
I asked, “Is Mike coming?”
“Oh, yes. He’s bringing a guy he works with whom I’ve wanted a little liaison for quite some time. I’m the bait. TJ is coming too, and he’s bringing a date, but that’s all I know.”
I speculated, “Ivy will be sorry she missed this party, but I suspect she’ll be involved in some party of her own back east. I heard Fran and Sheila cooking up some get together just before I left. There may even be a swinger’s party the same night as ours.”
Brenda said, “Someday soon I want to go back east with you to one of those parties and meet the rest of your crew. I feel as though I know them from your talking about them and seeing a photo or two, but it’s not the real thing.”
Just then my iPhone vibrated alerting me to a text message. I glanced at the screen and there was a sexy photo. The pic had been taken the night before I surmised; it was a point of view photo showing two naked females lying next to each other on their backs each with a cock in their pussy. The females were Ivy and Ally, and the cocks were Aidan and Matt.
I showed the picture to Brenda. Her eyebrows rose. She said, “You get great text messages. Do you know who’s who?”
I nodded and explained what I thought was going on. We were laughing.
Brenda thought for a moment and asked, “If I hike up my skirt to show my bare pussy would you take a picture of me?”
I grinned about a mile wide. I asked, “With or without cock?”
Brenda strolled over to the door, and locked the door so we wouldn’t be interrupted. She turned and said, “With cock, but we can’t do a full fuck right now. It’ll just be for show.” She pulled her cellphone out of her purse and set it on the table next to mine.
Brenda reached up under her skirt and yanked down her boy shorts that she wore as underwear and stuffed them in her purse. I found them sexy. She then hiked up her skirt and tucked it into her belt, totally exposing her pussy. She then gave a little boost and sat on the table next to where I’d been working.
I stood, walked over to her, and pulled my cock from my pants. Brenda massaged it a little until it started to have some serious heft to it. As she fondled my cock, I took a picture, but after checking I realized I had to hold the phone lower to get the best angle on both pussy and cock. I took another, only by this time, Brenda had me getting really hard. I took another picture.
Brenda kept fondling me and soon we were looking in each other’s eyes. I leaned in and kissed her. I whispered, “You are such a hottie. Are you sure you don’t want me to do a full fuck with you?”
“No, I’m not sure ... in fact, I’ve changed my mind. Put it in, but make it fast; not one of your two-hour fuck sessions. We’d get caught for sure.”
Brenda had me ready by that point. She rubbed my mushroomed head all around her pussy lips, lubricating up the head, and then suddenly I lurched forward and slid every inch of my shaft into her hot pussy.
Brenda moaned so loud I thought security three floors away would hear her. We fucked for a couple of minutes, and I just allowed every wonderful sensation from her moist love tunnel to surround my organ and bring me closer and closer to climax. We did take some pictures.
I didn’t want to cum until she did, so I held off. I started to rub her clit with my thumb, and a dreamy look came over Brenda’s face. A minute later she whispered, “I’m almost there ... building up ... just a little more ... almost ... THERE! NOW!”
As Brenda came, I allowed myself to explode my cum deep inside the executive. I came in buckets, thinking of both our pleasures, and already thinking about how to best clean her up so she could make it to the ladies room. Before we parted, I grabbed each camera and took a snapshot of my cock in her cunt. A few drops of white cum had seeped around the edge of our coupling.
After my surges ceased, I extracted and took a pic of her messy and leaking pussy. Brenda knelt in front of me and inhaled my cock, with the obvious intent of cleaning me up. As she squatted a cup full of my cum ran out of her pussy onto the carpeted floor. She looked up at me with my cock in her mouth and I snapped another picture. I got the angle just right and the photo also showed the puddle of cum dripping from her pussy.
Brenda stood but with her legs spread. I said, “Want me to get paper towels or something. I could lick you clean, too.”
She cocked her head to one side and said, “No, I want to enjoy this all day if I can. I’m just going to slip my panties back on and go back to my office.” She kissed me passionately and said, “See you later. I do want to see you later – a lot. We’ll do this right the next time – a nice, long fuck with more orgasms. Let’s swap photos. I want to send a couple of them to Mike to get him cranked up.”
“He’ll be cool with this?”
“Oh, hell yeah. He’s got a little honey in his office who he fucks occasionally, so this won’t be the first time we’ve traded photos: this was a first for me, but not for him. He owes me. He likes you anyway, so he’ll be cool. It’ll give him a laugh. He’s always telling me I should find a way to relax at work anyway ... and, oh, God, you really relaxed me. You are such a hot fuck.” We shared a passionate kiss.
On that note, Brenda and I gave each other clothing checks and then she slipped out of the conference room. It took me fifteen minutes to get my head back into working. Sex does that to a guy. Of course, fifteen minutes after that, four pictures of Brenda’s pussy mostly with my cock buried deep inside arrived on my iPhone as she sent them to Mike and me. They were hot. I passed them on to the contingent of lovers I had in Boston under the title ‘Coffee Break’.
In reply to the sexts, I got two up-skirt pictures, neither of them particularly sexy since they both had panties on, but they got the point across. One was titled ’Boring Day, Can’t Play’ and the other ’Waiting for the Weekend.’
Despite having warm and loving female companionship in Denver for ten days, I was glad to get home to the east coast to the other set of female companions, one of whom was my fiancée.
The Denver trip had included a Saturday-to-Sunday swing party at Brady and Edie’s home. This time Jane, Marge, and I had stayed over making the party an eighteen-hour fuck fest that nearly defied description, but as they all do. The party will remain a most memorable experience.
At that party, I’d met four new women who hadn’t had the Big Steve Experience yet. Brenda was there too and wanted the same. Thus, over that time period I gave five women the most intense orgasmic pleasure of their lifetime, so intense that each of them briefly passed out in what I’d come to learn was called La Petite Mort or LPM as I’d shortened it to.
As usual, the by-product of LPM were four new women who’d fallen madly in love with me and wanted me as a life partner under practically any conditions I wanted to apply. I would have counted Brenda, but she was already madly in love with me. Dana Seymour, one of women from TCI who Brenda brought to the party, was another. A couple of days later, Dana had come by Jane’s conference room where I was working, locked the door, and fucked me royally for a half-hour just before lunch. She’d gotten Marge to stand guard over the ‘very important, no interruptions meeting’. No one asked to see me anyway.
I again got a hero’s welcome back home in Cambridge. I realized as that thought crossed my mind that I had multiple homes around the country now: Cambridge, New Jersey, and Denver. I felt a bit like the character in an old movie called Frequent Flyer, where the main character was an airline pilot who ended up married to three women in different cities until the whole set up fell apart. I said a little prayer that my life wouldn’t fall apart; unlike the movie, all my lovers knew about each other. At least, all the women knew about each other and many had met.
I knew something serious was afoot within sixty seconds of walking in the door that Friday evening. After all the kisses and hugs, Fran said the four words that strike terror into every able-bodied man in the universe: “We have to talk.”
The talk turned out to be about the wedding. The five women in the apartment – Fran, Sheila, Ally, René, and Ivy – along with Jean, the sisters’ mother, had spent hours planning the wedding. I apparently had been a distant thought, especially since I’d been away for almost two weeks.
Fran had decided on a spring wedding. After considerable thought and discussions with her sisters (now including René, Ivy, and Jane) and her parents, she’d planned a ‘destination wedding.’
“Where?” I asked, thinking of something like Cape Cod or the coast of Maine, only an hour to so from Boston.
“We’ll be coming off of winter and everyone will be questing for warm weather, so we thought about someplace in the Caribbean.”
I know I gulped. I could even feel my Adam’s apple bobbing up and down, as I did. I said slowly, “Oooooookay. Have you picked an island?”
Fran continued, “No. You and I are going to do that this weekend with a lot of time on the Internet, but we’ll also have to make calls about availability and rooms.”
I asked, “How many people are you thinking about – how big a wedding party?”
Fran turned to the side table next to the sofa and picked up a pad of paper and passed it to me. There were one hundred-twenty-four names listed. I glanced through the pages, and I knew all but about a dozen of them. I saw my brother Doug and his wife Sheri on the list with their children, so I guess I would have an automatic best man.
“Do you want to tell me more about my wedding?” I teased. I knew that Fran’s mind was really on our getting together and not on wedding plans.
Fran said, “Not until tomorrow. Right now, you’ve got five eager pussies that want to be fucked, and that’s going to take you the rest of the night if you do it right. I’m your starting pussy and your ending pussy, and I want to go to sleep with your arms around me and your spent cock inside me.” She smiled up at me and then kissed me in a tender but hot way. Next, she pulled me up to the amusement of the other women in the room, and then herded me into the bedroom, slowly undoing her blouse as we walked.
By midnight I had indeed provided a satisfying orgasm or four to each of the five women now living with me on a full-time basis. Fran and I did have the last ‘interlude’ of the evening, and it was kind of messy because we both came in buckets. We made the moves to ignore our drips and the wet spot and drift off to sleep. Someone had other plans. After cleaning the two of us up orally, Ivy also nestled into my other side with her erect nipples digging into my back, sighed in contentment, and drifted off to sleep.
In the morning, I sat with Fran and Sheila, and the preliminary planning for the wedding came up. This time Fran pulled out a bright white manila folder, and the first page in it she placed on the table in front of me. It was a checklist of all the things that a bride (and her mother) and groom had to consider in planning a wedding. I about choked.
Fran said, “So, here’s the deal; I’m responsible for all the stuff highlighted in pink, we jointly have to decide the stuff highlighted in yellow, and you take the rest. Later today, I’ll break the page up into three separate ‘To Do’ lists.
I looked at the major points on the joint and hubby-to-be list, but it wasn’t too long.
Prepare invitation list (joint) Notify friends to hold particular date for the wedding Coordinate with parents and relatives Pick best man and groomsmen and let them know Set up honeymoon (joint) Help set up catering (joint) Arrange travel and any insurance Pick and book band or DJ (joint) Gift registry (joint) Shop for wedding rings (joint) Decide on dress for wedding and guests (joint) Set up joint bank accounts Arrange ceremony, including any readings or poems Buy gifts for best man and groomsmen Get marriage license Thank you notes as required
As I scanned the list, Fran told me, “I have some ideas and I’ve talked to Mom about it. A lot of what we need to decide will depend on the venue for the wedding. A destination wedding would probably limit the guest list to those willing to travel and take more than an afternoon and evening of their lives. There would also be the cost.”
Fran continued, “I want this to be the party of the century for us. This is a one-time blast we’ll never forget.”
She laid some printouts from an Internet sit in front of me. “I picked this place, but want to talk to you about it because it’s very risqué and some of your conservative relatives might be there – like your parents.” Fran slipped a couple of pages printed off the Internet in front of me.
The online brochure was for a place called the Club Orient on St. Maarten’s in the Caribbean. All through the various photographs of the resort, nude or nearly nude people strolled the grounds, frolicked in the pool, or played games with one another. I was intrigued but wondered how I’d sell this to my parents. I wondered if I should spring this on them, or just let them find out when they got there. I laughed at the two possibilities, reveling in the discomfort I knew they’d feel.
Fran said, “A lot of the crowd from around here want to go, and we want to turn the place into Orgyville for a week.” She thought for another moment and added, “Oh, we have one minor problem too – about money, at least I want to raise it.”
“What’s that?” I had the feeling I’d had the good news and now for the bad news.
“I don’t think we should make Mom and Dad pay for all of this. It’s not like we’re just starting out and need a little push. We both have healthy savings accounts, and I think we should blow a bundle on this and not let them do too much.”