I Had My First Threesome at Age 48 and Learned 5 Crucial Things

I ended up in my first threesome at age 48: cis, straight, and stone-cold sober on a Sunday at 11 a.m. The spoiler? It was pretty amazing.

My East Coast boyfriend, Mr. Rockefeller, texted me during my hot midmorning stroll, "Kelly wants to meet you." I understood what that text meant, so I stopped short. I was unsure if this was the threesome I wanted because I had never had one before. I only once felt a brief, five-second attraction to a woman across a packed bar.

I wrote back, "I'm nervous," but my true meaning was "I Am Very Straight." I asked myself, "What if I feel intimidated, excluded, or turned off?" What happens if I am caught in the comparisons no-win trap?

Kelly lives in New York, but I don't. He frequently plays with her around town, and they have engaged in many threesomes, foursomes, and even moresomes. I've never had any—so when I put on my mask, packed around six hundred cleaning wipes, and met Mr. Rockefeller earlier that week, I hadn't considered this possibility.

After eight weeks of solitary quarantine, I had reached a breaking point and could not bear to endure another day of crippling solitude and anxiety. I needed someone to show me love (or something similar), touch me, console me, or fuck me. Who better to assist me than a man who makes me feel as happy as Christmas at Rockefeller Center? I needed to feel human again. His moniker has nothing to do with geography or ancestry.

Since we first met almost a year ago, I've known that he enjoys group sex. Yes, I have had fantasies of having multiple men in my bed, but Kelly wasn't my imagination; this was real life. I stood there looking at my phone while soaked in perspiration. I enjoy trying new things, but—

"She's fantastic," he added. Extremely affable and charming. You two ought to grab a coffee. They all had a good time when she and I played with straight women in the past. However, we can avoid it. Alternatively, you may meet her later this week. Or never.

"I don't say no," I answered. I've learned from experience that many things that I initially thought sounded terrible—like a Brazilian wax, anal play, even a little light choking—can be incredibly enjoyable. "All you have to do is hold my hand a bit."

This is how, on a Sunday at 11 a.m., I found myself in my first threesome (FMF) at the age of 48: cis, straight, and completely sober. The spoiler? It was pretty remarkable. I also learned a few things from it.

1. Say Everything

After Kelly picked me up for coffee, we would return to my hotel room to meet Mr. Rockefeller if Everything went according to plan. We've fucked in this car so many times that I had to have the upholstery professionally cleaned, so I was shocked when she started referring to herself and Mr. Rockefeller as a "we" right away. I assumed her sole responsibility was to calm me down. We adore that; we're into this and virtually twins since we share so many things."

It felt more like she was claiming her territory and making sure I knew I was on the outside, but perhaps she hoped the stories might appeal to me. After ten minutes, I was prepared to cancel the entire event. I didn't realize that she might have some feelings about my arrival and that it was also my responsibility to make her feel comfortable since I was too preoccupied with feeling uncomfortable, out of place, and undesired. I chose not to become defensive since I knew the only thing I could control was my response. I did a lot of blurting instead.

"Just because I showed up today, I feel like it's weird that we're all assuming you want to fuck me," I remarked. "Yeah, you enjoy ladies, but it doesn't imply you're particularly drawn to me. Additionally, I'm afraid you'll feel rejected if I don't want to touch you. In addition, if I say yes and then change my mind, I'm worried I'll ruin the party or come across as a prude. Furthermore, I don't want a major drama, so how can I quietly leave if I choose?

Kelly grinned and said, "All right." Then, as if by magic, she was the mentor I needed. All of the tension vanished, and we suddenly became friends. She stated, "I want to fuck you first and foremost, so cross that off your list."

She looked at me as I blushed and stumbled, then burst out laughing at my inability to flirt with a cis-woman. Finally, I felt anxious in a positive way.

You don't need to touch me. Nothing you don't want to do has to be done," she remarked. However, I was well aware of this. I'm not the type of person who feels compelled to perform or endure unpleasant circumstances, so choreography was a problem for me.

"How does it work, literally?" I inquired. "What happens if we're all in the room, the music is playing, he enters, and we're all looking at one another?"

She remarked, "He'll take the lead because I'm usually submissive." He'll probably kiss you. He will touch you, and I will participate if you desire. He'll do anything you want, and we'll all be nude in the end. I'll pay attention to him while he's paying attention to you because we both enjoy pleasing people. If you want, he and I can double up on you. We can double up on him, you and I. You don't have to worry about me; he will provide me with anything.

I sipped my coffee several times, imagining various situations. Although I avoided it, I appreciated the amount of eye contact she made. She had beautiful eyes. "All right," I replied. "And I'll just go to the pool if I'm not enjoying myself."

As we entered the motel, she responded, "Of course." "But I don't think that will occur."

I made a mental note. Make an exit plan. Everything seemed easy with that strategy.

2. Trust Matters Most

As Kelly had predicted, our first scenario went as planned: I offered Mr. Rockefeller and myself a splash of bourbon, but Kelly refused. He told her, "I have amazing breasts," as we made our way to the bed. He knows I'm conceited about them, so it was the ideal move.

I nodded when she asked whether she could see. He dropped my dress and unhooked my halter. I nodded once more when she begged to touch me. I told her no when she asked to kiss me. As they both teased my nipples, keeping them firm and getting me moist, she chose to kiss Mr. Rockefeller instead.

If a) I am STI-free and b) Mr Rockefeller is STI-free, and he sleeps with Kelly, then I can be sure that c) Kelly is STI-free. This dynamic is similar to the transitive property. According to the sex-transitive, she and I could trust each other in the same way if we could both trust Mr Rockefeller with our bodies to the extent that I was utterly helpless.

I assumed it was the first lesson when Kelly started rimming 10 minutes into a 69 with Mr. Rockefeller. A Venn diagram with four overlapping circles for communication, chemistry, openness, and giving produces positive outcomes.

3: Boundaries Can Change—Or Not

We experienced about twelve orgasms as a group during the following three hours. Although Mr. Rockefeller's tongue on my clit would have helped, I decided against kissing Kelly and instead thoroughly enjoyed our makeout, even though I never touched her in any of the obvious erogenous zones. I wasn't any less straight after having one threesome, but I was freed from some pointless anxieties.

It didn't matter that I frequently didn't know who was doing what to me.

The simplest thing was to become lost in the haze of entangled limbs, hands, and lips. I didn't care about anything else, but two mouths and four hands were twice as pleasant as one and two.

That day, none of my other boundaries changed, and I was glad not to feel constrained by the confines of my experience or attraction. I believed there must be a lesson. It's not necessary to make a big deal out of meeting folks where they are.

4. Give Everyone What They Want

Mr. Rockefeller always has a toy bag with him. He can assist you if you want to experience what it's like to have candle wax drop over your most sensitive skin. Let's say you want to try a curved glass dildo made to target the G-spot, a blindfold, a spreader bar, or handcuffs. Let's say you wish to become buddies with a heavy, thuddy flogger or engage in some anal training.

He will take care of you. He is aware that my G-spot can be picky and that I enjoy a lot of pleasure but not agony; Kelly enjoys impact and a lot of G-spot. As usual, he was ready for both.

When he pulled out a toy for Kelly that he had never used with me, I thought, "Oh, right." Even if it's a communal experience, customize it. Saying it aloud makes it seem so clear.

5. Group Sex Can Be Intimate

The hedonistic pleasure was Everything I anticipated: cold crystals on sweaty skin, orgasms so strong that she squirted, he shook, and I sobbed. That was not surprising at all. Intimacy—strong emotional interactions between Mr. Rockefeller and me—was something I hadn't anticipated.

My thoughts strayed just once that day; he wasn't staring at me, but he sensed a change in my energy, and there he was, placing a hand on my chest and looking directly into my eyes. Too low for Kelly to hear, he muttered, "Are you okay?"

I nodded and sensed that I was back in the room, in my body, in the middle of the event. He remained with me until he realized I was here to stay—and I experienced a wave of emotion. It was somewhat similar to love.

Although I never witnessed them—I wouldn't have wanted to—I'm sure he and Kelly also had similar moments. They also have a right to their own experience. She was also entitled to feel completely cared for and seen, as well as good and well fucked.

Later that night, when I was tired and sore in the finest ways, I reminded myself to remember that, if nothing else. Being there for everyone in the room is the true lesson of today.