Chapter 4: Why did my threesome FAIL MISERABLY?
I already know what you are thinking. You are wrong. This is going to be the ridiculous, ratchet part of this book. Be prepared for this ADULT CONTENT.
You have been warned.
There was this girl I knew named Carey. She was nice, trendy and about 10-15 years older than me (I was in my late 20s early 30s when this happened, so do the math). Carey always wore the latest fashion and she was a true free spirit. She did what she wanted, when she wanted. She was my spirit animal. I wanted such freedom. I don’t know why I thought being her friend alone would get me there, but what do I know about achieving such things?
Carey was 5’6” and maybe 100 pounds soaking wet. Which was very different from my taller, curvy girl frame. She was bi-sexual which in my mind went along with her free spirit lifestyle. We were both employed career girls and both were in relationships on and off. Occasionally, we would do a girls night out or go shopping but that was about it. I may have seen her in person once every few months, but we talked on the phone more so it was a good fit with my constantly busy schedule.
Carey wasn’t shy about the fact that she wanted us to hook up and have some “sexy fun”. I politely declined over the years, laughed it off and moved on. It was no offense to her, but I just honestly didn’t see the point. I mean, she was missing some vital features that I love about men. Tall, broad shoulders with er-uh (pauses to think of an appropriate word) blessings below the belt. Don’t get me wrong, Carey was cute as a button. And if I were interested in girls, she is who I would imagine I would pick. A true girly girl like myself.
One day, Carey called me at work. I was about to get off so it was no biggie. She was excited as if she had some juicy gossip (spill the tea!) so I closed my office door to hear what she had to say.
“Girl, we should have a threesome!” she said with excitement.
“What the hell, are you smoking weed again before 5pm?” I asked in shocked.
“Well, yeah but, that has nothing to do with it. What do you think?”
“Ain’t nobody trying to do new things.. We ain’t in college anymore!” I said while packing my things. It is definitely quitting time and this girl done gone crazy. I may need to call for back up.
On my drive home she reasoned with me about her idea. We were both single, which was rare for both of us to be single at the same time. We weren’t hurting anyone and it would be fun.
“When do you ever do anything exciting and new?” she demanded.
She was right. I am pretty square when it comes to such things. It all started when my mom was trying to prevent my sister and I from falling into the same teenage pregnancy thing many girls that age were doing. My mom wasn’t a prude or anything, but the messages I received was if I looked at a boy I would get pregnant and my life would then be over. Pregnancy was to be avoided at all costs because it always leads to something disastrous. Always. And now as an adult, there was still a quiet fear lurking in the back of my mind around scandalously sexy behavior.
And trust me, this falls squarely into scandalously sexy behavior.
I think I am being peer-pressured at this point and it was working. When do I do something wild and crazy. The fact that I think a threesome was in fact wild and crazy was an issue in itself, but that is for another book or the sofa in a therapist’s office. Let’s stay on topic here.
Ok Carey, let’s do this.
Carey screamed with delight. It was as if she had hit the lotto. Meanwhile, I sat confused. Since this was her suggestion surely I would just show up and magic would happen right? Wrong.
“Carey, what guy are we going to call for this?” I asked because, well, I don’t know how this shit works. I need help.
“I don’t have anyone I can call. Don’t you have someone?”
I paused. How do you select a guy to have a threesome with? It isn’t like this topic EVER came up in any of my conversations with my guy friends. Hell, my guy friends probably thought I was too much of a prude to even bring this up. And they would have been correct.
So, what did my forever planning, business minded butt do? I took a logical approach to plan my first threesome.
“Well let me hit up my address book and see” I said. I started with the “A”s:
Aaron - no, his “blessings” were quite small in size.
Alvin - no, he wouldn’t go for it and I forgot to call him back that one time.
Andrew - no, he is out of town on business.
“I got it! Let’s call Brian!” Hooray for me, I figured it out! I helped!!!
Like she knew who I was talking about? No matter, I would call Brian today and see if he was open to this idea.
I called Brian. After exchanging pleasantries, I told him about this idea. He was super excited and wanted to take action right away.
I don’t know why I thought I would have to convince a guy to be with two girls but I digress…
The plan was to meet at my house on Friday night. There we would have drinks. Brian knew what I looked like but not Carey. We wanted to give him a chance to meet and see Carey. If everyone was attracted, we would schedule a time the following week to actually have this threesome.
Sounds like a plan don’t it? I told you I was business minded 24 hours a day 7 days a week!
Friday came quickly. I found myself in my kitchen making apple-tinis when the doorbell rang. It was Carey. She wanted to come over first and get some good drinking / fun in before Brian arrived. We were laughing and talking for about an hour before another ring of my doorbell.
I looked at the time. Of course Brian is early. I bet that is one of the few times men will consistently be early somewhere. He walked in and I led him into my dining room where we were having our drinks. I introduced him to Carey. They shook hands and exchanged “Nice to meet you” greetings before Brian sat down.
I thought this would be awkward and maybe it was for me. Brian and Carey were the new people in this situation so why was I the one nervous? I offered to prepare Brian and drink and hurried through the swinging door that led to the kitchen. The door swung shut abruptly behind me. I carefully poured him a martini wondering if he would even touch such a girly drink. I went back into the dining room by pushing through the swinging door.
I almost dropped the drinks in my hands.
There was Carey sitting on Brian’s lap. She was kissing him while he was removing her blouse.
What the heck? What happened to our plan?? What happened to the meet-and-greet with the scheduled threesome next week??
Plan gone to hell. Threesome is happening right now!
I have to get myself together, I thought. Here is your chance! Your opportunity to be a risk taker, a cool person, someone who explores and is sexually free. Who am I fooling? This isn’t me! I looked at them kinda going at it and wondered why I was putting so much thought into something that was supposed to be spontaneous and fun. I have on cute panties… let’s go!
Before I could complete my thought & organize my priorities, I was being pulled over to the group by Carey. Apparently, my breast in her mouth was her priority. I walked over to the group hesitantly. All of a sudden, it seemed like everyone was kissing all over everyone else. This seems confusing. Then suddenly, the party moved to the sofa.
Carey was definitely in control and Brian wasn’t opposed at all. We quickly moved to the living room and clothes were flying everywhere. Carey was causing Brian’s eyes to roll into the back of his head with her mouth skills, and I was taking in the view. It was like watching live porn. Actually kinda hot if I want to be honest.
When Brian was standing at full attention, Carey turned her attention to me. As she began taking off my panties, Brian was putting on protection. The moment he finished, he was inside of Carey who screamed with delight. Carey instantly started moving her face toward my …
That is when it happened. Everything instantly stopped. What the heck happened, I thought. I looked up at Brian who was frozen with a fearful look on his face. Carey jerked up in complete disgust. Brian was experiencing some equipment failures and Carey wasn’t pleased. She turned around to repeat what she was doing earlier. It worked before, so I guess she figured it would work again.
Brian standing back at attention to Carey’s satisfaction meant game on. She turned and winked at me as if everything was back under control. Brian, who regained confidence, found the condom and busied himself sliding it on. Carey anticipating our threesome finally gaining traction moved into position. I am still sitting on the sofa. Carey is in front of me just like the first time, moving quickly towards my waist. Brian is inside of Carey and is staring at me while thrusting himself into Carey. Once Brian found a rhythm, Carey began lowering her head from its position near my waist.
Carey jumped up with purpose. Brian’s er-uh equipment failure had returned. Without saying a word, Carey pushed me away and began furiously giving Brian the business. She was on him like she was starving and he was the last piece of chicken at the cookout. And when Brian failed to perform a third time, Carey’s patience was over.
She grabbed my arm, pushed past Brian and away we went. Carey stormed up my stairs headed straight to my room. She slammed the door and threw me on the bed. Determined to make the best of this situation, Carey started kissing my breasts and touching me everywhere.
Just then my bedroom door swung open. It was Brian! He walked quickly with purpose to my night stand, pulled out my sex toy and threw Carey on the bed nearly knocking me off of it. Brian began furiously jamming my sex toy into Carey who apparently was amazed by it. I stood in the corner in horror (mental note to self, burn that sex toy).
This went on for a few minutes. I was frozen. I don’t know if I was more shocked this was going on, confused as to how Brian knew where my sex toys were, or angry he was using them on HER! Before I determined an answer, Carey let out a loud long scream indicating her orgasm was complete. Brian dropped the toy which made a loud thud on the floor. Carey jumped from the bed and proceeded to curse Brian out. She called him all sorts of names and threw insults at him repeatedly for failing to perform. I sprung from my corner and gave her a piece of my mind.
“I don’t give a shit what Brian did or didn’t do, you will not speak to him like that in my house. It’s time for you to leave!” I stated plainly.
Carey was outraged. She must have thought I would have her side in this issue. Emasculation was never my thing and I wasn’t standing for it. So he got a little over stimulated? No need to go after the poor guy’s manhood about it.
Carey ran downstairs to get dressed. I stood there, half dressed myself, trying to gather the courage to look at Brian. I couldn’t imagine what he was thinking or feeling. We heard Carey slam the door on her way out. Brian quietly thanked me for standing up for him and left the bedroom. Soon, I heard the exterior door close softly.
What the heck just happened? Is this what all the hype was about around a threesome? How in the heck did my experience get so out of hand? And where the heck is that sex toy?
I need some gloves to clean all this up…