The day that followed, I found myself thinking about last night with Jenna a lot. I wondered if she was right and I too could take both Eric and Rob at the same time. I also wondered about the plan Jenna mentioned, what did she mean a plan? I had never had anal sex before let alone double penetration. Start slow and have a goal, Jenna had said. What did she have in mind, I wondered. The next day when I saw her again I found out.
She called and said she was coming over and before I could say anything she hung up. About ten minutes later she knocked on my door. I answered it and found her holding a plastic bag with something inside.
"Okay, so I did a little shopping," she said walking into my place.
"For what?" I asked.
"For you know... the goal."
"The what?" I asked.
"The goal to do DP with Eric and Rob. I'm going to help you get ready," she said sitting on my couch and putting the plastic bag on the coffee table.
"You're what? I don't know, Jenna... I'm not sure I want to do that?"
"Yes you do. You just don't know it yet. Trust me if you do it right and prep beforehand it is so good... you'll cum harder than you ever have."
"Really, so what's in the bag?" I asked.
"Funny you should ask," she giggled and started rooting through it.
Out came a rectangular box that I could tell from the back was some kind of adult toy. "This is to get you started," Jenna said turning it around.
What I saw before me was easily recognizable. Three different sized buttplugs all blue rubber.
"We'll start small and work up to the big one," she said, setting the plugs on the table.
"Then once you can handle the plugs we'll progress to this," she said, pulling out the last box which had a large fake cock made of rubber. "When you can handle this monster you'll be able to handle both guys easily."
"Holy shit, Jenna! That thing is huge."
"I know, but it is better safe than sorry. We need you accustomed to having you ass penetrated before we let the guys at you. They have a tendency to get over excited and that could be bad if you aren't prepared."
"Fuck, this is crazy. I'm not sure about any of this."
"I know, it's scary. I was scared my first time but the results are so so good, Lacy. I want you to experience it like me. I want to pay you back for the other night with the guys. Letting me join you, you know?"
"That's not needed."
"Maybe not but I still want to."
"Can I think about this first?" I asked.
"Sure. I'll leave these with you and maybe you can try the small plug out by yourself or I can come over tonight if you want some help. The first time is crucial that it is a good experience though so maybe I should be here."
"Tonight? That's soon, doesn't give me much thinking time."
"Well, I want to right now but I have to go to work," she laughed. "Think about it and text me. I get off at five.
I reluctantly agreed and she jumped up, hugged me and left quickly for work. I turned back around and stared at the adult toys sitting on my coffee table. I already had a vibrator but never thought about buttplugs or a huge fake cock almost as big as my arm. Jenna was a nut and she was getting me into things I was nervous about. It was kind of my fault though since I started it all by fucking Rob and Eric and then telling her about it. I was thinking it might have been better if I hadn't told her.
Jenna had left the plastic bag on the table as well and when I picked it up I heard the receipt, she had left inside, crackle. Taking it out, I learned how much she had spent and where she had purchased the items. I packed it all back into the sack and drove to the adult store and returned everything. I planned on returning the money to Becca when I told her I wasn't interested in her helping me prepare my ass for double penetration. It was too weird to think about, especially when I wasn't in the moment. I wanted to be spontaneous. If it happens it happens but I wasn't making it a goal like she wanted me to.
After I returned the toys, I headed to work. I can pretty much make my own hours and come and go when I want as long as I get my stuff done. When I had had enough of work, I headed to the gym, grabbed my clothes from the backseat of my car and went in. I changed in the locker room and started working out. With my headphones on and focused on my workout, I got into my routine, working up quite a sweat and feeling good and strong. I didn't notice that Rob had come in the gym as well. He never said anything and went to his own workout and left me to mine. It wasn't until I was pretty much done that I noticed him. I took out my head phones and said 'hi' when he finished a set of pullups.
"Hey, how's it going?" he asked.
"Good, just finishing up," I said. "You?"
"Almost done I have a few more sets."
"No Eric?" I asked.