This story was written in two parts. One by me and the other from my wife's point of view. She and I often wrote these "love letters" to each other and now I want to share them with you. I hope that you enjoy the different accounts of the story. All characters are at least 18 years of age and consenting adults.
Caroline is a freak of nature. I mean the woman cannot get enough sex. After our intense session in the shower, she gives me an incredible blowjob while her brother is in the next room. What was that finger in the ass trick? Holy crap, I never knew that it was so intense. I came like crazy and that was after cumming two other times earlier today. I have to get my ass home before Bobby catches us and who knows what happens.
When I got home, I lay on my bed replaying the whole scene again and again in my mind. If my cock, ass, and balls weren't aching, I would swear that it was all a dream. I knew that I needed to play it cool and not look to desperate when it comes to Caroline. She is an experienced woman and she will let me know if and when we will hook up again.
Well, over a week had gone by and there was no sign that Caroline and I were ever going to get together again. I think that I only saw her twice all week and she was running out to the mall or something like that. She said "Hi" and smiled and even gave me a wink, but that was all, at least until today.
I got home from preseason football practice and saw that there was a walkie-talkie on my desk. It wasn't mine, but it didn't take long for me to guess whose it was. I turned it on and said "Hello?"
Caroline's voice came on the line and said "Hello, How was practice?"
"Good, can you see me?"
"Yes, and I need you to be a very good boy for me. Can you do that?"
"Yes."
"Ok Danny, I need you to turn around and walk to the window and take off all of your clothes except your underwear." I did as I was told waiting for more instructions. I was so exposed standing there where anyone could see. I was getting nervous but I was definitely turned on. "Good, I can see you better now. Good, good. You really have filled out, look at your chest and stomach. OK, now take off your underwear." Once again, I did as instructed. Standing there with a chubby that was growing to a hard-on. "Ok, now turn around and bend over so that I can see your ass from behind." I turned and mooned the whole neighborhood. I was starting to feel really stupid.
"Ok Danny, you passed the first test. I want you to look in your desk and see what I left there for you. I need you to take it out and show it to the window." I sent into my drawer and found a hard rubber tapered cylinder that had a wide ring near the end. I brought it to the window and showed it to whoever was watching.
'Good Danny, now go to your bathroom and open up the window. Now go in the medicine cabinet and get out the Vaseline. Stand on the toilet and I will tell you what to do next. Good, now smear a bunch of Vaseline on that butt plug and a good amount around your ass."
I was shaking because I was nervous and because of the anticipation of what was to come next.
"Good boy, now slowly work the plug up your ass for me. I'm going to need you to squat on the john like you're going to the bathroom. Except instead of something coming out, something is going in. Take your time and I will talk you through it OK?"
"OK" was all I could get out of my mouth.
"Now I need you to crouch down low so that your ass is as open as possible. Now slowly push the tip in. Good boy, that's good. Look at my strong boy taking it up the ass like that. Does it feel good?"
"No, it kinda feels like I gotta go to the bathroom."
"Ok Baby, now just relax and keep pushing. That's it baby just like that."
I pushed until the stopper hit home, and my sphincter grabbed the smaller narrow neck. I just looked out the window and gave the OK sign.
"OK Danny, now put on your sweatpants and no matter what happens that thing stays in your ass. Now walk downstairs and come over to my backyard. We're going to play Simon says. Now Simon says come over to my house and come around back."
The plug in my ass felt a little comfortable, but I was getting used to it. I started down the stairs slowly, so that it didn't come out. I found that I was clinching too much and that if I just relaxed, it was going to stay put and it felt a lot better. I walked around the side of the house and opened the gate to the picket fence in the back yard. I held the walkie talkie to my ear waiting for my next instruction.
"OK, Simon says now stop. Simon says to slowly do some deep knee bends like in football practice. Simon says go slow down then slowly up."
I was in the center of her back yard and I started to squat down and then come up. As I moved up and down, the plug worked its way in and out. It felt strange at first, but it was really starting to feel good. I was getting really turned and my movements were getting lower and I was moving faster.
'That's it Danny, OH fuck yea. That's my baby, Simon says do it some more go ahead and fuck that virgin ass of yours. Simon has a secret, I have a plug in my ass also and I'm doing it too. I know just how it feels and I'm here baby, keep going, I promise it will feel great."
I did keep going and it did feel great. At this point, I was rock hard and I was looking for some relief. I could hear Caroline on the walkie talkie, and I was ready.
"Simon says walk towards the back of the yard. Simon says look up!"