Introduction:
Jenn came to me initially for help and advice on a sexual "problem." She wanted to give her anal cherry to her boyfriend, John. I am not usually in the advice giving business, being more interested in dominating submissive women and controlling their sex lives. But Jenn was sweet and naΓ―ve and easy. She agreed to my standard set of rules and I adopted her. You should be able to easily infer what my advise was, and it was fun to push her to couple it with some beginner exhibitionist tasks. Jenn is very much a beginner in this field, so I had to start her off with very basic dares. If you are looking for wild and off-the-wall kinks you will be disappointed. If you enjoy watching a newbie struggling with her desire to please, and testing her sexuality, I think you will have fun. I know I am.
This account of Jenn's progress is in three parts. Her beginnings at preparing her ass for use by John, her initial foray into public sex, and her second step in that same arena β sexual contact. For experienced exhibitionists these events would be duck soup (whatever that means). For Jenn, these were major steps, and I think you can see the emotions they elicited from her mind and body.
Please tell Jenn through your feedback how you feel about her, and her willingness to share herself with you in this public forum.
Susan James
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Part One: Preparing for an ass fuck
Sexy Susan,
How are things with my naughty girlfriend? I thought I would update you on my "anal" progress. That sounds so kinky. I am so excited about my weekend coming up with John. He has no idea that I am going to give him my ass. The anticipation has me masturbating a lot lately. And your instructions about how to prepare my ass for him have me hot all the time.
I found an adult toy store that has a women salesperson. Went in and talked to her about what I was doing. She was so sweet. She helped me pick out small, medium, and large size butt plugs. The large looks awfully big but she assured me that by the time I worked up to it, I would thoroughly enjoy it. She also helped me with a good lube. She picked out one to use with the butt plugs and then she recommended another one for when he enters me. I am not sure what the difference is still. She gave me the second one as her treat. I think she was a little excited with the idea herself.
I am starting to get used to the small one now. The first few times felt really strange. It felt a little like I needed to go to the bathroom. I could not keep it in very long at first. I started inserting it in the evenings and wore it as I did things around the house, reading, and checking email. I found myself really squirming in the chair feeling it move in me. The first time I wore it out was to the grocery store. Even though I knew that no one could see or tell, I was a little self conscious that I might be walking funny.
After getting a little more used to walking around with it in, I decided to take your suggestion. I put it in before John and I met some friends for dinner Saturday night. Oh my god, Susan, I felt so naughty knowing that I was sitting there talking, laughing, and eating dinner among a group of people, in public, no panties, with a butt plug in my ass. By the end of dinner, I was so horny I could hardly stand it. I was so hot that on the way home I started rubbing John's cock in his pants while he drove. He wasn't sure what had gotten into me (If he only knew, wink!). When we got parked in the driveway, I pulled his cock out and started giving him a blowjob right there in the car. I didn't even care if the neighbors could see us. When we made it into the house, I went to the bathroom and removed the butt plug so John would not see it. I was so hot and horny. John could not believe how wet my pussy was when he spread my legs to lick me. I just smiled at him, thinking about my little secret. We had absolutely incredible sex. Wow, what a night!
I am going to start working with the medium sized one now. The first time I eased it in this evening, it really stretched me. It stung a little at first but then I just felt really full. I do feel very sexy and naughty when I am bare-assed and wearing the plug in public.
As for your dare....I am still working on my courage. At first I was thinking, no way. But you have me thinking and doing things that I never thought I would do. I get really turned on thinking about your suggestion. I will keep you posted.
Time for a nice hot bath.
Naughty dreams,
Jenn
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Part Two: Confronting a stranger.
Hello Susan,
As for your dare, you naughty, naughty girl, I did not think that I could ever do anything like that in public, especially with a complete stranger. However, I found myself thinking about it more and more, and getting a little (more like a lot) turned on by it. It took a while but my love for erotic adventure finally won over.
I woke up Wednesday morning and decided that this was the day. I called in sick to work, and then took a long hot bath. My body was tingling with the thoughts running through my head. I dolled myself up, and put on my sexiest little sun dress. I took a few minutes to insert the butt plug and get used to the full feeling while I finished getting ready. I stood in front of the mirror, checking to see that everything was just right. I gave myself a little wicked grin and then headed off to the mall for some 'shopping.'
I felt so naughty and kinky walking around the mall bare-assed, especially knowing what I was up to. My ass was becoming very sensitive to every movement of the butt plug. Oh my, I was feeling naughty! My mind was racing with anxious anticipation the whole time I was trying to shop. As I was walking out of one of the stores, I saw him. He was casually walking by himself. He was maybe in his early thirties, and very good looking. I took a deep breath, and walked over to him. I touched him on the arm, and looked into his pretty blue eyes. And just like I had rehearsed over and over in my mind I said, "Excuse me, sir, I know you don't know me, but I needed to tell someone that I am not wearing any panties, and I have a butt plug in my ass, and I feel so sexy."