Jenn No.3, Finger fuck and blow job with a stranger. Dare No. 3.
Introduction:
You've seen Jenn prep her ass for a fucking, and confront a stranger about the toys in her ass (Jenn No.1). Then you saw her give her body to a stranger for his enjoyment, in a public mall. She had her pussy caressed and her breasts fondled (Jenn No.2). Now she has moved up a step and has accepted a third dare: to give herself to another stranger for intimate sexual contact. Jenn is moving along nicely, taking a bit more risk each time. Here she is, first in an email to tell me she has done it, and then with the full account of what she did.
Jenn was a newbie up till now. And now her trajectory is heading for real sexual fun and depravity. Ya gotta love a girl like this.
Susan James
**************
An email from Jenn:
My dear sexy Mistress,
I hope everything is well with you during the holidays.
Sorry, it took me a while to report back to you about my third dare. I have been so busy during the holidays. Actually, I really wish it was over.
I am still so excited about my trip and the events with Rick. He was really hot. I have never cum so hard from a man's fingers. He was good. That little scissor motion he did with his fingers was awesome. It sent me into orbit. You should really have someone try it on you. My pussy gets wet and tingly every time I think about it.
Finally, I was able to get it all written down for you.
I know I have told you so many times, but you make me feel so sexy, so confident, and so erotic. Thank you so very much!!
Your sexy exhibitionist,
Jenn
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Dear Mistress Susan,
I so much wanted to accomplish my next dare. You wanted me to approach a stranger and have him masturbate me to orgasm, or give a stranger a blowjob, or if possible do both. The more I thought about the challenge, the more turned on I got. The thought of a strange man fingering me to an orgasm is intense and extremely erotic. I definitely like the thought of having an orgasm, but I think it is only right that if he gets me off then I should offer to blow him. So my goal was for both of us to orgasm.
Well, I just got home and wow what a trip. It was so incredible, Susan. I still can't believe the day and night that I had. First of all let me explain that I had a business trip coming up. I was going to be traveling alone so I scheduled an extra day for myself, maybe do a little "shopping". My boss would not know the difference. I thought this would be a great opportunity to do this dare. I would be away from home, no chance of anyone recognizing me. It would be a perfect setting. I packed some extra "sexy" clothes and headed out.
When I left my last business appointment I was feeling really good. Everything had gone well. I ate dinner, then was going to the room and passed the hotel spa. I noticed that they had a Jacuzzi isolated in the corner of the pool area. It really looked inviting, and the thought of relaxing in the warm water after a long day was irresistible. The only problem was that I had not brought a swim suit. It was getting late and there did not seem to be anyone else in the pool area, so I went into the locker room, stripped down to my bra and panties. What's the difference right? I grabbed a towel, turned the jets on and crawled into the Jacuzzi.
Wow, the hot water really felt good. I laid my head back and began thinking of my dare. (It was your dare when you gave it to me, and when I accepted it, it became mine.) I played it over and over in my mind. Finding the right guy, approaching him, and how he would react. Where would we go so that we would not get caught? I was getting really nervous again. I relaxed a while longer and then climbed out of the water. I was feeling a little frisky, so I took off my wet bra and panties, wrapped the towel around my breasts, grabbed the rest of my clothes out of the locker room and headed for my room with nothing on but the towel. The towel was enough to cover my breasts but only covered about half of my ass. Anyone catching me in the elevator or hall would definitely get a nice view of my naked bottom.
Susan, I was actually thinking of you at that moment. You would have been so proud of me. Something I would have never done before you came into my life. By the time I got to my room, my whole body was tingling. I was high on adrenaline; it was such a rush.
I woke the next morning, got up and headed for the bathroom to get ready for my day. I took a little extra time shaving my legs and pussy. I wanted everything to be soft and smooth for my stranger's hands and fingers. After a nice warm shower, I fixed my hair and makeup. I got dressed, pulling on my short skirt but leaving my panties lying with my bra. I would not be wearing them today. I had packed a nice button-up blouse with a low cut neck line that is very good for showing my cleavage. I even left the top couple of buttons undone so that my bare breasts were not hard to see as I moved and turned. Everything looked perfect. I checked myself in the mirror. A hint of my nipples was already visible through the thin fabric of my blouse. I was getting excited and I hadn't even left the room yet.
I headed for the local mall. The weather outside was cold and brisk. Obviously my outfit was not one for winter, but was perfect for what I had planned today. I wore an overcoat but left it open in the front so that all my assets would show. Speaking of ass-ets, the air was nippy on my bare bottom and pussy.
After shopping a while and checking out potential candidates for my dare, I finally picked a guy that I was going to approach. He was a very nice looking guy, probably in his thirties. Everything was going well; I took a deep breath and walked up to him. Excuse me sir, I need your help. I am trying to complete a dare. If I do not accomplish it, I will be punished. I am not wearing any panties. Would you be willing to rub my pussy and finger me until I orgasm?
He looked at me with a shocked expression and said, "Are you crazy", turned and practically ran off. Wow, that was not what I was expecting. I guess it had to happen sometime. I was not sure if he would notify security on me or not, so I quickly left the mall.
After that disaster, I decided to stop in at a little coffee shop in a small shopping center not far from my hotel. I needed to regroup anyway. When I walked in, I looked around the room noticing that it was not very crowded, and saw a very nice looking guy seated at a table by himself. I located a table on one end of the room that would let me flirt with him or any other person in that general area. This might be the opportunity I had been waiting for.
I removed my overcoat and situated myself so that when he looked in my direction he would have a great view of my bare pussy. I reached into my purse and pulled out a book. I pretended to read while observing him and a couple of other men in the room who seemed to have noticed the view under my skirt.
My nipples were beginning to tingle, and I could feel a warmth and wetness starting to develop between my legs. I was getting hot, but I was also very nervous. I had never so blatantly exposed myself to a room full of strangers. As I reached for a napkin I had "accidentally" dropped, I spread my legs a little farther apart.
There was a conflict going on inside me. On one hand I was really getting off on exposing my most private parts to the gaze of strangers, and on the other I felt shame and fear for doing it. My stomach felt like it was full of butterflies, pardon the cliché. My hands were trembling slightly and my underarms were damp. I felt a single bead of perspiration run down my rib cage.
As I sat there staring blankly at my book (it could have been upside down for all I knew), I realized I had finally gotten my guy's attention. He was staring right up my skirt at my naked pussy!!! It took all I had to not slam my thighs together. His stare felt like a laser, heating my labia with its power. More juice leaked out of my slit and I wondered if he could see that, too.
I realized after a few moments that I was not breathing, and I inhaled sharply. His glance jumped to my eyes, but he didn't look away as most men would. But I did, and felt my face instantly heat up with my flush of shame. But steeling myself, I not only didn't clamp my legs closed, I slowly widened the distance between my knees. Oh god, this was incredible. I was so excited that I worried for a minute that I might wet myself.