Showing Myself Ch. 04

I doubt if anyone remembers me, but I wrote some stories here about myself back when I was around 19 or so. A lot has happened since then which is why I never finished, and I'm sorry about that. My husband found someone more exciting several years ago and left me, so I became engrossed with my work and just hung out with friends once in a while. I didn't realize it to its full extent back then, but I think I started writing down my adventures because my husband was neglecting me and probably finding fun elsewhere already. I still don't get it because I never say no to sex and would have done anything for him, but it was his choice. Oh well, it happens.

I was also looking through the comments to my stories and was kind of surprised that so many people liked them, and for those that are not familiar, I am just a normal person that has a strong exhibitionist streak, and wrote down some of my adventures when I was just coming into my own sexuality. I wasn't even sure I still had the login information, but I found it right away. Also, I am not a polished writer, and just write what comes to mind.

So, for this story, I'm jumping ahead a few decades and describing what's going on in my life right now, but if someone wants me to continue with the stories I started back then, just let me know in the comments.

Anyway, I was traveling on a business trip two weeks ago in Chicago, and one evening I was sitting at the hotel bar having dinner, and a nice looking gentleman sat down near me. He was in his mid to late 30's, whereas I am now 56, but he still struck up a polite conversation with me. Mind you, I take care of myself and everyone says I'm attractive, not that I was looking to meet someone. He was about three seats over, and after making small talk, I said he could move over if he likes. I'll call him Jim, and if anyone is wondering, this is absolutely true.

We talked, and he was extremely polite and classy, which I liked a lot. I just glossed over the issues I had with my ex because I don't like to bring out drama, and we just had a normal conversation. When I finished my glass of wine, he asked me if I would stay longer if he got a bottle and joined him in the lounge over by the fireplace. I couldn't refuse that, so we moved over and continued our conversation.

After another glass of wine, we started laughing about the craziest things we have ever done, and I explained to him there was no way he could top me because I remember when there were no cameras around and you could get away with anything. He said he would be the judge, and to try to shock him.

Without going into everything I have ever done (much that I haven't told here either), I told him about the times when I would go in the adult theater and remove my clothes slowly and put them away in a corner so I wouldn't be able to quickly dress if people came in. I described how I would prop my feet up on the back of the seats in front of me and run my fingers through my wetness, and how eventually some men would sit beside me or in front of me and masturbate until they came. I told him I did it regularly, and some days I would see more than ten men cum, although none ever touched me.

He just looked at me, and said, "Ok, you got me, I don't have anything that crazy. But I love that you weren't afraid of taking control. It shows in how you carry yourself."

I thought to myself, "He is just too charming. He didn't call me a freak or anything", so I decided to fill in some details.

"But, I never directly played with any men and there was never any touching, and this was before I met my husband. I did make a couple of regular friends though. There was one guy who really liked me, and we used to sit together and he would masturbate with me. There were a couple of women who liked me a lot, and I actually met them for lunch and shopping sometimes, although I never did anything overtly sexual with them. They wanted to though."

"Not overtly sexual? But a little bit sexual? You know this is every man's fantasy."

I laughed and said, "Well, there was the time in the dressing room when we shopped, but that is a story for another time. I'll just say she enjoyed helping me try on some sexy things."

By now I was quite uninhibited, and I said, "You know what? I like you. There is a half bottle of wine left and our glasses are almost empty. I'm going to suggest two choices, and I want you to respond with what you are most comfortable with. The first choice: If you would like to continue chatting down here, then fill our glasses and we'll do that. The second choice: If you would like to come to my room and watch me lay back on the bed and slowly remove my clothes and make myself orgasm, then stand up and take the wine and glasses, and we'll head for the elevator. Your choice, no judgement, and either one would make my night because I really find you charming and kind."

He sat silently and looked at me, and finished the last sip in his glass before he spoke.

"One question. Is this a setup? I'm not married so I don't care about that, but there isn't going to be someone there that is going to rob me or beat me up or something like that, is there?"

"You know, I never even considered that, and I actually admire that you're being cautious, because it means you would look after me too. But, there will be no contact anyway, and no money involved. So no, it isn't a setup. Let me try to convince you."

I looked around, and there was no one in the lounge area, and no one at the bar area was looking in our direction, so I pulled my skirt up as discretely as I could and slid my panties off. Thankfully I was wearing something sexy, and I tossed them to him and they draped over his glass. I couldn't have done that again if I had tried a hundred times.

Flustered, he quickly grabbed the panties and tucked them away, and said, "Are you crazy? You could have just said it wasn't a setup, I would've believed you!"

"Well, I wanted you to be sure so you would be completely at ease. Now feel my panties and see how wet they are. You see how excited you made me? So now, either pour the rest of the wine and we'll finish our evening here, or stand up and we'll head to my room. You'll even be able to wrap my panties around your cock and watch me if you want."

He stood up and took the two glasses and the bottle and said, "I'll follow you."

We got in the elevator, and I whispered, "You have no idea what the cool air feels like on my bare pussy. If there wasn't a camera right in the corner, I would be lifting my skirt up and rubbing myself right now."

The elevator stopped and the door popped open, and we walked towards my room. I can't even describe how excited I was, having a much younger guy walking with me.

We entered the room, and being the gentleman that he is, he poured us the rest of the wine and said, "You really don't have to do anything if you don't want to. We can also just relax and talk some more."

"That's very kind, but I'm beyond that now. Pull that chair over and place it in front of the bed and watch me."

He sat down and I stood in front of him and slowly unbuttoned my blouse. It hung open, and he could see my bra pushing up my full breasts as I started to reach around to unbutton my skirt. But just then, I suddenly felt very insecure.

"Look, I'm much older than you. Are you sure you won't laugh at me? You could have any girl."

"No, I won't laugh, and I think you're gorgeous. Just keep going."

Feeling relieved, I loosened my skirt and it hung on my hips. Thank god I tried to take care of myself and still had a flat stomach, so at least I had that going for me. I unsnapped my bra, and the cups fell forward, and my blouse barely covered my breasts. It's funny, all those times years ago I had no problem at all strolling around in front of every completely naked and even sitting on a stage and masturbating, but now I was nervous. But I couldn't stop myself now, and shrugged the blouse and bra off and let the skirt fall to the floor.

Standing there completely naked in front of him, I asked if he liked what he saw.

Rubbing himself through his jeans, he said I was amazing, which really warmed me up. I fell back on the bed and drew my feet up and spread my knees to expose myself completely. I keep my lips shaven, and am natural otherwise, although it is trimmed neatly. I ran my hands over my body and cupped my breasts, and asked him if my pussy looked like it was excited.

"Yes, I can see that it's damp. Can I get a closer look? I won't touch, I promise."

I nodded, and he knelt down in front of me and looked directly at my pussy. I couldn't hold back anymore, and reached down and slipped my fingers through the lips and gasped. The memories from years ago came back, so I told him to pleasure himself if he wanted to, because I wasn't going to stop.

He stood up and pushed his jeans down and exposed his hard cock. I responded by rubbing myself in small circles as my nipples became hard and my chest flushed.

"Take the panties I gave you and wrap them around your cock and stroke yourself. Pretend you're inside me, because that's what I'm doing."

He wasted no time and draped the panties over his cock and started masturbating. I didn't want this to be over too soon, so I told him that in order to prolong this, I'll give a command to pause once in a while. We continued our pleasure, and then I said, "Stop!"

He released his cock, and the panties remained draped over it. I squeezed my legs open and closed and rubbed my body and caught my breath before telling him to start up again.

We did this two more times, and then he finally said, "I'm going to cum, and can't help it. How do you want us to finish? Together?"

In the past, I didn't let the guys cum on me, but he had been so nice and I trusted him, so I said, "I'll kneel in front of you and you shoot it on my chest while I rub myself. Hold off until I start to orgasm."

I took my position in front of him and he started to quickly stroke his cock. My fingers were doing the same on myself until I told him, "Let go, I'm about to orgasm."

Jim stopped stroking and leaned forward slightly and pointed his cock at my chest as he started to ejaculate. I must have excited him, because it was so much! At the same time, I started to orgasm, but unlike him I kept rubbing myself until I finally came back down to earth. Isn't it funny how men and women are different like that? I brought myself to my feet and looked at his cum dribbling down my body, and collapsed on the bed.

He looked at me and said, "Sorry, should I get a towel to clean you up? I didn't know it would be so much."

"No! I want to just lay here and feel it! I want it on my body when I sleep tonight! Come here, finish undressing and lay down next to me."

I was so happy that he didn't just leave, and we talked about what just happened while we sipped the rest of our wine. I told him what a feeling it was to have him watch me when I did myself like that, and that I hoped he didn't feel less manly or anything since all I let him do was stand there and masturbate. He said he didn't feel that way at all, and that he was more than happy that he could excite me.

He was laying next to me and I was gazing at his body, and I said, "Can we do it again? Start stroking your cock, and we'll just lay next to each other while we play, ok?"

He took his cock in his hand, and I saw it grow hard again. I spread my legs and let my fingers wander, and let the middle finger rub my clit. My other hand teased my nipples, and I told him to see the effect he was having on me.

Then I had another idea, and asked him, "This time I would like to slip on some panties and have you cum all over them so I can wear them like that tonight. Do you mind? You've seen everything anyway, and that would make it a little more taboo."

He said he didn't mind at all, so I rummaged through my bag and took out a pair of light green lacy panties. I put them on and laid back down, and pulled them to the side so I could continue masturbating. He got on his knees on the bed between my legs while stroking his cock and told me he wouldn't last long like that. Sure enough, in a few minutes he asked how he should orgasm this time. I told him to cum on my panties and drench me.

Quickly, he assumed the position and stroked hard until he once again came to a stop and let his cum start flowing. Just as I wanted, it landed right on the light green material of my panties and made them turn dark from the wetness. I took my fingers and rubbed it in and I could feel the soft hair underneath my panties become wet. I don't know why that turned me on so much, but it did.

He collapsed beside me, and we gently kissed. I found it kind of funny that we had both orgasmed already, but we hadn't kissed yet, but it was wonderful.

I asked him how much longer he would be in Chicago, and he said one more night after this. It turns out that he is from Indy and I am about an hour from him, so we made plans to see each other the next night and then maybe some time in the future. I told him not to worry about me falling in love or anything because I'm well aware of the age difference, and I would be content to share his company. And if he already had a girlfriend, it's ok, I won't be jealous. We talked some more and pressed our bodies close to each other, and agreed that we would fall asleep like this, and he could just slip back to his room whenever he woke.

The next day, I was definitely distracted from the events of the previous night. We had exchanged numbers, and I hadn't heard from him by 10, so I sent him a quick text: "That was so much fun last night. Hope you didn't think I was too weird. I wish you could read my mind right now."

He replied immediately, "You weren't weird at all. I'll do anything to make you feel good. You still want to get together tonight?"

"Yes! Why don't you come to my room first, and then we'll go downstairs for dinner, ok? But, let's do this: I'll put one of my room keys in an envelope and leave it at the front desk for you. You pick it up, and when you come to my room, just walk in and say 'Room Service!' We'll play it by ear from there, ok?"

"You are so bad, but I like it. 7:00?"

"Perfect, see you then!"

The day dragged on, and I finally made it back to my room and showered and picked out an outfit. I was trying to figure out exactly how it should play out when he walked in at 7, and I decided I would keep it simple. So, I didn't even bother getting dressed and instead laid back on the bed and started masturbating, knowing he would walk in in me.

The minutes ticked by, and finally I heard the sound of the lock in the door, and he walked in, saying "Housekeeping! You needed extra towels?"

I pretended to be shocked and tried to cover myself, and said, "You don't even knock first? And you don't even have towels with you!"

"My mistake, I'm sorry. After all, you do seem quite wet."

"Well, at least let me finish and then you can bring me a towel from the bath. That will have to do."

I opened my legs back up and resumed my pleasure, looking him straight in the eye. I could see him getting excited, but he just stood there as though he was really a housekeeper doing as he was told. I continued my dialog.

"You know, there was a man here with me last night, and he was so out of control! He came all over me not once, but twice, and I fell asleep that way. I had to take an extra long shower the morning just because of him."

He started to rub himself, and I didn't want to tease him too much since he was so nice.

"But, I plan on going out to dinner and can't let that happen again. It looks like you need to take care of yourself too just like he did, but don't dare cum on me."

He took the hint and stepped closer while taking out his beautiful cock. Neither of us said a word, and I just stared at him as he started to masturbate. I thought back to the times many years before, and was feeling the same euphoria that I couldn't explain.

We both continued and he finally said, "I can't last any longer!"

I rolled off the bed and knelt down in front of him and said, "Cum in my mouth. I want every drop."

Just like the two times previously, he stopped stroking and I wrapped my lips around the end of his cock as his cum streamed into my mouth. He groaned and squeezed the last drops out and stepped back.

I stood up and looked at him and took his hand and placed it on my pussy, saying, "Finger me and make me orgasm."

I held onto his shoulders as he rubbed me, and within a minute I started convulsing and I collapsed against him. When my breathing finally slowed down again, he gently eased me back on the bed and crawled next to me.

He whispered, "So, I thought there would be no touching?"

"Honestly, that was my intention, but I guess the fantasy took on a life of its own when I saw you standing there. And we really are going out to dinner and I had just showered, so that seemed to be the only option."

He laughed and said, "Why does it seem like you were the one that controlled me even though I am the one who came in your mouth?"

"You make a good point. But, we aren't done yet. I want you to watch me get dressed now. Please, don't take your eyes off me for a second. I want to feel your stare."

I took the panties I had picked out, and slowly stepped into them and pulled them up to my thighs. I stopped and let my finger slide through my wetness and then brought it to my lips before I finished putting them on. I picked up the bra and slipped it on, making note of the fact that it is nearly see through. The dress I picked out was a button up sundress very similar to the one I wore the first time I went to the theater so many years ago, and I very slowly buttoned it up while he watched.

"Are you ready? You have no idea how wet I got just getting dressed in front of you."

"Yes, I'm ready. But I'm going to borrow your line from the morning, and say that I wish you would read my mind right now."

We went downstairs and took a table in the almost deserted restaurant, which was perfect. Before he could say anything, I asked the waiter to give us about 30 minutes to discuss business before we ordered.

After the waiter left, I said, "You know what I wish you would do? Drop your fork and then go under the table and pull my panties off."

"I can't do that! They would see that for sure!"

"Ok, what if I go to the restroom and take them off, and then you drop your fork and you take a look at my pussy?"

"Sure, that might work."

I went to the restroom quickly, came back and dropped the panties in his lap. He scrambled to hide them in his pocket.

"I should have known", he whispered.

"You haven't dropped your fork yet. My pussy is waiting. It craves your gaze."

"Give me a few minutes at least. I was wondering if your stories were really true, but now I'm convinced."

"Yes, they are absolutely true. I wish you were braver and would slip under the table and plant kisses on the inside of my thighs."

"I would love that, but it would be awkward to get thrown out of the restaurant in the hotel where we are staying."

"Ok then, tell me one of your naughty fantasies . It seems like I'm doing all the work."

"Hmm, you drop your fork and crawl over and unzip me and take my cock in your mouth."

"Gee, that's original. However did you think of that?"

"You inspire me."

"You have a wit about you that I like, really. You have been a very nice companion the last 24 hours."

"Likewise, and I meant it when I said you are gorgeous. And forget about the age difference, we look great together."

"You know what I want tonight? I want to straddle you and feel you inside me. Does that excite you? The vision of me hovering over you?"

"Yes, to be honest I've already fantasied about that."