Dan's Dilemma Ch. 02

Story Info
Dan goes farther with his fantasies -- and I let him.
3k words
4.57
111.7k
41

Part 2 of the 3 part series

Updated 10/18/2022
Created 09/16/2010
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
MarleeM
MarleeM
713 Followers

Background (from Dan's Dilemma)

My nephew Dan is in his mid-thirties now and I am about ten years older. From when he was a baby until his early teen years, I was Dan's regular babysitter and we spent a lot of time together. He was like a little brother.

Dan had called rather unexpectedly and asked if we could get together to talk about something, but he did not tell me what. He picked me up at work and we had a wonderful meal.

I was happy to see Dan, now grown. We had a lot of catching up to do, and I was curious about what he had to talk about. After Dan took me home, he told me what was on his mind.

Dan had developed a pantyhose fetish. As he explained, when I was his babysitter, I often wore skirts and pantyhose. He would always rub his hand on my legs, enjoying the texture and feel of the hosiery.

Dan explained that this had led to his feelings of pantyhose to the point where he regularly wore pantyhose himself. He was embarrassed to tell me, but he had kept his feelings bottled up for quite a while and thought I would be the best person he could talk to about his fetish. He did more than talk, however.

I was curious about how he looked in pantyhose and also wanted to make sure he understood that he had nothing to be embarrassed about. I suggested he get a pair of my pantyhose and put them on.

Once Dan had the pantyhose on, we kept talking to bring ourselves up to date. Finally, I asked if he was excited and he admitted that he was. I actually asked if he would show me, and he did.

Before I knew it, I was caressing his pantyhose-covered thigh and he was rubbing his cock through the pantyhose. He came and made quite a mess in my pantyhose. After cleaning himself off, he had to leave but we agreed to have dinner again the next night.

That evening

After Dan left, I was in quite a state. When he stood before me with his beautiful erect cock, it was all I could do to control myself. I had been able to limit myself to caressing his nylon-covered leg while he rubbed himself until he came, but I had so wanted to do more. I had been so tempted to touch him and to taste his warm cum, but I held back.

I was so excited by the time he left that I had to make myself cum before I even left the kitchen where we had been talking. As soon as he was out the door, I lifted my skirt and slid my hand inside my pantyhose and panties. I already was wet and it did not take too long before I had a wonderful orgasm. I made myself cum one more time after I was in bed.

Today

This morning, I was trying to decide what to wear to work, knowing that Dan was going to pick me up again. I wanted to wear something he would appreciate. I had always enjoyed seeing the lengths to which guys would go to look at my legs. I also enjoyed watching them to see how they would react to seeing something they thought they were not supposed to see. In Dan's case, there was something very special and very exciting.

I had several shirt dresses that I wore to work. On most days, I wore a slip under them, but occasionally I would not. These dresses buttoned all the up the front, so I could show more or less cleavage and more or less leg as I chose. Another "feature" of these dresses was that there might be gaps between the buttons where someone might be able to see inside the dress. I noticed more than a few guys noticing these gaps and trying to strategically place themselves for the best view.

I decided to wear one of these dresses for Dan. Depending on my mood, I could show him as much or as little as I liked, all the while looking very prim and proper. I was not sure how Dan would feel after telling me his secret.

I knew how I felt, however. I was married, and Dan was my nephew. These things kept warning me that I had to be careful. But that cock! I was so tempted by it. I wanted to touch it, to feel it as it got hard and as it came.

I had been so tempted to tell Dan he had to leave my pantyhose when he left last night. If he had, I knew I would have tasted his semen and probably would have licked my pantyhose clean. I felt like I had missed a golden opportunity. I hoped I would not feel the same way tonight.

In spite of any misgivings I might have, I knew I would go farther tonight. The idea of playing with Dan had me very excited. I wanted to have some fun, but not go too far.

Sitting at my desk, I kept unbuttoning my dress and then buttoning it again. I was very nervous about Dan's reaction and very anxious. I should not have been.

Shortly after lunch, Dan called. He seemed much more relaxed and open than he had the day before.

"Hi!," He said, "how are you this afternoon?"

"Hi Danny Boy," I said, smiling, "I was afraid you were not going to call."

"Why would you feel that way?," he asked.

"Well, we had quite an evening last night and we had a very personal moment," I said.

"I know," he said, "I was there, remember?"

"I don't think I will ever forget," I replied.

"Good," he said.

"In fact," I admitted, "if I wasn't married and if you weren't my nephew, I might have done more than just watch and I might have touched more than just your thigh."

There, I said it.

"That was the most exciting thing I have ever seen," I said, "I'm surprised I was able to resist."

"I wish you hadn't," he said, "I've been dreaming about wearing pantyhose with you for years. Last night was like a dream come true for me. I want to share my passion with you."

"Oh, Dan," I said, "I can't go very far with this."

"I know," he said, "I wouldn't want you to. But I'd like to play around a little."

"Well, I might be able to do that without feeling too guilty," I said, "I want to touch you, but we can't go farther."

"Just touch?," he said, laughing.

"Well, touching so you cum again for me," I admitted, "so it'll be more like rubbing."

I was blushing.

"That would be heaven," he said, "it's what I dream about."

"About me specifically, or women in general?," I asked, curiously.

"Well, sometimes about different women, but I always find myself having fantasies about you," he said.

I was taken aback. We hadn't seen each other in quite some time.

"Even after all this time?," I asked.

"Yes," he said, "you are always in my fantasies."

"What sort of fantasies?," I asked.

"Well, I often think of you in pantyhose without panties on," he said quietly.

"Oh my," was all I could say.

"So, when are you going to be here?," I asked after a quiet few seconds.

"Probably in about an hour," he said, "I'm waiting for my new pantyhose to dry."

"Okay," I said, laughing, "I have a few things to finish here anyhow."

"See you then," he said, and hung up.

Just the thought of being with Dan again was getting me excited. I started to touch myself to see if I was getting wet when the idea came to me.

"Girl, you are his fantasy," I said to myself, "take those panties off for him!"

I did. I closed my office door and unbuttoned my dress to the waist. Reaching in, I took my pantyhose and pulled them down, stepping out with one foot. Then, I reached up and took my panties, sliding them down my legs and stepping out of them. Finally, I put my pantyhose on and made sure they were on as far as they could go.

"I guess I was getting wet," I said to myself as I felt my panties.

I sat down to finish the work I had to complete. The feeling of my bare bottom inside my pantyhose was new and very arousing. I counted the minutes until Dan arrived.

Finally, he arrived. I handed him an envelope.

"What's this," he asked.

"Open it and see," I said with a smile.

"Oh my God!," he said quietly, "does this mean what I think it means?"

"Do you think so?," I asked, smiling more broadly.

He took the panties out of the envelope and then held them out to look at them.

"Wow, these are sexy!," he said.

"Should I put them back on?," I asked, smiling again.

"Actually, I don't know that you really took them off," now it was his turn to smile.

"How can I prove it to you?," I asked trying to sound innocent.

"Well, I think you should let me investigate," he said, "is that okay?"

"I guess so," I said, walking up to him and expecting him to unbutton my dress. Instead, he took me by the shoulders and turned me around so I was facing away from him. Grasping the hem of my dress, he slowly lifted it until my bottom was exposed. Thinking of my plan to have fun, but not go too far, I did not protest.

"Dan!," I said, "my office door is open! Someone could walk by." He dropped my dress like it was burning his hand.

"Oh my God!," he said, "I'm so sorry. I don't know what came over me."

Dan looked like he had been hit. For a minute, I thought he was going to cry. Then I smiled.

"You should close the door first," I said, "and while you're at it, you should lock it so we won't be interrupted."

"I was afraid you were mad at me," he said, "I'm sorry -- this is all new to me."

"I know how you feel," I replied, "I am not used to doing this sort of thing, but after last night I wanted to do more. We just have to be careful that we don't go too far. Now, where were we?"

"I was about to fulfill another fantasy, if I remember correctly," he replied, now smiling again, "once I got older and remembered how I had felt seeing you, I began to think of things I wish I had done or seen. I always wondered . . . ."

"Well, Big Boy," I said with a grin, "you just might get your wish."

With that, I moved closer to Dan and turned around. I felt him take hold of the hem of my dress and felt is slowly lifted. I was becoming more and more excited.

"I hope you like what you see, L said, quietly, "I'd hate to disappoint you after all this time."

"You are beautiful" he said, "more beautiful than I dreamed. This is almost enough to make my fantasy become reality."

"What is your fantasy?," I asked, "I'd love to make it come true."

"Can I just show you?," he asked, "I'm afraid I'll chicken out if I try to explain."

"Okay," I said, feeling very curious and excited.

Dan led me to my desk and had me stand next to it. As we moved, my dress fell back down.

"Lean over, please," he said, positioning me so I was leaning onto my desk.

Dan moved directly behind me. I felt my skirt being lifted again. Dan's hands ran softly over my thighs and bottom. The feeling was electric and I felt myself getting excited. "I wore my new pantyhose today," Dan said.

I heard the sound of a belt buckle and the unmistakable sound of a zipper being lowered. I began to worry a bit about exactly what Dan's fantasy involved., but my sense of excitement overcame any worries.

"I usually don't wear pantyhose under my slacks because I get too excited and I'm afraid I'll cum in my pants," he said, "but after we talked today I thought I'd take a chance."

I heard Dan move again and realized he was removing his slacks. I looked behind me. Again, I saw him standing wearing only his dress shirt and what had been my suntan, sheer-to-waist pantyhose. He was not fully erect, but as I watched, he began to grow.

It was a wonderful sight. Then he moved behind me and I could not see him. Suddenly, I felt his hands touch my hips. He slowly moved them up and down my hips and over my bottom. His light touch was driving me crazy. His hands moved over the backs of my thighs, then I felt him touch first one thigh then the other with both hands.

Dan alternated his caressing of my thighs with two hands. His fingers caressed the inner and outer thigh while the palms of his hands caressed the back of my thighs. My legs, almost of their own accord, parted slightly so his fingers could slide between my thighs. His light touch was very exciting and I knew, if he slid his fingers to my upper thighs, he could feel how wet I was becoming.

Being exposed to him like this and being massaged was an intensely erotic experience. I almost forgot where I was and who was making me feel this way.

Then, Dan moved closer and held my hips again. I felt his legs against mine as he straddled me. He was still for a minute, and then I felt him.

I felt his cock, hard now, on my bottom. His flesh and mine, separated only by two thin layers of nylon. Even with the pantyhose covering me, he was able to spread my bottom enough to create a nice friction. Pulling on my hips, he rocked his and slid his cock up and down. It felt wonderful.

"Oh God, Oh God!," Dan moaned, even more than he had the previous night.

"Yes, Baby!," was all I could say.

I loved the feeling of his pantyhose-covered legs against mine. I pushed back against him with my bottom and tried to move along with him, but his grip on my hips was too strong.

I was getting wetter by the second. I could feel his strong legs squeezing mine together.

"Oh, Oh, Oh, Oh," was all he said.

I pressed my bottom back against him and felt him thrust harder. His cock seemed to grow as he kept sliding against my bottom.

There I was, leaning over my desk with my dress pulled up over my waist. My nephew was rubbing against my bottom and I waited for the inevitable eruption. I was on the verge of my own orgasm as he pressed into my bottom.

Then, he stopped. I was not sure what had happened -- his right hand released my hip and he pulled back a little.

"I have wanted this for so long," he said.

I was able to look back and saw out of the corner of my eye that he had reached into his pantyhose with his right hand and pulled his cock out. He was stroking his cock with no pantyhose covering it. His moans grew louder.

"OH, OH, OH, MMMMMMMMMM!," was all he said.

I continued to run my head to try to watch. I could not see completely, but did see enough to notice his cock getting even harder and his strokes becoming more rapid.

"AHHHHHHH!," he almost screamed., as he came.

I could feel him push hard against me and then felt the hot fluid surging from him and splashing on my bottom. He put both hands on my hips again and began sliding against my cum-covered bottom. I could feel his hot semen running between my cheeks and between my legs -- drenching my pantyhose. He was still hard and I was close to orgasm.

"Dan, Dan, Dan!" I said aloud as I pushed back against him, "I love this! I love you!!"

As my orgasm hit me, I pushed back against him and moved my bottom -- trying to stroke him with it. Now, I was the one moaning -- moaning his name.

"Oh Dan, Oh Dan, Oh Dan!," I moaned, "I am cumming!"

At that, I felt Dan's body stiffen and he thrust against me. I could feel his cock throb as he sent spurt after spurt across my bottom and lower back. Spent, he fell against me.

"Oh God," he said, almost laughing, "that was the most amazing thing I've ever done. I waited so long and it was better than I imagined it would be."

"I am so glad," I said, "I didn't want to disappoint you today."

"You definitely did not disappoint," he said, "but I think I made a mess of your backside. Some even got on your dress." "That's okay," I said, "you marked me. I am yours, at least for now. But do one thing for me."

"Anything," he said.

"I want you to spread your cum all over my bottom and between my thighs," I said. "I want to feel you all over me."

"Gladly," he said, "but don't you want to get cleaned up -- or don't you want go to dinner anymore?"

"I still want to go to dinner," I said, "and I don't want to clean up. I want to be out in public with you knowing I am covered with your cum."

With that, Dan gave me a nice cum-lubricated massage as he rubbed his juices into my backside. As he did so, I reached between my legs and was able to capture a dollop for myself. Sliding my finger into my mouth, I finally was able to taste what I had been thinking about since last night.

"Oh oh," Dan said, "you seem to have quite a wet spot on the back of your dress right over your bottom."

"That's okay," I said. "If anyone says anything I will just say I must have sat in something. Now, pull my dress down and take me to dinner."

MarleeM
MarleeM
713 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
9 Comments
MeanOralSexToy4womenMeanOralSexToy4women3 months ago

This story sounds like a real life/ fantasy combo. The babysitter scenario could be real. The office scene is a little too risque for real life.

Panyhosemaniac123Panyhosemaniac123about 2 years ago

As a lover of pantyhose too, I wanted to be in that office with you!!! Your story called out one of my favorite pantyhose fantasies!!!

Panyhosemaniac123Panyhosemaniac123about 2 years ago

I wanted to be in that office with you!! As a lover of pantyhose, you called out one of my many fantasies. This is a great story!!!

AnonymousAnonymousover 5 years ago

love it!

SlutMom1975SlutMom1975about 10 years ago
Wet pantyhose pussy

Wow I am so hot and wet after reading this story. My pantyhose covered pussy is so wet and I had to rub myself while reading.

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

A Mother and Her Son Romance, love and sex between mother and son.in Incest/Taboo
Linda's Discovery Mom discovers her son's secret.in Incest/Taboo
Making Out With Mom He gets to know his mother REALLY well.in Incest/Taboo
Late Night on the Loveseat with Mom Mom and son get under the blanket and, well . . .in Incest/Taboo
Road Trip with Mom Ch. 01 Busty mom and well-hung son go on a cross country road trip.in Incest/Taboo
More Stories