Early Onset Dirty Old Man Syndrome

My name is Bruce. I am 45 years old and currently without a significant other. I am divorced, but I have had several friends-with-benefits in the past. Now there is just one that I can call for a date whenever I want to.

The problems with her are this; she allows me to have sex with her, but only straight-forward missionary position vaginal intercourse. That can be pleasant but boring. She thinks taking my penis in her mouth is disgusting, and once when I just touched her anus she screamed as if she was being raped.

She also wants to move in with me, and she says she would like a commitment from me. Fat chance.

So I call her occasionally, but usually I just take care of myself, if you know what I mean.

I don't consider myself old at all, but I seem to be acquiring the traits of a so-called dirty old man.

Whenever I see an attractive woman in public I fantasize about seeing her naked and having sex with her, usually wild and kinky sex. I don't think this does any harm, as they say you can't go to jail for what you're thinking.

For example, one time when I saw a great looking young woman ahead of me in line at a fast food place my thoughts were about sodomizing her. I spoke the words to myself, "I would like to pull your pants down and bend you over." Of course, I didn't try to speak to her and I would never say that to someone like her.

I have thoughts like "God, I would like to fuck you" or "I would love to cum in your mouth" or similar unspoken thoughts whenever I am near a good-looking woman.

Maybe I should get some professional help, but I just need some exciting sex and I don't really think I have a mental health issue. My guess is that many men think thoughts like this, but they would never admit it.

I had to do some grocery shopping one day and it became very interesting.

I grabbed a cart inside the front door of my favorite supermarket and began to shop.

I picked up several items that I needed or at least wanted, and then I saw her.

Tall, slender redhead, long legs, tight jeans, butt-crack visible. At least 10 years younger than me. I had to follow her and get closer.

She went down the Pet Food aisle and I followed even though I do not own a dog.

My imagination was working overtime and I visualized her naked. God, she was hot.

I had an erotic thought and I inadvertently mumbled it to myself.

"I would like to shove my cock up your ass all the way to my balls."

Please understand, I mumbled this so softly that I was barely able to hear it. I did not want her or anyone else to hear it.

To my surprise, she stopped and turned to look at me.

I stopped also and gave her a friendly smile.

"What did you say?"

I feigned confusion and said, "What?"

"I asked you what you said."

I gave her my best blank expression and said, "I didn't say anything."

"Yes you did, and I heard it. Admit it."

"I'm sorry, but I do not recall saying anything to you. I may have just been thinking out loud and talking to myself."

"I understand that, but you were referring to me. Something you wanted to do."

Oh my god, is she going to call the police? I don't think she can prove anything, it is her word against mine, and I will just say I was not speaking to her.

"Well, pretty lady, the only thing I can say is that I was not speaking to you. I am not sure what you think you heard, or how you could hear me from that far away."

"Alright, if you won't say it, I will. You said you wanted to shove your cock up my ass. I believe you said all the way to your balls."

That was like a kick in the stomach. She did hear me, although I don't know how. Am I going to be arrested?

"I apologize if that is what you heard. Believe me, I meant no harm."

She gave me a smile that was almost a smirk and turned and walked away.

I breathed a sigh of relief. I do not want to explain myself to the police or even store security.

I continued with my shopping, and I was picking up some frozen dinners when I saw her walking my way. Is she going to cause trouble?

She walked up close to me and said, "OK, so you meant no harm. But did you mean what you said?"

How in the hell do I answer that? Sure, I meant it, but if I admit it can she use it against me? I didn't think so, because again it is her word against mine, there were no witnesses.

"Yes, of course I meant it, but I didn't intend for you to hear it."

She nodded her head and thought for a moment.

"But if I didn't hear it, how could you expect me to agree to it?"

Is this another trick to trap me?

Finally I answered, "That's a good point. And I did hope you would agree to it."

She absorbed that for a moment.

"OK, you are finally being honest with me, so I will be honest with you. For some time now, I have been intrigued by the idea of having totally anonymous sex. It has become a favorite fantasy of mine."

After an appropriate pause I said, "Well, we are complete strangers. So maybe I can fulfill your favorite fantasy."

"How do I know you are not some nut-case that will tie me up, have your way, and then murder me?"

"I don't know how I can reassure you on that. I am just a law-abiding guy who would like to find a woman that would want and enjoy the same things that I do."

I thought of a solution.

"How about this. You must have a smart phone, everyone does. Take a picture of me, and take a picture of my Driver's License, and send the pictures to your best friend. Tell her that if anything happens to you or if you just disappear she should get them to the Police. If I was a rapist or a murderer I don't think I would give you the evidence to send me to prison."

She said, "That's clever. Let's do that."

She got a close-up shot of my face, and then a super close-up of my Driver's License with my name and picture and address. She texted them with a message and said, "Done."

"Alright, now that you have incriminating evidence on me if I do something bad, how about it?"

After an agonizing silent moment, she said, "I don't like to admit this to someone I don't even know, but my relationships have all eventually gone bad. I want to be more adventurous about sex while I am still young. I'm ashamed of myself, but I have even had thoughts and fantasies about what you said you wanted to do to me."

I moved a little closer to her, but not too close. I wanted to be careful not to offend her by coming in physical contact. I think she was still a little bit leery of me.

"You are being totally open which is brave, and I admire you for it. I can only give you my word that I would not do anything that you didn't also want to do. I think you should have your adventure and experience your fantasy."

I decided not to say another word, and just wait her out. Awkward moments passed.

She quietly said, "Then let's do it."

I almost fell on the floor.

Is this even possible? Could all my horny thoughts finally pay off?

I knew it was my turn to speak, and I didn't want this to slip away.

"Let's go to my place. I live just around the corner on the next block."

She nodded in agreement.

We wheeled our carts up to the checkout stands where there was a long line at each register.

"You know what? I don't really need this stuff."

"Neither do I" she said, and we left our half-filled carts and walked out the door.

I walked to the store, but she drove, so we got in her car for the short trip to my condo.

I directed her to park in one of the visitor's spots, and we went into my front door.

We stood there for a few moments, not knowing what to do next.

She said, "I have never done this before. I hope you have. I hope it is not uncomfortable or worse."

Right, I thought. You are just an innocent virgin who lets herself get picked up at the grocery store.

"I have had some experience. Just trust me."

I gently led her to the bedroom and started to undress. She modestly looked away which I thought was cute, and she began to strip down. She stopped with just her bra and panties on, and I signaled to take those off too. I wanted her completely naked.

I got naked first, and if I do say so I am in pretty good shape. I play tennis two or three times a week and that keeps me trim. I don't know what her secret is, but she is gorgeous. Slender body, small but nicely shaped breasts, beautiful long legs, and a closely trimmed bush. She could be an underwear model.

I helped her onto the bed, and she said, "Like this?" lying face-down.

"Yes, perfect."

My cock was so hard I could use it for a hammer and drive some nails.

Her gaze was fixed on it with a look of both lust and apprehension. She reached for it and grasped it and investigated it from the head to my balls.

"I don't know if all of that will fit in me that way. Will you stop if I ask you to? About here?"

She encircled my cock with her thumb and forefinger at approximately the half-way point.

"Sure," I lied as I visualized how I would pin her down if I had to. If I get just the head in I am getting it all the way in.

I explored the butt-crack I had seen through her jeans at the store. I found her tiny asshole and tried to insert my middle finger. She squirmed and objected so I stopped.

She really is a virgin at this!

I went to the bathroom and came back with a tube of lube. I put a large dollop on my fingertip and found her asshole again. This time it slid in.

She murmured but did not say stop. I continued pushing until it was in up to the last knuckle. I finger-fucked her for a minute or two, and she seemed to like it.

I pulled my finger out and climbed up on the bed, hovering over her. I took both of her hands and brought them back to her butt, indicating that she should spread it.

"This is very embarrassing. I wish we could turn the lights off" she said as she pulled her silky-smooth butt apart, exposing her pink asshole.

She still wants to play the modest innocent one. Or maybe she really is modest about exposing her asshole to a strange man. Women seem to feel that their asshole is more private than their vagina. Maybe that's what makes anal sex so intimate.

I like it with the lights on. Her asshole has a fine fringe of hair forming a halo around it. Her pussy lips are moist and open, and she is obviously aroused by what is about to happen.

I put the tip of my hard-on against her tight hole and began to push. Her anus resisted for a while and then surrendered, and the head of my cock forced it to open and accept me.

Her response was to flinch and to grunt "Uhh!"

"Relax. Let it slide in."

She softly whispered "OK."

I worked it into her a fraction of an inch at a time.

She acted like it was becoming uncomfortable and said, "Is it in up to where I indicated yet?"

I lied again and said, "Not yet. Hold still."

She did, and I pushed the last few inches into her. She exhaled with another soft grunt.

In an accusing tone she said, "That's all of it, you liar."

"Yes. I knew you could take it all."

"It feels so big inside me. And so far up in me. Just do whatever you want."

She was so aroused that heat was rising off her body, and the musky fragrance of her cunt filled the room.

I began to fuck her with slow, gentle strokes. Her asshole was tighter than anything I had ever experienced.

Our breathing was almost synchronized, and the bed creaked and squeaked as I rhythmically humped her. Her head was turned to the side with her eyes closed.

I asked if she was OK and she whispered, "Yes. Don't stop."

With each thrust I pulled all the way out to the head, and then pushed back in all the way. She was still spreading her butt-cheeks, so she got the entire length of my hard-on up into her belly. She didn't say anything, but it was obvious that she loved it.

My seminal fluid added to the lube and my cock slid in and out easily. I had a clear view of her asshole stretching and accepting my stiff cock as it went all the way in. The tight ring of her anus gripped my cock tightly.

I was hoping I could screw her for an hour, but I couldn't. I tried to force myself to hold back, even biting my lip so the pain would distract me.

She sensed what I was doing and said, "Don't do that. Let yourself go."

Through clenched teeth I said, "Here it comes."

I stopped fully embedded and blew my load. I masturbate occasionally, but I hadn't had actual sex for weeks so the cum squirted and spurted into her relentlessly.

Her eyes snapped open, surprised and curious at the sensation.

I huffed and puffed as I emptied my balls in her. My ejaculation was so intense it felt like one of my nuts might shoot out with the cum.

I supported myself on my elbows and knees, so I didn't crush her. I kissed her neck and ear.

I started to get off, but she stopped me, saying, "Stay in me. Rest for a while. Don't leave."

We stayed together for several minutes, and then she began to squeeze my cock with her anus.

"Do you think you can do it again?"

Come on, lady, I'm not twenty years old.

But she is the most beautiful woman I have ever had sex with, and to my surprise and pleasure my hard-on never went away. I began to work it in and out slowly, and then a little faster.

My load of cum provided lubrication, and soon I was fucking her like a porn star.

This time with each thrust in the head of my cock hit a soft obstruction that must be a twist or turn in her GI Tract. So my cock is the perfect size for her; if I had one more inch she wouldn't have been able to take it. I'm going to tell her that.

I quickly reached the point of no return and blew another big load into her.

It didn't surprise her this time, and she made sounds of ecstasy as she experienced the sensation of my warm jism gushing into her.

I regained control and withdrew my still-hard cock. She whimpered with disappointment when the head popped out and her asshole closed shut again.

I flopped down next to her and put my arms around her. We were both hot and I was kind of sweaty, but she didn't seem to mind.

She said, "Like I told you, I have never done that before. Oh, I have had sex of course, but not, umm..., you know, umm..., in the ass." She had trouble saying the last three words out loud.

I smiled and kissed her.

"I have wanted to try it for some time, and when you said what you said in the store I saw my chance. I hope you didn't mind that I was inexperienced."

"Not at all. Men like to be first."

"You got it so far up in me. And then when you, umm..., finished, that went even farther up into me."

I just listened, wanting to hear more about how it felt to her.

"I am still so turned on, just remembering what it was like."

"You need to finish too. Let me do it for you."

It took her a moment to understand that I wanted her to turn over. She finally did, and I dived down to her crotch.

I said, "Your turn" and ran my tongue over her pussy-lips. She quivered with excitement and I went to work. I love to make a woman cum this way. I love it when they lose control.

It didn't take long. I know how to flick the clit as hard as I can with the tip of my tongue, and that usually does the trick. It did this time and she had a convulsive, leg-shaking orgasm.

We held each other side-by-side and slowly calmed down.

She became pensive and said, "My little a-hole will never be the same. It's not little anymore."

"I liked it so much. I guess I am an anal slut, and now I know it."

I answered, "No, you are not a slut. It is perfectly normal for you to like it that way. Most women do once they have experienced it. Some just resist trying it which is too bad."

"Thank you for saying that. And thank you for doing it to me so well. I hope you didn't encounter anything unpleasant."

"Nothing that a little soap and water won't fix. I am planning to take a shower."

We stayed together for what seemed an hour, and then she said, "I should go."

She got up and got dressed.

"I hope my jeans don't get a wet spot in the back. I think you are starting to ooze out of me. People will stare at me."

I remained in bed naked. My cock was still half-hard. She couldn't take her eyes off it. It was clear she wanted more of it.

I said, "We should do this again. Would you like to?"

She teased me by not answering right away, acting coy, but then said, "Sure. I would love to."

I said, "Should I look for you at the grocery store again?"

"No. Let's exchange contact information - phone, email address, etc."

Then she said, "But first, by the way, what is your name?"

I broke out laughing. I just fucked this woman in the most intimate way possible and we don't even know each other's names!

"I am Bruce. And you are?"

"Barbara. Nice to meet you."

We both laughed at that, and we exchanged contact info.

I said, "I will call you tomorrow."

"OK, we can talk. But I might need a few days before we get together again. Right now I don't think I can sit down."

God, I'm glad I went shopping today.