Birthday Boy

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Older man enjoys young escort for his birthday.
3.3k words
4.51
7.5k
6

Part 1 of the 2 part series

Updated 09/23/2023
Created 07/24/2023
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Birthday Boy

Written by ArseGratiaArtis

As will become obvious, everyone in this story is over 18.

It was my fiftieth birthday, and my girlfriend Carol arrived right on time, at 3:00 in the afternoon. We had planned to have hot sex for a couple of hours, and she would take me to dinner at our favorite sushi joint, then a movie, probably followed by more sex. That was not what happened. I'm not going to give the details of exactly what did happen, but after 10 minutes and us not even getting undressed, she stormed out the front door and slammed it behind her, furious. If I told you, you wouldn't think it was that big a deal, but let's just say Carol was the jealous type, virtually always without reason, and there was no reason this time or any of the other times she had blown up at me. She apologized a couple of days later, but it was too late. The relationship was over. I can take only so much craziness.

And so there I was, all dressed up, so to speak, and nowhere to cum. I considered my options, like calling an ex-girlfriend and seeing if she wanted to go out, or calling a male friend or two and hanging out with the guys. But the hurt was too fresh, and I didn't figure any woman would want to be the rebound choice. I

didn't want to talk to any of the men I knew; at that point it would sound like me being sorry for myself. I thought about going to dinner alone, then to a bar, but I don't like that scene and I've had very little luck picking up women in bars.

I went to my computer and brought up a porn site, which got me nice and hard as I watched a cute redhead bend over and take it from behind. But that wasn't what I needed. I needed to have actual human contact. Why did Carol have to be so volatile? I had been faithful to her since we started dating, but she knew I had a past. Most divorced men my age do, and she did too. Maybe she was looking for a reason to dump me.

I looked at personal ads on a local web site, but all I saw were fakes, probably looking for my credit card number. Then I found another site advertising "personal services." Perhaps a massage would help, perhaps something that turned into more than a massage.

An ad by a girl who called herself Clarissa caught my eye. She was half my age, 25, and looked very nice, even though the photos didn't show her face clearly. She said she would "relieve my stress" for $200 an hour.

I was torn. I had absolutely no experience with escorts, or whatever the polite term for a prostitute is, although I knew a little about the protocol from reading. I had been tempted occasionally, even approached in Paris and Vancouver, but never gone through with it. It just felt weird, and I also knew that many women in that profession had been abused and didn't like men very much. I had also read that many were drug addicts. And I had never needed to pay for sex. Once I was past my twenties, willing, even eager, women were fairly easy to find, just not on short notice. I also had some minor moral qualms, all the more because of my relatively high-profile job.

On the other hand, I was incredibly horny. You might think a man my age would be past his sexual prime, and I was. However, my prime had been pretty amazing, and I had kept myself in excellent shape by eating right, not smoking, not drinking much, and good exercise. I had a great job, so I had enough money to afford a

nice house with a heated pool, and I either swam or ran nearly every day.

I looked at Clarissa's ad again and found others by her, and I looked at other ads. I kept coming back to Clarissa and did a little research, but she covered her tracks pretty well, which made sense. It was illegal, and she probably had family and

friends who would be shocked. I looked at other ads again, then back at hers. I thought long and hard about it, and in truth I was both long and hard.

Finally, I nervously dialed the number. I heard a pleasant voice on the other end say, "Hello." Nothing sexy or overdone, just a simple greeting.

"Hi. Is this Clarissa?"

"Yes. Who's this?"

"My name is Jack. I saw your ad. Are you going to be free in about 45 minutes?"

"You know I only do sensual massages, right?"

"Yes, that's what your ad said, and I really need one."

"Good. I can see you in an hour. Where are you coming from?"

I told her where I was and she texted me her address. I knew enough not to say anything about sex, anything suggestive at all, on the phone.

I got out an old wallet and put $350 in cash and my driver's license into it, and nothing else. I found a couple of condoms in a drawer that were still good even though I didn't use them with Carol. One of the good things about being in a relationship is that you usually don't need them, and I didn't like them. Carol was on the Pill. However, I was sure Clarissa would require them, and I wanted to be safe. I had a key ring with a house and car key but nothing else, and brought that. I figured everything would be okay but I'm cautious by nature.

I found the place easily enough, an older but upscale apartment building in a nice part of town, and parked two blocks away. I swallowed, pushed her button, and heard her voice. "It's Jack," I answered, and she buzzed me in. I walked up to her apartment (I don't like elevators) and knocked. She opened the door almost immediately, and I saw an extremely attractive girl in a white blouse and short black skirt smiling at me. I entered and she closed and locked the door behind me. After saying hello, I got out my wallet, took out two crisp century notes, and put them on the coffee table without saying a word.

"Can I get you something to drink?" she asked politely.

"Nothing now, thanks. Perhaps later." I could feel her sizing

me up.

As a way to make conversation she asked, "What kind of work do

you do?"

"I'm an engineer," I replied without elaboration. The truth was more complicated. Yes, I had a stack of engineering degrees and did engineering, but it went beyond that. No need to explain, and she was just making small talk anyway.

"Cool," she replied. I don't think she really knew what that meant, or maybe she thought I drove trains.

After a moment she said, "You look down. Are you okay?"

"Yeah," I said, "I'm fine."

She could tell I wasn't, but took me by the hand and said, "This way," as she led me to the bedroom. There, she took off her blouse to reveal a sexy red silk bra. She took that off and treated me to the sight of some of the prettiest tits I had ever seen. They were a full C cup, but firm and not in the least saggy, with big nipples and small areolae, exactly what I like. And as best I could tell, they were real. Her body looked exactly like the pictures on her Web page. I took a long look and smiled as I started to unbutton my shirt.

I saw her look at me as I removed my shirt and put it on a chair. I had a guess many of her clients weren't in very good shape, that she had had her share of fat old men. Then her eyes went down to the bulge in my jeans; I was already hard. She reached over and stroked it a little, smiled, and said, "Nice," then started undoing my belt and unbuttoning the jeans. I stroked her breasts, cupping them, gently pinching her nipples between thumb and forefinger. She felt very nice, but part of me felt like I was just going through the motions.

Once she had my pants undone she looked up at me and again said, "What's wrong? Are you not into me?"

I explained, leaving out the messy details, that it was my fiftieth birthday, that my girlfriend had dumped me, and so on.

"Oh, a birthday lay. Well, you should have a birthday spanking, too," she laughed.

I laughed too, and that broke my somber mood. "Maybe I should. I don't think I've ever had one."

"Then let's get those jeans off and get over my knee, big boy," she said as she had me sit on the bed, took off my shoes, and helped me out of my pants. I was rock hard, my prick standing straight up. She took off the skirt and put it on a chair, then bent over with her ass to me to take off her red thong. I gave each of her cheeks a light smack.

"Hey, you're the birthday boy," she smiled as she got on the bed and stretched her legs out, her back against the headboard, propped up by a pillow. She patted her upper thigh and said, "Now you lay here and be a good boy."

I'm normally the one in charge, but she just took over and I let her. I lay on my stomach across her thighs with some difficulty because of my hard cock. She stroked my ass lightly, then hit me, not too hard. She counted "One." She gave me ten good swats and stopped, massaging my warm ass. She stroked down my crack over my nether hole and between my balls a little, then started swatting me again. "Ten. Eleven." At twenty she stopped and massaged me a little, as before, and fingered my tight hole again, a little deeper. When she got to 50, she had slipped her little finger most of the way in and I thought she was going to give me a prostate massage. Then one more good hard swat. "Fifty-one."

I got off her legs and onto all fours, smiling. My ass was warm but it didn't really hurt, and I was even harder than before and dripping pre-cum. I sat back next to her and said, "Wow. I would never have thought, despite what I've read, that spanking could be so erotic. And your touching my balls and hole felt pretty amazing too."

"Yeah, you look pretty turned on," she said as she reached over and stroked my cock, getting pre-cum all over her hand.

She went on. "What were you and your girl going to do today that got you so worked up?"

"We both really liked the three-hole treatment." I figured I could explain graphically, without euphemisms. "I'd fuck her pussy for a while and make her cum a few times, then pull out and fuck her ass, and cum there. Then clean off thoroughly and she would suck me off and swallow it all. Then I'd need to recover, so we'd go for a swim, go have dinner, and come back and I'd take a long time in her cunt, and finally fill her with cum."

She looked at me, wide eyed. "You'd do all of that? At your age? You're kidding me."

"No, I'm not. We didn't do that all the time, maybe every month or so. Usually it was just straight sex for an hour or two."

"And she dumped you. She's an idiot." She paused, looking thoughtful, but I couldn't read what was on her mind. "What do you want to start with?"

"Before we start, do you have anything after this, in case we take longer than my hour? I can give you a little extra. And if you don't do anal, we can take that off the table."

"No, I'm free until ten," she said. It was 4:45.

"Then suck me off." I moved to the edge of the bed and spread my legs. My prick stood straight up, the tip glistening with pre-cum. She got out a condom and lube and knelt on the floor between my thighs. Instead of putting the condom on my cock she put it on the middle finger of her left hand, and applied lube to it.

"Ever had a prostate massage? I think you'll like it. You seemed to like a little attention there."

"No, but I know what it is, and you can try. I'll tell you if you need to stop."

She started sucking the tip of my prick, then deeper and deeper. I felt the cold of the lube on my asshole, then probing in, then out, then in a little deeper. I tried to relax, concentrating on how good the tip of my prick felt. As my prick went deeper into her mouth, her finger went deeper into my ass. After a couple of minutes I felt myself getting close, and stopped her.

She looked up, my prick falling out of her mouth, and said, "Something wrong?"

"No," I replied, "Just getting close to cumming and I don't want this to be over too soon. It feels incredible."

"Where do you want to cum?"

"In your mouth, with you sucking hard. No facial." She nodded and took me back in her mouth. I've always thought facials were idiotic. If I want to stroke my own cock, I can do that without female help. The pleasure is from cumming inside a woman, not just cumming.

We went on that way for at least 15 minutes, her finger working in my ass, stroking my prostate, her mouth and right hand on my prick, stopping when I got close. Finally I said, "I need to cum," and she quickened her pace, taking my seven inches nearly all the way down her throat, and I shot. I could feel my prostate contract, my prick explode. I moaned and thrust uncontrollably as she swallowed it all, not letting my cock leave her mouth. It had been one of the hottest orgasms of my life. I felt her finger slip out of my ass.

When I could focus, she was smiling. "How was that?"

"Simply incredible. You're amazing."

"And you're still pretty hard. You take anything to stay that way?" She stroked my softer cock a little.

"No, never needed to. Give me a minute to catch my breath."

She got a couple of tissues and took the used condom off her finger, then cleaned the lube off my ass.

We talked about how she decided to become an escort and I got good and hard again.

She got out another condom and slipped it over my prick. "How do you want it?"

"Get on the edge of the bed. I want to have a good look at your pussy." She obeyed, and brought her legs up. I fingered her clit and wet slit a little. She was beautiful down there, with big inner lips and good-sized clit. She also had a very pretty little anus, not too dark, and tight-looking. Too bad it was off limits. I knelt on the floor and eased the tip into her pussy, teasing her, playing with her nipples as she looked up at me. At that angle she felt very tight. Then I went in hard, deep, giving both of us a little shock, and she moaned as if she were almost cumming, but of course she wasn't ready. After about 10 minutes of this I was getting close, and pulled out. She looked up at me, a little surprised.

"Lie on your back. Good old missionary is best." She obeyed, and I knelt between her legs as she brought them up. She moaned as I played with her clit. I treated her as I would have any woman I had, wanting to pleasure her as well as get my own pleasure. I rubbed my prick in her slit, the tip stroking her clit, before positioning it at the entrance and easing in. After less than a minute I felt her contract around me and she yelled softly, "Oh God." I thrust harder and felt the intensity of her climax increase, feeling her contracting around my cock, sucking me in. The condom made me less sensitive, so I wasn't at risk of cumming too soon. I slowed down and let her recover, then started thrusting again.

"You're incredible, and really big. I almost never get to cum," she whispered. I knew she was telling me I was big because she wanted a big tip, and not just the one in her cunt, but it still was nice to hear. I'm sure she had had bigger.

"You did today, and I'm not nearly done." And I quickened my pace again. We lost count of her orgasms, until I finally couldn't hold back any longer. "I'm gonna cum," I moaned in her ear as I thrust harder and deeper. And I shot my somewhat smaller load into the condom, felt her contract on my throbbing prick, and collapsed on her.

I got up slowly and made sure to hold the condom onto my softer but still firm cock as I pulled out. She took the condom off with a tissue and threw it in a wastebasket with the other one. "That was amazing," was all she could manage. "Now I see why she was so jealous."

"Thanks," I smiled. "I bet you get a lot of minute men."

"Yeah, I do. Are you okay now?" she asked.

"Better than okay. You've given me an amazing birthday."

I went to the bathroom and cleaned up with a washcloth. She was already dressed when I came out. I got dressed while she watched but we didn't say anything. I got out my wallet and put the other $150 on the table. It was just after 6:15.

"Thanks for everything," I said.

She gave me a kiss on the cheek. "No, thank you. Come back any time. And when you come back, maybe you can fuck my ass."

"That's a very nice offer. I'll think about it." I smiled.

She let me out and I walked down to the first floor, thinking about what had just happened. Part of me wanted to see her every week, maybe more. Another part said that she was a professional, only in it for the money, and I felt somewhat weird for having been a party to that. I had had at least had some connection with the

other women I had had, something in common, some affection, even the one-night stands. While the sex had been incredible, I couldn't see having a connection with someone half my age who would be having a dozen other men before I could see her again. She was very sweet, not at all the hard-bitten kind of woman one often associates with practitioners of the world's oldest profession.

On the bright side, I wasn't horny, I had gotten what I physically needed, and she was young and hot. It was a real quandary. Maybe I'd see her until I found another girlfriend. Or not.

And as I drove home I wondered about her, had thoughts of being a hero and rescuing her, and so on. I knew how "rescues" work out from experience. You earn their undying hatred. However, she seemed to enjoy her work and didn't seem to be in trouble or on drugs. I also thought about my position and the repercussions should someone find out what I had just done. But it wasn't like I was picking up streetwalkers or harassing women at work or anything. I had just had a nice time with a new friend, I rationalized. And nobody would find out.

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5 Comments
Sara_Navy_WifeSara_Navy_Wife3 months ago

You and I had discussed "first person writing" and obviously you have mastered that art! I liked the conversation also, and the fact that you had considered her feelings as well as your own :) I would imagine that "escorts" get treated like dirt a lot. Maybe I am wrong about that :) As one comment said, the story was actually sweet :) There was no hint of "revenge sex" in the story. You treated her as well as you would a girlfriend :) I'll definitely bookmark this story! Well done!!!

LandParkWriterLandParkWriter9 months ago

This was a really nice story. It’s actually kind of sweet.

ArseGratiaArtisArseGratiaArtis9 months agoAuthor

Thanks for the comments. I appreciate the feedback. Mike, I had not considered a sequel, but I have an idea for one. I also have a few other stories in the works..

MikeOrMikeyMikeOrMikey9 months ago

5 stars. Please let them meet again.

OGHMNWOGHMNW9 months ago

Thank you for this Wonderful Hot Erotic story that is very true from a personal experience of my own. I chose mature escorts closer to my age for a GFE. Thanks again!

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