Smartucus99
On the Prowl
I was recently in San Diego, La Jolla to be specific. My best friend Joe was renting a beautiful beach house on Bonair Ave. I was about to have a boner with a rent boy/escort. Joe has a lot of money and encouraged me to get a rent boy that night. He generously offered to pay. I'd never done it before. I am a gay man over 50. I am in good shape. Most people think I'm in my early forties. Joe is straight, but bi-curious if that is
a thing.
So Joe went to lay out on the beautiful beach in front of our beach house. I went to my laptop/Mac Book Pro to find a hot, sexy man who hopefully was into older guys. After an exhaustive search, I texted two guys. Both got back to me right away. Andy sent me a very sexy naked photo. Caleb sent me a similar photo, but more of a teasing pose. They both cost about the same, $300.
I scheduled a meeting with Caleb for 5:00 Sunday night, which was tomorrow night. I can't put into words how excited I was. I was in the middle of a LONG dry spell. Like years. Because we had an amazing beach house Caleb gave me slight travel discount. He was coming here and I could not wait. His body looked amazing in his online photos. His reviews couldn't have sounded better if they had been written by him. Caleb was super hot and were were going to get it on in about 24 hours.
Sunday at 4:00, I started preparing the extra bedroom for our rendezvous. Lube, water, candles and anything else I could think of. Caleb texted me at 4:30 that he was gonna jump in the shower. I texted back a thumbs up and "...ooh, that sounds hot." I watched for him out the back window of our house. He pulled up in a new Toyota truck at 5:01 and texted me that he needed the security code to the door. I had already texted him it, but texted him *5869 and I could hear him coming up the steps in only seconds.
My heart raced and yet I was still fairly calm. I wore shorts and a Steph Curry NBA jersey. Caleb knocked, I opened the door and immediately liked what I saw. Caleb was even sexier in person.
"Damn, you're fine!" I said
"Thanks," Caleb responded.
"I am pretty excited for my blissful escape," I quipped.
Blissful escape was Caleb's headline on his profile on the website I found him on. Caleb smiled and I remember thinking how lucky I was I had him for the next hour. A little info I learned about Caleb. He fits my fantasy of a. really smart/athletic dude. He is 26, works out. Has a degree in engineering from a large midwest university. He played football and baseball in HS and wrestled and did track and field. I joked about him in singlet and he offered to wear it next time. My heart about melted after that comment. Caleb was about 5'10" and 160 pounds. His hair was longer on top and short on the side, light brown. He had that perfect skin that guys who work out regularly do.
We walked into the living room and Caleb was in awe of the ocean view. I let him take in the view and he asked if he could take pictures.
"Yes, but there is a fee, you know copyright laws," I said trying to be funny.
"Ha-ha, funny guy," Caleb replied as he whipped out his.....camera and took a few photos of the Pacific Ocean 30 minutes before sunset.
He said he has a boyfriend and I remembered that I could have had four hands instead of two tonight. Meaning Caleb was willing to come over for a threesome with myself and his boyfriend Jake. Too much $ for me, but the fantasy of the three of us is pretty dame hot.
I mentioned how much respect I have for sex workers. I also asked if he was into older guys. He said yes, but what is he gonna say there, no? He seemed generally intrigued by the fact that I was over 50. Caleb said he has serviced guys over 50 and that we are easier to deal with because we know what we want.
Caleb and walked to the spare bedroom I had prepared earlier. He bought a small Nike backpack with sexy toys? I wondered what was in it. We got the bedroom and talked a little more. Caleb started to strip and I started to get hard. WOW! My own private strip show! His chest was muscular and hairless/smooth. Definitely a wrestler's body. He slowly removed his shorts and stood there in his black Nike briefs. He was at the end of the bed near the window and I was at the other end wondering what was under those briefs. Shaved? Natural? Cut/uncut? 6-7-8 inches. I'd soon find out. We talked price again. If he was going to fuck me it would be extra. I have never bottomed - but figured Caleb would be a perfect first. I check out Caleb's body. Broad shoulders, perfect chest with sexy nippled and an absolute 8 pack for abs. His deck was so sexy. Flaccid it was four inches, thick and cut. I like my bacon thick cut, lol. Small batch of light brown pubic hair and perfectly round balls. Just the way his cock hung straight down with that perfect mushroom head, had me hyperventilating.
"Can I take your picture?" I asked suddenly.
"Not Sure, are you gonna post it anywhere?" Caleb asked.
"No way, come on Caleb I let you take photos of the view, how about a photo of this beautiful view?"
Caleb laughed and agreed and I quickly ran across the hall to get my phone. When I walked in Caleb was taking of fhis underwear. I liked what I saw and clicked. He actually posed and smiled while I clicked away. He was enjoying this. I told him how hot he was and felt like a pornographer. With his clothes at his feet, Caleb asked me if we should start the massage. I dropped my Adidas shorts and pulled off my Curry jersey faster than Steph shot his threes. I set my phone on the expensive dresser and took a deep sigh. He checked me out and didn't frown or anything, so that was good.
Here we go! I laid flat of the bed, face down, ass up. Caleb climbed on top of me. OMG, I could feel his but and balls on my back as he began to squirt oil all over my back. He started on my shoulders, of course. His strong hands worked their way down my back and we continued talking about my life a little.
When I rolled over, I was totally hard, not a guarantee at my age. Caleb had gotten hard too, and his oh so hot cock was now pointing north but he was working his way south of the border to my rock hard 7" cock. He began stroking and I could tell I wasn't gonna cum for awhile, which was good. He was sitting on me around my knees and I was playing with his nipples and rubbing his rock hard abs. Damn, I was so in to this.
Clearly, Caleb was as well.
I bit my bottom lip and swallowed hard. We were both hard and I wanted to bottom. First, I desperately wanted to suck his nearly perfect penis. Caleb slid forward and shoved his massive piece of meat in my mouth. I licked the head and shaft as his dick entered my mouth.
END of part ONE
a thing.
So Joe went to lay out on the beautiful beach in front of our beach house. I went to my laptop/Mac Book Pro to find a hot, sexy man who hopefully was into older guys. After an exhaustive search, I texted two guys. Both got back to me right away. Andy sent me a very sexy naked photo. Caleb sent me a similar photo, but more of a teasing pose. They both cost about the same, $300.
I scheduled a meeting with Caleb for 5:00 Sunday night, which was tomorrow night. I can't put into words how excited I was. I was in the middle of a LONG dry spell. Like years. Because we had an amazing beach house Caleb gave me slight travel discount. He was coming here and I could not wait. His body looked amazing in his online photos. His reviews couldn't have sounded better if they had been written by him. Caleb was super hot and were were going to get it on in about 24 hours.
Sunday at 4:00, I started preparing the extra bedroom for our rendezvous. Lube, water, candles and anything else I could think of. Caleb texted me at 4:30 that he was gonna jump in the shower. I texted back a thumbs up and "...ooh, that sounds hot." I watched for him out the back window of our house. He pulled up in a new Toyota truck at 5:01 and texted me that he needed the security code to the door. I had already texted him it, but texted him *5869 and I could hear him coming up the steps in only seconds.
My heart raced and yet I was still fairly calm. I wore shorts and a Steph Curry NBA jersey. Caleb knocked, I opened the door and immediately liked what I saw. Caleb was even sexier in person.
"Damn, you're fine!" I said
"Thanks," Caleb responded.
"I am pretty excited for my blissful escape," I quipped.
Blissful escape was Caleb's headline on his profile on the website I found him on. Caleb smiled and I remember thinking how lucky I was I had him for the next hour. A little info I learned about Caleb. He fits my fantasy of a. really smart/athletic dude. He is 26, works out. Has a degree in engineering from a large midwest university. He played football and baseball in HS and wrestled and did track and field. I joked about him in singlet and he offered to wear it next time. My heart about melted after that comment. Caleb was about 5'10" and 160 pounds. His hair was longer on top and short on the side, light brown. He had that perfect skin that guys who work out regularly do.
We walked into the living room and Caleb was in awe of the ocean view. I let him take in the view and he asked if he could take pictures.
"Yes, but there is a fee, you know copyright laws," I said trying to be funny.
"Ha-ha, funny guy," Caleb replied as he whipped out his.....camera and took a few photos of the Pacific Ocean 30 minutes before sunset.
He said he has a boyfriend and I remembered that I could have had four hands instead of two tonight. Meaning Caleb was willing to come over for a threesome with myself and his boyfriend Jake. Too much $ for me, but the fantasy of the three of us is pretty dame hot.
I mentioned how much respect I have for sex workers. I also asked if he was into older guys. He said yes, but what is he gonna say there, no? He seemed generally intrigued by the fact that I was over 50. Caleb said he has serviced guys over 50 and that we are easier to deal with because we know what we want.
Caleb and walked to the spare bedroom I had prepared earlier. He bought a small Nike backpack with sexy toys? I wondered what was in it. We got the bedroom and talked a little more. Caleb started to strip and I started to get hard. WOW! My own private strip show! His chest was muscular and hairless/smooth. Definitely a wrestler's body. He slowly removed his shorts and stood there in his black Nike briefs. He was at the end of the bed near the window and I was at the other end wondering what was under those briefs. Shaved? Natural? Cut/uncut? 6-7-8 inches. I'd soon find out. We talked price again. If he was going to fuck me it would be extra. I have never bottomed - but figured Caleb would be a perfect first. I check out Caleb's body. Broad shoulders, perfect chest with sexy nippled and an absolute 8 pack for abs. His deck was so sexy. Flaccid it was four inches, thick and cut. I like my bacon thick cut, lol. Small batch of light brown pubic hair and perfectly round balls. Just the way his cock hung straight down with that perfect mushroom head, had me hyperventilating.
"Can I take your picture?" I asked suddenly.
"Not Sure, are you gonna post it anywhere?" Caleb asked.
"No way, come on Caleb I let you take photos of the view, how about a photo of this beautiful view?"
Caleb laughed and agreed and I quickly ran across the hall to get my phone. When I walked in Caleb was taking of fhis underwear. I liked what I saw and clicked. He actually posed and smiled while I clicked away. He was enjoying this. I told him how hot he was and felt like a pornographer. With his clothes at his feet, Caleb asked me if we should start the massage. I dropped my Adidas shorts and pulled off my Curry jersey faster than Steph shot his threes. I set my phone on the expensive dresser and took a deep sigh. He checked me out and didn't frown or anything, so that was good.
Here we go! I laid flat of the bed, face down, ass up. Caleb climbed on top of me. OMG, I could feel his but and balls on my back as he began to squirt oil all over my back. He started on my shoulders, of course. His strong hands worked their way down my back and we continued talking about my life a little.
When I rolled over, I was totally hard, not a guarantee at my age. Caleb had gotten hard too, and his oh so hot cock was now pointing north but he was working his way south of the border to my rock hard 7" cock. He began stroking and I could tell I wasn't gonna cum for awhile, which was good. He was sitting on me around my knees and I was playing with his nipples and rubbing his rock hard abs. Damn, I was so in to this.
Clearly, Caleb was as well.
I bit my bottom lip and swallowed hard. We were both hard and I wanted to bottom. First, I desperately wanted to suck his nearly perfect penis. Caleb slid forward and shoved his massive piece of meat in my mouth. I licked the head and shaft as his dick entered my mouth.
END of part ONE
