Heather s Special Weekend
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The Bellhop Weekend free porn video
The Bellhop Weekend
By BossDaddy
Once or twice a year I have business in NYC and I heard about a hotel in Tribeca called the Duane Street Hotel who caters to gay clientele. So, I booked a long weekend. I flew in on Friday for a Monday meeting and I was planning on flying home Tuesday. That left me some time to myself to have some fun in NYC. After I checked in at the desk the young bellhop took me and my bags up to the room. This guy was cute. He looked 18 or 19 years old and was slim built and had a cute ass on him. In the elevator on the way up to the room he asked me why I was in town. I told him my plans and said I was looking to have a good time and asked him for some suggestions. He thought for a second and then asked me what type of fun I was looking for. I said I was looking to meet some young people to get to know them and hang out.
We got to the room and he went out of his way to show me everything in the room. It was obvious to me that he was trying to feel me out and see if I was interested in him. Finally, I took some money out of my wallet to tip him and I gave him $100. He said that was too much and I said “how do you know? I haven’t told you what you need to do for it yet”. He got a big smile on his face and said, “I don’t have much time before the front desk will miss me”. I told him to “stop wasting time and strip”. He took his clothes off and I did the same. He was a skinny small frame pale young man with a cute smallish cock. He walked over to me and started rubbing my cock. I asked him what his name was, he replied Dillion.
We kissed and his smooth skin and soft mouth telegraphed his young age. I came to realized that he was up on his toes to reach my mouth. I really liked that. It stretched out his lean body even more. My hands groped his ass, spreading his cheeks and pulling him in to me. I tried to move my finger into his asshole just to see how tight it could be. Oh, this was going to be a fun tight ass to fuck. Our cocks now both erect where grinding against each other. My cock was twice his size of his and that turned me on.
I managed to pull away from his mouth and said “get sucking”. A big smile came to his face and down on his knees he went. He grabbed my cock and I slapped his face hard. “No hands!” he looked startled. “Just your mouth, and go deep on each stroke. Right down to my balls”. He struggled to get my whole cock into his mouth. It was clear to me that he doesn’t have much experience and I liked that. If I played this right I could train this boy to do things the way I like it.
He was eager to suck me and he kept trying to grab my cock and he was rewarded with another slap. I finally said “put your hands behind your back and keep them there or I’ll tie them behind you”. He got into a rhythm and took my cock deep. I could feel the pressure building in my balls. Looking down at him his saliva was all over my cock and his face. It dripped down on to his hairless chest. His cock was bouncing in rhythm to his sucking.
I had enough of this and I bent him over the bed to fuck him. I couldn’t resist eating his smooth pale white ass first. His asshole was pulsating in anticipation. I put the head of my cock to his tight asshole and pushed but it fought me. It wouldn’t open for my cock no matter how hard I pushed. I thought great, let’s get a finger in this tight hole and loosen him up. I heard him squeal a little as I worked my index finger in. Oh boy he was tight. I could imagine how good this would feel once I got my cock in. I felt him finally relax his asshole a bit and took that as my opportunity to stick my cock in.
I was trying to be kind to him and ease it in but it felt so good on my cock I thought hell lets’ just get this over with and I shoved it as deep as I could into his ass. I was balls deep in this young ass and it felt great. I was on autopilot just fucking with long hard deep strokes. He was moaning with each stroke. I made it a point to fuck him as deep as I could and give him a little extra push when I bottomed out, that shook his whole body. It didn’t take me long and I busted deep in his ass. I laid on top of him for a minute leaving my cock in his ass. I rolled off him and he immediately started sucking me. I let him clean my cock and squeeze every drop of cum out of me and then got up off the bed. He stood up too and starting getting dressed. I watched him and admired his young firm body.
I walked him to the door and couldn’t resist grabbing that ass one more time. As he leaves I asked him to come back later that night. He said yes and if I wanted he had a young friend that could join us. “Hell yes”, I said, “bring him and let’s have a party”.
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Later that night the two bellboys show up with a quiet knock on the door. I look through the peep hole and see Dillion and another young bellhop standing there. I open the door and Dillion says hello and walks in to the room. As the other young bellhop passed me I gave his ass a quick squeeze and said “what’s your name?” Looking startled he squeaks out, “Alan”. I closed the door and push him up against it. “What are you doing here?” I asked him. Looking confused he said “I’m friends with Dillion”. “That’s not what I mean”. I asked him again… “What are you here for?” He swallowed hard and said. “To get my ass fucked”. I said, “well good, come on in”.
Dillion was standing next to the bed where a few hours ago I fucked him so hard and Alan walked over and stood nervously next to him. I walked in and didn’t say a word. I just stood there. Ten seconds of total silence. I finally said “what are you waiting for… strip!” The two boys looked at each other and Dillion was first to start to strip naked and Alan was quick to follow.
I made the two of them stand there nude. I wanted to admire their young bodies. Alan was even skinnier then Dillion and he too had a cute small cock that was semi hard at just getting naked. I walked over to Dillion and commanded him to get down and suck. He did without hesitation. He remembered to only use his mouth this time and not his hands. I looked at Alan and put my cupped right hand out and said, put your balls in my hand. He took a step forward and got up on his toes and dropped his smooth almost hairless balls into my hand. I gave them a firm squeeze and saw his face react. These two boys were mine.
Dillion was doing a good job getting me hard and then I order them both to get on their hands and knees on the bed. “Ass Up Boys”. The two did as I asked Dillion looked over at Alan and I hear him say “Just relax and let it happen” in a reassuring manner. I walked up behind Dillion and grabbed him by his hips and yanked him back. I smacked his ass leaving a red hand print on his ass cheek and said “give me that hole”. No lube, I just forced my cock into his ass with one stroke. Alan looked over to see my cock in his friend’s ass and I said “you’re next”. I fuck Dillion for a few minutes but I couldn’t wait to try Alan’s ass. I pulled out of Dillion and walked over to Alan’s ass. “You ready boy?”. Some kind of a sound came out of his mouth but I couldn’t tell what it was. I spread his cheeks and spit on his asshole. Oh, it looked so good, so tight. Without hesitation I pushed into his ass. Loud moans came out of his mouth. I couldn’t tell if it was pain or pleasure. Dillion turn around to watch me fuck him. He put his face right next to Alan’s ass. I knew what he wanted. He wanted me to fuck Alan’s ass and then put it in his mouth to suck on it. I did just that. Fucking Alan’s ass and stopping just long enough to let Dillion suck me and lube my cock up for more ass fucking.
I took turns fucking the two of them all night.
The next morning, I was in the shower with Dillion giving him a good morning fucking and then Alan joined us for a quick fuck. Dillion said they both had to work but they would be done at 4 o’clock and would join me as soon as they could. For the next two days I was fucking both and sometimes each of the bellboys separately. This trip was turning into one of the best I’ve ever had to New York.
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I had to go to my meeting first thing on Monday morning and mid meeting I started daydreaming about the two bellhops waiting for me back at the hotel. I cut my meeting short and head back to the hotel. I see Dillion in the lobby and asked him to come up to the room. He said he couldn’t until his lunch break but he would give Alan a call and since he was off today he would meet me as soon as possible.
I go to my room and get ready for Alan. I decided that since this was my last night with the boys I wanted to really cut loose and have some kinky fun. I got naked and waited for Alan to arrive. Suddenly a quiet knock at the door. I was fully erect and answered the door. Alan looked shocked as he sees me standing there hard and nude. He quickly pushed into the room so no other guest could see. “Take your clothes off”, I ordered. “You made me wait and I don’t like to wait for boys”. Alan was quick to get naked then I took the tie that I was just wearing and tied his hands. “Face down on the bed”, I ordered, and Alan obeyed without hesitation.
I went into my suitcase and took out my leather belt and folded it in half. I walked back over to Alan and said, “You made me wait for that ass and now that ass needs to get punished. Alan’s face was both excited and a little fearful. I showed him the belt and his eyes got wide. I gave him two quick whips on his ass. Bright read welts appeared on his ass cheeks. My cock jumped in excitement. Two more even harder lashes came next. Alan buried his face in the bed and screamed. I jumped on him and mounted his ass. I whispered in his ear, “Do you want more lashes or are you going to give me your ass?”. Without hesitation he said, “Take my ass. My ass is yours”. I thought to myself, good answer boy but you’ll going to get my cock and the belt until I’m satisfied. I fucked and whipped him until Dillion showed up during his lunch break.
I opened the door for Dillion and he knew something was up. He turns the corner of the bedroom and saw Alan laying there on the bed with his hands still tied together. “Come on get naked”. Dillion strips and waits for me to tell him what I would like. I grab Dillion’s cock and say you ready to fuck Alan? He said nothing and just nodded yes. Dillion climbed up onto Alan and mounted his ass. Alan’s ass was well lubed from my two cum loads I just deposited in him. Alan pushed into his friend’s ass and soon he was fucking Alan’s ass with long deep strokes. I stood there and just watched them fuck. Dillion came in his friend’s ass and pulled his cock out slowly. I grabbed his arm and pulled him straight out of bed. I sucked Dillion’s cock clean. His small cock and both balls fit easily into my mouth.
Dillion said he had to get back to work but I told him to come back as soon as he could because I was going to have a party that night in both of their asses. Dillion got dress and left the room. As the door closed with a loud clack. I turned back to Alan and said “flip over boy we are just getting started”.
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I called a few friends that I knew in NYC and invited them over to the room to party with the bellboys. Me and three of my friends took those boys in every position we could think of. By the end of the night we were all satisfied and the bellboys were too.
I checked out the next morning and the manager asked me if I was satisfied with my stay. I had the biggest smile on my face when I said yes. The manager said he would get a bellboy to take my bags to the cab. He looked around and saw no bellboys. He got on the radio and called one to come to the desk. A young black bellboy came over and took my bags. I was wondering why I hadn’t seen him before and I asked him his name. He said it was Luke and it was his first day. I couldn’t help but notice he had a huge bulge. That look like a big cock he was working with. I told him I was coming back in two months and I was looking-forward to getting to know him. I asked Luck if he knew Alan and Dillion and he said yes that they were good friends. I gave Luke a $100 tip and told him to remember me.
By BossDaddy
Once or twice a year I have business in NYC and I heard about a hotel in Tribeca called the Duane Street Hotel who caters to gay clientele. So, I booked a long weekend. I flew in on Friday for a Monday meeting and I was planning on flying home Tuesday. That left me some time to myself to have some fun in NYC. After I checked in at the desk the young bellhop took me and my bags up to the room. This guy was cute. He looked 18 or 19 years old and was slim built and had a cute ass on him. In the elevator on the way up to the room he asked me why I was in town. I told him my plans and said I was looking to have a good time and asked him for some suggestions. He thought for a second and then asked me what type of fun I was looking for. I said I was looking to meet some young people to get to know them and hang out.
We got to the room and he went out of his way to show me everything in the room. It was obvious to me that he was trying to feel me out and see if I was interested in him. Finally, I took some money out of my wallet to tip him and I gave him $100. He said that was too much and I said “how do you know? I haven’t told you what you need to do for it yet”. He got a big smile on his face and said, “I don’t have much time before the front desk will miss me”. I told him to “stop wasting time and strip”. He took his clothes off and I did the same. He was a skinny small frame pale young man with a cute smallish cock. He walked over to me and started rubbing my cock. I asked him what his name was, he replied Dillion.
We kissed and his smooth skin and soft mouth telegraphed his young age. I came to realized that he was up on his toes to reach my mouth. I really liked that. It stretched out his lean body even more. My hands groped his ass, spreading his cheeks and pulling him in to me. I tried to move my finger into his asshole just to see how tight it could be. Oh, this was going to be a fun tight ass to fuck. Our cocks now both erect where grinding against each other. My cock was twice his size of his and that turned me on.
I managed to pull away from his mouth and said “get sucking”. A big smile came to his face and down on his knees he went. He grabbed my cock and I slapped his face hard. “No hands!” he looked startled. “Just your mouth, and go deep on each stroke. Right down to my balls”. He struggled to get my whole cock into his mouth. It was clear to me that he doesn’t have much experience and I liked that. If I played this right I could train this boy to do things the way I like it.
He was eager to suck me and he kept trying to grab my cock and he was rewarded with another slap. I finally said “put your hands behind your back and keep them there or I’ll tie them behind you”. He got into a rhythm and took my cock deep. I could feel the pressure building in my balls. Looking down at him his saliva was all over my cock and his face. It dripped down on to his hairless chest. His cock was bouncing in rhythm to his sucking.
I had enough of this and I bent him over the bed to fuck him. I couldn’t resist eating his smooth pale white ass first. His asshole was pulsating in anticipation. I put the head of my cock to his tight asshole and pushed but it fought me. It wouldn’t open for my cock no matter how hard I pushed. I thought great, let’s get a finger in this tight hole and loosen him up. I heard him squeal a little as I worked my index finger in. Oh boy he was tight. I could imagine how good this would feel once I got my cock in. I felt him finally relax his asshole a bit and took that as my opportunity to stick my cock in.
I was trying to be kind to him and ease it in but it felt so good on my cock I thought hell lets’ just get this over with and I shoved it as deep as I could into his ass. I was balls deep in this young ass and it felt great. I was on autopilot just fucking with long hard deep strokes. He was moaning with each stroke. I made it a point to fuck him as deep as I could and give him a little extra push when I bottomed out, that shook his whole body. It didn’t take me long and I busted deep in his ass. I laid on top of him for a minute leaving my cock in his ass. I rolled off him and he immediately started sucking me. I let him clean my cock and squeeze every drop of cum out of me and then got up off the bed. He stood up too and starting getting dressed. I watched him and admired his young firm body.
I walked him to the door and couldn’t resist grabbing that ass one more time. As he leaves I asked him to come back later that night. He said yes and if I wanted he had a young friend that could join us. “Hell yes”, I said, “bring him and let’s have a party”.
----------------------------------
Later that night the two bellboys show up with a quiet knock on the door. I look through the peep hole and see Dillion and another young bellhop standing there. I open the door and Dillion says hello and walks in to the room. As the other young bellhop passed me I gave his ass a quick squeeze and said “what’s your name?” Looking startled he squeaks out, “Alan”. I closed the door and push him up against it. “What are you doing here?” I asked him. Looking confused he said “I’m friends with Dillion”. “That’s not what I mean”. I asked him again… “What are you here for?” He swallowed hard and said. “To get my ass fucked”. I said, “well good, come on in”.
Dillion was standing next to the bed where a few hours ago I fucked him so hard and Alan walked over and stood nervously next to him. I walked in and didn’t say a word. I just stood there. Ten seconds of total silence. I finally said “what are you waiting for… strip!” The two boys looked at each other and Dillion was first to start to strip naked and Alan was quick to follow.
I made the two of them stand there nude. I wanted to admire their young bodies. Alan was even skinnier then Dillion and he too had a cute small cock that was semi hard at just getting naked. I walked over to Dillion and commanded him to get down and suck. He did without hesitation. He remembered to only use his mouth this time and not his hands. I looked at Alan and put my cupped right hand out and said, put your balls in my hand. He took a step forward and got up on his toes and dropped his smooth almost hairless balls into my hand. I gave them a firm squeeze and saw his face react. These two boys were mine.
Dillion was doing a good job getting me hard and then I order them both to get on their hands and knees on the bed. “Ass Up Boys”. The two did as I asked Dillion looked over at Alan and I hear him say “Just relax and let it happen” in a reassuring manner. I walked up behind Dillion and grabbed him by his hips and yanked him back. I smacked his ass leaving a red hand print on his ass cheek and said “give me that hole”. No lube, I just forced my cock into his ass with one stroke. Alan looked over to see my cock in his friend’s ass and I said “you’re next”. I fuck Dillion for a few minutes but I couldn’t wait to try Alan’s ass. I pulled out of Dillion and walked over to Alan’s ass. “You ready boy?”. Some kind of a sound came out of his mouth but I couldn’t tell what it was. I spread his cheeks and spit on his asshole. Oh, it looked so good, so tight. Without hesitation I pushed into his ass. Loud moans came out of his mouth. I couldn’t tell if it was pain or pleasure. Dillion turn around to watch me fuck him. He put his face right next to Alan’s ass. I knew what he wanted. He wanted me to fuck Alan’s ass and then put it in his mouth to suck on it. I did just that. Fucking Alan’s ass and stopping just long enough to let Dillion suck me and lube my cock up for more ass fucking.
I took turns fucking the two of them all night.
The next morning, I was in the shower with Dillion giving him a good morning fucking and then Alan joined us for a quick fuck. Dillion said they both had to work but they would be done at 4 o’clock and would join me as soon as they could. For the next two days I was fucking both and sometimes each of the bellboys separately. This trip was turning into one of the best I’ve ever had to New York.
-----------------------------------
I had to go to my meeting first thing on Monday morning and mid meeting I started daydreaming about the two bellhops waiting for me back at the hotel. I cut my meeting short and head back to the hotel. I see Dillion in the lobby and asked him to come up to the room. He said he couldn’t until his lunch break but he would give Alan a call and since he was off today he would meet me as soon as possible.
I go to my room and get ready for Alan. I decided that since this was my last night with the boys I wanted to really cut loose and have some kinky fun. I got naked and waited for Alan to arrive. Suddenly a quiet knock at the door. I was fully erect and answered the door. Alan looked shocked as he sees me standing there hard and nude. He quickly pushed into the room so no other guest could see. “Take your clothes off”, I ordered. “You made me wait and I don’t like to wait for boys”. Alan was quick to get naked then I took the tie that I was just wearing and tied his hands. “Face down on the bed”, I ordered, and Alan obeyed without hesitation.
I went into my suitcase and took out my leather belt and folded it in half. I walked back over to Alan and said, “You made me wait for that ass and now that ass needs to get punished. Alan’s face was both excited and a little fearful. I showed him the belt and his eyes got wide. I gave him two quick whips on his ass. Bright read welts appeared on his ass cheeks. My cock jumped in excitement. Two more even harder lashes came next. Alan buried his face in the bed and screamed. I jumped on him and mounted his ass. I whispered in his ear, “Do you want more lashes or are you going to give me your ass?”. Without hesitation he said, “Take my ass. My ass is yours”. I thought to myself, good answer boy but you’ll going to get my cock and the belt until I’m satisfied. I fucked and whipped him until Dillion showed up during his lunch break.
I opened the door for Dillion and he knew something was up. He turns the corner of the bedroom and saw Alan laying there on the bed with his hands still tied together. “Come on get naked”. Dillion strips and waits for me to tell him what I would like. I grab Dillion’s cock and say you ready to fuck Alan? He said nothing and just nodded yes. Dillion climbed up onto Alan and mounted his ass. Alan’s ass was well lubed from my two cum loads I just deposited in him. Alan pushed into his friend’s ass and soon he was fucking Alan’s ass with long deep strokes. I stood there and just watched them fuck. Dillion came in his friend’s ass and pulled his cock out slowly. I grabbed his arm and pulled him straight out of bed. I sucked Dillion’s cock clean. His small cock and both balls fit easily into my mouth.
Dillion said he had to get back to work but I told him to come back as soon as he could because I was going to have a party that night in both of their asses. Dillion got dress and left the room. As the door closed with a loud clack. I turned back to Alan and said “flip over boy we are just getting started”.
----------------------------------------------
I called a few friends that I knew in NYC and invited them over to the room to party with the bellboys. Me and three of my friends took those boys in every position we could think of. By the end of the night we were all satisfied and the bellboys were too.
I checked out the next morning and the manager asked me if I was satisfied with my stay. I had the biggest smile on my face when I said yes. The manager said he would get a bellboy to take my bags to the cab. He looked around and saw no bellboys. He got on the radio and called one to come to the desk. A young black bellboy came over and took my bags. I was wondering why I hadn’t seen him before and I asked him his name. He said it was Luke and it was his first day. I couldn’t help but notice he had a huge bulge. That look like a big cock he was working with. I told him I was coming back in two months and I was looking-forward to getting to know him. I asked Luck if he knew Alan and Dillion and he said yes that they were good friends. I gave Luke a $100 tip and told him to remember me.
Wynona
- 01.12.2021
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