A Vacation REality
Introduction:
My family vacation when I was 13 turned out to be an erotic nightmare that introudced me to gay sex.
I was busy getting packed for our annual summer trip. We were going to Chicago this year, because my dad had to do some work before we could do much actual vacationing. I was upset and did not want to go on this trip because my cousin was not allowed to come with me. We usually spend every moment we can together, and in past years we have been able to vacation together as well, but not this year thanks to dad’s business. Just the night before, my cousin and I took our masturbation session to a new level. We had been jacking each other off for quite some time now, and this night was not going to be any different.
Steve was spending the night as usual, and we were camped out in the basement while my parents were up on the second floor, affording us plenty of privacy! We stripped down naked and lay down on our makeshift bed. Almost as soon as we lay down, Steve’s hand was rubbing my thigh. For some reason, I never got the festivities going! Steve’s hand slowly started rubbing up and down my thigh, inching closer to my dick, which was throbbing and rock hard! Before Steve actually touched my dick, he grabbed my hand and moved it onto his balls. His balls were warm to the touch, but they were asking for a good rub down. His hand finally found my dick and started gently rubbing up and down. Steve took his hand away for a minute, and when it was replaced, it was slick with spit. This created a much more intense rubbing situation, and he was swirling my cock head with his palm. It was unbelievable; I have never felt anything near this. I had been rubbing Steve’s dick with my hand, and I was rubbing pretty fast with the amount of pleasure I have been feeling. I didn’t think this first session would last too long, but they never did. We tried to start slow, but it didn’t matter, we always ended up furiously pumping away at each other. Right as I was about to hit my orgasm, I put my head back and closed my eyes. Steve suddenly stopped rubbing, and I almost screamed out I was so frustrated, but he was shuffling around. Next thing I knew, he was on his hands and knees above me, and my dick was in his mouth. This was the first time this ever happened, and actually the first time I ever even thought about it, but it felt great. Without even knowing what I was doing, I took his dick into my mouth as well. I just mimicked what Steve was doing to me, and it felt great, and I am assuming it felt good for him based on his moaning. It didn’t take long and I was blowing my load directly into his mouth. My orgasm subsided, I started to feel kind of weird about what just happened. Steve swallowed my cum, but I wasn’t sure if I wanted to do the same! Before I even had the chance to say anything, Steve blew his load into my mouth. It took me by surprise, and I started gagging. I swallowed part of his cum on instinct, but the rest sort of dribbled out of my mouth. Steve got up and brought his face close to mine and licked his own cum off of my mouth and chin. I was so shocked, I didn’t know what to do! We ended up going to sleep without saying much to each other, and I just kept dreaming about sucking his cock.
It had been a whole day since our cock sucking experiment, and I had determined that I would like to try again, and maybe go a little further. My curiosity was peaked, but I assumed we would get more time to try things out on vacation. We were eating dinner and I asked if we had to take Steve home to pack his bags, and my mom almost spit out her food!
“I’m sorry honey, I forgot to tell you that Steve isn’t coming. I assumed you guys had talked about it, but he has to go to football camp this week, and we are staying on dad’s company money, so we can’t take anyone extra around” my mom informed me.
How stupid am I? I just assumed that he would be coming, and I never put two and two together that he was off to football camp and we were off to vacation. I came back to reality as I finished packing, and we were getting ready for the five hour drive to Chicago. I took one last opportunity to jack off before the car ride because five hours without masturbation was almost unbearable. I tried to sleep as long as possible on the trip. We arrived at the hotel and got settled, and I was still in a bad mood. I was extremely horny, and extremely curious about my experience with my cousin. We at our lunch, and my mom had all these shops she wanted to go see. I was still irritated, and I told her that I didn’t feel like shopping. My parents are pretty cool, so she told me I could stay at the hotel and swim for the day. I was cool with this and told her to take her time, I wouldn’t be lonely (at least not for her company!) and that I would be fine. She informed me that she was shopping and then meeting my dad after his business was over for the day at a fancy restaurant for dinner, so she wouldn’t see me until around 9 pm. She took off, and I stripped my clothes off and dug out my bathing suit. I found my suit and towel and headed down to the pool. To my disappointment, there was a hotel employee that let guests in. Although I had a room key, he informed me that I would not be allowed in unattended because I was too young. I knew I had a major sad look on my face because a gentleman was walking in with his young kids and wife turned and gave me a look of pity.
“He can come in with us” the man said. The hotel employee said that was fine, and I was allowed in.
I really didn’t know what to do. I was now in alone, and the man and his family was setting up at a nearby table. He had two young boys, or at least they were younger than me. They looked to be about 9 or 10, but it was hard to tell. I was standing there starting to feel stupid when the man turned around and approached me. I was a little nervous at being here alone and being dragged into discussion with a stranger, but I tried to think quickly.
“Thanks” I told the man. “I would have been bored if you wouldn’t have brought me in with you. I am kind of hanging out on my own today.”
“No problem” the man replied. “My name is Daniel, and you can call me Dan. That is my wife Lindsay over there, and those are my boys Jack and Eric. They are 9 and 10 respectively. You can’t be much older yourself?”
“I am 13” I stated indignantly. How dare this guy compare me to a 9 and 10 year old? “And my name is Mike” I added quickly, not wanting to sound rude or ungrateful.
“Why are you by yourself” Dan asked.
“My dad is here on business, and my mom wanted to go shopping. I am bummed out because my cousin Steve couldn’t come with me, so I decided I would just go for a swim and keep to myself” I answered.
“Well, I won’t stand for it” Dan said. I wasn’t sure what he was talking about. “You can hang with us. We are here all week.”
Things seemed to be looking up. I went over and met Dan’s family, and I instantly loved them. They were a ton of fun, even the boys. They hung on my every word and every action, which is what most younger boys do, but I didn’t really mind since I was actually bored and lonely. We splashed around in the pool and Dan jumped in and we all started to wrestle. I was having fun, but I was starting to get hard. I was sure that someone would notice in such close quarters, but nobody said anything. I was afraid that Jack or Eric would feel my boner and say something out loud, not knowing any better, but they never did. We continued wrestling, and I stayed hard the whole time. Dan kept coming after me, and the boys and I ganged up on him. We were starting to get tired, and Dan suggested that we go relax in the hot tub. We had the pool area pretty much to ourselves, outside of a couple young adults hanging around. We started to get out of the pool when I realized my problem would stick out like a sore thumb, so I stayed in the pool. The boys were already in the hot tub, and Lindsay was joining them, as well as the young adults. Dan turned around and noticed me still in the pool, and came over.
“What’s wrong” he asked.
“Nothing” I answered, pretty embarrassed.
”Something is wrong. You can tell me” Dan said.
“Promise that you won’t laugh” I pleaded.
I finally told him after he agreed not to laugh, and he did chuckle. I immediately started to get angry until he told me it was no big deal, it happens to him all the time. He told me to stick the tip of my dick slightly into my waistband, and it wouldn’t be noticeable while I was walking. He then reminded me that the hot tub would be bubbling, so no one would notice. I did as he said and I made it to the hot tub without embarrassment. When we arrived, Dan got into the hot tub and sat down next to Eric, and there was only one more seat between Dan and the stairs. I sat down and let the bubbles wash over me, and I was relaxing a little after my potential situation. Dan and I were relaxing, the boys were splashing around at each other, and Lindsay was talking with the young couple who we found out were there to get married.
I was contemplating leaving to go to the room and relieve my sexual tension, when I felt a hand touch my leg slightly. I thought it was an accident, maybe a floating hand or something, but I started to think of my experience with Steve and our little cocksucking episode. I came out of my fantasy quickly when I realized that I wasn’t imagining the touch, and I looked to the side and saw Dan looking at me. This older man was touching my leg, rubbing his hand up and down. I was surprised, but Dan looked confident that I wouldn’t say anything, and I knew that I wouldn’t because it felt too good. He started moving his hand up to my waistband. He expertly undid my ties and stretched my waistband out. He took his hand away for a minute, and then reached over and took my hand and stuffed it into his pants. My jaw almost dropped into the water. His cock was huge! I have never felt a cock other than Steve’s, and his was about the same size as mine. My first thought was that Dan’s dick must have been 12 inches, but I quickly came to my senses and realized that it was about twice as big as mine (six inches) but much thicker! I loved the feel of this huge dick in my hand. I started to explore his groin, and I moved my hand down a little further. His balls were huge! They felt like softballs to me! Dan’s hand found its way back into my pants, and he was playing with my balls as well. He slowly started jacking me off, and he had moves that I never knew existed. He was slowly jacking up and down my shaft, and every few strokes, he would stop just below the ridge separating my shaft from the head and rub his fingers around in a circle. I have never felt anything like that before! I knew that I couldn’t last too long. It had been like seven hours since my last jack off session, which was a near impossible feat for a horny 13 year old boy. I was mimicking his movements onto his own dick, and I could feel the buildup of his orgasm. His pace and buildup was matching my own, but he hit just before me. I could tell because his cock got super stiff and slowly started to soften as I kept rubbing. My orgasm hit next and I gasped. He gave me a quick look and I coughed to cover it up before anyone noticed. I just let the pleasure run through my body until my dick got soft again, and I just leaned back. I decided to tie my shorts back up, and just in time because the bubbles stopped shortly after. I glanced over and Dan had already done up his shorts. Has he done this before? How odd. We decided that we would get out of the hot tub before we shriveled up into prunes.
Lindsay informed us that she was going to get something to eat with the boys and the young couple and asked me if I would join them. I told them that I couldn’t because I wanted to make sure I was around in case my parents came back. They were easy going, but I have a feeling they would draw the line at their 13 year old son going to dinner with complete strangers.
“Actually honey, I am going to go lay down. I am pretty tired from all the swimming and the hot tub, and my stomach is upset” Dan told Lindsay.
“Okay she answered, we will be back in a few hours” Lindsay said. “Mike, what room are you in? I want Dan to make sure you get back safely, and I want to come meet your parents tomorrow. Maybe we can do something together this week.”
“I am in 615, and that really isn’t necessary. I will be fine, but you can definitely come and meet my parents tomorrow. This will give me something to look forward to” I answered.
“615” Lindsay said. “We are in 616! How funny?”
Lindsay and the boys took off to get changed because they had to meet the couple in the lobby to go to dinner. We stayed behind and gathered up all the towels and toys. We were about to head toward the rooms when I had to run to the bathroom. I went and took a nice long piss. I was heading back out to help Dan with the stuff, when I suddenly had to crap. I was in the stall for a few minutes when I heard the bathroom door open and Dan asked if I was okay. I told him I would be out in a minute. When I was finished, I went back by the pool and we gathered everything up and started walking to the elevators. We met Lindsay and the boys coming out of the elevator car and told them to have a good time. We got to the sixth floor and passed my room and stood outside of 616 while Dan fished for the key. I followed him into his room since most of the stuff I was carrying belonged to his family. I asked him where to set everything and he pointed to the corner. I sat everything down and turned around and Dan was completely naked!
I immediately started staring at his cock which looked even bigger than it felt to me! I couldn’t stop staring at his body. I was fascinated by his huge cock, supple balls, and his body hair, all of which I lacked on my immature 13 year old body.
“I know you enjoyed what we did in the hot tub” Dan said. “Now we are going to have even more fun.”
I was a little nervous. It was one thing to do this with my cousin Steve, who was the same age as me, but this was different. Dan was a nice guy, but he was in his thirties and a lot bigger than me. I was nervous, and the situation just seems wrong.
“I did enjoy what we did Dan, but this seems weird” I told him.
“Don’t worry about it Mike, it is no big deal. It will feel good, and you owe me for helping you with your embarrassing situation back at the pool. Besides, don’t think I didn’t notice how you were staring at Jack and Eric, and they are younger than you” Dan told me.
I didn’t know what to say! I didn’t know anyone noticed my staring and my occasional “accidental” touch of their butt. I eventually agreed.
“Now take your shorts off” Dan almost demanded.
I slowly complied, and when I stood upright, I noticed Dan’s dick was once again rock hard. It still looked so huge and I was really nervous. Dan told me to come over to him and sit on the bed in front of him. His tone was almost angry, and I was getting scared. He stood in front of me, and his cock was standing right in my face.
“Lick it” Dan said.
I wasn’t sure, but I did as I was told. I slowly stuck my tongue out and touched it to the tip of his dick. I was greeted with a salty, sweaty taste. I didn’t really enjoy it, but I didn’t dislike it either. Dan was starting to thrust his dick against my mouth, and he caught me by surprise. His six inch dick parted my lips and the head slipped in. When his cock slipped into my mouth, he lost control. He started shoving more and more of his man meat into my mouth, and I didn’t have time to protest. I was caught completely off guard. My teeth rubbed against the head of Dan’s cock, and he yelped in pain. He pulled his dick out and slapped me in the face.
“Don’t let you teeth touch my cock again you filthy boy slut” Dan yelled. I was completely scared now, and I didn’t want to piss him off.
“I am sorry, it won’t happen again” I half sobbed.
He told me that it better not, and he grabbed the back of my head and brought his dick back to my mouth. He told me to open up and I complied. He shoved his dick back into my mouth putting all six inches into my mouth this time. I was once again caught off guard, but I was focusing all my senses on keeping my teeth away from his dick. I finally managed to get my lips to cover the teeth up, and this drove Dan wild. He kept thrusting into my throat, and I was so scared I couldn’t even gag. I was afraid that he might kill me if I did. He continued throat fucking me while he gripped the hair on the back of my head. I really wasn’t doing anything, and not too long later, Dan picked up the thrusting. His dick was once again getting even harder under the sensations provided by my body. Dan took one final thrust deep into my throat to the point where I wasn’t able to breathe. He shot a spurt on cum down my throat and started to pull his dick back out of my throat. His second spurt landed on the back of my tongue and he pulled his dick the rest of the way out of my mouth. His next four spurts of cum landed on my mouth and chin, and I quickly swallowed what was in my mouth. I am surprised that I didn’t choke to death, but somehow I managed. He pushed me back on the bed, and leaned over to lick his own cum off of my face.
“Let’s get you cleaned up” Dan said, back to his friendly tone. This kind of caught me off guard, but I didn’t want to upset him again, so I quickly agreed. We stepped into the bathroom still naked and got the shower going. We both got in, and Dan grabbed the soap. He started lathering up and handed me the bar. As I was getting some soap, Dan started cleaning me up, rubbing all over my body. I followed his lead and started rubbing his body as well, avoiding his dick. I did not want to get him hard and horny again because I was afraid he would get mean. Finally, he finished cleaning everything, including my three inch cock which was now rock hard. I started to panic, but he didn’t seem to notice, and he finished cleaning his own cock. We stepped out of the shower and dried off, then headed back into the bed area of his room. I was still naked, and I decided to ask Dan if I could take his towel to get back to my room so I didn’t have to put my wet bathing suit back on.
“Sure, that’s fine. But maybe we should take care of your little problem” Dan chuckled. I then noticed that my dick was still rock hard.
“No, that’s okay, I should really get back to my room. My parents should be back soon” I lied, knowing it was only about 6:30 pm.
“Don’t worry. You said they wouldn’t be back until 9:00 pm” Dan said. Curse his memory! “This time it will be all about you! I will make you feel good, and you will be free to go!”
I hesitantly agreed, scared of him getting mad again. He backed me into the bed and lightly pushed me down. I sat on the edge of the bed, and he gently pushed me back into a laying position. He half lifted me, and scooted me further back on the bed as if I was going to sleep. He slowly started rubbing my thighs, and finally pushed them apart. My cock was standing at full attention, begging for pleasure. He moved his head down, and started licking my thigh right above my knee. His tongue slowly worked its way up my thigh and jumped to my ball bag. This feeling was driving me wild, and the cool sensation left behind from his tongue was intensifying the pleasure. He slowly licked up my shaft, around the ridge of the head of my cock, up to my piss slit, and finally engulfed my cock into his warm, waiting mouth. He expertly bobbed his head up and down, and used his tongue like he was trying to trace letters onto my dick. Every once in a while, he would stop and lick at my balls again. Once, toward the end of my pleasure time, he stopped sucking my cock to lick my balls. His tongue found its way down to the bottom of my ball sack and into the crack of my ass. This was a new experience, and it felt great. He licked up and down the crack of my ass, or at least what was available to him. He pushed my legs up into the air, and pushed my knees down by my head. My ass was pointing straight up into the air, and he had complete access to my rosebud. He plunged his tongue into my shit chute and started tongue fucking my asshole. He was drooling all over my ass, and his tongue slid in and out very easy. This sensation pushed me over the edge, and I had a massive orgasm. My cum came out so strong that it shot into my own mouth, which was hanging wide open from the surprise feeling. I quickly swallowed my own cum, as Dan stopped fucking my ass with his tongue. He looked me in the eye, and stood up. I quickly noticed that he had yet another raging hard on, and I was terrified at the sudden demented look in his eyes
Dan kept my legs pinned down with my knees right next to my head, and my 13 year old virgin ass was still pointing straight up into the air. I did not like where this was going, and I gave Dan a pleading looking staring him straight in the eyes.
“Please don’t do this” I begged.
“Don’t worry, I won’t hurt you” he said, brushing off my request.
Dan spit into his free hand and rubbed his saliva onto his cock for lube. My ass was already kind of loose from his tongue fucking. After he put enough spit onto his cock, he got up on top of me and placed his knees on either side of my ass. He positioned himself so his cock was at the opening of my ass. His cock tip was touching my virgin bud, and he slowly started to push in. He took it slower than I expected, pushing in inch by inch as if he were worried about hurting my asshole. He kept pushing in slowly, and it wasn’t too bad, but it was really uncomfortable. Finally, after what felt like an hour, I felt his pubic hair rubbing against my ass cheeks. Once he was completely in, he lost control. He started pumping in and out of my ass rather quick. It was still uncomfortable, but I was starting to get used to it a little bit. At this point, Dan took his cock almost all the way out of my ass and slammed it back in all the way to his balls. This hurt, but he was way beyond the point of know return. He started slamming into my asshole like a piston, coming completely out on more than one occasion. I was now sobbing and my ass was sore, but I was sort of aroused at the same time. It could only be the raw sexuality of the situation, because I didn’t think I was enjoying this. He kept pumping harder and harder, and eventually my ass got kind of numb. Shortly after, his cock swelled up, and he unloaded his cum into my bowels. The hot, sticky cum hitting my anal walls and the continued pounding as his dick went soft was pushing me close to the edge. His now limp dick popped out of my ass with a squelching sound, and he pushed my ass down and took my dick into his mouth. Dan gave me a quick blow job to finish me off, and when I went soft he stood up, picked me up into his arms and took me back to the bathroom. We once again cleaned up, and I was spent. Dan wrapped my towel around me, led me to the bedroom, rifled through my shorts and retrieved the key to my room. He took me back to my hotel room and led me inside. I got dressed in my PJs and lay down on the bed. Dan was about to leave, and he apologized for being so rough, and kissed me on the forehead. He went to the door and turned around.
“See you tomorrow Mike” Dan said. “I am looking forward to meeting your parents, and maybe we can spend some more time together. It seems like Lindsay likes Jill and Zack so she will probably spend a lot of time with them. That leaves you and I with Jack and Eric”
That last part brought a strange smile to his face as he left the room. I heard his door open and shut, and suddenly I was looking forward to the rest of my week! I drifted off to sleep as my parents were coming in, and I had the most pleasant dreams!
