New York Trip Ch. 01

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DISCLAIMER: The following story is FICTIONAL. It contains descriptions of sexual activities between a teenage boy and a man. If you are not over 18 years of age, or if you find this type of story offensive, or if viewing this material is illegal where you are, then please DO NOT READ IT If you like it, please feel free to let me know. My email address is available through the link below.


It was Christmas break and we were off from school. I was 18 and in my senior year of high school in the mid-60s in Southern California. I was a pretty good looking guy I think, 5’9″, slim, cute face. Of the groups at school I was considered one of the brains and hung out with other kids that were in the advanced classes. My parents were divorced and I used to live with my mom until a year ago, but she died and I now lived with my dad in an apartment near my high school. He had remarried, but his wife was living in a retirement area now while he continued to work.

When I lived with my mom, the house was always a mess (she was always a poor housekeeper and when she was ill she did very little). The apartment my dad and I lived in was nice, but very small. Neither place was a place where you would want to have friends over, so I didn’t have a lot of friends. I never went to the parties at school. I never had either the clothes or the transportation, so I stayed home. I was generally perfectly happy at home with a good book and some nice music.

So since I didn’t date, I was still a virgin and likely to remain that way for a good while. Was I queer? (gay wasn’t a term we had back then) I didn’t know. I knew I was excited by boys’ bodies. But then I like str8 porn I was sometimes able to get my hands on. On camping trips with the Boy Scouts, some of the guys used to do things in tents, but I never found out what because they never invited me to join them. I think I was too “clean” and too brainy for them – not that I ever put anyone down, it’s just the way it was. So except for masturbation (which I did a lot), I hadn’t had any kind of sex.

To get to the story, my older sister had joined the army about a year before and had been discharged about 6 months later. It seems she was a lesbian and I guess the army found out. So she had moved in with another girl she knew in Brooklyn and was living there and working in New York. I guess she missed me, because she invited me to come out at Christmas and spend my Christmas break with her. Her place was big enough and I had a bed to myself. She and her roommate worked, so I took care of my own meals during the day and we’d meet in the evenings and often go to a show. I prowled all around New York, mostly by myself. I tried to find some porn theaters that I could go to, but I guess they couldn’t advertise and I didn’t know where they were (and they probably wouldn’t let me in anyway), so I spent most of my time riding the subways and shopping for things.

One night though, we got home and a guy they knew from somewhere was going to spend the night. He was a sailor on leave and was about 20. He was slim and very good looking and I was extremely attracted to him. He moved so smoothly and had a really cute grin. He was about 2 or 3 inches taller than me. It was late when my sister and I got home, so I didn’t get to talk to him much. But he was going to spend the night on the couch in the living room and then move to a friend’s house for the rest of his leave. As usual, I read until 1 or 2 am and then went to sleep.

The next morning when I woke up about 9, my sister and her roommate had gone to work and I was left home alone with him. I was wearing pajamas back then and looked in on him before I had some cereal. He was sleeping in his briefs and I could see his chest and flat stomach moving up and down as he breathed. He had only a little hair on his chest and the hair running down from his navel into his briefs. I watched him for a few minutes, wishing he would wake up, but he kept sleeping. I returned to my room in my pajamas and lay in bed reading.

After about an hour, I heard the noise of the bathroom door closing and then the toilet flushing, so I knew he was up. Then there was some noise in the kitchen and a few minutes later he was at my door with a glass of milk.

“Hi Greg,” he said.

His hair was tousled and he was still just in his briefs. He still looked sleepy, but his body was sooooo nice.

He said, “I didn’t really get a chance to meet you last night and I’m not going to be here long today, but I’d like to get to know you a little. Do you mind if we chat for awhile?”

“No, sure,” I answered. “Pull up a chair. I’m not doing anything special.”

This was certainly true, but more importantly, it gave me a chance to look at him some more. Not only was his face very attractive, but his chest was well-defined, although not muscular, with a small patch of hair in the center and a thin trail of hair leading from his navel down into his briefs. His legs were yeşilköy escort long and attractive, again not muscular, but well built, more like a runner’s legs. And lastly, I couldn’t take my eyes off his briefs. I really couldn’t see anything, but for some reason, I was terribly turned on by looking at them. I tried not to be obvious about looking at his body, but it was hard for me to look anywhere else.

He picked up the chair by the dresser and brought it over, sitting close to the head of the bed with his knees almost touching it. I was still in my pajamas of course, but not under the covers. I put my book aside and sat up, leaning my back against the wall, my pillow on my lap and laying my arms on it.

He asked me about where I lived and so on and I gave him the basic details about my life. He was a great listener and he was very easy to talk to. All the time though, I couldn’t keep my eyes off him. Not only did his legs turn me on, but his chest and arms were so damn sexy. I longed to be able to touch him, but I just wasn’t sure how he’d react.

“So,” he went on, “what did your sister tell you about me?”

“Not much,” I answered. “She just said you were a guy she knew who was on leave from the Navy and needed a place to stay for the night.”

“She didn’t tell you how we know each other?”


“We met at a club for gays and lesbians,” he smiled. “We don’t have a lot in common but when I said I’d need a place for tonight, she offered to let me stay. She said her kid brother would be staying with her and that I might like to meet you. Besides, she knew I liked young guys like you.”

“You mean you’re gay?”

“Yes,” he said, “does that bother you?”

“Uh, I don’t think so, I … I don’t know. I’ve never met a gay guy before. You mean you have sex with guys? Blow jobs and things like that?”

“Well, yeah, I’ve done things like that. A friend introduced me to gay sex when I was 16 and I’ve never regretted it. But back to you for a few minutes if you don’t mind a personal question. You’re a very good looking guy, Greg, but I noticed you haven’t said a word about dating or sex at all. Don’t tell me you’re a virgin?”

“Uh – yes, I am,” I said sort of embarrassed. “It just hasn’t worked out for me to do much. I don’t have any transportation and all the intelligent, pretty girls already have boyfriends.”

“Do you go to school parties or other activities?”

“No, I just pretty much stay at home and do things with my father.”

“Then your father isn’t doing you any favors, Greg. By the time I was your age, I had had sex at least 10 times. You’re certainly old enough and you ought to be doing something about it. You’re at the age when you ought to be having sex regularly – and with your looks it would be really easy for you. Sex is a really great thing and unfortunately you’re missing out.”

“But what can I do about it? I just don’t have any opportunities,” I answered.

He smiled. “You have many, many opportunities. Become friendlier with the girls, flirt with them, go to parties, just socialize more. It isn’t easy and like most things it takes practice before you get good at it. But if you never try, you’ll never get any better. So do it.”

“Or if you like guys, you just have to hang out in the right places. You live in California? Near a beach? Go there, wear a sexy swimsuit and just walk up and down until you see a guy watching you. Then sit down near him for awhile and see if he pays any attention to you. Be a little obvious that you would like him to talk to you – or start a conversation yourself. Or you can go to swimming pools or the gym, especially in winter. Hang around, make yourself available. Just remember, you’re not looking for friends, you’re looking for guys that look hot to you and that you’d like to have sex with.”

“I’ve noticed you looking at me,” he continued, “in fact you can’t seem to take your eyes off me. Do you find me attractive?

“Uh …,” I was confused and had no idea what I should say.

After a minute or two, he said, “It’s all right, don’t be shy.”

“Uh …,” still not getting anything out.

“Do you want to touch me? I don’t mind.”

I sat up on the edge of the bed facing him and reached out with my hand and touched his leg lightly, letting my hand rest just above the knee.

“Do you like that?”

I nodded.

“Do you find it exciting?”

I sort of choked out, “uh, yes.”

“Don’t be so damn shy,” he said. And he took my hand and placed it on his crotch. I could feel his semi-hard cock inside and squeezed softly with my fingers. He watched me intently while I did this.

“Maybe you’ll find this even more exciting.” He stood up and pushed his briefs down and stepped out of them. His cock was halfway hard and was rising. It looked like it was 7″ or a little more. I couldn’t take my eyes off of it, it was so beautiful. It continued to rise as I watched. There was a dark bush zeytinburnu escort of hair all around it (I find pubic hair very exciting.) He took my hand and wrapped my fingers around his almost hard cock. It was amazing. I looked straight at it and rubbed my fingers around the head. The head was slightly purple and was leaking some clear fluid.

He removed my hand and put his hands on my head and pulled my face towards his crotch until his cock was almost touching my lips.

“Go on,” he said, “take it.”

It had a slight musky odor and I couldn’t help parting my lips as he pushed it forward towards them. My mouth wasn’t fully open when it touched my lips, but I let the head slide in until I could run my tongue over it.

“Ahhhhhhhh,” he moaned, “that’s it, Greg. You’re doing so good. Take a little more of it.” He pushed, sliding it in about half-way and then he slowly began fucking my mouth.

After a couple of minutes, he pulled off my pajama top and began playing with my nipples. This really got me excited. He pushed me back onto the bed, his cock falling out of my mouth, and grabbed my pajama bottoms and yanked them off so that I was completely nude too. He laid down beside me, kissing me and playing with my nipples, making them harder than they’d ever been.

“Are you enjoying this, Greg?” he whispered.

I answered, “It’s fantastic!”

And I immediately moaned as his fingers found my cockhead and began rubbing it. He sucked on my nipples and then kissed his way from my chest to my neck and to my lips, pushing his tongue between them and opening my mouth to his passion. At the same time, he had been stroking my cock and, as his tongue went into my mouth, I began to cum.

He continued to kiss me with his fingers sliding on my shooting cock, making me cum even more. The cum shot up onto my chest, some hitting at the base of my neck, the last shots in my pubes. He stopped kissing me, but his fingers kept still milking my cock with cum still dribbling out. He raised up a little looking down at my body and the cum in spots all over it.

“Very nice, Greg! I love making a guy shoot like that.” His fingers traced some of the cum on my chest while I was still catching my breath and then he licked them, amazing me.

“I think we might want to clean that up a little before we do any more,” he laughed. He got up and walked out of the room bare-assed and came back with a roll of toilet paper. “Here clean yourself up while I go get something.”

I took some of the toilet paper and wiped all the cum off me as well as I could. I still felt sticky, but that was OK. I put the toilet paper on the floor and laid back, enjoying the feeling of what I had just been through.

Jon came back in again with a bottle that he said was lotion that he always carried with him.

“OK, Greg, roll-over, I’m going to give you one of my famous back rubs,” he smiled.

I rolled over and he positioned me in the middle of the bed, but up near the top. He opened the bottle and poured some of the lotion over my shoulders and upper back. He straddled my back and then leaned over and began rubbing the lotion in very smoothly. I could feel his balls and cock on my back as he did this. He started very lightly and then somewhat harder, making me groan as he worked on my back muscles. He slowly moved lower and lower until he was sitting on my legs and rubbing lotion into my ass cheeks. This felt so good and was such a turn on that I was getting hard again and I lifted up to re-position myself.

He took advantage of this and had me raise myself up on my knees so that my ass was more in the air. He used his knees to spread my legs and then leaned down and began kissing my ass. He reached under and massaged my balls as he kissed along my ass crack. When he got to my hole, he used his tongue to lick around the rim.

Needless to say, I’d never even imagined that someone would do this to me and it felt wonderful. I lifted my ass up to his mouth and he spread my cheeks wider as he licked at my hole. He stuck his face in my ass and began probing with his tongue, pushing it in as deep as he could, over and over again. As he tongue fucked me, his hand was rubbing my cockhead. I moaned louder, unable to contain the feelings he was giving me. He kept licking at my ring and probing with his tongue, getting my ass really wet with his spit.

He got some more lotion and rubbed it around the rim of my hole with his index finger and then began pushing it slowly into me.

“What are you doing?” I gasped, feeling this strange intrusion into my body.

“Just showing you another one of your erogenous areas, Greg,” he said. The ass is one of the hottest things about a guy and you’ve got one of the sexiest I’ve ever seen. Close your eyes and feel what I’m doing to you.”

He pulled his finger out, put some more lotion on my hole and then pushed it inside me with his finger. It felt strange yet good as his finger anadolu yakası escort bayan went deeper and deeper and he massaged the walls of my asshole. He was still stroking my cock and he must have massaged my hole with his finger for a couple of minutes before he put a second finger in, using both now, turning and twisting them, pushing them in and out until I began to move my ass in rhythm with them, pushing back each time he pushed them in. His fingers were sliding easily into me now and every time he went deep, they touched a spot which felt so wonderful that I shivered each time it happened.

I was enjoying it a lot. But he pulled his fingers out and moved up between my legs, bending over my back. I was still on my knees and elbows and it was easy for him to reach my hard cockshaft and my hard nipples with one of his hands. With his other hand, he took his cock and slid it up and down my crack, pouring some lotion on both as he tweaked my nipples and kissed my back and neck.

I don’t know why, but as his cock slid lower and lower in my crack, I opened my legs wider and lifted up until his cockhead hit my hole. He held onto my shoulders and pushed his hips forward, his cockhead pushing against my hole.

“Greg,” he said softly. “I want to make love to you. You’re a very sexy guy and I can tell you need it.”

He pushed a little harder and I could feel my ass opening up to him. I moaned a little, wanting it but not sure what it would be like.

He kissed my neck and shoulders some more, still playing with my nipples.

“Tell me you want it, Greg. Tell me you want to feel my cock in your pretty ass.”

“I, uhhhh, I w—want it,” I choked out. “But d…don’t hur..rt me, p..please.”

“Good boy,” he said.

He applied more and more pressure until the head went into my hole, eliciting a groan from me as it forced my ass open more to accommodate it. It felt weird and not too bad until he had about an inch in and it started to hurt.

“Stop it, Jon, it hurts!” I cried.

He stopped pushing, his cockhead lodged in my ass.

“It’s ok, Greg,” he said softly, rubbing my back and kissing my neck lightly, “it always hurts at first. Relax, breath deeply and just let it happen. It’ll feel better in a minute or two as your ass muscles adjust.”

I breathed deeply and tried spreading my legs further. Jon kept kissing my neck and reaching under and playing with my nipples. I guess he sensed I was ready for more because he pushed his cock into me further. It was easier now and he rocked back and forth a little, the head going a little deeper each time. He reached down further and found my cock and stroked it. As it hardened I felt him going in further and further until he grunted and I felt his pubes up against my ass cheeks.

“God, I love a virgin ass,” he groaned as he held his cock deep inside me.

He held me close for a minute or two, our bodies wrapped together, his chest against my back. Finally, he began moving his hips slowly, his cock pulling out a little and going back in. I’m not sure how I felt. I think I was overwhelmed that I could give this wonderful guy pleasure with my body and I welcomed his cock every time it went into me.

He grabbed my hair and pulled my head to the side and kissed my cheek. His hips started moving faster, his cock going in and out of my ass, over and over. It was sliding in and out easier now and I started pushing back against him each time it went in. There was still a little pain but my body was responding to being taken by him, by his cock making me feel a part of him. I wanted more and more.

He must have fucked me slowly like that for about 10 minutes, our bodies rubbing together, his cock making slurping noises as it slowly went in and out of my ass.

Then he grabbed my hips and pulled them up higher and began moving his cock in and out of me faster, his pelvis hitting my ass harder each time. I tried squeezing my asshole when he started to pull out just to see how he would react.

“Oh yeah, Greg! Squeeze that hole, suck my cock with your ass! I’m gonna plant my seed in you soon! I’m gonna shoot a ton of sperm deep into you!”

“Fuck me, Jon! Make my body yours! I want to feel your cum in me!!!”

He slapped my ass and pounded his cock into me until I almost forgot there was another world, I was so deeply into it.

“OHHHHH FUCCKKKK!”, he shouted and he froze as his cock began pumping his juice into my hole. He held my hips tight and shoved his cock as deep as it would go as his body jerked and deposited his seed deep inside me.”

I was overwhelmed with feeling and knew I’d somehow never be the same again.

He bent over me, his cock still deep inside of me, and kissed the back of my neck and shoulders, breathing heavily.

“God that was good,” he said softly. “Are you alright, Greg? I didn’t hurt you too much did I?”

“Yeh, I’m fine. I liked it,” I answered. “That was awesome!”

He pulled back and his cock slipped out of my hole.

“Hold it there, Greg. Let me get a towel so we don’t get too much on the sheets.”

He came back a minute later and wiped my ass off. I could feel his cum oozing slowly out of me.

He laid another towel on the bed and turned me over on top of it. I stretched out and he put his arms around me and held me.

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