You may be breaking a law in your state or country by clicking on Nifty, then clicking on Gay, then clicking on adult youth, then clicking on Newspaper Ad. This is a story that has sexual content between an 18 year old man and as young as a 9 year old boy. If you are under 18 you definitely do not belong here. It is your choice to stay or to leave. If you are here legally and are of legal age then Welcome from sgtxray@mailcom.
This story is pure fiction, never happened, hopfully never will.
The next morning I got up thinking to myself, today is Saturday and my last Saturday babysitting job with Jason. Even though I loved the kid like a brother I still would like to have an occasional Saturday off. I don't even know why? It just seems only right not to work on Saturday.
I went downstairs and was having my normal morning chat with Mom and Karen but knew it was Saturday and even though I had to work tonight I really had the day much to my self. I thought about just riding around and people watching. Just as I was getting ready to leave the phone rang. My mother said it was for me. When I said, "Hello" it was Mrs. Haines the attorney calling. This kind of scared me for a minute, had I done something wrong or something she found out about?
"Hello Jay, I was wondering if you would do me a big favor. I have a client that is 14, yes people get in trouble young these days, anyway his mother has to be gone next Monday night an d since he is on probation he can't stay home by himself. Would it bother you to watch a 14 year old, Jay?"
"No not really, would it pay the same?"
"Oh yes, I will pay you and add it to their bill so you will make $50 as usual."
"Well then I would be glad to "Hang Out", that's what I call it with that age, with what is his name?"
"Oh yes his name is Doug. I think his mother refers to him as Douglas but I am sure he would rather be called Doug.
"Yes I'm sure he would," said Jay. "By the way what is the address and phone number."
"They live at 837 Wildwood. Are you familiar with that street Jay?"
"Yes Mame, and the phone number?"
She gave it to him and he told her he would be there. "What time do they need me?"
"About 6 and I think she will be gone until late like 2am or so. I will tell her you sleep on the couch until she gets home after Doug goes to bed."
"Thank you Mrs. Haines I appreciate your trust in me."
"You have earned it Jay. You do such a good job with my boy your all he talks about. and don't forget us next Thursday at 7."
"Don't worry Mrs. Haines I have it on my calendar."
Jay was really happy with this assignment as he liked kids closer to his own age. He decided to go on out people watching as he called it. He went to the Mall first and hung around for awhile but seeing no one he knew that got old in a hurry. So he rode over to the ball field to see it deserted too. Well he was just about ready to go home and play video games when he looked up and saw the adult book store. Since there weren't any cars parked there he decided to go inside and look around a little more.
He hid his bike behind the dumpster like he did the last ti me and went on in. He found some things that he hadn't seen last time since he was so nervous that time. Back behind all the video's he saw some little cubicles and he decided to look and see what they were. There was a man inside one watching a video of a naked guy giving head to another naked guy. Jay was astounded he didn't know they even made videos of such things. He decided to stand there and watch as the man obviously wasn't looking out his eyes were glued to the screen. Jay got a massive hard on watching that scene. When it was over the guy who looked about 20 came out of the booth and saw him.
"What's happening dude." The guy said.
"Jay felt like a kid caught in a cookie jar and said, "Oh not much I was just looking around. This is only the second time I have been in here and I didn't even know this section existed the first time."
"You look younger than me even, how old are you?" the guy asked.
Jay stuck out his chest and said "I'm 18, how old are you?"
The guy answered, "I just turned 20." Jay was impressed with this guy as he was sandy blond, fair skinned and had a swimmers type slender body. And from the back view of him he had been looking at had the most awesome ass for a 20 year old Jay could remember.
Jay said, "Gosh we are almost the same age. I've never seen you around town before."
"Yea I just moved here from Texas and got a job at the feed store."
"Well my name is Jay glad to meet you." Not knowing anything else to say.
"My name is James, you say you have only been in a place like this once before?"
"Yea, just once."
"Do you want to watch a video with me in a booth?"
"That sounds cool." Jay said as he looked down and saw th at James had a Hard on also.
They both stepped into the booth and James fed the machine a coin and pushed the start button.
Jay was real nervous as all this was so new to him.
James said, "I see you have the same problem I do we are both hard." And with that he reached down and rubbed his hand across Jay's hard on.
Not to be out done Jay reached down and rubbed his hard on too. Then as he felt James start squeezing his he started squeezing James back. It wasn't long before Jay had unzipped James and reached in and felt his dick through his boxers. It felt so warm and good.
James unzipped Jay's pants and reached in and pulled Jay's dick out and then kneeled down and took it into his mouth. Jay thought he was going to loose it. Jay responded by getting his dick out and stroking it as it was uncut. After about 5 minutes of this James said what you say we go over to my apartment, it is only a couple blocks from here.
By now Jay would have said yes to anything. So he said, "I'm on a ten speed can I follow you."
"I'm just walking we can walk together and push the bike to my place."
Jay agreed and they went on their way to James' apartment. It was small, one room with a hide a bed and a bathroom. It had a very small area that served as his kitchen with a small refrigerator and a four burner stove with an oven.
James hadn't made up the hide a bed so that is where he guided Jay. When they sat down it was instant kissing which lasted and lasted. Jay really like this as he had not had sex with someone older than himself yet and was enjoying every minute of it.
James stood up and took off his shirt and pants then slid out of his boxers and was standing there nude. Jay followed suit. Then it was back to the kiss and foundling. Jay asked him if he had any Vaseline and James went to the bathroom and returned with some. Jay took some on his finger and went up in James ass with his middle finger. James said, "Oh I've never had anyone do that to me before it feels kinda good in a way."
Jay being very experienced didn't let up but went right to two fingers and started two finger fucking him pretty fast.
James said, "Oh man if you keep that up I'm gonna cum."
Jay said, "How many times have you been with someone?"
James replied, "Not many since I was 14 and 15 when I had a boy friend."
Jay said, "Have you ever had anal intercourse?"
James replied, "No I just never had a chance."
"Do you have any rubbers?" Jay asked.
"Yea I have had some around for years and never used them. Here let me ge t up and I'll get them for you."
Jay found he was having a hard time breathing as he was so sexually excited. More so than he could remember being with any of the younger guys. When James brought the rubbers Jay took one and put it on his massive hard dick.
"James since you have never had experience, do you have any water based lubricant?"
Again James went back to the bathroom and said is this what you mean?"
"Yea dude this will work." Jay squirted some on his fingers and started three fingering James.
"Oh that hurts when you do that Jay."
Jay said, "That is normal but the hurt will stop in about 30 seconds and your anal muscles will have adjusted to the new size entering it."
"Oh OK." James said kinda scared like.
Now don't be nervous James I am experienced at this and I will not hurt you OK?"
"OK," was all James replied.
Jay continued with the three fingers until he was taking them easily. Then he pulled out his fingers and immediately replaced them with the head of his dick. Telling James to push out like he was going to crap he pushed his dick in about 2 inches. "How does that feel James?"
"It's OK it's starting to feel a little good now. Push harder."
With that remark Jay was all the way in in about two seconds. Then Jay started slow fucking James and continued with that until James was completely relaxed and said, "That feels pretty good now doesn't it dude?"
"Yea fuck me Jay I'm really getting into this now. I never knew it would feel this good."
Jay started long fucking him and was able to keep himself from cumming and ruining his first experience for like 15 minutes. But then James let out a holler and said, "Oh God I'm cumming."
When James went into orgasm that was all she wrote for Jay for the feeling his dick was getting from the muscles massaging it as James came set him off. He pushed in as hard as he could and let rope after rope of cum shoot up into James as far as he could. When he finished he collapsed on James back and hugged him real tight.
James said, "That has to be the most awesome thing I have ever in my life experienced you got my cherry Jay."
Jay said, "Yea I sure did and enjoyed every minute of it. Now let's rest until we recharge and I will let you do me."
"Gosh that would be my first time to do it to someone else too. I guess I really am a virgin to anal sex. All I have ever done with guys is give and receive head."
Jay said, "Do you have anything cold to drink or we can go down to the store and get something."
"I guess we better go down to the store as I don't have anything in the house.
On their way to the store James confessed to Jay that the reason he had never had much sex with guy his own age is he was always afraid to approach them. If you hadn't reached down in the booth and unzipped me probably nothing would have happened except feeling each other up. I don't know why but because of this fear I have always had sex with guys much younger than me, even in their pre-teens. You can tell I trust you Jay or I wouldn't be telling you this. But you know a guy like me has to have someone to talk to. It is so hard holding all of this inside me.
Jay said, "I know what you mean Jay as I have also had sex with guys younger than me too. Mainly because offear of being found out. as I am in the closet too. The young guys don't talk.
James said, "Yea I know they keep it their deep dark secret."
" James I baby sit for extra money to save for college. So I am in contact with several underage kids every week which doesn't help me much either."
James said, "Maybe I shouldn't ask this but do you ever get sexual with the guys you baby sit with."
Jay wasn't sure he could trust James with that information yet so he answered, "Well I do let them sit on my lap and I help them in the bath but that's about all James. After all I am working and I wouldn't want to take the chance of one of their parents finding out."
James replied, "Yea I see what you mean."
"Here is the store and boy am I thirsty" Jay said.
"Yea me too. You know I feel so much lighter after talking with you Jay," James said.
"I'm glad you let it all hang out as I trust you more knowing you put your trust in me." Jay answered.
They went into the store and Jay picked up a six pack of Pepsi and paid for it. They asked the guy that checked them out to please open one of the bottles for each of them and they swallowed almost half a bottle in one swig. Then they went out and headed back toward James apartment.
Jay was curious so he asked James, "How old were you when you had your first sexual experience?"
"I was 13 and the kid was 8. I just started talking about the stuff I look at on the Internet and he got interested. I showed him a few pictures and saw that he had a real woody. So I told him these pictures made me hard too and took his hand and put it on my dick. That was all it took Jay we messed around for a good hour. Nothing much just rubbing each other. I showed him how to jack off and stuff like that." replied James.
"Sounds familiar I guess we are all the same in some ways." said Jay. "I have done that too. "
"Really, I bet we could swap stories all evening." said James.
"Yea I wish I could but I have to work tonight. Which reminds me can I use your phone to check and see if I have received any more calls from my add in the paper?"
As they walked in the apartment James said, "It's over there I just had it hooked up yesterday."
Jay dialed home. His mother answered and informed him Mrs. Cary had called and said that since they were so close to approving a budget for next year they had decided they could do it on their regular Friday night meeting next week so she won't be needing a sitter tonight. Jay said that was fine. He was happy because it now gave him his evening free with James. He told his mother he had a new friend and was over at his apartment talking with him and that if she needed him she could call and gave her the number. That ended the c onversation and left Jay feeling so elated that he finally got a day off and if things went well he would have tomorrow off too. He relayed this information to James and he could tell this made James very happy too.
"Jay do you think you could spend the night here tonight. Would your mom be OK with that?"
Jay answered, "Oh yea, my mom is real understanding and let's me do pretty much as I please within certain limits."
"That would be so awesome said James."
"Yea I think so too James."
They had finished their pop and so Jay knowing he would have to take the lead took hold of James and started kissing him. He stuck his tongue in his mouth and it wasn't long before they were tongue sucking. This of course made them both hot and so James reached down and took hold of James dick which was hard. James recuperated immediately by doing the same to Jay. Jay said, "Why don't we get undressed?"
With that statement they were both nude within a minute. Jay lay him back down on the bed and told him to take the Vaseline and prepare him with one, then two, and finally three fingers, that he was going to take his other cherry and let him fuck him. Jay was a little uncertain about this as he was much bigger than himself. His dick was about 7 inches or bigger and much bigger around than Jays. But Jay knew that with all the dildo experience he had had in private he could manage it.
James went ape shit. He had never done anything like this before and was even shaking a little. "Tell me if I hurt you Jay. You know I am new at this."
With that and seeing how nervous he was Jay said, "Listen James I know you are nervous but I want you to relax. This isn't my first time and I can take what ever you can put out so relax. OK?"
With that the middle finger went in all the way and Joe grinned as it felt so good with James doing it. There was something magical about being with someone their first time maybe that's why he enjoyed teaching the kids things.
Then came the second finger and with James big hands Joe could feel it. After a few minutes of finger fucking him with the second finger in went the third. Joe let out a moan as now it was hurting a little but he couldn't let on and scare James. Soon the pain dissipated and it was OK again.
Then Jay said, "OK now James put on the condom and lubricate it with the water base stuff."
James had trouble putting on the condom as it was his first time so Jay reached over and helped him giving him a kiss on the lips to encourage him. Then Jay helped him lubricate it. When J ames was physically ready Jay lay down on his back and put his legs up feet to his ears exposing his entire ass.
James said, "That isn't how you did me."
"I know James it would have hurt you more as you were a beginner and in this position the dick can go further up in the guy." Jay replied.
Now put your dick on my hole. James followed directions. Now I am going to push out when you hear me grunt you push in OK? Jay said.
Jay made a grunting sound and James started in. He got about two inches in and said, "Is that OK Jay?"
Even though it hurt like hell being so big and round Jay said, "Yea just wait a minute and then push it all the way in."
James waited a minute and then started in and kept going until he was balls to balls with Jay. "Are you OK Jay?"
Jay could hardly answer because he was indeed in a l ot of pain but he again answered. "Y..Yea just w..wait a m.Minute and then start slowly."
James waited a minute and felt Jays anal muscles relax more and then started out real slow when he got just about to the head he started back in. It felt so good to him. He had never felt anything so tight and so warm, it was almost hot in there.
Jay was starting to feel real good now and so he gave the command, "Fuck me James!"
James didn't have to be told twice he started in and out and speeded up with each thrust. Soon James was going faster than he had ever believed he could move and it felt so fucking good to him he didn't ever want to stop. Since they had both come within the last hour it lasted a good 30 minutes. Sweat running down both of their faces when Jay said, "I'm gonna give it up, I'm cumming.
James had never felt an orgasm from inside before and it caused him to r apidly get closer to cumming himself. When he knew he couldn't hold it any longer he pushed his 7 inches clear up in Jay to what felt like his stomach and let rope after rope go deep inside of Jay. Jay of course couldn't feel it because of the rubber but he knew from the swelling of the dick and the look on James face what was happening.
James fell over onto Jay's stomach still embedded deep in him and kissed him for what seemed like the longest time. They were tongue sucking when James dick finally got small enough to fall out. James sat up and said, "I don't think anything in the world could feel that good Jay. Thank You so much for the education and your ass."
Jay replied, "Well don't think it wasn't a trip on this end. Boy you sure give a good fuck. That was the most wonderful experience I think I can remember too."
They both got up and sat hugging each other and then decided to take a shower together. They washed each other like Jay was used to by now but James said he had never showered with anyone before and he loved soaping each other down. They both had a semi hard on but neither was up to a full wood yet.
They turned the bed into a couch and sat and arm in arm watched some TV. They also got more talkative about previous experiences but Jay still kept his baby sitting activities a little private as after all he was dealing with some pretty special kids there and didn't want anything to ruin that.
They were becoming good friends and Jay was so happy to have a friend his own age that was also gay. Jay called him mom and got permission to stay the night and so after the movie around 10 PM they made the bed back down and both of them slept in the nude. There wasn't any more fucking that night as both of them were sore. But Jay was able to introduce him to 69 which they did until they both came again. Then exausted they both fell asleep.
Thanks for your email I do appreciate it. Here is the updated states and countries that have written me after only 6 chapters. I am now working on chapter 16.
Hawaii; UK; London England; Wales UK; Saskatchewan Canada; Orlando Florida, another Florida; Winchester UK; Omaha Nebraska; Texas; New York City; Arizona, Washington, Missouri, Austrailia, England; Greenvile Tenn; Rome Italy; Las Vegas NV; NC; Lousiana; Long Island, NY; Winchester, VA USA; Los Angeles, Calif; Holywood, Florida; Cape Town, South Africa; Pheonix, Arizona; Queensland, Australia; Sydney Australia; Gerogia; Carbondale, Illinois; Oregon; Brookings, Oregon; TENNESSEE; Nevada; Omaha, Nebraska; California; Berlin, Germany; England; Jacksonville, Florida; Adelaide Australia. Alberta, Canada;Rome Italy;San Francisco, Calif;Lake Ridge V irginia USA ANNAPOLIS, Maryland; Wolverhamton, UK; Bangkak, Thailand;Mt. Wolf, PA; Union, Connecticut; San Jose, CA; Monterrey, Mexico; Montreal Canada; delaware; Chico, California;Plymoth, UK;Norway; Denver, Colorado; Ontario, Canada;Chateauguay, Quebec, Canada;
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