All characters engaging in sex are 18 years or older. This is a work of FICTION. Any resemblance to real persons is coincidental. If you like this story, please vote, comment, and let me know what you liked, you can look forward to many more stories from me. A big thanks to CongoloBistone for the editing.
Hello, first of all, let me start with a little background about me and my family. My name is Jackson Miller. I am 18 years old and in my first year of college. I am 5'9" and 160 pounds.
Growing up I loved to swim and run.
I ran track in high school and was on the swim team. I only did it because my mom asked me to, she thought it would be good for me and help with making new friends. I ended up loving it.
I was an only child and my mom was always overprotective of me and didn't let me go out with other kids much.
My mom is Kimberly Miller, you can call her Kim. She is 35 years old and I got my love of swimming from her. She is 5'6" and 110 pounds with large breasts and a tight body and an amazing ass from all the swimming she does.
My Dad is Jeff Miller. He is 40 years old and 5'6 and 220 pounds. Dad travels a lot to check on his businesses and is away a lot. My dad started his own car dealerships when I was 1 year old, with the money he got from my grandfather's life insurance after he passed.
One turned into two to four to ten. And he now has several large apartments and hotels in his name.
Around the time I was 8 years old we moved to a large house and I got everything I ever wanted. But dad was never around. It was only me and mom I think that's when my crush on mom started and never really stopped.
I got into a good college four hours away from home. My first year of College was fun. I had made some friends and even got a girlfriend for a short time and ended up hooking up with lots of girls. But I always found older women hotter than the college girls that I was fucking.
I told my best friend one day, as we got high that I liked older women. But it was hard to find them in college. He told me about several websites that he use to find girls for a quick hook-up, and that older women or couples go on it to find younger men or women to hook up with.
The next day I checked it out and couldn't believe how many couples and older women were in our area looking for people to hook up with.
I made an account and put up a profile with a fake name " Run4it ". but I didn't put up a picture of myself, as I didn't want anyone to know it was me.
Profile: 18 year old college student new to this looking to meet like-minded people for fun.
I found several older women that looked like my mom and sent them a message. I waited for days but didn't get any reply.
After a week I got a message back from a couple going by the name of Jack and Jill asking for a picture of me.
I asked my friends what Kind of picture should I send them and he told me to send a picture of my body and dick and don't show my face.
I did what he told me and I got a reply back several hours later. They asked to meet up in a couple of hours at a hotel.
I was surprised from not getting any reply to one so fast. I was happy to finally get my chance to be with an older woman and that she looked like my mom.
I got to the hotel they told me, and of course it had to be one of my dad's. I asked them which room and I went up. I was so nervous walking into the room but the couple was nice and made me feel relaxed and comfortable, they told me that they were looking for a bull for a while, but didn't like any that had messaged them. I looked at them. I was new to all this and didn't know half of what they were saying.
Me: " What's a bull? "
Jill: " You are silly. "
Me: " I am sorry I am new to all this, I don't know what a bull is, I did see people post about it but didn't know what that means "
Jill: "Oh, ok you are new to this aren't you. A bull is a guy that has a large cock mostly it bigger than 8 inches."
I looked down and got shy as they told me.
Jill: " So that's why you didn't post as a bull if you did you would have gotten a lot more people wanting to have fun with you. So how big are you anyways".
Me: " I don't know I never thought about it or Measured it".
Jill: "Well we will find out soon, so should we get started we don't have a lot of time, we only got a babysitter to stay till 9".
I sat there as she got undressed and I got my first look at what a hot older woman looked like. She asked me to get undressed and I did.
She got on her knees and took my cock in her hand and looked at it.
Jill: " It's got to be at least 10 inches we got lucky with you".
She started by jerking me off and then sucking on the top of my cockhead. It was amazing what she was doing, most girls in college suck a dick to get it hard. But she was enjoying what she was doing and so was I.
I looked over at her husband who was sitting there jerking off and I could hear him telling her to suck harder and to take that big dick and she did.
She sucked my dick for 10 minutes, before she told me she wanted to feel me inside of her. which I was more than happy to do. She got on the bed and laid down as I got on top of her and slowly pushed into her wet pussy.
Jill: "Go slowly baby I never had a dick that big, I'll let you know what to do ok".
Me: " I'll follow what you say".
I slowly pushed half of me into her and started to fuck her going a little more with every single thrust I made. She was so wet and moaning loudly as I fucked her. Her husband got on the bed as kissed her as I fucked her.
I finally got all the way into her and they seemed to be happy about that. She told me I could fuck her however I wanted to and that to finish inside of her and that she was on the pill.
I fucked her hard and fast and had her screaming out. She kept telling her husband how good this felt as she started sucking his dick. It was amazing how good it was. My dick was covered in a thick white cream from her pussy.
I told her I was cumming soon and she told me to go ahead. I filled her up and she told me to come up to her so she could suck my dick clean. As she sucked and licked me clean I saw her husband get between her legs and lick her pussy clean and suck out my cum and swallow it down.
We fucked three more times that day before they had to go but I got her number and a date for next week with them.
As I got home my mom called me to ask how everything was going and if I was going to come home anytime soon. I told her I would be coming back soon and that everything was going great.
I got online and changed they profile to bull with the pictures that I sent them with my body and dick in it.
The next few weeks I had more messages than I knew what to do with. I now had the opportunity to pick who I wanted from all the people that sent me a message asking to fuck.
It got Busy for me but with my classes being easy I had all the time I wanted. I had a date for every day of the week sometimes two, and had my first threesome with two friends that I meet. And I even had a women offer to let me do anal if I picked her. I stated to use condoms after the first time and got checked every two weeks to be safe.
I knew the holiday was coming around and started to look for women or couples back home. I didn't put up my profile there in case someone I knew was on it and they knew my mom and dad.
I was checking every day to see if someone new came on or if someone Caught my eyes. Two weeks before I was to go back home I saw a new profile was put up at 2 am. And the woman was so hot and sexy she didn't show much but had several pictures in sexy underwear. She reminded me of my mom with her bubble butt and large breasts and tight body. I had to get her before anyone else did.
Sexyswimmer profile: " First timer looking for young hot male to live out some fantasies. Message to get to know each other before meeting up".
I sent her a message and told her I was going to be in her city in two weeks for a week for Thanksgiving. And would love to get to know her more and if it went well to meet up and that it was all on how she wanted it to go.
I check and her profile was down almost as soon as it went up. I thought she had got scared and taken it down.
The next day I got a message back from Sexyswimmer and we started to talk.
Sexyswimmer: " Thank you for answering my ad can you send me a picture of yourself".
Run4it: " You are welcome, you took down your post fast".
I sent her a picture of me holding my dick. And one of me fucking one of the women doggy style with a condom on to show I was safe and how much cum was around my dick.
Sexyswimmer: "Omg! you are so big and that women look like she is enjoying it so much. I got Nervous and took it down before anyone saw it but you did and sent me a message".
Run4it: " Yeah, everyone loves it and we all have fun but keep it safe. I did the same the first few times I put up my post ".
Sexyswimmer: "That makes me feel better about my post. One of my biggest worries about doing this is to make sure I am safe, but am allergic to condoms so I don't know how it will work".
Run4it: "In that case if this gets to that point, we get tested a couple days before and show the test results with the date of the test to each other with names blacked out. And the only other thing is to make sure that you're on birth control In case of accidents".
Sexyswimmer: "Ok that makes me feel better about this. And I can't get pregnant anymore".
Run4it: "Ok, so now comes the getting to know each other part, I'll ask questions and you ask questions and we tell the truth".
So why did you want to get into this in the first place? And can I get a picture back? you don't have to show your face if you don't want.
Sexyswimmer: "I guess my biggest reason is that My husband has to travel a lot for work and we don't get time together and we miss having sex the most. We talked about it and decide that when he is out he can have sex with anyone he wants and so can I as long as it's safe and it doesn't get more than just sex. Now for my question, you're young and in good condition and I knew the girls would love that big dick so why are you here".
I got some new pictures of her one topless showing off her nice big breast and one was an ass picture I got hard looking at it. It looked so soft and firm I could tell she worked out a lot.
Run4it: "Thank you for the picture you have an amazing body. Yes I didn't have trouble getting girls. But I always had a thing for older women. I think it comes from my crush on my mom. What kind of thing are you into?"
Sexyswimmer: " Every boy has a crush on their mom at some point in time in their life and some moms have a crush on their sons. Am into normal things sex ways I never tried anal but don't think I will. I love doggy style the best. Would you ever make a move on your mom if you had the opportunity?"
Run4it: " I can do normal. If I knew my mom would be into it without a second thought, but I would have to be 100 percent sure she is before I could make a move on her. The last thing I would ever want is to mess up the relationship we have. And you if you? have a thing for your son and would you make a move".
Sexyswimmer: "I guess my answer is the same as yours if I knew it would go well and not hurt our relationship with each other than a big yes. Have you ever spied on your mom"?
