Jay's Prom

A month ago, I was out at our cottage. I stop by every few weeks, just to make sure everything is ok. I always check all the windows and doors, to make sure no one has broken in. I also like to check to make sure the furnace and other mechanical things are all still working. If I am lucky, I run into either Frank or Jay.

Frank is my neighbor on one side of the cottage. He is in his early 80's and has been a widower for many years. On several occasions, Frank and I have had sex. I have written about a few of these times (Memorial Day part 2 and Frank's present). If you are interested in old men and younger woman then these might interest you.

Jay is my neighbor's son from the other side of the cottage. I have several times over the last couple of years had sex with him and once with his two older brothers. I have written about this in Memorial Day part 1 and 2 and a Day at the cottage stories. If you are interested in older woman and younger guys then these might interest you.

The first time I did anything with Jay was with his two brother, at my Memorial Day party. My husband and I often have what we call adult type fun parties. We were outside playing around with some friends. Four men were holding me down on top of my picnic table. They had just opened my dress, so I was completely nude.

I knew that the teenagers were in their yard watching but let the guys start to play around with me anyways. I was at the time very drunk and love to show off when I have been drinking. Knowing that these teens were watching really turned me on.

Before the guys started to do anything to me, I heard Bob telling the boys to come on over. I looked at him and told him no way, we cannot have these kids take part in anything like this. He told me to shut up and sit still. I was warned that if I do not, he would gag me. He asked the youngest boy how old he was. He said he just turned 18. I did not believe him, with the way he gave his answer. I also thought he looked too young to be 18. Still I did not have much of a choice, so I let it go. Look at my other stories if you want to know what happened.

So back to the present, I was finishing going through the cottage, when I heard a knock on the door. I opened the door and found Jay waiting outside. I let him in and asked what was going on. He said he came over to ask me for a favor, but first he had to tell me something. He hoped that I would not get mad at him. I told him not to worry that I am an easygoing kind of girl.

He started by saying that he never meant to do anything wrong. He told me he had for years fantasized about us have sex. He always wished he could take part in our parties. He told me that when he finally got a chance back a couple of years ago at the Memorial Day party I was having, that he lied when asked how old he was. He said he knew that if he told the truth that the guys would have made him leave. He told me that he had just turned 16 and that his two older brothers were only 17 at the time.

I started to freak out a little and yelled at him. I said, "Are you telling me for the last 2 years I have been having sex with a minor. That if we were caught I could have been charged with statutory rape. I cannot believe this." I asked him if he realized how much trouble we all could have been in if someone found out. What I did not tell him is the actual age of consent in my state is 16 and that we would not have got in any trouble. I did not want to let him off the hook. I looked this up shortly after the first time I had sex with Jay, just to be safe.

He tried to apologize for what he did. He also tried to tell me how much he had wanted to do stuff with me after spying on our parties. He told me that any teenager would have done the same thing. After a few minutes, I started to cool off and realized that he was right. I am sure most teenagers giving that kind of chance would have done the same thing. I know back in high school, many of the guys I ended up doing stuff with were just as eager to get in my pants as Jay was. I am also sure any one of them would have loved to do something with a hot old neighbor given the chance.

I asked him why he was telling me now. He said that he was here to ask a favor. He told me that his 18th birthday was 27th and his school prom was the 28th. He said he did not have a date for the prom. His girlfriend broke up with him, because he was always trying to get her to do stuff with him and a few of his friends. He told me that after all of the stuff he had done with us or seen us do, that he wanted to do the same kind of stuff with her and his friends.

He told me the last time they were together that the two of them plus three of his friends were sitting outside on the dock. They had all been drinking. He said he was making out with her and started to remove her top. She stopped him because people were watching. He tried to get her to show her tits to his friends but she just got mad and made him take her home.

I asked what did that had to do with your birthday, prom, and me. He told me that he and his four friends have tickets to the prom but only one of them had a date. He said that they were hoping to have their own party to celebrate his 18th birthday. The plan was to go to the prom and get their pictures taken. Then they hoped to find a place to party.

I told him I was still not seeing what that had to do with me. That was when he said, he had this idea for a while. He was hoping to have a private prom with the five of them and if I was up to it, maybe I would be willing to join them. He then quickly added in, and maybe a few of my friends.

I said, first you tell me that you lied about your age for the last 2 years. Next, you turn around and ask me to let you and your friends come party with me after you go to the prom. I then said, "To top it off, you want me to invite some of my friends to come over so you and your horny friends can have us be some kind of sex toys for you". He tried to tell me that is not how he was thinking about it.

I asked him if he had been telling all his friends about what he has been doing at my house. He had promised me a long time ago he would not do that. At that point, I was starting to get interested in his idea, but did not want to let Jay know that. The thought of me and several horny 18-year-old guys sounded like a lot of fun.

He immediately told me he never told anyone about what we have done. He said that he had not even told his brothers about anything we had done, after that first time when they were there. He told me that he only thought about how exciting it is when we do stuff with him. He would love it if his friends were there to watch and possible join in.

I said even if I agreed, I doubt that your pal's little girlfriend would be happy. Once she watched use doing anything together, I would think she would react the same as you girlfriend. He told me she would not mind. He said she is actually open to doing a lot of stuff. He told me, she had not let any of them touch her, but she lets her boyfriend do stuff to her in public. On several occasions, she let her boyfriend show off her tits to the group. He told me, she had even sucked off her boyfriend in plan site of them. He thought that she would be really into watch someone else do stuff.

I spent several more minutes, telling him I did not think this would be a good idea. I was giving him crap about why would I do this after the lies he had been telling. In my head, I already decided it would be too much fun to pass up and that I was sure I could get Lisa and/or Kelly to come along.

Lisa is my husband's niece in law and Kelly is her best friend. They are both in their early 20's and could pass for dates for these guys, better than I could. I just had my 30th high school reunion last fall. I have been working out harder than I ever have to maintain my body. Even if I have to say so myself I look better now than I have ever in my life.

After letting him squirm for a while, I told him that I would think about it and let him know. We agreed I would call him sometime during the week. As he started to leave, he moved closer and started to kiss me. He then ran his hand between my legs and up my skirt. Just like he has done for the last few years when leaving. As his fingers got to my wet panties and slide inside them and over my clit, I pushed his hand away. I told him that I do not let little boys under 18 touch me like that. I could see the sad look on his face and the large bulge in his pants. I told him sorry, he will just have to go home and take care of himself. I let him know that I would have to go upstairs to my room and get myself off on my big bed all alone now that he had got me so worked up.

After he left, I went up to my room and turn the lights up bright. My bedroom windows are across from Jay's room. I did a slow strip tease in front of the window, making sure to show off as much as I could. I could clearly see Jay in his room watching me. He had his cock out and slowly worked his hand up and down on it. I then laid on my bed with my legs spread out wide facing the window. I started to rub my pussy with my right hand and pinch my nipples with my left. I knew Jay had a clear view of me through the window. He has told me many times how he loves to watch me in bed playing with others or myself. He also loves to video tapes me so he can jack off to it later.

It only took me a few minutes to get myself off. When I was done, I moved over to the window and could see Jay still watching me. I could tell he had already finished himself and was just relaxing, while I finished. I slowly put my cloths back on, turn out the lights and left.

When my husband called that night, I told him what happened at the cottage. He said that he was always very suspicious of Jay's story about being 18. He said that he did not know how to find out without causing an issue. Even before, I told him I would like to accept Jay's request, he said so are you going to the prom or just having them come over afterwards.

I told him I had not made up my mind if I was going to accept yet. He told me, there was no way I was going to pass up the chance to have four young guys all over you. I kind of laughed, and told him he thinks he knows just what I might do. He told me after this many years, he know precisely what I would do.

I called Lisa the next day and told her about Jay's request. She said, she would be interested but not Kelly. She told me Kelly had started dating a new guy. He is nice but defiantly not into anything kinky. She suggested asking her brother's girlfriend. She said that the two of them and her had played around a few times. I asked her, how old his girlfriend is. She told me she was 19, and that she had just graduated last year from the same high school Jay goes to.

After our call, Lisa gave Samantha (Sam) a call to see if she would be interested. Lisa told me later that Sam actually knew Jay and the group of guys he hangs around with. She told her that Jay used to date one of her friends. Sam said her friend told her he was a bit too freaky and was always trying to get her to do things she was not comfortable with. Sam on the other hand always thought he was somewhat attractive and after hearing her friend talk, thought it might be fun to have gone out with him. I now had my other two dates for the guys.

I waited to Thursday to let Jay know. I told him that Lisa and one of her friends agreed to go. I told him it was up to him and his friends to come up with the transportation. I let him know that I would be getting a large suit at the Hyatt for the night. No big deal for me, my husband has over a million points with them. The last part of the demand on Jay and his friends was that they keep whatever happens after the prom quiet. He total agreed and said he was sure his friends would agree.

The plan was for the three of use to meet at my house and get ready. The guys (Jay, Troy, Brian, Lucas, and Lucas's date Sherri) would pick us up at 7pm in a limo. We were going to stop off at Carrabbas for diner, at the guys expense. After diner, it would be onto the prom for pictures and maybe a dance or two. Finally off to the hotel to end the night.

Around five Lisa and Sam showed up at the house. I was completely stunned when I saw Sam. She was absolutely stunning. She was at least 5'9" tall and was wearing 3-inch heel. I can tell she was mostly Indian by her deep rich dark skin and hair. She was very thin maybe a size 4 or 6, but had great breast, I would guess to be around a c cup. Lisa was almost as tall but a complete opposite of Sam. Lisa is very lite skinned with an athletic build. Her hair is almost a white blonde. She has beautiful green eyes to top it off.

Sam went to work on Lisa and my hair and makeup. She is currently working on her license for cosmetology. She put my hair up and did some very lite make up with a pink tint. It helped me look a little younger but I still thought I was a little too old looking to be doing this. She did Lisa's hair and makeup similar to mine. Lisa could easily have passed for 18 or 19.

I put on my new outfit. It was a two-piece outfit with a nice gap at my midriff to show off my abs. I have been work hard on them and can start to see some muscle striation. The outfit had a white halter-top without a bra. The halter-top had appliques across it with an Asian theme. The material was lite enough to see my nipple poking out but was not transparent at all. I also had a white flowing chiffon shirt with a slit up the side that went to the mid-thigh. The skirt was so lite and transparent that I decided to skip panties. I had a nice lace panty picked out but could see the lines once the skirt was on. I did not want them to show through so I took them off. I top it off with some three-inch silver strappy pumps. I was still a few inches shorter than either of them.

I had my finger and toenails done during the week with French tips and rhinestones on each. When I looked into the mirror, I thought I look good and hoped that I could at least past for Jay's older sister or something. Lisa and Sam both tell me not to worry about it. They both said any guy there would love to have me as a date.

Sam had an Indian inspired dress. It was a black two-piece with halter-top with gold flowers on it and a black long skirt. Over one shoulder, she had a black netting wrap that hangs down almost to the floor. The wrap covers most of her tummy so not to show off to much skin. She told us this was her dress from her junior prom. She did not think anyone there tonight would have seen it.

Lisa had on a simple A-line pink chiffon dress with a knee length skirt. The top had sleeves that fell off the shoulder and had a wide dip front that showed off plenty of her bust. She had on some 3-inch heel with open toes. I noticed that she also went with no panties.

We headed down stairs when we were finished. My husband was in the living room and gave us a whistle when we walk by. I moved over by him and asked him what he thought about my looks. He said Jay was one lucky guy to be able to take me to the prom. He told me he knew from person experience, as he had taking me to our prom. He tells me that if Jay's prom is anything like ours was that everyone else was going to be very happy as well.

Our prom was very crazy. After the prom, we ended up at my husband's house. His parents were out of town at the time. It was just him and I at first. I can remember coming many times, as my husband ate me out for what must have been an hour before he finally fucked me. As the night went on and our friends had taken their date's home for the night, they came to his house. Most of them had no luck with their dates and were very happy to see me. By then end of the night, I had been fuck by ten different guys.

The guys showed up a little before seven. Jay was the first one in the door and looked good in his tuxedo, as did the other guys. Sherri was the last to come in and she had on a beautiful blue dress similar to Lisa's. She was a little shorter than me maybe 5'1" or so. She looked like a little tom boy, with short hair and thin build. Her tits may be an A cup. Even though her dress was like Lisa's, she was not showing off nearly as much cleavage as Lisa was.

I introduced everyone to my friends and Jay did the same for his friends. Jay was first to notice Sam was a girl from school. He told her it was great to see her again and cannot believe she was here. After a few minute of talking, we all paired up. I let Sam go with Jay, as she had wanted to before today. Lisa paired up with Troy. I had picked Brian first anyways. He looked like your typical farm boy. He had a cute face and a body that looks like he has worked out a lot. Each of the guys gave us a corsage and we headed out.

On the trip to the restaurant and through most of the meal, we all took part in small talk. Each of us was trying to get to know one another. Watching the guys was fun because each of them were checking us out, but trying not to look to obvious. At one point, Troy asked Jay how he knew us. He looked at me before he answered. I told him go ahead and tell them how we meet. I first told everyone that they should not let it get around. I asked them to promise to keep quiet about what they hear. They all agreed that should not be a problem. Jay then told them about the first time we meet. By the time he was done, all of the guys were looking at me like there was no way that happened. I told them it is true but remember you promised not to let it go any further then this group.

On the way to the prom, we each split into different conversations. Brian was asking me more about what kind of things I had done. He wanted to know when I started doing these types of things. I told him that my husband and I started dating in the 11th grade. Shortly after we started to date, we started to play around with others. I told him that we both looked at sex as something fun to do. I told him neither of us gets jealous of what the other does and that most times we are together when we do play around. I told him to night was a little different because Jay asked as a favor would I be willing to join you guys to night.

As we were talking, I was leaning in to him. I took his left arm and wrapped it over my shoulder. I started rubbing my hand up and down on his thigh and had my face only inches away from his. By the time we got to the prom, Brian and I had been kissing for a while. My hand had a firm grasp on his rock hard cock through his pants. Brian had been rubbing my tits, taking time with one and them moving to the other. I looked around and everyone else was doing the same things. Troy may have been a little further ahead with Lisa because he had his hand up her dress. I was sure he was fingering her.

We all climbed out of the limo and headed into the dance. I did notice the people taking the tickets look at me funny but did not say anything. We all headed in and found a table in the back corner. The guys got us drinks and we all sat around the table talking.

After a few minutes we all went to the photo booth and got our pictures taken by a photographer. They also had a photo booth with a bunch of props to try on. The booth is the kind that gives out a sheet with the four pics it takes of you in the booth. The trick for us was to make sure we picked up our pictures before anyone else could see them. We all play around while picking out props.

Brian and I went in as the third couple. I selected a feather boa as a prop and Brian picked a bowler hat and a big fake cigar. For the first picture, I sit on his lap and had my boa wrapped around his head. I pulled his face down in front of my tits with it. The next pick I pull him closer and he had his fake cigar pushed down my top between my tits. The third pick I moved so that I was straddling his lap and had my pussy pressing on his cock. He had his face buried in the middle of my tits and his hands on my tits holding them on the side. For the final picture, I reached up and pulled my halter up. I let my tits come out and pulled his mouth to my nipple. He started to suck on it just as I heard the click of the camera. I quickly pulled my top down and told him he better be quick and get those picks before anyone can see.