Best Laid Plans

I met Colleen on the train while commuting to my job in the city. It was one of those things where you see someone every morning and over time you have kinship even though you've never spoken a word.

After over a year of just nodding good morning we found ourselves sitting next to each other one day. I introduced myself and she responded with smile, but didn't seem interested in chatting so I left it at that.

It was several months after that during an unusually hot spring day commute home in a train where our car had no air-conditioning that she passed out from the heat. There were several good Samaritans, yes they still exist, they helped her.

We both get off the train at the same stop, so when we were walking to our cars I walked over to her and asked her if she felt better. She told me she was feeling light headed and was concerned about driving home. I offered to drive her and much to my surprise she accepted. She lived closer to the train station than I did so basically dropping her off was on my way home.

She had a beautiful home with a well manicure lawn and landscaping. I pulled into her circular drive way right up to the front door. I asked if her husband was home yet and she told me she's been widowed for 10 years. I asked if she wanted me to help her inside, but she thanked me and told me she was feeling much better. She said she would love to have me come over for cocktails sometime after work and I told her I'd love to. I waited until she was inside before I drove away.

She was more talkative during our ride than when we first sat together.

She's 53 years old, but looking at her you would think she was much younger. She wasn't slender, but you could tell she wasn't carrying any extra pounds, a woman with curves I've heard the guys say when referring to her body type. Her hair was a deep red and worn short. She worked as an administrative assistant for an insurance company and liked her job.

The next morning when we got on the train she sat next to me and thanked me again for the ride home. I asked how she got her car home and she told me her married daughter lives not too far from me actually, and she and her husband picked up the car and drove it to Colleen's house. She blamed her passing out on the heat and skipping lunch that day and she was back to normal now.

I told her a little about myself during the trip into the city, happily married, 45 years old, a son 16 and a daughter 14 going on 23. She liked that joke saying she a two daughters and one son, adding the boy was a dream to raise and her daughters were a handful. I told her I was from a family with 2 boys and 4 girls and my poor Dad always said he wished he had all boys. He said that jokingly, but we knew there was a lot of truth in what he was saying.

Over the next several months when possible, depending on the number of people on the train, we would sit next to each other and mostly just exchange small talk about work or family stuff.

I found I liked Colleen and my curiosity was killing me to know more about her personal life. She never mentioned if she was dating or any social gatherings she might be going to.

One summer evening on the train I mentioned my husband was on a business trip and my kids were going to the shore with my sister, so I was free for the evening. She asked me to come to her house for dinner. I suggested why not go to a restaurant so she wouldn't have to cook, but she said she loves to cook and can whip up something quick and easy, so I accepted. We drove to her home, each in our own vehicle.

Her home looked like it was laid out for a fashion magazine shoot, absolutely stunning. She told me decorating is a bit of a hobby for her.

She was a whiz in the kitchen and made us a delicious dinner. I'm a better bartender than cook, so I made us each a cocktail from a very well stocked bar in her solarium.

We ate, drank and the conversation flowed freely.

That's when I asked her if she has a boyfriend or girlfriend. She laughed at the girlfriend part, I decided then not to mention I was bisexual.

She told me she didn't see anyone for several years after her husband died from a heart attacked. Then she had a few dates, but she wasn't all that thrilled with the guys so she hasn't seen anyone in a couple of years. I kidded about not having sex for so long, but she said she has a full supply of toys and fantasies to keep her content.

The martini's seemed to be kicking in, for both of us. I went on to tell her I still masturbate on a regular bases and I have my share of fantasies too. She admitted she masturbated when she was married too.

She asked me what one of my fantasies was and I told her I love to fantasize about young men looking at me while I'm naked. She gave me an odd look so I thought I might have shocked her with my fantasy and I asked her if I did.

She said no, she was surprised because that's one of her fantasies and she thought she was a pervert for having such sexual thoughts and was surprised and pleased she wasn't alone.

We talked about some the scenarios for our young men fantasies and it was surprising how similar some of them were. The conversation was starting to get me hot and I saw a flush in her cheeks.

I then told her, martini's talking again, about a few experiences I've had with a young man that stays with us from time to time. I'd give him a few "accidental peeks" and would masturbate later thinking about him looking up my skirt or if I let the top of my robe partly open.

I asked her if she ever acted out one of her fantasies and she told me, no she hadn't. Her kids were grown so there weren't any younger guys around, plus she wouldn't know how to even go about it. She said it never dawned on her to do anything like that back when they did have friends over.

She then asked if I ever saw my house guest naked and I told her about the time I walked into his room and he was lying on top of the blankets asleep, naked with a hard on. She told me she though that was so hot.

She confessed that she has looked at some websites that featured young men, but she never seen a young man's cock, well, since she was young. I was getting the feeling she was fishing around for me to come up with a suggestion. The drinks weren't helping my thought process, so I didn't immediately suggest anything.

We realized we were getting hammered, so we had coffee and cake and chatted about other topics for the next two hours. When I was sober enough to drive we said our goodbyes and I went home.

The next couple of weeks we would sit together when possible, but the "fantasy" topic never came up again.

Then one day out of the blue she asked me in a whisper if I saw my house guest nude again since we last spoke. I told her I didn't, but sure would like too. She said she thought about it a few times and she wished she was lucky enough to see a young cock. This wasn't how she usually spoke, so I was guessing she was getting very horny. I told her I would try to figure something out so she could, if she would like me to try. She whispered that she would like that.

Her question and her acceptance to let me set something up was so out of character for her, like I said before, I just figured she was horny at that time and she probably now felt embarrassed she even brought the subject up, so I didn't pursue it.

A week later she mentioned it again and I told her I didn't act on it and I gave her the reason why. She laughed and said it was true that she was feeling sexy that day, but she's been feeling like that often since I told her about my experience.

She said she doesn't want to be involved in an orgy or any sexual situation, just thought it would be exciting to see a naked guy or be seen by one. She just needed a little spice in her life and she thought I could help; she didn't want this to be a project for me if I didn't think it was a fun idea. I told her it could be fun and I'll try to think of something, but also told her if she has any ideas to let me know too.

I knew the only real and somewhat safe way to put this together was to work something out with Jason. Jason is the 18 year old boy that stays with us when his parents go on business trips. We've shared a few voyeur, exhibitionist moments over the years.

Jason was alone in our den looking at television, so I took the opportunity to talk with him.

"Hi Gloria, what's new," Jason asked.

"I have a little favor to ask," I said

"Anything for you," he responded with a grin.

"I have a friend that wants to look at a young naked guy and have him look at her," I said.

Jason had a big grin on his face and said," is she hot?"

"She's very attractive, but this is just a show and look deal, you're not going to get laid." I said, "and Jason, don't give me a hard time, no pun intended, just do this for me and I'll let you look at me when this happens," I said.

"You know I would do it, I was just teasing you," he said.

"I'll give you the basics and you can wing it from there, I don't want her to know that you're aware that she wants this."

I sat with colleen on Monday and asked her if she could take Wednesday off and come to my house for the day. I told her it could be fun, no promises, but she might get what she asked me about.

On the ride home we were in different train cars, but she met me in the parking lot at the station and said she got the day off. I told her to bring her bathing suit and suntan lotion because we were going to lounging around my pool. She smiled and said it sounds good already.

She arrived at my house mid morning on a beautiful warm sunny day. It was the first time she was at my home, so I gave her a tour of the house. We walked to the rear of my home and I showed her the pool area and took her to our pool house so she could get into her bathing suite. I was already in my suite so while she changed I went to the outdoor bar and made us each a mimosa to start the day off.

We met back at pool side and I was surprised to see how great she looked in a bathing suit. It's not that I didn't think she had a nice figure, but she dressed conversably which really didn't show off her assets. Her breasts were full, flat tummy, round butt and long lean legs. She had a slight tan and a smattering of freckles. Her lavender bikini looked perfect with her red hair. I think I'll have to see if she's at all interested in being with a woman.

I was wearing my black bikini with a yellow wrap that goes around my waist.

We applied our suntan lotion and sat back by the pool to enjoy the beautiful day and our drinks.

"Gloria, so makes you think I can have one of my fantasies fulfilled today," asked Colleen.

"Jason the boy that stays with us when his parents are away is spending the next four days here. He always play's tennis today, then if it's hot he comes here for a swim," I said.

I no sooner said that when I heard Jason saying hello. When I looked over he was with his friend Chance, that, I wasn't expecting. Chance is also 18 and goes to the same high school as Jason. He's a very handsome, well built African American boy.

"Hi Jason, hi Chance, I would like you to meet a friend of mine Colleen."

Colleen gave them both a big smile during the introductions and I could tell they both liked what they were looking at.

Jason asked "is it alright if we swim today, we don't want to ruin your relaxing day?"

"No go right ahead we won't mind having some company would we Colleen?" I asked.

"Why would I mind being around two handsome men," Colleen said with a smile, the boys liked her response.

"One small problem ladies," said Chance.

"What's that?" I asked, already knowing the answer and guessing Jason filled Chance in on our plan.

"We don't have our bathing trunks, we usually go skinny dipping when no one is home," said Jason.

"You guys can get out of your tennis clothes in the pool house and when you're ready to jump in the pool we'll close our eyes okay?" I said.

"Sounds like a plan," Jason answered.

"Are you going to peek?" asked Colleen, as the boys walked to the pool house.

"You bettcha," I answered.

"This is so sexy Gloria and I haven't even seen anything yet," Colleen said while laughing.

"You can bet that they'll try to find a way for us to get undressed too," I told her.

"Okay we're coming out," Jason yelled.

"Colleen, don't even try to cover your eyes, let's just stare at them," I said with a grin.

Both boys paraded by us completely naked, at first they seemed surprised that we weren't covering our eyes, but quickly broke out with big grins and walked within 2 feet of us and then dove into the pool.

"Oh my God Gloria that was so sexy. I haven't seen bodies' like that in years," said Colleen.

"I know, from the looks on their faces I think they liked us looking at them too," I said knowing full well they boys loved every minute of it.

The boys swam around for a while then swam over to the side of the pool were we were sitting.

Jason said" ladies I thought you were going to look the other way."

"Jason honey, we just couldn't resist looking at two young handsome studs like you guys," I said with a wink and a smile.

Chance I found to be a little more, I guess you could say forceful, than other boys his age. Not in a pushy way and probably not even noticed by most, but I find his demeanor very attractive.

Chance spoke up and said" Gloria, Colleen it seems you ladies are one up on us."

"What do you mean?" I asked.

"Well you've seen us butt naked and you two are sitting there fully dressed," Chance said.

Colleen wasn't saying anything just waiting to see how this was going to work out.

I said" Chance we're in bikinis, you make it sound like we're completely dressed."

"True," he said," but you're both sitting down and we can't get the full effect of those lovely bodies."

Even though Jason and I discussed how the afternoon might go, Chance seems to have taken over the talking part.

I stood up and so did Colleen. We turned around and did some exaggerated model type poses while laughing and enjoying the positive comments from the boy's.

I then whispered to Colleen "let's give them something to really look at," and removed my bikini top. Colleen just smiled and took her top off also. I just love having people seeing me nude or partially dressed. Colleen seemed to be enjoying herself too.

"Oh my God, you women are so beautiful," said Jason.

Chance just gave me a look I can't describe, but it gave me a sex chill up my back.

We both say back in our chairs and off course left out tops off.

"Boy's, we'll stay like this, but find something to do besides just staring at us," I said.

"Hard not to just look at you," Chance said.

"Did you say hard?" said Colleen. We all looked at her, she laughed and we all joined in.

Jason said "I'm hard, I can tell you that."

"Can't tell honey with you in the pool," Colleen said.

"Why don't you boys get out of the water and show us," I said.

Without even replying both boys swam to the pool ladder and climbed out. They walked over to where we were standing, their beautiful young cocks standing straight up.

"Look how beautiful they both are," whispered Colleen.

"Enjoying your self?" I whispered back to her.

She just gave me a great big smile.

Chance walked right up to me and said, "Do you want to touch it?"

I looked over at Colleen and she already had Jason's cock in her hand.

I reached out and took his cock like I was shaking hands. It was so hard and thick and felt oh so good. I couldn't take my eyes off of it, but when I did and looked at Chances face he had a smile and a look like he had me hooked, frankly he did.

"You like my young black cock don't you Gloria?"

"Chance don't get too ghetto on me for Christ sake, your half Hawaiian and your parents are doctors, but yes I do like your cock," I said amused by him trying to be a gangster type guy.

I looked over at Colleen and Jason and damn if they weren't kissing. This little plan was going way faster than I ever thought it would.

However, that didn't stop me from giving Chance a long sexy kiss.

"Okay boys get in the pool to cool off please," I said without much conviction, but I had to slow things down.

The boys dove off the side of the pool and swam to the other side.

"Having fun Colleen?" I asked with a smile.

"This is so freaking sexy, I can't believe it's really happening," she answered.

"It's happening alright, but I didn't think there would be any touching and kissing, just us looking," I said.

"Touching and kissing is fine by me. I'm not sure if it should go further than that," Colleen said.

"Okay, we'll set the rules with the boy's, so this doesn't turn into a full fledged orgy. Do you mind getting completely nude? I asked.

"I was hoping we would," she said laughing.

"Hey boy's, swim over here," I yelled across the pool and they both swam over.

"Okay boy's here's the deal, we would like to spend the next couple of hours with you naked, but we won't have sex with you. Can you handle that?" I asked.

The boys knew in advance that I would be telling them that so I wasn't expecting a problem. They moaned and groaned for effect, but agreed. I know it seems odd to go as far as this and drawing the line at having sex.

I'm an exhibitionist, and doing more then that is pushing it, so I set up the rules when needed.

What Colleen limits are, she'll have to discover on her own.

The boys were in the pool next to us when I said

"Colleen, let's take our bottoms off for the boys,"

"Boy's do you want to see my pussy?" Colleen asked.

"Yes," answered Jason, and he could barely get that out.

We both wiggled out of our bikini bottoms with the boys looking up at us. Then we dived in the pool to join them.

Chance immediately swam up to me and Jason went right to Colleen. I don't know if they planned who would go with whom, but it worked out well as far as I was concerned.

His hands went right to my butt and he pulled me right up against his hard cock. God, it felt so good pressed against my pussy. The rules I just laid out for everyone a few minutes before already seemed impossible.

"Let me put my cock in you Gloria," Chance said to me.

"I can't let you do that," I answered.

"You know you want me inside your cunt, don't deny it," He said.

"Not now honey, some other time, I promise, "I said and then kissed him.

I looked around the pool to see where Jason and Colleen were and I caught a glance of them heading into the pool house. I guess I found out what Colleens limits were.

"God damn Gloria, look they're going to get laid and you're just making me promises," said Chance and he was pissed.

"Maybe they're not going in there for sex, let's go look," I said.

We went to the pool house and quietly walked in. Well so much for them not having sex because there was Colleen laying on a swim raft on the floor and Jason on top of her pumping away. Chance and I didn't say a word as we stood there watching them. At one point Colleen opened her eyes and saw us, she just gave me a big smile.

Chance stood behind me and was reaching around and playing with my breasts. I didn't have the will power to stop him. I was so horny. I was totally enthralled watching Jason, a boy I've been having sex fantasies about for years, getting laid in front of me. I was feeling kind of jealous, like he was cheating on me.

I guess that's why I got on all fours and let Chance enter me doggy style. Nothing was said between us to let him know it would be okay, but I guess when you see a woman raising her ass in your direction everything else comes naturally.

The four of us were screwing our brains out on the floor of the pool house. Great plan Gloria I was thinking to myself, but damn that cock felt good inside me.