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.
