This story goes back to 1987, back when I was a youngish widow. My husband had tragically died in an accident two years earlier, and I was able to use his $100,000 life insurance to pay off our house and put money aside for our two sons' college education. I was 38, too young to be a widow with grown children, but I got an early start.
It was a particularly lonely summer for me. My second son had graduated from High School and joined my other son for a summer of tree planting. They made good money, but they worked in remote camps for months on end. Both would be away in college in the fall, and I knew I had lots of adjustments to make.
I worked in the office of a factory, and this summer they had shut down for some major refits and laid off many of the workers, including me. My job would re-start in September, and I had enough money set aside that I wasn't hurting.
On a Tuesday in June, I attended the widow's support group that I often went to. It was good to be with other women in similar circumstances. During the social time I got talking with Marie. She had an 18-year-old son who was knew my youngest.
"I don't know how to deal with David" said Marie, "I know he's still hurting from his dad's death, but I wish there were something I could do to get him out of the house and into a different mindset! He spends all his time watching TV and reading, but he really doesn't see anyone. He's starting a summer job next month, but I wish he'd do something more! Add to that, I really have a hard time talking to him about relationships. I don't know if he would like a girlfriend or is just too shy! He might be gay for all I know."
"That's tough" I responded, "What about you, are you able to do what you want to do?"
"I'd like to go visit my sister, but I'm not comfortable leaving David behind, and he really doesn't want to go." Said Marie.
"With both my boys gone, I could do with someone else around home." I suggested. "Any chance he'd like to stay with me for a week? Perhaps he would open up a bit more with someone familiar but not related?"
"I like that idea," said Marie, "but I don't want to impose on you. Are you sure about that?"
I stirred a little inside. My loneliness was a hole that needed filling, and a reserved young man could be seen as a challenge. I'd love to give him a chance to open up, possibly even express his sexual feelings.
And so it was settled. On Friday evening, a week later, Marie came by with David. I'd met him before, but I'd forgotten how handsome a young man he had become.
"Welcome David! I hope you don't mind keeping me company for a week."
"Thanks Mrs. O. If you have cable TV and a comfortable place to read, I'm sure I'll be fine here."
"We've got a VCR as well," I suggested, "Perhaps we can watch a few things together."
"Mom works all the time, I guess I'm not used to watching movies together, but I'm sure I can handle it." Responded David.
Marie and I talked for a few minutes, then she headed out for a well-deserved break with her sister.
"Let me show you around, David." I offered. "You'll be staying in the guest room. I've got a few clothes stored in here, but there should be plenty of room for your things." He dropped his small backpack on the bed. "You didn't bring a lot with you, did you?"
"No, Mrs. O, just a few clothes and some books."
"Can you call me Linda? That would make me more comfortable, we're both adults you know!"
"OK, Mrs. O, I can try to do that."
"Let me show you the rest of the house. Did you bring a swimsuit? We've got a pool in the yard."
David sighed. "I didn't. I should have, I didn't know you had a pool. I do like the water."
"I'm sure we can find you something to wear." I suggested as I winked at him.
I gave David some time to settle in as I puttered around the house. When it was getting dark, I knocked on his door. "David, would you like to watch a movie with me?"
"I suppose I could do that, I'll be down in a few minutes."
I looked through my collected of videos. I had some pretty raunchy ones, but I wanted something that was X rated but actually had a plot to it. I wondered how much he could open up.
David came downstairs wearing his Jeans and a t-shirt. I had gotten comfortable, wearing a thin shirt and matching pyjama shorts. I wasn't exactly showy, but it wasn't hard to tell that I was not exactly constrained.
"Would you like a beer or glass of wine?" I asked.
"Um, I'd be happy to try a beer." David responded hesitantly. "I've only had a couple before, but if you are offering."
We started the movie and chatted a little. As the movie went on, and started to get more sexual, I could tell that David was getting a little flustered. When the lead actress poked her head into the room, then walked in topless, David was very unsure how to react. I could tell he was very aroused, but he was also uncomfortable.
"David, you don't seem to be very comfortable, how come?" I asked. "It's perfectly natural to find this attractive, and nobody is getting hurt, why does it seem to bother you?"
"I know Mrs. O, but I'm so conflicted right now. My father was, shall I say, a prude. Every time I see something like this, I hear him lecturing me on how evil it is and how it will rot my brain -- and how I will end up in hell if even let myself think about women like this!"
"I'm sorry David! You are a young man, and it is perfectly normal to react to attractive women! If you are going to hell because of it, then every other man will be there with you! Do you want to keep going, or are you too uncomfortable with the movie?"
"Thank you, Mrs. O. I really don't believe the things he said to me, but it is really hard to move away from them. My biggest discomfort is actually my jeans. Do you mind if I just wear my boxers?"
I laughed. "You'll be wearing about the same thing as me!" as I pressed play.
It wasn't long before there was a loving, extremely sensual bedroom scene, all under the covers. David was mesmerized and he also had quite a tent in his boxers. The movie continued, making me very horny, and I couldn't imagine what it was doing for David.
"After that, I suspect you might want to go upstairs and relieve yourself!" I suggested.
David blushed. "I can't pee like this, no matter how full my bladder is!"
"That's not what I meant David!"
"What do you mean then?" he asked.
"I though you would want to relieve the sexual tension in private." I suggested, not sure how to phrase things.
"I, um, I'm not sure quite what you mean." He replied. "Do you mean like, a wet dream? I have those sometimes."
"Well, no, I was thinking of masturbation, do you do that?"
"I'm not really sure what that is Mrs. O. Every time I've heard about it, I was told that I would go to hell if I did it -- and I'm not even really sure what it is!"
I didn't know how to respond. I didn't realize how sheltered David was. No wonder he didn't get out much.
"Well, I think we should go to bed David, it is getting late."
I knew I also wanted to have a session with my vibrator before I fell asleep.
I put on my satin nightie and went out to brush my teeth. David was coming out of the bathroom, wearing just his boxers. "Goodnight David! Can I get a goodnight hug?"
The embrace was soft, but I could feel his erection in my stomach through my satin nighty.
"Sleep well!"
"Goodnight Mrs. O!"
An hour later I was woken by the house shaking. A violent thunderstorm was going over. I have never liked thunderstorms, and I like them even less by myself.
"David, I'm scared of the storm, can I crawl in bed with you?" I asked as I crawled under his blanket.
David didn't move, I could hear strange sounds coming from him as he tried to speak but couldn't find the words. I quickly discovered why as I snuggled up behind him.
David was wearing a bra and panties.
"ooh" I said, "you found my overflow of underthings I see. How does it feel to you, it sure feels good to me!" I said as I rubbed his satin clad bum."
"Mrs. O, I, I, I, what do I say, I'm so embarrassed right now! I'm wearing your clothes without permission, and it feels so incredibly naughty yet so, so good! When you climbed in bed, I thought that you were going to kick me out of the house and send me out into the storm, and all of a sudden you are teasing me. I, I'm just not used to anything like this!"
"David, it is perfectly natural to want to try new things! There is no reason to be embarrassed!"
Just then the window lit up and the house shook with a huge boom of thunder.
"Turn around and hold me David, I don't like thunder!"
The main thing I noticed when he turned around was that my panties were not very successful at containing his erection. I wanted it so badly but didn't want to push him too fast.
"David, I can help you with that if you want to be more comfortable" I suggested.
"How?" asked a very sheepish David.
"Like this" I answered as I gently wrapped my hand around his penis and started to rub him.
David was breathing heavily. "Mrs. O, that feel so good! Oh my God, I've never felt like this before!" and with that, David had his first intentional orgasm, coating his belly with rope after rope of semen.
It took him a minute to catch his breath. "Now what do I do Mrs. O?"
"Go to the bathroom and clean up, leave the bra and panties on though, I like that! And you can wear my underwear all you want this week."
Together we fell asleep, wrapped in each others' arms as the thunderstorm blew over.
I woke up first in the morning. The sun was shining, and I knew it was going to be hot. I slid out of bed and went downstairs to make coffee. I wasn't there for long before David came downstairs.
"I hope you don't mind me borrowing your robe, I didn't want to get dressed yet." He said as he pulled the light green satin robe around himself. He was still in the bra and panties.
"You look comfortable." I suggested.
David laughed. "Well, it feels good, whether that is the same as comfortable, I'm not sure. Is the coffee ready?"
"Coffee coming right up! Would you like pancakes or bacon and eggs for breakfast?" I asked.
"I usually just have an Eggo or two, but if you are making pancakes, that would be great."
David and I talked about a lot of things over breakfast. Me wearing a thin satin nightie, him wearing a satin robe over a bra and panties. He relaxed more and we talked about his lack of sexual experience, and how he felt so scared to have gotten to this age without experiencing anything, but also feeling vestiges of his late father's wrath when he ventured into anything sexual.
It was late morning before we were ready to move on. "It is hot out David; shall we spend it by the pool?"