This site is so helpful and fun.
My divorce was recently final and I had been dating some. While they were fun dates, the ladies just did not seem to be what I was looking for. This is a story about one relationship that grew into a very good friendship that helped me explore a part of my sexuality that had been suppressed in my marriage. This was about 2003 when internet dating sites were really starting to get going and chat was just becoming more popular as a way to connect with others. Y...... chat was my favorite, even though at times it was an empty connection because it was easy not to be truthful and really not get to know someone. But, it was better than watching TV or a movie. It also helped break down my defenses and inhibitions to deal with my shyness.
One lady I met on the internet lived in the area and she was interested in chatting. We connected and started chatting for an hour or more immediately. After many hours of enjoyable chat and over a number of days and weeks, we developed our own way to get to know each other better. We asked questions that could be anything and everything. The only rule was if you did not answer, you tried to explain why and we agreed that there would be judging. We accepted it was the way it was. She liked that a lot. Sometimes, the answer was too painful to discuss, but often we would open up on the subject over time. I learned many interesting things about her including that her Ex thought she was boring in bed and she wanted to experience oral sex and learn how to please a man. She felt this was a major issue that caused her divorce.
One of the last things she learned about me before we met was that I was in such a repressed marriage that now, I wanted to shed my clothes at any opportunity I would get to be naked. This was an area of my sexuality I wanted to learn about and explore. I thought I wanted to be naked with others and explore going to nudist camps and be nude around others in an acceptable way. But I was shy and inhibited. I almost always was naked at home after work. I wanted to try to be nude outside, but rarely had an opportunity. My chat buddy marvelled at these ideas. She asked if I cared if I was naked with others who were dressed and many other questions. I said I had not had much opportunity to be naked around others but that was what I wanted to learn and know about myself. I thought I would be comfortable being a nudist if I had the opportunity, but did not know how to go about it.
We decided to meet and setup a meeting at a neutral spot. We agreed one that was close to her and happened to be about two blocks away. We had a few beers and hit it off right away. Something was familiar about her and when we exchanged names we realized that we grew up only a couple streets away. Her name was Janice. Because of our age differences, we knew of each other's families, but not each other well. As previously agreed, we left the Bar and went home and as it turned out, she lived only two doors down from me so I walked her home, then returned to my house.
When I got home, I shed my clothes and checked the chat. She was there and asked if I was naked yet. I said I was. I asked if she was naked and that is when she told me her daughter, 21 y/o lived with her, so no, but she did only had a thin nightie on which did not hide much. That night we chatted for a long time about masturbation, blow jobs (She never gave one or tasted semen) and many other sexual things. It really opened up our ability to talk more freely now that we felt more comfortable. We also arrived at the mutual conclusion that our relationship was a friendship and not going to be romantic. But it was a very good friendship and something we both needed more than a relationship.
One night after getting home and we started chatting, she ask if she could walk down to see me. I said sure. She asked if I was going to get dressed. I said probably. She said, 'well, if you are going to try being a nudist, you have to start sometime!' I was now confronted with my own truth or dare. I took the dare by typing, 'ok, but please understand I don't know what to expect'. She said, 'I don't either, but I trust our friendship.'
When I answered the door, I stood behind the door so she could not see my nakedness. She walked in and watched me close the door. There I was naked and she looked and smiled. She commented that I was a good looking guy naked and should not be worried. I was still nervous and fearful but soon began to relaxed and to ease the tension tried to do normal stuff and offered her drink. I got us some wine and we sat talked. I grew hard as I moved around and talking and she asked very politely and tentatively if I would stand up for her so she could take a good look at my penis. I stood and moved closer to her. I was now very erect, pulsating and starting to drip pre-cum. She looked and asked if I was uncomfortable and I said was doing better and beginning to enjoying it. And then she smiled and said, 'No, I mean do you need some relief, if you want to masturbate that is ok with me and I would like to watch?'
When I started to get close I started to go for some tissues, but she took one last gulp of the wine and said, 'here, just cum in my glass.' I did as she held it and it was a pretty good load. I excused myself to pee and when I came back the wine glass was empty. I offered some more wine, and she accepted. I assumed she drank my cum because she did not seem to have moved from where she was sitting. I was then able to relax and talk about stuff and watch some TV more normally, as if I were clothed and sitting with a friend. After about an hour she left for home. This became normal for us for 3 to 4 nights a week and not everyone involved masturbation, I me nude. But on a number of occasions she did drink my cum in front of me and commented on how good it tasted. She told me it was something she always wanted to be able to do without it being gross. I thought I was really cool.
This went on for days combined with several more dinners and drinks. Then one night I logged on with and saw she was on and I typed, 'Hi, this is your naked neighbor!', but did not response right away like I usually do. Then what appear on the screen caused an 'oh shit' moment for me and it was, 'Hi, this is her daughter, Janie, mom is in the shower and I was using the computer for a while. I didn't mean to snoop, but she left herself logged in.' I typed, 'Oh, I am so sorry and embarrassed.' She typed, 'That's ok, she has been sharing stuff with me and I know you from going to school with your daughter. Everything is cool, please no worries.' I was a little worried and concerned still until I talked with Janice. It was cool with both of them.
Now her daughter joined us at the Bar with my invitation and dinner. We never discussed what we did in front of her daughter as I did not think it was appropriate. Then one weekday night, there was a knock on the door and through the window light, I could see it was Janice so I opened the door and realized her daughter was with her. I excused myself and closed the door, pulled on some short I kept nearby and opened the door and invited them in. I offered both some wine and they accepted and we all sat with our drinks. After a bit of small talk, Janice said, 'you know I have been sharing with my daughter what we do and chat about'. I asked everything? She nodded and repeated, 'everything;'. I nodded in fear of what was to come. She continued, 'I hope that is ok, I figured you knew anyway and she has expressed an interest exploring nudism also. So, is that ok?' This was the next truth or dare moment for me and I agreed because we are all adults and we could see how it went.
I was really nervous and a bit fearful. Janice's daughter, Janie said, 'I have done a lot of reading on naturism and nudism and I know it is normal for both men and women to be aroused and take some time to get......comfortable. So if you want to try, I would like to try also.' They went on to explain how Janie met a guy who is somewhat a nudist also and if she was going to have a relationship with him, she had to figure out if she wanted to be a nudist. So we had mutual interests and concerns. So she thought this would be a good first step. I agreed Janie stood up, and on her mother's count of three, I dropped my shorts showing my semi-erect penis and Janie pull off her summer type dress with nothing on underneath. She was clean shaven with full, wet pussy lips and her nipples were pert and aroused. Janice stayed seated and I asked her how come she was not going to join us. She begged out for now. They were both slender and pretty but Mom was about 20 lbs heavier. I got us more wine and sat. I tried not to look at Janie much, but she was so attractive and young, my erection grew.
At one point, Janice said, 'Well it looks obvious to me that you are both uncomfortable. Why not get some relief.' I looked at Janie and saw she was already beginning to spread her legs in response to the comment when before they were tight together. Then I said to Janice, 'You must join us, even it is just getting nude.' She did and she had nice full breast and her pussy was shaved also. I became so hard it was no going to take much. I stood and when I did, Janice sat in front of me and held out her empty glass. Janie was rubbing away and making noises. While Janice held the glass with one hand, started to rubbed herself as I pumped. Oh wow was this so cool. We all climax around the same time and my cum was in the glass. Janice said, 'cheers' and drank it down in front of her daughter and I Wow....... I was on fire in no time.
Mom and daughter and I were routinely nude together and now and then one, whenever we feel the need, we masturbate, sometimes together. We enjoyed our nakedness and the ability to masturbate when we had the urge.