A number of years ago when I was about 17 or 18 a met a girl that was a year or two younger than myself and lived across the street from my brother. I went to my brother's house often and ended up dating this girl for the summer.

This girl was no raving beauty but I enjoyed our time together. She lived with her grandmother. She never mentioned her parents and I didn't ask. I just know that it was just her and her grandmother.

I remember that when I picked her up for our second date, she wore a dress. Before we left to go to the movies, her grandmother grabbed the hem of her dress and lifted it right in front of me exposing her white cotton panties. The girl quickly pushed her dress down as her grandmother scolded her and made her go to her room and put on a girdle. I think her grandmother felt that this was a sort of chastity belt for her. At any rate it really embarrassed the girl.

After the movie we went to my favorite parking place. Neither one of us could wait to make out. It was obvious that this girl had never touched a cock or even been felt up herself. I tried to get my hand in her pants (girdle) but it wasn't going to happen. She would let me rub her crotch a few times, though, through her dress. She didn't balk though when I pushed her hand to my crotch. I had to help her but she finally got the idea. As I laid on top of her, I pulled my pants down and she rubbed my dick until I came on her dress. I apologized a number of times but she assured me it was okay.
I explained how she had made me feel and told her she could do that to me anytime. I remember sitting next to her in the car with no pants on while she was fully dressed. She finally asked me if I was embarrassed sitting there like that. I told her that I wasn't because I thought maybe she didn't mind it. She said she really didn't. It was the first time she had seen a boy with no pants and she was enjoying it. When I told her she could jack me off anytime she wanted, she didn't hesitate to reach down and start playing with my dick again and got me off a second time. I was exausted and she was grinning from ear to ear.

The next day when I went to her house, her grandmother was gone. We turned on the TV and I put my arm around her. She automatically reached down to my crotch without any coaxing. She didn't want any sex. She just wanted to jack me off. I quickly got out of my pants and stretched out on the couch. I was in heaven. She got me off twice again that day. She never took her clothes off but she sure like to get mine off. She loved seeing me come.

The following Saturday I showed up at my brother's house. He asked me if I would go outside and water his plants while he finished some inside work. I picked up the hose and watered his garden. Later that day I went across the street to visit the girl and her grandmother. They were both giggling like schoolgirls. When I asked what was so funny, they at first wouldn't tell me. Then the girl's grandmother finally said that they watched me watering my brother's plants and from where they were watching, it looked like I was peeing on the plants. They knew it was a hose but it looked like I was holding my "weiner" as her grandmother said. They both laughed and laughed.

I told them that I wish it was as big as that hose. Then her grandmother started in on me asking "Well, how big is it?"

Finally, I just said big enough. But her grandmother wouldn't drop it. She even asked if I played with it to make it bigger. I think she was totally embarrassing her grandaughter. Then she popped the question and asked if she could see how big it was. I couldn't believe how bold she had gotten. I think she had a couple of beers in her. I told her no. Then I couldn't believe my ears. She said that if she could see it, she would see how big she could make it and make my little stiffy shoot. I starred at her and asked if she would really do that for me. I was always up for a handjob but this was bizarre.

She assured me she would. Now I could see that her grandaughter was a little pissed but knew better than to say anything. She just kept her mouth shut. Her grandmother just came over to me and undid my belt letting my pants fall to the floor. She bent down and pulled them completely off leaving me standing there in nothing but a tee shirt. I remember my dick being half hard. Then she sat down and both her and her grandaughter just starred at my dick. I started to protest but she just wanted to look a while. Then she had me lay down on the couch and had the girl go get a towel. Her grandmother pulled a chair up next to the couch and took the towel from her grandaughter and layed it on my stomach. The girl sat at my feet on the arm of the couch with her leg tucked under her.

Her grandmother started jacking me off. She cooed at how it was growing. I'm not particulaly big and the grandmother kept calling me a little boy. She would say things like "look at your little weiner grow". I had closed my eyes and this woman knew what she was doing. When I opened my eyes and looked at the girl, her eyes were fixed on my crotch. I could see up her skirt and she noticed this but her grandmother didn't. When she saw me looking at her panties, she slowly slid it up so I could get a better view.

Her grandmother slowly jacked me. She took her left hand and cradled my balls. Then she did something that about made my eyes pop out of my head. She slowly massaged my anus. I had never had this done before. After about a minute of that she curled a finger and pushed it in me about an inch. Her grandaughter saw this and put her hand over her mouth. In about five seconds I had the most intense orgasm I ever had. I normally just dribble a load of come but this time I shot all over the towel on my stomach.

She knew how to pull every drop out and it was obvious that she was proud of herself. I just laid there a minute with my legs apart giving them a show and then asked for my pants. She rejected that request. When I protested she explained that I had nothing to hide since they had both seen my weiner and watched me make my "little" mess. She also explained that if I left my pants off she would do it again as soon as I felt up to it. Needless to say, I took her up on her offer.

This is a true story as well as I can remember. There is more to it but this is the condensed version.