This is a true story and happened pretty much the way I tell it.
I was 17, a junior in high school and really getting into being the team trainer for the school. I wanted to go to a camp that was being put on by one of the guys that worked for a professional football team but Mom couldn't afford to send me. She said if I could save enough I could go. But how the hell was I going to save 400 bucks out of my allowance and what little I made from my paper route. So I decided I would see if I could get people on my paper route to maybe donate. I worked on the project after school and the first couple days raised 50 bucks. I was encouraged and could almost see my self at the camp.
One afternoon I was headed home when I passed Mrs. Wilson working in her yard. I stopped and chatted with her and then asked if she would help me. She looked at me and smiled and said
"Would you like a soda?"
I excused myself and said I really didn't have time, that Mom was expecting me for dinner in about 10 minutes.
"Well come in for just a minute," she said and led me into the house. I felt sort of funny because she was acting sort of funny. She looked me over and asked me to turn around and then took a tape measure and measures my chest and head and wrote stuff down.
Finally she said, "Come back around 2 Saturday afternoon and I'll see about helping you out."
Then she walked me to the door and I rode my bike home, one completely confused teenager.
Saturday afternoon came and promptly at 2 I rang her doorbell.
"Come in Byran," she said as she opened the door. "I am so glad to see you. I wasn't sure if you would show up."
"You said you'd see about helping me out so of course I would come back."
Let me tell you about Mrs. Wilson. She is mid 50's with hair just starting to turn grey. She had taken care of herself over the years and is still a very hot woman. She has been a widow for about 3 years and to my knowledge hasn't gone out with anybody.
Mrs. Wilson took my hand and led me to the living room. On the coffee table was a soda for me and a glass of iced tea for her. Then she explained.
"My birthday is today and I want to buy myself a present. And you are it. But you have to promise that anything that goes on here today will be between just the two of us and that you will do anything I request. If you do, I'll give you $300 dollars toward the entry fee for your camp."
I was blown away. I couldn't imagine what she wanted me to do that would be worth $300 but who was I to argue. Of course I readily agreed.
"If you are very, very sure, OK," she replied.
I said I was more then sure.
"OK then, follow me."
She led me down the hall and stopped before a closed door.
"On the bed are some cloths I want you to put on. When you are dressed come down to the room at the end of the hall, I'll be waiting."
She turned and went on down the hall. I opened the door and went into the bedroom. On the bed were some girl's cloths. Bra, panties, skirt blouse and wig. I didn't understand but for $300 I didn't need to. I stripped and started to put on the cloths. I had a hell of a time with the bra but finally figured it out. I picked up the false tits and looked them over and then put them in the cups. I was beginning to feel sort of funny and started getting a hard on. Then when I slipped the panties on I really got hard. The blouse and skirt were easy but I didn't know what to do with the bulge in the front of the skirt. I guessed I'd just have to wing it. Then I put on the wig and checked myself out in the mirror. I looked just like a guy with girls cloths on. I don't know what I expected.
I looked into the open door to the other room and Mrs. Wilson was spread out on the bed in a sheer red short nightie and matching thong. My cock got harder yet.
"Oh come in my darling little girl," she said. "Come lay by me."
I could see the dark nipples that poked into the fabric of her nightie and could see the small patch of hair just above her pussy. The money for my camp was the furthest thing from my mind. I was a horny teenager looking at a beautiful woman that in my mind was just begging to be fucked. I didn't care what I had on or what she had in mind, I just wanted to get on with it.
I did as Mrs. Wilson instructed and laid next to her on the bed, face to face. It was really weird cause all the time she was speaking very softly to me she was rubbing my body. Her hand was all over my face and then down across my chest, squeezing my falsies and then down to my crotch. She talked crazy stuff about how beautiful her little girl was and how I was growing into a very sexy young lady and then when her hand started rubbing my cock, how large my play thing was. But I could care less.
I decided to find out how far she would let me go so started playing with her tits. I had never played with a girl before but had talked a lot about it with my friends. And it just seemed natural.
"Oh yes my little darling, play with your mommies tits. Squeeze them and pull on the nipples," she whispered.
The more I played the more she liked it. Then she said,
"Take my nipple between your lips and suck."
I willing did as I was told and really got into playing with one tit with my hand while sucking on the other one. She had her hands on my head pressing my face hard into her tits. I continued to suck on one and then the other as my hand worked its way down her stomach and into her play zone. I sort of laughed to myself as I thought, go directly to jail, do not pass go.
I slide my finger lightly between the lips of her pussy and she lay back, spreading her legs to give me full access. As I explored this unknown territory she instructed me on what to do where. Soon I had zeroed in on her clit and she was flopping around and telling me what a great little girl I was to give her mommy so much pleasure. Then she pushed on my head and told me to use my tongue instead of my finger.
Now I had heard of a guy eating a girl's cunt but wasn't real sure I was interested. But for 300 bucks, what the hell. I didn't think it would kill me. So, I moved down between her legs. I guess instinct took over because I licked the inside of her thighs and all around here neatly shaved pussy before penetrating her love canal with my tongue. What ever I was doing must have been right because she was moaning and groaning and saying yess, yesss, yessss and don't stop and other stuff.
She put both hands on my head and started pushing her pussy hard against my face. Then she hollered, "I'm going to cum, oh yesssss, I'm cumming."
As she said that she held my face in her cunt and started shooting. My mouth was filled with hot liquid. At first I thought it was piss but then realized she was cumming. I drank at her fountain till there was no more. She realized the hold on my head as the convulsions from her climax resided. I was in a daze, not really sure what had just occurred but knew for sure that she had enjoyed it as much as I had. I moved back up beside her and cuddled, placing on hand on a tit.
"Oh my darling little girl, that was wonderful," she whispered. "So wonderful." With that she started rubbing my boner and said, "Now it's my turn to give you some relief."
Mrs. Wilson gently rubbed her hand across my chest and played with my nipples for a bit, rubbing and biting and sucking. Then her hand slipped down to my crotch, hooking my panties with her fingers as it went. She pushed them down and lifted a leg so she could take them off. Then she started the most wonderful routine on my hard boy cock. I looked down as she worked and thought it was bigger and longer then it had ever been. Her fingers stroked as her tongue licked. Then her lips incased the head and hugged it gently as she lowered her face down. I could feel her chin against my balls as the entire shaft disappeared down her throat. Of course I ruined the whole thing by almost immediately shooting my load in her mouth. Mrs. Wilson looked up at me and licking her lips said,
"You are very tasty my little darling."
She slipped up by me and pressed her lips to mine. Then her tongue pushed between my lips and found mine. She had saved a little of my cum for me and let it drizzle into my mouth as we kissed. Then with a start she said,
"Look at the time. It's after 4 and my kids are coming at 5 to take me to dinner. I've got to get moving."
I headed down the hall to the other bedroom to change cloths. When I was ready I met her in the living room and she handed me 6, fifty dollar bills. I looked at her and smiled and said,
"This is too much."
"Keep it," she replied.
"But really," I said, "I think I should work this out."
She smiled and asked, "On what terms?"
I grinned and said, "How about a dollar a time?"
She laughed and said, "OK, see you tomorrow."