Lady Next Door
Ms. Johnson, the lady next door, asked me to clean her pool once a week. It was an easy job; she had a machine that did most of the work. I only had to push it around a little and then clean the filter. The pay was decent, but I worked for reasons other than money. When I usually arrived, Ms. Johnson would still be swimming. She always wore a white bathing suit and when it was wet, I could see her nipples and hairy mound through the thin material. That was more than enough for a horny 18-year old guy like me, even if she was 45 and 6'1" and 190 lbs.
I had been making some progress with my girlfriend who, like me, was about to graduate high school. She was the prettiest girl in school and I being only 5'5" and 125 lbs was happy with Susie. We had sex, but she wouldn't satisfy me the way I wanted. I wanted to be fucked with a strap on. She would play with my cock and ass, but nothing else. I felt frustrated night after night. I had to masturbate just to feel some release. We were going steady and planning on attending the same college in the fall, but she had these damn rules. I ended up writing about my fantasies of getting fucked with a strap on in a notebook. I often carried it in my pocket, for those moments when my time with Susie left me lusting for more.
It happened one week, when I had gone over to her place to clean the pool, Ms. Johnson got out, I had my looks at her and that swimsuit, and she went into the screened-in porch. Once inside she unhooked the straps on her bathing suit, pulled it down, and dried off with a towel, and I got an even better look at her body.
It happened again the week after.
The third week I was ready and I was almost certain that she was doing this for me to see her. I watched until she put on a big fluffy white bathrobe and then I went over and knocked on the screen door. She opened it quickly, her robe giving me nice view of her cleavage.
"Come in Bobby, come in," she said, "Can I get you something to drink? Maybe a beer?"
"Sure Ms. Johnson, a beer would be great."
"Oh don't call me that. Call me Gail. Everybody else does," she said with a smile as she walked into the kitchen and opened the fridge.
I had no doubt that she wanted to show me her breasts as she bent over to get the beer off the bottom shelf. Her robe was open at the top and she made no effort to close it. I was starting to get a bulge in my shorts.
We walked back out to the porch and she motioned me to a chair. She sat down across from me and crossed her legs. Her robe dropped open, showing off a generous amount of thigh. She caught me looking.
"Do you like my legs?"
I must have blushed because my face felt funny. "Well ... I ... yeah, I guess."
She placed my notebook down in front of me. I must have dropped it last week while cleaning her pool. "I saw you looking at me dry off. You left this book your last visit and I have already read all about your strap on fantasies."
I had guessed she knew I was looking before, but I was still embarrassed. I said nothing.
"Here," she said, "take a better look."
With that, she stood up and took off her robe and stood there bare breasted with a strap on. It was the first time I had ever seen a woman with a strap on and she just stood there letting me gaze. Then she lifted her arms up and put her hands behind her head, pulling her elbows back.
She had beautiful tits- big and creamy white with luscious silver dollar nipples that were starting to stand up. Her belly was not as flat as Susie's, but her tits had to be twice the size. Her pussy had thick, curly brunette hair, so different from fair haired Susie. My cock was rock hard and straining to be let loose.
"Your girlfriend is still young. She doesn't have enough experience in fucking yet. Come over here, Bobby. Come over here and feel of my tits."
As though I were in a trance I got up and walked over to her and began to feel of those beautiful, heavy tits. She reached down and started to massage the bulge in my pants. She opened my belt and unzipped my shorts and let them drop to my ankles with my boxers. My cock sprang up hard and ready and she took it in her hand and stroked it.
"Here, baby, let me put one hand down here," she said as she moved one hand down to my ass. She put my right foot up on the chair, spreading my legs. Then she put her fingers on my asshole and shoved them inside.
I started to moan as her finger moved in and out of my ass. It was a lot bigger than Susie's finger. She was kind enough to lubricate my tight ass with Vaseline, which made it wet and slippery and I thought about how easily her cock would slip into me.
She pulled me down on the soft mat covering the floor and positioned me between her legs and she began to suck my cock. I had persuaded Susie to do this a couple of times, but Gail's mouth was hot and her tongue working on the head of my dick felt like nothing I had ever felt before, she was experienced. I thought I was going to come, but she caught my hand and made me sit on her. With her cock in her hand she positioned it between my asshole and made me slide down on her. She started to fuck me. This is what some of the guys at school had talked about. It felt wonderful as the toy slid in and out of my ass. But I couldn't hold it any longer, my cock stared to tremble and I started to pump sperm onto her thick thighs.
Gail caressed my face and kissed me gently on the mouth. . I started to get up but she pulled me gently back down and sat me down on her thigh. She reached and started to play with my balls very gently and after only a minute I was hard and ready.
Then she made me sit on her cock facing her. I started to ride her and pump my hips to meet her with every thrust. She was fucking me hard and I was thinking about cumming again when I started to moan and hump harder. Then my whole body started to tremble as I felt her entire cock slide into my ass. I felt full; it was a feeling I had never felt before and I looked at her face. Her eyes were closed tight and she seemed lost. I had heard about it from the guys at school. This must be what it feels like to be fucked by a woman with strap on. She kept pumping me harder and deeper and I quickly had another orgasm, spilling my load onto her breasts. I collapsed on her body and rested.
It was at least full ten minutes before she spoke. "It was your first time, wasn't it?"
I was embarrassed. I wondered if I should I try to brag. But I figured she would know. "Yes it was my first time. I've played with my girlfriend Susie but she won't ... ah ... you know."
Gail chuckled. "She won't fuck you."
"Yeah," I said, "she won't."
"If you treat her right she will," Gail said smiling. "You have to know how to do it. It's hard for a girl to do it the first time. So many people have told her she shouldn't."
"How do I treat her right?"
"Don't worry, baby. I'll show you. She'll be willing to fuck your ass for you any time you want before the month is out." Gail laughed as she said it and reached down to play with my ass again. "You'll be using this lovely thing like an expert before you know it."
We got up and she put her robe back on. This time it covered her properly. I picked up my shorts and got dressed. She came over to me and planted me on her hip and kissed me gently on the mouth. Then she whispered in my ear, "Come over here tomorrow afternoon. I'll give you your first lesson on how to treat Susie right."