The Lady Next Door

I moved into a new suburban neighborhood. I'm not the real social type so I didn't go out of my way to meet the neighbors. I'm in my mid 50's and I noticed that I did have a lady living next door that was probably about my age, but she could have been a little older. I saw the young children that visited the house during the holidays, so she could have been a grandmother but didn't have the body for it in my mind. I hadn't really met her yet, just a glimpse and an occasional wave when I went out to grab the mail or get the newspaper.

Anyway I was working in my upstairs office one afternoon. I saw my neighbor setting out a lawn chair. My room oversaw part of her backyard. She put a towel on the chair and laid out in her bathing suit. I watched for a minute and then went back to my work. But moments later I was looking again as she took out the tanning oil and began to rub it on. The usual, the arms, shoulder, face were getting oiled. I looked away but was drawn back for another peek. She undid her top and was oiling her breasts. It was being done so erotically I could see how much she was enjoying it as well. This was clearly more than just sun protection involved; it was an erotic process. My god, she had her nipples in each hand rubbing them, then her breasts and back to the nipples. I was getting quite hard.

But it was just starting, as now she now poured a puddle of oil on her midsection and began working it in. Her hand casually slipped into the top of the skimpy bikini bottom she was wearing. Cleary it is not a spot that was going to see much sun unless I got a real show, I thought with a real grin on my face. Those oily palms began to really put some oil on her thighs as she worked it in quite roughly. Her hand now began to pull aside the crotch of the bikini bottoms. She was working her hand on herself in a very brisk manner and obviously enjoying it. I found myself watching intently her every move. My god I could see her.....she was waving at me and smiling......

My head snapped back and I left the room. My heart was racing. I certainly felt like a boy that had his hand caught in the cookie jar. When I caught my senses I began to think rationally. She was smiling when she waved, so I'm probably not in trouble. Anyway I hid out for a number of days. I think I would have been too embarrassed to meet her eye to eye right now. If I left the house, I left early and came back late. A few weeks went by, but the thoughts of what I saw kept running through my mind. I had fantasized about it so many times I wasn't sure what was fantasy and what was reality. The thought of meting her face to face was more one of humiliation and shame rather than erotic desire. Yet she had been the source of numerous orgasms for me.

The doorbell rang Saturday morning. I saw the Fed Ex truck had pulled up. I was expecting a delivery so I went to answer it. There she was holding the package.

She just walked in the house coming very close to me." I told the fed ex guy I would drop it off for him. I don't think we've ever met. Hi I'm Jenny. I thought you would come down and help me out the other day, but you just ran off. Your not afraid of me are you?'

Err...Uhhhh.....no. I felt my face burning red and that confident look I was trying to put on my face was nothing more than a silly smile and I'm sure a real sheepish guilty look. She looked me dead in the eye. She won, I glance downward, hard to meet her glance eye to eye. But she was so close it was if I looked right down her blouse on purpose.

Oh so these are what you were interested in, she said, opening another button on her blouse. My kind of guy, maybe we should get together and get to know each other, she said awfully seductively.

Yeah sounds great. I said wanting to desperately break this spell she had over me. Maybe we could do a dinner and a movie sometime, I said.

Not exactly what I had in mind, she said, but sounds good. She said. I'll see you this evening at 6. She winked at me as she turned and left. It was strange being told when we were going out.

As she walked off I couldn't help but stare at her ass as it wiggled out my door. She turned her head and caught me staring again. She just smiled and let out a loud laugh..

Tonight I thought. It was if she could read my mind and see through walls. She could see all my perverted little thoughts. How did she know when to turn around and catch me staring at her ass?

At promptly 6, I was at her door. I had made reservations for a restaurant and had the movie listings in my hand.

She was wearing a very short skirt and a very open silk blouse. I started some easy talk.

She interrupted me.... did you enjoy the show in the backyard the other day? MMMMM

I laughed...I don't know what to say, I...

A simple Yes, Maam or No, Maam will do.........

There was a quiet silence...Well did you enjoy it? She asked again

Yes

Maam, she replied.

Yes, Maam, I quickly followed.

Good boy. You know I may be a little older than you but I am not a prude. Do you find me attractive?

Yes Maam. My face was a burning red yet again, and it seemed to just egg her on

Would you like to fuck me?

Again the quiet...... With a lump in my throat, I didn't know what to say but I answered... yes maam. It came out in a whisper and a most terrified tone. She knew where she had me and where she was taking me. The only problem is I didn't know where it was going. I felt like a freshman schoolboy out on his first date with an older woman, but she is many years ahead of me. I tried to exude some confidence and make some reply. But her reply floored me and had me on the defensive again.

Do you think I'm easy? Her voice tone changing as she said it.

Oh..No...No, Maam. I just thought.....well....you said....but I really ment...I'll do whatever you want.

Did you jerk off while you saw me in the backyard?

Red faced and feeling like a little boy........no maam, I said shaking my head. I think I really wanted to leave. I felt very uncomfortable. I was being tossed around at her will. I was like a small boat caught in a violent sea that she had stirred up. The sexual adrenaline and yet her intimidation and humiliation that she was causing me just with a few words were addicting. Why didn't I just get up or say something. It was like my jaws were wired shut and my body in a cast. But when she asked, I answered. When she exposed I looked. When she shamed me I felt humiliated.

She laughed and hugged me bringing my head to her breasts. You boys are all the same. I would love to have you spend the night with me. Don't be ashamed. Besides I think you fibbed to me about playing with yourself....mmmmm....and I don't want to send you home to take care of it by yourself. But since I'm not easy... I want you to prove to me that you just won't fuck me and then tell the whole neighborhood how easy I am. I'm sure that makes sense to you.

No.....Ma'am I wouldn't dare

Well that's good but I think you already have shown me you have an ability to fib about things. Then you won't mind a good spanking to prove it to me will you?

What?

Come on you're not that naive I'm sure you know spanking games are a form of foreplay. I'll bet you enjoy it and shoot you're cum all over my lap. Now if you want to tell all the neighbors and friends about our sex life I can tell them about your spanking. Sought of makes us held at each others mercy in a sense.

I don't......

Come on how can you loose. If you get to cum then it must have been a great spanking. If not, I'll give you a blowjob. That sounds like a fair bet. You do like blowjobs don't you?

Yes.

Great, it's a bet.

A bet? What did I just agree to I asked myself.

If my naughty little boy doesn't have an accident and shoot his nasty stuff all over my lap he gets a world-class blow job from your truly; if not you owe me another hot spanking.

You mean a second spanking?

Sure your certainly not one of those little sissy boys that is going to shoot on my lap while being spanked. Or Are you? What are you worried about. So you're probably just going to get a little spanking, a great blowjob and you can fuck me later. Any problems with that scenario? Ok then let's go upstairs and take care of that spanking and then we can make it in time for the movie. That will leave us time to play after the movie.

She made it seem like she had done it a thousand times as she lowered my pants and underwear. A firm grasp of my ear led me across her lap as she sat across the end of the bed.

It was an erotic sensation to be there across her lap. But it was humilliating to be led like this. No, the real humilliating part is that I was accepting it all so easy. Her hand slapped my ass cheeks with an even tempo. It was firm, but it wouldn't be too hard.

Well that's what I thought as she reached under the pillow and pulled out a paddle. Ten minutes later I was getting a real warm bottom. She began questioning me whether or not I had really jerked off while she was sunning. She just whacked harder when she knew I was not telling the truth. I told the truth. I told her that I had masturbated many times. She said that since she put on a show for me worthy of at least half a dozen hand jobs, tomorrow I would dress up and put on a sunbathing show for her. Any objections?

She shamed me into saying no objections and I agreed, several times. Not knowing what I was getting into.

Then she stopped. She had me stand up and grabbed my cock firmly. She took a bottle of baby oil and squirted it across her thighs. A handful was rubbed on my cock. I was led back across her lap, with my cock firmly planted between her thighs. Her hand pushed on my ass with a firm slap to get me in a humping motion. She now began an erotic hand spanking on my very red ass.

"Let's see how bad you want that blow job boy. " I humped her lap as that palm came down. It was shamefully erotic. I was about to cum when she said Remember you get another spanking if you cum.

It didn't deter me from cumming, but it made it a bittersweet moment, because my shame.

Another dozen swats on my ass were given after I had cum. She reached down and grabbed my underwear and wiped her thighs clean. She also used then to wipe me clean. I'll find you another pair to wear to the movies she said. We better hurry or we will be late for the movie. I don't think you want me in a sour mood when we get back here tonight. I expect you to do a good job and put out for me. Understand. She had a very stern look on her face.

She opened a draw and tossed me a pair of panties. She also saw the look on my face. "Don't give me an argument, you already owe me another spanking."

I don't know if it was the threat or the fact she was changing herself and her very well rounded ass was just a few feet in front of me. I had just cum but already there was another stirring within me.

As soon as we sat in the movies I had a drink in one hand and our shared bucket of popcorn in the other. Her hand easily rested on my inner thigh as we made easy conversation.

As the theatre filled she switched the conversation to our events earlier in the evening. But with the closeness of the other people it became a game of hints. "Are you ready to take care of me tonight?"

Certainly, I said. I was feeling a little cockier in this public environment.

Good, because I don't want a poor performance, she said with a smile on her face.

Nothing but the best for you Ma'am I said, finally able to show some confidence around her. Of course my hot ass and the tightness of the panties were a real reminder of what happened. But then I was assured I was going to be fucking her as soon as this movie was over. And after that great orgasm I had earlier I wasn't going to have that anxiety about Cumming to soon. That was a real relief because she had a habit of humilliating the hell out of me.

MMMM...I'll hold you to that she said. If you don't do an excellent job you might be due another dose of what you got earlier, she said with a smile. I'm not talking about the one you owe me either. Buy the way is your seat comfortable?

As best as can be expected Maam. What is this I had already grown to accept her spanking me? The other thing, I am a polite guy, but what is with all this maam stuff. It's like I've grown to expect that if I didn't say it she would slap my face and then giggle at my shame. But she seemed to be able to read my mind and know when I would give in.

You know we could have avoided all this foolishness if you came down and met me the other day instead of running away. Oh and then that little story about not taking matters into your own hand, if you know what I mean. That was so precious...... I'm expecting a little show of how you did it. We'll do it out in the backyard tomorrow so you know how I felt.

All the while she had one finger was very discreetly running up and down my cock making me very hard.

Bill, why don't you get me a refill on my drink....(whispering in my ear) I want you hard when you get back, or else..... Now go.

The bulge in my pants was probably more obvious to me, with the panties she had me wear. They were a lot tighter than my normal jockeys.

When I got back, she threw her sweater in my lap and thanked me for the drink. Her finger was making a little scratching motion on my cock all during the movie. At one point she grabbed my hand and put it on her thigh and slowly pushed it up her skirt. It was only mid thigh but again she whispered—do you want to kiss me down here? She was sure my hand was kept there during the movie. I took the initiative to begin to move it further up her thigh, but she slowly began pinching the head of my cock through my pants. I couldn't figure out what I was supposed to do. If I took the initiative she made it known that wasn't what I was supposed to do. If I just sat there doing nothing it was as if I was being ridiculed.

Walking out of the movie she held my hand. I don't believe the intent was amorous, but that kept me from putting my hands in my pockets to hide the bulge and the beginning of a wet spot from the dripping. On the way home she pulled off on a back road. "I want to show you what might have happened if you had won that bet and didn't have so much fun on my lap". So there we were in the front seat of her car. She took her lips and put them in the crotch of my pants. She breathed heavily as I felt the heat of her warm breath. She also moaned giving a most erotic feeling with the vibration, not to speak of her lips rubbing up and down my khaki covered shaft.

Maam. I'm going to cum.

"You better not", bringing her to an abrupt stop. She started the car and began driving.

We were just moments from her house and we soon arrived. Once inside she asked me to remove her panties. It's an operation that requires one to get down on my knees. So I found my self down on my knees peeling down her panties. Once at her ankles I was on my knees and now bent over. Why don't you keep your head down there and kiss my foot while I get undressed. I felt her skirt and then her blouse drop on my head.

Stand up, boy, she said.

As I did she was naked and sitting in front of me on the couch. She undid my belt and lowered my pants and the panties to my ankles. She had me remove my shirt. I felt sought of silly with all this stuff bunched around my ankles and my shoes on. It made me feel more naked than if I had nothing on.

A few strokes to my cock and I was clearly dripping.

Now honey do you still want to fuck me

Yes maam

And you promise to please me, no wham bam quickie here.

Yes maam, I'll try my best. I said, now almost panting

I don't care how hard you try, I want you hard and I want a good long fuck; no excuses. Now honey if you stick your little thing in my pussy and it shoots off like you did across my lap, Jenny is going to be awfully mad. Do you understand?

Deflated I said yes maam

Now I want you to open that closet door and grab what is hanging on the back of the door.

I had to waddle with the pants bunched around my ankles. It was a very ominous black leather razor strap.

Now honey do you think you can fuck Mistress like a big boy, or are you going to make a mess and earn a severe strapping. She was holding my cock in her thumb and forefinger slowly pumping as she asked.

Hell if she didn't stop I was going to shoot in her face.

Don't worry Jenny owes a good fuck and she is always good for her promises. Now let me know; do you want it the big boy way or the sissy way. You better not disappoint me.

God I wanted to fuck her pussy. But I knew that I was already seconds away from cumming. I almost couldn't believe it when it cam out of my own mouth.

Look I'm so close know I not sure that I could...

Not sure you can give it to me like a man? So you going to give to me like a man and take the consequences if not, or.....the sissy way honey.

I was about to cum. I tried pulling away and she just grabbed tighter.

What is it?

The sissy way I think, I whispered almost with a whimper.

I thought you would from the day I met you, she said. MMMMM....do you want to go over my lap again or do you want me to do it the special way with my hand.

Whispering even lower, and not wanting the humiliation of going over her lap again, the special way maam. I hoped this was just a matter of completing the hand job.

Ok turn around. What a cute bottom. Now bend over. Hands on the coffee table. Now if you hands come off that table you're going to get a workout from that strap, anyway. She reached behind my legs and grabbed my cock. She pumped it just to the edge numerous times. We were there a long time. Eventually she pumped me so I shot in her hand.

Exhausted her hand full of cum was in front of my face. I think she wanted me to lick it. But she didn't say anything. In a matter of moments she forced it all over my face.

"Most boys decide they would rather eat it then wear it. But whatever you want, it's your cum. Stay there while I make my self a drink"

About 10 minutes later she came back. Honey, I want you to spent the night and please me. Are you good with your tongue? If it wasn't, I learned till late in the night. My face felt used and like a glazed donut when she appeared to be satisfied. She seemed adamant about having me wear her scent on my face all night. It was more than just scent, she squirted a few times and parts of my hair where actually wet. She also had a shaved pussy, but it wasn't smooth. It was like she had shaved it that week, almost like a 5 o'clock shadow. As a result my face felt like it had a sunburn from her grinding my face with it. At times she straddled my face and just rubbed and rubbed. It wasn't as if I could even service her, she was just using my face for her pleasure. Early in the morning, she grabbed and handful of hair and pulled my face between her legs and she had me do it again.

We showered and had breakfast. I was nervous as she seemed there was more when she had the soapy fingers between my ass cheeks, but she just laughed. Plenty of time for that later she said. That shower felt good I had worn my cum and hers on my face for quite a while. Over breakfast she reminded me I promised her a sunbathing show. She had me dress up in a bikini and wanted me to go out and lay in the sun. Was she serious? I tried talking my way out of it. But she waved a wooden spatula at me and said do you want to have a talk about it.

Maam I can't do that someone might see. I said with real concern.

MMM you're right. But she led me to the chair and handed me the oil. I rubbed it on me. But she had some other ideas. She blindfolded me and told me that after I went out in the backyard , she wanted me to rub oil all over myself as she had and then lower the bikini bottoms and to jerk off she told me she was going to play with herself until she came and thought I should do the same. There was a piece of dread to all of this, yet her encouraging me to rub the oil on my cock was erotic. I couldn't believe I could even get it up again after all we did yesterday.