The Landlady Ch. 2

We were walking along Thames Street in downtown Newport RI. A tourist trap if ever there was one. A street full of little shops and such with the occasional fisherman’s bar thrown in for good measure and a LOT of restaurants.

I had on slacks and a Polo shirt, Ellen, well Ellen had on a button up dress, heels and a smile. The dress was white, with brown buttons and a belt to add shape although Ellen didn’t need to add shape. She was good looking enough as it was. Oh, did I mention she only had four of the buttons fastened?

The dress was full and every time she took a step you would see her long legs right up to within two inches of her totally shaved pussy. Her rather substantial bust was in no need of a bra and the button on the top were undone to just below them. Allowing anyone who stood at her side to view the creamy alabaster skin that was there.

I swear the dress was so thin you could see the red marks of the paddling she got that morning too. It was quite a sight.

As we walked along I got a thrill out of seeing this lady who so obviously was older than me. Ellen is in her mid 40’s and I’m 19. She looks like late 20’s or early 30’s and I look a little older because of the way I carry myself but it’s obvious she has a few years on me. Maybe just a rich lady with a young stud muffin. Yeah right.

We had just finished walking through one of the shops when I noticed the owner watching us closely. I told Ellen I think the owner has the hots for you. Looking up to see what I was talking about she saw a very attractive lady about her age who was doing her damnedest not to appear obvious. You could tell she noticed Ellen’s lack of under garments. You could also tell she was staring at her ass.

Looking up she noticed that I was watching her and she got beet red knowing she’d been caught. I asked if there was a question.

“No, I just notice a pink stain on that lovely white dress” she replied.

Turning Ellen around so her back was to the lady, I gathered her dress and pulled it taught across her bottom. Sure enough, you could see the contrast of the her gloriously red bottom and the white skin of her thighs.

Reaching down further, I took the hem of the dress and slowly raised it, watching the store owners eyes get wider, the higher the dress came up and then licking her lips as if they were dry when the bottom of Ellen’s ass cheeks were displayed.

Looking at her I motioned her to come closer and then when she was close enough I continued to raise the dress. Ellen’s red ass was fully on display now. I told the owner of the shop that Ellen had been punished for a misdeed that morning and that this was the partial result of that punishment.

Ellen’s ass was so red and you could almost feel the heat coming from it. I reached out and took the shop owners hand and placed it on her ass.

“See, still warm from the warming,” I said.

“Yes, I can tell,” she replied. Not removing her hand but instead brushing her fingers gently over the bottom of my lady.

Dropping the dress back in place, I took the lady’s hand and then pulled her closer to Ellen. Placing her hand inside the dress Ellen had on, I then cupped her smaller breasts with my hand, quickly finding the nipples. I pinched lightly, then harder, until her eyes opened wider and she sucked in her breath. Letting go of the nipples of the shop owner I then removed her hand from the inside of Ellen’s dress.

Letting her hands drop to her side we left the store with a promise to come back soon. As we left the store and continued walking down the street Ellen said that was the first time a TOTAL stranger had felt her up.

I just said that if I want someone to feel her, she will allow it. If I want to do the feeling myself no matter where we are I will do it. And with that, I pulled the top of her dress out far enough for me to see her entire breast and slowly reached behind her and gave her a loving swat on her already red ass, while leaving my hand on her bottom as we walked along.

We were in an area of the downtown section where there were plenty of restaurants. As we went onto the dock of the Landing restaurant I was feeling pretty good. We were taken up stairs to the upper deck and seated. Being on the bay, there was a constant breeze and when we sat down that lucky breeze just went right up Ellen’s dress and parted it like Moses parting the Red Sea.

Here she was sitting there with her dress open to her pussy and the breeze catching it every once in a while to make it seem like a white flag drawing attention to her legs which were exposed as far as possible.

Ellen started to pull her dress closed when I stopped her. Shaking my head slowly I wanted to see how far we could play this. The server came over, a pimply faced 18 yr. old and he could hardly get the menu out he was staring so hard, torn between the legs that were on display or the breasts which were so obviously unencumbered. We ordered a chowder each and continued to watch the folks on their boats in the harbor and the tourists all around us.

Bringing the bill, the waiter seemed to be lingering. So I just counted out the amount and stood up. Helping Ellen to her feet, I then told her to give the boy his tip. Looking at me she almost said no, then with a mischievous twinkle, she calmly turned to the waiter, and pulled open the entire top of her dress, exposing her lovely breasts to him, she moved her hands under them for un-needed support and pinched her nipples until they were the 1/2 inch hard little berry’s I love to suck on. Then calmly she covered herself up and said thanks for a wonderful meal.

As we left we turned around and the poor waiter was still standing there with a dumb look on his face. Wondering did that really happen?

We had decided to return to the house when we heard Ellen’s name being called. Turning around we saw Liz, one of Ellen’s acquaintances just getting out of her car.

I was right the first time. She had great legs. As she got out she bent over to put a shoe on her foot that left her impressive cleavage visible to me all the way to her nipples. Straightening up she took the few steps to us and did the air kiss thing again with Ellen.

“It’s good to see you out here” she said, “ I so wanted to invite you and Peter to the house for a little get together next weekend.”

Before Ellen could say anything I very quietly moved next to her and put my arm around her waist. This caused the top of her dress to gap a little showing that she was wearing nothing under it.

Liz almost choked when she realized that while standing still her friend looked normal, but she wasn’t wearing a bra. She had no idea that the dress was opened almost to the waist. From both north AND south. You could see the gears turning as she stammered for something to say.

I took the initiative and removed my arm and taking Liz’s hand in both of mine, I held it lightly and said we’d love to come and what time and what should we wear?

Liz never realized I was holding her hand as she continued to stare at the cleavage Ellen was showing. She simply said she would expect us on Friday around 8 ish.

Let me say that Liz, while good looking had NOTHING on Ellen in that department and she seemed VERY impressed with her store-bought boobs so as I was chatting with her and Ellen I slowly raised the hand that I was holding. With my hand on top and here’s in between, soon I was at the bottom of that large breast that was very noticeably excited.

Just as the back of my hand meet her breast she seemed to come out of her trance and dropped my hands. I noticed also that the nipple was extended even farther as a result of that brushing touch or possibly as a result of the skin that was staring at her right there on the street.

Moving back to Ellen’s side, I placed my arm around her and rested my hand on her hip. This allowed me to pull her dress back slightly and showed even more smooth thigh through the opened front. As Ellen’s dress came open more and more you could tell that Liz was starting to let her gaze wander lower to see what else would be exposed. Ellen tried in vain to hold her dress together but a slight pressure from my arm around her waist was all it took to stop her. Not one to disappoint her, I shifted my hand again and the dress was opened all the way up with only an inch covering Ellen’s shaved pussy.

Liz was noticeably licking her lips in lust and just as she was about to say something else, I said we must be getting home. See you Friday night. To say Liz was at a loss for words would be comedic.

As we continued to walk down the street we drew our share of looks and several double takes as Ellen was stepping out and showing enormous leg through the dress. We continued to where we parked the car and I mentioned to Ellen that she was doing very good except for the one time she tried to hold her dress together.

Ellen looked at me and said she was sorry. Sorry doesn’t get it with me.

As soon as Ellen was seated I reached in and completed the unbuttoning of her dress and then held out my hand. Give me the dress. Ellen held it together but when I said NOW, she shrugged out of the dress and handed it to me.

After getting into the car, I drove up and down a series of one way streets until I saw Liz, strolling along looking at shop windows. Pulling up behind her, I sounded the horn. When she turned around I handed the dress to her and told her I would pick it up Friday, then drove off to the apartment and Ellen’s house.

Pulling into Ellen’s drive I got out and held her door as she walked to the stairs of the apartment. Following her up the stairs gave me that view I had grown to love.

Going into the apartment I immediately told Ellen to kneel. She dropped like someone had shot her. I then told her to remove my clothes, starting with the shoes.

Slowly she slipped each shoe and sock off, then undid my slacks and after stepping out of them she stood to remove my shirt. Once we were both nude, I told her that from now on, when she was with me she would at all times be naked, and if I so wished on her knees when in the apartment. When we were out she would not touch any of her clothes except to smooth them when she sat down.

When asked if she understood and agreed, she said, “yes Sir.”

Good then, go lean over the chair. I had never moved the overstuffed chair to it’s proper place and Ellen immediately went to the back and leaned over.

Going to the closet, I selected a flail. A 36 strand, deer skin whip that was butter soft and would NEVER cut.

Offering it to her to kiss, I told her that the act of holding her dress together was not allowed and she would taste the flail for the first but NOT the last time.

Taking my hand back I let go with a full swing. The swish as it whistled through the air in the small space was amplified and sounded like windstorm through the trees. As it landed with a satisfying thwack, I noticed how her ass vibrated and quivered. Drawing back again, I let it pass through the air so just the noise of it’s passage filled the air then landed another perfectly aimed stroke on her ass. The bad thing about a flail this soft is you must comb out the strands every other stroke so there would be no knots striking flesh. This just enhanced the anticipation of the next stroke.

Fifteen strokes later Ellen’s ass looked like a red Christmas light. Moving to the other side (we don’t want to be uneven) I applied fifteen more strokes.

During this whole ordeal the only sounds I heard from Ellen were gasps and a low moan when I finally stopped.

Going into the bathroom I retrieved the lotion I kept there and came back with a handful warming in my palm. Applying the lotion to her abused bottom I slowly stroked and petted her and massaged the lotion into her leaving a good portion of it in the crack of her ass to act as lubricant for the butt plug I planned to use.

Instructing her to remain where she was, I went to the closet and retrieved a butt plug that was about three inches in diameter and sharply tapered to it’s base. Using the excess lotion to lubricate the plug I slowly inserted it.

Feeling the unfamiliar shape beginning to invade her bottom, Ellen started to straighten up but a firm hand on her back held her in place as I used the plug to fuck gently in and out of her until the widest part was at her spincter, I then drew my hand back and delivered a sharp slap to her ass cheek while at the same time I pushed the remainder of the plug into her ass. With a gasp, she realized she had taken the whole thing and the unfamiliar stretching in her bottom only caused minimal discomfort.

Taking her by the hand I had her straighten up and then told her it would be her responsibility to ensure that she was “plugged” when ever she was with me. This included when we would meet for lunch or any other occasion when we were to be together.

Nodding her head she responded correctly. Then looking up at me asked if I would care for dinner tonight here or at her place.

I told her I would enjoy a nice quiet dinner, and if we were in her house she could remove the plug.

Looking up at me, she said, “Well I guess I’d better bring the spaghetti up here to fix.”

*****

It seemed as if the week just flew by and before I knew it, Friday was upon us. Wondering what kind of “get together” we could expect, I asked Ellen what Liz was like and what kind of parties she hosted.

Ellen said that Liz was a wanna be player. Always on the edge of things but never in them. If she had a party just about anything could happen but Liz always seemed to be a non-participant.

When asked if we were required to “Dress to Impress”, Ellen only said that she would wear something nice but a total dress up was not required. That being said, I just reminded her of our arrangement and dress code.

When I knocked on Ellen’s door at 7:55, I saw she was wearing a skirt that came just above her knees and a transparent blouse that displayed her ample bust line, red lipstick on a mouth that was slightly open. I also noticed she had gone to a boutique and purchased a new bra. Giving her a quick hello hug and kiss I copped a feel. A sneaky way to check for the non existent panties. It was a 20 min. drive so we left, planning on getting to Liz’s a few minutes after 8.

On the drive over, I asked Ellen if she was comfortable with the way we were progressing. She was NOT property but she was controlled, by me. If I wanted to dance with someone else she would allow it and if someone approached her it was only with my permission that she could proceed.

She took all this in stride and asked if I was going to try to make Liz.

That depends on Liz, I replied. She would be fun to watch but I had a feeling it was all for Liz. Nothing for anyone else.

As we walked up the stairs to Liz’s apartment, I was thinking, what would happen?

After knocking on the door, and hearing someone call to come in, I knocked again. After a few minutes, the door opened and Liz stood there. She must have spent all day at the tanning salon and the beauty shop. She did look good but behind the eyes there was something going on. She was dressed in a low cut dress that showed skin to just above her naval and was so short that if she sat down she would have to do so with both hands on the hem to keep it from going around her waist. She had on 4 inch heels that raised her to an inch above my 5’10” and did look good.

As we walked into the room there were three other couples and Liz said that a few more were coming and would get there sometime later on. As we were introduced, someone else knocked on the door and the other two couples walked in. I couldn’t help but notice that Ellen was the best looking woman in the room with Liz a close second. Of the other five couples the best that could be said were the women were, “pleasant”. Almost as if Liz had stacked the party with ordinary or homely women so she would shine.

Music was playing on the tape deck and we were all getting along well as one then the other couples started to pair off for dancing or just talking and getting to know each other. I asked a couple of the ladies to dance and was rewarded with firm bodies beneath the ordinary looks. I deliberately avoided asking Liz to dance, just to piss her off.

As Ellen and I were returning from a nice slow dance, Liz made her move, coming up to me and asked ME to dance. Sure I said, as we walked to the cleared living room.

We were dancing “politely” that is nothing too close, when I noticed one of the men ask Ellen to dance. Looking at me for permission, I nodded as he took her hand and led her to the dance area.

As the song was winding down, Liz asked if I would care for a tour of the place.

Thank you, I said and off we went. The obligatory tour of the kitchen, den, spare bedrooms and ending in the master bedroom. Looking at the over sized bed Liz just turned and as she started to lean into me, I grasped her hips and pushed her back a little.

Turning her around to face the bed, I put both hands around her waist and raised my hands up to cup her breasts. Then pulling back a bit I drew back my hand and gave her a resounding swat on the backside lifting her off the floor.

Still with one arm around her waist, I pulled her back to me and with my lips close to her ear, I whispered if she wanted to play games she chose the wrong person. Either come out and say it or leave it, but there was a price to pay for anything she hoped to get.

I then turned her to me and as my lips met hers, I slowly captured her lower lip with my teeth and bit gently down until she couldn’t pull away. With one arm around her and my hand stroking her ass I pulled her pelvis into mine. I raised one hand and pinched the erect nipple of her breast until her eyes widened.

Quickly releasing the captured breast, I stepped back, thanked her for a wonderful evening and left the bedroom.

Walking out into the living room, I looked for Ellen. She was involved in conversation with two of the wives that were there, so walking over, I told her we were leaving.

One of the women she was talking to just looked at me when Ellen replied with her standard, “Yes Sir”.

Liz was just coming into the living room when we walked over and we thanked her for the invite and hospitality. Before we could say another word, Liz asked if we could come to dinner the next night, just the three of us.

I told Liz we had plans but she should come to Ellen’s on Sunday afternoon at 2:00 PM. I also said I was a stickler for punctuality. Without waiting for an answer, I escorted Ellen out and down to her car.

Arriving home I told Ellen to go to my apartment. Upon entering Ellen immediately went to the bathroom and when she returned I noticed her bra was missing and she stood waiting for my approval. With a nod and a smile I motioned for her to have a seat on the sofa. I went to the fridge and grabbed a couple of beers and a glass and sat down.

I wanted to let Ellen know that she had a say in the way things between us were progressing. I also wanted to emphasize that being a sub was NOT the same as being submissive and that the line we were walking was indeed thin. She agreed with what I had to say and also wanted to progress more. This being said, I told her that she would be “tested” a little the following day.

As I stood I held out my hand and we went into my bedroom. Standing before the bed I told her to strip while I watched. Slowly she removed her blouse then the dress as she laid them on the chair next to the bed, I had her lay down with her eyes closed.

I then removed my clothing and laid down next to her, slowly caressing her skin as I explored her body. Giving small kisses as I tasted each inch of her breasts. Finding my fingers at her sex, I slowly slid one then two into her. Then as she was arching herself to meet me I rapidly flicked her clit with my thumb bringing her to a quick but shallow orgasm.