It all started innocently enough when I sold Eileen her retirement home. She had been widowed a few years and was downsizing.
She had sold the family home and now buying a smaller two bedroom condo and she wouldn't have the yard work etc to stress over.
I spent a great deal of time with her making sure she understood the whole process and felt comfortable, even going over things again and again. I wanted to be really nice to her because she was an elderly person and I was always taught to be kind and respectful to people older than me. Plus I was feeling sexual attraction for her. I was turning up the charm because one has to be prepared. You know the old phrase, luck favors the prepared.
During the transaction as I got to know more about her, I began to notice her cleavage among other things. I noticed how curvy
her body was for a woman of sixty four. I made an effort to touch her when appropriate. I would gently touch her arm to guide her. I would pull out chairs for her and then gently pat her shoulders when she sat down. She was soft and warm to touch. She commented on what a treat it was to see such a well mannered young man, saying how rare it is to meet young people today who weren't rude or hostile.
I visited her often even after she had moved in. I had offered to help her move, but she had hired professional movers. I helped her understand her security system as well as her new modern appliances. She was always hospitable and always eager with tea and snacks. We got to know each other really well over the next couple of months. By now I was really wanting this lady. I found myself picturing her when I was giving it to my girlfriend. I couldn't keep from ogling her form every chance I got. I always tried to sneak peeks down her blouse or between her legs and more than once I wanted to attach my face to her plump round behind.
I put my arm around her waist one day as she looked out her kitchen window admiring the little garden she had started on her little deck. She didn't move away so I just caressed her there on her side feeling her warm rolls under her blouse. I leaned into her touching my head to hers and telling her how wonderful it was to see her getting settled and making a home of her new house. Well she leaned back into me, so I gave her a kiss on the cheek. She then turned and faced me and gave me a hug. It was a pleasure having my body against hers. I gave her a little squeeze and pushed my groin forward a little so she was sure to feel my hard cock. We stayed like that long enough that I was able to caress her back and she caressed mine telling me that I'm a special friend and she's happy to know me.
Well my cock wanted to explode right then and there. I kissed her on her forehead as my hands worked their way down to her soft warm plump behind.
I said, "I like you very much Eileen, you are a special lady and I'm happy to know you as well," before she gently backed away to get the kettle which had reached its boil and had started to whistle up a storm. Damned kettle!!
Nothing like the storm in my pants let me tell you! Nothing but tea happened that day, but I was now kissing her as opposed to polite handshakes. I also had my hand on her ass, even for a moment, and she didn't disapprove. That, I was definitely going to push further! It was a kiss on the cheek and a hug as I left, and I put my hands on her plump ass again. She didn't move away so I caressed her buns as I told her it was a pleasure seeing her today and again that I'm very happy to know her, then patted her cheeks as I headed out the door.
I went back the next day with some roses I scammed from one of the girls in the office. I had clients booked all day but I wanted to see Eileen to reinforce the connection we made the day before. She leaned in and kissed my cheek as I gave her the roses, oh she smelled good! She quickly rubbed the lipstick off my cheek with her thumb then turned to go get a vase. I followed her and put my arm around her waist. In the kitchen she bent down to get the vase from a lower cupboard and man I could not control myself, I had to act. How could I not do something with the wonderful gift before me.
Seeing that warm plump ass bent over in front of me was too much, I acted. I put my hand on it and rubbed. "Oh, Tristan you....," came the response.
That's it, that's all she said. My cock was hard, I wanted to have her just like that! I got behind her, she didn't come up right away. She seemed to freeze as I pressed my hardon into her ass and held her hips. I waited for her to respond while enjoying the feeling of my hard on pressed against Eileen's plump round ass. I know I sensed her push back. This was it, but I was booked up all day with appointments. I didn't want a three minute quickie with this wonderful lady. I wanted us to be lovers. What seemed like minutes I'm sure were only seconds.
She's an older lady and just how long could she stay bent over into a cupboard right! I released her and stepped back. She stood up and brought the vase with her. She glanced at me and said, "Tristan, I don't know what to say." My mind began to race trying to decide what to do next. I didn't have time to play this out today.
This opportunity was not expected. I had to delay it till another day. I decided to give her back the upper hand, express remorse and make HER apologize to me. Then she would want to talk it over.
I politely apologized saying that I was sorry that I acted so badly and turned, adding that I better go. "I'm not myself today, I have too many things going on today. Again, I'm sorry Eileen. If I'm not welcome here anymore, I'll understand."
By then I was at the door stepping into my shoes. "Oh stay Tristan, don't be so hard on yourself."
"You flatter an old lady."
"And that's just the thing, I'm way too old for you."
"Are you not happy at home Darling?"
I said, "really, its a long story Eileen, and today is really not a good day because I'm booked with clients, I only wanted to stop by for a minute, I don't even have time for a coffee."
She put her finger to my lips saying, " You're always welcome, just call me when you have some time to spare." She hugged me and gave me a kiss on the cheek as my hardon again pressed into her again. Again she stayed against my hard cock. Again I held her.
I kissed her on the forehead and said "thank you Eileen."
I wanted to stay, my cock was ready to explode. I wanted to make love to this lady. I was getting closer to that goal, but I was too busy today.
"Its okay Tristan, come back and see me when you can."
Well that was it. That's what I wanted. But it would have to wait.
I went back to work, my head swimming with thoughts of what had transpired earlier. It was difficult to concentrate with thoughts of making love to this arousing woman I had come to know and lust after in the worst way. Then there were the doubts that wanted to take it all away from me. It was a really tough afternoon to get through. I called home around supper time and told my wife that it would be a late evening as I was going to be with clients. So now my evening was clear. I gave Eileen a call and told her I was feeling really badly about earlier and apologized again. She said, "enough about that Tristan, I'm busy just cleaning the floor right now, but come see me when you can."
About a week later I called Eileen to say hello. I had caught her doing housecleaning. She said she was almost done and going
to take a hot bath right afterward. That gave me a hard on and got my mind thinking about her naked. I asked her if she'd mind some company, not knowing if she'd catch my meaning. Well she replied that she would put the kettle on. I left the come on out there for her to do with as she wished.
That was the visit I accidentally spilled hot tea on my shirt and in my lap. Man what a guy won't do for pussy! She suggested I get my shirt cleaned right away and went to get soda water saying I should take my shirt off. I did, and followed her to the kitchen handing her the shirt. I stood there in only my pants as I fretted about what a klutz I was.
She just brushed it off saying "these things happen, its no bother."
I suggested that we should do my pants as well to which she agreed. She told me to give her the pants and I could get a towel from the bathroom. Not wanting to pass up an opportunity to be naked with a woman, I undid my pants and stepped out of them. My (thong) underwear was wet too and I mentioned this to her. She chuckled and asked if I wanted her wash them as well. I was only half turned so she saw my buns when she glanced over at me.
" What are you wearing dear boy, Women's underwear!"
I replied, "no Eileen, men wear these too." My cock was hard and bulging in the tiny thong as I turned around and gave a view of my ass cheeks and then a full view of my bulge.
"Goodness, that doesn't cover much."
I told her I could just carry it in my pocket since it was wet. "you should try a pair Eileen," I suggested to her. I told her that it only takes a short time to get used to them, I was thinking how nice it would be to see her in a thong.
She laughed saying, "I don't think so, I'd be too embarrassed to even buy them, much less wear them." At that moment I decided to get her a pair of ladies thongs, and maybe boyshorts as well! I was going to present them to her and ask her to try them on so I prove to her they looked great.
I said "I'll buy you a pair then," as I walked to her bathroom to get the towel. I love this this seduction game and stretch it out as long as I can last. We continued the banter as I stood there wrapped in a towel, my thong air drying in the sunlight of her kitchen as she rinsed off my shirt and pants. My cock was a bulge the whole time and I made every opportunity to let her catch a glimpse of it. She wasn't shy about glancing over at it from time to time.
When she had finished working on the stains she decided to toss them in the dryer for a quick spin so they'd be dry. I carried the shirt and she carried pants to the dryer. She put the pants in and I bent down to put the shirt in. That's all it took and the towel dropped to the floor. I didn't even attempt to stop it from falling. My cock was aching and needed release. The little head was beginning to take charge now and he was going to get what he wanted. There I was bent over into the dryer with the towel on the floor and my hard dick pointing at my belly. "Whoops," is all I said. I heard her gasp. I looked up to see her hand at her lips as she stared at me. I deliberately stood up to give her a better view. She didn't take her eyes off my cock poking straight out. I knew I had her. I knew it excited her to have me there naked. She wasn't going to resist now. I wanted nothing better than to get her naked as well.
