It felt like a pretty normal day to begin with. I wasn't expecting anything out of the ordinary. It was evening and I had just left my house, walking to the shops after work to pick something up for dinner.
One street away from my house I heard someone behind me and turned to look. Behind me was a woman with dark red hair and a dark coat, the sound of her heels tapping the pavement. She clocked me looking back at her and smiled. As I turned back to face away from her she called out "Don't worry honey, I'm not stalking you."
I turned back. She must have been in her 30s or early 40s and looked good. In another context or in more light I might have been interested.
I gave a lame reply: "it's ok, you don't scare me."
"Is that so? Maybe you should be more scared!" She laughed. I laugh. It's awkward. "I like your coat, very stylish," she comments.
Like an idiot I tell her that its not that great or new.
"Perhaps it's just you that makes it look good then." Was she coming on to me? "You don't have to walk with me. I'll just keep walking behind you enjoying the view. You have a nice bum."
I'd never really come across a woman this forward. I wasn't really sure what to do. My natural shyness took over and I kept walking. "Thanks," I called out. I walked in awkward silence, knowing that she was watching me walk, hearing her footsteps behind me.
I reached the shop and entered it, holding the door open for her.
"Ah, a gentleman too. Very nice." She gave me the look up and down that older women can do so well. And I felt the stirrings of an erection at the proximity of this undeniably attractive older woman who had complimented my ass. She slowed as she passed, allowing the moment to last for a bit, then swept on into the store. I lost sight of her for a while in the store and began to forget about her as I picked out the stuff for my evening at home. I didn't see her until I was getting to the checkout. She was just finishing having her bag loaded ahead of me, doing her lipstick in the mirror. I was briefly fascinated and captivated by her lips as she flexed them, admiring her attractive face in the bright lights of the store. She saw me and winked as she began to leave the store.
I paid for my things and began to follow her a minute later. Emerging onto the street I saw her only a little way ahead. As she walked I saw something small and cylindrical fall out of her bag to the floor. I rushed to pick it up and found that it was her lipstick. I called out to her "excuse me lady, you dropped something."
She turned round and stopped. "Thank you. Wait, are you stalking me now?" She approached closer and took the lipstick from my outstretched hand. "This is my favourite one."
"Oh, sorry, no I'm not trying to stalk you."
"Haha, it's ok love, I'm just messing with you. You can just let me thank you." We begin to start walking again. "This is going to be awkward, we're going the same direction, and you've only just met me. You must be thinking I'm an absolute wild person. I'm just very extroverted and love to chat to cute strangers."
"Oh um thanks. You can go first." I gesture for her to go in front.
"Still such a gentleman," she giggles, "unless you're just trying to check out my ass now."
I start to object but she holds up her hands. "No, fair's fair, I checked you out." And she begins to walk ahead of me, her hips swaying in that way that classy ladies can do.
Not far from where my street where I would be turning off, I see her drop something that she has been holding for a while. She bends over to pick it up and I can't help but admire the way her coat and skirt hug her ass as she bends. With her stopped and bent over, I quickly catch up to her.
"Oh I'm so clumsy tonight. Did you get a good look?"
"What?"
"Did you get a good look... at where my key went? Ah, here it is. DId you think I was asking you if you got a good look at my bum when I bent over? Did you like what you see?" By now we were standing close under the streetlight and I could smell her scent. "I think you did like it," she says glancing down and I become aware that I am sporting a semi which is tenting my trousers. I move my bag of shopping in front of my crotch before realising how obvious that makes things. Her smile is almost predatory. "You'd better get that package home," she bumps my bag of shopping with her hip. "You go ahead, I'll follow and make sure you don't get any crazy ladies assaulting you on the way."
She follows closely as I head down my street and we arrive at my front door. I turn round and thank her for a weird but pleasant walk. "It will be a pleasure," she replies, flashing that wolfish grin as I turn and start to go up the steps, taking the key out of my pocket and unlocking the door. I'm about to turn a final time to watch her walk away when I feel her hand push between my thighs and slide quickly up and she grabs my balls. I gasp as she squeezes them and begins to push me inside the house. "Oh honey, you didn't think the evening was over did you? I've only just started with you pretty boy."
She pushes me up against the wall and closes the door. Then her hand dives into my trousers and pulls my semi erect dick out. "It feels like you want me to take care of you tonight, doesn't it." My cock is rapidly growing to full erection in her hand and her other hand is over my mouth, stopping me from responding. Her hand reaches down to cup my balls and squeeze them again. "Oh baby, you are in desperate need of some milking. We're going to have to take care of that for you." With that she grabs my cock and leads me by it into the living room.