Miled

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.

She strips her coat off and pushes me up against the wall. This close and without a coat I can get a good look at her. Her dark red hair fell to just below her shoulders and she was wearing a short black dress that hugged her slim figure, black stockings and black high heeled boots.

She pulled my trousers down to my ankles and my boxers down a little to let my shaft spring fully out and erect. Then she sat down on the couch, crossed her legs, allowing me to see the tops of her stockings and began stroking the shaft of my cock with the toe of her boot.

"Now, what's your name honey?"

"John. What's yours?"

"You can call me whatever you like baby. You just need to know that I am here to help you experience more pleasure than you've ever had before John. You are such a gentleman, a nice cute guy, and you deserve a reward for that. I'm here to give you your reward. And I'm going to enjoy every second of it because not only are you cute but you have an excellent cock John, so lovely and hard and long." She brings her heel up to gently probe my ballsack. "And you have these big full balls which are so desperate for milking. When were they last milked John? When did someone last make you spurt your hot creamy cum?"

"Um I don't have a girlfriend Miss."

"Oh Miss, I like that! You're going to do very well at this John, I can tell already. You're perfect. I bet you've been having to take care of that lovely cock all on your own. When was the last time you jerked off baby?"

"Five days ago Miss."

"Mmmm, you are in a real desperate need of some serious milking. You'll be so glad you met me. Oh John, you're in for a real treat."

Her voice was almost a purr and my cock was responding to her voice and her skillful stroking and teasing of my cock and balls with her heels. I was as hard as I'd ever been, my cock throbbing in anticipation. I was nervous but more aroused than I'd ever been before.

Suddenly she stopped her foot stroking my shaft and stood up.

"That really is a lovely cock John. You are quite the turn on." She lifts up her short dress showing, first the top of her stockings, then her matching lacy black panties. She slides two fingers inside and moans seductively as she strokes her pussy. "Mmmm John, you are making me so wet."

My mouth was probably open by this point. I had never come across a woman so assertively seductive and I didn't know how to respond. Luckily it didn't seem to matter as she effortlessly took charge of me once again. She began to slide her stockings down her legs, one at a time, kicking her heels off. "I could tell you find me attractive John. Even before I saw how hard you were getting, it was the way you looked at me. And now I can see from how you are so hard and throbbing that you want this so bad. You want me to take charge of you." Her feet were now bare as she sat down again. "I can tell how much you want me to touch your massive erection." Her bare feet begin to stroke my cock again and she sandwiches my pulsing shaft between her toes and begins to wank me with her feet in a way that was impressive and very arousing. "If you want this, I just need you to do one thing."

"What is it?"

"Get naked for me. Strip off those clothes." I begin to undo my shirt buttons. "Faster! I want you butt naked and on your knees in front of me now!"

I practically tear off my clothes, stepping out of my trousers and pushing my boxers down. Now completely naked, I sank to my knees on the rug in front of her.

"Mmmm, good boy. Very nice. Now we can have some fun."

She began once more to play with my dick with her feet, her toes pushing down on it as her other foot began stroking along the underneath of the shaft, pausing occasionally to probe my balls with her toes.

"Now lie down," she instructed, and I did, my cock sticking straight up in the air. She got down and pushed my legs apart, taking her position in between my legs. Grabbing my erection, she licked her lips. "Such a delicious looking cock." She kissed the tip of it before sucking the whole head into her mouth. Her cheeks went in as she sucked and I moaned, then moaned again as her tongue began to caress the tip of my dick. She let me pop out. "Fuck John, you are so ready for this. You want this so bad. I can already taste your precum and we're only just starting." She grabbed my balls. "Look at these things. So full of cum. So pent up and ready to explode."

And she began to jerk me off, her hand firm as it tugged on my erection. One hand remained on my balls. She alternated between tickling and teasing my balls, drifting all around them and down to my perineum. She would also grab and tug on them, pulling them away from my body. It was the most intense handjob I'd experienced and she was incredibly skilful. I could feel her bringing me closer and closer to orgasm. Her tugging on my balls became more and more insistent as I got closer to exploding, making my testicles fight to retract. I could feel the pressure building and building.

I was quickly approaching the point of no return. In between my moans of pleasure I called out that I was about to cum.

She leaned over me, a gleam in her eyes. "Resist it John. Fight it. Don't you dare cum yet."

I let out a groan as she tugged harder on my balls while her hand continued to milk me inexorably closer and closer. I began to shake and spasm as I tried to hold back from cumming. "I can't hold it!"

Her hand speed increased even more, her tugging insistent. I was panting with exertion. "Oh shit, I'm cumming!" I yelled out.

Immediately her hand stopped stroking and squeezed the base of my cock, her other hand still holding my balls. I thought for a second that I was going to explode, then that she had stopped too soon. Then I let out a roar as I felt my orgasm ripping through my body as my penis began to convulse in her hands. The cum began to jet out of me in big spurts, shooting high up in the air before splattering over my naked body. My body shook as I tried to thrust through her vise like grip but she held me tight as my cock spasmed.

"Oh John, that was so much cum! Mmm, you really really needed that didn't you baby."

I was still panting and couldn't reply. My cock still stood firmly at attention.

"And you are still hard. Very impressive John. Now that was very messy because you gave such a big load. I think you might have got some on my dress. Do you mind if I take it off?"

I could only shake my head. She stood up and pulled her dress up to show me her panties and her ass again.

"I know how much you like my ass, you were watching it all the way home." She faced me again. "Do you want to see my tits?" She began to pull the top of her dress down, showing off her bra. "No need to answer, let me feel the answer." She dropped to her knees again and took my cock in her hands, feeling it pulse, still hard and excited.

"Oh yes, you are so excited. You really want more of this John and I want to give it to you." She rubbed my dick over her cleavage leaving a trail of cum on her smooth skin. Then tugging on my cock she made it obvious that she wanted me to stand up with her and I did so, wondering what was coming next. Reaching behind her back, she unclasped her bra and pulled it out from under her dress. Then she draped it over my erect cock, stroking me a few times with the soft material folding over the tip of my cock. It fell to the floor and she pulled the front of her dress down, letting her tits pop out and her nipples bare.

Her tits weren't massive but they were perfectly formed with sexy pert nipples jutting out, aroused and stiff. She grabbed hold of my head and pulled it down to her breast and I responded by fastening my mouth onto her nipple, suckling on it and flicking my tongue over it, making her moan.

After a minute of my attention on one nipple, she pushed my head across to her other nipple and I continued to stimulate her as she let out sounds of enjoyment. While one hand continued to hold my head in position, her other hand dropped to her crotch. She slid her fingers inside her panties and into her wet pussy. Her moans got louder and more frequently as I could hear her fingers thrusting in and out of what sounded like a very wet pussy. Suddenly she began to shudder and I drew back to see her panties become quickly sodden as her juices flowed out in her orgasm.

"Mmmmm, I don't normally do that, but you are so sexy John. Now, hold these in your mouth for me while I take off my dress." She slips off her soaking wet panties and stuffs them into my mouth. The smell of her juices filled my nostrils.

Right in front of me she stripped completely naked, pulled the panties out of my mouth and threw them aside. Then she grabbed my cock and pulled me in close to her, lips teasing and almost kissing, my cock pressed against her smooth flat stomach.

"Mmm, time for round two baby."

She led me to the bedroom and pushed me down, making me lie half on the bed, my ass on the edge and my legs stretching over the edge.

She bends over and begins to lick her way up and down my cock, bringing me from hard to throbbingly and achingly erect. Pulling some lube from her handbag she began to coat her hands with lube before smearing it all over my throbbing shaft. Then she bent over again and as her tongue probed my balls her hand grabbed my cock and began to jerk me hard and fast.

"Oh John you really do have a fantastic cock. And these balls are still churning with cum. Mmmm, let's help you with that."

She pushed my feet up and onto the bed, spreading my legs wide. Slowing the pace of her jerking, her tongue worked its way lower and lower until she began to tongue my ass, rimming it with her tongue before slipping it inside my ass. I gasped and my cock convulsed in her hands.

"Oh John, are you a virgin?"

She kept hold of my cock, anchoring me in place, refreshed the lube on her other hand and began to slide her oiled fingers around my exposed butt. She tickled my balls making me squirm then traced her way down to my ass, sliding her finger slowly into my ass. She reached the knuckle and I felt her finger curl inside me, rubbing me in a way I'd never felt before. My cock twitched and jumped as she slid her finger further in and then out again. My cock was so hard and I could feel a pressure building in my balls.

Soon she was jerking me off with her middle finger in my ass, sliding gently in and out, curling, stimulating me until I could barely think. To make matters worse, she was clearly keeping an eye on my arousal and every time I approached orgasm, she would slow down or stop. I began to moan and thrash around as she brought me to the brink again and again.

Occasionally as she held my cock, waiting for my orgasm to subside, she would push in close, letting her nipples brush past my balls. "Oh John, this is such a nice cock and you are so turned on right now. Soon you're going to cum the biggest load for me. I know you want to. You want to release this massive load. So much pent up cum just waiting to be pumped out of your massive cock."

With that she began to pump my cock and finger my ass once more and I felt the familiar twitching as I quickly built towards an orgasm. Her grip got tighter and her pace faster as she wanked me harder and more, her fingers now constantly rubbing my prostate. Suddenly I was past the point of no return.

"Ohhhhhhhhh fuuuuuck!" I began to spurt my load and she continued to milk me, fingers and hand pumping me and milking me while I spurted cumshot after cumshot. It spurted all over me and ran down my cock and over her hand. I lost count of the number of times I spurted and still she kept milking me, her skilful fingers and hand squeezing more and more cum from me until finally I was just dry orgasming.

"That's it baby. Well done. Doesn't that feel good. We'll have to make sure to do this again for you soon." That was all I heard as I passed out exhausted and fell asleep.