After helping a colleague get pregnant, life took a very open status with me. I was open to more interesting relationships and roles. Women I dated, liked that I was easy to talk to – and a gentleman. I would invite to my dinner or my place once they were comfortable – would ask very polarizing questions which would indicate their deep inner desires, sometimes even question the relationships they were in. I salute many of them for walking out on such proposals. But this story is about one who never questioned my advances.
F (name changed) confided in M(me) later that she thought I was a cop and was in fact scared of me when we first started talking. But I asked if she wanted to go out for dinner a few moments after we struck a conversation.
M: “Get in”. I said as we passed my car.
F: …. (Didn’t say a word and got in)
M: “So what do you want to eat, what time do you have to get back?”
F: “You decide”.
In this day and age – who says something like that I thought. She was staying with a group of her colleagues, who all had boyfriends – and she was 34 and not planning to get married until 40. I listened to this career woman who clearly had a lot on her plate.
F: “Are you a cop?”
M: “Do I look like one?”
F: “No my manager thought you were when you walked in, and me too. I’m scared of cops”
M: “Then why did you come with me?”
F: (Silence)….. ” I don’t know”
This was exciting for both of us. I could have been a dangerous pervert. Or one of her demons. Which is why she thought this was exciting. It was already 9 pm – and I offered to go to a pub walking distance from my house.
M: “I stay there. (pointing to a building ) and we’re going here. ”
F: “Ok, you stay here…”
M: “Ya we can just walk back to my place once we’re done”
It was a subtle move. And she didn’t object. I decided to up the role play but wanted to enjoy a good dinner and drink at the same time.
We had a nice time talking about various things and started showing me photograph’s and telling me about her life. and also took a photo of me to send to her friends in case she doesn’t come back tomorrow. That was funny – and it showed that mixed with the smile was some concern.
M:”Sure”
She showed a lot of photos from her family, and how she had worked hard to provide for her siblings from a very early age. Across many different kinds of companies mainly in admin kind of roles. A lot of her photos had her in a one-piece dress – and I guessed that was one of her favorite. She looked amazing that night as in those dresses. Curvy at all the right places, and silky smooth skin that glowed. Almost unaware of how pretty she was – and what kind of attention she got when she smiled.
I paid the bill and stepped out. The manger smiling because he had seen me quite a few women now. it was chilly. She clung to my elbow as some cars approached quickly as we were crossing. I felt a responsibility to protect, wrap her that crossed my mind. Here was an accomplished career woman who wanted to be protected, feel loved I sensed.
She was again scared what the watchmen were judging as we parked in my apartment society. We entered my flat which was much bigger than what I needed but was great to have parties, and friends over.
I excused myself and came back in just my jocks and a t-shirt. We popped open some beers while. She was in jean shorts the whole time. And there were a lot of sofas all around.
I commented on how smooth her hands and legs were. Started kissing her hands. And she was caught little off guard when I swooped down to plant a kiss on her lips. She was next to me and slipping lower on the sofa.
We spoke some more and started holding hands. I was done with my whiskey. She came to my kitchen and said she would wash the glasses. To be honest – while I’ve been a long time ISS reader – my servant never turned me on and I had no such plans. (Although a new cook from the neighbour looking for additional work once did offer to wake me up with tea. anyway).
F: “No, no. I like doing this. You just sit there until I’m done”
That’s when I realized I had a submissive in my flat, who didn’t just want to pretend to be one – I guess she had enough of responsibilities at work. Outside work – she really was one. (Or perhaps at work too, anyway).
She was at the sink. I sat bag on my chair and watched her. She smiled and happy to see me relax.
I went behind her and although it was a big kitchen, stood right behind her, feeling my hardness grow between her small shorts. She didn’t say a word. Almost completely oblivious to someone taking or about to take full advantage of her. She seemed to have accepted the fact that this date wasn’t going to just stay at first base.
I stretched her t-shirt around her shoulders equally on both sides. revealing her bra. It was wicked. Like a hot knife cutting through butter as she continued to dry the glasses attentively as my mouth was now tasting her neck and shoulder blade.
Wow, her skin was so soft. I had all the time in the world as she completely accepted all my moves. Eventually moving hands to her bare waist, pulling in towards my crotch – as if challenging to distract her. But as I moved my hands further up – she let out a moan and closes her eyes.
F: “Oh my god”,
She said softly, as I started pinching her breasts. Slowly raising the shirt from below. She started breathing more heavily. I turned her around and took her back to the sofa.
I pulled her. and in one swoop – she was on top of me – with her boobs sticking out. As if surrendering herself. Her crotch on time of mine. The dim lights leaving the perfect setting for my dessert.
And I started licking, biting, and teasing her nipples for a good 10 minutes. She loved all the different mauling that resembled a lion eating out a helpless deer. Meanwhile, my hands were playing with her ass. Raising her with my arms once in a while and dropping her hard on my hardness under my jock.
M: “You don’t like kissing?”
F: “No, I like how you’re sucking and eating my boobs…”
Slowly got fingering her wetness. And before long we got down to our inners.
She then got on her knees and wanted to give me a hand job. This woman was a pleaser!
She found the coconut oil from the kitchen and got to work in her bra and panties kneeling before me and stroking me, finding the nerves. She had definitely done her research.
After ten minutes, she looked unhappy – I said I don’t cum like this. She was disappointed.
M: “I need to bang you”
She didn’t say a word, but got up and followed me. We moved to the bed and got naked. And she helped put on the condom and then I switched places, pinning her down with my hands. She was significantly smaller than I was. And I didn’t hold her hands. I pinned them down near the wrist with my weight. I will never forget that look on her face. Helpless and wanting to satisfy me. With half my dick inside her – she opened her mouth and took it in no further, wanting to relish the continued surprise later. Pulling back and forth with my pelvis, but not more than half. And then once lubricated in one swoop – started banging, the whole mattress and her bouncing under my weight helplessly, and her face becoming red and I loved showing her no mercy.
M: “You came with me – from the beginning because you wanted to get fucked. didn’t you” – I rhetorically whispered into her ear.
Tears now coming from her eyes, and just taking my pounding.
M:”I’ll wake my pet up any time I want and fuck you when you’re sleeping”
M:”You better learn to wake me up with a blow job”
She came for the second time, and so tried a bunch of positions. Once done – she had a bath and changed back ready for me to drop her. When she asked if we could do it one more time.
Wow. Stripped her again. And this time she was on top and I gave her just one instruction.
M:”Fuck me”. I spread my hands and legs far apart. Only her pussy in contact with me.
She started bouncing, and I was loving sucking my favorite – her breasts.
M: “Want me to milk your breasts every day? Twice a day, and then get fucked? ”
M:”I can’t wait to tie a leash around your neck as you clean my house everyday naked”
She came again. Had bath again. And I dropped her back.
We met the next night and couple of times here and there. She waits for my message.
M: “Time to milk you”.
F: “Ok.” she replies.
And now we don’t even speak. She knows what time I will pick her up. She makes sure she wears one-piece dresses that I like. That gives me access to her panties as we drive. We go straight to the flat and I pound her.
Nowadays she loves when I pull her long hair as I fuck her doggy style of the missionary; stick a wax candle in her ass as she gives me a blowjob; etc. It’s interesting to see far this will do.
Thanks for reading.