This is a fictional story, but the women is loosley based on my own partner.
CHAPTER 1
I had never been the one being pursued before. But here I was on the brink of 30 and recently single. I haven't had an uneventful sex life, but this was different. This was an older woman, and she seemed so sure of her self, which was already a turn on. She was 42, so not a "older" woman but someone with certainly more life experience than me. She was in real estate, had two kids and had been divorced for several years. Besides that I didn't know much else about her. She did mention though that through some life experiences she learned that she wanted to make sure she pursued what makes her happy. And sex was one of those things.
From the first conversation on the dating app (initiated by me) it was apparent that at most she was looking for a reliable hook up. But this was not just any booty call. She had lots of questions for me and often controlled the conversation. Asking me about my own dating and sexual history. We strictly used the app for communication until we decided to meet in person did she give me her number.
It was an afternoon date. Which the timing felt more like an interview despite already somewhat getting to know each other through messages. I arrived at a coffee house around 3pm. It was fall, so golden had hour started earlier.
The large store front windows filled the front of the shop with sun light. I sat and watched the traffic a bit before checking my phone. I hear the door open and I look up to see the face from the picture on her profile enter the room. The same face with big brown, eyes, pronounced cheek bones and full lips. Her brown hair was short and fell just above her shoulders, slightly curled, and perfectly complimented her fair skin and faint freckles. She looked great. She strategically did not have any full "body shots" as most of her pictures were from the waist up and while her outfits were flattering, they were not revealing, almost as if she was hiding something. But she seemed quite confident in herself. And now looking at her in the warm sunlight, I realize she was hiding her body, but only to keep a vail of mystery.
She was petite, probably 5'3" or 5'4". She was thin but had some "mom hips" and somewhat thick thighs. Not a "thick" woman but no Barbie legs, pear shaped. Her legs were encased in some tight high waisted black jeans. She had a petite waist covered by a thin grey turtleneck tucked into her jeans that made her butt and her hips look amazing. Picture a in-real-life version of certain superhero mom from an animated film. You get my drift.
Her flat tummy lead up to a pair of small, but beautiful breasts, probably a B or C cup if I had to guess. They didn't have the perk of a 20 something year old girl, with no kids, but had the bounce of a woman, which was so much sexier. I looked at her and imagined what her nipples might look like. What kind of underwear she was wearing. Is she shaved down there, or natural? Clearly getting ahead of myself.
She hadn't even made it to the table and I was hooked. We greeted, got some coffee, and a pastry and talked for a bit. Finally she sighed and looked at me in the eyes.
"Ok well I think we know why are here. This conversation has been sweet and reassuring. You seem like a nice guy. And I want to see you again...but in a different context." She pauses holding my gaze in her big brown eyes. She continues. "My kids are with their dad for the weekend and I got a room downtown."
"You really thought this out, huh?" I replied.
"Well to be honest I don't really do this very often...or ever. So yeah I thought about it a lot." Staring right through my soul.
Trying to not to sound to eager I replied "Well I am in. When and where do you want me? Can I buy you dinner?"
"Just come to my room tomorrow around 6 and we will go from there."
I walk her out of the coffee shop and exchange a brief and awkward hug good bye. I can't believe this is happening.
That evening I get a text from her:
"Looking forward to tomorrow"
Next a picture loads. It's a photo of a big bed in a luxurious hotel room. On the bed laid out is a dark blue equally luxurious lace lingerie set.
I could barely respond "Can't wait" before my hand was wrapped around my cock, masturbating to the picture and the image she has painted for me. I cum all over my own hand and stomach. Laying on my back covered in my own cum, breathing hard. I slept well that night.
CHAPTER 2
The next day rolls around. I nervously get dressed to head downtown. I hadn't heard from her yet so I was anxious she was going to back out. 5pm, I finally got the text. "Hotel xxxx Room 2641".
It took me about 20 minutes to get there, but it felt like hours. The image of the lingerie burned in my brain. Finally I step off the elevator in the hallway walking to find her room. At the end of the hall I see 2641.
I gently knock on the door. My heart is racing now. She opens the door with a smirk. She's in a robe. Her make up is done, her toes are painted. She invites me in with a bubbly smile and tells me to have a seat.
It's a corner room with two walls of windows over looking the city, with a couch up against one set of windows. There is a big oversized bed in the center and folded neatly are the black leggings and green tank top she must have been wearing earlier.
She had disappeared to the bathroom and we exchange small talk from the other room. After a few minutes she calls me in. Again my heart starts racing. I turn the corner of the bathroom to see her wearing a dark blue romper. Her legs looked great. It showed off her hips, her petite waist and her ass. It had a deep v-neck which showed some cleavage. She had on a black bra on with some lace detail. I know this because the back was open and she called me into zip her up. I think she probably could have gotten it herself but I'm glad she used the opportunity to tease me.
Standing behind her I catch a glimpse of us in the mirror. To be honest, I think we look great together. I was wearing a tight blue button down that showed off my arms a bit and some grey chinos that did nothing to try and hide my own assets. This was my own attempt at flaunting. Soon we went out and to find a cocktail bar with small bites and drinks.
We had gotten to know each other a bit but the vibe was a lot less formal. She was very loose and seemed comfortable. Our conversation had moved past the "interview" part of our "dating" and it felt like more like friends. She is also very funny. But every once in a while she would grab my hand or I'd feel her leg rub against mine and it would remind me this was more than a buddy comedy.
The night could have been over and honestly, I would have been happy....Was my thought as I was sitting at our table with a view down the length of the restaurant. She had gone to the restroom. In my opinion I had the hottest date there that night. When she emerged from the back I got to watch her stride across the room. Her curled hair bouncing with her steps.
Sitting back down, this time next to instead of across from me. She reached over and grabbed my hand puts her lips near my face and says quietly but directly. "I would like for you to take me back to my room now." With this phrase she also guides my hand to rest on her upper thigh. I turn and kiss her deeply. Gripping the soft skin of her leg.
"Yes ma'am" I reply. "I'll get the check"
My stomach sank on those words with excitement. Suddenly I felt my cock swelling in my pants. The pants and underwear I chose were already snug and I felt good in them, but all of a sudden I was very aware of how tight they were. Leaving the bar we walked hand in hand back to the hotel. If anyone was paying attention they would certainly see the outline of my hardening cock walking down the street.
At one point while waiting for a red light I kissed her again. I didn't know if this was the right move but the drinks certainly helped encourage me. To my delight she responded with a great kiss. I felt her tongue meet my lips and dart around with mine. It was incredibly sexy. I also couldn't help but think about my theory: those who are great kissers can also do other great things with their lips and tongues.
CHAPTER 3
We were now at her room. I used the restroom and washed up, trying to keep my compisure. She passed me leaving the bathroom and this time she kissed me.
"Wait on the couch, I'll be back in a few" The door closed behind her and I sat patiently gazing at the skyline, waiting in anticipation.
Suddenly the bathroom door opens she steps out into the glow of the only light on in the room. A can light near the entry door provides a great spot light. Gone is the romper. In its place were tan nylon thigh highs held up by a deep dark blue lace garter belt, and her black high heels. Below the belt was a matching high waisted set of sheer thong panties that showed a dark triangle of pubic hair. It was a bit of an old school look, and it was insanely sultry. Like an old school pinup girl of my dreams.
Her tits, however, were bare. And they were beautiful. Perfect tear drops with big, but not too big, puffy pink nipples. They bounced and swung with every step.
"Wow" I say sitting up straight.
"I thought you might like this. I decided to leave the off the bra. I hope you don't mind."
"I couldn't be more pleasantly surprised"
"I saw you stealing looks at them. I thought I'd give you a little treat right off the bat."
She strides across the room to me and turned around displaying her plump ass.
"Touch me", she commanded. I obliged, still seated, and ran my hands down her lower back and over her ass feeling the material of her sexy lingerie. She turned around, her nipples now eye level with me. I gently grab each breast with my hands and she steps forward putting them in my face. I am now kissing her belly just below the underside of her breasts while fondling them with my hands. Her nipples are hard and protrude out like they have been used for breast feeding. Long nipples are a bit of a fetish of mine.
"Stand up and take off you clothes." I do as I'm told and strip down to my black tight briefs. I can tell she liked what she saw which was a rock hard buldge with pre-cum seeping through the material.
She took the liberty of coming over and running her nails down my chest and stomach. Then over my throbbing bulge in my underwear. I gasped at the mere touch of her hand on my cock. I could feel her fingers gripping my balls through the material. She then takes both hands and slowly slides her fingers in my waist band allowing my cock to spring out. She smiled and grabbed it firmly.
She then leaned in for another passionate kiss all while holding and gently stroking my cock. She then drops to her knees lifts my cock up with one hand and starts gently caressing my balls with the other. Kisses my thighs and my stomach. Still gripping my dick. Then sticks her tongue out and licks my balls and slowly, following up the shaft to the tip. Now cradling my hard dick against her cheek she gently kisses and licks the pre-cum from the tip, looking up and smiling at me.
"You are incredible" I say through my groans.
