(All characters in this story are 18+ and consenting adults.)
This going out and partying on Friday nights thing was new to me. Then again, working was new to me.
I wasn't even working fully yet, just a 21-year-old intern, barely a month into my first ever job. I already hated working, and I hadn't even graduated yet, that would be in 4 months or so, if I passed my exams. But I could get used to these Friday nights, because I never paid. I only got drunk and tried to hook up with women (unsuccessfully).
Not that I was brave or anything, I just stared at women and hoped that I could speak to them in a drunken state (yes, I know now it's creepy). But today we were at my college hangout bar and I actually knew a few of the girls here so maybe I would get lucky, at least that was the plan.
Around my colleagues, it was proving to be near impossible. But they would all leave soon if the patterns of last few Fridays followed and then maybe I could go join some of my cute juniors sitting at another table.
In about an hour my assumption was proving correct and when they were all gone, I went to the bar to get a fresh drink, the plan was to grab it and ask if I could sit with them while I grabbed a couple more drinks. That was until someone tapped me on my shoulder.
When I turned around I saw this gorgeous woman, and she was smiling at me.
'Heey, do you remember me?'
She had beautiful eyes that twinkled, full lips that curved into a smile, long wavy black hair with a few streaks of grey that flowed onto her boobs. They were quite big under the red (wine coloured?) dress she wore. The dress had no sleeves, it began at her boobs and finished mid thigh. It accentuated her hips and boobs.
As much as I had wished I knew this woman, there were no bells ringing in my head.
'Umm, sorry, I'd love to buy you a drink but I can't place you.'
'Oh, is your name Glen Coelho?'
'Yeah! That's me! Do I know you?
Then she reached over to my ear, she grabbed it and twisted it while saying, 'Show me your knuckles Glen or I'll give you a spanking!'
a
'OH MY GOD! Miss Sanjana? I didn't recognise you, I'm so sorry!'
How was this my school teacher? Did I not realise back then that she was a babe or did she have some sort of a transformation?
'Phew! I'm so glad I didn't assault a stranger.'
I laughed and said, 'Looking like that, most strangers might welcome it ma'am'
'Thanks', she said, as she blushed.
I spread my arms wide going for a hug and she obliged. I think I might have pressed her closer than I would have otherwise but I was 3-4 drinks down and I wanted to feel her boobs.
When I stepped back I said, 'Let me buy you a drink, to make up for not recognising you.'
'Sure', she said, as she looked to the left and signalled to her table that she would take 10 minutes. I looked over and I hadn't noticed it before but they were all older women on the table.
'Your friends?'
'Yeah, we're having a bit of a reunion, we all used to go to St. Keaton's together.'
'Oh me too! When did you go?'
She reached over and gave me a little slap as she said, 'A long time before you.. we graduated in '93'
She paused for a second looking unsure, then continued.
'You'll still buy an old lady a drink, no?'
'Of course, I'll buy a hot lady a drink, you look very beautiful Sanjana ma'am'
'You're so sweet. Thank you'
We ordered our drinks and stood at the bar and spoke to each other for a while (more than 10 minutes). She told me how she was now in a different school and that her husband and she had a divorce 2 years ago and she didn't wan to work at that school anymore.
I told her all about my new internship and that I was due for graduation in 4 months or so.
We then reminisced about old times and spoke about my classmates from school and where they were. Which sparked a question in my mind.
'How did you even recognise me, ma'am?'
She blushed.
'My friends have been checking you out since you came in and after a while I realised that it was you... I told them to put it out of their minds and that you were too young for them...'
I looked over at them once again and now that I'd heard this from Miss Sanjana, I could see them stealing glances.
'Too young? I'm a 21 year old man, ma'am'
She put her hand on my shoulder and leaned in.
'I said for them.'
I smiled, met her halfway and kissed her on the cheek and then we both looked towards her friends. They seemed to be in various states of celebrations and smiles. We laughed.
I looked at Miss Sanjana who was flashing me a broad smile. I leaned in close to her ear and asked 'Care to turn this into a date?'
She was already nodding when I withdrew, 'I thought we were already on one.'
We then spent most of the night just catching each other up on the many years that had passed since we last met. Turns out we didn't live too far away from each other and I found out that my former teacher was a trained dancer. When I asked her to show me some moves she said she put up some of her dance videos on Instagram. I made a mental note to go check them out later.
Some time after a few drinks she asked, 'Do you like older women?'
'I don't know really, I'm attracted to you though, I don't know if age makes that much of a difference to me.'
'I think I must be twice your age though... How old are you?'
'Just turned 21 this year. But...'
'Gosh! I'm nearly 50, I mean I'm not but I'm over twice your age!', she exclaimed, as she put her hands over her face and laid her elbows on the table.
'Ma'am, relax...
I extended an arm to lay on her knee to comfort her. She was sitting to my right, so I couldn't really see it and had to guess. I landed on her thigh, which was bare, the dress must've pulled up a bit when she sat because I could feel the hem of it.
'...I think you're really pretty and I haven't thought about your age at all this evening.'
'Really?' she said as she took the hands off her face. I nodded, and she put her hand over my hand which was on her thigh and gently pressed it.
'You're really sweet, Glen', she said before she kissed me on the cheek. As she did, she had to slightly rise from her chair. When she sat down my hand had slid slightly under her dress. I pulled away and put my hand back on the table. She held it in hers and put it back under the table... Was that her pussy? Definitely, it felt moist and I was feeling it through her panties. She definitely had hair down there so it must be her pussy. She let a couple of seconds pass and said, 'Should we get out of here?'
I nodded.
We were holding hands as we walked towards her place. It was past midnight so there was nearly no one on the street, just people who we leaving bars. We took a side street to avoid people and a little way down the road she pulled me on to the side of a parked car so she had her back against it and we kissed.
I could feel her hands on my ass and back. Mine were on her hips and neck grasping and exploring as we kissed. We broke off only when we saw a light in the periphery of our vision which meant a car was in the vicinity. Now I couldn't wait to get home. We weren't far now.
We walked a little further down the road and turned into another one. Once again, she pulled me to the side and pushed me up against a minibus, this time she had her back to me and was grinding on me so I reached around and started to cup and feel her boobs. She arched back so I could access her neck and I started kissing it while I fondled her tits. I'm not really sure what I did but her dress kind of slipped and I could feel her bare boobs.
It spurred something in me, I put her back against the bus and started licking and sucking on her boobs. Her hands were in my hair and one of them guided my hand to her pussy. I rubbed it over her panties as i sucked on her tits and kissed her.
'Fuck me, fuck me, lets go I want you to fuck me..', she said.
She broke it off and corrected her dress. Now we were speed walking to her place.
'I'm not usually like this honey, I just haven't had sex in a while, and...'
'It's okay ma'am, I'm having fun, I hope you are too.'
It took a few minutes but we got to her apartment. As she found her keys and fumbled with the lock, I grabbed her ass.
'Just a bit more, we're there.'
She turned on the light and turned to me as I shut the door behind me. We kissed again, her arms were around my neck and i was holding her by the ass.
I started to let my hands roam, touching her back, feeling her neck and caressing her face as I began to then kiss her lick and earlobes. She moaned and said something about her shoes, I think she wanted to take them off but I assumed she meant she wanted me to take them off. So I pushed her on the couch and kicked off my own shoes.
I knelt on one knee in front of her and took her foot and placed it on my knee. As I did, it gave ma glimpse of her black panties. She saw me look and smiled.
I took off her shoe and started to kiss her leg going up to the inside of her thigh. Then I stopped and did the same with her other leg, this time going all the way to her pussy and kissing her under wear. She then stood up and unzipped her dress on the side, letting the top of her dress open up like a flap.
I stood up and she started to unbutton my shirt so I helped her. The she caressed my dick through my jeans before beginning to slip them off too. The underwear sort of came off with the jeans.
She knelt and planted a kiss on the side of my shaft and the got up and walked to her bedroom. She paused in the doorway and without turning around peeled her dress off, leaving it on the floor. Then she looked around and winked, I followed.
I came up behind her next to the bed and held her from behind, once again fondling her boobs and kissing her neck. I then slipped one hand in her underwear to rub her pussy.
I could hear her gasping in my ear which just made me hornier. So I bent her over, rolled her panties down and knelt kissing her ass from behind and rubbing her pussy from in between her legs.
I could hear her panting and moaning. She laid down on the bed face up.
'Can I go down on you?'
'Mmmhmm' she said, nodding.
I licked the lips of her pussy and then her clit while holding onto her thighs. I would break it up every few seconds to look at her pinching her nipples or squeezing her boobs as I licked her. She whispered breathy instructions like, 'lower, or faster, or just yess'. After one prolonged yessss-unh-unh-unh, I started to finger her.
Her legs were over my shoulders straddling my head. I extended myself a bit so her legs got pushed further towards her torso and raised her pussy allowing me to fuck her pussy with my finger. I put a couple of fingers in her mouth and as she sucked on it I kept finger banging her.
I took my wet fingers from her mouth and used them to caress her nipples.
'Unhh, fuck, keee--uuunh keep going babyyyee'
I lowered myself again and licked her clit while I fingered here. She let one of her legs fall back onto my shoulder but held the other one and with her free hand she held my head.