Tag: Girlfriend

Long time reader. This is my first story.
July 2022. It was a very busy summer at our office. Everyday
seemed to bring some kind of crisis or another. But at least things were
somewhat back to normal. After two awful, pandemic-wrecked summers, we were in
the office 3 days a week. Back to work but also back to the after-dinner drink
and the client lunch and all of the little things that sometimes made work a
lot more bearable and a little less routine.
 
As a way to thank the team for our efforts the last few years,
our CEO decided to throw a big July bash on the roof of this new NoMad hotel.
(I Work in New York City.) Our firm has branch offices in Omaha and Nashville
so the people from those offices would be flying in for the party and spending
the night in the city. The party was on a Thursday night, everyone would eat
and drink at the hotel and then the adventurous among us would venture out for
the after-party. After a brutal few weeks leading up, I was determined to make
the most of the evening.
 
My long-term girlfriend and I had broken up in June. It
wasn’t one fight or betrayal or anything like that. More like we both somehow
slide into a gradual state of total ambivalence about it. In the end it has
been a blessed relief to be done with it. I’d thought about Tinder but wasn’t
quite ready for that scene yet.
 
I tend to avoid person entanglements in the workplace so I
didn’t really have any expectations for the party. But I have to say I was
excited to go out and hang with girls again, the excitement of an evening with
possibilities.
 
The day of the party was hot. I mean, one of those putrid
mid-Summer days in New York City. Add humidity and sweat. So of course, the
whole roof party aspect was a mixed bag. Drinking in the heat is always risky,
and quite a few people were fairly well in the bag by 7pm. I tried to stay near
the bar where there was some shade but after a few hours was dying to get out
of the sun. I had been slowly drinking beer as well as guzzling water to stay
hydrated.
 
At 8 the party ended and a small group of us moved over to a
bar a few streets over. I managed to get a seat at the bar with a few
colleagues. I ordered a gin and tonic and relished the drink’s coolness. More
people form my company were streaming into the bar, including a handful from
the Omaha office. People were starting to dance too. It may have been early for
the other patrons in the bar, but we had already been partying for hours.
 
It was very loud and I was getting tired of having to shout
at my colleague to be heard so we gave up on talking and I swiveled my barstool
around so my back was to the bar and watched the festivities. I’m not much of a
dancer but I did enjoy watching my friends and colleagues let loose. Across the
room, a group of five or six colleagues from our Omaha office stood and danced
amongst themselves. One of the girls was wearing a black pantsuit, white
blouse, and heels. Her brown hair came down slightly below her shoulders. She was
thin but not skinny. Watching her dance so effortlessly with no wasted motions,
I could tell she was very likely a good athlete. She certainly was fit. She
looked over at me and caught my eye. I looked away, embarrassed at having been
caught checking her out. I turned my stool to order another gin and tonic.
 
It was busy and hard to get the bartender’s attention. I
felt someone squeeze in next to me. I thought nothing of it until I looked up
and saw the girl from across the room standing next to me trying to also get
his attention. Now that she was next to me, I recognized her. I had met her
when I went on a trip to our Omaha office last year. Her name was Jackie. I
remembered her being quiet and polite and extremely cute but not much else. Well,
it had been a year ago, I thought. I leaned over and basically had to scream to
offer her a drink. She looked grateful for not having to get the bartender
herself.
 
“Martini. Dry. Olive,” she said.
 
I finally got the barman’s attention and got her martini and
another gin and tonic for myself. I handed her the drink and we tipped glasses.
I turned back to the crowd of my co-workers letting loose. More had arrived. I
had expected Jackie to go back to her Omaha friends. But she didn’t move. Just
stood pushed against me in the packed bar. Since it seemed like she wasn’t
planning on leaving, I offered her my seat. She shook her head no and smiled.
 
Ok, well this was getting interesting. Slowly she leaned in
closer to me. We still hadn’t said more than a couple of words. I smiled over
at her, and she looked me straight in the eye and moved closer to my lap. I
scooted back a bit and she stood directly in front of me, leaning her ass back
into my knees. I could smell her perfume, something understated and lightly
floral.
 
I cautiously put my hand on her hip, not squeezing just
lightly tracing. She leaned back further. It was at this point that I realized
my dick was rock hard, poking down the side of my pants. I was shocked at what
was happening here but wasn’t about to look a gift horse in the mouth, as the
old saying goes. I looked around but nobody seemed to be paying any attention
to us at all. She must have thought the same thing because she reached back and
started rubbing my thigh.
 
Seemingly, it had gotten even louder and I couldn’t hear a
thing. I was starting to sweat a little. My heart was beating rapidly and my
cock was not getting any less hard. I took a chance.
 
“Do you want to go somewhere where we can actually talk?” I screamed.
 
“Sure,” Jackie yelled, not even turning around. “As long as
they make a better martini than this.”
 
I laughed. She screamed in my ear. “I’m going to the lady’s
room. Meet me outside.”
 
I waited a few minutes outside. I wondered if maybe she had thought
better of this whole thing. Then she opened the door and stepped out. I walked
over to her.
 
“I know a place down the street,” I said. She merely nodded
and we walked side by side. Now that we could hear each other I wasn’t sure
what to say next.
 
“I just need to text my friend and let her know that I’m
ok,” she said.
By the time she did that we arrived at the bar. This was
more of a lounge. I knew it got very busy around midnight but it was only 9:30
now and the place was mostly empty. It was perfect. Dark and moody with nice
cushy seating in the back. I ordered us drinks and we went and sat in one of
the velvet sofas along the wall.
 
We drank and talked. She was shy on the surface, but once
you had cracked that, she was all witty repartee and flirty asides. She worked,
ran marathons, loved her dog, and was getting over a recent breakup with her
boyfriend who she had been with since college.
 
“I can’t believe I stayed with him as long as I did. I
wasted some good years,” she said.
 
“How old are you,” I asked.
 
“Twenty-eight”
 
“Well, you have plenty of time to make up for those years.”
 
“I know,” she replied seriously. “I’ve already begun.”
 
She turned to me and I kissed her without thinking. She
immediately kissed me back, her tongue in my mouth urgently. We made out like teenagers
for 15 minutes or so, hands clawing at each other’s backs.
 
“Do you want to come home with me,” I asked finally.
 
“How far away?” she responded.
 
“40 minutes at this time of night.”
 
“Fuck that, let’s go back to my hotel room.”
 
I paid the check and we practically ran to her hotel. We got
off the elevator and over to her room and I slammed the door behind me and we
were on the bed in seconds, my tongue in her mouth. She was breathing heavily
through her nose. Jackie started clawing at my shirt and I sat up and pulled it
off. She collapsed onto her back and lifted her hips in that little motion that
women do and pulled down her pants and panties before throwing them in a ball
on the floor. I fumbled with the buttons of her blouse before she helped me
lift it over her head. Her bra was next and then we were both naked.
 
She was amazing naked. Probably 5-7 without heals. Legs
skinny but muscular. Her pussy was shaved. She was smiling. He had cute little
dimples. The whole package was perfect. I looked over at myself in the mirror.
Been shaving my head since 21, I think it helps keep me young looking. Body
still good at 36, though not quite a muscular as pre-pandemic, when I went to
the gym three times a week. Still I was looking good. I looked down at my cock.
I couldn’t remember the last time it was so hard. 
 
Jackie didn’t waste another second. She pushed me down on
the bed and sat on my dick. She was soaked so I slid right inside her. She
sighed and closed her eyes. She put her hands on my chest, her nails digging in.
She was so tight. She moved up and down a few times. I knew I wouldn’t last
long. I closed my eyes, which is a little thing I sometimes do to keep my mind
calm. It’s easier to last when not staring at the beautiful woman bouncing on
my cock.
 
Luckily it wasn’t really an issue because she moaned and
started shaking almost immediately. I could feel my dick get even wetter. I opened
my eyes. She had hers closed, biting her lip. She moved up and down again in a
jerky motion and I slid out of her. She was almost wailing now as the orgasm
coursed through her. She leaned against me panting.
 
“Fuck I needed that,” she said.
 
I didn’t respond. I just grabbed her and pushed her her
back. I thrust myself back inside her and moved in and out and fast as I could.
She wrapped her legs around my waist. I wasn’t going to last much longer. Her
face was flushed but her eyes sparkled.
 
“Where should I cum?” I said, thinking for the first time
that I didn’t have a condom on.
 
“On my stomach. Please shoot it on my fucking tits.”
 
That did it for me. I could feel the muscles in my legs
clench, and I pulled out my dick and stroked it over and over. Cum shot
everywhere, most of it landing on her tits and stomach.
 
“God, it’s so much,” she said.
 
Before I could catch my breath, she had scooped my cum off
her tits and was greedily shoving it into her mouth. It was so fucking sexy. I
watched her in amazement. She looked sheepishly at me and said, “Sorry I just
love the taste.”
 
“Please don’t apologize,” I said. I was sincerely flattered.
 
We lay quietly for a few minutes. The bed was a mess. We
were a mess. It occurred to me that I desperately needed a shower. It had been
a long hot day and an even hotter few minutes.
 
“Do you mind if I shower quickly,” I asked.
 
“Be my guest.”
 
I walked into the bathroom and turned on the water. The
shower was cold, but I didn’t mind. I quickly soaped up and started washing. A minute
later she was in the bathroom. Her hair was up in a bun. I could see my cum
still sticking on her parts of her chest. Without a word she came into the
shower. I grabbed the soap and started to lather but she pushed my hands away.
 
She turned to look at me and took the soap and started to
lather her body. She didn’t break eye contact with me. I looked at the soap
running off her tight body. God, she didn’t have an ounce of fat. When she was done,
I turned off the water but before I could step out she was on her hands and
knees. She took my cock in her mouth, moving her tongue along the shaft. I was
rock hard again and loving the feel of her mouth, but after a few minutes I got
impatient to fuck her again.
 
We toweled off and headed back to the bed. She had turned
the AC on and it was nice and chilly now. We lay down and I pulled the covers
over us. We kissed slowly, savoring each other’s taste. I slowly moved my hand
across her hips and thighs. She purred. I could feel the heat coming off of her
pussy and reached down and started rubbing her clit. I moved my mouth over to
her breast and sucked her tit slowly and gently and then just a little roughly,
lightly running my teeth over her nipple. She gasped. She softly stroked my
cock, the light touch making me shudder.
 
My dick was aching to be inside her again but I wanted to
take my time with this. I started kissing my way down her body. Slowly.
Lightly.
 
She was almost humming again.
 
I teased her for a bit, kissing the inside of her thighs. I
kissed around her pussy before finally licking her clit. She wrapped her legs
around my head. She was shoving her hips off the bed, pushing her pussy into my
mouth. I kept the same pressure on her clit before sticking a couple of fingers
inside her. Her hums became moans.
 
“Please keep doing that, fuck. Fuck fuck fuck. I’m going to
cum”
 
She moaned and twisted her head from side to side before
eventually falling silent. I crawled back up her body. She looked me in the
eyes, grinning mischievously. I kissed her again.  My dick poked her belly, just inches from her
wet pussy.
 
“I want to fuck you now”, I said.
 
“Yes. Don’t worry about a condom. I’m on the pill”, she
replied breathlessly.
 
She reached up and grabbed my cock and slipped it inside
her.
 
I went slowly at first, giving her a chance to get
accustomed to my dick. We stared at each other silently. Part of me still
couldn’t’ believe this was happening. I went harder. Her hands were at the back
of my head. She smelled like soap and sex. She pushed away a brown lock of hair
out of her face. We started groaning.
 
“How old are you,” she said.
 
“Thirty-six”, I replied.
 
“I’ve never fucked anyone over 30 before.”
 
“Oh wow” I replied. I didn’t really know what to say. “Do
you like it?”
 
“So far so good. Your quiet confidence is hot. But I want
more. Can you do that?” she said.
 
That made my dick even harder, if that was possible. I
pulled out of her and roughly flipped her over onto her belly. I stood on the
floor, dragged her onto the edge of the bed, and slid my penis back inside of
her. She groaned. I grabbed her hips and started fucking her as hard as I
could. She was so hot in this position. Her ass was literally perfect. We got
into a good rhythm, the only sound the slap of our bodies connecting.
 
On a whim, I pulled her hair back and gently yanked it
towards me.
 
“Now I’m really going to fuck you,” I whispered in her ear.
 
She moaned. “Yes, pull my hair. Please, please, please.”
 
I gripped her hair and pulled. She was moaning again. We
continued to fuck. I reached forward with my left hand and felt her tits and
tight stomach. Runners body, I thought again. I let go of her hand and slapped
her ass. She came then, her breath catching, her body suddenly going slack. I
could feel the beginnings of my orgasm. I spread up my thrusts. I think she
could feel that I was close.
 
“Cum inside me.”
 
I grunted and let go, squirting off into her warm pussy. It
was perfect I pulled my dick out and lay down next to her, completely spent.
 
We were quiet for a few minutes. Her breathing got
shallower. She pulled the covers over her. My mind was still too blown to fall
asleep yet but I held her.
 
Before drifting off she murmured, “Think I’m going to have
to find me some 30something men in Omaha.”
 
“Lucky bastards,” I replied.
 
I woke up before her. It was 8pm. We had to be back in the
office for a company breakfast at 9. I started getting dressed. It was going to
have to be in yesterday’s clothes. I went to the bathroom to get changed and
brush my teeth. (I keep a brush and paste in my work bag for situations like
this that may arise). When I came out she was standing in her panties and
putting on her bra. I always thought it was sexy watching a woman get dressed
in the morning.
 
“You’ve got to leave,” she said. “And quietly, I don’t want
my co-workers to see you coming out of my room.”
 
Not wanting this to get around the office myself, I figured
this was prudent advice. I said goodbye and tiptoed out in the hallway, holding
my breath until I got to the elevator. It was hot outside again today. When I
saw Jackie in the office later, she gave me a shy smile, her cheeks reddening
slightly. I said goodbye when her and her colleagues left for the airport.
 
That was the last time I saw Jackie. We had emailed a few
times but were both really busy. In September I saw an email from our HR
department saying she had left the firm for a new opportunity in Chicago. I
still think of her fondly, maybe the next time she is in New York….