A few years ago, it was a sunny August day and I was preparing for my company’s summer party. At the time, I managed a team of ten salespeople.

I was 47 and had been married for years, so the work night out was often the only fun I had all summer — a chance to get away from the wife and let loose.

In the team were five women. My favourite was Gina, a twenty-eight-year-old feisty half-Italian and a real cock tease. She was about five foot tall, with cute Italian looks, long black hair, big juicy boobs and a tasty tight arse. She had a perfect sexy body.

In the office she would wear the tightest dresses, showing off all her curves. She loved to tease me and all the other guys; even after getting married, it hadn’t stopped her. 

I spent hours wanking over her social media pages, imagining bending her over my desk, pumping into her hot wet pussy and shooting my hot cum deep inside her. Then telling her to clean my cock and get back to work. My mind ran wild with filthy thoughts.

My latest fantasy was to fuck her at the summer party. I imagined her running up to me with her arms out, finally realising she’d always wanted my cock. We would then sneak outside for hot, intense, dirty sex as she screamed my name. I wanked over this fantasy for weeks. 

The other four women in my team were in their thirties, all pretty average-looking at best. Jo was a big girl — loads of fun but not my type. Maja was Eastern European, kind of sexy but had three kids. Ruth was a bit too curvy and plain-looking. Then there was Jenny, who worked under Ruth. She was a bit plain-looking, not a bad body, a bit chunky but with nice big boobs.

Jenny never really spoke in the office. All I knew about her was that she was a single mum. She did the admin, so she wasn’t as loud as the others in the team.

On the day of the party the whole team were in the office talking about what they were going to wear. I was imagining Gina in a short, tight dress, stockings and suspenders underneath, pussy dripping wet. My mind was on overdrive.

I thought, If she was my wife, she wouldn’t be allowed out of the house — she’d be in bed all day getting that Italian pussy pounded and filled with cum.

The day went slowly, my mind filled with filthy thoughts of what I might do to Gina if I got the chance — fuck her in the toilets, maybe outside, sneak her back into the office. I was hard all day thinking about the different scenarios.

After work we all headed home to change and then back out to meet at seven at a local restaurant. My wife Sarah was out, so before leaving I had a wank over pictures of Gina on social media, shooting my cum all over my phone onto a picture of her slutty-looking face. Fuck, it felt good.

I dressed in my best outfit — jeans and a shirt — and covered myself in aftershave. Off I went to the restaurant. I was a bit late. When I arrived, everyone was there except me and Gina.

I said “Hi” to everyone and started mingling, having small talk with the team. Mainly talking to the lads about football, going through the usual motions.

Eventually Gina arrived. Wow… She looked amazing. She was wearing the tightest and shortest dress I’d ever seen her in — bright orange, showing off all her curves. Every guy in the restaurant looked as she walked in; the waiters nearly spilling drinks. She looked incredible. I just wanted to grab her, bend her over a table and fuck her right there.

I had to play it cool, so I let her talk to the rest of the team. All the guys were all over her. She knew she was hot and every guy in the team wanted to fuck her.

As I drank and talked football, my mind was racing. I wondered if her husband had fucked her before letting her out. Maybe he’d come inside her, and she still had cum dribbling down her leg, or he’d come on her face, and she’d licked it up. I got another drink and tried to focus on the night.

We all sat for the meal, and I somehow got bumped to the other end of the table with the geeks. I had a boring guy called Alan opposite me and single mum Jenny, who never spoke, next to me. Great, I thought. Gina was up the other end with a couple of guys desperately trying to impress her.

We had drinks and food and the night rolled on. I didn’t say much. Alan and Jenny were talking about work and it was really boring me.

I just looked up the table at Gina, staring at her amazing boobs.

The meal carried on as the wine flowed. I started to look at Jenny sat next to me. The seats were tight together and I could feel her thigh pressing against mine. She was wearing a short black leather skirt and a white tight top, opened just enough to see some cleavage. Those big juicy boobs were starting to get my attention. After a few drinks she was starting to look half attractive.

Alan was now moaning to someone else, so me and Jenny started chatting. She told me a long story about her ex — he had been a shit and cheated on her, and she had been single for over a year. She lived on her own with her kid. She then started talking about work.

“I love my job,” she said. “I think the team are great and you’re a great manager.”

“Thanks,” was all I could think to say. My filthy mind was thinking, I bet she’s gagging for some cock.

The meal ended and we all headed to a bar. I’d still not had a chance to speak with Gina. In my mind I was still going to have her tonight.

Eventually I spotted her stood alone. Just as I was walking up to her, she gave a big wave, then turned to a guy, kissed him, and he led her out of the door. Her husband had come to pick her up.

I’d never met him before, but he was about 6’2, a big Italian-looking guy, very athletic. He gave her a kiss, and they left together.

I was crushed. My fantasy came crashing down. It was now time to just drink and go home to my wife,  no-sex Sarah.

I got a beer and sat at a table on my own. The bar was full now and the team were either blind drunk or dancing.

I imagined Gina sucking her husband’s cock in the car on the way home, then riding him all night, his big fat cock filling her with cum. Fuck, I wish it was me.

Not sure how long I sat there dreaming, but eventually someone said,

“Hey Tom, all alone?”

I looked up and it was Jenny. She stood so I could now see her full body. Her leather skirt was short, showing her full legs — they were a bit chunky but sexy. Her big boobs were struggling to stay inside her top.

“Hey Jenny, I’ve lost the team.”

“I’ll join you then.” She squeezed next to me, pressing her body against mine.

“Gina’s gone then,” she said, smiling.

“Has she? I hadn’t noticed,” I lied.

“Hmm, I thought you fancied her.”

“Me? No, she’s just one of the team.”

“Okay Tom, it’s just that you stared at her all night, like you do every day in the office.”

“Err, not me.”

“Okay Tom,” she laughed.

“You know her husband is a big guy.”

“Yeah, I noticed.”

“No, I mean a big guy… like in his pants! She’s shown me pictures.”

Jenny seemed a bit drunk, and I wasn’t sure why she was telling me this. I really didn’t need to know Gina was going home to a monster cock.

Then quiet Jenny who never spoke leaned in and whispered,

“I bet I suck cock better than her though.”

I spat my drink out. I wasn’t sure if I had heard her correctly.

“Err… What?”

She smiled and responded, “You heard me.”

“Err, Jenny…”

She then discreetly ran her hand up my thigh under the table.

“I’ll take your mind off Gina.”

“Err… Jenny,” was all I could say. My mind was racing now. What was happening?

There was a crazy look in her eyes.

“Come out the back door and meet me outside in five minutes,” she demanded.

“Err… I can’t.”

She walked away.

My mind was spinning. Did quiet single-mum Jenny just tell me she wants to suck my cock?

I thought maybe it was time to go home. The rest of the team were either drinking or dancing in their own worlds. I could just sneak out.

Sarah would be awake and might fancy some hot sex? That wasn’t happening.

I decided to go talk to Jenny. I wanted to tell her to go home and help her get a taxi.

I walked outside to the back of the bar. Only Jenny was out there.

She had undone two buttons on her top and her big boobs looked desperate to get out. She actually looked quite hot in the dark.

“Look, Jenny, I’ll get you a taxi,” I said, trying to use my authority.

She grabbed my arm and pulled me into an alleyway next to the bar.

“Jenny, it’s time to go home,” I demanded as she pulled me into the dark.

She pushed me back against the wall and whispered, “Imagine I’m Gina,” before dropping to her knees in front of me.

Fuck, what’s she doing? This was now out of control.

“Jenny, stop,” I demanded.

She wasn’t listening. She undid my belt and unzipped my jeans in one slick movement.

“Jenny, just stop,” I shouted, but she was on a mission.

My jeans and boxers were pulled down, leaving my soft cock to fly out into the warm air.

By now my head was spinning. This needed to stop, but I did quite fancy a blowjob. My defences were slipping away.

She leaned forward and grabbed hold of my soft cock. Her hands were so warm. With a soft movement of her head, she opened her mouth and slid my cock deep inside her hot, wet mouth.

Fuck, it felt good. Her warm mouth instantly woke up my cock.

“Fuck… Yes,” I moaned as I got hard in her mouth.

She started bobbing her head up and down, sucking, licking and wanking my rock-hard cock.

Fuck, it felt good. My wife hadn’t sucked my cock in years, and after a night of frustration watching Gina, this was just what I needed.

Jenny looked up at me with her big eyes. She looked hot with my cock in her mouth.

I was paranoid someone would see us, so I kept looking around. Jenny was lost in the moment, sucking on my cock like she had never seen one before.

She sucked and squeezed my balls like a pro. I thrust deep and hard into her hot wet mouth, holding her head and fucking her throat, getting rid of all my frustration. Fuck, it was good.

It had been so long since I’d had a good sucking so I couldn’t last long. After a few more long sucks, I felt my cum ready to explode. I grabbed her head and pushed my cock deep down her throat. One more thrust and I shot a hot load of  cum deep into her mouth.

“Mmmmm fuck,” I moaned.

My whole body exploded. My wife hadn’t made me come like that in years.

Jenny swallowed the whole lot, even squeezing the last few drops out of my balls.

She stood up, pressed her body against me and leaned in for a kiss. As I kissed her back, I could taste a mixture of alcohol and cum in her mouth.

My jeans were still round my ankles, my cock still throbbing after shooting.

We kissed drunkenly, both still horny. I could tell it had been some time since she’d had any interest from a man.

I ran my hand over her big juicy boobs, squeezing them tightly over her top, then pulled up her skirt and ran my hand up her smooth thighs.

Her legs were chunky, but I didn’t care at this point — it felt good, I had a thing for slightly overweight women. 

She tensed as I moved my fingers towards her pussy. It’s probably been a while since this was opened, she must be gagging for it, I thought to myself.

She pulled her skirt up higher to give me better access. I could feel she was wearing nice lacy panties as I rubbed the outside of them.

Our tongues were still locked together, kissing and she was running her hand all over me. My cock was still recovering as she started to stroke it again.

I then slipped my hand inside her panties, moving a finger to her clit and slowly starting to rub it. I felt her body start to tense and she pushed harder against me.

I ran my finger up and down her pussy lips. Juices were already dripping out. I slipped two fingers deep inside her hot wet pussy.

“Yes, Tom,” she moaned.

Her pussy wasn’t very tight, so I easily slipped two fingers inside and started rubbing her G-spot. She responded by rubbing my cock even faster, making it rock hard again.

I fingered her pussy hard and fast. This made her moan louder and kiss me deeper. She was loving it.

My mind was a blur. What the fuck was I doing fingering Jenny from my team in a dark alleyway? It was so wrong. I thought about stopping but it was too late for that, this pussy needed action.

My fingers felt so good inside her. A few more fast finger blasts and she suddenly let out a scream. I felt her whole body explode as she came hard over my hand.

She stopped kissing me and put her head on my shoulder.

“Fuck… Tom, that’s good. Just what I needed. I’ve not cum like that for ages.”

I licked her juices off my fingers, stood there with my jeans around my ankles. My cock was now rock hard again. I was so horny.

“Face the wall, Jenny,” I told her.

She did. I pulled her panties down, held my hard cock at her entrance and slid straight into her soaking wet pussy in one smooth thrust. I grabbed her hips and started pounding her hard from behind.

I really needed this.

It started pounding her pussy hard and fast, going as deep as I could. 

“Yes, fuck me, Tom,” she moaned. I reached around and rubbed her clit while pumping in her. This was really dirty outdoor sex.

Her legs buckled and she dropped to the concrete floor. I kept my cock inside her, now knelt behind her, and continued pounding her doggy style. The floor was hard on my knees, but I didn’t care at this stage.

After a few intense minutes, Jenny looked back at me. “I need to stand up, my knees are hurting.”

Mine were too.

I stood her up, leaned her against the wall facing me and slammed back inside her, pumping harder and faster into her soaking pussy. It felt so good to be inside that pussy again.

We kissed and she put her arms around my shoulders as I lifted one leg to get better access.

I couldn’t hold out for long. After a couple of minutes of drunken fucking I was ready to shoot.

I felt her body tense again. She came hard again with a loud scream.

I couldn’t take any more. I shot a massive load of cum deep inside her, filling her up. Fuck, it felt good.

I pulled out, and she immediately grabbed my cock, wrapping her fingers tightly around it and wanking me fast and hard.

“Fuck yes.” Her juices had lubed me up. She squeezed every last drop of cum out of my balls.

I let out a loud moan. “Fuck, that was good, Jenny.”

“Mmm, I’ve been waiting for that, Tom.”

I pulled up my jeans as she put her panties back on and pulled down her skirt. Then without speaking, we headed back to the party, trying not to look suspicious and hoping we had not been seen.

I went and got a drink, sat down and thought about what had just happened. What the fuck had I just done? My head was spinning. 

About twenty minutes later, Jenny came over and whispered, “That was just the start. I’ll blow your mind next time.” She walked away smiling.

This night had not turned as planned, but I sensed this was just the start of my fun with Jenny.