Penny's Pub

It was a late fall Friday night and a group of us from work were out for a few drinks at a bar near the office. As time passed, people drifted away and the only ones left were myself and a woman named Penny who worked in the same department as me and was a couple of years younger. She had a really sweet personality, a quiet, dry sense of humour, and I found myself getting attracted to her as we quietly conversed. She also played on the infamous office softball team, but usually left right after the games and I really didn’t know her well. She was a bit plump, but that didn’t bother me in the least - I love big boobs and butt on a woman and always have.

We were getting a bit bored with this particular bar and Penny suggested going to a neighbourhood pub that had recently opened near her parent’s house in Burnaby (Penny still lived at home to save money). It was easily accessible by bus, so I agreed. Off we went and soon we were ensconced in the new pub. Penny was getting a bit flirty and I decided to make a move on her. There were a fair number of motels in the area and I suggested getting a room, as Penny had already said her parents were at home.

“Look, I’d love to get it on with you, but I have my period and I think I’ll just head home later. Maybe some other time,” she gently suggested. I guess my disappointment was obvious, because she said she’d “take care” of me in “another way,” and made a subtle jacking motion with her fist. I asked where we could “do the deed” and she said to follow her. We went out the front door of the pub and walked around the corner to an access to the pub’s dark outdoor area. It was rainy and quite chilly out, so the patio was empty.

There was a small bench against a wall of the pub, concealed from direct window view from the pub by a corner and sheltered from the rain. We sat on the bench and started a hot necking situation. Despite her quite demure, shy appearance Penny was a great tongue kisser. She guided one of my hands to her big boobs and I enjoyed a nice feel - even through her top and bra, I was able to enjoy the softness and heft of those most excellent titties.

While I kind of felt her up, Penny dropped her hand to my rock-hard cock and squeezed me through my suit pants. “Let’s get these out of the way,” she said and undid my belt. She worked my pants down to my knees and took my throbbing meat in her hand, barely able to encircle my girth. She started a steady, gentle, agonizingly slow stroke, even as our tongues kept up their slashing, probing dance. Penny would occasionally drop her hand to my balls and give them a bit of a squeeze. I was getting close to cumming and told her so. “Colleen (from the softball team) told me you have lots of cum. I want you to jack off in front of me so I can get a good look,” Penny asked.

I stood a little awkwardly (didn’t want the suit pants to fall to the wet patio bricks) and started to give Penny a jackoff show. I stroked my cock long and slow, but soon got to the point of no return. I speeded up my jerking and told Penny to rub my balls. As soon as she touched them, I came magnificently. Nearly overcome with pulsating pleasure, I jacked out six or so big, creamy ropes of semen into a nearby plant pot, nicely visible in the light from the street lamps. I milked myself dry and Penny wiped off my hand and cock with a handkerchief from her purse. We went back inside the pub and sat down at the bar for a nightcap before returning to our homes.

I was to have another ST-suitable session with Penny that I’ll write up later.