Second Time with Co-Worker

I had written about a former co-worker, Jen, before and how we wound up in bed together. We had a good time but we both knew it wouldn't last. She got a boyfriend and I found a girlfriend closer to my age. I also took a job at a different company. Jen and I still remained friends and often got together for drinks after work. Most of the conversation was about how she hated the company she was working for and her boyfriend and her were having problems.

For those who have not read my prior story I will describe Jen. Jen is not the typical lady I would be attracted to. She is 5'7" slender build. Small chested. I prefer blondes with a little bit of meat on them. She has a beautiful smile and when she laughs she is sexy for some reason.

She would ask how my life was going. I felt guilty telling her that things were great. I loved my new job and my girlfriend and I were in a great relationship.

Three weeks ago I get a text from Jen. "Want to meet for Happy Hour?"

I text back, "Sure when and where?"

She texted back, "Usual place, 3:00."

Usual place meant $2.00 strong drinks until 6:00.

My girlfriend knows about Jen as being a close friend. Jen helped me a lot when I lost my wife. I didn't want to live anymore and I drank way too much. She was a true friend then that turned into a little sexual relationship. However, I didn't tell my girlfriend about the sex as that was well behind us and was never going there again.

I left work early and met Jen that Thursday and met at the bar. She looked sad and was two drinks ahead of me.

She greeted me with a hug and said, "Hey Bri, thanks for coming. Guess I might as well tell you right away, my boyfriend broke up with me via text this morning."

After talking a bit we resolved she was better off and it was time she moved on with her life.

Jen had a habit of wearing lose fitting tops and a bra a size too big for her. I suppose since she is barley a B cup it might be hard for her to find a good fitting bra. However, every time she would lean forward I would get a partial glimpse of her nipples. This sent memories back to when we had sex. I was starting to feel horny.

"Well Bri, it's after 6. Happy Hour is over. Let's go to my place I have what we are drinking there.

"All right. I are you ok to drive Jen?"

"I am fine."

I followed Jen to her place. Once inside she said, "I have to go to the bathroom. Mix us some drinks."

I made us our drinks and then went to use the guest bathroom. I figured she was using her bathroom in the bedroom since the guest bathroom door was open. I walk in and Jen is sitting on the toilet. She laughs and said, "Oops, guess I should have closed the door. I am used to living by myself."

I didn't know what to say or do. I stood there motionless for a few seconds. Then she stands up and pulls up her pants. I get a glimpse of that neatly trimmed pussy I once enjoyed and I started to get hard.

"I am done, it's all yours." She says.

I go over to the toilet and start to unzip. Jen is standing at the door watching me. I figure I will shock her like she shocked me and I pull out my semi hard cock and start to pee. She continues to talk to me like it was no big deal.

I finish up and we go to the kitchen and sit at the counter and start talking and drinking. I get a text from my girlfriend asking how Jen is.

I reply back. "Her boyfriend broke up with her and she is pretty drunk."

"How about you, are you drunk?"

"I am a bit, but I am done drinking."

"Ok hun, but if you spend the night there let me know. You are a good friend to her."

Jen convinces me to have another drink before I go. This turns into 3 more drinks. I text my girlfriend I am spending the night on her couch.

Its 10:30 and we have had plenty. I help Jen to her room and she lays down on her bed and passes out. I grab a blanket and head to the living room. I strip down to my boxers and curl up and fall asleep.

An hour later I wake up to Jen calling my name. It's dark so I don't throw any other clothes on and go into her room.

"Bri, I want to thank you for being such a good friend. Can I ask a favor of you and have you rub my neck?"

"Sure Jen, you feel ok?"

"Yes I just have a kink in my neck."

I rub her neck and we continue to talk. My hand wanders down a bit and I am rubbing the top of her back. "MMMM that feels good." She says.

I switch hands and move my hand under her shirt from the bottom and I am massaging her back. While massaging her back I lean forward and kiss her gently on the cheek.

With one hand I unhook her bra and it falls to the side. By now my cock is rock hard and the tip is poking out of the bottom of my boxers wanting to be free. I am glad it is dark so she can't see it.

"What are you doing?" She asked.

"Your bra was in the way."

"Ok, just don't try grabbing a boob!"

"Like this?" My hand slides around and under her and I cup her right breast. Her nipple is already hard and I roll it between my fingers and tug it slightly.

"Oh fuck, you are making me horny."

She rolls over and I lean in and kiss her deeply as I am now massaging her breast and nipple. Her hand travels up my thigh and finds my hard cock poking out of my boxers.

"Fuck, you have a nice cock. You are so much bigger than my ex and know how to please me. He would never give me oral. Brian, will you eat my pussy again?"

I was beyond the boundaries and couldn't say no. I helped her out of her clothes and took off my boxers and moved between her legs.

I gently licked her slit and her lovely taste and scent was as good as it was before. I put my tongue deep as I could into her pussy and worked my way to her hard clit protruding from her folds. Her hands held my head in position and my hands found her little breasts and hard nipples.

It didn't take much before she said, "Oooooohhhh Fuck, I am coming."

With that she came hard with her body all tensed up. She relaxed after a bit and I moved up and kissed her sharing her taste.

My cock was pushing gently against her wet lips. She spread her legs a bit and I slowly entered her. She was wet warm and felt like velvet wrapped around my cock. I was in over drive and I knew I wouldn't last long. She wrapped her legs around my waist pulling me deep inside her. We were both moaning and groaning and in a matter of 5 minutes I released my seed inside her in a couple of strong spurts.

I laid on top of her feeling her pussy tighten up on my draining the last of my seed. She whispered, "I didn't come yet. You know my favorite position."

I pulled out and she rolled over and put her ass up in the air for me to fuck her from behind. I was starting to lose my erection but the view of her skinny ass and wet pussy begging for me to enter started the blood flow back into my cock.

I entered her pussy with one big hard push. I knew she liked it hard, deep and fast. I fucked her like that for a good 20 minutes. It was hard to even hold onto her as we were both wet from sweat.

"Oh fuck, oh fuck, oh fuck I am coming." She said. She came hard and collapsed on the bed. I was close and I was still inside her. A few more hard pumps and my seed filled her a second time.

I rolled off from her and cuddled up behind her with my limp cock resting between the crack of her ass as we spooned.

Jen said, "Thank you for being my best friend."

Next morning I got up and left without waking her. Nothing was said about that night. But I am having drinks with her tonight!