Sex With Coworker

I have had several office sexual relationships but two were the most exciting. This is about my most recent experience I had with an employee. Her name is Jen. Jen is 5'6" tall. Very thin, shoulder length brown hair, B cup at best. I prefer more meat on the bones and a B to D cup. Jen was not my type at all. But she was cute and when she smiled it was a turn on for me. However, she rarely smiled.

When I started as the manager for this office it was a nightmare. It was me and 5 women. Most of the women didn't like each other. They would actually get into a yelling contest with customers in the lobby. Jen was one of them. Jen was also going through some tough times as she was getting divorced. Occasionally we would talk and I would offer my advice.

During this time Jen was being a friendlier with me and the staff since her divorce was coming to an end. I noticed she started to wear loose fitting V top shirts. When she would lean over my desk I could see bra and breast. Occasionally the bra was to loose and I would get a glimpse of the top of her areolas. The best times when she would have me come into her office and show me a project she was working on the computer. I would stand next to her and she would be leaning over looking at the computer giving me the best view down her top. I usually would bring a file in with me to hide my growing erection!

After her divorce we had been working together for 3 years. I was getting to know Jen well. Several times we went out after work and had a drink then I would head home. She seemed a lot happier being divorced but missed being with a man. We talked about sex occasionally. I learned what she liked.

One time I was shocked when she told me "I like a long thick cock. I like to get on top of it and ride it until I come."

I joked to her, but it was true, when I said, "Wow, I would be perfect for you."

Jen said, "Yea, right, plus you are 20 years older than me." Jen had already said she didn't want anyone more than 4 years older than her once before.

It was her 35th birthday and I suggested we all should go out for a birthday drink. I also invited a friend and customer of mine. Everyone had a drink and left but me, Jen and my friend. We left an hour later when my friend called me and asked if it was ok if he asked Jen out. I said go ahead.

They went out on several dates when they decided to be a couple. Jen and I continued to go out occasionally after work for drinks. She would say things about her sex life like "I wish he had a bigger cock and could go longer than 10 minutes. I have to finish myself off with my finger."

During this time I considered her as an employee and a friend. Then I lost my wife due to a tragic accident. She was there for me. We went more and more after work for drinks. Our good bye hug at the end turned to a hug and a kiss on the cheek. I found myself getting more and more attracted to her. She even started to working out after work so she was adding some muscle to her slender body. In fact day I was playing with my Go Pro camera in the break room when I got a customer came in that needed to see me. I left the camera in there with plans on going back. As it turned out I forgot about it until Jen went in and closed the door to change to go to the gym.

I know it was wrong but I couldn't resist. I took out my phone and turned on my GoPro remotely. I finally got to see her perky little breast and dark brown nipples. She had told me she kept her pussy hair neatly trimmed. But as she removed her panties she had turned and instead I got a nice view of her ass instead. Now I knew I really wanted her badly.

One evening after the bar we went to her place for a few more drinks. We had done this before. Her boyfriend always trusted me and even said, "Brian is harmless."

Jen even said she is not attracted to older men." We had a few more drinks at her place while we watched some tv and visited more. It was apparent I was too drunk to drive home. She told me I could sleep on the couch. So we had a few more drinks. She decided to call it a night and stood up to go upstairs to bed. She handed me a blanket and pillow.

Jen said, "We have to have our good night hug" We hugged and had a kiss on the cheek. But she held the hug and then kissed me on the lips. Jen giggled and said, "I always wanted to do that to see if you were a good kisser."

I told her, "That wasn't much of a kiss." I leaned in and kissed her longer. Her lips parted and our tongues found each other and we had about a 2 minute heavy kissing session.

She broke off the kiss first then she said, "Fuck that was better than I ever fantasized about."

I said, so you have had a fantasy about me?"

Jen replied, "Yes, but this is as far as we go. I don't want things to be awkward between us at work and you are my best friend."

I agreed. We had one light kiss on the lips and then she went to bed.

I stripped down to my boxers and lay down on the couch. I thought what it would be like to put my lips and tongue between those long skinny legs and lick her pussy. I was getting hard so I started to jerk off. I was hoping Jen would come back stairs and catch me, but it never happened.

Next morning she came down and woke me up. The blanket didn't cover me up much and she said, "Nice sexy boxers Brian"

I blushed a bit and said, "Hey I am not showing anything more than I would at the beach."

Jen replied, "I have never seen you at the beach yet even without your shirt off. You are in good shape for an old man!" She said, "I already showered, you can shower if you want too."

I took a quick shower and put on my clothes in the bathroom. Hopefully nobody will notice at work I wore the same clothes. My house is 50 minutes to work and I had no time to change. I came out of the bathroom and saw Jen in her bedroom sitting in her bra and panties putting on her makeup. It caught me by surprise and I said, "Wow!"

Jen quickly replied, "Oh hush, I am sure you have seen a few women in underwear before."

I said, "Yes, but not 20 years younger than me." I told her I was heading out and would see her at the office.

Things really didn't change much except our good- byes after drinks now was a quick kiss on the lips. Then one day Jen said she was moving in with her boyfriend. Her boyfriend traveled a lot. Plus he was only 15 minutes from my house. We got together a lot more either at her boyfriends place, a bar in their town, met half way at a bar or she came to my town.

One day after work we stopped at a bar not from work. We had 4 quick drinks then headed to her town. We stopped at a bar near her house and 6 more drinks. We then went to her place and had another drink. She fell asleep or passed out on the couch. I picked her up and carried her to the bedroom and tucked her in. She mumbled "Can you let my dog out before you go?"

I took her dog out and when I returned she was sound asleep. I kissed her good night and she didn't even move. That little devil appeared on my shoulder and said, "Now is your chance to see and feel her boobs." She had on a sports jacket along with her shirt. I cupped her breast on the outside of her clothing. She didn't respond. I was about to unzip her jacket and unbutton her top when the good angel appeared on my shoulder and said, "You don't want to get her this way." With that I left and went home and jerked off thinking of how sexy she is.

Time went on with no new developments except she decided to move back closer to work. Thus cutting down on our times we would get together. Then I got a better job offer at another company. I took it. After 2 weeks Jen sent me a text saying,"Hey I miss you! Let's get together for drinks then come to my place so I can show you my new home.

We met at our favorite dive bar where drinks were $2.00 from 4 to 6. We had 4 drinks then headed for her new place. She fixed me a drink then gave me the tour. We sat outside on the patio furniture as she had not moved her living room furniture yet. It was getting late and the bugs were coming out. Plus we were both pretty drunk.

I said," I better be heading home."

Jen said, "Why? It's Friday, no work tomorrow."

I replied, "I know, but I am not going to be in any shape to drive if I drink anymore. In fact I really shouldn't be driving now."

Jen said, "You can stay here. I have a big bed and I trust you."

I walked over to Jen and took her in my arms and hugged her. Then I kissed her. Then we did the passionate kiss that we hadn't done once before, that seemed to be an eternity ago. Then I broke our kiss and said, Jen I know you trust me, but I don't trust me. I have had a fantasy about doing something to you for a long time and I know I would try something."

Jen looked at me then said, "Now I am curious. What is it you wanted to do to me?"

I swallowed hard and said, "Ever since you told me you kept your pussy hair neatly trimmed and how your boyfriend doesn't like to give oral, I have wanted to crawl between those long legs and give you several orgasms from oral sex."

Jen smiled at me then said, "Ok if it is just you giving me oral sex and nothing more I am game!"

I said, "Really? But one more thing, I want to fondle your boobs during oral."

Jen laughed and said, "There isn't much there to fondle, but we will see how things go." Then she took my hand and led me to her bedroom.

When we got to the bedroom we kissed some more and Jen removed my shirt. I stripped her down to her bra and panties then lowered her onto her bed. I started with kisses on her belly and worked my way down to her thighs. I slowly removed her panties and tossed them on the floor where they belonged. There before me was the treasure I had been seeking for 3 ½ years. It was just as I imagined it.

I began with gently licking her slit and letting my hot breath heat her up more than she already was. When my tongue tip gently stroked her clit her body twitched from the pleasure. My tongue explored into her wet pussy. It was as if she was expecting it and she put something sweet inside her as she tasted like candy.

By now my cock was rock hard and very uncomfortable in my pants. With one hand I removed my pants and let my cock have some breathing room inside my boxers. Jen began to moan as my tongue and lips explored her pussy ever so slowly. I sucked her clit inside my mouth and ran my tongue around it sending shock waves through her body. Her hips started to rise and fall to the rhythm of my licks and sucks. I reached up and slid my hands under her bra. Jen didn't try to stop me. Her breasts were small but reacted to my touch as her nipples got rock hard. I really wanted to suck those nipples but Jen was close to coming.

Sensing her closeness I concentrated on her clit. Her fingers ran through my hair then pulled my head tight to her mound.

Jen said, "Oh fuck, oh fuck, oh fuck Brian I am going to cum. She let loose with a deep throat low moan and came hard with her body shuddering and shaking for what seemed like a good minute. I moved up her body and kissed her so she could taste her sweetness. Then I moved down to those hard nipples I desired.

I was not disappointed as her nipples were very sensitive and reacted to my sucking and nibbling. I then worked my kisses back down her body.

Jen said, "Brian, what are you doing?

I told her, "I am going for number 2."

Jen said, "Honey, I am one and done. I can't take two of those."

I looked up at her and said, "My fantasy is two give you multiple orgasms." With that I moved down.

Jen said, "Oh God, help me!"

This time I started the same way as before but while licking her clit I inserted a finger a rubbed her G spot. It responded quickly as it became hard and wrinkly like a large raisin. I could tell by the change in her moaning she really was enjoying this. I inserted another finger and applied pressure down towards her anus. She also seemed to enjoy this. With my mouth teasing her clit I switched my fingers back and forth to G spot to lower wall. She was getting very wet but was not close to have her orgasm yet.

I decided to step it up a notch. I removed my left hand from her breast. My right middle finger was rubbing her G spot. I slid two fingers from my left hand into her pussy and pressed down.

Jen said, "Oh Brian, that feels sooooo good."

I pulled my fingers out and replaced them with my thumb. I slowly teased her ass with my wet middle finger. I inserted my finger up to the first knuckle. She moaned deeply. I slowly slid my finger as far as it would go. I slowly finger fucked her ass while my thumb worked her lower wall and my other finger worked the G spot.

Jen moaned, "That feels so good. I have never had this done to me before.

Her breathing was getting heavy and her pelvis was grinding away. She held my head tight against her pussy and grinded on my mouth to where I was worried I was going to get a fat lip! When she came I wasn't sure if she squirted or not, but the sheets were soaking wet. I moved up and kissed her deeply. She said, "Thank you Brian. You said you were good at oral sex and I thought you were just bragging." I was lying on top of her and my hard cock was pressed against her thigh.

Jen then said, "You also said you have a big cock, it feels pretty big against my leg. I want to see it." I got up on my knees and she slowly pulled down my boxers.

Jen's eyes grew big and said, "Fuck just oral, I want that." She had me lay on my back and she slowly lowered her hot wet pussy onto my pulsing cock. She slowly rotated her hips taking me deep. I could feel my cock hitting her cervix. I pulled her down and kissed her then gave her nipples a little nibble. She then started to ride me hard. I knew she was a one time and done so figured she would need extra help to reach orgasm number 3. I rubbed her clit and pinched her nipple as she got close. It worked as she collapsed on top of me. My cock was still throbbing as I did not cum. I always had a hard time having an orgasm in that position.

I rolled her over so I was on top in missionary. I started to stroke ever so slowly. She was still catching her breath. After a bit she started to respond to my slow in and out motion. I could feel her pussy gripping my cock. I was about ready to explode but I knew she wasn't even close. I put my cock deep inside her and just held it there as I kissed her deeply for a few minutes. Then I began to pump her wet pussy faster and harder. The pressure was growing again and I could see Jen was close. I lifted her legs and put them over my shoulders and began to pump hard and fast. I couldn't hold back any longer and I spilled my seed inside her. The timing was perfect as she came at the same time.

I laid down next to her and said, "Thank you Jen. I never thought this fantasy would come true." As I spoke to her I continued to play with her breast and nipples.

Jen replied, "This would have happened a lot sooner if I wasn't hung up on the age thing." Then she said, "You seem to like my small boobs"

I told her, "Ever since I saw your nipples I wanted them."

She looked at me and asked, "When did you see them?"

I told her about the down blouse views and confessed the GoPro Cam view.

Jen said, "Wow, well I purposely was teasing you with the cleavage view. I didn't know you could see part of my nipple. But the GoPro Cam was naughty, but yet hot."

At this time I was now spooning her and I was cupping her breast and pushing my erection against the crack of her ass. Jen then reached back and felt my cock and said, "My, you are still hard. So you were not lying when you said you like to cum 2 to 4 times?"

I said, "No, and my record is 7 times but it was 3 hours of sex."

Jen replied, "Well I am done in for the night. Maybe tomorrow morning we can do two more."

I said, "Ok, I am going to hold you to it."

But I continued to fondle her breast and push my cock into her ass. I kissed the back of her neck and her back. I nibbled on her ear. She began to moan. Then I moved the tip of my cock between her legs and at the opening of her pussy. She didn't stop me as I slowly entered her still wet pussy.

I rolled her onto her stomach and entered her all the way. Jen got up on her hands and knees and ground her ass into me. Looking down her long skinny body and small ass I wondered, how she can take my big cock so easily. Regardless we sure seemed to fit well together. I put my hands on her hips and began to fuck her hard and deep. I reached around and played with her clit a bit then pulled her up and kissed her and ran my hands up and down her body only to enjoy those hard little nipples a bit more.

I took her hand and led it to her clit and we rubbed her clit together. I went back to grabbing her hips while she rubbed her clit. My pace was now hard, deep and fast. Her hand was going to town on her clit. She came again. Her orgasm seemed to last a long time. While she came I was trying to hold back to push her to another one but I couldn't. I erupted like Old Faithful inside her. She reached back with her hand and gently squeezed my balls while her vaginal wall squeezed my cock tighter. I shuttered again and came again in a matter of seconds. She continued to squeeze me and milked every drop out of me.

She curled up next to me with her head on my shoulder. She whispered, "This was never supposed to happen. We need to talk about this in the morning." She kissed me and we fell asleep.