I work in the tech department at a firm. I’m your usual office guy. I’m brown and easy-going. I visit the gym often and go for runs, so I would say I’m quite athletic. I’ve been working here for around six months; it’s a role I’m enjoying, so I always try to remain professional and work at a high standard. Anyone that works in this field will know that there is a high ratio of men compared to women. We had plenty of women in other departments in the office, but very few in ours. At the time, we had a vacancy in our team, and we were hiring.
I got into work on a Monday morning. Our manager reminded us we had someone starting today. Her name was Nancy. Of course, I thought. I had forgotten about the new starter; it was a girl’s name and for the first time, we would have a female in our team. I don’t know why, but that excited me. So later on in the morning, the HR lady, after her usual induction, walked over with Nancy to our team. Our manager introduced us all to Nancy.
“Nice to meet you,” I said, as I offered a handshake.
Nancy looked, if I had to guess at the time in her late forties, white, shoulder length blonde hair, about five foot three inches, brown eyes, friendly smile, curvy and the usual middle aged weight in some areas. She wore some kind of a loose blouse with a cardigan on top and loose fitting jeans. She was just like your mum next door type woman, she had a cute innocent smile and was very softly spoken.
“Nice to meet you too,” she said in a quiet, delicate tone.
As time went by I would sometimes make sure Nancy was doing fine as she was new and had a lot to get up to speed with. Nancy was quite smart but over the days she would ask me to help her with very simple things and would then start conversations with me. We had very different interests and felt like we were from different worlds sometimes. She had a very soothing sexy voice so I did not mind listening to her.
“She could make a fortune doing phone sex,” I used to joke to myself.
It turns out she lives in the countryside and has quite a long commute every day as she lives in a different city. She was living alone and it sounded like you were a bit lonely.
Nancy started to give me many hints she would tell me she liked my company but like most guys, I don’t get hints. She would comments such as
“You look good in that blue short,” and, “I like your hair today,” while smiling and tapping on her keyboard.
She was eager to work alongside me so would find a reason to call me over to her. The desk next to her was unused so it was always available for me to use. I just felt she needed someone to talk to so lent an ear.
Shortly after she started we were planning a team night out, it was on company expense as a reward for a massive project we had finished recently. Even though Nancy was not involved in the project she was still invited as she was in the team.
We had a team meeting to organise the event. We tried to find a Friday night where everyone was free but that was unsuccessful. Considering this night was already delayed before, we decided on a weekday so everyone could make it.
Nancy had her doubts about going as that would mean a long commute back for her late at night and she had to return to the office the next morning. She had asked me if she could stay at mine for a night. I had to decline and apologise. I still lived with my parents and siblings and I felt it would be too weird for her to stay at mine. I tried looking down her blouse during the meeting but she sat up straight. That was probably the closest I got to a peak as she was always dressed modestly. I kinda saw this as a rejection and thought maybe that her liking towards me was her just being nice and nothing sexual.
You see I’ve always had a thing for mature women. As I said Nancy was your normal “woman from next door” type, always dressed modestly and most importantly a colleague that works with me. For the last reason alone she was off bounds but I couldn’t help but start fantasising about her. She wasn’t helping by always trying to socialise with me at work and at times stare in my direction. I was starting to have naughty thoughts about her. My mind started wondering about her during my masturbation sessions.
It was the day of the work event, I was sitting next to Nancy as we were working on something together.
“I’ll be coming along tonight after all,” she said. Her face gleamed with a smile.
I asked about travel issues and in a kinda naughty way she lowered her tone and said:
“I’ve booked a double room for the night”. It felt like a loud whisper and there was a naughty expression on her face
It turns out that it was the hotel close to the office and as it was a weekday during the winter it was for a very good price.
The fact that she mentioned it was a double room had me curious. Naughty thoughts entered my mind and I was imagining myself in the room with her.
At the end of the day, we were calling a taxi to take us into town. I had my car so my manager asked if I could take a few people with me. I accepted considering it was at the company’s expense.
“I’ll go in his car!” Nancy said as she jumped and pointed my way.
So it was her, myself and a couple of other colleagues in the car, we listened to music and then stopped off at the restaurant for dinner. While seated I managed to get a brief glimpse of her cleavage down her blouse, she caught me and I looked away. She smiled but I felt a little embarrassed at the time.
We chatted, and Nancy was telling me a lot more about her personal life. She had children that are now in university and she had been divorced for a long time. From our chat, I gathered she must have been around fifty give or take some years. Although curious, I didn’t ask her age (because that’s just rude I thought). She said she was grateful for being a good friend to her.
“Damn it!” I thought, “I’ve been friend-zoned.”
It was a fun night, good food and we saw theatre-type play. I didn’t drink on the night as the dedicated driver so once the entertainment was finished I decided it was time to go. My colleagues were planning to hang around and get drunk.
When Nancy saw me going she asked if I could drop her off but only if I was going her way. I accepted as it wasn’t much of a big deal, might increase my journey by five mins. She seemed sober, I don’t think she drank much. To avoid awkward silence I asked her about the hotel room and if it was nice and comfortable. She explained it was very nice, comfortable with a double bed (another hint I didn’t get).
As we got there, she asked if I could park next to her car as she had a heavy bag in her boot she needed to carry upstairs. I volunteered to help carry it for her which she instantly accepted.
I grabbed Nancy’s bag from the boot of her car which wasn’t heavy at all. As we walked into the reception she handed me her key card and asked if I could take her bag to her room and she’ll join me soon. She went over to speak to the lady at the reception.
It felt like I was in the room for a while, it was a nice looking spacious room. I took my jacket off as it was warm, used the bathroom and roamed around. Nancy finally knocked on the door and asked to let her in.
As she walked in, she smelt good and her hair looked tidy, it looked like she cleaned up a bit. She took off her jacket and cardigan, she had her usual loose-fitting jeans on and just a blouse.
For the first time, I could see the shape of her boobs and my cock was starting to harden. She walked over to me, we were standing in the middle of the room talking about something I don’t remember and preserving eye contact. I was waiting for her to do something because mature women always take control right? Well, at least they do in my fantasies. But no, it felt like she was never going to make a move. I thought what’s the worst that could happen here? She revokes my approach and I apologise and walk away saying I got the wrong end of the stick. I leaned forward, grabbed her head on each side with my hands and attempted to kiss her, and she started to kiss back.
While we were kissing, I decided I was gonna have to be in control and started pushing her towards the bed, she fell on the bed on her back and I got on top of her and carried on kissing her. I started kissing her on her face and then went down towards her neck. Our hands were all over each now, I wanted to touch her down there but she sort of moved me away and stood up, I was wondering if I did anything wrong. She turned the main lights off and left the two dimmer lights on each side of the bed on.
She came on to the bed, kissed me gently and started to unbutton my shirt. She took off her blouse and had a white bra underneath. I took my jeans off and was wearing some really tight boxers, my boner was throbbing wanting to escape. I saw her unbutton her jeans and I stood up and pulled her jeans off her legs. I made her lie down and started kissing her on her stomach, shoulders, neck and mouth. She decided to sit up and asked me to take her bra off, I started kissing her on her back while taking it off. She had a C-cup breast which was a little saggy, but it was really fun to play with. I kissed and sucked them as her breathing got deeper.
I then started kissing her thick thighs and started to go higher. It was my hint that she needed to take her white panties off and she complied.
“Take those off,” she said pointing to my boxers.
I was so busy concentrating on her that I forgot I still had them on. It felt good to take off my tight boxers as it finally freed my throbbing cock which was suffering.
Her vagina wasn’t too hairy but it did look like she went some time without shaving it. I decided to use my fingers down there, she then grabbed my fingers and directed them to the top of her vagina and instructed me to rub her there. While my fingers were rubbing, I started kissing and licking between her legs. Nancy started to moan slightly and I felt like the bed was vibrating which got me feeling even more eager.
“Ugh,” she gasped. I could hear her breathing getting heavier and deeper.
After some time she gave out a louder moan and pushed my head away. Her thighs were squeezed together to indicate she had climaxed and was too sensitive for me to go on any longer.
She started wiping and cleaning my mouth with her hands and then kissed me.
“You’re good at doing that aren’t you?” she said.
“I hope you enjoyed that,” I replied.
“I certainly did,” she muttered under her breath.
“Stay laying down,” she firmly ordered. After a little rest, she climbed on top of me.
My pubic areas were neatly trimmed recently but not my chest. It didn’t bother her as she was kissing me there. I’m very ticklish on my stomach so I got a bit jumpy when she was kissing me there. I was startled.
“Are you okay?” she asked.
“Well, erm…. it tickles a little when you do that,” I reluctantly admitted. We both had a little chuckle.
When she got to my cock she was holding and kissing it and then she took it in her mouth. I could feel her soft wet tongue first on my tip as I felt it enter. The feeling was so good I wished it could stay in her mouth for much longer but after a short time, I knew I could not go on for much longer. The sensation was too strong so I thought I better tell her.
“I’m going to…” she knew it before I could finish my sentence
She switched to stroking my shaft with her hands and after a few strokes there were stream loads of cum on my stomach and some on the sheets.
I stayed laid down as I came back down to earth. Nancy went and grabbed her handbag, she got out some wet wipes and started to clean the cum from my stomach. I felt like a small child that had made a mess and had to be cleaned up. She lay down next to me and we cuddled for a while. I then felt her hand fiddling with my flaccid cock, and it didn’t take long for it to come back up.
“Do you have any condoms?” she asked.
“Erm, sorry, I don’t,” I glumly replied. I was feeling stupid for not being prepared for such situations.
She reached out to her handbag and brought out a condom – my guess is, she must have brought them from the machine earlier or maybe she carried them around. We did a bit more foreplay and she grabbed the condom from the side and handed it over to me.
I’ll be honest, I was hoping there would be no need for a condom for a woman of her age but I respected it. I got on top and entered her, I lasted much longer this time. We were in a missionary position, I was admiring her body while sliding in and out.
I asked her to go on top for a while but she got a little tired and I kept slipping out of it so we switched back.
We were now back to the position where we were both comfortable. I was thrusting passionately and we were both moaning as her fingers were digging into my back and I eventually exploded while I was in her. A few more thrusts to empty myself. All my strengths had gone as I collapsed on her.
Afterwards, we both cuddled and chatted.
“That was wonderful,” said Nancy. “It’s been so long I really needed that”.
I kissed her on the head while she was resting on my chest. Now, I’m a fairly fit guy but this woman just took away all my stamina. I was tired but happy and satisfied.
“I’ve always thought about sleeping with you but I’d never thought you’d be interested in an old lady like me,” she said.
“Nancy, you’re super hot, I hope you know that” I assured her.
I checked my phone and saw a text from my mum to check if everything was fine. I wasn’t normally out this late on a workday. I decided to head home as I wanted a shower and a change of clothes before work tomorrow. I got up and got dressed, kissed her on the cheek.
“Thank you for a great night, Nancy,” I said.
The next day at work, we acted like nothing had happened. Everyone was just talking about the night out.
Sadly, not long after this, Nancy handed in her notice. Her reason was that she had found a job closer to her that pays good and no need for a long commute. As she was still in her probation period, she could leave within a week.
I’ve worked with many people in my life now throughout the years. I only worked with Nancy for a month, but I’ll never forget her and that night we had.
After she left, I sent her a Facebook request. After a few days, I received a notification that she accepted my request.