Older Woman from Work

I was 28 years old and owned my own place. I lived alone in the two-bedroom house following the break up with my girlfriend the month before. Most nights I would masturbate before going to sleep. As I lay on my bed jerking off, I thought about a number of women. There were women at work, a local girl from the same street and of course the barmaid at the pub just round the corner. Often I came back to someone I had seen that day and very often this was one of the older women at work called Diane. She was ten years older but had the best body I had ever seen. She dressed well and every so often would have on a nice skirt that showed what an amazing backside and legs she had. There was something about the way she moved, her shape and her movements that just filled me with desire for her.

Diane was very easy to talk to and I often found myself making conversation with her. She worked in the customer returns department and it wasn't difficult to find an excuse to go and check her out each day. I don't know if she had any idea how attracted I was to her but she was very friendly. She was also married and sounded like a bit of a doormat. Her husband was a lorry driver and she seemed to do a lot of running around for him. She would often miss drinks after work and evening events because she had to be home to prepare a meal. She often talked about him but it seemed to be with a hint of discontentment. I got the feeling she felt her husband didn't pull his weight.

I carried on with my wank thinking about Diane. I imagined her bent over and running my hands up her legs. I thought about how much I wanted to stroke her pussy and then fuck her brains out. Of course if could never happen. It was just a fantasy.

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After a particularly successful month, the boss took a large group of staff out for a Chinese meal. I ended up seated with my back to the wall in the middle of a long table. As other people arrived, Diane moved along and we were sitting next to each other. I was well pleased with this and even more pleased that her top was quite revealing. Her tits were big but not massive. They were that wonderful shape some thirty something women develop into. We talked quite a bit during the meal. I explained to her about my house and my recent relation shipbreak up. Diane giggled when I hinted at missing the physical side of living with someone.

"Wait till you get to my age," she joked. "I wish I could get my lazy slob of a husband to make more of an effort. If he isn't driving, he just watches telly."

I don't know why but I didn't feel brave enough to continue this line of conversation. I wasn't going to pry into her marriage even though I was thinking how little I would watch TV if I was married to someone with a body like Diane's. In fact my cock hardened as I sat there speaking to her. Fortunately the table and cloth covered my state of arousal. I quite enjoyed sitting there with a hard on talking to her and decided a wank when I got home would be just the thing.

We carried on talking and Diane brought up her husband again saying how possessive he was. I was trying not to pass comment but then Diane said, "I think its because he knows I could find someone else if I wanted to."

"I know," is all I could answer. It was sort of an admission that she was attractive.

Diane smiled at this complement and we carried on talking. Nothing more happened that evening and she made a point of telling me how she was getting a lift home from another woman in her department. I wanted to give her a lift home. I wanted to get her alone and wait for things to develop. I didn't have massive amounts of confidence with women and my pulling technique was rarely direct. I would often bumble along waiting for signals or signs of encouragement. I know now looking back that I should have been a lot bolder in my younger years.

When I got home that night, I fantasized about Diane. I thought about giving her a lift home and her inviting me in, as there was no one home. I thought about going inside and talking some more. Then maybe kissing her on the cheek to say goodnight and it developing into a full on kiss. Then I would undress her and get my hands on her tits. I would feel all up her legs and it would develop from there into a full on fuck. That was the fantasy.

About six months later Diane's life got complicated. I didn't really know the facts as she confided more in her female colleagues but I did work out that her husband had cheated on her and she wanted to leave him but had nowhere to go. I sort of pretended I knew nothing about this when we finally did strike up a conversation and she started to moan to me about how hard things were. When she said she had nowhere to go, I offered her a temporary solution. I said she could always stay with me if she was stuck.

I could see she really thought it over but she said no but thanks. She touched my arm as she said thanks. I like it. I like her touch. I felt electricity in my body. That night I jerked off twice reliving the conversation and replaying it with a different ending. I wanted Diane to say yes and then I would fantasize about how we could fuck at my house.

The next day Diane came to look for me. "Things got worse last night. Is your offer still open?"

I was stunned and sat there in silence. I was wondering what could have got worst but she thought I was looking for a way to say no. "It will only be for a few nights," she said trying to persuade me. There was nothing flirtatious or suggested by her request. She was genuinely a woman in need and I told her of course she could stay.

Diane moved in that evening. She bought two suitcases and a reading book and not much else. I showed her to the second bedroom in my two-bedroom house and then showed her round the rest of the place. We ended up sitting in her bedroom. I was leaning against the windowsill and she was sitting on the bed. It was a little uncomfortable for both of us and we talked about how strange it felt. We were getting on well and I decided that even if nothing happened physically between us, I was going to enjoy having her here.

I reluctantly said good night and left her to unpack the rest of her things. I got ready for bed as it was gone eleven when we finished talking. I often slept nude and walked round the upstairs with nothing on, but I covered up now I wasn't alone. I chose boxers and a robe even thought it was summertime and quite hot.

Lying in bed that night in the room next to Diana, I stared at the ceiling and listened. I could hear her moving round in her room and I thought about her body. Of course my hand was stroking my cock and I didn't even realise it. I was too busy thinking about Diane. There was no way in a million years that I would have the confidence to go back to her room. I just lay there stoking myself. Then I heard her door open. Diane had to walk past my door to get to the bathroom. I could hear her footsteps and then the bathroom door shut. She pulled the light chord and I could here running water from a tap. I wondered if she might be naked and got up out of bed. I crept over to my door and peeped out. The bathroom door was an old 1970's retro job with a full length frosted panel in it. I could barely just make out Diane standing at the sink with her back to the door. She was dressed in a robe too.

All this time my hand was automatically stoking my cock that was sticking through my boxers. I could only see a shape through the frosted glass but it was Diane's shape and it turned me on big time.

I slowly sloped off to bed when I got worried that she could finish in the bathroom and catch me spying on her. I lay in bed and listed to her turn off the tap and switch the light off. Then I heard her footsteps. She knocked gently on my door.

"Are you awake?"

I panicked and quickly pulled the duvet over my naked cock.

"Come in," I said.

"I won't come in," said Diana poking her head round the door, "I just wanted to say goodnight and thanks for everything."

"That's ok, good night." I answered.

She closed the door behind her and I carried on stroking my cock. For some reason I fantasised that she was naked when she poked her head round the door. I couldn't have seen even if she was but I liked the idea that she was naked and I could see her. Of course I knew she had the robe on in the bathroom so it was purely fantasy.

I couldn't sleep for thinking about her and after about an hour, I got up to take a pee. I opened the door and looked back at her door. It was ajar but the gap was too narrow to look in and get an angle on the bed.

I went to the bathroom and as I was peeing, I noticed her robe on the floor in the corner. She had taken it off. Maybe she had been naked when she put her head round the door to say goodnight. This was too much. I hadn't turned the light on as I was trying not to make any noise but I decided to flush the toilet.

I returned to my room and fell asleep after spending time wondering if she was naked. The next morning, Diane was up before me and was already dressed when I went downstairs. We exchanged the usual pleasantries and agreed that I would give her a lift to work.

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On the second night I went out to the pub leaving Diane at home. All the time I was in the pub, I could only think about her at home. I ended up staying till quite late in the pub and was a little drunk when I got home. I went straight to bed. All the lights were off and I assumed Diane was fast asleep so I got undressed and made my way to the bathroom completely naked. It was mostly out of habit rather than any plan to flash my new lodger. Again I didn't turn the light on but just the orange glow from the road outside through the bathroom window was enough for making out the sink and toilet. I took a pee and brushed my teeth. As I was leaving the room I was startled by Diane coming into the room. I was even more startled by the fact she was naked. We bumped into each other and my cock hit her thigh. My arm brushed her tits. We both stepped back. She was very sleepy.

"Oh," she said, "I didn't hear you come in."

"Sorry," I said and quickly went to my room.

I lay there in my bed, stunned by what had just happened. Diane and me both naked. We had touched. She was still naked in the bathroom and I listened to her flush and then heard the floorboards creek and she crept back to her room.

The next morning was a little uncomfortable. We made small talk but neither of us mentioned our naked collision the night before. All the way to work the atmosphere in the car was very muted. I was worried that she thought I had done it on purpose, that she had seen me and was shocked, that she wanted to move out and a whole load of other stuff.

Diane had also told me that she was going to be late home that night. I spent the evening by myself and by eleven pm Diane still wasn't home so I took myself off to bed. I lay in bed reading but not really concentrating on the book. I could only think about Diane and her naked body. My cock twitched at the thought of it touching the bare skin on her thigh. I hadn't seen her pussy but I imagined it. I did get a glimpse of her tits and my arm had touched one. All these thoughts were flying round my head.

Then I heard the front door and I knew she was home. I heard her come up the stairs and go into her room. Then Diane went to the bathroom and I heard her walking along the landing past my room. She knocked. I called hello and told her to come in. She peeped round to check I was decent and then she came in. She walked slowly over to my bed wearing the robe. I wondered if she was naked underneath.

"I want to apologise for last night," she said.

"No need," I replied.

"It's your house and the last thing you want is to bump into middle aged women in the nude at all hours." Diane couldn't have been more wrong.

"You are my guest and I must remember to consider you also," I responded. "The last thing you want to see is me naked when you are trying to use the bathroom."

"I dunno," she quipped. "It's been a long time since a saw a fine body like that with no beer belly"

"I'm working on growing a beer belly," I joked back.

"Trust me, you look better without it," she said. The mood was light and we had cleared the air. She sat on the bed and we carried on talking. Her butt was pressing next to my leg and I was starting to get aroused.

"An old woman like me could get all hot and bothered seeing a naked man walking round the house." Diane was using a very jokey tone but I started to think she was flirting a little. I apologised and explained I usually slept naked. At that moment, Diane realised I was naked under the covers. She sort of looked me over and then changed the subject. We talked a little more and then she got up to leave.

"Anyway, I'm glad we cleared the air and you weren't embarrassed."

"I wasn't embarrassed at all, just worried that I had shocked you," I answered.

"That's sweet, I wasn't shocked or embarrassed." Diane turned and smiled. Then she joked in her self depreciating way, "I better make the most of it, don't know when I might see another naked man."

"Anytime you like," I said. I couldn't believe I had said it. She turned and walked back to me. She allowed her robe to open slightly and made no attempt to close it up. Diane sat back on the bed in exactly the same place. She didn't say anything but was thinking things through.

"This is mad," she said. "You are here and I am here"

"That's right," I agreed. There was tension between us. We both stared at each other.

"No one must find out," she said.

"Find out what?" I asked.

"You know," was all she would answer. There was silence and she asked, "Can I see you again?"

"You are seeing me now," I answered. It was a stupid thing to say. I wasn't making this easy for her but I was so nervous myself. Then I tried to recover the moment by saying "Anytime you want."

Diane just stared and leaned forward. She reached for the duvet and slowly pulled it. Slowly my chest became bare. Diane stopped looking right at me and looked down to the edge of the duvet as she pulled it. My initial reaction was to stop her but I was frozen. I was also hard as a rock and very soon she was about to see how hard.

The duvet slowly travelled down my naked body. If anything she pulled slower and almost stopped as she reached my abdomen. Past my belly button and then she started to reach the top of my cock. It was lying flat on my belly and was now really hard. The head soon appeared and she whispered a faint gasp. She was determined to see it all and she slowly pulled the duvet the rest of the way along its entire length.

Soon I was lying completely exposed to this woman who I had fantasized about for so long. As soon as the duvet had cleared past my cock she sped up and pulled it down to about my knees. Then she ran a hand slowly up each leg and bent further forward as they reached up. She was lying across me and I moved my hands to her back to embrace her. Her mouth reached my chest and she kissed it. Then she slowly started to trace downwards with her mouth and kissed her way to my cock.

The anticipation was killing me as she took it in her hand to steady it and plunged her mouth over it. Diane was sucking me off. I couldn't believe what was happening. She broke away and looked at me. "I have been dreaming about this since last night," she said.

"I have been dreaming about this since the day I met you," I said. It seemed so natural to say it at that moment. I would never have imagined confessing how much I had fancied her for so long. It had been my secret crush on an older woman but there is something about a blowjob that does away with any notions of secrecy.

Diane stopped the blowjob and stood up. Staring right at me and smiling, she opened her robe a revealed a naked body except for the skimpiest of thongs. Her tits were fantastic. I couldn't wait to touch them. I sat up but Diane pressed me back. She raised her leg over me and sat across me. Her thong covered pussy was right over my cock as she pushed her tits into my face. I sucked on her nipples as both arms reached behind her to pull her against me. Diane ground her chest into my face.

"Suck me, suck my tits, that feels so good." She moaned into my ear.

I moved my hands lower down her back and hooked my thumbs into her thong. She moved her hands to her thong. I thought she was going to help me remove them but she held them in place.

"I'm not ready for that. Just kiss my tits," she said. I wasn't too disappointed. Diane had a way of saying things. I like her voice. She could say anything to me and it would sound OK.

As I continued to suck gently on each nipple in turn, she moaned and ground her pelvis into me. Her legs were astride me as I lay there on the bed and I push my cock to make contact with her thong covered pussy. I could feel the tip of my cock against the material. Diane seemed to push back. She was enjoying it and becoming more adventurous down there. I again tried to remove her thong but she shook her head. Then a smile crossed her face and she plunged back down, kissing her way until my cock was close to her lips. I lifted off the bed to help my cock reach her mouth and she licked it all over. I pushed her head down and she took it into her mouth fully. Then without any warning, she deep throated me. I was rooted to the spot in awe of this woman. My cock had never been in a throat before. Sure I had enjoyed a fair few blowjobs in my time but nothing could prepare me for the feeling as she bobbed her head back and forth as I slipped in deeper than ever.

I could hold back no longer and soon my cock throbbed and spasmed and I came. Diane caught the first jet of cum in her mouth but then pulled back. Soon she thrust her tits at my cock and the next two jets of cum hit her chest. She was above me and the cum ran a little off her tits and then hung from them. She smiled and stared at my cum before noticing my cock had stopped spurting. Then she was back on it licking and sucking the tip. It was too sensitive so I pushed her off me onto her back.

Diane looked so beautiful as she lay there almost naked on her back smiling at me. "Did you like that?" she said, knowing full well it had been amazing for me.

I didn't even answer but just started to kiss her tits again. Diane held the back of my head and pushed me against her tits. My hands started to wonder and one soon worked its way down to her legs. I explored her and rubbed her and soon was trying to open her legs. She held them still and I turned to look at her with a quizzical expression on her face. Then she smiled, still staring at me and opened her legs. My hand was free to explore and she was giving me access to he most precious treasure. I rubbed her over her underwear but soon slipped a finger in and was rubbing her pussy lips. Diane moaned out load as a slipped a finger into her pussy. She arched her back and thrust against my finger as a slowly explored and caressed her soaking pussy.

I had never really lost my initial erection and was now back to full hardness. I sensed she was reluctant to fuck. Perhaps she was old fashioned and wanted to take things slow. Hardly, I thought. That blowjob had killed any idea of old fashioned.

I could wait no longer and made my move. I slid over her and was soon on top. Her legs opened and I rubbed my cock against her pussy lips.

"We can't," she whispered. "We mustn't."

I said nothing but kept rubbing and nibbling her neck. Then she opened her legs and reached behind me pulling my backside towards her and in doing so, guiding my cock to her pussy.

"I want you sooooo much," Diana purred. "Please, put that inside me."