Anna Ch. 09

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More sex with other women as well as Anna.
6.4k words
4.41
42.9k
14

Part 9 of the 11 part series

Updated 10/31/2022
Created 06/30/2008
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Anna drove me to the office that Lisa's husband kept about 6 miles from where I lived. On the way there, Anna was giving me the inside info on Lisa's husband and his firm. The business was called KC's Imports and the building was mostly a warehouse with some office space for admin. There were other similar businesses on the same road. Anna warned me in a playful way about working with all the women in the office. I think she was trying to suss out if I was likely to play around. I told her that none could measure up to her and as long as I had Anna then I wasn't interested in other women in a sexual way. This was a complete lie of course and even as I said it I could only think of Anna's beautiful younger sister Lisa.

When we arrived at the office I suddenly felt a little nervous. Anna showed me inside and Lisa's husband quickly met us. His name was Dave and to be fair, he seemed OK. I really liked him, quickly grew to respect him and enjoy working for him. He was friendly, smart and hard working. He seemed devoted to his wife and also loyal to his staff. In the first few weeks with the company, I learned a lot just watching how well he ran things and managed the everyday problems of staffing levels and changing workloads. Dave worked long hours and often stayed late. I was sometimes asked to stay late and he always made a point of expressing his appreciation.

What I haven't mentioned yet are the other people who worked there. They were all women. Now....this being Literotica and all, I wish I could report that the first few days were a sex filled adventure as I sowed my oats around the building looking for clues about Dave's infidelity. I wish I could describe a good dozen blow jobs and fucks with a selection of the women who work there but the truth of it is; there was none of that. The first two weeks were work, work, work and more work. I did get to meet all the people there and half of them were what you would call attractive with lots of potential but I can't say that I spent much time thinking about any of them except for maybe the odd wank. I also fucked Anna a couple of times on the pretence of going round to update her on my findings re Dave's supposed infidelity. This was nice. We had slipped into a mutual understanding that we could both initiate a good fucking anytime it suited. I was living the dream. 20 years old and fucking a lovely married woman about twice my age. We were extremely compatible and loved to make each other cum. My only nagging doubt was that Anna was finding it harder to keep her feelings in check than I was. I decided to stop worrying and enjoy the sex.

Within a couple of weeks, Anna was telling me that Lisa was growing impatient and was not impressed that I held Dave is such esteem. I told Anna that maybe Lisa and I should meet to discuss it. Anna overcame her natural possessiveness and agreed to set up a meeting. Dave was travelling to the Far East for a couple of weeks so I was told to go and see Lisa at her house one evening. When I got there, Lisa nearly stopped me dead in my tracks. She looked stunning and obviously paid far more attention to her appearance than Anna did. Don't get me wrong, Anna always looked good but Lisa was something else. I think she knew the effect she was having on me but she certainly didn't give anything away. In fact, she was a little off with me when I told her I had nothing to report. When I continued to say how much I appreciated Dave's support and the opportunity to work for him, she was really pissed off. I said she should be relieved there was no reason to suspect he was cheating but Lisa couldn't agree with me. She didn't buy the workaholic angle and felt sure he was cheating on her with one of the younger women in the office.

Lisa sat on the sofa in a relaxed but poised way and I was trying to check her out. She was dressed very smart in a business skirt and blouse. Her legs looked great and her tits filled the blouse perfectly. I could hardly concentrate on our conversation and spent most of the time mentally undressing her and fucking her in my mind. Lisa was being assertive with me, she told me to start digging. "Get close to some of those women in the office and see what you can find out," she ordered.

I agreed to do my best and promised I would leave no stone unturned. For some reason I didn't dare tell her that Dave had travelled to the far east with his admin clerk, Gina. Now Gina was about 23 and very attractive. She had long dark hair and dressed very casually in a way that most women would feel was a little too laid back for work. Gina could pull it off though. I don't know why I didn't tell Lisa about Gina travelling with Dave but something just instinctively told me to keep that from her. Lisa didn't ask so I assumed she already knew or Dave had told her he was travelling alone. I didn't stay long at Lisa's. I tried to drag the conversation out and talk about other things but Lisa was a very cool customer. Sexy as hell, but very cool with it. This made me want her even more. I returned home and wanked a couple of times thinking about her. Then it was back to work over the next couple of weeks.

When Dave and Gina returned from their business trip to the Far East, Gina was showing off a lovely gold watch she had bought at the airport. She claimed she had used her bonus to pay for it but really everyone thought that Dave had bought it. Could Gina be the one he was fucking behind his wife's back. She was certainly fuckable. Gina was one of those women that create an instant impression and then the more you see her the more you want to see even more. I would bump into her several times a day and each time I was only ever thinking how good she looked. Her and I built up quite a rapport and often shared a joke. I would say Gina was the first 'friend' I made in the office and started to talk to each other about life outside work. Gina had a boyfriend but they argued a lot and she was often in need of cheering up. I was more than happy to take her mind off things with a steady line in office banter and one liners. Things were moving along nicely with Gina and I told her I was single but occasionally had a casual thing with an old girlfriend that suited us both. I didn't want her to think I was a sex starved saddo.

One morning, Gina was crying. I walked into the office where her desk was and couldn't help but notice. Gina was trying to compose herself but there was no hiding her upset.

"What's the matter?" I asked putting my hand on her shoulder. This was the first time I had ever touched her. Electricity shot through my arm as I rested my hand on her. I could only think how badly I wanted to put my arm round her but I managed to control my urge and just concentrate on consoling her. Through the tears she managed to tell me she had finally split up with her boyfriend and he had just called to tell her it was completely over. Apparently he thought Gina was cheating on him. At that moment Dave walked in. He gave me a look and I gave him one back with a shrug. It was a blokes way of asking what was going on and the other blokes way of saying it was nothing much. Dave walked out. Gina was pleased he had gone, as she didn't want anyone to see her crying. I asked her if she wanted to go home but she said she was better keeping busy at work. "I have get back to work, tell you what......let me buy you lunch." Gina smiled as I suggested this and thanked me for being a friend. A friend was the last thing I wanted to be but lunch was set and off I went for the rest of the morning. I thought that if Gina's ex was right then it might be Dave who had been fucking Gina at work. It didn't bother me. I sort of liked the idea of Gina being up for a bit of fun so hoped in a way she was prepared to dabble at work. Lunchtime couldn't come soon enough.

Gina looked a lot better when I saw her for lunch. As we got into her car we made a pact that we wouldn't discuss her break up. She wanted to just spend an hour laughing and joking and not feeling sorry for herself. I was more than happy to oblige and we went to a nice pub and enjoyed a very pleasant 45 minutes chatting. I was trying to be flirtatious and felt she was reciprocating. When we got up to leave we nearly bumped into each other. We stopped, stood very close and just stared at each other. Gina had been laughing and she smiled straight back at me. We both said sorry at the same time for nearly bumping each. We smiled at each other warmly. I put both my hands on her upper arms and stared at her still smiling. She carried on smiling back. I went to kiss her and moved my head forward. She kissed me before I had a chance with just a closed mouth and said thanks for being a friend. She could see I wanted a proper kiss but insisted we got back to the office. When we got the car we both sat inside and put our seat belts on. Gina didn't turn the ignition on but instead just sat there thinking.

"Did something just happen then?" she asked referring to the brief kiss.

"Nearly" was my reply.

"Hmmmm!" she said. Then she unbuckled her seat belt and leaned over to me slowly. This time it was her wanting a kiss. I wasn't going to pass up the opportunity and soon we were kissing passionately. She broke off the kiss and sat back in her seat.

"That was more like it!" I said. Gina smiled and turned the ignition on. We hardly said a word as we drove back but just smiled and enjoyed the moment. As I was getting out of her car she asked me if I wanted a lift home. Naturally, I accepted and I told her I would come and find her as soon as I finished work. The afternoon really dragged as I clock watched my way through the hours looking forward to seeing Gina. I received a text from Anna asking to see me that evening but I didn't reply. I was only thinking about Gina and decided Anna would have to wait.

Eventually the day ended and I went to find Gina. She was waiting for me and greeted me with a huge grin. We pulled out of the car park in her car and she started to drive.

"You seem happier than this morning." I said breaking the silence.

"It's thanks to you," said Gina. "When a relationship comes to an end, some people need to be alone but not me, I just need to be with someone."

"Glad I can help!" I said sounding a little used.

"Don't get me wrong, John. You're not here to help. I really like you and I'm now free to take our friendship further if we both want."

"What have you got in mind?" trying very hard not to make it sound like a leading question.

"Come back to my place. Spend the evening with me and lets see how things go. We can get something to eat and talk and see where that takes us" explained Gina with such confidence that I didn't even consider saying no. I received another text from Anna but carried on talking to Gina as she drove to her place.

Twenty minutes later and we were at Gina's flat. An hour later and we were eating a bowl of pasta salad that she had created as we chatted in the kitchen. As we both finished our food, Gina stood to collect the plates. She walked around the table to where I was sat but instead of picking up my plate she leaned over and kissed me. I kissed her back. She moved her face away from mine but stayed close, about 2 inches. Then Gina whispered, "Lets make love!"

She took my hand and I followed her into her bedroom. With no conversation at all Gina started to undress. I marvelled at the way she was revealing her naked body as each piece of clothing was discarded. With a little nod from her, I began to do the same and soon we were both naked and falling onto the bed. We hugged and then climbed under the covers. Gina was smiling and complementing me on how much she had wanted to do this since the day I joined the company. We didn't get started for over half an hour but instead just talked and kissed and stroked. My cock was hard and I think she enjoyed feeling my arousal against her leg. With almost no prompting I knew that the time was right and I just climbed onto her. She stared into my eyes and opened her legs fully. I had been gently rubbing her clit a little earlier and my cock was now resting against her wet pussy. She adjusted her position and I slipped into her. There was almost no need to thrust and the entire length slowly sunk into her. Then we made love. I couldn't call it fucking because it was just a slow gentle motion that never really speeded up but just became more and more intense. Gina reached orgasm and moaned in total pleasure as I maintained my rhythm. After she had cum, she changed a little and became less active. She was sort of just lying there as I made all the moves. My mind started to drift and I was thinking how different this was to sex with Anna.

With Anna, her and I had begun like animals our first few times, but with Gina, I just couldn't imagine a hard fuck. Gina was too lovely for that and during our conversation she had explained how she hated calling it fucking or screwing. She couldn't easily use the expression "having sex." Gina only wanted to call it "making love". After she came, she sort of stopped trying and I lost interest. I was also used to receiving complements on my cock. Anna and Rachel always openly appreciated my fine upstanding todger but Gina never even acknowledged it. She just quietly enjoyed letting it make her cum. I still hadn't finished with Gina during our love making session when I decided I wanted to get round to Anna's and get my rocks off there instead. Gina was a gorgeous young girl but nothing compared to Anna in bed. I gently slipped out of Gina's pussy after a little while. She didn't even remark that I hadn't cum.

"That's the first time I've made love to anyone from work. I hope you can keep this secret!" she said. I believed her and felt pleased with myself that I had some information for Lisa.

I smiled and took in the site of Gina's naked body. We chatted for a little while and then we got dressed and she took me home. A lingering kiss on the lips and a calm "see you tomorrow" was how we ended our evening. It wasn't the end of my evening though. I got straight on the mobile to Anna who was happy to hear from me. She asked where I had been but I said I would tell her later.

As I walked up Anna's driveway, my cock grew hard anticipating the sex I was hoping to enjoy.

"What can I do for you?" asked Anna opening the door and letting me in. I didn't even bother to ask where her husband was and just assumed he wasn't at home.

"Amazing sex, charming company and more amazing sex" I answered.

"Can't help you with the company!" she laughed, "So it will have to just be the sex!"

I grabbed her and we kissed. We were soon in her room and for the second time that night I was undressing in a woman's bedroom and climbing naked into bed with her. I stopped Anna from sucking me off as I didn't want her to taste Gina, instead we just fucked each other to exhaustion for about 20 minutes. I slipped out of her and took great pleasure in shooting cum all over her tits. Anna was happy to rub my cum all over them. A little later she did suck my cock and I was waiting for her to notice a little taste of Gina but she didn't.

As she sucked my cock I loved the site of her head bobbing up and down with her butt sticking in the air. I soon made my move to enter her from behind and gave her a second good fucking. Again I withdrew just before climax only this time I came all over her back. She remained on all fours as I jacked out my cum all over her. She was slightly out of breath and her body heaved. I just stared at the cum on her back and then wiped my cock against her cheeks. She wiggled back against me and my eyes were drawn to her arse. I wiped my cum around her arse and against her hole. I think she wanted me to fuck her anal style and I teased her more by rubbing my cock head into the cum and then toying with her opening. Then she fell forward onto her front and the moment was lost.

Anna rolled over onto her back and I thought about all that cum being wiped on the sheets. I fell on top of her and we kissed.

She couldn't keep her hand off my cock and she stoked it staring at it. "Such a lovely cock," she said.

"What do you like about it?" I asked.

"It's so hard and just the right size. It fits perfectly"

"Sure does," I agreed.

Anna adjusted herself so she could lift a leg and she slipped my cock back into her. "See that? Perfect!" she said.

Then we fucked gently for a little while and the slow movement reminded me of Gina. I decided whilst fucking Anna that I would like to try Gina again. I just needed to bring out the wild side in her and I wanted to get her to complement me on my cock the way Anna does. Anna reached between her legs and took control of my cock. She used the swollen head of my cock to rub all along her pussy lips and she pressed it against her clit. By controlling the pressure she could increase the pleasure and she came again. As she did I drove my cock into her and her legs wrapped round me and held on tight. I pumped against her body and came deep inside her as she continued to grip me with her legs.

We later went downstairs to the kitchen and sat drinking water and coffee. We talked about my job but I didn't tell her about Gina. I honestly didn't know how Anna would feel if I said I had been fucking someone else. I pretty sure she wouldn't have been very happy if she knew it had been earlier that evening. Besides, I mind my own business and don't mind anybody else's so I didn't really even consider telling her. She did tell me that Lisa wanted another update so I told her to arrange something. I still wanted to get inside Lisa's pants and another meeting couldn't hurt although I didn't for a minute think I could ever crack Lisa.

..................................................

The next day I got a call from Anna saying we were to all meet at Lisa's house at the end of the week. Lisa's husband, Dave was travelling again and would be away for the whole weekend. I think Lisa wanted some company as much as a progress report from me. Anna took me to Lisa's. My cock swelled as I sat in the car on the way. Anna of course knew this and rubbed me commenting she hoped we would get a chance later. Lisa's house was in a more rural area down some country lanes I thought we would probably be able to find somewhere secluded on the way back to pull over and fuck.

Once through her electric gates and down a long driveway, we arrived at Lisa's and she answered the door looking immaculate as ever. She gave Anna an affectionate sisterly hug but I only got a cool hello. She showed no warmth to me at all and although I found her extremely attractive, the cool bitch routine as starting to piss me off. Lisa didn't ask for an update straight away but instead opened a bottle of wine and we all sat and talked. At first she wanted to know how the job was going and then we talked about Dave. I told her that I still had no evidence but I had eliminated one suspect from my enquiries. I didn't confess to fucking Gina but explained that we had become good friends and via her confidence, I was very sure there was nothing between Dave and Gina. Lisa didn't get quite so angry this time. She sighed and probably concluded Dave wasn't fucking anyone at work. I thought this might be the end of my spying escapades but I valued my job a lot now and didn't want to blow it.

We were well into the next bottle of wine. Lisa and me were both getting a little tipsy but Anna was holding back cause she was driving. The whole time I was checking Lisa out whilst trying not to give Anna any indication of my interest in her. Then suddenly all the lights went out and Lisa screamed. It was a power cut and it turns out Lisa is terrified of the dark. Not just a touch surprised like most people but totally petrified. I quickly pressed a button on my mobile and this provided a little light. As our eyes adjusted we were able to see quite a bit. Lisa calmed down enough to stop screaming. Anna was reassuring her and explaining to me Lisa's huge fear of the dark. I looked out of the window and could see no lights. The whole area was out of power. Being out in the country, dark was dark. Without my phone we wouldn't be able to see a thing. Lisa was still petrified.

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