My secretaries – overview

[stockinglover21]

She climbed off me and slid between my legs. She took me in her mouth. Despite climaxing hard I was still semi stiff. She licked and sucked me. She took each ball in her mouth and gently sucked. She alternated between caressing my balls with her hand teasing the head of my cock with her tongue and just taking me whole in her mouth.

I could not believe it. I was hard again. No rest, no recovery time. She did not waste it. She climbed back up, put me inside her and rode me furiously. She was warm, wet and tight and gripped me like a vice. This was not slow love making. She was fucking me hard. With hardly any warning I erupted again and spurted even more of my spunk in her. This time I went soft and slipped out of her.

I told her to lie down and moved to go between her legs but she stopped me and said not yet. Hold me, kiss me and tell me how happy you are that I am your secretary. Make me feel loved and wanted and treasured. Hold me tight.

I did. Her bare breasts were hard against my chest and I held her head in both of my hands whilst I kissed her on the lips and said “you make me feel so happy I could burst with joy, thank you for being with me”. She started crying. I tried to comfort her but she just sobbed and sobbed. Full on tears and a heaving chest. I just held her tight and waited for the tears to subside.

What is wrong? Nothing she said, I am just being silly. I don’t believe that tell me I replied. The words came tumbling out of her mouth.

I love my husband very much and when I think of what I am doing I feel a wh*r*. But I do not want to stop. It is not just the money and the life you have helped me with. I love you too. It is not the same. It is a different kind of love. I feel wanted, desired, cared for and yes I want your cock inside me all day long. I feel alive and so naughty when I am with you. I think of you all the time. I wonder what you are doing. My husband fucked me last night and I had to stop myself from telling him to do what you do to me. All I could think of was hurry up and cum so I can plan what I will do to you in work today. I do not want to leave my husband and I do not want to jeopardise your marriage either but I need to know you really care for me and that I am not just a woman who you pay to fuck.

I held her tight, I kissed her gently on the lips and I said I think you are great, you are sexy, intelligent, caring and just lovely. I think about you all the time and I pinch myself every day because I cannot believe you want to spend time with me. I love you in a similar way you love me. Now hold me too, so we can enjoy this moment.

[stockinglover21]

We have had a huge amount of fun. More orgasms than I can count and sexually I have never been happier. She has grown in confidence as a secretary and has evolved sexually.

Once when she had done a mistake she insisted that I spanked her. Did nothing for me but she loved the fact that I was disciplining her. She has discovered that she has both submissive and exhibitionist tendencies.

The wine bar near the office has good food and we often go there. It is part of a chain and one of the waitresses there is great fun. We have developed a rapport with her and she often chats if quiet. Secretary 4 loves to play with my cock through my trousers or lift up her skirt so that the waitress can see she is wearing just stockings and no underwear. I would like her to take out my cock but she is nervous of going that far. I have fingered her to climax a few times.

We have told the waitress that we are secretary and boss and that I am paying for the additional benefits and she is fascinated. She has joked she wants to work for me and whilst secretary 4 plays along with it she has made it clear that my cock is for her alone and not any other “employee”. We have fun and I am happy.

There are mishaps. The day the sofa bed arrived we fucked all day well into the evening. There was a big gap when we just cuddled and I used my tongue and fingers to make her climax. I could not manage a fourth time and stayed only semi hard despite hours of caressing and sucking. However before she left it sprung into action and she jumped on me and I climaxed inside her. The fourth time that day.

The time had flown by and it was very late. She changed into her going home clothes and left. When she arrived home hubby was horny and started fondling her as soon as she arrived. Her pussy was soaking wet from all day climaxing and 4 loads of my cum and she managed to evade his grasp by saying she needed to pee. She cleaned up and thought she had managed to get away with it but her wet knickers were in the laundry basket and he must have been suspicious because he brought them into the living room and started ranting.

She played the innocent and said they were from the day before when he had fucked her but he said they could not be because they were too wet. She called him a moron and did he think she had had a quickie at the train station and he said no you are fucking your boss. She stormed off to bed calling him mental and of course he was not 100% sure and he was horny and so she made him apologise profusely before she let him shag her.

From then on she always cleaned herself up before going home. She was sure he checked the laundry basket every night but there was no evidence.

A few weeks later he turned up at the office unannounced (which meant he had taken an afternoon off work and travelled in 30 miles) but as luck would have it we were genuinely frantically busy on a project and it was crystal clear we were working hard. He made some feeble excuse about a romantic surprise date night in London but she made him wait in reception for two hours whilst we finished the project. He saw first hand how hard she worked and of course we were super professional.

She was in the bathroom when he arrived and heard me greeting him. She managed to change out of her sl*tty work clothes into her home clothes but had to stuff her work clothes in the cistern in case he needed to use the bathroom. He did and saw nothing.

That was a very lucky escape.

A bigger lucky escape was when her period was late (usually very regular). He had only cum inside her once that month (she has deliberately decided to make him cum from her hands or mouth - he does not last long and then he falls asleep before he can get inside her) but I had come inside her about 30-40 times.

She was not pregnant and we breathed a sigh of relief.

[stockinglover21]

The weirdest experience was meeting her mother. She had a hospital appointment in London and arranged to meet up with her at the office.

Her mother insisted on meeting me and saying how grateful she was to me for helping her daughter. She asked her daughter for a cup of tea and whilst she went out to make it her mum spoke to me.

She said her son in law is convinced you are fucking my daughter. I have told him he is being silly but to be clear I am not stupid you obviously are. She has more confidence and is more mature by far, and constantly speaks so well of you. Nobody helps a new employee out as much as you have without a reason and that reason is pretty obvious.

She said you are obviously paying her well and treating her well and she is happy. Don’t screw up her marriage. Be more careful and try and leave her with some desire to fuck her husband because he has complained to my other daughter’s husband that since she has worked for me their sex life is about 90% less and she is clearly not happy having sex with him.

My secretary at that point came in with the tea and her mother acted as if she had not said a word and just chatted generally. I did not know whether to mention anything but decided her mother was an ally and would calm down my secretary’s husband provided we were not caught. So I continued the pleasantries and kept quiet.

[pantysniper]

Loving it Keep them coming!

[Horny Dog]

Thoroughly enjoying this thread. Looking forward to the next update

[Bluetrueuk]

Your tale was so exciting, and erotic. It's a fantasy I'm sure many of us dream about. I have really enjoyed each and every adventure, each building up the suspense of what happens next, and my imagination was running wild as I pictured that delightful girl teasing you so much. It's very rare that a story gets me hard, but yours definitely does.
Thank You.

Originally Posted by stockinglover21

Our first day of full sex had come to an end.

I left that evening feeling fantastic and could not believe how many times I had ejaculated nor that I had managed to satisfy a young woman so many times.

This was the start of a 9 year adventure. There are so many stories and so much fun. From now on my descriptions will not be so detailed. In truth there is little variation between one blowjob or intercourse than another and if I keep describing them we will all be bored.

Instead I will post about the situations we found ourselves in and what she wanted to do and where. Without giving away too much. The idea of being paid for sex made her so horny and brought out an adventurous and exhibitionist streak that she did not know she had. Living 30 miles away from where she worked allowed her to have two separate lives and she was determined to play up the sexy/slightly sl*tty secretary to the max.

As she said in her own words “Cock sucking, cum swallowing, pussy flashing mistress each day - wet wipe carrying, food making and clothes washing mother each night and weekend”.

More adventures to follow.

[Bluetrueuk]

Superb, really enjoying your experiences with this delightful and sexy secretary of yours. So happy that she is experiencing proper knicker wetting sex now with you. No girl should have to put up with 'wham bam thank you ma-am' sex, the husband doesn't know what he's missing,

[stockinglover21]

I have mentioned before how we had become friendly with a waitress in our local wine bar. I would love to describe threesomes and riotous sex with her but there has not been any.

However, we have flirted with her shamelessly and she has participated. My secretary, virtually every time we are in the wine bar and it is quiet, hitches up her dress so that she can see she is wearing stockings and suspenders and no underwear and often will stroke me when she is talking to us. Usually through trousers but sometimes she unzips me and fondles my hard cock directly. Never pulls me out but it is obvious what she is doing.

I have fingered her to climax a few times and the waitress has always stayed to watch and has a huge smile when my secretary tries to keep the conversation going whilst she is climaxing from my fingers.

She has told her my fingers could make a stone orgasm and my tongue is amazing. She has told us she is engaged and happy with him but she has said she is fascinated by our dynamic.

We have had one experience with her. It was my birthday and my secretary invited her to celebrate with us. No expectations about sex but she promised her great fun, food and wine. The only condition was that the waitress had to wear a dress and stockings/hold ups and had to prove at some stage in the evening that they were stockings/hold ups and not tights.

She agreed and the night was set. Cocktails at the Savoy, a great dinner in a cosy restaurant and late night drinks were agreed upon.

She turned up in a little black dress and so did my secretary. They had obviously co-ordinated their clothes. They both wore a plain gold necklace and black nylons. I quickly discovered my secretary was wearing black stockings and no underwear but I was respectful of the waitress and did not ask or allow my hands to wander.

Cocktails at the Savoy were superb. We drank three in quick succession and were in a great mood. We had fun. We chatted mainly about our time together and how it had started and the waitress asked many questions and seemed genuinely interested.

We left the Savoy for the restaurant and in the taxi the waitress slid up the side of her dress to prove she was wearing hold ups. We all laughed and the mood was great.

In the restaurant we had a booth and my secretary insisted we all sit on the same side with me in the middle. My secretary went in first and as she sat down she hitched her dress to her waist so I would have full access. The waitress gasped but we reassured her nobody could see. The table cloth was long and we were both next to her.

I explored throughout the meal but made sure it was gentle and occasional so that the waitress did not think she was a third wheel. Two bottles of wine later and the alcohol was affecting all three of us and we were laughing and giggling constantly.

My secretary then said she needed the bathroom and as is usual both women went together. I did too but was back before them. When they returned my secretary said they were changing places and to my delight and surprise the waitress hitched up her skirt to the waist and sat down. I had the briefest of glimpses as she quickly sat down but I still saw that she was wearing hold ups with a lace band, no underwear and there was a thin pencil line of hair leading up an inch from the top of her pussy.

I looked across at her and smiled. She said she had never done anything like this before. She was not going to fuck me or even touch me but she had masturbated so many times to the stories my secretary had told her that she had to experience some of the fun. I could touch her but no kissing. I looked at my secretary who was beaming and mouthed “happy birthday”.

I ordered a bottle of champagne and the conversation continued as before except now my hand was wandering up the stockings of the waitress along the bare white skin to her exposed pussy. My fingers traced her pussy lips. She was already wet. I nibbled her ear and asked if that was allowed at the same time as my finger found her clit and caressed it. Mmm, she said, which I took as a yes and spent the next 35 minutes drinking champagne chatting to both women, stroking the waitress’ clitoris and pussy lips whilst my secretary had unzipped me and was fondling my cock casually. Every time the waitress was building to a climax I slowed down and teased her lips or caressed her thigh. The tables were turned and she was now struggling to maintain a conversation through shallow breathing and the build up to an orgasm.

I had my own issues though. My secretary knew what I was doing. She tried to time her stroking of my cock to my stroking of the waitress’s clitoris. We were all slightly drunk at this point and the timing was out. It was great fun though and we could not quite get off. The waitress squirmed and gripped my fingers but she was not quite there. I stopped. I thought this was just not going to work.

The waitress turned to me and said in a deep slightly menacing voice. Don’t you dare stop. I need this now. That focused me and I renewed my attention to her clitoris. My secretary slowed down my fondling and I concentrated on making the waitress climax. I did not have to wait long. Her breathing became more rapid. Her pussy started contracting. She was stifling a moan and then it happened. She convulsed. She really shook. Her face contorted and she just blurted out F…U….C….K and kind of slumped. She was loud. The people in the booth across heard and looked. But of course they could not see anything.

My climax was building too. My secretary had speeded up and was intent on me ejaculating. I tried not to but it was futile. I groaned and spurt after spurt jetted out of my cock. She caught most in her hand but some was in my underpants and a wet spot quickly formed in my trousers. She took out her hand showed the results to the waitress and then licked my cum off her hand and dried it with a napkin.

We were all silent for a minute and then the waitress said I need another drink. I gave her mine and ordered another bottle of champagne. We chatted as if nothing had happened. We laughed and had a great time.

Nothing more happened. I arranged separate cars to take us to our respective homes and that was the end of a fabulous night.

It was never repeated. We remained friendly with the waitress and flirted but she did not want to come out with us again. She said she had a great time and an unforgettable experience but at the end just before she climaxed she wanted my cock inside her. If we continued again she would want to fuck and that would screw up her relationship and impending marriage.

My secretary also did not want to repeat it. A lovely birthday present for me but she has been there. So aroused by my fingers that only a cock would do and she knew that the waitress would want me to fuck her and she did not want to share me with anyone else.

[stockinglover21]

One Monday the new sofa arrived. It was placed in the filing room.

When they arrived she had only a shirt on - no underwear at all and only two buttons done. We had not locked the door. We rarely have visitors and just did not lock the door and so when they walked in they had a good eyeful. Her shirt just about covered her pussy and bum but it was clear she was not dressed for work.

It was 2 middle aged guys and they stood and stared and then one recovered and asked where she wanted the sofa bed. He emphasised the bed. She directed him to the filing room and she followed them in. I went as well.

The sofa bed was covered in plastic and she asked if they could wait a short while whilst she took off the plastic and would they please take it away. They quickly said yes. They were enjoying the view.

She went over to the sofa bed and bent from the waist pulling at the plastic. Her shirt rode up and her very pert naked bum was completely visible. I was instantly stiff and guessed they were too.

She asked one of the guys to pull the plastic off the left side whilst she pulled it off the right and both guys rushed to the left hand side. Of course they were now seeing her bare breasts down her shirt and I could not see but I expected they could see her bare pussy too.

With all the plastic off she asked them to show her how to convert it into a bed which they did. She then jumped on it bouncing up and down. Her bare pussy was now clearly visible and they were mesmerised.

She said to me boss, you need to come and try this out and at that point I think one of the delivery guys was about to have a heart attack. Enough though I wanted to fuck her, I did not want an audience.

Later I said, these guys need to get back to their deliveries. Let me show them out, lock the door and then you and I can really try out the bed. The guys were smiling and as I showed them out, one of them said I will be thinking all afternoon about you two trying out that bed. I laughed and said whatever you imagine I promise you it will be even better for me.

It was but the detail will have to wait until my next post.

[stockinglover21]

I let out the delivery men, locked the door and returned to the filing room. My secretary was already naked, on the sofa bed, with her legs wide open and one hand rubbing a breast and the other rubbing her clitoris.

I am wet, honey and I want you to fuck me hard now she said. No delay just pull your trousers down and get inside me. So I did as I was told. I climbed on the bed undid my trousers and put my cock inside her. I was hard from her show and I just thrust away hard and rapidly. She was very wet but could still grip me and within a couple of minutes I knew I was going to cum. I pulled out intending to go down on her but she said don’t stop get back inside me. I did and started thrusting again but as soon as I did I could feel my orgasm approaching and I groaned just shooting my sperm inside her.

Sorry, I said but you told me to get inside. She laughed and said I wanted you to cum quickly. It will take you a while to get hard again and until you do you can touch and lick and bring me off many times.

Kiss me first she said, so again I did as I was told. I kissed her full on the mouth, our tongues probing each other’s mouths. I nibbled her bottom lip I kissed and caressed her neck and ears and then I moved down between her legs. I spread her pussy lips and just explored with my tongue. Her outer lips, her inner lips, her clit. They all were lavished with attention. Her breathing increased, she started to writhe, I had her attention now. I focussed more on her clit and she produced even more juice. My face was very wet and she was writhing noticeably now. The moans were starting, she was enjoying it and I had no intention of stopping but wanted to last it out. She was either hornier than I thought or I mistimed it because she shook and groaned loudly. Her first orgasm of the day.

I did not stop. I wanted her to have more and I just continued. She continued moaning. I wanted her to have a second one but it was not happening yet and so I varied the pace, I teased I probed and the I found the right spot and the right rhythm and she became very vocal. Yes, yes yes, that’s it don’t you dare fucking stop. Yes yes yes. She climaxed with force. Her legs gripped my head as she did and she said stop. I need a break.

We cuddled and kissed. I played with her hair she ran her hands over my chest and we talked. I needed that she said. My husband fucked me twice last night. Trying to prove a point. I did not climax once despite thinking of all the things you do to me. I ended up going to the bathroom and finishing myself off.

I do not want to get out of this bed today. I need you inside me again so let me get you hard again and I will get on top. She did. It took about 20 minutes of using her hand and mouth before I was hard enough but she did it. She got on top of me put me inside her and used my hard cock as a dildo. She just thrust down on me and back up fast and repeatedly. She was breathing hard and so was I. She climaxed first but did not stop until I did. It was so good I could not think of anything but how good it was. She had done all the work but I was exhausted.

She got up and went to her bag and then came back. Go to the bottom of the bed she said and watch me. I did and she took the handle of her hairbrush and put it inside her. She thrust it in and out. She pressed it against her clit and teased around her lips. She had a good rhythm established. She quickened her pace and I could see that she was building up to a great orgasm. She did. She shook she groaned she gripped that hairbrush like it was in a vice.

I was hard again but she said she needed a break and so she spent the next 20 minutes sucking me and playing with my cock. I was not about to cum and her jaw was aching and so we just cuddled. I fell asleep and she woke me by sucking me before she had to leave to go home. What a way to wake up. This time she just continued until I spurted and she swallowed every drop.

We kissed again and she cleaned up and changed into her wife clothes to go home.

Another great day at the office.