Written by wildchildtammy

24 Jul 2015

My name is Tammy. My profile is under ‘’wildchildtammy ‘’. This is a diary entry.

You can read about my job (so the diary will make more sense) in my profile

The events in my diaries are true, other than that names have been changed.

Just before I went to Europe to work on the charter described in my last diary, my boss hosted a formal part at the house for 30 people.

My main job of course for the family is as au pair to the two small children, but I also look after the running of the house, like the monthly budgets, groceries purchases, staff and so on. My background in the hospitality industry on the charter-yachts is a good fit for this, so when there are parties and so on, I am roped in to do the arranging, leaving my boss and his wife to see to the guests.

This was to be a full formal function- black tie, ball gowns, and so on, and a guest list of note. There was a small band, several waiters, valet parking, and a bargirl (-lady? -man?).It was to be held in the formal dining room, opened to the enclosed patio to accommodate all the tables.

Many of the guests have security staff, so the first part of the day before was seeing to them, showing them around the estate together with our own security guards. Then getting the waiters sorted out, the bar set up, and so on and on. I had 2 assistants to help me, so it went reasonably smoothly.

(Odd people, these security people- guns, radios, crew-cuts, and VERY big! They all seem to be made from the same mould!)

Anyway, I saw to the preparations, and the day (or rather the night) of the party arrived. Guests were due at p.m., so after making a last check, I went to the cottage on the estate where I stay when I am working late or early, had a bath and got changed.

For work with the children, I have a uniform- a blue skirt , pants or long shorts (depending on the weather and what we are doing) and a white blouse or white t shirt, with shoes or sandals to match. For the party, that was not going to be right- much too casual, as I would be seen by guests as I supervised the event.BUT,if I dressed in a formal dress, it would look like I was a guest.

So, as I did for the Cape Town function, I found a compromise- a black knitted dress with a very low front, which showed a lot of cleavage,(and no bra) and quite short, but not mini, black high heels, and very sheer tights. The dress is too clingy to wear underwear, as it will show, but I had tights on so it was fine. I thought it looked sexy but not too much so, but also suitable for my work-role.

I was back at the function at 6. All was in order, the band ready, the drinks ready, the snacks warming in the kitchen. I got the candles lit, and turned the lights in the dining area down. Guests would arrive in the entrance hall, and go into the reception room to have drinks. Then at 8, they would get asked to go in to dinner. After dinner, there would be speeches, then desert, then back to the reception area while the dining room was cleared, so they could dance there later. All fairly normal stuff.

The guests had all arrived, and were having drinks. I was standing near the bar, just having a look to see that the waiters were doing their job. A man approached the bar to get drinks (the guests could either order from a waiter or get it themselves if they wanted.) He was very good looking, around 45-50, with beautifully cut dark hair, and a very expensive dress suit. When he reached for the drink, I saw he had a Patek Philippe blue and gold watch- wafer thin. It’s one of my favourite watches, but at around e12,000 (R200k?) a bit out of my price range! He had a most stunning smile. He reminded me of George Clooney or a young Sean Connery. That sort of confident, manly, rugged yet sophisticated look. He smiled at me as he got 2 drinks, and I watched him walk back to the far corner where he was standing with a slim blonde woman in a full-length backless red sheath dress. As he gave her a drink, she turned slightly, and my mouth dropped open.

It was my friend Anne!!

(You will need to read my diary of “Anne and Jono” of 2 FEB 2015 to appreciate my reaction.)

I had no idea what she was doing there! i knew she had been there befroe with her husband, before we played, but not since, and i did not know she would be there that evening. And I was concerned. I don’t like it at all when my “other life” comes into contact with my normal day-job, and I take a lot of trouble to make sure it doesn’t, but here she was! I stared at her, making sure it was her- and it was. She was obviously with the man who had come to the bar, and I had no idea who he was either.

She looked stunning- she had a full-length red dress on, soft and flowing, with a strappy top. Her blonde hair was tied up, and she had only a little make-up on- she looked like a model.

There was nothing I could do, so I left the reception area, and went to get the seating plan- when they went in for dinner, I could see where he sat, then get his name from the plan, and then work out who he was and why Anne was with him.

At 8 p.m. my boss asked the people to go through for dinner, and I watched from the serving passage, seating plan in my hand. I identified where he was sitting, and looked him up. He was listed and Mr… and partner, so HE was the guest, and Anne was with him, but it clearly was not her husband.

Dinner was served, speeches made, and they broke for drinks before going back for desert. I was standing near the kitchen prep area, which is off a passage which leads to a bathroom, when I heard a voice call me.

I turned- Anne was standing at the end of the passage, smiling at me. I walked to her, unsure.

To cut a long story short, she said she had been invited to accompany her escort, Michael, who was an old friend, known to her family. Her husband was overseas, and it looked like he would be there for several months- (I got the impression that it may be permanent, but I did not pursue it) so she was available, and there was, at face value, nothing wrong with him asking the wife of a friend, knowing that she was not busy. He was divorced, and was often asked to escort a single woman in his social circle to functions. She finished talking, and I just waited. I knew there was more, and often silence is a great way to find out the rest!

Sure enough, the rest came out! Yes, was sleeping with him (who wouldn’t, as she said!), AND she knew I would be there- when we had met, I had chatted a bit about my job, and she recognised the names of the children I look after from a charity function she and my boss’s wife had attended .She was not sure, she said, but from my description of the house and the family, she was fairly sure where I worked. Her ‘’date’’, Michael was the Chairman of a company that did business with one of my boss’s companies, which is why he was there.

So- there we were.

A while later, I saw Anne again at the dance floor- Michael had gone to have a cigar outside with some of the men. I went over and sat next to her.

“Michael is really good looking”” I said

‘’Isn’t he just? And he is very good at other things too!”” she replied with a grin.

“”Does he know you play “” I asked

‘’Yes. I told him about you, me and Jono, but without mentioning your name l. He was so turned on, it was one of the best fucks we have had! He kept trying to get me to tell him who you are, but I did not. It would be fun to play with him here!’’.


‘’yes’’ she said ‘’why not?’’

’’I can think of several reasons’’ I said, ‘’not the least of which is me getting fired!’’

‘’only if we get caught. Relax. If you are game, I will set it up. Do you know of a private place here? Let’s make it a surprise for him!’’

‘’no kidding it will be a surprise!” ‘I said.’’ The only place private enough would be the cottage where I stay here. But that would only be after I am off-duty. You can get to it via its own entrance round the corner. Where is his car parked?’’

‘’the valet parked it’’ she said ‘’I don’t know where’’

‘’ok, then it’s already in that area- the cars are parked on the lawn next to my cottage, so you could walk there, then drive from there home’’

I left the dance area, unsure what to do. On the one hand I would not mind playing with Anne and the guy, but to do it at work was very risky. Then again, with all those people, and everything working well, the chance of anyone finding out was slim.

About 11 p.m. I was standing near the Port and Cigar bar, when Anne came over, Michael on her arm.

‘’Tammy dear, I have been telling Michael so much about you, and about this lovely home. Won’t you show him the art-works and the Chinese pottery collection?’’

(My boss has a world-class collection of ancient Chinese pottery, and some rare and original art in a display room)

Michael was looking at me, with a lot more attention than previously. As I looked away, I caught him eyeing my boobs, looking me up and down. All he needed to do was to lick his lips, and he would look just like a dog that has seen the Sunday roast! I got the idea that he now knew who I was.

We went downstairs to the lower level, where the art- room is. On that level are only 3 rooms, one of which is the art-room. Next to the art-room is a small study, which is not used at all- now and then mrs boss uses it, but not often. I led them to the art- room, and we went in. They looked at the art and the pottery. While Michael was at the far end of the room, Anne whispered to me :

‘’I told him who you are. He is so horny now- I could see him getting hard as I told him!’’

Anne and I were looking at a particular pottery jar, when Michael came up behind us. He stood behind me, looking at the jar, and then put his arms around my waist, tentatively. I didn’t move, and he lifted his arms, his hands higher now, just under my boobs. Anne looked over her shoulder at him, and smiled.

He cupped my boobs in his hands, fondling them gently. My nipples got hard, and he played with them a bit. I could feel his body pressing against me, and I felt his cock against my bum. He lifted my hair and kissed the back of my neck. It was so erotic standing there, Anne watching him caress me.

He took the top of my dress, and pulled it down slowly, exposing my boobs and my hardening nipples. Before he could touch them, Anne leaned forward and started to nibble on my nipples, first one then the other.I knew I had to get out of there quickly-much more of this and we would be fucking on the floor with all the Chinese figurines looking on!

It’s at times like this that my peculiar sexuality really strikes me. Many women say they are ‘’bi’’, or more commonly ‘’bi-curious’’, whatever that may mean (is it like oysters- you are not sure if you will like it, but you will try it once?), but standing there with the strong maleness of Michael behind me, his hands, his body , his cologne and slightly rough beard, and in front of me Annie, her soft lips, her hair tickling my boobs, her perfume- I really could not say which I preferred. If I had to make a choice, which would I choose? No idea! And it’s not just ‘’which would I fuck’'- it’s which would I/could I love, be with, stay with. Not a clue! I guess that’s what being truly bi means- confusion.

Anyway, we needed to get out of there before things got out of hand.

I gently pushed Annie’s head away from my boobs, lifted my dress back up, and led Annie by the hand out of the display room. Michael followed, smiling like the cat that got the cream.

Going back upstairs, I explained to Annie where my cottage was, and how to get there.

‘’there are 3 cottages’’ I said. ’if you go out the front door, turn left, and follow the path around the side of the house, you will see a tall hedge. The path goes through an archway in the hedge. Keep on the path, and you will see the three cottages at the back of the estate. Mine is the one on the right, as you approach them. There is a high wall around them, with a gate to each one’s garden in the wall. I will leave the extreme right-hand gate open. Come in, and you will be in the cottage garden. Don’t fall into the little plunge pool, and my stoep door will be open.I will let you know when I leave the party. You can say goodbye to my boss, and say you will walk to your car. He will probably tell you about the path I have just told you about, because the cars are parked on the grass between the cottages and the hedge. They can’t see the cars from the house because of the hedge, so they won’t know whether you have actually driven out or not.’’

An hour later, some of the guests had started to leave, so I found mrs boss and asked if I could go now. She agreed, and I said goodbye to mr boss. I saw Annie with a group of people, caught her eye and indicated with my head that I was going.

She nodded slightly.

I walked along the path to my cottage, and went in. Putting on the gas fireplace, I dimmed the lights and put on some Blues music softly. I was not sure what to do about my dress. I didn’t want to get it damaged, but I figured that I could be careful, so I left it on, and just touched up my makeup.

10 minutes later there was a soft knock on the stoep door. I opened the curtains, and let Annie and Michael in. I offered drinks, and once we all had a drink, I sat next to Michael on the couch. Annie had kicked her shoes off, and was curled up on the carpet against his legs (the cottage has under-floor heating, so sitting on the warm carpet is lovely in winter.)

The music was soothing, and after a long a tiring day I was tired. I lay back on the couch, content to let the music wash over me. Michael put his arm around me, and I snuggled into him, warm and relaxed. I had my eyes closed, and I felt him gently stroke my face, pushing my hair back. His hand moved down, resting on the top of my breasts. Turning to me, he began to kiss me on my neck and throat, then on my cheek, then on my mouth. I opened my mouth, feeling his tongue probe, his lips nibbling on mine. His hand slid under by dress top, stroking the top of my breast. He pulled the dress down, off my boobs. My nipples were hard and ready, and he bent forward and kissed them, then sucked on them, making the areolas pucker up.

I put my hand on his leg, then on his crotch, feeling his cock, hard and erect, straining against the fabric. I undid his belt and lowered the zip. His cock filled his jockeys, the tip of it visible at the waistband. I pulled the underpants down- his cock was rigid, big and hard already. I stroked it, my hand around its thickness.

I stood up, stepped out of my dress and put it on a chair. I turned and stood for a moment in just my stockings, facing him. I was sure he could already see that I was wet, through the stockings!

Ann, who had been sitting at his feet watching this, stood up now. She undid the top of her dress, unzipped it, and let it fall to the floor in a puddle around her feet. She unclipped her very sheer bra, and stepped out of her tiny panties, also facing him, her pussy shaved smooth and completely hairless like mine. I pulled off my stockings also. Michael looked from the one to the other of us.

‘’an embarrassment of riches!’’ he said with a smile.

‘’well’’ said Anne’’ now you have what you wanted- both of us !’’

He stood, undid his tie and shirt, and threw them onto the chair next to the couch. Sitting again, he removed his shoes and socks, then his pants and underpants, till he stood equally nude in front of us. He had a really nice body- very toned and firm, no fat, and he clearly worked out a lot. His was (surprisingly) shaved, and his cock stood out, big and hard.

Annie took the initiative, taking him by the hand, and leading him to the chaise longue. She sat him down on it, and pushed him gently onto his back. He lay there, arms by his sides, his cock pulsing every so often. I went up behind her, and put my arms around her, hugging her to me.

‘’are you wet yet? ’I asked her

‘’why don’t you find out?’’ she said with a giggle

I slid one hand to her pussy, tracing a line along her slit. She WAS wet, her lips opening as my finger rubbed them. She parted her legs slightly, and I let my finger go inside her pussy lips, feeling the slick wetness. My other hand I put between my own legs, and felt my pussy as wet as hers. I pushed one finger in and out her pussy, slowly, touching her clit as it came out each time. She reached behind her back, found my pussy, and slid a finger into me immediately, making me gasp.

Michael was still lying there, watching us fingering each other. He was masturbating himself, the veins on his cock standing out. It was really thick, more than I had realised.

Annie went over to him, straddled him, and, stroking his cock, guided it into her cunt .He immediately started thrusting into her quite quickly- he was obviously very aroused by now. She arched her back, and rubbed her clit with one hand.

Michael looked at me. I had two fingers in my pussy, and was fingering myself quite rapidly, getting very turned on. He motioned to me to come closer. I did so.

‘’come up here’’ he said, indicating the chaise longue. I was not sure what he meant.

‘’sit across me’’ he said

I sat over his chest, my pussy facing him. He began to stroke my pussy, putting one finger into me, then two. Annie reached around from behind me, and played with my nipples as she rode up and down on Michael. He took his fingers out of me, and held my hips, pulling me towards his face. I lifted myself slightly. He pulled me closer, until my pussy was at his mouth. Parting my lips with his fingers, he licked along my slit. I was soaking wet, the outer lips of my pussy glistening with my juices. He thrust his tongue into my pussy, licking my clit hard, then thrusting deep into me. I moved back and forth, almost grinding my pussy into his face.

It was an exquisite sensation, Michaels tongue deep in me, Annie elegant fingers tweaking my nipples and stroking my boobs. Annie took one hand away from my boobs, and felt between my legs. Her fingers found my bum-hole, and she took some of the wetness and rotated her finger in my hole, pushing it a little way in.

Now the sensation was overwhelming- all of me was being stimulated. Michael took his mouth away from my pussy, and drove his fingers into me, deep.

Annie took her finger out of my bum and away from my boobs and gripped Michael’s hips, and suddenly began to rub her cunt hard backwards and forwards, jerking her hips, almost slamming into me. Michael thrust up and down, and she came, yelping and moaning. She seemed to keep cumming for a long time, the movements getting slower.

Michael was still fingering me, alternating it with licking my pussy, even as she came.

When she was done, she got off him, and stood next to us.

‘’what’s your favourite position?’’ asked Michael

‘’reverse cowgirl’’ I said

‘’ok, cowgirl, climb on board! ’He said with a smile, still stroking my pussy

I stood up, got a condom out of my bag, and rolled it onto his slick wet cock. Then I got onto the couch, stood over him, and squatted down, my back to him, taking his cock and letting it slide into my wet and swollen pussy.

I was not kneeling, but squatting over him, so I could move a lot. His cock filled my pussy even though it was very wet. It felt great. I rode his cock for a while, getting more and more aroused. Annie came and sat at the foot of the couch, facing me. She reached to me, and began to rub my clit, her other hand between her legs, fingers in her cunt.

Michael was thrusting hard now, as I jerked my hips back and forth, grinding down on his cock. Annie rubbed my clit harder, fingering herself almost violently. I felt I was going to cum, and I stopped going up and down, and just went back and forth. As I started to cum, Michael gave a series of quick jerks of his pelvis, and began to cum inside me. Annie was so aroused by this that she came again, her fingers flying in and out her cunt, her hips bucking. Michael and I came for ages, groaning and thrusting. We stopped cumming almost at the same time.

We slowed and stopped, and I sat with my weight on him, his cock still in me.

When I had recovered, I got off him. His cock was still quite hard.

Was sat there for a while, naked and exhausted.

Then Annie and I took our clothes and went to the bathroom to clean up.

When we came back, Michael went.

We sat and had coffee, still all warm and relaxed. They left at around 2 am

I have seen Annie since then, on her own. I think we are going to be good friends!